Sissy, Heels, Cuckold Stories

88,578 results
Orientation
Length
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Infinite Scroll

Dominating Sugar Daddy

by LittleDickSissy on Jul 3, 2018
Erotic Couplings

The sissy cuckold was at the ATM withdrawing cash for his Mistress. He needed cash for her nails, her new dinner attire, and makeup. As he made his withdrawal his little dick dripped precum in his purple lace panties. He always got turned on every time his Mistress provided strict instructions to him, and of course whenever she played without him. "Now tell...

Powerless

by siscuc on Sep 16, 2017
Transsexuals & Crossdressers

I was alone in the house, Tina was at work. It was 4 in the afternoon and i was looking over some pictures when the phone rang. It was Tina, "Hi Sweetheart" i said. The tone of her voice was harsh "Start getting ready, tonight you will be my sissy, you can choose to wear any of my clothes except the ones in the top drawer, I'll be wearing them." That was all...

Cuckolding Ricki

by mmms_ricki on Sep 17, 2017
Loving Wives

MMM's HotTub Party & Cuckolding ricki MMM had not been back to Oregon for over 8 months and was anxious to spend some time with her best girlfriend Jill and her significant other Roger. Mary was sure that Roger had a crush on her and was anxious to take things a little farther if Jill approved and Mary made the opportunity occur. MMM had been training her...

The Cuckold is Black This Time

by Samuelx on Sep 11, 2017
Transsexuals & Crossdressers

After months of hesitation and much soul-searching, a momentous decision finally got made. The big Black dude burst into Mistress Chocolate's den in downtown Ottawa, Ontario, and told her of his rather unusual request. The six-foot-tall, gorgeous Black Canadian female dominant listened to him, and then agreed to make his most forbidden fantasy come true. It...

Dreams do Cum True

by eviltwin52 on Mar 30, 2020
Loving Wives

"Wait, what?" I said raising my face out of my wife's cum filled pussy. "He wants you to suck his cock johnnie," Cin hissed. "Thomas said that if you like eating his cum from my pussy, you might like getting it from the source. Now finish what you started my dear sweet cuckie and get the rest of the gift Thomas sent you." With that my beautiful wife of 8 y...

The Making of a Mistress Pt. 04

by EiryCGar on Jul 13, 2020
BDSM

Author's note: The saga of Mistress-in-Training Marie and her sissy Charles has reached the point of their marriage. After the ceremony, Marie achieves her ambition and becomes a hotwife, making Charles a cuckold in the process As in all my fictional stories, all characters are over the age of eighteen, and all sexual practices described are performed conse...

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...

Becoming a Sissy Cuckold Ch. 02

by Pantieslave on Mar 26, 2019
Fetish

Beth was now fucking Jerry every 2 or 3 days and each time they had sex Dan was required to be dressed in girly clothes and made to watch them as well as to video them. Beth loved watching the video's with Dan on those days that she didn't have sex with Jerry. Dan was also required to suck on Jerry's cock getting it hard so that he could fuck Beth and Dan wa...

Kissing Crossdressers Pt. 02

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

I awoke the next morning still dressed in Carla's purple panties, stockings and matching bra. The rampant rabbit and the dildo were beside me on the bed. There were traces of the lip-gloss on the duvet and the heady, pungent smell of cum. Carla's panties were stained with the stuff. I figured I had a lot of cleaning and clearing up to do. I felt a sense of...

Big Black Cock: A Sissy Surprise

by silkstockingslover on Feb 13, 2018
Illustrated

Summary: A wife joins her husband as a slut for a teen BBC. Note: This is a 2018 Valentine's Day story so please vote. Note 2: Thanks to Tex Beethoven, thor_p, Robert and Wayne for editing this story. WARNING: If you hate gay stories, interracial submission, sissification (not a word I know) or cuckolding please don't read. If you do like those themes.....