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He didn't want to think about what had just almost happened with Elena, he didn't want to think about what had happened with her death wish having brother-

-and most of all he didn't want to think about what had happened with Katherine, but he couldn't stop it all swirling around in his head. He'd come this close to turning it off. If Stefan hadn't chosen that exact moment to come charging in and stopped him he may well have ripped her cold dead heart from her chest and ended it once and for all. Apparently, Stefan had been following Katherine to make sure she got out of town and didn't try attacking Elena or anyone else and realised she’d doubled back and headed to the boarding house. Katherine had done what she did best and fled at record speed even for a vampire when Stefan vamp sped in all hero hair and judgment lecturing him until he removed his hand from her chest, regrettably leaving her evil heart where it was.

Stefan had gone into full annoying little brother mode about how stupid he had been to let her get to him. He'd convincingly lied through his teeth that he was just trying to scare her and had no intention of turning it off but Stefan sadly not only didn't believe him he started yelling about how his tendency to lash out already put Elena in danger and if he turned off his humanity he could do anything to her including killing her and the only way that was happening was if he went through him.

As if he couldn't,  -but Stefan the squirrel drinker was right, a judgemental, self-righteous pain in the ass, yes, but he was right. Turning it off right now was crazy. The entire founder’s council was on the warpath for killer vampires. It was hardly the time to flip the switch on his humanity and by extension his self-control and do something reckless. The idiots at the council didn't know about daylight rings and if he was going to keep it that way he had to continue his game of misdirection, particularly with his new bestie the sheriff, not to mention Mrs Lockwood who like him wanted answers about her husband’s death, why had a vampire weapon worked on human anyway?  

‘I wouldn't I laced it with Vervain’.

He sniffed his drink, yep Vervain alright. He must have been seriously distracted over his idiocy with Katherine and the irritating conundrum of what happened with mayor Lockwood to not notice his drink was spiked and Jeremy Gilbert was sitting in a chair looking shady as all get out.


Sooo, Jeremy Gilbert had been planning to kill him, -he would have to punish the little brat for his insolence. His obsession with vampires wasn’t going to end well. First he'd willingly drank a Vampire's blood and now he was trying to get one to big brother him. Well, it was time little Gilbert learned what Stefan would gladly tell him, -most of the time he sucked at being a big brother.

‘So you laced my Bourbon with Vervain, whittled that big stick all by your lonesome, stole an Abercrombie and Fitch model's hoodie and came in here to kill me huh?'

‘Yeah but then I thought-

‘I don't care what you thought little brat, you made a big  mistake coming here, and a bigger mistake confessing. I told you what I would do if you crossed me, or did you forget our little chat at the carnival?’ Damon moved closer walking around Jeremy in a predatory circle. ‘Snapping your neck wasn't enough, threatening to shove a mystical ring up your ass wasn't enough’.

‘Guess I'm gonna have to punish you little Gilbert, until you learn your lesson'.

‘No- what do you mean?’

‘I thought so’. Damon murmured as he grabbed Jeremey from behind, 'I thought something was off when I threatened you at the carnival, fear, anger, yes, but there was something else, you're into being roughed up aren’t you little Gilbert?’

‘What? No, that's crazy’.

‘So that's what you're after hmm? Interesting, and here I was just going to kick your ass, but apparently I can do something much better to it’.

‘No,  no. You got this all wrong’.

‘Sure I do’.

Damon turned Jeremy around and stared into his eyes. 

‘Don’t’ Jeremey murmured breaking eye contact, ‘look maybe you're right okay, but just don't, that's not why I came here, and besides it doesn't work okay’.

‘And how would a little brat like you know something like that?’

‘I just do alright’.

Damon grabbed Jeremy's jaw and forced him to look at him. ‘I have had it up to here with Brunette's playing games with me today, so don't even try the mysterious act with me little brat'. Damon's eyes narrowed, ‘somebody else has had at you right? enough to make you know you like it rough?’

Jeremey looked away. 

‘let me guess, Lockwood, right?’

Jeremy's eyes flew back to his panicked, ‘How did-

‘-You  reeked  of him at the carnival, I'm not sure what's going on with that family but I'm pretty sure they're freeks of some kind, oh and fyi, if you don't want anyone to know your banging Tyler Lockwood maybe don't show up places threatening people when you have his stench all over you. -Come to think of it you also reeked of adrenaline when I grabbed you.

I thought it was because you realised just how stupid threatening a vampire was, but now I'm thinking I was just the icing on your stupidity cake that day; so what happened?’

‘One minute we were just talking’.

‘Then he just got really mad over nothing and the next thing I knew he had me by the throat and he was really strong, I mean like you are strong’.

Interesting, what was the deal with that family?

-‘and suddenly we went from arguing too... I mean he just started kissing me, but not like real kissing more like… I don't know it was really aggressive, and…’

‘Did you like it?’

‘… Yeah, but I don’t think it's a good thing that I did because, well, it just escalated and we ended up... He was really freaked out afterwards and I pretended that I was freaked out as well, but I wasn't, because I finally understood something about myself, but that doesn't mean I have to go with it’.

‘Well, I can take no for answer’.

‘Thanks, I guess’.

‘Yeah well, taking advantage of messed up teenagers is just the kind of thing that makes people think I'm a bad guy, and I think I'm kinda trying to turn over a new leaf’.

‘Because you have the hots for my sister?’


‘You know I'm not okay with that’.

‘Yeah, I know’.

He had been about to let him go, he really had, but then he had to mention his damn sister, who just like Katherine had been stringing him along to get what she wanted and as soon as she did she dropped him like a bad habit.

Yeah okay so he'd snapped her brother's neck, she had every right to be mad at him, but she should have left it there instead of playing him like a fool and making him believe that she was going to forgive him when she had no intention of doing so. And he was sick of her pretending there was nothing going on between them just because she wanted Stefan more. He was sick of all of it, how long was he going to be a slave to that face? He had to break out of the trap he had dug for himself, he had to do something...

He eyed up Jeremy. ‘second thought, I can't just let you go unpunished, what if you decide to do it again?’

‘No-no I won't’ Jeremy looked at his ring and gripped it.

‘Relax little Gilbert, I'm not going to kill you, nothing that obvious, no I'm going to do something that will prove once and for all that I don't care what your sister thinks’.

‘I don’t under-

He was in front of Jeremy before he had a chance to move, sinking his sharp fangs into his taunt neck as he cried out and struggled, but he only allowed himself a taste. He meant what he said he wasn’t going to kill him.

Damon backed him up against the wall and slid his hands between the wall and his body palming his ass, before turning him around and bringing his hand down hard on his ass. ‘Need it rough’, he found himself panting 'so don't take it easy on me’. Damon's smirk as he vamp sped them up to the bedroom and pinned him down one hand holding his wrists the other sliding down his body was pure evil, proving once again that something was wrong with him as it made him shiver uncontrollably.

Don’t move’, Damon growled in his ear while unbuckling him, ‘not a muscle do you understand or I'm going to punish you harder for disobeying me’. Damon was stripping them both at super speed and he suddenly felt vulnerable and exposed as Damon stared down at him and not for the first time he realised that Damon wasn't just handsome he was really beautiful and he had the most perfect lips. He suddenly wanted Damon to kiss him, what was wrong with him? -he wanted to kiss a man, a creature, that had killed him in cold blood only a few days ago, and who he'd been planning to murder in revenge just hours ago.

He was messed up … It was just everything hurt so bad since Anna, he couldn't stand to think of her burning to death like that, she must have been so afraid, so alone. He hadn't been able to save her, and Vicky,  he didn't even know what happened to her, but he knew it was bad no matter how much everybody lied and treated him like an idiot child.

He knew about vampires from Anna, he knew about compulsion, it didn't take a genius to realise the major gap in his memories of Vicky -when he had loved her so much that her death was killing him, had to courtesy of his sister getting Stefan or Damon to make him forget. in fact, sometimes he thought he had dreams where he begged her too.

He couldn't blame her for wanting to help him, if the positions were reversed and he had a way to ease Elena's pain he would have done the same thing, but he still couldn't help wondering if the not knowing was worse. Then again knowing what had happened to Anna wasn't making it any easier to accept. 

Logically it seemed Stefan was who his sister would ask, but something about the way Damon's voice affected him when he spoke to him now, how it felt kind of intimate like Damon had been inside him somehow made him think it had to be Damon. Maybe Damon was stronger or better at it or something and that's why he was chosen. Either way, compulsion hadn't taken away the feeling that something horrible had happened to Vicky, he knew something had, he just couldn't remember what.

So here he was messed up about Anna, messed up about Vicky, and if he was honest just not right since his parents had… Anna's death had just been the last straw. He'd taken her blood half hoping it would just kill him so he wouldn't have to feel like this anymore. Drugs didn't work, alcohol didn't work, even what happened with Tyler had only taken the edge off for a moment and it seemed like Tyler scared himself with how far it went, how rough it got, he doubted Tyler was ever going to want to touch him that way again, and he didn't really want him to because he wasn't even into Tyler, he'd never been more than the rich asshole jock at school with the hot temper.

The only other option was Matt, and there was no way that was happening. Matt just wasn't the aggressive type, not if the way he moped after his sister was any indication, also Matt was a pretty blonde, not his type at all, and he was his sister’s ex-boyfriend, and judging by a conversation he'd overheard between Elena and Caroline that he wished he hadn't, the guy she lost her virginity too, gross.

But Damon was also… no, not really, he wanted her but he couldn't have her. He wasn't her boyfriend no matter how much he clearly wanted to be.

He knew Elena had rejected him the night Damon killed him, he also knew Damon was drunk and lashing out at her by hurting him, just like he was doing now, he'd pretty much said so…  well he needed to lash out too , but unlike Damon he didn't have any outlet, he couldn’t just go around snapping necks without consequences, he couldn't even commit petty vandalism to blow off some steam because damn near everything a person even thought about graffitiing or smashing around Mystic Falls was some kind of founder's relic, monument, artefact, or heirloom.

He'd never minded before, never thought anything much of being a member of a founding family, but now it was like it was strangling him, the entire town was stifling with his parents gone- he was in constant pain and there was nothing he could do, it had got to the point where he didn't even feel like he could breathe. He couldn't go on like this, he couldn't take it anymore. He was drowning, desperate to cling on to something, anything.

He moved his head up to touch his lips to Damon's whose eyes narrowed as he moved his head away. ‘Disobedient little Gilbert. Hard punishment it is then’.

Damon turned him over and lay over his back pressing up against him hard and insistent.

‘Wait, I’- he wasn't ready for it right this second! After Tyler, he knew how much it hurt if you weren't prepared.

‘Be quiet’. Damon hissed straddling his legs and bringing his hand down hard on his bare ass.

‘Ah, god, that's- you're not going to punish me, punish me?!’

‘Oh, yeah I am, and you have no one to blame but yourself. Now if you are good and keep the count, I might, might take it easy on you and just fuck you after 30 lashes, but if you drop a single count I will start again until you have it right do you understand?’

‘I-…’ what had he got himself into? -could he do this? He had a good amount of sexual experience for his age maybe, but that didn't exactly mean he was up to taking on Damon Salvatore in bed.

Damon's hand came down on his bare ass and he yelped.

‘I asked you if you understood?’.


Yes what you insolent brat?’

‘Um, yes sir?

‘That's more like it. Now after every lash you are going to give the count and say Sir do you understand?’

‘Yes Sir’.

Damon ran his hand over his ass almost soothingly for a moment before he heard some rustling. The loud snapping of a belt made him jolt, but Damon pinned him down hard with a hand in the middle of his back, and he couldn’t move, was helpless against Damon's superior strength, just like his life he was helpless and at the mercy of things he couldn’t control.

‘N-no, with your hands, not with the belt please’.

‘From now on you will only speak when I tell you to do you understand?’


-Damon's hand came down harder making him cry out at the sting. ‘The longer you defy me, the longer it will take before we even start your punishment; now are you going to obey? …Good boy, I didn’t tell you that you could speak. You may answer’.


Damon's hand came down hard enough to make him shake as he sobbed out ‘I mean yes,  sir ’.

‘Good. Now remember to keep count . I give you permission to speak for that, if you say anything else I'm going to punish you even more severely, you may answer to say you understand’.

‘Yes sir’ he whimpered helplessly ‘I understand’.

‘Good let’s begin. Oh, one more thing’ Damon lay over his back his soft lips at his ear ‘ you're not allowed to come under any circumstances ’.

He opened his mouth to say he wasn’t hard, and it didn’t seem likely he would come from having the hell beat out of him with a leather belt for trying to stake him and then being stupid enough to admit it, but he clamped his mouth shut because he wasn’t allowed to speak and didn’t want to get punished even more.

‘Turn your head more to the side I want to see your face’. Damon whispered darkly in his ear. ‘That’s it. Now, are you ready to take your punishment Jeremy? You may answer if you are’.

‘Y-yes sir I'm ready’. He sounded miserable even to his own ears, but he knew better than to try and escape this. Damon had chosen to make him pay for crossing him in a way he might survive, this could easily have been a secondary neck snapping without his ring and he knew it. But that didn’t mean that it wasn’t difficult to just lie still and wait to be beaten.

He tensed as he heard the belt swish through the air and screamed at the top of his lungs as the unforgiving leather lashed his skin.

‘I told you to count not scream’. Damon's tone was menacing and he tried to reign in his cry of pain.

‘One, sir’.


Damon brought down the belt again and he howled in pain, ‘Two, sir’ he sobbed out as Damon whipped him mercilessly, until he began to feel light-headed, until he didn’t know where one lash ended and another began, but he kept the count no matter how much it hurt, and it hurt , because the alternative of starting again would be worse.

He knew it was leaving deep red welts on his back and ass, even if Damon didn’t keep saying how it looked like a beautiful work of sadistic art.

Around lash sixteen when he was fighting the urge to pass out and Damon made it clear what would happen if he did, something strange started to happen. Damon's dark velvety commands urging him to keep count even as he was running his hands over him for longer between lashes and making him say he was ready for the next before delivering it was starting to get to him. Somehow, by lash seventeen or eighteen, even though he was in agonising pain, he was inexplicably growing hard and he realised Damon had been hard the entire time.

Damon suddenly increased the pace of the lashes mercilessly until his cries became one long wailing howl:

‘Nineteen sir!’

‘Twenty sir!’

‘Twenty One sir!’

‘Twenty Two sir!’

‘Twenty Three sir!!!’

‘Twenty Four sir!!!’

< span class="font-red"> ‘Twenty Five sir!!!’


He was crying in earnest as Damon stayed his lashes, rubbing his hands over the raised welts on his skin.

‘We’re not done yet little Gilbert. You know what to do to make this end, now say it’.

‘Yes sir’

Damon brought the belt down harder than ever and the agony became excruciating, completely breaking his threshold of pain, his voice strangled high-pitched and desperate as he barely managed to cry out ‘Twenty Seven Sir, -oh please god stop, I can't take any more ’.

‘If you say anything other than the count and sir I will start again, and I will whip you bloody So far I've been restraining myself by not breaking your youthful skin, that could change, now keep count’.

He took a deep shuddering breath, his skin was alive with pain, he couldn’t take anymore.

‘Jeremy. Are you ready to continue?’ Damon ran his hands over his stinging welts making him suck in his breath harshly. ‘You may answer if you are, but you may only say yes sir or no sir’.

He was wrong, he couldn’t survive this.

‘If you do not answer me in the next five seconds, we will start again from count one, and this time I will be using the belt buckle. Now for the last time are you ready to continue?’

‘Y-yes sir’.

‘Twenty Seven sir’ he howled as the belt lashed his battered over-sensitised skin.

‘Twenty Eight sir’ he screamed, sobbing and crying in pain.

‘Twenty Nine sir’, he wept.

‘Thirty Sir’.

He heard the belt hit the floor as Damon tossed it aside laying over his back, his abused flesh screaming in protest as his tears flowed. Yet as he shifted his position trying pointlessly to ease his pain he felt the sheet rubbing against his swollen length, he was still hard, certain proof he had gone off the deep end and couldn’t understand the difference between pleasure and pain anymore.

‘You took that so well little Gilbert’ Damon was purring in his ear. ‘Do you want me to fuck you now little Gilbert? or do you want me to heal you first, you’ve paid for crossing me, and you took your punishment so well I don’t mind rewarding you with healing before I fuck the juvenile assassin tendencies out of your ass’.

… so good ’ Damon purred, ‘still obeying the rules of the game, I like that little Gilbert so I'm going to give you a reward. You're free to say what you want’.

‘It hurts, please- please heal me’.

‘mmm something’s missing’

‘Please heal me sir’.

‘Since you asked so nicely you can have some of my blood, but, you're going to have to take it yourself’.

He couldn’t be serious, he didn’t have fangs, he couldn’t-

Damon turned him over and the pain made the decision for him as he launched himself at Damon's wrist, but Damon pushed him back and shook his head, ‘no not from there, little Gilbert’. He looked at Damon's neck but Damon smiled and shook his head slowly, ‘not from there either’.

Then where could-

Damon's eyes travelled downwards and he understood.

Vicky and Anna hadn’t really done it to him a few well-placed kisses and some comments about not wanting jaw-ache, and he hadn’t done that with Tyler, in short, he didn’t know how.

‘I thought you were in terrible pain’ Damon purred mockingly ‘you want to heal right?’

Damon was watching him in that disturbingly intimate way he had before snapping his neck,  and he had to be turning into a completely masochistic danger junkie because it was as inexplicably dangerously hot as it was terrifying.

‘Personally, I could fuck you just as you are right now, with tears in your eyes, and red welts all over your skin, it’s a hell of a turn on.

He couldn’t take the throbbing searing stinging pain a moment longer, so he took Damon into his mouth and bit as hard as he could, surprised when he didn’t draw blood, Damon's hands tugged painfully on his hair and he yelped as Damon pulled him up to eye level, ‘listen brat, your meant to  bite  not chew so watch the damn molars! They're for crushing not biting and if you try that again, I'm going to show you how I crush things between my teeth, got it?’

‘S-sorry, haven't done this before’.

‘Obviously. Now this time use your incisors to bite’.

He let Damon shove his head down and sucked him back into his mouth at a different angle so he was biting into the side of his cock careful to use his incisors this time.

‘Harder’ Damon growled.

He would have thought it was easier than this, but other than trying to get Damon to let him use a blade on his dick, which he just didn’t see happening, his only option was to… oh, okay- he sucked him fully into his mouth while grasping Damon's hips and pulling him forwards.

‘Now you're getting it’ Damon purred thrusting into his mouth, he placed his hands on Damon's hips trying to control the pace while Damon's hands gripped his head, fucking his mouth hard and fast as he tried not to choke, his incisors nicking his hard cock and drawing blood. He tried to slow Damon down by holding on to his hips so he could drink enough to heal, but Damon shoved him on his back straddling his face and fucking into his mouth at super speed, his incisors drawing more blood as he sucked it down greedily desperate to be healed.

He thought Damon would come in his mouth and it would be over, but Damon slid down his body until he was laying on top of him biting his neck hard until he was shaking as Damon was drinking him down making savage growling noises.

Damon wiped the blood off his mouth and stared down at him, and all he could think was Damon had eyes like a wild predator, beautiful but deadly.

‘Are you ready to get fucked?’

Was he? … he might be healed but he was exhausted could he really take more of whatever the hell Damon would do to him?

Answer me or am I going to have to punish you again?’