Dr. Lilith's Retreat Part 5: Hard Limits (Patreon)

The club smelled like cinamon and incense when Stephanie pushed through the door into the small alcove with an empty ticket window.  The next door was propped open.  In the middle of the day there was no cover.  
Stephanie had shed her business suit for a black formfitting body suit and tight black jeans topped off with a short black leather jacket.  She had traded her heels for combat boots but she still carried the same attache case.  
Inside, the club had black walls and a high ceiling with exposed duct work and light pipes.  It stretched back from the entrance in a series of segmented spaces. The first was an empty dance floor.   Through an Arch she came to a “play space.” A polished wood St. Andrews Cross was hung inside a roped off area.  The wall beside the cross was decorated with hanging whips, flogs and paddles.  A set of tiered bleachers were against the wall for spectators.

The next space held the bar and tables, a Severe black-haired woman who reminded Stephanie of her own mother sat clad in skin-tight black latex.  Her right hand rested on a riding crop that sat on the table.  In her left hand she held a leash that ran to the collar of a man wearing a blond wig, makeup, a french maid outfit and thigh high stockings.  She smiled when she saw Stephanie.

“Come in young Miss Lilith!” She called. “Have a seat!” She gave the leash a quick jerk and let go. The Sissy-maid quickly clacked on 7”platform heels around the table and pulled out a chair.  Stephanie.

Stephanie accepted the seat and let the sissy push it in for her.  “Thank you.” She said.

“Please!” The woman said. “There is no need to thank her for doing what is expected!”  
The Sissy returned to the woman’s side and handed her the leash.

“Present for disciplin!” The woman demanded.

The Sissy turned toward the bar and bent over.  She lifted her skirt up around her waist revealing a pair of pink frilly panties.  Which she pulled down to expose her ass, bruised wand striped with welts.  Stephanie could see a silver ring around the base of the sissy’s scrotum but her cock was not visibele, though she was sure it would be caged.  A Large purple jewel decorated the exposed flared base of the sissy’s butt plug.

The air hissed and a new red stripe appeared on the sissy’s ass.

“Thank you mistress!” came the sissy’s deep manly voice through her crimson painted lips.

The crop whined through the air once more and another welt appeared.  The sissy thanked her mistress once more.

“Cover!” The woman demanded.

The sissy pulled her panties back up and let her skirt fall once more as she stood up and awaited instruction.

“You failed to offer our guest a drink!” The woman demanded.

The sissy bowed low.  “I am sorry mistress!”  She turned to Stephanie. “Would the lady like a drink?”

“Whisky Sour” Stephanie responded and enjoyed watching the sissy prance away to the bar.  “Charge it to your tab!” The woman called after the sissy as she left. “Mary never learns!”  she said to Stephanie.  “I’m sorry, I don’t think you and I have ever met, though your mother has of course spoken about you.  I am Charlotte Rosa and this is my club.”

“Thank you Mis. Rosa.”  Stephanie said. She nodded toward the sissy behind the counter. “Is that our client?”

Charlotte smiled. “Indeed it is.”

Stephanie looked at the sissy and then back at Charlotte.  “If this is a consensual transition, we can accommodate her without the trappings of the retreat.  I am sure my mother…”
Charlotte held up a hand to cut her off.  “Mary well, Martin is not transgender.  He thinks this is all roleplay. He is a misogynist with a humiliation kink.  He gets off on gender play, because in his mind there is nothing lower than a woman.”

“Ohh!”  Stephanie said.

Charlotte continued. “When a perspective client applies for my services, I look into them. Background check, social media, lifestyle, you know, all the stuff I need to know to keep myself and my other clients safe.”  Charlotte grew silent and looked coldly at the sissy as she brought over Stephanie’s drink and set it on the table in front of her.  “Mary,” Charlotte called.  
The Sissy snapped to attention.

“Scrubbing the toilets is women’s work, See to it!” Charlotte said without looking at her.

“Right away mistress.”  the sissy replied and then dissapeared into the next room.

Charlotte waited to hear a bathroom door open and then continued.

“This guy was a real piece of work! Based on his social media, I was going to just deny his application and move on, but then my PI told me how he treats his wife.” Charlotte said.  “Constant verbal emotional abuse.  She’s not good enough, she’s stupid, she’s ugly, she’s fat if you can think of a shitty thing for a husband to say, he says it. His wife has been so beaten down and degraded over the years that she just took it and apologized, until three months ago, when it all came bubbling up and she was admitted to the hospital for a nervous breakdown. When I found that out, I decided that I was going to go above and beyond.  She smiled.”

Stephanie nodded. “So what’s our cover story?”

Charlotte shook her head.  “We won’t need one!”  She picked up her riding crop and played with it as she spoke. “Marty has been coming to me for a five hour session every week for the last eight weeks. In that time, I have built this Forced Feminization roleplay dynamic and negotiated with him that we are completely in character for the duration of each session.”

“So?” Stephanie ventured “He’s going to think this is just play?”

“Right up to the moment you chop his dick off!” Charlotte gloated.

“Uh…” Stephanie shifted a little as she remembered watching her own penis shrivle into the tiny clitorus she now had. “We don’t actually chop anything.  The treatment just repurposes existing tissue in new ways”

“But you could!” Charlotte insisted. “Your mother says it heals everything!  So you could chop it off and then heal Marty a new pussy in it’s place.”

“I, uh..I suppose” Stephanie said.

“Good!  Cause I want a trophy!” Charlotte announced.  “Maybe I’ll have it bronzed so she can fuck herself with it when you’re done! That’s my special request!  I want his actual cock turned into a dildo and his balls preserved for display.”

Stephanie paused for a moment, then reached into her bag to retrieve a notebook computer.  She connected to the private chat with the retreat staff and her mother and passed on the request. After a few moments, littl bubbles showed that her mother was typing.   Stephanie looked up at Charlotte and smiled while she waited.  The computer chimed and her mother’s response appeared.

Dr. K: Take a plaster cast before removal, then freeze dry it after.  Make a resin replica using the cast and sink the penis jerky into the resin so the subject will always be able to see their shriveled member when they use the dildo.  Easy!

Stephanie shivered for a moment, as someone who used to have a penis, the whole thing was shockingly sadistic.  She looked up at Charolette, encased in black, flexing the riding crop in her hands. Sadism was exactly what this sponsor wanted for her subject.  She turned the computer around and showed Carolette her mother’s response.

“Ohhh, that’s perfect!” Charlotte exclaimed.  “Maybe I’ll make her use it nightly!”

Stephanie turned the computer back around.  “So, we are going to tell him exactly what we plan to do to him and you think he will sign up?”

Charlotte smiled. “The great thing about doing the unimaginably cruel thing is that no one can imagine you actually doing it.  He will assume it’s all part of the game.  Even the part about the dildo will just sound like me pouring on the fantasy.”

“What about the wife?”  Stephanie said.  “Is she out of the hospital?  Will she come looking for him?”

“After my first few sessions with Marty, I met with the dear wife and showed her what her Dommineering Husband got up to when he was paying a sex worker.”  She set the crop down and leaned forward. “Ironic, that after years of being crushed under his boot, subjected to all the worse of toxic masculinity, the thing that finally turned her against her husband, was a glimpse of submission and feminity.”  She leaned back.  “Wife’s in our corner, in fact, she plans to have Marty declared dead.  She gets the inheritance, I get a custom made Barbie-doll. Win-win!”

“Unless you’re Marty” Stephanie finished.

“Unless you’re Marty.  Well, once the paperwork is signed, her name will officially be Sissy from now on.”  Charlotte grinned wide.  “So shall we do the deal?”

Stephanie closed her laptop and tucked everything away into her bag except the admission packet.  She pushed that over to an empty chair at the table.

“No!” Charlotte said. “Sissy will do her work on the floor.”  She pointed to a bare spot.

Stephanie set the papers and a pen on the floor.

“SISSY!” Charlotte shouted.

Stephanie heard Marty’s heels clack, clack, clack on the wooden floor before she saw him come swishing through the door.

Charlotte pointed at the floor and then held her hand out.

Marty quickly clacked over to the indicated spot, put his leash in Charlotte’s hands and then knelt in front of the papers.

“Sissy Marty, We have determined that you are unfit for manhood.  You will sign these papers and renounce your right to have a cock!”  Charlotte announced.  “Head down, Ass up, get to signing!”

“Thank you mistress” Marty said and then went down on his elbows with the papers between his arms,  He pushed his butt up in the air revealing his frilly silk panties once more.

Charlotte traced her finger across the ruffles.  “Hurry up and I’ll peg you till you sissygasm”.

“Yes Mistress!”  Marty said as he looked at the top form.

<SNAP> The crop bit into his thigh.

“I DIDN’T TELL YOU TO READ IT!  I ALREADY TOLD YOU WHAT IT SAID! DO YOU THINK I LIED ABOUT YOUR PATHETIC COCK?”  Charlotte yelled.

“No Mistress! I just want to be careful!” Marty said.

Stephanie could feel the hair on the back of her neck stand up.  Three signings without incident and the sissy maid is going to be trouble?  She tapped her smart watch in quick rhythm.

Charlotte, yanked Marty’s panties down and swung again <SNAP!> <SNAP!> <SNAP!> “I said sign you little bitch!”

Marty winced under each one,  a bead of sweat rolled off his brow and fell on the paper.  “This looks real!” He grunted.

<SNAP!> “You don’t trust me?” Charolette’s voice was getting hoarse.

“RED!!” Marty shouted.

Charlotte froze mid swing.

Marty stood up, pulled up his panties and then picked up the stack of papers.  He looked over at Stephanie.  “Are you a fucking notary?”

Stephanie tried to play it off. “Only if mistress wants me to be.”

“Don’t bullshit me.”  Marty’s voice had dropped to a baritone and the lisp was gone.  He stood straight backed, adopting a manly posture despite the maid dress costume.  “What the hell are you trying to pull?”  He flipped through several pages “Power of attorney?”  He tossed the paperwork on to the table.

“It’s supposed to feel real.” Charlotte said.

“Feel real, I get.” Marty said as he reached behind him.  He shifted and then produced a silver buttplug which he wrapped in a napkin before setting it on the table. “My signatures on these papers would be real enough to ruin me!”  He said.

Charlotte was silent.

“I want the keys to this thing” He lifted the front of his skirt and pulled the panties down to reveal a cramped cock-cage that was anchored to a ring around his scrotum.

Stephanie had been tapping codes into her watch while this exchange took place.  She looked to Charlotte and nodded.  Charlotte smiled.  “It will come off, with your cock”

Stephanie lifted the watch to her mouth. “NOW”

The Front door of the club burs open and light poured in around the three broad shouldered men from Stephanie’s snatch team.

Marty turned and ran toward the back, only at half speed due to the heels he wore <Clack> <Clack><Clack>

He stopped as two more large men emerged from the kitchen in front of him.

“NO!” He yelled as the men closed in around him.  “LET ME GO!”

Charlotte raised her eyebrows at Stephanie as the men struggled with the flailing sissy.

“RED!” Marty yelled.  “STOP THE SESSION!  LET ME G—“ Marty’s cries were cut off by the ball-gag forced into his mouth and locked behin his head while the other men forced him to the floor and pulled his wrists and ankles back to hog-tie him.

Once Marty as securely bound, Charlotte stood up and walked over to stand over him.  She placed her toe on his shoulder.  “This is no session Marty.  This is justice.  After all these years of tormenting Wendy, you are going to find out what it’s like to be a woman.”

Marty’s eyes went wide at the mention of his wife’s name.

“Oh yes.” Charlotte said. “We’ve spoken.  She knows exactly what we are doing to you.”  Charlotte bent down over him.  “You’re going to be a girl, completely and forever.  Big tits, little waist, and no cock, unless some real man puts his inside you.”

She moved her foot to the side of Marty’s head, turning him to the side and then pressing it down against the floor.  “You could have signed, and had two final weeks to enjoy manhood.  Maybe Wendy was prepared to give you one last sympathy blow job.”  She pulled her foot off him.  “Oh well,  I guess you’ll never use that pathetic cock again!”

One of the snatch-crew men turned for the door.  “I’ll move the van around back, we can load the sissy there.”

“MmmmmfffffMMMMM” Marty cried out into the gag.

Charlotte made eye contact with Stephanie and winked.  “Oh, Marty, you almost forgot something!”  She snatched up the wrapped buttplug and turned back toward the helpless sissy.  Stephanie saw the napkins fall away as Charlotte decended over him.  Then she saw Marty’s eyes grow wide “MMMMMMMFFFFFFAAAAAAAMMMMM” He screamed into his gag and his hands and feet flailed in their bonds.

“Oh dear Marty.”  Charlotte said as she stood up.  “You should have relaxed more”.

She nodded to the four remaining men of the snatch team who lifted the whimpering sissy off the floor and carried him to the back door.

Charlotte turned back to Stephanie.  “That could have gone better.”

Stephanie nodded.

“Drinks?” Charlotte asked as she walked to the bar.