Sissy Sex Caption Stories

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Sissy for a Day

by silkstockingslover on Oct 16, 2018
Fetish

Summary: With his wife's help and support, a man becomes a sissy for black cock. Note 1: This is a Halloween 2018 Contest Story. Be warned: this story involves sissy sex, obsession over black cock and a bukkake. If this isn't your thing, please don't read any further. Note 2: This is dedicated to the real Paul who requested this story. Note 3: Thanks to:...

Sissification 101: Ch. 01

by silkstockingslover on May 4, 2020
Fetish

Summary: Straight guy is caught watching sissy porn and...Note 1: Thanks to Eric who requested and helped plot this lengthy story. Note 2: Thanks to Tex Beethoven and Robert for editing. Note 3: All characters are at least 18 years old. Sissification 101: Ch. 01 1. MY SISSY CURIOSITY I've always liked nylons. I grew up when they were still popular and...

Hotel Mix-up

by Woulditkillyou on Sep 13, 2017
Loving Wives

This story deals with Cuckolding, sissy, and impregnation. Please do not continue if any of these subjects offend you. This is a work of fiction, meant to be enjoyed. Please click back if this does not suit your style. In a fantasy, there are no STD's, and pregnancies become nothing once you stop reading. Sorry it is so long. I get carried away with the deta...

Pretty Chris-tine Ch. 02

by jealouscuck on Sep 26, 2017
Fetish

My wife, Sharon, and I were lifelong friends. We eventually began dating and then got married. The idea that eventually shaped part of our sex life was her grandmother remarking that I was too "pretty" to be a boy. She thought that my complexion and clean looking face was attractive. One time as a lark, Sharon asked me to let her put makeup on me. I initiall...

Internet Meeting

by Stillherer on Sep 16, 2017
Fetish

We met on the net. How modern. He was shy and nervous, very much like I was though if anything even more cautious. Being a closet cross dresser with a life outside my apartment door my main aim was discretion and major fear -- discovery. Charles appeared to be perfect for my yearning to fulfill my fantasies and spice up my solo adventures. We chatted online...

How I Became a Chastized Cuckold Ch. 08

by gizzard on Sep 26, 2017
Loving Wives

**Warning** This fantasy story series contains or will contain elements of Male Chastity, Orgasm Denial, Female Domination, Cuckolding, Interracial Sex, Bi-sexual Innuendo and Tendencies, Teasing, and BDSM Activities. If any of these topics are offensive you to, I recommend not reading. * Thin rays of golden sunlight glimmered through the bedroom window bl...

The Botanist

by Carnal_Flower on Sep 19, 2017
Erotic Horror

Q: Why do you write erotica? A: Because if I didn't put sex in my stories, no one would read them. --Anonymous Part One. The Master hated these trips into London, but they simply could not be avoided. The Thief, so peculiar in his demands, would not meet with anyone else. This was perhaps understandable in the beginning, when he was completely unknown,...

A Latex Crossdresser's Dream Pt. 05

by shinyglove on Nov 18, 2019
Fetish

Please read A Crossdressers Dream parts 1-2-3& 4 before moving on to this story. *** The party was certainly in full swing as we had all seen some sort of action. The room smelled entirely of sex and latex, I was very happy with this as the aroma of rubber turned me on. Every time I opened the bag where I kept my latex collection the smell coming from it w...

Discussing Terms and Labels

by XplrgMDCpl94 on Apr 14, 2020
Reviews & Essays

The author of "Fifty Shades of Gray" did an excellent job of playing on the words, her main character's name and the concept expressed by "fifty shades." There are so many variations expressed, most especially when it comes to sexuality, that fifty is probably too small of a number. That said, I was thinking about various terms in common use and how they cou...

Montana Rhapsody Pt. 01

by Egmont0409 on Sep 16, 2017
Novels and Novellas

CHAPTER 1 Hard-faced commissioning editor Ruby Street looked at one of the publishing company's premier writers of soft romances that were laced with mild naughtiness. She smiled bleakly, thinking the success of this attempt to wrench Paris McCoy out of her comfortable rut to hit the bookshelves with a sexy sizzler were about as good as finding a hundred bu...