Predator and Prey Pt. 02

Predator and Prey

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

by Tawny Suede

Chapter 2 - First date

I was going to have to play a bit of a long game. I figured it would take about six months. I didn't make a plan as such, but my mind played around with how to go about this over the next several days and a general way forward worked itself out.

I was going to have to corrupt the mother. I didn't feel bad about that at all. She had something that I wanted and I was going to have to get her to let it go. And the son.... sweet Taylor.... I could seduce him. It wouldn't be hard. But it also wouldn't necessarily be as enjoyable as forcing him to submit to me. It was always better when they were reluctant and I had to force them a bit. Or a lot.

And maybe.. Maybe I could work it out so that the mother actually gave me her son. Knowing that I wanted to fuck him and turn him into my pet sissy. Yes, that would be nice. The thought of having her spread his asshole so that I could take his anal virginity made me incredibly hard. I so wanted that beautiful kid!

So I was going to have to work my way into their lives. Which meant spending evenings with Carol-Ann, playing the new boyfriend. And that meant not going to the bars as much, and would cut into my income. So I'd have to get it back out of her somehow. That made me smile. I knew several ways to get money out of women.

I'd find excuses to not invite her back to my place. We would spend time at her house. My apartment was usually not very clean, and was not in a nice part of town. Carol-Ann would not think as much of me if she saw my place. Or if she saw my current sissy. I'd had Juanita for about six months now. She was an eager femmeboi, but she needed to be disciplined a lot. So she usually had bruises on her face or on her arms. And though she was only twenty, she was starting to look a bit scraggy. I guess that's what happens when I regularly loan her out to my friends for a good ass pounding. Another reason it was time to get myself a new sissy.

Which meant I needed to start planning how I wanted to get rid of Juanita. Well there was no hurry on that score. It would be several months before I was ready to move Tiger into her room, and Juanita was still a great fuck every night when I came home. Incredibly tight ass. And I could deep dick her throat!

My first step was to send Carol-Ann some flowers, which I did a few days later. When I had left her place I had grabbed her phone to get her number. I am pretty sure she thought of me as just a one night fuck, and that is all she would have been to me too, but once I saw Taylor.....

I had to wait until evening to get a reaction. She didn't see the flowers until she got home and found them beside the front door. I put my number on the card and so received a Thank You, They are Lovely! by text message. I arranged to take her to dinner on Saturday night, but made it an early dinner. I told her it was because I had an early appointment on Sunday, but my plan was for dinner, then fuck her, then hit the clubs to sell drugs before everyone went home.

I dressed as nicely as I could and she dressed up nicely as well. I took her to a place that wasn't too expensive but did have table cloths. She told me that she hadn't expected to hear from me again, but was surprised and pleased. As we talked I found out she was a legal secretary working at a large office downtown. It didn't pay a lot but it gave her enough income to support herself and Taylor without having to run up a lot of debt. Well, if my plan went right, she'd soon be swimming in debt!

She didn't smoke, didn't do drugs (I'd change all of that soon!) and had been a virgin on her wedding night. Since her husband passed away four years ago she had dated a few men, but not found anyone who could hold her interest. Her husband had been her only lover before marriage, and only one of her recent dates had ended up with some sex, and not very good sex. So she was frustrated and horny, then I had come along. Only the third man to get in her pussy, and the best, or so she said.

She also told me that she felt a bit lost. Her husband had made all of the family decisions, including finances. And after four years, she was still floundering. She had discovered she had little self control, including when it came to money. As a result she had a bunch of credit card debt. And seemed to be sinking further into a hole.

She sighed and said she found it refreshing to find someone she could talk so openly with.

And that was part of my charm. I didn't really have much use for women, except as holes to stick my cock into, but I knew how to talk to them and more importantly, how to seem to be listening to them. I was just handsome enough, and also just rough enough, to intrigue almost any woman that I wanted to snare.

I told her that I was in construction. I had my own house, but I was doing renovations and so it was a mess and not suitable for taking people back to. I told her that I also had a friend who I helped out making late night deliveries. She asked what kind of deliveries, but I just smiled and deflected the question.

I didn't tell her that I made most of my money selling drugs, nor that I had a latina sissy with a limp cock tied up in the extra bedroom at my apartment (not a house - that was embellishment), with a vibrating dildo shoved up her ass. Which reminded me to reach for my phone and open an app to change the vibration setting. I could just imagine Juanita moaning as her limp dick drooled more watery jism onto the bed sheets. Well she'd get a good fucking when I got home in several hours.

I told Carol-Ann that I had enjoyed our previous fuck session (well, not quite so crudely) and was looking forward to a repeat if she was up to it. She leaned over and kissed me, and grabbed my dick under the table at the same time. So I guess that was a yes.

She had Ubered to the restaurant. As we drove back to her place in my truck she leaned against me and almost cuddled up to me. Seat belts made that a bit awkward. When we got to her house she did not hesitate about introducing me to Taylor since he was in the living room, again playing video games. One of the reasons I had made an early date with Carol-Ann was because I did want to talk with Taylor and start getting him used to me being around.

Carol-Ann was a bit tipsy as she led me up the stairs. I looked back at Taylor and met his eyes. I gave him a grin and he grinned back, and then gave me a thumbs up. I don't know if he was saying thank you for being nice to his mom, or if he was giving me a guy to guy sign to say - way to go, you scored!

But then he brushed some of his long hair away from his face, his hand tucking the stray blond hairs behind his ears. Such a feminine gesture. So gorgeous. And I was instantly hard. I wanted to march back into the living room, throw him on the couch and fuck my cock into his sweet mouth. But that was for another time.

So instead I took his mother up to her bedroom and I fucked her. Before we started I went into the bathroom and brought back a glass of water, using the glass she used when brushing her teeth. I took a gulp and then handed the glass to her with a couple of aspirin, telling her to take them so she did not end up with as big of a hangover in the morning. She looked a bit puzzled but swallowed the tablets and downed the water.

One of those tablets was aspirin, but the other was a knock out pill that would take about half an hour to work. It wouldn't leave any bad effects so when she woke up in the morning she would actually be refreshed and think she had slept naturally. But she would be completely zonked out for eight hours, which is exactly what I wanted.

I have to say that Carol-Ann was a pretty good lay. She sucked my cock like a pro and I reciprocated by going down on her. I'm not usually much for munching a rug, but as I licked her out she was squealing and panting and swearing up a storm. She had to put a hand over her own mouth to stop from screaming as she came. She didn't want to alarm her kid. She was getting a bit drowsy when she spread her legs and I shoved my cock in her pussy. I deep dicked her for five minutes, kissing and mauling her neck. She's have a hickey to explain at work on Monday!

When she drifted off unconscious her cunt loosened up and wasn't tight enough around my cock for me to cum. I thought about showing my dick up her ass. That would be tight enough even with her being unconscious and I would not have hesitated if this was a one night stand. Heck I had done that often enough. But I was playing a long game here.

I actually tucked her underneath her sheets and wiped some drool from her mouth. Sleep tight, Carol-Ann! I thought, as I got my clothes on and went downstairs to spend some time with her son. Nah, not what you're thinking, at least not yet.

Taylor was playing the same video game that I had seen him play the first night I had brought Carol-Ann home. At least, I think it was the same one. I don't know these games, so it could have been different. I went to the fridge and rummaged around and found a beer. I also grabbed a coke, popped the caps off both of them. I dropped a pill into his coke and then plopped down on the sofa beside the kid, handing him the bottle. He waited for the right moment in the game, then took the bottle and said "thanks"

I introduced myself as Luis and he said he was Taylor. He concentrated on playing the game, while I watched. I kept a reasonable distance between the two of us. I wasn't trying to make any moves. First I just had to get him comfortable with me, then later I could work on getting him to let me into his personal space. But I inhaled, and he smelled good. Boy fresh I call it. Just a hint of body sweat to create a personal odour.

After fifteen minutes I asked if he wanted another drink since I was going to get another beer. He said he was good for drink, but it would be great if I could grab the bag of chips. I did. When I brought them to the couch he paused the game. We chatted for a few minutes about nothing in particular. I told him his mom was wiped and had fallen asleep. I just needed a bit of wind down time before I headed home. He said that was cool, and again he made that gesture where he pushed some hair behind his ear. And again I got an instant boner.

This kid was fucking gorgeous. Well, at least to a femmboi lover like me. His lips, his cheekbones, that beautiful white blond hair. His long legs. It was summer so he was wearing shorts. There was only a bit of fuzz on his legs. As a runner he was fit and his legs were lovely.

And he had long eyelashes for fuck sake! God I so much wanted to pick him up and just thrust him down on my cock and kiss those beautiful lips while I jack jack jack jack jackhammered his ass! And one day I would. But not tonight.

I asked him about the game and what he told me made no sense at all. I asked if he had something simple that two players could play. He looked at me shyly, almost batting those gorgeous eye lashes, then said sure. So for the next half hour we played some silly driving game. He beat the pants off me, which made him feel good. His laughter as he mocked me made me actually go so rigid that I squirted a bit of piss in my pants! God I was in lust with this kid.

Well, I say kid, but Carol-Ann had told me he was legal age. So I wasn't going to be breaking any laws when I finally made him my fuck slut. Well, not too many laws anyway.

At a respectable hour, I packed it in. I gave Taylor a pat on the head that turned into a pretend hug... very very brief and then I left, having accomplished what I need to this evening - getting the kid comfortable with me.

I had planned to hit a few bars and pass a bit of dope around. Put some money in my wallet. But Taylor had really gotten me worked up and I had not cum inside his mom. So I headed home to Juanita. She was just where I had left her, tied up on her bed, a vibrator jammed up her asspussy.

I dropped my pants and yanked out the vibrator. I didn't stop to untie her. She moaned a bit as her limbs twisted in directions they weren't meant to as I lifted her ass up and then jammed my cock straight up her ass chute. She protested feebly. My cock was dry. Her ass was dry. But I didn't care. I needed to get my cock deep in her ass. I fucked her hard and then harder. She was sobbing when I jammed my dick fully inside her and then dropped a giant load of cum into her shitter. Her cock didn't get hard since at the moment it was locked up tight in a small cage. Not that she ever got hard any more. A lot of sweet boy juice had drooled out of her piss slit onto the bed.

Her mouth had been covered with the tape I had put there when I left for my date with Carol-Ann. I didn't need her shouting or trying to draw the attention of my neighbours. In this building no one would give a fuck, but well, you never knew. So when I went out I usually shut her up.

I ripped the tape off of her mouth. It was covered with tears and snot from her nose and so had been hard to grip. When I got the tape off, I shoved my dirty cock into her mouth and made her clean me up. She protested but I knew that this was actually her favourite part of the evening. She loved sucking and cleaning my dick. Even if she pretended to cry when I finally untied her and then left her on her bed.

I had won Juanita in a poker game. I had got rid of my former sissy a few months earlier and took a fancy to the latina sissy when I visited a mate an hour south of me and he had invited me to a poker game above a garage. Juanita was under the table most of the night nursing on her owner's dick and I took a fancy to her.

When he handed her over to me, he told me she was still a bit raw and at times was resistant to training. This is why she had no balls or ball sac now. Just ten days after taking her home she bit my cock and actually took a swing at me! So I tied her down with her legs spread and made her watch as I anaesthetized her balls and then snipped her ball sac and fished them out. She had fainted when I puffed up the end of my cigar to a bright blowing red and then pressed it against those exposed nuts. While she was out I cut them out and stuck her testicles in a glass jar.

I did know what I was doing. When she came around, I fucked her ass pussy while blood dripped from her ball sac just so she got my point. Then I took her to a proper doctor who converted the impromptu castration into a proper orchidectomy. It had taken her a couple months to heal but she was a much more enthusiastic sissy after that, Juan becoming Juanita. Whenever she resisted I would threaten to cut off a finger or her tongue and she was fully co-operative.

Before going to bed I lit a cigar and stood out on my balcony, looking out over the parking lot at the back of my building and the surrounding buildings. Not a great part of town. Pretty rundown and lots of crime, mostly neighbours stealing from neighbours. But fuck, it was my home!

I started to feel a bit bad about how I had treated Juanita. I'm not normally one to get sentimental, but she was a good sissy and I was as fond of her as I had been of any of my other femmeboi sluts.

I went into her room. She was asleep but woke up when she heard me. She pulled back a bit almost as if she feared me, but I knew that could not be the case. I picked her up gently and took her to my room. I told her to clean up a bit in my bathroom, particularly to clean up her mouth in case it still tasted like shit.

When she came out, I had her get in bed beside me and then I kissed and cuddled with her for five minutes to get her to relax. She told me she loved me, many times. I unlocked her dickie and played with it, even kissed and sucked on it for a bit. She couldn't get hard any more but she still got pleasure from the attention, especially when I slipped two fingers up her ass.

"Fuck me, daddy" she whispered in my ear. I looked her in the face. Other people might have thought the expression on her face was fear, but I knew it was love. For me. So I fucked her like she had asked. I turned her on her side and slipped my hard cock up her ass. I wrapped my arm around her and pulled her tight against me. I slow fucked my sissy bitch until I fell asleep with my cock still in her ass.

I woke up during the night to take a whiz. When I climbed back in bed, Juanita cuddled up against me and we fell asleep like that, me cradling my soft sweet sissyboi.

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Hi luvers

Many more chapters to cum!

Please leave me some feedback. The more you write to me, the more I write for you.

I love all you gorgeous sissies and hunky men out there!

--Tawny