Caught Sissy Stories

167,051 results
Orientation
Length
Source
Infinite Scroll

Ode to a Redhead

by naughtywriter2 on Sep 13, 2017
Loving Wives

He tapped the toe of his shoe on the black and white linoleum floor beneath the booth, as he watched her every move. She sat across from him looking so seductive, so fuckable. Her tousled red hair and deep green eyes sent waves of electricity surging to his groin. Her attention was focused on the thick chocolate shake she sucked contentedly through a red and...

The Warrior

by KillerRomance on Sep 19, 2017
Romance

Warning: Those who don't like bittersweet romance, short stories or Asians, please leave now. Still here? Well, I hope you enjoy this one! It's short but I wouldn't want to change a damn thing about it. Lillian. 1700s, China. Lee dropped his armor onto the bed, uncaring to the damage that the spikes could do to the feather-ticked mattress. His muscles w...

Roger's Mirka Ch. 01

by masked_maiden on Sep 13, 2017
NonHuman

Mirka was running though the woods. She did not know where she was or where she was going. But she knew what was behind her and she would not go back to that. The chains on her arm, legs and neck were heavy, but she kept running carrying them the best she could. Thorns caught on her legs and arms, leaving scratches. But she kept running as she stumbled and f...

The Millenium Party

by Chuck Wood on Sep 12, 2017
Loving Wives

My wife and I have been married for seven years. We are both in our thirties and have no children. She is an accountant and I am an attorney. We both work for large firms and spend a lot of hours working. Beth is 5'5" with a cheerleader's athletic build. Her ass is nice and round and firm. She had breast augmentation surgery two years ago and her tits are to...

Ellie Forever Ch. 03

by delmar100 on May 27, 2019
Novels and Novellas

My mom and Maddie were setting the food on the table I was sitting at. "Hush girls and sit and eat" Maddie said. "Jack, you too." Mom echoed. The two giggling girls sit across from me, hardly making eye contact with anyone but each other, except sneaking a look at me and giggling again at each other. No doubt that Ellie already spilled the beans to Addie,...

The Sable Masquerade

by hellenberg on Apr 8, 2019
Sci-Fi & Fantasy

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** Marethil, aspiring drow matriarch and part-time queenmaker of the underground realms, looked curiously at the stranger in the appealingly minimalist mask. "So what should I call you?" "Toranel." That was so obviously a surface-dweller name that Marethil nearly doubled ove...

The Black Seas Ch. 06

by JoeBarnosky on Sep 16, 2017
Novels and Novellas

Antigua, 1702 The months at sea seemed like ages for Jack Rackham. Every day was like a lifetime away from Anne and every day he couldn't wait to return to her arms. The day came when his ship returned to port. Upon seeing the town from the distance he rushed below deck to pack his few belongings and rushed back up to finish up his tasks. Helping the rest o...

Aurelia's Night Out

by Cybelle333 on Feb 11, 2019
Erotic Couplings

Aurelia was going out. It was summer, and the air of the early evening was warm with the heat leaving the stones of the city. As she dressed, and had one of her parents' slaves style her hair, she fell into thinking. She needed a change, and she knew it. She was living in her parent's house, for the love of the Gods; and while her father Mettius was in th...

Wife Watching and Wanking

by cruiser_2015 on Feb 12, 2019
Loving Wives

My name's Kathy. When our son left home for university my husband Steve and I decided to make some extra money by letting out rooms in our house on Airbnb. It worked out very well and we have a steady stream of guests. Steve and I have a full and varied sex life. One thing Steve's been into since early in our relationship is taking naughty pictures of me p...

The Master's Servant

by pinkcandy99 on Jul 3, 2019
Non-Erotic

Please note that the story is labeled as non-consent due to the themes of slavery and indentured servitude. The first chapter is setting the stage; no overtly sexual content here! Future chapters may involve more non-consent and sexual elements. As always, this story is intended only for audiences 18 years old or older. All characters depicted are 18 years...