Predator and Prey Pt. 12a

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Corrupting mother. Converting son to sissy!
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Part 13 of the 24 part series

Updated 04/15/2024
Created 03/06/2023
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Hi, all you gorgeous sweeties!

A bit of an apology before we start. Once again I am posting just one-half of a chapter. That is because the chapter has gotten to be so very long, and I don't want to keep you waiting!

Why is this just half of a chapter? Well, that's because my intention is that each chapter includes something significant in the seduction and feminization of Kitten and also something significant in the degradation and corruption of his mother, Carol-Ann.

So this half-chapter will disappoint many of you because it focuses on Luis and on Carol-Ann. There is very little Kitten in this half chapter I am afraid.

I know, I know. All of your little dickies are just yearning to get hard reading about how Luis pushes sweet young Taylor to become his femme sextoy Kitten.

But the good news is that the last half of this chapter, my next posting, will be 100% all Kitten. As you can tell from the title of this chapter, Luis will finally get some gratification from the gorgeous sissy!

In the meantime, please enjoy as Carol-Ann sinks lower and lower and just imagine what Luis might have in store for her next!

As always, my sweet pets, please do think of your caramel Mistress as you spurt your own cummies over this half-chapter and, after you've cleaned your hands, please do leave me your delightful comments,

Smooches to you all,

Mistress Tawny

Predator and Prey

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

by Tawny Suede

Chapter 12 - Carol-Ann hooks, Kitten sucks

I had originally told Taylor that I could not pick him up at his house on Saturday night. However Latisha informed me that Carol-Ann would be meeting her and their "dates" early and so I texted Taylor that I would pick him up at eight. I had told Carol-Ann I was going to be out of town that weekend, which was a lie. But I wanted to give her more incentive to accept Latisha's invitation, and also to have Taylor to myself for the evening without explaining to Carol-Ann.

I would reveal my relationship with Kitten to Carol-Ann very soon, but not quite yet. There was still time for something to go wrong with my plans, so I still had to be careful. However from my texting with Taylor, I found out that his birthday was just three weeks away, and I developed big plans for that night, involving both mother and sissy son.

My texts with Taylor, or Kitten as I now was calling him, were filled with little reminders of how pretty he was and how much I liked kissing him and making him cum. I called him sweety and lover. He was shy and hesitant in his replies, but eager to be complimented. He told me that he was continuing to polish his nails and use his moisturizer and was wearing the pairs of panties I had bought for him.

He told me he was enjoying the most recent memory stick while he jerked off and asked me to bring him more of the same boy/boy and boy/man material. Oh, and he was eager for me to bring him more weed. He was almost out of what I had last brought him, and he did not have his own supplier.

Even though I was "out of town" for a construction job, I did talk to Carol-Ann in the evenings. We had gotten to the boyfriend/girlfriend point where we texted a few times every day and talked on the phone at night. Each time we talked at night, Carol-Ann's speech was slurred and her mind wandered. Booze and weed. She was really overusing both to try to get through her troubles.

She also continued to moan about her financial troubles and how she was desperate to come up with enough cash to make her mortgage payment on Monday. She told me that she had agreed to help Latisha, essentially trading sex for money, in order to get money for that payment. But just this one time. She was not going to do repeat.

I was pleased. This was just as I had planned.

But she didn't tell me everything. I had to find out from Latisha that she and her friend Derek had gotten Carol-Ann to use crack cocaine on Wednesday night. And about the additional rings that were now in her labia. Fuck, I really wanted to see her pierced cunt lips and run my cock past them as I fucked her, but I was "out of town" and so would have to wait. I dropped into the conversation that I would be back some time on Sunday, so I could drop by to see her on Sunday evening. That pleased Carol-Ann.

She told me about the tattoo just above her ankle, but she knew it needed a couple of days to heal and so she had not removed the bandage. She had no idea what was under the bandage since she was so strung out on crack at the time that she had no memory of getting it.

On the Thursday night, she told me how late she had arrived at the office and as she thought would happen, her boss Bert Matthews had immediately called her into his office. Everyone else at the office thought that Carol-Ann was once again going to be threatened with being fired, but as soon as the office door was closed, he had had her strip off her top. He had been amazed at her new larger nipple rings and played with her tits for several minutes before pushing her down on the floor, straddling her chest and then telling her to push her large tits together. He had then spent several minutes fucking his average sized dick between her large jugs, before finally pushing into her mouth and cumming as she sucked his cock.

As she had put her top back on he had told her that they would again get together the next Wednesday night, same hotel, so he could fuck her.

Things were spiralling out of control fast for Carol-Ann. Knowing about next Wednesday night gave me an opportunity to push things even more extreme. And that was what I needed to set things up for Kitten's birthday in a few weeks.

The next day I called Carol-Ann's office and as usual Sherry answered. She was the receptionist, after all.If you don't recall, Sherry is a "friend" of Carol-Ann who I took out on a date a short while back in order to let her steal some compromising photos of Carol-Ann from my phone. Those photos found their way to Bert Matthews and he was using those and the threat of losing her job to blackmail Carol-Ann into being his sex toy. I told Sherry that I wanted Bert Matthew's home phone number and his wife's name. Sherry said that was easy because Louise Matthews was a friend of hers -- she would be happy to give those to me, but only if I took her out on another date - which really meant that she wanted me to fuck her again. She'd been a pretty good fuck, proving to be a dirty girl, so I agreed to meet up with her early the next week.

My soon-to-be full time sissy Kitten and I had jerked each other off on Wednesday evening. Our next get-together would be Saturday night and I had plans to cum several times that night. On Thursday night I satisfied my sexual needs behind one of the regular bars I was selling drugs at. It was in a, shall we say, less desirable part of town. But then, most of the bars that I sell drugs at are not very classy. I was passing drugs off to two regulars and at one table I noticed three kids, probably from the local college, who were doing a good job of getting blasted on booze - two guys and a girl.

One of the guys spotted me handing a baggie off to a customer and a few minutes later he approached me near the washrooms. He asked me if I had any weed to sell. Normally I don't deal with strangers so directly, but I was carrying a bit extra that night. We talked price for a few minutes and as we did his two friends walked over. He was short on the cash that I wanted, but the girl while not pretty, did have intriguing eyes. So I told them I would sell them the weed for the cash that they had but the girl had to come out to the alley and blow me. The two guys really wanted the weed, but the girl refused.

The guys tried to convince her, then she turned to one of them and said "You're the one that wants the weed, so you blow him!" The guy looked startled. I looked at him and then the girl and I made eye contact.

This could be interesting I thought."Sure I'm game for that. In fact, if you suck my cock, I'll toss in a molly tab for each of you."

"But I'm not gay!" he protested.

"You'll do it!" said the girl. The other guy smirked at his friend.

I have no problem having sex with guys, but I prefer them femme. I have no interest in guy guys, if you know what I mean. He was cute enough, but...

"Have you got lipstick in your purse?" I asked the girl. She nodded. "Give it to me." When she did, I handed it to the guy and said, "Let's go!" I hadn't expected it, but his friends followed.

Outside I had them give me the cash part of the price, then it was time for the rest of the payment. "Put on some lipstick and get on your knees here." I pointed to some cardboard on the ground. The girl took the lipstick back and applied it to the guy's lips.

I lit a cigar and leaned back against a wall. I was going to enjoy this. I always liked being the first inside a newbie's mouth. I pulled my cock out of my jeans and held it in front of his lips. He put his tongue out a bit and swiped it across my dick head and then opened wider and sucked on the head of my cock. His guy friend looked smug, but the girl's eyes were round and open as wide as the booze would let her. I'm sure she knew that at the end of the evening she would get fucked by one or both guys, but she hadn't imagined seeing one suck cock.

After a minute, I was sure this was the first time Cocksucker had sucked a cock. His technique was not good, and for some reason I was getting impatient. So I grasped his head and I started fucking his face. While I did that the girl reached into his buddy's pants and pulled out his dick. She began wanking him, but her eyes were focussed on my dick ramming Cocksucker's face. Cocksucker began to struggle as he was finding it hard to breathe, but I didn't care. He thought he was there to pay the rest of the price for the weed. But he was really there just as a means for me to get my rocks off.

He struggled to get his breath and tried to push me away. But fuck that! I pulled my dick out and then gave him a hard slap across his cheek. He pulled back, startled. I gave him another hard slap and he looked like he was going to cry. The girl had a smile on her face and a glint in her eyes as she said, "Hit him again!" Cocksucker looked at her in astonishment. "Hit him!" she said again. And I did, hard.

This time he did start crying. I couldn't stand the blubbering so I grabbed his head and jammed my cock back in his mouth. The girl's eyes gleamed as she grasped Standing Guy's cock tightly and began to jack his dick more furiously.

I held Cocksucker's head very rigid as I fucked his mouth hard. Tears from his eyes ran down his cheek and mixed with the snot streaming from his nose. I pulled back a bit and he gasped for air and then I jammed my cock in again, pushing to the back of his throat. I pounded my cock deep and almost got into his throat, but not quite. That was okay because I was ready to cum. Cocksucker's face was turning a bright read as I spewed my first load of cum into his mouth. I pulled out and shot the rest of my load on his face.

He cried. What a pussy, I thought! Standing Guy was getting close to cumming. The girl surprised me by turning Crying Cocksucker's face and pushing it down on Standing Guy's dick. The girl stood behind Cocksucker and jammed his head down on Standing Guy's cock. She jammed his head up and down until Standing Guy blew his load into Crying Cocksucker's mouth.

I put my dick away and tossed the baggie of weed and molly tabs to the girl. As I walked away, Cocksucker was still snivelling as Standing Guy wiped the rest of his cum on his face. The girl was clapping with glee. I wondered if by the end of the night she might manipulate one to fuck the other. A girl after my own heart!

On Friday night I didn't pick up any woman or get my rocks off until I got home. I realized that it had been a couple days since I had given Juanita any special love. Sure she sucked me each morning to wake me up; at least, when I did not have her locked up in her own room. But I hadn't fucked her in a couple days. I realized this was because my mind was already thinking of her as my ex-sissy. I knew that within a few weeks or a couple of months I would have Kitten living with me. It was just a matter of time before I had Taylor completely converted to Kitten and stolen him from his mother.

I knew Juanita would have to go, and so there was no sense in continuing to try to train her, and break her. She definitely still needed breaking. She had never fully accepted that she was just a fucktoy for men to use. And by men, I meant me, and anyone who I would lend her out to. After all, she was my property. I had won her in a poker game when she was still mostly just Juan. I had removed her balls when she was particularly rebellious. But that defiant streak had never really left her, no matter how much I beat her.

I had discussed Juanita with my friend Sally, who agreed that I was unlikely to find a new master for the little mexican boicunt and Sally said she would move her on to a sissy whorehouse when I was ready to part with her.

Juanita has been my third full time live-in femmeboi. Both Alice and Dawn had been enthusiastic sissies and I had been very fond of both of them. But when I got tired of each, I moved them on to other masters and took my next. I had been two months without a sissy when I won Juan in a poker game. I was motivated at that particular moment because the little latin minx had been under the table with my cock in his mouth, looking up at me with fearful eyes. Looking back I think her former owner lost him/her on purpose. Juan had never fully accepted being Juanita, and while she was a talented cock sucker, and had a nice tight ass, she was always talking back and complaining.

When I left for work or to go out in evenings, I usually had to lock her in her room, and usually had to cage her dicklette so she did not play with herself. I had lost track of the number of times I left home without caging her and have come home and found that she had played with her dick all day!

On Friday night I was feeling particularly affectionate to my soon-to-be-gone sissy. When I got home late after hitting the bars, I went to her room and undid the ropes that had bound her all day and pulled out the medium size butt plug from her ass. I allowed her to go to the bathroom and then I gave her the happy meal I had brought home for her. She gobbled up the burger and fries and slurped the coke. I had bought her an apple pie as well and it had cooled enough for her to eat right away. Nothing was too good for my little femmeboi slut.

Then she went back into her room for a few minutes. When she returned she had tidied herself up and lubed her ass. She was expected to always be ready for an ass fucking.

I was sprawled on the couch, smoking a cigar, with a beer in hand, watching something mindless on tv. She came straight to me, straddled my groin and sank her boipussy right down on my hard dick. I muted the sound on the tv, pulled her head to me and kissed her hard and then put my hands on her waist and helped steady her as she raised and lowered herself on my dick. I kept telling her what a good girl she was, and she kept softly calling me "Daddy Luis" as she fucked herself on my dick and her own dicklette bounced around limply.

I took her cocklette in my hand and worked it. Slowly it rose to erection and she smiled and purred at me as I jerked her. But then I released her cock and she pouted. But she raised her arms and ran her hands through her hair, trying to look sexy for me. "You love Juanita?" she asked me. I told her that of course I loved her and kissed her hard.

Of course, I was eager to get rid of the little bitch. But she did not know that, yet, and I wouldn't tell her until the last moment.

A few minutes later I pulled her down hard on my dick and shot my jizz deep in her ass. She moaned and quivered and then shot her own load onto my chest. After a few moments grinding her ass down on my dick, she dismounted and then got on her knees. First she licked up her own jizz from my chest and belly and then she sucked my cock, cleaning it with her mouth and tongue. She had cleaned herself out well before we fucked, so there was very little foul matter for her to clean off of me.

I made her go rinse her mouth before she came back and cuddled with me on the couch. A half hour later I picked her up and took her to my bed. I put her on her back and fucked her again, hard. I could tell she had forgotten to lube herself again, but I didn't care. I could see her grimacing in pain a bit, but that was her problem. So long as she kept a happy smile on her face, and she did, though I could see a few tears fall down her cheeks. I came a second time in her ass. I then pulled her to me and we slept cuddled together. She wouldn't get up to clean out her ass until the morning.

Saturday morning I texted with Taylor reminding him I would pick him up at eight. I told him to shower, put on a pair of panties and also the white blouse and dark pants I had bought for him. I also reminded him to refrain from smoking any weed as I wanted him clear headed at least at the beginning of the evening. In our couple of text conversations, I tossed in a few "sweetie", "dear" and "honey" to emphasize my affection for him.

On his side, a couple of his messages mentioned how much he loved our kissing and cuddling and was eager to get together. He pestered me about what we were going to do that night. I finally teased him by telling him that our first stop would be Terry's beauty salon. He texted back that he was nervous, but excited. I in turn told him that I loved exciting him, especially with my hand. I could imagine him blushing when he read that, but also getting hard.

I also told him to let me know when his mother had left the house.

She had a date with Latisha and two out of town gentlemen. She was supposed to meet them at a downtown restaurant at seven pm.

I later pieced together Carol-Ann's evening from what each of Latisha and Carol-Ann told me in the next few days.

Carol-Ann was extremely short on money. That was after all why she had agreed to this date, which she was going to be paid for. But she called an Uber to take her downtown. That wouldn't cost her any cash, just some of the very small room she had available on her credit card, room that was possible because Luis had loaned her some money to make a payment. God, that man was so good to her, the thought!

She didn't want to drive her car, both because it would mean having to stop and put gas in the tank -- using up credit -- but also because she planned to get wasted. She wasn't so concerned about getting caught driving drunk or stoned, as the thought of damaging the car which she really needed.

Since she wasn't driving, she had her last joint and a couple of large glasses of rum while she finished dressing and waited for the Uber. She had been surprised to find the rum in her cupboard. Normally she bought vodka or perhaps gin. The whiskey from the other night had been real nice, but somehow she had left the bottle at Latisha's place, or perhaps they had finished it. She didn't remember. These days there were a lot of late nights that she did not remember. She was regularly getting so drunk at the end of evenings, but she did enjoy the booze -- and the weed, and the pills! She smiled thinking about how much better her life was now that she wasn't such a straight laced prude!

As she rode to the restaurant, she smiled at the Uber driver as he checked her out in the mirror. She knew she was worth the lustful glances from him. She wasn't a beautiful woman, but she was attractive. Latisha had suggested that she not dress too slutty for their date, but Carol-Ann did apply her make-up a bit heavier than she had in past. Not slutty, but certainly tarty, she grinned to herself. Latisha had suggested that she wear a low cut top, and Carol-Ann's choice showed lots of cleavage. She had chosen not to wear a bra and so her nipples and the large nipple rings were visible as outlines.

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