Crossdress Stories

204 results
Orientation
Length
Source
Infinite Scroll

Barrack Room Betty Ch. 09

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Nine - Pink Pussycats All good things come to an end and the six-week Reduced Operations Period at HMS Chelmsford ended on 15th January 1974. The Wrens and Leading Recruits were very busy as that day approached. The Depot needed to be de-winterised and preparations made for the return of the Ship's Company, the recruits, and the Wrens from their l...

Recruiting of a Sissy Maid Ch. 15

by Sissy_Chantel on Dec 22, 2017
Transsexuals & Crossdressers

Chapter Fifteen: Life Changes but Normalizes Monday morning, Carl and Chantel are up and at it, breakfast in the hotel restaurant and then a shopping excursion to an are Jewelry store for Carl to buy Chantel her engagement ring. Dressed sharply but casually Carl in a white button down shirt, Khakis and black walking shoes. Chantel a white turtle neck, black...

Lisa and Jack: Crossdress Fun

by CDWife on Sep 12, 2017
Transsexuals & Crossdressers

First of all, if you are looking for some story about a guy who turns into a cockslut - this isn't for you. Our main character doesn't dress up for the first time and realise that he is really a girl either. And just to make sure, the wife is not sleeping around or trying to magically turn him into a girl either. This is a story about a couple looking to e...

Becoming a Sissy Maid & Slut Vol. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Title: How I became a Sissy Maid and Slut for a Dominant Master. Preface: I would like to begin by thanking all who will read my story here. This is a sissy story based on many thoughts I have imagined, many times throughout my life. These erotic thoughts have been enjoyed for a long while in my life. Like many sissy girls, stories like the one I will wri...

Barrack Room Betty Ch. 14

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Fourteen – Supergirls Bangkok "I've fucking had it with Jason!" Michele spat at Rod Latham "That fuckwit tracked me down and found me in a bar in Naples and created an absolute shitfight. And every night I'm here in the club he carries on like a petulant child whenever I work a punter and in particular Lieutenant Steve Winters who is one of our...

From a Husband to a Dutiful Sissy Ch. 02

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Two: My reveal, a true reveal for the sissy in me. I reach to the bottom of the stairs and at the front doorway entrance, Helen and Jenny are standing and looking at me in my black maids dress, white tights, black velvet 5 inch spike heel pumps, wig and makeup. The look on their faces seeing me dressed as such is priceless. This is the first time He...

Giving In To Desire Pt. 01

by jpbiguy on Sep 11, 2017
Transsexuals & Crossdressers

First time interracial gay anal mmm threesome BBC gay crossdress drugs pot ecstasy coke bi-curious - If you don't like that stuff, you can't say you weren't warned. ***** I am a pretty average guy; six feet, maybe a bit thin at one-fifty-five, but I've got a killer butt that attracts both women and men. I've never actually been with a man, but with all of...

The Good Wife

by komrad1156 on Sep 13, 2017
Transsexuals & Crossdressers

Chapter One "Let's go! Dig deep!" Jason told himself as he passed the nine-mile point. Just one more to go—for today. Running was one of his four biggest passions in life. He also loved his job more than most people. At least he thought that was the case based on the way most people talked about "work." For Jason, work was fun. He couldn't wait to get there...

The Witch's Slave

by jacklangston on Sep 19, 2017
Transsexuals & Crossdressers

My nights are spent as I assume most twenty year old male's nights are, playing video games and watching porn. I usually seem to sleep better when I get a good load out before bed. It's hard, because I still live with my family, which is why I can only do certain things at night. Or when I'm home alone, those are the best. Sometimes my family goes shopping,...

The Marriage of Martin Hastings Ch. 15

by rik581 on Sep 12, 2017
Transsexuals & Crossdressers

M artin was in stunned silence as he walked hand in hand with Dorothy back to the house, their fingers interlocked. As they reached the house, Dorothy turned to face Martin and then, lowering his lashes, took Martin's hands in his hands and raised them to his lips and kissed them. "Good luck Martin," Dorothy said as he pulled Martin close. He kissed Mar...