Sissy Game Stories

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Orientation
Length
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Infinite Scroll

Bewitched, Bothered and Bewildered Ch. 03

by trevorm on Aug 30, 2017
Fetish

Part Three RULES OF THE GAME Where Vivian's mother lays out exactly what she expects from her son if he wants to keep her onside and help him to achieve his dream. Vivian went into the bedroom with a towel wrapped around his waist. He was whistling, there was a spring in his step. "You've been ages... hello, what's this?" His mother indicated the towel....

The Writer's Secret Ch. 09-10

by AnnMichelle on Sep 16, 2017
Transsexuals & Crossdressers

Chapter 9: Laura's Mall Odyssey Loren was sweating bullets by the time Stephanie finally parked the car. He expected they would go home. They hadn't. Instead, they were parked outside Raycine's, a department store at one end of the Valleyview Mall. The mall was only five miles from their house and they shopped here occasionally. "I can't go in there." "Yo...

The Prostate Exam Pt. 08

by His_fag_wife on Sep 25, 2017
Transsexuals & Crossdressers

Please do not read on unless extreme sissification and forced gay and bi scenes, watersports and cum eating, really flick your switches. I don't want to offend anyone so thought this comment might help. ***** It'd all started with a routine visit to his Doc for a simple prostate exam. His Dominant female doctor had pushed her finger just into his ring and...

Exposed Sissy Slut

by MarkRoberts64 on Sep 16, 2017
Exhibitionist & Voyeur

I've always been turned on by exhibitionism, and especially by so-called "forced" exhibitionism. The last few years, I've noticed more and more that I love the game of taking risks in public, where I could possibly get caught being submissive, or slutty, or a sissy. I'm not interested in just exposing myself, or strutting around with a slave collar on. What...

Something New Something Old Ch. 03

by dorian87890 on Sep 25, 2017
Fetish

Ted's life had been turned upside down in the last five weeks. He was currently on his hands and knees in the bed of his neighbors' Josh and Nancy. A pair of pink panties were at his ankles and he was wearing a matching pink bra. His cock dangled between his legs trapped in a cage. Nancy was behind him with a strap-on. She was fucking Ted mercilessly. Josh...

The Drop-Off

by Longo_Afar on Nov 18, 2019
Transgender & Crossdressers

"Where's my comb, Mommy?" Margo sighed. Sissy could be so needy at times. And was there even a brain underneath that pile of blond curls? "I'm sure I saw it on your nightstand. But if you can't find it in all the junk you've piled up there, I'm not surprised!" Yes, Sissy's nightstand was a clutter of lipsticks, rouge, mascara and numerous other skin care...

Attack of the Yellow Convertible

by 4glory6 on Sep 1, 2017
Group Sex

Gail nudged Sam's body off her stomach and to the side. He was lost to the world. She had about ten minutes she figured before he started to snore and she'd be forced to get up and go to the guest room. The mention of "guest room" got her off on the cryptic e-mail message she'd gotten from her cousin, Faye, earlier in the day: "Landed in PBurg. Docking soon...

Pink Panties

by DrLuverotica on Mar 27, 2019
Transgender & Crossdressers

It all started with a pair of pink panties. It was sometime after midnight when Jo arrived home from being on-call at the local hospital. She'd received a phone call several hours earlier about a bleeder and had to rush in. Recently her workload had become almost unbearable, but we needed the money so she was working her sexy curvaceous ass off. By the ti...

So Many Poles, So Many Holes!

by dirtyjoe69 on Aug 29, 2017
Group Sex

The room was dark and humid; all the bodies raised the temperature to that of a steam room. If one was to stand back from the group we would look like a pile of garter snakes coming out of hibernation. Limbs were everywhere, flailing and twisting in the throes of passion. I didn't even think it possible to have that many people on one bed. Five men and five...

Hotel Cum Sissy

by closetbecky on Sep 14, 2017
Transsexuals & Crossdressers

I was on a business trip in central Pennsylvania and decided to stop for the evening and get a hotel room before I continued on the early the next morning. I stopped at a hotel just off the exit of the state highway around 7:15 and checked into a room. I had noticed that there was a small bar open just off the lobby while checking in. I arrived at the room,...