Tricked Into Sissy Cumslut Stories

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Playing Pregnant

by theonewhowas on Sep 16, 2017
Transsexuals & Crossdressers

I'm a sissy. I used to be a femboi, then I was a crossdresser, and now I'm a sissy. The main difference between the crossdresser and sissy phases was the attitude; before I was a guy doing this for fun and to be admired, sexually – to confuse straight and gay boys alike. But now, as a sissy, I was devoted firstly to my master and love, Noah, and secondly to...

Cockland Island Pt. 04

by Sissyhalo1 on Dec 16, 2019
Transgender & Crossdressers

It was one of my first lessons as a sissy that I learned on my own. New girl only appealed for some men. And there were all sorts of hotter sissy girls there just working it in the food hall and other places. With real breasts or close enough, with great asses that were getting attention. And as femmed up my brain was there was still this sort of competi...

Teen Cocktease Babysitter

by CharlotteUnicorn on Jan 22, 2020
Fetish

What a day! Project meetings all day long, from 9am to 9pm, with really intense demo testing, barely half an hour for lunch, and I was on point for the whole day as the lead system analyst. I was sooo tired when I got home. Opening the door, I hoped my kids were asleep and there would be no crises to deal with. I couldn't hear a sound. Yay! April had co...

Tales of Sub Asian Sissy Ch. 01

by subASIANsissyJADE on Apr 3, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** (I'm new here and this is my first post! I'd soooooo love to hear any feedback, questions, or comments! Many thanks, xxx, Jade) ***** I wore exactly what he demanded - he told me to dress like a regular girl... he told me he had nosy neighbors and, being a married man, he...

Bi Cuckold Humiliated and Fucked Ch. 03

by DaveLoveAss on Dec 16, 2019
Fetish

Part 3. If you haven't read the first one you should do that and learn how the cuckolding began. People keep asking for more so here it is, the second night... * Work that day was long and painful. Every step was a gentle reminder of the pounding Abe had given me the previous night. Every time I sat down was excruciating as my ass never seemed to fully clo...

Girl's Night Pt. 10

by DifferentBreed on Sep 14, 2017
Fetish

This story contains adult fetish themes between consenting adults that may be upsetting for some readers. There are also scenes with vulgar language that some may find offensive. Please proceed with caution. ~ thank you for your patience ~ The sleek black towncar maneuvered through the downtown streets, the darkly tinted windows giving no hint to the passe...

The Flume at Falcon Rock

by KenNicottii on Sep 13, 2017
Erotic Couplings

* * * A Chance Encounter: My sister Erin glanced over as she eased her car from the arrivals curb at the Dallas-Fort Worth airport. "So how was your flight?" Actually, it was pretty shitty, now that you ask. She had just driven over a hundred miles to pick me up so I wouldn't be tormented by a three hour wait to take the next Greyhound bus home. I knew...

Sister Mistress Ch. 15

by LilLindaMelons on Sep 19, 2017
Transsexuals & Crossdressers

Pulling back Kathy patted Jenny's still sore cheeks. "Catch ya later girlfriend." "MMMMM bye, you know I'm going to dream about you Mistress Katherine." "I hope so Baby." After watching Jenny disappear through the garage Kathy walked up the service steps and into her bedroom. She was eager to checkout the surveillance of her mothers' bedroom. Deborah ha...

Insatiable an Appetite

by AlinaX on Apr 25, 2018
Sci-Fi & Fantasy

Dear Cassandra, I leave you my grandmother's ring, an ancient heirloom passed down through generations. Your mother begged me to destroy it rather than leave it to you. She was sure that it is cursed, but I suspect it is cursed only by the fears of men, and not from some intrinsic evil - unless all witchcraft be so. I have never dared wear it myself, being...

Halloween Party Aftermath

by Sabnock on Oct 19, 2020
Transgender & Crossdressers

Oh my GOD I'm so hungover. I creak my eyes creak open, and immediately regret doing so. Everything hurts. My head is pounding. My mouth tastes like something died in it. I try to sit up, pause, flop back onto the couch. At least I've got blanket. Wait... I'm not in my bed. Where the fuck am I? I rub the back of my hand over my eyes, feeling a weird, heavy...