Sissy, Heels, Cuckold Stories

88,578 results
Orientation
Length
Source
Infinite Scroll

At Home with(out) Abby

by hagendaz on Sep 17, 2017
Loving Wives

When Abby walked in the front door my whole world stopped. The woman I adored was home. As always she looked more beautiful to me than I could imagine any woman ever being. All night I had been waiting to for her arrival. I had been anticipating the chance to hold her and kiss her after what had been a long day without her company. She stood in the doorwa...

My New Life as a Cuckold

by CuckHubby1 on Sep 11, 2017
Fetish

I didn't start out as a cuckold. When me and my wife decided to become swingers it was going to only be single women since my wife is bisexual. We did that a few times. It was hot, but never memorable. Then we decided to try a full on swap with another couple. The first couple of times were OK. The other couples were just all right looking and the spouses ne...

Betrayed Ch. 02

by AngelCherysse on Sep 19, 2017
Transsexuals & Crossdressers

Chapter 2: Shop 'Til You Pop The sex was torrid and went all night. I worshipped every inch of her magnificent body with my lips, tongue, fingertips. She did the same to me. I took her from behind, entered her doggy-style. I fucked her pussy with long, languid strokes even as I was stroking her meaty clitty with one hand. I willed her to cum, dared her not...

Easy and Hardy

by Tiberius_Daniel on Aug 6, 2019
Loving Wives

Don't miss this modern fable. It's a fictional story, has nothing in common with reality. Please don't suppose anything; I give you only original stories. For local flavor, I used English and London words and phrases. (Example bare means a lot, fag= cigarette.) ***** First chapter For today we have two couples who lived in Chiswick, where rents are high...

Discussion with a Wife of a Cuck Ch. 01

by wantyou on Sep 12, 2017
Interracial Love

This is what I believed to be a true story of e-mails that passed back and forth between a black man who was a friend with a white guy that wanted to see his white wife get fucked by another man. As it turned out his wife and he talked about it one night and she told him she had always had this fantasy of fucking a black guy. So if they were going to try the...

Born to be a Cuckold

by W_MA_DWM on Sep 11, 2017
Fetish

This story starts off slow, however it does lead into some very explicit sexual scenes. So be patient -- it gets hotter. It all began over twenty years ago when I met Lizabeth, the girl who became my wife. I had no idea what Mother Nature's plan was for me in those early years. I did realize that I was different than the other boys and felt that I neve...

Wife Turns Slut For Husband Ch. 02

by Dirty Slut on Sep 26, 2017
Group Sex

The Worm Turns Intro: As you remember in the last saga my husband had begged me to turn him into a cuckold. As things turned out I found out that he wanted to see me fucking other men, and not just any men, but black men with big black cocks. It was a torturous decision for me, but as I loved Billy so much I finally made contact with a black man on Billy’s...

Letter from Iddlesleigh Harbor

by justincbenedict on Sep 9, 2019
BDSM

Dear Shoeblossom-- I am a townie bitch from a crappy beach village, and I snared a rich little piglet, and I just recorded one of our more pitiful conversations! Stephanie "Stalki" Sendack "I don't think you did that badly, Crates. You actually seem to howl more when I cane you, you know." "Stalki, it feels so marvelous when you stroke...oh it's so nice...

English Slaves Submit to Dom

by royalsuite on May 4, 2020
BDSM

Weekday Evening Plans It was a regular weekday evening in May in Sussex county, south-east England, UK. The weather was turning barmy and evenings were lasting that bit longer indicating the arrival of summer. Thirty-two year old Sara Jones was on her commute home on the train thinking about her work day and wondering how Ken's (her 35 year-old husband) day...

Coming Home, Coming Out Pt. 09

by EiryCGar on Jun 1, 2020
BDSM

Author's note. As this saga continues, aspects of sadism, slavery, cuckoldry, lesbianism, denial and general bdsm are explored. All characters are figments of the author's imagination, and all characters consent to every aspect of the activities described. As always, all characters are aged over 18. Chapter nine. Saturday morning dawned, and Sara slipped f...