The Sissy Investment Ch. 02

As Colin leaned back onto his calves, another fresh load of hot man-cum slipping down his throat from giving Justus his regular evening release, the Master began to peruse Colin's daily report while the slave stared intently at his deflating cock...exactly where his eyes were required to be focused at all times unless otherwise instructed.

"As usual slut, you have done a very thorough job of accounting for your time today. And as a reward I have some new instructions for you starting tomorrow. From now on, for at least ten minutes every day, you will log on to some porn websites from your office computer. I will send you the sites you are to visit each day by email in the morning, and when I inspect your browser history in the evening, I will expect to see that you have been obedient and done exactly as you were told."

Justus could see that Colin was visibly uncomfortable, and already knowing what he was going to say, relished the anxiety his slave was going through when he gave Colin permission to speak.

"But Daddy" Colin pleaded "They monitor our browser use at work and the IT department will know that I have accessed porn sites and I will get in a lot of trouble." Colin was near tears now, very unsure of what to do next.

Justus simply smiled, cocked his head to one side, slid his leather belt out from his opened jeans, and replied to his slave with one sentence. "Then slut, I guess you had better decide whether you want to be in big trouble with your Boss, or with your Daddy." With that Justus snapped the leather belt on itself with such a crack that Colin's body jumped from the sudden startling noise.

Slowly nodding his head in agreement and telling his Master that he would rather face discipline at work than at home, Justus patted his slut on the head and said "good bitch...and I think we'll make it twenty minutes of porn per day at the office since you're such a stupid worthless bitch who needed reminding about who really matters in your life...your boss at work or your Daddy who owns your ass. Any issues with that slut?"

Colin shook his head no, with tears beginning to form at the corners of his eyes.

The porn however, had not been the only adjustment the Master had planned for his slave when it came to behavior at work.

Cupping his slave's face in one of his massive hands, Justus squeezed hard enough to squish Colin's cheeks but not enough to cause pain...only to make his recently fucked mouth squash into a juicy pucker. The slave could then taste something fruity being applied to his lips and could see the big Black man working a small tube round and round in front of his face.

"Go look at yourself slut" Justus ordered.

When Colin looked in the mirror what stared back was his face, with shiny wet-look gloss on his lips. There was a slight sparkle to the gloss as well, and it was unmistakable that he had cosmetics painted onto his mouth. Not only that, but his Master now loomed over top of him from behind and announced that he'd made an appointment the following day for Colin to get some other work done that would start to give him a look that matched his status...that of a cock-slurping sissy cumslut.

"I've decided to change you gurl...into a fully functioning boy-sissy. I'm gonna completely femme you out, and then turn you out as the horniest and dirtiest little gurly-whore this town has ever seen. Won't that be fun?!"

Laughing out loud, Justus spun around on his heels and made for his bedroom, leaving Colin crying fresh tears of humiliation in the mirror. "Don't stay there admiring yourself for too long slut...Daddy's horny again and wants to stretch that boi-pussy of yours. Get your ass into the bedroom -- I'm gonna bust open that cunt and load you up for the night."

For nearly forty minutes Justus rode Colin's ass in a variety of positions...taking the 22-year old from behind with him on all fours, making him bounce up and down on Daddy's big Black tool, folding him in half and pounding him missionary with the skinny White boi's ankles pinned beside his ears, on his side, and the current favorite for when he blew his load, laying on top of his slut with the bitch smothered beneath his 300 lb frame, thrusting his 9-inches home with so much force that Colin's hole felt like it was being dilated around a pop bottle.

Roaring in ecstasy as he climaxed, Justus creamed the bitch's insides with hot cum from his huge hairy balls -- six thick shots expelled from his satisfied meat like they were fired out of a pump action shotgun.

As Justus allowed his snake to slither out of Colin's swollen inflamed hole, he beamed with pride at the fact that it could not close right away but instead began to belch and ooze sperm onto his waiting cockhead which would soon be deposited into Colin's mouth for cleaning and worship before dispatching the slave to the closet that was now his bedroom.

"Alright cunt...have your midnight snack and then get into your box. Daddy wants to go to sleep and needs to make sure his bitch is all stored away safe and sound for the night."

Having lovingly cleaned and suckled on Justus' flared helmet, Colin openly wept as he heard the click of the padlock on the outside of the door of his closet/bedroom, and slowly drifted off to sleep covered in his threadbare blanket as he listened to the former janitor at his office snoring, comfortably enveloped in what used to be his expensive down-filled duvet.

Morning had come quickly, and after bathing his Master, dressing him, preparing his breakfast and tidying up the loft, Colin was advised to go into the bedroom and get dressed as Daddy was taking him out on some errands that would take several hours.

When Colin looked on the bed at the outfit that Justus had selected for him to wear on their outing, he was horrified. It was only the thinly veiled threat called out from the other room that he had ten minutes to get changed and get his ass out of there that made him snap to attention and put on the outfit he had been ordered to wear.

Justus was more than pleased when Colin emerged from the bedroom...the absolute picture of sissy-boy slutiness.

On his feet were 4-inch platform Converse Chuck Taylor high tops in bubble-gum pink with a bright white rubber toe cap. Ankle socks in blush pink, capri-length cotton pants to match, and a tight white t-shirt with a deep scoop neck and cap sleeves trimmed with pink grosgrain ribbon completed the look.

Beckoning his slave to approach, Daddy Justus once again smeared the lip gloss around Colin's mouth and this time added some dark eyeliner around his big puppy dog eyes.

Colin was humiliated, and once buckled into the passenger seat of what used to be his car, was devastated to learn that their first destination was a downtown mall very near the office. Any one of the other Interns who routinely worked weekends to make up their hours would be likely to see him all tarted up and out on display as the janitor's plaything.

Parking at the far end of the mall, Justus made Colin walk through the food court and past all the shops before arriving at the day spa establishment called "A Girl's Dream" where he was forced to check in for his appointment. Every other patron was female and sitting in the waiting room open stares and even some laughter at Colin's expense could be easily overheard.

"Colin Spencer?!" the shop assistant announced when it was time for him to meet his stylist, and the bitch was led through to the back of the store to meet with Gwen...one of the owners of the shop, who had been fed a story and a half by Justus over the phone when he made the appointment on Colin's behalf.

"So, let's see here now" Gwen said turning her attention to Colin...

"Says here you want a hair color change to a bold platinum blonde, both ears pierced, facial electrolysis, and your eyebrows plucked. My goodness and a new hairstyle that it says here you want some advice on with respect to what might look good on you. I think a nice pixie cut or maybe a page-boy type bob might look work for you...nice and feminine and will go great with your new eyebrows and hair color."

Colin was mortified as the stylist continued her chit chat... "I think it's wonderful that you have such a caring father who not only supports you making this change young man but was even willing to call and make the appointment himself detailing all these new directions in your look. You really are a lucky young man...er...I guess I should say lucky young girl shouldn't I?"

Gwen disappeared down the hall to retrieve some supplies while Colin sat in utter defeat, knowing that he could not tell the stylist the truth without incurring the wrath of his new Master, and therefore had no choice but to let this woman feminize him and alter his appearance as Justus had instructed under the guise of it being his own choice.

By the time the appointment was over, and Colin walked out of the day spa the only resemblance to the version that had walked in was the clothing. She now sported gleaming blonde hair cut into a page-boy style with pink barrettes holding it away from her face on either side, thinly plucked arched eyebrows, and sparkling zirconia studs in both ears. When it came time to pay, Daddy Justus handed her one of her credit cards and the final humiliation was that the nearly $500 dollar bill for her modifications was billed to her former self...Colin Spencer.

She was then paraded back through the mall and re-installed in the car to be driven to their next port of call.

Once they had arrived, Daddy Justus again did all the talking in the seedy little tattoo parlor -- chatting with the biker-looking artist as if Colin was not even present in the room.

"Like I said to you on the phone...I have a new little White sissy that wants to be marked as my bitch...as slutty as possible...and she wants me to choose her tattoos for her. It gets her off see, being controlled and displayed like this in public as my little gurly-fag."

The fat ugly biker nodded and laughed and grabbed Colin by her skinny little arm and swung her into the chair while the two men talked further about what might look good on the little cunt.

Colin sunk deeper into a well of shame as she heard her owner agree to a tramp stamp on her lower back, Justus' initials forever inked on the back of her neck just below her hairline, and a rock-hard cock -- in Black ink -- preceded by an "I" with a heart next to it, on the outside of her left ankle.

The tramp stamp was to read "Sissy Gurl Fag" in stylized script right above her buttocks so that the top of each letter would be clearly visible above the line of her panties.

The process of being inked was new to Colin, and very painful. She gritted her teeth and winced as the needle pierced her flesh over and over, crying out in pain several times to the delight of both her Daddy, and the biker doing the artwork.

When it was over, once again it came time to pay the bill...but this time instead of simply handing over the credit card, Daddy J did some "bartering" on Colin's behalf.

The bill for all three tattoos was $700, and the biker stood patiently waiting for either the sissy-slut, or her owner, to make payment.

"I wonder" said Justus, "if you might be open to a flexible payment option for my slut's new ink." Intrigued, the biker asked the big Black man what he had in mind.

'Well, certainly she could pay you the whole $700 right now and be done with it, but this little whore really loves cock...I mean REALLY loves cock...and she'd be happy to offer you some use of her holes if you'd prefer that to settling the bill in the traditional way. With the bill being an even $700, and a fair price on the street for a quick blow being $50...I'd say we could offer you $600 now, as well as the opportunity for you to pump a hot load of cum down her throat and another one up her ass. How about it? A double shot for only $100 bucks? Hell, I'll even promise to bring her here for all her ink in the future and if you like the sample today, we can work out a more suitable arrangement in the future...whaddya say?"

It took the biker two seconds to shout "Deal!" as he groped his crotch through his well-worn filthy jeans.

"Excellent" said Daddy Justus. "You go on and take her into the back room just now while I watch your shop for you, and you just give me a holler when you're all finished with her. Take yer time...she ain't got nowhere to be and nothing else more important right now than worshiping your cock bro...do whatever is necessary back there to remind her of that."

The biker dragged Colin to the back room of the tattoo parlor and hammered her down onto a low table with her head hanging off the edge. Unzipping his fly and lowering his pants only far enough to expose his buttocks, his already hard seven-inch uncut meat was stuffed into Colin's mouth all the way into her throat in one thrust.

Leaning forward and pinning the whore's wrists to the table with his hands, Colin had no way to fight off the biker or his cock, and thought she was going to choke to death as he pumped and thrusted himself in and out of her gullet.

Justus could hear his bitch coughing and choking and struggling to service the aggressive biker and mentally checked off another milestone of transforming the former financial Intern into nothing but a useless slut.

Thick strings of throat slime were now coating Colin's face and dripping down towards the floor as the oral assault continued without relent. It took the biker fifteen minutes to achieve climax, grunting and shoving his dick home while he pumped belch after belch of cum down Colin's throat, cutting off her oxygen supply as he did so. It took thirty seconds for the tattoo artist to come down off his high, and as he pulled himself free from Colin's windpipe the sissy-slave spluttered and gulped in much needed air for all she was worth.

During the time it took for the tattooist to recover his hard on, he manhandled Colin over to a small bed and the little sissy had the distinct impression she was not the first slut to get used in the backroom of this tattoo shop.

Ordered to get on her back and spread her legs, the hairy biker produced a 10-inch black rubber dildo and smeared the tip of it around in a dirty looking canister of lube sitting by the side of the bed. "I can tell by the look of your pimp slut that you've got a thing for big Black cock...so let's see what that little pussyhole can do with this before I fill that snatch with a hot load of cum."

Colin could feel the hard blunted end of the dildo trying to split her open and gain entry to her insides as the biker shoved and twisted it against her anal lips. Slowly the lube slathered all over its tip coated Colin's sphincter and overcame the resistance her muscles had been mounting, and the black rubber cock plunged inward. Colin screamed, and Justus became instantly hard out in the front-end of the shop.

The tattoo artist ground the column of hard rubber into the little bitch, stuffing all 10 inches into her and prying open her pussy walls. Long-dicking her with it, steady strokes in and out reamed out her hole preparing it for him to bugger with his hard cock. The dildo was forced from side to side as well as in and out to fully stretch her she-male labia and open her up to gaping proportions.

The biker full-on fucked Colin with the large dildo, making himself rock hard again in the process so that when he dropped it onto the floor with a thud, mere seconds elapsed before he had replaced the fake dick with the real article.

With the images and thought of the slut spread open wide for him and the hard black rubber cock sluicing her sissycunt, the tattooed biker reached his second orgasm remarkably quickly. After only 10 minutes of rutting and grunting on top of Colin, his body began to quiver and the slut could feel his uncut cock thicken and spasm as it exploded inside of her, impregnating her with an impressive volume of sperm considering it was the biker's second load inside of an hour.

Exhausted, and fully degraded, Colin sat disconsolate in the passenger seat of his SUV which was now all but owned by Justus the Janitor, miserable at what his life had become in just a few short weeks. He'd gone from being a promising Intern with a life of family and industrial wealth and privilege in front of him, to a feminized sexual plaything for a sadistic Black Master nearly three-times his age.

So lost in thought was Colin that he didn't even realize that the vehicle had pulled into their last port of call for the afternoon. The parking lot of Dr. Farhan Siddiq, Plastic and Cosmetic Surgeon.

Frog marched up to the medical office with Daddy J's hand on the back of her neck, Colin breathed a sigh of relief when she saw the "closed" sign on the door. After all, what medical offices are open on weekends? "Don't get comfortable slut" Justus announced... "just for you, today the doctor is in!"

The 300lb Master pushed open the door and shoved the slender sissy right through it, causing her to stumble and fall right in the middle of the lobby. When she looked up, standing before her was a slightly built very pensive looking Egyptian man with wire rimmed glasses and a white coat.

"I take it, that THIS is the whore you called me about Mr. Hill?"

Dr. Farhan Siddiq was an Émigré from Cairo, having lived abroad most of his life, but never very far ideologically from his strict Muslim upbringing. With a voice dripping with disdain the doctor gave Daddy Justus an order, to "bring her", as he spun on his heels and retreated into his clinic.

"Put her here" the doctor commanded, pointing to a reclining exam chair while he also retrieved some heavy nylon webbed straps from a drawer. "Hold her" was the next order, and with one massive hand around Colin's neck Justus squeezed and cut off the slut's oxygen supply causing her to grab for Daddy's hand while at the same time pinning her helplessly to the chair while the Middle Eastern doctor secured straps tightly around her chest to bind her.

Once secured with a couple of straps, Daddy J let go, and Dr. Siddiq continued applying more straps -- around her waist, her thighs, below her knees, at her ankles and across her neck and forehead. Daddy Justus took the initiative of tying Colin's hands to the chair with ropes so tight they instantly began to cut off the circulation to Colin's fingers.

With the sissy-whore secured inextricably to the chair, Dr. Siddiq turned his attention once again to Daddy J, and simply said "I take it our existing arrangement is still valid, Mr. Hill?"

"You bet Doc...as long as you make her look like a circus freak bimbo slut...you bet."

"Good...good..." the doctor replied, turning now to address the terrified gurly boi strapped to the exam chair.

"Just so you know you disgusting creature, your owner here actually offered me the use of your body for what I am about to do to you. An offer I assure that I found nearly as repugnant as your existence. In my country, you would not be tolerated for your abomination of a lifestyle...but here in this country your kind are treated differently. So be it. Well...no one is going to protect you from me."

Now Colin really was frightened beyond reason and began to quake at the thought of what this madman doctor might do to her. So scared in fact, that the fear of Dr. Siddiq overrode her fear of Daddy Justus.

"Please!" Colin begged... "he's crazy and he's done all of this to me against my will...I'm a prisoner and he's blackmail...." -- that was as far as Colin got before Daddy J's huge hand was once again on her throat, with his enraged face staring down at her saying "You're going to pay like you cannot even imagine slut for that outburst".

Struggling to breathe, Colin could not finish her sentence and in fact could barely remain conscious. As she nearly blacked out the last thing she saw was an evil grin on her owner's face getting off on the fact he was choking his whore knowing that her very existence was now in his hands, and that she was very shortly going to be transformed beyond any point of return into a fagified tranny whore for his use, enjoyment, and profit.