Sissy Prostate Stories

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Making a Sissy Jock Pt. 02

by Sissyhalo1 on Jul 6, 2020
Transgender & Crossdressers

I stared at Robin's card for an hour sitting in my truck completely freaked out and every time I touched my lips I felt that friction of Robin's cock. I tasted him. I got slammed with the realization I drank his cum and it was inside of me. I sucked cock and drank cum and just like the sissy porn stuff said I liked it. I was beyond freaked in going to th...

Letters to Michelle Ch. 01

by stevemike08066 on Oct 16, 2018
Letters & Transcripts

Dear Michelle, I hope it's ok that I email you like this, I found your email in the company database. You're a very sexy woman, and I'm not sure if you noticed me staring at you. I mean, I couldn't help it, seeing your ass in those jeans, I couldn't help it, and your breasts wrapped up in that sweater, I wouldn't mind having a couple of hours to worship...

The Wedding Ch. 05

by betamale08 on Mar 30, 2020
Transgender & Crossdressers

(Patti Cake part 3) Chapter 5 -- Femdom, Fucking and Femininity... At the end of our time spent with Ms. Walsh, I was left with a lot of questions and I wasn't sure how to deal or cope with any of it... But one thing was for certain, I was starting to see more of the old Patti bubbling back to the surface, being direct and without compromise... The whole d...

My Wife's Sissy Panty-Sniffer Ch. 03

by cuck3995 on Sep 12, 2017
Fetish

Pete emailed me a few hours later and asked me how my little cock felt. I told him I had laid there for a while, and eventually lowered my wife's panties a bit and jerked my little cock. I told him I used his big load as lubrication, and came very quickly. His response back came quickly, and he told me to make sure my wife gave me a blowjob later that day. H...

Recruiting of a Sissy Maid Ch. 02

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Two: Onto Her Training and Breaking Down. The feeling of fear and dread falls over Chantel as she sits on the flimsy bed in what is for now her prison cell. Totally alone and isolated except for the fact that Mitch and Nate Burrows will lord over her as they orientate, train and ultimately break Chantel from a fantasy sissy to what will be a living...

Lace and Love Ch. 04

by vaultdweller111 on Sep 19, 2017
Transsexuals & Crossdressers

Jake walked back to the living and was happy to see Alice in her second position, on the knees with her arms crossed behind her back. She was waiting in front of the leather sofa chair where Jake would sit. Jake walked up behind her as he noticed all the toys laid out on the coffee table. He bends over and grabs her long black ponytail and lightly yanks her...

Recruiting of a Sissy Maid Ch. 10

by Sissy_Chantel on Nov 23, 2017
Transsexuals & Crossdressers

Chapter Ten: Changes Continue for Chantel as Her Relationship with Carl Grows. Awake and having a great breakfast superbly made by Carl, Chantel enjoys her morning with him. He has her in one of his robes as they talk about things and their future together. After breakfast Carl says, "Put on a pair of my jeans with your white satin blouse, you can wear yo...

Neighbourhood Terror to Sissy Pt. 06

by Fibaro on Apr 9, 2019
Transgender & Crossdressers

Mark's night ended up being a very restless one. The constant rubbing of his sheets against his nylon covered smooth legs as well as the feeling of the silky material of his panties all around his bottom and chest felt very sensual. He was embarrassed to admit it, but it actually turned him on. The worries combined with the horniness formed a potent combo to...

Shopping and Sucking

by Subkoksukr4u on Mar 2, 2020
Fetish

Matt was in the kitchen as usual preparing breakfast. He'd been instructed to prepare all the meals according to a specific menu plan each day. He finished the sauce for the eggs Benedict got on his knees and waited. He was wearing frilly pink crotchless panties and a matching bra, his bright pink CB 6000xs chastity device was barely peeking out between...

Wife in Control Ch. 07

by wifetoy on Sep 25, 2017
Fetish

This is the seventh chapter of my wife's fulfillment of the punishment poem I submitted suggesting ways to atone for my inability to control my orgasm. Please read the earlier chapters for the full poem and the humiliations I have been forced to endure because of my failure. I am grateful that my wife loves me enough to exercise the total control over me tha...