#undertaker x shawn michaels

[tameodesza]

To All the Men Shawn's Ever Loved

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 🤭

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. 

#divider cr: @cafekitsune #hartbreak #bret hart x shawn michaels #marty jannetty x shawn michaels #kevin nash x shawn michaels #undertaker x shawn michaels #triple h x shawn michaels #bretshawn #hbtaker #shawnter #shawter #alternate universe #wwe fanfiction #shawn michaels #bret hart #marty jannetty #kevin nash #undertaker #triple h

[sleepy-achilles]

'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 :)

#wwe #shawn michaels #the undertaker #wwf #hbtaker #undertaker x shawn michaels #shawn x undertaker

[take-taker-taken]

For @theundertakeriscoming - a little bit of HBTaker fluff.

Movie Night

“C‘mon, everything’s ready to go in here!”

Taker shakes his head with a smile as he runs the damp cloth over the countertop. Shawn loves it when they have a movie night - setting up the room, planning what they’re going to watch, organising snacks… He walks into the living room and there’s his blue-eyed boy, curled up on the couch beneath a blanket. One arm pokes out, aiming the remote at the TV as he turns and grins.

“We’re starting with Karate Kid!” He says excitedly. “Get under,” he adds, flipping back the blanket.

Taker snags the popcorn and sinks on to the couch, balancing the bowl on the arm of the sofa until he’s comfortable and the blanket is tucked around them both. Shawn nods in satisfaction and then hits play before diving his hand into the bowl that’s been relocated to his partner’s lap. He wriggles a bit as if to settle himself deeper into the couch cushions and then rests his head against Taker’s arm.

They pass comments to one another as the story unfolds and they only make it to twenty minutes in before Taker’s hand slides along the back of the couch and he starts to gently massage the back of Shawn’s neck. The smaller man moans softly, enjoying the attention and then he turns his head and kisses along Taker’s jawline, breathing in the clean masculine scent of his skin. Shawn sighs happily as he’s pulled in closer to his lover’s body and held tight as lips seek out lips and then it’s soft, lazy little smooches with no real purpose other than for the sheer joy of it. There’s the occasional deeper kiss with tongues gently stroking together but lust isn’t the aim here and so they enjoy the ebb and flow, never becoming breathless but floating calmly in their warm sea of contentment.

“We’re supposed to be watching the movie,” Shawn murmurs eventually. “Movie night, remember?”

“Sorry,’ Taker says and there’s no flippancy to his reply. He draws back until just the tips of their noses are touching. “Just so cozy, and you taste so good.”

“Mmm, you too. Popcorn and chocolate,” He adds with a soft smile.

“Hey, this is one of your favourite scenes,” Taker says as a fight breaks out on screen. Shawn turns his attention back to the movie and the big man can’t help but smile as he feels the blonde tense a few times in reaction to what’s taking place. He cuddles Shawn - now sprawled half across his lap - close as the rest of the film plays out, stroking a hand gently through his hair until the final credits start to scroll.

“What’s next?” He asks, gently manoeuvring Shawn back into an upright position.

Shawn grins. “Figured we’d go old school… it’s The Birds.”

It’s Taker’s turn to smile - trust Shawn to queue up his favourite. “I’ll go make a fresh batch of popcorn, shall I?”

“Uh huh. And can you bring me back a soda? Cherry flavour?”

Taker nods but says, “You know that stuff turns your lips unnaturally pink, right?”

Shawn shrugs. “We’re home alone, it’s dark.” He gives his partner a cheeky wink as he adds, “And you can always try kissing it all off?”

Taker gazes down into twinkling blue eyes and quirks a brow. “I’ll be right back with it. Don’t let my spot under that blanket get cold.”

TTT

#the undertaker #undertaker #this character lives in my head rent free #shawn michaels #hbtaker #fan fiction #undertaker x shawn michaels #undertaker fanfic #Shawn Michaels fanfic #TTT Tumblr Asks

[heartbreakertaker]

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

#I NEED IT #like look at the material #taker is so cute in that pic omg #hbtaker #undertaker x shawn michaels

[achillessleepy]

The other one is on @sleepy-achilles this is the one I've only posted too tumblr, it's bascially a remake of the video I made awhile ago.

#shawn michaels #wwe #the undertaker #undertaker x shawn michaels #hbtaker #shawn x undertaker #wwf

[sanman2022]

Just some random gifs of people

#the undertaker x reader #the undertaker #john morrison #shawn michaels #hbk #bucky barnes #sebastian stan #chris evans #captain america #bret hart #kenny omega #jey uso #wwe raw #wwe #wwe smackdown #marvel #aew dynamite #aew #wwf #nxt #wwe nxt #the usos

[intravenus]

He’s so babygirl honestly

#shawn michaels #hbk #wwe #wwe superstars #wwe hall of fame #wwe raw #nxt #heartbreak kid #shawn x undertaker #triple h #wrestling

[dilanmoodboards]

New hyper fixation

These are shit but I thought maybe I should share it

#WWE #WWF #d-generation x #dx #hbk #heart break kid #shawn michaels #triple h #hunter hearst helmsley #the undertaker

[rock-on-the-radio]

💔HBK Discord💔

💔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 😭

#wwe #wwf #shawn michaels #triple h #the undertaker #hunter hearst helmsley #shawter #shawnter #hbtaker #bret hart #kevin nash #dx #d generation x #hbk #hhh #chyna

[wrxsslin-hours]

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.

⠂ ⠂⠄⠄⠂☆

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.”

#wwe fanfiction #wwe headcanons #shawn michaels x triple h #shawn michaels x bret hart #shawnter #shawn michaels x kevin nash #shawn michaels x undertaker #shawn michaels x razor ramon #shawn michaels #bret hart #marty jannetty #diesel #kevin nash #razor ramon #sensational sherri #sycho sid #the undertaker #writing #dividers by: cafekitsune

[littlegalaxychild]

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!!!

#yandere the undertaker #yandere wwe #shawn michaels x reader #triple h x reader #triple h x reader x stephanie #the undertaker x reader #wwe undertaker #incorrect Darling’s quotes

[sleepy-achilles]

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.

#wwe #shawn michaels #the undertaker #wwf #hbtaker #undertaker x shawn michaels #shawn x undertaker #triple h #kevin nash #scott hall #kevin x shawn #kevin nash/shawn michaels #the og husbands #og husbands

[take-taker-taken]

For those that asked (and those that didn���t), here’s the scene spawned in my head from the GIF…

Over & Out

“Felt like you were asking for something tonight right after Kennedy tossed you over the rope.” Taker leaves the bathroom with a towel wrapped around his waist and wanders over to sit down on the end of the bed.

Shawn pokes his head back out the bathroom door as he vigorously towels his hair. “What d’you mean?”

Taker raises an eyebrow. “All that crawling around my feet - had a definite… grovelly feeling to it,” he clarifies.

Shawn shrugs with one shoulder. “Well. I was sorry about taking you out like that - genuine mistake on my part,” he says. He walks out into the bedroom gloriously naked and Taker can’t help but admire the smaller man’s muscles bunching under that tanned skin, still damp in places. A rivulet of water runs down his back as he walks past to rummage in his gear bag and Taker imagines lapping it up… his towel begins to tent.

“I hope you’re not thinking about putting any clothes on,” he comments and Shawn looks back over his shoulder with a crooked grin.

“You want me to get cold?”

Taker untwists the edge of the towel and lets it fall away from his lap. “You ain’t gonna get cold boy toy - get over here.”

Shawn drops the tube of hair product back into the bag and saunters over to the big man, stopping in front of him. He notes the burgeoning erection and his tongue darts out over his lips but he doesn’t make a move.

Taker watches Shawn’s gaze and lets out a low, knowing hum. “I knew it. That’s what you wanted the minute you landed at my feet out there, isn’t it?”

“Yeah,” Shawn’s voice is quiet and Taker hears him swallow. “Yeah, I want it.”

Taker leans back slightly, supporting himself on his arms. “So what are you waiting for? Get on your knees and get to work.”

Shawn loves it when Taker gets all demanding like this, especially after a match when there’s still vague traces of his character hanging about. Ordinarily his response would be some kind of snappy comeback but not now - he just gives a small nod and lowers to his knees as Taker spreads his legs to accommodate him. Shawn kneels between them and runs his hands up the strong thighs as he leans forward and then wraps one around the cock, beginning to stroke and enjoying the feel of it hardening fully. He teases like that for a while, stroking slowly and spreading the beads of wetness over the tip with his thumb.

He sneaks a glance up and sees that Taker’s head has fallen back and his fingers have bunched into the sheets. He gives one more twist of his wrist and then shuffles closer and opens his mouth, huffing a warm breath over the spongy head. That elicits a short moan from above and so he closes his lips over the tip and gives an experimental suck before going to work in earnest. He swirls his tongue around the head and then lifts off to plant wet, open-mouthed kisses down the shaft before working his way back up the other side. This time when he takes the cock back into his mouth, the big man’s hand lands on the back of his head and grips into his hair.

“Enough teasing - suck it, boy toy.” Taker growls, thrusting his hips up slightly. “Show me how bad you want me.”

Shawn moans at the combination of pulling on his scalp and the gruff words and renews his efforts. He slowly pushes down, taking as much as he can into his mouth and down his throat and this time when he looks up Taker is looking right back at him. His own dick is hard by now but he concentrates instead on his partner’s pleasure. He raises up again and teases the crown and frenulum firmly with the tip of his tongue and this earns him another thrust into his throat. He swallows around the delicious obstruction and Taker grunts and gets to his feet without relinquishing his hold on the smaller man.

“Such a good little cocksucker aren’t you, boy toy?” He wraps the blonde hair around his fist and carefully pulls him away, smirking when he actually whines. “Gonna let me fuck that pretty face and cum right down your throat, huh?”

“Uh huh… gimme,” Shawn’s a little out of breath but the lust has taken over and all he wants is Taker’s dick back in his mouth.

The big man happily obliges, pushing back into the warm wetness as he holds Shawn still via the grip on his hair so that he can set his own pace. He starts off with slow thrusts, angling them beautifully to slide into the waiting throat and then as he starts to chase his orgasm he gets rougher, holding the blonde in place awhile to feel the fluttering throat muscles grip his cock.

“Jerk yourself off,” He says, breathing heavily himself now. “Want you to cum with my dick buried in your throat.”

Shawn doesn’t need telling twice and takes a firm hold of his leaking dick and starts stroking, his eyes closing as he succumbs to the sensations wracking his frame. He quickly climbs to the peak, teetering on the edge while he’s held up like a rag doll, getting his face fucked.

“Now… do it… I’m gonna cum down your throat, boy toy…”

Shawn feels the first heavy shot hit the back of his throat and he lets himself fall, spurting over his knees, the carpet and covering his hand as the cum bubbles over. He swallows repeatedly, drinking his lover down and only getting to taste the small amount that hits his tongue. The grip on his hair loosens, both hands moving to his arms and Taker slips from his mouth and steps back towards the bed, drawing Shawn up and with him. They tumble down together, the larger man dropping small, light kisses to the blonde’s mouth as a way to soothe him after the rough treatment.

“All better now?” Shawn’s voice is a little rough and so he grabs a bottle of water from the nightstand, gulping half down before passing it over.

“Much,” Taker answers, finishing up the bottle. “Took a hell of a lot of willpower not to drag you up right there in the arena and start something, y’know.”

Shawn giggles, his shoulders scrunching. “You’re so darn easy, you know that?”

Taker snorts and tosses the empty bottle in the direction of the trash can. “You’re not exactly hard to get yourself, boy toy.”

“And you’re the lucky one that gets to have me,” Shawn says, turning so that he can rest his head on Taker’s chest.

Taker glances down at the blonde and smiles. “The luckiest.”

#the undertaker #undertaker #this character lives in my head rent free #wwe #taker smut #shawn michaels #hbtaker #top!taker #hbtaker land #the GIF made me do it #undertaker x shawn michaels #heartbreak kid #the heartbreak kid #hbk #TTT Tumblr Asks

[motherknuckers]

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?"

#wwe #the undertaker #shawn michaels #triple h #degeneration x

[littletroubledgrrrl]

#shawn michaels #wwf #1997 #90s #d generation x #dx #the undertaker

[heartreformer]

wrestling maymay compilation by yours truly

#see ! i can be funny ! ish ! #also wow something other than art ... beginning of a new era #wrestling #shawn michaels #chris jericho #the undertaker #chyna #jeff hardy #triple h wwe #the rockers #90s wrestling #marty jannetty #professional wrestling #pro wrestling #wwf #wwe #the heartbreak kid #d generation x #hunter hearst helmsley #bret hart #oh yeah ive had these in my folder forever . so take them from my hands #not art