Chastity Sissy Cuckold Stories

18,147 results
Orientation
Length
Source
Infinite Scroll

The Wedding Ch. 02

by betamale08 on Mar 31, 2020
Transgender & Crossdressers

The Wedding (Patti Cake Part 3) Chapter 2 -- Party in Pink Purgatory... "Oh Wow Dale! You look fantastic! Very -- Very pretty... I can hardly tell that you're my boy anymore! Really sweetie I'm so impressed -- and Patti you look gorgeous too... I knew that dress would look stunning on you -- but Dale -- my pretty -- pretty -- son... That dress is perfect;...

Getting Nailed

by jbirdman on Sep 25, 2017
Fetish

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), cross-dressing (CD), mild bondage, Trangender (TG) and a few other fantasies of mine. I hope you find it entertaining, but if you might be offended, stop reading and do something e...

Sandra and Stevie Ch. 42

by Goodhusband on Sep 19, 2017
Loving Wives

Note: This story is the forty-second installment in a series entitled "Sandra and Stevie". If you have not read the previous forty-one 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...

Fucked a New Hotwife Pt. 01

by MattieG on Sep 14, 2017
Loving Wives

Last night I met a new Hotwife/Cuck couple for the first time. He is very submissive to her, and she was craving someone very dominant that she could let go with. We had chatted by text for a couple of days and I figured we would meet in a few days have coffee and maybe meet and play in a couple weeks. With all of the talk her cuck was super excited and was...

Don't Stereotype Cuckolds

by eviltwin52 on Apr 27, 2020
Loving Wives

Let me start by saying that I am a cuckold and a happy one. It was my choice and I found a Woman that would lead me down the path to unbridled satisfaction. Unfortunately too many Lit readers either disregard our lifestyle altogether or deride those of us who are strong enough to give our Women what they want and thereby meeting our own needs. But what are...

Coming Home, Coming Out Pt. 09

by EiryCGar on Jun 1, 2020
BDSM

Author's note. As this saga continues, aspects of sadism, slavery, cuckoldry, lesbianism, denial and general bdsm are explored. All characters are figments of the author's imagination, and all characters consent to every aspect of the activities described. As always, all characters are aged over 18. Chapter nine. Saturday morning dawned, and Sara slipped f...

Letter from Iddlesleigh Harbor

by justincbenedict on Sep 9, 2019
BDSM

Dear Shoeblossom-- I am a townie bitch from a crappy beach village, and I snared a rich little piglet, and I just recorded one of our more pitiful conversations! Stephanie "Stalki" Sendack "I don't think you did that badly, Crates. You actually seem to howl more when I cane you, you know." "Stalki, it feels so marvelous when you stroke...oh it's so nice...

My Transformation

by paige_silk on Sep 16, 2017
Transsexuals & Crossdressers

It all started during puberty as these things often do. I can distinctly remember watching a TV programme about a shop that would dress men up as a woman and getting really turned on by it but not really knowing too much more or what to do with myself. These feelings occasionally came back over the years but with the restrictions of living with parents the...

The Women in My Life Cuck Me Ch. 02

by Philyssis on Mar 18, 2020
Fetish

Continued from part 1, right in the middle of a sex club... I was relieved when my wife grinned. Then I was a bit concerned as it turned into an evil grin. "Wow Phil" my wife said to me. "I knew you had a dirty mind, but I didn't know you had THIS in you!" Amy, my wife's little sister, leaned over and kissed me on the cheek, then looked at Tara, "I'm s...

Male Chastity Device

by CuckoldGuy on Sep 12, 2017
Toys & Masturbation

Janice and Mike (not their real names) are a married couple in their mid forties. Married about twenty years. About ten years ago they started playing with a male chastity device and discovered they were having a lot of fun with it. They have been using it ever since. The device is a stainless steel or plastic tube about three and a half inches long and abo...