Cheating Anal Stories

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I Met s Lady Buying Cigarettes

by Mysteria27 on Sep 16, 2017
Anal

What a night! I was having flashbacks from the night I had just had. I felt like I had been to hell and back. I was hung over and not feeling good at all. I wasn't sure if I had a dream or if what had just happened really did. My body felt like it wasn't a dream. My heart told me it wasn't a dream. I was hanging out with my buddies at our favorite watering...

Dear Diary #01

by ceb35 on Sep 12, 2017
Anal

Dear Diary. Wednesday. Today was an ordinary day I suppose. I went to work (a little late since I am the boss). Now you need to understand that I am 46, and curvy with graying waist length hair that I wear in a single braid down my back. I prefer to wear short sleeve blouses that only hint of the 36D breasts underneath. During the workday my husband and I...

Dawn's Orgy Ch. 03

by SplitLicker69 on Sep 16, 2017
Transsexuals & Crossdressers

Dawn always tried to invite new exciting guests to her annual orgy. One year she invited beautiful transvestites. Another time she invited female body builders. Over the years, she provided male and female strippers, drag queens and porn stars. This year topped them all. Nobody spiced up the gathering more than the beautiful transsexual sisters, Michelle and...

Almost Caught

by sexxobject on Sep 14, 2017
Anal

A boy named Bubba took my anal cherry. I had met him at a church youth group. My parents made me go. I was also going out with another boy at the time. Bubba and I had been flirting, but the other guy beat him to the punch and asked me out first. Since Bubba had only been interested in going out with me as a means to get in my pants, the other guy loved me...

Can't Rape the Willing Ch. 04

by MadisonMaven on Mar 17, 2020
Anal

I can't believe I told him yes... He's going to take my anal virginity! My mind is reeling, my pussy soaked and throbbing, as the much-older man I've been chatting and fantasizing with online, gets ready to make another fantasy come true. He strokes three fingers in and out of my ass, twisting them, stretching my tight backdoor, still pinning me to his che...

First Oral, Anal, Spanking Pt. 03

by FrankHarris1 on Dec 24, 2019
Transgender & Crossdressers

It was getting late. The two lovers lay entwined on the soaked, tangled sheets, sharing another tumbler of wine. James played idly with Dana's cock and balls; the latter leaned over and delivered a succession of feathery kisses to his lover's groin. Dana was uncharacteristically talkative; the evening's encounter seemed to have freed him of much of his natur...

The Boss Pt. 02

by SammySS on Sep 28, 2020
Anal

Boss pulled his cum covered cock out of my ass, my legs still shaking from his hard pounding. "Go get something to clean me up," he snapped. "Hey, your husband always carries a handkerchief with him doesn't he? Go get that from him," he said. A mean, wicked look in his eye. "Yes sir," I responded, my ass still over full with his cum, as it trickled down t...

Feeling Good

by DFWBeast on Sep 18, 2017
Loving Wives

Author's Note: This is a pretty simple betrayal and recovery story. However it's unique for me since this will be the first time I've attempted to write a graphically explicit sexual encounter. It's also the first time I've ever used one of the ladies found here on Literotica as one of the main characters. My thanks to Debbie for her very candid replies, the...

Kinky Little Clary Ch. 04

by MTL17 on Aug 20, 2019
Celebrities & Fan Fiction

Disclaimer: I do not own Shadowhunters. I do not make any money from the writing of this story. ***** Clary Fray would have described herself as a little kinky and more than a little obsessed with Izzy's butt before she took her girlfriend's anal cherry, but afterwards it was just embarrassing how consumed she became by everything to do with that big beaut...

Cuckolded by Disgusting Neighbor Ch. 06

by vyasya on Sep 12, 2017
Loving Wives

Continued from Chapter 5; please read earlier chapters to get the context. * I couldn't understand if that was a smile or smirk. However, I could sense that she was deriving great pleasure in feeding my insecurities. I pushed the thoughts out of my mind as my tongue ravished her vagina lapping up their mixed juices until she could no longer withstand and u...