Sissy Stories

6,529 results
Orientation
Length
Source
Infinite Scroll

Black Man One Ch. 21

by Weak_White_Wimp on Sep 19, 2017
Interracial Love

It was apparent from the start that we had not rehearsed what we wanted to say to one another. It was more obvious that Julie didn't want to be there at all. I had not expected to be having this embarrassing opportunity to speak to her at this time. Nor, did Julie expect to be speaking to me. The conversation began rather slowly and tentatively as we "danced...

Life as a New Hire Ch. 15

by FinalStand on Sep 18, 2017
Sci-Fi & Fantasy

This story plays fast and loose with Ancient History and Linguistics; be warned. Just as echoes pollute sound, the echoes of our histories pollute our view of the World. I had to fall back on a dedicated group of readers for editor assistance. The faults are mine. ***** (Wednesday Night) Yasmin had a kink I hadn't really had to deal with before. She lik...

More Tales from the Guilds Ch. 01

by voluptuary_manque2 on Jan 1, 2019
Sci-Fi & Fantasy

"Wizards and witches always know when they will die," Havelock Vetinari proclaimed to his 'friend' Lady Margolotta, Ruler of Überwald, over dinner one evening, "unlike the 'Differently Alive' who mostly have no reason to believe that they ever will." "Qvite so," she responded archly, "und your point is?" "I'm just musing on the fact that while the Watch,...

Life and Time of Lady Vargos Ch. 10

by rik581 on Mar 25, 2019
Transgender & Crossdressers

Chapter Ten "The Vow and Portrait Ceremony" It would be a night to remember for the guest that were arriving at the manor and a night Martin would never forget. Martin sat in a comfortable chair with his hands on the arms, his legs crossed as he listened to Phoebe's questions. The only other person in the room was the photographer, who had already snappe...

Hotel Club Ch. 05

by pantywriter on Jan 6, 2020
Transgender & Crossdressers

I woke up from a fitful night's sleep. The slow, soft, wet and sloppy blowjob I had given Cindy did not improve my mood, not after the fight with my...wife? Ex-wife? I sat up in bed and rubbed my face hard. The increased blood flow felt good but did nothing to quell the rising anger. I showered angry. Brushed my teeth angry. Dressed angry. Ate breakfast an...

Staying Dead

by Skippy47 on Jan 16, 2019
Loving Wives

Grayson Marshall was flying over rebel territory in an observation plane. He had been recruited by the CIA from 5th Special Forces where he was a language expert. He was looking for a cocaine operation run by a group of Communist rebels to fund their revolutionary activities. One area began to look suspicious. The foliage looked real but was different than t...

My Friend Ashley Ch. 08

by jealouscuck on Sep 23, 2019
Transgender & Crossdressers

After my anal cherry was surrendered, I had no remorse other than the soreness the following day. Sheila and I had taken full advantage of our passage and enjoyed each other over and over. I returned to Ashley's the following morning and got some much-needed sleep. I was a total mess. I had not bothered to do my makeup when I got up that morning and I just w...

Ella Cucks Her Patient Ch. 03

by CuckFantasy69 on May 7, 2019
Exhibitionist & Voyeur

I arrived at Ella's office on a Sunday. The door was locked but after less than a minute of waiting Ella and Nathan came along and greeted me. Ella had pale makeup with black lipstick and black nail polish on while wearing a black trench coat and heels. She looked like a dark vixen ready to shoot a porno. Nathan was carrying a duffle bag with him, I immedia...

Paul's Birthday Gift: My Wife's IUD

by donaldelliott11 on Jun 1, 2020
Group Sex

[The idea for Paul came from a Reddit post. The author, who has since deleted his account, gave his approval for me to expand, elaborate, develop, and publish this story as my own.] ***Our First Bull*** I'd wanted this for so long: a hard young teenage dick for my wife. She laughed about it, didn't take me seriously. Called it my "frat-cock fantasy," or my...

The School Tramp

by tawnysuede on Sep 19, 2017
Transsexuals & Crossdressers

(From "Boy" to " Boy oh Boy!!") Chapter 1 - The School Tramp I was a virgin. I did not want to be a virgin. I asked my sister for help, and that was a mistake. Well, at the time I thought it was a mistake, but it turned out to be the best mistake that I ever made. I was nineteen years old at the time and entering my junior year of high school. Yes, my ju...