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#shawn michaels x undertaker
wrxsslin-hours · 5 months
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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!
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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.
⠂ ⠂⠄⠄⠂☆
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%
⠂ ⠂⠄⠄⠂☆
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.
⠂ ⠂⠄⠄⠂☆
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.
⠂ ⠂⠄⠄⠂☆
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.
⠂ ⠂⠄⠄⠂☆
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.
⠂ ⠂⠄⠄⠂☆
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.”
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dilanmoodboards · 13 days
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I Need to share my agenda
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tameodesza · 6 months
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To All the Men Shawn's Ever Loved
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Headcanon about Shawn’s dating history in some random AU in my head, lol. Inspired by this post by @piratewithvigor about Shawn and his 5 boyfriends 🤭
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Marty: 7 years ―୨୧⋆ ˚
Shawn dated around a lot in his youth, but Marty was his first long-term serious relationship
They met at the start of their careers before teaming together in smaller promotions. Marty chased after Shawn rigorously, the blond being hard to get.
It wasn’t that Shawn didn’t find Marty attractive, but he’d made a promise to his brothers that he’d never date a wrestler. They didn’t have the best track record in relationships, and Shawn’s older brothers didn’t want him to get his heart broken. If only he’d listened.
Marty eventually won Shawn over with how sweet he was, and how interested he seemed to learn about Shawn rather than deducing him to just a pretty face. They took things slow and Shawn finally said yes to the idea of a relationship after Marty had kissed him after leaving a show.
Things were pretty good in the first few years, but the relationship eventually became super toxic, especially around the time Shawn began to gain more popularity and success than Marty.
But they still tried to make it work, Shawn more so than Marty, because of how long they’d been together. Shawn wasn’t willing to give up so easily on a man he considered the love of his life.
But love wasn’t enough to combat their constant relationship problems – trust issues, jealousy, fighting, cheating, etc.
After another pointless argument, Shawn had enough and asked for a break.
✦ .  ⁺   . ✦ .  ⁺ . ✦. ✦ .  ⁺   . ✦ .  ⁺   . ✦.
Kevin: 3 years ―୨୧⋆ ˚
Shawn wasn’t used to being a single man, and after meeting Kevin, his “break” with Marty swiftly turned into an official breakup.
Shawn was attracted to Kevin the moment he saw him on WCW in that ridiculous Oz gimmick. When Kevin came to the WWF, everything just seemed to click between them. They got along well, Kevin didn’t care about the heat Shawn had backstage, and they seemed to have the same sense of humor with Kevin being just as goofy as Shawn.
Kevin had only been there for two weeks before they got together, Shawn determined to scoop him up before someone else could. Being with Kevin was the freest Shawn felt in ages. It was definitely an adjustment to go from his previous relationship to someone who was so laid back, gentle, caring, loving, and protective in a non-possessive way.
Kevin helped to build back up the confidence that Marty had torn down. He was the perfect man for Shawn and it should’ve been a perfect relationship. But in true Shawn Michaels fashion, nothing could ever be that simple.
Despite being with a man that treated him better, Shawn carried over the toxic traits he’d learned from his previous relationship with Marty and basically self-sabotaged his relationship with Kevin. Their problems usually stemmed from Shawn’s lies, jealousy, and trust issues. Which eventually progressed to him picking fights with Kevin just to get a reaction out of the man.
But Kevin was nothing like Marty, and he was too mature and level headed to fall for Shawn’s antics, which only seemed to make Shawn angrier. But Kevin had learned not to feed into the anger, knowing that Shawn would eventually cool off and apologize before crawling into his awaiting arms.  
Their relationship reached a boiling point when Kevin told Shawn he was leaving for WCW. Shawn barely registered Kevin’s explanation before he was yelling at the man, saying he was selfish, that he was abandoning him, that Kevin didn’t love him and was only chasing after Scott.
That caused Kevin to lose his cool, his frustrations spilling over as he cursed out Shawn, offended that the blond would question his love for him and insinuate something between him and Scott. The argument ended with Kevin calling Shawn clingy, which was more of an honest observation than an insult, and Shawn telling him to go fuck himself. Who was Kevin to call him clingy? He’d show him clingy, alright.
That night sealed the fate of their relationship when Shawn did the unthinkable and cheated on Kevin with none other than the hitman, Bret Hart.
✦ .  ⁺   . ✦ .  ⁺ . ✦. ✦ .  ⁺   . ✦ .  ⁺   . ✦.
Bret: 1 year ―୨୧⋆ ˚
My fav ship, but they don’t have a happy ending in this timeline 😭 (sorry hartbreak fans!)
Marty and Shawn’s relationship walked so Bret and Shawn’s could run, both men being equally as toxic but somewhat addicted to each other.
Their relationship had not-so-humble beginnings that spawned from Shawn’s infidelity. And what started from sex eventually grew into an unhealthy codependent relationship with both men using each other to fill some kind of void, Bret fresh from a divorce and Shawn still heartbroken from Kevin dumping him.
It may have been Shawn’s shortest relationship, but it was hands down the most intense relationship he’d experienced on so many levels. 
The love was intense, both men love bombing each other as soon as they were official, quick to let everyone know the other was off limits. Bret specifically made it his mission to show excessive PDA with Shawn whenever Kevin was around, and he continued to do so up until Kevin left for WCW. Shawn was often unaware, just happy to receive Bret’s affection.
Their fights were intense, others often thinking the two would kill each other if someone didn’t step in. They’d gotten kicked out of hotel rooms on multiple occasions due to noise complaints or damage that had been done due to one of them throwing shit around the room. Many of their fights had centered around Kevin, Bret’s jealousy leading him to believe that Shawn was still in love with the man, and Shawn’s annoyance at Bret constantly bringing up his ex.
And best, or worst depending on how you look at it, was that the sex was intense. Shawn had been introduced to so many new kinks, toys, and sex positions because of Bret, and his orgasms were unlike anything he’d ever experienced, the blond often coming multiple times before Bret’s climax. Shawn found that the sex was best when they were mad at each other, thus beginning his unhealthy obsession with riling up Bret, leading to an explosive fight and the most erotic hate sex. It was almost as good as the passionate makeup sex that followed.
Overall, sex was really what kept each other coming back. But beyond their attraction, there wasn’t any substance to the relationship. They hadn’t learned anything important about each other like birthdays, favorite colors, likes/dislikes, etc., which one could say led to many of their arguments because they didn’t really have a good understanding of each other. 
Shawn made the mistake many times of comparing Bret to Kevin because, honestly, he’d never gotten over the man. And deep down, he wished to work things out with him, but Kevin had made it very clear that he wanted nothing to do with Shawn after what he’d done.
So he settled for what he could get, but Bret wasn’t Kevin. He didn’t have Kevin’s patience and wasn’t one to tiptoe around his words to protect Shawn’s feelings.
But just like with his relationship with Marty, Shawn was hesitant to rip the band aid off despite how bad things had gotten between them. He’d grown accustomed to dysfunction, and he’d much rather put up with that than being alone.
The relationship only ended when Shawn got a taste of his own medicine. They say you lose him how you get him, and those words were never truer when Shawn found out that Bret had cheated on him with Sunny.
No surprise, the breakup was messy. Bret and Shawn had argued in front of the whole locker room, almost getting into a fight before Hunter and Chyna pulled Shawn away. But Shawn was a spiteful man and wasn’t going to let that be the last of it.
He keyed Bret’s car in the parking lot and threw a brick through the driver’s side window as an added bonus. Bret didn’t find out about it until the end of the show when leaving the arena. He was pissed and this led to him and Shawn actually fighting in the bathroom backstage the next week, Bret ripping out a few strands of Shawn’s hair in the process.
But Shawn got the last laugh in Montreal when Bret was screwed out of the WWF title.
✦ .  ⁺   . ✦ .  ⁺ . ✦. ✦ .  ⁺   . ✦ .  ⁺   . ✦.
Undertaker: 4 years ―୨୧⋆ ˚
Shawn was as a broken man after his breakup with Bret, and even more so after the screwjob. Aside from DX, no one in the locker room wanted anything to do with him regardless of him telling people he wasn’t involved in screwing Bret out of the title (a lie no one believed).
It was the loneliest he’d felt in some time and certainly the longest he’d gone being single, which he had a hard time dealing with. Being the third wheel of Hunter and Chyna certainly didn’t help.
Undertaker had gained the same disdain towards Shawn as many of the guys had after the screwjob, steering clear of the blond at all costs. But he was also a professional and was willing to put his pride aside to do his job. So when Vince came to him about a possible feud with Shawn and a casket match, Undertaker agreed to it, albeit begrudgingly.
Ironically, their relationship began after Undertaker had injured Shawn’s back on that casket.
He felt absolutely devastated after hearing of Shawn’s upcoming back surgery that was a result of the casket clipping his back. When the words ‘career-ending injury’ began floating around, he felt sick to his stomach from guilt, blaming himself for the accident.
After Shawn’s surgery, Undertaker sent numerous ‘get well soon’ cards and flowers to Shawn’s hospital room. Shawn initially thought it was from his family or Hunter, but the cards never identified a sender. It wasn’t until Undertaker visited him in the hospital, the only wrestler outside of Shawn’s friends to come see him, that everything came together.
Undertaker was expecting to receive anger, insults, a spew of curses, anything other than the appreciative smile Shawn gave him when he sat at his bedside. The conversation was light, pleasant even, ending with Shawn telling Undertaker not to blame himself for his injury. He didn’t blame him, so the dead man shouldn’t do the same.
The visits became more frequent and once Shawn was released from the hospital, Undertaker had even taken some time off the road to look after Shawn in Texas. It was during that time at Shawn’s home that they officially got together. 
Being with Undertaker was vastly different than Shawn’s previous partners. It was almost a bit odd being with a man that was so thoughtful, yet also not afraid to call Shawn out on his shit. Undertaker had a very no-nonsense demeanor that Shawn respected and was drawn to.
At that point in his life, Shawn was done playing games, no longer interested in the drama of relationships. He didn’t want to pick fights or throw hissy fits. He wanted something easy. Simple. And that’s what they had.
During his time with Undertaker, Shawn had matured the most. Undertaker helped him better understand his emotions, reflect on his past, and realize what wanted in life going forward. It may have also helped that Shawn was completely sober due to him taking medication, which Undertaker made sure he wasn’t misusing.
Undertaker was very instrumental in helping Shawn train to go back to the WWF, now WWE, in 2002. A lot had changed in Shawn’s absence, and he was honestly insecure and a little bit scared to return. He didn’t know if the fans would even care about him returning. And he knew a few of the boys backstage wouldn’t be happy. But Undertaker was always there to kiss away his worries, ensuring him that everything would be ok. They would be together, and he wouldn’t let anything bad happen to Shawn.
Shawn didn’t know their relationship could get any stronger, but it surely did after his return to the company. For the first time, Shawn was able to see what it was like to have a healthy relationship on the road. Undertaker didn’t question him of his whereabouts backstage or hover over him at the bar. He trusted Shawn and Shawn trusted him, knowing that they’d always end the night in each other’s arms at the hotel.
They broke up some time in 2004. The breakup was amicable, and there were no cars keyed in the parking lot this time. Shawn wanted to take some time to focus on himself and his career, which Taker completely understood as they’d both been putting their career over their relationship. Undertaker also needed to focus on his own personal issues, especially with his brother Kane. As much as he didn’t want to admit it, it was best for Shawn’s safety for them to be apart for the time being.
As mutual as the decision was, it was still a painful breakup for the two. They really loved each other, and always would, but they had their own paths in life that didn’t seem to involve each other at the moment. They figured if it was meant to be, they’d find each other again. 
✦ .  ⁺   . ✦ .  ⁺ . ✦. ✦ .  ⁺   . ✦ .  ⁺   . ✦.
Hunter: 2006 - Present ―୨୧⋆ ˚
To be honest Shawn should’ve seen this one coming.
Hunter had been Shawn’s best friend since 1996. He thought Shawn was the most beautiful man he’d ever seen when he first met him, and he’d almost made a move on the blond until he learned that Shawn was dating Kevin. Hunter settled on being good friends with Shawn and began dating Chyna shortly after.
As he and Shawn grew into best friends, his interest in the shorter man never wavered. Unfortunately for him, he never had an opportunity to pursue Shawn in their younger years as either he or Shawn always seemed to be in a relationship while the other was single.
And the one time that they were both single, they weren’t on speaking terms. They’d gotten into a heated argument where Shawn called Hunter a backstabbing friend and accused him of using him to get to the top. Hunter was fed up with taking the brunt of Shawn’s anger and they both didn’t speak to each other for over a year after that.
Surprisingly, it was Kevin that reunited the two, encouraging Hunter to talk to Shawn and hear him out. After hearing about Shawn’s injury and back surgery, Kevin was quick to call the blond, concerned about his well-being. Though they hadn’t ended on good terms, he would always care for him.
They’d kept in touch sparingly since then and through their short conversations, Kevin learned of Shawn’s falling out with Hunter. Shawn was a stubborn man and Kevin knew that no matter how sorry Shawn sounded over the phone, Hunter would need to make the first move to fix their friendship. And after learning how sorry Shawn was, that’s what Hunter did.
He still held a bit of anger towards Shawn, but he missed him. And after a tearful reunion, their friendship was back even stronger, and so was his feelings for the blond. Feelings that had never left. But Hunter soon learned it was too late to pursue anything as Shawn had been dating Undertaker.
So just as he had in 1996, Hunter settled on being a good best friend to Shawn. And he was ok with that. They had so much to catch up on, and Hunter was just happy to have his buddy back.
Shawn and Hunter didn’t get together until 2006 after DX reunited. They’d already been close after rekindling their friendship but being DX once again and constantly being surrounded by each other while also never getting sick of the other really solidified their feelings for one another. That and the kiss Shawn gave Hunter on New Year’s Eve. 
For the first time, Shawn felt confident as he went into his relationship with Hunter. He was in a better headspace, had matured, and instead of carrying over toxic traits of past relationships, he carried over the lessons he’d learned over the years, determined to make this relationship last because he not only cared for Hunter as a lover but as a best friend. He’d already built up an immense amount of love for the man, and he didn’t want to ruin their relationship again. Also, Shawn was getting up there in age and was ready to settle down.
Being with Hunter made Shawn wish he’d made the decision sooner. They just got each other. Many times Shawn wouldn’t need to say anything, just give Hunter a look and the man would know what he was thinking.
Hunter was always so tender with him, probably afraid that Shawn would break or revert to his old ways at the slightest hiccup, which Shawn wasn’t going to allow to happen.
Shawn loved that Hunter was very affectionate, always touching him in some kind of way whether it’s holding his hand, hugging him every chance he got, playing with his hair, or tugging on his pocket to bring him closer.
Their fights were minimal, or at least they fought the least out of any of Shawn’s relationships. But when they did fight, it wasn’t the usual screaming matches Shawn was accustomed to. They talked to each other calmly with level heads, both hearing each other out before making a point. And they’d always end the conversation with a hug and an ‘I love you.’
Shawn’s sure Hunter’s the one after the man gets injured in 2007. Seeing Hunter in the hospital in so much pain and not being able to do anything about it broke Shawn.
He took time off the road to help Hunter with his injury, much like Undertaker had done for him. Being with Hunter every day so close in such an intimate setting of Hunter’s Connecticut home made Shawn realize he wanted to spend the rest of his life with him. And any man that could make Shawn endure the cold Connecticut winters deserved his heart.
The proposal was impromptu, Shawn whipping out the ring after Hunter’s physical therapy session. It was bittersweet, more sweet than bitter, since Hunter wanted to be the one to propose first. He’d been planning on doing it and would have done it sooner had it not been for his injury. 
But as he looked into Shawn’s beautiful teary blue eyes, he said yes, of course, and they were married on New Year’s Eve of that year, sharing the same kiss that started their relationship.
Looking back on the past, as painful as it was, Shawn wished he could thank all of the men he’d ever loved for teaching him how to love and helping him grow into the husband he was today. 
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sleepy-achilles · 2 months
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'I totally lied through my teeth to him. Cause I felt bad, because I care so much for him now'- The Undertaker on the Stone Cold Podcast, talking about Shawn Michaels.
Enjoy :)
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take-taker-taken · 1 month
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WARNING - the chapters that comprise this section of The List will contain CNC (consensual non-consent). It will mention rape. There will be humiliation. It will involve weapons. This particular part is mainly corporal punishment. The sub will not always be treated / spoken to kindly. If you’re happy to read such things then feel free to continue.
The List - CNC - Part Four
As you huddle on the floor, gradually getting your breathing back under control, you become aware of the curious feeling of being surrounded. You lift your head and peek around and sure enough, two pairs of boots are inches away.
“I knew you’d choose those,” Mark’s voice floats above you.
“So I’m a tit man - sue me,” comes Shawn’s reply. “Already know what you’re gonna do next.”
Mark huffs out a laugh. “Yeah,” He says. “She doesn’t though.”
Shawn nudges you with his boot and when it makes you huddle in even more he curses and does it again, but harder. “Get on your back, slut - should be familiar.”
You slowly roll over on to your back with your knees raised up and cross your arms over your chest. In response he kicks lightly at your knee so that you drop your legs flat and then he follows you down and sits astride you. He takes hold of your arms and works to pull them away from your body; you do your best to resist but he’s far too strong and he easily forces your hands up and over your head before his gaze roves hungrily over your breasts. As soon as he lets go you begin to move them again and so he grabs them and shoves them back down, holding them there as he looks down at you with a stony expression.
“Leave ‘em there, or I’ll get him to stand on ‘em.” He warns with a nod over to where Mark is standing. “Probably break your fucking wrists.”
You swallow a whimper and just lay there as he slowly lifts his hands away, watching to make sure you’re going to obey. He reaches behind his head and removes a silver chain that’s draped around his neck. At first you think he’s taking his necklace off and then as he lifts it free of his hair you grit your teeth - it’s a set of clover clamps. Fuck… this is going to hurt.
Keeping the clamps in one hand he uses the other to toy with your left nipple. Not viciously like he did before - it’s a gentle, teasing touch and of course the bud turns hard under his ministrations. You’re expecting him to put the clamp on right away but instead he takes his time to play with the other one, until both have been coaxed into firm peaks. He leans down and traces the tip of his tongue around each of them in turn and you whimper as the skin tightens further.
He shifts his head so that his mouth is next to your ear and whispers, “I think you enjoyed that… didn’t you, fuck toy?” He raises up again and you close your eyes briefly as your stomach flips over at the name but say nothing; when you open them he’s dangling the chain over your face as he smirks down at you. “Know what these are?”
Deciding to play dumb, you shake your head and he traces his fingers over your breasts again.
“Remember me saying I wanted to hear you say ‘please’ some more?” He doesn’t wait for an answer as he rattles the clamps in your face. “These are gonna make that happen.”
Without any further preamble, he deftly attaches the clamps to your nipples and as the pain lances through your flesh you scream. It’s the sort of reaction that you’d normally work to keep a lid on but no such pretence is needed here. Before you can move he lunges forward and holds your wrists to the floor as you struggle beneath him.
“Fuck! Take them off, please! Take them off!”
He looks down at you and smiles, running his tongue across his teeth before shaking his head. “Nuh uh - they look real pretty.” He moves a hand in order to pinch the chain between thumb and forefinger, holding it loosely though it sways some. “And the best part? If I give this here a little pull… they’ll get tighter - wanna try?”
You shake your head and your voice cracks a bit as you speak. “No… please don’t… please!” You’re breathing hard as you try to cope with the pain, your hands clenching repeatedly into fists though you leave your hands over your head for fear of reprisals if you move. You close your eyes and let yourself feel the fear, the helplessness, the pain and yes… the arousal.
“You said she kicked you earlier?” Your eyes open when Mark speaks, though you’re still mostly distracted by the sharp pain in your nipples and the fact that Shawn still has hold of the chain and thus controls whether it goes up a couple of notches.
You gain a couple of degrees of relief when he lets the chain go and kneels back up in order to look at Mark. “Yeah, when I was putting her in the truck.” He says and then gets to his feet but continues to stand astride you. “She was mouthing off with some BS about people coming over and then she slammed her foot right into my kidney, little bitch.”
“Well, that sure ain’t the kind of behaviour we expect. Get her up here.”
For a frightening moment you think Shawn is going to drag you up via the clamp’s chain but as he bends over he’s reaching towards your arms and unthinkingly, you bring them down from over your head to aid the task. Given that it’s achieving his aim he doesn’t rebuke you for moving and just hauls you to your feet and you stand there with your head down, teeth gritted against the pain in your chest. You gasp as a hand goes into your hair to drag your head back and you find yourself looking up at Mark. You again have a moment of wonder at how he’s emanating this air of being a stranger but then you have to concentrate because he’s speaking.
“So you’ve been cussing, being violent - and you even spat at him,” he’s saying, indicating Shawn with a nod of his head. “Can’t be letting you get away with all that now, can we?”
You don’t say anything because even though it’s clear to everyone that your actions over the course of this scene were entirely to be expected, you know that no good will come of answering back.
“I’m kind of an old fashioned guy,” he goes on as he releases your hair and his hands move to his waist. “So I’m gonna give you some old fashioned discipline.” Your breath catches as he unbuckles his belt and slides it from the loops - it’s an aspect of impact play that’s been as yet untouched on your list, though not for much longer. “Get her bent over,” he says to Shawn and as the blonde walks by you he pats your cheek but you shy away from his touch which makes him huff with laughter.
There’s another table at the far end of the cabin, pushed up against a wall and next to a door that you notice for the first time. You briefly wonder where it leads to but then Shawn’s back and setting the table in question down a couple of feet away.
“C’mon, get over.” He pulls you by the wrist to stand beside it and then pushes on the back of your neck. You go quietly into position, though set your forearms on the wooden surface to prevent your clamped nipples being squashed against it. Without relinquishing his grip on your neck, Shawn runs his other hand firmly down your back and on to your ass cheek which he squeezes hard and then smacks. You whimper but this time it has a different tone because it’s becoming harder to play act against the rising tide of lust.
“A good dozen should do the trick, what d’ya think?”
You swallow, wondering whether the question is directed at you and then feel relieved that you didn’t try to speak as Shawn smacks your ass again and replies, “For starters.”
There’s a brief silence and then you feel Mark’s huge hand between your shoulder blades. You have a mad thought that it’s weirdly comforting to have both of them touching you at the same time but that’s quickly driven from your brain when the belt comes whistling down and lands squarely across your backside. For a second you feel virtually nothing and then as the sting spreads over your skin you gasp and then cry out. There’s a pause that you recognise dimly as an opportunity to call red but you decline. Shawn’s hand is still on the back of your neck holding you down, and then you feel Mark’s lift from you and hear him changing his stance. In that moment you realise that first stroke had just been a taster and ball your hands into fists beneath yourself as the leather snaps down again.
“Ahhhhhhh, FUCK!” Still held in place by Shawn’s powerful grip, you stamp one foot against the floor as though it will shake off the pain.
“Still cussing, girl?” Your outburst seems to have earned you a break just two strokes in as you hear him issue another order. “I don’t want to be getting my ears assaulted all the way through this - can you gag her, please?”
“Sure can,” You hear the reply and then you feel Shawn’s fingers at the waistband of your panties and he has them down and off before you can react. Next thing, his grip is back in your hair as he drags your head up, pushing the material at your mouth. “C’mon bitch - open up, you’re good at that.” You begin to make a muffled protest that never gets the chance to be anything else as he forces your panties into your mouth. You taste yourself on the fabric but then get distracted by his other hand worming its way under your chest. You try to pull away, certain that he’s seeking to mess with the clamps but then you feel a totally foreign object being urged against your fingers. You move your head and realise that it’s a golf ball and then you understand - you can’t speak right now to use your colours. You clutch on to the ball and he gives your hand a quick, gentle squeeze before withdrawing and pushing your head back down. “That’ll shut her up,” he says and you hear Mark make a noise of satisfaction.
He doles out another four hard strokes with the belt and you squeeze the golf ball for dear life and yell into the makeshift gag. Through the pain your brain starts to swim in that beautiful, serene way and in your mind’s eye you see yourself as they probably see you - bent over with your pussy dripping as a leather strap strikes your pale skin in such an intimate way. You can picture the welts, bright pink with the edges oh, so slightly raised up. You scream into the fabric as the leather connects twice more and then your head is raised again by Shawn and he’s looking right at you. You meet his gaze and then after a few more seconds he lets your head fall and the belt snaps across the back of your thighs once, twice and then another mighty crack across your ass.
You scream one final time, your head lifting up as the blow sears into your flesh and then it drops again and you hear and feel the thump as Mark sets the heavy belt down next to your head. There’s a moment of silence and you’re dimly aware of Shawn’s hand gently kneading the back of your neck. The very second you find it comforting, it leaves you and you hear him speak again, his voice back to that dark, sneering tone.
“Get her upright; it’s time to get those clamps off. I wanna hear her begging again.”
TO BE CONTINUED…
Previous | TBC
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sanman2022 · 2 months
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Just some random gifs of people
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intravenus · 10 months
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He’s so babygirl honestly
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rock-on-the-radio · 8 months
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💔HBK Discord💔
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💔Description: hi everybody!! I feel like the fandom has been kind of dead and it’s been hard to find other mutuals to gush over our favorite wrestlers with. So I decided to make a discord so we can joke around in and share our ideas, headcanons, and RPs. :))
💔If you’re interested in Shawn Michaels, Triple H, Undertaker, Kevin Nash, Bret Hart, Chyna, D-Generation X, the Kliq, shawter, hbtaker, Kevin nash/Shawn Michaels, Bret Hart/Shawn Michaels, or any other wwf/wwe ship, then is server is for you!!
💔Please join I need more attitude era wrestling fans 😭
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littlegalaxychild · 9 months
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Incorrect quotes of the main 3 darlings
Persephone- The undertaker darling
Royal - Stephanie and Triple H darling
Aphrodite- Shawn Michaels darling
Persephone , whispering to Royal, who’s on the phone with Aphrodite: Ask them something!
Royal: How are you feeling?
Aphrodite: Fine.
Persephone : Something personal!
Royal: At what age did you first get your period?
Persephone : What do you think Royal will do for a distraction?
Aphrodite: They’ll probably, like, make a noise or throw a rock. That’s what I would do.
*Building explodes and several car alarms go off*
Aphrodite: ... or they could do that.
Persephone : Aphrodite and I are having a baby.
Royal: That's gre-
Persephone , slamming adoption papers on the table: It's you, sign here.
For context, Royal is the youngest among the 3 (Aphrodite is the oldest and Persephone is the middle child)
Persephone , driving Royal and Aphrodite: So how was your day?
Royal: We almost got surprise adopted!
Persephone : What?
Aphrodite: We almost got kidnapped.
Persephone : Oh, okay.
Persephone : *slams on the breaks* WAIT WHAT?!
Persephone is the only one who has a drivers license but it barely get used cause she is a passenger princess
Royal: If I accidentally sat on a voodoo doll of myself, would I be trapped forever in that position, doomed to starve to death?
Royal: How am I supposed to know?
Aphrodite: You say, as if we don’t use you as a source of knowledge of the occult.
Persephone: *sighs*
Persephone: You wouldn't be trapped.
Persephone : Royal and I were crossing the street, and this dude drove by and honked at us
Aphrodite: *Sighing* What did Royal do?
Persephone : They chased him to the next red light, then reached into his window and...
Royal: Who wants a steering wheel?
Royal might be slightly feral
Persephone : If you had to choose between Royal and all the money I have in my wallet, which would you choose?
Aphrodite: That depends, how much money are we taking about?
Royal: Aphrodite!
Persephone : 63 cents.
Aphrodite: I'll take the money.
Royal: APHRODITE!!!
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motherknuckers · 3 months
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I was showing my auntie and cousin some of the undertakers most iconic matches with shawn michaels.
Triple H: *comes out to drag a bloody Shawn Michaels out the ring*
Auntie: "now who the hell is this"
Cousin: "I don't know... Thor?"
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wrxsslin-hours · 5 months
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In your post about Shawn’s messy love life, you mentioned how undertaker was a gentle giant to shawn. Could you write about some of undertaker’s gentle giant activities? Love your writing!
Taker Has a Soft Spot for Shawn, headcanons
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The Undertaker x Shawn Michaels
a/n: anon, writing this added 3 years to my life. Thank you for requesting! Hope you enjoy ;3c
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| Despite Shawn being the most annoying man in the locker room, Taker managed to tolerate him enough to spend more than 5 minutes with him. Shawn thinks it’s because he’s too pretty to ignore, but it’s actually because Taker only knows two places backstage: the locker room and the parking lot. If he did manage to wander off to other rooms, Taker would get an earful from Bearer. Between his manager’s squeak toy voice and Shawn’s constant ramblings about how pretty he looks, Taker would choose the latter. Shawn only started actively gravitating towards Taker after his fallout with Diesel. Taker is not a brick wall, as much as Shawn wants to believe. For the first time, Shawn was left speechless by Taker’s voice, prompting a double take.
"What’s up with you and Diesel?" Taker asked, towering over Shawn as the blonde ranted about how good it is to finally have a hotel room all to himself. "We’re not on speaking terms. From now on, this doll is sold separately," Shawn blinked, then added, "Wait. You can talk?!"
| Taker began to enjoy Shawn’s company, much to his own surprise. It reached a point where Taker would wait for Shawn to freshen up after shows so they could go to the hotel together. This meant Taker had to spend a solid hour sitting in the now-empty locker room, listening to Shawn’s distant singing of his "Sexy Boy" theme in the showers. Most of that hour was just Shawn trying to find where he kept his shampoo and whatever else he used to clean himself. As a favor (more for his own sake than for Shawn's), Taker would prepare Shawn’s things on the bench beside him. Shawn greatly appreciated it and mentioned that Taker didn’t have to do that. However, for the sake of Taker’s boredom, he would happily do it if it meant they could leave earlier.
| Taker would let Shawn wear his entrance gear. Shawn gets a kick wearing Taker’s overly large necktie and purple gloves. It would usually go as Shawn getting his hands on Taker’s gear after their matches and wearing it for the rest of the show backstage. There was a time when it was raining and Shawn’s rented car was in the middle of the parking lot, and that meant they would get wet just running towards it. Not wanting Shawn’s hair getting ruined, Taker plopped his wide-brimmed hat on Shawn’s head and used his coat to cover the smaller man as they booked it to the car. That was the moment when Shawn started to fall hard.
| Shawn liked to party a lot; Taker knew that well. Whenever Taker had to book Shawn’s hotel room for him (since the blonde was too busy dancing on tables and tormenting Lawler by the bar immediately after shows), he would scribble down the hotel room number on a piece of paper and bury it in Shawn’s front pocket for the blonde to find later. But when Taker knew Shawn would be too drunk to differentiate his lefts and rights, Taker would find out where Shawn is drinking and wait for him outside the bar. Taker would have to carry Shawn all back to the hotel and make sure he’s all clean and tucked up for bed. Shawn would often find ibuprofen and a glass of water on the bedside table, and his clothes from the night before would be folded neatly on a chair.
| Shawn would often have to stand on the tips of his toes to whisper something to Taker, and the dead man would unconsciously lean down to make it easier for Shawn. That led to Shawn accidentally kissing Taker on the cheek. Shawn easily waved it off, but that was a moment that haunted Taker’s mind for weeks.
| Taker would subtly stand in front of Shawn whenever Diesel passes by.
| Taker would notice if something was bothering Shawn. He would know if it’s something that really bothers the blonde when his ear isn’t being talked off. Whenever that happens, Taker would just scoot closer to Shawn while they’re sitting on the bench, not saying a word, and offer his arm for Shawn to lean his head on.
| Shawn found out that Taker gives the best hugs. Sometimes, Taker would think Shawn doesn’t like it too much since he doesn’t really give off any warmth—since, you know, he isn’t alive. So, Taker wears his coat before hugging Shawn to give some sort of heat. But he decides to forgo the coat when Shawn says he likes feeling his skin.
| Taker carries Shawn around when he’s too sore to move. Shawn worries about it, protests that it doesn’t hurt that bad. But Taker wants to hear none of that and continues to carry Shawn around on his back.
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dilanmoodboards · 19 days
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The Breakfast Club
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Dear Mr. Venon. We accept the fact that we had to sacrifice a whole Saturday in detention for whatever it was we did wrong. But we think you’re crazy to make us write an essay telling you who we think we are. You see us as you want to see us: in the simplest terms, in the most convenient definitions. But what we found out is that each one of us is a brain…
…and an athlete…
…and a basketcase…
…a princess…
…and a criminal…
Does that answer your question? Sincerely yours, The Breakfast Club.
The 1,2,3 Kid as the brain;
Bret Hart as the athlete;
The Undertaker as the basketcase;
Shawn Michaels as the princess;
Razor Ramon as the criminal.
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littletroubledgrrrl · 10 months
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deeznutzz69 · 1 year
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sleepy-achilles · 11 months
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Yeah,
Hunter x Shawn x Taker is cute.
It would just be hunter and taker having a dominance battle whilst Shawn just sat back and watched.
And yeah
Kevin x Shawn x Scott is cute.
It's like sunshine protector x Sunshine x Chaotic sunshine protector.
But you know what really works for me?
Kevin x Shawn x Taker.
Protector x Sunshine x Grumpy Guard dog.
Kevin protects them both mentally whilst taker protects them both physically.
Also..
Big x Smol x Big.
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heartbreakertaker · 1 year
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Finding this pic of young taker awoken the need inside me to read an AU on him and shithead 90s shawn, who’s desperately trying to seduce him
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