Granny Stockings Stories

43,233 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...

Drummer Boy - Down to Earth Ch. 02

by Lady_Dysprosia on Sep 25, 2017
Sci-Fi & Fantasy

Hello guys! Not much sex in this one, but a lot of necessary character-building. More depravity to come! - Lady D. ***** When Jason opened his eyes again, it was with extreme difficulty. The reward for his effort was a blurry image of his bedroom. He was laying on his crushed bed. Next to him was Granny, also laying on her back, with her eyes closed. On...

Sissy Lesbian Rita Meets Lisa

by maturesubmale_for_F on Apr 22, 2020
Transgender & Crossdressers

Dear readers, This is a continuation of my two already published stories: 'Miss Johnstone's Lesbian Sissy Slut' and 'Further Training as Sissy Lesbian'. I sincerely recommend reading these stories first as it provides background for this one. My stories have been well received and I would like to thank you all for the positive response! Enjoy and please ta...

My Pet, Fi Ch. 01

by Llyr_Heretic on Sep 24, 2019
BDSM

I walked in the door and there she was; sitting exactly as I had instructed: Blindfold on, hair braided in two braids, new dress, makeup done perfectly, except for nude lipstick. Pet always liked to show her sassy side somewhere. She would get her punishment for this later. Continuing on down: stockings (ah, my pet was trying extra hard to please me. It ha...

Worth The Wait Ch. 02

by ElderDirt on Sep 14, 2020
Romance

Author's Note: The first chapter of this story was told from Jimmy Romano's point of view. Written from Alyssa's point of view, this story describes Jimmy in greater detail and spans over five years beginning with friendship and culminating with...well...you have to read it to find out. Enjoy the telling. ~ ~ ~ ~ ~ People have told me that "love-at-first-...

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...

Drummer Boy - Back Into Hell Ch. 04

by Lady_Dysprosia on Jan 7, 2019
Sci-Fi & Fantasy

Drummer Boy: Bat Out of Hell II: Back to Hell Hello again, ladies and gents, Lady D here! I'd hoped to get this a bit earlier, but you know, holidays. Nevertheless, let's cap this year with the next part of the tale. Enjoy! * * * * * Jason found, to his surprise, that he wasn't falling. Or rather, if he was falling, he was doing a rather poor job of it. I...

Friends & Family Ch. 05

by kingswede on Sep 25, 2017
Mature

NOTE: This is one of the ongoing chapters of me growing up in the Midwest in the late spring and early summer of 1971 before moving to AZ to live with my grandmother and attend college. All persons in this and any of my stories are of at least 18 years of age and the names have been changed to protect the innocent. These chapters cover the times that I w...

A Tale of Two Grannies

by goodyearman on May 29, 2018
Mature

Probably my last fact-based story, happening during the four years before I finally got married for the second, and last, time. My first marriage didn't last for various reasons, but I am not going into that. I've ended this with a "cliff-hanger"! Obviously, I know how the events ended, but I'd really be curious to know what YOU think I found when I went ro...

Sissy Jessica Kinky Office Shagging

by Sissy Adele Howells on Aug 18, 2017
Fetish

Hi to all you kinky readers out there. I have been transported into a fantasy world, which resembles the office, in which I work. The women, that I fantasise about every working day, are about to reek humiliation on me for my past behaviour. Tied to a chair naked in a small box room, is not a comfortable way of spending your time over the early part of a col...