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Tranny Stories

August 1, 2014 5:47 pm
A couple of months ago, I was contacted by a crossdresser here at Xhamster. She has asked me not to reveal her identity. We arranged to meet one night at a motel near the Pittsburgh International Airport. I arrived at the agreed time, but when I knocked on her door she told me she wasn't ready yet and asked me to wait half an hour. I agreed. Half an hour later, I returned to her room, but she still wasn't ready. She was apologetic, and asked me if I would rather come back in another half hour, or would prefer to wait in the room while she finished dressing. I told her I would like to wai... [read more]
Added by: shemale lover | Views: 4137 | Read full Story
July 31, 2014 5:47 pm
Tyrone is a tall skinny black guy 22 years old and his Mel is short and pudgy. I am an older white sissy. I wear female clothing under my regular clothes all the time. Saturday morning I went to the small house they rent and brought an overnight bag. Tyrone opened the door and I walked in. I sat down and we talked about him being single and his roommate and then his job. I had brought a small bottle of whiskey and took it out of my bag. Get us a couple of short glasses and this will get us in the mood. Tyrone told me he was always in the mood as he got up and went into the kitchen. He... [read more]
Added by: shemale lover | Views: 1314 | Read full Story
July 29, 2014 5:47 pm
I breathed in his musky scent while I squeezed and pulled his ample ass cheeks. I could smell that uniquBusiness and Pleasure: Seduced CD Pt. 2e man scent coming from between his legsBusiness and Pleasure: Seduced CD Pt. 2,Business and Pleasure: Seduced CD Pt. 2 sweat, moisture, precum, cologne all together. I tried not to gag as he continued to push his thick cock inside my mouth back and forth. At the same time I could feel my flower opening, as I squatted, knees out, my asshole seemed to open and I felt like i needed it filled like never before, the desire consuming me. My clitty was swolle... [read more]
Added by: shemale lover | Views: 1243 | Read full Story
July 27, 2014 5:47 pm
I was always interested in women's clothing. I don't know what it was but it just made me wonder what it was like to be a girl. When i was 15 i finally gave into my curiosity and wanted to browse my s****rs clothes. I went into my s****rs room when the house was empty and opened up her closet. I saw all of her nice shirts, blouses and dresses, i looked around pulling some stuff out and eventually made my way to her dresser and saw all the panties and bras. I wanted so badly to try on a whole outfit but i was terrified of getting caught. Then i got an idea. I picked out the clothes i wanted ... [read more]
Added by: shemale lover | Views: 2625 | Read full Story
July 25, 2014 5:47 pm
Why did I keep making bets like that, was the only thing I could think of while in line. Why did I keep making bets I was destined to loose, and then have outcomes like...well, this. I was standing in line to go to a cosplay convention, and was in full costume, but of the wrong gender. I was dressed up as one of those Vocaloids, with knee length blue pigtails, A black skirt that was barely at my knees, a set of black and blue boots that went up to my thighs, a sleeveless vest like shirt, a weird belt thing, weird glove-like sleeves (that left my armpits and upper arms open for the whole world ... [read more]
Added by: shemale lover | Views: 1446 | Read full Story
July 23, 2014 5:47 pm
I was driving down the Pacific Coast Highway one day in my pickup. It was sunny, and beautiful, a perfect California day. Only problem was the traffic. You could barely move. Still, you could hear the waves and the gulls and I was feeling good. I had noticed the blond in the convertable next to me. I could look down at her from the cab of my truck, and she was showing off her spectacular cleavage in a red bikini top. Her tits were big and full, and you could see them all the way to the nipples. Her wavy blond hair blew lightly around a cute face. I couldn't stop looking... [read more]
Added by: shemale lover | Views: 3022 | Read full Story
July 21, 2014 9:40 pm
So, after being made up like a slut, left glued to a pair of silicon breast forms, and caught sucking-off my best friend, I was pretty sure my day couldn't get any worse, but I had come nowhere near the end of my torment, as Michelle now had something else planned that I was probably not going to like. Brittany got all tarted up to go clubbing with her friends. Michelle and I ordered pizza, flirted with the delivery guy like a couple of teeny-boppers at a sl**p-over, and killed time by playing video games. I got my ass kicked more than usual because I couldn't stop staring at my reflection ... [read more]
Added by: shemale lover | Views: 2656 | Read full Story
July 21, 2014 9:40 pm
It was the height of summer, and my girlfriend was out of town for 2 weeks. I'd had a handful of experiences with guys before, but ever since I dressed up like a slut for the first time, I couldn't stop thinking about meeting another crossdresser for some horny mutual fun. I had been faithful to my girlfriend, but after that halloween party where she dressed me like a slut, I realized that there was a whole side of me yet to explore that lay untapped. My partner knew I was bisexual, and was into me crossdressing occasionaly when we had sex, so I felt comfortable telling her about my secret fan... [read more]
Added by: shemale lover | Views: 1662 | Read full Story
July 21, 2014 9:40 pm
Few years back I was in a bar in London getting a round in for the lads before we hit Fabric. I will be the first to say I'm not the fittest of guys and rely a lot on my charm. I took the drinks back to the table and returned to the bar to grab mine when a stunning Asian girl caught my eye and smiled at me. She glided when she walked, a smile that made your heart melt and a body to die for, why was she heading over to me....? We chatted for a while and I agreed to meet my friends in the club a little later so I could get to know this amazing angel. We chatted, flirted and laughed until th... [read more]
Added by: shemale lover | Views: 3220 | Read full Story
July 21, 2014 9:40 pm
8:20am Monday Morning --------------------------------- "...You can't be serious, Mike. There is no way anyone is gonna believe me," I whispered intensely. I was sitting in the school office dressed in the patently ridiculous outfit Michael had picked out for me that morning, waiting to see the principal over my "disruptive" behavior. I just glared open-mouthed at Mike as he patted me on the head and smiled. "It's gonna work great, Andi. Just trust me," he said, and then walked out of the office. I watched him walk down the hall back to class, and it was then that I saw my mothe... [read more]
Added by: shemale lover | Views: 1168 | Read full Story
July 21, 2014 9:40 pm
Post-Op Transexuals Are A Lot Of Fun Too Here is another story about an experience with a post op t-girl named Krysta. I have had quite a few experiences with her, here are some of the best. The first time I visited her, Krysta gave me a prostate massage, something I had never really tried before. I was sold on her description of the experience I would have and it created the most powerful orgasm in my life. Left my legs shaking for 5-10 mins, seriously. My second experience was just as enjoyable, I tried her 'strap on' experience (I believe she called it 'pegging'),... [read more]
Added by: xanykeyx | Views: 937 | Read full Story
July 21, 2014 8:06 pm
Why did I keep making bets like that, was the only thing I could think of while in line. Why did I keep making bets I was destined to loose, and then have outcomes like...well, this. I was standing in line to go to a cosplay convention, and was in full costume, but of the wrong gender. I was dressed up as one of those Vocaloids, with knee length blue pigtails, A black skirt that was barely at my knees, a set of black and blue boots that went up to my thighs, a sleeveless vest like shirt, a weird belt thing, weird glove-like sleeves (that left my armpits and upper arms open for the whole world ... [read more]
Added by: shemale lover | Views: 445 | Read full Story
July 21, 2014 8:06 pm
after failing to loose my virginity,i decided to try again. my man friend love to fish and would make his way to inch early every sat morn. being a creature of habit he always returned at the same time. one sat evening i accidently on purpose bumped into him on his way home. standing at the side of the road he stopped and offered a lift. knowing rightly what i was doing i told him i was just out for a walk. asking if i was ok after our last encounter and seeking reassurance, i told him that i really would like to do it again.he told me that he hoped id say that and he had a surprise for me at ... [read more]
Added by: shemale lover | Views: 1186 | Read full Story
July 21, 2014 8:06 pm
We had been chatting online for a few weeks , when Tamanna said she would love to come it with me. The doorbell rang at my flat and I wobbled on my stripper shoes to the door. The butt plug Imwas wearing made me squeeze my ass cheeks together and gave me a wiggle in my black latex dress to die for. I opened the door and there she was for real. She looked gorgeous, a red headscarf framed her cheeky smile and her pink lippy set off against her rammed skin, made her sooooo kissable. We kissed on the cheek and she came in. Her red shoes went beautifully with her outfit and I just wanted to ju... [read more]
Added by: shemale lover | Views: 922 | Read full Story
July 21, 2014 8:06 pm
All my stories are based on my own experiences After my first experience with a shemale (also pasted on here, She was a He) I wanted to have a second, but this time for me to knowingly know what I was about to do. I trolled chat rooms and dating sites for a few months, getting to know a few girls and then approached the subject. I soon was going to go on my first date with a shemale. We meet at a local station and she was as stunning as her pictures and so convincing, she was even turning heads as we walked down the road. The evening was lovely and the food was great. We connected an... [read more]
Added by: shemale lover | Views: 1137 | Read full Story
July 21, 2014 5:47 pm
Derrick really took advantage of having me captive that first weekend. He spent the entire time making me watch porn videos, and then had me recreate the scenes with him. He said, that he needed his girlfriend to be fully versed in all the ways he liked to be pleased. His appetite for sex was unreal. The only time we ever really took a break was to eat. And I have to admit, he made the most amazing strawberry milkshakes to go with the food. It was almost worth the humiliation of being fucked sideways by my best friend's b*****r just to get those shakes. By Sunday night we were both exhauste... [read more]
Added by: shemale lover | Views: 896 | Read full Story
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