Sissy Boyfriend Stories

60,292 results
Orientation
Length
Source
Infinite Scroll

Little Larry Ch. 02

by pantywriter on Oct 9, 2018
Transgender & Crossdressers Stories

The transition from sleep to wake came rather early for Larry the following Monday morning. He rolled over and sat up, and winced as a blinding flash of pain hit him. "Owwwww fuck me," he moaned as he quickly adjusted his sitting position. When he stood it was slowly and carefully, and it wasn't until he had walked through his apartment getting ready for Mon...

From a Husband to a Dutiful Sissy Ch. 06

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Six will compress time a bit more forward in moving the story through time. It will be set two months forward from the original start date of the story in Chapter One, when Helen found out her husband Phil enjoyed crossdressing and fantasized about being sissy maid and a sissy slut. It all picks up with bit of recollecting from Phil who is now Chante...

Mistress Sharon Pt. 01

by corduroysissy on Sep 5, 2018
Transsexuals & Crossdressers

Dana had just finished moving his corduroy girly clothes from the washing machine to the dryer when the phone rang. Being a closet fag and having a corduroy fetish, he not only dressed often but jerked off with his wardrobe on a daily basis, sometimes two or three times a day. As you can imagine that created a lot of sperm stains, and his skirts and dresses...

A Sissy's Halloween

by Evangeline_E on Oct 29, 2018
Transgender & Crossdressers

Disclaimer/authors not: All characters in this story are over the age of eighteen. This is my first story so criticism is wanted as long as its constructive. I make these stories based on what I want and my own sexual fantasies. Thank you 😊 . * To tell this story right I need to start at the very beginning, the time where I first started to question my se...

The Proof is in The Pudding

by desireethtttv on Sep 16, 2017
Transsexuals & Crossdressers

When my girlfriend of two years mentioned she liked to watch female impersonators perform, I seized the opportunity to confess my lifelong addiction to cross-dressing. The expected reaction of disbelief was no surprise but her reply of, "Well, let me see you dressed," was although welcomed, a bit of a setback. I'd not planned the truth to be revealed at suc...

Melody the Maid

by nohbdy88 on Sep 14, 2017
Transsexuals & Crossdressers

Melvin had been out of work for six months now. After being let go from his previous job, he had promised his wife Susan he'd find new work soon, but soon fell into lazily living off of Susan's income. At her request, Melvin had started helping out with the housework even more. One day, a package arrived in the mail for Susan. "Honey, I have a gift for you...

Helping Jess Pt. 05

by mski on Sep 25, 2017
BDSM

I slept well that Sunday night which surprised me, though I guess I was probably exhausted. I woke up with my normal hard-on a bit before 5am, well it would have been a hard-on but for the cage. My penis was certainly trying. I never found it an uncomfortable feeling, just frustrating that there is no ending and I could not jerk off, and now who knew what wa...

Cream Puff Ch. 03

by RubixStu on Mar 25, 2019
BDSM

I was naked except for my wig, my makeup, my stockings and my heels. I sat on Roger's lap, his erect cock deep inside my ass. He was watching a nature program. My legs were spread and his arm was wrapped around me while his hand lazily toyed with my little boy parts. He wasn't fucking me, he was simply impaling me, filling me with his masculinity while I rev...

Camboy's New Mistress

by pluggedforlife on Jun 5, 2018
Transsexuals & Crossdressers

His heart was pounding with passion. The big black dildo slid in and out of his well-lubed butthole, tickling his prostate. He could feel the large black penis glans squeeze out a drop of precum as he exhaled a moan of lust that was building up in his lungs. His steel chastity cage was flopping up and down, hitting his smoothly shaven crotch. His silver ho...

Loving Wives

by NemosFolly on Sep 14, 2017
Reviews & Essays

First of all, it must be noted that I am not a writer of erotica. I find it much more fun, and erotic, reading stories where I'm not sure exactly what's going to happen (even if it's pretty clear from the direction of the story so far) than writing ones where I have such absolute control. But I am an avid reader, and I have read many stories in each of the c...