Tricked Into Sissy Cumslut Stories

349,013 results
Orientation
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Infinite Scroll

Be My Bitch

by purekink on Aug 20, 2019
Transgender & Crossdressers

I'm so glad you agreed to be my slut – I've been searching for a crossdressing hussy I can train to be my personal tart for some time now, and I'm certain I can teach you to fit the bill. I understand your fantasy is to be dressed as a sexy sissy and have your manhood and your cherry fucked right out of you. This pleases me, as I enjoy nothing better than u...

Porn Shop with Gloryholes Ch. 01

by Sinful_whispers on Sep 14, 2017
Fetish

Chapter 1: Her 1st experience w/ Gloryholes The darkness of the night was settling in as she parked her car, exited it, and began walking across the parking lot. The black macadam was empty, all but two cars and one was her second shift employee Dave. The night lamp lights began to flicker on and off then popped on fully as she reached out and curled her fi...

Sissy Crissi Ch. 01

by sissycrissi on Sep 11, 2017
Transsexuals & Crossdressers

Chapter 1 -- One Dreamy Night Like most Friday nights, my roommate Erika would be gone tonight. She and her new boyfriend, Leroy, were taking off for a private weekend. Erika and I had met about two years prior, when we were introduced by a mutual friend. Being fresh off a divorce, I was in need of a place to stay, and Erika was in need of someone to help w...

Girl's Night Pt. 06

by DifferentBreed on Sep 14, 2017
Fetish

This is a continuation of an earlier story. It contains themes of feminization, humiliation and other fetishes that don not appeal to all. If you are a fan of these, please read on and leave comments as to how to improve the story. Hope you enjoy it. ~ DB ********* Fisher climbed up the stairs to the brownstone, Sophie's jeans creeping down his ass for wha...

A New Life Ch. 05

by sissycinnamonswirl on Sep 18, 2017
Transsexuals & Crossdressers

I remember that night I drove myself home from work after getting her phone call filled with humiliating demands and insinuations. I was in an absolute panic. I had no idea if Mistress Sally was serious about all of this, or if she was just playing elaborate games with me. But I honestly feared the worst, and my fears were realized as I pulled into my drivew...

Mindy's Moving Day - CFNM Ch. 02

by BuckyDuckman on Sep 25, 2017
Interracial Love

Author's note: I think this works as a stand-alone. I get my lily white ass reamed by a big black bull in front of my wife, her friend and my swim team. Delicious humiliation! Mindy's moving day signaled a huge change in her life and the relationship I have with my wife, Debbie. That was the day we put on a real life show of me offering up my sissy ass wh...

Haven the Sissy Slut Ch. 02

by CSK on Sep 11, 2017
Transsexuals & Crossdressers

As the water poured over me, washing away the remaining cum and pee from my young, nubile body, I stood up and removed my drenched clothes placing them on the floor of the shower. I grabbed the girly body wash and lathered my body down, making sure every inch of my man-pleasing body was squeaky clean especially my "pussy" as I was positive it was going to be...

How I Became a BBC Sissy Slut

by Satanicsissybitch on Feb 12, 2019
Transgender & Crossdressers

I wasn't always a black-owned little slut if you can believe it! Can you believe, at one point in my life, I actually refused to sleep with black men? I can't even wrap my head around it honestly. These days I belong to a number of hung black guys who use me whenever they want and now I refuse to sleep with white guys altogether! If it's not a black cock I d...

You're Like a Little Boy at Times Ch. 03

by Myneed on Aug 30, 2017
Fetish

This is a slight twisted femdom love story that will make most sense if the chapters are read in order. The characters don't seem to want to engage in safe sex, but in the real world we should. Enjoy. All characters are over 18. ***** My heart ached for Mel. It had been another long week another long week of edging and chastity at Mel's instruction. Th...

A Photo Session, My First

by keptsissy on Sep 18, 2017
Transsexuals & Crossdressers

When he called and said "We're going to something special today, sissy boy." I got instantly wet in my panties. He arrived at my house and stripped out of his clothing almost before I had a chance to close the door. I feel his large hand cup my penis and balls. He covers them completely and easily. I'm small, less than 3" erect, baby-like. I feel my little...