Sissy Cuckolds Stories

7,178 results
Orientation
Length
Source
Infinite Scroll

Valentine's Day Party

by cuck2serveU on Sep 16, 2017
Interracial Love

As I explained in the Super Blow Party story, our group of 6 cuckold couples each take turns hosting holiday themed parties. Second party of the year was hosted by the youngest couple of our group, twenty-somethings Kari and Jeff. They are small business owners who have had descent success and as a result have a pretty nice home out in the country. Plenty of...

Opening Him Up Ch. 08

by humbleboy on Sep 14, 2017
BDSM

A couple of days had passed since they boarded Rachel's ship and they had the gangbang. It was almost dinnertime and Amy was in C5 with her slave. He was tied up and gagged. Amy was in a comfortable dress sitting on a chair across from her slave pondering what things were going to happen to him. There was a knock at the door. It was the Captain. Amy yelled,...

My Cheating Wife Ch. 02

by vagabond678 on Sep 12, 2017
Loving Wives

When Colin woke up the next morning, Michelle was still asleep, which was not surprising, given the state she was in last night. He had taken a shower, and was dressed for work when she sat up, rubbing her eyes. "Good morning, hon," he said cheerfully. She squinted at him through sleepy eyes. "What happened last night?" she asked. "You got home at 1:00 in...

Make Your Wife Cuckold You

by BJayCool on Sep 19, 2017
How To

I have seen certain articles advising women on how to turn your husband into a willing cuckold but not found a decent one which could guide husbands on how to get their wives to cuckold them. The strange part is it's always the men who initiate or want cuckolding and usually not the women, the women may cheat but they don't harbour the fantasy of cuckolding...

Cuckold

by CuckoldGuy on Sep 12, 2017
Reviews & Essays

The true stories that I've posted here on Literotica.com about my cuckolding have generated many emails to me. Some hateful and some asking me to coach or mentor them but most with questions or comments so I thought I would post some of them here. Anyone seeking advise from me, I make it clear that I'm not a psychiatrist or psychologist. I'm an engineer but...

Cuckolding was Me Totally Pt. 02

by ACTDrew on Oct 13, 2017
Fetish

Jill had settled into the new situation with us perfectly and I think I enjoyed it even more than she did. I had taken control of her web sites and had also created a few personnel sites to help her find men to play with (all with big cocks). At home Jill was slowly taking control of the house and turning me into the primary domestic role for the house and...

AliExpress and Sissy Downfall Pt. 02

by His_fag_wife on Oct 15, 2017
Transsexuals & Crossdressers

Charlie had really done it this time, deciding on his first big self bondage session in his hotel room after picking up all his kinky goodies he bought on AliExpress. Then his wife had surprised him by joining him for the weekend and found him, fully dressed as a Sissy slut, make up, wigs, high heels the lot. Locked in bondage at his own hands. Now she was a...

The Making of a Mistress Pt. 06

by EiryCGar on Sep 14, 2020
BDSM

Author's note: 'All things must pass' and I feel that this series has reached a natural conclusion. As always, I must point out that all players in this fictional saga are aged 18 or older, and all sexual acts are consensual. The Making of a Mistress Chapter 6: Cwm Pechod's Cuckold Community The invitations to the party for the combined wedding anniversary...

Cuckolding Gets Moist Ch. 02

by Imgoingallnatural2 on Oct 19, 2020
Loving Wives

I never wear deodorant. Having smelly, all-natural armpits has health benefits, but it also helps me easily separate the men from the boys, or the Bulls from the cuckolds. Last week, I went to the local gym. I was wearing my usual: a cotton sports bra and shorts. I noticed the air conditioning was off. After about half an hour, I was drenched. The creases u...

Cathleen Encouraged Ch. 11

by nocluescooby on Sep 12, 2017
Loving Wives

This is part of a continuing story which features hard core, Black into white interracial cuckoldry as a central theme. This theme is not for everyone. If this theme offends you, I don't suggest reading this particular story, or any other chapter in this series. * Once Randy had invited me to witness his sexing my wife Cathleen the mood in the house became...