Sissy Stories

6,529 results
Orientation
Length
Source
Infinite Scroll

My Indian Slut Wife Vidya Ch. 08

by spankedboy on Sep 23, 2019
Loving Wives

Mr. Sarun visits us and stays for a week, enjoying my wife's hospitality. – Rajesh Author's note: This is a story of a cheating wife, of adultery, of cuckoldry and small penis humiliation. If that is not your thing, skip this story. And remember while adultery can be a great source of enjoyment in fantasy and erotica, in real life it damages souls and dest...

Mike & Karen Ch. 14

by BiscuitHammer on Jun 12, 2019
Romance

Mike & Karen Disclaimer: All characters are 18 years of age or older while actively engaging in sexual activity. This story is a prequel/sequel (sprequel?) to my other work, Alex & Alexa. As always, many thanks and gratuitous panty shots from Freja and Jeanie to my long-suffering editor and beta-reader for their assistance in polishing up and improv...

The Descending of Jessica Ch. 17

by Jessie92 on Sep 19, 2017
Novels and Novellas

Welcome back readers, thanks for coming on this journey with me. I know it's been a while, but life has been, well interesting of late. By my count this is the 17th chapter in what was supposed to be a three or four chapter story, and it's still not quite done. Well, the second part isn't done, obviously since these last few chapters were originally epilogue...

The Sissy Mark

by Son_of_Battles on Nov 2, 2020
Transgender & Crossdressers

This is my story submission for the Literotica Halloween 2020 Story Contest. I ask that you forgive any errors you might find, I literally just finished 12 hours before the deadline, and have zero time to get it to my editor before submissions close. As soon as Skye can get a chance to edit for me, I will repost a freshly edited update. Thanks, and don't for...

The Sultan's Hospitality Ch. 02

by Dariander on Sep 13, 2017
Erotic Couplings

Prelude I had originally not intended to write a second chapter for the story of the Sultan's Hospitality, but several people asked for more. In the end, what I wrote became so long (too much sex!) that I've had to split it into at least two chapters. This simple one chronicles Alex's journey back to the Sultan's palace. The next chapter, which is already m...

Georgie Girl Ch. 16-18

by coaster2 on Sep 18, 2017
Novels and Novellas

This story was edited by ErikThread and DaveT with my thanks and appreciation. Any errors are mine alone. Previously posted on another site. ***** Chapter 16 Discovery I slept that night, exhaustion and a lack of sleep the night before having finally caught up to me. I didn't remember my dreams although I'm sure I had some. We had eaten at a nearby restau...

American Mom Ch. 20

by Hardplay on Sep 25, 2017
Celebrities & Fan Fiction

Having left Afghanistan in the cloak of darkness, an unmarked CIA Lear jet approached company headquarters in Virginia early Monday morning. Arriving home a full week early following his successful mission, Stan Smith was literally shaking at the thought of seeing his wife Francine now that they had entered a breathtakingly exciting new phase of their rela...

The Gloves of Libedine

by embracelust66 on Dec 4, 2017
Sci-Fi & Fantasy

NOTE: All sexual acts described involve characters over the age of 18. ***** Fiona Diggs pulled open the heavy glass door of the thrift shop and stepped through, passing a couple of elderly women toting canvas bags stuffed with what looked like sewing fabric, socks and assorted books. She stood just inside the entrance, ignoring their disapproving glances,...

New Year's Party Favors Ch. 01-03

by SEVERUSMAX on Nov 8, 2017
Group Sex

Chapter 1 "Honey, do you mind if we play a new game tonight?" Stacey, my girlfriend of just six months, asked me rather abruptly as I trimmed my salt and pepper beard a bit to look more presentable for the New Year's Eve party that she had convinced me to throw on her behalf that year. "What, during the party? Are you wanting to add some cosplay or someth...

Jealousy

by jack_straw on Sep 13, 2017
Loving Wives

You read about and hear all the time about the husband who comes home unexpectedly, or shows up some place where he's not supposed to be, and sees his wife doing something he wasn't supposed to see. You always think it's going to happen to someone else, until that fateful moment when it happens to you. I wasn't supposed to come home from that particular bu...