Sissy, Heels, Cuckold Stories

88,578 results
Orientation
Length
Source
Infinite Scroll

Sheila and Penny

by Sheila_TSSub on Sep 19, 2017
Transsexuals & Crossdressers

Part 1 I had been upstairs that morning doing my chores. I was dressed in a cute little yellow summer dress and leather heels with 4" wedge heels. When I came downstairs I found Mistress Tina (my wife) and Princess Gina (our daughter) in the den. There was a man there that was unknown to me. "Come here." Tina commanded. I went in and knelt beside her cha...

First Time Cuckold Ch. 04

by Angelscuck on Sep 14, 2017
BDSM

Oscar could smell her vaginal juices from his proximity kneeling between her legs. Her delicious cunt beckoned his waiting mouth. "I do need to warn you dear that I'm a squirter!" Bea cautioned. "Once my floodgates are opened its head for the high ground!" "Let it pour!" Oscar replied as he buried his face deep between her thighs and tasted he sweet guim....

The Sexy Cuckold Couple Pt. 14

by cuckcpl4play on Sep 26, 2017
Fetish

Part 14 Pool I As we departed the room, I was utterly shocked that Master was in fact going to make us walk through the hotel as we were. He walked with his slut in front and I brought up the rear, but following closely in tow. I kept my head down but could feel the stares and after walking by a large group I heard the individuals bellowing at our predicame...

My Teasing Hotwife Ch. 03

by footslave85 on Mar 25, 2019
Fetish

Part three - the dreaded choice My wife and Mistress is now dressed beautifully and ready for a fancy meal and a few cocktails at a rather expensive restaurant and bar. I met my wife in our spare bedroom where I immediately see what has been laid out on the bed. There are two outfits, one is my nicest blue suit with a new shirt and tie that my wife has obv...

Sam's Story Pt. 08

by Shadykingcolor on Jan 29, 2020
Fetish

As Mel and Steph leave the room only my caged cock is on my mind. It's burning like mad and balls are in agony from the cage. I try to massage my balls where the base ring is applying the most pressure. But having no joy. I get off of the bed, maybe a shower will help. I think to myself. As I start to leave the room I noticed a dildo on the floor. It mus...

My New Life as a Cuckold Ch. 02

by CuckHubby1 on Sep 14, 2017
Fetish

We got home from our night of fun and I couldn't stop thinking about it. Was I gay now? Bi? What changed so much in my wife that now all she wants is big cocks? I had a knot in my stomach and had a hard time sleeping. I kept sleeping fitfully until my wife asked me if something was wrong. "I'm curious about our sex life now," I confessed. "Are you not happy...

Becoming a Sissy Cuckold Ch. 01

by Pantieslave on Mar 27, 2019
Fetish

Beth and Dan were married very young, just 20 years old each. As such both were virgins when they married. Beth wasn't an outstanding beauty but very attractive with a nice body and very nice breasts, 36D. Dan, on the other hand, was rather feminine looking and wore his hair long, in a ponytail. Being slightly built, on more than one occasion he was mistaken...

Wife in Control Ch. 08

by wifetoy on Sep 25, 2017
Fetish

This is the eighth and final chapter of my wife's fulfillment of the punishment poem offering humiliating punishments to atone for my inability to control my orgasm. Please read the earlier chapters for the full poem and the humiliations I have been forced to endure because of my failure. I adore and cherish my beautiful wife. She not only tells me how much...

Types of Cuckolds

by cuckwhofucks on Sep 14, 2017
Reviews & Essays

What does it mean to be a cuckold? It actually means many different things to different cuckolds. But let's start at the beginning: The truth vs. the Truth. The Truth, or an absolute Truth, is actually unnamable, or rather it exists, but when you try to interpret it and put words to it, it becomes one of very many truths, as many truths as there are peopl...

Jasmine Fucks My Wife

by cuntenslaver on Sep 12, 2017
Transsexuals & Crossdressers

Hello, my name is Tim. I am a 30 year-old married man. I have been married for five years to my wife Danielle. She is an absolute beauty of a woman. I remember when we were married, I felt like I was the luckiest man in the world. Since I am no hunk myself, standing at just five foot six and extremely lanky, I felt like I didn't deserve such a nice, gorgeous...