The boss' assassin (Mob boss!AU, Tom Holland)

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Requested by _miedelas: Tom is a mob boss, and Y/N is his best assassin. She uses her beauty and sexiness to kill, and one day, she comes back from a mission with a hickey on her neck, which she hasn't noticed. This starts to make Tom jealous since he has feelings for her, and then later he hears her joking about how hot the target was, and that she could have slept with him before killing him. Tom gets really pissed off and jealous and they fight, in which Tom calls her a derogatory name. Y/N gets really upset by this and threatens to quit, so Tom reveals his true feelings for her, and they end up getting together.



I walked into the mansion, my heels clicking against the marble floors and my previously white dress now soaked in blood as I walked through the grand building. I walked past Tom's staff, none of them phased in the slightest by the sight of me covered in blood as I sauntered towards my boss' office. As I got to it, I gently knocked my fist against the door.

"Come in." His muffled voice sounded. I opened the door, making my absolute god of a boss look up at me from his work as I walked in. He raised his eyebrow and sat back in his chair, one of his fingers rubbing against his lower lip as he looked up and down my figure with the eyes that I had truly fallen in love with by now.

"I assume that that's not your blood, sweetheart?" He checked. I scoffed and returned the raised eyebrow as I pulled the skirt of my dress up. Immediately, Tom's eyes flicked to my now bare thigh, my heart fluttering in my chest at the attention that he always showed me as I pulled my also soaked knife from my thigh holster.

"How long have I been working for you, Tommy? Of course it's not my blood." I scoffed again and nodded as I casually started to wipe the blade against my dress to clean it.

"That's my girl." He smirked, making me return it and bite my lip as I thought back to the mission that he'd sent me on today.


I yelped out as the man threw me against the wall, his hands immediately taking my face and his lips pressing to mine as we kissed. I returned it and let my eyes flutter shut, as usual using my attractiveness to get my target exactly where I needed him as he gripped my hips harshly, and kept me pinned to the wall. He broke the kiss and moved his lips down to my neck, making my eyes flutter shut, and my fingers tug on his hair as he nipped and bit at my skin. But the only reason why I was enjoying this so much was because I was trying to imagine that the guy who had me like this was actually Tom. After all, I was truly in love with the dangerous man who happened to be my boss. Tom was the most notorious and feared mob boss in all of London, and in a strange series of events, he had hired me to work for him as an assassin...after I had been sent to kill him. He was the only target who had ever gotten away, but Tom wasn't arrogant enough to think that that was because I couldn't kill him, no. I had let him live. And I was grateful to myself for that fact every day, given that he'd hired me on the spot after I had admitted what I had been there to do. I had been working for Tom for three years now, and it was no secret that I was his best and favourite assassin. I wouldn't lie, I was pretty conventionally attractive, and so I used my body and my looks to seduce both male and female targets alike. I had no problem getting myself into situations like this, where the target thought that I'd let them fuck me, before I'd pull out my blade and cut their throat. And I had no problem with it because I knew that I'd go home to Tom, the boy who I also pictured in my head when doing this. Because of course, I had fallen for the absolutely stunning man in my time working for him, and so I'd continue to picture him, and just hope one day that he'd feel the same.

"God, you're so fucking hot, I can't wait to be inside of you." The target growled into my neck, making me roll my eyes as I subtly inched up the skirt of my dress, and pulled my knife out.

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