Anal Streching Stories

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Anal Sex: The First Time

by PositiveThinker on Sep 15, 2017
Anal

"It won't go in. You're too tight. Bend over more and stick your ass up higher so that I can get more of a straight line run at it. Yeah, that's it. Now hold that position. Fuck! It's not working, it just bends. Every time it starts going in, it bends itself out." "Try it again but be more forceful, but gentle this time." "Okay, try spreading your ass chee...

A Better Master

by WFEATHER on Sep 17, 2017
BDSM

How many times over the years had He made use of my ass, either with His own thick cock or with one of the anal toys in the collection? i could never begin to count, but i would guess that it would be over one hundred times during the first two years of marriage, plus perhaps another fifty times while dating and while engaged. Without question, He loved fi...

A Guide to Great Anal Sex Pt. 03

by celesteandjim on Sep 26, 2017
How To

Thanks to everyone (particularly women) who have wrote, expressing gratitude to us for raising their comfort level with anal sex. We want everyone to find what works for herself within her comfort zones. Just to review the areas of intense anal stimulation for a woman, there are four key elements: 1) the exposed head of the clitoris; 2) its tip ends; 3) the...

Big Black Woman On Campus

by Samuelx on Sep 1, 2017
Group Sex

My name is Fabiola Valentia Etienne. I'm a big black woman of Haitian descent. I'm a five-foot-ten, large-breasted, thick-bodied, wide-hipped and big-bottomed black woman who is very proud of every inch of her body. I weigh exactly two hundred and sixty pounds. I'm healthy, happy, and successful. By day, I'm a student-athlete at Bayden State College in the w...

Give up the Ass

by zechs195 on Aug 2, 2020
Fetish

Jennifer is a high school senior known for being a nerd and a drama geek. That all changed one day when she was asked out by a popular jock. Jennifer’s new boyfriend, Scott, has an ex-girlfriend. Scott’s ex-girlfriend, Jamie, has a passion for the dark arts. Jamie also does not believe in anal. Scott considered that a deal-breaker so he decided to go out wit...

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A Guide to Great Anal Sex Pt. 01

by celesteandjim on Sep 26, 2017
How To

My name is Jim. Celeste, my wife of thirty-two years, and I are almost exclusively ass fuckers. Anal intercourse for us is not a once in a while event, but our preferred method of expressing our deep commitment to and love for each other. This is for a very simple reason. Celeste would openly tell you that the weakest orgasm she experiences when I am in her...

Freddie Gives Gayle Anal

by BOSTONFICTIONWRITER on Sep 14, 2017
Anal

"Hi, Freddie." "Oh, hi Vinnie." "What's wrong? You look down in the dumps." "I'm stuck writing a story." "You? Stuck? Are you kidding me? You've written a million stories already. You've written so many stories that I can't keep up with you. It makes my head hurt to read that much. Besides, I had to take a break because my finger is blistered from going...

Eating from Her Ass

by Analmatt on Sep 12, 2017
Anal

Like most people, when I first started having sex, I didn't consider ass play as something to include during lovemaking. It just never occurred to me that there was any sort of pleasure to be derived from that particular region of my body. Then a girl I was seeing threw me a curveball during a blowjob, maneuvering up underneath me and sticking her tongue in...

An Ordinary Man's Life Ch. 39

by FrankjrBauer on Sep 19, 2017
Romance

This chapter was kindly edited. Great job. Thank you Mike. ***** It took almost a month after the sex party before Dan, Jack and Peter finally came to the conclusion Todd had no intention of breaking the rules of their friendship. Todd saw them visibly relaxing and their observation what he was doing waned. They had realized Kate and Megan kept him sexua...

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...