Free Granny Crossdresser Videos And Stories Stories

1,000 results
Orientation
Length
Category
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com
Create your own smut fantasy with AI

First Time Slut

by playtime2728 on Sep 14, 2017
Illustrated

The following is the true story of my first experience with a man: Where to start? For the longest time I didn't realize I was bisexual. I'm pretty sure it started with porn. When we turned 18, one of the first things my buddies and I did was make a trip to the local porn shop on the seedy side of our town. It was incredible. Looking at all the toys, linger...

Magnolia

by FantasyXY on Sep 14, 2020
Loving Wives

Our radios had been squawking like a mob of magpies for at least half an hour. That amount of chatter was unusual for that time of day. Something big must have happened. "Unit Twenty-Four, what's your ten seventy-seven for Magnolia?" That was the latest thing from dispatch to come over the squawk box. Ten Seventy was a request for how long it would take to...

Just Do What The Nice Man Says Honey

by Michele Nylons on Apr 22, 2025

Julie Cashmore followed her gentleman caller downstairs and escorted him to the front door. She opened the door and looked both ways up and down Clifton Road and seeing that the street was deserted she nodded to her gentleman caller who bustled past her most ungraciously and quickly strode away. He did not want to be seen leaving 32 Clifton Road; none of her...

Paq'o's Potion (Jacy is Bored)

by JonThomas_ on Sep 15, 2017
Sci-Fi & Fantasy

Jacy Etergen is the heir to the throne of a defunct Inca tribe. Add that fact to three dollars and sixty five cents and Jacy has the exact amount of money she needs to pay for a Grande size caffe latte. But it's still better to be a queen, than it is to not be one," she thought. Jacy always buys caffe latte when she's stressed, and needs to be comforted. Th...

Granny Babette's House

by Samuelx on Mar 6, 2018
Mature

Meet Babette Grissom, also known as Granny Babette, a sixty-year-old black woman living in the City of Ottawa, Ontario. At first glance, Granny Babette looks like any of the charming old ladies you might run into your local black church. She's lovely, friendly, well-dressed, and deeply concerned about her community. Granny Babette doesn't have a family, so c...

Drummer Boy - Back Into Hell Ch. 02

by Lady_Dysprosia on Jul 25, 2018
Sci-Fi & Fantasy

Drummer Boy: Bat Out of Hell II: Back to Hell Howdy boys and girls! We're finally back in Tarterus! And they say you can't go home again. Enjoy! * * * * * "Okay," Leanne said. "That's a new one." "You've never heard of this Thing in the Way?" Jason said. "No, I haven't," Leanne admitted with a thoughtful look on her face. "Does explain a few things...

Our Own Little World

by silverfox_granny on Sep 12, 2017
Mature

Note: I wish to thank the many that have written to say you've thought of starting your own local seniors swinging group. I wish you well in this adventure. We seniors have to have a place to enjoy ourselves in these "Golden years" To the two ladies that have been writing I think you're on the right path. I'm a widow also and yes, I see no reason you shoul...

Granny Calls Young Male Escort

by Hotnjuicy on Mar 6, 2018
Mature

I had a female friend who ran an escort service. One winter night she called me and asked if I'd do her a big favor. She had just received a call from a 66 year old widow who wanted to have a man visit her and asked if I'd call her. I had never done anything like this before, but was excited by the idea. I told her, "Yes." I' was 22 years old at the time....

Free Spring Break Accommodations Ch. 02

by acup on Sep 25, 2017
Romance

LEGALESE: Don't read this if you are underage, if it is illegal in your area, if it is offensive to you, or if you cannot distinguish fiction from reality. This is a work of fiction. All sexually active characters are above the age of consent on their planet of origin. Copyright (c) 2016 by Acup A word of warning, I write good stories, I hope, with some d...

Latina Granny Ch. 02

by BilboMerkin on Sep 15, 2017
Mature

A big thanks to those who made comments. You helped me realize how important Trent is to the story. ***** "I am in control. I know what I'm doing. I am in control." I kept repeating this over and over to myself. It was my mantra. I was in control. I knew what I was doing. I would not lose control. "Then why," I asked myself, "Am I dressed in one of my...