From Boss to Slave

By davdar192

Published on Aug 3, 2021

Gay

This is an authoritarian story of a desperate man selling himself into slavery to rid himself of his debts and the humiliations he experiences as he accepts his fate.

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If you're enjoying this story, please let me know davdar192@yahoo.co.uk, Thanks

After we had returned to the house my former colleagues decided to have beers on the deck overlooking the garden which I had to prepare, I was left standing to the side of them while they chatted.

My head was reeling from the news that my masters had orchestrated my downfall and buying me as a slave, I didn't know what to do.

If a slave was found to have lied to get their masters convicted, it could lead to permanent slavery as property of that master or being sold to another master permanently. If a master was found guilty, a slave could be freed and given all the masters belongings including the master as a slave to be either kept or sold.

It was a huge risk, but could work out very well for me if I could find a way to work this, but did I want to? I had really started to enjoy this lifestyle now I was used to it, no worries or concerns and I really enjoyed serving my Masters.

I had some information to start an investigation, but I needed to find a lawyer and the older gentleman to stand up for me.

The huge question I had for myself though was did I want to end my slavery? I was enjoying what I was doing now, no stress or worries. I'd always been embarrassed about my size and didn't have much of a sex life because of it, I just used to jerk off a lot. The little sex I did have I would always be the bottom and I was getting plenty of opportunity for that these days. I was now quite proud of being a slave and showing off my body to everyone, but my Masters were worth a lot of money, if I was successful I would be very rich and have two slaves to myself.

I couldn't stop thinking about it while my former colleagues enjoyed themselves and got drunk on the beers I was serving them, it felt good waiting on them with the butt plug, I wasn't even listening to them unless my name was called for more drinks, I had enough on my mind.

I heard a round of laughter, then Master Edward called me over.

"maggot, there's a blindfold in your box, go and get it and bring a bath towel as well, you can take out that tail butt plug now too"

I went inside and removed the butt plug then went to the box wondering what was in store for me and returned with the blindfold and a towel from the linen cupboard.

I stood in front of Master Edward with the towel and mask.

"OK maggot, put the mask on"

It covered my eyes, the mask fitted tightly, no light came in at all. I heard Master Edwards voice.

"OK everyone, lets all swap places"

I heard them all get up and move around, then Master Edwards voice again talking to someone.

"OK, put the towel over your crotch so we don't all see your dick and pull your pants down"

I heard rustling then I was guided somewhere

"Kneel maggot"

My head was guided forward and under the towel, I could smell a musky masculine scent, someone pulled my hands back and fastened them behind my back.

"OK maggot, your job is to suck each cock that's guided into your mouth, get it hard, suck it off, then taste the cum. Once you've sucked us all off, you guess who each cock is. Get it wrong and you have to drink that mans piss and service his cock for the rest of the day, he also gets to spank you ten times with the paddle after each piss, this will help you learn who is who. If you get it right that man gets to choose a toy from the box to use on you as a treat"

This could be fun for me, but I really didn't want to suck off my two friends, this was so humiliating, but I had no choice.

I moved my mouth forward stuck my tongue out and guided the dick into my mouth, it was soft and had a foreskin, I slid it into my mouth and could feel the weight of it on my tongue, I tightened my lips around it and pulled the foreskin back, I started sucking and sliding my mouth up and down, my nose was in some bushy pubes and I could feel the hair from the balls on my chin. The dick started to grow, it was a good size, much bigger than mine, I knew instantly it wasn't either of my Masters as it was smaller than theirs, and it definitely wasn't Adams huge cock, so it was either Mark, Jason or Scott, I had no idea. I'd sucked Mark before, but couldn't determine whether this was his or not. The thought that I had one of my friends dicks in my mouth was really turning me on, I could feel a phantom erection.

I slid the hard cock in and out of my mouth, then I felt the balls on my chin tighten and the muscles on the underside of the penis twitch as the load was pumped into my mouth, a hand grabbed the back of my head as it was pushed further onto the cock and I heard a groan, it sounded like Jason, I couldn't believe I had just sucked my friends cock.

There was a little cheer from everyone, but I couldn't tell if anyone's voice was missing, then I heard trousers being pulled up and someone else sitting down, then a zipper being undone, trousers pulled down and my head guided under the towel again, as soon as the cock was in my mouth I recognised it as Master James, this one was easy, I knew what he liked too, so he came quickly. As he started to zip up I couldn't help myself.

"Thank you Master James"

There was a round of laughter, then I heard Master James talking with a smile on his face.

"Well done maggot, I wouldn't have been happy if you got that one wrong."

I felt a pat on the head from Master James big hand, then someone else sat down in front of me, again the zipper came down, my head was pushed under the towel and I moved my head forward until I could feel pubes on my nose, then manoeuvred the dick into my mouth, again, it had a foreskin and felt almost identical to the first, as it grew it felt a bit thicker, the pubic hair felt softer on my nose and the balls weren't as hairy. I had no idea who's dick this was, he pushed my head down onto his dick hard and a minute or so later started pumping his load into my throat, as he let out a groan I was sure it was Scott.

The same happened again, this time the cock was circumcised, I but other than that it felt exactly the same, less pubic hair though, maybe it was trimmed, again he got hard, and seemed a similar size to the first one, not as thick as the last one, he came quickly, I knew it wasn't Adam or either of my masters, and it couldn't be Mark as he wasn't circumcised, but this didn't sound like Scott or Jason, I was confused.

The next cock was definitely Master Edward, I knew straight away again, I did the same when I had swallowed his big load of cum.

"Thank you Master Edward"

I heard a clap

"Well done maggot"

I heard them changing seats again, I knew this last one was Adam, he was semi hard when I took him into my mouth, he was so big his cock was going down my throat and I was struggling to breath, I gagged a couple of times and heard giggles. He grabbed the back of my head as he forced his cock in, I felt the muscles at the base of his dick twitch after his balls pulled up, but he came straight down my throat, so I didn't get to taste his cum. He zipped up and left the chair, then I heard Master Edward.

"Right maggot, take the blindfold off and stand up"

As I stood up, I looked down at my little hairless dick, it was the only one that hadn't cum I looked around at my former colleagues now all fully clothed, I just had my nose in their pubes and their dicks had just cum in my mouth.

Master James looked at me.

"Well done maggot, so who do you think number one was?

I had to take a guess, it was probably Jason

"Was it Jason Master?"

They all laughed, especially Mark, I guessed too late that maybe it was him.

"OK maggot, who was number two?"

"That was you master"

There was a small round of applause

"and number three"

"Was it Scott Sir?

another round of laughter, I realised I'd gone wrong, the other one I hadn't been sure about couldn't have been Mark as he wasn't circumcised.

"so number four then maggot?

I knew it was wrong now

"Was it Mark Sir?"

they all laughed, again.

"and number five"

"Master Edward Sir"

"and number six was Adam Sir"

They all gave me a round of applause.

Master James stood up to announce the answers.

"one was Mark, two was James, three was Jason, four was Scott, five was me and six was Adam"

"So you're drinking piss from Jason, Scott and Mark with ten spanks each time and Me, Ed and Adam get to choose a toy to use on you"

I realised I was going to be busy and have red buttocks by the end of the day, they'd already drank a lot.

Mark stood up

"I need a piss"

I walked over to him and got on my knees, I'd drank his piss before, but not in front of my friends, he pulled his dick out of his trousers and I wrapped my mouth around it, the flow started, Scott got out of his seat for a closer look as I gulped down Mark's piss.

"Oh my god, he is actually doing it"

I felt my cheeks blush, he finished and I sucked up the last few drops and stood up as he put himself away.

Master James told me to get the paddle for Mark, so I ran inside, got it then went back outside and gave it to Mark and bent over, I didn't need to be told, I'm a good slave.

He gave me ten hard whacks, five on each buttock, it didn't hurt much, it was more about the humiliation in front of my friends.

I stood up, Master Edward instructed me to go inside and get my box of toys, when I returned, they were all laughing about something, I guessed it was me.

Master Edward looked in the box first, he pulled out a stainless steel magnetic ball stretcher, then he passed the box to Master James, he was looking through the box for a few minutes then pulled out a large pink cock shaped dildo with balls included. Master James passed to box over to Adam who kept laughing to himself as he went through it, eventually he pulled out a remote controlled vibrating butt plug.

He looked at it

"This looks like it could be fun"

I seemed I was going to be the entertainment for the afternoon, Master Edward beckoned me over to him.

"Let's get this on you then maggot"

He grabbed my balls and pulled them down, everyone was looking at them as my foreskin pulled back, the ball stretcher clicked into place, it felt really heavy on my tight balls.

Master James held the big pink cock, he waved it at me.

"Here you go maggot, put this on the decking and lower yourself onto it"

He looked in the box again and pulled out some lube

"lube yourself up first"

I squirted some lube onto my hand and started working on my ass in front of my friends and colleagues. Once I was lubed up, I lubed the dick too, then put it on the ground and squatted over it, they were all watching me as I guided the dildo into my ass.

Master James picked up his phone

"Let's make his dick look like he's enjoying this a bit more"

I felt my dick get hard as I slid myself onto the dildo, the head of my dick was now completely exposed as the ball stretcher pulled on my scrotum and my hard little dick visible to them all as the dildo completely entered my hole, I could feel the balls touch my ass.

Then I heard Scott say

"I need a piss"

I got up and moved over the Scott, the dildo stayed in place. I was excited to have his dick in my mouth again and to know it was him this time, I knelt in front of him and undid his zip, to pull his cock out, I wrapped my mouth around it, it took a few moments for the flow to start and I looked up to see him looking down at me, he smiled.

I was on my knees with a hard dick and a big dildo in my ass with his dick pissing in my mouth and it felt amazing.

"I'm done, I wasn't as desperate as I thought, it was only a post cum pee"

I stood up, handed him the paddle and bent over, he patted his left leg.

"Over my knee maggot"

I bent over his knee and felt him reach around my body with his left arm as he grabbed the ball stretcher, and held it firmly so I couldn't move.

He went in low and hard with the whacks and didn't try to avoid the dildo, so each whack was felt in my ass as well, I could feel my hard dick bouncing with each stroke.

When Scott finished, he let go of my balls and I stood up and stepped away, I was embarrassed that I'd really enjoyed that!

Master James laughed.

"Lie on the ground on your back and show us how you would like to fuck yourself with that dildo then maggot"

I lay on my back with my knees spread and bent so everyone could see my ass and reached around and started sliding the big dildo in and out, it felt amazing, why hadn't I tried fucking myself with something before now! I looked down at my hard dick, it was pointing up and leaking precum, I realised I was groaning, I was really enjoying this, even with the six of them watching me. I was desperate to play with my dick and make myself cum, but I knew it wouldn't work.

Jason broke my fantasy

"I need a piss now too"

He moved away from the group and stood with his back to them, I knelt undid his shorts and I took his dick in my mouth, as the warm liquid started flowing, I gulped it down again, I could feel my hard dick twitching. I felt his dick growing as he finished peeing.

"You might as well suck me off again while you're down there"

It was a pleasure, he came quickly again and I swallowed his load, as he finished I heard Scott's voice.

"I think I need a bit of that now"

He stood up and walked over to where Jason was, I moved over and undid his shorts and pulled his dick out, he was already semi hard, he was a good size, I looked down at my own erection as a comparison which only made me feel inferior, but my dick was still rock hard and oozing precum.

Once I had made him cum I zipped him up. Jason had sat down again.

"Don't forget your spanking maggot, get over my knee"

I bent over his knee and he quickly grabbed my balls to keep me still, I could feel my dick on his thigh as he spanked me with the paddle, when I got up, I could see my precum on his leg, he noticed it too.

"Yuck maggot, that's disgusting, lick that up"

I got on my knees and started licking his inner thigh, what had I become? I was thoroughly enjoying this though.

Adam held up the butt plug.

"Can we try this one now?"

Master James told me to take out the dildo and put the butt plug in, I did as instructed, it went in easily after playing with the dildo.

Adam held the remote.

"Get on your knees, hands behind your head."

I did as instructed, then the most amazing sensation started in my prostate, the vibrations were incredible, I started moaning my hard dick was oozing more precum, I was desperate to touch myself, Adam was constantly changing the intensity of the vibrations and was keeping me on the edge of cumming, I hadn't cum in months apart from a controlled release at the slave center. I didn't care that everyone was watching, I looked at my Masters.

"Please Masters, I beg you, please let me cum"

They all laughed.

"Please Masters, please let me cum"

I looked down at my hard little dick, I could feel the weight of the ball stretcher, I didn't care that everyone was looking at me or how desperate I seemed

Master James took the remote off Adam.

"Time to stop now Adam, he's getting way too excited"

I hadn't noticed Scott had got the garden hose and blasted my dick with icy cold water, Master Edward removed my erection.

They all laughed as I went soft again.

The afternoon continued, I enjoyed being kept busy drinking all afternoon, my buttocks were burning and my balls had a dull ache, but I was making my masters proud while having to pee a lot myself.

I was quite enjoying the humiliation in front of my old friends now, it was good be on my knees with so many dicks in my mouth. Jason continued to enjoy it, he wanted to pee little and often and like the others he always had a semi erection when his dick was in my mouth, by the end of the pee it was more hard than soft, I made sure I gave his dick a last lick as I pulled my mouth away from it each time. Jason came in my mouth twice more that afternoon.

The afternoon turned into evening, they ate barbecue, my belly was too full for me to eat my slavefit.

My masters dismissed me before the others went to bed, I was left with the butt plug though, but I slept well with it in.

I woke my masters the following morning with the usual routine then followed them down to breakfast, I had been hoping they would remove the butt plug for me or instruct me to do it myself, I was really needing to go to the toilet, maybe they would allow me after breakfast.

They all ate while I waited on them, Mark had the idea that they should have a game of tennis in the morning before everyone left in the afternoon, my masters volunteered an hour with me to do whatever the winner wants before we leave, they also announced that I could be ball boy for the game.

As we all arrived at the tennis court, I couldn't take it any more.

"Please Master James, Master Edward, can I take the butt plug out so I can go to the toilet"

I should have asked earlier, it was so embarrassing asking to go to the toilet with the others watching on.

Master James looked angry

"Go on then maggot, take it out, do your business and give yourself a good clean out and bring back the large butt plug"

I thanked him and ran to the toilet to sort myself out.

Once I'd finished I cleaned and put away the plug I'd been wearing and got the bigger one and ran back out to them.

As I ran to them Master Edward shouted

"About time maggot, we're waiting to start and we need our ball boy, now turn around, bend over and put that plug in your ass, whoever wins you will want that ass ready to take their dick"

I bent right over so my dick and balls would be visible and stretched my legs as far as I could to give a good view to Jason, Scott, Adam, Mark and my Masters and slowly eased the plug into my ass.

Once I had finished, the game started, they paired up and the loser of each game was out they were all really quite good apart from my masters who were first out, then Adam followed by Mark leaving just Jason and Scott to win, they had played hard, it was obvious they both wanted to win.

It was really uncomfortable running around after the ball with the large butt plug in my ass, but everyone seemed to be enjoying watching me.

In the end Scott won by a point.

he looked at me and smiled as he walked off the court dripping in sweat.

Was he just going to take me to his room and we could sit and chat or was he going to use me, it didn't take long for me to find out.

I followed him inside where he went to my box and took a couple of things out, then I followed him up to his room he closed the door behind us, I didn't know what to expect.

"Bend over the bed Darren"

I bent over the bottom of the bed

He took the blindfold and put it on me, then he fastened my hands to the back of my collar, pulled my legs apart and attached them to the legs of the bed.

I heard him undressing, I was shocked that he was doing this to me, I wondered how long he'd thought about this.

I felt his dick at my ass, then it was pushed in and he fucked me hard.

When he had finished he undid my legs and turned me over, so I was lying on my back, he released my wrists, then fastened them to my ankles and attached a leg spreader, so my legs were in the air spread apart.

Suddenly I felt soft skin on my face.

"Get your face in there and rim my ass maggot"

I stuck my tongue out and started working on him, I could hear him jerking his dick as I licked his ass, he suddenly pulled away.

"Suck my balls bitch"

I opened my mouth and two hairy balls were on my tongue, I licked and sucked, this felt great, before I knew it his dick was in my mouth and he was pumping his load, I heard him sit back on the bed he didn't speak at first.

"look at you Darren, you really like this don't you"

I couldn't disagree.

"Yes Sir, I think I've found my calling, I love it"

"I'd never realised how small you were, you managed to keep that well hidden, and I never realised I'd not seen you naked, you do look like a proper sub slave"

I felt him hold my dick

"Thank you Sir, I try my best"

I did always try my hardest now, at first it had been difficult, but I know loved the total control over my body and everything I did.

He stood up, I felt his cock push into my ass, once he'd finished he dressed then took the mask off and sat on the bed. I now felt really exposed, tied up on my back with my legs spread in the air in front of him, I saw a glimpse of my image in the bedroom mirror, I looked good bound and naked with him fully clothed, I liked this position.

He looked down at me.

"I'm still amazed what you've become, I'd never have thought it, but you seem really happy"

I was so content now, this was my life.

There was a knock at the door, it was Master James.

"Come on Scott we need to head back"

Scott opened the door and Master James entered.

"Ah, you've had a bit of fun, he looks good like that, but he's got a bit of cum on his chin"

Master James scooped it up with his finger and put it in my mouth

"Thank you Master James"

"lets get you untied and get moving then maggot"

He released me, and I packed their belongings while they all chatted downstairs, when I came down they all said their goodbyes and we left, I'd really enjoyed the weekend it had made me realise how happy I was, now, even in front of former good friends I just wanted to serve. But I wasn't sure what to do with the information I'd been told, it might be fun to get some revenge on my masters.

to be continued....

Next: Chapter 16


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