Boytoy Bill Ch. 05

Story Info
Bill gets a treat and makes mistakes.
3.7k words
4.26
7.1k
6
0

Part 5 of the 8 part series

Updated 02/28/2024
Created 08/30/2023
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Shock Jock

Bill's something of a Luddite. He wasn't always, but since he stopped being a person and became our personal fucktoy he's developed a strong dislike of technology. If it involves electricity, it's almost certain that Bill's lip will start to quiver just a little bit when he sees it coming towards him.

The cattle prod. The violet wand with it's pretty lights. The clamps with red and black wires leading from them and the 'shock box' they connect to that lets us dial the current, voltage and frequency for a fun bout of torture. The amusing toys like our 'quiet time' microphone that turns his outbursts and sobs into painful jolts on his nipples or balls or feet. Hell, he doesn't even like the TV, since it's usually playing some video of him taking a strap-on in his bussy or a whip across his chest while he begs for mercy.

Today, though, was going to be interesting for Bill. He'd been extra obedient lately trying to get on our good side, and it worked. He didn't know it yet, but an hour from now, he'd quickly go from being terrified to begging for more.

First, though, he had some work to do.

"Mmm. Perfect, sweetie, right there," Lori moaned, looking down at me. I was on my knees on a cushion, facing Bill. He didn't have a cushion, slaves don't deserve them.

While I lapped, suckled and fingered my lover, our slave was burying his face into her butt, working the other end, groaning as I used my free hand to pinch and pull his nipples one at a time. Bill's hands were wrapped around Lori's thighs, he needed the leverage to really get in between those cheeks of hers.

Lori was getting that glazed look she gets right before she cums, and I helped by twisting one of the slaves nipples to get a good scream going. She wrapped her hands in my hair as she came, as much to hold me in place as to avoid falling over. I slowed down as her climax subsided, and eventually stood up, planting kisses up her tummy and breasts as I worked up to a kiss on her panting mouth to let her taste herself.

Bill stayed where he was, acting like the cure for slavery was inside her butt.

"Phew! Oh. Jeez." Lori managed to get out. I smiled at getting her good enough that she couldn't speechify well and planted a peck on her cheek.

"My turn," I said, and broke away to go get a strap-on. I chose a nice thick one, and handed it to Lori to suit up. I spoke to the slave: "Get over here, slut. Head on the couch, butt on the floor." I patted the edge.

Bill crawled over and I took position staddling his head, facing the back of the couch, and he got busy applying himself to my already wet pussy. Once Lori was ready, she stole him away for a second to gather some spit from his mouth for lube, and entered me. It didn't take long at all until the deep fucking Lori was giving me and the slave stuck under my clit brought me to orgasm. Lori gave me a playful slap on the ass as she pulled out, then had Bill deepthroat the dildo before taking it off her and placing it in the cleaning bucket for later.

I snuggled with Lori for a bit on the couch. Bill was kneeling on the floor, watching us in silence, and when he caught my eye I said "And what about you, slave? I suppose you want a go, too? Maybe a nice double blowjob? Maybe a rimjob like you just gave Lori?"

He knew I was joking, of course. We'd never given him a proper blowjob and would certainly never lick his butt.

"Please give me whatever you think I deserve, Maam. My only purpose is to make you happy," he said, not even blushing. Like I said, he'd been so perfect recently, degrading himself so totally.

"Hmm, what do you think, Lori? What does he deserve?"

Lori got up from my side and stretched, arms up. "Hmm, how about we stick him on the sawhorse and see what comes naturally?" Bill knows the sawhorse usually means a butt-fucking, and his shoulders sunk just a little, but he kept a brave face.

"Always a good place to start!" I agreed. "Grab the belts, slut, I don't want you trying to slide away somewhere if the going gets tough."

"Yes, Maam," Bill said, and stood, walking over to one of the toy chests to collect thick, brown leather straps, and taking them into the room with the sawhorse.

I had him bend over it, his torso flush with the top and the crease of his hips flush with a length of steel tubing right at the edge of the sawhorse and a few inches higher than the top pad. Two of the bigger straps were wrapped around his waist and the top pad, and very tightly secured. I lifted first one and then the other of his legs up to the sides of the sawhorse, up high until they were almost in line with his torso, and secured his thighs to the nearest attachment points, then his calves right below the knee, and his ankles as well. Lori meanwhile put some cuffs on his wrists and attached them forward and down. Not too tight, we wanted to be able to lift his head up and access his face. Because he was so far back, there was a good foot and a half of space between his head and the end of the sawhorse. Lori had him lift his head so she could pop the last two pad segments out and click a wider pad into place, more comfortable for us to sit on and give him something to do with his well-trained tongue and lips.

The end result was that Bill's butt hung out into space begging for attention, his back with a slight fuck-me arch leading down to the straps around his midsection. He couldn't move even slightly forward, and the straps on his legs kept him from being able to move backwards, either. I couldn't resist giving his tush some nice hearty slaps, rubbing the reddening skin in between strikes. Lori left the room to grab his toys for the evening.

Smack! Smack!

"Well, slave, wanna guess what's in store for this whole situation back here," I asked, pulling gently on his balls, tapping his cock.

Smack!

"Oww! Whatever your mood says, Maam! Aaah!"

Smack!

"Mmm, and what do you think my mood is?"

Smack!

"Ah! I thought it was good but I must have displeased you, please... Ah! Please have some mercy, Maam" he said in between slaps.

Lori came back into the room, the door located behind Bill. She dropped some equipment behind him where he couldn't see, then placed the shock box on the pad right in front of Bill's face.

"No, please! Why?! What did I do?" our slave started panicking.

Smack! Smack!

"Scared, slut?" Lori asked. "We're gonna do things to you that you've never experienced. Should be a fun night!" We smiled at each other, enjoying making our slave tremble and worry.

"Fucking... fuck! There's no point!" he let out, dismayed that all his best behaviour was only earning him an appointment with one of his least favourite implements.

"Oh, can it," I replied. I grabbed a hold of his Reminder and slowly pulled it out of his ass, then put it in his mouth. I could tell he briefly thought about keeping closed before deciding he'd just make whatever was about to happen worse. He gave it a few sucks while I twirled it around in his mouth, before putting it down under the sawhorse, and leaving to grab the strap-on Lori had just finished using to fuck me.

Lori moved the shock box down to a side of the sawhorse, clicked some leads into place, and ran the power cable to an outlet. The leads ran to two nearly identical loops. The first went around his junk at the base, around both his cock and balls like a cock ring, and a simple rubber slider moved to keep it snug. Bill made wordless protest at feeling something go to that particular location, probably hoping it would have been his buttocks or feet getting shocked. The second loop was similar, but wouldn't attach until Bill was erect.

My strap-on in place, I went to Bill's side and lifted his head up by wrapping a hand into his hair. I stuck four fingers of my other hand into his mouth and face-fucked him a bit, pushing his tongue down so he'd cough up some natural lube. I applied it to the dildo and got behind him, putting one of my legs up on the bottom pad to make sure Lori had room to work on his cock.

Bill was quiet, probably psyching himself up for what he assumed was going to be some horrible sensations through his balls, of which he'd experienced plenty of since becoming a slave. I pushed the head of the dildo into him, and started slowly fucking my way deeper and deeper into his backside, getting in a little further every stroke. Bill can't pretend he doesn't enjoy being butt-fucked anymore, not since we used the plethysmography machine to force him to admit what a slutty butt-slut he'd become under our tutelage. He hates being used like this, and the pleasure he gets from it makes him feel ashamed at his body's betrayal.

As I worked up to a proper depth and rhythm, Lori was giving him a little bit of a dryjacking, and teasing him all the while.

"Just another day for our perverted slave, getting abused for our sadistic pleasure. Do you think you'll be able to have a prostate orgasm through all this?"

Bill didn't answer, until Lori gave his balls a light punch.

"Gah!" he groaned. "I don't know, Mistress, depends how bad it is."

"Well, I believe in you. Oh look, getting a little hard already. Nothing fazes you, anymore, does it? Ash could use Sriracha as lube and you'd probably still try to cum, haha! So horny." Bill just shook his head, face down and forehead on the pad.

Lori pulled back Bill's foreskin and held the exposed portion of the second loop to his frenulum, such a sensitive part of the male body. That got his attention.

His head lifted up and he looked straight forward, then tried to crane his head around to get a look. "Uh. Uh," he let out, deep grunts.

She took it off.

"Hmm, slut? Something to say?" I asked, currently sliding all the way out to let his little asshole pucker up completely, and giving him some fresh smacks on his quite red cheeks.

"What the..?"

I spread his cheeks with both hands and thrust forward, pushing all the way in in one slow stroke.

"Ooh, getting really hard just off that?" Lori laughed. She again pressed the lead to the base of his sensitive glans.

"Oooh, jeeeeez," Bill groaned. Lori kept it there for a half minute while I slowly churned his insides, before taking it off again.

"And there we go," she said, proudly. "Fully erect just like that. Who needs blue pills?"

Bill was used to the sharp zap of the shock box, to the intense pain of current being fed through his nipples via clamps or balls through the stim pads, or various other places we'd attached it. Even his tongue, kept exposed by a ring gag. This, though, was new to him. It was configured differently now, such that low, ebbing and peaking waves of current flowed from the lead at his base to the one at his tip, causing very intense pleasure throughout his shaft and head.

Lori hit pause on the box, pulled his foreskin back fully and placed the loop around the bottom of his glans, the elastic slider and gravity keeping it in place. She ran some of the excess wire upwards then around his cock and balls a couple times to make sure it didn't try to fall off.

"Ask nicely and I'll turn it back on."

"Oh, please Mistress, it feels so good."

"Hmm. Ask better, say something humiliating," Lori demanded.

"Err, please Mistress, I'm just a horny piece of meat you can use for anything you want, please fuck my butthole and make me cum!" he blurted out, trying to look back over his shoulder and blushing just a little.

"Haha, I bet you even meant half of that!" She hit resume, and turned a knob, bringing the intensity down quite a bit so he didn't cum right away. She lifted the shock box up and placed it on the small of his back, arched so slightly and tightly by the straps, then brought a tall stool over to the head-end of the sawhorse. She sat on the wide pad, lifted his face up, and scooted forward so her muff was in his face. Leaning back and supporting herself on the stool, Bill started his ministrations, eyes locked on Lori's.

"Mmm, slower slave. We're gonna be here a while and I don't want to get all fucked out before I get a turn at bat."

The shock box could be programmed in all sorts of ways, but it was all manual right now. I turned it all the way down to it's lowest setting, and spent a good ten minutes giving our slave a thorough ass-raping, before deciding it was time to stop teasing him. I turned the appropriate knob up to about a quarter.

"Oooooh!" he moaned into Lori's pussy, and didn't need to be told to pick up the tempo of the head he was giving.

I kept my hand on the dial, and timed short bursts of thirty-five to forty percent with my deep thrusts into his bowels. When his grunts and groans told me he was starting to cum, I turned it up to sixty percent and buried the dildo balls-deep inside him.

It was overload for our slut, and he started shaking and crying. I started slow-fucking him again and turned the intensity down to about half, as the pleasure turned to post-orgasm torment.

"Oh, uh, pleathe" he said into Lori's pussy. "Doo muth!"

We both laughed. "Oh get real," Lori said. "You know it's gonna be too much for too long. You aren't getting out of here until there isn't anything left in those balls. I'm almost there, keep going."

After Lori came, bucking her hips into his face as she did, she got up to take her turn. I pushed deep into him and unclipped the strap-on, holding it in place as Lori got into position. Before she could get everything adjusted to her size and resume fucking him, Bill was cumming again. I was just pushing my muff into his face as his moans of pleasure turned, again, to groans of agony.

Lori flicked the intensity up to max.

"Pfffff, fff, ffff" was the only sound coming out of his throat as he lost sense of whether he should be inhaling or exhaling. I pushed my hips forward and he blew raspberries into my clit. Good start.

His eyes were pinched shut as the current mixed pleasure, too much pleasure, and simple raw pain through his dick. I allowed it given the circumstances, but as Lori turned the intensity back down, the dummy kept them closed. That'd cost him.

"Eyes closed while you give me dome? That's five strokes with the big paddle," I said. He quickly corrected and opened them up wide. "I'm going to add one more stroke for every time you blink, now suck."

We figure at least two more orgasms got pulled out of him before I got my own, wrapping one leg around the back of his head and squeezing his face into me as he sucked and licked. Lori slowly turned the intensity down to zero before turning it off entirely, then slid out of him and removed the leads from his abused genitals. There was quite the puddle of jizz underneath him, though he didn't piss himself like he sometimes does while being so aggressively milked.

"Whew, that was a good first half. How many times did you cum, slave?" I asked, dismounting from the seat.

"First half? Please, I can't do anymore, Maam! I think maybe five orgasms, please don't. I like it but it's too much, please I need a break!"

"Well," Lori said, taking the strap-on off and placing it on the sweaty pad in front of Bill's face, "I think I need one, too."

"I suppose," I agreed, "I could use a shower and a sammy. But first...." I went to the wall and grabbed the big paddle Bill had earned himself. It's a solid piece of oak, about the same size as a cricket bat, but flat on both sides. "By my count," I said, using the end of the cruel object to lift the slave's chin up, "you blinked thirteen times. Lets round it up to twenty." Any post-nut glow Bill had was instantly erased.

I took a place right perpendicular to his butt, so that each stroke would hit both cheeks, while Lori had a seat on the stool in front of the sawhorse to enjoy the show, an anticipatory smile already on her pretty face. I wound up and struck, the paddle sending a visible wave across his cheeks even in this stretched position as it landed with more of a thud than a crack.

"Aaaah! Fuck!" Bill screamed.

Thud!

Smack!

Thud!

Thud!

I paused at five strokes, while the poor slave howled incoherently. I was hitting just slightly different places each time, trying to paint his entire ass with the bruises that would soon come, deep in colour and painful for many days, already dreaming of ways to take advantage of it. I walked to the other side, and the next five strokes were angled slightly upwards to get at the bottom part of his butt cheek before his dangling balls got in the way. I didn't want to hit those, that would just be mean.

Thud!

Thud!

Smack!

Thud!

Crack!

As I listened to Bill sing, I ran a hand over the site of the first strokes, already glowing red, the edges of the paddle well defined. I knew they'd turn blue and purple over the next hours. I went to his side and knelt down to to look at him level, his face contorted in pain, covered in tears, sweat and pussy juice. He looked gorgeous as his scared eyes switched from Lori to me.

"That's ten. You're halfway there slave. Keep in mind what this is all for and learn your lesson. Which is...?"

Bill was mewling and sobbing, but managed sniffle his nose and say "Always have my eyes open and sniff always look at you or Mistress."

"That's right! It's so easy, I don't know why you forget sometimes. Lets get these last ten done so you remember."

I got back behind him and considered my options, deciding to spread the last ones out across the backs of this thighs with some upward strokes. I tried a few practise swings, just caressing the area I was about to hit. Winding up again, I swung it like a golf club, bending my knees to get down to the correct height, and landed the full length of the paddle on his right thigh, from just above his knees all the way to his butt.

Smack!

Bill went wild, shaking and crying, his body trying to break out of the bondage but barely moving in the slightest save for his arms, shoulders and head.

Smack!

Smack!

Crack!

Smack!

I didn't give him a rest, just switched my stance and tried a couple practice swings on his left thigh, harder to do with my off-hand but manageable.

Smack!

Smack!

Crack!

Smack!

Thud!

The last one was a bit of a miss but I don't think Bill noticed, judging from the protest he was putting up. I decided to be merciful and not take a mulligan. I put the paddle back up on the wall, grabbed a bottle of water and a blue pill from the dresser, then went to stand behind Lori, who I think was having second doubts about needing a break from the way she had moved a hand in between her crossed legs. Putting my chin on her head and giving her a hug, both of us smiled and watched Bill try to slowly get control of himself.

When I figured he was about composed enough to think straight I asked "And what's the lesson, again, slave?"

He took a few deep heaves and lifted his head up to make eye contact, tears streaming down his cheeks, a puddle of them on the pad in front of him. "Always look at my owners, Maam!"

"Good! See, even a dummy like you who only thinks with his cock and butthole can figure it out." I approached him, unscrewing the lid on the bottle and tilting it. "Drink up, sweetie, you need the fluids."

While he drank, I lovingly wiped his cheeks, and when he'd had his fill I gave him a nice long kiss, letting him suck my tongue while I tenderly stroked his jaw. I brushed a place dry on the pad in front of him and placed his dick pill there, where he could just barely reach it if he stuck his tongue out. I pointed at the clock on the wall.

"Lori and I are going to go upstairs to freshen up and have a bite to eat. In thirty minutes, eat this pill, and we'll be back right after to make you cum some more. Aren't you lucky to have such loving owners who give you such good orgasms?"

12