Sissy Stories

6,529 results
Orientation
Length
Source
Infinite Scroll

The Teasing Air Hostess Ch. 05

by footslave85 on Dec 29, 2017
Fetish

The week after my Goddess gave me the chastity cage was a very strange one, I would get home from work and put it on, then spend the evening trying to go about normal things and not have any naughty thoughts. It was really difficult at first, every time I moved and felt the cage in my pants it made me instantly think of my Goddess and I started to get arouse...

The English Ranch Pt. 01 Ch. 06

by slave_william on Sep 19, 2017
BDSM

(Warning –this and later chapters describe William's participation in Pony play and describes heavy BDSM and pain scenes which may not be enjoyed by all readers. Do Not Read if you cannot handle this type of fantasy and please remember, it is fantasy. If you do not enjoy this story or any of my writings, I'm certain that there are thousands of other stories...

The Waitress Ch. 10

by goldsssnake on Sep 19, 2017
BDSM

You cannot use this story for any commercial purpose, and you cannot publish it in any website other than Literotica. Respect original writing. Thanks. ******* I dedicate this story to Connie the Hot Cunt, and its conclusion to miss X, there in Alabama. Thanks very much to all the readers that heartily agreed with me in my points of view that I expressed...

Art Deco Pt. 03

by Sputnik57 on Sep 14, 2017
BDSM

As they drove back across the causeway, he felt like he was home. It was great to get the fresh salty air back again after the heat of the ranch and enjoyable and intimidating as the other women had been- especially the formidable Carole- he still felt as though Dolores was his true mistress and owner. "I'm going to take you right back to my house, we are g...

Cream Buns After The Party

by Cumfusion on Sep 16, 2017
Transsexuals & Crossdressers

It was seeing Tony that really made me feel embarrassed. To be honest I had hardly met some of the others before. Gavin had been to the same school as the rest of us but he was several years older. Clive had actually been in my class but was generally seen as a bit of a swot, a sort of 'teachers pet' if you like. He wasn't as physically handsome as the other...

Larry's Cougar Ch. 08

by aimili_sage on Sep 17, 2017
Celebrities & Fan Fiction

September 2015 "I'm gonna fuckin' kill you, Harry," Tanalei said into her phone. "What is it?" he said worriedly. "Can you tell me why I'm starin' at a home pregnancy test and it's showin' two pink lines?" Silence. "Are you sure?" She took a picture and sent it. "Does this fuckin' look like I'm sure!" "I thought you were going back on the shot?" "My p...

Manning the Yard Sale

by AntaeusQ on Aug 18, 2017
Fetish

[Generously edited by CopyCarver from Literotica.] * My wife Susan spent all Friday getting ready for the yard sale. She painted the signs, typed up the Craigslist ad, and alerted her Facebook friends. She has a couple hundred of those, most her age, and a fair number recent mothers or pregnant. I used to give her grief about all the time she spent online,...

Crossdresser's Rassling Dreams

by footqueen99 on Sep 17, 2017
Fetish

The following is an email chain between two crossdresser's who enjoy wrestling. All persons depicted in this writing are well over 18 years old. ***** I wish i could have been there! I would love to see a few pics if u can share. I love pro style fantasy matches. I love all the holds, drama, trash talking and victory poses where u pose with your stocking...

Black Man One Ch. 13

by Weak_White_Wimp on Sep 19, 2017
Interracial Love

My insecurity continued to grow with each passing day during the next three weeks, as did the insecurities of the other 12 white husbands in our little condo community. Each day during the work week while the husbands worked, the young black stud had all of our wives hanging around him at his soon to be gym. The white wives continued assisting and preparin...

Black Man One Ch. 02

by Weak_White_Wimp on Sep 19, 2017
Interracial Love

My military career was challenging. The workouts were exhausting but somehow I got through it. For a period of time I even learned the sport of boxing, which was basically pushed upon many of us by our staff sergeant. I was 28 at the time. Staff Sergeant Williams seemed to have a way to persuade us to do anything. He was really tough on us. Generally, he "pi...