Sissy Stories

6,529 results
Orientation
Length
Source
Infinite Scroll

Sister Act

by Cat_photobuff on Sep 15, 2017
Group Sex

Cat hated to fly. Rather unusual for a former space flight engineer. Flight simulators were okay, but she just didn't trust the commercial airline industry. Probably a result of listening to disgruntled aeronautical engineers and mechanics complaining about how much they hated their employers. Oh and lets not forget the pilots who sit in airport lounges drin...

April's Fool

by AuroraErotica on Mar 23, 2020
Erotic Couplings

Chapter 1 March 31St - The day before. April is a therapist, specialising in couple, and marriage counselling. She was from the city, and was on a short break from work, in a country town named Daylesford. Daylesford is well known as a place to seek spirituality, meditation and relaxation, and April was in the mood to indulge in a week of pampering. She...

Bill and Linda's Vacation Ch. 03

by pascofun1234 on Oct 12, 2020
Interracial Love

Recommend you read chapters 1 and 2 to get a feel of how we got to this point. This includes interracial play, mild domination by a woman and bisexual play. If this is not for you please move on to the next story. No need to berate this story because it includes themes that you don't enjoy. All involved are over 18 years old ======================== Lin...

Trailer Trash Tranny Ch. 07

by Travel_by_day on Sep 26, 2017
Transsexuals & Crossdressers

Chapter 07: Odyssey Jeannie boarded the bus in Omaha, excited to be finally moving to New York City and starting her dream. In her hand, she was clutching her tickets to New York and a catalogue from a school in New York that offered a fashion design degree. She could feel her heart beating quickly in her newly enhanced chest. Unlike the clothes which Jean...

Same Time Next Year

by DG Hear on Sep 12, 2017
Loving Wives

There is very little sex in this story. I do want to thank my editors LadyCibelle and Techsan for making my story a much better read. * A while back a couple of friends of ours stopped by to visit. We've known Bob and Maria for most of our married lives. Maria worked with my wife, Trina at a large well-known travel agency. The company has offices in a numb...

Courtesan Ch. 23

by Goodhusband on Sep 19, 2017
Loving Wives

This is the twenty-third episode in a series entitled "Courtesan". If you have not read the previous twenty-two episodes of this series, I encourage you do so before beginning this chapter. "Courtesan" is romantic story about a dominant hot wife and her submissive cuckold husband. While they have a deep and abiding love for each other they do lead an altern...

Sometimes the Good Guy Wins Ch. 08

by Scorpio44a on Sep 19, 2017
Novels and Novellas

Kathy said, 'About three hours ago I was having dinner with three women I work with. They were talking, complaining really, about the love they aren't getting. They are married and wanted to know if I shared their feelings of loneliness, of not being taken care of. I told them I touch base with you every day and that every time I touch base I know I am loved...

My Cuckold History

by jj62 on Jul 18, 2018
Loving Wives

Hi to all I am a member of both a cuckold forum and a chastity forum where members have been able to read about the relationship my wife and I have enjoyed. I hope Literotica readers will welcome the same opportunity. I have unashamedly cut and pasted my story from the forum postings, where it has been up for quite a while. But since it is my own work then...

An Interview with Superman

by FrancisMacomber on Sep 13, 2017
Loving Wives

He didn't look that weird when he walked into the room. Actually, he had a nice face with a pleasant smile, and it was clear that he worked out regularly. But there was no getting past the blue spandex suit, the red cape and, of course, the big S on his chest. For at least the tenth time I silently cursed my editor for assigning me to write a story about a...

Chloe's Story Ch. 01

by MandyM1 on Sep 16, 2017
Novels and Novellas

The Dilemma As the tattooist's needle pierced my delicate skin and the painful process of inscribing the company logo above my bare pussy proceeded, I began to think again of all the chaos I'd recently caused. Derrick's bankruptcy and impending incarceration, the rapes of Carla and Amber, and the anguish that awaits my husband. I knew too what awaits me, th...