Spanking Sissy Stories

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Neighbourhood Terror to Sissy Pt. 06

by Fibaro on Apr 9, 2019
Transgender & Crossdressers

Mark's night ended up being a very restless one. The constant rubbing of his sheets against his nylon covered smooth legs as well as the feeling of the silky material of his panties all around his bottom and chest felt very sensual. He was embarrassed to admit it, but it actually turned him on. The worries combined with the horniness formed a potent combo to...

Dinner Date with Mommy Pt. 01

by SissyStoryTime on Nov 20, 2018
Transgender & Crossdressers

This is Part 1 of an update on the sissy Sophie and her cruel but loving Mommy, Amanda from the story Meeting Mommy (https://www.literotica.com/s/meeting-mommy) It contains numerous perverse and offensive themes that I'm sure you'll all eat right up. This story includes the following: Femdom, strap-on, implied forced-bi and cucking, enemas, butt plugs and...

Neighbourhood Terror to Sissy Pt. 04

by Fibaro on Mar 25, 2019
Transgender & Crossdressers

The next morning Mark was woken up by a loud mechanical voice. "Wakey wakey sissy, time to start your day, and what better way to start it than with another wank." Mark groaned loudly but he did as the voice said anyway. With a sigh he grabbed the boxers of his night stand and Pulled them over his head once more. Since this had started he had spent countle...

I Become Wendy's "Wife"

by Quietoldie on Sep 16, 2017
Transsexuals & Crossdressers

After the amazing weekend I thought things would settle back down to our usual routine. She was out working all day so I had to wait until the next weekend to go shopping with Wendy for my new wardrobe. In the meantime she allowed me to wear any of her clothes that I liked but most were a bit too big for me and Wendy had only a few dresses and skirts to choo...

Samantha's Panty Boy Ch.02

by PinkPantysBoy on Sep 13, 2017
Fetish

Special thanks to Angel Love for editing. Samantha opened the front door and slammed it hard so Jack would know she was home. He had drifted off to sleep with his pink panty still on and her panty crotch on his face. He heard the door shut and immediately got up. He heard her coming up the stairs and did not have time to change back into his own underwear s...

Sissy Training

by kendra13 on Feb 13, 2018
Fetish

I am a blue collar manager type and live a pretty work a day life during the day, but at night, I have a rather interesting sideline. I am a sissy trainer. You see, many sissies are married and end up coming out to their wives. To most couples, this just creates a fun little fantasy for play during sex, but for some, it becomes more. For these couples, at so...

I Learned My Lesson Well Ch. 03

by Angelscuck on Sep 2, 2017
Exhibitionist & Voyeur

Well the weekend had arrived. My Fiancé, Angel, had given me a complete makeover at the salon. I looked ridiculous in my maid's costume with full makeup, heels, stockings, garter belt and leach with collar. She looked amazing with her slutty makeup, hair worn up and completely naked under her trench coat. We were on our way to her gangbang. Her black maste...

Kinky Dentist Sian And Sissy Rachel

by Sissy Adele Howells on Dec 12, 2018
Fetish

Most people hate going to the dentist, but I get a sexual pleasure every time my appointment comes around. That is because my dentist is the sexiest women, that I have ever set eyes on. Sian Harris is in her late thirties. She is of medium height with short, brown, mousy hair. Sian is very pretty, with a smile to melt any perverts heart. Sian's husband worke...

Sissy Training Vol. 01

by depositdutchess on Nov 27, 2017
Fetish

Being feminine is taught. Correcting your nasty masculine behavior with feminine manners and class is what you need. Being a sissy is your new reality. I am going to make you the pretty little girl you have always dreamt of being. You need to be taught ho live your every day life properly. You can only dream of being as sexy, girly and attractive as a real w...

Transforming Brent Pt. 05

by sissymissyct on Dec 2, 2019
Fetish

I awoke early, partially due to the pressure of morning wood in the chastity. Once I settled down, I showered and slipped on a robe and quietly made my way to the kitchen. I quickly familiarized myself with the layout and, finding what I needed, started cooking a nice breakfast for my mistresses and myself. Ham and cheese omelet, OJ, toast and sausage, along...