Sissified Stories

213 results
Orientation
Length
Source
Infinite Scroll

Fetish & Fantasy Pt. 01

by GavinIsaNuisance on Jul 13, 2020
Transgender & Crossdressers

This work is completely fictitious, any similarities to any persons living or dead is purely coincidental and entirely unintentional. All persons depicted in naked/sexual acts are 18 and up. Down and out aspiring model Taran Kilkenny becomes the hottest commodity in an escort service for trannies! But first he's gotta get trained by his new and domineering b...

True Desires Unleashed Pt. 04

by CuckedbyBBC on Jul 24, 2018
Interracial Love

I recoiled in a sideways fetal position for a minute or so to catch my breath and let the pain subside. The concrete was not only hard and rough but it was hot as hell on my near naked body. I was writhing back and forth while putting pressure on my balls and lower stomach in an attempt to work through the pain. The uncomfortable ridges were digging into my...

The Spanking Couples CFNM Party

by reddbunnz on Sep 17, 2017
BDSM

Chapter One: Two days after one of the monthly Spanking Parties, Debbie and Marion were sitting in Marion's home office discussing their sexual appetites. Both were dressed as normal when relaxing in one of their respective houses. Both had casual clothes – for them, at least. Both sported normal, everyday bras and tops, but were butt naked below the waist...

What a Night

by Anoun_Ymous on Sep 17, 2017
BDSM

It all started out innocent enough...here I was laying in bed next to my wife on this cold winters night, just two nights before Christmas. We had arrived on time to her parent’s house with nothing unusual happening on the way. It had been a pretty dull night and with her parents having gone to bed the two of us and her younger sister had decided to get comf...

Flowers in Her Hair Ch. 06-07

by NSEW1 on Dec 11, 2018
Fetish

Warning: this is a loving wife story involving a dominant wife helping a man come to terms with his repressed desires to be cuckolded, punished, and sissified. If these themes don't appeal to you, don't read. Thanks. ***** Chapter 6 Lace and Pastels The next morning, Victor could not find the boxers he had packed in his luggage. He ruffled around but to...

Helen Ch. 06-07

by Philippasubmaid on Jan 2, 2018
Transsexuals & Crossdressers

This story is a graphic tale of a Dom and his very submissive transgendered male and a n other. If you are offended by tales of BDSM and sex between consenting adults then read no further ......... other wise enjoy It is best if read with previous chapters. Feel free to leave honest comments or suggestions, it really does encourage those of us who write t...

Making Francesca Ch. 01

by Spango on Sep 12, 2017
Transsexuals & Crossdressers

Author's note: I originally posted this story on another site under the title "Kidnapped and Sissified" a few years ago. I have decided to pull it out, dust it off, do a little editing, slap on a new title that I like better and share it with you fine folks here. Enjoy. Frank was an ordinary guy in his mid-twenties; of average height and build, loved col...

An Afternoon Tea

by suzette_la_soubrette on Sep 13, 2017
Transsexuals & Crossdressers

Scene One: Backstage "Ah, there you are my pretty pet! All nice and comfy on your pretty perch, are we?" I hear Miss Debra's cheerful voice from behind me. I scan the large, ornate, gold-framed mirror hanging on the wall before me, straining my corseted neck to determine her whereabouts. I quickly spot the reflection of her pretty face, as she playfully...

The Valentine Surprise

by rogkw99 on Sep 16, 2017
Transsexuals & Crossdressers

(This is not fiction or fantasy. It is a true accounting of what happened to me last Valentines Day. Even if you think it is fiction, I think you will enjoy it. I would enjoy it if it were about someone else and not me!) I can't help but think of Valentine's Day last year, a day that forever changed my life. In the weeks leading up to that day my wife Ama...

My Girlfriend's Sissy Roommate Ch. 04

by SEVERUSMAX on Nov 21, 2017
First Time

"So, you softened up faster than I expected on the issues of fellatio and vaginal sex, babe. Not that I mind, as it's between you and Rain, and I think that it's rather sexy, anyway, but what prompted that? Just the knowledge that Rain has meekly accepted his lot and will be a loyal husband to you? I wouldn't go so far as to call him a cuckold in the typical...