Sissyboy Stories

140 results
Orientation
Length
Source
Infinite Scroll

My New Life

by gbr2004 on Jun 1, 2020
Fetish

This story is totally fictional and involves forced fem, discipline, interracial sex, among other kinks. Kind of a long story with probably too much dialogue and not enough sex but I hope you enjoy it. *** I'm not going to take any more shit from this asshole. I'm talking about my stepfather. Sure, he's nice when Mom is around but when she isn't here, he t...

Courtesan Ch. 10

by Goodhusband on Sep 19, 2017
Loving Wives

This is the tenth episode in a series entitled "Courtesan". If you have not read the previous nine episodes of this series, I encourage you do so before beginning this chapter. "Courtesan" is romantic story about a dominant hot wife and her submissive cuckold husband. While they have a deep and abiding love for each other they do lead an alternative lifesty...

Sandra and Stevie Ch. 30

by Goodhusband on Sep 19, 2017
Loving Wives

Note: This story is the thirtieth installment in a series entitled "Sandra and Stevie". If you have not read the previous twenty-nine 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 stron...

Courtesan Ch. 38

by Goodhusband on Sep 19, 2017
Loving Wives

This is the thirty-eighth episode in a series entitled "Courtesan". If you have not read the previous thirty-seven episodes of this series, I encourage you do so before beginning this chapter. "Courtesan" is romantic story about a dominant hot wife and her submissive cuckold husband. While they have a deep and abiding love for each other they do lead an alt...

Courtesan Ch. 14

by Goodhusband on Sep 19, 2017
Loving Wives

This is the fourteenth episode in a series entitled "Courtesan". If you have not read the previous thirteen episodes of this series, I encourage you do so before beginning this chapter. "Courtesan" is romantic story about a dominant hot wife and her submissive cuckold husband. While they have a deep and abiding love for each other they do lead an alternativ...

The Sexy Domme Next Door Ch. 03

by rickiee_2002 on Sep 19, 2017
BDSM

Ch. 3 Carissa takes the initiative "Mr. Lewis, you're niece is here to see you" announced my secretary. I started thinking ... my niece ... my niece never visited me here before. I thought it was kind of odd. "Send her in" I replied As I looked up upon hearing the door knob turning, I saw Miss Carissa enter my office with a smirk on her face. "Hi Uncle...

Casey's Submissive Journey Pt. 03

by corduroysissy on Dec 16, 2017
Transsexuals & Crossdressers

Angie & Debbie (Fag Night) Part One Audrey was dressed in a pair of tight black mid-wale corduroy jeans and had an 18" dildo sticking out through the fly of her pants. She laughed maniacally and grabbed Casey's balls. "I own you sissyboy. First I'm gonna yank on your sissy balls til you beg for mercy, then I'm gonna fuck your sissy ass with my big cock...

Courtesan Ch. 22

by Goodhusband on Sep 19, 2017
Loving Wives

This is the twenty-second episode in a series entitled "Courtesan". If you have not read the previous twenty-one episodes of this series, I encourage you do so before beginning this chapter. "Courtesan" is romantic story about a dominant hot wife and her submissive cuckold husband. While they have a deep and abiding love for each other they do lead an alter...

Robin and Jimmy Olsen - Sissies Ch. 04

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

The Date Continues (finally) ***** Just as Ollie and John began to wonder what was keeping their dates, they spotted the delectable pair of sissies returning from the rest room. When they reached the table, both men stood. Their politeness was rewarded by a brief kisses from the pretty lads. Each girlyboy also managed to run her hands across the crotch of...

Balls On The Line In City Trading Ch. 02

by gomorrah on Sep 16, 2017
Transsexuals & Crossdressers

So with much apprehension, I turned the handle on the blue door. Stepping through, I struggled to adjust my eyes to the brilliantly white light streaming out of the other side. I raised my hand to try and filter the glare, and heard the door click shut behind me, and then double-click again. Instinctively, I tried for the handle on my side, but there was no...