The Sissy Investment Ch. 03

Story Info
Colin's life is taken over and a sissy-whore is born.
3.1k words
4.38
17.5k
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Part 3 of the 5 part series

Updated 06/11/2023
Created 08/04/2022
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The inevitable arrival of Monday morning came, and Colin was silently begging Daddy J not to make her go to the office dressed as she had been all weekend. The hair, earrings, lip injections and shiny glittery gloss would surely be humiliating enough to satisfy her owner's craving to humiliate and degrade her beyond comprehension. Not to mention her agonizing asshole.

Sadly however, Colin was wrong.

Daddy J produced a women's business suit that had been tailored to fit Colin -- all at the slave's expense via credit card -- and insisted it was the right look for such a gurly-fag to wear to the office.

The snickering...the staring...the outright laughing as well as derisive insults that were hurled at Colin as he moved through the office that day were beyond mortifying. At one point she heard two female Interns talking... "see...I told you...I saw Spencer at the mall on the weekend with his big Black boyfriend...who knew the little weirdo was also some kind of sissy-fag homo. He was dressed like a horny little slut!"

By the end of the work week, it came as no surprise to Colin that he had been summoned to a meeting with Senior Leadership - a meeting also being attended by the Manager of the IT department in the firm.

The long and the short of it was that while sensitive to employment and Constitutional rights held by all people, and the fact that they could work with the feminized attire and transition within the company - the use of company time and resources to watch and download the most perverted filthy pornography imaginable was simply unacceptable.

Colin was fired on the spot.

To keep things quiet, Colin was given a Cashier's cheque for a year's salary - nearly $90,000 - that he was forced to turn over to Daddy Justus after arriving home and telling him what had happened.

Sobbing, Colin knelt beside the computer as she watched Daddy J deposit the cheque and then transfer the money in one lump sum into his own account using Colin's passwords that had been extracted early on in her slavery.

Justus hadn't planned on Colin getting fired quite so quickly so he needed a way of managing the little slut during the day while he was at work until the final phase could be put into action. Arriving quickly at a potential solution, Justus put Colin on her knees between his thick thighs and had her deep throat his cock while he made the telephone call.

That 90K windfall was going to come in handy as the call he was making was moving up his agenda by a number of weeks. The telephone connected... "Dr. Siddiq?...this is Justus Hill..."

It was going to take the janitor a few weeks to get his retirement paperwork in order and to complete his three weeks' notice that he had to give the firm in order to access his benefits. He couldn't risk Colin having all that time on her hands each day which might allow the fag to develop a bit of a backbone and challenge some of the control that had been cultivated so carefully. The perfect solution was to have Dr. Siddiq start working on the slut's body now, and the rest would fall into place in due course.

Kept in a drug-induced haze for the bulk of the time that she had been resident in the extremist doctor's private surgery, the day when Daddy Justus arrived to collect her was the latest turning point in the humiliating drama that her life had become.

Standing naked in front of the two men with no way of covering or hiding her body, she had no choice but to listen to her owner compliment the sadistic fuck of a doctor on his craftsmanship.

"Holy shit Doc...you are a fucking miracle worker. She looks like the sluttiest fucking whore I think I've ever seen. Fucking A! Amazing job Doc, simply amazing."

Dr. Farhan Siddiq replied by stating that it had been a pleasure to work on and modify such a vile little whore as the Black man's gulry-slave, and detailed every single alteration that he had performed on the youth over the past month.

"First, Mr. Hill, are her tits. You said that you wanted a serious set of boobs for her, and we discussed medium projection implants with I believe 600 cc of silicone enhancement. I did start with those but decided in the end that even though it would painfully stretch her skin for a time and forever be onerous on her back to haul around an even larger set than we discussed...I went with high profile implants and stuffed her full...800 cc per breast.

These have much more projection, are extremely firm, and I assure you will stand up to extreme use and abuse of any kind that you wish to apply to them."

The laundry list of changes made to the former Intern's previously male body included alteration of her areolae to make them much more broad at 5-inches across as well as deep purple in color, thickening and distention of her nipples to stand a full inch away from her chest and be as thick as Daddy J's thumbs, hormone-induced shrinkage of her sissy-balls so that each of them was no larger now than a blueberry with similar minimization of her cock so that it now resembled an extremely large clitoris, tightening of her scrotal sac so that it looked like a miniature version of a real man's ball bag, shaving of her vocal cords, refinement of her nose to make it smaller and more shapely, re-injection of the lips on her mouth to enlarge them even further, and similar treatment to her anal lips to make them permanently swollen and distended without sacrificing their elasticity for stretching.

Once Justus had paid the bill...nearly two-thirds of the severance payment that Colin had received...Master and slave were on their way home where Colin would see that the janitor had not been idle in his off hours while winding down his last few weeks of employment for Freemont & Tait.

During the drive, Colin sat in humiliated and degraded shame as her owner outlined even more information that the surgeon had shared before they left his office.

"Turns out slut that Dr. Siddiq was able to do some work inside those giant new tits of yours to make those sow-teats you're sporting as sensitive as electric live wires. He manipulated the nerves somehow so that when those jugs get some attention from a brother, we'll be practically peeling you off the ceiling. Did the same thing apparently to that gigantic new clit and said that I'd really get a surprise the next time I had something buried ultra-deep inside that hot juicy cunt, too. Daddy can't wait to take this new body of yours for a test drive yessiree."

When they arrived at the loft, Colin was perplexed and disoriented as the layout had changed and new walls had been erected in what had previously been a completely open-plan space.

"I know what you're thinking gurl" Daddy J said as he studied the look on Colin's face... "now what did Daddy go and do messing with his big beautiful wide-open loft!" Colin smirked silently to herself...his loft...HIS loft...all of this rightfully belonged to Colin!

"Well, I needed to create a proper bedroom for my gurl -- can't have you sleeping in a walk-in closet for the rest of your life now can we. And we needed a photo and video studio for your new website and on-line videos that you're gonna be making to generate an income for your Daddy and make him some serious cash. Of course, constructing all of this in just a month took the rest of my severance package that you earned for Daddy when you got yourself fired, but I think it will be a good investment in the end. Gotta spend money to make money isn't that right slut?!

Let's go look at your bedroom first."

Colin's head was spinning as Daddy J walked her into her new room. It was a bondage fetishist's wet dream come true. A king-sized bed fitted out with latex rubber sheets and pillows was set up against one wall, with the remaining furniture consisting of a pommel horse, fuck bench, St. Andrews Cross, and bondage chair.

Shelves covering one wall had every kind of sex toy imaginable lined up and ready to be used to torture and abuse the sissy-gurl's surgically altered body, and there were tie down points everywhere Colin looked. In a small closet hung rubber and leather sleep-sacks and straight-jackets, and on the inside of the door an array of floggers, whips, paddles, and crops were neatly arranged so that a Dom could peruse the implements available before using them to decorate the slut's milky flesh with welts and bruises.

"If you think this is nice gurl...go check out your bathroom!" Daddy Justus crowed.

Colin sheepishly entered the bathroom to find a toilet, a bidet, a rim chair, a vanity with a single basin, and a large walk-in shower with two upper shower-heads as well as two spigots on the wall -- one about shoulder height for the sissy and the other level with her knees.

By the time the big Black man had led his sissy through the rest of the renovations she was a wreck. The video and photo suite was nearly an identical copy of the bedroom but with hard-wired wall mounted cameras everywhere, and a bare section of wall with various pull-down screens faced by a tripod topped with a high-resolution digital camera.

Daddy J explained that her bedroom was where she would sleep each night if she was not underneath him being forcefully impregnated, as well as where she would entertain special paying customers who wanted to enjoy some personal time with her.

The video suite was something else altogether. Colin was to become an on-line phenomenon for a community of perverted men who liked to see she-male sissy-whores used and abused to tailor-made scenarios that they themselves could help construct as paying members of her fan-club.

A simple $20/month membership would buy five video views, while $50/month and $100/month buy-ins would unlock access to much more content. For a whopping $500/month, an "influencer" as Justus called them could dictate activities that the sissy would be subjected to for their viewing pleasure, as well as choosing particular outfits, toys, positions, and levels of intensity for what the slut would be put through.

"You'll be happy to know, bitch, that even with what your Daddy has posted on-line advertising your site which will be going live in the near future, you've already got five "influencer" level members and a bunch of other brothers lined up in the other categories which all together is gonna earn me about 80K per year. Just a beginning of course - with a bit of exposure you'll bring in way more than that and the in-person customers will be paying a pretty penny for the use of that body as well. I figure you'll be clearing me 200K in no time.

Should make Daddy J a comfortable retirement nest egg before you're too used up to be much good for a steady income. When the money starts to dry up I'll just sell you on to recoup one last chunk of change from that slutty she-male body of yours. After that, I'll just relax here in my new loft and decide how to spend my time and money I guess."

So, this was it. What Daddy Justus had been doing to her from the very beginning was to build towards this moment when he would make her a full-time whore with him raking in cash by having her degraded and used and abused by perverts near and far who wanted to see her suffer for their pleasure.

"Pay attention bitch!" Daddy Justus barked at her, "we got some legal shit to take care of before we can get busy setting up your new life as my cash-slut. Sit your ass down at the table. Daddy has some papers for you to sign."

The first thing Justus put in front of Colin was the deed to the loft as well as the registration on the Range Rover. With two signatures, Colin owned neither her home, nor her vehicle any longer -- both now belonged to Daddy Justus.

What followed was a sweeping power of attorney declaring that Colin did not feel capable to make her own bodily or health care decisions and that she was voluntarily declaring Justus Hill as her legal Conservator, empowered to make all decisions on her behalf.

The document of course stated that she might re-assume these responsibilities in the future, but Daddy would never let her get near a lawyer or another document to rescind what she had just signed over - basically her whole identity - to the big Black Master.

"Well..." Daddy J declared, "now that you've made me responsible for all the important decisions owing to the fact that you're just a stupid little White cunt, for my first official act I've decided to change your name, and your gender gurl...officially."

Colin's jaw dropped open when she heard Daddy J utter those words. Just like the rest of the day's events so far, this had all been planned.

Once Colin had signed over legal decision-making power, what the big man was about to do was entirely within his authority.

By the time Justus Hill was done signing HIS stack of legal papers that afternoon, Colin Spencer had legally been replaced with Colleen Spencer, and the 22-year-old that had been a "he" for over two decades in the stroke of a pen became legally, a "she".

Colleen's passport and credit cards were cancelled, her meager company pension earnings were signed over to Justus, and the post office had been advised that all letter mail addressed to her would be bundled up, re-routed, and delivered to him. Effectively, Colleen was now completely isolated and legally dependent up on Justus Hill -- ex-con, and janitor, in order to survive.

And Justus planned on making sure she would never forget that fact.

As Colleen's body needed a bit more healing time and there was plenty of cleaning and tidying up to do after all the renovations, the sissy spent the next week thoroughly cleaning Justus' new home clad in a skimpy French Maid's uniform made of black and white latex rubber.

For his part, Justus firmed up the connections with who would become Colleen's video and photo producer, and her booking agent for all of her in-person private sessions. It was a friend of his from his prison days who was a technological wizard and needed a leg up.

Michael Reyes had been born Michaela and had grown up being victimized almost daily as a trans person in the inner-city Black community. He was the only child of a Haitian mom and a Black Portuguese father, and had never fit in to any community he might have had access to as a birthright.

Introverted and brilliant he became a computer whiz and had eventually ended up on the inside found guilty of hacking several government agencies on-line.

In prison, Justus had taken a soft spot for the fledgling Michael and offered him protection for free as opposed to the standard sexual services that were normally required for that type of thing.

They became friends, and when Justus reached out acknowledging he needed some help organizing his new slut-slave's on-line career, Michael jumped at the chance.

Bitter and jaded, the opportunity to humiliate and abuse someone who was changing genders albeit under threat and coercion in this case, appealed to Michael's sense of balance in the universe. He would do all of Colleen's photo shoots and had set up secure methods of payment processing and booking personal time with the sissy for perverted paying John's that would completely evade the notice of any formal authorities, including the tax-man.

Only a fraction of Justus' income from selling Colleen's body would officially be declared as proceeds of a shell corporation, while the bulk of the cash would be tax-free proceeds of flat-out prostitution and slavery.

With his "model" plied with liquor and quaaludes, Michael was getting some excellent shots to use as promotional material to grow the number of subscribers to her video channel which would exhibit Colleen being used for the most seriously degrading sexual exploits imaginable.

Topless with her enormous tits projecting from her chest, Colleen was tweaking one of her prodigious nipples with one hand while sucking on the thumb of the other, drooling all over her naked chest and decolletage. She had whorish make-up on her face and shiny gloss on her balloon-like lips, while her platinum blonde tresses were held away from her face with a pink hairband detailed with a shiny satin bow.

Her clitty-cock was exposed but locked in a tiny pink chastity cage making it look like a little nubbin, and her feet were buckled into sky-high heeled strappy sandals that she could barely stand in without toppling over in her impaired state.

Daddy J "touched up" her mood on a regular basis with various substances to keep her ultra-compliant and disoriented as well as to routinely demonstrate to her his total control over her body.

Stuffed in her ass was a huge black butt plug, and her tramp stamp reading "sissy gurl fag" was clear to read in many of the pictures. At Michael's suggestion, the plug was routinely swapped out for enormous black dildos of varying shapes and sizes for some of the shots, and one was repeatedly shoved down her throat to force her to gag and choke and splutter up copious amounts of thick throat slime that now slicked her face and body.

She was also fucked in the mouth and cunt by Daddy J in several photos, with his enormous cock being the only part of his anatomy visible in the shots. Colleen's face, however, was shown as plain as day and the pics would become advertisements hawking her wares to any sadistic fuck in cyber-space with some money to burn and a desire to see a she-whore gurl slut degraded for his amusement.

The shots were XXX-rated and extremely graphic with swollen pussy-lips, dripping cum, and creamy facials prominently pictured among the images. Almost as soon as the photos hit the quiet corners of the web where potential customers lurked, membership sales started to explode.

"Time to get ready for your guest sissy" Daddy J called out to Colleen. "You can finish your chores later...for now it's time that you got dressed...Judge Carver has made some very specific requests for your outfit this evening."

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5 Comments
Tracey_FrillyknicksTracey_Frillyknicksover 1 year ago

Excellent welcome Colleen I can't wait to hear about your adventures as a sissy whore. This is the lifestyle and treatment that I have always craved to have.

AnonymousAnonymousover 1 year ago

Ahaha I genuinely love that Justus is so respectful to Michael. like yeah, he may be a psycho who imprisons, rapes and force fems an innocent man, but he's no transphobe.

Renee_BRenee_Bover 1 year ago

I love this story!!

AnonymousAnonymousover 1 year ago

I'm admittedly confused as to why it was planned for the sissy to eventually get fired. He was already making bank and the daddy was profiting from it. Why search porn at work and lose his swanky job? This chapter even explicitly made clear that transitioning at work was perfectly okay and he just got fired for the porn. Sure they're apparently going to make money whoring out but why not still have the high paying job and whore on the side. I just don't understand.

AnonymousAnonymousover 1 year ago

Wow. It just gets worse and worse and worse.

Its worse than a snuff movie.

Please seek help

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