Accidental Penetration Sex Story Stories

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Accidental Gangbang: Blindfold Orgy

by silkstockingslover on Jan 20, 2020
Group Sex

Summary: Before the wedding they have a 6-person orgy at the church. Thanks to: Tex Beethoven for editing and to xxx who requested and sponsored this sequel. Note 1: This is another sequel to 2014's Accidental Gangbang (which was originally intended as a stand-alone story, but after over a million reads and lots of requests, I went back and re-read the rat...

Your New Life

by Whatsisname0 on Apr 22, 2025

You were Mike Doe, a 21 year old college student living with your parents. This was until you were shot, when a burglar tried to break into your home. At the end you closed your eyes, and felt your life drain from you. “Time to wake up sleepyhead”, said an unfamiliar voice. You slowly open your eyes to see a young woman in a chair in front of you. You start...

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Petition for Exchange of Sex

by Decayed Angel on Sep 16, 2017
Letters & Transcripts

Petition for Exchange of Sexual Congress State of Texas County of Harris Court Fifth Circuit Sexual Practices Docket No. Fifty two forty five (5245) In re: Exchange of Sexual Congress Name of Petitioner: Justin Aaron Fitzgale Name of Petitioned: Janet Elaine Siewalls From: Initial foreplay To: Final presumed mutual orgasm(s) Petitioner makes t...

Accidental Bisexual

by FiftySomething on Sep 12, 2017
Group Sex

Author's Note This story stands alone, but it is a continuation of "Accidental Threesome" in the Group Sex category. That story was also posted under a different title in the Loving Wives category, but the environment there is toxic. Even though this storyline fits the LW category I won't be posting there anymore. ***** About a month had passed since the...

A Legal Romance

by Decayed Angel on Sep 1, 2017
Humor & Satire

"I tell you Angie, it was the most romantic thing anyone has ever done for me," Christine said excitedly between mouthfuls of Caesar Salad and sips of Chardonnay. "Well, tell me all about it girl," Angie replied. The two women were sharing lunch on the one hundred and fifty second floor of the Liberty/Porterfield Building, in the most expensive restaurant...

Five Positions Two Loads

by lynntg0444 on Oct 21, 2019
Transgender & Crossdressers

It took six months from my first blood test until surgery was prescribed. Unfortunately this was only a slightly feminizing surgery - I was diagnosed with prostate cancer, and the simplest solution was a radical removal of the whole organ. Needless to say, this was extremely depressing as I had become accustomed to mind-blowing orgasms through prostate stimu...

Accidental Anal

by FiftySomething on Jan 15, 2019
Group Sex

A sequel to "Accidental DP"... We still had a few quickies and I enjoyed a blowjob at least once a week, but in the two months since my wife had collected our two cocks in her pussy at the same time, another double pussy penetration was all I could think about. Since then whenever the three of us got together — me, Mike, and my voluptuous and sex-craved bet...

Twenty-One More Questions

by silkstockingslover on Jan 1, 2019
Reviews & Essays

Summary: Jasmine responds to the most frequent questions asked by readers. Thanks to: Tex Beethoven, Wayne, and Robert for editing this essay. This isn't really a sequel, although it's a second part, as it addresses questions I didn't answer in 2017's Twenty Questions. 21 More Questions After 2017's 20 Questions, I received many more questions. I have n...

My Husband & I Get Kinky Ch. 01

by Davie46 on Sep 11, 2017
Fetish

John and I were married many years ago, and both of us were virgins on our wedding night -- sure a little heavy petting before the marriage -- but that was all. In the first few years, it was pretty much just missionary position, but I rarely found it pleasurable and never had an orgasm from vaginal penetration. John's cock is pretty small, certainly by porn...

Our Awakening Fantasies Ch. 2

by rickandyoko on Sep 12, 2017
Loving Wives

As we drove home, I could not keep my eyes off of Yoko. She obviously was not ready to discuss our experience, as she turned on the stereo and hid behind her sunglasses. The drive home took an hour and a half, and she hardly spoke at all. The sex that night was incredible. As soon as we got home she headed for the shower, leaving a trail of clothes in her...