A gay adult story: Amazing Night With A Sexy Crossdresser by markerss ,
Kassie had a great body, a little taller than I would have liked, but her smooth white skin and her little boy titties, and limp little cock were such a turn on. I could see she didn’t have anything on under her skimpy little tops, and when I saw her little nipples poking out past the crisscross and fishnet, I immediately wanted to feel on her.
This happened a while back now, but the experience has stuck with me and I wish I could be with her again. At one point, I had become very interested in transsexuals and cross dressers and had even been with one that I met on Craigslist and another I met at a bar. Don’t get me wrong, I enjoyed being with girls too, but from time to time, I just had this urge or fascination to be with a tranny. Any ways, it had been awhile, and I wasn’t in any sort of relationship at the time, and the thought of being with a tranny again had started to be on my mind. Luckily, this was before Craigslist dropped its casual encounters section, so it was relatively easy to look for hook ups, and being there was a TS/Crossdresser section, I could easily contact one.
I remember looking through postings, hoping to find one that was attractive enough, because as I’m sure you know, many cross dressers and tranny aren’t exactly very pretty. However, as I looked through the postings on Craigslist, I came across one that looked very attractive and she wasn’t asking for a “donation.” She was white or Latina and looked to be young, which I liked, and from her pictures and de***********ion, she seemed to be small framed, which I also liked. I wasn’t sure if she was actually a tranny or a crossdresser, in either case, i decided to contact her.
Like always, with online encounters, there is a hesitation I feel, not really knowing what I was getting into, but eventually I wanted to meet up with her. Her posting simply said, “Come play with me… – t4m,” and in emails when she told where she lived. It happened to be just across town, and when she suggested we should meet up at a coffee shop on that part of town, I was excited. Yea, I knew the area, but had to look up where it was, because it wasn’t a name brand place. As the time came for us to meet up, I became a little nervous. I wanted to make a good first impression, because from her photos, she looked to not only have a pretty face but seemed to have a nice body too, and being I had sent her a few pics, we knew what we were getting into.
I think we were both anxious to meet, I know I was, and as I pulled into the parking lot and searched for her car, there it was. Parking a few spots over and looking her way, she leaned toward me and waved. Smiling, I immediately waved back and when she gestured for me to come over to her car, I quickly got out and went over there. She rolled down the window and after exchanging pleasantries, she said, “Why don’t you come sit in here, it’s hot out there.”
Looking in, I could see she had on a skimpy little black top and a short black skirt that showed off some great looking legs. Smiling, I quickly went around and as I sat in the passenger seat we shook hands. She had a feminine voice and she really was pretty, kind of sexy, which again made me a little nervous. She had a piercing in her upper lip, a diamond stud, and it looked like she had on a lot of makeup that I don’t really think she needed.
She had shoulder length dark brown hair and I could see some dangling silver earrings that accentuated her facial features. As I continued to check her out, casually looking down, I could see she had on one top that was black fishnet material over another black one that was kind of crisscross patterned. Catching myself, I looked up and seeing she was smiling, it was obvious she had caught me too, ur as we looked at each other, she immediately said, “My name’s Kassie.”
Turning slightly to face her, I shook her hand and smiling I asked, “Why do you go by the name of Ms. Cumms?”
This made her smile, and after explaining it was just an AKA, she smiled and subtly leaned over the console, giving me a hug. Surprised, I hugged her too and as we sat back and looked at each other she smiled and said, “I’m a little nervous.”
I was nervous too, and when I told her, she smiled and again leaned over giving me a hug. She was definitely flat chested, at least from what I could see and feel, and she wasn’t as petite as I thought she would be, but in any case, after talking for a little bit she asked, “Wanta go over to my place?”
Of course I did, and after saying, “Yea, sure,” she smiled and told me to follow her.
As I got out of her car, I quickly went back over to mine and as I followed her, I started to worry about what we would do. I knew what to expect and eventually telling myself, “Just be open minded,” I smiled and continued to follow her.
It had started to give me a hard on, thinking about being with her and then pulling into her apartment complex, I tried to shrug it off best I could. Parking next to her, I got out and as we met up in front of our cars, she said, “This is it!”
It was a modest complex with only two floors, and being she was on the second floor, we had to walk up a flight of stairs. She was wearing black high heels and as we turned to go up the stairs, I said to myself, “She’s tall,” as I looked at her from behind. She did have nice legs, and I couldn’t help but look at her ass in that short skirt, and think about being with her.
Going inside now, I looked around, trying to get my bearings, but she had a nice place with a living room, a small kitchen area and a short hallway that must have led to her bedroom. Moving over to the living room area, she said, “Go ahead and sit down, if you want to.”
Smiling, I sat down on the couch and as I continued to look around she asked, “Do you want anything to drink?”
It was the afternoon and when she said, “I can make you something, what do you like to drink,” I asked, “What to you got?”
Pausing, Kassie said, “Are you okay with vodka?”
Smiling, I said, “Sure,” and when she suggested, “How about some cranberry and orange juice with a splash of vodka,” I Immediately said, “A splash?” trying to poke fun.
“Okay, maybe a little more than a splash,” she said, which made me smile.
I now heard the ice maker and after a few minutes, she came back holding two drinks. Handing me one, she sat in the chair that was adjacent the couch and as we talked, Kassie asked, “Have you ever been with a tranny?”
Smiling, not wanting to give away just how much I liked being with trannies I simply said, “Yea.”
Kassie now smiled and asked, “How many times?”
Taking a big drink, I replied, “I don’t know, a couple I guess.”
Looking over at her, she immediately said,“And?”
Smiling, not saying anything right away, Kassie asked, “Why did you contact me then?”
It made me nervous, and when I blurted out, “I thought you were really attractive, and …” but before I could finish she said, “Thanks, you’re very handsome too.”
Smiling, she put her drink down on the table, and then standing up, she came over and sat next to me. As we looked at each other, she said, “Why don’t we go in the bedroom.”
This was what I had wanted but when I hesitated, Kassie took my hand and after a simple kiss she said, “Come on.”
It was obvious she knew why I contacted her, I’m glad she did and as we both stood up, and smiled at each other, we headed toward the back of her apartment. Holding her hand as she led me toward her bedroom, I smiled to myself and then letting go of her hand, I boldly put it on her butt.
Kassie immediately look back, smiling at me as we continued down the short hallway and as we went into the back bedroom, she stopped and turning to face me, she smiled. Kassie then quickly started trying to take off my shirt and as she pulled it up, I lifted my arms over my head. Throwing it on a nearby chair, she again turned to face me. Instinctively, I reached up and as I felt on her tits, she said, “Hang on.”
Letting go and looking at her, I could see she didn’t have anything on under her skimpy little tops, and when I saw her little nipples poking out past the crisscross and fishnet, I looked back up at her. She was smiling and then as she took off the fishnet top, leaving just the black crisscross one that would actually turn out to be a body suit, I reached up again to feel on her tits.
She had a great body, and it was really a turn on to see her, and now as she moved over to the side of the bed, she kicked off her heels. Climbing on, her skirt hiked up, which revealed little black panties. She was very light skinned and when I again looked up at her, and she saw me staring, Kassie undid the zipper. Laying to one side, and taking off her skirt, I could see the bulge of her cock. Kneeling again, she pulled the bottom of her body suit to the side, and when her cock flipped out, I was shocked. She was shaved, which I liked and seeing that her cock was uncut as she stretched it out, I wanted to feel it.
Watching her as she rubbed it, trying to get it hard, i instinctively looked up. She was smiling and when she asked, “What do you think,” I couldn’t help but look down again.
Smiling, Kassie now adjusted her top, trying to hide her little titties, which was unsuccessful. Continuing to watch, she now reached a hand down and unsnapped the bottom of her body suit. Her cock still wasn’t hard, but watching her rub and pull on it again, I too wanted to feel it.
“Oh my god,” I thought as I watched her, and yea she said something to me, but I have no idea what it was.
Kassie, seeing me staring and feeling on my cock through my pants, she took off the body suit. She happened to turn and bent over slightly, as she took off the body suit, and seeing her ass, I wanted to fuck her. Turning back now, she seductively laid down and looking over at me still rubbing her cock, she said, “Why don’t you take off your pants.”
Kassie had a great body, a little taller than I would have liked, but her smooth white skin and her little boy titties, and limp little cock were such a turn on, I smiled and quickly got them undone. Letting them fall to the floor and pushing them aside, I could see that Kassie was watching intently and as I adjusted my cock, Kassie looked up and said, “Why don’t you take those off too.”
Blushing, I pulled down my boxers and as I got them off, Kassie said, “Come over here.”
Kassie was smiling slyly and when I got close to the bed, she leaned over, and started fondling my cock. I was kind of hard but as she rubbed and pulled on it, and then took it in her mouth, I instantly got hard. It felt good and as I watched her slurping it in and out of her mouth, I thought about wanting to cum.
Feeling on her shoulder briefly and looking at her ass as she leaned into as she sucked my cock, I reached out feeling on her ass, Squeezing her ass cheek for a moment, I then reached down, trying to feel for her cock. When I got my hand on it though, Kassie raised up and said, “Um, I’m not really into that,” as she continued to stroke my cock.
Smiling she laid back and scooting up to the top of the bed she continued by saying, I’m mainly a bottom,” and then said, “I hope that’s okay.”
Looking up at her as she again started rubbing and stroking her cock, I smiled. I wanted to fuck her, and as I climbed on the bed, and moved up until I was on top of her, we kissed. Immediately realizing I needed to take charge, I again went in for a kiss. Kassie now closed her eyes and as we kissed, I pushed my tongue into her mouth. I was so hard right now and as we continued to kiss, I pressed my cock against her. I could feel she was smiling as we continued to kiss, and then leaning away a little, I reached my hand up to feel on her puffy little tits. Looking at her for a second, I smiled, and then moving down to suck on them, I eventually found myself drawing her little tit all the way into my mouth.
Tonguing her nipples and sucking her little tits, I again pushed my cock against her crotch. It made her smile and then feeling her reaching down for my cock, I leaned up, giving her better access. Awkwardly rubbing my cock, Kassie smiled and then said, “Move up.”
Smiling too, I got on my knees and then moving to the side of her, she started rubbing my cock. Taking my cock in her mouth again, sucking it, I instinctively reached for hers. I didn’t grab it, instead I just put my hand around the base, which made her subtly say, “Aaw ah.” which I took as stop.
Moving my hand to her thigh now, gently rubbing it, I wanted to cum, but not yet. It felt good to be in her mouth and hearing her sucking me as she stroked it, I had to make her stop. Moving back down, Kassie let go, and then spreading her legs with my knees, I got between them. Leaning up to kiss her, she raised her legs, obviously exposing her tight little hole.
I wanted to fuck her and when I leaned back up, kneeling in front of her and looking down, and she grabbed her legs exposing her butthole even more, I looked up at her smiling. Seeing her tight little hole, I wanted to be in her, and as I rubbed my cock and we looked at each other, Kassie asked, “Do you want to use a condom?”
That remark made me nervous but when she said, “I’m good either way,” I stupidly decided it was probably okay, but in the back of my mind I knew there might be a chance of getting a disease.
Without thinking though, I smiled and as I moved closer, I watched as she spit in her hand. “What is she doing,” I thought, but then as she reached down and wiped it around her butthole, I knew why.
Continuing to look down at her tight little hole as I rubbed my cock, I nervously thought about how it would feel, but when she shifted a little and said, “Go ahead,” I looked up.
Smiling, I too got some spit on my hand, and then smearing it on the head of my cock and on her butthole, she again grabbed her legs, holding them up. Leaning into her, pushing the head of my cock against her hole and guiding it in with my finger, it suddenly slipped in. Surprised how easily it went in and hearing Kassie immediately say, “Oh fuck,” I looked up at her.
She pulled away slightly as she raised up, and looking at me she said, “Go slow.”
As she again laid back, I knew she was trying to relax and when I pushed into her a little more, my cock seemed to be drawn in. I couldn’t believe it, and as I watched her ass envelop my cock, I leaned up to kiss her. I was in her, it felt so warm and seeing her smiling, I slowly started fucking her.
Moving my cock in and out of her, she inadvertently let go of her legs and when I went up to kiss her again, my cock slipped out. Reaching down and grabbing my cock, she again grabbed her legs, and I immediately pushed it back in. I wanted to cum, and I wanted to face her, but it was awkward and thinking I should have put a pillow under her, I again tried to fuck her.
It felt so good in her, and it must have felt good for Kassie too, because she started to jerk herself off, obviously wanting to cum. However, when she again happened to let go of her legs, my cock slipped out. Looking at each other, Kassie said, “Sorry.”
Immediately, I grabbed her legs and as I tried to hold them up myself and guide my cock back in her, I became frustrated. Looking at her for what I should do next, Kassie moved up and as she did, I knelt in front of her. She now rolled over until she was on all fours and then looking back she said, “Come on.”
Kassie again spit on her hand and after wiping it in her crack, she reached for my cock, pulling me close. Leaning down and letting my spit drip directly on her hole as it gaped, I grabbed my cock and tried to push into her again. Kassie now reached back and as she pulled on her one cheek, spreading her ass for me, my cock slipped back in her. Forcefully pushing all the way in her this time, she pulled away saying, “Ow, don’t.”
Pulling back a little, she looked back smiling and again said, “Go slow.”
Rubbing her ass as I pushed into her a little, Kassie put her head down and reaching back to my thigh, giving it a little squeeze, I gradually started fucking her. She really had a nice ass and as I watched my cock going in and out of her, I stopped feeling on her ass and instead grabbed her waist.
Putting her head down and bringing her hand up above her head she said, “Yea, that’s it.”
It felt so good to be in her and when I felt her rocking back and forth too, I tried to fuck her a little more vigorously. Hearing my cock going in and out of her and my body slapping against her ass, trying to cum, she again reached back touching my thigh.
Continuing to fuck her, I could feel Kassie had started jerking herself off again, because I could see her moving her arm as I pounded her ass. It made me smile, I wanted her to cum but I needed to focus on cumming too.
As I got close and I tried to concentrate, I didn’t want to stop, and hearing her start to moan and breathe hard I felt she must be cumming. It excited me to know, and when she again rocked back and forth, and said, “Cum in me,” I pushed deep into her.
She pulled away slightly and then as I casually leaned over her and pushed into her again, I reached around. I wanted to know if she actually did cum and after holding her stomach briefly, I quietly moved my hand down to her cock. Immediately feeling it was wet and a little sticky, I let go, and smiling to myself, I subtly wiped my hand on the sheet, and leaned up. I now tried to concentrate, deliberately focusing my thrusts so I could cum too, I gave her a couple deep thrusts.
Feeling I was close and breathing hard I thought, “Oh yea, I’m going to cum.”
Continuing to fuck her, I whispered, “I’m gonna cum.”
Kassie continued to try to rock back and forth, trying to help, wanting me to cum. However, as soon as my cock started to buck inside her, I grabbed her and holding her close, I told her, “Stop!”
As she stopped, I’m sure she could feel my cock jerking faintly, as cum flooded inside her. I was done now, but as I subtly started to move my cock in and out of her again, and I kissed her on the back, she leaned up.
It really felt good to have cum, and when my cock started to go limp, I backed away, letting it slip out. Sitting back, I looked down, and seeing cum had started to seep out of her and run down her balls, dripping on the sheets, I nervously felt on her ass. I know I had cum a lot, and seeing Kassie was trying to push out whatever was still in her, I grabbed my cock, trying to squeeze the last little bit out of me too.
There was a large spot of translucent light brown looking cum that had dribbled down on the sheets, and feeling a little embarrassed, I leaned up and subtly rubbed her ass cheeks. Kassie continued to try to push out whatever was still in her, when she inadvertently farted, and cum bubbled out, it made her giggle. Rolling to lay next to her, she leaned over and seeing me smiling, she kissed me and asked, “Did you like that,” and then immediately said, “I know I did.”
Looking up at her smiling, I said, “Oh yea,” which made her smile too. Kassie then grabbed some Kleenex off the nightstand, and after wiping her ass, and trying to clean off the bed, she laid next to me too.
I wanted to leave, that’s what I had done with the others, but I didn’t want her to feel it was a one night stand. I liked her, she was different and as we lay there she asked, “Do you want to leave?”
Smiling, I leaned toward her nod giving her a hug I said, “Can I stay for a little bit?”
Holding each other as we lay there and kissed, I thought about wanting to do it again. It was nice, it felt good with her, but I did eventually leave, and as I did, I asked, “Can I see you again?”
Looking at me hesitantly, Kassie said, “Are you sure or are you just saying that?”
Smiling cautiously, I kissed her and said ,”Yea, I like you, of course I wanta see you again.”
She was obviously thinking about what I had said, questioning if I really meant it and as I got dress to leave, Kassie said, “Yea, if you want to.”
Standing up, I took out my phone, and after making sure her number was in there, I said, “How ‘bout next time, we can go out for dinner.”
This seemed to make her smile and as she got up and wrapped the cover around her, I in fun said, “And maybe we can do some different stuff too.”
Looking at me questioningly, Kassie said in a defensive tone, “What do you mean?”
Smiling, I shrugged my shoulders and then heading toward the front door, Kassie of course followed me.
Opening the door, I turned, and then after a hug and a little kiss, I left. As I started down the stairs, I turned. She was still there and after giving her a wave, and seeing her smiled, I headed down the stairs.
Being with her really was awesome, and we have talked on the phone a couple times, but as of late, because she is always so busy, we’ve kind of lost touch. I have continued to want to see her and when we did eventually lose contact, I started searching for her on social media and the internet.
Finally, I found her and was shocked to see she was actually a silent video porn star. “Noway,” I thought, but it was true and seeing she had appeared in a few videos, I knew what had happened.
I think about her a lot and hope we will connect again, but as of now, I can only think about what we had and watch the video clips of her.