Boytoy Bill Ch. 01

Second meeting

"Hey guy, we need to talk."

Bill was dumbstruck. It had been more than 7 months since I took him back to his place and fucked him senseless, the first and last time he'd seen me. Back then, I'd had a tight and toned belly, now it was the round curve of a very pregnant woman. It was fake, but Bill didn't know. I was waiting for him in the parking lot outside his apartment, where we knew he parked, when we knew he'd be alone.

"Oh, uh... wow. Umm," he managed to stammer out, no doubt his mind racing to figure out what to say and not finding anything. I almost smiled at how effective the ruse was, but capitalized on it to get him inside quickly.

"Yeah, tell me about it. Inside? It's cold," I said as I started walking towards the side entrance, less chance of being seen.

"Of course," he said, managing to get ahead of me and unlock the door. The half flight of stairs to the second floor and a few steps to his door were crossed without any talking. I followed him inside and closed the door behind us. As he started to say something, his back turned to me as he removed his shoes, I snuck an arm around his neck and grabbed the crook of my other arm, the hand of which was pulling Bill's head forward. A textbook rear naked choke, something Lori and I had practised countless times, and something we both did at our BJJ classes. He tried to say or yell something, tried to fight back but couldn't get a hold of anything. A few seconds later, he lost consciousness.

It was easy. Besides the grappling training, I was taller than Bill's 5'8". And considerably stronger, even more-so than I'd been when we met last spring when I'd still been bigger than him. We'd tried out and tracked quite a few candidates before choosing him, an attractive young man of 20, shorter in height without much muscle without being too skinny-fat. His best features were his soft blue eyes, generous attitude, and nice big cock.

I'd first spotted him at a grocery store of all places, putting some ramen into his basket, sure enough sign of a bachelor. I shot a 'met a thing, ttyl' text to Lori, then an hour later after chatting him up over a coffee in the deli, we were back at his place, and I was pleased to find the bulge that had been showing through his shorts was a grower, a girthy uncut 8." A trimmed but a bit overdue bush. I spent the next few hours giving him the best sex of his life, and some of the last 'normal' sex he'd ever have, if my glance at his pad was any indication of a regular girlfriend. On round three, after inquiring about Bill's bill of health, I let him go raw, and when he tried to pull out I wrapped by strong legs around his hips. All part of the plan. I left that night while he slept, with someoneelse's phone number written down on his nightstand.

When I felt him go limp in my arms, I carefully let him down. From my purse I pulled out my rope, gag, choker and blindfold, and in short order had him trussed up. I went back downstairs and let Lori in.

We gathered up a few things from the place, gave him a small shot of ethanol and GHB, then stuffed him into a comically large piece of luggage, into the van, and settled in for the long drive home, well outside the city. Bill slept most of the way.

Some months later

"Rise and shine, sleepy!" I said, giving Bill's house a good knocking. It was a metal box with a door, and inside there was nothing. Nothing except Bill, a warm butt plug, and a can for him to piss in.

"Good morning, Mistress" he answered. Anything else earns him a punishment, and Bill doesn't like his punishments, despite the effort we put into them. Bill used to spend entire days in pain, until he learned his place in the world. He's much better, now, and usually only gets hurt for our amusement.

I unlocked his door, and let him out to do his bathroom duties. A shave, a poop, a shower and an enema. Sometimes one of us will watch him, but today Lori was upstairs busy with a Zoom meeting, and I had to catch up on some reading.

Bill wrapped up quick, as he always does. Once when he tried to dawdle, I asked him if he'd like to live in a bathroom, and he was confused. Later, Lori and I pissed on him through the vent in his house while he was sleeping, and he stewed in it overnight. He doesn't dawdle anymore.

Naked except for his decorative "butt slut" collar and his Reminder, I beckoned him over to my chair and treated myself to one of his now-stellar headjobs. He got right to work, gently removing my underwear, sucking and licking exactly how I like, without ever taking his big blue eyes off me, caressing one or the other of my perfect breasts. I ran my hands through his hair, and soon grabbed hold of it to move his face around as I came on it. He licked me clean of any saliva and juice, and I even stood up to let him lick my asshole, too, the lucky boy.

It was still early, too early for anything more vigorous, so I asked Bill if he'd like a favour and he asked to take his Reminder out, like he always does. I said no this time, but let him watch some television instead. Sitting on the floor of course. Bill doesn't get to use people furniture.

All things considered, despite not being a person anymore and finding himself in all sorts of painful predicaments, Bill had it pretty good. He could have been enslaved by a man (Bill doesn't like cock, but he's learning) or some ugly people, instead he had us as his owners. Lori and I are beautiful. She's shorter than me, a raven-haired Filipino to my blue-blonde Caucasian, tits on the smaller side, but more than made up for with an amazing booty and cruel mind. We were a match made in heaven, one of those rare pairings of people who really are perfect for each other, no 'rounding up to The One', compounded by the statistical rarity of two sadists meeting and falling in love. The only problem in paradise was that switching isn't ideal, and finding new girls and boys to use wasn't just a hassle, but so inhibiting when you have to let them go later. We needed something more permanent, less restrictive, and now we had Bill.

We even let him cum pretty often. Usually after a long session of being whipped or beaten or fucked in the ass, but not always. We're generous.

Lori brought down his breakfast as I was working out, giving him a break from his daily stretching yoga routine. Bill needs good flexibility to fit into some of the situations he gets into around here.

With her hair back in a ponytail, and only a red thong and a matching bikini top, Lori had all she needed to look great. She came over and gave me a smooch at the top of my deadlift, and asked if I had any plans for the day.

"Just the regular, honey. You?"

"All wrapped up for now, but I'm in a mood. My fuckup assistant fucked up again, I think I'll have to replace her."

"I hate incompetent people." Turning to one, I said "Did you hear that, slave? Lori's in a mood," I laughed. The slightest smile crossed Lori's lips as she gazed at our toy.

"Yes Mistress. I'm sorry, Maam." Bill answered, finishing up his shake. He's not allowed to use our real names and he never hears his.

"I need a distraction, slut," she said to him. He was already looking a bit sad that his day was unlikely to be limited to more bearable fare. "Luckily, I'm ready. Go to the big room, there's a new thing in there. Sit on the stool and it should be obvious where everything else goes, don't make me do all the work."

"Yes Ma'am."

After he left the main room, Lori turned to me. "Coming? I will be."

I laughed, "of course, sweetie" and gave her a hug.

"Ew, go shower."

When I got back downstairs, sporting a matching thong and bra to Lori's, Bill was in position. The 'new thing' was a thick wooden post attached firmly to the floor, about 4 feet tall and 10 inches to a side. Against it was a stool, where Bill sat back to the post, looking very nervous. Around his neck and bolted to the post was a thick metal collar, about 3 inches tall, not tight enough to choke him but with very little wiggle room. His arms were back and fully extended down the sides of the post, where his wrists were each held in place by cuffs, also bolted to the post. I smiled at the thought of Bill sitting down and tightening the bolts around his own neck and one of his arms, preparing himself for his own torture.

Lori was asking him which he preferred to be struck with, the singletail whip or the cane. She held both, and was using the end of the cane to poke around his belly and make him squrim.

"I don't know, Ma'am."

Lori pulled the cane back and smacked him on the side of his thigh, quite hard. "Answer the question or I'll use the cattle prod all day."

"Ooow, sorry. The cane, I prefer the cane."

She smacked him in the same spot, on the other leg. "This one?"

"Gah, yes, that one."

"Maybe you should have answered right away. I'll use the whip." Bill's bottom lip trembled just a little, but he knows better than to cry from something so minor.

Putting the cane back on the wall, Lori stood in front of him with the narrow whip.

"Ask me to start whipping you, slut."

Bill took a deep breath, and calmly asked "Please whip me, Ma'am."

Swish. Thwack! The strike was across his naked chest.

Bill grimaced, but counted "One."

"You don't need to count, slut."

It was going to be a long session.

It took fifty or so strikes before Bill started whimpering, and another twenty for the whimpering to turn into groans.

Swish. Thwack! The thin red marks were starting to accumulate, turning his previously barely-marked chest red. The whip isn't a heavy one, but it adds up.

Swish. Thwack! Lori was wide-eyed and smiling, I loved to watch her work, and knew she was getting wet. But she has self-control, she'd hold off on using his cock or tongue until later.

"I'm getting tired of standing here. I think I'll sit down while I do this. Gimme that stool, slave."

Lori grabbed the stool Bill was sitting on, forcing him to hold himself up using his legs, and now I saw what Lori had done. The collar around our toy's neck was too high. If he tried to get to his knees, the collar would press into his jaw, holding him a little bit off the ground. Bill was forced to struggle to hold himself up using only his legs, and it was hard.

Lori sat in front of him on the stool, legs crossed, smiling.

Swish. Thwack! Now Bill was just crying. After only a minute, his legs were trembling. He was positioned as if he was sitting on the stool still, calves perpendicular to the ground, using his legs to push his back against the post. Quite the workout for his quads.

Swish. Thwack!

"Please, Ma'am, I can't! I can't hold myself up!" Swish. Thwack! "Ooow, please, please, can I have the stool back?"

Swish. Thwack! Now he was faltering, trying out new places to put his feet but finding his muscles already flooded burning at the strain.

"No, I don't think so. But I'll get you something to kneel on." Lori got up and left the room, and I took the opportunity to stand and run by hands over Bill's welts, eliciting some fresh cries and begging looks. Lori was coming back, so I pumped my fingers into the slave's face hole to get some lube to stroke off with, and went back to my comfy master's chair.

Lori was carrying something Bill is familiar with. We often make him stand or sit on it. It's a wooden board, 4 square feet in area. The bottom is flat, but the top has sharpened wooden spikes made out of 1 inch dowels. The spike are half an inch tall, and not so sharp that they puncture, but are very uncomfortable.

Lori stuck the board under Bill, and helped him bring his feet back and behind the post. Now, our slave could kneel without being choked, but the spikes jabbing into his knees and the fronts of his calves might have blunted his appreciation.

Lori went back to her stool and raised an eye. "Ask me to continue, slut."

Bill was shaking his head back and forth and pleading with his eyes, but managed to sniffle and say "please whip me, Ma'am."

Swish. Thwack! "Oh god," Bill mewled as the strikes kept coming, only a few seconds apart from each other.

It had only been thirty minutes, he's such a whiner sometimes.

From my position to the side, I was lost looking from Lori's face, lost in ecstasy, to Bill's chest, now a mass of red lines from the tops of his armpits to the bottom of his ribcage and across to the other side. I swung one leg over the arm of my chair, pulled my thong aside, and started slowing playing with myself. Lori noticed, and smiled wide.

Swish. Thwack!

"Look at how horny you're making your Mistress, slave. You're so sexy right now."

Bill saw an opening, he's not totally stupid. "Please stop, I'll eat your pussies, please! Everything hurts so much!"

Swish. Thwack! "No," Lori said, "this is just what I needed."

Swish. Thwack!

Bill cried and screamed for another twenty minutes of whipping, until Lori decided to give him a break. She looked to me, still slowly masturbating, not fast enough to reach orgasm. "Want to use his face?"

"Absolutely!" I stood up, removed my thong, and stood in front of the crying boy, feet just astride the spiked board. "Beg for it if you want it, or maybe I'll try that whip out."

"Oh please Mistress, please let me pleasure you, I want it so bad!"

I took another small step forward and let him dig in. His pretty eyes looked up at me, bloodshot and wet, as he licked and sucked on my clit. Nothing in the world feels more empowering and exciting than crying slave cunny.

Lori, meanwhile, wasn't resting. She had gotten some string and a short metal pipe, and was now standing behind the post. She brushed Bill's hair back, admiring the work he was doing, then leaned forward to give me a long, tongue-y kiss. I was in heaven and on the edge of a big one.

Lori pipled up: "Pace yourself for a minute, Ash."

"Mmm, now you're torturing me!", I said, but pulled back a little and told Bill to stick his tongue out, occasionally moving my hips forward to slide the length of my pussy along or just poke at him, keeping myself close.

Kneeling down, Lori got to work with her implements. She put the pipe across the poor slave's calves then lifting and arranging his legs to be as far back as possible, until the pipe was tight against both the back of his knees and the post. This left less spikes poking into his sore legs, increasing the discomfort and the amount of wordless complains coming from Bill. Behind the post were a line of hooks set into the floor, just beyond the slave's feet, she'd fully planned this one out. Lori tied the string around one of his big toes, then pulled it tight to a hook, then across to another hook, and back to a pinky toe. Back and forth until both feet were drawn tightly back, with nowhere to hid. Bill must have figured out what Lori's next target was.

"Well slut, I think we're done with the whip for now, it's time for that cane you wanted" she announced, almost skipping to the wall to grab it and bounce back, excited to continue.

"Go ahead, babe, let him scream into you while you cum" she instructed me. I leaned for a kiss from my lover, then stepped forward once again so our slave could get back to work.

Whack! Whack! Whack! She was standing to the side of the post and us, watching me squirm on the screaming slave's face as she struck his feet over and over.

Whack! Whack! He was still trying to make me cum, but Lori's ministrations were distracting him, though the vibration (and sound) of his screams almost made up for it - at least physically. Mentally, I was lost in it all, finding it hard not to let my eyes back in my head as the thrill of his pain drove me wild. I grabbed a handful of the slave's hair and held him in the right spot for the moment.

Whack! "HhhhhrrrrrRRRR!" he let out, eyes wide open and locked on mine, so automatic for him now.

And I was off, cumming hard and leaning over the post, the hand not gripping Bill's head was holding onto the top of the post as I struggled to stay upright. Whack! Lori was running her free hand through my hair, telling me how much she loved me. Whack!

After a long come-down, I let go of Bill's head and nearly stumbled off of him. Pussy off his face, he was now just openly screaming and begging Lori to stop, filling the room with music.

"Aaaah! Please fucking... Please stop! Gaaaarrr!"

Whack! I was back on my comfy chair, regaining my breath, while Lori took out her frustration on the poor slave's feet. She went at it for another minute, not long, then announced she was done. Putting the cane up on the wall, she grabbed a Hitachi and went back to the wet, sobbing slave. After a few slaps and gropes of his chest (only bleeding in a few spots), she turned around, peeled her thong off, widened her stance and bent forward slightly, telling him to get to work on a quality rimjob "if you know what's good for you." The vibrator flicked on and didn't take come off until she'd had a double.

Lori stretched, put the Hitachi in the cleaning bin for Bill to deal with later, then sat on my lap in the chair and we snuggled for a few minutes. Afterwards, I untied the slave's toes, we gave him his stool back and Bill blubbered a thank you to us for not leaving him on the spikes. We both went upstairs for a nice cool shower together.