Cuckold Sissy Stories

12,909 results
Orientation
Length
Source
Infinite Scroll

Tony's Ascent Into Cuckolding Ch. 03

by Cuckyboy3 on Sep 12, 2017
Loving Wives

She called Brad that evening to let him know that I had come around after some convincing. They chatted for a while, during which she told him about my misbehavior. She moved away from me and talked softly for a while from the other room. Finally, she came back to me. I heard her saying, "Do you promise? You'll do that for me?" Then she listened for a while...

Lost in Lore

by OtakuFoxx on Sep 26, 2017
Fetish

You're at the gateway of a sexual adventure with some of history's greatest mythological creatures.What's next? I am a male. I am female. (Foxxs Comments) What's next? I am a male. I am female. (Foxxs Comments)...

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Letting My Wife Cut Loose Ch. 03

by weaponx on Sep 17, 2017
Loving Wives

I couldn't believe what had just happened. What I thought was to be a great little vacation, turned out to be a total nightmare. I thought that by letting my beautiful wife Beth have some fun on vacation it would do her some good. Little did I know what was going to happen. I didn't think that letting Beth cut loose a bit and have some extra drinks would tur...

Quarantine Slave Ch. 01

by grizzley123 on Jun 9, 2020
Fetish

I was lonely. Only 4 days into the quarantine I was assigned to after testing positive for COVID-19. I was barely ill, but I didn't want to infect the world, and the world certainly didn't want me to share. I was supposed to stay out of the world and already I was going nuts. I was also horny as all hell. And then I got a text. Need Anything? I didn't kn...

After The GangBang

by Angelscuck on Sep 17, 2017
Loving Wives

I woke up about 8am. I was sore all over. My ass hurt and burned like hell and my jaw ached. Then it all came back to me. Angel's gangbang. Or should I say Angel and my gangbang. Sure, she was fucked in the ass, mouth and cunt by over twenty guys, but I took my share of cocks too. I was caked all over with dried cum. I felt her stir next to me. She was a...

My Dom's Decisions

by davesubboi on Oct 12, 2017
BDSM

The thought of being submissive and letting another superior being guide, direct and change me has become one of my driving desires. Over the past 15 years I have realized I am much better at pleasing others and have determined based on numerous online doms/master/mentors that I really should not care about my own pleasure if I can serve another and give the...

A Small Problem

by Rbhy2 on Mar 2, 2019
Cheating Spouses

"Hey baby I'm home" you said as you walked into you apartment. The building wasnt much, just an old converted motel that you and your girlfriend Kay had scraped enough money together from your menial, part time jobs to afford. "Hey babe I'm in the shower" you hear coming from the bathroom on the back. "I'll be out in a sec" You...

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How did It Come to This? Pt. 01

by tazsis1 on Aug 13, 2019
Loving Wives

I drove my wife C to the airport. She was going to be away for a week at a conference in Paris for work. "Pull into the layby just ahead." I did as I was told and we came to a halt. Two cars were parked ahead of us, traffic flying by at speed on my side of the car. We sat in silence for what felt like a long time. C looked out of the window on her side of...

Ultimate Sissy Fail

by cdbrittany4bbc on Feb 12, 2019
Transgender & Crossdressers

This is the story of the perfect sissy getaway. This story contains subjects of crossdressing and interracial male sex acts if this offends you please don't read. Everything except one or two events happened, Now, there is some embellishment. I had to tell someone. I decided to tell everyone. A little bit about myself. I am in my late 50s. My adventures in...

Carol's Gifts

by Belongs2Beth on Sep 16, 2017
BDSM

Authors note: This is the third story featuring characters introduced in "Carol's Christmas." In this installment Carol give's Jack his Christmas gift one night late with the help of Irena, "Marcia" and several well hung younger men. The sex action in this story is unrestrained, and since the tags are at the bottom of the page, I will issue the following mil...