Revenge on the new boss

The gay gang have the dildo drill ready to use on Joe as part of his lesson, will the drill help to teach him?

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  • 14 Min Read

The following story contains content that may not be suitable to all readers, including (but not limited to) physical violence , non-consensual sex or emotionally damaging behavior. This story is fictional and does not portray real events or real persons. Reader discretion is advised.


“No! No! You can’t put that up my arsehole no!” Joe pleaded.

“Yes we can and we will!” Jordan laughed and he continued to rev the drill.

“No I don’t want anything up my arse! No I won’t be able to take it!” Joe begged.

“We don’t care how you react to it, it’s your punishment!” Logan informed him.

“We’re getting your arsehole nice and loose so we can all give you a good fucking later!” Terry grinned.

Jordan was pulling a bottle of his bag which Joe didn’t approve of “No! Put that fucking bottle back in your bag, don’t you dare use it on me whatever the fuck it is!” Joe threatened.

Jordan looked around at everybody. The gay gang shrugged their shoulders and Terry said “I mean… to be fair Jordan we haven’t really given him much of a say in anything, perhaps we can let him have this one say in this don’t you think?”

Jordan smiled and said “okay yeah fair enough” he then walked over to Joe show him the bottle, “we were going to go a bit easy on you and lube up your arsehole first so it wouldn’t be as bad. But if you don’t want any lube then we’ll just drill you in raw instead.” Jordan shrugged and put the bottle of lube back in the bag and we all laughed.

Joe was now desperately pleading “no no no no no! I take it back! I take it back! Lube me! Lube me! Please!”

“Gosh Joe really wants it!” Scott was amused.

“No I don’t want it!” Joe roared.

“Oh so you don’t want the lube again now?” Scott continued to tease.

“Yes! No! Arghhh!! I don’t want any of this! Fuck off Scott you fucking know what I mean!!!” Joe was furious.

“Now now Joe, don’t get all angry, the more tense you are the more it will hurt!” Scott laughed. He clearly wanted Joe to be as angry as possible so that it would hurt him more.

“FUCK!” Joe shouted.

“Let’s get him bent over lads!” Terry was excited.

The gay gang bent Joe over so that his arse was facing the ceiling. His arse was big and peachy with some orange/brown hair going down his crack. The colour of his arse cheeks was still a faint pink from when Nick had spanked him earlier.

“Let’s get that hole spread nice and wide!” Terry said.

Terry and Steve had spread Joe’s arsehole apart whilst Jordan proceeded to insert the dildo drill up it. About a quarter of the dildo had gone inside Joe’s arsehole which caused him to make moaning sounds which grew louder as Jordan pressed his finger on the trigger and began to drill him.

“AHHH! AHHH! AHHHHHH!!!!!” Joe yelled. The sound of the drill was loud and it was going deeper and deeper into his arsehole until half of the dildo was now inside.

“OHHH! GET IT OUT GET OUT! OHHHHH!!!!” Joe pleaded.

“You’re going to have to speak up Joe, nobody can hear you over the loud drilling noise!” Scott joked.

The other employees were cheering the gay gang on as they continued to drill Joe’s arsehole “Yeah!” “Drill him!” “How do you like that Joe?!” The noise of the drill was so loud and Jordan showing Joe not mercy as now nearly the whole of the dildo was inside him!

“OHHHHH!” Joe’s moans were now louder than ever, almost matching the volume of the drilling noises. Eventually Jordan took the drill out of him and showed us all Joe’s newly reshaped hole.

“Nice and wide, ready for a good fucking later what do you all think?” Jordan asked us.

“Yeahhh!!!!” We all cheered.

“No! No!! No!!! You can’t do this!!!” Joe pleaded.

“You scared Joe?” Scott teased.

“I’m never fucking scared!” Joe retaliated.

Joe clearly was afraid of what was to come though. His body was shaking and the way that the other employees would shake whenever Joe so as much as made eye contact with them. Good. Let him be afraid.

“Joe might just get so afraid then he may end up pissing or shitting on the floor!” Scott laughed. “Do you think he’d be made to clean it up?”

Logan overheard him and answered “oh yeah! If he has any accidents he’ll be using his tongue to clean it, the floor should not be left dirty when there’s a worthless slave to clean it up!”

We all grinned at his response and we were looking forward to getting to fuck Joe. But before we gave Joe his fucking with our dicks, the gay gang let each and every one of us have a turn at using the dildo drill on Joe’s arsehole. There were times where Joe would try to quieten down his cries of agony to not look as weak but he couldn’t help himself at times and his screams would be louder than the sound of the drill at times.

When it was my turn, I took the dildo drill and began to insert it into Joe’s arse. “OHHH!” He moaned as I inserted it deeper and deeper. Joe managed to let out a threat before I began to drill him “you and my dad will be the first to pay!”

I ignored his ridiculous threat and began to drill him. “AHHHHH!!!!!” Joe called out. The vibration of the drill felt soothing in my hand and I gradually let the drill penetrate Joe’s arsehole even further. The more Joe yelled out, the further I drilled him. I gave Joe’s arse cheeks a slap with my other hand to keep them nice and pink from the spanking that his dad had gave him early. His arse cheeks jiggled with each slap I gave them which amused the crowd.

“Hit him harder Ben!” Ryan encouraged me.

I gave Joe’s arse cheeks an even bigger slap where he reacted with a yelp which made everybody laugh.

“STOP!” Joe pleaded.

“Shut it boy!” Terry told him.

“How about we now give the boy a good fucking with the real things this time?” Steve asked us all.

“Yeahhh!!!” We all cheered.

“I’d be delighted for him to take my 8 inches!” Mike was excited.

Just then, the door opened and Nick entered. Nick looked at Joe who was bent over and then to me with the dildo drill in my hand. “Ah I wondered what all the noise was!” Nick said with a smile, he seemed happy that Joe was getting his comeuppance. “To show my appreciation to you all for the lesson that you are teaching my son, I thought I would make you all some lunch, do you care to join?”

“Are you for fucking real!?” Joe shouted. Nick’s smile dropped and went back into disappointment.

We all agreed to have lunch but realised that somebody would need to stay to keep an eye on Joe.

“He’s naked, handcuffed and has a couple of belts tied across his upper body so it’s not like we’d need to worry about him getting anywhere” Brad explained.

“I know but it’s more just in case he finds a way to break the cuffs or does something awkward, it’s just best to have somebody keep an eye on just in case, Jason would you mind? Once of us comes back, we’ll keep an eye out and you’d be able to have your lunch then.” Terry asked.

“Okay fine, that works for me” Jason replied in a tone that suggested that he’d much rather be having lunch now instead.

“Perfect” replied Terry.

Everybody had made their way out of the room. “Are you coming Ben?” Ryan asked me.

“In a few moments” I reply, “I just want to speak to Joe.”

Ryan gave a slight disgusted look and said “not sure why you’d talk to that thing but hey ho! Come and join us when you’re ready” and he made his way to leave the room. Nick looked at me puzzled so I gave him a reassuring nod to suggest that everything is fine and he smiled back before leaving the room.

Jason tackled Joe to the floor and kept his foot planted on Joe’s upper body. “There’s no fucking need!” Joe yelled.

“Listen boy, I keep my foot on your chest or I can plant it on your dick and balls instead, your choice?” Jason barked.

Joe didn’t acknowledge him and turned to me instead asking “and what are you here for prick?!”

Good question, what am I here for? I was having the time of my life giving Joe his due but it’s Nick that I care for and Joe learning his lesson would be the one thing that would make Nick really happy. I think about how happy Nick was when he saw how Joe was being punished and how his smile had soon dropped when he saw that Joe was still talking like his usual self. The quicker Joe learns, the better it will be for Nick, I need to talk some sense into Joe somehow.

“I wanted to talk to you” I tell him. “This doesn’t have to continue you know, we just want to know that you’re sorry. Apologise to everybody, reverse these new rules you’ve put into place and we’ll get you some clothes to put on, nothing more needs to happen to you.”

Jason gives me a confused luck. Joe replies by saying to me “there’s no point… I think we’re at little past now that don’t you? I’m getting fucked by you fags either way.” Jason raised his eyebrows and curved his lip as if to say “he’s right it won’t make a difference.”

Joe continued “besides if it did make a difference. I will never apologise!”

Well I’ve got to hand it to Joe, he’s just given me the confirmation that this is just a huge waste of time, I shrug my shoulders and reply “fine… guess you’ll just get what’s coming to you then” I turned to walk away when Joe calls out.

“Hey! Come on Ben don’t go acting like you’re one of them! I know you’re not like them, you’re better!”

I stop and turn back to him, intrigued to hear what he has to say. Joe continues “I understand you Ben, I really do. I know what you want, you just want to be accepted. You went all hard on me with the drill and smacking my arse because those fags loved it! That made you feel accepted and that you were one of them but you don’t need their love. I meant what I said earlier about all the money I have, I could give you so much money, you’d be able to spend it however you please. You could have your own business, a big house, a nice sports car oh people will love you! Best part is, you don’t have to make anybody suffer to get it, more people will love you more for it!”

I shook my head “we’re punishing you Joe, there’s a difference!”

“You’re raping me” Joe answered.

Rape… that was a word I did not want to use but this is exactly that. Joe is trying to make me feel guilt and remorse but I can’t show that to him so I say “if the punishment fits… you’ve had opportunities to get yourself out of this situation Joe but you’re too stubborn to do that, so where do we draw the line about the rape part here?” I say sarcastically, Jason grins.

“Well that’s exactly what I’m trying to do now” Joe says and he turned to Jason and says “everything I’ve just said to Ben, that applies to you too. If you both let me out of here, I will give you so much money. Ben is just looking for acceptance and you were just following orders.”

Jason does not like this response from Joe. He plants his foot onto Joe’s cock and balls instead.

“AHHH! AHHH! OHHH! NO HEAR ME OUT PLEASE! AHHH! I’M SORRY!” Joe pleads in place. Jason stops and places his foot back onto Joe’s chest instead.

“Okay I get it wrong choice of words!” Joe says “but the point still stands though, I know you wanted to go for lunch with the others but they just told you to stay here and watch over me instead. Brad was right though, I’m naked and all tied up, I won’t get far will I? They’re just using you, ordering you about, the only difference is you get to have a choice as to whether you get to keep your clothes or not! You want to help yourself? Take my offer and you can have all the money you want for people to follow your orders instead. I may not agree with homosexuality but hey! If you want to like start your own gay gang or something where you’re the leader instead then go for it!”

Okay so Joe is happy to let somebody else get raped instead if it means that he will be spared, this guy has no consideration for anybody other than himself. “Don’t listen to him Jason don’t let him get into your head, he’s manipulating you he won’t give you a penny! You saw the way he tricked his own dad earlier” I say.

Joe shakes his head “my dad… the one who cut off my underwear and fed me to you all. Of course I tricked him! You two are not like him though! Ben you’re better than him, you like to do the right thing and that’s why you’re talking to me now, you’re trying to help him. He’s not worthy of your help, you see what he does to his son! And Jason, you’ve been given this story about how much of a bad guy I am so that stripping me naked and humiliating me would be a fitting way to bring me down, I don’t take it personally as that’s just what they wanted you to do. Please undo my cuffs and get these belts off me and help me escape. You can stick with me until you know I’m not going to try anything, I’ll leave you out of this I promise. You’re a big strapping guy I know it’d be stupid of me to try anything with you, I’ll make sure you’re well rewarded for it” Joe pleads.

“He’s lying!” I yell. “I don’t believe in money Joe, I believe in justice! You’re getting this punishment because it’s exactly what you deserve for all the pain and misery you’ve caused everyone! Take your money and shove it up your newly stretched naked arsehole!”

“Your loss Ben!” Joe shouts. “Offer still stands for Jason though, do the right thing Jason I know you will and as for you Ben… I was wrong about you, you’re just as scum as the rest of them! I was right about one thing though… your need for acceptance, all these people love you and you’re loving every second of it. You know something else? I think that’s why you’re so attached to my dad too, my dad is practically your daddy isn’t he? I know what this Ben… your own dad isn’t around anymore is he?” Joe laughed.

He’s just done it, he’s crossed the line. Rage builds up inside of me. I walk over to the one of the gay gang’s bags and pull a flogger out of it. I nudge Jason off Joe and I begin to flog Joe hard.

“AHHH!!! AHHH!! FUCK!!! AHHHHH!!!” Joe yelled in pain with each flog that connected with him. He was moving around frantically on the floor and his body grew redder and redder with each blow that I landed on him.

Not yet feeling satisfied, I pull up a chair near where Joe was laid down and I pull him up onto my knees, bent him over and proceeded to flog his arse.

“AHHHH!!! OWWW!!!” AHHHH!!!!” Joe yelled.

Jason went over to me and took the flogger off my hand “hey hey Ben it’s okay it’s okay… come on mate he’s not worth it” I pushed Joe onto the floor and Jason placed his foot back onto Joe’s chest and he wrapped his arms around me.

I hug Jason back and tell him “you’re right Jason, I shouldn’t have let him get under my skin like that, I let him win for a brief moment there but I won’t be doing that again.”

Joe was laid on the floor laughing “oooo hit a nerve there did I Ben?”

“Ben’s right, you can stuff that pathetic offer of yours boy and take what’s coming to you!” Jason told him.

I was relieved to hear that me and Jason were on the same page “you know what Joe, if your mum was still alive she would be absolutely ashamed of you” I replied.

Joe continued to laugh “like I care, she was just as pathetic as my dad was, let the bitch rot!”

I shook my head and said “I’m going to go and have lunch with the others, I’ll see you later Jason” before I left I walked over to Joe, pulled out my 8 inch dick and said “I hope you’re ready to take this in the arse Joe.”

Joe stopped laughing and looked a bit scared. I leave the room smiling, keeping that image of his face in my head. Jason bid me farewell as I left the room and I went to join the others in the kitchen area where everyone was seated around a long wooden table having their meal.

“Ah there are you Ben, come and sit down my friend, we’ve saved a seat just for you” Nick smiles at me gesturing to an empty chair.

“Thanks Nick” I smile back at him and take a seat.

“Is everything okay?” He asks me.

I then tell them all about what has just happened, Joe trying to strike a deal with me and Jason, the way he got under my skin and what I did to him. Nick hugged me and said “oh Ben I’m so sorry that he said all that to you and for him to talk about his mother like that, she absolutely loved him to bits I can’t believe he would say such a nasty thing about her. It’s okay Ben he will learn his lesson!” I’m not sure if Nick is trying to convince me or himself there.

“That’s right, we’re going to be absolutely brutal with him!” Terry says “good on Jason for not getting tempted by the offer too, he’s always been so loyal that man! We are so proud of him!”

Once we’d eaten, we had a good chat with each other and talked about how we were going to go about fucking Joe. Each person was debating whether they preferred to be sucked or to fuck his arse or a bit of both!

“Mouth… after anal” Scott beamed.

We laughed and Jordan then spoke up and said “we best save poor Jason from him, I’ll go and relieve him of his duty and I’ll keep a watch on Joe” and with that, Jordan left the kitchen.

A few moments later, Jordan sprinted back into the kitchen, he was holding a pair of handcuffs and 2 belts. We are all left feeling confused.

“Jordan what’s happened? Don’t tell me…” I had a bad feeling.

“Joe’s escaped… Jason too!” Jordan was incredibly anxious.

So Jason struck a deal with the devil after all then, this was an absolute shambles.

Terry slammed his hand on the table and said “let’s find them and make them suffer… both of them!”

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