Crossdressing Stories

1,097 results
Orientation
Length
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Infinite Scroll

Wannabe Cuckold Gets Found Out

by tombrennen on Jan 20, 2020
Fetish

A little about myself before I start the story. A trim 35 year old man that would probably be diagnosed as a sex and porn addict. As long as I can remember, I've been extremely sexual. Starring at cleavage and tight pants, led to porn mags and the occasional video, led to the internet. Once the internet exploded, so did my sexual fantasies. Shemale porn, and...

Working Late Ch. 02

by S_Hollister on Dec 24, 2019
BDSM

Claudia had a busy enough Christmas, between family and social obligations, giving some as much time as she could afford and others just enough to seem polite. In the evening she spent her time reading. She hadn't really bothered with feminist literature since reading The Second Sex in college. Her discussion with Jay at Petra told her she had a lot of catch...

I am Number Four

by princessnocturne on Sep 18, 2017
Transsexuals & Crossdressers

I stood silently in the middle of my living room, surveying my very own new apartment with a weary satisfaction. I still had boxes of small stuff to unpack, dishes and books and the like, but the furniture and appliances were all in place, and the heavy lifting was more or less done. I felt a warm glow of pride as I saw it take place before my eyes, my first...

The Reunion

by thrillerauthor on Sep 14, 2017
Transsexuals & Crossdressers

© 2015 by Thrillerauthor Twenty years! It's hard to believe that much time has gone by since I limped out of Grover Cleveland High, at the bottom of my class, prospects zero. My sole achievement was the dubious designation as Class Clown, in recognition of outrageous pranks which got me suspended twice and almost expelled. The last, which nearly ruined the...

Girlfriend with Testing Device Ch. 03

by Razmagurk on Jul 10, 2018
Transsexuals & Crossdressers

Author's Note: This is part three of my smutty little romantic comedy series. This chapter starts off the Mall Arc, which runs until chapter 6. One of the longer chapters, it's a little lighter on the smut, but a little heavier on the swaps, and I hope you'll find it no less sexy. Please leave a comment! I really do love hearing from readers! Even when I'm...

Afro Stress Relief Ch. 03

by llts1970 on Apr 23, 2018
Transsexuals & Crossdressers

The morning arrived too early I hadn't had much sleep but got up, showered, shaved myself everywhere, should I have blue eyeshadow or green I wondered; I startled myself, I was going to do my main job not the other one, prostitute and black cock slut, this was all getting too confusing! With my ass cheeks and asshole still sore I went to work, once there I...

The Device: Media Bias

by Razmagurk on Aug 24, 2020
Transgender & Crossdressers

Warning: This one is all about big weird swaps and reality manipulations. It contains boobs, tits and other mammaries, institutional femdom, greek statues, slutty boys, fashionable chastity, alternate histories in the making, cunt-boy x futa, marathon fucking, celebrity m-preg, work place drama, explosions, horse cocks (girls with), cultural feminization, sl...

Julia, Ben and Lisa Ch. 11

by chloejacobs83 on Mar 9, 2020
Transgender & Crossdressers

Ch 11: Friday A few quick notes: 1. this is the eleventh chapter of a longish story, a novel in many chapters 2. everyone is 18+ 3. there is no safe sex here - cause it's a fantasy, not an instruction manual 4. crossdressing and gender bending, not everyone's cuppa tea - be forewarned Julia and I had a nice breakfast together. She was dressed college-c...

Afro Stress Relief Ch. 10

by llts1970 on Mar 30, 2020
Transgender & Crossdressers

I woke up on the Saturday, not believing what I'd got up to in the Beer Bust and not sure what to do, now everybody knew what I was, a little white sissy bitch that worshipped black dick! How would everyone treat me on Monday at work, Elizabeth had said not to worry as 'what happens at the Beer Bust stays at the Beer Bust', however how could I tell my black...

Divination and Manipulation Pt. 02

by bigrusker on Jul 30, 2019
Transgender & Crossdressers

This is the highly delayed and much anticipated sequel to my original story "Divination and Manipulation". I recommend you start there to learn more about how exactly Sam and Jenn got here. I hope you enjoy! ============================================= I awoke the next morning, groggy and alone. I sat up slowly, wincing at what felt like a rock rolling ar...