Sissy, Heels, Cuckold Stories

88,578 results
Orientation
Length
Source
Infinite Scroll

Exposed as a Sissy Cuckold

by lapitup65 on Sep 18, 2017
Loving Wives

Last Friday we had a date scheduled. We were going out to dinner to meet Jay and we had a room booked at a nice hotel. Mandy and I checked in early. We relaxed for a while, sipping a glass of wine before Mandy headed off to take a bath and start getting ready. Just as Mandy settled into the tub, Jay sent her a text. I didn't read the text, I just took her ph...

Financial Difficulties

by tazsis1 on Sep 12, 2017
Loving Wives

We got into some financial difficulty a few years ago. I'd borrowed a lot and Elaine and I spent too much over one Christmas on the kids and family. And then I lost my job. It was all very difficult and, as these things do, it affected our marriage profoundly. While we kept our troubles from the kids, Ellen and I talked about little else -- driving out all p...

My Cuckold Fantasy Pt. 04

by love_tights89 on Jul 24, 2018
Fetish

Quite what she was planning would clearly have to wait, she wasn't going to tell me now. I watched as Chris came out of the shower with just a towel draped round his lower half, Charlotte walked over to him and kissed him deeply. Her hand resting on his chest. He gave her bum a firm pat and squeeze as she walked past him into the bathroom. All through the ni...

The Ex's New Toy Pt. 02

by Urtoy2be on Sep 15, 2017
Fetish

Dearest Dana, I am writing to talk to you about things that I am unable to say to you face to face. I want to go back to when we were still married and come all the way up to current date. Maybe you will, hopefully, like what I have to say. Maybe we can come to an agreement/arrangement that could be mutually beneficial and satisfying to everyone involved....

Sissy/Cock Sucker Dictionary

by silkstockingslover on Jun 12, 2019
Reviews & Essays

Summary: A list of terms to aid in understanding the activities and nature of sissies and cock suckers. Note 1: The author's source material isn't Webster's Dictionary or anything similar, but is drawn from many years of interest in matters sexual and countless conversations, both spoken and online, with other perverts. Note 2: Thanks to Tex Beethoven and...

A Toy Party Story

by lushusboobs on Sep 11, 2017
Transsexuals & Crossdressers

Toy Party Story Recently I met with a person whose sole desire was to be fully dressed and transformed for me. We spent quite a bit of time on the phone discussing why feminization was such a powerful fantasy for him. He explained that he felt so vulnerable and powerless as a woman and that it was exactly the opposite of his everyday life where he held mu...

The Ranch

by lonerancher on Sep 17, 2017
Fetish

My wife Brenda came home and confessed to having an affair at work with Robert a black man. She said he made her cum so hard and apologized to me. Then she said Jess if I slip again will you leave me I said I would cross that bridge if it came. We had been married for two years, both with good jobs and great house bought life looking good then this affair. I...

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...

Sin of Vanity Ch. 01

by Belongs2Beth on Sep 12, 2017
BDSM

Author's Note: This story continues the story of Vance, Marcia's friend introduced in "Marcia Goes Back to School". I have made an effort to make sure that this chaptered story can be read as a stand-alone or as an episode in a continuing series of stories set in the fictional town of Torquay, Connecticut. Readers of my earlier works will be familiar with Mi...

Intervention

by Angelscuck on Sep 13, 2017
Transsexuals & Crossdressers

My fiancée's girlfriends were becoming a little apprehensive about the changes Angel was exhibiting since we had started dating. They had noticed her attire had become much more suggestive, and her make up more severe. There were other changes too. She was now sporting a tattoo on her right shoulder, an angel/mermaid holding a heart with my name on it. Sh...