Sissy Truth Or Dare Stories

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Truth or Dare Takes a Turn Pt. 03

by Cutiepie183 on Sep 21, 2020
Transgender & Crossdressers

I pull up in Luke's driveway and get out of the car, I retrieve my suitcase from the boot and make my way over to the back door, only to be stopped and greeted by Brent before I can enter the house. Brent leers at me and says "hey there sexy little cocksucker" before he pulls my pants and panties straight off me, locking my cock back in the little pink chast...

Snap! to it Divina

by DivinaTellsAll on Feb 12, 2019
BDSM

Writer's note: The following story is 100% true THE DRIVE The drive to Austin was 8 hours in good weather. Today it had been raining, and it was going to be 11 hours in the car, by arrival time. I was acutely aware of how long the car ride had been so far, for several reasons. The biggest of which was the overly-tight pair of pink sissy panties, curren...

Neighbourhood Terror to Sissy Pt. 07

by Fibaro on Apr 23, 2019
Transgender & Crossdressers

Mark regained consciousness when Stephanie pressed her lips against his and started pushing his load of cum in his mouth. He had only just sucked a load off of Linda's toes and now he was swallowing yet another one. Every time he came here he seemed to get stuck with a taste of cum in his mouth. Only made worse by the way in which he was fed the load. Well a...

Neighbourhood Terror to Sissy Pt. 10

by Fibaro on Jun 10, 2019
Transgender & Crossdressers

Chapter 12 Mark had just about time to put his dildo down before the door to his room opened. His hand was still wrapped around the base, and well there was no real way he could ever hide anything of what had been going on. He was caught red-handed and could only really look at his girlfriend, or rather his ex-girlfriend in horror. After all, why else than...

Mass Sissy

by Jman236 on Sep 16, 2017
Transsexuals & Crossdressers

Well my mistress wanted me to post this short story of my latest sissy humiliation for even more humiliation so here goes... So it was a typical Saturday and I was on my way over to my mistresses' house, she wanted me there bright and early. I arrived at her house promptly at 4:00am and when I arrived I was informed that I would be spending the entire weeke...

Dancer Turns me out Pt. 03

by pantiepervMI on Sep 28, 2020
Transgender & Crossdressers

After a restless night, I finally dragged my tired and sore body out of bed. My asshole was on fire and I could feel the pain with every step I took. I thought about skipping the insurance sessions to catch-up on my sleep, but after tonight I did have to return to my real life, my job, and my asshole boss. I downed several cups of coffee and got dressed in...

Trained by My Aunt Ch. 01

by Misslexia on Aug 18, 2017
Fetish

It was my Aunt's suggestion that, when I left home and got a job, I moved in with her. Although my job was a few miles from her house, I had my bike and the renting a flat in the city was not an option. Secretly I was delighted. Aunt Suzy was my mum's younger sister, jokingly described as an 'afterthought' or an 'accident'. Fifteen years younger than my mum...

In My Dad's Panties

by britneyfan on Sep 11, 2017
Transsexuals & Crossdressers

I knew my parents hadn't been getting along at all well recently and I had even begun to fear that they may some day be getting a divorce, but still the discovery that my father could be having an affair came as both a shock and something really quite distressing. It was the first time I had to confront the truth that my parents' split was a very real possib...

Truth or Dare Takes a Turn Pt. 05

by Cutiepie183 on Oct 19, 2020
Transgender & Crossdressers

The rest of the week flew by in a blur of pure bliss. I really settled into my new role as Luke's little sissy slave. I would wake him up each morning with a hot, passionate, sloppy blowjob and give him breakfast. After that we would shower together and I would wash Luke's whole body for him and Luke would give me a golden shower in return before letting me...

Sissy Bitch Ch. 01

by sissy_memories on Sep 12, 2017
Transsexuals & Crossdressers

After I moved out of my parent's house, I found an apartment with my a girl called Laura. I was nineteen, she was eighteen and, as one of the few left in town after everyone we knew took off for college, we had little choice for room mates. I didn't even know Laura that well: we had mutual friends and that was about it (though I did know she was good fun aft...