Anal Stretching Stories

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Infinite Scroll

Buttfuck Buddies Ch. 01

by ZenZerker on Sep 16, 2017
Anal

Author's note: This is a work of fiction. All characters are eighteen years or older. Don't expect realism and you won't be disappointed when you don't find it! Enjoy! ***** Cursing under her breath, struggling with the lock until she managed to get the key to turn and the door to open, Ashley let herself inside her boyfriend Josh's apartment. She knew th...

A Is For Anal

by velvetpie on Sep 13, 2017
Anal

Inspired by Sue Grafton's alphabetical series. "So?" Betty Simmons stared across the lunch table at her friend, Carol Whyre. Carol had taken a bite of her egg salad sandwich and was chewing thoughtfully, smiling as she purposely ignored her friend. "So?" "So, what?" "So what's it like?" Carol took another bite, still smiling. "What's what like?"...

Transsexual Journey 02

by walterio on Sep 19, 2017
Transsexuals & Crossdressers

DAY TWO OF THE CRUISE TO BARCELONA Jay woke up leisurely on Sunday morning and lay in bed for a while thinking about his encounter with Caridad the night before. He was still somewhat shaken by his willingness to have sex with a transsexual but more so, that he had enjoyed it so much. She was so damn pretty and shapely that it had been way too easy. Her bod...

The Warlock & The Wizardess Ch. 08

by ZenZerker on Sep 18, 2017
Sci-Fi & Fantasy

Author's note: This is a work of fiction. All characters are eighteen years or older. This story features anal sex and group sex, so be warned in case you're not into that sort of stuff. Consider this just a silly, smutty parody of a few fantasy cliches. Don't expect epic tones or anything even vaguely resembling seriousness and you won't be disappointed whe...

Wet Encounters Ch. 12

by BlackJackSteele on Dec 2, 2019
Loving Wives

INTRODUCTION TO READERS WET ENCOUNTERS is a novel-length story of love, lust and betrayal that takes place on a tropical Pacific island during the second half of the twentieth century. It's seventeen chapters pivot around a single event that takes place when two people are forced to take refuge in an abandoned cabin when they are cut off by rising floodw...

Sweet Morning, Sweet Ass

by chubbycute27 on Sep 11, 2017
Anal

As I woke up, slowly feeling my senses come back to me, a slight fuzzy light hitting my eyes, a slow ringing in my ears, a bit of a parched throat, I tried to get a sense of my bearings. I hate mornings like this. So discombobulated in those first few moments, needing to piece together the details of last night. Clearly I had had to much to drink, clearly I...

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...

Maestro Dominates Marie's Ass

by AuntClimax on May 20, 2019
Anal

The best anal I ever had happened the same afternoon Maestro fucked me in the stairwell. We returned to our hotel room, a bit tired and weary from repeated bouts of fucking and eating. The pool party scene continued on, but we skipped the drinks and dance music in favour of a little SNAP. Sex and a nap - that's what one of our former work colleagues called...

Roberta & Patrick's Next Bet Ch. 02B-1

by BONNIEBREA on Sep 15, 2017
Loving Wives

This story is presented in a total of five parts. There has been chapter one, and a two-part chapter 2A. This is the first part of chapter 2B, with a second part still to come. I think the story hangs together fine on its own, but I think having read the stories Roberta & Patrick's Bet and Roberta's Bet will increase your enjoyment of this story. The story i...

Anal Orgasms

by penbeatsword on Sep 26, 2017
How To

Okay, from a guy perspective, I love doing anal. Is it because of the taboo thing? Probably somewhat. But it also feels so damn good! Mostly, I've been the penetrater, but lately I've also been getting the urge to get fucked myself. I've never been able to stimulate my prostrate from the inside (had my partners' fingers and a dildo up there before to try it)...