Gay Sissy Stories

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My Husband a Pornstar Ch. 03

by gtanya on Mar 20, 2018
Transsexuals & Crossdressers

Please read the previous two stories to fully understand and enjoy this chapter. If you don't want to read them, here is a brief description of what has happened till now: *** My husband was conned by me into exploring his sexuality and he finds out that he is bisexual. He also agrees on being a porn-star to earn a hell lot of money for us. After shooting...

Fifi La Femme: A Pansy at Last Ch. 02

by pris69696 on Sep 14, 2017
Transsexuals & Crossdressers

Chapter 2- Missing Big Frank Coming Out Telling our wives wasn't easy especially for me who had seduced Shirley's gorgeous hetero husband by dressing up in my wife Doreen's lingerie and make-up and offering him full homo sex as a limp wristed effeminate lady-man. It was my first experience as a queer and when Frank asked me to marry him; to be his gay wi...

Stevie's Journey Ch. 03

by gbr2004 on Dec 2, 2019
Fetish

I get up and put on some of my regular clothes, workout shorts and a t-shirt and flip flops. Try to digest what happened yesterday and how everything just spiraled out of control and now I find myself in this impossible position. It's like all choices have been taken from me and this group of people took over my life. It was exciting but I can't be doing the...

Darling Nikki Pt. 02

by Latexsissy69 on Sep 25, 2017
Transsexuals & Crossdressers

Chapter 1 - The Morning After The next day, Nick awoke thinking it was just a really messed up dream. When he got out of bed and found that Samantha had unlocked and removed the dress, panties and shoes, but everything else was still on, he was pulled right back to reality. He looked in the mirror on his wall and saw that he was standing there in a very tig...

A Shell of A Man

by uppishcarrot on Sep 13, 2017
Transsexuals & Crossdressers

Six years ago, I was doing well enough to finally afford my dream apartment. It was a studio apartment on the upper side of town. So, I had the job, the apartment, the money... but I was lonely. Very lonely and very horny. Not only would I get all hot and bothered from looking at all of the pretty women at work, but there were also plenty of hot women who li...

Jasmine - Sissy Slut Transformation Pt. 01

by BillyBaroo4you on Jun 1, 2020
Transgender & Crossdressers

A Sissy Cumslut Transformation Part I - The First Taste (of cum) Nervousness crept into his mind like a snake, slithering its way down toward his stomach. He felt scared, worried about the night ahead, worried about how this one night would change his young life forever. His gentle hands began to tremble as he applied the hot pink nail polish to his finger...

Developing Emma Ch. 04

by Sputnik57 on Sep 19, 2017
Transsexuals & Crossdressers

Emma took comfort in the shoes he'd bought her as the days passed, and as she slept she thought hard of the warm suitor's face and kissed her pillow; her anus tingling sweetly on the butt plug, imagining the beautiful sensation she'd experienced when he'd mastered her for the first time. She yearned for him and hoped he'd not just used her for a moment's ple...

Sissy Boi

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

COFFEE "Thanks for me, Raquel, I'm at the end of my tether and I don't know what to do with Dan anymore." I was meeting Raquel, one of my colleagues for coffee. She knew I was struggling with my husband, but didn't know the problem was in the bedroom. "That's alright, Jo. My pleasure." "Look what I've got to share with you is deeply embarrassing, so I beg...

Mistress Commands Me in the Office Pt. 03

by Tracy69 on Dec 3, 2019
Transgender & Crossdressers

First a little clarification, if you've been reading parts one and two (I hadn't kept this quite straight up to this point). Here are the correct character names: Bob, or Robert, or Dick (or whatever my mistress decides to call me): Me Rick: My boss Brad: An office co-worker Rod: Office co-worker in an adjacent cubical, very buff, quite manly Wilson: Of...

I"M Not, Really, I'm Not Pt. 02

by gbr2004 on Sep 14, 2020
Fetish

It's Saturday and I can't stop thinking about having to go out this evening and having dinner with Mr. Grant but I know there is no way out of it. I'm watching a game on tv when the doorbell rings. When I answer it, there are two men standing there. One is holding a couple clothes bags and the other several boxes. 'Are you Steve?' and when I answer in the a...