Sissy Cuck Stories

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Mistress Morgan's Sissy Husband Pt. 03

by corduroysissy on Dec 16, 2017
Transsexuals & Crossdressers

Robin arrived home from work about 5:30 on Thursday, he still felt a little apprehensive about what happened Tuesday night with his sissy friend Patty, and he hoped he might get to talk about it with his wife Morgan. He really enjoyed wearing the corduroy skirt outfit she bought for him, and he loved being a sissy whore for his wife and Patrick, her "boyfrie...

The Cuckold's Babysitter

by yumacd on Sep 26, 2017
Loving Wives

Hi, I haven't written in a while. The set-up for the sex is probably too long. I'm thinking of continuing the story. Hope you enjoy it. YumaCD === My wife, Tami, has been cucking me for a couple of years now. Most of you Literotica readers have heard the story before... - It started when I revealed my fantasy of watching her with another man one night...

Carol, Candy & the Ex Pt. 02

by corduroysissy on Mar 26, 2019
Transgender & Crossdressers

(Will Candy make a good cuck?) Davie was standing at Carol's front door dressed in a pair of copper brown wide-wale corduroy dress trousers, and a beige polo shirt. Oddly enough, he felt more nervous than he did the night before when he was in full drag, and he attributed it to the ex-factor. Last night Davie as "Debbie" was there to meet Robbie as "Candy"...

Madam Molly Pt. 01

by corduroysissy on Feb 6, 2018
Transsexuals & Crossdressers

It all started in a chat-room, "Closet Sissyboys." Jesse had been spending a lot of time in chat-rooms in the six months following his divorce. He wasn't looking for love, he just liked to drink and have cybersex while jerking off with corduroy. Yes corduroy. Jesse had a corduroy fetish his whole life and now at the age of 36 it was stronger than ever. He...

Sissy Manners Classes Ch. 01

by fridaysissy on Sep 12, 2018
Transsexuals & Crossdressers

It was late night, I am 10 km away from my room waiting for sharing cab or auto service to reach my room at last I joined a sharing auto service with two members including me. The other passengers stop came early, and I remain alone in auto waiting for my stop to come. Driver said he is stopping the service and returning to his home and asked me to get down....

Carmilla the Succubus Queen

by Hornyonion007 on Apr 29, 2025

Fwap fwap fwap fwap fwap fwap fwap “Aahnn, ugh, nnngghh… p-please… ooogh…pleee-ease help me, saa-ave mee…!” You hear echo in the distance, down these dark unhallowed halls. For years the lands had been ravaged by unholy demons, terrorizing the innocent and the faithful, either by storming the gates of cities and keeps, killing and torturing everything in the...

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Cuckold trial

by Crazywriter on Apr 29, 2025

As I scrolled through my phone watching cuck porn I saw an ad Do you want to be cucked ? Are you worried about the consequences? Do not worry as you'll get to experience a baggage free cuckolding experience, choose your appropriate cuckold package I was curious and clicked on it after browsing about the website on Google and reddit and confirming it is legit...

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Madam Molly Pt. 02

by corduroysissy on Feb 11, 2019
Transgender & Crossdressers

Molly & Jessie's conversation lasted about twenty minutes, and by the time it was over she'd made it quite clear that when it came to obedience her expectation were very high. She then informed him he was going to be her little slave-boy and amuse her for a while. When she was ready to get laid she'd summon her cuck Tracy back and Jesse would resume his boyf...

Anklet Adventure Pt. 02

by dometoo on Oct 29, 2018
Interracial Love

Day two of our cruise started with the sun shining through the open balcony slider and a slight, warm breeze dancing over our naked bodies. The rhythmic sound of waves breaking against the hull was memorizing, almost hypnotic. My beautiful wife of 20 years and I lay exhausted on the cum stained sheets she and her bull made without me last night. We were both...

Zamindars Pt. 02: Thakur & Champa

by prithvik1947 on Jun 18, 2019
Group Sex

In Zamindars Part 1, I had described the situation that I witnessed on arriving at my friend Vivek's estate. His father, Subhash (The Thakur) was openly having a sexual relationship with Champa who was 20 years younger to him and the wife of his driver. Part 2 is more about what I saw between Subhash uncle & Champa. Champa was sitting in uncle's lap while h...