Our Lady in Black

 British Man to Older Italian Mafia Boss Woman TG

Jack's lips squirmed, his built young male body sweating and sticking to the simple black dress he had been somehow fitted into.

"I'm a nobody, come on, let me go!" He said with clear little confidence. The two well-dressed henchmen looked between each other with an equal lack of confidence, but then shrugged. One of them checked their watch and motioned to leave. The door slammed a moment later as he was left alone with fading light.
"I'm just a day tourist. Let me go!" He screamed half-sobbing. He was told Sicily is a beautiful place where if you don't go looking for trouble you won't find it. He felt bad even telling a white lie, but somehow, sometime, he had offended these people. Were they going to bury him alive? Oh god, the dress. They dressed him up like a woman. This was like some kind of a rape ritual? They were going back with the whole gang to... no.. no no no. He fought the chair in panic, screaming nonsense into the blackness. Then he stopped.

I suppose this dress suits me. He heard a whispering, an older, smoky and sexy voice. It sounded like she was just rousing from a year of sleep.
"Wh-who's there?"
His mind began to ring out with Sicilian words. First like the baby's first mutterings. Talk of a dolls, dirty ripped dresses and greasy food. Shouting and arguing and wishing it would stop. The thoughts of a little girl. Then more poured in. Dirty thoughts and fantasies,  the filthiest and secretive slang of a teenage girl from Palermo.
"Gahhhh, where is it coming from? Too many. Did I forget so much?" He said, unsure even of why.

His skin began to crawl as barely controlled wrinkles appeared. He let out a yelp from the burning, as it took on a weathered skin-kissed look from years of the Sicilian sun. Ten years... twenty years.  He tried to push down all the thoughts of a life that wasn't his own. But more and more seeped in from the dress. This is... I'm a man. I was born in England. I was born a bloody boy. Why am I so confused all of a sudden? My name is J..my name is Ja...Jabina... Sabina! He gasped as he felt the energy and strength drain from his body. The flesh shifted and squished, as his arms and legs became curvier, less muscular and admirably feminine. Hair fell from his sliver of a beard. His legs and arms followed suit, all perfectly waxed and soft. Just like the lady Venus. The weakness troubled at first, as if robbed of something, but then it felt perfectly normal. As if he had never know what it was to be any stronger or bigger. What would it feel like to be as strong and tall as a man. To be able to fight and protect like one?

"What are you doing to me you bastards?" He recoiled at the foul foreign  language coming out of his mouth. He sounded like the locals. Shit what if they heard me? Oh.. good. I can see if they got any guts! He felt passionate rage he had never felt before in his life. It felt  liberating.
"Pieces of shit. Apes. You know what's gonna happen to you when I get out here?"
A real bitch. Yes... they call me a bitch, but I have the respect I deserve! I was always the toughest girl in the neighbourhood. Beauty queen with a hard edge. And then he met up with her handsome Filippo. The man for him!
"WHO THE FUCK IS FILIPPO??" He shouted. He felt a pang of grief. How dare I ask that? My husband sacrificed everything for the Cardone family. Now he's rotting in a cell thanks to the cowardly shits! Memories came to him of watching someone being tortured, his face beaten to a pulp. He knew he should be repulsed, he hated violence didn't he? But instead he felt the pride of duty. Filthy snitch.

He roared in pain from the crunching of bone, digging his lengthening fingernails into the chair. His body contorted as his hips cracked out. His stomach pulled inwards while the sides of his torso drew in. Cheekbones raised while his nose thinned. His lips puffed out, but clearly lacked the kissability they had years ago. Skin pulled in different directions around his eyes as they grew grand, beautiful and seductively dark. His bright blonde hair turned luscious dark brown as it descended down onto his shoulders. He sniffed at the air with his new nose. He could smell differently now, smell more, fuck, I stink so badly!

His head swayed. He had something extra down below. Something that didn't fit, sticking to his groin. "No! Why do I have a fucking cock and balls? Oh god! Did I grow a cock? Disgusting. It didn't work.. I'm a freak, how will he love me now?." Wait, I always had one didn't I? He felt a sense of panic as his mentality began to narrow into that of an older female mind, one that couldn't comprehend this strange thing dangling between her legs. Nor the weightlessness of her chest. He couldn't even remember being a bare-chested little girl without his breasts. Is that what this was? Was he a little girl again now?

 He sat stunned and then tried to twitch his cock.  He bit his new lips. "I guess some might call that a cock!" As he punctuated the last word. He felt like someone had grabbed his adam's apple in his forefingers for a moment. He heard a snip, a grind. Then when he spoke, the rumble he was used to was gone. He let out a mocking high-pitched cackle in his new voice. He loved hearing his sultry voice. The voice that made men drool and squirm. Hu...no, this exotic slutty voice isn't mine! This Sicilian language! Camurria! I'm not a slut! Those are lies! But it is my voice. Men once loved it when he called their name. Even at his age he was still a wild screeching fuck. He tried to imagine doing a woman, but it felt boring, lazy, a chore. It wasn't right for him. He wanted something deep up his arse now, something a little rough. Some hairy balls slamming right on the cheeks. His nipples stiffened and the raw dollops got wider and wider. He pulled his thinned hands out from the bonds and began to knead one of them.  Doughy fat began to pour into the chest as they swelled to a hefty size. They were still perky and untouched by a surgeon's knife. No matter what they say about that. It's a lie! The women in my family all had big ones!

He kept indulging his well-grown breasts, then let out a purr. They seemed to have dried up a bit these days mmhmm. He sighed at his cock struggling to harden. Looks like it didn't care for tits anymore. Oh... ohhhh, he felt like a velvet gloved hand was slipping him one. His thoughts turned to power and sex. Of being penetrated by a dominant powerful man, but also controlling them. Ugh, but lately the only thing inside her had been a thick dildo! The last of Jack's male self tried to struggle on. He should be the one with his dick wrapped in a pussy but... being filled felt so good. She liked being on her back.. most of the time. It was her place for her husband. Measured up to fearless man like Filippo she had never been much of man really, almost laughable. A weakling tax bureaucrat  The invisible hand pulled faster and faster, then he let out an agonized sounding horny shriek as creamy white burst over the silk of the dress. His now forcefully aged and wrinkled penis started to thin and wither into a nub. It let out another pathetic transparent squirt, the last of his cum. Then the deformed throbbing cock shrunk down into the throbbing experienced clitoris of an older woman. The loose lower lips and insides formed beautifully, despite having once given birth to a departed son. My poor boy... my... she let out a throaty dry wretch as her eyes rolled to the back of her head. She convulsed violently, then an instant later, she passed out, her last memory of bullets going through her chest and head. Blood filling her mouth and...

"Mother and saviour. It worked!" He gently pressed on her breasts. She slowly opened her eyes and stared at him. Blinking only once, before slapping him across the face.
"Of course it worked giuccu. God! Took you long enough you worthless dog." She tried to hold back a scream of delight. Maravigghiusu! It seems Grandma wasn't as insane as they said.
A dumbass she didn't recognise came over and bent down. His mouth stuck open, his wide-eyes darted all around her face. "Fuck! There was a fucking guy there. This is wrong, a crime against.."
She grabbed him by the collar. "There was NEVER a man here. You got it?"
"But..."
"But what?! You see this face? I am Sabina Cardone. Say nothing, just fucking nod."
"Yes madame Cardone." He fell backwards a bit, still shaking his head in disbelief.
"Please, forgive him madame." Antonio said. She put up a hand and tilted her head downwards.
"This doesn't leave the room."

Her dainty feet slipped out of the restraints. As she stood up, she groaned at the wet patch of cum on the inside of the dress. She creaked her neck then took in some slightly strained breaths. "What a shame it couldn't make me younger. I suppose being saved from the fires of hell is enough for now."
"You're still beautiful!"
"Yeah beautiful madame!"
She tried to smile, but part of her wondered if her soul really had been saved, or if she was just that man pretending to be herself and wearing her fucking skin. Either way, the soldiers  had their lady of war back. And she could see their revenge with her own eyes.
"I want the fucking Turturro to suffer. My husband will be out of jail soon. Every fucking one of them will have a grave for him to visit by the time he gets out."
"Of course of course. We're ready. The kids are watching the streets for them." Antonio said. They pulled out their phones and started making calls.
She smirked and grabbed some of the silk dress between her fingers. She gave it a kiss. With a little cleaning, why not?