Anal Virginity Stories

59,983 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

One Special Spring Day Pt. 06

by Connie_Ann on Sep 16, 2017
Group Sex

Ratman39 provided proofreading and editing of this story. Thank you, Ratman39 - you totally rock! ***** Just as Mike is about to take Bonnie's anal virginity, he is distracted by the sound of heavy footsteps approaching the door from the hallway. Mike realizes from the sound of those footsteps approaching there is more than one person about to enter the o...

A Wedding Night Pegging

by pwlrstr on Sep 12, 2017
Fetish

"It would be more of a big deal if it was the first time," Jon had said, instantly regretting that it sounded a bit negative, when his fiancée Naomi had asked if he was looking forward to their wedding night. "I mean, I don't really believe in saving yourself for marriage or any of that crap. I think it's definitely been a good idea to have lots of sex first...

Dear Angel Ch. 01

by Goldeniangel on Sep 12, 2017
Reviews & Essays

Welcome to my version of "Dear Abby". I've found that a lot of readers often have questions about me, my stories, or just sex in general and that many people ask the same questions or variations of the same questions. So this is my solution to that; send me in a question and I will answer it and post it in the general forum. I would prefer just general quest...

BBW Anal Virginity Auction

by Samuelx on Sep 12, 2017
Anal

My name is Adriana Ellen Wellington. I'm a student at Blackstone University in the city of Newton, Massachusetts. Life these days couldn't be better. I mean, I'm attending one of the best schools in the world, and it's all for free. The benefits of being a student-athlete at a major school. I'm a member of Blackstone University's all-new Women's Varsity Wres...

Anal Virgin

by dr_luvs_shaving on Sep 16, 2017
Anal

This is a romantic story of how I helped an ex-lover fulfill her desire to have anal sex. I am a businessman who in the 12 years since graduating from college has started and built and very successful business. Part of my success comes from my willingness to travel over 50% of the time. This schedule allows me to stay in touch with friends and old acquainta...

Lessons In Love Ch. 01

by velvetpie on Sep 16, 2017
First Time

Grant took a chair and tried not to stare at the other people who occupied seats in the classroom. He had spoken with only one other person when he entered and he was too embarrassed to introduce himself to any more. After all, what would he say to someone else who had the same problem as he did? He pulled the brochure from the pocket of his jacket and busi...

Breaking in Kira's Ass

by Cesmina36 on Oct 30, 2018
Anal

Kira shivered as she read the request. There was nothing noteworthy about the invitation itself, but the reputation of these clients preceded them. They were a group of business guys who threw these parties, hired escorts, and were known for their love of anal sex. The girls Kira worked with only had positive reports from working those events, but she hesita...

Emily Goes Black Ch. 02

by ashsmith on Sep 26, 2017
Interracial Love

Emily slowly stirred the next morning as the sun began to stream through her bedroom window and fall on her pale, nude figure. Panic gripped her for a brief second when she realized she was not alone in her bed but just as quickly, she remembered the events of the night before. It had been three months since her husband left on deployment, and this was the f...

My bi experiences

by RoundAss30 on Apr 22, 2025

Pick an experience below.What's next? My anal virginity taken by a black man with a big cock Cumming on a huge dildo while gagging on another one Ad Go into another direction with AI...

Open in Reader

Big Girls And Big Guys Orgy

by Samuelx on Sep 1, 2017
Group Sex

Angela Baron smiled as she walked to the door. Finally, her friends were there and the party was about to start. For the last time, she checked herself in the mirror. What she saw pleased her. At the age of twenty, this brown-skinned chick stood six feet tall, chubby but sexy, with a voluptuous body, large breasts, thick legs, wide waist and huge, round butt...