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A oneshot where Hunter finds out about Shawn's messy love life

a/n: I saw this art post by @seraphskater and my hand slipped. Also inspired by that one good ass fic by @tameodesza go check em out!

Hunter Hearst Helmsley was a man of taste. He preferred the finer things in life, those wrapped in gold and silk. He had the tendency to follow around what he believed was good enough for him. This was how Shawn found himself being shadowed by the blueblood every second of the day. Shawn didn’t mind it; the hawk-nosed blonde was easy on the eyes if Shawn squinted hard enough. Hunter was posh to a fault, Shawn found out, but he didn’t complain as long as Hunter made him feel like a million bucks; it did wonders for his already inflated ego. It didn’t take long for Hunter to start pursuing Shawn for something beyond his little schoolboy crush. All it took was a bouquet as big as Shawn and toothachingly sweet words (and the dirty tricks he had to do to keep Shawn WWF Champion, but Hunter digresses).

Shawn was easy to please which was why Hunter already expected the other man’s colorful love life. What he didn’t expect was how really messy it would be.

“Wait, you dated Ramon?”

“Dated is a strong word.”

Shawn snuggled closer to Hunter’s side; his legs wrapped with Hunter’s own. He pressed a kiss on the corners of his lips, hair still tangled with the leaves and petals from the behemoth of a bouquet Hunter gave him hours ago. “You know, if you want to date me, you have to deal with my seven exes.”

Hunter sputtered, “Seven?” The smaller blonde pouted, his nose scrunched, “I’m hot merchandise, everyone wants a piece of the heartbreak kid.”

The blueblood pulled Shawn closer to his chest and Shawn was more than happy to lay on something bigger than the hotel bed pillows. “And who exactly has gotten a taste of the heartbreak kid?” Hunter asked, curious.

Shawn hummed in thought, mind scraping for all the details he may have already forgotten, “Well.”

જ⁀➴

Marty Janetty

- If Hunter had to ask Marty, the former rocker would say that he was Shawn’s first everything. First kiss, first love (Shawn begs to differ), first lay. It was only natural for them to get together after starting out as a tag team.

- The chemistry between them in the ring translated into their personal lives. Marty was the more laid-back, easygoing one, balancing out Shawn’s flamboyance. Their opposing personalities seemed to complement each other well. Keyword: seemed.

- They dated for most of their time as The Midnight Rockers. Seen each other at their lowest when sharing half a granola bar for dinner, Marty being Shawn’s shoulder when the high demands of traveling from show to show took a toll on him.

- Marty found that chasing after Shawn was way harder than chasing after tag team gold. It took him months to convince Shawn to have them share a bed, let alone to get a kiss from him. Hunter could see why.

- Marty wasn’t a dead ringer for Shawn’s taste in men. He wasn’t tall, shorter than Shawn clearly. He wasn’t big either. It makes Hunter wonder how they became an item in the first place (“He was the only guy I spent time with for more than a show,” Shawn explained, “I have needs y’know”).

- Marty had a controlling hand, easily jealous, and it left a sour taste in Shawn’s mouth. Shawn lost count of how many times they had an argument that sparked from Shawn looking at another man for longer than a few seconds. Shawn wasn’t that much of a fan of being trapped in a cage. So, it was safe to say that their relationship was doomed from the start. But Shawn let it go on anyway.

- Tension built up when Shawn was given the green light to start his singles career. He knew how Marty would react to the news, so Shawn decided not to tell him anything about it until he had to throw Marty through the barber shop window.

- Shawn broke off the relationship after that. Not much love was lost between them since there wasn’t that much to begin with. Now all their interactions involved Shawn immediately turning the other direction when they made eye contact. If it wasn’t for Diesel, Shawn’s newly hired bodyguard, Marty would’ve tormented him relentlessly, or worse: wanted him back.

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The Sensational Sherri

- Shawn had this sugar mommy thing going on with Sherri. It was short-lived but it was the best few months Shawn’s ever experienced. She fed into Shawn’s ideas of his over-the-top ring gear and has bought him his endless array of jewelry.

- It only took Shawn to bat his lashes for Sherri to go on and convince the Million Dollar Man to give her the money to buy what Shawn wanted. From earrings to hats to luxury hotel rooms, Shawn got it all.

- The Sensational Sherri gave Shawn direction after being split from Marty and Shawn wasn’t quite sure how it would play out. But Shawn’s uncertainty was stomped out from Sherri’s experience. She raised his stock, so to speak.

- From an outsider’s view, they definitely had a thing going on. Shawn wasn’t even aware that he was in a sugar mommy relationship until a few years later.

- Shawn got pegged, 100%

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Diesel

- The two met at a convenience store of a gas station in the middle of nowhere. Shawn saw the top of Diesel’s head poke beyond the metal shelves of liquor and soda cans, and like a moth to a flame, Shawn hunted the other down.

- He was huge, was Shawn’s first thought. All legs and muscle. The moment Shawn had to tilt his head up just to make eye contact with the man, it was over for him. Braincells gone. He wanted to climb that man like a tree.

- Shawn did the most cliché thing imaginable to try and get the other man’s attention. And it involved him “accidentally” bumping into Diesel and spilling the bottle of water in his hands. “Oh! I’m so sorry!” Shawn exclaimed in the most fake-friendly voice he could muster. “Let me buy you another one; I’m so clumsy.”

- Diesel was taken aback. Was that deep ass voice coming from that guy? Christ. He didn’t even try to fight the laugh that escaped his lips when Shawn started pawing at the wet stain on his shirt's sleeve, obviously coping a feel of his bicep.

- “You’re really tall, do you wrestle?” “I truck.”

- The blonde pouted, hand wrapped around Diesel’s arm, “You ever get lonely?” he asked, not-so-subtly. Diesel, bless his heart, was a weak man when it came to blondes. Shawn was a hundred ways of pretty, and Diesel would be stupid to refuse the other’s advances. He does get lonely, thank you very much.

- And that was how Diesel found himself with a naked blonde man sleeping on the makeshift bed in the back of his ten-wheeled truck. That post-nut clarity hits him real strong.

- They had breakfast in a diner and, through the moment of spontaneous confidence, Shawn offered him a job. A bodyguard gig. The offer left Diesel in a pause, the soggy eggs on his fork slipped and fell back on the plate with a splat. “A what?”

- Shawn’s smile widened as he nodded in a way that reminded Diesel of the bobbleheads he collected on his truck’s dashboard. “Come on Big Daddy, you got the build.” Shawn tried to convince, “Pays better too.”

- Diesel hadn’t been given that big of a decision since he made the choice to dye his hair black. His eyes traced from Shawn’s beauty mark to the skin of his chest that peeked from his too-large shirt. The silence that followed it made Shawn pout. The blonde grabbed a napkin and scribbled his number before he tucked it in Diesel’s hands. “I’m not kidding about it, y’know,” he kissed Diesel on the cheek, “Give me a call when you make up your mind.”

- Diesel watched the man disappear beyond the diner doors and he was left with his thoughts.

- It didn’t take long for Diesel to actually call him back. And Shawn was absolutely ecstatic.

- So, there he was, following Shawn to the ring and watching his new employer dance around. They got together soon after. But it was short-lived, the two decided they were better off as friends instead of lovers. The breakup ended miles better than Shawn’s last one. Good on them.

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Razor Ramon

- Shawn thought Razor was the most annoying man alive. And Razor didn’t have any good words to say about Shawn either. They were both stubborn and didn’t know how to take “no” like proper functional adults. It only took Razor spitting his toothpick on Shawn’s lap for them to start squabbling every chance they get. Diesel became their impromptu babysitter whenever that happened.

- They had this situationship going on that confused everyone to no end. One second, they were best buddies; then the next moment, Razor was trying to choke Shawn for mocking his accent. It went on like that for most of their budding friendship. There always seemed to be this tension between the two that was heavy and pungent.

- They boned. No surprise. It was a friends-with-benefits, no-strings-attached thing. They wouldn’t call themselves an item by any means. They always found themselves in bed together after every match they had. And there were no complaints from either of them. The morning-afters seemed to be the sweetest, with Shawn ordering hotel breakfast for the both of them while Razor would untangle the knots in Shawn’s hair made from the night before. It was a moment of comfortable silence, only broken by the rustle of the bed sheets and the noise of the television.

- They started being friendly the more they spent time together, and that led to Razor becoming a part of Shawn and Diesel’s ragtag crew. They made some sort of system together, having each other’s back whenever it calls for it. Best believe, the trio became everyone’s problem in the locker room afterward.

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Sycho Sid

- Even Shawn wonders how he had the audacity to even consider Sid as a potential boyfriend. Shawn had the aching suspicion he made that decision when he was black out drunk one night.

- This all happened after an argument Shawn had with Diesel, and in a sorry attempt to make his former boyfriend jealous, he got himself a new bodyguard in the not-so-mentally there Sid.

- Shawn tried to make it work. Tried.

- But Sid was more interested in the gold wrapped around Shawn’s waist than Shawn himself.

- It was a fruitless attempt on Shawn’s part and he immediately stopped trying when Sid laughed all on Shawn’s face. The blonde can still remember the smell of his breath and it still makes him gag to this day.

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Undertaker

- Shawn can’t even wrap his head around the idea of how he managed to convince the Undertaker to date him. He’d like to think his good looks did it for him.

- In true Shawn fashion, the blonde saw one wrestler that towered over him, and it was over. He was afraid of the Undertaker at first, but in all honesty, who wasn’t? He was an enigma. Came into the wrestling scene wearing all black, hair covering most of his face, and a tub-of-lard of a man following him around with his squeak-toy voice. Maybe Shawn’s thing for taller men overshadowed all the other red flags that said men might carry.

- Shawn didn’t believe the Undertaker was essentially a walking corpse, but after laying his head on his bare chest and hearing no heartbeat, he started to rethink his life choice. (“Okay, it was kinda hot.” Hunter made a face, “Shawn-“)

- Despite their odd pairing, Shawn and the Undertaker surprisingly hit it off. The Deadman turned out to be a gentle giant, and Shawn couldn’t help but be drawn to him. To Shawn's surprise, Taker knew a thing or two about motorcycles. Lord knows how he got into it in the first place.

- Their relationship started off as Shawn treating Taker as some sort of wall, talking on and on about anything and everything. And Taker, not knowing how to respond to Shawn's endless rants, never bothered to interrupt him. That was how Taker got up to date with the latest locker room drama, which to none of his surprise, had Shawn as the center of most of them.

- Shawn became a permanent fixture in Taker’s somewhat dreary routine. Shawn’s deep voice was a nice contrast to Bearer’s and Taker welcomed the change with open arms.

- They decided to end their relationship when Shawn realized that Taker still had some of his own stuff to figure out, particularly the brother-related ones. It was a quiet affair, both in good terms. But that still didn’t stop Shawn from talking Taker’s ear off.

- When come the time that Taker’s heart starts to beat again, he was sure that Shawn was one of the reasons for his second chance to life.

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Bret Hart

- This was one of the relationships where Shawn genuinely saw himself loving Bret for the rest of their lives. They started out as friends when Bret, like the angel he was, offered some encouraging words to a still-green Shawn Michaels back in the early nineties. It meant more to Shawn than Bret realized, especially considering that Shawn was in a rather low moment in his career, unsure of how he was going to be used in the business. He’s heard of all the stories of how new talent became jobbers immediately after they debuted, and Shawn was worried he was going to be one of them. But Bret had more trust in Shawn than Shawn had in himself. The blonde can still remember how Bret complimented his form. It made the Texan blush a whole bright shade of red.

- They didn’t start out as all-out friends like what happened between Diesel and Shawn. They were acquaintances in the locker room, sharing small waves and the occasional “Nice match.” They had this unspoken respect for one another, and it continued to bloom as the years went by.

- Shawn had the tendency to fall slowly and hard. As much as he wants to deny it, his small spark for Bret was there since the very start, and it only got bigger when he entered the WWF championship scene. Shawn made a name for himself big enough to be a contender for gold. And that meant he spent more time with the Hitman.

- Their time together in the ring extended out of the ring too. It started small, sharing stories in the locker room and drinking together in bars after a show. And then they went on dates, sharing hotel rooms, and sitting next to each other during those long-hour flights.

- They shared their first kiss one random night while sharing a bottle of beer on the balcony of their shared hotel room. And it continued to something more in bed.

- It was afterward when they decided it was best for both of them if they only did hookups. Mostly because neither of them could ever bring themselves up to admit their feelings. Maybe it’s arrogance, maybe it’s a fear of commitment. Either way, they stayed casual, and it was neither of them wanted.

- They fell off like how they fell in love: slowly. They started arguing, having fights more than anything else, and it all collapsed on itself. Sometimes, Shawn would wonder what would happen if they did confess.

- This was one of the relationships that actually hurt.

જ⁀➴

Hunter stared at the ceiling, listening to Shawn’s voice fade in and out of sleepiness. The smaller man yawned, “But that was years ago,” he assured. And Hunter hugged him tighter. The blueblood smacked his lips after a stretch of silence, “They won’t just start beating up when we tell everyone of our status, would they?”

“I don’t think so.” Shawn placed a kiss on Hunter’s lips and smiled, “But I’m pretty sure Sid would beat you up just because he feels like it.”