First Time Unplanned Chuckold Porn Stories Stories

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Penny's Promiscuity Ch. 07: Complicity

by JennyGently on Sep 26, 2017
Loving Wives

The buzz of excitement that followed my first Official Hotwife Date was almost tangible. Though my affair was well over a month old, Monday evening's date had been the first time my lover and I had met with my husband's full knowledge; the first time he had fucked me with Pete's not-entirely-unreserved-but-helplessly-excited acquiescence. After over a yea...

Cuckold Jack

by stoner94105 on Jul 24, 2018
Loving Wives

When I returned from lunch and saw the large mailing envelope on my desk I knew exactly what it was. For just the briefest moment I hoped that perhaps it has been sent to me by mistake, but I really knew it wasn't. The real question was who sent it to me. I sat down, picked up the thick envelope and examined it more carefully. The envelope was addressed...

Penny's Promiscuity Ch. 20: Phone

by JennyGently on Oct 10, 2017
Loving Wives

Normality! Sweet, contented normality! The next few days passed as if the previous tumultuous months hadn't happened. My husband Pete and I got up together, had breakfast together and went to our separate places of work where, for the first time in weeks, I was able to concentrate properly on my job and not my impossibly complicated private life. We had di...

A Conspiracy to Deceive

by enovelist on Sep 16, 2017
Novels and Novellas

Part II of the Barry and Carol story As way of introduction, this is the sequel to "A Conspiracy to Commit..." It would be to the reader's advantage to have read that first segment of the Barry and Carol drama. "A Conspiracy to Commit..." That story was my first submission to Literotica and I was very pleased with the response that I received to story. Bo...

The Black Power Virus: Multiplier

by amb_anonymous on Feb 6, 2018
Interracial Love

Welcome back BPV fans! Here is another stand-alone story. If you hadn't noticed before, impregnation plays a major part in the story. This story is mostly focused on it. Series Note: I understand that not everyone loved the futa stuff in the main chapters, but I told the story the way I wanted to and finished that arc. There won't be any more of that in th...

Bed and Breakfast Hotwife

by donaldelliott11 on Mar 9, 2020
Loving Wives

[Note: The hotwife in this story is, well, a wife, right? That means she has a husband. When she gets hot, he becomes a cuckold. You following this, Annony? Get over it, or read a different story. Oh, yeah, one more thing -- BTB is a fetish and has no place in Loving Wives.] *** Tracy and Don Elliott, empty-nesters in their late 40s, supplement their incom...

Penny's Promiscuity Ch. 50: The End?

by JennyGently on Mar 31, 2020
Loving Wives

Chapter Fifty They say all good things must come to an end. That might be true, but sadly the same isn't true of all bad. Although in hindsight the outcome was predictable, its beginning came from an entirely unexpected direction and at a time when everything else in my life seemed to be running smoothly. I should have known it was just the lull before th...

Jan's Boudoir Photo Shoot - The Aftermath

by cuckold308 on Jun 16, 2020
Interracial Love

My original desire was to have an erotic yet elegant photo album created for Michael, my significant other, as a surprise birthday present. Michael loves and adores me, treats me like a goddess, so I really wanted to do something special for him this year. However, what happened at the photo session was totally unexpected and unplanned, the furthest thing...

Filling the Glass Ch. 01

by mdp_2004 on Sep 14, 2017
Loving Wives

At times throughout my life I've played both sides of a tried but true metaphor. It's the one about the glass of water and when my glass is half full, I'm usually happy with myself and my lot in life. I focus on what's important and go about my business without worrying about lives surrounding me. When my glass is half empty, I am unsatisfied with my life an...

Penny's Promiscuity Ch. 22-29

by JennyGently on Oct 9, 2018
Loving Wives

Author's note. After a long break and in response to many recent messages, Penny is back! The whole story is being turned into full length novels so the style is slightly different but it's really Penny and it's really me writing. I hope you still enjoy it. Chapter 22 "Can you see?" the young radiologist asked, running the square plastic sensor over my lo...