Whatever You Want To Be

Weekend pt. 2 [M]

A/N: mature content ahead! flashback of the weekend monty spent at winston's house.

Monty's POV

I woke up the next morning naked and confused. When I looked over to my right, all the memories of the night before came flooding back. I couldn't help but feel embarrassed, remembering what I told him yesterday. I groaned aloud before realizing I should try not to wake him. As quietly as I could, I got out of Winston's bed, and started to look for my clothes. I picked up Winston's clothes too, and put them on the nightstand next to him.

Should I leave? But I told him I would stay. Fuck it. Might as well, since I don't even try to do my homework. I padded down Winston's stairs, wondering if he'd mind if I got something to eat. I decided against it because I was afraid he might get mad at me. What if he wasn't a morning person, or regrets what we did last night? Shut up, brain. He invited you to stay. That means something.

To entertain myself while waiting for Winston to get up, I started to look at my phone, which I had left inside my jean pocket. I realized that Bryce had blocked me on everything. Annoyed more than anything, I glared down at my phone.

Just then, I heard noise on the stairs. Winston walked into the living room looking tired and amazingly attractive. His eyes were half closed and his hair was all disheveled. He also had a sight blush painted across his cheeks. I found myself staring at him for a little too long. When Winston's mouth spread into a smile upon seeing me, my entire facade melted away. He was beautiful.

"Good morning," he said. Even his voice was attractive. "Morning," I replied. "Do you want anything to eat?" he asked. Yes. You. I want you. "Sure," was what I ended up going with.

We ate our cereal in silence, but I didn't feel the pressure to talk. "So what do you wanna do today?" Winston asked. I looked at him with a smirk, feeling my flirty side come out. "You." I can't believe I just said that. Jesus. When I saw Winstons blush though, it made me want to flirt more.

Winston cleared his throat, trying to gain some composure and failing. I inched closer to him, looking between his eyes and his lips. Winston closed the distance, slipping his lips onto mine. He instantly sighed with the contact. I wove my fingers in his hair and pulled his face closer to mine, deepening the kiss. I brought us both to our feet and walked him to the stairs, not breaking the kiss.

Winston pulled away from me, only to take my hand and lead me up to his room. We fell onto his bed and continued making out. We were all over the place, kissing sloppily, our bodies moving on their own accord. Winston started to slow down the kiss, making it more intimate.

I opened my eyes slightly for a second, looking at him. He was right here. I rolled on top of him and took off my shirt. He eyed me with desire, and I started kissing him again. The kiss was deep, our tongues intertwining. I rode my hands under Win's shirt, feeling his soft skin under my fingertips. I took it off of him and pressed my chest to his. Winston moaned as I gently pushed my knee to his groin.

He ripped off my pants with eagerness, and I couldn't help but smirk. "Wow, someone's patient." Winston glared at me, making me smirk even more. He grabbed my neck harshly and brought my lips to his. While kissing me, Winston took my dick in his hand. I moaned slightly, and he used the opportunity to slip his tongue in my mouth. There was so much going on, and my body was buzzing with pleasure.

I pulled down Winston's pants, so that we were both fully naked. I held myself above him, panting, and staring at his beauty. "We should actually prepare this time." I found the words coming out of my mouth before I could stop it. Last night, he sounded like he was in pain, and I didn't want to hurt him. Winston blushed even deeper, and smiled up at me. "That would be smart," he said.

He handed me the lube, and once again, I just sat there like an idiot, not knowing what to do. He chuckled, noticing my lack of knowledge, and reached to help me. Winston squeezed a generous amount of lube onto my finger and laid back down. I was still confused. Winston smiled again, making my heart beat faster. He grabbed my hand and led it to his entrance, and I finally realized what I was supposed to do. Gently pushing my finger into him, I saw Winston's face contort in pleasure. I liked making him feel good.

I gently continued loosening him before Winston told me to add another finger. I did what he said, and he bit down on his lip. "You okay?" I asked. "Yeah, just need to get used to it. I'm still sore from last night." I felt bad all of a sudden. If he felt pain from two of my fingers, how much will it hurt when I put my dick in him? Why didn't he tell me that he needed to be prepared before?

I started to get drunk on the sounds Winston was making under me. I got into a rhythm, and watched with fascination by the way my fingers were being swallowed up by him. "I think I'm ready no- " Winston's sentence was cut off by a loud moan that escaped his lips. "Sorry, did I hurt you?" "No." He could barely form a word. "You're just," he gasped. "hitting my prostate right now." He barely got the sentence out before moaning again.

Prostate huh? I brought my fingers to the same spot again. Winston moaned. I did it again, and again, and again. Winston started to shake. "I'm g-gonna-  Monty, S-stop." I didn't. I continued to pound my fingers into his spot and he stopped protesting. I reached out with my other hand to jerk him off while continuing my attack. His body convulsed violently and he moaned loudly. I covered his lips with mine as he came.

Winston looked like he was in heaven. I did that. I made him feel like that. Completely satisfied with myself, I laid down next to him. "What about you?" Winston managed to breathe out. "What about me?" "You know. I should return the favor," Winston started to protest. I cut him off saying, "Dont worry, we still have time for me to fuck you."

"I- ju- wha," Winston stuttered. My smirk found its way back on my face. "No need to be embarrassed. I know you want this." I gestured to myself. After a split second of him looking at me, and me trying to act sexy, we started laughing. I was laughing so hard that I could feel tears coming into my eyes.

He made me feel amazing. I felt like I could act like myself around him, even though I barely even knew who I was. That tends to happen when you spend your life faking your entire identity and pretending to be someone you're not.

(edited)