Stockings Jerk Stories

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Orientation
Length
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Infinite Scroll

Leg Worship

by Dark Stranger66 on Sep 12, 2017
Erotic Couplings

I get to your house and ring the doorbell. You greet me in a lovely blue dress that does little to cover those beautiful legs that flow from your hips to the floor. "Come on in." you say warmly with a big, sexy smile. "Sit down for a minute, if you have time." I sit in a chair in the living room, watching as you pour yourself onto the couch across from me, c...

Room 1524

by Marcothegod on Sep 1, 2017
Group Sex

The bar was fairly quiet when we got back after the dinner and after three hours of being on my best behaviour, following my cover story and smiling at everyone, I was looking forward to a nice large single malt and then a couple of hours between Mrs Morganite's thighs. She was looking as sexy as ever, a low cut cocktail dress that buttoned all the way dow...

Stealing 30 Minutes

by bluewaterguy on Sep 14, 2017
Erotic Couplings

He watched as she came down the walk in her usual hurried pace, closing the cell phone just as she opened the door of my Lincoln Town car. She sat down in the spacious front seat with a nervous smile on her face. She looked tiny sitting there and also slightly mischievous, like she had a secret that only she knew. "I just called your husband to tell him th...

Catherine's Girl

by kingkeywriter on Sep 16, 2017
Transsexuals & Crossdressers

Catherine Roman's chauffeur pulled in front of my house in a black Escalade to transport me to Mrs. Roman's country estate for a weekend visit. Because of a surprise snowstorm, I had canceled my Friday appointments. Nevertheless, I wore my business suit and traveled lightly at Mrs. Roman's behest. Climbing in, I nodded toward the SUV. "Strong and elegant, li...

Maggie Gyllenhaal Is My Mistress

by Inamanica on Sep 19, 2017
Celebrities & Fan Fiction

Remember that movie, Secretary? Maggie Gyllenhaal was a secretary for a lawyer played by James Spader. Maggie Gyllenhaal's character, Lee Holloway, was introduced into the world of BDSM by her boss Mr. Grey. Well I worked on the set of that movie. I was a gopher. I did whatever was needed. From sweeping floors to going on food runs. It was a way to get into...

High Heels and Stockings Tryout Ch. 02

by neon_noodle on Sep 11, 2017
Transsexuals & Crossdressers

Chapter 2: Bi-sexual Sluts in Stilettos Author's Note: Thanks to all who read and enjoyed my first story. I hope you like this one too, and get so excited by it you have to jerk off and blow a big, wet load. Enjoy! * After my first semen-splattering cross-dressing experience, I was hooked on dressing up like a slut, and masturbating in stockings and high...

Anal Training Ch. 01

by Catchandrea2397 on Jan 20, 2020
Transgender & Crossdressers

This is the first in a series of sissy JOI training instructions. I want to provide real instructions that can be followed and enjoyed by anyone (well by any submissive sissy wanabee). Please only read this however if you are over 18. Feedback is welcome *** Day 1: Hello pet. Are you ready to have some fun? Are you ready to begin your training? Get...

Betty Finds My Story

by JackorJill on Sep 12, 2017
Fetish

The office was quiet at this time of the morning. I came in to get some paper work done. The phones never sounded better. I had put some coffee and stopped for a bagel. The applications on my desk had been piling up and that was a good thing. I never heard Betty until she was standing behind me. "Hey, you're early. Knock'em dead big guy." She was older then...

Call Me Katie Pt. 02

by KrierWitz on Sep 18, 2017
Transsexuals & Crossdressers

This is the second 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. ***** Ten minutes later, I find myself with a shaven head as my mistress is placing a wig on my head. Tiny needles go...

Nine Years of a Life Sentence

by munkin224 on Aug 29, 2017
Erotic Couplings

'Til death do us part. Those five little words. To some, they mean a life sentence only to be paroled through divorce. To others, something you suffer through because "parole" is the unthinkable...through better or worse...it has to get better, right? To me?... I never really dated anyone in high school. I was just too awkward and dorky I guess. I did go to...