Old Maid Stories

180,134 results
Orientation
Length
Source
Infinite Scroll

Naya and Gary

by pikestaff on Jun 25, 2019
Exhibitionist & Voyeur

Here's how I once changed the entire outlook on sex for a workmate, after his divorce, with the help of an "Old Maid." Working night-shifts on security was boring as hell, sometimes. It was okay when there was trouble to deal with, but most nights were spent sitting around the guardhouse trying to pass the time. One of the other guards I got along with - a...

Missed 02: Ffordes Castle

by oggbashan on Jul 15, 2020
Romance

Copyright Oggbashan June 2020 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. This is a sequel to Missed: Fenian Outrage. **********************...

The Maid and the Pizza Guy

by hollandguy on Sep 13, 2017
Transsexuals & Crossdressers

My name is Ryan I am 33 years old. I am 6'1 #200 with auburn hair and brown eyes. I am not in the best shape anymore but I wouldn't call myself fat either. I have been cross-dressing since the age of eleven. It started with just panties but has evolved to full dress over the years. I work as an electrician and take on side jobs when I can. With the recent...

Becoming a Sissy Maid & Slut Vol. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Title: How I became a Sissy Maid and Slut for a Dominant Master. Preface: I would like to begin by thanking all who will read my story here. This is a sissy story based on many thoughts I have imagined, many times throughout my life. These erotic thoughts have been enjoyed for a long while in my life. Like many sissy girls, stories like the one I will wri...

Revenge Is Sweet

by fantasygirl30 on Sep 1, 2017
Humor & Satire

Geena was so mad she wanted to break everything in her house. Dave had used her, but she didn't see it until now. Actually, she didn't want to see it until now. Those smoky eyes, his easy-going laugh, how he charmed her into having sex with him. Not just one time, but many. And Geena, always aiming to please him, gave him blow job after blow job when he ra...

Fat Frank

by LustyLee77 on Sep 12, 2017
Group Sex

Joan kissed her husband Tom goodbye and told him to have a good day at work. She poured a second cup of coffee and wondered what she was going to do today. The chime of the doorbell interrupted her thoughts. Opening the door, she was pleased to see her friend and neighbor Laura. They sat at the kitchen table chatting and drinking coffee and juice. "How is y...

Becoming a Sissy Maid & Slut Vol. 10

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Seventeen: It's time that Chantel Earned Her Keep. Well it's the morning of a Saturday, to where by night time I will soon be doing some true sissy slut street walking and now truly begin to earn my keep and begin to earn some serious money for my Master. I awake like all other mornings at 7:30am and follow my morning routine, enema, shower, shave...

The Neighbour Ch. 02

by mw0212 on Aug 30, 2017
Fetish

Jessica was on her knees in front of her master. Naked but for her knee high cream coloured boots and one singular leather glove which now was wrapped around the first cock she had ever seen, let alone held or tasted. She slowly worked the cock into her mouth, tasting the salty pre-cum which had formed around the tip. She felt two hands on either side of her...

Sissy Chantel, New Reality Ch. 05

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Five: Oh, Oh, My Surprise. "Ohh, Ahhh...Wha...what." I say as I wake up and am lost with where I am and what is going on. "What the... What the Hell? Where am I and what is this? Huh, what the Hell? Why am I chained and padlocked around my waist?" I'm groggy and very confused as I look at the room, dimly lit with a single hanging light bulb, I'm on...

Dark Assassin Ch. 04

by zinfer on Sep 14, 2017
Sci-Fi & Fantasy

As I mentioned in my last chapter, this chapter and the next two will explore some of our darker characters (King Slynt, the Drow King, and Talia). This is your warning There is a scene of dubious consent in this chapter. It is not vital to the plot, but displays an important character trait of King Wyatt's. It involves the use of a position of power for s...