Sissy Hypno Stories

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I'm Still "Straight" Right?

by Curiousissy on Apr 4, 2018
First Time

For me, the rabbit hole started when I first got into futanari. I just found it so hot watching a girl with this big thick cock plowing another girl. I told myself I was straight because it was two girls. Then I stumbled upon futanari x male and that solidified the direction I was headed in this rabbit hole. I was so turned on various futanari on male seri...

Cockland Island Pt. 06

by Sissyhalo1 on Jul 6, 2020
Transgender & Crossdressers

I woke up and I was sucking that realistic dildo cock like a soother and it was so weird and right and made me smile as I pulled it out trying to make my lips do the pop you can do sometimes with suckers. I giggled and did it a few more times then pumped it in and out of my mouth trying to get that dick lips feeling going on. That's a sexy sissy trick, all...

Sissy Cuckolded by Girlfriend Ch. 01

by SaraRurik on Sep 16, 2017
Transsexuals & Crossdressers

My name is Josh and I'm a 19 year old white guy with a beautiful girlfriend. Her name is Angel and she is the best thing that has ever happened to me. I love her with a passion and intensity that is hard to describe, she is everything a man could ever ask for and more. She is caring, sexy, understanding, kind, intelligent, and totally a bad bitch. We have...

Feminizing First Step Ch. 06

by antares34 on Jun 1, 2020
Transgender & Crossdressers

(All characters are age 18+) Today my mom was having her friends over for a pool party in our backyard. They had been here all afternoon --mainly lounging around the secluded swimming pool and patio area. Michelle had been first to arrive. She was my mom's old roommate from university and came wearing a black bikini and floral print sarong. Next was Kendra...

Under Mommy's Direction Ch. 05

by MommysHypnoSissy on Apr 13, 2020
Transgender & Crossdressers

The rest of Jaime's day had been a whirlwind of tasks and chores to complete before his Mother got home. His online Sissy Trainer, who demanded that he refer to her as 'Mommy', had given him a myriad of tasks. First it was cleaning up his Mother's bed and sexy toys, putting everything back how he had found it. Then it was back to his room to dispose of his b...

The Feminisation Initiative Ch. 02

by Slipperylock on Oct 30, 2018
Transgender & Crossdressers

The room was quiet and dark - the only illumination spilled from the Observation Room window over the eight beds and their occupants. The only sound in the room was the whirring of the machines, and the occasional muffled moan. In the Observation Room booth, the Director of the F-center fiddled with the control panel nervously and jogged her leg. The Presid...

It's a Sissyful Life

by sliderx on Aug 23, 2015
Fetish

John sat in the basement, football on the TV, 4chan on his laptop. The game was pretty much a blowout, so he wasn't really paying attention. He was, however, greatly interested in the adult gifs (although 90% of the entries were webms) page he was on. There were a few threads that were catching his eye, girls playing with their asses, deep throat, but he was...

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Intruded and Blackmailed

by hosiery_cumslut on Sep 16, 2017
Transsexuals & Crossdressers

It all began this one summer, a few months after I turned 19. I had just finished my first year of university in a small "university town", as they call it. I signed a house lease with 3 other friends for the next school year, and we had to pay rent for the four months of summer even if we weren't going to live there. My three friends had all left for home...

The Prostate Exam Pt. 04

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his naturally submissive tendencies by not being able to resist pushing back against her finger, forcing her finger deeper into asshole. At that point his female doctor had decided to test just how submissive he was. She gave him the option to back out if he...

Sissy Girl Forever Pt. 03

by sissymissyct on Sep 18, 2017
Transsexuals & Crossdressers

Sissygirl forever continued. Sara stood there laughing at me as Mistress explained how things would be for the near future. She told Miss Andrea that if I wished she could fill them in with the red right now if I wanted. But Mistress said no. She was looking forward to my rushing off to work at times forgetting to polish them. Or eating out with friends and...