Training Eileen Stories

37,048 results
Orientation
Length
Source
Infinite Scroll

Birth of a Slut Pt. 01

by Njcdslutgina on Oct 6, 2020
Transgender & Crossdressers

Recently I decided to share my story of how I became a cross dressing slut. While always turned on by stockings and heels my first real chance came after I turned 18 and went to my first adult costume party. A little more about myself. At 18 I was 5'11", 175. I had long hair which was the style of the day cut in a shag. My cock is small, 5 inches but I have...

A Fantasy about Love Pt. 14

by Buzios1971 on Mar 2, 2020
Romance

Chapter 51: A Tranquil Takeover I changed seats and let her drive back to Sydney. She had put the hood down and with her funny little hat looked the perfect rich young society lady. We arrived home before Maureen and Jenny immediately put everything away. She left, got flowers and fresh food, and I looked after the music. Then we waited. Suddenly I felt Ma...

Her Blue Dodge Minivan Ch. 01

by ohio on Sep 13, 2017
Loving Wives

[Author's note: This story is inspired in part by an incident from one of the many terrific stories by Harddaysknight. I hope he'll forgive me; after all, as Mark Twain should have said, "plagiarism is the sincerest form of flattery".] [Author's note #2: The continuation to this story will probably not appear right away.] * There are certainly lots of blu...

Wild Girls In House On The Hill

by Hornyman69WithU on Sep 16, 2017
Group Sex

Back in the late 70s, I had just transferred my sophomore year in college to a new university where I knew practically no one. I was taking a way-too-easy Spanish class and spotted a pretty good-looking girl on the other side of the room. She had a really pretty, Eastern European face, was of medium height, and had long, perfectly straight brown hair down to...

Northern Lights

by Wark2002 on Oct 5, 2020
First Time

Northern Lights By Richard Wark August, 1975 Deliberately, noiselessly, careful not to awaken the four guys in the tent, I zip the door shut and take a few steps into the woods. Even with the flashlight in hand, I have to pick my way carefully through the trees and bushes. Once I'm behind a row of trees, halfway down to the lake, I snap off the flashlight...

The Student Teacher Ch. 02

by The Style Guy on Sep 12, 2017
Mature

Thanks to Nstygirl for her continued assistance with my story. I greatly appreciate the feedback, comments and encouragement I received from chapter 1 and hope this chapter is worth the wait. There will be a final chapter 3. Other than some back ground and character development, it's not necessary to read chapter 1. TSG * I woke early on Tuesday morning...

Eileen

by _Lynn_ on Sep 14, 2017
Non-Erotic

Frank was gone. He packed his belongings and left. Eileen thought he loved her, that he was looking forward to having children with her, growing old together. A stockbroker by trade, Frank was intelligent, funny, and handsome. Her career in accounting brought in a decent income too, together allowing them to take exotic vacations and drive nice cars. Yet Fra...

Denise and Eileen Pt. 05

by Pocketrocket2 on Nov 16, 2020
BDSM

In part 4 we left the two ladies having had incredible oral sex. For Eileen it was her first time for both receiving then giving with a woman, then Denise, on a whim decided to give the peeping tom across the valley a final flourish. The ladies sat and continued to look through the huge binoculars at the masturbating goliath across the little valley. They...

The Group Ch. 02: Steve Impresses the Members

by DarkDeliciousDebauchery on Nov 4, 2019
Group Sex

This is the second part of the series titled "The Group." After being persuaded by Eileen, Eve, and Susan to let their Group use his Loft, Steve gets to meet the rest of the Group's Members. Feedback from readers will help me decide which direction to go with the story in the future, as well as which characters to develop. Thanks for your input. ***** "...

My Naughty Neighbour Ch. 09

by BiscuitHammer on Sep 25, 2017
Erotic Couplings

Chapter 9 - A Surprise Treat Lynn's note had given me the address of very posh strip club in Chicago's lively night district. Pretty sure my Hugo Boss attire is what got me in because lots of guys were being turned away by the bouncers at the door and said rejects were universally wearing jeans and t-shirts. The bouncer nodded to me and let me in without s...