Page 17, Gay Crossdresser Stories

Fighter Pilot's Pussy

By Clark Wayne 4 Apr 2020

Bi fighter pilot comes home to find his fighter pilot fuck-buddy waiting for him in sexy lingerie.

9.3 (125) 13042 25 Min Comments

The end of a perfect night out as a sexy woman

By Bob Long 1 Mar 2020

This was the last but ultimately the best part of evening when my girlfriend took me out to a gay club, dressed as a woman just to test the water and to assure me that I not only very passable but also pretty damn hot. I got way much more than I imagined

8.4 (12) 3533 11 Min Comments

Sweet Chrissi (ch. 3)

By Mikal 19 Feb 2020

Bored and in need of some dick Chrissi gets a surprise visit from a fellow sissy boy friend Daisy and it leads to a three way.

8.2 (13) 1073 7 Min Comments

Broken

By Clark Wayne 17 Feb 2020

Straight man is attracted to an alpha. He becomes the alpha's toy. He tries to rebel but his new Alpha has decided to fix his attitude and humiliate him. If the closeted straight guy wants to get fucked, he'll have to wear some panties to show his devotion.

8.7 (113) 12627 6 Min Comments

Before she turned me out

By Bob Long 10 Feb 2020

My girlfriend who fostered my obsession with crossdressing and living as a woman, trained and made me into one hell of a beautiful woman who eventually sucked a mans cock and loved it

7.8 (30) 8485 51 Min Comments

How I got started (ch. 3)

By Bob Long 5 Feb 2020

Our continuing story of the greatest time of my life exploring and fulfilling my deep seated desire to be a woman through crossdressing and learning about my sexuality with the best teacher in the world my mom

8.3 (17) 1314 19 Min Comments

How I got started (ch. 2)

By Bob Long 4 Feb 2020

This is a continuation of my glorious introduction to crossdressing and sex

7.8 (6) 2226 23 Min Comments

The Skin of Things (ch. 16)

By Chris Lewis Gibson 4 Feb 2020

He could still feel Ezekiel's mouth on his, and on his neck. He could still feel Ezekiel's chest and stomach against his back, Ezekiel in him, and through him, his penis, swelling and pumping in his mouth, the warm touch of the palm of his hand.

9.6 (9) 244 11 Min Comments

Condo for Sale

By Habu 3 Feb 2020

Sex helps sell expensive San Francisco condos.

8.8 (42) 2473 18 Min Comments

My First time with a man

By Bob Long 2 Feb 2020

An encounter that just happened after years of repression

8.4 (83) 6921 14 Min Comments

Parking lot blowjob

By Bob Long 1 Feb 2020

This is the story of how my ex girlfriend, made it her mission to get me to suck a guys cock

7.3 (40) 9872 25 Min Comments

How I got started

By Bob Long 30 Jan 2020

This is how I began my life as a crossdresser, encouraged by my mother who lovingly guided me and embraced my desires to dress as a women

8.0 (131) 10740 12 Min Comments

Crossdressing

The Art of the Sissygasm

By cock whore kimmy 26 Jan 2020

Little CD fuckdoll has his first sissygasm and his life changed forever!

8.5 (49) 10751 3 Min Comments

Sweet Chrissi (ch. 2)

By Mikal 22 Jan 2020

A new tale about the continuing adventures of Chrissi.

8.2 (20) 1605 5 Min Comments

Caught crossdressing

By SandyCD 6 Jan 2020

Caught by daughter with me dressed as woman

8.7 (85) 15455 12 Min Comments

Big Sissy

By Nils Huim 28 Dec 2019

A gay sissy bottom receives a surprise birthday gift

7.8 (16) 10903 10 Min Comments

Amateur Crossdressing Prostitute

By Kristen Kross 23 Dec 2019

crossdresser's first time prostituting first timer

8.8 (92) 21329 10 Min Comments

A Sissy’s Dream Comes True! Again and again!!

By FishnetSissy 21 Dec 2019

2 blonde bimbos help a little sissy faggot become the girl he always wanted to be and Introduce him to a man who knows just what to do with a special girl like this!

7.8 (72) 34782 29 Min Comments

My New Apartment Manager

By Kristen Kross 21 Dec 2019

cd sissy meets her apartment manager

8.7 (67) 6360 9 Min Comments

Starbucks

By Nils Huim 16 Dec 2019

Two ex-cons have anal & oral sex and then plot (?) a robbery

7.7 (21) 1779 10 Min Comments

Living my dream

By SissyBoi 9 Dec 2019

A true story about me finally giving in to my deepest desire to become a cum addicted slut that loves being fucked and used as a toy, worships huge cocks and eats cum for breakfast.

7.4 (30) 8265 6 Min Comments