Sissy Plug Stories

24,564 results
Orientation
Length
Source
Infinite Scroll

Chrissy the Sissy

by Ide32 on Sep 14, 2017
Transsexuals & Crossdressers

Part 1 The Bank Job Chris or Chrissy as he calls himself has the job of his dreams, he works at a sperm bank for futas. His job is to dispose of samples that are non-viable, low sperm count etc. All day long he dreams about the creamy, yummy cum from futas waiting for him to dispose of it. While he is supposed to put it down the sink, he has a preferred met...

Mistress and Master

by davemacc65 on Sep 16, 2017
Transsexuals & Crossdressers

I had been to Mistress Elaine's and Master Johns several times but today's visit was different. Mistress Elaine had buzzed me in the gate but it was James their butler who waited for me at the door. I had not met the staff of the house properly but I had heard them moving around and cleaning. I had wondered if Mistress had more slaves but the people I had br...

House Rules Pt. 02

by GavinNuisance on Mar 16, 2020
Transgender & Crossdressers

Terry laid naked on Lana's couch, face down with his ass sticking up. Her cum had dried. Drowsy, and still a bit tired, Terry began to move, and stretched as he adjusted his eyes to light. He noticed the sun was setting and he was clearly there for at least a few hours. He rubbed his eyes, but noticed a peculiar feeling in his backside. "What the fuck?" He...

Internet Meeting Ch. 04

by Stillherer on Sep 16, 2017
Fetish

I tried to appear casual as I wandered about the busy mall wishing to remain anonymous, discrete. Beneath my attempt at normalcy my body seethed with frazzled nerves as I checked out Charles' appointed meeting place. Charles had selected a toilet in a quiet secluded corner of one of the upper floors. I hesitated at the door, casting a nervous glance over my...

Wife in Control Ch. 08

by wifetoy on Sep 25, 2017
Fetish

This is the eighth and final chapter of my wife's fulfillment of the punishment poem offering humiliating punishments 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 adore and cherish my beautiful wife. She not only tells me how much...

High School Dilemma Ch. 06

by LaurenWestley on Sep 15, 2017
Fetish

(Authoress's note: of course all disclaimers are still in place regarding characters etc. PLEASE DON'T READ THIS IS YOU HAVE AN AVERSION TO PEE SCENES AND EXTREME HUMILIATION. This is only a fantasy story XXX+. I only wish there is enough here to make each of you happy. To those who have given me constructive criticisms as well as those with praise thanks. I...

The Wedding Ch. 04

by betamale08 on Mar 30, 2020
Transgender & Crossdressers

The Wedding (Patti Cake part 3) Chapter 4 -- Teaching, Teasing and Testimonials... I was a little stunned and leery after reading my version of this contract which wasn't all that different from Patti's... From changing my name to rescinding my rights to wear male clothing while in the employment of Darren and Carol -- or Ma'am and Sir, and also, not to f...

Black Cock Smoking Sissy Slut

by Lisa_Fuckslut on Sep 14, 2017
Transsexuals & Crossdressers

I left the club early. No luck tonight in getting my ass laid. Where were all those hot young studs with their big swinging penises and cum-filled balls when you need them? I had dressed in my sluttiest gear. 6 inch 'fuck me' heels, fishnet stockings and a tight little leather dress. Heavy makeup. Long, thick false lashes to flutter at the boys. Long, sexy,...

Sissifying Addictions

by Sissyhalo on Nov 25, 2017
Transsexuals & Crossdressers

They say you're born gay, they say you can't catch gay, that you can't be made into something you don't want to. That somewhere deep, deep down you really want it. It's somewhere in between and none of it either. It's actually so much like dominatingly slick, sinking, drowning...so very like that first time you sink into sweet sissy ass. It started for me...

Clara Bow's Academy for Ladies

by Sputnik57 on Sep 15, 2017
Transsexuals & Crossdressers

Peter had had no choice in the matter from an early age. As he car drew up to the huge ivy clad castle-like building, having entered through electronic gates in a ten foot wall, he felt doomed yet excited. His cock was erect in the tight panties his Stepmother has chosen for his introduction, his anus tingled and gripped the soft rubber plug she'd also chose...