Cuckold Sissy Stories

12,909 results
Orientation
Length
Source
Infinite Scroll

Pretty in Pink Ch. 03

by jealouscuck on Sep 18, 2017
Transsexuals & Crossdressers

After our trip out of town, Jessica and I had an even better sex life, if that was even possible. One night we ate out as man and wife and she made me stop at a dark, lover's lane type place. I had not really noticed before, but she had dressed rather conservatively. I just assumed that it was some of her new work clothes. When we got parked, she said, "Oh,...

Alternate Reality Ch. 02

by grgy56 on Sep 12, 2017
Transsexuals & Crossdressers

"Shit! Shit! Shit!" I screamed to myself. "How the fuck am I supposed to get out of here?" I am stuck in a virtual reality scene. I am my avatar, Krystal. The developers of SIM: Slut City offered to me a try-out of their new VR body suit. After putting it on I was completely engulfed and only aware of my life-like surroundings within the game. Unfortunately...

Bad, Bad, Boy

by AfroerotiK on Sep 16, 2017
BDSM

Working for an advertising agency has its advantages. At the drop of a hat, for barely any reason at all, there's cause for an after work get together with free-flowing drinks for all. On this particular Friday evening, there was reason for celebration because Michael Shield's company signed a major client and glasses were being raised all around Schmidt's B...

A Slut's Triangle Pt. 15

by Kantarii on Sep 19, 2017
Transsexuals & Crossdressers

My whole body is trembling as adrenaline courses through my veins. My ribs are hurting and I'm scared. Face down on the pavement, it's everything that I can do to shield myself from Kryss kicking me again. Just hearing Brenda's voice echo through the night air gives me a glimmer of hope. There are plenty of things in my life I take for granted, but my frien...

Paying Rent Ch. 03

by JailBird Dreamer on Sep 16, 2017
Transsexuals & Crossdressers

I woke up in the morning, still on my mattress on the floor. My boy pussy was on fire and my panties were soaked with lube and cum. I went to our cell's toilet and let out a stream of my new master's cum. I couldn't believe I still had that much in me! I looked around for Jermane, but he wasn't in the cell. I figured he must have gone to his job in the kitch...

Sissy Plays the Game of Thrones

by SissyKelly on Dec 1, 2017
Celebrities & Fan Fiction

Kelly Waters, fucking Waters I thought to myself as I shook my head. I think the worst part of being a bastard is knowing you could choose any last name, but having it dictated still by birth. I knew not who my parents were, in fact I only knew I was Kelly Waters thanks to the man who raised me, Lord Petyr Baelish. I was born in his house, his whore house,...

The Meeting - His Point of View

by bifemdom81 on Aug 29, 2017
Group Sex

We talked about finding a third person to join us for awhile. We agreed that it didn't matter if it was a man or woman, just so long as we saw a picture and we met at a public place prior to the encounter. We posted a few ads on the internet here and there but proved to be pickier than we originally thought. We finally decided to settle on a man - young, in...

Bird of Prey Ch. 05

by Sputnik57 on Sep 11, 2017
BDSM

Gordon watched the pencil-skirted Penny strut into the house with her attaché case, drop this into a chair and strip. She smiled broadly as she returned across the lawn, naked, as though this were routine. Gordon's back stung like hell but his cock rose as even the scent of the three naked women took control of him now. The assertive blonde smiled down at th...

Brian's Sleepwalking Adventure Pt. 04

by SirBosk1 on Sep 15, 2017
Novels and Novellas

This story is based on what may be an urban myth from my college days. A fraternity brother told me about the incident after my own adventure, described in my story "Pledge Class Payback" so I believe it to be true. When I asked about it, no one could remember the actual names or years or the fraternity. However, it fed my imagination and inspired me to writ...

Women in the Workplace Pt. 02

by MissKateKees on Sep 19, 2017
Exhibitionist & Voyeur

The sound of a scuffle returned Laura to business, Miranda and a group of girls were struggling to drag Ryan onto the stage. He was wild with anger, flailing his arms and shouting in protest. A primitive barbarian. Laura walked over and simply threw her heeled foot into his groin. He went down hard and was dragged long the stage to begin proceedings. "Somet...