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Disclaimer: All characters are 18 or plus years old. Please note English is not my first language, so you might stumble across a few spelling mistakes. This is also a fetish/kinky wedgie/humiliation story. Strong language. No major spoilers here! - Wade Wilson, better known as Deadpool, had planned a surprise encounter for Captain America. He knew Steve Rogers was a symbol of righteousness and all that, but he just couldn't resist the temptation to humiliate the pride of America. If he could hit the United States most famous butt, it would mean that no one would be able to stop him. Wade stalked the blonde for days, waiting for the perfect opportunity. That moment presented itself one day at Captain’s America private gym. After some preparation and quick setting up, the anti-hero could finally set his plan in motion. Deadpool knew his way around security systems, and breaking into Cap's private gym was a cakewalk. He silently crept inside, finding Steve mid-workout session, his muscular form gleaming with sweat. Roger was shirtless, revealing a godlike physique sculpted by years of rigorous training and his enhanced abilities. The sight of the hero's bare chest and powerful muscles only fueled Deadpool's mischievous intentions, especially when his eyes wondered at the tight blue shorts of the blonde. Unable to hold back, Deadpool announced his presence with a smirk, "Ahh, so this is where the star hero of America works out? Pretty neat, Cap." He leaned against a nearby wall, his tone filled with sarcasm. Captain America paused his workout and turned to face Deadpool, immediately recognizing the masked mercenary. "Deadpool, how did you manage to get in here?" Wade shrugged, casually replying, "A little bird told me about your private gym, and I just couldn't resist paying you a visit." He walked closer, eyeing Steve’s physique. "And damn, those abs are on another level, you know that?" Despite his surprise and annoyance at Deadpool’s intrusion, Steve maintained his friendly demeanor. He wiped the sweat from his forehead and responded, "Appreciate the compliment, Deadpool, but you could have just called instead of breaking into my gym." Deadpool chuckled, enjoying the fact that Captain America was maintaining his cool demeanor. "Where's the fun in that, Cap? You know me, I like making an entrance." He approached a nearby punching bag giving it a quick strike. Steve raised an eyebrow, watching Deadpool’s antics. “True, you do have a knack for showing up unannounced. But why are you really here, Deadpool?” Deadpool feigned innocence, pretending to examine the gym equipment as he walked around. "Can't I just pay a social visit to my favorite patriotic hero?" He then turned to Captain America, a sly grin under his mask. "But alright, I admit I do have something to ask..." Steve crossed his arms, his expression a mix of curiosity and slight suspicion. "Go on then." Deadpool sauntered closer to the blonde, a mischievous glimmer in his eyes. "Well, Cap, I've always been curious about one thing... How do you manage to keep how do you keep your underwear from riding up during all your heroics? I think we all know your suit needs an upgrade, ASAP!” Steve's expression transformed into a mix of surprise and amusement, not expecting such a question. He chuckled lightly, appreciating the humor. "Deadpool, seriously? You broke into my private gym just to ask me about my undies?" Deadpool couldn't help but chuckle as well, enjoying the lighthearted moment. "Hey, can you blame me? It's a genuine concern! You're out there saving the world while fighting crime, and I can't shake the feeling that you're walking around with a wedgie all day." The blonde rolled his eyes, but a smile tugged at the corner of his lips. "You know, Deadpool, you have a unique way of bringing up topics. But for your information, it’s a well-tailored suit, and I’ve never experienced any, um, wedgie issues." Deadpool feigned shock, putting his hands on his hips dramatically. "What?! No wedgies at all? Damn, that's almost un-American! We can't have our symbol of freedom without a little cotton-induced discomfort." Steve couldn't help but laugh at Wade’s antics. "I’ll keep that in mind for my next upgrade. But seriously, is that all you broke in here to ask me?" The anti-hero leaned closer, a mischievous grin on his masked face. "Not quite, Cap. You see, I have decided to embark on a wedgie crusade of sorts... Care to guess my next target?" Captain America sighed, knowing where this was going. "Let me guess, you plan to give me a wedgie?" Deadpool nodded, unable to contain his excitement. "Bingo! I just couldn’t pass up the opportunity to give the symbol of America a wedgie. It’s like a right of passage in the anti-hero community. Plus, it’s for the sake of the American people!” Steve shook his head, a mixture of disbelief and amusement. "Deadpool, this is ridiculous. I'm not allowing you to give me a wedgie just so you can have some twisted sense of satisfaction." Deadpool tsked, feigning disappointment. "Oh, come on, Steve! Don’t be a buzzkill. Think of it as a bonding moment. I’ll give you a wedgie and you will become just a little bit more relatable. It’s a win-winning situation!” The hero couldn’t help but chuckle at Deadpool's persistence. "Sorry to burst your bubble, but no way. I’m not trading my dignity for you to check a box in your hit list." Wade pouted, clearly enjoying their little back-and-forth banter. "Aww, c’mon, Steve! Where is your sense of humor? Think of all the laughs and stories we’ll have later. Plus, you can add ‘Experienced a Wedgie from Deadpool’ to your list of life achievements." Cap crossed his arms again, his expression a mix of amusement and stubbornness. "Nice try, but is not up for negotiations. I've fought aliens, creatures from the multiverse, and terrorist groups. I am pretty positive I can handle a wedgie-attack from Deadpool." Deadpool feigned offense, putting his hand on his chest dramatically. "Oh, really now? Wait, let me show you something!” Deadpool patted himself down looking for his phone, pulling the device out, and finicking with it for a minute. “What could you possibly show me that would make me—-“ “AHA! Here, here, here! Look!” Deadpool raises his phone screen, displaying a video of Spider-Man’s hanging wedgie state (see Deadpool Wedgies the Marvel Universe #00). Steve's expression changed to shock and disbelief as he looked at the video. "Is that ...Spider-Man? Being suspended by his underwear?" Deadpool's laugh rumbled. "Indeed it is, Cap! I gave him a wedgie for the ages. And let me tell you, ol' Web-Head didn’t take it well." he said, enjoying the effect the video was having on Cap. “Now imagine if this gets out— it will go viral in less than a minute! Imagine what people would start saying about the Avengers!” Captain America’s eyes widened, his pride as the leader of the hero group and role model shaken by the thought. "You wouldn’t dare," he said, his voice firm but showing a hint of uncertainty. Deadpool gave a sly smile under his mask. "Oh, but I would, Cap. One press of a button and that video is all over the internet. The mighty Avengers falling into my wedgie trap, one hero at a time." He made a big show of reaching his finger to the ‘upload’ button on his phone. "So, what’s your choice, Steve? Are you ready to end up as the newest victim of my wedgie collection?" The blonde stared conflicted. On one hand, he knew Deadpool's threat was real and had an obligation as a member of the Avengers to maintain their image, but on the other hand, he couldn’t allow himself to be humiliated in such a way. He let out a sigh, realizing he was stuck between a rock and a hard place. "Fine, you've got me, Deadpool. You win. But the video stays unpublished, you got that? The mercenary laughter filled the room. “Atta boy, Cap! Knew you’d make the right choice. I’ll honor the deal. Now, let the wedgie fun begin!” He approached the muscular man, a menacing grin under his mask. “Now… what kind of wedgie would suit the perfect patriotic hero like yourself?” Steve clenched his fists, bracing himself for the imminent humiliation. "Just get it over with," he said through gritted teeth. Deadpool circled around him, contemplating the perfect wedgie. "Hmmm... I want it to be a worthy one... Wait! I got it. How about an atomic wedgie? Seems fitting for the man who fought in WW2 and all." Captain America winced at the suggestion. "An atomic wedgie...? Seriously?" Despite his attempt to sound composed, he couldn’t hide the hint of anxiety in his voice. Deadpool chuckled, clearly amused by his target's unease. "Oh, come on, Cap. It’ll be legendary! Just picture it – the Captain America, hero of America, with his tighty-whities hoisted up over his head, a true symbol of vulnerability." Steve clenched his jaw, his face reddening in embarrassment. He couldn’t believe he was about to let this happen. "All right. But you better keep to your words and make sure that video stays unpublished." Deadpool gave a mock salute. "Scout's honor, Cap!” Deadpool fiddled with the waistband of Captain America’s shorts, only to pull it down a little, revealing the hero’s American-themed briefs. The fabric was designed with the United States flag, with horizontal red, blue, and white stripes. “Who would’ve guessed?” Wade watched as his comment made Steve’s ears go red out of embarrassment. He wrapped his fingers in the spandex fabric of the exposed undies, feeling the accumulated sweat of the workout Steve was working on earlier. With a swift tug, Deadpool pulled back on the elastic of the undies, giving Captain America a sharp wedgie as the briefs started riding up between his muscular and fatty cheeks. “HHmHgg— gHhmn…” Steve grunted in pain and surprise as the wedgie took shape. The strong wedgie, caused by Deadpool’s powerful pull, felt extremely uncomfortable for Steve, as the fabric assaulted his asshole with a sting of pain. He shifted his weight standing on his tip-toes, trying to alleviate the burning sensation, only to be lifted off the ground by another sharp yank. Deadpool chuckled at the sight of Captain America in distress. “Havin’ trouble staying on your feet, Cap?” He asked in a mix of mockery and sadistic glee. The blonde tried to respond, but his breath escaped him as Deadpool started to bounce him by his underwear. “D-AHH-Hn—mnh!” He could only manage to let out strangled grunts and moans as the wedgie continued to bite into his flesh, lifting him higher off the ground. Every pull, every bounce of the wedgie brought a shockwave of pain to Steve's ass. The wedgie was almost unbearable, but he gritted his teeth, not wanting to give Deadpool the satisfaction of hearing him beg for it to stop. "What’s the matter, Captain? Worse than the aliens and robots?" Deadpool teased, enjoying the way Steve was helplessly dangling by his briefs, as his toes stretched to reach the ground at every pull, and his shorts traveled down his huge tights. Rogers let out a frustrated grunt as Deadpool continued to bounce him. “HghMMH! MMhg! AhHh—“ Every pull of the wedgie felt like a hot branding iron on his sensitive skin. It was taking all of his willpower not to break down and beg for mercy. "Shut... up," he managed to bite out between clenched teeth. Deadpool chuckled, continuing his sadistic game. He pulled even harder, the elastic of Steve’s underwear almost reaching his neck. “C’mon buddy, this is a gym, right?? I have to get my reps in!” Each pull from Deadpool seemed to bring the hero closer to the brink. His body was trembling after each shockwave of pain coming from his ass, as his cheeks jiggled and was set apart by each yank. He gritted his teeth, trying not to cry out in pain, as Deadpool continued to stretch his spandex briefs for the next few minutes, leaving little to the imagination. Steve could feel the sweat dripping down his face and the burning sensation in his butt cheeks was becoming unbearable. He knew he couldn’t take much more. "HnnGh— Deadpool, p-please..." he managed to gasp out between his whimpers. Deadpool paused his bouncing wedgie-attack for a moment, hearing Steve’s plea. "Well, if you insist, Cap," he said, his voice laced with mischief. Deadpool moved to the front of Captain America, then made a final yank at the briefs, pulling them up and over the blonde’s head. The force of the wedgie caused the fabric to stretch over Steve’s face, as Deadpool moved the fabric side to side to give him a noogie with his own underwear. “AHHGHNMNNH!!! MHHHNNHMM!!!!!” Captain America let out a strangled cry as the wedgie reached its peak. The tight, elastic fabric was painfully squeezing his head and his face was burning hot with humiliation. He could only wait for Deadpool to finish his torment, feeling utterly helpless. Wade chuckled at the sight of the trembling man, his face printed against his own sweaty underwear. "Well, that's one for the history books! Captain America himself, with his briefs on his head! How does it feel, Cap? You’ve been well and truly atomized by my wedgie-jitsu." Deadpool circled the hero, watching his behind, which had a “V” shape by Steve’s striped briefs, exposing his pale ass. “AA-aHh—hmn… I-It’s so d-deep… mhhn…”Cap grunted in discomfort, the feeling of the stretched fabric over his head, as well as the strain on his backside, was starting to become too much. He tried to raise his arms to take the offending underwear off but found himself unable to do so. “Just get it off…" he mumbled through the stretched elastic, struggling to keep what was left of his dignity. Deadpool chuckled at Steve’s plea, amused by the fact that the mighty Captain America was at his mercy. “Sure thing, Cap! First things first, I have to immortalize this moment!” Then, he patted himself for a moment and grabbed a permanent marker from his pocket. “And I think it needs an autograph.” Deadpool signed his name on one of Steve’s asscheeks, each letter a cold and sharp sting against the hot flesh. On the other cheek, he wrote “America’s Wedgie-Butt”. Then, he grabbed his phone, holding it so that both Cap and himself were in the frame, putting one of his arms over the hero’s shoulder. He gave a wide grin, making a peace sign with his hand. "Smile, Steve! Say ‘cheese’!" Captain America groaned, his face still muffled by the fabric of his own briefs. He felt a mix of frustration and helplessness, knowing that he couldn’t do anything to stop Deadpool from taking a photo of this humiliating moment. "C-Cheese..." he mumbled through the elastic, his voice a mixture of resignation and resentment. Deadpool chuckled as he captured the photo, enjoying the sight of Captain America in his most embarrassing state. "Great! That’ll make a nice addition to my photo album! Maybe I’ll even put it as my phone’s wallpaper." As the anti-hero stepped away from the selfie, Captain America could only hear a few other loud clicks, as the anti-hero took several more pictures. Wade then approached the blonde, holding his package with one of his hands, and squeezing it a bit. “Oh-oh, man! Did your nuts travel inside of you?” Steve flinched slightly at the sudden touch, the sharp pain of his wedgie still making his lower half incredibly sensitive. He let out a deep sigh, his voice coming out as a strangled whine through the tight elastic. "N-No... they’re still... in their place," he mumbled sheepishly, embarrassment heavy in his voice. Deadpool grabbed the front of Steve’s briefs that were pressing against his stomach, giving them a strong pull, and pulling them up to the hero’s massive pecs. The fabric split his balls in the middle and even made his dick fall to the side since there was no room for it anymore in the string of fabric. “HHNMHGGGHHM!!!! MY BALLS!!!” Captain America moaned loudly, being muffled by his underwear covering his face. Deadpool chuckled, amused by Steve’s loud cries. “Oh, how the mighty have fallen…” he teased, then gave one last hard tug, leaving the front of the briefs clinging to Steve’s lower chest. Wade took one last picture to admire his handiwork, before turning to leave, capturing Captain America’s crossing his legs in shame and painting out of exhaustion. “Well, that was fun, great work out Cap! But I’ve got business to take care of. You just... stay here and enjoy that wedgie. Ciao!" Captain America could only listen in horror as Deadpool walked away, leaving him alone in the gym, trapped in the most embarrassing pain and humiliation of his life. He could only manage to let out a few pathetic sounds, as his briefs still covered his head and stuck to his body. "H-Hmh... h-how am I supposed to get out of this...?" he mumbled weakly, grasping the waistband over his head and failing at removing the wedgie stuck on top of his head. With Captain America crossed off the list, Deadpool knew exactly who his next target would be— someone that would fight back no matter what.