Sissygasm Story Porn Stories

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First Multiple Sissygasm Today

by JessC on Sep 16, 2017
Transsexuals & Crossdressers

I had my very first multiple sissygasm. I own a fucking machine. It has been the source of much pleasure since I bought it. I decided recently to try for a really great sissygasm. For those of you that don't know, a sissygasm is having an orgasm with a soft cock from ass/prostate stimulation. Well, I decided that I was going to prep myself to have a nice la...

Sissy Pills Pt. 02

by Sissyhalo1 on Jul 6, 2020
Transgender & Crossdressers

There's nothing like waking up like this. This being after being fucked. Not fucked but riding a dildo until you have a sissygasm. And yet that's not the first thing in my brain waking up. It's the cum. It's that eating my own cum. And really feeling this need sort of burned in my brain from the semen and the pills. I really, really want to suck a co...

White Boi Learns his Place Ch. 06

by sissyashley4bbc on Oct 31, 2018
Transgender & Crossdressers

Sunday arrived and vacation was over. As I sat in the backseat of the Jeep with Daddy, I could help but think of how much had changed. 4 days ago I was a straight guy on the mend from a breakup just looking to start fresh by getting fucked up with some new friends. While that definitely happened, so much more did too. I was completely seduced by Daddy and...

Simone

by Sissyhalo1 on May 11, 2020
Transgender & Crossdressers

I'm so sick and tired of my life. It was like I'm cursed. I wasn't a great looking guy in high school with bad skin and bad grades because well... I was poor. My old man was a night watchman and mom was a stay at home mom because she was poor and had no real education past junior high when she started popping us out. So everything was tight and for the m...

A Date with Destiny

by StarrOftheNite on Aug 20, 2018
Transsexuals & Crossdressers

Most people like to have a mind's eye picture of what the narrator of a first person story looks like, and since this is a true autobiographical story about my personal quest for gender identification, sexual orientation and self-realization, it's probably important to the narrative, too. Physically, then and now, I'm almost six feet tall, broad shoulders, n...

Cuckold Hypno Assignment

by DivinaTellsAll on Jan 1, 2019
BDSM

My name is Divina. I serve Goddess K. and Madam Vega. I am on a journey to become their perfect sissy girl, and a cuckold slave to Goddess K (who is my wife). The following is a true story of an assignment given to me by Madame Vega, and carried out with Goddess K. Assignment: Watch cuckold hypnosis video pornography, with my chastity cage locked and and...

Making Holly

by Sissyhalo on Sep 19, 2017
Transsexuals & Crossdressers

My name's Jamie and I moved back to my hometown. I had a lot of bad memories here and most of them stemmed from being bullied in high school and a lot of that came from Holt Thompson. A loud mouthed jock in school he was the center of the basketball team and really, really arrogant. I was a geek, a comic kid and dungeons and dragons kid and all that stuf...

White Boi Learns his Place Ch. 02

by sissyashley4bbc on May 30, 2018
Transsexuals & Crossdressers

I slept like a baby that night after the fucking I just received at the hands of Steve's big black cock. It was hard to believe that earlier that day I was a straight white guy sitting at my desk at work looking forward to a boozy cabin weekend with an old (and some new) friends. Now, I'm being little spoon for a black man who just took my sissy virginity, w...

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...

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...