Sissy, Heels, Cuckold Stories

88,578 results
Orientation
Length
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Infinite Scroll

Cuckold Striptease Game

by Iftheshoefits on Sep 12, 2017
Fetish

I'd forgotten my damn key again. And my wife was taking forever to answer the door. What was she doing in there? I was mildly irritated by the time she finally opened up, but before my lips could even form the words to some smart-assed remark about how long I'd been standing there, my senses were overloaded with the sight before me. I gave her a once ove...

Heiress MMM gets Her Cuckold

by mmms_ricki on Sep 19, 2017
Loving Wives

Mary had recently inherited a rather large family fortune and become a multi-millionaire. As a result She was feeling extremely Independent and Powerful. Now that she was independently wealthy she had the urge to release Her Female Supremacy and Female Dominance side. She especially looked forward to showing off the Power She had over Her sissy submissive hu...

Caged!

by yvetteinpanties on Jun 19, 2018
Transsexuals & Crossdressers

I was a late blooming sissy. Like most sissies-to-be, I had early incidents of trying on my sisters clothes and enjoying the way they felt, but I always viewed myself as a heterosexual who just liked to imagine stroking a nubile female underneath the lingerie I was wearing. It was much later in life that I took the serious turn from being a heterosexual cros...

Whoops

by CuckyJimmy on Sep 25, 2018
Fetish

Having strong cuckold desires can lead you down an unpredictable path. So be forewarned. If you do not like cuckoldry or fetishes like SPH or cock worship, you may want to take the other fork in the road on a different literary path. This work is a product of very little reality and mostly fiction. Be careful, otherwise, Whoops Oh shit. Yes (my two fingers...

A Cuckold Earns His Horns Pt. 02

by lapraline70 on Sep 16, 2017
BDSM

This is part 2 in a series of letters about my cuckolding. For context, read part 1. We open with O/our Bull knocking at the door on the fateful evening. ==== Already on my feet, i walked to the door and, fumbling with the handle a bit, opened it to see Him. Our eyes met. i saw His immediately slide down my nightgown as His grin widened. "Ah, good evening...

Sorry Sissy You Lose Pt. 04

by LittleDickSissy on Apr 10, 2019
Fetish

Slave had been busy. Spending hours looking online for things for his Mistress. His little dick always swelling and throbbing as he went through pages of web sites, looking at heels, lingerie, hose, dresses, jewelry, etc. Mistress had tasked her slave. He was to purchase various outfits for her to wear on an upcoming trip. A work trip for his Mistress, but h...

Story of a Sissy Cuckold

by HughJanus on Oct 24, 2019
Fetish

Hi there, my names Michael but everyone just calls me Mike, i'm a 46 year old guy, i was an average guy living an average life, married to the love of my life, her name is Samantha. Shes my high school sweetheart, we dated all through high school then when we graduated we got married. She still has a smoking hot body, even all these years later, she works ou...

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Angel Learns My Secret

by Angelscuck on Sep 16, 2017
Loving Wives

My wrists strained at the ropes that bound me to the chair. The vibrator taped to my cock was driving me mad while I watched my leather clad bride mount her lover's huge black cock. Angel smiled at me teasingly, knowing the pleasure and pain I was experiencing.... Suddenly I heard her key in the door I quickly turn off the magic wand, put it in the desk dra...

Ms. Tanaka Fixes Me Ch. 02

by chenwanli on May 4, 2020
BDSM

Chapter 2- Ms. Tanaka Takes Charge Ms. Tanaka stood up, straightened her sheath dress and bowed to her daughter Hiroki to say goodbye. They exchanged a few final words in Japanese that I didn't understand, gesturing at me and smiling then Ms. Tanaka laughed throatily and demanded the rest of my clothes. I took my pants off from around my ankles and gave her...

Sam's Panties Ch. 02

by Quietoldie on Sep 19, 2017
Transsexuals & Crossdressers

At the end of their holiday the two couples exchange email addresses and phone numbers. Jean and Ken live in the North East part of England whilst Mike and Sam live near London. The 250 miles separating them is no bar to them meeting up from time to time when Jean can enjoy her new found desire for extramarital sex with both Mike and Sam. Her cuckold Ken is...