Okay I wrote this for LJ Kink meme and had no plans of owning up to it but since I've done 2 parts now I figure I might as well post it up here to make it easier to read.

Yes it's a scary Shawn/Vince and later JBL thing. Don't blame me it was a request from someone. I just wrote it :P

Shawn took a deep breath and walked into Vince's office. It was now or never.
"So Shawn sit down. You wanted to see me?" Vince said as he took his place back behind his desk.
"Yes. I wanted to talk to you about Wrestlemania. I've got a proposition for you. I'd like to be the one to end The Undertaker's winning streak, and I'm prepared to do anything for it"
Vince raised an eyebrow. "That's a huge ask. We have big plans to continue that streak. What in the hell do you think it is you can offer to make me change my mind"
Shawn looked into Vince's cold calculating eyes and smirked "I know what you want boss. All these years I've seen the way you look at me, don't bother trying to deny it. I'm prepared to give you what you want"
Vince grinned "And you're prepared to do anything I want hmm"
Shawn shuddered dreading even the thought of being with Vince sexually, but sacrifices had to be made. He would get his revenge on the Undertaker. He had been dating Mark for a year when he caught him out having sex in the locker room with Jeff Hardy, breaking his heart. And now he would get his revenge because he knew just how much that winning streak meant to Taker.
He nodded at Vince "Anything" He said again.
Vince sat there for a minute, thinking it all through. Then he looked back over at Shawn hungrily and Shawn knew he was going to give him what he wanted.
"Alright. You've got a deal. You are aware of the way the boys on the roster are going to react to this? You're prepared to put up with the backlash"
"Don't worry about me boss I can take care of myself. I didn't come in here offering myself lightly. I know what I'm getting out of this and it's worth it. I want it in writing first - I'm not letting you screw me out of it - literally" Shawn said as he leaned back in his seat.
"Fair enough" Vince agreed and quickly wrote up a statement and then signed it and handed it to Shawn to read and sign.
Shawn glanced over it and then picked up a pen and signed his name next to the devils. The deal had been made. Vince got up and walked behind Shawn to lock his office door and then turned down the blind before walking back to his desk.
"Take off all your clothes" Vince ordered first.
"We're going to do this here? I was expecting a hotel or something..." Shawn frowned.
"We do it here. I want anyone walking past to know exactly what's going on. You want taker at wrestlemania then you take off your clothes right now" Vince growled.
Shawn thought for a moment. Was his thirst for revenge worth this? He thought of how he felt seeing Jeff being fucked by The Undertaker and his anger was renewed. He threw his hat on the ground and then proceeded to strip as requested.
Vince just sat there watching. When he was naked Vince stared at him a moment. He couldn't believe he was finally going to fuck Shawn Michaels. This was a trophy fuck to top all others. He unzipped his pants and freed his half-hard cock. He saw the look of distaste on Shawn's face but that only made him harder knowing Shawn didn't want to do this.
"I've got two words for you. Suck it" Vince said with humour. He'd said that line in his fantasies about Shawn and was amused he finally got to use it.
Shawn got down on his knees before Vince and closed his eyes before taking Vince's cock in his hands and licking the head. "Eyes open Shawn. You're not gonna sit there fantasising about someone else while you do this. Oh no" Vince demanded.
Shawn shuddered again and opened his eyes to look at the wrinkly old cock in his hands and groaned with reluctance before he took it into his mouth.
Vince threw his head back and shoved Shawn's head down on his cock harder, breathing heavily as Shawn went to work sucking his dick like he did it for a living. "That's it Shawn just like that" Vince moaned and petted Shawn's hair. One hand moved to cup and roll Vince's balls in his hands as he sucked and licked the now rock hard cock in his mouth, occasionally releasing it with a 'pop' to lick and nibble the head before letting Vince ram it back into his mouth. Vince felt himself getting close, and had no intentions of letting his fun end anytime soon, but then he decided that if he got off first he'd last a lot longer the second time around and then let go, making Shawn swallow his load.
Then Vince proceeded to loosen his tie and start to undress and Shawn knew their time had only just begun. He had been hoping Vince being an old man that once would be the only time he could get it up. He saw the look on Shawn's face and said "I take viagra Shawn I could go all fucking day if I wanted to. And I'm warning you I'm going to make this last. I'm getting my money's worth. I always do. Now go bend yourself over that desk and put that tight little ass in the air" Vince spoke as he took off the rest of his clothing.
Shawn lay himself down over the desk and heard Vince open a draw and the squirt of liquid and thanked himself lucky Vince was at least going to lube up first.
He felt Vince's fingers rim around his asshole applying the lube and fought to keep from enjoying the feeling. But by the time Vince started fucking him with 3 fingers to stretch him he was hard against the desk and groaned with disgust. "This is going to be worth every cent" Vince purred huskily against his ear before he started to slide into Shawn's now slick passage.
Shawn shivered as he fought to keep from enjoying the slow possession of his body but then Vince's hand came around to slide over his cock and he pushed back against Vince yelling "Oh fuck"
"Yes that's the spirit Shawn. You're going to be screaming my name loud enough for the entire locker room to hear by the end of this" Vince growled as he started to pump in and out of Shawn at a slow pace. Shawn felt as if he was being tortured with pleasure. He needed it hard and fast so it could just be over and he could forget he ever did this but Vince continued so slide all the way out and then in again so agonisingly slow he was soon moaning and groaning beneath Vince like a slut. "Yes you want it harder and faster don't you? Then beg for it Shawn. You're not going to forget this. It's going to be ingrained in your memory and every time you look at me from this day on you're going to think about my cock up your ass and you're going to want it again" Vince vowed.
"No fucking way!" Shawn replied and forced himself to accept the slow glide of Vince's cock and not beg for the hard fucking he needed to cum. But Vince was rubbing the head of his cock with his finger and rolling his hips to continue changing the angle of his too-slow thrusts and soon Shawn was whimpering with need. "Say it Shawn" Vince purred knowing how badly Shawn needed it.
"Oh god fuck me hard!" He finally shouted. "Fuck me hard Vince. Say it" Vince insisted.
"Vince! Fuck me hard!" Shawn moaned and Vince slammed into him hard enough to move the desk. "Oh Fuck!" Shawn cried with bliss and moaned "Ah! ah! Ah!" as Vince pummelled him, pounding into him like a jackhammer while his hand jerked his cock in time to his thrusts. Vince started licking and sucking on the skin of Shawn's neck and he moaned knowing Vince was going to leave a mark there for everyone to see as proof, but by now he didn't care he just wanted release.
But just as he was about to cum Vince stopped. "What the fuck! Vince!" Shawn moaned and writhed beneath him trying to get Vince to move. But Vince just went back to his slow thrusts from before which wasn't enough to send him over. "Ohhhhh please fuck me hard" Shawn sobbed, slamming a fist down on the desk.
"When I'm ready, I'm enjoying this too much for it to be over so soon" Vince chuckled. He pulled out and sat back in his plush leather chair and patted his lap. "Sit on my cock Shawn and ride me if you want it hard" Vince commanded.
Shawn, desperate for relief, quickly impaled himself and started rocking up and down on Vince. Vince groaned and moved his hands to Shawn's hips to speed up the pace as he went back to biting and licking Shawn's neck.
In this position their now sweaty chests rubbed against each other and Shawn was too far gone to be repulsed. Instead the friction just added to the pleasure and soon Shawn was fucking himself on Vince's dick so hard he felt like he was going to explode once his orgasm hit. Vince finally was getting too close to let things draw out any longer and he ordered Shawn to scream his name as he came or he would deny Shawn the right to cum.
Vince's hand wrapped around Shawn's dick and he screamed out "VINCE!" As he came so fucking hard. He felt Vince groan and shudder beneath him and fill him with cum and was shocked when he came yet again. "Ahhh Vince!" he cried, splattering their stomachs with cum.
He was too weak to stand straight away and sat there for a moment with Vince's cock still up his ass and groaned realising he'd got more than he bargained for. Vince was right in that he wasn't going to forget this as much as he wanted to.
Finally he stood up, groaning as he felt Vince's cock leave his tender ass and he put on his clothes after wiping the cum off his chest with tissues. Vince just sat there watching him, enjoying every moment of Shawn's humiliation.
"Well Shawn you're free to go. If you ever want to make any other deals you know where to find me" Vince said finally getting up to clean himself and dress.
Once they were both dressed again Shawn took his written contract and left, doing the walk of shame out to the carpark past all the wrestlers that had clearly heard him being fucked by Vince. He didn't look at their faces, he knew what he would see. Everyone would be disgusted. But now he was going to get his revenge. Undertaker's winning streak would soon come to an end - by him!
And as for the sex he'd had to endure to get it, well he wasn't going to think about it, but he knew he was going to dream about it for a long time to come and shivered. But would it be a fantasy or a nightmare?... He didn't want to answer that.