Sissy, Gameshow Stories

6,598 results
Orientation
Length
Source
Infinite Scroll

Jenny Gets a Guy

by ScottWood on Sep 1, 2017
Fetish

Jenny was trying to read and not doing very well. Every time she thought she was getting into the thread of the story, there was a new noise or a particularly hard jolt of the bed. Lady Astoria climbed onto the deck, she read. The wild sea wind took hold of her flowing locks and streamed them out, like the wild flights of her dreams. She -- "Oh God fuck y...

TIS: Sentosa Ch. 02

by LindaMichelle on Sep 13, 2017
Erotic Couplings

Still humiliated from the hard face fucking the Bike Shop Uncle gave her, Linda mounted her bicycle carefully, trying her best not to expose her sweet young pussy as she did so. However, her short denim skirt was so tight and so tiny that her attempt was an utter failure. Already a few passers-by had stopped to observe her the moment they noticed that a hot...

Willa Ch. 21: Twin Pack

by SZENSEI on Sep 14, 2017
Exhibitionist & Voyeur

"Eve? Why on Earth are you naked?" Willa Pryce and her new best friend "Ashleigh" alias, "Eve" Thomas, converse with the Lady of the Benson Manor, "Claire Benson". Via Skype from Israel. Every few days Claire while away would commit to seeing her lovely baby, "Grace". Willa as her Nanny held the child lovingly. The nudity of Eve next to them on the Sofa cau...

Fantasy or Reality

by mcfbridge on Sep 16, 2017
Reviews & Essays

The following is a comment I actually received on the final chapter of one of my stories. Specifically, you can find it attached to the epilogue of the Gameshow series. What a crock of crap. Nancy was right in the first place. Having a guy's dick shoved in the "out" door is painful. Period. You may get used to it, but if you don't like it the first time, 95...

A Day at the Races

by goodnnnight on Sep 14, 2017
Erotic Couplings

I was given a double ticket for a day at the races by a happy client. Entrance badges, free lunch, free racecard, looking good for an enjoyable and classy day I thought. My wife told me she had arranged to go on a trip with her sister, as they often do, so couldn't come and suggested I offer to our friends. Our friends Neil and Debbie are the same age as...

Find That Guy: Porn TV's TG Gameshow Round 02

by EyeSoreASite on Sep 16, 2017
Transsexuals & Crossdressers

Round 2 This Time It's Vaginal Synopsis: Freddy and Sue entered a sex based game show, were Freddy was transformed into a woman and the group of males competing against the couple must use the series of sex based challenges to determine which of the two is a real woman. The first challenge was Oral based, and a crashing disaster for our protagonists, due in...

Controlling Wife Ch. 03

by AllGiveNoTake on Oct 5, 2020
Fetish

This is a story of how my wife and I started down this fetish lifestyle. It is based on truth with elements of fantasy mixed in. There are now some definite elements of domination/force/loving lifestyle/humiliation. It is my first attempt at writing anything, please feel free to leave suggestions and comments. I just wanted to take a moment to thank everyb...

Clarissa's New Job Pt. 06

by Lisa_Sweety on May 15, 2018
Erotic Couplings

Thanks for reading my story. This won't make much sense if you haven't read the other parts. :) ***** A few days had passed since my appointment with Jay and Emma and, overall, it had been good. Emma and I had seen each other again a couple of times and I'd also seen a steady stream of clients in my apartment. All had been OK and just the usual sex request...

Sissy Gets Punished

by MsMorrigan on Sep 16, 2017
BDSM

Once upon a time there was an overly eager sissy girl. This sissy girl loved her mistress. She loved her so much she tried to anticipate her every whim before she needed to even speak the words. One day the sissy girl was vacuuming, dusting and general cleaning. She was openly lamenting on how her overly large pathetic sissy clit was getting in her way. How...

My Sissy Life

by snorn on Nov 26, 2017
Transsexuals & Crossdressers

I love being a sissy. I have been in permanent chastity since 27 Sep 2016, and am loving it. I have sissy training rules that are focused on keeping me doing the household chores and training me to be rented out as a cheap sissy whore/maid, a list of sissy motivational sayings which I listen to on repeat whilst doing nightly chores, and service rules for th...