Crossdresser Gets Creampied Story Stories

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From a Husband to a Dutiful Sissy Ch. 07

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Seven will also advance the time of my story here a bit. To move my story along into a lifestyle changing story I will have this chapter set seven months after Phil was outed as crossdressing sissy named Chantel. Over the last seven months, life for Chantel has become entrenched as a sissy maid and slut. The sex video productions put up online have...

Creampie Novice

by rick_oh on Sep 3, 2017
Fetish

"We have a novice here this evening," Joy announced in her low voice. She paused for the party to quiet down. "For his benefit, I'll explain the rules. All the guys will go to the other room. Then all of us girls will roll the dice. The highest score will get the new guy. Then, she will go get her guy, and bring him out here. Now, he's got to get her nice an...

Cabin in the Woods

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

Finally, I get to give you another TRUE story after a WAY too long 'dry spell'. This story is completely true (and may be a little boring maybe...would love any feedback). Only the names have been changed to blah blah blah... Anyone who is familiar with my writings knows my stories are true and not made up unless I openly state at the beginning that it's a...

Valena the Witch

by drelord2102 on Sep 12, 2017
Group Sex

Valena liked things disciplined. When she entered her bedroom she saw everything in place. Harold came towards her in all fours and quickly placed himself between her legs and with an open tongue reached for her hairy crotch, which she allowed by parting her legs slightly. Lack of any undergarment under her skimpy and short nightdress allowed Harold the desi...

Lake Tahoe Test Drive Ch. 01

by Ear2Ear on Sep 25, 2017
Anal

FEEDBACK appreciated. Make sure to read PROLOGUE to this story as well, published 8/15/15. ***** During a trip to Lake Tahoe, the narrator is starting to see the dominoes fall as his plan to initiate his girlfriend into pornstar-like anal sex, double-penetration and creampie gangbangs with big-cock studs comes to fruition. ***** "No disrespect but gimme...

Home in the Hills Pt. 01

by ValoryG on Dec 10, 2019
Transgender & Crossdressers

All names and characters in this story are fictional and have no connection with any actual person living or dead. ***** Jonathon Worley is in his sophomore year at Onanoma State University, majoring - at least for the time being - in art history. He's the third child in his family, and after his parents paid for the first two to go to college, there was...

A College Cuckold & His GF Pt. 01

by youngasiancuck on Sep 19, 2017
Exhibitionist & Voyeur

This is the story of how my first girlfriend and I ended up in a long-distance relationship and what we ended up doing to make it all work. I've changed the names but everything else remains the same. *************** My name is Jason and I am a cuckold to my girlfriend, Stella. She and I have been dating since we first met back in high school and at this...

Promotion/Demotion Slips

by pikapache on Apr 29, 2025

The promotion/demotion slip is one of the strangest types of magical item throughout the multiverse. They are A5 sheets of paper with four bits. At the top of the page was a bit to put the name of the person that is being affected, different people with the same name are not affected as only the person the writer of the slip is thinking about is affected and...

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Your inner femboy

by SkirtSkirt on Feb 10, 2021
Transsexual

The first thing you have to ask yourself is, who are you Are you an ignorant boy about to be turned into a little cum slut?But then who was there to show you who you really are?Or did you do it to yourself? Or are you already a cum dumpster about to reveal themselves? Or maybe you want to be a slutty crossdresser that's secret gets exposed,one throat fuck at...

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Recruiting of a Sissy Maid Ch. 01

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

[Welcome to my next story. This story has become a little different in how I planned to write it as compared to my previous stories. It has been fully written up already, as of this first uploaded chapter. Doing it this way allows me to better proof read and adjust for future chapters before uploading each. I will submit uploads on a regular basis for my rea...