The Sissy Investment Ch. 04

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Colleen's anal lips were hugely distended, purple in color with areas that were actually pulsing and throbbing from the intense amount of dilation.

Rock hard, Justus hauled out his cock and placed it at Colleen's pussyhole and nearly blew his load just from realizing that he could place the whole head of his cock inside of his bitch without touching any part of her anal walls.

She was opened, stretched, and fully dilated...frothy lube was steadily leaking out of her pussy and running down her taint. The sight of it was all too much for Justus as he stroked himself to orgasm and aimed his cock's eye right at the gaping target and pumped out seven healthy shots into Colleen's wide-open hole.

Adding a hot load of his piss for good measure into his rent-gurl, Justus slipped a large-sized egg plug into her pussy and pulled her limp arms behind her to be secured with a zip-tie, and turned out the light as he left her there to sleep off her session with the Judge.

She could clean herself up and tidy her room up in the morning. After all, she had a gang bang video to make with five big Black boys the following evening. A sissy-whore's work is never done.

"Good morning slut!" Daddy J beckoned as he sauntered into Colleen's room to find her on the floor where he'd left her last night...although now she was now fully conscious and begging with her eyes for some compassion and relief.

"Let me deflate that gag filling your mouth first gurl" Justus said, attaching the rubber bulb and twisting the metal knob to allow the butterfly gag to shrink enough for him to remove it from her numb and thoroughly punished mouth, with thick strings of saliva clinging to its surface.

She slurred out that she needed to use the bathroom.

"Ask properly bitch, and Daddy will let you empty out that cunt. You must be bursting with that hot load of my cum and a full bladder of your Daddy's piss all up in you for the whole night. Go on...ask real nice and proper."

Having sufficiently pleased Justus, he unlocked her collar but left her wrists bound behind her with the zip ties. "Ain't gonna need your hands gurl to empty out and get cleaned up."

Once Colleen was kneeling in the walk-in shower, face pressed against the tile floor and her distended pussy pointing up and back towards the wall, Justus pulled her plug and watched the enema he'd drained into her last night pulse and spew from her hole.

Mingled with cum and the j-lube that judge Carver had used to slick up her walls, the mixture had thickened and plopped out of her insides in gelatinous globs and slowly slithered down the drain.

"Ugh, you certainly need to be cleaned out bitch. You've got a very busy day ahead of you and that stretched out cunt needs to be back in shape before your co-stars arrive. Their cocks are big...but not as big as your fucking cunt-hole is right now that's for sure. Back it up slut...get yourself plugged and mounted on your douche."

The lower spigot in Colleen's shower room had been positioned at the perfect height for her to be impaled on when she was on her hands and knees. Once its bulbous tip had been fully enveloped by her lips, Justus applied a broad black rubber collar to her neck that had two D-rings one on either side.

Chains from the rings were stretched back towards the wall with the spigot and clipped to metal loops built into the tile. Prevented now from moving forward and freeing herself from the spigot, Daddy J turned on the tap and adjusted the temperature...warm but not hot.

The rubber flange on the spigot inflated and deflated on a pressure-controlled mechanism. When water pressure backed up against the spigot the rubber seal would inflate and remain that way for five minutes before shrinking back to size. It caused Colleen to fill, be sealed and retain the fluid for a cramp-inducing length of time, and then gave her one minute to empty herself before the next tide rolled in.

Six-minute cycles that Daddy J subjected her to every morning like clockwork to keep her squeaky clean for deep insertion and fisting play that so many of her clients enjoyed.

"I think we better go six cycles this morning instead of your usual three gurl...the Judge was up in you but good last night and your pussy is stretched to shit right now. We need to make sure you're spotless back there before you go on camera tonight."

After nearly forty minutes of cyclical enemas sluicing out her cunt, Colleen was feeling surprisingly restored. Daddy Justus came back and cut the plastic ties binding her wrists, allowing her time to shower, dry herself, and get properly dressed before greeting him in the living room.

"Get down on your knees gurl and take care of this morning wood and then we can have a chat about some decisions Daddy has made for you."

Knowing that this could not be good, Colleen did as she had been ordered and positioned herself in front of Justus' throbbing nine-inch cock.

Having become expert in exactly how the janitor like to have his meat worshiped, Colleen immediately set about suckling and slurping on the giant head of her Master's cock, slicking it up with enough spit for it to be dripping and forming puddles on the floor along with strings of his glistening pre-cum.

Justus liked long slow blow jobs in the morning and had trained Colleen to work her mouth and throat like a sleeve, sliding them over his boner and swallowing his whole cock until her blown-up dick-guzzling whore lips were planted around the base of his shaft.

He liked her to hang out there for a bit...stick out her tongue and lick his ball sac...and then slowly withdraw until just the tip of his cockhead was poised at the opening of her mouth balancing on her pillowy lower lip.

Once there, she repeated the whole process never losing rhythm if she knew what was good for her. By the time Daddy J would hold the back of her head while she was fully impaled and deliver his seed straight down her throat, his cock was coated in viscous slime from the inside of Colleen's throat and the smooth slick slippery feel was like heaven for the big Black man.

Morning feeding completed, Justus had Colleen sit back on her haunches and listen up while her advised her of a decision he had made on her behalf.

"Now slut I know you ain't got any friends, and that you're reliant on me to manage your day-to-day life...but there is one detail that we've been neglecting...and that is having you come out to your family as the tranny-whore that you've always wanted to be. Daddy J has been very patient with you in this regard but it's time that you were honest with your parents about the life you've chosen for yourself."

Colleen was aghast, and thoughts crashed about within her head upon hearing what her Master had just said. The reason she had no friends left is because he had taken over her life...her email...her phone...and told them all to fuck off and leave her alone as if the messages had come from Colleen herself who was still Colin at that time.

It seemed like a lifetime ago. She had not been allowed to contact her family, and when messages did come in from her parents he had made her watch as he opened them all to ensure they would register as having been delivered, and then delete them without a reply.

"After you make your film tonight slut, we'll contact your father and send him some pictures of you as well as some of your videos and let him know that I've agreed to look after you despite your whoring lifestyle."

"I'm sure he'll be happy to have finally heard from you, and hopefully he won't be too upset when you threaten to expose yourself to all his upper-class friends as an insatiable sissy-whore if he doesn't buy you off with a pile of cash. Luckily though he'll be rid of you at that point since you'll be promising to never contact him again after he pays up."

So, there was the final nail in the coffin.

Daddy Justus was planning on making her blackmail her own father and she knew full well that he would be disgusted with what she had become and would probably pay anything to be rid of her and never hear from her again.

Colleen began to openly weep which brought a broad grin to Justus Hill's face.

He leaned forward and through gritted teeth and full of disdain said to his slave -- "I told you cunt that I owned your ass, and once I'm finished making sure anybody you ever knew won't care shit about what happens to you, you're gonna be my cash whore until I decide that you're done. You...belong to Daddy Justus now bitch."

The janitor broke into peals of laughter, stood and pulled up his jeans around his meaty thighs and generous girth, and strode away leaving Colleen crying on her knees.

"Get your ass busy bitch -- this whole place needs to be cleaned and my meals need to be prepared. You won't be eating today by the way -- your co-stars will be here about 7:00pm, and I don't feel like having to clean out that pussy again so the empty stomach should make you hungry to guzzle down their cumloads."

That evening, the sixty-year-old stood back and admired his handiwork. Colleen looked like the quintessential horny little sissy-bitch by the time he had her ready for her photo and video shoot.

Putting the last touches on her look with the ribbons in her hair, the big Black man marched her out of her bedroom and into the studio where Michael was waiting to get her pictures done before the video action could begin. This was going to be hot!

12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
3 Comments
DiaperboyMiDiaperboyMi10 months ago

I want that enema device. Please use me 😍😍😍😍😍😍😍😍😍😍

Renee_BRenee_Bover 1 year ago

This story is AMAZING! I love it! But I get the feeling Daddy Justus is in line for some karmic intervention?

AnonymousAnonymousover 1 year ago

I’m enjoying this story. Great narrative and descriptions. Looking forward to seeing what’s next in store for Colleen. Would be great to see a link back to a now heavily modified Patti from Santa Rosa Slut - maybe some kind of group shoot / shared rubber experience?

Share this Story

READ MORE OF THIS SERIES

Similar Stories

Trapped and Trained Ch. 01 Man is drugged, then dressed up and trained to be a slut.in Transgender & Crossdressers
Making of Tina Ch. 01: Caught A story about forced feminization.in Transgender & Crossdressers
The Night That Would Never End Pt. 01 A sissy gets used and abused in a motel.in Transgender & Crossdressers
Prison Sissy Cuckboy Ch. 01 Beta bitch joins a gang as a sissy cuckboy.in Transgender & Crossdressers
Journey to Girlhood Ch. 01 Steve begins a journey after an encounter with a bully.in Transgender & Crossdressers
More Stories