Requested by flowerbomb1692: Y/N is an upcoming actress and gets invited to an event. She's a huge fan of Tom, so when they meet, they start flirting and hitting it off immediately. They decide to go out for drinks afterwards and things get steamy.

I stepped out of the car, a smile immediately forming onto my face as I was confronted by the rapid flashing of dozens of cameras. I stood up straight and put my hand on my hip, my purple lips smiling at the paparazzi as I walked along the red carpet. I was slowly but surely making a name for myself as Hollywood's biggest upcoming actress, and so I had been invited to this year's Oscars Awards. The Oscars that Tom Holland was also attending. I'd been a huge fan of Tom since I'd seen him in movies like "Spiderman" and "Edge of Winter", and to say that I had a massive crush on him was an understatement. And so when I'd been invited to the Oscars, knowing that he'd be here too, I knew that I had to look my best. I sauntered to the photos section, my black dress sweeping the floor as I stood there to take photos.

"Y/N, OVER HERE!"

"Y/N, LOOKING STUNNING TONIGHT!"

"Y/N, GIVE US A SMILE!"

"TOM!"

My eyes widened and I looked to my side. My breath hitched, my heart jumping in my chest as Tom walked towards me. And my god, he looked good. He was wearing a standard black suit and tie with a white shirt, but he looked a lot better than other guys did. He smiled and bit his lip as he walked towards me.

"Hope you don't mind me jumping in here for a photo op with a beautiful girl." He teased, making me smile and bite my lip as he leant down and kissed my cheek.

"I'm Tom, it's great to meet you. You're Y/N, right?" He checked. My eyes widened slightly, my heart fluttering at his words. He knew my name. Tom fucking Holland knew my name.

"Yeah, that's me. It's amazing to meet you too, I'm a huge fan." I admitted, making him smile at me as the cameras continued to flash.

"I can already tell that I'm going to be a fan of you too." He flirted subtly. I smirked and bit my lip, looking down as I tried to hide my blushing cheeks.

"What do you say to giving the paps some nice shots of us meeting?" He chuckled as he curled his arm around my waist and pulled me into his body.

"I'm up for that." I smiled, making him return it and bite his lip as I draped my arm over his shoulder.

"You two look cute together!" One photographer yelled, making us laugh and look at each other.

"Hopefully it won't be the last time that we're photographed together." He continued to flirt. I smirked and bit my lip as I looked back at the cameras, Tom's gaze staying on me as I looked at the paparazzi.

I walked around the reception of the Oscars, a glass of champagne in my grasp as I greeted everyone.

"Y/N." I turned around and smiled as Zendaya walked towards me.

"Hey, girl, how are you?" I laughed as we hugged.

"I'm great. So are you, apparently." She smirked. My eyebrows furrowed at her.

"What?" I chuckled.

"Word has spread about you and Tom meeting in the pap bit. Apparently the flirting was real." She nodded. My eyes widened slightly and I chuckled again as I felt my cheeks heating up.

"I won't lie, Z, he was nice, and he looked good." I admitted.

"He thinks the same about you. He's been talking about how hot you look." She nodded. My eyes widened further.

"Oh my god. You're not telling me that I might actually have a chance." I shook my head.

"That's exactly what I'm saying." She smirked, making me return it and bite my lip.

"He's at the bar now, babe. I say go for it, this could end very well for you." She encouraged. I looked behind me and bit my lip again as Tom stood there, waiting for a drink.

"Fuck it. It's now or never. And if it goes tits up, I never have to see him again." I shrugged before raising my glass of champagne to my lips.

"Attagirl." she smirked as I downed the alcohol. I winced slightly as I finished drinking it and my eyes flicked back to Zendaya.

"Wish me luck." I nodded. She returned it and winked at me as I started to head towards the bar. I arrived next to Tom, making him look at me as I got to him.

"Hey, darling. Good to see you again." he smirked, his body leant against the bar as his eyes flicked up and down my body.

"It's good to see you too, Tommy. Fancy buying me a drink?" I asked as I put the empty champagne flute on the bar. His smirk widened and he nodded as he stood up straight.

"I'd be happy to. But, um...not here. How about we go to my hotel's bar, and, well, see where the night takes us." he shrugged. I raised my eyebrow at him.

"Where are you expecting it to take us?" I teased.

"I don't know, but I want to find out." he flirted back. I smirked and shook my head before looking back at him.

"Alright then. I'm all yours." I nodded. He returned it and bit his lip, my heart jumping as he gently took my hand into his before pulling us away from the bar and out of the reception.

"Yeah, 'Cherry' was pretty insane to do. It was amazing, don't get me wrong, but it was my toughest role ever." Tom shook his head, me nodding along as we sat in his hotel's bar, talking and drinking.

"It looked hard to do, but it paid off. You and Bravo were incredible in it." I smiled.

"Thank you. I saw your most recent movie too, you were insane in that." he returned.

"Thanks, but I don't know. My co-star and I definitely lacked the chemistry that you and Ciara had." I chuckled.

"It's all about how well you get along with them, I guess. I reckon that we could go and play a couple right now given how well we've hit it off." he teased, making me raise my eyebrow at him as he raised his glass to his lips.

"I bet that you're just saying that because you want to kiss me." I flirted back.

"That too." he admitted with a nod, making me laugh and shake my head. Tom continued to look at me gently, making my smile dip slightly.

"Can I kiss you?" he asked quietly as he slowly but surely started to lean in. I gulped, my smile completely disappearing as I leant in too.

"Please do." I mumbled. He gave me a small smile and nodded as his hand raised to cup my cheek. His gaze flicked from my eyes to my lips before he leant in and gently kissed me. I returned the kiss, my hand also raising to cup his cheek as his hand moved to my waist. I couldn't help but smile into it, making him smirk as he deepened the kiss and gently slipped his tongue into my mouth. We started to make out, our drinks long since forgotten about as things started to get heated between us. He broke the kiss and touched our foreheads, my eyes fluttering open and looking into his as I gulped.

"Do you want to go up to my room?" He mumbled quietly. My eyes widened slightly. Was I really to have sex with Tom Holland? The answer was yes. I nodded and bit my lip, making him smile and peck my lips before he stood up.

"Come on." He spoke, making me smile as he took my hand and pulled me up too.

Tom smashed our lips together, the two of us stumbling into his hotel room as he shut the door with his foot. He gripped my hips, my hands holding his face and gently pulling at his curls as we stumbled around the room. He quickly tugged his jacket off of his shoulders, the garment falling to the floor as we continued to make out. I squealed against his lips as he lifted me up and wrapped my legs around his waist. He smiled against my lips, making me smirk and continue to kiss him as he put me down on his bed and crawled over me. He broke the kiss and moved his lips down to my neck, making me breathe out and arch my back into his chest as he started to kiss my skin.

"You're so beautiful, love." He mumbled as his hand moved around to my back and unzipped my dress before starting to pull it down my body. I bit my lip, my heart pounding at his words as his lips trailed down to my chest. He unhooked my bra and threw it across the room, leaving my chest completely bare to him as he trailed his lips down to my stomach.

"Tommy, hurry, please." I begged, making him smirk and look up at me through his eyelashes as he pulled my dress the rest of the way off and exposed my thong. He bit his lip, his eyes glued to me as he pulled my thong down too.

"You're already so wet for me, babe. Good to know that you'll be easy to please." He teased, making me suck in a breath as his finger gently started to move over my folds.

"I'm with you, Tommy, of course I'm wet." I flirted back. He smirked and shook his head before leaning down and attaching his lips to my clit. I gasped, my back arching and my fingers tugging harshly at his curls as he started to eat me out.

"Jesus, Tommy." I choked.

"You taste amazing, darling." He mumbled against me, making me harshly bite my lip as him speaking sent vibrations through me. His lips sucked on my clit, his tongue dipping in and out of me as the knot already started to build up. His hands curled around my legs and landed on my stomach, pinning my body to the bed as he continued to eat me out.

"Fuck, babe, this feels amazing." I moaned as his tongue continued to flick against me. I gasped, my eyes squeezing shut and my back arching as he gently inserted a finger into me

"Tommy, fuck!" I cried out, making him smirk and speed his finger up. My head lulled back, my hands gripping his hair with all of the strength that I had as he continued to eat me out and his finger pumped in and out of me. The knot in my stomach continued to build with every movement, moans leaving my lips as I got closer and closer. My back arched, another gasp leaving my lips as Tom added another finger.

"Fuck, shit." I moaned loudly, the boy's movements feeling amazing and pushing me closer to climax. Until I was there. My legs shook, my orgasm hitting me like a truck as my toes curled and the waves of pleasure washed over me. I sighed in relief, Tom removing his fingers and mouth from me as he stood from the bed and started to unbuckle his belt.

"That was amazing." I panted, making him smirk and nod as he undid his trousers and pulled them down, along with his boxers, to reveal his now completely hard dick.

"Yeah? You got enough in you for another one?" He teased. I smirked and bit my lip as he grabbed a condom from his wallet before crawling back over me.

"Only for you." I returned the flirting, making him chuckle and shake his head as he ripped the condom packet open with his teeth before rolling it on. He leant down and pressed our lips together again, me returning it as I curled my hands around his neck to pull him closer. We breathed out against each other's lips, my eyes fluttering shut as he slowly pushed into me.

"Fuck, babe." He sighed against my lips as he bottomed out.

"Move, Tommy, please." I nodded. He returned it, his head dropping to my neck as he started to thrust his hips. He quickly picked up the pace, his hips snapping against mine in seconds as he started to fuck me. Quiet moans and sighs left both of our lips, my eyes squeezing shut as the knot started to build up already.

"Jesus, angel, you feel amazing." Tom moaned into my neck, making me smirk and bite my lip as he started to leave open-mouthed kisses on my skin.

"So do you, Tommy, fuck." I choked. He returned my smirk and raised my legs to hook around his waist, making me cry out as the new angle allowed him to get even deeper inside of me. The sounds of our moans and skin slapping together filled the room, the smell of sex surrounding us as Tom fucked me into oblivion. His lips continued to work on my neck, surely leaving me with plenty of hickeys to cover up tomorrow as his hips snapped against mine. I held my lip in between my teeth, my eyes squeezed shut as the knot got unbearably tight.

"I'm getting close." I nodded.

"So am I, darling, so close." Tom grunted into my neck. Suddenly, his hand leant down between our bodies and started to rub circles on my clit, making me cry out and arch my back into his chest. The extra pleasure sent me over the edge, the knot exploding in my stomach. My legs shook again, my second orgasm of the night sweeping through my body as I came harshly around Tom.

"Fuck, babe." Tom moaned, him being pushed over the edge too as he filled the condom. His body halted, a sigh leaving his lips before his hips gently started to thrust again to ride us both through our highs. He stopped and collapsed on top of me, both of us panting heavily as he gently pulled out of me. He rolled off of me, our chests rising and falling as we lay there.

"That was amazing." he shook his head, making me smirk and look at him.

"It was. Best sex of my life." I teased. He laughed and bit his lip as he curled his arm around my waist and pulled me into his body as I rested my head and hand on his chest.

"Best sex of mine, too. Question is, what is it going to lead to?" he mumbled as he kissed my head. My eyebrows furrowed and I looked up at him.

"What do you mean?" I asked. He shrugged and looked down at my lips.

"Well, I don't want this to be just a one-time thing, or something. I've been flirting with you all night because I like you, and I think that you're really beautiful." he admitted. My eyes widened slightly, my stomach exploding into butterflies as he admitted that he liked me back.

"You don't even know me, Tommy." I teased.

"Which is why I want to take you out, I want to get to know you. And you know, see where this goes. Hopefully into a relationship." he smiled, making me return it and bite my lip.

"So, what do you say, darling? Can I take you out?" he mumbled, his hand gently rubbing up and down my back as he gazed at me with adoring eyes. I returned the look.

"I'd love that, Tommy." I admitted quietly. He breathed a sigh of relief, making me laugh and shake my head as I cupped his cheek and kissed him again.