Elderly Man Sissy Stories

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Simon Sissy Slave Ch. 04

by Timewarp10 on Aug 20, 2019
BDSM

Simon staggered in for work the day after the slave auction, his body stiff and sore. Mr Berne and the others in the post room were shocked to see the sissy's bruised and lacerated buttocks. Barry's stiff cock betrayed his feelings; whipping and torture excited him. His sadistic nature relished the thought of thrashing Sissy senseless. Sissy was his fuck t...

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,...

Sissy Chantel, New Reality Ch. 07

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Seven: At 'The Agency' and I'm Off to a New Start In My Sissy Life. "Girls this is your new dorm mate, Sissy Chantel." one of the security staff says. The other staff member adds, "You shall take her into your group, help her set up her things and then take her around on a tour of the facilities and such. Report to the office after doing so, OK?"...

Sissy College Ch. 03

by MasterJW on Sep 11, 2017
Transsexuals & Crossdressers

Standard disclaimers apply. I'm indebted to Puzziboi for writing the first half of this chapter: Thank you! I really do enjoy your feedback, so please keep it cumming! Lastly, I encourage you to read the previous chapters before you delve into this one. Mr. Blackwood slapped his large veiny cock against Lenni's smooth lily white face with an audible smac...

Spanking Night Ch. 08

by Angelscuck on Sep 14, 2017
BDSM

As I held Master Dan's cock steady for my wife to sit down on I noticed her eyes were staring directly into mine. She had an amused smile as she licked her lips. Her labia were moist and dripping as they parted to accept the head of his cock. Her breathing quickened and a soft moan escaped her lips. Her eyes seemed glazed over and half shut as his huge m...

Sally, Tim have Elderly Neighbours Ch. 01

by MaryGrangerx43 on Oct 15, 2018
Fetish

This story is a complete fantasy and no association with real life whatsoever. No one is under the age of 20 and there is no physical hurt or pain. ***** Chapter 1 - Introduction My name is Sally Banks and I am 28 years of age and have been married for over 7 years to my husband Timothy Banks. We have always been reasonably happy, but over the last 12 mon...

A Sissy Saga Ch. 21

by Snurge on Sep 15, 2017
Novels and Novellas

The next morning Jennifer Hancock went down the stairs with her hair piled on top of her head and wearing a crumpled pale-blue linen overall to be amazed when Lulabelle said she looked as fresh as a daisy. Her mother was talking on the telephone, and when Jennifer appeared in the sitting-room she clapped her hand across the mouthpiece. "I've been negotiatin...

Call Me Katie Pt. 01

by KrierWitz on Sep 18, 2017
Transsexuals & Crossdressers

This is the first part of a story following Kent Wiltshire and his journey from an independent man to a submissive slave girl. Please let me know what you think, and if there is any themes you would like to see incorporated in the future. ***** My name is Kent, I'm 22 years old and live in a two-room apartment in Stanley, Idaho. It's a small city, with ju...

Seducing Kevin Ch. 04

by Spango on Sep 14, 2020
Transgender & Crossdressers

Dear Internet, Oh. My. God. That kiss. Time seemed to stop while Kevin kissed me. The crowded dance floor melted away and there was just the two of us, in our own little bubble of space and time. The only thing that mattered was his lips pressed against mine. As his lips flowed into mine, it felt like we were melding into one person, one soul. I had read ab...

It Only Gets Better

by ElderDirt on Sep 14, 2017
Romance

Author's Note: This is a story about how a chance meeting led to a much younger woman becoming an intrinsic part of an older bachelor's life. Readers be warned that if you are looking for raunchy and frequent sex, you will be disappointed. The sex that follows is just the spice added to the meat and potatoes of the love story This is my first venture into...