Anal Surprise Stories

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Chronicles of the Special Stretch

by AngelPie4Mongo on Sep 14, 2017
Anal

CHRONICLES OF THE "SPECIAL" YOGA STRETCH My boyfriend/ live-in lover/ best friend of three years had mentioned anal sex many many times. We had tried it 2 or 3 times and had to stop because it was VERY painful for me! A few weeks ago, I had a short discussion with him that I didn't know if we'd ever be able to have anal sex unless I went through some "anal...

The Fifth Wheel

by LaceyDresser on Feb 6, 2018
Mature

When I originally wrote this it was intended to be a two part narrative of our second foursome with David and Cindy. Then I decided to condense it for the sake of brevity. I hope you enjoy, and comments are always welcomed as long as they are constructive. Thank you. ***** Our second foursome with David and Cindy was finally upon us after numerous cancella...

One Gloryhole Outside Breeding, Kentucky

by targetthyself on Nov 24, 2018
Miscellaneous

Somewhere, in the cosmos, lies the truth of our existence. It's siren song drives us forward, forward into the unknowable reaches of space, and time. Hoping to boldly discover their secrets. What is it about the unknown that drives us so? What is the appeal of knowing? Is it the value of the knowledge we will gain? Is it the thrill of the risk we take? Or is...

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The Good Neighbor Ch. 03

by Marijke on Sep 13, 2017
Erotic Couplings

Maggie's predictions proved true; David wrote five best sellers in the next three years. They had sex at every possible opportunity but decided not to actually move in together. Once in a while they would spend the night at one house or the other and weekends in his cabin happened at least once a month. Maggie was happy with this arrangement but she knew tha...

Surprise!

by downulit on Sep 14, 2017
Anal

It all started with a text message I received from my wife. "Don't be late home I have a surprise for you." Well how was I expected to get any work done or concentrate for the rest of the day with a message like that? I sent a reply back trying to get some information out of her but I got nothing. I love my wife, but she is not big into surprises, so this ha...

Anall Sex Can Be Fun

by wcf on Sep 13, 2017
Anal

This is one of a series of stories that are true life experiences my wife and I have shared. My wife and I have had anal sex a few times. Sometimes enjoyable, other times not so enjoyable Our first time was before we were married. I was trying to get her to give me a blowjob, or at least lick my cock. Do to her strong catholic background she could not brin...

First Ass

by Tepin on Sep 19, 2017
Anal

Linda and I met about a month ago at a friends party, we had both been drinking, but weren't really drunk and we just hit it off right away. We left the party around 2am and she ended up going back to my place where we had some of the hottest sex I'd had in a long time. I usually don't pick up girls at parties, and wasn't really looking for one that night, b...

Someone Else's Toys Ch. 01

by pjhughes25 on Sep 14, 2017
Toys & Masturbation

It was a crisp fall evening, just about the point where winter is going to start. My girlfriend, Katherine or Katie for short, and I were visiting her mother in Maryland. Here's a little background on Katie and myself. Katie is 21 years old and 5' 10" tall. She has straight brown hair, with gorgeous brown eyes and is slightly above average with weight. Her...

Jessica, Anal Bitch Ch. 04

by ifry on Apr 22, 2020
Anal

Friday after work, Jessica decided she'd had it with working from home. She decided she would make the drive up to visit her parents. She felt it was time for some human interaction...the kind that didn't involve getting off any number of cocks, not that she minded it. She discovered that she had a craving for cock that could only best be described as the b...

Mariella's Bottom

by Otazel on Sep 13, 2017
Anal

With apologies to anyone whose online username I have accidentally stolen. 'Fantasy is fun and porn makes me playful'. Mariella smiled to herself at her own silly thought as she settled into her chair, adjusted her bathrobe a bit more comfortably around her nicely rounded frame, and switched on her computer. It was her habit, at least two or three times ea...