Tranny Surprise Stories

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Infinite Scroll

The Virgin Tranny & the Bride Ch. 08

by yano on Sep 25, 2017
Transsexuals & Crossdressers

My transvestite friend Roberta writes to tell me that recent surrender of her boy pussy to her Master was, sadly, not for love but as a means of gaining embarrassing video footage to use as sexual blackmail. Master John is now teasing Roberta and she is about to embark on a new career as a call girl and prostitute. She writes: With the lining removed and m...

Friends Always

by trigudis on Sep 14, 2017
Transsexuals & Crossdressers

She's cute, really cute. She's an eighteen-year old high school girl with silky, straight brown hair that she wears in various styles, depending on the season and her mood. Sometimes she parts in the middle, with the front sweeping across her forehead. Other times she puts it up in pigtails for that adorable, little girl look. In winter, she lets it grow lon...

A Close Encounter of the...

by Art on Sep 12, 2017
Transsexuals & Crossdressers

Another great tape and another great yank of the crank. Yea, she-males were pretty hot, Tom thought as he hit the eject bottom on the tape deck, but where on earth would he really find one? He had little doubt that if he did find a place where they hung out that there would be more than a few with a serious case of ugly. The chances of finding one like the o...

High School Friend Has A Secret Ch. 02

by horneyguy99 on Sep 12, 2017
Transsexuals & Crossdressers

It had been a little over a month since my first transsexual encounter and it still felt like it was yesterday. My night with Michelle had been a night of many firsts for me but I regretted nothing about it, only that I had to hide it from my girlfriend. I wasn't the cheating type and it did bother me to a certain extent that I was keeping this from Brittany...

M Is for Mandi

by BethanyJ on Sep 16, 2017
Transsexuals & Crossdressers

********** A series of stories with transgender themes which I hope will be of interest to those who like women, or would like to be a woman. Which includes me! ********** That night, that Friday, had been highlighted on the kitchen calendar for weeks, though my wife didn't know the reason why. OK, so she was off to her sister's for the night and that wa...

Why, She's A "He"!

by libidinal on Sep 14, 2017
Transsexuals & Crossdressers

Tina had mentioned to Dave a bar she’d heard about that catered to certain sorts of sexual adventurers and suggested she and Dave visit one night to check out the scene. A friend had described it to her and said she occasionally liked to go there with her husband. These two were old fashioned ‘swingers’ and Jane had told Tina that this bar catered to those l...

The Virgin Tranny & the Bride Ch. 04

by yano on Sep 25, 2017
Transsexuals & Crossdressers

Continuing the story of young transvestite Roberta and her adventures with Margaret and John. I have also received the following letter which is a little worrying. Dear Yano, I'm very sorry it has taken me so long to send the next part of my story, things have been very strained over the past few months and particularly between me and Margaret since I got...

Birthday Surprise

by Booblover56 on Sep 14, 2017
Transsexuals & Crossdressers

David came home for his birthday dinner with his wife Sarah to find her sitting at the table with another woman. She introduced her as Casey, a friend she met a few weeks ago and she came over to help with his birthday present later on. Was she going to do the threesome he always half jokingly asked for? Was she going to do the girl on girl things he wanted...

Wedding Plans Made

by Catytheghost on Sep 16, 2017
Transsexuals & Crossdressers

Allison Well, let's see...we have 100 invited guests to the Cambridge wedding and 200 for the one at home--talk about a zoo! Who to include who not to? Gee. The surprise was when the governor's daughter said she would be attending the one at Lucy's. Seems her daddy, the Governor, owes Lucy big time for his last reelection. Seems Silver is a licensed pre...

Twenty Questions

by DrLuverotica on Sep 19, 2017
Transsexuals & Crossdressers

THURSDAY I was just settling down to watch a movie when my wife arrived home after a night out with her girlfriend's. "You're home early," I said. "Lucia had to be back by ten. She's on the early shift." "Meet anyone else?" "Just a couple of hunks - they're coming over for supper later." "Very funny." "Actually I wanted to come home because I was feel...