Sissy Boyfriend Stories

60,292 results
Orientation
Length
Source
Infinite Scroll

Auntie Jean Drummond Lloyd

by Sissy Adele Howells on Aug 31, 2017
Fetish

I had been caught red handed. My kinky secret was now known by the stewardess of my local club. At 45 years of age, without a girlfriend, my world was about to change. Of course this was a fantasy dream, but everything was so real. Stewardess Jean Drummond Lloyd was 58 years of age. Sixteen stone of obesity, with short, blonde, curly hair. This was going gr...

Black Sissy For White Goddess

by Samuelx on Sep 16, 2017
Interracial Love

Finally, I feel like I am where I belong. Picture this, if you will. A big and tall, muscular Black man clad in a pink tutu and frilly White panties, my face fully made up and my lips properly rouged. I am kneeling before a six-foot-tall, slender red-haired White chick and sucking her strap-on dildo. My Mistress Amelia Heinrich smiles at me as I suck her dil...

Katelyn's New Sissy Pt. 01

by bluesbirds on Dec 25, 2018
Transgender & Crossdressers

I remember she made me try the Sissy Peni-Pacifier in the store. It was a humiliating day outing, meant as "my" Christmas gift. Dressed up in a tiny bright red sexy elf costume with marabou trim around the edges that ended at my sissy clit, black fishnet stockings and 4" black heels, with a ridiculously large shiny red bow in my hair, surrounded by mirrors a...

Miss Guided Pt. 04

by MissMarianne on Apr 9, 2019
Transgender & Crossdressers

The next morning I went to Dr. Emily's office for my appointment and reuniting with Charles. When I arrived There were two people talking to the receptionist and I couldn't see her face. Then, I realized that the receptionist was Charles! I heard one of the patients address him as "Charlene." He looked just like a woman. Dressed in a conservative skirt s...

Caught by My Bully and Exgf Ch. 02

by CindyTightass on Sep 15, 2017
Transsexuals & Crossdressers

This is second chapter of story about young crossdresser who is discovered by his ex girlfriend and masculine bully from high school. All protagonists of this story are consenting adults. ***** "Your face is a one big mess Cindy," said Michelle giggling, "let's go to the bathroom and clean you up!" She helped me to get up from my shaky knees and led me to...

Adult Bookstore Whoring

by nancyvasquez on Oct 15, 2017
Transsexuals & Crossdressers

Crossdressing sissy Terilyn Bardot arrived at the adult arcade around 6:10 p.m. The city was having some kind of carnival on the waterfront, and so most of the parking spaces were gone. Teri went in and stripped to just a 2 piece bikini and her high heels. She freshened up her hot red Revlon lipstick and greased up her anus with Vaseline. Then she waited. An...

Lock And Key

by ksu328 on Sep 1, 2017
Fetish

As the first snow of the season started to fall on my small hometown, my sex life started to make a turn just like the seasons. Well, I guess since I've never really had a sex life besides jacking off my little pee-pee, you could say that my sexual freedom was changing. The little box (ironic that it came in such a small box) arrived on a Wednesday and as m...

Thank You Miss 'Nessa

by Cleverlicious01 on Sep 13, 2017
BDSM

Of one thing, Vanessa was most certain: She savored the feeling of taking a typically, naturally dominant man, and turning him into a servile sissy. By chance, Mike already happened to have the secret calling encased in his DNA. His alpha male appearance, with lean muscular physique and beaconing hazel eyes, would have made any other woman weak in the knee...

Merry ChristmASS, Bitch Boy!

by humbleslave on Sep 16, 2017
Celebrities & Fan Fiction

The holidays were upon us. I had spent the last three months of my life as the personal sex slave of Brittany Andrews and Chantz Fortune. By now I was used to the chores, and the beatings, and constantly servicing and being fucked by their various strapon dildos. However, I never got used to the humiliating situations that they placed me in on a daily basis....

Cable Guy

by Girochen on Dec 10, 2017
Erotic Couplings

Sometimes I write little snippets, sometimes they are longer. Like snapshots of life, they occur to me and I must capture them. This is one that I wanted to share because I like it. It has some weird in it, man on trans man-girl, and some regular sex. But the real story is in between like a waffle holds the butter and syrup but isn't anything without the act...