Cuckold Sissy Stories

12,909 results
Orientation
Length
Source
Infinite Scroll

The Sleepover Pt. 01

by RoyWilliams on Sep 18, 2017
Group Sex

I am a married black man, early 50's. This is my story; a reminiscence of real thoughts, feelings and events of my life. My decision to write it was born out of a private personal need for erotic expression - an outlet for sexual frustration. My decision to share it is an extension of that expression, but not an invitation for anyone else to use it in whole...

I Chauffeured My Wife and Her Lover

by EllisEmmitt on Sep 25, 2017
Loving Wives

From the dark corner of the bar, I watched as my wife, Sarah, was chatted up by a strange man. They sat close together in the booth, and Sarah was clearly enjoying his attentions, laughing at his jokes, and frequently putting her hand on his when she did so. Once every few minutes or so, she shot a glance in my direction. I was wired tight with nervous ten...

Indian Wife Gone Bad Ch. 06

by aurelius1982 on Sep 26, 2017
Loving Wives

I woke up to the sound of my cellphone ringing. With half-open eyes, I reached for it and answered. "Hello?" I said. "Hello Arun, this is Dev." the voice from the other end was that of my Boss. "Yes Dev? Tell me." I said. "Tell you? You tell me!" he sounded annoyed. "Where the hell are you? We are supposed to go on that big sales call together!" "Oh, y...

What Happened To My Life Ch. 03

by vastiesmith on Sep 17, 2017
Loving Wives

I couldn't believe it. I was completely naked lying on the bed in the hotel room that Ray had reserved. Ray was naked too and kneeing between my open thighs. His cock was only a foot or so away from my waiting and oh so very wanting pussy hole. I said, "Come Ray. Oh come on and fuck me!" He didn't move. I said, "What? What's wrong baby?" Again he didn't mo...

He Fucked My Girl Ch. 09

by xleglover on Sep 25, 2017
Loving Wives

Every now and then all three of us went out. Part of it was my need to be with Jen. I was seeing less of her (since she was with Ricky a lot), and I missed her. Of course, part of it was my need to see them together. I was so conflicted about this. I guess I gave her mixed signals. She saw both my angst and excitement. Often we sat in a booth, with Jen bet...

Cocksucker: Master & Mistress

by silkstockingslover on Sep 25, 2017
Transsexuals & Crossdressers

Summary: Crossdressing cocksucker returns home to one last surprise You do not need to read the first parts to enjoy this story of a straight man who gets submerged into the drag queen world of San Francisco. (but obviously it helps). In case you are curious how this straight married man got into this predicament here is a brief summary of the first six ch...

Marabogo: Cuckold Island Ch. 02

by eeric on Aug 29, 2017
Fetish

"Hold the elevator please." Megan and Joshua heard a woman's voice just as the elevator doors were about to close. Joshua quickly held out his arm to so the doors wouldn't close. Through the small crowd of newly arrived guests, they saw a very scantily clad and rather chubby young woman coming at them. She was slightly jogging, her huge chest and big belly...

That Phrase... Sylvia Ch. 02

by mikoli5763 on Sep 18, 2017
Loving Wives

Due to the lateness of the hour, my internal clock let me sleep till 7 that Saturday morning. I was as quiet as I could be as I left the house, picked up my car from the neighbors, went to the gym, showered there after my workout, stopped at a little diner, and went to the main branch of our bank which, unlike the branch near the house that only opened the d...

The New Client Ch. 01

by TuWatchu on Sep 19, 2017
Loving Wives

********************************** This is a revision of the first story I submitted to Literotica. This is the first of series with Lynn and her cuckold husband. The main themes of my stories involve wife infidelity and cuckolding, voyeurism, etc. Your comments and suggestions are appreciated. *************************** I have always had voyeur fantas...

Reunion Ch. 04

by amofiga on Sep 26, 2017
BDSM

For Melissa and Gary, the week that followed the evening at Jason and Karen's was filled with more sex then they had shared for a long time. They had more of every kind of kinky sex in those few days than they had for the previous year. Gary's libido had been kicked into overdrive and he had done a 180 turn from his previous cuckold role of living vicariousl...