Granny Sissy Stories

8,964 results
Orientation
Length
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Infinite Scroll

The Domme Club: The Fucking

by NancyPan on Sep 14, 2017
Fetish

This story will likely be most enjoyable if it is read after reading The Domme Club and one or two other stories in the series (for background of Tom and Monica's relationship and how Tom has previously been humiliated in front of the Domme Club.) Respectful comments are appreciated. ***** Mistress Monica left Tom the standard list of chores to do while s...

Suspected Affair

by 69Jance on Apr 21, 2020
Transgender & Crossdressers

I had suspected for a while but recently found confirmation, not that I would blame her. I know we loved each other but I also knew there were needs the other could not fill. I found evidence she was having that need I could not meet, met by someone else. I was a bit jealous but in a strange way. There was no anger but a bit of arousal as I imagined her love...

Another Day at the Office Ch. 01

by mslstoy on Sep 12, 2017
Transsexuals & Crossdressers

Until that Monday I would never have believed what life changing events could happen on such a dull autumn day. The alarm had gone off (as it always did) at 6:30, time for a shower and work, it didn't even cross my mind that I hadn't had time to do any washing that weekend, or at least it didn't until I went to get dressed. "F@#k, what am I going to wear no...

A Sissy's New Daddy Ch. 04

by sissyneko on Sep 25, 2017
Transsexuals & Crossdressers

It was with great pleasure that I am finally able to upload chapter 4 of "A Sissy's New Daddy" I have spent the better part of a year working on this chapter. I was surprisingly hard to get down on paper. I want to thank all the readers that have taken a time to comment and rate the chapters of this story. It has meant a great deal to me and has at a few dar...

Sissy Blane's Liquid Assets

by EvelynT on Sep 14, 2017
Fetish

ONE The Plumrose Dossier I became familiar with the Plumrose Dossier one cool February morning when it was read to me in the private rooms of Madam Harding at the Clinic. I'd arrived that morning for my weekly 'therapy' and had only enough time to hang up my outer clothes in the Sissies' cloakroom and don my Eva Gabor wig before a facilitator poked her he...

Lois Lane's Night Out

by exxxidor456 on Aug 13, 2017
Fan Fiction

As with all my stories, I welcome other authors to add chapters! Remember to like and bookmark your favorite chapters! Regular chapters with 5+ likes get a sequel, chapters with 10+ likes get two. End chapters get an epilogue with 10+ likes. Chapters with the most likes & bookmarks get updated first! All characters in this story are at least 18 years old...

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Mistress Chronicles Ch. 05

by MistressMtoyou on Sep 25, 2017
Fetish

Background: This story involves my on-line subject Nancy, who I introduced in Mistress Chronicles 4. We've had no in-person relationship. In fact, in all of our sessions Nancy has never actually seen me. I have sent him pictures that I have told him look similar to me, but never an actual photo. * By way of background, Nancy is a computer nerd. Brilliant...

Lynn and Leif Forevermore Ch. 45

by mich80new on Sep 15, 2017
Interracial Love

Dear Readers, Thank you for your feedback as you are reading the story. Your comments keep me going. I appreciate the patience of each and every one of you who is sticking by this story and enjoys reading about the sexuality and emotional growth and development of these two characters. I'm writing the story for each and every one of you....

The Making of a Mistress Pt. 05

by EiryCGar on Sep 14, 2020
BDSM

Author's note: Marie has married and taken possession of Charles, now known by his initials as Cunt. She has become an official Hotwife; Cunt is now a true cuckold. This chapter deals with their honeymoon on Felicity's island, and the momentous decision that is taken when she and Cunt return home. As always in my fictional stories, all sexual acts take plac...

I was Wearing Panties When We Met

by anonymouspeggy on Mar 2, 2020
Transgender & Crossdressers

It started when I was young. I guess that's how it works for everyone, right? I had a sitter-a hot, older girl who was the object of my young dreams-who was into theater. We'd spend afternoons putting on plays. Sometimes she had the boys play female roles. She even dressed us up. I guess something about it just felt right. Something stuck. Of course, a grow...