Granny Sissy Stories

8,964 results
Orientation
Length
Source
Infinite Scroll

Scales like Stars Pt. 06

by DragonCobolt on Jun 4, 2018
Sci-Fi & Fantasy

Bex Thresh, of the Singularity Principalities, knelt low and touched his snout to the obsidian floor of the Pulsar Castle of House Xosh's freehold. His palms spread and despite hardening his scales for the kick, the impact of the Bryaugh bruiser that stood to the left of him still felt like being hammered by a gravity-drill. Bex rolled and tumbled, then came...

A Sissy Saga Ch. 02

by Snurge on Sep 15, 2017
Novels and Novellas

When Jennifer went out onto the terrace William was nervous but relieved to be with someone his own age and gender, even if that person had been sissified just like himself. The two eighteen-year-olds regarded each other and their feminine attire silently for a moment before Archie at last broke the tongue-tied awkwardness. "Better make a start," he said,...

Sue Oliver: Gilf Goddess

by Samuelx on Jun 25, 2019
Interracial Love

Meet Joseph Marc Antoine, a young Black man of Haitian descent living in the City of Ottawa, Ontario. Joseph is a brother with something of a dilemma. Lots of brothers have a predilection for chasing White women, and that's far from uncommon. Still, Joseph's situation is fairly unique. He doesn't like today's lively, fearless and outgoing young White women w...

Second Chance at Love Ch. 08

by andy_r_14456 on Sep 13, 2017
Mature

Before they went to the university together, Alice and Eric invited a few of their friends and family members to a picnic at their home. At that picnic, Art, a friend of Eric, and Dorothy (Dot), Alice’s mom, were introduced to each other. Art found Dot to be a beautiful elegant woman, about 5’ 3’’, 130 lb., who appeared to be younger than her 63 years age. S...

Grandma's Friend

by rapidone on Aug 1, 2018
Mature

So Gramma and her friend have a habit of washing themselves in the creek that flows through our family's farm. I had seen this for years and thought nothing of it, though I always tried to watch them, being a horny 18 year old. It didn't matter to me that they were old or that one of them is my own Gramma. I've seen Gramma lift up her loose skirt and wash h...

Fuck You TV Ch. 02

by DickThePimp on Dec 2, 2019
Celebrities & Fan Fiction

"OH MY FUCKING GODDDDDDDDDDDDDD!!" Jamie Lee Curtis leans back, riding my fourteen inch cock, on my brown leather office sofa, while I look at some program notes my wife Kim Kardashian handed me when she walked in about two minutes ago. Jamie Lee's eyes roll back in her head, her body smack dab in the middle of a full body orgasmic spasm. My cock gets that...

The Wedding Ch. 02

by betamale08 on Mar 31, 2020
Transgender & Crossdressers

The Wedding (Patti Cake Part 3) Chapter 2 -- Party in Pink Purgatory... "Oh Wow Dale! You look fantastic! Very -- Very pretty... I can hardly tell that you're my boy anymore! Really sweetie I'm so impressed -- and Patti you look gorgeous too... I knew that dress would look stunning on you -- but Dale -- my pretty -- pretty -- son... That dress is perfect;...

Mrs. O'Malley's Golden Juices Ch. 09

by milfleglover on Sep 25, 2017
Fetish

Susan watched young Amy kissing Alana and smiled as best she could, what with her mouth locked around one of Alana's wrinkled old tithes. Amy's eyes were closed and she moaned as she thrust her tongue into Alana's mouth, the age difference of 46 years not bothering her in the least. Nor did whom she was making out with - her grandmother, whose own eyes were...

Friends & Family Ch. 06

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...

Home Gym

by Bob_6 on Sep 13, 2017
Loving Wives

Phone rang early on Saturday morning; I was still asleep, it was my weekend off work and wanted a lay in. I wasn't going to answer it but when I looked at who was calling; it was my brother's home number. I answered the phone, "Hello," in a groggy morning voice. It was my brother's wife Tracey. Tracey was twenty-two and an athlete, a four hundred meter run...