A Sexual Progression

Finally. The moment I had been waiting on for since I turned 18. I could move out now as I had just graduated high school. My boyfriend of the last 5 years had arranged for me to move into a very reasonably priced apartment under a restaurant in a secluded industrial section of town where we could continue our love affair without prying eyes of neighbors or family asking questions.

I was so excited; a place to explore ourselves!

We had initially met 8 years earlier when Fred, Kay's husband who was the lady who babysat me frequently introduced us. Fred had never been nice to me as the sight of me being diapered by his wife into my teens disgusted him. He said that for he thought I was a girl when they first started babysitting me as mother would usually have me in one of my sisters old nighties and a diaper already on when I was dropped off for the evening. Later when I was 10 or so mother just dropped me off before work in training pants and Kay would change me into an overnight diaper and dress me in my sisters old nightgown just before bedtime.

Harry was a friend of Fred's who would come over occasionally in the evenings to make contacts on their ham radios and have a few drinks in a room above their garage. Kay would encourage them to allow me to watch and sometimes leave me with them for an hour or two. This went on for a while as mother worked evenings and father was seemingly always working on the road doing contract construction.

With a sister 11 years older and a brother 8 years older mother had always called me the "little mistake" whenever she referred to me with her friends. She had also told all her friends that I was going to be a girl and reminded me constantly that I should have been one. My sister took care of me when I was young and would play dress up with me in all her and her friends old baby clothes and dresses after bathing and changing me. I liked the attention and was disappointed when she stopped playing with me at about seven I think. Being it was 1966 Mother even let my hair grow out in a long "Beatle" cut, dressing me as a little girl when we went out shopping downtown, She said it was easier to change me if needed in the women's restroom. My brother had also been in diapers off and on until probably age 11 or 12; my earliest memories are of the screaming fights many night as he refused being diapered after again wetting the bed. We shared the same room but I was diapered in the crib and put to bed an hour or so earlier and pretended to sleep as I cried. I learned that resisting what mother said would result in a beating and end up in a diaper anyway so I never talked back when it was my time. I was only left alone with him a few times when mother would leave a short time during the day. One of those times I asked him if he would play dress up with me when I was five and surprisingly he said yes but only if he could put me in my sisters old blue Baby Doll nightie and frilly diaper cover. I was so excited; it had been ages since I had played with my sister. We actually played a while and then I kissed him like I would do with my sister all the time; he kissed back. Then he tickled me until I had completely wet the diaper and had started to cry. He got real mad that I had wet and said he wouldn't change me unless I did him a favor......... After I was finished doing what he told me he was very nice; I told him he tasted good and laughed. He washed my face then gave me a model airplane of his I always wanted, He also told me it was our secret and he would hurt me bad if I ever talked about his "favor" I did to anyone. That was the only time that would ever happen.

One evening at Kay and Fred's house several years later when I was 11 things were seemingly not quite right. Kay had just finished diapering and dressing me in that same blue baby doll nighty when I heard Fred yelling at her about something. Kay went to talk to him but he pushed her down and slapped her. She ran crying out of the house and I thought I heard the car leave. I was still on the bed and scared to death. Then I heard Fred walking to the room swearing as he threw open the door. I curled up on the bed and was crying so hard I wet the freshly pinned diaper. He told me to "stand up you little sissy girl". I did as I was told still crying so hard I couldn't breathe. He looked me over completely and made me turn around once. He sat down on the edge of the bed and told me in a soft voice to come over to him and sit on nice uncle Fred's lap. His soft voice was a little less scary so I went over to him and straddled his leg facing him. He leaned over me and gave me a kiss on my forehead saying everything was alright and aunt Kay would be back in a couple hours. His breath was real strong with what mother always called "booze breathe". I pushed away and he became very angry again yelling at me to come back; then he reached out and yanked me back into his chest and then kissed me on the lips. Now I was terrified and not knowing what to do I just blurted out that I knew a secret that would make him very happy. By the time Kay finally came back into the bedroom to check on me a few hours later I had been washed clean an hour earlier so she just woke me enough to change the very soaked diaper. Fred had fallen asleep on the sofa I guess. I still had the taste in my mouth; different from my brother but still good.

I never asked if Fred had told Harry about our secret but for some reason he had taken a special interest in me.

Mother had held me back a year for school even though I would have been one of the oldest in first grade if I started on time. I was still having daytime wetting accidents and wore a diaper and usually a dress at home because I was easier to change wearing one. Mother had full control and would give out her love when she felt it was required to ensure I never questioned her commands. Not like that was going to happen based on how my brother had been treated when ever he questioned her authority in any way. Sometimes I would be in my room by myself for hours on end reading.  When I was 12 I just started crying and she would come in and ask why; always checking to see if I had wet yet. I was alone with her by then as both my sister and brother had cleared out about the day they turned 18 and they didn't come back much. Father continued to work away from home for long periods but had moved up in the company enough that mother no longer worked. I was her primary focus; I was 12 and she was 48. It took me many years to figure out why that timing would be significant.

I had no friends from school as I had been "special" with a couple other kids who were allowed to go to the restroom whenever we wanted and had to spend lunch recess at the school nurses office getting a diaper change if needed. I was in training pants into junior high and always was excused with a doctors note from any phys-ed classes. Most kids thought I was retarded but I always did better than them in school grades as I had nothing else to do but read and study. in my room avoiding confrontations with mother.

I was still at best "petite" by the time I turned 13 which was a significant age as mother started to let me change and pin my diapers on my own. She would come in and inspect then put on the plastic panties if she thought I had done well. I was even allowed to try out regular underpants a few times but usually had an accident.

Sometimes she would check me before she went to bed and if I was wet she would change me. By this time I become used to enjoying the feeling of being pampered and having mothers hands clean then apply diaper rash cream over my rear and little penis that had been going hard for several years by then. One Valentines day night mother came in to change my wet diaper in a very sexy blue baby doll nighty. I didn't notice at first as I was so use to the normal routine and the pleasure of her touch that I usually kept my eyes closed. As she changed me she told me that absolutely no other girl would ever be interested in a skinny little girly boy that had to wear a diaper and had pimples that had started to break out as well. She had told me over and over for years that the only one who would ever love me was her; every year at Valentines day at school I would make her my Valentine and give her a present as I had done earlier that day. Of course by the time I had been changed I was completely relaxed; the "stiffy" as mother called it had been taken care of and I was in a clean, dry diaper. It was then that mother cradled me in her arms and gave me a bottle to suck on. She had done this many times before, usually the reason was to get me to take some medicine in the formula. This time though was different; I felt really good. After I finished the bottle she offered her breast by pulling down the strap of the baby doll; I took the nipple and suckled on her milk until I fell asleep. I really liked the taste and would often ask if I could have more which she sometimes said yes until one day I asked not knowing one of her friends was in the next room.

It was about this time frame that Harry suggested to mother that I go with him on the ham radio exercises that practiced emergency conditions should there be a natural disaster that knocked out normal communications.  Even father thought that was a good idea so a couple weekends later I was going with him in his "Ham Van" into the wilds while they set up a communication network and practiced refining the emergency response procedures. Harry knew about my wetting problem as he had seen me for years in diapers and he let mother know he was well equipped in the van to discreetly deal with it. Mother was less enthusiastic than father was as he was looking for something he could say his sissy, pimpled and diapered teenager was doing other than hiding in his room. I was allowed to go!

Harry and I went out on the first weekend and had a lot of fun; I mostly took care of changing myself in the van and the other guys were real nice to me when we were all together. He even let me talk on the radio some even though I was not qualified.

Harry worked in a pharmacy supply company and was married to a nurse who worked nights and swing shifts. They lived 20 minutes away so the only time I saw him was when we did the ham radio club events.

Harry was married to a high school girl when he got her pregnant as a senior. They lost the baby and his wife had become quite rotund over the 7 years of marriage. She worked nights in a nursing home and was rarely around when I was there which also was very rare. Harry who was maybe 30 was as average as it gets; a little overweight and both were regular church goers which my parents were not.

It was during one of the ham weekends we were out that a severe storm broke out and caused some flooding that stranded us a couple extra days. We did a great job along with the others but it was going to be a while before we could get out as the rain continued. It got much colder so Harry said we should both sleep in the back bed area of the van to share body warmth. I was starting to get a little scared so I readily agreed. It was so cold out harry stayed in the van while I tried to diapered myself after stripping to a T-shirt with the last dry diaper mother had packed. I had stuck myself with a pin and started to cry like a baby. Harry instantly came and held me close and said he would finish putting the diaper on. By the time he was done and put the plastic panties on me I had stopped sobbing. When he got in bed with me I hugged and kissed him; first just on the cheek as I told him I loved him then I kissed him on the lips and told him he was the first person who had ever really been nice to me, He kissed me back and said he loved me too. We started kissing much more passionately as I helped him undress. When I saw his erect penis we both stopped and looked at each others eyes. Eventually I reached out and pulled down the front of his underpants revealing a penis larger than my brothers but smaller than Fred's. I started to lean down to please him like I had done to the others but he stopped me. He said I did not have to do that and he would still love me even if I didn't continue. What Harry didn't know then was that I really loved the total attention he would give me for at least a few minutes and that I really loved the moaning, groaning and feeling of total control I would have until I tasted my reward.

By the time we were able to drive out Harry had allowed me to please him multiple times.

We continued this way for over a year but as I turned 14 the acne became worse and I became more depressed despite Harry's efforts to cheer me up. One day he told me about a pill I could take once a week to help get rid of the acne. He had easy access to it at the pharmacy and had some with him now. It was called estrogen. I of course was completely excited as my life had become hell with mother regularly making me lay my head on her lap while she popped my pimples. It would hurt so bad I would wet my pants so she would put me in a diaper before she started. She would even decide to do this in front of neighbors. The one time I told her I was going to make father tell her to stop she responded by making father kneel down, put his head in her lap while she popped his "blackheads" in front of me. I was old enough to get the message and  never tried to resist her commands again.

I was taking as many of the estrogen pills as Harry would let me and within a month the acne had reduced dramatically. I also felt more relaxed and noticed that my chest was getting a little "sensitive" and I was less likely to get a "stiffy' the few times mother still diapered me. She even said she thought my little pee pee was disappearing which proved to her I was supposed to be a girl all along; mother was always right.

By the time I was close to 16 I had developed pert little titties, a shapely rear and had lost almost all my body hair which had been minimal to start with. The shrinking of my pee pee was more than offset to me by the benefit of much clearer skin.

I continued to have daytime wetting accidents using a folded diaper in my underpants and plastic pants. At night I did my own diaper, which I usually did without mothers help. She would still sometimes come unannounced into my room and check if I was wet at all then fully clean, cream then diaper and me on the spot, saying she didn't want me to get a rash.

On my 16th birthday Harry picked me up at the house and took me out for dinner as my parents were both busy. After dinner we drove to their house which I had only been in a couple times in the 3 years we had been together. He said he had a special birthday present for me in the basement where he had his radio equipment. there on a fold out sofa bed were 3 pink and 1 blue boxes with bows. He kissed me and told me to open them; the largest one first. I undid the bow and opened the box to find a beautiful blue mini-dress that was lace from just above the breast line to a collar with a little bow on the front of the collar. It was lace in a vee in the back down from puffy shoulders to where a zipper came up from below the tight fitting gathered waist. I said it was beautiful and began sobbing but Harry quickly kissed me and told me to open the other boxes. The next one had 3 padded bras and 3 panties in white, pink and blue along with a garter belt and 3 sets of matching stockings. the last pink box contained 2 pairs of high heels. I was completely in love with him and wanted to put it all on right then. I hugged and kissed him until he calmed me down a little and then told me to open the blue box. He sat next to me as I opened it. Inside was a make up case with several lipsticks, rouge and eye shadows. Under that was a royal blue satin and lace Baby Doll Nighty with matching lace bikini panties! I kissed him lightly and took the make up, nightie and panties into the little basement bathroom.

What Harry did not know was that Fred who I had continued a relationship with since their baby sitting time would occasionally invite me over to see his latest ham radio gear. I knew what that meant and was ok with with pleasing him as I really enjoyed the temporary power and the tasty reward.

Fred had noticed the changes in my body as the estrogen made its effects apparent and had become more aggressive in his demands each time we were together. As the next door neighbor who knew all my secrets he had substantial power.

Only a week before Harry was to give me my birthday presents Fred had taken me. It was something Harry and I had talked about for almost 2 years, culminating our love with full penetration and deposition of his seed inside me .  As much as I enjoyed his orgasms in my mouth and the taste of his satisfaction I desired the feeling of him doing the ultimate act of love with me.

This feeling was robbed of me by Fred in an afternoon act that lasted at best 30 minutes.

Fred saw me coming home from school on a day he knew no one was home and told me to come on over in a way I knew he needed to be satisfied. Kay was no longer much of an influence as she and mother had discovered Darvon.

I went over directly not bothering to drop my school stuff. Days from being 16 I had beautiful long hair, very nice firm tits and an absolutely perfect ass. Actually I was proud of my body at that point; zits were minimal and Harry said I was gorgeous which is what was important to me.

Fred and I did the usual "hows stuff" stuff that we always did before I sucked him off. This time he had other plans. Kay was away and he immediately lead me into their bedroom where he started pulling off my  clothes. I did not put up much resistance as I had learned long before that it was futile. When he pulled off my baggy jeans he saw that I was in lace panties.

Mother had noticed a year earlier that my body had changed as my acne problem went away. She would come into my bedroom or while I was taking a bath any time she wanted. Once she came in and took a look at me drying off after a bath she stated that I was indeed a girl the side affects of the acne treatment was true. That caught me off guard; Harry had gotten Mothers permission to give me the estrogen..... She asked me if I was confident enough not to wet my pants that I could wear girl panties sometimes; I said yes.

From that time mother gave me girl panties to wear any time I wanted, She said she was so tired of changing diapers she was happy to have a dry undies sissy who would make it a point not to wet her panties.

Fred saw the white lace panties and became obviously  erect even with his pants on. I tried to undo his trousers and perform the usual service but he threw me back on the bed and dropped his pants and underwear in one motion. Only seconds later he was on top of me and pinning me down  while spreading my legs. I actually resisted some and received a backhand slap that dazed me enough that I went limp for a few seconds. By then he had me secured and began the insertion of his cock into my little boy pussy as he called it and he slowly tried working it in and out as I cried in discomfort and fear he was hurting me. He climbed off of me and told me not to move. A minute later he came back with a jar of Vaseline, told me to spread my legs wide then pushed a glob up my little boy pussy with his finger. Then I saw him smeared more on his erect penis.  I knew what was about to happen and went into total submission as he raised and spread my legs again.....

This time his insertion attempts were slower and more rhythmic as he kept telling me to relax and enjoy his cock. Fortunately we was not real big and when he finally pushed through into me I let out a moan which evidently pleased him a lot. The feeling wasn't pain but it wasn't pleasurable either. His breathing became labored and by now my legs were just spread on the bed with him pumping on top of me. He laughed when my pee-pee started to get hard from weight of his body rubbing against it and told me I must really be enjoying the ride. I couldn't stop my erection and I started to come in several spasms that evidently made him climax several times before he just collapsed on me. As soon as my erection started to go limp I was peeing myself which made Fred get off me and stand there cursing at me. Crying and reaching for the towel he had laid under me to dry myself I went to my knees in front of him and looked up into his eyes. I had stopped sobbing as I knelt  and he stepped towards me. He tasted like cum, body odor and pee as I sucked and licked him to clean up the mess. Fred immediately became stiff again and held me by my long hair until he again spasms several times before depositing a little load of cum into my mouth which the taste which suddenly made me feel calm and relaxed.

Fred took me into the shower with him and he cleaned me up and then had me redress so no one would suspect what he had just done to me.

So a week later I am with Harry who I really love and he loves me now dressed in a sexy blue baby doll nightie with a little lipstick and eye shadow ready to step into what we have talked about for years. I have been wanting to feel Harry penetrate me and own my body which he has helped create with the carefully regulated estrogen. I hoped Harry had no idea that Fred has already broken me and I am scared he will wonder why it is so easy to penetrate me. After Fred I was so sore I kept using Desitin at night (with full diapers and plastic panties to cover the odor) to soothe my sore boy pussy making sure it was up inside as well. It didn't take too long before I felt better and went back to my girl panties during the day.

When I stepped out of the bathroom into the basement Harry just said wow. He walked up to me and put his arms around me as I kissed him passionately on the lips throwing my arms around his neck. He reached up and cupped my firm breasts then lifted me onto the fold out bed covered in the blanket from the van. I sat on the edge and began hungrily undoing his belt and unzipping his pants. As he took off his shirt I pulled his undies down and his cock popped up and hit me in my lips. Harry's cock was a bit bigger than Fred's but not by much. I instantly knew he would be able to make love to me without causing any more discomfort than I had felt with Fred. After I had sucked him for a few minutes, Harry went and brought out a tube of something called K-Y jelly. He said it would be better for both our pleasures. He laid me down and gently spread my legs then applied some to my rosebud. He did the same to his erect penis then put it down, looked me in the eyes as he told me he loved me and lowered himself down on my quivering body. I barely had said I loved him too as I felt his cock reach my entrance then with only a little thrust he penetrated and slid gently into me. He stopped several times to ask if he was hurting me and kept adding more of the jelly so I would not be hurt. It didn't hurt; but I acted like it was just a little to make him less suspicious it wasn't my first time. It felt almost good especially after the experience with Fred. Harry started the same rhythmic stroking that Fred had gone into but this time I was enjoying Harry's tender kissing and hands caressing my breasts, waist through the baby doll's lace. I somehow instinctively wrapped my legs around him as he sped up his pace and his breathing became faster. Again I could not stop nor did I want to stop my own erection and as I cried into orgasm he lifted up from me a little so he could look into my eyes. He again said I love you then did maybe three more thrusts before moaning loudly filling me with multiple squirts of his warm cum. He rolled off to the side and I leaned over and gave his quickly relaxing cock a brief cleaning with my tongue but not so much stimulation that he was disturbed from total ecstasy of the moment. After a few minutes lying and holding one another catching our breath we went to the shower together.

I had learned from the earlier Fred fucking that I needed to have as little water in me as possible as the penetration made me wet pretty heavily, especially after my mini-boner went flaccid. I smiled to myself that the only thing dripping wetness was my boy pussy from all the cum he had seeded me with. Once in the shower we soaped each other up and played a little while kissing; he quickly got erect so I stroked him several times then turned around and bent over offering him my wiggling ass if he wanted. I felt him grab my waist as he easily slipped back into my still well lubed pussy; it felt great and I could feel my bladder completely let go which was just fine in the shower.

We both got dressed; me back in my boy clothes save for another pair of the new red lace bikini panties with a bow on the front.

All the new clothes Harry had bought me would need to be stored in the van as I had no place for them except maybe some small panties and 1 lace bra.

We saw each other at least once every week or two and would only occasionally make love, usually in the van. Every year there was a ham radio / electronics convention and one was scheduled about 4 hours away; Harry said we should go as his now rotund wife and my parents were fine with it. We would go to a campground nearby for 3 days! As soon as he picked me up in the van I changed into a simple shorter length side zipping pleated print skirt and a loose scoop neck pull over blouse covering a padded A cup bra. I had the usual diaper folded in simple white panties with plastic panties to keep the leaks contained. The pleated skirt covered the diaper easily and whenever we stopped at no one saw anything other than a 35 year old guy with a cute girl. I always used women's toilets and never had a problem; though sometimes dressed in boy clothes I would start to walk into a women's restroom!

During the 3 days we made love maybe a dozen times, going to the show just long enough to get our tickets. At the show I was easily the best looking girl in the crowd which began to make Harry nervous. I admit that I did flirt a little with the guys; it was exciting getting so much attention from strangers. So the last evening wore the sexiest dress Harry had bought for me as we were going out dancing after the show, It was a short black step into that had an open back and just had a strap that went around my neck to hold the front up over my breasts, The tight fitting waist showed off my curves perfectly while the skirt was short in the front and scalloped much longer in the rear that showed off my rear perfectly. I wore the French style stretch bustiere that had a padded push up bra and garters built in. Black lace stockings and dark red high heels. All of this Harry had bought me at K-Mart over the past year. I had decided earlier in the day that I would not be in a diaper this night so I was extremely careful to limit any fluid intake during the day. 

When Harry saw me he was a little concerned but before we went into the dance so I calmed him down with an amazing blow job that relaxed him but also gave me a little smell of recent sex to go with my perfume. Harry was now early thirties with a bit of a belly starting and his hair was noticeably thinning in the front. He was still much more attractive than what his wife had turned into. I was about 115 lbs and 5'3" and as tall as he was when wearing heels, We were a bit of a miss-matched couple I guess which I picked up as soon as we started dancing. Mostly the event was attended by 40 to 60 year old's and only a few wives and very few what appeared to be single women. Some of the matronly looking women wanted to start a conversation with me but I said very little acting shy. Several guys soon came up and wanted to dance with me; Harry had said earlier I was his cousin and they could see his wedding ring so it was hard for him to say absolutely not, When a slow dance came on the guys knew he wouldn't get close to his cousin so they hit on me for each one. They were all pretty nice only feeling me up a few times which I loved. This constant activity also kept me away from the prying matrons. 

One younger guy guy at the end of my favorite song "In my room" kissed me and he could tell I think that I had sucked someone off as he said I had been a naughty little girl.We decided to leave a bit early as Harry was concerned about the attention I had gotten. We had always been extremely discreet and we figured we were far enough from home no one would recognize us. We had made it out to the van in the back of the hotel lot and just before he opened the door for me I planted a wet kiss on his lips and as I was about to say I love him a flash went off.An older heavy set guy was there smiling with a Polaroid camera saying he wanted a picture of the best looking girl at the dance; and by the way Harry looked real familiar to him? He started talking about joint ham radio exercises and it became obvious he knew who Harry was. He also said that the kiss Harry had just got from me seemed a bit strange from a cousin especially since Harry's hands had gone up my dress to caress my panties and garters. He laughed correcting himself saying maybe we were really close "kissing cousins". We stood there stunned and said nothing until I asked what he wanted to get that picture back and never say a thing about the evenings events. He said he and two friends had a room ant the Hotel and if Harry loaned his "cousin" to them for an hour or so all would be forgotten and the Polaroid would be ours as a memento of the evening. 

Harry started to say absolutely no way but I took him aside and told him neither of us had any choice. Harry told the guy as he put his arm around me and we walked back to the hotel that he would kill them if they hurt me; all the guy said is Harry would see me in 2 hours.He kissed me several times as we went back to the room and felt up my dress and titties not really noticing my tiny cock all tucked in the tight panties. He knocked on the door and the 2 other guys said wow John; you actually did it! They wanted to play with me for a while so they put on some music and had me dance "real sexy" as they pawed and kissed me. That lasted maybe 5 minutes before they told me to stop and drop the dress. I knew they would see my little penis for sure once the dress was off because I had started to get a little hard. So instead to by some time I dropped to my knees and told John to come to me. 

They all cheered as he came over and I began to take his belt loose and unzip his pants, As I pulled them down his erect cock bounced into my face which I kissed and pulled all the way into my throat. He almost fell backward and yelled "shit; this girl is good!". By then the other 2 guys had their pants off and were masturbating in my face as well. John blew his load in less than 2 minutes so I moved to the next guy and went after him as hard as possible to get him to come as fast as possible. He didn't even make 3 minutes before exploding in my mouth. At this point the last guy was trying to get me into a position so he could fuck me while I was sucking the other guy off. I stopped long enough to warn them I was likely to get pregnant if they fucked my pussy but I really liked it in the ass anyway. We got on the bed me kneeling on the edge with 1 guy in front of me to suck and another behind me fucking my boy pussy. I also pulled the dress down so my cute titties were offered up for play and the dress pulled up to expose that perfect but in pulled down wet panties framed by garters and sexy stockings. John recovered and took a turn at my pussy while I sucked whoever was in front. 

This went no for over an hour until they were all fucked out so I went into the bathroom and cleaned up as much as possible considering the evenings events. As they laid there I took the Polaroid and said I had a great time and if they gave me their phone numbers I would call them next time I was in town. The fucking idiots gave me their names and phone numbers! As a final good night kiss I knelt and gently licked clean their now sore cocks, When I was about to leave I asked if I could take a picture for them to see what I would be able to let them play with next time. I made them turn around and promise they wouldn't look until I was gone. I went in the bathroom, lifted my dress, pulled down the soaked panties and took a picture of my little but obvious cock.Polaroids took about 5 minutes or so to develop so as soon as I took it I handed it to them and left; in a hurry.When I ran out Harry had the van at the entrance so I told him to leave; FAST.We drove all night back to home but I had not only the photo of us kissing but all the names and phone numbers of the three guys who had fucked me.

I told Harry what had happened and he said he was so sorry and he would never get me into a situation like that ever again. I cried some to make him feel better but actually it had not been all that bad. All 3 of those guys were 100% in my control as soon as I entered the room and were that way for the entire hour and a half.

We never heard another word from any of them again but I kept the names and numbers for possible future use.

When I had turned sixteen a job at the local electronics / hobby shop was made available to me by another guy in the ham radio club that owned the place. It didn't pay much but the hours were flexible around my school hours. I had no extracurricular activities or friends at school maybe due to the long hair /  real baggy clothes hiding my now extremely feminine features and I hated being home with the parents any more than I had to. So it settled into a regular kind of schedule of school, work, study, blow jobs and occasional fuck fest in Harry's van. The other guys who worked there would sometimes invite me to hang around with them as they were all nerds which I did a few times but I was usually busy with studies and Harry.

We would talk in his van after sex and he would say he was going to get a divorce and marry me; I said I would go for a sex change operation as well but it would be really expensive. He said he loved me just as I was.

Mother and father finally split when I was 17 and left mother evidently enough income that she could keep the house and live fairly well. I had my own money and had even bought my own car with insurance. The car was where I now kept my growing collection dresses, panties, bras, stockings, sex lingerie and shoes. Mostly from Harry but I would buy some from Penny's mail order and pick it up at the catalog counter in the local store. Mother never saw it not that she would have cared much anyway by then. Penny's also had a "Home Health" catalog that carried adult diapering products that quickly replaced the old diaper and plastic panties that I had always been tied to. One special pantie for women was all satin and lace with a plastic lined crotch area that used washable inserts; I bought 3 pair in black, white and pink that looked really sexy in my normally short dresses and skirts when I was out in public with Harry.

When Harry wasn't available and mother was gone sometimes for a week or more with new "boyfriends" I would dress up at night and think about going out on my own.I finally had the courage to call up one of the phone numbers of the 3 guys from the conference a year earlier; all but 1 had their number changed by then. When I told the one I finally got a hold of he asked me what I wanted to stay quiet. I told him I was very horny and needed to suck some cock and maybe even get a good fucking if he was up to it. Of course he knew for sure I wasn't a girl which is why the others probably changed phone numbers and disappeared as much as they could. I couldn't even remember which one he was but they were all about the same; in their 50's with a paunch, an average cock and probably a fat bitchy wife like Harry's. I knew he was 3 hours away so I said I could meet him in a town about an hour away from me; he agreed on a motel near the interstate I could easily find. It was summer before my senior year so I had weekdays available so we picked a Wednesday to meet in the evening. I spent 3 hours getting ready shaving what little fuzz I had on my face, arms and legs making sure my pubic patch did not show outside the Bikini panties. 

I went with just a simple blue lace bra that matched the panties and sheer nylons without any garter belt. The print dress had puffy shoulders that vee'd in front but was high cut in the back, It fit tight under my breast down to a belt of similar material that had a bow in the front then flowed into a pleated short skirt that would flare out enough if I spun around to see my panties. Dressed this way I could be in a diaper until I arrived then easily change into the panties for a few hours of fun. By now I was good enough with make up and hair that I could walk in public with only appreciating looks from guys and disinterest from the women. When I arrived and spotted the truck he told me to go to I parked far enough away to change out of the diaper, clean up, put the panties on and adjust my hair and make up. The hotel was adjacent to a truck stop and it was not quite dark so several truckers noticed me getting out of my car and walking to Steve's truck; one whistled at me.

 Steve came out of the truck and quickly lead me to the motel room saying I was gorgeous and shouldn't be dressed like that in this place . He had already had drinks ready so we sat a few minutes and talked. I told him I wanted nothing from him other than as much cum and fucking he could stand for as long as he could last. I gave him a kiss and put his hand on my breast as I sat next to him on the bed then I took his other hand and put it on my little now leaking penis. He massaged both my titty and my crotch until I rotated down to the floor on my knees and unzipped his pants. By the time I had his cock out the pre-cum was showing so I took him in all the way cupping his balls gently then began to suck and draw him in an out of my lips. He took about 10 minutes to finally go spasmic and deposit a nice load of cum into my mouth which I let run down past my lps and onto my chin before I released his cock and gave him a French kiss with his own cum being transferred to him by my tongue. While he lay there and recovered I freshened up in the bathroom and put a pantie diaper on as I was hungry and needed to get some dinner. 

Once Steve was up and out of the bathroom we went out to a nearby chain restaurant that served alcohol. We were seated in a booth so no one much noticed us much other than the younger waitress that knew I wasn't in any way related to this guy or his wife as he had his ring on. In this place I wasn't way over dressed so we kept it low key, paid our bill then went back to the motel for another 2 hours of fucking and sucking before he had to leave. He told me I could stay the night if I wanted to as it was already paid for, We kissed a little as he left but I was no longer much interested as my pussy was dripping and I had gotten a decent amount of cum to drink. I decided to shower and put on a pull over gathered waist dress with a clean bra and the diaper pantie with a dry insert. I packed my bag, put on some sandals and decided to drive back. As I was walking to the car I heard some guys talking and they called to me to come over; I told them I had to go but 2 more guys came from behind my car and walked me over to the other group near the trucks. 

They wanted to know "how much?" but I told them I wasn't a prostitute to which they said great; it would be free then as they had been watching Steve and me all evening. So between the two trucks I was dropped to my knees while they unzipped and then began giving six blow and hand jobs which turned into one continuous blow job. They told me not to cry out as they would beat me but I had little chance as they slipped one dick right after another into my mouth. After a few minutes they all started cumming mostly in my mouth but also in my face and in my hair. I don't know how long it was but several of them left. Then a car shined its lights in our direction that finally made the last couple take off. I gathered up my bag and quickly made it to my car and drove off soaked in cum glad they had not decided to fuck me as they might not have appreciated my extra equipment.

After that experience I gladly went back into the same somewhat boring but secret routine with Harry, school and work saving up as much money as possible to be able to move out after graduation day. Amazingly no one really noticed or maybe just didn't care as I had absolutely no other social life spending all free time reading books.I had turned 18 months before graduation and could go to bars as well as drink 3.2 beer. Harry would take me to bars on the other side of the city as long as I dressed very conservatively, usually in longer length hippie type peasant dresses all from Penny's catalog of course. I liked them as I could use a full diaper which I needed if I was doing any beer drinking. 

We had a lot of fun dancing and talking but it was rare when we got together with both our schedules and his wife who was becoming less willing to let him out at all. That is when wie started looking for an apartment for me.That day of graduation was the last day at home as I had already moved all the girl clothes in after paying the rent and deposit. Clean but not fancy it was so secluded no one would even know I was there. Harry could come over any evening he could get away and feed me his cum and fill my pussy with his love. At least for 6 months it turned out.I hadn't seen or heard from Harry for an entire week whch had never happened before. He called me one evening sobbing uncontrollably saying that he couldn't see me anymore. I asked why and he replied that his wife was pregnant? Really? He told me he couldn't stand the sight of that fat nasty bitches stinky pussy as it made him sick to the stomach. Evidently that was not the case as I knew no one else would fuck that thing. 

Even though I was not 100% faithful I still loved him and I truly believed he loved me as well. But before I hung up on him he told me there was another issue; I had to move out of the apartment by the end of the month. Harry had been paying half the rent but had quit 2 months earlier so I had to leave. The place was already rented so no other option was open. I was so in shock of what was happening; Harry had been the only person who had been nice to me and cared for me. I suddenly realized I had flooded my diaper and came back to reality long enough to tell him I understood and had to hang up. I cried for 3 days, not going to work or to community college that I had a full tuition scholarship due to my grades. 

I had never done that before as school, reading and Harry were the only real positive things in my life other than the sexual addiction to semen and satisfaction of men cumming in me. On a Thursday before the end of the month I had already packed everything noting most of my clothes now were feminine with just enough boys stuff to do work and school figuring I would move back home for a few days to figure something out,. Guys I worked with were all dork / geeks with no girlfriends so they never questioned why I didn't have one. No one at school cared for the most part as it was a commuter college where everyone had other stuff going on. I was always treated better dressed as a girl as long as I kept it hippie level; not too much displayed....

Friday evening and make things right; he asks if I have the dress we went to the dance in the one trip out of town and I said yes, of course. He asked me to wear it when he came over at 7:00 Friday. I said I would and told him I still loved him; he just said he would see me tomorrow. I was so excited I had to change my pantie diaper into a regular but I didn't care because maybe he decided to dump that fat pregnant (maybe??) wife. When I got home from work on Friday I showered and shaved everywhere massaging body lotion on pretending it was Harry's hands caressing my breasts and now well rounded ass. He always loved my flat tummy and cute waist putting his hands there to hold me when he fucked me either on my back or doggy style. I did the bustierre, garters with the  fishnet stockings, bikini panties making sure I had nothing to drink since noon that day. The dress fit a bit more snug than it had that night but actually it looked a lot better with my more filled out figure. 

My hair was still straight and was conditioned to a beautiful sheen feeling almost heavy; instead of just letting it hang straight I pulled it back on one side to put in a flower clip above the ear kinda like I saw the Hula girls do. The fanciest clip-on earrings Harry had bought me and a pair of stiletto heels I had practiced walking in for months finished the ensemble. A touch of Channel No. 5 in strategic spots was the final touch. I was ready to hit a romantic dinner and Disco into the early morning hours!I barely had a chance to relax when the knock came on the door; There was Harry but a very large man was with him. I again was stunned as no one knew about us and we were always super careful no one would find out which was why we rarely went out to party at all after the ham convention incident. I would have wet I am sure but the shock was paralyzing as I just opened the door and let them both in.the large guy shutting it behind him once he was in. 

As I stood there Harry introduced the Hulk as Mac Donovan who quickly offered up his huge hand which I instinctively took. He lead me to one of the 2 chairs I had while he and Harry sat on the old couch that was there when I had moved in. From here on pretty much only Mac talked saying Harry had told him everything about our relationship from the time I was still a child. I could not believe Harry had betrayed me, actually us so badly to a strange person. Mac began to berate Harry telling him what a piece of shit he was for stringing me along for years knowing he would never follow through with all the promises he had mad. Harry occasionally tried to say something but Mac told him to shut up so forcefully I still wet some. 

After Mac calmed down a bit he smiled at me and asked me to please stand in front of him and slowly turn around. With Harry totally humiliated and me so full of emotion of hate toward him I decided to do the sexiest turn around I could considering the stilettos. It was a quick spin that made the dress rise up enough Mac could see the garters on the stockings just a peek. Mac smiled and stood up coming over to me before turning to Harry telling him he had given up the best thing that would likely ever happen to him. Harry started to stand up but Mac told him to sit which he did immediately. Mac then came up to me and put his hand under my chin to gently make me look him in his dark green eyes. While he did that his other hand began exploring the small of my back before sliding down to my ass which I encouraged a little by giving out a sigh. Then he took his other hand down my neck cupping my breast as it moved to my waist. When he had both hands on my rear he pulled me in close so I could tell he had a huge erection before leaning down and kissing my forehead. 

Now I was completely confused; I asked what was going on? Mac took me to the couch to sit beside him while he put his arm around me and told me the deal. Mac and his wife would put me up in there house free of charge until I could save up to get a decent place of my own. Food, utilities and even laundry would be included. Mac and his wife were into foster care for a decade but had stopped a year or so earlier but missed the company provided by the kids. On my pnot need to attend any other church functions unless I wanted to. Also, I was to only be dressed as a girl when on the premises except for going to wart I would have to do housework and show them my grades were kept up and my savings were growing. I would also need to attend church with them every Sunday but would ork or school. I looked at Mac and said that sounded fantastic and absolutely I would do it! Mac then asked if I was really over Harry and I hesitated enough that he said I needed to prove it to him, Harry and myself. 

He motioned for me to get up from the couch and told Harry to sit next to him. He then began motioning to me to come over to him seated on the couch. When I was standing between his legs he gently put his hands on my shoulders pressing down on them saying prove you are over Harry for him to see up close. I dropped to my knees while he unbuckled his belt while I unzipped his trousers. Once unzipped the boxers he had on could not contain the by far biggest cock I had ever seen. I worked it back psst the waistband of the boxers and then it sprung straight up into my face. I had to put both my hands around the upright shaft with only the head exposed just to confirm its size in my brain. I stopped and looked into Mac's eyes for a second before saying "goodbye Harry" than began licking and kissing the tip of the monster of a cock. It took fifteen minutes of sucking and pumping and licking while Mac pulled my dress down to my midriff to play with my breasts making them so hard they almost hurt. 

All this was finally getting Mac to the moaning stage. He was mostly quiet until he tensed up and started bucking a little as he filled my mouth and throat faster with his pungent cum, way faster than I could swallow forcing cum to squirt out of my cheeks making an gurgling type sound.With my mouth dripping Mac's cum I asked Harry if he wanted a last goodbye kiss; Mac chuckled a bit at that then told Harry to get out and go back to his fat nasty wife and likely a fat nasty kid soon. And by the way, do not ever try to contact either of us again unless he wanted to pay back all the rent money Mac had paid up and have his past exposed.Once Harry cleared out Mac handed me a tissue to wipe my mouth then we had a drink of whiskey he had in a flask from his coat pocket. The whiskey burned going down and he again chuckled a bit asking if I ever drank, I said he already knew about my wetting issues so I rarely had anything to make it worse; he said I was a smart girl.We talked a while giving me his address and phone number telling me to be there by noon tomorrow. 

He would be gone for the next week but his wife Margee was expecting me and also knew the entire story.I arrived at the gate of the house in their obviously upscale neighborhood with all my worldly belongings packed in the old car. A voice asked who it was and I replied "Alaina" and the gate magically opened. As I drove up to the house a lady asked me to park around back and come to the side door near the garages. By the time I was parked the same lady who introduced herself as Margee greeted me with a big hug telling me she  felt really bad about my horrible betrayal by Harry. She had me sit down at the kitchen table and said I had to share a bottle of wine with her to celebrate my new beginning that she and Mac were looking so forward to participating in. Margee was was an average size woman a bit plump with some attractive features including enormous breasts. As we sat and sipped the wine she told me about she and Mac being unable to conceive which eventually led them to taking in foster children for many years; they had even built this house with that purpose in mind. Eventually with the proliferation of drugs they couldn't deal with the kids as they got a bit older. At that point she showed me where to put my clothes in the laundry room as they all had to be washed before being allowed in the rest of the house; a precaution from the foster process. 

My other few items pots, pans and a 13" B&W TV were put on a shelf in the garage as they had everything else in the house I would ever need and I was free to use it.The talk included the rules of the house; I was to always be scrubbed clean dressed in clothes Margee laid out for me each morning, I was to call Mac "Sir" and Margee "Ma'm" and only speak when spoken to. Any hint of drugs or consorting of people Mac did not approve of was also forbidden. I was to keep the house spotlessly clean and serve Mac as he requested. In exchange I would have no expenses whatsoever other than my car and school tuition. Again I said I was in full agreement wondering if she was fully aware of what I had already supplied to Mac the evening before. 

Once all that was done she took me to the room I would be in temporarily while they set up a room for longer term. It was down a hallway that looked like the hotel hall I had seen at the convention. She took out a key and unlocked the door saying it had been a requirement for foster care. Walking in the room had no windows and looked like a hospital from TV. A single bed with steel head and foot board, a small white night stand and what appeared to be a large diaper changing table with a step up. A shelf on the wall had maybe a dozen cloth diapers and plastic panties folded neatly next to various cremes and powders. She told me to put my small bag of personal items on the night stand.I suddenly felt very wet as the wine took affect but Margee took the look as me maybe being hungry so she apologized saying of course I must be hungry and she was so sorry she had not offered any lunch. 

I said that yes a little food would be nice as I had skipped breakfast in the hurry to get out of the apartment.We went back to the kitchen where she made me a ham sandwich with a small salad; it was perfect. We finished the bottle of wine and I realized I was leaking from my daytime diaper so I said I had to change but my diapers were in the laundry room. Margee said not to worry as they had plenty as I had seen earlier. Then she asked if I had ever had a bubble bath, to which I giggled not that I knew of. She said to come with her down the hall to the bathroom between the foster bedrooms where she began running water into the tub sprinkling sweet smelling powder in the water producing thick bubbles. Once the tub was full we went back to my new bedroom where she helped me pull off my dress and my bra then asked me to please step up and lay down on the changing table. 

She pulled off my plastic panties then unpinned my diaper depositing it into a diaper pail I hadn't seen at first.. While I was on the table now naked she ran her hands carefully from under my ears to my toes carefully inspecting every inch of my bare skin sometimes pressing a little in some areas while watching my reaction. With the wine making me feel so relaxed I did not object to any of the attention. She asked me to turn over and did the same inspection on my backside before asking me to slowly get off the changing table. As I stood up with her steadying me I could feel the pee begin to trickle down my leg which she noticed and helped me quickly to the bubble filled tub.  As I sat in the tub she washed me and caressed me saying that I did have a remarkable figure for an amateur which I didn't understand at the time. As the bubbles began to fade she brought out shampoo and carefully washed my hair rinsing several times before applying a conditioner and working that in with a full hair and scalp massage. It was something I had never experienced before and it was mesmerizing. After a final hair rinse she had me stand up and completely showered me down in warm water before helping me into a warm fluffy towel. 

We went back to the changing table where I knew what to do without her saying a word. After I was lying on the table she took a diaper off the shelf, unfolded it, fluffed it a bit before bring it between my already spread legs. I lifted a little to allow her to slide it under me as I had done all my life. After  she applied  the rash creme liberally around my penis and pussy the diaper was pulled tight and pinned perfectly; not too tight but not baggy either. he plastic panties were next which were slipped on in one fluid motion as I lifted just in time for her to pull past my diapered bottom. What a good little girl you are Margee said as she helped me sit up on the changing table. She left for a minute telling me to sit there coming back with a pink bra, pink slippers and a white pull over dress that would easily hide the rather bulky diaper I was now in. Once dressed we went to a dressing table where she began combing and drying my hair with a blow dryer which was something I had never used. 

We continued to talk about my situation, school, work and a bit about the troubled foster children that they had cared for over the years. I did not ask many questions as I did not want to mess up what seemed to be a good situation developing. This was fully distracting me from the memories of 5 years with Harry I had to admit to myself as there was at least one other person, Margee, who seemed to be genuinely interested in me. After finishing with my hair she quickly applied a little lip gloss to my lips before taking me in front of a full length mirror in the hallway. I could not believe how full my hair was, it looked like I had twice as much and with just a touch of lip gloss I looked like an innocent 14 year old ready for church. Which is exactly what Margee reminded me we would be doing tomorrow morning. 

It was only early afternoon so we went back to the kitchen and continued to talk for several hours about my upbringing, my relationship with Harry and she spoke a bit about how she and Mac had met and ended up in this place. She seemed 100% straightforward and would occasionally interject things I needed to keep in mind while staying in their house. Mostly basic manners and etiquette but some other quirky type practices such as always do what Mac asks without any question or delay; something she did as well though she expected the same obedience to her instruction as well. Disobedience was not tolerated especially considering what they were offering in exchange and it would result in punishment or expulsion from the property. Considering the luxurious accommodations and the opportunity to save up money quickly, study and read my books in peace the choice was crystal clear. Plus, I had already experienced a bit of Mac's pleasure and wanted more....

As we finished a second bottle of wine Margee said we would go out to a local restaurant for an evening meal, I looked at her and she could tell I had wet again and said don't worry, I needed to change out of the church dress anyway for the pub we would be going to.We went back to the bedroom and she did the diaper changed and had me in a longer peasant style dress in in only a few minutes. We hopped into her BMW and drove a short way to a small pub and walked on in. Several patrons knew Margee as she was a hairdresser and assumed I was a foster child, but when they came up to chat Margee said I was one of the children they had fostered who was coming back to stay while attending community college. She basked in the approval of the people congratulating her on such an obvious success. 

We had salads and soft drinks which was fine with me as the wine was still having a strong affect. Going back to the house Margee asked me if I had ever had sex with a women to which I answered no, unless mother taking care of my "stiffys" was considered sex. She laughed and said technically it was not. By the time we were back it was getting late and with church on the agenda for the morning she said it was time to get me to bed. I was ready as well with yet another wet diaper due to the day of wine drinking I was sure. We went back to the bedroom and I was undressed with the wet diaper removed, put on the toilet to pee then put on the table. After a gentle cleaning she placed another soft, fluffy dry diaper under me then using disposable gloves applied a lot of diaper rash creme working it into my pussy while she spread my legs wide. What I did not expect was the large maybe 8" butt plug she pulled from the drawer then started to apply lubrication to in front of me to see. I looked into her eyes not saying a word and she responded by saying " you have experienced Mac in your mouth and know the size and power; we need to make sure you can handle him in your obviously tight little boy pussy". 

Moving one then several well lubed fingers in and out of me until I became fully relaxed she then quickly inserted the plug. While I was dealing with the wild sensations trying to relate it to Harry, Fred and the three guys from the convention in comparison she pulled up and tightly pinned the diaper on. Even though I had just peed I could tell I was peeing again even as she pulled up the plastic panties over the diaper. I was helped to sit upright on the changing table and Margee slipped a sweet smelling soft medium length nightdress over me. She handed me 2 pills and a glass of water, one was the familiar estrogen and the other was one that would help me sleep, I laid down on the bed and she asked me to spread my legs a little which as I did I felt a strap go around my ankle and get buckled. I gave her a puzzled look and before I could say anything she explained that all the foster children spent the first week this way until she and Mac were 100% sure both themselves and the child would not be in any danger overnight. 

That actually made sense to my calculating but completely relaxed brain so I let her do up and adjust the restraints so I would be comfortable while sleeping. They were adjusted so I could easily touch my nose with both hands but not so loose I could reach the buckle on the other wrist to undo it. My legs were spread a little more so I could be easily diaper changed during the night if needed. After pulling up the covers and tucking me in a plastic baby bottle was put next to me that I could easily pick up and put in my mouth to suck on if I was thirsty during the night. It had a formula with a mild sedative that also tasted excellent; she had me try a little while she held the bottle and indeed it was tasty. With a kiss on my forehead she said goodnight, turned off the light then closed and locked the door from the outside.I awoke the next morning when Margee entered the room with a cheerful "Good Morning love". I was a little groggy but felt pretty good except that my buy pussy felt very full; much more than I first felt when she had inserted the plug last night. 

As she was unbuckling the restraints she told me that I had to be changed during the night and as I was completely knocked out she taken the opportunity to use a larger butt plug seeing how easily she could stroke the first one in and out, Once all the restraints were off back to the changing table I went and the plastic panties, soaked diaper and the enormous butt plug was withdrawn but not before she worked in and out several strokes which made my little pee pee stiff to its maximum of maybe 3 inches. Margee giggled and said that that plug had given me a prostate message and asked me if it felt good to which I nodded a little. Back up and off to the shower with her where she made sure I was cleanly shaved everywhere including what little pubic hair I still had.Once dried, lotion applied and powdered where appropriate we went back to the bedroom where the clothes were already laid out. It was the dress and bra I had put on briefly the day before along with a fresh daytime thickness diaper. Once the diaper was snapped on and adjusted she gave me pantyhose to put on. As this was the first time I had ever used pantyhose she taught me how to put them on; they really held the diaper and plastic panties tight to my butt and crotch. The dress went on and pink slipper type shoes finished the dressing part before my hair was brushed and pinned back a little so the conservative clip-on earrings would be easier to see that matched the necklace with a small cross. 

We then went to the bathroom where Margee applied a little make up; some blush on my cheeks, light eyebrow pencil and eye shadow then a pale pink lipstick. I looked fantastic in an innocent vulnerable little church girl way; breasts were noticeable but not on sexual display and the dress was just long enough to be conservative but showed off my nice legs and maybe a little extra padded diapered rear. After a light breakfast I was handed a small white purse with lipstick, a small brush and tissue along with a little bottle of perfume as we went out to the car. Margee informed me the rules were the same at church; speak only when spoken to, use Sir and Ma'm when addressing anyone and stay by her side at all times. I was going to be introduced the same as at the pub the evening before; one of their foster kids who had done well and was staying for a while. Church was uneventful and as boring as I recalled from my early youth with mother. After it was over we stood in line and shook hands with the Minister and his family where they were all asking questions that I answered in a soft quiet voice not making too much eye contact but not saying anything that would lead to follow up questions. Evidently Margee was impressed with my performance and said I was going to be a great asset to them as they helped me achieve what I wanted; a college degree so I could be independent to be whatever I chose.

Back at the house I changed back into a shorter pull over dress, took off the hot pantyhose and the earrings leaving the necklace on as she requested. We sat and talked again for hours telling me I needed to go to their Doctor for a full check up and physical as soon as possible. I told her I had Tuesday afternoon off but didn't have money for that sort of thing to which she said they would cover all my medical and dental costs. I didn't recall the last I had been to a doctor and it had easily been 2 years since a dental visit. Tuesday afternoon I came back from school and changed into a long dress, dry diaper and flip flops and off we went to the Doctor. It was a woman Doctor who had taken care of the foster kids under their care so she assumed I was just another messed up adolescent in the system. 

Margee acted as the legal guardian so sat with me through the examination, We discussed history including the wetting issue and Margee gave my age as 16 on the forms. After the usual eye, ear throat examinations the Doctor asked me to please take off my clothes and put on the open back gown behind a screen. I did but as soon as I got up on the table she said the diaper had to be off as well but it would be OK if i wet as she would put an absorbent pad on the exam table.  As I was already on the table Margee told me just to lay down and she would take it off me, Fortunately it was not very wet. The Doctor then began to feel around on my body as I laid there asking me to breath in and out or raise my legs. She did spend extended time at my breasts and shrunken genitals finally asking what hormones I was taking and from where did I get them. Margee explained that I had been given them since I was 11 or 12 by a guy who had used me sexually for years until just a week ago who had easy access to estrogen. The Doctor was not entirely shocked and then asked me why I had not told anyone. I replied it was because he had been the only one who had been nice to me and had supported me plus I actually liked being an attractive girl better than a little skinny geek boy. Asking me several more questions about what I wanted it became clear to her I had made up my mind to live as a girl. 

The Doctor explained the entire transitioning process and risks along with the costs which was when Margee said they would be paying those uncovered costs for my well being. After taking blood and urine samples Margee helped me get the diaper back on and get dressed. When the Doctor came back in she gave Margee 3 prescriptions, a stronger version of the estrogen, a pill that blocked testosterone and another to take as a sedative as needed. She said I needed to be back in 6 months but call if the changes were happening too fast.Once back at the house we went back to my bedroom to change a now fully wet diaper. Instead of getting on the table she asked me just to lay on the bed on top of a changing pad she had put down. Okay, no real routine yet and I was being taught how to get along without any problems so I did as requested as I almost always had. Still in the dress she put me back in the already adjusted restraints then pulled the dress up past my waist and removed the plastic panties and wet diaper. She carefully cleaned me with a warm damp washcloth then began applying baby oil on my penis and massaging it up and down until I became completely hard to the full 3" I could achieve she leaned over and took my cock to her lips kissing the head lightly. Looking back at me she said as I had never had sex with a woman it was her responsibility to at least make me experience it once. 

Especially now that once I started taking the transition strength drugs I would likely never have the chance again. Still in her church dress she unzipped it in the back and let it drop to the floor. Plain white panties, a substantial bra and thigh high nylons were all she now had on. After pulling her crotch-wetted panties off she climbed on the bed and straddled my hips where she undid her bra allowing the large breasts to fall out as she leaned down letting them touch my lips that I instinctively tried to suckle. Reaching back between her legs she took my little cock and pumped it a few strokes before settling down and encasing my entire hips and crotch area with her soft warm hips and pussy. She had guided me into her wet slippery labia with ease though I could not tell if I had penetrated or not; not that it mattered or I would even know as she settled even further down and began rocking up and down methodically. 

The sensation was all warm and soft and wet as I had no idea if I was hard, limp or even completely inside her. This was way different than the rubbing of the guys plump tummies against my little cock that would eventually give me an orgasm that would wet the little front area of my sheer panties that I usually kept on during sex. Harry and the others wold just penetrate me by pushing the wet crotch of my pantie to the side whether I was on my back legs spread or I was being done doggy style. After a few minutes she started slowing the rocking motion and began taking little breaths. As I felt a rush of warm fluid oozing from our crotches I wasn't sure if I had started peeing but that thought was erased by Margee's loud moaning as she grabbed my breast squeezing them while pushing down on my surely still stiff little cock. That made me react with a whimpering orgasm of my own as she slumped completely down on me. After a few minutes she slid her now dripping pussy up to my mouth and directed me to lick her clean. With only a small neatly trimmed patch of pubic hair above her pussy it was obvious where her clit was as it was easily as big as my penis when limp. leaning forward a bit and forcing a couple pillows under my head she made it easy for me to access her dripping cunt. 

I started at the bottom near her rosebud which was sweet smelling with maybe a hint of strawberry. Her juice was thinner that the cum I was use to but not far off in taste as maybe my little contribution to the flood had an impact. I was directed by her as I licked my way up; "a little higher, to the left, lick faster, harder.." until I made it to the engorged red clit. "Gently kiss it, very gently" was the instruction which I followed as best I could. Evidently I had put just the right amount of pressure as she began cooing softly and saying my name. Only a minute or so in a warm wetness started flowing out of her pussy which was definitely not pee as I had thought during the intercourse a few minutes earlier. The moaning started again and suddenly she pulled back and used her hand to masturbate herself to yet another even louder orgasm. Sitting up on the edge of the bed she reminded me that part of the deal for staying with them expense free was that I had to do what they asked when they asked. She also reassured me they would never put me in danger or request anything illegal; immoral, maybe.

As I was already in bed and restrained she just diapered me then not cleaning up the mess she had made of me saying I would be wet in the morning anyway. I was unstrapped long enough to wash my face brush my teeth and take my pills then back to bed, restrains fastened and the formula bottle made available.

Next morning I was awake before she came in and unfastened me and had me go into the bathroom with the heavy, smelly, wet diaper and plastic panties still on. I was told to step into the bathtub where she pulled down the panties and unfastened the diaper pins both dropping to the tub floor at my feet. She ran  the tub water until it was warm and filling the tub then switched it to the shower head. I stepped back from the now almost floating diaper and panties and was told to shower as usual. I was also instructed to rinse the diaper and panties in the clean shower water before getting out then wring them out best as I could before putting the diaper in a covered pail and hang the plastic panties on hooks on the shower wall. This was to be my daily routine during my stay  never to be deviated from. Back in the room my boy clothes were there clean and ready so I could do work and school as usual during the day. As soon as I came back to the house I was to go to my room and put on whatever outfit Margee had put out for me. None of my old girl clothes were around, they had been replaced with obviously much better more stylish lingerie, dresses, blouses and skirts that ranged from sexy conservative to pure slut. Margee said it was all second hand for the most part but the panties and bras but most of it seemed new. We had a lot of fun the first week with Mac not there getting to know each other much better and she only requested me to lick her pussy a few times; usually after I was diapered but not yet put to bed it restraints which allowed me to go down on her more comfortably and suckle her massive tits. I even came in my diaper several times while tasting her orgasm juices that were not contaminated by my cum. It was really a pretty good deal for me; great food, no expenses at all other than the car and school. The sex was actually more enjoyable with the possible exception of the night time butt plugs though even that was no longer causing me any discomfort. 

Margee said Mac would be back Saturday afternoon and we would all have dinner together and then spend a quiet evening at home. Mac had not seen me since well over a week ago; Margee had done quite a job in changing my appearance with some minor hair styling, simple jewelry, make-up application instruction and of course the super nice clothes. She also was teaching me how to more move like a women; a sexy women at that. We even danced a few times and she showed me how to subtly flirt with my hair and dress. As she had me dress in high heels everyday while doing all the cleaning other chores I was even able to walk relatively well though dancing was still a challenge.Saturday came quickly and after doing the laundry, cleaning the kitchen, bathrooms, vacuuming and dusting the house I showered, put on a short skirt and ruffled blouse and flats we went out to the mall to do some shopping. We went to Fredrick's of Hollywood where we giggled at some of the more outrageous outfits and wondered just how uncomfortable they would be to have on. We both decided the discomfort would probably be overcome by pleasure pretty quickly. Eventually she stopped in front of a mannequin dressed in a ivory satin and lace zippered waist clincher, matching push up bra, garter belt, stockings and a gorgeous satin and lace pantie that looked delicious. 

Lace and satin gloves along with stiletto heels finished it off the look. We were both obviously taken by the display so when a sales girl came up she just said too bad that is being discontinued as being too old time wedding looking. The whole ensemble was being clearance'd out at 70% off. Margee asked if it was available in a size 4 which I knew enough from going through all the new clothes she had bought me to realize it was too small a size for her but would fit me fine. I sensed myself wetting at the thought of wearing this for someone; maybe for Margee? She paid a still high price for the outfit passing on the shoes which were not on sale. We continued power bargain shopping and came across a white fairly short satin wrap dress that had a big belt type tie at the hip with very open flowing loose sleeves that went down to around the elbows. Obviously a disco dress it was extremely flirty without being slutty. 70% off got it for less than $30. After a quick bite we were back at the house and Margee told me to go directly to the shower to bathe, wash hair and make sure I was shaved perfectly; she would meet me in the bathroom for hair styling, make up and to dress me for dinner with her and Mac.Dinner wasn't until 7:00 but she had some food prep to do so I had to be done up first. 

Margee wanted to make sure Mac was pleased with how I had progressed since he had last seen me a week before. She had not only refined the way I acted as a woman but also made sure to teach me subtle but important notes on social etiquette, manners and how to carry myself in the most sensual way possible when appropriate. This evening would be the time to be the appropriate time to be sensual. An hour on hair, 30 minutes on make-up followed by the ivory lingerie being carefully donned along with the required lace pantie diaper for now. This all required adjustments with multiple poses in front of the mirror. I had no idea who the beautiful girl in the mirror was! I was given a silk robe to wear until just before Mac arrived as Margee didn't want me to put on the dress until the last few minutes so I could do a grand entrance once he was home. I did some help with dinner preparations such as setting the table and making sure everything was spotlessly clean.Precisely at 6:30 we went back to the bedroom near theirs that had a make-up table where Margee had me don the dress, put on the silver high heels and do a final touch of make-up including rich red lipstick.I was to wait in the bedroom until called. 

About 15 minutes later I could hear Mac was home and I could overhear them talking; "you said she certainly has potential and I think you will be very pleased with a weeks work by your master wife" Margee said to Mac. She told him that the increased dosage of feminizing drugs had not really taken affect but the doctor assured her the changes would be noteworthy soon. "At least we now have one that won't get pregnant" was Margee's last words I could make out before they moved to the other room. Not long after she came into the room and took a quick look and adjusted my hair before taking my hand and leading me into the front room."Mac, please meet Alaina" Margee said as Mac turned around. I stood there looking down a little as Mac approached stopping in front of me then putting his hand under my chin tilting my head back a bit so I would look into his eyes as he turned to Margee to say "exquisite work my dear". 

He then took my hand and led me to a seat at the dinner table where food was already served. After a prayer we sat and ate with me only answering a few polite questions when asked; always with "Sir" or Ma'm". With dinner finished Margee said we should retire to the den for drinks and listen to some new music. The den was down some stairs in a well finished basement that included a TV a couple couches, a small dance floor and a bar; perfect for entertaining. We sat down, me next to Mac and Margee in a chair next to us and listened to music with drinks Margee made. Mac brought out a crude cigarette that even I could tell was weed and lit it before passing it to Margee who took a deep drag on it. She saw I was inexperienced so came over to me to show me how to smoke it properly. Of course I coughed when I inhaled too hard which made me wet my panties. After they both laughed she asked me if I needed to freshen up to which I nodded yes. We went into the bathroom behind the bar where she gave me the sexiest crotch-less panties I had ever seen. She helped me clean up before I put them on then told me to hang out with Mac and she would be back in a while after she put my wet pantie diaper in the wash. 

Mac was standing in the middle of the dance floor waiting on me as I came back out and twirled me around enough that my garter belt was clearly evident before pulling me close. His hands went immediately to my bottom under the dress as he felt his way around the lingerie while pulling me closer to feel that enormous cock against my flat tummy. We danced a little while as his hands went all around feeling whatever he wanted until he stopped and leaned me back to kiss me fully on the lips which I knew almost instinctively to passionately kiss him back; he slipped his tongue into my mouth that I sucked gently on for a while before I willingly dropped to my knees. I unzipped his pants, pulled down the boxers and was greeted with a throbbing 10" cock that was already oozing pre-cum that I could taste as I gently began taking him into me. Still fully dressed with Mac's hands caressing my hair I could sense Margee had come back downstairs. She was holding a video tape camera and was telling me what a wonderful girl I was not wasting any time while she was away. 

Mac pulled out and helped me up and then walked me to the back of the room where Margee was pulling back a series of bi-fold doors. Once opened and the light turned on I could see a big round bed with red satin covers and pillows. The three walls had mirrors as well as a big one on the ceiling. Mac walked me to in front of the bed and turned me back to the bed facing him as he undressed; the semi-hard glistening monster cock pointing at me. Margee started taping as he came toward me and began undoing the dress tie then brushing it off my shoulders allowing it to fall to the floor in a sweet pile of white satin. Standing in the lingerie so carefully adjusted by Margee earlier he pulled me to him as he lifted me up and laid me down on the red satin bed. He undid the front clasp bra and had me lift my arms up to lift it off. While my arms were above my head on the bed he reached down and brought up satin wrist restraints and fastened them.doing the same with my ankles once he moved back spreading my legs as he went. 

Margee moved closer in doing the video of the details and assuring me that I was a very good girl. Having a very good high going and being very use to restraints over the last week I just enjoyed the extremely focused attention I was being given. They actually told me to struggle a little in the restraints like I wanted to get away so I did so; at least until Mac climbed up on the bed and began messaging my pert little titties. His cock head felt like someone was trying to put a baseball bat in me but after only 2 or 3 thrusts he leaned forward kissing me gently as he penetrated deeply in one slow, long stroke. I moaned loudly gurgling a "0h God!" out then felt him begin pumping my previously well moistened pussy. I lost awareness of Margee as Mac pumped me harder and harder, picking up speed until I could feel myself climaxing what little I could. My orgasm was instantly followed by Mac shouting something as he arched his back picking my bottom impaled by his cock up as he was eight inches in me giving my body no choice as it was strapped to the bed. 

Collapsing on top of me he kissed me gently several times before moving up to allow me access to clean his drooping but still throbbing cock with my tongue and lips. As soon as he got off of me Margee straddled me and had me pleasure her for what felt like an hour as she had one orgasm after another while Mac assumed video duties. Once both were satisfied they sat thinking I  had passed out for a while. As I was drifting in and out of consciousness I could hear Margee tell Mac that indeed I was a great find especially considering the fact that I was very unlikely to get pregnant like the others had...... I felt the bed get warm as I realized I was wetting heavily.

Waking up the next morning diapered in restraints in my bedroom Margee helped me to the shower saying I had pleased Mac beyond his expectations and would be allowed into the main part of the house in a bedroom near theirs from now on, assuming good behavior of course.

For the next several months I did the housework in the evenings always in short dresses as Margee had laid out for me. When Mac was home he would ask me to regularly come over, kneel and service him making sure I swallowed all his jiism before licking him clean then carefully tucking his flaccid cock back in his pants; always to the right. If he was in the mood he would just come up behind me moving me over to a table or chair, lifting the dress pull the pantie diaper down  then bend me over and fuck me hard; pulling out while still hard and have me suck him clean. My breasts had enlarged by then to a solid B cup and were much harder to hide during the day at work and school but Margee helped with clothes and minimizing bras that were not too uncomfortable. That part of my life was stable and no one still took much notice of me; completely opposite of when I was out dressed as a women; I ate up that attention. 

I was only dressing as a man for work or school by then as life is so much better as an attractive woman than a geek boy.They also had a secluded pool that I was allowed to use; in fact encouraged to lay out and tan in a Bikini developing sexy tan lines that Mac loved. As the hormones and blockers took over my body there was no longer any way to fuck Margee so we just did the lesbian thing whenever the time seemed right. She taught me how to bring her to near climax then back off for a while while I probed her always squeaky clean rosebud. I usually had my diaper on when we had sex as there was no need for access except maybe a toy sometimes,  I was always completely soaked considering the wine we would drink after an hour with her making love on the big round bed while Mac was out of town, It was almost as good as being fucked by Mac and much easier to clean up afterwards as well.

School, work. weekly church and housework with a few errands to run for them was an easy life for a few months as I watched my savings grow spectacularly. With no expenses the trade off of the housework and constant sex that I quite enjoyed was something I wanted to extend as long as possible. I now was a mildly attractive slim young woman when not in make-up and straight hair that dressed in simple long peasant dresses could go anywhere with only occasional passes by the men I encountered. In make-up with hair done and a sexy dress I was apparently able to control a man easily it would seem.

3 months in Margee said to make sure I was available for a Thursday night dinner with Mac and some business associates that would be in town. No problem as I could get Friday off as I always worked it never having plans anyway.

Now in the bedroom near theirs when I came home early Margee already had clothes laid out and hurried me into the shower. Once out she did my hair and make-up; full black lace lingerie with a push up strapless bra, garter belt mesh stockings and stiletto heels that I had become very good at wearing. A very short backless red dress that slipped over me and tied in a bow behind my neck was set off with showy earrings and matching bracelets.Dinner this time was just pizza delivered that we moved to serving trays. Margee was also dressed as sexy as possible showing ample cleavage and a dress so short her garters and panties were always on display over her very ample thighs.

The boys had already come in and had gone to the basement room to drink, talk business and smoke cigars at the bar. We came down with the pizzas and the two guys with Mac greeted Margee warmly with hugs then both looked at me and saying to Mac, "what do we have the pleasure of gazing upon here?" Mac introduced me as Alaina, their house guest and would be serving them this evening. While we were sitting drinking wine eating pizza making small talk about my school and work Margee put on some dance music. We were pretty much done eating so she took my hand and we went up on the dance floor and danced as erotically as possible just as we did sometimes did just prior to having one of our marathon "lesbian" sex sessions. The two guys just watched us dance feeling each other and kissing as Mac went over to the big TV and put a video in the player.

 It was the video they had done my first time being fucked by Mac. Nothing I could do or would really want to do so we just kept dancing until one of the 2 guys cut in to dance with me while the other danced with Margee, While dancing with both guys Mac walked behind me and casually untied the bow holding the dress up around my neck that held it up dropping the top to my waist exposing my now quite full breasts being pushed up by the bra making my nipples point slightly up. Each of the guests took this as an invitation and began suckling while using their hands to pull the dress down over my full hips allowing it to fall to the floor. They both then helped me to the big round bed where they seated me in my panties, bra and stockings while they undid their pants enough to expose their average size though fully erect cocks. Seated on the bed I sucked one while jerking the other off alternating between them for a few minutes before they told me to get on all fours in the middle of the bed. This was not my first time with 2 guys but it was much more comfortable on the soft bed knowing I was safe and actually willing to please Mac and Margee by pleasing their guests. 

The two guys alternated between my mouth and my pussy maybe 15 minutes before one came in my mouth and the other in my pussy. As they sat down they asked if Mac wanted to satisfy himself; seeing as I had not yet cum I was thinking about myself more. Mac fortunately decided to finish me off and quickly slid his 8" into my well lubricated boy pussy. I gave out an guttural moan as he drove the entire length of his shaft into me in one thrust; he put his huge hands around my waist and began pumping me almost angrily as I called out "please fuck me hard; HARDER"! Mac started growling and suddenly I felt him squeeze me hard as he paused for a second then suddenly I felt his warm cum flood into me like a surging tidal wave. This set me off into an out of control crying cum / pee orgasm that lasted until Mac slowly withdrew his cock. I collapsed onto the bed in a warm swamp of cum and pee unable to do anything but sob and cry uncontrollably. I could hear the guests congratulate Mac for a great evening and a fantastic show as they dressed and went back upstairs. A half hour or so later both Mac and Margee came back down to check on me. I had gotten up, cleaned myself up some putting my dress back on and was sitting in one of the chairs drinking a glass of wine I had poured myself. 

They seemed quite surprised to see me sitting there especially when I asked them "how did I do?", Mac actually smiled a little as Margee said I was perfect; in fact Tom had asked them if I might be interested in going for a couple weeks on an all expense paid vacation with him to Key West. Tom was head of purchasing for one of the largest retailers in the southeast and Mac had been trying to break into that market for years. They told me to sleep on it and we all retired for the evening.The next day I let them know that I would love going with Tom to the Keys as I wasn't in school for a few weeks but I doubted I could get that much time off work as I was now assistant manager at the electronics store. Mac said maybe he could influence the owner a bit as he knew of him through a connection at church. The following week was the usual routine for the most part until Thursday when Mac let me know he was bringing someone home with him Friday after they had been out for dinner and drinks that I needed to be especially nice to if I still wanted to go to Key West with Tom. 

I dressed Friday evening as if I was going out to a disco to party with girlfriends that did not exist; a flirty print mini dress that had puffy gauze sleeves to my wrists.  A pink slightly padded bra, matching panties (with a mini pad in case I leaked a little) and low strapped heels. They showed up about 8:30 and I immediately recognized the guy with Mac as John, the owner of the chain of stores that I worked for. He of course had no way or recognizing me as I looked nothing like the geeky little assistant manager at one of his stores. I doubt he would recognize me even is I was in the boy clothes from work. Mac asked me if I would join them for a drink downstairs before going out dancing which I answered of course. Margee put some dance music on and said since we had 2 couples maybe we should just party here; I nodded that that would be fine for a while. As was the custom of the time several joints were passed around along with a pill or 2 to relax everyone and make our dancing a bit more decadent. It did not take John who was maybe late forties, beer belly and a receding hairline to begin fondling my ass through the dress to which I put up only token resistance. 

He took that as I intended, meaning he could be more aggressive. So when he decided to give me a kiss I let him and gave in to him slipping his tongue to me that I sucked on gently while I wrapped my arms around his neck as we danced. We sat down after a while on the couch and began making out while Mac and Margee did the same. Margee and I both went to the bathroom together to freshen up and she said they were going to go upstairs and they had already set up the video camera behind a one way mirror aimed at the big round bed still behind the folding doors. Freshened up we came back and Mac had told John maybe he should stay overnight as we had all been drinking so he went over and opened the doors revealing the bed. John asked me if I was still planning on going out and I said no as I was having much more fun here with him. After a little more dancing and small talk Mac & Margee excused themselves to the upstairs and left us alone. John then began to undress me and I let him get the dress off before taking him by the hand to the bed where I had him stand while I slowly undressed him as he caressed my breast through the bra. 

Once I had him naked I had him lay back on the bed spreading his legs apart. I pulled out the fur covered restraints and began fastening his ankles which resulted in him getting an instant hard-on from a drug dulled semi-hard cock. He didn't struggle as I did the wrist restraints as well while he asked me what pleasures I was going to give him. Once he was secured I knelt between his fully spread legs and slowly undid my bra letting it drop on his chest. Grasping his now very hard 6" cock with my hand I began slowly stroking him until I could tell he was nearing the slide to orgasm; backing off until he begged for more. After a few cycle of this teasing I moved up and kissed him passionately for several minutes before moving back down to begin a repeat of the teasing but this time using my lips, mouth and tongue. After bring him to near climax several times and ensuring his shaft was completely lubricated with my saliva I turned around facing his feet while I lowered my panties enough to expose my rosebud but not enough to allow my little pee-pee to be noticed from his viewpoint strapped to the bed. Straddling him I slowly guided his willing prick into my well lubed, well used boy pussy. Once he slipped in I just rocked back and forth slowly for maybe 5 minutes listening to his panting; if it began speeding up to fast I would almost stop until he settled down. When it felt like he might be wearing out I sped up and began moaning which brought him back in a flash. Within a minute I could sense he was going to orgasm so just as he came I stopped and felt him go through 5 or 6 spasms as he shot all his seed into me. I stayed on him until it was obvious he was losing the boner. 

As I got up I pulled off the soaked pantie and turned around so he could easily see my little shrunken cock dangling between my perfect legs. As he took in the reality that he had just been fucked by a guy I let him know who I was. He was still a bit shocked but I began sucking his now flaccid cock which soon became hard again as I cleaned him thoroughly with my mouth; he even came a little for a second time. I promised that this evening would be a secret between us forever as neither of us could suffer the many  consequences. I didn't bother telling him about the tape recording though; that was Mac & Margee's to do with as they pleased. After I removed his restraints he decided to leave getting dressed quite quickly; me helping him remove my lipstick and traces of my perfume so his wife would be less suspicious. Oh, and by the way; could I have a couple weeks of paid vacation next month? Absolutely; whatever you want was his quick response to me as I showed him to the door in a shear black lace nightgown that was always by that bed. Feeling the cum slowly ooze down the insides of my thighs I went to the shower.Needlessly to say the trip with Tom was on. He was different from all the other guys I had known as he was not married. 

That was about all I knew about him other than he had a very successful business that Mac wanted to be a part of. Margee had me out at their pool every chance we had making sure I had perfect tan lines as well as trying dozens of bathing suits from teeny bikinis to sexy 1-piece suits. She actually did my hair a little boy conservative saying that just before we left she would do a full girl styling that she would change once I was back to something that would work with my now limited boy persona. Margee packed everything; I had little input. Menstrual pads in panties were to be my primary protection during evenings out with the usual diaper panties at other times during the day travelling. Diapers were still the usual for nighttime once evening entertainment was over..... Simple pull over dresses, all quite short with only a couple long "hippie" ones for evening was the wardrobe; no boy clothes whatsoever. She also packed several extremely seductive sexual fantasy outfits that seemed a bit tacky for her usual tastes but she said that was a special request. Still it all fit easily in a regular suitcase and small accessory bag that had all the cosmetics, body lotions and hair care products I now knew how to use with great affect thanks to her teaching skills. The day before we were leaving Margee did my hair. If I had been a slim young woman with an average face and a decent body before after the easy to care for restyle of my hair I was elevated to full I want to fuck that status; even without full make-up. When Tom showed up to pick me I had been completely prepared by Margee in a sun dress and sandals with just enough make-up to fit the event. 

Tom had not seen the new hair style and comically asked "where is Alaina" to Mac and Margee. After kissing and we loaded my luggage into his Cadillac and off we went on the 2-day trip to Key West. I gave him a nice blowjob on I-95 making sure the truckers could clearly see what I was doing. Tom enjoyed the show I put on for the truckers for a while but we both decided to cool it after I told him the story of my experience with truckers a few years back. Staying in a very nice hotel with a pool was new to me and Tom made no pretense that I was not his young lover so at dinner or the pool we made out when we felt like it to the sometimes disgust of other guests. After we made love that evening I diapered, put on a baby doll nightie with frilly plastic panties covering the diaper and slid into bed next to him. He kissed me and we slept. Once at Key West we had a large 2 bedroom suite that overlooked a bay with a pool just a short walk from Duvall Street and all the nightlife that had recently become the norm there. We went out and partied at all the normal spots after watching the sunset from the pier. 

Wearing a short sundress and flip flops I was attracting admiring looks from the guys we pasted but I held Tom's arm tightly letting them know I was his but also giving them a look that "I would suck them off given the chance". Back at the room after the evening Tom asked me to change into the kinky school girl outfit Margee had packed. I did so without any hesitation also removing make-up that might spoil the school girl look. It was pretty authentic I thought with cotton panties and a plain white bra, pleated blue plaid skirt and a button up white blouse. When I came back out Tom introduced me to a guy he worked with; no name was given but I immediately knew what this trip was going to be about; I was being pimped out for 2 weeks to Tom's business associates. I basically did everything I could to make the experience as realistic as possible; acting shy at first until we started kissing then giving in to him as he grew impatient. He knew I had extra equipment so there was little need to hide my pee pee but I kept it tucked away until it could not be hidden. 

As he was about to enter me I started a little girl crying asking him to please not hurt me; not that it was likely with his 5" cock. After he was done with me and left I showered and dressed for us to go out for drinks and a little night life that Key West offered. About every other night I was out with another "associate or friend" many of them just wanting companionship for a day and evening in Key West with a young girl n their arm. If they did not make overtures for sex I did not try to persuade them too much. But I still was addicted to the taste of cum and enjoyed the total control over a man I had for at least a few minutes or sometimes a few hours! 

One day I came back to the condo unexpectedly with a very wet diaper and found Tom giving a blow job to some younger guy so I just walked quietly too my room and changed. I guess that may have explained why I didn't seem to have as much influence over Tom as I had with the other men I had been with. The next day at breakfast we discussed the situation a little and he asked me not to broadcast the event I witnessed as it could be bad for business; I said my lips were sealed and gave him a sincere kiss. He wanted to introduce me to his older sister Jen who now lived here and also owned controlling stock in the corporation. He had already briefed her on my background and extreme contributions to the company performed this week. 

The next morning there was a Southern style lace dress with all the puffy sleeves and full petticoat laid out for me to wear to the meeting; it had all been sent over by his sister that morning. A full lace up girdle along with matching bra, panties and stockings were included in the ensemble. I was first to go to a local hairdresser and be done up in a specific manner that I had no input into, which was fine by me. It was to be a late lunch meeting so I had all morning to get ready. It took all the time we had for the preparation; finally getting the bonnet adjusted just right as the limo pulled up for me. I was definitely a Southern Belle that was borderline Halloween Costume overdone even for Key West at that time. A long look at myself in the mirror gazed on someone else but I had become so use to that feeling as I really didn't have my own look anymore but again it didn't bother me a bit.The short ride to her Victorian style house ended with a servant letting me out of the car and into the house where I was seated in a perfectly decorated Victorian parlor. 

Only a minute or less later a stocky but conservatively well dressed older woman came in; I had stood up already and she said I must be Alaina and she was happy to meet me hearing all the good things I had done for Tom. We went to a back veranda and had lunch while I spoke of my school and job. By the second bottle of wine my maxi-pad couldn't hold anymore even though I had been to the ladies room several times. I did have an extra pad so I changed and put the wet pad in the waste basket. When I came back Jen took me by the hand, kissed me gently then lead me up the staircase to her bedroom. We kissed for what seemed like an hour as we slowly undressed each other until we were down to bras, panties and me in the corset and stockings. She undressed me in stages taking time to look and explore me as each layer layer was sensuously removed. 

Through her body language I could tell she wanted me to perform cunnilingus on her as I had learned to do so well for Margee after her multiple  teaching sessions. Jen came so many times the bed sheets were for once completely soaked by someone other than me, Other than kissing and caressing my bottom and breasts she made no other advances on me though I was invited and took advantage of suckling on her full breasts. After maybe 2 or 3 hours of lovemaking we put on nightgowns and had supper served on the front balcony listening to the music and partying going on on nearby Duvall Street. We stayed together the night with me in a little girl pink nightie. a full pin on diaper with ruffles on the pink plastic panties that had obviously been bought in advance in anticipation of my stay. I was cleaned and diapered by the servant lady who smiled and told me that Jen never had someone spend the night with her in her own bed; usually they were "kept in the special room". The next day after being cleaned and diapered by the servant lady we walked around town in casual sun dresses, floppy hats and minimal make up as were walked through shops stopping to listen to music wherever it was being played. 

By the time we finished dinner out my diaper was needing changed as I had been in it since morning and even though I had multiple potty breaks the drinking and walking had taken its toll. Once back at the house Jen gave me a drink then took me downstairs I thought to be changed but once down the stairs she diverted me into another room. I must have blacked out from something in the drink and awoke to being tied to what appeared to be an alter of some sort. Spread legs tied to stirrups with my wrists tied together to the alter above my head wearing only a short leather mini skirt and a leather open front push up bra. I was also wearing a leather mask with a ball gag secured in my mouth. Candlelight dimly lit the room and I could tell there were several people in the room making low small talk. Jen saw that I was waking up and came over to assure me that I was in no harm despite the decoration that I could now make out included Satanic symbols. 

I was to be a sexual sacrifice to the Devilish desires of the Coven; and I was very special as the first transgender sacrifice they had ever experienced. None in attendance yet knew there was a surprise under the short leather skirt. She asked me if it was OK to remove the gag and I nodded yes.  With it out she immediately kissed me and said she was the Grand Master of the Coven and would be controlling what could and could not be performed with me. Then she motioned for all to form a circle around me and join hands. I could count maybe 7 total that were all women in sheer robes of various sizes and shapes. They began chanting; swaying back and forth regularly drinking wine then began reaching out with one hand to caress me using the other to rub their own pussy's and breasts. Jen said something and they all took one step back as she told two of the women to begin suckling my breast and directed another to straddle my face. As they began sucking and the one on my face positioned herself to allow full access of my lips and tongue to her labia. 

As I began licking and kissing the very wet pussy and enjoying the gentle nursing of my breasts Jen had taken the remaining women to stand near her as she positioned herself between my spear and restrained legs. Once she had them assembled she pulled up the skirt revealing my unmistakable but puny penis. I heard giggles as Jen ordered one of them to begin sucking my flaccid maybe 1" cock. The women revolved around me for several hours sometimes having orgasms on my face or taking breaks on me to orgasm with the others of the Coven. Several were determined to make me cum using  vibrators and dildos quite exquisitely but the now years of hormonal treatment was working against them and me as well. In the short periods when I did not have one of them on my face I could see that I was maybe 2 or 3 inches and somewhat hard; I had not felt that way for months. Jen eventually knelt between my legs and began to stroke me slowly with the tips of her fingers from both hands that sent a shiver up my spine. 

Continuing to gently massage my now raw cock I began to quietly moan as an orgasm began to build in me. When I was about to cum she put her lips around my tip and took in the little semen that I could produce. She stood up to and had each of the women come up and kiss her to have a little taste of the semen she had been able to coax out of my tiny penis that the others had failed to do. After that each of the women kissed me, hugged each other then departed. After they had left the room the servant released me and helped me to the shower as I was still a bit groggy from the drugs and the recent rare orgasm. I was diapered in the pink nightie with ruffled plastic panties and led to Jen's room where I slept to almost noon the next day.Dressed back in a new mini dress the next day Jen walked with me back to the condo where I was staying with Tom. She kissed me and then handed me an envelope to open when I got back; something to help my education as a token of her appreciation. 

Also, if I ever wanted to come back and stay a while with her the door was always open.The last 2 days I was left on my own as Tom enjoyed the company of others and I was allowed to do as I wanted which was dance, drink and enjoy the Key's relaxed vibe. Sex with guys who knew I was trans was not as exciting as it had been with the older guys I was use to but the amount of cum was amazing. Sometimes by the time the evening was done I had not eaten but I was not really hungry having sucked off maybe 20 cocks during an impromptu party at some apartment. Though I had a generous "allowance" from Tom I used none of it as guys were more than willing to pay for anything I wanted considering what I was doing for them. Most used condoms when they fucked me but I always sucked them bare as the taste of their cum was why I was pleasuring them.The drive back we were both tired and only stopped one night where we slept in different beds.Once back at Mac and Margee's I was allowed a couple days off the usual chores to recover from my "vacation". Margee had however scheduled another doctor check up so we both went to that one morning.

 The Doctor did a full physical including a rectal exam noting that I was obviously very sexually active and that I needed to take care and have my partners always use a condom; I nodded that I understood. Her overall opinion was that I had developed as much female characteristics as I was likely to get with over a year at the dosage I had been taking. She commented that I seemed quite well adjusted to being female and was impressed with just how comfortable I was in public. Her professional opinion was that I was fully qualified to undergo sexual reassignment surgery if I so desired. The cost however was over fifty thousand dollars at that time which was prohibitive plus I wasn't real sure I really wanted to be just another woman. I kept that thought to myself for the next several months as we went back to the usual routine. School, work, cleaning house and entertaining Mac's business associates as well as keeping Mac and Margee satisfied whenever they desired.  All the while I was bankrolling most all my pay as now a manager thanks initially to a little sexual encounter but now I ran the most profitable store. 

One day I was in my closet and in a purse I had used in the Keys an envelope fell out; it was the one Jen had given me to open when I got back now over a year ago. When I opened it it was a letter detailing various stocks she had gifted me with a lovely thank you note hoping I could use these to finish my education. I took them to my bank and a manager did some research for me thinking it was a nice gesture as it was stocks in some company he had never heard of. I came back several days later and he immediately took me into his office and sat me down. Evidently the stocks were with some computer company and they were gaining value exponentially even as we sat there; if I chose to sell them right now I would get at least forty thousand for them but he recommended that I do not sell for at least another six months. He also offered to invest some of it for me but I declined to do anything at that moment as I was somewhat in shock. I put them in my safe deposit box and checked on my savings balance that was now over twenty thousand.About a week later on a Saturday evening that Margee had told me to be ready to party with them and guests but it was way past ten when Mac finally showed up. 

With him was a very thin young slutty looking woman and they both appeared to be drunk and maybe even coked up. Lately both Mac and Margee had become fond of "nose candy" but I did not care for it. I was dressed quite upscale classy as most of Mac's associates liked me to be. We all went to the basement room where after having Margee get us drinks Mac ordered me to dance with his lady friend. We did so and she treated me as if I was her bitch; calling me that and slapping me a little now and then. Mac interrupted us and told me to drop to my knees and give his new friend an orgasm RIGHT NOW. Doing as told she moved her pungent smelling recently fucked pussy toward my face grabbing my hair pulling me forward and ordering me to get to it. The smell of semen and urine from her panties was almost enough gag me but I did what was asked and after pulling down those sticky, smelly panties down began licking and sucking on her large clit. I did the best I could to hopefully get her to an orgasm as fast as possible so I could get away from that stench.

 In a short time she was convulsing almost falling over as she approached orgasm. But just as I thought she was going to climax she began peeing all over my face and beautiful dress. As I pulled back Mac ordered me to get back in her pussy and bring her to climax which I did. Staggering back after her orgasm she told me that maybe she should have borrowed one of my diapers but my hair and dress seemed to soak up all the piss pretty well. Mac grabbed his piss queen and took her to the round bed as Margee helped me to the bathroom.Turns out the skinny piss slut was Mac's new interest and would be moving into the house taking over my room as well. I would go back to the old foster child bedroom. The rest of the weekend was Mac doing coke with Shirley and drinking nonstop by the pool. Margee was not at all pleased with the situation. She told me that Mac had made her perform a similar act with Shirley in their own bed but they were both drugged up so it had not been as bad as what I had experienced. 

By Monday my mind was made up; less than a year to get my degree with plenty of money in the bank I was done with Mac and Margee. By Tuesday I had a deposit on a furnished one bedroom apartment in an upscale student housing complex that had an attached garage which was something I needed to come and go dressed however I wanted to be. Wednesday I left a note for Margee saying good luck and I wished her well; I left no contact information.It wasn't even six months later I heard that Mac and Margee had been busted for drugs and prostitution. I actually felt a bit sorry for them as even though they had turned me into their private prostitute it had paid off beyond any of my wildest dreams. The next year went very quickly; I used some work savings to buy a new car and continued to see the Doctor Margee had set me up with getting the prescriptions and advice I needed to keep looking convincingly feminine even in a Bikini. I still managed the electronics store continuing the geek persona that few (except the franchise owner...) ever questioned. 

I would dress and go out on the weekends to the discos dancing with the older guys who I knew were married. I would get reliably clean sex and no one for the most part trying to establish a long term relationship. I did little to hide that I was Trans and absolutely none of the guys refused to continue to go through with sex knowing I had a little penis under the thong pantie triangle of fabric. I saw several of my lovers wives on occasion; all were dumpy women who evidently had lost all pride in their appearance who maybe at one time had been better looking than me. Generally after a first encounter in the car or a secluded corner of the bar we would go to a motel after dinner and dancing and fuck to whatever fantasy they wanted to think of. I never asked for money but some of the guys would give me considerable sums as they said it made them feel better somehow. I established maybe 5 regulars that kept my need for cum satisfied that were extremely discreet. 

I only fucked married guys with kids as it was too easy for the others to leave wives for me; I had learned from my first love that lesson. For the most part I avoided the black guys, not that there were many at the clubs I would frequent. One night I was gassing up my car dressed to go out dancing in a very sexy short halter top disco dress when a black guy pulled in next to me and initiated a conversation. We flirted back and forth and I told him where I was headed and he rolled his eyes and said I should follow him to a "real" party. He was at least 6'4" and probably 275 pounds of awesomeness. He told me where it was in a respectable apartment complex party house I was familiar with so I said, that yeah; I would check it out. I followed him to the complex and parked next to him. We both got out and he came over to me and wrapped his arm around my waist then gave me a big kiss that took my breath away. 

He thanked me for coming along and as I gathered my thoughts I decided I needed to let him in on the secret before I was inside. Being next to my car I could I could make a quick escape if the reaction was bad; it wasn't! He gave me yet another kiss then said I was going to be his girlfriend for the evening then took my hand and led me inside. After dancing, drinking and a few tokes I was quite relaxed. One of the ladies came over to me and introduced herself and after a bit offered me up a little pill to enhance the evening that would help me relax and have even more fun.  I asked if it was safe and she responded absolutely; she would take one with me to prove that the "Lude" was completely safe. I washed it down with a glass of champagne. With so many sexy women around both black and white I was not really notable so only a couple other guys hit on me that Glenn quickly rescued me from. About an hour after we arrived he asked me if I wanted to see his apartment that was about a 3 minute walk away. Absolutely; I knew I was about to get my first black cock. 

As soon as we made it through the door we started undressing each other me not quite down to his shirt and jeans off before he had me down to my bra and pantie. He picked me up and I wrapped my legs around him as he carried me to the bedroom. He laid next to me and I rolled onto him sliding down to see the cock I was anticipating. It made Mac's look average at best as I put both my hands around that  already 10" shaft and began straightening it out to its full length. Pumping it with both hands I looked at it for what felt like a long time before bringing my lips and tongue to the uncircumcised head that I rolled back with gentle suckling. The musky odor and slightly bitter taste turned me on so much I began stroking until I had him far enough down my throat that only one hand could continue to pump as I used the other to caress his swelling balls. He caressed my bottom and held the back of my head gently against his now throbbing penis. 

Much sooner than I anticipated the pre-cum began starting; so much that I thought he was just cumming a small amount but no sooner had I thought that a gusher of cum flooded into my mouth which was fortunately back enough I did not choke on the massive amount. Had he been buried deep in my throat it would not have been pleasant at all. I tried to swallow as much as I could but there was just too much in a short period. As he fell back and began to relax a bit I continued to lap up the substantial puddles that were on his perfect heaving abs and thighs. After only a couple minutes he sat up saying that was fantastic but lets get dressed and go back to the party. There was cum well distributed over my body and his but we just toweled off the worst and redressed. My panties were soaked as well so I just put the Max-Pad in his bathroom wastebasket. Back at the party everyone could tell what we had been doing but many of them had been doing the same so no big deal. Glenn motioned for me to come sit on his lap for a while so he could talk to me. 

One of his buddies really wanted to fuck me and he would really wanted to watch. Back we went to Glenn's apartment where the bed was already soaked and I undressed down to the bustier, garter and stockings in front of both of them playing with my perfectly formed breasts and messaging my ass and turning to show it off to his friend as I leaned over the foot of the bed. I felt a decent sized cock up against my pussy but I turned around and quickly took it in my mouth to suck it some but also make sure it was well lubed before he penetrated me. I always prepared my pussy with lots of lube before going out as the Maxi-Pad would contain any leakage but more wet was better. I felt fully relaxed and didn't worry a bit about my little cock swinging as he slid easily into me and began thrusting into me with a rhythmic gentleness as he leaned forward fondling my breasts and kissing the back of my neck. 

The messaging of my prostate felt soothing and I began to breath harder and gently moan with each slowly intensifying thrust. I began uncontrollably leaking pee as I neared climax just as he paused and began short stroking me while he came into me with a loud "YES". At that point my arms collapsed ad with my ass still in the air and me regaining my breath there was suddenly another cock sliding into my dripping boy pussy. I managed to look behind me and I could make out several guys in the room; all naked and stroking their cocks...... By maybe the fourth or fifth guy fucking me I could not even hold myself with their help on my knees in the bed. I fell forward on the soaked bed and for a minute it seemed like the gang bang was over but they spread my legs while I was face down and another big black cock slid into me to deposit yet another flood of warm, sticky cum. It felt great as I was buzzed and their movement while fucking me made my penis rub on the wet bed eventually arousing me to several orgasms; something I rarely experienced. 

Daylight eventually woke me up and a large black women said "Honey; you best put something on right now and get the hell outta here as the dude who lives here has no idea we trashed his place!" Groggily I found my dress, slipped it over my cum covered lingerie, grabbed my purse and headed into the dawn to the car still leaking cum down the inside of my legs. Several weeks later I got a phone call from Glenn asking if I wanted to party again. Evidently I had given him my phone number which was something I had never done before. Remembering the seeming gallons of sperm I had swallowed and the multiple orgasms as I was repeatedly fucked and filled with black cum on the bed I had to say yes. 

He said that everyone had talked about what a hot uninhibited sex bitch I had been that night as even the women I pleased said it was the best pussy licking they had ever had. I didn't even remember doing women but maybe that was why the fat girl helped me get out of the apartment. I told him I would meet him at his place as I was still careful about keeping where I lived private. I dressed similar to what I had been wearing when I showed at his place but when I arrived there were three black girls waiting to take me upstairs and they would dress me "properly" for the evening. I was stripped own to my pantie with the Maxi-Pad and slowly dressed in all leather. A back laced corset that had a built in push up bra, leather garters to fishnet stockings and supple leather gloves that went almost up to my elbows. 

A collar with silver rings that matched all the rings on the other garments was fastened around my neck. Over this was a tight leather front buttoning vest and finally a micro-mini leather skirt; all of it in black. Heavy eye make up and red lipstick was applied before they stood me up in front of the mirror and admired their hour long effort. I noticed that the outfit smelled real "musky" but the girls just reassured me it was the type of leather and no one would really notice so no perfume was needed as guys really liked the leather odor. For fun they gave me a matching leather cowboy hat to have on when we arrived at the party. 

I rode with the girls who were equally wildly dressed in hot pants and mini-skirts taking a few 'ludes and drinking wine as we drove out into the country. Arriving at a house in the woods a party that was fully underway in a big barn behind the house several guys met us as we parked. "Is this the one?" they asked as I got out. They said yes I was and the guy said great, let's party then. I danced, drank and eventually started sucking cocks and going down on a couple recently fucked girls. After maybe around 2 am a fair number f people had left but maybe 20 or so. mostly guys were still there. One of the girls went with me to the bathroom in the house as I was pretty high and while inside gave me some panties to put on. Mine were completely soaked with cum and pee as several guys had fucked me while I was standing at the party so I accepted and put them on. I didn't notice they were kinda sticky wet as well. No matter; probably leaving soon. We slowly stumbled back out to the barn and the dance floor was empty other than a strange looking elevated padded bench in the middle. Another girl took my other arm and helped lead me to the bench where I was pushed face down onto it my head back and chin resting on a padded rest. 

Before I could react I heard multiple clicks of clasps being fastened to the rings on my leather collar, corset, boots and gloves. Secured kneeling with legs spread on top of the narrow bench that only my chest and top of my tummy was on I could  move a little but I was completely restrained. I wasn't real uncomfortable and thought I was about to be used for pleasure by the remaining guys and maybe girls as well as my head was positioned in a way I could do a man or a women. Someone unzipped the short leather skirt and took it off of me. Glenn I think was the first to penetrate me while one of the girls put her wet pussy in my face and commanded me to "Lick Bitch". After a few minutes and all they stopped using me and it got extremely loud with the barking and howling of dogs not far off. 

One of the girls I had come with knelt down next to me and said she was going to now tell me why the leather smelled funky. One of the guys down the road bred Pit Bulls and always made sure the juices from bitches in heat were rubbed into this particular ensemble. And the panties I had put on just a few minutes earlier? well they had just been rubbed in the pussy's of 2 bitches that had just come into heat. The barking by then was right behind me as the pick-up with the dogs drove into the barn. I heard Glenn say something like "Let Spike have at it man" and a dog was brought up to me to see. It had a huge dick hanging between its legs and was drooling heavily as he walked it around me letting it lick and sniff where it wanted.  A couple others told him to get on with it as there were 3 more dogs still caged. I felt what was left of the panties get the crotch cut then slid up my waist so the strong scent was close to my pussy. Spike was guided on top of me with his front legs hugging my corset while I felt him begin to wildly thrust at my ass. 

The guy with the leash was talking to Spike and pushing him side to side until suddenly I felt the penetration of my dripping rosebud by a fairly small wet cock. Spike either pulled himself or was pushed forward up my back and the penis was wildly moving at a rapid pace in my pussy, drool dripping onto my back between the laces on the back of the corset as he panted above me. Within a few seconds the cock thrusting slowed as I felt it grow quickly inside me. A guy yelled out "he's tied with this bitch!"! Even with the drugs and alcohol I had done that evening I began to get alarmed at what I was feeling; It was though a football was inflating in my bowels; as it grew it made my bladder completely empty on the barn floor to everyone's delight it appeared. I had taken many a large cock in my man pussy but this was by far the fullest I had ever felt. I started crying to stop it but it was way too late and fortunately the expansion stopped but had pressed truly into my prostate that triggered my penis becoming erect enough all could see it. "Man, this bitch really likes it" someone said as I started cumming uncontrollably. I almost passed out from my own orgasm but was brought back by the flood of doggy sperm being pumped into me for what seemed like forever. .I could feel it running in a stream down the inside of both my thighs puddling at my spread knees. 

Suddenly Spike pulled out; his penis was still swollen so once it popped out another gush of doggy cum spurted out of my now very loose rosebud. I relaxed almost enjoying the empty sensation when I was again mounted by yet another beast. Knowing what to expect this time I was less apprehensive and proceeded to moan "take me; I'm your bitch" as I knew the people watching were after just that reaction. I was starting to lose consciousnesses by the time this stud had filled me with his jiis so I had no idea that a third dog had taken me as well; except for hearing someone say they were out of videotape so three was all there would be. I awoke to the big women helping me up and stripping me of the completely soaked in everything leather ensemble. She helped me up and into a shower then gave me a towel. When I got out of the shower she gave me the clothes I had taken off earlier; giving me several Maxi-Pads as she was sure I was going to need them all before I made it home. 

The sun was coming up as she dropped me back at my car giving me another kiss and just saying take care of yourself. For several days after that party I had to take off work as I could not control my bowels suddenly dirtying my diaper  and had to be extremely careful in public. Glenn called several more times offering me substantial sums of money to do more videos for him but as he didn't yet know where I lived or who I really was I declined even though just the memory of the experience would make me wet myself enough I would need a new pad. After Glenn would not stop calling I finally change my phone number never to give it out again to any of my casual sex partners. About 6 months later I was in the store when Tom walked in. He stayed just long enough to discreetly ask if I would meet him for dinner at a very exclusive & expensive restaurant Saturday dressed as Alaina. I of course said yes as it had been through him and his sister that I was able to become completely independent of anyone. Tom didn't know where I lived and didn't ask so I would meet him there at 7:00 pm. The other guys at the store asked who it was but I just told them it was an old friend of the family. Tom had always been nice to me and I had never mentioned his homosexuality to anyone so we both trusted each other; for me I probably trusted he and his sister more than anyone I had ever known. 

Having been betrayed when I was 18 had made me learn not to trust anyone as everyone wanted something which I was willing to give if I received even more back. For the dinner date I was made-up and dressed in a relatively conservative fashion, a sea-foam green belted dress with a padded bra to enhance my hourglass figure. That figure was a bit enhanced lower down by a regular diaper / plastic pantie held securely in place by the pantyhose I thought I might need if the night went long. Tom was neatly dressed in Slacks and a sport coat when we met in the parking lot before going in as a couple. After a few drinks and catching up on what had happened the nearly two of years since the Key West trip he got to the point as we finished dinner. Would I pose as his wife for several months? His sister had passed away unexpectedly and he was about to possibly inherit the entire business but the board of directors was unsure of his "personal life" as they considered it unsuitable for a 40 year old in their opinion. 

We would need to go through a well documented "wedding" and honeymoon along with several months of provable matrimony. He had a well thought out plan; a surprise Mexican wedding after a few months of "dating" again, with a marriage license plenty of pictures to record the event then a few months in the south of France. I would accompany him to all the company social events for the following months until the board of directors transferred ownership of the company entirely to him. For my "services" I would receive $100K per year with 1 year paid as soon as we married. After the first year I was able to decide if I wanted to continue for another year should we both decide it was working. The Miami apartment would be our home but he traveled so much I would mostly be on my own other than the required company and family functions. All expenses were covered including the Mercedes convertible which I could use to stay at his sisters house they still had in Key West. Tom would be able to continue his sexual life with his friends and I could do what I wanted as long as it was discreet and did not impact the family business. 

He told me to think about it but considering that I was graduating college and my secret life had become much harder to hide in the area it was an easy choice as I actually trusted Tom. I leaned over, kissed him gently and said it sounded like a lot of fun and absolutely I would do it! A month later with a degree in hand I was ready to go. Tom made all the final arrangements and gave me the itinerary. I went to my Doctor and asked her to set me up with a new Doctor in Miami so I could continue treatment. After telling me there were many choices there she again asked if I was ready for reassignment surgery. I was now 22 and it would be harder the longer I waited but still even with the money being no problem I could not commit. After all, once that was done I would be just another women of average looks (without make-up...) and my experience proved everyone wanted to experience a tranny at least once. Also the upkeep once transitioned was much more involved that just a few pills and an occasional injection. The fact that for the next couple of years I wouldn't need to do the "man" role would tell me if it was a lot easier just being a woman. I told the Doctor not yet. 

We started dating again as soon as I was moved to Miami staying in the apartment and making all the clubs. I had cut all ties with Atlanta not really having many other than work and sold my car as soon as I had arrived. We had sex when he was in town but some nights we both had partners in the separate bedrooms. I was a pretty easy sell to his family and business associates as his sister had told all of them about Tom and his girlfriend who had come down for vacation before she had passed. Even though he was almost 20 years older than me it was somewhat tolerated in that social level. Several of his co-workers would hit on me but I was always true; it was too good a deal to mess up over some cum. after a month we pulled the trigger, flew down to Mexico one weekend and got married. We spent a week doing tourist stuff taking lots of pictures of ourselves everywhere; me in sun dresses, big hats and of course in my Bikinis. 

I had let my hair grow out as soon as I left Atlanta as I didn't need to dress as a boy anymore. I could afford the best stylist so I always had gorgeous hair. I came very close to having breast implants but I had a solid B cup and didn't want to lose any of my sensitivity I had heard could happen. We even took a few shots of Tom fucking me and me sucking his cock so he could show any guys who questioned his straightness. After a few weeks back and several congratulatory parties we were off to France for a month. A hotel on the Riviera was quite the experience with many trips to the mountains, towns and sites in the area. One of his company's suppliers set us a gift of several nights at the Hotel Paris in Monte Carlo along with entry to the Casino. Evidently it was one of the guys who had flirted with me at a company event. At the hotel, the room had a Tux for Tom and several sexy evening gowns for me with all the the associated incredible French lingerie. I prepared the entire next day having my hair and nails done then trying n all the combinations of clothes and undies in front of Tom letting him decide what to wear. That evening was an experience beyond imagination. Everyone knew our names and treated us as royalty it would seem. 

Dinner, dancing then some time at the casino though neither of us were gamblers lasted almost until the sun was coming back up. We slept together, me putting on a very comfortable French adult diaper I had purchased at the apothecary near the hotel. The month flew by and we were back in Miami settling down into a relaxed relationship that worked great for both of us. I would make frequent trips to the house in Key West sometimes going out and partying with locals. By this time the Gay community was quite active there but I stayed separate as much as possible but still enjoying as much sex as possible. Usually I targeted older married guys out with buddies to take back to the house and have fun with. 

They never tried to hunt me down the next day! In Miami at the clubs I could get fucked twice on the dance floor with hardly anyone taking note. Cocaine, Quaalude's and LSD were rampant so most people didn't notice a thing. My boy pussy would be dripping in the taxi home each night but I never brought anyone to the apartment from the clubs. I had met several middle aged average looking married guys in the neighborhood I would hang out with and sometimes have sex with at the apartment when I needed to taste cum again. I spent time at the beach, shopping and generally being decadent as I had plenty f money and no job other than be available to Tom when required, After a year of this we sat down and discussed what we would do next. The company was now fully in Tom's control so the reason for our charade was gone. He had no problem with continuing if I wanted but in any event the next $100K was mine; already deposited in my private account. 

After yet another loving kiss that I actually meant I told him I had an idea. Several of the asshole board members had expressed interest in me during the time we had been together so what if I started fucking them one by one; taping it with him finally finding out then divorcing me? He thought about it a minute then laughed so hard he wet himself which made me pee my diaper as well from laughing. He asked me how I came up with that idea; All I said was remember Mac and Margee? I was somewhat bored anyway so this would be a fun release from needing to be so discreet with my sexual escapades. We picked the three guys who had called Tom a perverted queer several time as our targets. 

I would somehow be available, alone when they were here in town alone as well. Tom would suggest they say hello and maybe have dinner with me while they were here. The rest was up to me. They each took the bait so easily it almost made me laugh. The first guy I invited back to the apartment for after dinner drinks almost raped me before we made it to the bedroom where the camera was set up. I gently fought him off and served him a spiked drink then lead him into the bedroom as he undressed me and I undid his pants and sucked on his cock as he fell back on the bed. He passed out not long after I had climbed on top of him and I felt his little hard on go limp in my boy pussy. 

No matter; video was captured. The next one similar but I lessened the drink spike as I wanted to at least get a decent fuck as well. The last one was only maybe 60 or so making him the youngest but fattest of the three. I talked him into letting me restrain him on the bed so I was able to perform the entire sexual repertoire on him for the video. None ever knew I was not a woman, but even if they did I knew they would never, ever say a thing after seeing their videotaped evening with me. The sex with these guys was not memorable with the best arousal for me was thinking of their reactions when they played the video tapes that Tom would mail them if he decided to. Actually now at 23 I was not as into all the sex with the average older married guys that were easy prey with my still very attractive body and decent facial features. Even with all the hormonal treatment I was beginning to get taller and voice becoming deeper though Tom thought it was even sexier sounding.

 I was also tired of the hour long make-up and dressing rituals any time I went out even just to get a few groceries. Remembering that if I decide that transitioning was the way to go it would even be more complex so again I considered a complete change. We planned the breakup of our "marriage" to be at a company sponsored barbecue where all the board of directors would be present.  I was dressed to kill in a country-western micro-mini skirt with high heeled cowboy boots and a puffy white low cut blouse.  It didn't take long after a few dances and drinks for one of the younger associates to invite me back to a bedroom to get a blowjob. I let Tom know so he and several of his associates could discover me there bringing this guy to orgasm. His timing was perfect and 2 of the guys with him were the bastards I had videotaped fucking me! The looks on their faces was pure horror, thinking that maybe Ton knew about them as well. With cum dripping from my lips he began shouting accusations that I was a slut who was probably fucking everything in sight. 

This was followed up with me finally sitting on the floor crying....a perfect show. The Mexican divorce was done in a week.  A few months went by as I enjoyed life in the Keys and travelling on a whim knowing if not set for life with money from investments I was at least good for a decade if I managed the money well. In Europe the trans community was easy to enjoy and there was little chance of complication so I spent many weeks there. During one stay I received a phone call from Tom; he was very sick in a Miami hospital and just wanted to talk to me. I flew back and went the next morning to the hospital to see him. He was extremely thin and had IV's in him everywhere. I went to give him a kiss and he refused saying don't even touch him. Taken aback, I asked what was wrong? All he said was "it's AIDS." He said I needed to get checked as son as possible but he wanted to tell me first that he had left all his assets to me if he should not pull through this thing. I told him I didn't need anything as he had already given me more than I ever dreamed of having. 

He responded asking if he should just give it to charity or let the board of directors what to do with it? I said OK but I was sure he would pull out of it  and be fine. I was there with him a week later when he died. The funeral was only attended by six people; me in the expected black dress and veil. He was cremated with his remains interred next to his sisters and parents in their family mausoleum. I had my Miami Doctor check me thoroughly after telling her the situation with Tom and I was given a clean bill of health. I asked what would happen to me if I stopped all the female hormones and the male hormone blockers. She said I would need to gradually reduce them over a six to twelve month period when I could expect tho see changes in my body and mindset develop gradually into a male appearance and mental attitude. Just quitting could kill me; either by physical reaction such as a heart attack or a mental breakdown leading to suicide. She also said my sex drive would become much stronger but some of the body changes would be permanent; larger beasts and buttocks being the most obvious. 

Hair would begin to grow more but it would not return to normal male levels. Seeing all the news reports on the AID's epidemic and seeing several of the older guys in the neighborhood I had regularly fucked die of it I decided to go back to being a male. I had noticed back in the hospital that they were using disposable adult sized diapers on Tom and others there to contain the possible contagious pee and poo . They were only available through hospital supply stores in bulk but I managed to get several cases. Though a bit noisy without plastic the panties they were incredibly more convenient and didn't need a dress to hide them. 

They became my daytime diaper (I still used cloth with plastic panties at night) with the pantyhose keeping them silent. A registered letter arrived a month later that informed me of the reading of Tom's will in Miami. I arrived dressed in a short sexy red dress, stilettos and black fishnet stockings made-up like it was going to be my last fling as a sex kitten. Because it was. All the Board guys I had videotaped fucking me were there and seemed surprised that Tom's ex-wife would bother to show up as we had put on a pretty convincing performance that we truly hated each other during the lead up to our "divorce". The lawyer began reading the will and it listed various amounts to various charities, a few trusts set up for cousins children's education then in came to the remaining assets being read off in a long and impressive list. At the end of the list he said the board of directors could continue with their current compensation and name a new Executive President but all other assets would go to me; Alaina. There was shock and outrage by several in the room but the three senior members of the board who had fucked me on videotape just came over and congratulated me. One told me the tapes had only showed up after Tom had passed; he never used it against them prior so they knew something was up as they had all bragged to each other that they had fucked the bosses wife. 

That was the last I ever saw anyone who was with the company. I was staying in the Miami apartment for a while when a hurricane hit the Keys. Once I was finally able to get back I found the house had been completely destroyed. I had the few clothes in the Miami apartment (now mine) and the Mercedes. All the clothes, art and items I had collected travelling were gone. I let Tom's, now my lawyer handle it with the insurance companies. I hopped in the Benz, lowered the top and headed west.The disposable diapers made travelling so much easier in men's clothes and as I slowly backed off the dosage of the feminization drugs I began to so slightly begin to fit in male cut clothes a bit better. I decided to rent a condo on the Pacific off Santa Monica not far from the Pier. I just hung around a few months meeting a few interesting people as I slowly transitioned back to a more male appearance. Facial hair returned pretty quickly but I stayed clean shaven. 

After six months the bras no longer were required but the breasts were still very pronounced. My gorgeous ass was still shapely but did fit in the looser jeans and overalls I preferred to wear over the required diaper and plastic pantie. One day I was out n the Pier in some short shorts and a young thin hippie type woman came up to me to tell me my diaper was showing. She said she had been watching me for several weeks trying to figure out my story but had come up with no reasonable explanation. We sat down for a few drinks after that intro and I said I was left a trust fund and could live where I wanted and yes, I had needed to wear a diaper as far back as I could remember. She mentioned she had a friend with the same issue to deal with and he knew several others as well who could maybe offer any support if I wanted it. She asked me flat out if I was gay but I said I was bi-sexual the "rare" times I had been given the opportunity. My look was quite androgynous which was accepted at that time. She then told me she was bi as well then asked me if I wanted to fuck her. I could actually feel my little prick begin to harden in the now wet diaper. I said I would love to but I was a bit wet and wouldn't want to be unclean with her. 

She said that was not a problem as we would shower first. Her apartment was around the corner. Oh; and by the way her name was Cynthia. I told her I was Alain and off we went. We stripped and I put the wet disposable in her covered bathroom trash can as we jumped in the shower together. Cynthia was amazed at what she saw with my pert titties and shapely ass and a small but erect penis surrounded by peach fuzz pubic hair. She was shorter and much thinner than me and her titties were probably smaller than mine. We washed and played with each other before drying off some then jumping into the small bed. I began to go down on her like I had been taught years ago and Cynthia was moaning in ecstasy within a minute or two. Just before I sensed she was about to come I moved on top of her and inserted my three inches of manhood into her pulsating dripping pussy. I only lasted a few strokes after she let go with a series of orgasms that did all the movement needed to get me to cum. Rolling off of her I realized that fucking a girl could be fun.