Chastity Sissy Cuckold Stories

18,147 results
Orientation
Length
Source
Infinite Scroll

Marabogo: Cuckold Island Ch. 03

by eeric on Jan 21, 2019
Interracial Love

A crowded lobby stood in front of Joshua as he began to drag the suitcases towards the elevators. Luckily two of the cases had small wheels on them, which made it a lot easier. Though the laughter he got from the women he passed made the whole matter a lot more humiliating. Joshua could hardly fathom how this had all happened. Just a few days ago he had go...

Being Made a Cuck

by Blueboy1965 on Sep 28, 2020
Loving Wives

This is a true story involving my ex-wife and I. We enjoyed a few times with other couples but this is about me being made her cuckold. Sue would often take our daughter to school and talk about men or women she had seen and fancied. As you may of guessed she was bi-sexual. On this occasion she had noticed a man working on the school whom she found attrac...

The Wedding Ch. 04

by betamale08 on Mar 30, 2020
Transgender & Crossdressers

The Wedding (Patti Cake part 3) Chapter 4 -- Teaching, Teasing and Testimonials... I was a little stunned and leery after reading my version of this contract which wasn't all that different from Patti's... From changing my name to rescinding my rights to wear male clothing while in the employment of Darren and Carol -- or Ma'am and Sir, and also, not to f...

March Madness Ch. 09b

by jbirdman on Sep 13, 2017
Transsexuals & Crossdressers

This story is not intended for children and if you are not old enough to read sexually explicit material, go away. This story features some elements of female domination (femdom), teasing & denial, chastity training, mild bondage, creampies, cuckolding cross-dressing and a few other fantasies of mine. I hope you find it entertaining, but if you might be offe...

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...

Letter from Turkey Thicket

by justincbenedict on Sep 15, 2017
BDSM

Dear Shoeblossom... Inspired by Grant and Lyla's "Letter from Fritters, Alabama" I send you this! I bade Vince good night, kissing him on the cheek. Vince looked a bit dazed. "Troyce, you don't have to end it here. Your husband is clearly not what you want...you like me, right?" It was hard for him, my sudden distance, since my tongue had been plunging i...

Adult Trip Pt. 04

by cuckcpl4play on Jul 18, 2018
Interracial Love

Master released me from the tree and quickly positioned both hubby and me on our knees next to one another. He handed me a brief and simple contract and ordered me to read it aloud. Obediently I read the contract as demanded. "You have agreed to be Master's dirty married white whore for the remainder of Master's trip, subsequent trips to this hotel where...

The Marriage Contract

by Seahawker on Jul 4, 2020
BDSM

I have spent the last 3 years with the most amazingly beautiful woman that god has ever graced this earth. Oh before I forget let me introduce myself, my name is John and my wife's name is Jane. We met at a dinner party that was being put on by her parents in order to raise funds to build a new Shopping and entertainment center. I was immediately taken by he...

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Sandra and Stevie Ch. 45

by Goodhusband on Sep 19, 2017
Loving Wives

Note: This story is the forty-fifth installment in a series entitled "Sandra and Stevie". If you have not read the previous forty-four episodes of this series, I encourage you do so before beginning this chapter. This is a dominant wife humiliates submissive husband story. That is the kind of story I write. If you do not enjoy these types of stories, I stro...

To Cuck or Be Cucked

by rc206 on Oct 30, 2018
Cheating Spouses

You and Jesse have been dating for six months now. It's been going great on an emotional level, but sexually, there have been some problems. Jesse is fantastic, but she was a virgin when you started dating. You were her first and she always doted on you because of that. She's clearly inexperienced and you've had to teach her most of what you've known, which...

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