Sissy Get Anal Stretched Stories

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Sissy for a Day

by silkstockingslover on Oct 16, 2018
Fetish

Summary: With his wife's help and support, a man becomes a sissy for black cock. Note 1: This is a Halloween 2018 Contest Story. Be warned: this story involves sissy sex, obsession over black cock and a bukkake. If this isn't your thing, please don't read any further. Note 2: This is dedicated to the real Paul who requested this story. Note 3: Thanks to:...

Sissy Shopping

by Candour on Sep 25, 2017
BDSM

My first story, finally edited and tidied up. I hope you enjoy it, I enjoyed writing it. --------- You were standing in your local department store in the make up section, looking for foundation. Not too sure what you are doing, and must have looked a little lost as one of the sales girls came up quietly behind you. She was a delightfully pretty 18 year ol...

Phone call interrupted Pt. 04

by ambise on Mar 9, 2020
Group Sex

Jill groaned as she started to release the nipple clamps, the blood flowed rapidly back into her nipples, she felt the exquisite pain she now relished. A new sensation surged through her clit, as under Jenna's instruction, she quickly pulled the new clamp off it, fortunately it comprised two small magnetic metal cones but she still screamed only partly in pa...

Francie and Graeme's Defloration

by skriblur on Sep 12, 2018
Erotic Couplings

The odd-numbered parts have the sex. The even-numbered parts have the love story. ~1~ Francie likes what she's seeing -- her feminized husband. All slutted-up in strappy heels and frilly socks, a cute cornflower blue skirt and white cotton blouse, kneeling in front of the living room couch, sucking off one of Francie's boyfriends. Francie (wearing nothin...

A Sissy Saga Ch. 17

by Snurge on Sep 15, 2017
Novels and Novellas

Titled people were a weakness with Miriam Hancock. She frequently spoke of them with harsh condescension, but the snob in her heart secretly rated them higher than wealthy businessmen, and so it was with some delight she agreed to the visit of the ennobled Marchioness of Wiggleswick. The delight had doubled when she discovered that in both Debrett's Distingu...

Simon Sissy Slave Ch. 03

by Timewarp10 on Jul 30, 2019
BDSM

Mr Berne watched with satisfaction as the sissy paraded in the post room. Sissy walked gracefully in high heels. His ballet training made it easy. He knew how to walk like a woman. He had practiced, and he could walk with a book balanced on his head. It gave him poise, and the high heels gave elegance to his calves. The skirt was short enough to look slutty,...

Getting Nailed

by jbirdman on Sep 25, 2017
Fetish

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), cross-dressing (CD), mild bondage, Trangender (TG) and a few other fantasies of mine. I hope you find it entertaining, but if you might be offended, stop reading and do something e...

Slave Ch. 02

by slaveheathen on Sep 25, 2017
Fetish

Chapter the Second Just a note: This story contains bisexual sex, fisting, bondage, piss play and more. That's why it's in the fetish section. If this isn't your cup of tea, don't read it. If it is, enjoy! Now, on with the depravity... As I knelt there on the piss soaked blanket in my piss soaked clothes, I tried to gather my wits, not to mention catch my...

Don't Lie Ch. 02

by Scribler on Sep 16, 2017
BDSM

Saturday Dawn and I had breakfast in bed before she road my cock though two orgasms. For some reason I was not allowed to cum. We then decide on what I was going to make for dinner before Dawn went to the store. While she was gone I was to clean the house and do the laundry. I never realized how much Dawn did in the house. Though I did some work around the...

Simon Sissy Slave Ch. 02

by Timewarp10 on Jul 30, 2019
BDSM

Simon's arse remained sore for days, a constant reminder of his new role in life. Over the weekend the pain was severe, but the overwhelming feeling of his humiliation was compensation enough, and produced a warm glow through his body. His mind had been in turmoil all week-end. Sometimes the pain was unbearable, but he bought a cream at the pharmacy that rel...