Sissy Party Stories

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Orientation
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Mikey becomes Melodie Ch. 02

by tiffanyfoxe on Jul 14, 2020
Transgender & Crossdressers

I lay there under this incredibly beautiful fully transformed girly-boy, her lipstick covered lips still softly and tenderly kissing me, kissing my lipstick covered lips, my rouge covered cheeks, my eye shadow covered eyelids and my mascara coated lashes, showing how much she loved having me under her, her huge still hard cock buried deep inside my pussy/bot...

A Natural Sissy Ch. 02

by harv069 on Sep 15, 2017
Transsexuals & Crossdressers

Author's note: This is a story about a woman who turns an older man into a compliant, sissified plaything. If that idea doesn't appeal to you, don't read the story. If you like the idea, read on, and don't forget to vote and leave a comment. You will need to read the previous chapter to see how we got where we are in this one. More will be added if comments...

Panty Posers Ch. 06

by EROTICbearscribe on Oct 19, 2020
Transgender & Crossdressers

We entered our building and bumped into our downstairs neighbor Jerry. He was taking his trashcan back to his apartment. He set it down at the landing and gave us each a good look. He wasn't at all phased by our appearances. "Little early for Halloween, isn't it...boys?" he asked. We both were fully aware Jerry knew we were sissies. It was fairly obvious...

Kyle, The Party Dog

by Mixedwritings1993 on Sep 17, 2017
BDSM

After calling his little brother by his name, Brandon got a little pissed off when no one responded, "Damn, that boy is sleeping once again, man, can't he even stay awake for few hours at a stress?" He stomped on the floor hard on entering his little brother's room and was amazed to see even the loud stomping noise didn't wake up his brother, Kyle. Brandon...

Proud To Be A Sissy Ch. 09

by Kary_M on Sep 26, 2017
Transsexuals & Crossdressers

"I hope you like them," daddy stated cheerfully as he lifted the towel from my face while handing me a bra that was laced with trim, matching my panties, "they look great on you sissy." Looking down I saw two flesh toned swells that weren't there before and sitting up I could feel a slight weight pulling down. I jumped off of my bed and stood in front of th...

Halloween Pool Party Pt. 05

by sissymissyct on Sep 14, 2017
Fetish

We arrived home and Annie greeted us warmly, then stepped back to get a good look at me from head to toe, having me turn to see the full look. Satisfied with what she saw, I was told to bring in my clothes, put them away and then pick something pretty to wear as dinner would be ready shortly. Miss Maddy and Annie headed into the main house and I went about m...

Virus S

by thisisnttaken8 on Jan 17, 2021
Bisexual

"FUCK ME YOU STUD!" the slender new trap screamed in agonizing bliss as the muscular stud pounded him from behind. Connor could see the brute's body changing by the second. He arms grew more muscular and his jaw grew more angular, but even stranger was his cock. It seemed to be growing thicker and larger as he plowed the twink's ass. The bull wasn'...

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My Beloved

by quotidian01 on Aug 30, 2017
Fetish

"My Beloved, I am your dedicated lover and I will do anything for you. I thank you for letting me make this web site, where I can feel the whole world watching me. Everything I do here is for you, Beloved. And in pleasing you, I am pleased." My voice sounded a bit tinny in the cheap computer speakers. I knew I was displayed while the voice spoke: sometimes i...

The Awakening of a Sissy Pt. 10

by sissyjolie4u on May 11, 2020
Transgender & Crossdressers

Best I could tell, neither one of us had moved an inch from the position that we fell asleep in. The urge to pee woke me quite early, like 4 AM early. A smile came to my face as I realized I was still holding Tim's cock. While barely awake, I made my way to the bathroom and took a seat to pee. While sitting there peeing, it hit me that I should probably do a...

Getting Some Helping Hands Inside

by Cumfusion on Sep 14, 2017
Anal

[This is a sequel to 'Cream Buns after the Party'] It had been scary towards the end of the party as I knew, if any of the hotel staff had walked in, I would have been instantly dismissed in disgrace. That's kind of not what you need in your first job after college. I had been asked to be bar tender in one of the hotel function rooms. I didn't know it wa...