Jennifer Milking Stories

28,500 results
Orientation
Length
Source
Infinite Scroll

When she comes home from work

by erinpiers on Jul 30, 2019
Transgender & Crossdressers

"I'm heading to work," my wife called out, I came to the lounge room to kiss her goodbye, the joys of days off. She looked the epitome of business sexy, knee length black pencil skirt, white blouse and black jacket, her hair relaxed down to her shoulders, the blouse accentuating her figure, tan Cuban heel stockings would be buckled onto a garter belt and b...

Wife Pounding

by oriondog on Dec 24, 2019
Loving Wives

Think about this. You're on top of my wife. Your hard cock is moving slowly in and out of her slippery, soaking wet cunt. Your cockhead might be going straight in, but you flex it upwards. So it presses against her innermost & upper part of her of her hungry pussy on the way out. The both of you have developed a slow, steady, and hot rhythm. You both work to...

Personal Time

by jjgarces on Dec 9, 2019
Erotic Couplings

I have never been one to dream up situations in my head where I end up with a woman that I barely know or know only on a professional level. But that all changed not too long after I started seeing this girl named Melissa for employment sessions. Everyone told me that the affection she seemed to show towards me was just her way of being nice to one of her...

Hunting Trip

by Brian6588 on Dec 9, 2019
Mature

Three years ago I headed up North to the cabin for deer hunting. I was meeting a group of guys there but decided to go up early and get the cabin ready. The only source of heat is a wood burning stove. We winterize the cabin but have an outhouse for use when we shut the water off. It was cold in the cabin and I got a fire going. While the cabin warmed up I...

Olivia & Travis Celebrate Xmas

by TravisOlivia on Jan 21, 2020
Erotic Couplings

Welcome readers. This is a true account. I hope you enjoy the story. *************************************************** Travis had worked at the hardware store for 10 years. Five of those years were spent in close contact with Olivia, the store manager. She had long, beautiful black hair. Sexy brown eyes made even more alluring with the dark eye shadow s...

Discovering One's Self

by warotto on Dec 23, 2019
Mature

I still remember it like it was yesterday. The sun was shining on a warm upstate New York summer day. As was typical, a bunch us would get together and hang out. Growing up in the 70's and 80's without video games, you had to have friends to do things with. Little did know, nor expect, that it would lead us to this day. There I was, an 18 year old guy who j...

A trans threesome

by mrtranstastic310 on Jun 8, 2020
Transgender & Crossdressers

Author's Note: It's a build up story, so if you're looking for a quick fix, this probably won't do it for you. :) Additionally, the below includes references to transmale genitalia using traditional "feminine" language. ____ Wiping the steam from the mirror, I stepped back. It's been almost 8 years since my first dose of testosterone, and still, this body...

Bodyguard to the Stars Ch. 01A

by Scarredheartangel on Jun 1, 2020
Celebrities & Fan Fiction

Matthew watched Kit Harington swing the sword with a few practice swings, then turned his attention to his client. As usual, she looked phenomenal. Long, slender legs travelled all the way up to a perky, firm ass. Her stomach was toned and her breasts were small but pert. She was wearing a sky blue silk dress, her dirty blonde hair braided for her upcoming...

Little Lost Puppy Pt. 06

by Tombescent on Aug 24, 2020
BDSM

Alex got up early, made breakfast for himself and Bubbles, got her situated in her crate, and then sped off to his office. As quickly as possible he took care of the last few things that needed to be taken care of, attended what seemed like the longest client meeting in the history of the world, verified with his boss that his vacation started Monday, and wa...

Slut Barbara

by JuiceSpot on May 21, 2019
Exhibitionist & Voyeur

All characters and events are purely fictional. All sexual acts are among consenting adults that are 18 years or older. ***** Barbara was petite, blond and had finished college. Her marriage had ended and was quickly put behind her, however, the one thing that she did miss was the frequent sex. She was accepted to a prestigious business school in Florida...