Sissy Plug Stories

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Orientation
Length
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Infinite Scroll

Sissy Whore Ch. 04

by DebbieDublin on Mar 14, 2018
Transsexuals & Crossdressers

I stumbled to the bathroom to fix my face, my head still spinning. I reapplied my lipstick and dusted off my foundation. Wiped away the mascara stains from my cheeks and reapplied. When I was done I returned to the living room. 'These are for you.' He said when I approached. He reached into his jacket, extracted a pair of large gold coloured hoop earrings...

Sissy Plays the Game of Thrones Pt. 03

by SissyKelly on Dec 13, 2017
Celebrities & Fan Fiction

I felt the shocked and angry eyes of Jamie Lannister staring at me. My twitching butthole. My balls. The base of my cock, the rest of it buried in his sisters pussy. His lovers pussy. "What the- what are you?" Jamie asked, I couldn't speak. I pulled out of Cersei's pussy and fell next to her on the bed, she sat up and smiled at Jamie. "Oh little brother,...

Letter From Franklin Cluster

by justincbenedict on Jan 15, 2018
BDSM

Dear Shoeblossom, You might remember my mom's letter (how long has your column been going?) "Letter from Pecan Grove" about how she trained me to dominate my dad, or "Letter from Dubuque" when I was living in Iowa with my slave boy, Brantley, Senior...RIP. I believe the author of "LETTER FROM AMES" another part of Iowa, referred to his initial femdom exper...

My First Crossdressing Ad

by NerdySissyHippie on Dec 8, 2017
Transsexuals & Crossdressers

Growing up, I had always been a weird, lanky nerdy with long hair and a quiet demeanor. Even when I signed up to play sports in middle school, I was never what anyone would consider to be masculine and preferred hanging out and talking with my female friends than getting rough and dirty with the other boys. That's not to say I was particular effeminate eithe...

My Father-In-Law's New Bride Ch. 02

by regina_allen55 on Sep 25, 2017
Transsexuals & Crossdressers

He was in complete control and I would be forced to do what ever I was told as I didn't want anyone let alone Donna to find out my dark secret. As I moved closer his hand reached out and he pulled me to him. He pressed himself against me and I could feel the bulge in his trouser pressing hard against my thigh. His arms were around me as he pressed his lips r...

Punished Asian Shoplifter Ch. 11

by asianspankee on Sep 15, 2017
Anal

It's now time for my second to last punishment session at your office. It's going to be another after-hours one, which hints that something unusual is going to take place again. I cringe at the thought of what else could it possibly be that I haven't been subjected to already? Well for starter, when I walk into your office there's an odd-looking wooden benc...

A Sissy is Born Ch. 04

by 0ra11yfix8ed on Sep 16, 2017
BDSM

As this is an obvious continuation of a previously submitted story, reading the first three chapters will enhance your understanding and enjoyment of this chapter. * You pick up a bag from behind the bar and place it on the bar. You toss my keys next to my bag. "Your car is in the garage; you're free to leave any time. But I'd really like you to stay and...

Cuckold Nite Out

by newstylewife on Aug 17, 2017
Fetish

My name is Karen, I am the hot wife. I am 30 years old, a true blonde with a fantastic figure if I say so myself with pert 36 C cups. I am Alan the cuckold husband. I too am 30 years old quite an attractive fellow but blessed with a submissive nature and small willy. Introductions made let me start with the story. I arrived home on Friday night to find A...

Michael's Destiny Ch. 02

by CrossdressingDestiny on Sep 16, 2017
Transsexuals & Crossdressers

By the time Ashley and I were upstairs, my sniffling had stopped, though I was no less distressed. Ashley obviously already knew... hell she was the one who saved my ass from my homophobic parents when they almost caught me last time. But still... Destiny is a private side of me! Only I know her- really know her anyway- my followers just see a cute sissy boy...

Slave Ch. 07

by slaveheathen on Sep 25, 2017
Fetish

Note: As stated in previous chapters, this is a story about a bisexual submissive man, exploring all his (and mine) kinky fantasies. There are elements of truth in this story, and elements that are things I hope to explore in the future. There is therefore bisexual sex, as well as piss play and much more. If this is your cup of tea, read on! If not, no big....