Flag vs. Flag

My New Gear

My first custom pro wrestling trunks were patterned off the Canadian flag. Red panels on the side. White panels in the middle, front and back. And a red maple leaf dead center over my bulge and butt. When I wrestled pro-style, I added shiny patent leather white pro boots, red knee and elbow pads, and sometimes a white lace-up mask with a red maple leaf that framed the eye and mouth holes. My love of superheroes even had me using a large Canadian flag as a cape for a more dramatic entrance.

I wasn’t an actual pro, just a weekend wrestler cruising the personals sites for submission or pro-style matches. I’d like to say my motivation for these trunks was national pride or maybe having a piece of home after I moved to the US, but that really wasn’t it. No, my inspiration to cover my crotch in my home country's flag was the stable of Canadian heels like Petey Williams and Bobby Roode dominating TNA at the time.

I loved looking at myself in my full gear. That was unusual for me. I wasn’t vain about my looks. I was vain about other things, like my ability to kick ass on the mats, but I let other guys worry about how I looked sitting on their chests, flexing my biceps, and counting the pin. I was 28, 6', and 215 lbs with a smooth and solid wrestler’s body. I looked good enough to have a steady stream of guys contacting me, skilled and powerful enough to win a lot, and fun enough to earn rematches and recommendations.

The Canadian gear only increased my queue of pro-style opponents with offers for both competitive and fantasy matches. In my new gear, I also heard a lot more from jobbers. Even the supposedly competitive matches quickly turned into squashes with me naturally falling into the dominant role. It suited me fine because sex stakes were offered more frequently, too. I’d been a 100% top since I left university and wasn’t looking to change that. More wrestling led to more hot wrestler ass.

Best investment I'd ever made.

Eventually I bought a gold title belt off eBay. After all, if I couldn't lose, I should have something to show it. It was a great time. My look, attitude, and experience level all finally matched my physical strength. For the most part, I stopped wrestling submission or in any of my other trunks – I was a full-time Canadian pro heel. In the back of my head, I knew that it was just a matter of time before I wrestled an American in flag gear, but surprisingly, it took a while before that happened.

A New Challenger

The first guy who contacted me for a private match in American gear was Joe. He was steered my way by Shawn, a great guy that I’d wrestled (and beaten) three times. I recently squashed him convincingly in a mask vs mask melee. His mask was hanging on the wall behind me, perfectly framed for my web camera as a warning about wagering gear against me. Shawn told me that Joe had recently jobbed for him in a hot match. That was good enough for me to work toward finally getting a flag vs. flag contest.

Over the next week, Joe and I exchanged quite a few messages. I'm usually on the slower side to respond, but Joe’s patriotic look and provocative banter got my full attention and moved him to the top of my priority list. The trash talk was so good that it quickly elevated into embarrassing stakes for the loser and dominance for the winner. I didn’t have to work at all to convince him on sex stakes which was great. If he jobbed for Shawn, I knew that he must be a submissive dude.

Joe was big and beefy (6'1", 250 lbs) and mature (mid-50's, roughly twice my age). In the pic he sent with his challenge, he looked perfectly jobberific in a US flag ring jacket and skimpy American flag trunks. He said it wasn't his usual look anymore, but that when he saw me wearing my Canadian stuff, he pulled it back out just for our match. He wanted to “wear the flag while he kicked my Canadian ass”. As he would be the first America-themed wrestler I faced, I was overly excited about the gear and his threat. We each added our trunks onto the stakes. Since he was wearing old trunks, he obviously didn't mind losing them. I’d proudly put them beside Shawn’s mask.

With the jacket, I couldn't see much of his upper body, but he did have salt/pepper fur covering his chest. The trunks showed some nice thick legs and his trunks looked like they were filled out by a good-sized package. He looked handsome enough – kind of rugged looking, square jaw, salt and pepper beard, and thinning silver hair. Body-wise, I looked at his other profile pics that showed he was thick and a little soft. It all looked good to me. Joe was definitely hot, but given the trash talk, I would’ve fucked him no matter what he looked like. I’ve always been more about attitude and action than a guy’s looks.

I was stoked. We agreed to a “competitive” match, but Shawn told me again that Joe was a total jobber. Despite his considerable size advantage, soft beef was no match for young muscle and he’d never match my stamina. Even from his messages, I could tell where it was headed with all his patriotic trash talk. Joe was definitely giving me cues on how to humiliate him. It’s a jobber trick – they say, “I’ll make you lick my boots,” which means they want you to make them lick your boots. With every message, I got more excited to dominate the older American jobber as he basically gave me a sexy guide to owning him.

Close to our meeting, Joe suggested something radical (at least for me) - he said that since we had references, knew so much about each other, and seemed to be on the same page on rules, limits and stakes, why not skip the normal pre-match chit-chat and get right into it? It would make the scene seem more real and more intense if we weren’t palling around beforehand. I was blown away. Maybe others did this all the time, but I never had. I usually like to feel the guy out, have a beer then move to my basement mat room. However, I did feel good about our match, so I agreed. It would be like a real match - no friendly conversation, no acting. We would meet as cross-border adversaries on the mats. My juices immediately started overflowing at the thought.

Exactly on time, he arrived. I was ready in my gear, visualizing the fun of the after-match stakes. I heard him come right in my unlocked front door, lock it behind him, and start to get ready in the privacy of my living room. I moved downstairs into the rec room, where I had the thick 12x12 wrestling mat laid out, surrounded by smaller foldable black exercise mats. I stretched a little but mostly, I paced.

The anticipation of this blind match was making me crazy, knowing he was upstairs getting ready. I bounced around the room for what seemed like forever. I had to work at not getting too excited. I kept the basement overly warm, for comfort since we wouldn't be wearing much, but also for extra sweat during the match. Well, it was working - my excitement and the heat had already given me a sheen of sweat and a semi-hard cock. I waited. I told him he could grab water, beer, or pop (he tried to correct me to say 'soda') from the kitchen, so maybe that’s what he was doing. Fuck. He had to be close to ready by now.

Finally, the door to the basement opened. Yes! As he descended the stairs, I saw his black leather pro boots then thick hairy tree trunk legs then tiny, painted on trunks then the jacket and finally his face. It was really happening.

Pre-Match Fun and Games

At first, I was stunned. Not for any bad reasons. All for good reasons. Joe wore the same gear from the pic – the jacket, trunks, pads, and boots. In his mouth, he clenched an unlit cigar. In his right hand, he was carrying an open bottle of Budweiser, and in his left, the rest of a six-pack he must have brought from home. I wouldn’t have that piss in my house, but I was happy to see him committed to his role as the all-American jobber.

Anyway, what stunned me is that he looked so much better than I expected - his pics did not do him any kind of justice. Joe was very masculine, very handsome with piercing green eyes and the rugged features and square jaw I mentioned earlier. His head was shaved, which took years off, and his beard was only a tight goatee - not very jobbery, but so smoking hot. Fuck, the man needed new profile pics, because the Joe who showed up was a smoking hot daddy bear.

Joe set the five-pack on my bar, took the unlit cigar out of his mouth, and chugged the open beer. I admired the show. He looked me up and down, just smirking and nodding. I stood there trying to look imposing, arms crossed, not moving. He turned away from me, still not really acknowledging me at all. I admired his flag-wrapped ass, which looked firm and muscular, perfectly built for my younger cock. He opened a second beer and then put the remaining four in the fridge behind the bar.

I snorted and said, “So you’re the pride of America? Glad to see you bought some water,” referencing his choice of American beer, “But you might want to take it easy. Even flavored water like that can dull old reflexes. I don't want this to be too easy.”

Joe squared up to face me. He drank down half his second beer and then put it down. He finally spoke - this was the first time I heard his voice, and it was perfect - deep and strong with a slight Chicago twang. He replied, “I’ll finish this one after the first fall. I bet you won’t even last long enough for it get warm.”

Joe fished out a lighter from his jacket and put it with the cigar on the bar. He said, "Victory cigar."

Instinctively I said, "Um, no smoking in my house." Damn, I immediately wanted to take that back. It sounded so fucking whiny. And why was I conceding he had a chance of winning? I should’ve said something like, “You’ll never get a chance to smoke it.” Or something like that.

Joe picked up on my regret. He said with a confident smirk, "I guess you'll have to try and stop me."

With that, Joe removed his jacket, and I finally got a good look at his body. WOW! He was more solid, with a bigger chest than in his pics, even thicker arms and legs, and a larger package. Again, his pics didn’t tell the whole story, but in the reverse of most guys – he was infinitely hotter in person. The scene also made it so much hotter. The gear, his entrance, the stakes – my mind was spinning. It was all so real. I was so excited to dominate this All-American stud that I was ready to attack him now.

My cock must have shown it, because he pointed at my trunks and said, "So kid, I guess you're not used to seeing real men up there in Canookia. Eh?" I didn't appreciate the mocking way he added the "eh" at the end. Or the way he called me kid. Or the fact that he insulted Canada. Yeah, this was going to be good.

I replied, “You’re going to see what a real Canadian man can do.”

Joe laughed. He pointed at my still expanding pouch, “You’re pretty excited for a guy who’s about to lose his gear and his ass. Kid, I’m gonna teach you to have some respect.”

I replied, “Bring it on, old timer.”

I took the flag off my shoulders, letting him take me in the way I took him in. He licked his lips and I saw a twitch in his pouch. I guess he liked what he saw, too. Smiling, I turned around and hung my flag on the wall proudly. Before I turned back, I felt Joe’s breath on my neck and his hand unsnap my title belt, letting it fall to the floor. I turned around, surprised he could move so fast and so quietly - Joe was right there in my face, looking me in the eye and smirking arrogantly.

Joe used my surprise and his weight advantage to catch me off guard and push me back against the wall. BOOF! We stood there, face to face, chest to chest, cock to cock. He moved his hips, grinding his cock into mine. I was pinned, but I didn't want to overreact to his games. I acted calm and in control, even as my cock swelled a little more, pressing against his package.

Joe stepped back slowly. WHACK! He flipped his hand to the side, swatting my cock lightly, taunting me. I was surprised by his attitude. I expected an easy squash job with a horny old face/jobber, but if this guy wanted a competitive heel vs heel bout, I was game for that, too. I actually preferred it to guys who just rolled over. Topping a top was one of my favorite things to do and the guy was acting like a total alpha top. I was gonna love teaching this old dog some new tricks.

The sexy hairy beast spread his arms to his side. He motioned "come on" with his hands. I didn't need to be asked twice. 

The First Fall

I moved in. We locked up in a tight collar-and-elbow grip. We pressed against each other, each pushing and maneuvering. UNH! UGH! We grunted as we strained, muscle vs muscle. We each tried maneuvering the other into a headlock or a takedown, but we were both able to counter the other, feeling each other out. We broke the lock and circled, both of us smiling and already a little sweaty.

We locked up again, but this time, Joe immediately used his weight advantage. He launched forward and muscled me across the mat. His momentum bulldozed me back against the wall again, this time hard. BAM! I was a little stunned from the impact. He moved forward and lifted his knee into my lower abdominals. WHOMP! When I bent forward, he locked on a front facelock and pulled me back to the middle of the ring. He drove two forearms across my back. THUD! THUD!

Joe's arm around my head was like a vice. URGH! I was starting to realize he was more than I expected, maybe the strongest guy I had ever wrestled. I couldn't break free, so I delivered a series of quick fists into his stomach. POW! POW! POW! My hand bounced off his harder than expected muscles, but after a few more hits, I did finally get his attention. He reached for my wrist before I could deliver another fist, grabbing it tightly, but allowing me to pull my head free. I used his tight grip on my wrist to pull him into my raised knee. THUD! OOF! He let go and backed up. I could see some red from my fists on his midsection, which pleased me. Joe was many things, but soft was not one of them.

Even though it had only been a few minutes, both of our cocks had swollen with excitement and were straining against the spandex flags that covered them. We moved in close, not locking up, but instead getting right in each other’s face in a hot silent challenge. While I was focused on the staredown, Joe slipped his hand forward and smacked my cock with his right hand again, this time a little harder. THWAK!

I twitched more in surprise than pain, but Joe had outsmarted me - the distraction was all he needed. He reached around my waist and grabbed me, pulling me close into a bearhug. Our chests and cocks were pressed together as he crushed my sides and back. I was pushing on his shoulders when he shocked me again - he bent his knees, adjusted and lifted me off the ground! ARGH! The pain increased exponentially. I lifted my feet and braced my knees on his thighs. While this relived the stress of gravity on me, it also made it easier for him to hold me aloft.

UNH! AHHHH! I couldn't believe what was happening - I had never wrestled a guy who could lift me for more than a few seconds before, so I didn't really know what to do. Joe bounced with me in his arms then shook me. My sides and my back were actually starting to hurt. I leaned back, which put more pressure on my back, but allowed me the room to pound two short forearms into Joe’s barrel chest. WHUMP! WHUMP!

The blows staggered Joe enough for me to get my white boots back on the floor, but not enough to break the hold. Joe shook me back and forth again, breaking my concentration and shooting more pain through my back. When he stopped, it took me a second to get my focus. That second was too long, as the American stud released the bearhug lowered his right arm between my legs and picked me up across his chest!

WHOA! I was once again in new territory, up in the air for the first time ever. Joe turned me over, body slamming me to the ground. BOOM! He didn't do it too hard, but it was enough to disorient me. When I opened my eyes, I saw the stars and stripes over his ass coming right at me - Joe dropped down, using his 250 lbs to reverse schoolboy pin me, positioning his flag covered ass right on my face.

With my shoulders pinned to the mat by his shins and my face smothered by his soft, round glutes, Joe was in total control. POW! THUD! POW! He pounded my abs, harder and slower than I had done to him earlier. I let out a yell, but my voice was muffled by his ass. I instinctively lifted my knees, which Joe grabbed. He wrenched them up, wedging my boots under his sweaty armpits. I was folded in two and my ass was pointing straight up. I muttered a muffled, "No, no, no," as I guessed what was about to happen. 

I felt the dominant American's hands slide under the leg holes of my trunks. He yanked them up, into my ass crack, wedging them up and exposing my butt cheeks. My prized trunks were turned into a painful thong. I squirmed, but 250 lbs of grade-A American beef is not easily moved. I had no leverage as Joe spanked my bare ass. SMACK! SMACK! SMACK! I felt the combined burn of the spanking and the sheer humiliation of the incident. My American jobber was proving to be anything but the beta bottom I had expected.

Even though the spanking was bad, Joe knew he wasn't going to spank a submission out of me. He rolled me back, putting more pressure on my shoulders, face and neck. I needed to focus and summon every ounce of strength I had. I kicked my legs forward and the force added to the sweat in Joe’s armpits toppled him forward. I squirmed back to the edge of the mat to catch my breath. I noticed my abs were bright red from the punches and slaps. I could only imagine how red my ass was. Joe came at me, but I dodged, rather than engage. I scrambled to my feet and moved back. I needed to catch my wits.

I had to leave my trunks wedged up my ass. Joe was aggressive, looking for any opening, so every time I started to reach back to unwedge them, he darted forward. Arms raised and knees bent in a defensive posture, I circled around, avoiding the American musclebear who, so far, was dominating me in a way I wasn't used to. I had never been manhandled like this. I needed a moment to think.

I could see that Joe’s thick cock was raging in his skimpy trunks. He was definitely getting off on what was happening. He was also getting cocky. As we circled, he paused and raised his arms, flexing, emphasizing his superior power. We moved to lock up, but this time, I made the first move. I maneuvered him into a hard headlock. I tightened my grip on his bald head, squeezing hard. Joe slammed a forearm into my back. I didn't wait for him to do it again. I pulled forward, flipping him over onto the mat, holding onto the tight headlock. SPLAT! I continued to squeeze hard as he moaned, a sound I appreciated.

As I considered my next move, Joe thought faster. He tightly grabbed the narrow side of my wedged trunks and rolled me over him and onto my shoulders. The move allowed his sweaty, bald head to slip out of my headlock. As I rolled back to my knees, Joe clotheslined my chest, driving me back. WHOMP! He moved on top of me, but I moved fast enough to grab him around the back of his neck in a front facelock. I swung my legs up, scissoring him. I had a firm lock and he grunted again. I held him tightly, but I couldn't get any force on my scissors.

Before I could adjust into a better submission position, Joe demonstrated his power again. He reached under me and somehow lifted me up. The strain on his neck must have been high, but I wasn't up for long. He slammed me down on my sore back, driving his weight down on top of me. BAM! I held on, so he did it again. BAM! My grip on his neck was lost and he pulled back, kneeling, with my poorly positioned scissors still around his waist. He looked at me, lying back, legs wrapped around him and smiled maniacally. I squeezed my useless scissors, but he just pounded my stomach. THUD! OOF! My legs parted, but Joe kept abusing my midsection. THUD! POW! THUD!

After a few fists, he opened his hands and actually came in for a claw! ARGH! I had used and felt a claw in pro-fantasy, but thought it was a fake move. Not the way Joe applied it. I grabbed his wrist and tried to pull his hand free, but it was like trying to lift a fence post anchored in concrete with your bare hands. I arched my back, lifting my hips, but it didn't help. My face was contorted in pain as I struggled in vain. I gyrated helplessly against his fingers digging into my body. So far, his strategy of repeated hits on my back and abs were wearing my core down, whereas I didn't seem to have any game plan at all.

After a while (I had no sense of time, just pain), Joe slid his free arm under my raised hips. He finally released the claw, grabbed my left leg and spun me over, sitting back in a single leg crab. He wrenched back as I grunted in pain. I pounded the mat in frustration. Fuck, this daddy bear was killing me. I tried bridging and kicking my leg forward, but his weight seemed to grow exponentially while he was on top of me. Not satisfied with the crab, Joe reached down and squeezed my balls. AAHHH! I hated letting Joe know he was hurting me, but I couldn't contain myself. Still, I stubbornly refused to give in. Despite it all, I wasn't lying when I said I could take punishment. I focused my will and withstood the assault, periodically trying to bridge, twist or kick my way out and failing every time.

When I didn't submit, Joe knew he had to move on. He released my balls and my leg. I crashed down, free, but I was slow to move. With agility that defied his size, Joe spun around and drove two quick elbows into the small of my aching back. He then planted a knee in my back and reached under my chin. He pulled back and stretched me out again. It hurt, but I still wouldn't give in.

Joe again gave up his hold, but I just couldn't react fast enough. He dropped his entire body on mine, driving the air out of me. I felt him grind his hard cock against my ass. On top of me, Joe slid his hands under my arms and locked on a full nelson. He rolled me over, on top of him, locking in the full nelson. He wrapped his legs around my waist to control me.

Joe wrenched the full nelson hard. My chin was pressed against my chest and my shoulders were stretched back. UNH! OOHHHHH! ARGH! I moaned as I tried to power out, but it wasn't happening. Joe was simply too strong. If he had proved nothing else, it was that he was not some soft older muscle jobber - he was hard power, and I would never overpower him to get out of this.

I felt his thumbs undoing the knot of my mask lace as I was trapped. The loop came undone, and I got worried. No! My mask was not coming off! With no chance of powering out, I went in a different direction. Using my powerful legs, I bridged up, lifting our hips off the mat. I slammed down, simultaneously driving my hips into his and flexing my arms as hard as I could. After the second time, Joe’s legs parted, and his hands lost their grip.

Finally free on my terms, I wasted no time trying to turn things around. I flipped over and drove a forearm into his lower abdomen. The air left him. I scrambled up and dropped another, this time higher, elbow on his midsection. With Joe finally on the defensive I quickly leapt up and came down, torso on torso. I slid my legs outside and beneath his, locking my ankles under his calves. I parted his legs quickly into a grapevine while I planted my hands on his forearms (I know, I know, but I couldn't reach his wrists), holding them down. His muscular forearms were so thick, I couldn't really grab them tightly, just push down on them.

Joe had a grimace on his face as I stretched his groin as wide as I could. At the very least, I was giving my back, abs and shoulders a rest. But I also thought that I might get a submission. So far, Joe had outsmarted and overpowered me at every turn, but he couldn't be more flexible than me, not at his size and age, right? I didn't get a chance to find out.

Joe looked me right in the eye and I felt hypnotized. Man, his eyes were so hot that I almost leaned down for a kiss. With my attention focused on the staredown, he quickly flexed his mighty arms and yanked them swiftly down. They slid right out from under my hands. Joe drove two fists into my sides. He bucked wildly and we rolled to the left. I lost my lock on the grapevine. We rolled around, struggling to get into a dominant position. Our two beefy bodies struggled and squirmed. Joe tried to use his weight, but the heat in the room and the struggle had made the mat slippery, allowing me to slide out from under him several times.

We struggled in a series of arm locks, face locks, scissors and other grappling positions, but nothing took. With his power and (I hated to admit this) skill advantage, Joe finally got on top of me, but I managed to bring my legs up and under him. He went for the obvious and tried pinning me with his shoulders under my knees, but I turned our position into a tight head scissors. Joe’s head turned red as I squeezed my legs together. His head was perfectly placed in my crotch with the strongest part of my legs crushing his head and my ankles locked tightly. I applied the pressure, and he went down groaning, flat on his stomach, with my feet on his back.

Joe brought his hands up, punching my legs, but my muscles were flexed and firm. He tried reaching around to claw at my abs, but I grabbed his wrists and held him at bay. I had beaten quite a few guys with this move. Everyone I wrestled, even earlier on when I did nothing but lose and learn, acknowledged that my legs were really powerful weapons.

I could tell he was weakening. His hands were opening and looking close to tapping. I squeezed and squeezed, tighter and tighter. I managed to slide my boot into the waistband of his American flag trunks. I hooked it over my toe and pull up as I stretched back, applying as much pressure as I could to the scissors. My boots were wedging his skimpy trunks up. I knew this would be painful, given how hard his cock was and it was passive on my part, requiring zero energy to inflict real pain.

The hairy beast was trying to hold out, maybe hoping I would give up on my hold like he did, but I could keep this up forever and had no intention of letting go. I was finally in control, and he was going to submit. If there was a real jobber anywhere in my American daddy bear, it would have to come out now. With his nose full of my musk and the humiliating wedgie, all Joe needed was a push.

"Give it up, old man! You're done ... first fall to Canada!" I mocked him and squeezed as hard as I could.

I wanted to demoralize him, since he had been so dominant, but my taunts had the opposite effect. RRROOOOOAAAAAARRRRR! Joe screamed a battle cry and brought his knees up under him. Soon, he was up to one foot. I just squeezed harder, convinced I could still beat him with this move. His hands were free, as I moved mine to pull his head deep in my crotch. I focused all my strength on my legs. He unhooked his trunks from my boots. Fuck. With incredible resolve, the American stud stepped over, flipping me onto my stomach. My scissors actually failed me, and his sweaty bald head slipped out.

Joe grabbed my legs, lifting them up and locking on a full Boston crab! I couldn't believe it. I was trapped and helpless again. I moaned and groaned, pounded the mat, but couldn't do anything else. I tried bridging, but my back was in too much pain. UNH! AAAHHHHH! I couldn't suppress my cries of pain.

"Who's done now, bitch? Got something to say?" Joe yelled at me.

"N-n-no," I weakly said.

"I can do this all day ... the longer you hold out, the easier the second fall's going to be. Although couldn't be much easier than this one." Joe boasted. Joe cranked harder. "That's American muscle, bitch, bending you in half!"

I tapped the mat, but Joe either ignored me or couldn't tell if I was tapping or just pounding the mat again. I didn't want to say it, but I had to -

"Okay, okay ... give. I give!"

“YEAH, YOU DO!” Joe yelled and immediately released the hold, letting my legs collapse down. I reached for my back, rubbing it and looked up to see him walking away to the bar. Joe grabbed the beer he opened earlier and chugged it.

Joe turned to me and said, "Still cold. I knew you wouldn't last long enough for it to get warm, little Canadian boy."

What could I say? I rolled to my knees, still rubbing my back. Sweaty and pumped, Joe looked stronger and more impressive than ever. Damn, already down one fall and if anyone was getting worn out, it was me.

"One more fall and you're all mine, boy." Joe flexed his right arm and adjusted his ever-growing package with his left hand to emphasize what I was in for. It didn't look good for me, but I refused to give up.

We had agreed on two minutes between rounds ... ready or not, time was up.

The Second Fall

I climbed to my feet and finally unwedged my trunks from my ass. As we circled for round two, with my confidence shattered, I tried to develop a plan (I know, I should have taken this more seriously and thought about that pre-match instead of fantasizing about after the match stakes).

Joe moved in and I lifted my arms for another lockup, but he fooled me (again). Joe dove under my arms and wrapped his arms around my waist, lifting and turning me. SLAM! He threw me down to the mat, hard and rolled me onto my stomach. Joe held me down with one hand on the back of my neck while he reached down and grabbed my trunks. He pulled them up hard and fast, reapplying the wedgie. My flag trunks went deeper up my ass this time, the maple leaf completely disappearing. I let out a yelp.

Joe got off me, stood up and moved back. I couldn't believe it - he was so confident he could waste a surprise move and advantage just to humiliate me. I realized that this wedgie wasn’t about winning. It was revenge for the one I applied. It was showing me how superior he was, and it worked. Fuck, I was completely outclassed.

Joe raised his arms and opened his hands to challenge me to a test of strength. I rolled up to my feet, not bothering to even think about my trunks. I rolled my shoulders and lifted my arms, accepting the challenge. Why not? My mind was full of doubts, but if I backed away, how could I look this guy in the eye? How could I look myself in the eye? Plus, I looked at it as a chance for my back to recover some more.

We locked hands and it was on. I strained to keep him from forcing my hands back. We crashed chests, arms extended. I have no idea if he was giving it his all (that's how deep he was into my head, I wasn't even giving myself credit for lasting ten seconds against him), but I was holding my own as we moved around the mat. His coarse chest hair felt like sandpaper against my smooth pecs, but it felt good. We grunted and strained, man vs man. I knew that this was as much about position as strength, so I kept moving and flexing my wrists and forearms to maintain an equal position.

Joe stepped back and crashed forward, slamming his chest into mine. He repeated the move and immediately pushed down. My wrists bent back, and I was brought to one knee. I pushed up, but he now had too much leverage. Joe stepped in and pulled me forward, slamming my face with his pouch. Only his spandex stars and stripes separated my face from his cock. I got a nose full of him and it was intoxicating. Joe stepped back and really applied pressure to my wrists.

I had lost another challenge, but I wasn't submitting or giving up. I prepared to head butt his gut, but instead, I was pulled into his waiting knee against my chest. WHOMP! UNH! Joe let go of my hands and grabbed my mask. He forced my head between his legs and closed up. I knelt there, suddenly in pain with my head locked in a hard standing head scissors. I braced my hands on Joe’s massive thighs - man, were they solid. The good thing about a standing head scissors is that there usually isn't as much pressure as one on the ground. But that didn't mean I wasn't trapped. As I thought about what to do, Joe grabbed my wrists, which were resting on his thighs and brought my arms up and back, twisting them into painful armlocks. He accomplished two things - removed my arms from the equation, making me more trapped than ever and applied pressure to my shoulders.

Joe kept up the pressure. Even my back started to hurt as I was bent over in an awkward position for minutes that seemed like hours. I could do nothing but moan and steel my will not to give in. Once again, he realized that I could take some punishment, because he let go of the head scissors. But not my wrists!

Joe brought my arms together behind my back and deftly gripped both wrists together, switching his grip. He stepped over me and pushed my arms forward. Suddenly, I was crouched, face forced to the mat with this American beast behind and over me.

Joe moved back, pulling me with him. He planted a knee in my lower back and used my arms to bend me back. The pressure was intense, my back still feeling the hurt from the first round and my shoulders cramping in agony from this extensive and lengthy punishment. I moaned and grunted, but did not submit, as he twisted me back, bending my spine and shoulders into directions they were never intended to go. Once again, I didn't free myself through any strength, smarts or skill, just stubbornness and refusal to give in. Joe released the hold, throwing me forward, flat on my face.

I tried to crawl forward and rise to my knees. STOMP! A hard stomp to my lower back with the black sole of his black patent leather boot ended that plan. STOMP! STOMP! Another two ensured I didn't move while he stepped over me and got me into position for whatever he planned to do next.

Joe grabbed the back of my still wedgied trunks. He lifted my hips off the ground and dragged me around the mat. I couldn't do anything but slide where he wanted to take me. I will say this – I bought some high-quality trunks, because they held as he used them to lift my 215 lb carcass around.

Joe finally dropped me, releasing his grip on my trunks. The next thing I felt was Joe reaching under my arms and pulling my shoulders off the mat. He slid them over his knees as he sat on my ass then slid up to plant his butt on the small of my back. He wrenched me up and back. When he was satisfied, he locked his hands under my chin and pulled my head back.

NO, NO, NO! I was in the camel clutch from Hell! ARGH! I was in agony! I started to give immediately, even I couldn't take this, but as I started to speak, Joe eased up and let me come forward. I thought, maybe he'll give up again, but no, I wasn't going anywhere. He moved his hands from my chin, and I felt him pull on the laces of my mask. He had untied it in the first round, but now he was pulling it out completely! I shook my head, in a futile attempt to stop him, but I couldn't. Within seconds, the lace was out and only gravity was protecting my identity.

With that done, Joe taunted me with light smacks to the back of my head. He said, "Give up, boy."

"No."

Joe’s hands slid under my chin, and he wrenched me back again. "OKAY, OKAY, OKAY, I GIVE, I GIVE, I GIVE!"

Joe let me slide forward but didn't release me. He said, "Now, let's make a few things clear around here. You ever gonna wear another country's flag while you're in America again?" When I didn't immediately answer, he pulled back slightly.

"No! I won't. I promise!"

"You gonna live up to our stakes or you want to go another round? Best 3 out of 5?"

I wanted to accept his offer, but I knew better at this point. I said quickly, "I'm done, I'll honor the stakes. Please, just let me go. My back ..."

"One last thing, you Canookian jobber boy ... what are you gonna call carbonated drinks from now on?"

I thought, what? Then Joe eased me back and I remembered fast. I said, "Soda! Soda! I'll call it soda."

"Good jobber boy."

Joe let me fall on my face. As I lied there, I felt him grab my trunks again. This time, they weren't going up my ass, but coming down my ass. He was taking his prize. Just the first of many, but the most symbolic. He slipped them over my boots, and I knew that they were gone for good. My Canadian heel days were officially and irrevocably over.

The Aftermath

Fuck. The heat in the room was now oppressive as the realization of my total loss hit me. I was sprawled on the mat, eyes closed and motionless. I was completely drenched in sweat, mine and Joe’s, exhausted and destroyed. I had lost before; I'm not going to pretend otherwise. But never like this. I had been thrown around, picked up and generally manhandled. I had submitted, twice, and not gotten even close to getting a guy almost twice my age to submit.

I had lost my trunks. Fuck. And I was probably going to lose a lot more than that. Double fuck. Our stakes were clear and open - Joe could pretty much have his way with me and I would have to see how far he would go. I rolled onto my back and just lied there, recovering and waiting. My cock was semi-hard and leaking - Joe was a hot man and his cock looked good in his trunks. I rationalized that it's not like sex with him would be bad. If someone is going to flip me, at least he earned it.

After a few minutes, I felt Joe’s boot on my chest. I looked up to see him towering over me, holding my belt in his left hand. He had his cigar in his mouth. It was lit and stinking up the room. I didn't say anything - he had earned the right to smoke his victory cigar. He had another beer in his right hand. He grabbed the cigar in his fingers and took a swig from the beer as he looked down at me and shook his head.

"Pathetic. Get the fuck up. You have work to do. Put this on me," the champ ordered. He tossed the belt down at me.

I rolled to my side and started to stand, only to have Joe push me back down with his boot. I looked at him, confused. He said, "Stay on your knees."

I rolled over and got to my knees. I moved to go behind him, but he grabbed my untied mask and shook his head. He was making me reach around him to fasten it, my face pressed into his bulging trunks as I leveled the belt and snapped it snugly around his waist. I felt so humiliated that he still had his trunks, while mine were gone. I finally noticed that my Canadian flag was down off the wall, too. Crap.

I sat back on my knees, stared at my, no, his, belt, and hoped that was it for my punishment. Or maybe I didn't. In spite of everything, my exposed cock was throbbing and standing at full attention. A part of me had to admit that I was getting a thrill from all this. Joe was all man and hotter than ever. I wanted to bring out his submissive jobber side, but he had ignited mine.

Joe slid his boot under my hanging balls and bounced them up and down. It sent a chill up my spine as he taunted me, taking his time. He took a few puffs of his cigar and a few more swigs of beer. My balls just kept bouncing. Finally, when he finished both beer and cigar, he pulled his boot back. He walked to the bar, stubbed his cigar out in the sink and put his beer on the counter, grabbing a fourth beer.

When he returned, he pointed at his boot. I had leaked pre-cum onto the side when he was bouncing my balls. "Clean it up." I leaned forward and licked it off, cleaning his boots with my tongue. I had no choice. He had dominated me in every way, and I wouldn't shirk from our stakes. If I had won, I planned to do this to him and more. He didn't stop me until I had licked every inch of the shiny black leather. I don't know how long it took, but I was his for the rest of the day and night, if he wanted. As I finished, I felt Joe’s fingers slide under the back flap of my unlaced mask and pull me up until I was eye level with his bulge.

“Let’s get that mouth and throat loosened up.” Joe pushed my head back and tilted the beer bottle over. About half the beer washed over my mask and down my body before he shoved the tip against my lips, forcing me to chug the other half. Not like I couldn’t do it, I’m Canadian after all, but it wasn’t pleasant. When the beer was empty, he put the neck of the bottle in my mouth, mocking me by fucking my face with it.

Joe slid the bottle free and tossed it aside. Standing in front of me again, Joe reached down, pulled the front of his trunks down, wedging them behind his bull balls, releasing his throbbing cock. It was a gorgeous, thick, rock-hard piece of manmeat that exceeded mine in length and girth. Great, another area where he had me beat.

Joe shoved his cock through my mask’s mouth hole, over my lips and deep into my mouth, driving it in until the head of his cock hit the back of my throat. He used my loose mask to control me and hold me close. I felt my nose brush up on my belt ... I mean, my former belt. I closed my eyes and got ready to suck.

"Eyes open, my Canookian jobber boy!" Joe ordered. He wanted me to see my - damn - HIS belt and the edges of his trunks - the stars and stripes - while he fucked my face. And make no mistake, that is what was happening ... he held my head tightly and controlled the pace, depth and speed. There was no technique on my part, no pleasure for me in the act - my mouth was nothing but a wet open hole at that point.

Joe pulled my mask forward slowly with every thrust. I felt his body shudder and a second later, he shot his load down my throat. It was a lot, but I swallowed every drop like a good jobber boy. When he pulled his cock out of my mouth, my mask went with it. I looked in horror as I realized that the mask dangling from his cock by the mouth hole was another thing he had now taken from me.

"Look at me, loser. Show me that pretty face." I did. He said, "Mm, cute. Just like I thought, you're just a fresh-faced jobber boy who likes to play heel. Well look at me. This is what a real heel looks like, kid." I had to agree, and my cock showed it. He pulled my mask off his dick and tossed it aside like it was garbage. He stood there, cock and balls still hanging out over his American flag trunks, title belt resting just above his package, black boots shiny and clean from my saliva ... I couldn't pretend he wasn't perfection at that moment.

Joe’s cock was swelling up again. I was impressed that he might be ready to go again, until I realized that my ass was probably his next target.

Joe circled me as I knelt there. He was surveying his prize. I have no idea if this was just theatre or if he was really trying to decide what to do with me. Either way, pre-cum continued to leak out of my cock. The pressure was really building, and I really needed to jack it, but there was no way he would let me.

Joe said, "Get up.” I did. “What are you?"

"I'm your Canookian jobber boy!" I said, head bowed. He waited, staring at me. I added, "Sir."

Joe moved in close, his hot, smoky breath on my face. I turned slightly. He didn't like that, because he grabbed my hair, held my head and kissed me long and hard. It was a great kiss, but his breath was foul. When he released me, I instinctively coughed.  He laughed at my discomfort. Despite his cigar breath, the dominant, powerful kiss had only made my hard on rage more. Joe grabbed my cock and balls and worked them. He squeezed and smiled at my helplessness. My purple cock head was still leaking, dripping long strands of pre-cum on my leg and down to the mat.

Joe grabbed my hair and forced me back to the mat. He said, “Get on your hands and knees, bitch. And start singing that thing you call a national anthem.”

“O Canada?” I asked, confused.

“Yeah.”

While I started singing on hands and knees, Joe grabbed a condom from the bar, one of the ones I had planned to use on him. I must have looked pretty pathetic, on hands and knees, only wearing my kneepads and boots, and singing O Canada. Joe moved in behind me and positioned himself. I finished the anthem, but he ordered me to keep singing and not stop until ordered.

I started again. “O … OOHHH!” His thick cock slid inside me, “Canada, our home and NAYYY-tive …” He thrust deep into my ass. I tried to keep singing as best I could while his thick cock worked inside me. My alpha top hole stretched out like the beta bottom I’d become for him. He worked at fucking me as I sang/moaned.

Joe said, “Yeah, keep singing. OH, FUCK YEAH. Every time you hear that fucking song, you’ll think of this, jobber boy. FUCK, TAKE IT BITCH! You’ll remember how an American heel beat you and fucked you. YEAH, FUCK!” Joe reached under me and felt my hard cock. He taunted, “Oh, you like being fucked. You love being my bitch. I bet you get hard every time you hear this from now on, thinking about me. YEAH!”

I just kept singing through his taunts, but he was right. How could I not think of this? Having burned off a load, he fucked me for a long time. I lost count how many times I sang the song. Finally, I heard his breathing get faster. He pulled out, ripped the condom off and shot his second load of cum up my back.

Joe rose and grabbed my hair again, pulling me back to my knees. He kissed me again, finally letting me stop singing. When he let go of the lip lock, he moved behind me and bent me back into a dragon sleeper, making sure my mouth was perfectly buried in his armpit. I bent back in pain – my knees were aching from all the kneeling, plus the move stretched my aching back.

Joe said, “Jerk yourself, Canookian jobber boy. I wanna see you shoot that worthless seed of yours while you suck on my pit.”

I eagerly started working my aching cock as I sucked his sweaty hairy pit. Within seconds, I was shuddering and shooting a huge load up my stomach and pecs, spraying as far as Joe’s arm. When I was finally done, Joe threw me to the side. He forced his arm in my face and ordered me to clean it. I obediently licked my cum off his massive arm. When I was done, he got up and I practically passed out I was so exhausted.

SLAP! I felt Joe’s hand across my face, waking me up. I looked up and Joe stood over me. He dropped to his knees, straddling my waist. Joe rubbed my chest then grabbed my pecs. He squeezed them hard, applying a rough pec claw. I had no resistance left in me. I moaned and squirmed.

Joe said, “No more Canookian shit for you. Got it, jobber boy?”

I meekly said, “Yes, Sir, I get it.”

Joe released the pec claw. “I’m gonna clean up while you think about things.”

“Yes, Sir.”

The hairy beast grabbed his trunks, my trunks, and his jacket. He walked up the stairs. I stayed on the mat, thinking about the match as instructed. I alternated between feeling humiliated and thrilled, finally landing on feeling humiliated that I was thrilled about being thoroughly used and destroyed by a real fucking heel. I heard the shower running upstairs. I put off cleaning the mats and decided to join Joe.

I never asked Joe or Shawn directly if this was a set up. I did thank them both for the hookup, though.

THE END