Pegging Bet Stories

66,541 results
Orientation
Length
Source
Infinite Scroll

Jessica

by Floydman1 on Apr 9, 2019
Transgender & Crossdressers

Author's note: This is mostly vanilla first-date stuff. The story starts out fairly extreme with BDSM, squirting, and fisting that's all SSC (Safe, Sane, and Consensual) but it turned out that her story was much more of a traditional "figuring things out" story of a transwoman, albeit an involuntary one. On that note, I am a cisgender male so if I got any of...

Partner Games Ch. 01: The Neighbor

by m_storyman_x on Jun 4, 2019
Loving Wives

It sucks to get old. When the old calendar ticked to the sixty mark this year it was almost terrifying. Not that I look that old. Most people that see us often guess we're in our late forties at most. My wife still looks every bit as good to me as the day we got married. Well shaped, a bit more sag in the fun bags, but almost no gray in her short cropped bro...

Housekeeper Pt. 03

by CrazyDaveTrucker60 on Jun 11, 2019
Loving Wives

You may wish to read parts 1 and 2 first, so things make sense... Or not, hey it's a free country. Nobody under age eighteen is in here, please remember it's a piece of fiction, not reality, any resemblance to persons living or dead is completely ridiculous. Try to be civil in your comments, please. Especially you Mr. Anonymous! ************ My soon-to-be-...

The She-Shed Ch. 02

by Brittni4u on Mar 25, 2019
Group Sex

When I awoke early on December 31st, I was careful not to wake my boyfriend Shane who slept soundly beside me. We were guests at Nancy and Joe's villa near Phoenix and had been there the last four days. I was happy that I had convinced Shane to loosen up and have sex with Nancy even though he was unaware of my total sexcapades the previous three days or with...

The Bet Ch. 01

by RandyCross on Nov 6, 2018
Erotic Couplings

** My first attempt at a longer piece - do let me know what you think! ** ***** I was always a patsy for being sent to conferences at short notice, the price I paid for being single, childless and pet-less. This particular conference, my boss reasoned I could drop everything and head to Liverpool at short notice, with a couple of hundred quid as a sweetene...

Creating Ginger Ch. 03

by Ms_Allison on Jun 1, 2020
Transgender & Crossdressers

Author's note: This is a story of a loving, married couple who wanted to expand their boundaries. It involves crossdressing, gender play and their foray into, cuckoldry, dominance and submission. If these are not topics you are interested in, then please move along. In the below story I refer to the male character several ways but try to maintain a consiste...

Finally a Princess Pt. 01

by fireandlace0533 on Sep 14, 2020
Transgender & Crossdressers

The first part, of what will be a multi part story, of a crossdresser who loves Disney getting to step out of the closet. I like to develop the characters so if you are hoping to get straight the sex you will likely be disappointed. Finally a Princess (Part 1) You could feel the excitement on the bus as it traveled along the highway. The video showed a bun...

Mom & Me Ch. 35

by Yechesem on Apr 15, 2020
Romance

Billy's First Date With Rachel Nicholson As I was walking down Broad Street I remembered I needed to go by the florist shop to pick up Rachel's corsage. I turned on Wright Avenue and made my way down to Main Street where I turned west and walked another three blocks before entering Marybeth's Flower Shop. A sales lady approached and asked me if she could...

Timid Neighbor

by shutterpsb on Mar 9, 2020
Mature

This story is a revision of a story I posted to Literotica several years ago. This story is a work of fiction and contains no references to any real persons or events. *** Tapping on the patio door caught my attention. I shouted for Rick to come in. I looked up at his footfalls and smiled at the teenager. The boy had a parcel in his arms. "It came, John....

The Bad Boys Club - Half Time

by JimAner on Oct 6, 2020
Fetish

This bondage and discipline story is a CFNM tale about women spanking their husbands. It is also a story that celebrates domestic discipline where the female, NOT the male, is the disciplinarian. If the thought of a woman using a paddle on her husband's behind upsets you, or if a story about men having to act as sex objects and sex toys offends you, do not r...