Spank Naughty Sissy Stories

1,000 results
Orientation
Length
Category
Source
Infinite Scroll

A Sissy Saga Ch. 02

by Snurge on Sep 15, 2017
Novels and Novellas

When Jennifer went out onto the terrace William was nervous but relieved to be with someone his own age and gender, even if that person had been sissified just like himself. The two eighteen-year-olds regarded each other and their feminine attire silently for a moment before Archie at last broke the tongue-tied awkwardness. "Better make a start," he said,...

Earning His Keep

by Compliant1 on Sep 19, 2017
BDSM

I punched in the code and waited. I knew that I was being charged $1.99 for each minute, but I didn't care. I listened to the recorded music until a woman's voice came over the phone. "Tell Mistress Monica, have you been a naughty little sissy?" "No, but apparently my husband has." There was a long pause on the other end. "I just spoke to the manager. He...

The Recipe for a Great Time

by lust4us on Sep 12, 2017
BDSM

Phew, I breathed a huge sigh of relief as I pulled into Four Seasons hotel. I knew I had to hurry, since my hubby was taking me out on the town. He had promised to take me to the best steak house in the city. Then after dinner we were going to go out, looking for the perfect piece of pussy, for me to eat and him to fuck. We were in Dallas and didn't know whe...

He Wears The Panties

by Quietoldie on Sep 19, 2017
Fetish

I like to put my wife in charge of things when I get home. I have a very demanding and difficult job which takes up a lot of my energy and it is nice to relax as I walk through the door of our house. The kids all have their own careers now and live quite a distance from us so we have entered into a new phase of our relationship and enjoy our new lives. Mary...

Girl's Night Pt. 09

by DifferentBreed on Sep 14, 2017
Fetish

*author's note* To the fans of this series I appreciate your patience as the chapters have been a long time coming. I am having difficulty fleshing out the club scenes that were to follow. I wrote this brief interlude which takes place immediately after the couple leaves the mall. Hope you will enjoy it. Thank you all for the positive encouragement and the...

Aunty's Toys Ch. 01

by novelcriss on Aug 21, 2018
Fetish

Simon rang the door bell, prompt at 2 pm, somewhere between nervous and excited and wondered quite how he had reached this point. He had met Sally in, of all places, a crowded cafe at King's Cross when all the trains were late. She'd pulled up a stool next to him , asked if it was okay to sit and started chatting. She was so easy to talk to, middle aged, n...

Aunty's Toys Ch. 02

by novelcriss on Mar 25, 2019
Fetish

**Thank you everyone for reading and taking time to vote on Ch. 01. Do please feedback. I hope you like the evolution in Ch. 02. It has taken a lot longer to get going than planned!** ***** Simon stared at his phone in his office, not quite comprehending. Sally or Aunty as she'd told him to call her had sent him a text. "Simmy dear, don't forget your app...

Stevie's Journey Ch. 03

by gbr2004 on Dec 2, 2019
Fetish

I get up and put on some of my regular clothes, workout shorts and a t-shirt and flip flops. Try to digest what happened yesterday and how everything just spiraled out of control and now I find myself in this impossible position. It's like all choices have been taken from me and this group of people took over my life. It was exciting but I can't be doing the...

Tony's Ascent Into Cuckolding Ch. 03

by Cuckyboy3 on Sep 12, 2017
Loving Wives

She called Brad that evening to let him know that I had come around after some convincing. They chatted for a while, during which she told him about my misbehavior. She moved away from me and talked softly for a while from the other room. Finally, she came back to me. I heard her saying, "Do you promise? You'll do that for me?" Then she listened for a while...

Sissy Boy Secretary Ch. 06

by Hotenuf4u on Sep 19, 2017
Fetish

When we got to the car Elaine said, "This won't do, you are missing something Sissy Boy. Kneel down here," as she pointed to a place just behind her car. I immediately knelt down, hoping no one would see. "Lisa my little Slut, remove your stockings and garter belt," it wasn't a question. As Lisa was getting done removing the items, smiling at Elaine as she...