Ultimate Sissy Weekend Stories

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Orientation
Length
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Infinite Scroll

Kasey's Confession Ch. 12

by KaseyLegs on Sep 14, 2017
Transsexuals & Crossdressers

The restraints Gary used to secure me, face down, on his bed were well-worn leather restraints attached to unusually heavy chain. Once I was restrained and helpless, spread-eagle across his bed, which was stripped off all blankets and sheets except for a single, very clean white sheet underneath me that felt like it was made of tablecloth fabric rather than...

BPH: A Pair of Goldilocks Pt. 02.1

by PrevertOne on Sep 14, 2017
Sci-Fi & Fantasy

Bears, Porridge, and Honey: A Pair of Goldilocks by The Preve Story Two---The Honey Trap: Part One 'Trinity Bridge Motel-Vacancy' "Good!" gasped Phil. "A life saver." Phillip Locke, college sophomore, returning to Midwestern after the worst spring break ever, pushed the hunk of shit, formerly his rented car, into the parking lot. All-in-all, the climax...

CD Mistress Weak for Candy

by MistressCheyenne on Sep 16, 2017
Transsexuals & Crossdressers

I have been a crossdressing Mistress for several years now. I have a petite body and always looked good in a dress. I take on many slaves but my favorites are other men who look great in dress. This is a story about my favorite slave I have ever trained. I had been anticipating the arrival of my new toy all week, and he was moments away. My new slave, eager...

Sheila's Training Ch. 01

by CeliaisAliena on Sep 15, 2017
Anal

Not for nothing are "Ghost World" and "The Doom Generation" my favorite films. I was made for a stark black bob long before I ever got one, before I saw those movies and even before I discovered black hair dye. Without it I might have ended up looking something like Lotte Lenya in "From Russia With Love." Goddess bless Manic Panic!! It's more than the hair,...

End of the Beginning Ch. 02-03

by Celticfae on Sep 16, 2017
Transsexuals & Crossdressers

The relieved pair headed to the shower. Matthew leaned over to turn on the water. Jamie realized she would have to remove her wig or it would be ruined. Matthew looked over at her inquisitively. “It’s a wig; I have to take it off.” Jamie answered to the unspoken question. “I hope you don’t mind, my hair is still growing back.” “I figured as much. It’s ok, I...

Obeying Mistress Sofia

by Halink on Sep 17, 2017
BDSM

I walk five steps behind, carrying her bags. She speaks to the taxi driver in a language I do not understand and she tips him with my money. She takes me to a bar you know, a place that is packed with people. I order a glass of wine for her and bring it obediently. She takes a sip and frowns at me. "What is this filth? This is terrible! Bring me something...

Becoming V

by SheerSilver on Sep 17, 2017
BDSM

*This is the next segment to Secret Voyeur. If you have not read that one you may not fully understand this story.* I groaned out loud and rubbed my temples. I had the worst headache, I felt like my head was going to split open and burst into flame. A deep clanging sound was ringing in my ears. Damn I was sore, everywhere! I really need to use my hot tub...

Robillard's Pain

by justincbenedict on Sep 13, 2017
BDSM

POOR, PUDGY ROBILLARD! As he brushed and stroked his beautiful goddesses curls, Robie's penis nearly wrecked itself, locked in the tiny casing. Would he escape it today... maybe? Robillard St. Croix finished coming Autumn's cascading blonde hair. He'd given Autumn a great comb over, and massaged his pretty cousin's shoulders till Autumn had purred. She'd l...

St. Clair Ladies Circle: Marlena

by 1946EW on Sep 16, 2017
Transsexuals & Crossdressers

22nd Century Imports was a fancy name for a distressed goods wholesale business. Edward "Ted" Hanratty bought the inventory of businesses that were going out of business for whatever reason, and either sold the inventory to other businesses in the same line of work, or through a chain of discount outlets he had in his own and two neighboring states. The "imp...

Parlor Panties Pt. 03 - The End

by Sanyo81 on Dec 2, 2019
Transgender & Crossdressers

I felt like the sharp nails were going to draw blood. The firm grip was so threatening. I could feel her hot breath on me as she whispered into my ear. "Shhhh, so pretty. Close eyes" More demanding than asking, I did as she commanded. Tingly brushes on my cheeks and hard presses on my eyelids. I dared not open my eyes for fear her nails would rip me apart....