Like Father, Like Son

The following story contains content that may not be suitable for all readers, including, but not limited to, drug use, physical restraint, non-consensual sex, or emotionally damaging behavior. This story is fictional and does not portray real events or real persons. Reader discretion is advised. Also, never mix poppers with Viagra. All characters are 18 years or older.

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Mr. Jackman

As I dragged my exhausted ass into the house and closed the door, I breathed out a heavy sigh of relief. While it had been an incredible evening at Hugo’s, I desperately needed a shower and a good night’s sleep. I had lost track of how many men had used me at the gang bang, but I knew it had been a very large number. There were only supposed to have been 7-8 guys at the party, but it felt like there had been three times that amount. With the last-minute addition of the neoprene hood and earplugs, I had no idea who had fucked me, and I wasn’t looking forward to going into work on Monday morning and trying to guess which of my employees had ridden my ass on the weekend. It might be easier guessing who hadn’t fucked me. While it had been exquisite torture being held horny and helpless on the bench while waiting impatiently for the next stroke, tease, and eventual fuck, I still needed to have a stern chat with Bruno and Hugo. The evening wasn’t at all what we had agreed to, and they had to know that they couldn’t do whatever they wanted without repercussions. Despite my submissive role in the arranged gang bang, I was still their boss.

That one complaint aside, it had been a lusty night that satisfied so many of my deep cravings. It had been a blur of one juicy cock after another pumping hot cum into my ass and mouth, and I know there had been at least one instance of double penetration. The inside of my ass felt tender and well-used, but who was I kidding? I couldn’t wait for the next fuck party. It seemed like the more outrageous these events became, the more I wanted. While Bruno and Hugo probably knew me better than I liked to admit, we still needed to talk. I also knew that at some point I would be asking them to set up another night where their boss’s ass was once again the main event. While my entire body ached and my hole was full of cum, I had loved being used and abused by my randy crew. I locked the front door and turned out the porch light as I headed down the hall to have a shower. 

As I passed by my son, Connor’s bedroom, I thought I heard a moan through his closed door. Pausing, I listened quietly until I heard more moaning. What was going on? I couldn’t tell if he was in pain or… having sex. Stepping carefully towards his room, I listened through the door. He was definitely moaning and calling out, “Stop… no… stop!” It sounded like he might be in pain. Was someone in there with him?!

Concerned, I knocked, but there was no answer. Unsure what to do, I listened as he groaned and grunted. As his groans settled into a steady rhythm and the volume increased, I recognized the sound of someone moaning in pleasure. In fact, I think I sounded similar when I was getting off. I was guessing Connor was either beating his meat or had someone in there with him. Either way, I decided to give my son some privacy. As I started to step away, I heard his bed creak and a loud moan before he said, “Fuck, Dad, fuck! I’m cumming!” What the hell? Had he said, “Dad”? Why would he say that?

Confused and unsure what to do, I called out, “Connor?” When there was no answer, I knocked on the door. I said, “Is everything okay?” Worried that I might be invading his privacy but concerned about his lack of response, I took a deep breath and quietly opened his bedroom door to discover my son lying naked on his back on the bed with the sheet tossed aside. In the light shining in from the hall, I could see that Connor had his eyes closed and his head tilted back as his body writhed on top of his bed. My eyes wandered down from what looked like a fresh load of cum on his heaving chest to his still twitching erection as it squirted a final thread of spunk across his flat stomach. Whoa! It looked like my son had just shot a big load. It was a lot to take in.

Finally sensing my presence, Connor’s eyes blinked open and I saw his face look confused and shocked as he spotted me in the doorway. Belatedly realizing how exposed he was, he quickly reached down and pulled the sheet up over his impressive hard-on, but the image remained seared on my brain. “Uh, hey Dad,” he said as he peered back at me guiltily. Did I just catch my son jerking off? If so, why hadn’t he answered me before?

Embarrassed, I said, “Um, hey son, sorry, is everything okay?” Connor had the sheet pulled tightly up to his neck, and I saw him trying to calm his breathing. He looked half asleep and unsure what to say.

“Uh, I’m good. I think I just had a weird dream. I may have drunk too much tonight.”

So he had been dreaming. Damn, this was awkward. “Oh, okay. I just got in, and it sounded like you were yelling and in pain… or something. Uh, sorry to disturb you.” I couldn’t believe I had barged in on my son in the final throes of a wet dream. I needed to get out of here. “If you’re okay, I’ll let you get back to sleep; I should get some rest myself. See you in the morning, son.”

“Night, Dad, and thanks for… checking in on me.”

Closing the door, flustered by what I had seen, I realized my own dick was rock hard. I didn’t think I had another erection left in me after tonight’s marathon gang bang, and also, why was seeing my son with a hard-on and a generous load sprayed across his torso making me horny? Also, what had he said in his sleep? It sure sounded like, “Fuck, Dad, fuck. I’m cumming!” in the seconds before I opened his door to find his shockingly large cock drooling cum on his tight stomach. 

While I had glimpsed Connor’s hard cock once before via a covert FaceTime session in a stalled construction elevator at work while a couple of my employees had their way with him, I had never seen him so aroused and exposed before. I knew that he liked men and liked to bottom from the incident in the elevator, so it wasn’t too much of a stretch to assume he had been dreaming about getting pounded, but to actually cum in his sleep from it - that was on another level. I thought only kids had wet dreams, and Connor was definitely all man from what I had just witnessed.

Also, I still couldn’t get over him saying what sounded like ”Dad” in his sleep. Maybe he had said “Brad” or “Chad” or something similar. Connor hadn’t yet come out to me as gay or bi, so it was possible he had a boyfriend with a name like Chad that I wasn’t aware of. That had to be it; why else would Connor shout out “Dad” while getting off? I felt my cock throb inexplicably as I pondered the implications of what I had just heard and seen.

My son and I had always been pretty casual about nudity and often just walked around in our underwear, so I knew his body well, and I was proud of the fit young man he had become. That said, I had to admit I couldn’t stop thinking about the size of his erect penis after seeing him in his full glory tonight. He was huge, and while I’m no slouch in the dick department, he had to have another inch or two on his old man, and he was thick. Bloody hell. Well, good for him I guess but it somehow seemed unfair to have a son with a bigger cock than you. 

As Bruno and Leo could attest, I was a connoisseur of big dicks, and son or no son, Connor had the goods from the glance I had caught of it in the light from the open doorway. He must be popular with the boys, or the girls, or both. Still, that didn’t adequately explain my hard-on. Connor was my son, not some go-go dancer I was drooling over at the bar. It must be the lingering effects of the Viagra that Leo had convinced me to take earlier in the evening before tying me up to the bench. That was an easier-to-accept explanation than me getting off on listening to my son bust a nut behind his bedroom door and catching him with a fresh load sprayed across his chest while his enormous cock flopped around on his abs.

I hobbled down the hall to the en suite in my bedroom to shower with my hard cock trapped upright in my jeans. I was so swollen, the thick head of my dick was sticking up above my waistband and oozing pre-cum into the fabric of my t-shirt. I entered the bathroom, stripping off my clothes and releasing my throbbing tool from its confines. As I stood naked in front of the mirror, I was pleased by what I saw. For an old guy, I was still in decent shape with a defined hairy chest, thick biceps, muscular thighs and ass, and a decent-sized cock.

As I turned in the mirror with my hard-on protruding outwards, I noticed some black ink showing on the side of my ass cheek and recalled feeling the tip of a pen on my butt after each hard fuck. Did the guys keep a tally of how many fucks they threw into me? Turning more so I could see what was on my ass, I was shocked to see my cheek was covered in names. The guys had actually signed my ass one by one after shooting their loads. I was shocked by how many names there were as I turned to the other side and found just as many names on the other cheek, along with “Cum Dump!” crudely written across my lower back above my crack. There had to be more than 30 names scribbled on my butt! Struggling to read the names in reverse in the mirror, I made out Bruno, Leo, Zeke, Danny, Bear, Jason… wait, what? I didn’t know any Jason other than Connor’s friend. Feeling my heart sink with unease, I kept straining to read the rest of the names, hoping there would be no additional surprises… Ryker, Gage, Bear, Biagio… Connor. No! It couldn’t be!

With a sinking feeling, I considered whether Connor and Jason had been at Hugo’s last night?! Oh my god! While I had been tied to the bench at Hugo’s with my ass spread and my hard cock drooling pre-cum, my son and his friend might have been hanging out with my crew? I felt my world spinning as I tried to make sense of this revelation. If it was true, I wondered how long they had been there and what they had seen. A horrible thought crossed my mind as I considered the full implications of my son and his friend partying at Hugo’s. Had either of them fucked me?!

Thinking back to my glimpse of Connor’s cock in his room, I shivered imagining that giant shaft plowing into my tight hole. That disturbing mental picture was followed by an image of Connor’s twinky friend Jason mounting me from the rear and riding my ass. I couldn’t believe Bruno and Hugo would stoop so low as to set me up like that. Based on past incidents, they were capable of a lot including practically raping my son, willing or not, in the elevator at work, but this was a step too far. If Connor and Jason had fucked me, my next question was, had they known it was me under the hood? This was all so fucking twisted. I tried to think back over the evening and the blur of cocks I had felt thrusting into my hole and wondered which one could have been Connor’s. Based on the size of the thing, it must have been memorable if it had happened. I couldn’t get the unsettling image of my son gripping me by the hips and fucking his dad while my crew stood around cheering him on out of my mind. 

Damn, if he had fucked me, I would have probably been moaning and pushing back against his cock like a whore, not realizing it was my well-hung son. Despite the late hour, I was tempted to call Bruno and demand some answers, but regardless of my horror at the situation, I was exhausted and not thinking clearly. I needed a hot shower before I did anything else, and maybe there was a logical explanation that did not involve my son and his friend pounding my ass. I prayed that was the case. As I turned on the water in the shower, I paused and held my phone’s camera up behind me and took a picture of both cheeks of my ass. I needed to take a closer look at what was written there in the morning.

For now, I stepped into the shower and let the warm water wash over me as I soaped off layers of oil, spunk, sweat, and… ink. The water felt great on my aching muscles as I worked the soap into my skin. Lathering up my cock and balls, I was dismayed to find myself hard and needy. As I lathered up with more soap and stroked my rigid shaft with my slippery palm, I thought back over the evening at Hugo’s. 

After what had felt like hours of teasing and ass eating from my crew, I remembered finally feeling the head of a big dick breaching my hungry ass before whoever was on the end of it rode me like a bitch. Fuck, after so much teasing, having someone finally rail me and completely fill my hole while slamming his balls against mine was a rush. With the extra doses of Viagra, the constant poppers, and the relentless pounding on my prostate, I wasn’t surprised that I came hands-free as I felt the mystery dick pump a thick load deep inside my channel. When I did speak to Bruno and Hugo, I needed to ask them who that was as I wouldn’t mind a repeat.

I also wondered if there had been any video taken as I considered whether Connor had pounded my hole with his dick or if his twinky friend had plowed his school buddy’s dad. While Jason was a small guy, I had noticed a healthy bulge in the snug corduroys he liked to wear and I wouldn’t be surprised if the little guy was packing. As I stroked my cock and pulled on my balls, it didn’t take long before I was blasting another load against the glass walls of the shower as my imagination went in unwanted directions. Damn, what was wrong with me? Disgusted with myself, I rinsed off the stall and stepped out of the shower to dry off before walking back into my room and sliding under the covers in my bed. I was furious with Bruno and Hugo and planned to have a serious chat with them both on Monday morning. They had a lot to answer for. Too exhausted to consider the implications of the evening further, I closed my eyes and promptly fell asleep, not waking again until the sun was high in the sky.

Jason

Approaching Connor’s house, I thought back over the previous evening and the hot daddy that had been tied to the bench in Hugo’s basement. He had seemed familiar, but it wasn’t until I spotted Mr. Jackman’s truck parked behind Hugo’s house when I was grabbing a smoke, I started to consider that it might be Mr. Jackman himself under the hood. It made sense in that it was his crew at the party, and he had a similar body type. 

While he had always been polite and friendly towards me, I have always secretly had the hots for Mr. Jackman. I was shocked to think that my friend’s handsome dad might have been tied to the bench with his giant ass cheeks spread and his swollen cock leaking pre-cum onto the floor while his crew pumped load after load into his desperate hole. I had even taken my turn fucking him after Bruno and Biagio had spectacularly double penetrated the poor man. Despite the combined breadth of their thick shafts and their generous loads, it had still felt amazing as I slid my shaft deep into his slippery hole with Bruno guiding my hips before easing his own thick shaft between my cheeks and fucking me from behind. I loved being sandwiched between the two big men as Bruno thrust deep into me, driving my own cock deep into Mr. Jackman’s greedy ass until I had emptied my load. I could feel my dick chubbing up as I thought back over the evening. I couldn’t believe I had fucked Connor’s dad, my dream DILF.

That said, what really blew my mind was that his son, Connor, had been the first to fuck Mr. Jackman after winning a door prize, and damn, had he fucked him! Mr. Jackman had been teased and stroked for so long by his men that he had reacted like a bitch in heat to Connor railing him with his big cock. I’m sure the extra doses of Viagra that Biagio had mentioned they gave him kept him horny and wanting more as well. I couldn’t believe Connor had screwed his own father in front of his employees, and what was really crazy was I don’t think either of them realized it. 

Bruno and Hugo obviously knew what was going on, and the fact that Connor won the door prize for first fuck of the night seemed highly suspicious to me. All the same, I had enjoyed pounding Mr. Jackman’s firm ass and would do so again in a heartbeat. While Connor’s dad was my dream DILF, Bruno was my all-around dream man, and I was so into his muscular frame and big dick, along with his mischievous edge, which in part explained his setting up Connor and Mr. Jackman. I would have to talk to him more about what actually went down last night.

For now I just wanted to check in to see how Connor was doing. I was hoping he hadn’t figured out what had actually happened at Hugo’s, but as an outsider in the know, I was getting off on the scene of my fit friend pounding the fuck out of his bottom-loving hunky father in front of his team. Knocking on the front door, I was unprepared to see Mr. Jackman himself open the door so soon after my mental recollection of fucking his sweet ass. I should have realized that he might be here; it was his house after all. Also, he was only wearing snug boxers, and he looked fucking adorable! “Um, hey Mr. Jackman. Is… Connor here?”

Mr. Jackman seemed equally caught off guard as he looked back at me in surprise before replying, “Oh hey, Jason. Connor never mentioned you were coming over. Sorry about my appearance. C’mon in. He’s doing laundry. I’m just making breakfast if you haven’t eaten yet. There’s more than enough for three.”

“Breakfast would be great. Thanks, Mr. J.”

I tried surreptitiously to check out the unshaven Mr. Jackman in his worn shorts as he held the door open for me. He was definitely the guy from last night. I should have recognized his furry, muscular legs and bulging arms instantly, along with his spectacular ass. In fact, I think I was still able to see faint rope marks on his arms and legs. I had fucked Mr. fucking stud-muffin Jackman and filled his hole with one of many loads of cum before writing my name on his ass like a brand. The contrast between the man I knew as Connor’s dad and the submissive, horny stud I had fucked last night was making me hard. I had to look away before I embarrassed myself.

Pointing towards the garage, he said, “Connor is just down the hall. Can you let him know breakfast will be in about 10 minutes?”

“Sure thing. Thanks, Mr. Jackman.” I walked down to the laundry room beside the garage entrance and spotted Connor folding sheets. “Hey dude.”

“Hey man! I didn’t hear you arrive.”\

“Yeah, your dad just let me in. He says breakfast is ready in about 10 minutes, by the way.”

“Okay, cool. I’m almost finished with laundry so we can study right after breakfast.”

“Awesome. Uh, so how are you feeling today?”

“Oh, fuck, man, what a crazy night! I’m good, although I’m a little hungover and tired. I don’t think I slept that well. I had some seriously bizarre dreams, including a wet dream, if you can believe it.”

“Dude, you had a wet dream? No way! I wouldn’t think you’d be thinking about sex at all after everything that happened last night with Biagio and Bruno at Hugo’s. What were you dreaming about?”

“Well… it’s kind of embarrassing, but remember what I said about wanting to try out being tied to a sling someday?”

“Yeah…”

“Well, I’m not sure where I was, but I was tied to a leather sling, and when I looked down, I was naked, and Biagio was fucking me. I was loving the feel of his big dick when Leo, the Black guy from my dad’s worksite, held up some poppers to my nose. I realized at that point that the rest of my dad’s crew was standing around us, and everyone was naked and hard.”

“Fuck, that sounds amazing. Biagio is almost as hot as Bruno,” quipped Jason. “What happened next?”

“Well, here’s where it gets weird. I’m not even sure if I should tell you. You can’t say anything to anyone, okay?”

“I won’t. Scout’s honor. C’mon, keep going...”

“Okay… everyone was encouraging Biagio to fuck me while he gripped the sling and pounded me with that big Italian cock of his. It was so fucking hot. Although no one was touching my dick, I was getting close to cumming when I thought I heard my dad coming home. It didn’t make any sense because I was in some strange room in a sling, but I still somehow knew that my dad had pulled up in the driveway in his truck. I was panicking, worried that he would find me like this, so I frantically asked Bruno to untie me, but suddenly it wasn’t Bruno anymore! Uh, he was, um… You know, forget it. I can’t tell you this. It’s just too fucking weird.”

“Connor! You can’t leave me hanging like this! C’mon, tell me! Besides, it’s just a dream; it doesn’t mean anything. Who was it?”

I watched as Connor took a deep breath, working up the courage to finish his story. Where was he going with this? Finally he continued, “Okay. Um, instead of Biagio, there was a guy wearing a black leather military cap, arm and wrist bands, chaps, and a harness that extended down to his cock and balls, forming a cock ring. He was your typical gay leather daddy, and he had somehow replaced Biagio, and he was riding my ass in the sling with a vengeance.”

“Oh, wow. That sounds hot; I think I’m jealous. So what’s the big deal?”

“You don’t understand. It wasn’t just a leather daddy; it was my actual dad dressed in leather. He had somehow switched out with Biagio and was fucking me in the sling.”

I gasped in shock. Connor had dreamt about his dad fucking him on the same night that he had fucked his dad. Maybe he did know that was his dad tied to the bench. “Oh… oh wow. Okay, that is a bit weird. Um, why do you think you were dreaming about your dad like that?”

“I don’t know, man, it’s freaking me out. It was so weird and so… wrong. I don’t think about my dad that way; that’s disgusting. Also, he wasn’t even acting like my dad, it was like he was pissed off and trying to teach me a lesson. He said something about me asking for it. The really weird thing was that it was so intense, I couldn’t ignore his cock banging into my prostate and pounding my hole. Shortly after that, I shot a load in my sleep and woke up gasping with my chest covered in cum.”

“Holy shit. Wow, just wow. I don’t know what to say, Connor.” Still curious about whether he knew anything about Hugo’s, I prodded further by asking, “Do you think it has anything to do with last night?”

“What do you mean? Because we were hanging out at Hugo’s with my dad’s employees?”

“Uh, yeah…” I was relieved that Connor seemed oblivious to having fucked his father at Hugo’s.

“I guess so. It just seems so fucked up. I’m kind of embarrassed, especially after my dad...”

“After your dad… what?”

After pausing for a moment, Connor continued, “Well, I guess I did hear my dad come home in my sleep while I was dreaming because just after I came, I opened my eyes, and my actual dad was standing in the doorway of my bedroom. I guess he had heard me moaning or talking in my sleep and was worried and opened the door. I was literally covered in spunk with my dick hard, having just shot a load. It was so embarrassing.”

“Oh jeesh, that sucks, man. What did you do? Did he say anything?”

“I covered up as fast as I could, but I’m pretty sure he saw everything. He pretended not to, but there’s no way he didn’t. I just hope I wasn’t talking in my sleep.”

“Damn, that is awkward. Maybe it was too dark to see much. Don’t sweat it, man. Also, do you remember that psychology course we took last semester where they talked about dreams? They said you have no control over what you dream about, and it’s just your brain’s way of doing some mental housekeeping. It’s not something you need to worry about. I’d be more concerned about the wet dream part. I mean, dude, you might have to start wearing diapers to bed if you’re going to jizz your sheets every night.”

Connor reached out and playfully punched me in the shoulder. “Fuck you, asshole. They don’t make diapers big enough for what I’m packing.” While I laughed at his comment, he had a point after what I had witnessed at Hugo’s. My friend was seriously hung. At that moment, Mr. Jackman called from the kitchen, letting us know breakfast was ready. We put our conversation aside and joined Connor’s dad for breakfast, less than 24 hours after we had both had him. Connor had literally fucked a load out of the poor man. While Connor still seemed unaware that he had screwed his dad, it was interesting that he had dreamed about his father fucking him. Freud definitely would have something to say about that; in fact, I remembered reading about an inverted Oedipus complex in last year’s course. Connor must have slept through that lesson. I wondered if Mr. Jackman had any idea that we were at Hugo’s last night. If he did, he gave no sign of it as I discreetly ogled his ass and reconciled this polite, respectable man with the “cum dump” from Hugo’s as he moved around the kitchen in his sexy shorts, although sadly, he had put a t-shirt on. I still couldn’t believe I had fucked Mr. J and wondered if I would ever get another chance to ride this stud.

Bruno

“Please tell me you didn’t bring Connor and Jason to Hugo’s on Saturday night.” Hugo and I were standing in the boss’s office. He had asked us to come in early, and he looked pissed as hell as he addressed us.

“Um, well, yeah, actually they were there for a bit…” I admitted.

“Really? I was hoping you wouldn’t say that.” The boss looked disappointed and angry as he continued, “I can’t believe you brought Connor and Jason to Hugo’s. I mean seriously, what the fuck were you guys thinking? Why would you bring them there?! You knew I was going to be tied up in the basement.”

“It wasn’t planned, boss. Biagio ran into Connor and Jason downtown and invited them without asking me.”

“Yeah, and you could have fucking well uninvited them, or you could have gone somewhere else, or you could have just told them they couldn’t come. I can’t believe you brought them.”

“I thought it would be harmless, and besides, I made sure they wouldn’t recognize you. That’s why I had Hugo put the hood on you.” 

The boss responded sarcastically, “Well, that was real considerate of you…” Taking a deep breath, he asked, “Did either of them fuck me?” When neither of us responded, he impatiently asked again, “Well… did they?!”

“Uh… maybe?”

“What do you mean maybe? Did either of them fuck me? It’s a pretty simple question.” The boss was practically yelling at us.

“Well, yeah, both of them might have, but it’s okay… You had the hood on.”

“What do you mean it’s okay? You drugged me, tied me to a bench in Hugo’s basement, and then brought my son and friend over so they could fuck me along with whoever else you invited over, and you think it’s okay because I was wearing a stupid hood! I can’t believe you guys did this. I was already angry with you about how many extra guys were there, but this is unforgivable.”

“Okay, I can see why you’re pissed. I thought it would be a lark, but I realize we went too far even if…” I bit my tongue, realizing now may not be the time to share my next thought, but it was too late.

“Even if what?!”

Oh boy, here it goes. Why couldn’t I keep my big mouth shut “Well, even if you both seemed to enjoy yourselves.” I could tell by the boss’s expression that he wasn’t happy with my answer, despite it being the truth. I couldn’t remember ever seeing him this angry.

“That is not funny. I’m almost afraid to ask, but do they know it was me?”

“Connor doesn’t. Uh, I think Jason figured it out, but he won’t say anything.”

“You mean if he hasn’t already!”

“No, he hasn’t. I was talking to him yesterday, and Connor doesn’t know, and he promised me that he wouldn’t say anything. Trust me, Jason will keep it to himself.”

The boss stared at both of us for a long time before saying, “I don’t know if I can ever trust either of you again. I’ll have to live with the knowledge that my son fucked me in front of my crew, but… if we can make sure he never finds out, I can try to put this behind us.” I glanced at Hugo, who hadn’t said much and appeared shaken by the boss’s lecture. I caught his eye and winked at him before turning back to the boss. Part of me did feel bad about bringing Connor to Hugo’s, but I sensed the boss wasn’t as upset as he was letting on. I was about to take a chance and find out.

“Okay, deal. We’ll make sure Jason never tells Connor that the guy he fucked after winning first fuck of the night was his dad.” The boss gasped when I intentionally revealed Connor’s placement at the beginning of a long line of dicks throughout the evening. I could see his mind working behind his shocked expression as he recalled the thick head of Connor’s cock breaching his oiled hole, stretching him wide as he slid in to the hilt. The boss had reacted like a man-whore, thrusting his big ass back against Connor. I knew he was replaying that first spectacular fuck in his mind as I continued without mercy, “I gotta say boss, I don’t think I’ve ever seen you take a fuck so well. You were grunting and meeting each of his powerful thrusts with that big muscular ass of yours like the greedy little bitch we all know you are. I don’t think any of us were surprised when you blasted your load without anyone touching your cock.”

The boss was shaking his head in denial and outrage, although he had to be thinking about the truth behind my words as he recalled his desperate reaction to that first fuck of the night while hopped up on Viagra and poppers. “No… you’re lying. That couldn’t have been Connor; you’re just trying to freak me out.”

“Oh, I think you know it was him. He won the door prize and was eager to get his dick wet. You’ve seen him in action in the elevator at work, and you know the boy is hung. Admit it, you were loving his cock like the true size queen you are, even if you didn’t know it was Connor at the time. Besides, Zeke caught it all on video, so you don’t need to take our word for it.”

“You bastard. I can’t believe you did this. I am so angry right now…”

“Bullshit.”

The boss looked at me stunned. “What…?”

“You heard me, I said bullshit. Sure you’re mad at us for setting you up, but I think you’re also getting off on knowing Connor, and Jason fucked you with their big cocks. You weren’t given a choice with the way it played out, but that doesn’t stop you from getting all wet about it. You may not want to admit it, but you love the idea of Connor’s thick cock plowing your tight hole and pumping you full of hot cum, and I bet you can’t wait to see the video.”

“How dare you! That is not fucking true…”

Ignoring my boss’s protests, I stepped forward and roughly grabbed him by his crotch. He gasped as I groped his hard cock through his khakis. “I knew it. You’re as hard as rock, you little fucker. You may be in denial, but your dick isn’t. You haven’t stopped thinking about this since you discovered Connor and Jason’s names written on your ass. I bet you’ve even jerked off to it a few times trying to replay it in your mind before you called us in to yell at.”

The boss definitely looked sheepish as he tried to protest, “No! I’m not, I just…”

Before he could finish his sentence, I unbuttoned the top of his fly and yanked his zipper down, roughly hauling out his hard cock and heavy balls from inside the jockstrap he liked to wear. “Check this out, Hugo! The boss has a boner over getting boned by his son and his little friend. It’s not even a semi; look how fucking hard he is. He’s dripping pre-cum!” I said as I slapped his hard dick. While his cock lumbered back and forth, the boss whimpered in embarrassment, unsure how to respond with the hard evidence in front of us. Before he could stuff his prick back into his pants, I spit in my hand and wrapped my slick palm around his cock, milking his traitorous organ. The boss closed his eyes and groaned before he could catch himself as he rode my fist. 

“Look at you, you can’t stop thinking of how great it felt to have Connor’s big cock pounding your needy hole after the boys teased you for hours. You probably haven’t stopped thinking about his dick and ass since you saw Hugo blowing him while I fucked him in the elevator at work. Trust me, Connor has a hot ass. Like father, like son! I bet you’d even like a go at his tight butt. I guess that would be fair given he fucked a load out of you last weekend.” There was no denying that the boss was horned up by what had happened last weekend and on the construction elevator at work. His cock had betrayed him, and he wasn’t even attempting to stop the handjob I was giving him while I painted a picture of him fucking his son as payback.  

“You’re so fucking horny right now, Hugo and I could throw you over the end of your couch and spit-roast you, and you’d love it!” He moaned again, and I knew it was true. Despite the time of day, with the bulk of the morning shift about to arrive, we could do whatever we wanted to the boss, as long as we got him off. Who was he kidding to act like he was in charge?

As I teased and edged his rock-hard cock, I said, “I think you’d love to see the video of Connor destroying your ass with that fucking giant tool of his, wouldn’t you? We all know what a sucker you are for a big, hard dick.” As the boss closed his eyes and thrust into my hand whimpering, I added, “Are you even sure he’s your kid? He’s gotta have at least 2 inches on you, and he’s thick as hell. Regardless, both of you seemed to be having the fuck of your life when he destroyed your ass last weekend.” As he whimpered, I teased the head of his cock with spit and pre-cum. “Here’s what we’re going to do… First of all, you can quit pretending that you’re outraged and come over to my place next weekend. If you’re a good boy, we’ll show you the video of Connor pounding a load out of you with his club dick before we strap you into the sling and take turns fucking your needy hole. Would you like that?”

I was roughly gripping his meaty dick and working his tool while describing next Saturday for him. I knew he was addicted to hanging out with the boys on the weekend. I could also tell that he was desperate to see the recording of Connor fucking him. The fact that he came without touching himself when Connor fucked him said it all. I would keep my promise to make sure Jason didn’t tell Connor about fucking his dad, but I wouldn’t do much more than that. 

When the boss didn’t respond to my question, I added more spit to my fist and repeated my question as I roughly jerked him off in his office in front of Hugo, “I didn’t hear you! Did you want to come over on Saturday and watch yourself get fucked hard by Connor on the big screen with the boys before we fuck you in my sling? If I don’t hear a yes in the next few seconds, I may rescind the offer and erase the video, so think carefully.”

As I slickly worked his swollen cock, the boss tilted his head back and groaned loudly as his dick began to pump thick cum onto my wrist and onto the floor as he came. “Yes, yes, I’ll come over...” 

This had gone better than I had imagined. Hugo had been worried about this conversation, but I knew the boss better than he did. “That’s the spirit. You’re not going to believe how hot the video is, and the boys are eager to have another go at your ass. Now stop worrying about Connor; it will be fine. I’ll get everything set up. All you need to do is show up at my place at 10:00 and follow instructions. Come to the backdoor, and don’t be late!” As I released the boss’s cock and wiped my cum-coated hands on his pants, I said, “Now, clean yourself up. You’re at work for fuck’s sake.” I called out to Hugo, and we left his office.

We closed the door behind us just as an elevator of men arrived for their shift. Hugo said to me, “Holy shit, Bruno, you’re fucking unreal.”

“Yeah, yeah. I told you not to worry. The boss is a nice guy, but he thinks with his dick too much, and we can always take advantage of that.”

“What are you going to do on Saturday? Are you going to keep your promise?” 

“Hugo, I’m shocked you would even ask that! Of course I will keep my promise, but there’s a world of opportunities around that one promise. This is going to be fucking wild, but first, I need to talk to Jason.”

Jason

I saw Bruno’s truck pull up at the curb outside of school. He had called me earlier asking if we could meet. Always happy to spend time with the big sexy stud, I readily agreed. Walking up to the truck cab, I opened the door and jumped in as he smiled and turned towards me, “Hey there, little man.”

“Hey Bruno. Good to see you.” Bruno leaned over and gave me a big, sloppy kiss. He was never the shy one, and I loved it. 

“Thanks for meeting me. I need to get back to work, but I wanted to talk to you about last weekend and this coming weekend.”

“Sure, shoot. Always happy to see you. I have another class in 30 minutes, but otherwise I’m free.”

“Cool. First things first, are you free this weekend? I’m thinking about having a party at my place.”

“By party, do you mean another sex night?”

“Uh, maybe?” he smirked at me under that big sexy mustache. I couldn’t get enough of Bruno, and he made me horny, so I was always happy to spend time with him.

“Then definitely count me in. Last weekend was so great.”

“I’m glad you enjoyed yourself. I wanted to talk to you about last weekend. You told me that Connor didn’t realize it was his dad tied to the bench, right?”

“Yeah, for sure. I didn’t even figure it out until I saw his truck, although I feel like an idiot for not realizing sooner. I’m certain Connor doesn’t know it was his dad. I asked him a few questions after he told me about his dream, and he’s clueless.”

Bruno raised his eyebrows, “Dream? What dream?”

Oh shit. “Er, um, nothing. I wasn’t supposed to say anything.”

Bruno smiled at me and reached over to place his hand on my lap as he rubbed my bulge through my corduroys and purred, “Jason… it’s okay. You can tell me. I promise you Connor wouldn’t mind.”

My cock was getting hard as Bruno stroked it through the fabric. As I looked around to see if anyone could see us, I realized he could ask me to do anything, and I would. I just couldn’t say no to the big hunk. Besides, in a strange way, I did trust him to do the right thing… eventually.

“Okay, but it’s a little crazy, especially after what Connor did to his dad at Hugo’s.” I proceeded to describe his dream about being tied to a sling and how it had switched from Biagio fucking him to his dad. I also told him about what his dad was wearing and how frenzied he was with fucking his son until Connor actually came in his sleep. I even mentioned the part about his dad catching him just after he came hard and covered in cum. Sorry, Connor.

“Wow, that is hot. Are you sure he doesn’t know about his dad being at Hugo’s? It seems odd to have a dream about his dad right after fucking him.”

“I know, maybe he knew at some subconscious level, but I basically asked him why he thought he had the dream, and he thought it might be because he was hanging out with his dad’s employees, that’s all. He hasn’t figured it out.”

Bruno grinned at me with that mischievous glint in his eye as he eased my zipper down and ran his thumb across the pre-cum-covered head of my cock. “This is perfect, thank you for telling me this, Jason. Bring Connor with you on the weekend, and we might be able to make his sling fantasy come true, if he’s still up for it.”

“That should be easy. Connor has already been asking me about the four of us getting back together, and I know he’s still considering the sling.”

“Perfect, I’ll get Biagio to give him a call as well. Why don’t you guys drop by around 9:00? I’ll coordinate with Biagio, and we’ll make sure you both have a great evening. Tell Connor we can hook him up in the sling with the boys, but that there’s no pressure. He can decide on Saturday if he wants to play or just watch. Either is fine.”

“Deal, I can’t wait.”

“Me too, Jason,” Bruno replied as he licked my pre-cum off his thumb. “Damn, you’re tasty. I’m looking forward to a bigger helping of this on the weekend, along with having another go at your sexy ass. Now, before you run off, tell me again, what exactly was Connor’s dad wearing in the dream?”

Connor

As Jason and I walked up to the front door of Bruno’s house, my heart fluttered in anticipation. It had been a full week since I had last seen Biagio at Hugo’s, and I couldn’t wait to see him again. We had messaged and chatted a few times, and he seemed as eager as I was to spend time together. He was also being very supportive of whatever my decision was about trying a sling tonight.

I hadn’t stopped thinking about it since the night I dreamed about Biagio fucking me in one. While that dream had ended disturbingly, it also resulted in one hell of an orgasm, a wet dream to be exact. I spent the following week imagining what it would be like to allow myself to be strapped into a sling at Bruno’s with men from my dad’s crew taking advantage of me. I knew they were a randy bunch that loved to play hard, and it made my dick ache just thinking about them having their way with me. 

Biagio had assured me that he would watch out for me if I decided to try out the sling, and I was thinking I was going to do it. I wanted to experience what the DILF had faced last weekend, being the center of attention and kept on the edge begging for a fuck until finally getting your hole destroyed, one dick after another. All I needed to do was say yes, and I would find out what it was like for myself… tonight. I felt my cock shifting impatiently in my jockstrap. This was going to be a night to remember.

Jason rang the doorbell, and Biagio opened the door wearing nothing but an open leather vest, leather shorts, and work boots. Fuck me. I grinned ear to ear as he smiled at me and pulled me in for a hug against his bare, muscular, hairy chest. My dick throbbed as I felt his bulge press back against me and remembered how he had fucked me with it last weekend. Whatever happened tonight, I wanted Biagio to fuck me, sling or no sling.

“Hey guys, you’re right on time.” We could hear the men laughing and talking in the basement. Biagio closed the door and hung up our jackets turning to me with a big grin, “So…?”

I looked back at the handsome stud, smiled, and said, “I’m going to do it.” 

Biagio immediately wrapped his big arms around me and lifted me in the air, spinning me around, “Yay! That’s fucking awesome. I’ll make sure you don’t regret it. We have everything ready in case you said yes. I can’t wait to tell the boys; they were all hoping you’d go for it.”

Unable to stop grinning, I said, “You made it an easy decision. Having you here takes away any unease I might have had.” 

“Cool. Did you and Jason want to mingle for a bit or get right down to it?”

“If we’re going to do it, let’s do it.”

“Awesome! I left something for you to wear in the guest room if you want to change. Jason can help you, and I’ll let the guys know you’re game and will come back up to get you when you’re ready. I can’t wait to see you all geared up.”

“Okay, great,” I leaned over and whispered in Biagio’s ear, “I’m already so fucking hard. I am so looking forward to this.”

“Me too, my little stud. Now go get changed. I’ll make sure everything is ready.”

Giving me a big wet kiss, Biagio bounded downstairs as we walked down the hall to Bruno’s guest room. I was curious about what he had put out for me to wear. As we opened the door, there were a bunch of items laid out on the bed. Stepping into the room, I spotted a black and blue leather chest harness, black armbands, a black and blue leather jockstrap with a removable pouch, bulky black and blue gym socks, black leather work boots, and a thick black rubber cock ring. My dick throbbed in anticipation of wearing this and walking downstairs to face my dad’s crew.

“Wow, you are going to look so amazing wearing this,” Jason commented.

“Thanks, man, I just hope everything fits. Can you give me a hand?”

With Jason’s help, I stripped down and started to gear up. Biagio had done his homework, and everything fit like a soft leather glove, although it was a challenge slipping my dick and balls through the triple rings of the rubber cock ring. Thankfully the rubber stretched, and I was able to get it in place. My dick looked red and angry with the snug ring holding it and my balls tightly. The other challenge was snapping the leather pouch of the jockstrap over my hard tool. Once in place, the pouch bulged obscenely with my cockhead poking out on the side. Good enough.

“How do I look?” I asked Jason. Thankfully he wasn’t shy about seeing me in my aroused glory. 

“Like a fucking stud. Biagio and the boys are going to lose their minds when they see you.” 

I heard a knock at the door and Biagio call out, “How’s it going in there?”

Opening the door, I said, “I think I’m ready.”

Biagio stepped into the room with a drink in his hand, looking astonished. “Holy shit! I’m not sure if I should take you downstairs or just toss you onto the bed and throw a fuck into you. You look hot as fuck, Connor!”

“Er, thanks,” I said, not sure how to react in front of Jason, “I like what you picked out for me.”

“You’d look amazing in anything, Connor,” Turning to Jason, he said, “Hey Jason, can you let Bruno know we’ll be down in two minutes and to make sure the sling is ready?”

“Sure thing. See you downstairs, Connor. Break a dick!” he quipped as he left the room, leaving us on our own.

Once we were alone, Biagio said, “Are you sure you’re ready for this, Connor? It’s not too late to back out.”

“No, I’m good. If you had any doubt, check out my dick.”

“Oh, trust me, I had noticed. Okay, that’s great. Let’s go over a couple things…” Holding up what looked like a rum and coke in his hand, he said, “Bruno made you a special drink similar to what we gave to Hugo’s friend last weekend. It will help keep you relaxed, horny, and ready to party. I know you don’t need it, but you saw how it worked on the guy in Hugo’s basement and how turned on you were on by it, but it’s your call…” Taking the glass from Biagio, I drank it back in one gulp. I wasn’t about to do this half-assed. Biagio smiled and said, “Good boy, you’re going to love how that shit makes you feel. Bruno is a great bartender… and pharmacist. I had a lighter version myself.”

Walking over to the dresser, he opened a drawer and grabbed a few more items. “This is a leather pup play hood. You’ve probably seen them around. There’s a gag you can wear under the hood as well, like we used last weekend.” I picked up the pup hood and was amazed at how well made it was and loved the black and blue leather combination that matched my jock and harness. I could picture myself wearing this with some anonymity while the guys had their way with me. “Also, this is a butt plug pup tail. You wear it where you think you’d wear it. As well as looking cute, it will make sure you’re nicely stretched and ready to take dick when the gang bang part starts. Lastly, this is a collar. I’ll walk you downstairs on a lead once you’re all suited up and take you over to the sling. What do you say?”

It felt like Bruno’s cocktail was already working its way into my system; I was feeling buzzed and horny as fuck. I was also feeling fearless and ready to face the boys. “I’m good with everything. Let’s do this.”

“That’s my boy; let’s get you suited up.” Biagio had me stand still while he placed the collar around my neck and positioned the gag in my mouth. Lastly, he pulled the pup play hood down over my head as he said, “See you soon, handsome.” I could still see, but I was unable to speak with the gag in place under the pup muzzle. “Oops, I almost forgot; let’s put your tail in place.” Biagio had me kneel on the bed while he lubed up the butt plug end of the tail and eased it into my hole. As I felt the butt plug pull itself into place, it sent a jolt directly to my dick. With a slap to the ass, Biagio said, “Done. Let’s take a look.” I stood in front of the mirror while he checked me over. The pup play gear mostly hid my identity, while the harness and arm bands emphasized my muscles. The bulge in my jockstrap with the cock ring and my hard-on looked so ridiculously large it looked fake, but it was all me. I was ready for my sling debut.

Jason

I knew my way to the basement from previous visits to Bruno’s, so I made my way down to the party room. I was chubbing in excitement for what lay ahead. While I didn’t know entirely what Bruno and Hugo had in store for Connor, I knew that his dad was arriving later on and that he would be part of it. I was feeling guilty about betraying my friend’s confidence about the dream he had about his dad, and I was second-guessing my role in the setup. Bruno had assured me that both Connor and his dad wanted something to happen, and his logic had seemed sound. Also, Connor had dreamed about his dad fucking him on the same night he had fucked his dad. That had to count for something! Bruno also told me that Mr. Jackson had watched Connor getting railed on the construction elevator at work via FaceTime and had really got off on it even after he realized it was his son. I hoped Bruno was right about all this.

Personal reservations aside, the horn-dog in me couldn’t wait to see what they had planned for Connor and his dad. I thought back to last weekend when Connor had aggressively fucked Mr. Jackson. Even if he hadn’t known it was his dad at the time, it still made me rock-hard thinking about my buddy fucking his dad and my favorite DILF. Bruno had hinted that there might be a flip-fuck tonight, and the possibility of Mr. Jackman fucking Connor made me want to cream my jeans. I knew it was twisted and wrong to even have these thoughts, but I couldn’t help it. As I entered the party room, I spotted Bruno adjusting one of two slings hanging from the ceiling near the center of the room. I wondered why there were two slings.

There were about two dozen men milling about the space, with drinks in hand and passing around the occasional joint. It was a similar crowd to Hugo’s last weekend with mostly men from Connor’s dad’s worksite. Many of the guys were shirtless or wearing next to nothing in jockstraps with a healthy mix of leather harnesses and accessories. It was a rougher BDSM vibe from last weekend, and I was loving the eye candy. I was almost jealous of Connor’s role tonight. Who was I kidding? I was jealous, but I knew Bruno would happily arrange something similar for me if I ever decided to take the plunge.

Similar to Hugo’s, the room was lit with red lighting, and there were also four big-screen TVs mounted on the walls near the slings showing explicit gay porn. The room already reeked of sex and poppers, and I spotted a few hard-ons and bulges amongst the schmoozing hairy studs.

As I said hi to a few of the guys and walked towards Bruno, he spotted me and smiled. “Jason, you made it. C’mere, you little stud,” as he grabbed me and pulled me in for a handsy hug and a sloppy kiss. “Fuck, I’ve missed you. I hope you’re ready for some action tonight. Papi needs some bussy.”

I felt my cock throb caught against Bruno’s hard muscular form as his bulge pressed against me. He was only wearing a chest harness, a worn jockstrap, and boots and looked hot as fuck. I was more than ready for anything he wanted to throw at me. Who knows, another night I might try being the center of attention, but tonight was Connor’s night. “I’m all yours, Bruno.”

Reaching down, Bruno wrapped his big hand around my straining bulge and said, “That’s my boy. Did you bring Connor?”

Pushing my hard-on into his hand and eager for more, I responded, “Yeah, he’s going to do it. He’s upstairs with Biagio getting ready. He should be downstairs in a few minutes. Uh, Bruno, are you sure we’re doing the right thing?”

“Trust me, Jason, Jackman wants this; he’s been walking around with a hard-on all week after finding out Connor fucked him at Hugo’s and catching his son with his big cock drooling cum in his bedroom. From what you told me about Connor, he has daddy dick on the brain as well. They’re both going to love what we have planned for them.” When I reluctantly nodded and smiled back at him, he reached down and unzipped my pants. “Did you wear what I asked?”

Happy to change the subject, I stripped off my pants and t-shirt. Underneath I was wearing a pair of assless black latex shorts that highlighted my bulge along with black suspenders. Reaching into my pants pocket, I pulled out a black domino mask that covered my eyes. I didn’t want my presence to clue in Mr. Jackman too soon. Bruno smiled and shook his head at my gear, “You look like Batman’s houseboy and good enough to eat, little man.” I should hope so! After running his hand across my chest and squeezing my swollen latex-covered bulge, he said, “You and I are going to spend some quality time together tonight after the main show. Don’t go anywhere.” As if. With that, Bruno turned to the men in the room and announced, “Our first guest of honor is due in a couple of minutes gentlemen. Smoke ‘em if you got them.” The guys let out a cheer, eager for the show to begin. Bruno turned to me, “Hey Jason, I’ve got a job for you if you’re up for it.”

“Sure, what is it?”

“Well, you told me you’d feel kind of weird fucking Connor so I wondered if you’d mind handling the poppers for him? Both Jackmans are popper pigs, and it will grease the wheels if you know what I mean.”

“Sure, as long as I can take a few snorts as well.”

“You can do as many poppers as you’d like. Maybe later on I can strap you into the sling and ride your sweet ass while you popper up, since you’ve left things open for business,” as he rubbed his big hand across my exposed cheeks.

As Bruno handed me two unopened bottles of poppers, I wiggled my ass at him and replied, “I will hold you to that.”

Over the noise in the room, I heard some cheering near the stairs and turned to see Biagio walking down the stairs looking sexy in his leather vest and bulging shorts. He was trailing a black leather leash behind him, and I watched as Connor obediently followed him wearing the gear Biagio had left out for him with the addition of a collar and a pup play hood that mostly hid his identity. I could see where this might be going when Mr. Jackman arrived. His cock was barely contained within the straining leather pouch of the jock, and I wondered if Biagio had already given him Bruno’s cocktail. I knew Connor was horny when we arrived; I couldn’t imagine what he would be like with the drugs and poppers. He looked to be as fucked up and horny as his old man was last weekend.

“Hey guys, say hi to my new whelp. He’s going to need some training, but he’s eager to learn. As Connor walked through the crowd led on a leash, some of the guys reached out to grope his hard-on, pinch his ass, or tweak his nipples. I suspected he was wearing a gag as he responded with moans, likely feeling the effects of the drug cocktail already. As he walked by, I noticed he had a tail sticking out between his big glutes to go along with his pup gear. Several of the guys were having fun tugging on it.

Connor’s eyes were wide and glazed behind the pup mask as Biagio led him over to one of the slings and helped him up onto the swinging leather platform. He removed his lead and carefully tied him in at the wrists and ankles. Once he was secure, he turned to the men and said, “Okay guys. He’s all yours, but… there are two rules. You can’t fuck him, and he can’t cum, otherwise, anything is game.” As the men let out a disappointed groan, Biagio clarified, “Oh trust me, you will be able to fuck him as much as you like, and he will cum many times tonight, but we have a special guest arriving shortly, and I want to save his ass and first nut for him.”

I saw Connor’s eyes widen in puzzlement, wondering who the special guest might be. I also knew by the time the guest arrived, he would be teased and edged within an inch of his life, and the drugs he had taken would be kicking in full force, keeping him hard and desperate. These guys knew how to keep a guy on the edge and begging for more. As Biagio unsnapped the removable pouch on Connor’s jockstrap, his big member flopped out and bounced on his belly. The cock ring was keeping his tool pumped full of blood as his dick leaked cum from the tip. As several hands reached out to pull on his balls and play with his engorged tool, I walked up beside his head and whispered, “Hey Connor, it’s me Jason. You look hot as fuck, dude. Blink twice if you’re doing okay.”

I was happy to see him blink twice as he looked up and recognized me behind the mask. I could tell he was loving this as his eyes drooped in pleasure while the guys worked him over. “Cool. Bruno has me on popper duty, so I’ll be right here if you need anything.”

The guys were taking turns stroking his hard cock, groping his heavy balls, and slurping pre-cum from the end of his dick. I could tell Connor was going out of his mind with the attention from the crew and loving being helpless in the sling. After a generous amount of teasing, edging, and some serious ass eating once his pup tail plug was removed, Leo pushed to the front of the crowd wearing nothing but nipple rings and black crotchless leather shorts with his big balls and cock swinging loose. 

He was standing between Connor’s legs with his hands gripping his raised thighs with his rigid, black dick poised at Connor’s tight ring. Leo seemed to be the designated warm-up act for these events, and he took his role seriously. Both his cock and Connor’s hole were well lubricated with spit, lube, and pre-cum. As the men watched, I saw Leo pull the sling towards him so that his blunt dickhead was pressed directly against Connor’s hungry hole. I heard a loud moan escape from Connor as he felt a thick cock poised at his ass ready to pound him. Leo smiled and said, “You want my cock in your tight little pussy, don’t you?” After Connor moaned and nodded, he glanced up at me, and I realized he was trying to tell him to give him a hit of poppers, knowing how big Leo was. I complied as I reached under his pup muzzle and pressed the bottle against his nose. Like his dad, Connor loved poppers, and he took several deep sniffs, hoping to make it easier to accommodate Leo’s thick shaft and loving how the poppers made him feel. Unfortunately for Connor, I knew Leo had no intention of giving him what he so desperately needed. That was coming later. 

With Connor’s body primed and ready for the fucking of his life, Leo teased him by dipping his cock into his hole, stretching the tight ring but only inserting about half of his bulbous head forward before pulling back again. He was deliciously teasing Connor as he lightly bounced the sling against his rigid shaft, lubricating his hole with his generous pre-cum and keeping him horny and desperate.

After a few minutes of this, I could tell Connor was incredibly frustrated as the teasing only made him ache for release. His cock-ring-bound tool was engorged with blood and tight as a drum as it extended rigid as a tire iron above his abs, big, red, and angry. I considered reaching down to give him a couple strokes to provide him with some relief, but the truth was, I was getting off on what Leo and the gang were doing to my friend, and I secretly wanted it to continue.

As Leo dipped his cockhead a little deeper into Connor’s entrance with each bounce, he began to shake on the sling like a child having a temper tantrum as he moaned in frustration. He badly wanted the full length of Leo’s thick black cock, but he had no ability to make it happen or articulate his desires. I could tell Leo was enjoying himself as a little more of his dickhead stretched Connor’s tight ring wider. He was dipping about three quarters of the blunt head into his hole, and I didn’t think it would be long before Connor’s tight ring clamped around the blunt ridge of his head. Knowing that Bruno wanted Mr. Jackson to have the first fuck of the night, I watched, curious about how far Leo would take this. 

As I gave Connor another deep hit of poppers, Leo allowed the full head of his cock to slide into Connor’s ass as his tight ring clamped down around the bulbous end of his cock. Connor moaned loudly, knowing Leo only had to lean forward or pull back on the sling with his strong arms to bury his shaft to the balls. Would he do it? I could tell by Leo’s expression that he was considering it, and I couldn’t blame him. He was never one to follow the rules, but I think Bruno realized the same thing as he walked over and gripped the sling chain, pulling Connor backwards, causing Leo’s wet cock to plop free and swing wildly in the air with a long strand of pre-cum hanging from the tip. “Thanks, Leo, great job. I think Connor is more than ready for our guest, which Hugo tells me has just arrived,” followed by a few cheers and whistles from the men.

Meanwhile, Connor was whimpering in frustration so close to receiving some welcome relief before Bruno rudely interrupted. There was a big puddle of pre-cum under his hard cock, and I could only imagine how horny and fucked up he was at this point. With Mr. Jackman about to arrive, I couldn’t wait to see both father and son’s reaction and how this would play out. 

I watched as Bruno walked over to the end of the room and disappeared upstairs while Connor looked around, wondering what was happening. I leaned over and said, “You’re doing great, Connor. Hang in there; you’re going to get some relief real soon. I promise.” As I heard some excitement near the stairs, we both looked over to see what was happening.

Mr. Jackman

I was super excited as I pulled into Bruno’s at the designated time. It had been difficult to concentrate at work all week knowing I was going to meet up with the guys tonight and finally have an opportunity to see the video of Connor fucking me with his big dick. I tried to kid myself that I just wanted to know what had happened with my son present, but I also wanted to see the incredible fuck I had felt. While Bruno had been noncommittal about what else was going to happen this evening, I was pretty sure I’d be tied up at some point and fucked hard by the crew, which was more than fine with me. That said, I had a feeling tonight wasn’t going to be your typical gang bang. Bruno had told me to show up on time, enter through the back door, and follow instructions, so that’s what I would do.

I had spent extra time preparing for tonight with a deep douche and a long shower before dressing and driving across town. I walked up to the back door and tried the door as instructed. There was no one nearby inside, but I could hear laughter and talking from the basement. Closing the door, I looked around and spotted a folded note leaning against a drink with the word “Boss” written on it. Opening it, there were brief instructions:

Howdy, Boss. We have a wild night planned for you. Before we begin: 

1. Drink the cocktail beside this note.
2. Go to the guest room, strip, and put on what’s laid out on the bed.
3. Come to the top of the stairs and wait for further instructions.

Your Crew

My cock was already hard in anticipation of what awaited me downstairs. I wondered if the boys were going to put me directly into the sling or have me walk around in whatever gear Bruno had left out for me first. Who knows, maybe they would strap me to the bench again? That had been an amazing night last weekend despite what had happened with Connor and Jason. I still couldn’t believe my son and his friend had fucked me, but at least Connor was unaware of the fact.

Spotting the drink on the ledge, I obediently reached for it and drank it back. It tasted like a rum and coke but with a funny aftertaste. I knew I shouldn’t be so trusting, but I just wanted the evening to start, and if it meant sucking back some drug cocktail that made me horny, relaxed, and up for anything, so be it. With the glass empty, I walked down the hall to the guest room. The volume of the cheering in the basement had increased, and I wondered what was going on down there. The men sounded boisterous, and I was hoping they would use some of that energy to thoroughly rail me tonight.

Entering the guest room, I closed the door behind me and looked down on the bed as I began to strip. Bruno had really gone to town this time with what I was wearing. It was all black leather and looked expensive from the chest harness to the chaps. There was also a military cap and armbands. It seemed an odd choice given my usual submissive role. Maybe the guys were trying out something different tonight. I would just let the evening play out.

Naked and hard, I stood in front of the dresser mirror and put on the chest harness. It had a length of leather that hung down the front with a metal ring attached to the end that was obviously meant to fit around your cock and balls. Although it wasn’t easy to do so with a hard-on, I managed to maneuver my swollen junk through the ring. I loved how the harness fitted around my chest, highlighting my pecs, and tugged on my dick whenever I moved. I slipped on the wrist and armbands and put on the chaps. The soft leather wrapped around my thick thighs, and I felt sexy as hell with my ass exposed and easy to access. There was also a pair of work socks and leather boots that I slipped on my feet. Finally I placed the cap on my head to finish the look and paused to look at myself in the mirror. Holy shit, I didn’t recognize myself. I looked like a BDSM dom ready to make my sub squirm like a bitch. I could easily picture Bruno wearing something like this and wondered again what was up. Whatever it was, I was excited to find out. 

I couldn’t stop myself from gripping my cock and stroking it in the mirror as I admired my new look. I was definitely feeling the effects of the cocktail as I pumped my hard-on into my fist. It almost felt like someone else was stroking me as I glanced at the stranger in the mirror. What had Bruno given me? All I could think about was getting off, and I was tempted to just keep stroking until I blasted a load on the mirror, but I remembered that I was supposed to go to the top of the stairs and wait. Wiping the pre-cum off the tip of my cock, I slipped my finger into my mouth and slurped it clean. I loved the taste of cum and was hoping I’d be eating a lot more of it tonight.

Forcing my hand away from my cock, I opened the bedroom door and made my way to the top of the stairs. It sounded like there were a lot of men in the basement. I could see a few guys near the bottom of the stairs otherwise, I couldn’t tell what was going on. I spotted Bruno making his way up the stairs with a big grin on his face. I grinned back, eager to get going. “Whoa, look at you. I barely recognized you, Boss. The boys are going to love this new look. Are you ready?”

“Oh, I’m ready; I’ve been ready all week.”

“Excellent. We have a surprise for you, so I want you to wear this to start with,” as he reached up and wrapped a blindfold around my head, tying it in the back. With it in place, he asked, “Can you see anything?”

“Nope, I’m blind as a bat.” 

“Perfect.” Without another word, I felt Bruno wrap his hand around my hard cock and pull me forward. “Watch the first step and follow me.” Loving the feel of Bruno’s firm grip around my aching dick, I let him lead me obediently as I felt for the first step with my foot, feeling buzzed and ready for anything. I felt so hot dressed like a butch leather daddy as someone led me by the dick like a naughty school boy.

Connor

Still horny as fuck from the intense teasing Leo had just put me through, before Bruno rudely interrupted, I lifted my head to see what was going on. The men were cheering as I spotted Bruno coming back down the stairs leading someone by their… cock! “Here he is, boys,” as the men cheered.

I struggled to see through my drug haze and the dim red light to whoever was following Bruno. With each step down the stairs, he revealed more of himself. It looked like he was wearing leather chaps over his muscular calves and thighs with nothing underneath other than a cock ring around his thick tool that was connected to a leather strap reaching up to a harness. As Bruno pulled him into the light by his cock, I watched as his strong hands revealed themselves with black leather straps wrapped around the wrists. I felt my dick pulse as I realized this might be the DILF from last weekend.

As he took another step, I could see his firm, hairy belly topped with leather straps that wrapped around the base of his chest, highlighting his big pecs. He was also wearing leather bands around his muscular biceps. Was this the guy from last weekend? There was something so familiar about him, and it was sending a direct charge to my cock. Suddenly I recalled my dream from the night of the gang bang. Looking back at his hands, I caught a glint of gold on his left hand. I remembered seeing the same familiar ring at Hugo’s, and suddenly it all came to me with a jolt: the DILF bound to the bench in Hugo’s basement, the man in my wet dream, and the leather daddy Bruno was leading into the basement by his dick were all the same person - my dad! How could I have not realized this before?

As the full implications of this revelation slammed into me like a semi-truck, I realized that I had fucked a load out of my bound and hooded dad in front of his employees at Hugo’s. Not only that, after I shot my load in his ass, I wrote my name on his cheek and spent the rest of the evening watching and cheering on his crew as they added their loads and names to mine. My friend Jason had even screwed him after Biagio and Bruno had put him through a sexy double penetration! 

As I looked on in horror, my dad stepped further into the light, so I could now see his familiar mustached face although he was wearing a blindfold over his eyes, which partially explained why Bruno was guiding him by his dick. What was almost as shocking as seeing my dad arrive at a gay sex party dressed in leather was that he was wearing exactly the same thing he had been wearing in my dream, including the leather cap. How was this possible? What was happening? “Welcome, Boss! You look amazing. The boys have been eagerly awaiting your arrival, and don’t worry, you will be taking a ride in my sling, but first, we have a surprise for you.”

What was going on? Why was he blindfolded, and what was the surprise? If my dad was my special guest, was I his surprise? I wanted to call out to him to let him know I was here but cursed the gag that was preventing me from speaking. Despite my predicament, I felt my aching cock throb and my hole clench. Was I getting off on this despite myself, or was it Bruno’s cocktail muddling my thoughts and keeping me hot and bothered?

While I knew from the incident in the elevator at my dad’s work site that he had fooled around with some of his staff, I was shocked to discover that he got together with a larger group of his employees and let them tease his cock and fuck his ass all night. I also realized that Bruno had brought Jason and myself to Hugo’s, knowing my dad was going to be there tied up and drugged in the basement. He undoubtedly had arranged tonight with the same twisted kink in mind as he yanked my dad towards me by his erection. For his part, my dad seemed eager to be led by Bruno until he was positioned between my legs. Bruno hadn’t let go of his dick but was now stroking it while my dad groaned and thrust into his palm. He seemed completely at ease and focused on his dick. I wondered if he had drunk the same cocktail I had.

At a signal from Bruno, a couple of the guys eased my sling back until I was held at one end of an arc. Bruno guided my dad forward until his hard cock was resting directly against my exposed hole. He gasped as his dick jerked from the slick, warm contact and said, “Oh fuck, what was that?”

“That Boss is your surprise. It is going to feel so good in a moment. I can tell you’re horny and eager to get your ass pounded. Don’t worry, the boys want it too, but first, there’s a little job I need you to do for me.” At a signal from Bruno, the guys started to slowly lower me until I felt my dad’s cockhead start to slide into my puckered hole. I was shaking and moaning trying to let him know he was about to fuck his son. 

“Oh yeah,” he groaned as my ass enveloped his cockhead. Tilting his head towards one side, he said, “I can hear someone moaning.”

“That’s your surprise, boss. You’re about to fuck his ass, and he’s very eager to feel your big tool. He’s been a naughty pup and needs a real daddy to train him.” The guys around us chuckled while I squirmed and shook in the sling trying to alert my dad that it was his son tied to the sling only managing to tease my dad’s cock with the motion. 

I looked up at Jason, pleading for his help with my eyes. He mouthed, “It’s okay,” as he patted my shoulder and tried to reassure me. 

Bruno reached up behind my dad and said, “Here, let me show you,” as he released his blindfold. My dad’s grin faltered for a moment when he saw someone wearing pup play gear tied to a sling in front of him with his cock lodged in his ass. Before he had a chance to take in much more, Bruno quietly said, “Now,” and the sling was released, swinging me forward and sliding the full length of my dad’s slippery cock into my ass. Both my dad and I groaned. 

Bruno turned to my dad and smiled at him, “It feels good, doesn’t it?” When my dad groaned in response, he added, “Go for it. Fuck him! Show him how a real dom disciplines an unruly pup. Fuck him like you’d like to be fucked. He wants it bad, trust me.”

My heart was racing while my dad looked from Bruno to me and geared himself up to breed me in front of his men. I couldn’t believe he didn’t know it was me under the gear, but it was dark in the basement, and neither of us was thinking clearly. He looked horny and thoughtful as he gripped the chains by my legs and pushed the sling away from his cock until just the head remained in my ass. With his cock poised to thrust back into me, he glanced around the room to the men watching, who were all encouraging him to go for it.

I heard Jason say, “Here, snort this…” as he held the poppers up to my nose. I realized there was nothing more I could do at this point and breathed in deeply. My dad grinned at me, knowing I was primed with poppers, and hauled back on the sling as my ass stretched open and accepted his thrusting cock. My dad was fucking me! The popper rush slammed into my body at the same time as I felt my dad impale me on his rigid tool. Every nerve ending in my hole was vibrating with his thick cock stuffed deep inside my hole.

Just like in my dream, my dad pulled back and slammed into me again with a snarl reveling in the dominating role he was playing. I could only groan in ecstasy as my disturbing dream came to life and I felt the thick ridge of my dad’s dick ricocheting past my prostate with each powerful thrust. Unsettling or otherwise, I could not deny that it felt fucking amazing to finally have a cock in my ass after an hour of teasing from his crew. I looked up at my dad’s face as he loomed over me. His eyes were glazed and his grin maniacal as he let himself give in to the moment. I don’t think he knew it was me under the pup hood, but I wasn’t sure he would even care in his current state. He seemed to be tripping on whatever the guys had given him and focused solely on busting a nut in the mystery pup’s ass. To be honest, I recognized myself in him from my time at Hugo’s last weekend when I had similarly let loose on the DILF.

I spotted Leo standing behind my dad pouring a generous dollop of lube on his giant, black cock and positioning his slippery shaft between my dad’s ass as he humped his crack. I knew Leo was more than eager to fuck someone after his earlier attempt. I could tell my dad was loving the feel of a hard dick teasing his crack as he moaned and pushed back against him between each thrust into me. It wasn’t long before Leo had angled his tool downwards and was pressing his slippery cockhead directly against my dad’s hole while Bruno held up a second bottle of poppers for my dad to inhale. I recognized the expression on his face as he held his breath and anticipated the moment when Leo’s black cock would breach his hole. It’s how I would react in the same situation. I could tell the moment Leo’s cock stretched past my dad’s puckered ring as his head tilted back and he moaned out loud. Leo was gripping him by his muscular ass as he slammed into him. 

While I was yelling, “No, no, no…” in my head, my body was enjoying the feeling of both men thrusting towards me as I swung in the swing and slammed back against my dad’s again and again. As in my dream, I felt like I might actually cum if the intensity of the fuck continued.

At that moment, the big screen TVs on the walls flipped from showing generic gay porn to one of my dad getting drilled by Leo on his office desk while he sucked off Bruno. Holy shit! As my dad continued to pound me while riding Leo’s cock, I glanced at the other screens to see one of me from Bruno’s point of view getting fucked in the construction elevator at the work site. I hadn’t even known that he had filmed me. The camera changed angles to show Hugo sucking me off while Bruno slammed into me.

Moving to the next video, it showed my dad gooning on Zeke’s big uncut cock as he slurped the big head obviously high on poppers. The final video of the four blew my mind because it showed me fucking my dad at Hugo’s last weekend. I was thrusting hard into him while he was bound tight to the bench. The camera had zoomed in on his drooling prick as my wet shaft slammed into his tight hole with our balls slapping together until finally, my dad began to blast a load onto the floor beneath the bench before Hugo jumped in to slurp up any remaining shots of cum from his spurting tool.

My dad had also noticed the videos and was moaning as he plowed into me while focused on the images of me fucking him. I was shocked by the raw, animalistic expression on his face as he continued to hammer his cock into me while Leo fucked him.

It was sensory overload with the combination of the videos, the recreated dream sequence, and the revelation of the DILF’s identity, all while my actual father was fucking me in a sling while he was getting fucked by Leo. My dad was trying to focus on the videos as well, but with Leo continually slamming his cock into him, he was struggling to take it all in. As much as I was getting off on what was happening, I still wanted him to let him know it was me under the hood, but I couldn’t even call out to him because of the stupid gag. 

In the middle of the action, Biagio walked up behind me and began to undo the pup hood. Finally. My dad was watching in mild interest, possibly curious about who he was screwing but enjoying himself too much to care. I felt Biagio reach under my muzzle to undo the gag before he pulled off both the pup hood and the gag in one smooth motion. I was fully unmasked with the gag removed as my dad rode me on the sling. I saw his mouth open in shock and confusion as he finally recognized me and realized he had his dick buried in his son’s ass. He was obviously not expecting to discover me under the pup mask. I was so close to cumming; any thoughts of calling out to him to stop were tossed aside. I didn’t want him to stop at this point; I wanted and needed him to keep doing exactly what he was doing. I was so close. 

He paused in his powerful thrusts to try and absorb what he was seeing and said, “Connor…?” just before Leo slammed into him, driving my dad’s cock deep into my ass and swinging the sling backwards. I could tell my dad was distracted by Leo’s thick tool hammering into him and forcing his cock into his son. He looked like he was trying to say something, but he kept getting pounded by Leo before he could form a sentence.

I was surprised to hear myself say, “Don’t stop…” 

I could see that my dad was trying to gain control of the situation and respond to my comment, but Leo would not give him a chance. He was making up for lost time from his earlier aborted attempt at my hole. I was moaning out loud, loving the intensity of the thrusts and feeling like my poor, swollen cock was two or three thrusts away from cumming. I looked around to see the men had all gathered around us, many of them with their dicks out, as they cheered and encouraged my dad to destroy my ass. Danny and a few others had their phones out and were capturing everything on video while Jason continued to feed me poppers.

My poor dad was still trying to speak and stop what was happening, but he was a helpless puppet as Leo gripped his wrists and thrust his cock deep between my dad’s cheeks while his own tool reamed my ass, over and over. I could tell he was losing the battle, as he could no longer deny how his body was responding to the ride between his employee and his son. With one more solid bounce against my prostate, I knew that was it as a blast of cum shot up from my balls and sprayed into the air. “Fuck, Dad, fuck! I’m cumming!”

My dad watched in awe as my thick shaft twitched and splattered both our chests with cum. It was too much for him as he groaned loudly and began to pump his seed deep into my tight hole. I could feel his cock pumping and spraying my insides, as Leo slammed into him once more forcing my dad’s dick deeper into my ass. Both men were yelling as they came together.

As my dad’s cock pumped the rest of his load into me, he half-heartedly called out, “No, no, no…” He seemed torn between riding out the rest of his orgasm and stopping now that he knew it was me, but any decision-making was out of his hands as Leo continued to torpedo his cock into my dad. Besides, he couldn’t undo what was done. As Leo finally started to slow down his thrusts, my dad collapsed on me in the sling, unable to take any more stimulation as his furry chest slid against my cum-coated torso. 

As he looked up at me, our eyes caught, and he said, “Connor, I…” He was cut off as Leo thrust into him once more, determined to drain every drop of cum from his thick licorice root. Both my dad and I groaned as his cock slammed into me. Leo was a fucking powerhouse. I could tell my dad was trying to make sense of what we had done and how he had gotten here while the video scenes continued to play on loop around us. While I knew this was wrong, whatever Bruno had given me was keeping my focus on my rock-hard cock as my dad lay on top of it. I could feel his hard shaft still twitching in my tight hole, ready for more as well. He looked torn between the horror of discovering he was fucking his son and wanting to do it again.

Before my dad could say anything more, Leo slid his cock free while Bruno and Hugo stepped over to help my dad up and walked him over to the other sling. I could hear him muttering to them that he was sorry and that he didn’t know it was me. He wasn’t making a lot of sense, but I too felt out of it as my thoughts wandered and my eyes kept returning to the video of my dad taking Leo’s thick tool like a bitch on the top of his desk at work while slobbering all over Bruno’s meaty dick. My dad was a fucking cockhound, just like his son apparently. I couldn’t stop watching the intense video showcasing my father as a willing submissive slut as he was spit-roasted in the middle of his office. Until recently, I had no idea he was gay, let alone a man-whore. The boys removed his chaps and helped him up onto the sling as they secured him to the chains. 

I was missing having a dick in my ass, but Zeke appeared with a long, black, flexible, double-headed dildo. It was thick and veined and at least 2 feet long. Oh fuck. He was squirting lube onto one end of it as he stepped between my legs and started to tease my hole with the rounded tip. Damn, this was more of what Leo had been doing to me earlier, and I could feel my frustration building. Just fuck me with it already, or better yet, whip your own cock out and screw me. “C’mon Zeke…”

“Easy, Connor, just be patient.” When he finally began to push the slick rubbery sex toy into my ass, I groaned in relief just before I felt the sling start to spin. As my feet bumped into my dad’s in the other sling, I realized my dad was as exposed as I was with our asses spread wide towards each other and our feet secured to the chains. The slings were close enough that our butts were only about a foot apart with our legs overlapping. I felt the dildo slide deeper into me as Zeke greased up the other end with lube and maneuvered the tip towards my dad’s ass. No! You wouldn’t... I looked up and realized Leo and Gage were behind me with Jason standing beside me. By the volume of the moan I heard from my dad, I could tell Zeke had slid the other end of the dildo into his hole. With our asses facing each other in the two slings, father and son were now connected by the big double-headed black dildo.

While Jason held up the poppers to my nose and Bear did the same for my dad, I could hear the excited chatter of the rest of the men as they anticipated the action ahead. Zeke reached forward and pressed something on the center of the dildo, causing it to vibrate powerfully, sending shivers up my hypersensitive hole. He gave the guys a signal as I felt Leo and Gage start to ease my sling towards my dad while Bruno and Hugo did the same on the other end. I could feel the veins of the greased dildo slide deeper into my hole as the same happened to my dad until both ends of the vibrator were buried to the hilt and the bare skin of my ass bumped into my dad’s. In unison, both of us groaned loudly as the guys cheered. I couldn’t believe the entire toy was buried between us.

Before I could catch my breath, the slings started to swing away from each other as the dildo eased out of our holes until only a few inches remained. The guys dutifully repeated the movement as father and son started to move back towards each other, driving the vibrating, slick, rubbery shaft deep inside again as our ass cheeks slapped into each other. My dad and I were fucking each other using the large double-headed dildo and neither of us had a choice in the matter. It felt so wrong, but it felt so fucking fine as well. I couldn’t stop myself from loudly moaning as I felt the vibrating, veiny surface of the toy stretch my hole while my cock throbbed. “Oh fuck...” My dad seemed to be enjoying himself as well as he groaned and arched his body in the twin sling.

As the motion of the slings sped up, Jason was holding the poppers to my nose again. I inhaled deeply, loving how the poppers opened my ass and amplified the sensations of the vibrator thrusting past my tight ring. My cock was bouncing on my stomach as I felt a wet hand wrap around my shaft while someone else started to play with my heavy balls. I was surrounded by hard, muscular, hairy men who were getting off on the deviant father/son scene playing out in front of them as we both bottomed the big black dildo. My dad’s hunky crew were crowded around us with their hard cocks out as many hands groped my overstimulated body. The room reeked of poppers, sweat, and spunk. Over the sound of creaking leather, moans, and the slick sound of lube, I heard my dad calling out, “Oh fuck, fuck…” It sounded like he was close. 

Trying to take it all in, I tilted my head back as my sling swung towards my dad and the dildo torpedoed my hungry hole. At that moment, I spotted Danny with his phone capturing the action. Part of me was mortified that sharing a dildo with my dad was being recorded, while part of me couldn’t wait to see the video. 

I started to groan as I felt another orgasm building in my balls. Some of the men were reaching out for the chains of the two slings and helping with the motion, driving the double-headed dildo harder and faster into both of us. On the next powerful swing, the veiny dildo bumped past my prostate, putting me over the edge as I could feel my load exploding from the end of my cock into the air and splattering the hands gripping me. It sounded like the same was happening to my dad by his moans. The slings continued to swing into each other while the hands groping and stroking my throbbing cock never let up as my load was slathered up and down my dick and across my balls. Several of the guys had also started to cum as well, and I felt sprays of hot cum rain down on me from all sides. 

Duke had been jerking his cock beside me and aimed it at my face as he began to unload. I quickly opened my mouth to try to capture the rest of his load directly from his dick into my mouth as the sling finally slowed down. I couldn’t believe that I had come again, and I was still struggling to get my mind around sharing a dildo with my dad after he had pumped a load into me earlier. The amazing part was I was still hard as I licked cum from my lips and looked around at the room full of hunky men.

Luckily the night was far from over as the men stepped back while Zeke slid the giant dildo out from us. The boys swung the slings so they were once again side by side, but this time my head was at my dad’s feet. I was flying on whatever Bruno had given me while my cock ached, eager for more attention. I looked over at my dad spread out in the matching sling with his beefy muscular legs spread wide and his body bound tightly. He gave me a sheepish look. Neither of us had had much choice in the evening so far, but we couldn’t hide the fact that we had enjoyed it as well. I could see he was still hard and had a fair amount of cum sprayed on him.

Biagio had walked up between my legs and was stroking my cum- and lube-covered cock while he dragged his big tool up and down my crack. Oh yeah, that’s the ticket. “You look sexy as fuck, Connor.”

I looked over to see Jason standing between my dad’s spread legs as he stroked his big cock and shyly looked up at him. I knew he had always had a thing for my dad and could only imagine what was going through his head. He looked nervous but determined as he politely asked, “Uh, hey Mr. Jackman. Um, I was wondering if it would be okay if I fucked you?” 

My dad looked like he was trying to come up with a response from his awkward and exposed position, but before he had a chance to speak, Bruno jumped in and said, “Jason, this bitch loves anything with a big dick. Don’t ask, just go for it.”

I was a bit surprised by Bruno’s comment given my dad was still his boss, but at this point, I guess anything was game, and by the focus my dad had on Jason’s thick cock, he was probably right. Bruno’s response seemed to embolden Jason enough to step forward, and tease his dick between his spread cheeks. When my dad moaned and closed his eyes, Jason took the opportunity to press forward eliciting a louder response from my dad. I think that’s your answer, Jason. I could feel Biagio doing the same to me as my tight ring stretched around his blunt tool, gripping his big cockhead. Oh fuck, oh yeah. Fuck me, Biagio. I’ve been looking forward to this all week.

My dad was moaning in ecstasy as my school buddy worked his thick shaft into him breeding him in front of his work crew and son. He was obviously enjoying Jason’s energetic thrusts while he unabashedly watched what Biagio was doing to me in the other sling. Danny and Bear had positioned themselves on either side of my dick as they greedily slobbered all over my engorged cock. They were hungrily riding their tongues up and down the shaft while exchanging pre-cum with their tongues when they met at the top. From this angle, I could see my dad was laser-focused on the wet blowjob I was receiving while Jason rode him. I couldn’t ignore the raw lust in his gaze as he looked on. At that moment, my eye caught his, and he quickly looked away. 

I didn’t know if I was getting off more on the thorough pounding Biagio was giving me or watching Jason rail my dad. Regardless, I was looking forward to a long night of studs using and abusing my dad and myself and knew we’d have plenty of opportunity to watch each other. It was strange to be sharing the slings with my dad, but at least we could put off having a chat until later. For now, I realized we were very much alike, as we both enjoyed being tied up and fucked hard. I’m not sure how I would feel in the morning, but for now I didn’t care.

Mr. Jackman

I had lost track of how many men had ridden Connor and me on the slings. The evening was a blur of thick cock stretching my hole, fucking my throat, or spraying volleys of cum. It was getting late, and some of the guys were heading home or had moved upstairs to find a place to crash, while Connor and I remained tied to the slings. Anyone who wanted to had fucked one of us or both of us. While it felt strange riding a big cock with my son beside me doing the same, I couldn’t deny that I was getting off on it.

I caught myself watching Connor more than once. He never seemed to tire of getting railed and while I had no shortage of guys eager to fuck me, the boss's son was definitely a favorite with the men. I lost count of how many times I had cum, but most of my orgasms had taken place while I was getting slammed by a hard cock while I watched my son get fucked, sucked, or jerked off. The videos of myself or my son continued to play around us, adding to the mood as well. For better or worse, there had been plenty of video taken tonight that would likely be added to the mix at future events.

With the evening wrapping up, Bruno and Biagio were untying Connor from the sling, who looked great despite the busy evening he had had. I couldn’t help but notice that he was still hard despite cumming a number of times that I knew of. The boy was a stud; like father, like son, I chuckled to myself. 

As they helped him down, Connor told them he was fine as he stood on his own. As the guys started to walk over to me to do the same, Hugo came running down the stairs. “Hey Bruno, Bear just took a tumble off the porch. Can you help? We can’t budge him.”

I saw a look of concern and frustration cross Bruno’s face. “Fuck, that boy could never handle his alcohol. Coming…” as he hurried towards the stairs. 

Biagio offered to help as well when Bruno said, “Thanks buddy, but you’d better untie the boss first.” 

Biagio looked torn between helping out with the Bear emergency and finishing up with me when Connor spoke up, “It’s okay, I can untie him.”

Biagio looked at Connor. “Are you sure?”

“Yeah, it’s fine. We’ve been through a lot tonight. What’s untying my dad from a sling? Go see to Bear. Go!”

“Thanks, Connor, we’ll just be a minute.”

With that, Bruno, Biagio, and Hugo hustled up the stairs to rescue Bear from the flowerbed. I was left alone with Connor in the basement with my limbs spread out and tied to the sling while he was now free. I saw him look at my mostly nude body in the sling and shrug his shoulders, putting aside any awkwardness with everything else that had happened this evening. He looked at me and nodded, “Dad.”

I looked back at him and nodded, “Connor.” With that brief exchange, he stepped forward between my legs to untie my legs. I was very aware of my son’s nudity and arousal as he moved about. I was spread out vulnerable on the sling and still hard as well thanks to Bruno’s potion as he reached for the ropes binding my legs to the chain of the sling. As he brushed against my spread cheeks with his naked hip, my cock jumped in response. I could tell Connor had noticed, although he tried to ignore it. “Sorry. I’m not sure why I’m still hard. It must be what Bruno gave me.”

“I feel you, Dad. I’m in the same boat. No worries.” I glanced down at Connor’s giant cock as it swayed in front of him while he worked on the knot. He looked as hard as he had when I had fucked him earlier in the evening when I hadn’t known it was him, although I should have recognized his monster cock. Jesus, he was big! How had I ever taken that beast at Hugo’s last weekend? I felt my cock lurch again as I recalled the pounding Connor had given me. I needed to stop thinking about sex this close to my son.

“You know, Connor, when this is all over, we should talk. There’s obviously a lot I haven’t shared with you about myself, and I’d like to talk to you about where you’re at as well. For me, it’s been a pretty recent revelation despite how crazy things have become.” I could tell Connor was embarrassed talking about this as he stood hard and naked between his dad’s spread legs. Could this get any more awkward?

“No worries Dad. I’d like to talk. Let’s just get you out of this sling to start with.” Connor had managed to untie one leg, although my leg was still suspended with my knee and foot supported by a strap. He’d have to get both legs untied before he could slip the straps free. Turning towards the other leg, I saw that he glanced at my throbbing cock oozing pre-cum onto my belly. Yep, your dad is a pervert on top of everything else. 

The next knot was tougher to undo, with the knot less accessible. Connor had to maneuver himself tighter into my crotch as he reached up to loosen it. He was brushing against my sensitive ass and balls as his hard dick glanced against my thigh. This was not helping my hard-on.

“Fuck, this one is tight. Was Bruno worried you were going to get away?” Connor asked sarcastically.

“Not much chance of that,” I wryly commented.

We both laughed, happy to break the tension and acknowledging the willing parts we had both played in the evening. As Connor inadvertently humped my thigh with his meaty dick, I tried to think of anything that might calm down my erection, but all I could think about was how close his thick shaft was to mine. This was torture. 

“Finally!” Connor announced with both legs untied. There wasn’t any point in removing my legs from the straps until my arms were untied, but I had some additional freedom of movement. “Let’s get your arms untied, and then you can get yourself down.”

“Thanks son.” We were still all alone in the basement as he reached upwards to untie the knots near my wrists. Rather than step around to the side of the sling, he was still standing between my spread legs, so when he reached over me, his dick brushed against mine as he stretched his muscular arms forward. It probably would have been easier to do this from the side, but Bruno’s cocktail was likely clouding his thinking.

“Damn, this is awkward. Hold on.” Holding my breath, I tried to ignore the fact that my hard cock was close to my son’s as he shifted once again and pressed his greasy shaft directly against mine. I couldn’t help myself and let out a quiet moan.

Connor looked down at me in shock when I explained, “Sorry, it’s not you; it’s just that damn cocktail. Keep going.”

Determined to put this awkward moment behind us, Connor pulled himself higher, struggling to undo the tight knot. In his current position, it was impossible to avoid touching me, so he gave up and focused on the knots while his rigid tool and heavy balls mashed into mine. Fuck, son or no son, I couldn’t ignore how good this felt as my cock jerked and pulsed in response. I had to force myself not to thrust my hips upwards, and I could tell Connor was trying to ignore how intimate this was. When he finally had the left wrist free, he said, “Just one more, Dad, hang in there.” I was desperately trying to ignore what was happening, as I didn’t want to embarrass myself or Connor further. 

Stepping back for a moment, Connor took a deep breath while he prepared to tackle the final knot around my right wrist. As he stepped forward, he was so focused on getting in position that he miscalculated and caught his lumbering cockhead under my balls, driving his shaft downwards between my lubed cheeks as he stretched forward. We both let out an oomph as his thick dickhead bumped past my well-used hole. The maneuver caught him so by surprise that he fumbled and fell onto my torso, driving his cock even deeper between my ass cheeks. I couldn’t help myself and let out a groan as my nerve endings were stroked and teased by the delicious friction. My son’s giant dickhead was firmly wedged between my ass cheeks with the tip of it mere inches from my hole. This was the same thick cock that had managed to make me cum last weekend without touching myself. Fuck.

“Oh shit, sorry, Dad. That was stupid. Hold on.” While he struggled to right himself, he inadvertently wedged his cock deeper before he managed to pull himself up and slide his tool free once again. As he reached for the final knot, his cock slid against mine once more, causing me to shiver in restrained excitement. While working on the knot, Connor glanced down at me and noticed my strained expression and asked, “Are you okay, Dad?”

“Yeah, I’m fine. Sorry Connor, I think I’m just messed up from whatever Bruno gave me. Just ignore me and keep going. Thanks for doing this; you shouldn’t have to see your dad like this.”

“No worries. I’m almost done.” Could he not feel his cock frotting against mine while he fought with the last knot? My dick was throbbing and oozing pre-cum as his giant lubed tool ground into mine. I felt like I might cum if this continued for much longer, and that would be embarrassing.

With the final knot undone, Connor realized the ropes were wound around my wrists several times and would need to be loosened. Eager to get this done with, he stepped back before gripping the chains near my arms and pulling himself forward so he could get to both wrists at once. This move resulted in his dick once more sliding downwards between my spread ass as his ridged head bumped directly against my sensitive hole.”

I saw his eyes widen in shock as I gripped on to the sling, realizing his cock was pressing against my hole. He started to apologize and was going to jump back down when I said, “It’s okay. Just finish up; I’m fine. You’re almost done.”

It was agony, madly gripping onto the chains with Connor’s thick cockhead teasing my puckered ring as his muscular form stretched over me and he struggled to unwind the ropes from my wrists. I could feel myself trying to maneuver my ass against his dickhead before I stopped myself, horrified by my body’s near betrayal. It was maddening to have that giant tool rubbing pre-cum and lube directly in and around my hole. I was glad my hands were still bound to the sling otherwise, I wouldn’t have trusted myself not to grab his meaty ass and try to drive his cock deep inside my hungry hole. What the fuck was wrong with me?

As Connor stretched forward once more to release the final rope, I could tell my wrists were finally free. At that moment, he paused and looked down at me with his muscular arms flexed, holding his broad torso over me, and with his giant cock angled downwards with the head resting directly against my puckered hole.

I could sense his restrained desire and the uncertainty in his eyes. This last week had been a roller coaster of events and emotions, with Connor fucking me at Hugo’s and me fucking him tonight, with neither of us realizing at the time what we were doing. We were now alone in Bruno’s basement, hard and horny, and my son had his impressive hard-on poised directly at my entrance. There could be no pretense that we didn’t know what we were doing this time if we gave in to this forbidden desire. I looked up at Connor struggling to hold my feigned indifference in place. I could tell he was searching for any sign from me as he strained above me with his lubed cockhead pressing into my puckered hole.

Unable to deny my feelings any longer, I arched my hips and ass upwards slightly against his dick, loving the feel of the slick head stretching my hole wider as it slid forward. Connor realized with that small thrust that I had acknowledged my own need, and with one brief moment of consideration on his part, said, “Fuck it,” as he let his body relax and gravity take over as his thick cock slid forward, stretching my hole wide until he was balls deep. I was no longer tied to the sling but I wasn’t going anywhere as I felt my son’s girth fill my ass.

As I tilted my head back and groaned loudly, Connor looked down at me with his cock buried to the hilt and said, “Fuck, why does this feel so good? What are we doing…?”

I interrupted my son, “Shh, we’ll worry about that later. Just go for it. I want you to and I can feel how badly you want to as well. Just fuck me, fuck me hard!” After a brief pause, Connor took me at my word, gripping the lower chains of the sling in his strong hands as he eased his thick tool out inch by inch. When just the meaty head remained embedded in my ass, he drove his cock back deep inside me. Oh yeah… “Just keep doing that, fuck.”

With the basement to ourselves, Connor took my advice, fucking me with a fury that I had rarely felt in all the time I had spent with my hunky crew. We couldn’t ignore the intimacy or the wrongness of what we were doing with no restraints or hoods in place as we fucked face-to-face. At one point, Connor grabbed a nearby poppers bottle and handed it to me. “I know you’re into these as much as I am.” 

With my hands free, I unscrewed the lid on the brown bottle and took several deep breaths while Connor continued to hammer his thick shaft into me. With my head full of fumes, I offered it up to him as he paused and took several deep breaths. With both of our cocks hard and throbbing, we looked at each other and grinned before releasing our breaths. Oh shit, here it comes. Knowing it was a relatively short-lived rush, Connor wasted no time in gripping the chains and slamming his rigid tool into me again, and again punishing my well-used cum-filled hole. Oh… yeah… fuck me! Both of our eyes were half closed as Bruno’s basement disappeared around us and we focused solely on the connection between my son’s meaty dick and my needy ass. I wrapped my hand around my hard shaft and started to fuck my palm as Connor energetically rode me. 

The room was silent other than the sound of the chains clinking, our labored breathing, and Connor’s cock wetly sliding into my hole as his heavy balls slapped against my ass. His big, ridged dickhead was hitting me in all the right places as I surrendered myself to the moment. I knew what we were doing was wrong, but I didn’t care. Nothing else was more important than the raw animal desire between us at this moment as my son destroyed my hole. As Connor fucked me, he reached up to grab my leather cap and placed it on his own head with a grin. My son was owning his dad, and joke or not, he wanted me to know it. 

We were definitely going to have to have a serious talk after this but for now, I wanted my son to breed his dad and fill my hole with his load as I jerked my cock and rode his shaft. 

Bruno

We were upstairs sitting around my living room watching the action in the basement unfold on my big screen TV. I was so glad Hugo had convinced me to install cameras near the slings. A lot of the guys had crashed or left, but Biagio, Jason, Hugo, Leo, and Bear were sitting around the TV watching Connor rail his dad. Bear was showing no signs of being inebriated despite his earlier alleged fall. The scenario had worked like a charm to leave Connor alone with his dad in the basement. Jason was sitting between my legs with his back against my crotch as I cuddled him and idly stroked his hard-on.

On the screen, Connor was aggressively fucking his dad as the sling wildly rocked suspended from the ceiling. From this angle, Connor’s heavy balls were swinging with each thrust as he drilled that giant cock into his dad’s big ass. The boss was untied at this point but he had no intention of going anywhere as he met his son’s massive cock with each thrust. He was jerking his own cock as he met Connor’s thrusts with his hips. Despite the wanton and reckless abandon of the evening, it paled in comparison to what we were now watching take place downstairs. Even I was shocked by the pace and fervor of Connor’s punishing thrusts into his dad’s muscular butt.

I heard Jason whisper, “Holy fuck,” beside me as the scene unfolded. I gripped his cock as he pressed his ass back against my hard dick, obviously turned on by the scene. 

I looked down at him and said, “What did I say? I told you they both wanted it.” I could see Jason’s mind working as he watched his buddy pile-drive his dad on the screen. Was he jealous of Connor fucking his favorite DILF, or of Connor’s dad getting plowed by his friend’s big hog, or was he picturing himself tied to a sling for his own night of debauchery with the crew? If the latter, I was already thinking of how we could make Jason’s gangbang a hot and unique experience. Maybe we’d arrange a surprise or two for him as well. I wondered if he’d be up for a double penetration with me and Biagio riding his twink ass together, or even hotter, Connor and his dad double-dicking him. Regardless, next weekend was available, and I knew of a few horny construction workers, including myself, that wouldn’t say no to a ride on his sweet ass.

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