Strapon Boy Stories

106,036 results
Orientation
Length
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Infinite Scroll

Happy Birthday Threesome

by mothman34 on Sep 4, 2018
Transsexuals & Crossdressers

"Happy birthday baby," my wife Tina said as she wiped my cum away from the corners of her mouth. "I hope you enjoyed your first gift." "My first gift??" I replied. "You'll see," she said with a mischievous grin as she got up from the bed & walked into the bathroom. Waking up to a blowjob from my beautiful wife, maybe this will be a good birthday, I though...

Tim and his Queen Pt. 01

by Queens_boy on May 12, 2020
Fetish

Day 1 (Meeting her for the first time) Tim exited the plane, excited he was finally going to meet Sass, his Queen. Walking through the terminal he didn't know what the next week had in store for him. He chuckled thinking back to just a few hours ago, The TSA agent going through his bag finding all his plugs and toys, ordered by his Queen to bring them, she...

Amy Finally Lives Out Her Fantasies Ch. 02

by LuvAGoodPegging on Sep 11, 2017
Transsexuals & Crossdressers

(Author's Note: This is a continuation of "Amy Finally Lives Out Her Fantasies -- Shy Amy uses her strapon on Kyle". Thanx to all who provided such great feedback. Hope you like part two. Warning: this story contains male/female strapon sex, cum eating, and as the category suggests, shemale sex. If those aren't your things, you won't enjoy this story. Love t...

The Cuckold Ch. 02

by sissyboycamille on Sep 13, 2017
Toys & Masturbation

Since that strange evening the sex with my wife had become very intense. We had gone from having sex once every month or two to a few times a week. She seemed to have discovered a new found interest in sex. Everything turned her on. A few times she came home very late and had me on my knees in the living room licking her pussy for ages, her pussy smelling st...

A Slave under Contract Ch. 04

by gynarchite on Jul 31, 2018
Sci-Fi & Fantasy

Chapter 4 – The city of Galos We left the house the next morning, flying the aircar to the airport. Long-distance travel needed a much bigger craft to make it efficient and safe, so my owners would take a supersonic plane to fly to the island city Galos, a thousand kilometres to the south. My arse was still sore from the pounding that Mistress Delilah's str...

A Week in the Life of a Cumeater Ch. 05

by Ilovetoeatsperm on Sep 13, 2017
Fetish

Saturday. While my wife and I were working around in the yard my wife asks are we going to have sex tonight. I say I don't think of anything that can stop us. She says good I need to run to the store later so let's finish our work. I tell her go ahead and clean up that I'll finish what we have to do. She heads in and showers, I keep working. She finishes and...

Chess

by ToferSixoErotica on Jan 15, 2018
BDSM

"You're not going to like this." Jason said smirking. Holding his bishop, delicately between his index and middle fingers. "That's what you think." Rachel said back. "I know I can win this time!" "Really?" Jason raised an eyebrow, "Because I know for a fact that once I make this move, I can check mate you in three more turns. But, I could always..." "No!...

An Uneven Christmas

by libertinaXx on Sep 13, 2017
Transsexuals & Crossdressers

By Christmas, Sarah and I had been 'dating' for a few weeks. If you could call it that. I had been spending a lot of my time with her but I often felt more like a servant than her boyfriend. Most couples might curl up together to watch a film, I was more used to curling up at her feet. Worse, I was sure my friends realised there was something odd going on. M...

Getting Kinky with Sarah Pt. 03

by Anoneemuss on Feb 12, 2019
Erotic Couplings

"Hey sexy, how does this look?" I turned and looked over my shoulder to see Sarah posing in the doorway, legs apart and hands behind her back, but it was what she was wearing which left me momentarily speechless. Shiny black hotpants with a zip-up front, matching stockings - latex I think - and high heels which were secured with padlocked ankle straps. Sh...

The Court: Last Resort Ch. 02

by Lottiessub on Sep 14, 2017
Fetish

I was released from the stocks and ordered to stand at defense counsel's table. My hands were uncuffed and I stood where I had many times before, but midst circumstances very unlike any I had encountered in my career. The Judge smiled from the bench and welcomed me to HER Court. "Counsel, it is nice to see you...all of you...in my Court today. You are, howev...