Sissy, Heels, Cuckold Stories

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AliExpress and Sissy Downfall Pt. 03

by His_fag_wife on Nov 2, 2017
Transsexuals & Crossdressers

Tim cupped Emma's arse cheek as they went into the hotel room, stroking her, sliding into the cleft of her cheeks, warming her up a little more, not that she needed it. Charlie didn't notice them come in at all. Not that she could really turn her head with the thick COCKWHORE collar padlocked tightly around her neck. The cords attached to the dildo were als...

Fun Day of Golf Turns to Cuckolding

by Red10Dog on Sep 14, 2020
Fetish

Me and the wife planned a golf tournament up north at a fresh golf course we never played before. While she takes a shower, I grab clothes for her to wear. She comes in the room and sees what I have laid out. White lace ankle socks with ruffles at the top, Black satin panties with bright pink wording reading "HOTWIFE cum inside!" A white loose mini skirt a...

A Weekend Away Ch. 01

by SluttyChrissy on Sep 21, 2020
Transgender & Crossdressers

My wife Tiffany had been hinting for a while about my birthday surprise. She wasn't great at keeping secrets, and I normally figured out her surprises in advance only to have to act surprised, but this time she was being super cagey. She asked if I would be able to leave work at noon that coming Friday so I figured we were going out of town for the long week...

Cuckolding Myself

by cr33pingd3ath on Sep 13, 2017
Loving Wives

I rolled off of my wife and lay beside her on our bed. The cum filled condom hung loosely on my limp cock which was quickly shrinking back to its flaccid state. Neither of us spoke a word for the few minutes that followed. By that time I was quite familiar with the dreaded silence that followed every time we had sex. In fact, we were both familiar with the w...

The Locksmith

by cdbrittany4bbc on Jul 18, 2018
Transsexuals & Crossdressers

I wish to thank thewinedarksea for editing this beast. Summary: Fantasy night goes awry. Let me start off by saying my wife Amy and I have been married eight years now. I must admit our love life has been waning, and sex — when and if we have it — is plain vanilla. Our anniversary weekend was coming up. I told her we needed to do something to reignite our...

Extreme Cuckold Fantasy Ch. 02

by Revan7 on Jul 29, 2019
Interracial Love

Prologue It's been two years since David and Jenny had started to fantasise about cuckolding. Two years after that jenny was pregnant with one of four black man's baby. They were on week away from a villa holiday in Spain with these four black men and were about to go out and get queen a of spades tattoos for Jenny. Jenny was pregnant with a black man's bab...

My Wife, My Boss, & I Ch. 02

by James Quiller on Sep 17, 2017
Loving Wives

After our short exchange of words, Candy got up and went to the bathroom to clean up, leaving me lying naked on the bed. I couldn’t think of anything to do at that point, so I cleaned up in the small bathroom downstairs, sat down to read a book and think about what had just happened. Despite the fact that I was thoroughly and erotically involved with what...

Black Cuckolding In Montreal

by Samuelx on Sep 11, 2017
Interracial Love

Never say never, I guess that's what the moral of the story is. When my husband Benjamin "Benny" LaCroix told me that he wanted me to cuckold him, I think my jaw hit the floor. Benny is six-foot-one, lean and muscular, with dark brown skin, curly Black hair and lime-green eyes. My darling husband is biracial, born in the City of Montreal to a French Canadian...

Discussion with a Wife of a Cuck Ch. 03

by wantyou on Sep 12, 2017
Loving Wives

1/25 E-mails I wrote: Hey babe! thanks for that. It's fun talking to you about all of this. You're making me hot baby. I have something to chat about with you. Alice wrote: Yes, this is lots of fun! I wrote: My lover does this when I leave. She showers and then she has her husband eat her pussy some more. I'm sure she tries or actually does hold my cum...

The Perfect Handjob

by Ricky_writes on Sep 13, 2017
Loving Wives

I've been married for 20 years. It didn't take my wife Tammy and I too long to figure out that I had a much stronger sex-drive than she did. Frankly I have thoughts of sex about 5 times an hour and my wife has the same thoughts about once every 5 days. I'm sure it is a rare occurrence when two married people have the exact same desired level for sex. The way...