Sissy Dare Stories

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Orientation
Length
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Infinite Scroll

Goddess Rules Ch. 02

by sub_boi on Sep 17, 2017
BDSM

I take him into my mouth and suck him with My soft, wet lips. When he is near coming, I grab his balls and pull down hard, letting his little cock slip out of My mouth. He moans in pain as My hand squeezes harder on his balls. "Now, My little slut, I have a surprise for you." I go to the closet and pull out a sexy little pink camisole. "Put this on, slu...

Lady's Sissy Bitch Ch. 01

by HorroticaWriterJCarter on Sep 16, 2017
BDSM

It was an exciting day. Lady was coming to visit and I knew I was in for a weekend of extreme pleasure mixed with extreme pain. It had only been ten months since we had met at a play party but it felt like she had known me my entire life. The minutes passed like hours and I could feel the desire growing inside of me like a wildfire. Lady was beautiful. Her...

28 Days

by tinywhiteboi on Dec 2, 2019
Interracial Love

28 days. That's 4 weeks since my last orgasm. And I was so horny, to the point of constant distraction. It was all I could think about. My locked little penis was dripping into my panties, and my little balls were swollen. Six weeks ago my wife, Angie, caught me jerking off to interracial cuckold porn, a video with the cuck locked in chastity. She'd come ho...

Ms. Alexandria - Interview No. 02 Pt. 03

by gasissynora on Nov 26, 2019
Transgender & Crossdressers

This is the fourth part of the Ms. Alexandria series, and the third and final part of The Second Interview. I believe it will stand alone, but will make more sense if you read the earlier parts of the story, particularly Part 2b. This part starts with the last paragraph of the previous part. ***** Ms. Alexandria: The Second Interview - A day out. Part 2c...

Sissy Life: Valentine's Day

by sissymark79 on Sep 19, 2017
Transsexuals & Crossdressers

This is a standalone story in the 'Sissy Life' universe. You don't need to have read any of the other stories to enjoy this one, but it does fit with those in terms of characters & themes. Consider it a 'Rogue One'. ***** 'Have you finished in the kitchen?' I had indeed. I'd cleared the pots and cleaned the surfaces. I couldn't talk with my ball gag in how...

Little Sex Toy Ch. 06

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

Squatting on my heels, feet just up under the curve of my cheeks, I can feel the ruffles on my sissy sox up against my bare legs. They would tickle if I weren't so afraid and focused on doing what he demands I do in front of these men. My knees pushed up toward him and spread wide, don't dare hold them together, don't want to get slapped, I feel his hand o...

Sissy Boy Chuck Becomes Just Sissy

by Krazy35 on Sep 14, 2017
Transsexuals & Crossdressers

A long time ago, I realized that I had a thing for women's clothing. I used to sneak into my sister, Jessica's room and get all dolled up in her clothes. She was a year older than me, but we were practically the same size. I got an incredible hard-on looking at myself in her full length mirror. I quickly undressed, put everything back the way I found it, the...

Sissy's First Trip Out

by thinksissy on Dec 24, 2019
Transgender & Crossdressers

*This is my first story so please comment as much as possible to let me know what you think. Thank you!* Kenny had always been obsessed with women's underwear. It all started out pretty innocently, well, as innocently as can be expected when masturbation is involved. He used to look through women's fashion catalogues and drool over the lingerie and bikini s...

Truth or Dare with Sisters

by sissyboy_stacey on Sep 18, 2017
Fetish

Ringgggggg... Ringgggggg... "Sean, can you get that?" "Hello? Hey Gina... what's wrong? Ok, hold on, I'll get her..." "Katie, your sister is on the phone. She seems really upset and said she needs to talk with you." When I heard my wife Katie pick up the phone in our bedroom, I pretended to hang up, but instead, I put my phone on mute so that I could eav...

Mistress Marisa's Estate Pt. 26

by keptsissy on Sep 15, 2017
BDSM

I am one of several slaves my Mistress Marisa keeps in her household. I am completely owned as are the other slaves that serve her. These episodes are written with her permission. It is my, our story... ******************************** When told 'Get to THE room!', I know what that means. 'The Room'. It is off the side of your basement playroom. It is the...