Chastity Boy Stories

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A Sissy Surprise "The House Warming"

by Simply_Sissy on Feb 6, 2018
Transsexuals & Crossdressers

My girlfriend Vicki had been really pushing me to go to her friend Mary's house warming party on Saturday night. Mary had been quite the bitch lately not like the two of us ever really hit it off. To make things even worse she is aware of my panty wearing secret. Vicki had shared this bit of information with her when she first discovered my little fetish abo...

The Care Girls Ch. 02

by Tomsparty on Sep 15, 2017
Transsexuals & Crossdressers

Chapter 2 - Magical nail varnish She half heatedly expects you to refuse, any normal boy would, but you're different and she knows you'll do anything to stay in her company tonight. She looks at your pathetic girlish frame and how you sit like a sissy. A cruel smile spreads across her face. Like the other girls at school she rather likes ridiculing you and...

Alien Experiments Ch. 01

by evanescent82 on Sep 19, 2017
Transsexuals & Crossdressers

Somewhere far above the Earth's atmosphere, an alien ship circled. The aliens would have left days ago - the planet was still far too primitive to merit a contact. But something puzzled them. The inhabitants of this particular planet were puzzling. The aliens, coming from a world dominated by huge oceans, were an amphibian species. As amphibians, they did no...

Caught Jacking

by movieye on Sep 16, 2017
Exhibitionist & Voyeur

Last summer when I went camping with the guys, we sat around the campfire, drinking beer and talking shit. After a couple beers, we started talking about sex, no surprise. And a topic came up that made me cringe. "Have you ever been caught jerking off?" "Once." I said to my buddies. "And I will never forget it." *** When I was 18, I was sent over to my...

Bloody Good Boy

by SmallPond84 on Sep 15, 2017
Fetish

I stood in his bathroom, brushing my teeth and thinking about how mirrors in California were much larger than on the East Coast. Blake moved into this apartment two days after I arrived for my ten-day visit. It was my input that decided this place and it was based entirely on the abundant wall-to-wall mirrors in the bathroom and bedroom. As a city girl, this...

Unexpected

by ShatterMe on Sep 16, 2017
Romance

Hello, everyone! Just a quick note, I'm planning to have a lot of build-up in this story, so there won't really be any sex until later on. Hope you enjoy it regardless, though! It's an idea I've had for a long while now. ^^ -~*~- Have you ever felt overwhelmed with so much joy that you started to question whether or not what was happening wasn't just a dre...

The Teacher Gets An "A" Ch. 8

by usm1carbine on Sep 14, 2017
Interracial Love

Gia practically fell onto her sofa as she stumbled through the door, she could still feel the cum oozing from her pussy and ass from her day’s activities. Her panties and bra were gone before the first bell this morning and she wondered why she even bothered to wear them anymore. Her obsession with black cock would be her ruination, she thought to herself as...

Favorite Memories: Making a Man Cum

by tevyus on Mar 20, 2018
Erotic Couplings

Dedication: To the honest women who gave me their answers to "What's your favorite memory of getting a man to cum?" Jana, age 26, Virginia: This is going to sound really perverse, but when my last boyfriend turned 25, I wanted to give him a sex present. So I invited Emma to join us in a threesome. My boyfriend Bobby was a breast man - and bigger is bet...

Sunday Service Ch. 01

by tUvLa on Sep 17, 2017
BDSM

ti ti ti ti... ti ti ti ti... *Shebang* That was my hand right there, spanking watson my alarm. "Thank you Watson, your services are no longer required," I said out loud. As my soul was awakening, it was very excited for the day up ahead. It is Sunday, and as every Sunday, my little sissy Sasha and myself have our weekly session. Sasha is a male in his...

Aphrodite's Curse Ch. 020

by Gaius8666 on Sep 15, 2017
BDSM

Back on Olympus, Zeus finally had arrived, so Persephone's party could get started properly now. Hephaestus got the grill going and had just tossed a couple of lamb steaks onto the fire, the smell of their sweet roasting flesh causing all of the Gods and Goddesses in attendance to salivate in hunger. Hephaestus, god of fire and the husband of never faithful...