Spanking Sissy Stories

28,144 results
Orientation
Length
Source
Infinite Scroll

Twenty-One More Questions

by silkstockingslover on Jan 1, 2019
Reviews & Essays

Summary: Jasmine responds to the most frequent questions asked by readers. Thanks to: Tex Beethoven, Wayne, and Robert for editing this essay. This isn't really a sequel, although it's a second part, as it addresses questions I didn't answer in 2017's Twenty Questions. 21 More Questions After 2017's 20 Questions, I received many more questions. I have n...

Patti Cake Ch. 09

by betamale08 on Jul 17, 2019
Transgender & Crossdressers

Patti drove me home later that morning, we kissed some in my driveway and I could see Mom's curtains rustling as we said our good-byes. We kissed again and then I went into my half of the house I shared with Mom – and as I had in Patti's arms the night before in her big bed, I went in and I slept... I'd slept like I never before, 15yrs of wondering and thin...

Being Sarah

by Alex_Lockheed on Sep 25, 2017
Transsexuals & Crossdressers

Please note, this is a story about a male-to-female crossdresser. It includes themes of bisexuality, dominance/submission, embarrassing erections, anal play, cunnilingus and cum-eating. If you like that, awesome. If you don't maybe it's time to check another post. You can't say I haven't warned you ;) **** There are many difficult decisions I've had to ma...

Courtesan Ch. 16

by Goodhusband on Sep 19, 2017
Loving Wives

This is the sixteenth episode in a series entitled "Courtesan". If you have not read the previous fifteen episodes of this series, I encourage you do so before beginning this chapter. "Courtesan" is romantic story about a dominant hot wife and her submissive cuckold husband. While they have a deep and abiding love for each other they do lead an alternative...

HypnoSissy: Cum Cravings

by silkstockingslover on Sep 26, 2017
Fetish

Summary: Videos entrench his hunger for cock and cum. Note 1: Thanks to hfernandez1983 for the story idea and the intriguing revelation that hypno sissy videos exist. Note 2: Of course, all participants are at least 18-years-old. Note 3: Thanks to TexBeethoven, Robert, and Wayne for editing this chapter. Apology: This part was originally announced as bei...

Reversals Ch. 14

by RachelClark on Mar 13, 2018
Fetish

CHAPTER FOURTEEN The Appointment "This is the place," Julia said enthusiastically as she turned off the highway. They passed onto a private road and headed towards a large corporate estate with a tall, looming brick wall surrounding it. Erica didn't want to be there. He felt lightheaded and nauseous, desperately worried about where Julia was taking him....

Hotwives Ch. 02

by Donna Williams on Sep 16, 2017
Transsexuals & Crossdressers

HOTWIVES II by Donna Williams ((Read the first part of the story in "Hotwives" first)) I was now a hotwife, Vicky was a pseudo hotwife, and John was a sissy, cock sucking cuckold. Everyone got what they wanted, if not more! * * * Once John had fallen asleep, Dave and Rick left as we had planned. When John woke that morning, he found me in the shower. "You...

Guarded Ep. 02

by GCStargazer on Dec 23, 2019
NonHuman

Tracey leaned against the wall of the dressing room, one knee bent forward from her boot planted on the wall behind her. "So a pair of scissors huh, you almost pissed yourself over something like that?" Leo glared at the wolf while sitting in the makeup chair. "I didn't p-!" His mouth snapped shut as the pink-haired llama doing his second layer, grabbed his...

Enslaving Elliot Ch. 07

by MTL17 on Sep 13, 2017
Celebrities & Fan Fiction

Elliot had been here before many times over the past year. She had come here to hang with her little group of friends and of course to see JD, who she had been into from the beginning, but only a couple of times she came here specifically looking for Carla. There had always been a connection between her and JD, Turk was easy to get along with, but Carla was...

Audition Ch. 05: Nanette

by craigool on Jul 13, 2020
BDSM

"Audition 05: Nanette" by CraigOOL BDSM -- A wanton virgin spy in the house of love [Author's notes: Warning! This is a BDSM sex story. There are strong Dominance and Submission themes in this story. There are some interracial themes in this story. This story has substantial male/female, female/female, MFM, FFM and group sex sexual contact. This hopefully...