Milf Sissy Stories

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The Seductive Seed of a Tranny MILF

by SugarandSalt on May 28, 2019
Transgender & Crossdressers

Jackson got home and immediately curled up in bed. He didn't want to move for the rest of the weekend. He'd finally worked up the courage to ask a co-worker out at work. She politely rejected the invitation. Then later on in the day, Jackson spotted her flirting with some musclebound blockhead. Seeing that was like having hot coals dumped over his head. Twe...

Walk a Crooked Milf Ch. 02

by MicheleNylons on Nov 16, 2020
Transgender & Crossdressers

Chapter Two - Don't Be a Sissy! "I'm not sure I like you referring to me as a MILF," Mrs Cashmore said. I had counted the hours until I was back in Mrs Cashmore's house. Much to my mother's regret I had not elected to go on to university and had taken a job in a hardware store to help my mother pay the bills. I had told her that I intended to continue my e...

Sinful Degrees of Separation Pt. 05

by shoguy on Sep 26, 2017
Mature

In this story best friend stacked, Jewish MILF attorney fucks 2 black studs and 18 year old German stud. Powerful MILF Attorney At 60 she was a mother of twin college aged girls who were in their first year of college. Not only sexy but she was one of the most powerful and feared attorneys in Los Angeles. She represented very wealthy clients in the commerc...

Topped from the Bottom

by cutebabysadie on Sep 14, 2017
Loving Wives

I have always been a stud. It was nothing new to me, it was just who I was. I remember, when I was little I ran the playground. In middle school, I was the only one dating a girl in High School. And in High School, I dated the prom queen and was a star in 3 different sports. I got a full ride to college and beat out a senior college quarterback to become the...

Swapna

by zorosav79 on Feb 6, 2018
Interracial Love

First of all, please forgive me for any spelling mistakes or for using simple words as English is not my first language. My name is Erik and this will be a story about real events that happened to me a few years ago. I was an exchange student in Northern California having arrived Austria. It was hard to live far from your family but being a student was alway...

Sissification 101: Ch. 01

by silkstockingslover on May 4, 2020
Fetish

Summary: Straight guy is caught watching sissy porn and...Note 1: Thanks to Eric who requested and helped plot this lengthy story. Note 2: Thanks to Tex Beethoven and Robert for editing. Note 3: All characters are at least 18 years old. Sissification 101: Ch. 01 1. MY SISSY CURIOSITY I've always liked nylons. I grew up when they were still popular and...

Confessions of a Tgirl Slut

by Sissypansyfairy on Sep 13, 2017
Transsexuals & Crossdressers

When the day started, I had no dates, no arrangements of any kind. But I was feeling horny. I needed cock. I'd gone over a week without sex and I am one cock hungry sissy slut. I'm getting on a bit but I know how to dress and do my makeup. I like to think I can embody a straight guy's fantasies and give him the sex his wife won't and dress in a way genetic w...

Real Life Adventure of a Cuckold

by stevecraigslist on Aug 18, 2017
Fetish

This is a true story of a recent adventure. Let me know if you like it at the address in my profile and I will post more. * I met Lydia from a posting on craigslist. I was in the habit of posting a variety of ads every week in the casual sex section, trolling for playmates. Sure, the odds of getting a date out of an ad were low, but what was the cost? And...

Micropenis Under Vesuvius Pt. 02

by Fella101 on Oct 8, 2019
Fetish

(Author's Note: The historical and archaeological details are generally accurate, but not immune from narrative anachronisms or oversimplifications. You'll learn a little bit about Roman culture and history, but nothing too educational.) ***** As if taunting me, a crudely gargantuan phallus had been etched into the lefthand side of the bathhouse doorframe....

HypnoSissy: Educated to be Pegged

by silkstockingslover on Aug 13, 2019
Fetish

Summary: Cock sucker's training is advanced to hypno videos on anal sex. WARNING PLEASE READ: -This is a hypnosis story with potentially influential subliminal messages within it. -The story also contains hypnosis video scenes. -So if you begin behaving differently after reading this story and all your friends start pointing fingers, don't come crying to...