Sissy Punishment Stories

36,576 results
Orientation
Length
Source
Infinite Scroll

Blackmailed Pt. 02

by cdsissybambi69 on Sep 18, 2017
Transsexuals & Crossdressers

What the fuck has happened to me? This thought had been making an appearance in my mind more than ever lately. I knew exactly what had happened to me although I am not sure why I enjoyed it so much, it was like a switch in my head was flipped and all of a sudden I was a new person. The devious bitch Hannah had forced me into dressing like this slut of a sc...

Claiming Marc

by MsJess2U on Sep 19, 2017
BDSM

Jenna was angrily shoving Marc's belongings into trash bags. Two full bags sat by the front door in the living room. He had never formally moved in with her, but somehow a ton of his belongs had migrated into her apartment. He burst through the door lugging the sacks of groceries she had sent him out for. A cheerful greeting froze on his lips as he spotted h...

Two Three One Ch. 04

by OneWhoAdores on Sep 14, 2017
Novels and Novellas

This story is very difficult to categorize within Literotica. As it is fairly long, written in nine chapters, I will post it the Novella category. It is mostly a story of love ... D/s, femdom, lesbian, communal ...and of three people, and their inner needs, as life brings them together and connects them ... or not. As with most of my stories it develops slow...

Taken at a Party Pt. 05

by johan26 on Sep 16, 2017
Loving Wives

After Aaron left I spent the day cleaning our apartment while Marta rested in bed. She occasionally called me in to lick her pussy to orgasm before kicking me out to finish my chores. After an exhausting day for me and a relaxing day for her we went to sleep. She spooned me as we slept. When we woke up the next morning Marta said, "you like being a cuckold...

BMOC: The Shopping Trip Ch. 01

by TripleL on Sep 12, 2017
BDSM

This is a stroke story. It's ridiculous and unrealistic. No one is worried about STDs, sizes are exaggerated, everyone is bi (or at least the women are) and people can fuck for hours without chafing. This chapter has simulated non-consensual sex and unsafe BDSM practices (seriously, people, use safe words). Caveat reader. --- It was a bit past two AM when...

Heidi and The Kaiser Ch. 01

by Selena_Kitt on Sep 13, 2017
BDSM

Heidi would do anything. That's what they all said. She was little more than a glorified go-fer, anyway, running across town to fetch props for the shoot and two dozen hot coffees, or lugging cameras and equipment and trudging after the photographer. There was also making sure the models had exactly what they wanted, when they wanted, and how they wanted i...

The Cage

by AngelicTani on Sep 19, 2017
Loving Wives

Part 1 It had been some months since Dom and Linda had played with others. After their last adventure, things went quite during the birth, recovery, midnight feeds etc. Dom however, missing out on a lot of that, grew ever hornier and more depraved thinking of new perversions to try and enjoy. Finally, they had resumed fun with each other and were getting k...

The T.V. Repairman

by Ethan on Sep 13, 2017
Erotic Couplings

I was very surprised to get a call from the Grayson house. I had installed our newest and most expensive home theater system in their home just the day before. I'd tested the system fully and had shown both Mr. and Mrs. Grayson how the system worked. The Exhibitionist SE was a monster system. It included a 65 inch projection screen, 16 remote speakers and pr...

Moonlight

by chained_bird on Sep 13, 2017
BDSM

I can see it when I close my eyes... You're lying in bed, asleep. The only light in the room is the moon, filtered through curtains. I can barely see your silhouette, peacefully composed; barely hear your breathing, quiet and rhythmic. I touch your hair, lightly stroking it, twisting the ends between my fingers ever so gently. Sharp, sweet longing pierces t...

The Toison D'or Pleasure Palace Ch. 02

by Romantic_Whispers on Sep 13, 2017
Erotic Couplings

Part 2 ~ Lillian Visits Again ~ Lillian is one of the many ladies that visits Lord Augustus. She usually spends the weekend on his estate and receives much of his attention. ~ [ My Lord is expecting Lady Lillian today. He will be giving her much attention this weekend. She will be meeting him in the dining hall this evening. The chef has prepared a six c...