Transsexuals+&+crossdressers Stories

12,315 results
Orientation
Length
Source
Infinite Scroll

A Sexy Monologue

by JaxRhapsody on Sep 16, 2017
Transsexuals & Crossdressers

I saw you in the atrium, all gussied up and sexy. Me? I was at the bar, watching the people, watching you. I contemplated talking to you especially when you saw me see you. I watched as you walked away to wherever the hell you was goin' to. I return to my drink and my nice conversation with the man next to me- getting twenty minutes drunker discussing the au...

A Thrilla in Manila

by EARTHFORCE on Sep 16, 2017
Transsexuals & Crossdressers

I finally got my wish. For the last twenty years or so ,I've had a secret desire for lady-boys. For the past few years, all of my masturbation fantasies have involved lady-boys. The fantasies involve sucking their cocks or having them enter me anally. Over the past several months, I had been e-mail pen pals with a beautiful lady-boy from the Philippines. I f...

Tender is the Day

by IcelandSpar on Sep 16, 2017
Transsexuals & Crossdressers

Lolita, light of my life, fire of my loins. He was making the final preparations for slipping into his role for me, before he got a call. "Yes, this is Leland", he barked awkwardly into the phone, feeling the full contradiction of the moment as I came up to him, naked behind him, and lightly stroked his arms on either side. "Mmmph", he moaned, as I lightly...

Conversation with Gabriella Ch. 03

by stacey_lynne on Sep 16, 2017
Transsexuals & Crossdressers

Gabriel prefers to be called Gabriella at night and on weekends when her real preferences come to life. Olga is his wife. Daniel, virile, strong, and masculine, was forced to become Danielle. The following day, all day, was devoted to training you for the evening ahead. It would be the last evening together and we were going to a very nice party. Actually,...

On School Grounds

by PenanceS on Sep 14, 2017
Transsexuals & Crossdressers

It’s amazing how good the cloth feels against your bare skin. I had never thought of myself as anything but a straight and regular Joe. I didn’t think that I’d get a stiffy wearing woman’s clothing like this. I looked at myself in the mirror, just to see if my padding was well, there. I had borrowed one of my ex-girlfriends bras and stuffed it with a pair...

CD Gets Fucked while House-Sitting

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

This is a true story that happened recently. I also recently submitted a four-part, runaway-imagination complete fiction story, hope you enjoyed. For anyone not familiar with me or my stories, here's a brief background. I'm middle age, white, a little overweight (hidden well with the right garments), and a married bisexual crossdresser who LOVES getting scr...

The Molly Virus Ch. 01

by Sissyhalo on Sep 13, 2017
Transsexuals & Crossdressers

That was the name of the one that infected me. I've no idea where this started and I haven't seen her since. And I can't stop it, can't control it, can't stop being Cherry and breeding more. I remember going to this party on campus and I wasn't a popular guy, overweight and kind of a nerd and I can remember seeing Molly moving through the crowd with this...

My Girlfriend's Sex Slave Ch. 01

by subboy4821 on Sep 25, 2017
Transsexuals & Crossdressers

I show up to my girlfriend's house after she had sent me a text telling me how much she wanted me. I knock on the door and she answers. She's a raven-haired beauty, about 5'10 with light brown eyes and a fairly thin but athletic build. "I'm so glad you're here, I've been thinking about you sooooo much!" she says. "But first, I'd like to tell you something....

Le Sexe Superieur Ch. 01

by ValoryG on Feb 7, 2018
Transsexuals & Crossdressers

Around seven a.m. is always a hectic time around our place. Got to get our daughters Avery and Whitley dressed, give them some breakfast, make their school lunches, and not least of all, dress myself, then quickly put on some makeup, fix my hair and grab a bite. My wife Hadley has already left around 6 a.m. because of her long commute. She's a civil engine...

A Birthday To Remember Ch. 01

by majorpayne_1342 on Feb 13, 2018
Transsexuals & Crossdressers

Editor's note: this story contains scenes of incest or incest content. * My name is David West. I'm currently 25 years old and 1 week away from turning 26. I lived a pretty normal life. Quite routine honestly. I work on Mondays, Wednesdays, Fridays and Saturdays here at the local supermarket. On Tuesdays and Thursdays, I go to school. I had nothing real...