Sissy Prostate Stories

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My Girlfriend's Sissy Roommate Ch. 02

by SEVERUSMAX on Sep 16, 2017
Loving Wives

"So, buddy, what gives? Or should I say, girlfriend, because, let's face it, we've always acted more like girlfriends in the platonic sense, well, minus your tongue going between my thighs. Other than that, you've been more like a female friend or a gay male one or something like that. Anyway, let's talk, openly now, about what Rain wants out of this relatio...

Humiliation Journey Never Ends

by Subkoksukr4u on Jun 25, 2019
Transgender & Crossdressers

Here I am once again looking up into the eyes of my tormentor, my superior in every way, especially his cock, 10 1/2 inches to be exact. I know because when I first met him he made me measure it with a ruler. He made me measure mine too. I was embarrassed, humiliated and shamed for being so small. It hasn't been called a penis or anything remotely masculin...

Neighbourhood Terror to Sissy Pt. 19

by Fibaro on Apr 13, 2020
Transgender & Crossdressers

Chapter 21 John had been looking forward to this very moment that he wasn't about to just get it over with. He was going to savour it as much as he possibly could. These contacts proved to be such a good find. They allowed him to stay anonymous as long as he didn't give away his voice while still not covering the sissy's face. A face even John had to admi...

A Man Has Needs

by StephaniePlayland on Aug 6, 2019
Transgender & Crossdressers

Another installment in Stephanie and Sir. Just getting home from a long hard day at work dealing with one person after another person's crises. I have had my fill of people today, just want to make some dinner, have a drink and kick back relax. That's when my phone chimes, a text message. Looking at it, it's Sir; he wants to know when I will be home? I rep...

Fantasies Fulfilled Ch. 02

by HerLittlePiggy on Sep 19, 2017
Group Sex

Sherry stood by the bed dressed in a black leather corset that accentuated her big 36dd tits, her tiny waist and her full hips and beautiful round ass. High healed thigh high leather boots completed her dominatrix outfit and a thick black strap on hung lewdly from her waist as she barked orders to me and the three muscular men in the room. It was September...

Caged!

by yvetteinpanties on Jun 19, 2018
Transsexuals & Crossdressers

I was a late blooming sissy. Like most sissies-to-be, I had early incidents of trying on my sisters clothes and enjoying the way they felt, but I always viewed myself as a heterosexual who just liked to imagine stroking a nubile female underneath the lingerie I was wearing. It was much later in life that I took the serious turn from being a heterosexual cros...

Rebound Sissy

by Sissyhalo1 on Jun 1, 2020
Transgender & Crossdressers

John had broken up with Angie, his girlfriend after what was like three years. They dated their first year of college then they moved in together and were serious for three years. And none of our friend circle saw the break up coming. And we sort of rallied around John as he tried to pick up his life. Which included going out and getting him to go out wit...

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...

Aficionado Gets in Trouble Ch. 02

by His_fag_wife on Jun 12, 2019
Transgender & Crossdressers

Mark cleared the clothes from the table, he wanted a truly clear picture of Pete being used in the stockade, knowing he'd get some great footage for his website selling the stockade frames, it would help sell some more without giving away Pete's identity from the side view. But he'd also get some head on footage for posting on the internet should Pete fail t...

A Freshman's Summer Class Ch. 07

by CapnSteelBoy on Jun 1, 2020
Transgender & Crossdressers

A Freshman's Summer Class **All characters are of legal age for adult content.** We Continue from where we left off with our brave hero, as his adventure continues during his summer of higher education learning! This is a continuing series I'll be releasing as my busy editor(s) help me clean up my keystrokes of mess.. Much thanks goes out to them, as th...