Shemales Stories

429 results
Orientation
Length
Source
Infinite Scroll

Up to Scratch

by spitzharder on Sep 14, 2017
Transsexuals & Crossdressers

Pushing away the coffee cup, the flash of my red painted nails caught my eye in a nearby mirror. Judging by the reflected sideways glances from men in the café my facial surgery had worked even better than I had thought. I was a 24 year old Shemale, with long dark hair and breast implants to die for. New in town due to a job transfer, I wondered what I shoul...

The Voyeur & the Frigid Wife Ch. 02

by gonzi2 on Sep 19, 2017
Loving Wives

My names Johnny, I'm fifty-eight married to Joan twenty years my junior. My wife's was frigid because of her church upbringing, sex being dirty unless it is done for procreation. I own a photographic shop, but because I wasn't getting sex I became a Voyeur, fixing up a C.C.T.V. link in the ladies changing room. I had an affair with my next-door neighbour b...

First Time with a Shemale

by BigAndy922 on Sep 13, 2017
Transsexuals & Crossdressers

I was living in LA and pretty fresh out of school, not to mention pretty naive in the peripherals of human sexuality. I'd been with a few girls growing up, but nothing ridiculous. I liked going out with my buddies, and we'd drink and there was the occasional recreational use of ummm, how should we say... party favours. I liked my share of porn, and as I had...

Hotel Club Ch. 05

by pantywriter on Jan 6, 2020
Transgender & Crossdressers

I woke up from a fitful night's sleep. The slow, soft, wet and sloppy blowjob I had given Cindy did not improve my mood, not after the fight with my...wife? Ex-wife? I sat up in bed and rubbed my face hard. The increased blood flow felt good but did nothing to quell the rising anger. I showered angry. Brushed my teeth angry. Dressed angry. Ate breakfast an...

Shortening His Sentence Ch. 02

by SugarandSalt on Sep 11, 2017
Transsexuals & Crossdressers

I knew when writing the first chapter that I'd get around to writing a follow-up chapter. This one definitely requires another installment sometime as well. I mentioned at the start of the last chapter that there wouldn't be tons of sex from the get-go, the same can't be said for this chapter. ;) * Foster's tongue lapped at Miss Julia's cock head. It'd bee...

She Thong

by mrstanley on Sep 16, 2017
Transsexuals & Crossdressers

Her name was Cindy and she had been born a male. Cindy was a beautiful woman is every way except one. She didn't like the term tranny and preferred being referred to as a shemale. She was truly happy living as a woman. She began taking light doses of hormones at 19 she had stopped hormones because she had difficulty maintaining a full erection. Cindy was bru...

This Story Sucks Ass

by YANKEE DAN on Sep 15, 2017
Humor & Satire

Part 1, The Intro Some very few of you may know who Matt is. For those of you who do not let me make a short story even shorter. Matt was sucked into a dimensional portal created by the meeting of two very special books, soon after he met up with some shemales who turned him into a girl and banged him. Afterwards, he ran afoul of a tribe of penguins, and fl...

The Creation of Amy

by michael1k on Sep 25, 2017
Transsexuals & Crossdressers

My name is Henry and my girlfriend's name is Amy. Amy is 18 and I'm 19 but I'm only slightly older by four months, we met in high school. This story is how Amy became Amy. You see Amy is not a girl in the traditional sense, when I met her she was a boy. I am what you would call a preppy guy, I was raised with money. I rarely saw my parents and was basical...

Three in Bed

by normadel on Sep 16, 2017
Group Sex

From my journal - Ray was out of town. I was horny, so I rented a shemale movie from our favorite adult video shop. When I got home I stripped and laid out my toys and lube for easy access and put in the tape. As I watched shemales having sex, I wondered why some could get hard and why some remained limp. Anyhow, I soon was wet and ready to play. I began on...

Heather in Leather

by Inktligent on Sep 14, 2017
Fetish

Dan walked into his video rental store and headed to the back section. As he moved past the curtain, he saw a good looking woman was also looking for some porn. It wasn't very often that he saw females in here, and he felt slightly uncomfortable. Starting on the opposite end of the XXX video shelves, Dan sifted through the hundreds of titles. He looked for...