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Tranny Stories

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Home Alone With Shemale
I sat alone at my kitchen table. I drank a cup of coffee, smoked a cigarette. I was wondering what to do with my day and then my cellphone rang. It was my girl friend Carla. She asked if it would be okay to stop by, with her new boyfriend. I sensed something in her voice, but I didn’t know what it was. I later would find out and so will you. I told Carla to come on over, bring her boyfriend along too. I didn’t care. I didn’t have anything planned and I was bored as fuck. I hate sitting around the house on a weekend. It makes life feel so worthless. I could be out at the di... Read full Story
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The Century Gurl
The Millennium was upon us. Y2K was about to hit, and I was given a job to fix the computers at a Marketing firm in a small city on the West Coast. I hadn’t been in a relationship for a few years, my Ex had run off with some missionary that didn’t like anal sex. Everyone there was afraid of the I.T. Guy. They thought I could hack into their lives by staring at them and didn’t want me to know what they were up to. So one afternoon, I was sitting out at the Lunch/Smoke break area, I was joined by one of the Managers. Hadn’t met her before, but I wish I had. She was Tall, about 5’11” almo... Read full Story
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A date to the sex shop
So last night I decided to meet up with a young shemale in Portland, now this is my first time ever with a trans and I was so nervous and excited all at the same time my face kept doing this weird little twitch. So we hang out for a little before we decide to go to one of those classic dirty sex shops with the booths. And the best part was they had ts porn to watch at the same time, so while I'm getting fucked from behind watching my favorite model "Aubrey Kate" I exploded all over the floor from An anal orgasm. Best night ever.... Read full Story
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The Beginning Of Penny
This story is about how I became Penny, the cock loving, tranny. I remember being a kid and jerking off to dirty mags we stole from my friend’s dad. The pics that always made me hottest were the ones in the ads in the back few pages for phone sex with trannies. Looking at those hot and perfect women with hard cocks got me every time. When I was a few years older I had a rather adventurous girlfriend. One time as she was sucking my cock, she slipped her finger up my ass and I absolutely loved it. From then on, every time I jerked off, there was a finger in my ass. As the years went on I acquire... Read full Story
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Motel Blackout
I always enjoy my sales trips. The trips fit into my crossdressing lifestyle and the thrill of being in a different town and different people. After a long day on the road, I had just checked into a motel just about 30-miles outside of Nashville, TN. For my overnight trips, I always bring my special suitcase that has my “girly stuff” (panties, dresses, makeup, lingerie, etc.). Sometimes I would just dress up pretty and cam or play with myself. On a very few occasions I would run into a very horny stranger, tease him, but not put out and be satisfied knowing that poor guy was back in is roo... Read full Story
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Dirty little restroom tgirl slut. Part 2
As I left the stall I was grabbed by the arm by my friend, he winked at me knowing that I wanted to tease them all, I pulled the hem of my skirt showing off my cute panties. The two bigger guys who were in the restroom came over to me, they both towered over me they unzipped their pants releasing two huge members, I gasped as I saw the size of their dicks, I moved towards them, their big hands pulling at my clothes, my two friends Andy & Tony started to undress me. I stood in the restroom in my underwear surrounded by big men all of their cocks were growing into12'' monsters, I s... Read full Story
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Dirty little restroom tgirl slut. Part 1
Hello I'm a very convincing tgirl 22 but told I look like I should be in school. 5'4'', 80lbs, short blonde hair, tiny titties & a tiny boi clit 3'' hard. Dressed in a tight white stretchy lace top, red suede micro mini skirt, over the knee white socks with red stripes, chunky trainers, matching red lacy hot pants & sports bra. I had been out for a drink with 2 guys who have been planning on getting me out alone with them. I was bursting for a piss so they stopped the car at some shitty dive of a rest stop, the girls bathroom was out of order so I heade... Read full Story
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Big cock shemale from Pune, India
I just saw her profile on Planet Romeo, her name is ID is Kaynat / Muskan. I saw her photos and got attracted to her. I am always a big fan and lover of Shemales or TS. I called her and fixed appointment by negotiating with her for 2500 INR. I went to meet her, she stays in a condominium in a small condo. I called her and she directed me with wing and flat no. floor etc. I pushed bell and she opened door hidden behind it. As soon as door was closed i saw her and instantly go a big hard on and her beauty made me crazy. She lead me to the bedroom, where a TV was on with romantic so... Read full Story
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Pune crossdresser Night Girl
Hi friends, I hope you liked my earlier stories. This is my new story about a lady boy / crossdresser / sissy boy. Around 2 years back I came across a profile on Planet Romeo with name Nightgirl. I sent her message that i found her sexy and attracted to her and wanna meet her. I am always crazy for shemale and sissy. I negotiated with her on her charges and took her address and went to meet her on weekend. she stays on rent in a small apartment. She opened the door and I was spellbound. she was so beautiful. she is around 5.7 tall, fair and smooth. sweet smile, absolutely gi... Read full Story
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Nancy the hot and sexy TS in Pattaya
Hi this is Ris, this is my third story. Well Last year I went to Thailand on lone trip. I went directly to pattaya and had rest and went to Walking Street in the evening. Was visiting many nude bars, ts Bars, dance bars. but while walking on the street one particular girl catch my attention. she was tall, beautiful, sharp features, hazel eyes and red lips. I felt like giving her complements for her beauty, so i went near her and told her that "Hey I just came to tell you that you are most beautiful female i saw on the earth". She smiled and said thanks. She insisted me to sit... Read full Story
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