Chapter 3: Ch. 3 - Jack part 1

Jack

“So, what did Kevin choose for his own initiation anyways?” I asked Daniel as we were busy packing our things back in our lockers inside the main office. Daniel had showered in the time I had been out with that cute, young stud…man he had a talented mouth, I would have fucked him then and there too if we had had more privacy.

“Oh. that. You should have seen it, he didn’t get off easy either way….he chose to pose as a bachelorette party stripper, but the guys made him record the whole thing as proof he had done it and then play it for the entire office, he was so red for the rest of the week!” Daniel side, smiling slightly.

“Wow, really?” I asked in amazement.

“Just ask him next time you see him, you’ll see, I’m told he got quite the amount of tips from it though, used them to buy those new tattoos on his arms and legs” Daniel said, before shutting his locker shut.

“I should probably suggest something that’s not as embarrassing and something I’m good at…” I said out loud to no one in particular.

I had only been on the job for a little while now, but I knew that the guys loved to make fun of each other a lot, the job itself was rather boring so the guys found ways to keep themselves entertained. That’s what started this whole ‘initiation’ ritual, I could only hope I’d find something to appease them, otherwise they might take matters into their own hands like they did with Daniel….

That’s when I got the idea.

“I got it! Why don’t I suggest a wrestling match with one of the guys?” I said.

Daniel’s brow furrowed and he had an intrigued look on his face, then said “huh, that’s a new one, they’ll probably add on things to help…make it more fun, but why not? It’s worth a shot” he said, before he nodded his head in a goodnight gesture and walked away, leaving me by myself.

After I finished packing up the rest of my own things I made to leave for the night, and I resolved myself then to go speak with Henry, our boss the next morning, I only hoped he’d find it as acceptable as the others’....

Over the course of the next day, I spoke to Henry, who was a 38-year old military vet that, despite the grays in his hair, was still remarkably built, in fact we each had very similar builds. Only I was taller and more agile while he had slightly more muscle mass. He had close-cropped dirty blonde hair, and hazel eyes, his sharp chin always imperiously looking up and down most people he spoke to. He had an air of authority but he was in reality very laid-back, perhaps a quirk as well as a familiarity with the boring desk job he mostly worked.

He liked the idea of a wrestling match, but he said he needed to be sure the others did as well, and told me to wait a few days for them to give me an answer. As I waited, it was nearly agonizing because whenever I passed them they would eye me up and down, then snicker as they walked past, it made me increasingly nervous what plans they were making.

After about three days, the day finally came when I was busy packing away my things for the day in my locker when they finally showed up, all of them so eager and grinning like fools, even uppity Daniel.

Henry, my boss, approached first, still smiling and said "we've talked it over, and we've decided it would be fun to try out this initiation idea of yours..." he said.

My heart soared, and I smiled in response at the news, but the mischievous looks in their eyes made me wary. "Alright, that's great! Who am I wrestling?" I asked.

"Now now, be patient Jack, we still haven't finished....we'll do it on two conditions: the first, we're going to make it a strip wrestling match, rules are simple, you start out fully clothed and your goal is to remove all of your opponents clothes before he can do the same to you" Henry said.

My eyes widened and my heart thundered in my chest at this, but I kept my composure as I gulped and said "and the second?"

"If you lose the match....you have to perform a forfeit of the guys’ choosing" Henry said, his smile so wide now my heart's pace quickened.

I knew full well what they were doing here, this wasn't your typical wrestling match, where I'd likely win against anybody in the office, no they did it this way to make the outcome more favorable...not to mention embarrassing.

A small blush bloomed in my cheeks as I considered what to say. I could refuse and be subject to whatever torments they cook up on their own...or agree and win this match by stripping my opponent...in the end the choice is simple.

"Alright....I can agree to that, now, have you decided on my opponent yet?" I asked, trying to change the subject slightly.

The others all snickered and smiled at one another as I agreed, and my heart sank as I hoped to god I didn't live to regret this.

Henry just shook his head and said "It's a surprise, come to the Rainbow Room bar in town this Thursday at 8, don't be late" he said before giving me a wink and walking away, and the rest of the guys followed suit.

As they left me alone, I slammed the locker shut and only one thought in my head escaped my lips as I contemplate my fate:

"Well....shit"

Thursday, 7:54 pm, just outside the Rainbow Room.

I arrived just before 8 o’clock, I had decided to dress in casual clothes, namely a blue plaid collar shirt, gray and black pants, and old, worn shoes. Underneath them all, I decided to wear some red briefs, which I hoped that during my match would never be revealed.

The Rainbow Room itself was the most popular gay bar in the town, and held special events like this at least twice a month, in fact I went here once during a volunteer stripper’s night, and I had caught quite an eyeful of so many sexy studs on the stage, one in particular was a tall brunette named Sebastian who had decided to bare it all, and he had the most beautiful cock I’d ever seen. The one who came after him though....was a shy but hot twink named Thomas, who had been the last performance of the night and everyone was enraptured by his magnificent bubble butt, his cock was great too, however…his slow tease of his back assets made my cock so hard in my pants that night I couldn’t help but vote that his had been the hottest show as a sign of how much I wanted to get my hands on him, among many others.

It made me nervous that the others not only knew of this place too, but had planned around it for me to do my initiation.

As I approached the front doors, I noticed the guys from the office coming up from the side of me, and as soon as they realized it was me, their faces all lit up and smiled, which made my heart flutter in my chest.

Henry, dressed in all black, walked up to me and shook my hand before he said “you're a good sport Jack, knew you’d make it on time” he said, giving me a knowing wink.

Daniel was there too, but was weirdly dressed in his security guard uniform still but well…that was Daniel for you, always so serious even when outside of work.

“Just glad you guys took me up on my offer, you guys ready to head inside?” I said, trying to mask how nervous I was and ignoring the sweat on my palms I went ahead and pulled open the doors, immediately feeling a cool breeze flow onto me.

The others followed close behind, each of them talking excitedly, all except for Daniel who remained solemn and…off, somehow.

The usual stage had been pushed back to make room for a large inflatable pool in the middle of the room where a large crowd had gathered around, some men, some women, almost all of them probably queer. Regardless, the pool itself was round and the floor inside was slick with what I assumed to be oil.

The sight of it made me visibly gulp. I had done oil matches in the past during my career as a wrestler, they always made things more interesting but frustrating too as they made your opponent and you hard to get a grip on. 

We didn’t have long until the host, the owner of the bar himself, a short, bald and flamboyant man named Ian wearing bright orange and yellow tonight emerged from the stage and started tuning up his microphone.

“Welcome back ladies and gents to our bi-monthly strip wrestling night!” he said, and the gathered crowd applauded in delight, this was clearly a popular event, much like the last one I visited.

“Yes, yes, settle down everyone I know you're excited to get started, but you know how this goes, first we need some volunteers…” he said. It was then that everything clicked into place as he finished speaking. They chose this time and place because a large crowd would be here to witness my potential defeat and humiliation. 

Keep it together, just trust in your skills and fight until my opponent is naked…I thought to myself as I tried to keep my confidence intact, especially in front of the guys who at any sign of weakness would pounce on it like sharks scenting blood in the water.

“You alright there, Jack? Not having any second thoughts now are you?” Henry said, a slight smirk on his face.

“No, not at all, just eager to get started” I replied, swallowing my nervousness and refitting the mask of male confidence firmly on my face.

“Good, because we got a little surprise for you…” he said, his eyes trailing off.

“...What surprise?” I asked hesitantly.

Henry didn’t respond, instead he pointed his chin up towards Ian on the stage, who by now was asking for volunteers from the crowd, so far no luck.

“Well? Surely at least some of you want to get down and dirty in there? Come on, raise your hands!” he said, flourishing his own hand in the air.

“We’ll do it!” I heard a voice near me say, as I turned to see Roderick, a 28-year old colleague of mine who was 6 '2 and rather lean, with dark hair and blue eyes raised his…and was also raising Daniel’s hands in the air.

My jaw dropped in shock as I gazed at the two, Daniel’s face was beet red despite hanging his head down. Ian heard them, pointed towards our group and said “excellent! We got our first volunteers folks! Come on up here and I’ll explain the rules” he said. Roderick led Daniel away towards the stage, and I kept having to contain my shock as I saw them climb up onto the stage, and Ian asked each of them for their names.

“Roderick Masterson,” Rod said, practically beaming.

“D-d-Daniel Heard” Daniel said, his voice stuttering.

“Well then Roderick and Daniel, the rules here are simple, you wrestle with your opponent and the goal is to remove all of their clothes before you lose yours, the winner gets to keep the losers underwear if they wish.” Ian said, the last part made Daniel blush.

“Also, there is to be no punching, kicking, biting, or any attempt to harm precious…sensitive body parts, if I or anyone else spots such disorderly conduct you will be asked to leave, understood?” Ian said, his tone shifting to something more serious. 

Daniel and Roderick both nodded their assent to which Ian’s face lit up with excitement and said “Wonderful! The stage is all set for you two, but keep in mind to try and not let this take too long, remember we want to see some skin!” he said, giving them both a wink as they each climbed off the stage.

Daniel walked to the left side of the pool while Rod went to the right, and each of them removed their socks and shoes before stepping inside the area. Daniel also removed his badge and name tag to prevent them from falling off and getting lost.

Both of them got on their knees and eyed each other, waiting for Ian’s signal that the match had begun. Roderick looked far more confident likely because he was taller than Daniel and was known for his strong grip among the guys. All he needed was to pin Daniel down and rip off his clothes.

Meanwhile, I saw poor Daniel whose face was now bright red, the sight of it made him look that much cuter and even turned me on a bit. I had to admit, a part of me desperately wanted to see him naked, so internally I was rooting for Rod to tear off all his clothes. The younger blonde kept his eyes locked on his opponent, but at the same time he looked confused, and nervous. He knew his best chance was to try to evade Rodericks powerful grip, and make his own attempts to pull away his opponents clothes.

“Alrighty then, on the count of 3, let the match begin…” Ian said.

The crowd tensed, including me, as we kept all our eyes trained on the two of them, especially when Ian began to count down:

“1”

Rod had his arms outstretched towards Daniel, who in response had his own bent upwards in an attempt to shield himself.

“2”

Daniel held his legs against the side of the pool, as if he was planning to attempt a lunge at Roderick who didn’t seem to react to the move.

“3!” Ian said.

As soon as the countdown was finished that was exactly what Daniel attempted to do, he used his legs to propel himself, his arms out as he sped right towards Roderick who was able to barely get away in time, instead Daniel only grazed the side of his shirt. 

Instead, Daniel landed flat on his stomach, the impact of which knocked the wind right out of him and the front of his uniform shirt was now slicked with oil as a result. Rod attempted to turn around and take advantage while Daniel was vulnerable, but the blonde was able to recover and dodge away just in time.

This went on for the first few minutes of the match, where each of them was testing the other and made attempts to grapple the other. I noticed that the problem with this was that they were too focused on each other, the target was their clothes after all. Roderick did manage to briefly wrap his arms around Daniel in a grip, and it looked like he twisted Daniel’s nipples through his shirt which made my cock twitch inside my pants. However, the oil let Daniel slip away with his shirt intact.

The two of them tussled back and forth, each attempting to grab the other’s clothing while trying to avoid being pinned, their bodies pressing against each other tightly as they both fought to strip the other completely naked.

Eventually, while trying to evade Roderick’s grip, the oiled floor made Daniel slip as he attempted to dash away while standing up, likely done out of panic. But, this let Roderick finally latch onto him, he used one arm to pin Daniel’s neck against him and the other grabbed the collar of his uniform shirt and the crowd cheered when a loud RIIIPPPP sounded and Rod let Daniel go but came away with large chunks of his shirt in his hands. Roderick wasted no time in ripping off Daniel’s uniform shirt, and now everyone saw his white tank top underneath.

“Fuck! You bastard!” Daniel said out loud, to which Roderick only smiled at him and shrugged his shoulders.

Daniel, in a fit of rage, used the oil on the floor to his advantage and propelled himself once again, faster this time as he slammed right into Roderick who was too slow to react. Daniel wrapped his legs around Roderick’s waist, making him unable to move. This gave Daniel the opportunity to use his hands to grab a hold of Rodericks’ gray tank top and he pulled each of them in opposite directions, tearing the top straps off.

But Daniel wasn’t done yet, he grabbed the loose ends of his top and pulled it straight downwards, exposing Roderick’s bare chest. A few whistles sounded in the crowd as everyone gazed at Roderick’s caramel-colored torso, his nipples like spikes on his chest in the cold air of the bar. He had surprisingly little chest hair, in fact it looked like he shaved it regularly. Regardless, once he recovered he pushed Daniel away from him who landed on his stomach.

Roderick, now furious, stepped forward before his foe could get up and grabbed Daniel’s legs and pinned them with his knees, then he reached down with his arms and held his hands above his head with one arm. 

“Now you're gonna get it” he said, growling.

He slapped Daniels ass through his pants, and again, and again, essentially spanking him.

“Dude-what the fuck?! Ow!” Daniel said, his face completely red as Roderick spanked him but he also bit his lip as is to stop himself from moaning…fuck, the sight of it was so hot, I had to prevent myself from reaching down to stroke my rapidly growing boner. 

Daniel’s cries stopped when Roderick suddenly changed tactics and he started spreading the seams of the fabric of the back of his pants. He started tugging and pulling until he managed to rip a tiny hole through which he slipped in a finger, gradually making the hole larger until he could fit in both his hands, small rips and tears of fabric could be heard as the crowd went silent to watch. Daniel tried to crawl away, but he was firmly pinned by Rodericks’ legs.

“You're not going anywhere boy, not until these are off you” he said, then with both hands he gripped each side of the hole with his hands, then pulled.

RIIIPPPPPPP

The crowd went nuts as Rod ripped open Daniel’s pants from the back exposing his black boxer briefs. Roderick then slapped his ass again, and again he seemed to enjoy spanking the young lad. Daniel’s cries as he did so sounded more like muffled or restrained moans this time around, and this continued until Roderick stopped, and he reached underneath and wrapped his hands around Daniel’s belt and we knew exactly what he was doing.

“Noooooo!” Daniel whimpered as he was powerless to stop Rod from undoing his belt, he desperately tried to move as Rod slowly and teasingly unbuttoned the front of his now torn pants. Rod was smiling wickedly as he lowered down Daniel’s zipper and did something else I couldn’t see, but Rod’s smile turned to a frown for a brief second. Whatever it was he removed his hand and grabbed the sides of his pants, and Daniel’s protests were for naught as his pants were  pulled down his flailing legs.

While free now that Rod had to get off his legs to take off his pants, Daniel is desperate now that he only has his black boxer briefs and tank top left.

His eyes looked crazed and he rushed to get up, looked at Roderick who was temporarily distracted by tossing his ruined pants away, and without warning Daniel lunged at him, the two of them tangling together as they each battled the other for dominance.

Wasting no time, Daniel stripped off the remains of Roderick’s shirt and gripped them in his hands tightly. In turn, Rod managed to make little rips and tears in Daniel’s tank top as they each grappled the other.

“Just give up, this match is mine!” Roderick said, laughing.

“Not even close!” Daniel replied and he twisted Rod’s nipples which made Roderick yelp in surprise and his grip on Daniel loosened. Using his arms he lifted Rodericks up above his head and with the strips of fabric from his shirt, he used the strips of it to tie Roderick’s hands together.

“Not so much your match now, is it?” Daniel said, tauntingly.

“Fuck you!” Rod said in response and despite his tied up hands he rammed right into Daniel, using his fingers and his legs to rip off the remains of Daniel’s tank top, leaving them both bare-chested.

Daniel was considerably paler than Roderick, like a stark white contrast in fact. As I suspected he didn’t have any body hair on his torso except for little blonde hairs coming from his armpits. 

The two of them continued to wrestle aggressively, the oil quickly got on their increasingly bare bodies and they soon started to shine and glisten beneath the lights pointed directly at the pool. This made any grab they made towards each other much harder, even while grinding their slick bodies together. 

Ian didn’t say anything about twisting in the rules, or humping, which became a common tactic for both of them as Daniel realized that Rods’ nipples were sensitive and Roderick in turn found out how distracted his opponent got when there was any kind of activity near his ass.

Even with his hands tied, Roderick still found ways to pin Daniel down, even trying to tug on his boxer briefs and despite the blonde’s efforts everyone could see the huge bulge he had going on. 

Finally, Roderick was dry humping against Daniel’s ass when the blonde stud managed to free one of his arms beneath him which allowed him to reach around and heavily twist one of Rod’s nipples.

“Ahhhhh!” he said and Daniel broke free and pounced on his opponent, their oil-slicked bodies slipping as they pressed tightly together. While pressed together, Daniel outstretched his legs to push away Rods, and straddled his bare chest, his ass pointed towards Roderick’s face and he used both his arms to hold down his legs, which had him virtually pinned down.

“Ready? It’s time to lose” Daniel taunted Roderick and, with his ass to Roderick’s face, he leaned down over Rod’s crotch and with his hands he undoes his belt. Roderick began to flail his legs in a vain attempt to reach at Daniel but it was no use as Daniel also wasted no time in unbuttoning his pants. 

Lifting himself up and off of Rod’s chest, Daniel grabbed both sides of his pants and before he could do anything, he pulled the garment down his kicking legs which revealed his green and black jockstrap underneath. But Daniel wasn’t done, no I saw he had the last strips of Rod’s tank top in his hands and while it was a struggle for him, Daniel managed to firmly hold his legs in place to tie them together.

“How’s it feel to be my bitch?” Daniel said, lightly slapping Roderick’s bulge which made him yelp. 

This time it was Roderick’s face that was red, he had been so assured of his victory and now all he had left was his jockstrap and was practically at Daniel’s mercy. The sight of the more lithe Daniel dominating Roderick gave me such a thrill, I would have broken the lad in two if I had been his opponent, oil or no. 

My cock throbbed in my pants and I couldn’t help but massage it as I watched Daniel flip over his opponent onto his stomach, showing off his bare ass cheeks. Daniel then brought his hands over his opponent and slapped his bare ass. Rod didn’t have very thick cheeks, unlike Daniel whose ass was plump. Daniel brought Roderick’s ass over his knees, and continued to spank him, Rod’s cries egging the crowd on and exciting them, including me…

Once Rod’s cheeks were a bit red, Daniel moved his crotch against Rod’s ass and started dry humping him. 

“Ah!....Fuckkkkk” Rod said as he clearly felt Daniel humping against his ass…and seemed to enjoy it too as he moaned slightly until Daniel reached around and covered his mouth with his hand as his hips slowly thrust back and forth. I couldn’t believe my eyes as I saw my two colleagues practically fucking right in front of me, the oil made each detail of their bodies stand out that much more too.

My cock was throbbing in my pants now as Daniel slowly grinded his crotch against Rod's ass and even with his mouth covered, Rod couldn't help but let out his muffled moans.

"You like that? that's a winner's cock against your ass right now, bet you wish it was inside you" Daniel said and did a hard thrust this time which made Roderick's body shiver, and he whimpered in response/

This match had only gotten increasingly erotic, and no one moved or said anything to stop it as the action only increased mine and the crowd’s excitement. Daniel stopped humping and brought his crotch right in front of his opponents face, his bulge more prominent now and I could tell he was huge just from that.

Rod tried to turn his face away from the bulge in front of him, but it was hard for him to move at all. He continued to taunt him like that with his concealed cock just a few inches away from his face, until finally, the crowd began to egg Daniel on to remove the jockstrap and strip his opponent fully naked. 

"Take his jock!"

"Yeah, make him naked!"

"Strip that loser!"

Were all cries from guys out in the crowd, and the guys from the office chuckled and I could have sworn I thought I saw a few of them rubbing their crotches as well...

“You hear that? Time to get naked” Daniel said in Roderick’s ear, and with both hands he gripped Roderick's’ own bound arms and pulled him up and steadied him on his feet. Standing him up before the crowd, Rod’s face is completely red as he is utterly humiliated, and it was about to get worse as Daniel circled him like a vulture, making him uneasy as to when he would strike.

The crowd didn’t stop chanting, even our coworkers were joining in, they were enjoying seeing poor Roderick get utterly defeated by the 2nd newest security guard. After circling a few more times, Daniel came up behind him and yanked his jockstrap down his legs…which revealed his fully hard 3-inch cock which flopped up and down out in the open, clearly Daniel’s dry humping had more of an impact than I first thought. Regardless, with his last piece of clothing stripped away, Daniel was the winner of the first match. 

The crowd erupted into cheers, and Daniel untied Roderick who sat there, utterly humiliated with his head in his hands, until Daniel said “you can keep your loser undies, seems like you don’t have much to show off anyways” he said and the crowd chuckled a little at that.

Roderick lost it at that, and while Daniel was facing the crowd he got up and without warning he lunged forward, grabbed the sides of his boxer briefs and yanked them right down his legs.

Mine, and everyone else’s jaws dropped as we saw Daniel’s cock slap right into view, he was semi-hard but his cock was at least 7 inches, while not that thick his full size was likely over 8 inches! He was hung like a horse! 

Daniel’s face quickly turned red and pulled his undies back up before giving Rod a furious look. Before they could say anything Ian tapped on his mic and said “Well well, seems like Daniel is our first winner of the night! And might I say he looks like a tall beanstalk compared to tiny Jack over here, what do you say folks?” 

The crowd cheered their approval and several of my coworkers snickered and muttered between themselves. They were totally going to use them as nicknames for both Roderick and Daniel. I felt sympathy for both of them, office antics can get rather intense.

The two of them meanwhile had left the pool and made their way back to us, both clad in just their undies. And of course, they were greeted to the calls of ‘Beanstalk’ and ‘little Jack’ which made both of them turn a shade redder than a tomato. 

I stepped closer to Henry, trying to ignore my raging boner and asked “Well…that was interesting…so, who am I facing?” I asked, trying to act nonchalant.

“Me” he said, smiling. And the color drained from my face as Ian called for the next set of volunteers and Henry proudly raised his hand in the air.

Well…no going back now…let's do this I thought to myself as I raised my own hand in the air and Ian pointed the both of us out and as I walked up onto the stage I only hoped I didn’t live to see myself reduced to an office nickname for the next few months.

Those hopes…were about to be dashed harder than I ever thought possible.

End of Chapter.

Author's Note: Thank you all for being patient, I really appreciate your support with certain parts of this latest chapter!

We saw Daniel manage to subvert expectations and defeat his taller and stronger opponent Roderick, can Jack do the same against his more experienced and muscled boss, Henry? find out next chapter ;)