Lost Bet Pegging Stories

182,901 results
Orientation
Length
Source
Infinite Scroll

Made to Obey Ch. 07

by madetoobey on Jul 10, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). Ruth, as a part of my punishment, was setting me tasks until Esther (who'd taken my laptop and mobile phone) could verify I'd never visited such sites before. I'd been forced into a chastity cage and m...

Stranger Fuck

by hfernandez1983 on Sep 13, 2017
Transsexuals & Crossdressers

It's been a while since I have written something. It's mostly because I have felt so uninspired and didn't know what to write. My main fantasies these days revolve around a man crossdressed while he is pegged by a woman who likes to dress as a man. My last story series Jenny & Mike got a decent reception and I wanted to write more. But like I said, I've...

Black On Black Pegging: Carleton U

by Samuelx on Sep 11, 2017
BDSM

For months now I've been subscribed to the website, and felt mesmerized by her presence. I've been into the BDSM lifestyle for a while now, but I've never really explored it. For me, it's the world of fantasy. I watch videos online, and I've got a small collection of BDSM erotic novels on my book shelf but that's about it. My day to day life is as vanilla as...

Rachel Ch. 05

by rachel_lethem on Sep 12, 2017
Exhibitionist & Voyeur

Rachel Ch.5 - A Morning At Home I’d decided to take a much needed day off from work. I’d been busy for what seemed like months now, and I was ready to have some time to myself. It was nice waking up naturally that morning, rather than being awoken by the harsh tones of my alarm clock. The late morning sunlight poured into my bedroom through the thin curtain...

My Neighbor Husband is a Jerk Pt. 02

by justme6996 on Dec 23, 2019
Fetish

The following story contains foot fetish, creampie eating cross dressing and pegging if those are not your things please look for a different story. As always i would love to read your suggestions ,comments and messages. -------------- That was our routine for the following weeks, she would stop by my apartment after her morning run, and I worshiped her s...

Down a Peg

by lustykisser on Jan 21, 2020
BDSM

I have always had a non-traditional exploratory approach to sex and sexuality. I've been in hetero relationships mostly but in the dry times fooled with men as well. The urge to feel receptive developed slowly but naturally. While I remained a masculine guy in day to day life, deep down I craved being receptive and feminine. I wanted to feel what a woman fee...

Somali Dominatrix In Nepean

by Samuelx on Sep 17, 2017
BDSM

As Salam Alaikum, people. The name is Maimuna Ismail and I've got a wicked story to share with you folks today. I was born in the Puntland region of Somalia and moved to the City of Ottawa, Ontario, with my parents, Hodan and Ali Ismail, in the late 1980s. I grew up in the Capital, and consider myself as thoroughly a Canadian as anyone. Home is where the h...

Tricked Into Pegging And Sucking!

by Everyday2 on Sep 25, 2017
Transsexuals & Crossdressers

It all started about two months ago when my wife and her two girl friends turned the tables on me and the two husbands of her friends. We had been getting together as a group for dinner parties with a theme for a long time. Always it was the guys who decided what the theme for the party was, and we had done football, hockey, pirates, Disney, monsters, etc. Y...

Mistress Chelsea Of Walmart

by Samuelx on Sep 17, 2017
BDSM

"Bet you thought I was soft and sweet when you met me at the front end of Walmart," Chelsea said softly, a wicked smile on her lovely face. Strutting her stuff, working the hell out of the red tank top and black leather miniskirt she had on, she looked hot, sexy and dangerous. Hands on her hips, Chelsea waited for her sub's reply. From the moment Chelsea la...

My Journey Ch. 01

by npanxx on Sep 19, 2017
Transsexuals & Crossdressers

I found myself in a midsized college town working on a problem that didn't want to be resolved. With assistance from my co-workers two and a half hours away I was finally able to correct the issue, and system operation was restored. It was late, I was more than three hours from home, and decided I did not want to make the drive. Instead I chose to spend the...