So, I went to my first transgender support group meeting ay the tender age of forty-five and met a lot of people like me – guys who knew something wasn’t quite right when they were born. I knew maybe when I started crossdressing when I was in grade school that something was up. I knew when I was taught how to masturbate by my cousin Randy and his friends that maybe I liked looking and feeling their cocks more that I liked the pictures in the Penthouse and Playboy magazines, but I couldn’t help myself from wanting to be like those women. When the first hardcore magazine with women sucking guys cocks was brought into our masturbation group, I knew I wanted to be like those women. When I started wearing panties during these masturbation get togethers and none of the guys said anything, I knew I wanted to be like these women. When my cousin Randy asked me to suck his cock during one of these masturbation sessions, I eagerly accepted but I had no idea why. When I finally made it into high school, when I didn’t have gym class or was playing sports, I was wearing women’s silkie panties. When my group of friends would be checking out the chicks in school, I was always wishing that I looked like those women in their sexy tight jeans, beautiful hair, and whatever sexy stuff that they were wearing underneath those clothes. As I got older, I would date women, sleep with them and nearly married one but those urges never went away. Finally, I am at my brother’s bachelor party at strip club, I watched two women have sex with each other on stage and I vowed that one day, I’d been doing that with another woman – as another woman…
And now, here I am with other guys who feel same way. Some are a little bizarre, and I try to stir clear of those trans people. Others are either educated professionals or work in some serious professions and are trying to figure out what is going on with them like I was. After I started hanging out with a few of them, I began to learn about laser hair removal, hormones, therapist – unlike today were you just need to say, “I’m a cat,” and a doctor will prescribe a little box for you without any questions – passing as a female, facial femininization surgery, breast augmentation and finally, gender reassignment surgery. Each of these was a pretty scary step but I knew that I had to take this journey.
As I progressed along this crazy journey, I made new friends and acquaintances and some of these became close friends. One of them was Denise, a male nurse who worked crazy hours and was transitioning along with me. She provided aftercare support for me after I had my facial feminization surgery, and I was there for hers as well. At the time of that surgery, I was a trans woman in my mid-forties who was going back to college and taking classes. I had my facial feminization surgery or FFS during the summer after my second semester. When I said that I would probably return for my third semester still as Steve instead of Kelly, she politely pointed out that not only had the hormones given me an extra, EXTRA B size set of titties, that the laser hair removal had removed my beard AND that I now looked like, well, a woman. Ooops, I guess that stuff was working! When it came time to have her FFS, she decided to have a surgeon in San Francisco do the work. I went with her to provide her after-care but for the first couple of nights, she stayed in the hospital so all I could do was visit. I knew a former work colleague who lived there with his husband, so I went to visit them as well. Though he never knew I was trans during the time that I worked with him, he was interested in my transition as well was his husband. I ended up telling them about some of my guy hookups that I had had before I transitioned and both of them became even more interested. I had a strange feeling that when they asked me to show them my new titties that the hormones had created, they had something else on their minds and I was right. Men ARE pigs but that lead to my first male, male, trans threesome but more on that in another story.
Eventually, we started to live our lives as who we were, preop trans women. Yes, I wanted to get into Denise’s pants and suck her cock BUT we were friends, and I knew that that would have ruined our friendship and both of us knew that. Because of her job, she had to stay closer to the downtown while I lived in the suburbs. The roommate that she ended up living with was another tarns woman named Jessica. Jessica was an obnoxious person, transgender aside from that. She was very outspoken, tended to say what she thought, regardless of who she was with or where we were. I mean overall, she was a nice person, just pretty bossy. But I was about to learn that someone like me, who was very submissive sexually, would need someone like that to take control.
It all started one night when I came over to the apartment and was waiting for Denise to get off work so we could go out after she got home. While I was there, Denise called Jessica and told her to tell me that she wouldn’t be out of work until the morning because she was pulling a double and to say that she was sorry. Jessica passed this on to me and was making a few rude sexual remarks about it, but I blew it off. Jessica then said that since I was here and that she was done with her homework that she had – she was back in college - why didn’t we kick back and watch a movie. I was like, whatever, why not, Saturday night was ruined anyway. So, Jessica puts on some movie that I have never heard of, and we kick back on the couch.
Now I need to set this up a little… Jessica is wearing just a nylon runners tank top with no bra, her hormone created titties are kind of poking through the fabric. She is also wearing a pair of nylon jogging shorts and not tucking anything so I can see her bulge but whatever. I’m wearing a tight pair of size 6 Levi’s jeans, some sexy nylon panties – man does it feel good when I bend down! – a nice top and a sexy sheer nylon bra that let my nipples show through when they get hard. That and I have my hair up in a high bouncing ponytail. Jessica really has no clue about my sexual past, me crossdressing and hooking up with guys for sex or the threesome I had in San Francisco. She thinks that I am some sexual prude and knows that things between Denise and I are strictly platonic. Jessica, on the other hand, has hooked up with men who like transwomen for money or, so I had been told. One time, I had to meet her at a hotel because she was there visiting “friends.” Part of me was disappointed that she didn’t ask me to perform with her for these men that she hooked up with, two trannys making it live would have been a money maker back then!
Anyway, so here we are. She brings me a glass of wine, and we start watching this weird foreign film which I really have no desire to watch. As we watch this, she leans over and pokes me in the ribs. I brush it off and she does it again and I tell her to knock it off. Next, she leans over and pinches my arm! “What the Fuck Jess, what’s wrong with you?!” “What, can’t you take a little teasing?” she replies. She then reaches over and grabs one of my titties. “Jesus Christ Jess, stop that! How would you like it if I did that to you?” “You’d never be able to do that! I dare you to try!” So, we are sitting there, and I can’t let the dare go without trying so I lean over and grab one of her titties. She slaps my had away and reaches in and grabs my other titty now. “See you aren’t fast enough loser!” she relies with venom. “Listen Jessica, let’s just watch the movie, ok?” “Whatever loser!” and she reaches in AGAIN! This time I slap her hand, but she is now twisting one of my nipples, so I return the favor. She then reaches for my crotch and starts to grab down there! I again return the favor, but when I reach over to grab her dick, I can feel that it’s getting hard! Now we are all mixed up and she is really tugging on one of my nipples and I start to feel a little heat in my own crotch.
We stop for a moment, and she reaches over and gently starts to tug and twist one of my nipples. The feeling of the seer silkie bra against my hard nipple as she is gently pulling on it is really starting to get me excited BIG time. “You really like this don’t you Kelly?” I reach over and start to gently rub her cock through the nylon jogging shorts and reply, “You kind of really like this too, don’t you?” Part of me is thinking, what am I doing with this obnoxious person? She was never really a person who ever turned me on sexually and here I am rubbing her cock through her shorts. This seems like some weird porno film where two women start a pillow fight and end up having hot lesbian sex but here I am and this is happening to me! She stops tugging on my nipple and reaches down to my crotch and starts to rub me down there and I find myself started to get uncomfortable because my cock in tucked into my panties and it is slowly starting to get hard. She grabs a hold of my ponytail and roughly yanks me toward her face. We are staring into each other’s eyes, and I am thinking that we are about to kiss when she pushes my head into her crotch.
“Kiss my cock, Kelly! I know that this is something new for you but kiss it bitch!” So now I am REALLY turned on, and she has no idea that I know what to do with a cock, especially when it's in my mouth! I start to caress it through the nylon shorts, gently kissing it as I feel it starting to get harder. I pull the nylon shorts away and her cock falls out and I slowly start to give it gentle kisses and quick licks with my tongue. While I am doing this, she is pulling my top off and reaching around to grab both of my titties in her hands and gently tugging and pulling on my nipples and I start to moan with pleasure. I slowly take the tip of her cock into my mouth, running my tongue around its head and licking up her precum. Now it’s her turn to moan. Finally, I start to take more and more of her cock into my mouth, enjoying the feeling of it getting harder and harder the more I suck it. She gently pulls me up by my ponytail and looks me in the eye. “You have had some experience with sucking a cock, haven’t you Kelly?” “I might have.” I replied as she planted a big, wet open-mouthed kiss on me. She starts sucking my tongue while she is pulling my ponytail and placing her hand around my throat. She pulls me away but leaves her hand grasp tightly around my throat. “Listen bitch, I never meant for this to happen but now that it has, you are to follow my instructions to the letter, you little tranny bitch. And after each instruction that I give you, you are to reply with “Yes Jessica.” “Do I make myself clear?!” “Yes Jessica.” was my only reply.
“Now stand up and get undressed but leave your girly panties and bra on! And do not untuck your cock you little bitch!” “Yes Jessica.” This was something totally new to me, in a sense. I have always been very submissive with my sexual partners, at least when I started having sex with guys. But it had always been gentle commands and movements, not one of them ever commanded me to do anything. “Kelly, get on your knees so I can shoot my load in your mouth.” was not a command, it was more of this is what I want you to do, and I always eagerly fallowed those instructions. This was different and I knew it and I was excited by it for some reason. As I stood there in my bra and panties, Jessica reached over and started to rub my silkie panty clad crotch. My cock was tucked deep into my panties and the more she rubbed my cock, the more excited I got. My cock started to get harder but in was restrained by my panties and was getting uncomfortable. “Kelly, these are such pretty panties. They are so silkie and smooth. I can feel you starting to get hard, is this getting uncomfortable bitch?” “Yes Jessica, it is.” “What did I tell you? You are ONLY to reply with “Yes Jessica” as she grabbed my cock. “Yes Jessica.”
The more she rubbed my tucked cock, the more it wanted to burst from my panties! She knew that it was causing me distress, but she kept on rubbing my folded over cock as it got harder and harder. Finally, she took her hand from my cock and grabbed both of my nipples through the sheer fabric of my bra and pulled me down to her face. It hurt like hell, but I wasn’t about to say anything! She kissed me gently on the lips and whispered, “Reach in and untuck that cock of yours but leave it in your panties!” “Yes Jessica.” She let go of my sore nipples as I reached into my panties and pulled my throbbing cock loose and kept it in my panties. “Hmm… I figured that you had a tiny sissy cock, but this is nice.” “Yes Jessica.” And then she leaned down and gently grabbed my tranny cock and kissed, licked it through my panties. “Maybe I’ll let you fuck me with this tranny cock if you behave Kelly.” “Yes Jessica.” “Now get down on you knees and suck my cock, Kelly.” This was something that I was born to do but she had no idea that I and any real experience with sucking cock, but she was about to find out! All I could say was, “Yes Jessica.”
By now, Jessica was fully hard and her cock was trying to bust out of those nylon jogging shorts. As Jessica had a tight hold on my ponytail, I gently kissed and licked her tranny cock through the nylon and pulled the shorts aside to reveal her beautiful six-inch cock. It was not like a few of the eight-inch cocks that I had deep throated in the past, so this was going to be a piece of cake. I licked, kissed, and slobbered on her gorgeous cock head and slurped up more of her precum before I finally started to deep throat her and she was loving it! “Kelly, you little whore, you HAVE sucked cock in the past!” she moaned. I lifted my mouth off of her cock just long enough to reply, “Yes Jessica.” I kept at it, and I could feel her legs start to tremble and buckle while I stroked my own rock-hard cock. She yanked my ponytail really hard and pulled me off of her cock, reaching down and grabbing by my throat. She pulled me up, looked me in the eye, and said, “Who said that you could play with your cock? Did I say that you could play with your tranny cock? I did not, DID I?” “Yes Jessica.” “Now suck my titties bitch and be gentle!” “Yes Jessica.”
I slid down a bit, lifted her nylon tank top, and started to kiss and lick around her big nipples while I was gently stroking her cock. I put one of her nipples in my mouth and I heard her softly moan, so I knew I was doing it right. I sucked, nibbled, and bit her beautiful nipples while stroking and rubbing the precum from her cock. Slowly, and gently, I worked my way up her chest and started kissing and nibbling on her neck. This was driving her crazy and she finally reached into my panties and pulled out my cock, gently stroking and rubbing it. Finally, we embraced in a deep, sloppy wet kiss that lasted for seemed like for hours, and we slowly rubbed our hard cocks together. We continued frotting each other, our precum mixing with each other’s cocks. After what seemed like forever, she reached up again and grabbed me by the throat, “No Kelly, we are NOT lovers. Do you understand?” “Yes Jessica.”
With that, she grabbed me by my ponytail and dragged me into her bedroom. “On your knees you bitch!” “Yes Jessica.” This was a request or a command that I never had an issue with, especially if I knew a tasty treat was instore for me! So, I got down on my knees, and she grabbed my ponytail, jamming my face onto her cock. I slurped, kissed, and sucked her cock like the good tranny whore that I was. “Oh Kelly, I never knew that you knew how to do this bitch! You are going to suck my cock ALL OF THE TIME BITCH!” I pulled my face off of her cock long enough to mumble a “Yes Jessica.” I could feel her tensing up as I caressed her thighs and stomach, I so wanted her load in my mouth!!! I had no idea what had come over me. This was a trans woman I barely ever thought about! She was my friend’s roommate and nothing more and now I wanted to follow her every command, swallow her cum and yes, let her fuck me and fuck me hard!
“Oh Kelly, you tranny bitch, that’s it bitch, that’s it, yes BITCH, that’s it!” She pulled my face off of her cock and said, “Kelly, open that mouth of yours bitch, I don’t know if you like cum or not, but you are swallowing this bitch! Do you hear me, Kelly?” I kneeled there with my head back, my mouth opened, eagerly awaiting her load, my hands clasped in front of me like a schoolgirl praying. “Yes Jessica.” As usual, the first load hit me in the eye and I loved it!! The next load hit me in the back of my throat and the next load started filling my mouth and the next load AND the next load AND the next load AND the next load! I had never met anyone who cummed so much!! Load after load until it was spilling from the sides of my mouth!! “No, don’t swallow it now Kelly, just let me look at it!” “Yes Jessica.” And she continued to shoot another two full loads into my mouth after that!! “That’s it you tranny bitch, show me my cum in your mouth! That’s it, now swirl it around, that’s it, that’s it! No, don’t swallow it until I tell you Kelly!” I nodded this time, enjoying the taste of her cum in my mouth more that I ever had at any other time. “That’s it bitch!” as she scrapped her cum from my face and dripped it into my mouth. “I cum A LOT Kelly, A LOT and you will swallow it all unless I shoot it up your cute little ass bitch!” I was still kneeling there with my hands clasped before my chest, nodding in agreement! “Now you can swallow it Kelly and swallow ALL of it!” I closed my mouth and swooshed her cum around my mouth like I was gargling, wanting to enjoy the taste of every drop! When I finished, I proudly opened my mouth to show her that I followed her command. “That’s my little bitch Kelly!! Now lick and suck my cock clean bitch!” Now that wasn’t a command that she even need to say because I was all over her cock, licking it clean and sucking the last of her cum from her beautiful six inch cum hose.
“Now lay down Kelly and stroke your cock, I’ll be right back!” “Yes Jessica.” When she returned, she had a small glass plate. “Kelly, you little bitch, you are going to jack yourself off, blow your load onto this plate and then lick it off. Is that understood?” “Yes Jessica.” I started to jack myself off with Jessica occasionally sucking my cock while I stroked her somewhat limp cock. Every now and then, she would spit on it to give me more lube, and I would take it from my fingers and put some of it in my mouth. “You like my spit, don’t you?!” “Yes Jessica.” “Open your mouth bitch!” “Yes Jessica.” She then started to spit in my mouth, and it was a big turn on somehow! I swallowed what I could and some I spit back out and rubbed on my throbbing Kelly cock. “Don’t tell me that you are cumming bitch, I just want to see it!!” “Yes Jessica.” It was everything that I could do to keep from screaming, “I’m cumming, I’M CUMMING” but I bit my lip and blew my load onto that glass plate!! “That’s it my tranny bitch, shoot that load, shoot that load! Yes, stroke your cock and get every drop out it!” Through clenched teeth, I shot my load and drained every last drop of my cum onto that glass plate. I had been swallowing my own cum for years, but I was excited to be made to eat it. Jessica took the plate full of my cum and played with it for a bit, swirling it around and lifting her finger up and then letting it drip back on to the plate. She swirled some up onto her fingers again and then dripped it into her mouth saying, “Your cum taste pretty good Kellygirl!” She then scooped up some and told me to open my mouth and she slowly dripped it in. “Do you like the taste of your cum Kelly, do you?!” “Yes Jessica.” “Ok, sit up and start licking this plate clean bitch!” “Yes Jessica.”
After I licked the plate clean from my delicious cum, I put the plate down and reached over and grabbed Jessic’s semi hard cock again and began to gentle tug it, wanting it to once more to fill my mouth with giant loads of her cum. “OH no Kelly, my tranny bitch, we are headed to the shower!” “Yes Jessica.” And with that, she grabbed my ponytail again and pulled me into the bathroom. She turned the water on and told me to get in. “Kelly, MY little bitch, we are going to get you cleaned up completely, especially that cute ass of yours. And when it is completely clean, I am going to fuck you bitch, do you hear me?!?!” “Yes Jessica.” And with that, she had me turn around and she spread my ass cheeks, so the water was running down my ass. She grabbed some body wash and soaped up my ass, running her hands all over it like I had never done before. Slowly, she worked her way to my ass hole and started to rub that with the soapy water, slowly inserting one of her fingers in there and then another until she had gotten three fingers in there. It was a little painful at first, but she wasn’t that much of a tranny bitch, I guess. She then rinsed it off and then started to kiss it and lick it, dancing her tongue around my anus and giving me a sensuous rim job. By this time, both of us were hard again and the gentler side of her opened up as she kissed me with deep, wet kisses as she rubbed our tranny cocks together and she slowly caressed me and slide her leg up me.
But that ended when she forcibly grabbed my hair, pulled my head back and told me to get down in my knees in the shower and suck her cock. “Yes Jessica.” Like that was a dreadful thing! I was enjoying my job when she grabbed my hair again, “Kelly, my little bitch, I need to pee before I fuck you so open your mouth!” “Yes Jessica.” With that, she reached over and shut the shower off, “Now you are going to drink my tranny pee, right Kelly?” “Yes Jessica.” She let lose a stream of pee that splashed all over my face and titties before she directed it into my mouth. “That’s its Kelly, let me see your mouth full of my pee. That’s it, now swallow it, my tranny pee tasted good, right Kelly?” “Yes Jessica.” She must have drank a gallon of water because I ended up with two more mouthfuls before she was done. In between mouthfuls, she was peeing in my hair and all over my hard cock. “OK, now get your cute little ass out of my shower and stand there so you can dry off!” “Yes Jessica.” While I stood there soaked in her tasty pee, she turned the shower back on and rinsed herself off.
I was fairly dry by the time she got out and dried herself off with a towel. I could still taste her salty pee in my mouth as she led me into the kitchen. I tried grabbing her hard cock, but she slapped my hand away, “You aren’t playing with my cock Kelly, it’s time I got to play with it!” “Yes Jessica.” “Now bend over the table and spread you legs a bit and stay there!” “Yes Jessica.” She left for a bit and returned with a bottle of lube but before she flipped the top on it, she got down on her knees and started to kiss and lick my ass again, togue fucking me with that hot togue if hers and driving me crazy with delight. She got up and I heard the cap on the bottle of lube open and felt her drip some down on my ass hole. She then started to rub that around and again, carefully inserted first one finger and then two into my tight asshole. “Kelly you tranny bitch, I am going to fuck you in your ass and blow a giant load of cum into that cute little ass of yours!” “Yes Jessica.”
Jessica then started rubbing the head of her cock against my hole and I shivered in anticipation. “Here we go Kelly and no telling me this hurts bitch!” “Yes Jessica,” I replied. And she slowly started to insert her six inch cock into my tranny pussy. Once she was fully in me, she grabbed my ponytail again and gave it a hard pull, “You like this Kelly, don’t you?” “Yes Jessica.” After that, she started going to town, smashing my ass until the table started banging against the wall in the kitchen, making a little too much noise. With that, she pulled her cock out of my ass, grabbed my ponytail again and dragged me back into her bedroom. She threw a towel over her bed spread and ordered me to lay down and out of instinct and previous fuck session that she had no knowledge of, I laid on my back and raised my legs. “Oh Kelly, you REALLY have experience in this, don’t you?” “Yes Jessica, I have and I love being your bottom!” I replied. She got between my legs and reached down and twisted my nipples really, REALLY hard, “It’s Yes Jessica bitch! But you can tell me all about your gay sex life later.” “Yes Jessica!” and she let go of my nipples and put her hands on the back on my knees and lifted my legs higher into the air as she slid her rock hard cock back into my hole. She resumed her punishing thrusting, slapping her body into mine as I kept mumbling, “Yes Jessica, YES JESSICA, YES!” “Kelly, I’m cumming bitch, I’m cumming!” as I felt her body tensing up and the warm cum filling my ass and man did she fill it! I did all I could to pull her deeper into my me, my hands grabbing at her hips and moaning as I felt the warm cum fill me up!!
Once she had dumped her load in me, she pulled out of my dripping asshole, put my legs down and straddled my chest, wiping her still cum covered cock against my lips and then sticking her cock into my eager mouth where I proceeded to suck the last of her cum and clean it up as I was told. While I was doing this, she had reached around and was stroking my rock hard cock where I felt her wipe some of my precum up and taste it. “You taste pretty good Kellygirl, but I bet that you are ready to cum, aren’t you?” I was more then ready when I nearly shouted, “Yes Jessica!” With that, she got off my chest and laid on her back and told me to straddle her. I positioned myself by her legs, feeling her still semihard cock against my ass again, “Now Kelly, you are going to shoot you tranny cum onto my titties, got it bitch?!” “Yes Jessica.” I started stroking my Kelly cock and within a few minutes, I shot my load onto her tits, rubbing my pulsating cock around on both of her nipples. “Now lick up ALL of your cum and start with my nipples and take a good long time cleaning them.” I didn’t even reply, I just did what I was told while she moaned with delight and said, “When you lick up the rest, do not swallow it!” as I continued to lick, nibble and bite her rock hard nipples. I then proceeded to lick up my cum from her chest and when I was done, she grabbed a handful of my lose long hair and told me to kiss her. No need to say Yes Jessica to that so I leaned down and started kissing her, deep, wet, kisses, her tongue and mine swirling the cum our mouths. She spread her legs and we started grinding our cocks together as she threw me on to my back. We continued to kiss, continued to grind our now hard cocks against each other, changing from top to bottom several times.
Finally, she rolled off me and onto her side and she pulled me over onto my side too. This time, she spoke to me softly, gently in between kisses, both of us gently tugging each other’s hard cocks. “So, Kelly, tell me how and where you learned to suck cock and be a bottom.” So, I told her my story about hooking up with guys and other crossdressers before I transitioned, swallowing my first load, learning how to deep throat, learning to drink piss and losing my virginity to Tom. While I was telling her this, she was running her fingers through my long hair, and we were gently kissing one another. She would laugh if I made a joke and would tickle me, this was a total 180 from the Yes Jessica that I had just gone through, like she was human again. We kept on cuddling and talking until we fell asleep in each other’s arms.
Both of us woke up with ragging tranny piss hard ons and as we were done rubbing the sleep from our eyes, I gently grabbed Jessica’s hard cock and started to gently stroke it. “You want this in you mouth again, don’t you Kelly?” “Yes, Jessica and I want a load of your cum for breakfast please, PLEASE?!?” And with that, she grabbed a handful of my messy long hair and dragged me into the kitchen. “We eat breakfast in the kitchen Kelly so sit down right here and get it!” So, I sat on the floor, my legs spread, leaning against the kitchen cabinets as she leaned on the kitchen counter and jammed her cock into mouth again. She was fucking my mouth, plain and simple and as I sucked her cock, my spit started dripping out of my mouth and onto my chest. Ever now and again, Jessica would stop and hold my head back as she spit into my mouth or onto my Kelly cock. I was really turned on by this as well as getting faced fucked in the kitchen and as my mouth drooled onto my chest, I was rubbing it onto my sore and tender nipples, playing with them as I stroke my cock and Jessica fucked my face. I could feel that Jessica was close to shooting another big load and so was I and we both climaxed at the same time. Jessica’s cum in my mouth and on my face, my cum on my stomach and chest. As we sat there with our cocks both twitching, who walks into the apartment but Denise! “Oh my God, what are the two of you doing? And in the kitchen?!?! My God, GROSS! Fuck this, I’m going to bed!” and she stormed off into her room.
Both of us laughed and were like what the hell! Jessica gave me a hand up off of the floor and pulled me into her arms, kissing me deeply and licking some of her cum off of my face. She then leaned down and licked my cum off of my stomach and then got up and kissed me again. This time she grabbed me by my hand and lead me to the bathroom and into the shower, “I really need to pee Kelly and you look thirsty.” So, I eagerly opened my mouth and swallowed her golden liquid and kissing each other with a mouthful of pee. I returned the favor to her, and we stood there in the shower, our hair and bodies wet with each other’s pee, kissing, cuddling, and giggling with each other. Finally, she turned on the shower and we soaped each other up, not missing an inch of each other’s bodies. She then dropped the soap and asked me to pick it up and as I did, I felt her hard soapy cock rubbing against my ass and I knew it was that time again. She turned off the shower, pushed my face against the shower wall, and fucked me royally. As this was going on, Denise walked into the bathroom, saw this and moaned again, “My God!” and walked out. Jessica pounded my ass again and shot loads of cum up my ass and when she was finished, she got down on her knees and sucked my cock until I shot my load in HER mouth. She got up and we kissed again, long, hot, wet, and deep cum kisses. We finished showering, dried each other off and went back to her bedroom where we kissed, tickled, giggled, cuddled, and napped some more. When we got up, Jessica brushed my hair, picked out some of her sexy panties and a bra, a cute skirt, a pretty blouse, and some leggings for me to wear. As she dressed me, she was rubbing my stiff cock and said, “Now you look like a pretty woman, not these nasty blue jeans.” I was like, “Yeah, a pretty woman with a boner!” I replied. “Yes, a pretty WOMAN with a boner silly and you LOVE it!!” and we both giggled like schoolgirls. As we walked hand and hand to the door, she scooped me into her arms, gently kissed me and said, “Kelly, I really did have a good time with you last night and this morning. I just assumed that you only played with women, I had no idea that you loved cock as well! Just so you know, You WILL be sucking my cock anytime, anyplace we meet, do you understand Kelly?” “Yes Jessica. I had a wonderful time too. I liked how you really took charge AND I LOVED the taste of your cum too!” I replied. She walked me down to the street and to my car where we kissed deeply again as she lifted my skirt and rubbed my hard tranny cock one more time. Did I care if people were looking? No, not after last night. As I drove the thirty five minutes back to my home, I was like WOW, that was totally unplanned and AWESOME. Jessica might be bossy but under the right conditions, it’s not really so bad. I reached up my shirt and under my bra and gave one of my nipples a little rub, they were really sore and was my ass and my cock, but it still got me excited enough that by the time I got home, I was hard again. I parked the car in the garage and rubbed my cock through my panties and leggings, shooting my load into both of them. As I reach into my leggings to scoop up some of my cum, I was like damn, Jessica might be pissed that I shot a load into her clothes. Then I thought, “Maybe she’ll punish me?” and I smiled, “Yes, that would suck, literally, if she DOES punish me.”
I few days later, I hooked up with Denise for lunch, and she really chastised me for sleeping with Jessica. “I don’t know how it happened, but you really have poor tasted Kelly! Jessica is a bitch Kelly and even before this happened, I had told her that she should find another room mate because she has really gotten on my nerves. And then you, my best friend, sprawled out on the floor of our kitchen with her cum all over your face, what were you thinking?!?!” I took it because I knew she was right but at the same time, I hadn’t had sex like that in a while. That and I was a sub, a bottom who needed “guidance” from someone like Jessica once and a while. That and Denise certainly wasn’t fulfilling that need, she was busy chasing some cis girl in her early twenties who was nothing more than a tranny cock tease and leaving me high and dry even after I had given her several hints. Denise and I never did hook up, but Jessica made good on her promise that I’d be sucking her cock anytime we met.
The first time that happened was at a transgender support group meeting. Halfway through the meeting, she elbowed me and indicated for me to follow her. She dragged me into the bathroom, pushed me into a stall, had me sit down as she stood and faced me. I knew what was expected of me and really loved cock so as lifted her skirt, pulled down her pantyhose and panties, I took her soft cock into my mouth, and let her face fuck me as soon as she got hard. It turns out that we started this just before they went on a short break and pretty soon, there were other people in the bathroom as well. Jessica slowed down a bit, but she didn’t care, she just kept on fucking my face and part of this turned me on even more, knowing that there were people knowing what we were doing. By this time, I was hard too so I made her stop for a second so I could hike my skirt up and pull my pantyhose and panties down around my knees so I could jerk myself off as Jessica fucked my face. Jessica finally shot her load in my mouth and on my face as well, stroked her cock until the last of her jizz came out and rubbed that into my hair. Then she just left, no thank you, no that was great Kelly, just turned around and left. I closed the stall door again and finally jerked my Kelly cock to climax, shooting my load into my hand, licking, and swallowing all of it. I took out my compact mirror, looked at my face to make sure I didn’t miss any cum and headed back into the meeting. I was bright red when I waked back to my seat and even brighter red when another trans woman pointed out that I had something in my hair – Jessica’s cum. But I didn’t get up and go clean it out, nope, I didn’t care. Pretty sure just about everyone knew what we did in the bathroom and part of me didn’t care because I loved sucking cock and thought that that was nothing to be ashamed of. Not that I would shout that out at the top of my lungs from a tall building but if people knew, oh well.
This continued for nearly a year. Sometimes I wouldn’t see Jessica for a month, sometimes she wasn’t at the monthly meetings, but she’d show up afterwards, at the restaurant that we’d go to. Yep, she’d give me the look, I’d get up and follow her to the restaurant bathroom, she’d point to a stall, and I go sit down as she locked the stall door behind her. And after she was done, she’d be like, nope, no jerking yourself off, do that when you get home and she would walk us back to the meeting knowing that my face was bright red. That was part of her power trip, and I guess I really didn’t mind. On one occasion, we decided to go out to eat with Denise, Denise’s sister Cindy, another trans woman, myself and Jessica. So, I get to the apartment, and we are all waiting for Jessica, sitting around, and drinking a glass of wine when Jessica shows up. “Hey, I snuck out of class early. When are the dinner reservations?” “Oh, we have little over an hour and the restaurant is only five minutes away.” Replied Denise. “Good, then Kelly can come help me get dressed.” was Jessica’s reply. As soon as she said this, Denise looked at me and rolled her eyes as Jessica grabbed my hand and pulled me along into her bedroom at the end of the hall.
Once inside of her bedroom, Jessica stripped down to panties and bra, sat in front of her mirror and told me to brush her hair. When I finished this, she asked me to rub her shoulders and as I was doing this, she gently grabbed my hands and slowly slid them down and into her bra. I could feel that her nipples were hard already and I gently started to pinch and twist them. I knew that this was what she wanted because she started to moan and was gently rubbing my arms and as I played with her rock hard nipples. She reached behind her and unhooked her pretty bra and let it drop into her lap as she turned around and faced me. “That’s it Kelly, play with my titties sweety, yeah, that’s it.’ she purred. As I was doing this, she was sliding her hands up and down my thigh highs as she hiked my dress up. Eventually, one of her hands reached between my legs and her other was rubbing my slowly harding cock through my silkie panties, driving me wild. “Hike your skirt up Kelly.” and I did as I was told. As I stood there holding my summer dress up, Jessica reached into my panties, pulling my tucked cock out and gently stroking it as she pulled my garter belt back and let it snap with her other hand. With one hand gently on my now rock hard cock, she pulled my panties down and slid her other hand between my legs. “Spread your legs, Kelly.” and doing as I was told, she gently slid one of her fingers between my butt cheeks and into my asshole as she continued to stroke my cock with her other hand. “You really are liking this aren’t you, Kelly?” “Oh God yes Jessica, YES, I REALLY am,” I moaned. “Well, we can’t have that now, can we?” as she ordered me onto my knees.
Once on my knees, she ordered me to kiss her own rock hard cock through her own silky panties. As I started doing that, I said, “Jessica, these panties are so pretty.” Knowing full well that she liked flattery of any sort AND her panties were really pretty. As I kissed her slowly harding cock, I saw a precum wet spot emerge I licked and kissed that as well. She then pulled her panties down until they caught under her balls and started slapping my face with her cock. I was so turned on by now, that I grabbed her cock without her permission and put it into my hungry mouth and I grabbed each of her hips and buried my face into her neatly trimmed pubic hair. If someone had walked in on us, we would have seen a pretty funny site, me on my knees, sucking Jessica’s cock while my summer dress was caught on my own hard cock that I was madly stroking as well. Tranny’s will be tranny’s, what can I say?! 😊 Again, using my ponytail as guidance, she pulled me to the edge of her bed, sat down, and rolled back a little and said, “Kelly, lick my ass bitch, give me a rim job baby.” Doing as I was told, I spread her cheeks, found her tranny buttonhole, and licked like crazy, tongue fucking her hole and again looking foolish as my cock was holding up my summer dress as I listen to Jessica quietly moaning. She rolled forward and just impaled my face onto her cock and holding it there for like forever but I didn’t waver. After she let me up for air, she told me to stand up, and I took this moment to unbutton my summer dress and dropped it to the floor. She spun herself around, got on all fours on the edge of the bed and said, “Kelly, I want you to rub you Kelly cock all over my ass, between my sexy cheeks and rub my tranny hole with it until you cum but do not fuck me, just shoot you cum all over my ass bitch!” I was so hard by then, standing there in my sandals, thigh highs, garter belt, panties, and bra so who was I to argue with her, I did as I was told and man did it feel good to hump her silky bottom. When I came, she was moaning as well, “Oh, Kelly, I can feel your hot cum on my ass, it feels so good Kellygirl!”
With out being told, I dropped to my knees and started licking up my cum and wiping some of it up with my fingers. I took two of my cum covered fingers, wiped some on her tranny hole and slowly inserted them into it. I was worried that she might be pissed but I was rewarded with her gentle moaning. After several minutes of bliss from Jessica, she had me pull my fingers out and she flipped herself back onto her back, lifted her legs a little and asked me to put my finger back in while I sucked her cock. Pretty soon, we got into a frantic rhythm, me sliding my fingers out of her tight hole as she thrust her hips up and down, jamming her cock repeatedly in and out of my mouth. As I felt her tensing up, I let up and eagerly waited for her to shoot load after load of cum into my mouth and I continued to stroke he cock, not realizing that she wasn’t just going to shoot load after load of her cum but BLOW load after load of her cum. It hit me in my face, in my bangs and into my mouth as she grabbed my arms and squeezed them with all of her might. “Oh my God, Kelly, OH. MY. GOD! I haven’t cum like this EVER. Give me a minute to catch my breath.” And she patted the bed, motioning for me to lay down beside her, “My God, I have never had anyone finger me and suck my cock before, that was CRAZY good Kellygirl!!” as we shared some warm and tender kisses.
“OK, how much time do we have Kelly?” I looked at my watch and said, “Twenty minutes Jessica.” And with that she got up, straightened herself out a bit and proceeded to don a really pretty bra and panty set, a really cute skirt and blouse, sandals and did her makeup. While she was doing that, I pulled up my thigh highs, reattached a garter belt that had come loose, slid back into my summer dress, and carefully tucked my cock back into my panties. She picked up the sexy panties that she was wearing when we started this tryst and said, “You know what Kelly, I am going to jerk off into these panties, all over the back and into the crotch and then I am going to give them back to you to wear.” “Hey, if it involves cum, I’m loving it, Jessica.” And just before we left the room, I turned and looked at Jessica and asked her if the little bit of makeup that I had on was ok and if I had any cum on my face or hair. “Nope, pretty as ever my Kellygirl.” and tenderly kissed each other again. And with that, we walked out of the bedroom, holding hands and smiling like friends sometimes do. I sat down next to Cindy, Denise’s sister, and poured some more wine in my glass, noticing the red marks on my arms where Jessica had grabbed me so tightly. Cindy looks at me kind of funny and says, “Kelly, it looks like you have a little something on your bangs and your cheek.” Denise just looks at me and rolls her eyes AGAIN and I give Jessica a death stare. Jessica just shrugged her shoulders, held up both her hands, “WHAT??? Well, after all, you said you really loved it, Kelly!” Well, she WAS right…
Jessica DID cum all over those panties and gave them to me, telling me to wear them to one of the support group meetings. So, the day of the meeting, I slipped into those kind of crusty cum stained panties, slid on my tight size six Levi’s jeans and headed of to work for a ten hour workday. Every time I went to the bathroom and untucked my cock, I was oozing precum, it really was a tun on for me. And when I went to the support group, Jessica had me go into the bathroom and show her that I was indeed wearing her cum stained panties. After the meeting, Jessica had me hop into her car and suck her off like I was some two bit whore, which I was around her. She returned the favor by having me pull my top and bra up, exposing my titties to anyone who walked by as she sucked and nibbled on them. She had me unzip my pants and gave me a hand job through her panties. After I shuddered and twitched and shot MY load into her cum filled panties, she would not let me clean up or even scoop up some of my cum and eat it. She ordered me out of the car, watched me zip up my pants with all my cum and then told me to lift my shirt and bra again and flash traffic with my titties. I DID get a few cars to honk their horns, and I ended up driving home with a giant wet spot in my jeans, getting home and jerking off several more times that night
Jessica and I did hook up just for blowjobs six or seven more times – blow jobs in as I giving and she was receiving - that year but eventually, she moved out of state to attend another college. She also made me wear those cum panties a few more times and I kept them for a while after she left. Nothing like sucking her cum out of her panties while I jerked my Kelly cock off to memories of Jessica…
To get in touch with the author, send them an email.
