Gay Crossdressing Stories, Page 12

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) 8071 51 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

8.2 (5) 2044 23 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) 9400 25 Min Comments

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) 10014 3 Min Comments

Caught crossdressing

By SandyCD 6 Jan 2020

Caught by daughter with me dressed as woman

8.7 (83) 13730 12 Min Comments

Big Sissy

By Nils Huim 28 Dec 2019

A gay sissy bottom receives a surprise birthday gift

7.8 (16) 10344 10 Min Comments

Amateur Crossdressing Prostitute

By Kristen Kross 23 Dec 2019

crossdresser's first time prostituting first timer

8.8 (90) 19556 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) 33232 29 Min Comments

My New Apartment Manager

By Kristen Kross 21 Dec 2019

cd sissy meets her apartment manager

8.7 (66) 6116 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) 1676 10 Min Comments

Un-Expected Threesome

By Kristen Kross 7 Dec 2019

CD, girl, and a stranger meet in a motel room

8.7 (16) 2757 25 Min Comments

holidays with grandad (ch. 2)

By Sisyboy 21 Sep 2019

Part 2 of getting caught

7.3 (44) 9110 2 Min Comments

Met Mistress on grindr (ch. 2)

By zeenatcd 14 Sep 2019

My mistress made me her slave and gang banged me with her friend Domino,Alisa and Mariana.

7.8 (11) 4246 6 Min Comments

When and How did I start (ch. 2)

By Crossy Arora 26 Jul 2019

How my life changed from imagination to reality

8.3 (22) 3637 2 Min Comments

Dressed for success

By Steve Webb 23 Jul 2019

A friendly tourist gets the surprise of his life. A fantasy

8.2 (60) 6630 6 Min Comments

The birth of Slutty Tanya

By Slutty Tanya 9 Jul 2019

A chance encounter leads an occasional cross-dresser down the path of becoming a full time slut.

7.2 (34) 3946 4 Min Comments

Roommate surprise

By Steve Webb 24 Jun 2019

A horrific moment turns into a dream night

8.4 (85) 11560 5 Min Comments

Cross dressing went too far

By fetishlover 20 May 2019

My love of wearing panties, stockings and tights went too far nad got me into serious trouble...

7.3 (54) 16450 6 Min Comments

My new body modification

By Lingerielover 25 Apr 2019

My mini cock and balls are driving me mad, so I did something about it !!!

8.3 (62) 7893 6 Min Comments

Girly

By bootlicker 22 Apr 2019

A small, weak, submissive man is feminized and abused by a trio of dominant perverts intent on transforming him into their sissy slave gurl.

8.4 (46) 28323 66 Min Comments

Dressed as an Easter Bunny, Fucked like a Rabbit

By Shy Stuart 19 Apr 2019

Me and my gurlie friends go to the local tranny club dressed like Easter Bunnies and get fucked like rabbits

8.4 (37) 8576 5 Min Comments

She turned me out

By Bob Long 13 Mar 2019

My girlfriend not only encouraged my crossdressing but how she turned me into the cock sucking whore I am

8.2 (50) 9507 27 Min Comments

First me then my wife become a black guys bitch (ch. 2)

By Shy Stuart 10 Feb 2019

I bottle out of going into Carlton house and he's not happy. However, a week or so later while in a drunken stupor I give Carlton my address and invite him around to fuck me.

7.6 (76) 14490 4 Min Comments

I was a man this morning, but now?

By fetishlover 20 Jan 2019

Girfriend gets revenge on her man after finding him with a gay guy

7.3 (54) 10416 8 Min Comments

Sissy Hypno Vids ... how I've changed

By need2btakenow 29 Dec 2018

I started watching sissy hypno about 3 years ago. Played with the idea of dressing up as a CD many times growing up and occasionally as an adult. But the fad would pass and go away for years. Not anymore...

8.3 (65) 14210 7 Min Comments

Getting dominated by an 9 inch cock

By Sissy Bitch 27 Dec 2018

Got dominated by a 9 inch cock while i was traveling

6.4 (78) 17458 2 Min Comments

How i became a bitch addicted for cock

By Sissy Bitch 23 Dec 2018

My history on how i became a little bitch that can not live without cock.

7.3 (95) 20191 4 Min Comments

Boy to College Girl

By Sissy Scarlet 29 Nov 2018

Charles has battled against his feminine features all his life. It takes a single experience with a dominant, alpha high school jock in the locker room to make him know his place in the world. ! ARCS Needed !

8.6 (85) 28712 23 Min Comments

I'm a Slutty Cheerleader

By Brett 7 Nov 2018

Daddy wanted to fuck a teen cheerleader and I wanted him to fuck me, so he bought the outfit and I got more than I could have hoped for.

8.5 (79) 15526 8 Min Comments

The making of a sissy

By Jamie Villa 13 Sep 2018

How my fascination with all things femme began

7.0 (68) 8793 3 Min Comments