Sissy Boy Post Orgasm Stories

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Sissy Stretching for Princess T Pt. 02

by Subboi23 on May 12, 2020
Fetish

Once I get home, I practically run to my room. Sitting in the car has pressed my plug deep into my ass and now my running causes it to wiggle around while still deep inside me. "Home Princess," I text as soon as I close and lock the door to my room. I quickly peel all my clothes off except for my panties and get on my knees. My toy is retrieved from a draw...

Wanderlust - Sabrina Pt. 05

by GeneraZ on May 11, 2020
Sci-Fi & Fantasy

5 - The Power Shift Paul's feet flexed painfully within the pink high heels. They weren't his, and they were much too small. With their lift he was exceeding six feet in height, causing him to loom over his beautiful blonde haired counterpart, but that did nothing to change the air of power she held over him. She giggled sinisterly as he, otherwise complete...

Hubby Drop To Thy Knees! Ch. 07

by Ashesh9 on Sep 14, 2017
BDSM

Ch.7 So where do we go from here...???? But the Royal lass & Her commoner beau couldn't keep their hands &... er... various body parts off each other in following days, weeks... months. Johnny boy usually got erect in Her voluptuous presence but was circumspect enough not to dare to take Royal Virginity that might create a Royal scandal which would create p...

Mom's in Town Ch. 06

by 1sfshermale on Sep 26, 2017
Group Sex

With one hand remaining on her head, holding her mouth on his cock, he used the other hand to pull on the stainless steel chain of the slut's nipple clamps. "OOOOOOOOOOhhhhhh" was all she managed to scream as her nipples stretched from the upward pull. She could not speak because her tongue was trapped under the slab of cock in her mouth. It could only feel...

Domination Ch. 02

by morenowagain on Sep 15, 2017
BDSM

Part I may be found here: http://www.literotica.com/s/domination-15 Chapter Four To be perfectly honest, I was a little overwhelmed by the possibilities. I mean, having another human being ready and willing to do whatever you ask? There are just too many things. Of course, my mind immediately turned toward the more sexual ends toward which I could put Jake...

The Jewelers

by mollycactus on Sep 16, 2017
BDSM

Author's note: my BDSM stories are mainly D/s in nature – there is no Literotica category for these, so if you do not like D/s, you can skip this story. ***** Molly had taken on a new submissive male, who had what seemed to her to be, a strange need. Kneeling before her, Robyn explained his desires. "Please, Miss. Cage my cock so you'll be completely in c...

Teacher Transformation

by Writer2000 on Dec 23, 2017
BDSM

Nasty Teacher, naughty girls Mr Smith really was an unfair teacher. He let the boys get away with murder, but he was extremely strict with the girls. He would punish the girls at every opportunity for the slightest misdemeanour, giving them detentions and extra homework. As well, he was in the habit of putting girls down whenever he could, making sly ambigu...

England, before Tanya

by Stillherer on Aug 18, 2017
Fetish

It was the late 1960's. I was a young lad traveling about Europe, running low on money. In desperation I ended up staying with family friends, Mr and Mrs Hull, in England. They were odd people and their plain Jane oldish daughter stuck in a small village house looking after her ageing parents was even odder. They made it pretty obvious from the start that th...

A Gift in Disguise Ch. 09

by Talespin on Sep 14, 2017
Novels and Novellas

Who in his right mind calls me on the phone at 7 a.m. on Sunday unless it's an emergency? "Hello." My greeting to whomever was calling was not exactly warm and fuzzy, but neither was it in-your-face hostile. After all, it could have been my mother. "Tom, hi. It's Kim. I'm at the airport. Did I wake you up?" I wanted to sound more civilized. Really, I did,...

Simon Sissy Slave Ch. 02

by Timewarp10 on Jul 30, 2019
BDSM

Simon's arse remained sore for days, a constant reminder of his new role in life. Over the weekend the pain was severe, but the overwhelming feeling of his humiliation was compensation enough, and produced a warm glow through his body. His mind had been in turmoil all week-end. Sometimes the pain was unbearable, but he bought a cream at the pharmacy that rel...