Sissygasm Chastity Stories

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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...

AliExpress and Sissy Downfall

by His_fag_wife on Oct 15, 2017
Transsexuals & Crossdressers

It all started with a visit to a TV Mistress on a work trip, Charlie had been cross dressing in some way or another since he was a teenager. First just his Mums used panties, then a lodgers underwear and finally he'd started to buy the odd thing himself. As time went on, BDSM was added into the mix, Charlie realising he was submissive and when he found Siss...

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...

Almost Damsel Almost in Distress Ch. 03

by shawnavinyltv on Aug 24, 2020
Transgender & Crossdressers

I felt Alex moving around the bed, I figured he was going to pee, and sure enough, he came back a few moments later and snuggled back into me. I did really want to ask him about last night's adventure and if he was my mystery lover or not. Though I was pretty sure it was him, the thrill of not knowing, made me wonder who else it might have been. The thought...

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...

Vanessa

by Floydman1 on Jul 13, 2020
Transgender & Crossdressers

Her name was Vanessa. She was very cute, about 5'4", slim, with big brown eyes and skin that was very clear and smooth. We had met online, of course. She had reached out to me for advice and friendship, as I was an experienced transwoman. After talking online first and then over the phone, we met in person. It was at her place, since she wasn't all the way...

Evolution

by sissygasm on Dec 23, 2015
BDSM

You wake up, glance at the clock and realise you've slept in its nearly 1 O'clock. You drag yourself out of bed and head towards the phone to call in sick. Something stops you, there appears to be something large and warm on top of you. Oh yeah, that's right, you brought this sweet piece of ass home last night and fucked into the early hours of the morning a...

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Proud Beta

by Sissyhalo on Mar 13, 2018
Transsexuals & Crossdressers

All parties are over 18 years of age. *** I'm a beta. And yeah for those that get what that is, we're real. I was a white kid that was on the skinny side and I was born and grew up with a little dick. And I was everything that came with being a small dicked little loser then. Bad at sports because that meant dressing rooms back in high school and never...