Lost Bet Strapon Stories

183,182 results
Orientation
Length
Source
Infinite Scroll

Night With Chantz Fortune Ch. 08

by lilguy on Sep 16, 2017
Celebrities & Fan Fiction

One night I met a woman of my dreams. Her name was Chantz Fortune. She was a strapon queen he use strapon on guys in many movies. She was blond haired and busty woman. She had the body of a porn start but the mind of the most sadistic dominatrix you ever seen. I met her as fan and she totally dominated me. I was her toy. I became a love slave and completely...

The Apartment Ch. 03

by bigjohn2501 on Sep 26, 2017
Exhibitionist & Voyeur

As I stood outside her door, I knew this was going to get me in trouble. It had "get your ass thrown in jail" written all over it. But it was just too good to pass up. After all the pent up hormones from the last couple weeks of watching Jill, my mind had officially lost it. I reached down and turned the handle on her front door and opened it easily, unlocke...

Mistress Monique Pt. 02

by bleedndkn on Sep 25, 2017
Fetish

This wasn't even my fantasy, I thought as I purchased the clamps, butt plug, heels and maid dress online with expedited shipping. The next day I brought the items in a backpack to Mistress Monique's apartment while she was at work. I put everything on then placed the butt plug in my ass and tightened the nipple clamps painfully so they wouldn't fall off, th...

The Surprise

by madengineer3 on Sep 17, 2017
Mature

Copyright 2008-09 by Madengineer3 All rights are reserved. Copies of this story can be downloaded for personal use only. Notice: When the word God is used as an expression in this text it is not meant to be blasphemous. It is an exclamation to God, not just a saying. My name is Jim. For many years now I have lived like a hermit. Within the last two mont...

Pegging Tales: Justin's First Time

by hfernandez1983 on Sep 13, 2017
Illustrated

*-*-* Pegging has been a topic that I have wanted to write about for a very long time. In my personal life, I have yet to do it. It has long been a fantasy that I felt has been left unfulfilled for a while. I have read a lot of stories on the topic and have loved most of what has been published on Literotica. So I thought it was time maybe I write a story o...

Sissy for Mommy's Nipple Cream Ch. 05

by ppeaks42 on Nov 2, 2020
Transgender & Crossdressers

The evening after Jaime's doomed attempt at seducing Julia found the young sissy crying into her pillow as she tried to reconcile herself to the whirlwind of changes she'd gone through. Less than two months ago "Jaime" had been nothing but a shared figment of imagination, a character he dressed as for his regular breastfeedings with his mother. When he'd tri...

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 College Professor's Discovery Ch. 03

by escriterra on Sep 26, 2017
Fetish

The driver who had met Sherrie on her first and second arrivals at the Christchurch airport was grinning at her as he waited at baggage claim while she made her way through a throng of people, all who seemed intent on being the first to retrieve their luggage. "Dr. Mathison! So good to see you again!" said the dark-skinned man known only as "Catchy" to Sher...

Sabine At School Ch. 15

by Sabineteas on Sep 15, 2017
Exhibitionist & Voyeur

I woke up the next morning with Melanie spooned up behind me, one breast in her hand and I felt so warm and relaxed. I loved having her hold me like this. It was sexy and romantic and it helped me forget everything else. But I couldn't help but remember last night and that I let a man fuck me in front of her and Erin. Let him come in my mouth and that I had...

Submissive's Journey 10

by mollycactus on Sep 15, 2017
BDSM

Okay, even Mistresses can get horny. This became very clear to me on that day. My first clue was when Barbara came breezing into the house and announced, "I'm horny." Susan walked over to her, gave her a big hug and a loving kiss, and affirmed, "Funny you should say that. My hormones seem to be raging this morning also." Releasing their embrace, they b...