Sissy Guide Stories Stories

1,000 results
Orientation
Length
Category
Source
Infinite Scroll

How to Become a Sissy/Cuckold

by Quietoldie on Sep 14, 2017
How To

This is a How To Guide for Sissies and Cuckolds. Please do not read this guide if you have no interest in the cuckold/sissy lifestyle. Like most couples these days both partners will be doing demanding full time jobs. Traditionally husbands have done gardening, cleaning the car, putting out the trash, performing do it yourself jobs around the house, drivi...

A Sissy's Date Night

by nadia603000 on Oct 19, 2020
BDSM

Author's Note: Mistress Pepper and Sophie are "anonymized" versions of me and my slave-girl. The real me. All of my stories are (or should I say will be) my memories of a session with a sub. Thus, they are true stories. Only in this version details have been changed to protect the sub. I do live in Mobile about 10 months of the year (the remaining two I spe...

Sissy Prince: Origin Ch. 02

by SatinSlip on Feb 6, 2018
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** "I'm sorry about this." Jentif whispers in the Elf's ear. Larallin gives a slight nod. The big red woman was actually quite nice, and the wife of his new friend Oliver. But, like the rest of the slaves, she would do anything their monstrous master ordered. The ginger, Elf man...

A Sissy Saga Ch. 09

by Snurge on Sep 15, 2017
Novels and Novellas

Miriam Hancock arose in the morning alone but feeling joyous and revitalised. But when her early toilet had been done her smile faded, and she frowned. On the dressing table lay the fat envelope she'd received that morning from the lawyers employed by Lady Diana. It enclosed a letter that was dreadfully succinct. '... Our client as brought to our attention...

Panty Consequences No. 03

by PantiesAndPies on Sep 14, 2017
Fetish

This series of stories are all standalone so can be read in any sequence. They are about my favourite fantasy --- my first time wearing, or first time being caught wearing panties. Obviously then they all involve lingerie wearing men and the consequences may include cuckolding, creampie eating or cock sucking men amongst other things. If any of these are lik...

2016 Literotica Reader's Choice Awards Winners

by Literotica on Sep 16, 2017
BDSM

The stories and authors below were chosen by our readers as the best of 2016, in voting which took place here. Though these are not the only wonderful authors and stories on Literotica, they are worthy of praise and recognition. Thanks to all of the writers for providing us with hours of hot reading, and to all of the readers for your input, support, and a...

Neighborly Relations Pt. 04

by grizzley123 on Mar 25, 2019
Fetish

Author's Note: As is true with all of my stories, this is a fantasy. The themes and ideas I find erotic might be different than yours, that's ok. Please leave comments, my ego will appreciate the positive ones, the writer in me will enjoy the constructive ones, and the submissive side of me will accept the berating ones. Enjoy! *********** It is best to re...

A Dream Come True

by MoogPlayer on Sep 19, 2017
Romance

Thank you all for everything you've said about my stories, I really appreciate it. Here's another one that I hope you all enjoy. It is a fictional story, as are all of my tales so; be sure to remember that anything CAN and usually DOES happen in a fictional tale. Oh, and don't forget to vote; and remember that, as always, I pray that you all find peace and G...

Gloryhole First Timer Pt. 01

by Urtoy2be on Aug 31, 2017
Fetish

I want to start by saying that all of my stories are purely fictional and in no way should be taken for more than erotic fantasy. Having said that I will say that the characters I write about are real people in my life that I use for inspiration only. Their names and personal details have been altered to protect their true identities. If you like my storie...

My Dom's Decisions

by davesubboi on Oct 12, 2017
BDSM

The thought of being submissive and letting another superior being guide, direct and change me has become one of my driving desires. Over the past 15 years I have realized I am much better at pleasing others and have determined based on numerous online doms/master/mentors that I really should not care about my own pleasure if I can serve another and give the...