How I got started

 I was an awkward sexually frustrated and confused teenage boy growing up in a rural part of the country who had a secrete fetish for women’s clothing for as long as I can remember so much so that the Sears catalog was a form of great pleasure and almost to the point of being pornography for my obsessed young mind. One day strictly by a matter of circumstance I found myself alone with my beautiful mothers vast assortment of underwear and lingerie I couldn’t resist the temptation and decided to become one of the models I so lusted after and dressed in a black bullet bra and matching panty girdle with a pair of seamed thigh high stockings. I was in a lustful state of bliss to finally know what it felt like. Do in part to my lack of caution and my mothers’ astute powers of observance I was caught after the fact. Much to my pleasant surprise she was not angry but quite the contrary overwhelmingly supportive. So much so she was giving me a personal one on one sexual education impressing on me that my feelings as much as publicly taboo at the time were perfectly normal and beautiful. To say my mother was progressively way ahead of her time was a gross understatement. Not a feminist in way shape or form she was more of a live and let live nonjudgmental person. As I stated I was sexually awkward, inexperienced and confused so much, so I had never successfully masturbated. Hard to believe a teenage boy who didn’t know the proper way to jerkoff but thankfully my mom showed me how. It may sound strange but to say it was one of the most beautiful experiences of my life does not do it justice. After some sexually promiscuous horse play her being the constant joker that she was, she was teasing me to the point of tears by tickling me while unbeknownst to me at the time dry humping me she finally relented to my begging when she stopped, after a few seconds she said just lay here while I draw your bath. I asked bath I always take showers mom. She said not today a young lady has to enjoy a bubble bath every now and then especially when she shaves her legs. I just looked at her with that look of astonishment, really, she said yes, I told you I had a special day planned a girl’s day together. What just happened wasn’t planned, completely spontaneous fun but not planned. She got up from the bed and kissed me on the cheek and said it will be ready in a few minutes just relax. I did just that rerunning the entire experience over in my head and could feel myself becoming aroused again, when she called out bath time.

I got up from the bed lust filled and feeling a new indescribable sort of sexual confidence if you will from an incredible display of ejaculation which even wowed and impressed my mother. I walked into the bathroom with my semi flaccid penis unsupported swinging with every step. My mom was sitting on the edge of the tub looking at my swinging member saying oh my now that’s no way for a lady to act and of course I looked down at it and half shamelessly almost said I was sorry but caught myself because I knew she would have corrected me so I was learning so I just looked at her and shrugged my shoulders. She smiled and laughed and told me to get in the tub. I had only faint memories of bathing in the tub way back when, so this was like a new experience and I have to admit the hot water and bubble filled tub felt really good and inviting. My mom proceeded to wash my back and places I couldn’t reach with an oversized sponge lathering me up from head to toe and it felt great. While bathing we talked and she asked me so how did it feel, I was a little lost as she could tell by the look on my face, she said your first time masturbating and cumming. I responded it was great I never knew anything could feel like that and then my inexperience so looked at her and said cumming? She laughed and said yes that what it’s called when you finally cum, release the sperm from your penis. Oh, I’ve heard guys talk about it at school but never knew what they were talking about. I asked her if women did, she gave a slight laugh and said yes, we cum do we cum and it feels as great for us as it does for you. I was all questions now oh really yes really, she replied. I asked her so do you masturbate mom. She hesitate a bit I guess taken aback by her son asking if she got off. She smiled and said yes, I do Buddy I masturbate, and it does feel great. I’ll show you. I responded oh and she said yes so you know how to please a lady someday. Looking at me smiling saying guess what I looked at her and she smiled and said you know while you were stroking your penis, I was pleasuring myself at the same time. I couldn’t believe the conversation she smiled and said yes because watching you and helping you with your first time was so exciting, I couldn’t help myself. I had recalled her hand between her legs but couldn’t see more than that.

 She smiled and said I told you I had a special day planned for us girls so let’s get on with it shall we, we’ll talk more about masturbation later ok. I said ok mom, she said ok now let’s shave your legs. I was shocked to say the least and had some hesitation all rushing through my mind at the speed of light, wait I’m a guy we don’t shave our legs, what if the guys see them, waits it summertime no one will see them oh crap what if I wear shorts. My mom with her mom radar in full swing said you don’t have to if you don’t want to, but me never wanting to disappoint my mom who I loved so much didn’t give it a second thought and said now its fine and lifted one of my legs out of the water. Mom smiled and supported my leg by the ankle with one hand sprayed shaving cream on my leg with the other lathering up and down my leg. She then took her razor and gently stroked my leg removing what little hair I had, not being an overly hairy kid or maybe verging on the edge of being less hairy than normal it wasn’t long before my leg was smooth as a baby’s bottom. She smiled and said very nice as she cupped some bath water and rinsed it off, ok now your turn as she handed me the razor. The look on my face was one of horror and what the fuck do I do. She smiled and softly said relax I’ll guide you. She instructed me to gently pull the razor towards he just letting it glide over my legs allowing the blade to do its job and reminding me to keep cleaning it off in the bath water. I completed my task without cutting myself and was quite proud. She ran her hand over my leg when she did, I could feel the stubble. She handed me back the razor and lathered me up again and said one more time. I completed my task and this time it was as smooth as my other leg. She smiled and said nice job young lady and held her hand out for the razor which I placed in her hand. She said ok now arms up I was like what? She said time to shave your armpits I did as requested of me she took a look and said never mind we can skip that part.

She said ok let’s get you out of there and get you all prettied up not knowing what was in store from me had me both terrified and excited, she took me by the hand and led me to her freshly painted bedroom and sat me down at her dressing table. She place both hands on my shoulders while standing behind me looking at me in the mirror saying You know Buddy I really do love this new color don’t you think, I smiled and said glad you like it mom its nice, and she smiled and said if you weren’t such and adventurous inquisitive young man we wouldn’t be having “this” special moment. I smiled and said I guess not. She reached around from behind me and give me a big hug and kissed me on the cheek and told me how much she loved me, and I reciprocated. She said I just want you to know that at any time if this gets uncomfortable just say the word and we can stop. I thought for a nanosecond and said no mom I’m good, I’m really having fun. Truth was my fun was fueled by my raging hormones and lustful hidden obsession with women’s clothing and especially under garments. She began brushing my long brown hair wither big silver hairbrush but not like I did. She held it in her hand and brushed it and combed it and did a bunch of different things with it. She sprayed something in it and continued he handy work. I couldn’t believe my eyes, but I was being transformed into a young lady. She parted my hair to one side and gave it a little curl and a wave a 100% feminine looks completely departed from my parted down the middle pseudo young rock n roller. The entire time my mom was behind me naked except for her radiant smile every once in a while her large breast would rub against my shoulders and head and I wanted so much to suck on them and kiss them as I had done earlier I don’t really think at the time this was done to tease me but rather because of our new found comfort level, I could by it she was enjoying herself and this made me feel even better about what was happening. She smiled and asked what did I think and I smiled back and said I think I look pretty good. Good she said you're downright beautiful, ok now for a little make up. She came around front and bent over in front of my pulling stuff from the draws and I had all I could do from reaching out and fondling her nice round ass and kissing her ass cheeks, my god it was so inviting I could feel my cock pulsing. She was standing in front of me and bent over at the waist so she could work on my makeup and her breast were hanging there like fruit right for the picking, I reached out and cupped her large breast in my hand gently she smiled and just raised her eyebrows saying you really like them don’t you, my almost instantaneous response was oh yes mom I do I really do. She began with a little eyeliner, some blush and finally some lipstick. A very soft pink. Mom wasn’t a big makeup wearing only on special occasions when she got all dressed up. I asked about the other stuff I had seen her wear and she said oh that when I really feel like getting dressed up, you’ll see one of these days we’ll dress you all up for a night on the town. I had no idea what she meant by this and just sat silently as she did her thing. She stood back to admire her work and by doing so gave me a full view of my new self in the mirror. I was in shock to say the least. I looked like me but not me I looked like oh I guess my sister who I didn’t have. I had an athletic build and still sort of do today. Not overly muscular, just toned no big masculine shoulders, taller and leaner so the transformation looked natural and not at all freakish or out of place. I actually looked like a teenage girl and a pretty one at that. Mom was beaming she said ok now let’s get you dressed.

She handed me a white bra, nothing overly sexy more modest than the bullet bra I had tried on, but it still looked sexy a white smooth material with a lace trim around the edges of the cups. As her mother intuition was always working, she said yes, I know not as sexy as the one you picked for your first time but it more every day and looks very nice on you dear don’t you think she asked I agreed and said yes mom I like it I really do. She smile and told me to stand up and handed me a pair of white satin panties here honey put these on, and I did as requested they felt really nice soft n smooth. She had me dress in pair of white shorts and a buttoned blue blouse. I dressed and looked at her for approval she smiled and took the ends of the top and tied them up exposing my navel I had seen her wear outfits like this my whole life, but this now took on a special sexiness. Mom put on a pair of white capri pants and red blouse, she was wearing a black bra that could just been seen supporting her massive cleavage as she had it button down just enough, she finished our dressing with a touch of perfume. Just enough to smell like a lady and not a French whore We left the bedroom and went down and had lunch we sat around outside on the front porch swing enjoying a nice summer day having girl talk as she said with her favorite daughter. They day was one of the nicest memories I have and before long it was time to go in for dinner but then she said oh it’s so nice out lets go for a drive. I was like mom what are you nuts or something. She looked at me and smiled saying gotcha. The entire dinner time we laughed, and she teased me saying the look on my face was priceless. She told me you know honey you look so feminine that no one would know. I said you really think so she smiled and said yes, I really think so but like I told you we’ll keep this our special secrete and winking at me for now. Let’s go have a lite dinner and then get changed into our night cloths. Immediately after dinner without even doing the dishes  or any of the evening chores she looked at me and said let go get changed. I didn’t hesitate and said sure lets go so off to the bedroom we went. When we got to the bedroom she went into her closet and came out with a box, she smiled and said I bought this and have never worn it I’d like you to especially seeing how we have the same taste. I opened the box to find a pair black satin panties with a leopard print panel, a matching bra and a garter belt I was speechless she smiled and said try it on honey, it may not fit great, but we’ll have to get you some of your own soon enough. I rushed to get my white outfit off so I could try on this new hot looking get up. She stopped me saying a lady doesn’t throw her cloths on the floor we lay them on the chair or place them in the hamper for now you can leave everything on the side table. I did as I was told and picked up after myself and set my cloths aside. I then began getting dressed first my bra and mom was impressed by my method of hooking from the front and turning it around etc. she smiled and said you’re a fast learner, I then slipped on my panties and then she grabbed my wrist and said nope panties on last, what if you have to pee, she looked at me and said don’t think like a man and just pull them aside ladies pee sitting down garter belt and stockings first. So, I slipped on the garter belt and mom helped me with my stockings and helped hooking them to the garters and lastly, she handed me the panties.

She smiled and said my you look beautiful; she fixed my hair a little and had me freshen up my lipstick and handed me a black robe she had in her closet and said I’ll see you downstairs we can watch a little tv if you like. I said sure mom and donned the long robe and headed downstairs my young cock straining at the material of my black sating panties. Well I wasn’t downstairs more than ten or fifteen minutes when I heard mom walking down the stairs and into the living room, she was wearing a long white robe that flowed like something you’d see a movie star wear at least that was my vison of her. She had on a robe, but it was open revealing her purple nightie the  lace trimmed cups barely covered her large breast supported by two thin spaghetti straps and that was It unknown to me until later on that my mom hardly ever wore panties even when she dressed for work. She realized they had a purpose abut she liked the feeling of freedom she got by not wearing undies but a wearer of stockings and garters she always looked classy but under her well-dressed ensemble she was pantiles. She came over and sat next to me on the couch and we made small talk about the show we were watching which clearly my mind wasn’t on. She poured me a glass of wine and we sipped as we watched the show, I kept glancing at her admiring how beautiful she looked and smiled. She looked at me and said what, I replied mom your beautiful, no mom your hot! You’re really hot, she laughed and said your just trying to make me feel good, I said no mom I swear you’re so hot I and hesitated short of saying I want to fuck you. She said what honey I said no I have to be treat you like a lady, she smiled and said oh baby you’re so beautiful I love you and I replied I love you too mom. With that she leaned in and kissed me. That was it, she had knowingly or unknowingly started the launch sequence. I kissed her back but not on the cheek or soft peck I just had no control and kissed her right on the mouth. She was taken aback at first but reciprocated with a tender but full on mouth kiss. We continued to kiss each other she began to stroke my hair; I instinctively softly stroked her face. Not having the faintest idea at what I was doing I just did what came naturally.

 I pulled her in closer to me and she didn’t resist so I began softly and gently exploring her perfect body with my hands. I knew her breast were ok as she had allowed me touch them before, I gently caressed her massive melons gently lifting them and supporting them with my hand through the sensuous feeling satin material as we continued to kiss. Her hands were running the full length of my stocking covered legs and she moved up to my bra covered breast rubbing and massaging them and she began playing with my nipples. I could not believe I was making out with my mom; her breathing began to increase, and she pulled away and said softly and gently honey, softly and gently. I continued to kiss her as directed my hand had never left her breast and I continued rubbing them through the purple satin material. I began kissing her more and more I could hear her breathing increase and she pulled away and leaned her head back with her eyes closed. Again, acting on sheer instinct I began to kiss her neck. I could feel her begin to melt as her body became more relaxed, I pulled at her straps exposing her big massive left breast. She began to moan oh Buddy oh yes, oh yes. I began to squeeze her breast and continue kissing her neck. She would confess to me later on that I had found her weak spot, kissing her neck turned her to jelly as she put it. She took my hand by the wrist and said mommy has two boobs remember and I didn’t hesitate to massage and expose her right tit and rolled her nipple through my fingers. Without warning she pulled away from my kissing and grabbed me and kissed me on the mouth but this time she stuck her tongue deep in my mouth. At first, I gagged, and she said its ok baby breath through your nose, I did as she suggested and gave into my animal instinct and stuck my tongue in her mouth and we French kissed I was to later find out that’s what it was called. I can only attribute it to the fact that my cock was restrained somewhat by my outfit that I hadn’t pulled it out and tried to fuck her even though I had no idea what fucking was all about at that time. She began to fondle my cock through my panties, she began stroking its outline up and down squeezing it. She slipped her hand in the top of my panties and said remember I told you panties last and proceeded to pull them down exposing my hard cock that now sprung to attention. She pulled them down the rest of the way and I kicked them off. She began softly stroking my cock and told me to kiss her again. I did as she asked and began kissing her but not as hard and intense at first, she just took my hand and I instinctively placed it on her breast and began massaging it, she told me to come from underneath as if I was lifting it up and run my hands across her nipples. The more I did this the more excited she got and the harder her nipples became. We continued this petting for maybe five minutes or, so she had been  increasing her stroking of my cock occasionally squeezing the shaft. With her free hand she pushed me back off her tits and said lay back and relax baby. With one fluid motion she slid off the couch and was kneeling in front of me marveling at my cock and its head that was glistening with precum. Without warning she engulfed my cock into her mouth. I was paralyzed with shock and extreme pleasure. Her mouth felt like warm velvet on my swollen cock. She began to take it deeper and deeper into her mouth almost swallowing me whole, then she would slide back up the shaft until just the tip was on her lips. She continued doing this and looked up at me marveling at what was taking place and I could see the pleasure and joyfulness in her eyes. She continued to suck my cock and she stroked it with one hand as she sucked it and squeezed my balls with the other. I winched a little and she released her grip. I said no mommy please don’t stop.  She was to tell me later just the word please mommy don’t stop got her totally wet. Her Squeezing my balls was just to let me know that even though a lady may have your cock in her mouth she is still in control.

 She continued her rhythmic sucking of my cock up and down and sucking harder and harder, she removed it from her mouth and licked up and down the entire shaft with her tongue she then put me back in her mouth but only the head as she sucked on it for all she was worth and began to stroke my rock hard shaft, she later told me she was fully impressed at how much control I had and had expected me to blow my load (my words not here’s) in a few minutes. She then fulling engulfed my rock hard swollen cock fully and began bobbing up and down on it faster and faster. My entire body began to shake and tense up and without warning  I began a cum explosion into her mouth. She intently swallowed as much as she could when she pulled back off of me, I was still shooting cum from the head of my cock and she went back down on my throbbing pumping member doing her best to catch every last drop but I couldn’t help spraying her face as my cock was pulsing like a bass drum with every beat cum spurt from the head. She sucked me until there was not a single drop of cum left in my balls. I was totally spent and was drained of every single ounce of energy, when she removed my still semi hard cock from her mouth, she looked down at her bare tits to see I had shot some cum on them as well. She laughed and said holy fuck Buddy that was beyond impressive. She knelt between my legs for a minute looking up at me saying are you ok, I nodded I was fine are you ok I asked she smiled and said I’m great and as if on cue my cock began to pulsate I saw a shocked look on her face and began to clench my ass cheeks as if to help pump me back up to full strength. She said Holy crap you’re getting hard again my god you’re an animal, I never she hesitated saying and got to her feet took me by the hand and said let's go upstairs and have some more fun now its mommy’s turn. As we walked up the stairs my pulsating cock bouncing with each step I didn’t resist my temptation like before and reached out and squeezed her ass, she squealed oh my Buddy and before she could protest I kissed her ass  and sucked on it, she squealed and laughed saying you’re an animal now let’s go.