First Time Crossdresser Xxx Stories Stories

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First Time Blowjob

by MyWhoreWife on Dec 10, 2019
First Time

I'm a man and I love crossdressing. I love the feeling of nylons on my legs and wearing strappy high heel shoes. While wearing them I would wonder what it would be like to suck a COCK in them. Kneeling between a man's legs and sucking his hard and meaty COCK. I started to go to adult cinema's in the downtown area after accidentally discovering their existen...

The Literotica Xmas Bash

by Touch_type on Dec 15, 2017
Humor & Satire

The Literotica Xmas Bash All characters in this story are over eighteen years of age. Any resemblance to any person, living or dead, is entirely coincidental. Except in two cases. But I've got so much dirt on them, there's no way they'll sue. I'm assured by management that everyone voting for this story will get an invite to next year's party in the post....

Dexter the Photographer

by Moonraker_Bond007 on Sep 14, 2017
Erotic Couplings

TO THE READER: this story includes several characters from the series of Jason Garrett stories; however, this story is not part of that series. Hi there. My name is Dexter Malcolm. I take pictures for a living. I used to ruin - or sometimes improve - people's careers for a living. I would take photographs of them in particularly compromising positions, and...

Taken by a Real Man

by gbr2004 on Sep 2, 2017
Fetish

Fictional work. Reading is at your option, sure you understand what this story is about. ***** Just got to my hotel room in LA. Nice room, 27th floor, good view, some floor to ceiling windows. My name is Steve, I'm 24, married, no kids, 5'8", 145. I am naturally pretty smooth and I'm in pretty good shape for my age with brown hair, longer than most, reachi...

A Latex Crossdresser's Dream Pt. 01

by shinyglove on Aug 6, 2019
Fetish

I had always enjoyed latex from even a young age, 16 onwards, and would always steal latex gloves from Dr Surgeries to use when wanking. Roll on a few years and endless watching of latex porn and also involving my wife in the purchase of several latex items. First it was just a latex miniskirt and she saw my reaction to this and so the collection grew. I ha...

A Latex Crossdresser's Dream Pt. 08

by shinyglove on Mar 17, 2020
Fetish

A Latex Crossdressers Dream. Part 8. "Rubber wife's Rubber Party Plan" I woke up early the next morning refreshed. I was quite an active guy so only needed a good 6 hours and I was good to go. I had left the girls downstairs and gone to bed and when I awoke there was no sign of the girls. Only 2 more empty wine bottles so I suspected they had gone to bed dr...

Carla Likes to Watch - Me Ch. 04

by Marlene on Sep 13, 2017
Group Sex

After Carla's and my gang fuck things were kind of weird for a few days. It was like we were avoiding each other or certainly avoiding any conversation about our raunchy play time. Finally on Friday night we ended up drinking a bottle of wine and smoking some dope which of course lowered our defenses and we talked. Both of us was afraid of what the other one...

My New Life

by gbr2004 on Jun 1, 2020
Fetish

This story is totally fictional and involves forced fem, discipline, interracial sex, among other kinks. Kind of a long story with probably too much dialogue and not enough sex but I hope you enjoy it. *** I'm not going to take any more shit from this asshole. I'm talking about my stepfather. Sure, he's nice when Mom is around but when she isn't here, he t...

HypnoSissy: Educated to be Pegged

by silkstockingslover on Aug 13, 2019
Fetish

Summary: Cock sucker's training is advanced to hypno videos on anal sex. WARNING PLEASE READ: -This is a hypnosis story with potentially influential subliminal messages within it. -The story also contains hypnosis video scenes. -So if you begin behaving differently after reading this story and all your friends start pointing fingers, don't come crying to...

Crossdresser's First Anal Orgasm

by ksha on Sep 16, 2017
Anal

A young man still experimenting with his body, found a new fetish he enjoyed quite a lot. He found the joys of anal masturbation. He had heard rumours of an orgasm so wonderful it would leave you shaking afterwards. He was in search of his very first prostate orgasm. This is the story of the first time this young man would discover the joys of prostate pleas...