Gloryhole Cuck Stories

2,001 results
Orientation
Length
Source
Infinite Scroll

A New Adventure... Ch. 02

by johnjinglez1 on Jun 6, 2018
Transsexuals & Crossdressers

This is a continuation of my "Sex Diary." For the better part of a year and a half I decided to try some new things in the world of CD / TS / Sissy boys. All stories are 100% real. *** After my first three encounters with TS and CD's left me feeling unfulfilled I gave it up for a few months and figured it just wasn't for me; I went back to having sex with...

The Perks of Being a Podcaster Pt. 14

by MrMaxLord on Oct 30, 2018
Celebrities & Fan Fiction

All of the following is complete and total fiction. Not a word of it occurred, nor would it. The Perks of Being a Podcaster by MrMaxLord (MF, MFMF, oral, cons, gloryhole) Chapter 14: Anna Kendrick ***** "Now folks, I bet you're wondering how we top last week's guest," I said to the crowd. "I mean, we had Alexa Bliss. We had the Raw Women's Champion, th...

Jennifer Likes Her Coffee Black Ch. 02

by rodryder44 on Dec 11, 2018
Loving Wives

Postcoital Bliss Jen sent her black lover home and is in postcoital bliss as she discusses the evening with her cuckold husband and tells him what he has to do to ensure she is the best slut in town. This chapter has references to interracial sex and ends with throat fucking the loving wife. Be forewarned if you have problems with cucks and IR stories....

Claire's Appointment with Mr Strong

by paulb85 on Sep 17, 2017
Fetish

My wife, Claire, and I had been married for 10 years. We were in what I thought was a normal happily married relationship and, although our sex life was not as plentiful as it had been in the first few years we both seemed to be happy and reasonably satisfied with our lot. This didn't mean that we did not occasionally fantasize and share our erotic thoughts...

CD Cum Slut

by pervasive1 on Sep 16, 2017
Transsexuals & Crossdressers

I shave my body smooth and get dressed up slutty in heels, nylons, garters, panties, short skirt, tits, wig, makeup, fake nails, etc. A ripped punk rock tank top and spiked belt complete the whore look. You pick me up off a street corner near my place, I hop in your car and before we say anything, your cock is out and its buried balls deep in my throat. We...

Married Lexi Gets Her Man...Again

by HotwifeLexi on Apr 13, 2020
Loving Wives

"Soooo you gonna fill me in funny girl" That was a text I got from Robert at about 3 am the night/morning after I asked him not to respond to my good news. Sheesh. So desperate. Lol If you haven't been reading along with the journey of Lexi (that's me! Hi!) and my husband Steve toward a cuckold marriage, there are three chapters waiting for you. Hurry up!...

Be Careful What You Wish For

by NonGenericBrand on Sep 19, 2017
Group Sex

Had we known it would have ended up like this, would we have still gone? Probably not. We wouldn't have been horny enough to think it would be fun. We would have thought about things too sensibly. We probably would have decided to just do something else kinky. I would have missed a chance to see my girlfriend completely used in the dark hallways surrounding...

Erotic Games Ch. 04

by jealouscuck on Jul 24, 2018
Loving Wives

I was totally taken by surprise when Meredith had me put on her panties and bring her to orgasm orally. Even more surprising than that was when she had me jack off into her thin panties and cum in them. Then she instructed me to go to sleep. I was intending to fuck my sexy girlfriend as long and hard as I could. I was that turned on. I guess when she told me...

The Two-Month Break Clause Pt. 03

by TheBiGuy on Apr 22, 2019
Loving Wives

This story should be read in sequence. Please read the other two stories first. This story contains bisexuality, femdom, humiliation and cuckold scenarios. If any of these offend you, please move on to another story. I decided to place this in LovingWives as I was instructed this is the most appropriate place for this story. ***** After walking past, Natal...

Madam Molly Pt. 01

by corduroysissy on Feb 6, 2018
Transsexuals & Crossdressers

It all started in a chat-room, "Closet Sissyboys." Jesse had been spending a lot of time in chat-rooms in the six months following his divorce. He wasn't looking for love, he just liked to drink and have cybersex while jerking off with corduroy. Yes corduroy. Jesse had a corduroy fetish his whole life and now at the age of 36 it was stronger than ever. He...