Spanked Sissy Stories

24,820 results
Orientation
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Infinite Scroll

Caught by the Lodger

by SuzieR on Sep 13, 2017
Transsexuals & Crossdressers

Having split up with my girlfriend about six months before, I was getting a little bored of living on my own. I'm a 29 year old guy living in South London and I thought it would be a good idea to get a lodger. I had a spare room that was empty, the company would be good and the extra money would come in handy. I put an ad in the local newspaper and within a...

Strip ...

by seekingsusie on Sep 16, 2017
Transsexuals & Crossdressers

"Strip. Get off all those ugly man clothes. Now." I looked around, saw the bathroom and started toward it and heard her stomp her feet. I looked back and saw her grimly shaking her head and pointing to the floor near her left foot. I stood in the designated spot and the look on her face was grimmer yet. She moved her hand slightly, indicating DOWN. I kneel...

Sissy Amy Loves Mummy Belinda Ch. 02

by Sissy Adele Howells on Sep 17, 2017
Fetish

Mummy Belinda Beynon was now in complete control, as she pushed my pram down the road. I snuggled against my satin sheets and was very content. Mummy Belinda removed my dummy every five minutes, wetting it with her saliva, before putting it back into my mouth. Staring up into Mummy Belinda's pretty face, was a dream come true. She would tease me, by blowing...

Samantha Finds a Dom Online

by SamanthaSatine on Jun 19, 2018
Transsexuals & Crossdressers

A true story - pre-chastity episode from this sissy slut.. It's Friday... It is 9.30am... Text message received "Are we still on for today" her reply "Yes, I believe we said 10am" Bag packed she takes the short journey across town to the meet. Samantha checks in for the final directions having been once before but it is a secure address with locked a...

My Strapon Fantasy

by libertinaXx on Sep 19, 2017
Transsexuals & Crossdressers

I woke up in the middle of the day and smiled; my girlfriend had gone to work a few hours earlier and promised me a really good time when she got back. I ran upstairs to shower and make sure I was hairless before getting ready for her. I wandered into her room to dress for her arrival. I found a purple sheer thong and matching bra in her underwear draw that...

Cosplay Wife, Cuckold Life

by SatinSlip on Dec 3, 2017
Exhibitionist & Voyeur

My wife and I were high school sweethearts. Kimberly was a brilliant, lovely girl. With big breasts and long curly red hair. Academic and popular. I was nerdy, and smart. A bit to feminine to be handsome. I was shy and weak. Neither of us had been with other partners and our sex life was pretty vanilla going into our mid twenties. Mostly missionary style...

A First Time at the OBGYN

by sissypt on Oct 19, 2020
Transgender & Crossdressers

I had been feeling under the weather but since everything had started getting into the doctors office was not an easy task. I had been staying at a friends house since i got kicked out of my mom and step dads for not "following the rules" there was more to it but that's for another time... Having had a sore throat sucked and with all the covid scare my fri...

A BDSM Sissy finds Daddy Ch. 01

by Secret_sissy712 on Jul 13, 2020
Transgender & Crossdressers

As I walked back to my van after finishing up the apartment complex two men pulled up in a van and park a few spaces away. As I open my door and I take my tool belt off my shirt rides up just enough for them to get a sneak peak at the red satin thong panties popping out the top of my jeans. The fact that they do is no mistake. I wear them high and the jeans...

Becoming Mindy Ch. 02

by mindyrose on Sep 18, 2017
Transsexuals & Crossdressers

Thank you for the positive feedback from my first story. As I recall things I wrote about in my diary, I am not going to be writing on all of them. Just the ones that are important to my story and/or just some memorable events (i.e. the first time I..). I hope I am able to write them in a way that you find as enjoyable reading as I had living them. I have se...

Just Like My Friend

by purekink on Sep 12, 2017
Transsexuals & Crossdressers

I suppose it all started after my friend told me his girlfriend liked to dress him in her clothes before sex. I couldn't quite believe it - he was masculine and muscular, a real man's man. He'd confided in me and I teased him about it unmercifully. I mean, really? Being dressed in women's clothes? That was supposed to be a turn-on? He seemed to think so, bu...