Sissy Fag Stories

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Humiliated Sissy Husband Ch. 03

by rik581 on Sep 14, 2017
Transsexuals & Crossdressers

"Come on Max, I don't have all day." Tanya was running the water in the kitchen sink making sure it was hot enough to shampoo Max's hair. Max stood just out of reach shaking his head. He was wearing a girdle, padded bra and a slip. He had a towel around his neck. He was wearing 6" red high heels because, that's what Tanya said sissies wore around the hous...

Night With Chantz Fortune Ch. 01

by lilguy on Sep 16, 2017
Celebrities & Fan Fiction

I had a won a contest to spend the night with Chantz Fortune. She was the star of the movie Boss Bitches 2. She was know as the Strap-on mistress. She would use this big strap-on on men. She was the most ruthless dominatrix out there. She was also the hottest. She look like a regular busty porn start but. "Take off you clothes. Go into the bathroom and do i...

A Weekend Visit to the Office

by Marty Fisher on Jun 4, 2019
Transgender & Crossdressers

I usually work from home as I have a very private place with a wonderful view and Lord knows I've put in more than my fair share of office hours over the years. But I do occasionally elect to make visits to the office both during normal office hours and off-hours to make copies, restock my home supplies and have a cup of coffee with a long-term friend or two...

My Girlfriend Made Me a Sissy Ch. 03

by libertinaXx on Sep 25, 2017
Transsexuals & Crossdressers

I lay on Jess' bed waiting for her and wondering what would happen for ages. She was in another room getting ready for her new lover, I was already dressed up. Pale blue, see through panties and matching bra, a short black skirt and a blue vest top. With my make up done to show off my pretty green eyes and my long brown hair styled wonderfully, I looked like...

Re-tooled

by Sissyhalo on Mar 13, 2018
Transsexuals & Crossdressers

Re-tool your life. Re-tool yourself. Sick of not getting what you should? Sick to fucking hell of all these assholes getting with hot people they really don't deserve? Sick to hell of Liberals and Feminists making impossible to jump through hoops so that only the privileged people get to be happy? Sick of being a goddamned incel? Look we all know that...

Casey's Submissive Journey Pt. 06

by corduroysissy on Feb 7, 2018
Transsexuals & Crossdressers

Homo Hubby Night – Part Two Note: In this continuing saga, Casey (Debbie) & Jamie (Angie) are closet crossdressers who are submissive to their wives Karen & Audrey (respectively), however in this section of the story there is no cross-dressing. Their wives are humiliating them by making the boys put on a homosexual sex show for their amusement. *...

My Glorious Transformation Pt. 01

by switchhitter420 on Sep 18, 2017
Transsexuals & Crossdressers

My first stab at erotic literature, let me know what you think! Part one of a serialized fantasy journey into sissy faggotry. ***** About ten years ago, I ended a pretty serious, 1-year relationship with a woman I had met while working at a bar. She was this classic beauty: elegant, dirty-blonde hair, thin frame, striking facial features, an amazing ass an...

Making a Sissy Jock Pt. 02

by Sissyhalo1 on Jul 6, 2020
Transgender & Crossdressers

I stared at Robin's card for an hour sitting in my truck completely freaked out and every time I touched my lips I felt that friction of Robin's cock. I tasted him. I got slammed with the realization I drank his cum and it was inside of me. I sucked cock and drank cum and just like the sissy porn stuff said I liked it. I was beyond freaked in going to th...

The Snow Sissy Ch. 01

by theonewhowas on Sep 16, 2017
Transsexuals & Crossdressers

Somewhere, in the frozen northern regions of our great globe, in the shivering mountains, there is a school of demon. Now, we all know what demons look like – they are creatures of immense, horrifying beauty. Even with their skin (which can range from Jet black, through fiery red, to the purest alabaster white) they possess inhuman and powerfully seductive b...

Shattered

by kayla_femboi on Sep 16, 2017
Transsexuals & Crossdressers

The following story is mostly true. I changed the names for the sake of privacy and maybe spiced up the details a bit. A little background about me: my name is Brian, although when dressed i feminize me name to Brianna. I was a closet crossdressing sissy. I had always been effeminate growing up and a bit confused sexually. I never really dated girls. Inst...