Sissy, Heels, Cuckold Stories

88,578 results
Orientation
Length
Source
Infinite Scroll

Life on the Ranch Ch. 01

by phoenixcinders on May 16, 2018
Transsexuals & Crossdressers

I can't believe those jerks threw cattle dung at me. No good, dirty rotten, a-holes. They got that shit all over me. That's not even the worse part... Well, that's up for debate. But to top it off we're out of hot water! I had to wash the bull shit off with freezing cold water. I hope to god Steph gets back soon. I wish I could tell her what those jerks did,...

Made to Obey Ch. 04

by madetoobey on Jun 24, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to a shemale porn site by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). Ruth, as a part of my punishment, was setting me tasks until Esther (who'd taken my laptop and mobile phone) could verify I'd never visited such sites before. I'd been forced into a chastity cag...

Busted Wearing Panties Ch. 04

by tonyl65 on Sep 18, 2017
Transsexuals & Crossdressers

I want to thank the readers for hanging in there with this story line. I also want to thank you for the wonderful comments. I appreciate you all for taking the time to send me an email or comment, I will respond to you all. Chris and Jessica had to leave for a dinner engagement which they could not get out of. Emily and I we wanted to be alone anyway so...

A Change of Heart

by d_fantasy on Sep 14, 2017
Fetish

My girlfriend Emily and I have a good sex life, I love her very much; she was the first and only girl I have ever had sex with. She is about 5'6", nice size tits (not too large), long black hair, she's half Phillipino, half English. I'm 6'1", I have long brown hair and a dark goatee beard. We've been going out now for about 3 years, with no serious problems...

The Slave and His Master Ch. 07

by loveandlust28 on Oct 7, 2019
BDSM

A note on subspace: ***DISCLAIMER*** I do not pretend to be an expert on bdsm but I have done my best to conduct thorough research, feel free to do the same. Dear reader, If you are not familiar with the term subspace or the effect it can have on an individual, then please let me enlighten you. Subspace, is when the submissive experiences a moment wher...

Deflowering the Boy

by JimBob44 on Jan 8, 2019
Transgender & Crossdressers

*Author's Note: Any and all persons engaging in any sexual activity are at least eighteen years of age. Disclaimers: This story has been edited by myself, utilizing Microsoft Spell-check. You have been forewarned; expect to find mistakes. *.* "Last year, last year, last year," Charlie Whitman muttered to himself as he trudged up the steps of Centennial Hi...

Nathalie's Makeover Ch. 07

by Cagivagurl on Feb 3, 2020
Transgender & Crossdressers

We continued to beat them to every contract. They had been bitten so hard by that failure they became more cautious which just made it easier for me. It was so easy in fact that it started to take some of the gloss off it for me. Paul had reduced Yves input, obviously holding him responsible for the failure. So things progressed easily for us, Mike was mor...

A Valentine's Day Cuckold

by secondsamuel on Feb 11, 2019
Loving Wives

A Dedication and Description: To my wife, mrssecondsamuel who requested I write her a story involving bisexuality, cuckolding, and pet play for Valentine's Day. This is a Valentine's Contest Piece, so please vote! Author's note: I am recovering from repeated surgeries on both arms to correct a degenerative nerve condition. To write this, I use voice to text...

Eenie, Meenie, Miney...

by FrancisMacomber on Sep 18, 2017
Loving Wives

Rachel Madison The prison guard came into the infirmary and closed the door behind him. Rachel smiled at him and he shyly looked away. Rachel knew he had a bit of a crush on her; most of the guards did, if for no other reason than there were few attractive women working at the Western Correctional Center. He cleared his throat. "I got a patient here to see...

Bill and Sally

by thecarolinadreamer on Sep 14, 2017
Loving Wives

Authors Notes: #1 This story is a work of fiction. All characters are 18 or older #2 WARNING!! This story is about a woman, who encouraged by her husband, screws another man. Therefore it is a cuckold story. I recognize many Loving Wives readers object to cuckold stories; although I'm at a loss on how to write a LW story that would fulfill the requirement...