Gillian Jacobs Stories

1,150 results
Orientation
Length
Source
Infinite Scroll

She Taught Me Well

by geronimo_appleby on Sep 12, 2017
First Time

I've heard it said that if you can remember the sixties, then you weren't really there. Well, I was 18 years old in 1964 and my memory is as clear as a bell. I freely admit that I was a naïve 18 year old – I'd never had any dealing with any of the mind altering substances that were in vogue throughout those heady years – I was still a virgin at my 18th birth...

Anna of Whitecliffs Hall Ch. 04

by SamScribble on Nov 4, 2019
Fetish

I know that meteorologists tend to consider that winter begins on the first day of December, but I've always felt that winter usually arrives about three weeks earlier than that. In my experience, somewhere towards the end of the first week in November is when the gloves and scarves come out. And so when, on the evening of the 6th of November, my friend Geo...

A Friend in Need

by aksarben on Sep 13, 2017
Erotic Couplings

I was having a horrible day. My girlfriend of several months, Isabella, had gone out of town to go to a conference. Usually, that wouldn't be a problem, but we had been having some issues as of late, and, for the past two weeks she had been texting another man. I had seen some of the texts over her shoulder and I had seen her sweet smile every time he text....

Gillian's Toys

by Apple_Jacks on Oct 5, 2020
Exhibitionist & Voyeur

Gillian pulled the large cardboard box into her living room, giddy with excitement. She tore it open like a girl on Christmas morning... It had finally arrived. She dumped the tangle of ropes and straps onto her bedroom floor. An hour and a half later, Gillian had assembled her brand new sex swing. With a smile, she texted a photo to Natasha. Natasha texted...

Gillian in Gibraltar

by oggbashan on Dec 24, 2019
Romance

Copyright Oggbashan October 2019 The author asserts the moral right to be identified as the author of this work. This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. Some of the dialogue is assumed to be in Spanish but the meanin...

Life, Death and Rebirth

by waif on Apr 18, 2018
Transsexuals & Crossdressers

This is my first attempt on this site. I originally wrote it for a contest on another story site. I hope that it will be well-received. ***** Gillian sits at her vanity, gazing into the mirror. Only her eyes are recognizable. The left side of her face is swollen as is her mouth. Her cheek bears the distinct pattern of a boot sole. Her eyes are puffy and sw...

Gillian's Justice Ch. 03

by MicheleNylons on Sep 23, 2019
Transgender & Crossdressers

Chapter Three - Cecelia Flick The oak-panelled courtrooms had been purposely designed to look imposing and foreboding to those appearing before the Justices at the Old Bailey but Gillian Dixon confidently strode into the dock looking like she owned the place. "Any chance you're going to show a little respect and servitude?" her barrister Brian McCaffey his...

Total Woman Academy 07

by bhuff on Sep 13, 2017
Novels and Novellas

Ned entered his residence suite to the sound of running water in the bathroom. Inside the steamy room, he saw that someone was using his shower. Her hands vigorously scrubbed around a head and hair covered in shampoo suds. With her eyes closed against the soapsuds and the drumming water masking outside sounds, she made no sign of noticing Ned's presence. Tur...

The Librarians Apprentice Ch. 02

by MrRusty2000 on Aug 30, 2017
Group Sex

Part 1 Jimmy had been servicing the needs and desires of Miss Pringle, the library manager, for nearly a month. Even after all this time and hundreds of ejaculations into her various orifices, Miss Pringle was still never familiar with him but always very stern and bossy. After he'd done her most perverted demands she would revert back to form within second...

Gillian's Spanking Addiction Ch. 02

by 123z on Feb 26, 2019
BDSM

Gillian Watkins arrived promptly at eight in the evening at the Pimlico apartment building of retired school master Mister Williams. The twenty six year old online stripper and cosplay model had resisted many generous offers of sex from her most ardent fans and had not taken to even having girl on girl scenes on webcam either. The vivacious brunette just enj...