Sissy, Heels, Cuckold Stories

88,578 results
Orientation
Length
Source
Infinite Scroll

March Madness Ch. 09a

by jbirdman on Sep 13, 2017
Transsexuals & Crossdressers

This story is not intended for children and if you are not old enough to read sexually explicit material, go away. This story features some elements of female domination (femdom), teasing & denial, chastity training, mild bondage, creampies, cuckolding cross-dressing and a few other fantasies of mine. I hope you find it entertaining, but if you might be offe...

Stephanie's Cuckold Ch. 01

by Superboytoy on Sep 17, 2017
Fetish

I want to thank Luckybitch22 for all her wonderful help editing this story who without her help would not have been possible. All persons are over the age of 18. This is all the work of fiction. Please enjoy and give me feedback if you all want it to continue. * Stephanie had known Glenn for sometime. She met him on line and knew instantly that he was what...

Black Cuckolding Dreams

by Samuelx on Sep 11, 2017
Group Sex

Sometimes what you're looking for is closer than you think. Take my fiancé and I for example. My name is Stacey Walton and I'm a young Black woman living in Milton, Massachusetts. I studied business administration at Bay State College and earned my MBA at the University of Massachusetts at Amherst. Presently I work for a real estate company in Brighton. I me...

Letter from Carker's Rents

by justincbenedict on Sep 24, 2019
BDSM

Dear Shoeblossom-- Since I taped this, I also have enslaved my brother-in-law Santiago and his basketball team. So I have real progress going on here in Carker's Rents! Love, Sugar Perez "Sugar, I am having a devil of a time getting these thorns out of my, um--" "Your diaper. Say it, Esteban." "Don't--don't you think it was punishment enough for me to...

Foot Cuckold for Isha Ch. 02

by cuck_for_isha on Sep 16, 2017
Fetish

Hey guys, Rahul is back with yet another cuckolding experience with Isha (goddess) and my master (Atul). This is Part-2 of the series. So I am back with the tale of another day of my life. I was cleaning the house as instructed by my goddess, who was out with her boyfriend, Atul, for shopping, with of course my credit card to handle the expenses. They had...

The Sexy Cuckold Couple Pt. 02

by cuckcpl4play on Sep 26, 2017
Fetish

While neither of us slept great, we did manage to get a little bit of rest before we were suddenly woken up with Jen's phone blowing up. She checked her text messages to see that Brian had requested we meet in his office at noon today. He made it clear that unless there was an emergency or other, he would expect to see us both there. We were a bit surprised...

Discussion with a Wife of a Cuck Ch. 04

by wantyou on Sep 16, 2017
Loving Wives

1/26 E-mails This chapter starts out with me answering Alice's question. I wrote: First my answers to your questions! Alice wrote: The story is fine, but you have not included anything about what I have told you so far. I will as the story moves move and more into your meeting and the sex and then afterwards when you start to see Tyrome. I answered: I...

Cuckold Wedding Ch. 2

by katt on Sep 15, 2017
Loving Wives

My thanks to for feedback which has given me ideas for the first part of this story * * * * * After the cuckold wedding (see part 1) we all adjourned to the garden where a buffet and drinks were served. I stood on the patio watching my wife hand in hand with her lover Bob go from group to group. They were laughing and chatting away and often heard various...

Butt Fucked

by Angelscuck on Sep 14, 2017
Anal

Brian loved to fuck his wife Sandy in the ass. He much preferred it to vaginal sex. He had always enjoyed anal sex. Giving, not receiving. He remembered even when he was twenty; he use to bully his eighteen and nineteen year old brothers into letting him fuck them in the ass. His wife Sandy preferred vaginal sex but could hardly feel Brian's four inch, penc...

Cuckold

by HerLittlePiggy on Sep 18, 2017
Loving Wives

She was a big woman, not fat mind you, but big none the less. She was about 5'11" and probably weighed a muscular 180lbs. Her height garnered attention but not as much as the way she dressed and how she carried herself. She was dressed in a short black leather skirt when I first saw her. A black and red leather corset was tightly laced over her torso to ac...