Sissy Caption Story Stories

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Infinite Scroll

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...

Being Jenny's Summer Boyfriend Ch. 02

by Lucas96 on Mar 5, 2018
Fetish

Disclaimer: This story contains cuckolding, humiliation, homosexuality, and incest. All characters in this story are above the age of 18. ***** Here I was, on my knees between Jenny's legs as she sat back on the couch. Slowly, reluctantly, I stuck my tongue out and moved it toward her naked body, dripping with my dad and brother's cum. I was so grossed out...

Lucas's Older Brother

by Lucas96 on Dec 2, 2019
Fetish

Disclaimer: this story involves cuckolding, humiliation, etc. *** Lucas and Emily, both 21 years old, had been dating for about a month. While Lucas had had previous girlfriends, he'd never felt the way he felt about Emily. They'd met in class at their small liberal arts college, hit it off immediately, and gone on several dates. After a week or two, Emil...

CFnm Adventure - 2nd Visit

by lovelicker99 on Sep 13, 2017
Fetish

Note: This is the second story involving encounters between me as a submissive male and a Dominant BBW who responded to an ad I ran online. These stories are fantasies, but some of the specific acts are things I have done and enjoy doing. If you are a woman or a couple that enjoys doing any of these things I would like to hear from you regardless of where yo...

Isabella's Reversion Pt. 05

by silverbackteddy on Sep 16, 2017
Fetish

Note from the Author: This is a story about ABDL. The first word being Adult. All sexual encounters center around Adults, above the age of 18. This story also contains BDSM, plushophilia, watersports, and various other fetishes. For those that are grammar freaks, please don't comment on my improper grammar use. I could care less. At least it doesn't have L...

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...

Lilly

by CumSlurpingCuckold on Sep 16, 2017
Loving Wives

My name is Louis. I'm White and I love my Vietnamese wife so much, but Lilly calls me "Daisy Lou, a Dick-sucker" nowadays, and she's 8 months pregnant from a Nigger-man named Jerome. She keeps me in her panties; it makes me feel good, feminine and servile. Since she doesn't wear panties anymore, now that she's a Nigger-loving wife, she told me I should wear...

Virus S

by thisisnttaken8 on Jan 17, 2021
Bisexual

"FUCK ME YOU STUD!" the slender new trap screamed in agonizing bliss as the muscular stud pounded him from behind. Connor could see the brute's body changing by the second. He arms grew more muscular and his jaw grew more angular, but even stranger was his cock. It seemed to be growing thicker and larger as he plowed the twink's ass. The bull wasn'...

Mistress Tanya Ch. 01

by Palancar on Sep 18, 2017
Fetish

This is the first chapter and is a little tedious without any actual sexual situations. Please bear with it. I needed this to set the stage for following chapters. I promise it will get much better. Also please remember it is only a work of fiction. I welcome critiques both good and bad but if the storyline isn't your cup of tea then don't read it. I see s...

My Friday Night: Switch

by honey28 on Sep 5, 2017
Fetish

Driving home on Sunday night, my phone rang when I was stopped at the light waiting to turn onto my street. Seeing Nick's name, I put him on speaker phone. Before I could say anything, he very loudly declared, "I want to lick your pussy." Hearing that deep, sexy voice usually makes me melt, but I had to giggle. Note to self: never answer his call on speakerp...