Sissy Humiliated Stories

21,486 results
Orientation
Length
Source
Infinite Scroll

Sarah was Humiliated

by SarahCD on Sep 16, 2017
Transsexuals & Crossdressers

I got myself into trouble the other day. I live on the second floor in a little apartment building. I was just starting up the stairs when I looked up and saw that my neighbors were out on the landing. She had her back to the railing and was talking to her boyfriend. She was wearing a short white cheerleaders skirt. I froze and stood there trying to look up...

The Sexy Cuckold Couple Pt. 02

by cuckcpl4play on Sep 26, 2017
Fetish

While neither of us slept great, we did manage to get a little bit of rest before we were suddenly woken up with Jen's phone blowing up. She checked her text messages to see that Brian had requested we meet in his office at noon today. He made it clear that unless there was an emergency or other, he would expect to see us both there. We were a bit surprised...

Sissy Gets Punished on His Birthday

by NSEW1 on Jul 3, 2019
Fetish

My lovely goddess of a wife had promised me a memorable treat for my birthday. I stayed on my best behavior that week, in anticipation of an exciting climatic night of pleasure. During the day she texted me 'hope u are ready for treats.' I wrote back to confirm and then told her I was doubly thrilled to get not just one but multiple treats. She responded bac...

Little Panties for a Little Cock

by SarahCD on Sep 16, 2017
Transsexuals & Crossdressers

It was Saturday morning and I decided to get my laundry done before going out for lunch. I took my stuff down stairs to the basement laundry room, loaded a washer and started the cycle. I was about to go back up to my place when I noticed a basket of laundry on the table. I went over and found a mix of girls and guys stuff, I guessed they belonged to the you...

How I Became Sissy Willow Ch. 01

by willow619 on Sep 12, 2017
Transsexuals & Crossdressers

Description: A married cross-dresser's fantasy to dress and serve becomes reality at the hands of his wife and her lover. Fern and I had been married for three years. Our sex life had become bland, routine, and, frankly, I preferred masturbation to the work it took to cum by intercourse. I was pretty sure that Fern felt that way, too. You see, my cock is, a...

The Neighbours Situation Ch. 02

by Missclo on Jul 3, 2019
Transgender & Crossdressers

I read the text over again and again, the feeling of fear still strong in the pit of my stomach from the last few minutes. What if she showed the photos to people? What other twisted commands had she got in mind for me? I decided I needed to get up and try and take my mind off of the situation the best I could. Surely this was the revenge for sniffing her p...

The Man That Owns Me Ch. 02

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

I feel a sharp slap on my left cheek. His strong hand comes down so hard across my butt it shakes the bed, it makes me cry out. A loud 'SMACK' reverberates off of the walls in my bedroom. "Please..." I hear my voice quiver, tremble as I look back over my shoulder at him. It's the fifth time he has hit my rear end hard letting each slap sink in before the...

Humiliated Sissy Husband

by rik581 on Sep 12, 2017
Transsexuals & Crossdressers

Content Warning: To Literotica readers. This is a story of degradation and demeaning of the male sexuality as retribution for an extra marital affair. It consist of a strong female character and a wimpy willing male character. The sexual hypocrisy built in the story is intentional an meant to be part of the demeaning aspect. There is "NO" gay scenes in the s...

A Natural Sissy Ch. 08

by harv069 on Sep 15, 2017
Transsexuals & Crossdressers

Author's note: This is a multi-part story about a young woman turning an older man into a compliant, sissified plaything. It is best understood if you read from the beginning. If that idea doesn't appeal to you, don't read the story. If you don't like this kind of story, but read it anyway, please don't bomb me. I warned you to go away. If you like the idea,...

The Public Adventures of Mark Ch. 03

by rik581 on Sep 15, 2017
Transsexuals & Crossdressers

"Come on Mark," Cindy said as they pulled up in front of the nail salon in the shopping center. "Time to get your nails done," she laughed and patted him on the shoulder. Cindy was so good at this public humiliation game that she played for Mark. It was because she cared so much about him and knew it was such a deep passion and turn on for him once she got h...