Predator and Prey Pt. 15

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Kitten further transformed; Carol-Ann further corrupted.
13.1k words
4.89
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Part 17 of the 24 part series

Updated 04/15/2024
Created 03/06/2023
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Predator and Prey

Corrupting a Mother and Taking her Son as My Femmeboi Sissy!

by Tawny Suede

Chapter 15 - Kitten practises, Carol-Ann crumbles

I started work early the next morning. We had a call to the construction site to fix some stuff that had gone wrong. We were given the choice of putting in for overtime pay, or taking a longer lunch or quitting early for the day. Just so long as the work got done on time. I'd received a text from Terry the day before, saying Taylor needed some different clothes, so I planned to pick some up at lunch time and drop them off. "Luis," he told me. "I'll lend you one of my gals to help pick out some appropriate clothing. Otherwise you'll have him dressing like a slut! What you two do after hours is none of my business, but while he is working here, he needs to be dressed properly!"

Taylor and Carol-Ann avoided each other that morning, Tuesday. Carol-Ann was feeling in a foul mood because she hadn't been fucked the previous night. She had had to tease herself with the strap-on cock that she was yearning to use on someone special, that someone being Melissa the young girl from the neighbourhood. She'd never had a lesbian experience until a couple weeks back and most recently the previous Wednesday night she and Latisha had a pretty heavy makeout session together.

Which reminded her to text Latisha. They had started getting together on Wednesday nights and she texted Latisha to suggest they get together the next night, after Carol-Ann fucked her boss. She assumed that because Bert Matthews had not lasted long last week, it would be similar this week. She could use a good fucking, but Bert was not a good fucker. Of course, if she could get together again with Latisha's friend, and pimp, Derek.... Now that man had a large dick and knew how to use it. At least she thought so. Each time he had fucked her, she had smoked some crack just beforehand and the details of the rest of the evening were fuzzy. But boy had she enjoyed the drug buzz!

Carol-Ann was glad to not have to face her son before heading to work. She was of mixed emotions about Taylor. Her sweet Tiger was not so sweet to her these days. Somehow their happy house had tumbled down over the past few months. She didn't quite understand why. But her finances were in ruins, she was in danger of losing the house, she had no room on her credit cards, her appliances and car kept breaking down. She barely had any cash in her purse.

Of course, what there was in there often went missing. She blamed Taylor for stealing from her, but she also knew she had been spending a lot lately on booze and smokes, and drugs from Jake. And from Derek now. God, she loved the buzz she got from the crack cocaine she got from him. They said it was addictive, but she knew she could handle it. Of course she could!

Tiger had turned nasty towards her, calling her a whore and blaming her for losing his college scholarship.

And what about him? He had been a wonderful son until the last couple of months. Now he spent all his time in his room, smoking cigarettes and joints. And stealing her panties. He probably jerked off in them. Through the door, she had heard the porno videos he seemed to be watching all the time now. When she went into his room, it smelled of weed and stale cum.

And now he had changed his hair and eyebrows and what he was wearing. Drunk the other evening, she had accused him of being a fag, a homo. She wished she could take those words back. She knew she had hurt him. But what the fuck was going on? He had always been a nice looking boy, even a pretty boy. But now he seemed intent on emphasizing that. Why would a boy want to be even prettier? How was he going to get a girlfriend, a wife?

Oh, where was Luis, her boyfriend? She desperately wanted to talk to him. She needed to figure a way out of her financial problems. She needed to talk to him about Taylor. He was a man. Taylor was a man, though still not much more than a boy. Luis and Taylor had started getting close, running and playing squash together. Maybe if Luis spent more time with Taylor, he could help her Tiger become the man he should be. Yes, she needed to encourage them to spend more time together.

But she also needed Luis to fuck her! God she missed his cock. Yes, Jake was a great fuck, and Derek was a great fuck (probably). But Luis was her boyfriend. She needed his cock in her pussy.. No, her CUNT. Luis told her to call it her cunt. And she loved it when he fucked her ass. She could not believe how much she loved an ass fucking!

Oh, why wasn't Luis answering her texts!

On the way to work, Carol-Ann had only two sips of gin from the small flask in her purse. And smoked one joint in the car as she drove. When she parked in the covered garage and was about to leave the car she stopped and looked around. Fuck it she thought, and wiggled and squirmed and took off her bra. Bert Matthews wanted her to look slutty at work, especially in two hours or so when he would have her on her knees sucking his cock, so what the hell, let's go full slut she thought! Whatever would help to keep Bert from firing her!

She had large breasts. Without the bra they sagged a bit, but they were still pretty firm for a woman in her late thirties (well, early forties). Her large thick nipple rings stood out against the material of her blouse when she stood fully erect and the material pressed tightly against her boobs. But most of the time, they were not noticeable, much. She would choose the right times to flash the men in the office, and maybe a couple of the women as well.

She giggled as she took one more sip from her flask. She stumbled slightly on the way to the car park elevator. Perhaps her judgment was slightly impaired, but if they can't take a joke, fuck'em!

God she needed to get through this day without losing her job. And she needed to find Luis! She needed his help. Taylor needed his help.

As Carol-Ann arrived at work Taylor was just leaving his house for the walk to the bus stop to go to work. He had woken early and had smoked his first joint of the day shortly after taking a whizz. He had planned to put on a bunch of videos and jerk off, but he had been pleased to find the text message from Luis saying they would get together after work. That made his cock get hard just on its own. He decided he wanted to save any cum for when they got together. He still did put the videos on, and he remained naked, but instead of jerking his cock, he instead got out some of the makeup that Terry had given him the day before. He'd also been given a table mirror to use for close makeup work and he set that up on his desk. He then spent the next fifteen minutes trying to put on his own makeup, in particular eyeliner and eye shadow.

He first applied some makeup and smoked while he practised. Some times the smoke from the cigarette dangling from his lips got in his eyes and he had to blink it away. As he worked, a few butts built up in his ash tray. He looked at them and the lipstick on the filters and shuddered. He had only started smoking a few days earlier, but he already felt the strong irresistible call of the nicotine, and the sexual allure of the smoke.

Videos played in the background of young men in makeup sucking thick man cocks, cum pumping into their mouths. Every once in awhile he paused with the makeup to watch one young man or another running their tongue around a cock head, or how they grasped a cock in their hand, and watched as the older men grunted and moaned as their cum spewed into the young lad's mouths. He marvelled as pretty finger nails gripped cock shafts or scooped up cum and slid it into lipsticked mouths.

Taylor gripped his own cock and his precum flowed easily from his pisshole and down across his painted fingers. He groaned and desperately wanted to pump, and to cum, but he stopped just short of the cliff edge. Tonight... tonight would be so much better if he waited.

After a shower and shave he took a pain killer even though his belly button piercing was not bothering him much. He also cleaned the piercings in his navel and his ears. He then resumed at the makeup table and after a few attempts and cleanups and reapplications, he was pleased with his eyes and decided to leave the makeup on his face. He also spent time brushing out his hair and applied some spray to hold it in place.

He rummaged through his closet, looking for the right clothes to wear. He had nothing feminine, but he did choose a plain solid coloured shirt and dark pants. He still had the cork heels from yesterday and wore those. No socks though. And underneath it all he wore black satin panties.

When he looked in the mirror he saw he had chosen well. The clothes were almost gender neutral. His face though was very feminine and the entire image was of a very pretty young man who knew he was pretty and wanted men to know it. After posing a couple different ways in front of the mirror, he undid two more buttons on this top and THAT made the look! Now anyone looking got the hint of bulges on his chest. Was it really a boy they were seeing or was that maybe a... a girl?

He smoked while waiting for the bus. He had accepted that he was pretty... no, very pretty. He stood with one hip raised, then the other. He blew smoke from his lips provocatively. Several cars slowed down as they passed, the male drivers gawking at him, trying to figure just who, or what, they were seeing.

Several people were waiting for the bus. One was a much older man who kept looking at Taylor with obvious lust in his eyes. Taylor smiled at him, and then looked down innocently, and then right back into his eyes. The man held his coat in front of his body and Taylor thought he knew why. Why was confirmed when they got on the bus. The man bumped an older woman out of the way so that he could follow Taylor onto the bus and as they all inched down the aisle on the crowded bus, the man bumped up against Taylor, repeatedly. Or more exactly, the man's hard bulge in his pants brushed up against Taylor ass several times.

The bus was headed downtown and so was quite full for the full journey. Taylor had to stand for most of the way, and the man stood right behind him. As the bus started and stopped in traffic, the man would push his hard cock against Taylor's ass. Feeling a bit naughty, and wanting to see just how far the man would go, Taylor pushed his ass back and the man's bulge fit nicely between his ass cheeks. Taylor looked over his shoulder and gave the man a sly smile. He also reached a hand back and briefly fondled the hard bulge, before needing to again hold onto a strap with both hands. The man put his hand around Taylor's waist and pulled him tightly towards him. Taylor wiggled and the man got a glazed look in his eyes. But then that old woman noticed and forced the man to move away.

The man got off several stops before Taylor. Taylor himself was quite hard and wet, thinking about the effect he had on the man. He knew the man would be looking for him tomorrow and on future days.

Samantha was already in the shop when he arrived. She looked a bit disappointed at what he was wearing and handed him a shop smock to wear over his clothes. Taylor busied himself with general tidying up in the place. When the other older woman Jade showed up she complimented him on his eye makeup, which made Taylor feel good, until she told him it was good, for an early attempt. The shop was slow at lunch time so she took him to a counter and they practised on his face together. Just for fun, she put a pair of false eyelashes on him, and Taylor was shocked by how even more sexy they made his eyes look.

When Terry arrived he tsk tsked about Taylor's hair and nails. They went into the office and Taylor pulled down his pants and his black panties so that Terry could give him his injections of "girl juice" in both buttocks. Terry still referred to the shots as vitamins, but Taylor was now convinced they were female hormones and he now welcomed those shots. If they would help him look even more pretty for Luis, for me,.... and for other men... then he was happy happy.

Terry also insisted that Taylor put on the taller heels that he had worn the previous days, to give accent to his shapely legs, even though they were hidden in drab boy pants. He needed practise in the heels!

Just after lunch time, the third assistant Jessie disappeared for awhile. Taylor was surprised when she returned an hour later and I walked in the door with her, both carrying several plastic bags which turned out to be clothes, for Taylor! Taylor squealed when he saw me. Terry gave him a sharp look because he was disturbing the two ladies who were having their hair and nails done. Terry nodded at his office. Taylor took my hand and dragged me into the office and closed the door.

He threw his arms around my neck and kissed me hungrily. Fuck, this boy had turned so quickly! He was a natural sissy! I sucked his tongue greedily into my mouth and grasped both of his ass cheeks in my hand. I was instantly hard and could feel that he was rigid in his panties as we briefly ground our cocks together. I so much wanted to push him to his knees, but I didn't have time. And, much as it meant depriving myself, I wanted to frustrate him, and make him even more eager for when we got together in a few hours.

Taylor pouted as I took his hand to take him back out of the office. But he paused me, looked in the mirror, tut tutted a bit and found a lipstick to repair his lips before we went out where everyone would see him. Such a sissy!

Terry joined us. He and I stood looking at Taylor for a few minutes, examining his hair and his fingers in particular.

"The eyelashes are a bit much, I think." I said.

"For every day, I agree." said Terry. "But so alluring. Perhaps for special occasions?"

"Yes, Saturday night." I told him.

Terry sent Taylor back to work. He pouted and gave me a quick kiss and went to help the women. I talked to Terry about how I wanted Taylor to look at the end of the day, and also about plans I had for Saturday night. Big plans.

Taylor had already taken two cigarette breaks during the morning. Tuesdays were slow at the salon. When he took an afternoon break and smoked, his mind turned to Luis, and his cock and looking at the lipstick on the cigarette he held in his fingers, he giggled as he thought about how deep down Luis' cock he hope to leave a lipstick ring, next time. As he looked at the cigarette in his fingers, he realized some of his nails were chipped a bit. This was rectified a short while later.

Samantha, Jade and Jessie eventually left and Tanya and Leslie arrived for the late afternoon and evening shift. There was not much on the schedule so Terry had Taylor take a chair and told Tanya to work on his hair. First she washed out the strawberry red highlights, returning Taylor's hair to the very pale blonde, almost white, that was his natural colour.

Terry walked up in front of Taylor and took his chin in his fingers. He turned Taylor's head slightly, examined the hair and then pointed to a spot high on the left side of the head. "Here!" he told Tanya.

Then to Taylor he said, "Don't be startled. Luis and I discussed this!" Tanya began brushing the hair on top of his head to the other side, and the hair from that point below, downwards, giving him a significant part in his hair and an elaborate comb over. It took several minutes and some hair spray to get the hair on top to not fall back to the side. Taylor watched all of this in the mirror, thinking it was so strange, but knowing there was an art to what they were doing.

And then.... and then Tanya took scissors and started trimming away the hair that hung down on the left, snipping it away, making it shorter and shorter. Oh my god, what was she doing! She paused, brushed hair in various directions, then resumed again. And when she had it very short, she took out some electric clippers and shaved the side of Taylor's head as short as she could. And then she brought out shaving foam and a razor and shaved Taylor so that there was no hair.

Taylor watched all of this in startled silence. "What have you done!" he exclaimed! Tanya worked on his hair more, sweeping all of the remaining hair across, and to the right, leaving his very bald scalp exposed on the left. Tanya continued to work on his hair, clipping and trimming, using spray. "When it grows back, we'll keep it trimmed real close. It will look better with very very short hair, almost stubble! And it will feel so nice in a man's hand!"

Taylor was moved to another chair where Leslie worked on his hands. Terry told him "Your nails are chipping too easily. Either you have not been using the strengthener I gave you, or it is just not working." Over the next forty five minutes, Leslie applied acrylic nail extensions to all of Taylor's fingers and thumbs, then painted them a bright red. The new nails extended about a quarter inch past his own nails and were nicely rounded, nothing excessive, but very feminine, and very erotic as he held them up and stared at them.

He was going to have to get used to them. Over the next hour or so, Taylor continued cleaning up after customers, restocking supplies etc. He constantly found his new nails getting in the way, and started learning when to use the pads of his fingers, or the very tips of the nails.

Simply holding a lipstick tube was a different experience. On his next smoke break he went into Terry's office and browsed a fashion magazine while smoking, learning to leave the magazine flat and flip the pages with the pads of his fingers.

When it was close to time for me to pick him up, Terry had him remove the eyelashes and makeup and try reapplying it. He then had Leslie remove and apply the makeup, but telling Taylor he had done a good job.

Leslie took Taylor into the office and went through the bag of clothes Jessie and I had bought at lunch time. She pulled out a pink and white outfit that looked very small but set that aside. She handed Taylor a black bra and helped him put it on. This was followed by a short red blouse that had only three buttons and she suggested he only do up the bottom one. This left plenty of chest visible. He slipped on a very short black skirt and a few other pieces. Taylor had a few problems with his long fingernails, but managed, though Leslie had to help him with a zipper. She replaced the two studs in his left ear, one with a small earring with a Hello Kitty character on it, and one that was long and dangly. These were very visible as he had no hair on that side of his head. She also gave him a pair of black pumps with four inch heels.

Taylor was surprised by what he saw in the mirror. His midrift was exposed so his pierced navel was visible. His bra was visible and you could tell that he was mostly flat chested, but there was a hint of mounds. The red and black outfit was stunning. But his face, and his hair... the makeup had been applied a bit more boldly. Dark eyes, almost white hair, bright red lips. Fucking gorgeous!

God, he needed a another cigarette while he waited. He grabbed his pack and lighter from his purse and lit up. He looked so fucking tarty with a cigarette dangling from his lips! His dickie was hard and he could see the outline against his tight skirt. Leslie walked up behind him and kissed him on the neck. She slid a hand around to his chest and squeezed a bra encased tit mound. Her other hand briefly brushed against the hard bulge at his groin.

He turned to kiss her, but she backed off. "Sorry, sweetie. I'd really love to play." Leslie said playfully, "I'm sorry I teased you. But Terry and Luis would kill me if I messed you up now. I think I hear Luis out there. Go and enjoy. Have a lovely evening!"

Taylor took a moment for one last drag on his cigarette and then snubbed it out under the toe of his high heels. Then he ran as best he could to the front and gave me an enormous hug! "Look!" he said to me giddily!