Sissyboy Stories

140 results
Orientation
Length
Source
Infinite Scroll

Steve and Monica

by Dolfyn7 on Sep 16, 2017
BDSM

It was Saturday night. Monica had spent the afternoon fucking but now it was several hours later and she was ready to go again. She knew she could probably find someone to help her out at the local club, but the action there didn’t begin until around midnight. With time to kill she decided she might as well douche out the afternoon’s stale cum and cunt juice...

Erika Blossoms Ch. 03

by SmoovB on Sep 13, 2017
BDSM

Note: This is chapter three of a very long story. 28 chapters so far. It is wide ranging and will eventually touch on interracial sex, dom women, lesbian sex, true love, revenge and much, much more. I hope you enjoy it. ***** CHAPTER THREE – Saturday Afternoon and Night That afternoon, my boyfriend had to go to the office for a couple of hours. As he wa...

Trixie's Chastity 03

by trixie47cd on Sep 19, 2017
Transsexuals & Crossdressers

By the time I pulled my car into our driveway, most of the semen coating me from head to toe had dried to a flaking crusty shell. I stuck to the driver's seat as I climbed out on wobbly legs. The sun was just coming up and I hurried to get inside the house before any neighbors saw me like this. I started a pot of coffee, put the gallon jug of sperm in the f...

Stuck in a Hotel with Friends Ch. 01

by eroswizard on Sep 14, 2017
Interracial Love

It had been a very good year for me business wise. Not only had I made excellent money on sales commissions, but had been top salesman three months in a row. This earned me a promotion to sales manager, which included two weeks of paid vacation. The Holiday sales season was rapidly approaching, so it needed to be taken soon. My wife Cathy and I began discus...

Roxanne and Willie Ch. 18

by Goodhusband on Sep 19, 2017
Loving Wives

Note: This story is the eighteenth episode in a series entitled "Roxanne and Willie". If you have not read the previous seventeen episodes of this series, I encourage you do so before beginning this chapter. This is a dominant wife humiliates submissive husband story. That is the kind of story I write. If you do not enjoy these types of stories, I strongly...

Sandra and Stevie Ch. 61

by Goodhusband on Sep 19, 2017
Loving Wives

Note: This story is the sixty-first installment in a series entitled "Sandra and Stevie". If you have not read the previous sixty episodes of this series, I encourage you do so before beginning this chapter. This is a dominant wife humiliates submissive husband story. That is the kind of story I write. If you do not enjoy these types of stories, I strongly...

Job Interview

by britneyfan on Sep 11, 2017
Transsexuals & Crossdressers

I was interviewing for a new secretary and it had nearly reached the end of the day with no likely successful candidates. There was just one to go, a Tracy Class, whose CV certainly looked impressive and seemed as if she would do pretty well for the job, but I had to wait and see. The company's receptionist, Paula, put her head around the office door to tell...

Sandra and Stevie Ch. 52

by Goodhusband on Sep 19, 2017
Loving Wives

Note: This story is the fifty-second installment in a series entitled "Sandra and Stevie". If you have not read the previous fifty-one episodes of this series, I encourage you do so before beginning this chapter. This is a dominant wife humiliates submissive husband story. That is the kind of story I write. If you do not enjoy these types of stories, I stro...

A Sissy Saga Ch. 21

by Snurge on Sep 15, 2017
Novels and Novellas

The next morning Jennifer Hancock went down the stairs with her hair piled on top of her head and wearing a crumpled pale-blue linen overall to be amazed when Lulabelle said she looked as fresh as a daisy. Her mother was talking on the telephone, and when Jennifer appeared in the sitting-room she clapped her hand across the mouthpiece. "I've been negotiatin...

Made Over Ch. 03

by gbr2004 on Sep 15, 2017
Fetish

This story involves forced cross dressing, gay sex and bdsm scenes. Don't read if not into these scenes. * I had met a man in my apartment building and he had invited me to join him at a club he goes to in LA. I was a naive boy from Kansas attending USC and I had no idea what I was getting into. The club ended up being a gay leather bar and before the nigh...