Sissygasm Stories

121 results
Orientation
Length
Source
Infinite Scroll

Falling into Being a Sissy

by Sissyhalo on Dec 12, 2018
Transgender & Crossdressers

My name's Sonny and well life's been pretty damned golden for me. I used to be a hockey jock in high school and was a defenseman so I was kinda big and tough and had all the usual good stuff going for me. Middle classed family, decent money for all of that, lots of high school pussy and even more in college. Being a jock in college doesn't prepare you for...

Self Destruction

by sissygasm on Jul 12, 2015
BDSM

Welcome to self destruction now lets blow through some quick questions so we can get startedWhat's next? Male Female What's next? Male Female...

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Sissy Dust Pt. 02

by Sissyhalo on Jun 4, 2018
Transsexuals & Crossdressers

*Before... "Spencer you don't have to pay me now I got off like four times, that's never happened to me." "I do, we had a deal and you missed fares and tips." He actually smiled at me. "Okay but under protest." I stepped up and kissed him my first kiss with anyone ever and Steven kissed me back and it became really passionate. We actually kiss walked to...

My Cuckold Story Pt. 02

by ohsubmale on Sep 14, 2020
Transgender & Crossdressers

Wife Plants Her Ownership Pole - It's been a little while since I last shared about my experiences, so I am sharing my second experience I believe worth sharing in my deep dive into the submissive cuckold I have become. This is based on my real-life experiences, so please keep that in mind if it doesn't tick off all of your fantasies at once... I know our li...

Inaugural Crossdress Sexfight Ch. 03.5

by danidhotcd on Sep 16, 2017
Transsexuals & Crossdressers

After losses to Tommi, Jaimie and Dani, it didn't take a genius to realize that I had become the defacto jobber of the Crossdressing Sexfight League (CXSFL). There wasn't a cock among them that hadn't been in my mouth or ass at some point and if we had kept standings, I would have been in dead last place. Unless I wanted to accept my jobber role within the l...

Helen Ch. 11

by Philippasubmaid on May 14, 2018
Transsexuals & Crossdressers

This story is a graphic tale of a Dom and his very submissive transgendered males. If you are offended by tales of BDSM and sex between consenting adults then read no further ......... other wise enjoy It is best if read with previous chapters. Feel free to leave honest comments or suggestions, it really does encourage those of us who write to continue......

From Her Ex-Boss to her Bitch Pt. 04

by His_fag_wife on Sep 25, 2017
Transsexuals & Crossdressers

This story contains extreme fantasies of Fem Domme, watersports, cock sucking, forced bi, if these aspects are likely to upset you please do not read on. ***** Pete had been taken in by Rachel his ex-employee, encouraged along the way, with a little titillation, a lot of flirting and confessions of her bisexuality. She'd used her submissive Claire to help...

Slave Gets Punished and Redeemed

by Femboy_Anna on May 20, 2019
Transgender & Crossdressers

Hello everyone. It's been a while I know but I'm back. Today or tonight, whichever you're in right now, we're delving into some serious BDSM sado-masochism Slave/Master dynamics. So if you're not exactly into sado-masochism punishment or are disgusted by it you've been warned now. Like 'Femboy Caught In the Locker Room' this story is a back and forth coopera...

Sissy Slave

by mikedoreilly1973 on Nov 24, 2018
Fetish

It was late friday night, and Mike had just gotten home from work, he was tired and filthy from work and decided to take a much needed shower, he went to the bathroom and noticed the door was slightly ajar, he peeked inside and saw his 18 year old daughter Samantha taking a shower. Samantha was his daughter from his previous marriage which had ended badly wh...

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The Prostate Exam Pt. 07

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

Please do not read on unless extreme sissification and forced gay and bi scenes, watersports and cum eating, really flick your switches. I don't want to offend anyone so thought this comment might help. ***** It'd all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his naturally submissive tendencies by pushing bac...