Lost Bet Strapon Stories

183,182 results
Orientation
Length
Source
Infinite Scroll

Keeping an Open Mind

by Templar_Writer on Nov 4, 2019
Fetish

Not much to say about this one, just an idea I have been meaning to get to. "Okay, now I'm asking you to keep an open mind." Having just finished a great meal cooked by my girlfriend, Seema, for our anniversary, I was in a good mood. However whenever she asked me to "keep an open mind", it didn't mean the same thing other people mean. When she uses that phr...

A Dickgirl's Birthday Present

by sajukno on Sep 19, 2017
Transsexuals & Crossdressers

"Happy birthday, Ann!" Charlene presented her long-time girlfriend, Ann, with a beautifully wrapped present. The two had been together since they were both freshmen in college. Ann was drawn to Charlene's beautiful smile and her wit. At first, Charlene hadn't been very receptive of Ann's overtures, but after a spontaneous drunken fling, Charlene had fallen...

Adult Comixx

by old_n_dirrty on Sep 12, 2017
Celebrities & Fan Fiction

"What a fucking day!" thought Dagwood, as he trudged up the sidewalk to the front door. The hum coming from behind the house must be Herb mowing his grass. "Fucker's probably using my mower," said Dagwood aloud. "Maybe I'll fuck Tootsie as payment!" Old man Dithers had chewed on his ass all day, and as a final insult, had transferred Dagwood's big-titted se...

Last Friday Night Ch. 02

by bitexwriter on Sep 12, 2017
Group Sex

The week after our amazing night with Rick and Tonya was interesting. Margo and I fucked like crazy, but there was a slight tension to it. We tried not to talk what happened about too much, but it came up frequently. Margo was worried that she had let everything get out of hand since she started the festivities, and I was worried that she wasn't comfortable...

A Strapon Tale Pt. 01

by damn_thats_me on Mar 2, 2020
Fetish

All the events in this story really happened, only the names have been changed. Warning: contains themes of pegging, femdom, leather & latex and chastity play. Alex (29) and I (36) had been seeing each other for about a year now. During our first date I immediately sensed that she had kinky potential. There was simply something about her looks and attitud...

Avery Dirty Date Night 03 - Sunday

by Hank_Avery on Oct 3, 2018
Anal

I slowly opened my eyes, waking from the deepest sleep I'd had in some time, as I felt the harsh cold of a stainless steel plug being pressed into my ass. I didn't resist, or even make any hint that I had woken, I just led there in bed on my side and accepted that Avery clearly had no plans to lay off of me today. I was relieved, but also somewhat disappoint...

Avery Hot Day by the Pool

by Hank_Avery on Mar 7, 2018
Anal

Since our return from our hot vacation, Avery and I had been wild with lust for each other round the clock, including the evening of filth we shared to celebrate my birthday last month. Today was saturday. Avery was home while I was working a morning shift. It was a glorious day, 30 degrees outside, sun blazing and not a cloud in sight. Work was the last pla...

Ragdoll Ch. 07

by CapriciousRain on Sep 16, 2017
BDSM

"Strip princess," Victoria commanded Violet. For the moment, Chelsea and Niobe lounged in sumptuous chairs and watched the scene play before them. It was a short time after the end of Brentwood's impromptu meeting, and the four girls were closeted away in Victoria's room. Victoria's tone was icy, yet laced with a dark sensuality. She was in a mood to play...

The Experiment

by Boone3030 on Apr 1, 2020
BDSM

THE ADVENTURES OF TIM AND LAURA: THE EXPERIMENT This is the start of a collection of erotic short stories about a couple named Tim and Laura and their adventures into exploring the world of BDSM and kinky play. There is no definitive timeline associated with them, as in some may be more vanilla and tame from when they were first getting into BDSM play while...

My Strapon Fantasy

by libertinaXx on Sep 19, 2017
Transsexuals & Crossdressers

I woke up in the middle of the day and smiled; my girlfriend had gone to work a few hours earlier and promised me a really good time when she got back. I ran upstairs to shower and make sure I was hairless before getting ready for her. I wandered into her room to dress for her arrival. I found a purple sheer thong and matching bra in her underwear draw that...