Shy gayish geek

We had to share a room on our family vacation. Mom wouldn't let him share one with my sister, said she wasn't ready to be a grandma. I'm not sure that it was going to help all the other times that they had been fucking, but mom was mom and only saw what she wanted.

"Yup, it's more comfortable. You should try it," he replied as I pulled off my Tshirt and shorts.

I slept naked all the time but tonight I left my underwear on. There was no way I was going to let him see my dick in case I got hard. This was already difficult enough. I got in the bed, he was almost right in the middle of it and didn't seem to want to move.

"Night, Gabe," I said, settling into my pillow and pulling the comforter over my shoulder.

"Night, buddy," he replied and wrapped his arm around me, pulling him into his naked body.

"Umm, what's up Gabriel?" I asked, blushing as I felt his warm body pressed against mine.

"I sleep better when I hold your sister, you don't mind do you?" He asked and snuggled into me, not waiting for my answer.

"It's a little weird," I said.

My heart was racing. Gabriel was beautiful and having him wrapped around me made my dick hard. His arm was dangerously close too and if he moved it down much more he'd feel it.

"Naw, it's cool. What will be weird is when you wake up to my morning wood," he chuckled and pushed his crotch into my butt. He may have not been hard but I definitely felt his dick against me. "Don't worry, I'll behave," he added and then kissed my temple.

I laid there and didn't know what to do. I didn't think I was going to be able to fall asleep but it was oddly comfortable and it felt safe in his arms. As time passed I heard his breathing change and figured he was sleeping. My whole body was pinned against him and slipped my hand in my briefs as I enjoyed the embrace. I had to move slowly so I didn't wake him. The last thing I needed was him to wake up and find me jerking off.

I moved my butt back into him. I wanted to feel his dick, I knew it would make me blow faster and I needed to stop.

"You horny, little buddy?" I heard his voice and froze.

He didn't freeze, he pushed his dick right against my ass and I felt it growing. He held me and began to hump his harding cock on me. He ran his hands on my stomach and chest and then down to my dick.

"Oh you're super horny," he chuckled and kissed my temple again. "Something about hotels really gets me going. You good?" He checked in on me as he pressed his body into mine.

"Yeah," I said softly, pulling my hand out of my underwear.

I reached behind myself and grabbed hold of his thick dick. He pulled away and let me grab and feel it.

"You like that?" He asked as I played with it.

"It's nice," I said, turning to gauge his face.

"I like this," he replied and pushed his hand in my underwear and right into my crack.

He immediately found my hole and began to rub on it. I was in heaven as my sister's beefy man pushed in. I let go of his cock and slipped my briefs off and let him put his cock between my cheeks.

"You know what makes me sleep even better?" He asked. "When I fall asleep with my dick in something."

He grabbed my left cheek and pulled them apart and put his dick in my crack and started massaging up and down, he must have been a leaker because it felt more wet with every pass of his dick.

"Are you sure about this?" I felt a tinge of guilt.

"Oh, I'm sure," he said and began pushing forward right at my hole.

I felt my ring slowly opening up as he made a humping motion, letting his cock lead the way. I relaxed and tried to let him in and with one more push I felt his cock pop inside of me. I hadn't been with someone in months and damn it it feels good having his manhood in me. He slowly pulled me in closer, his cock slowly pushing in.

"Does this mean I get to fuck you all week?" He whispered in my ear as I felt his stomach press against me, he was all the way in.

"God, I hope so," I moaned as I felt overwhelmed by how amazing he felt around and inside of me.

He gripped me tight in a hug and humped himself into me. He bit and kissed my ear as he started saying dirty things in my ear.

"You like that fat cock. Going to cum so much in that tight ass. I'll be dripping out of you at breakfast."

It was ecstasy, Gabe was a sex god and I was loving every second of it.

"Cum for me, baby," he said, grabbing my dick and stroking me.

He kissed my neck and thrust in harder. I couldn't take it and began spraying my load all over the sheets. He growled behind me and pushed in a few more times and then grunted and let go. My ass was in heaven as he put his load in me. Holding me against his body as his cock throbbed and deposited. His hand played with my dick as his face nuzzled my neck.

"Good night, baby," he said and drifted off to sleep.

“Fuck, why is this so good,” he finally said something once we broke apart for a moment.

“I don’t know. You’re fucking good at it though,” I told him and leaned up and kissed him again, I didn’t want to stop.

I could feel my boner pressing on his ass as he sat on my lap, I’m sure he could feel it too. I grabbed on to him and he didn’t seem to care as I slowly humped up against him.

“You hard too?” I asked him, looking down between his legs.

“Yeah,” he admitted. “What are we doing?” He asked.

“Just fucking around, I guess,” I told him and gave him a peck. “I’m so fucking horny now.”

“Me too,” he agreed.

“I could probably cum in my shorts if we keep making out and you let me hump into your ass,” I was more asking him to let me then telling him I could.

“Jesus,” my friend chuckled and then pushed his weight down on my lap.

I moved my hand and grabbed the front of his shorts and gave his dick a squeeze. I hadn’t touched a dick since my exploring years back in middle school but I’d do anything to get off, even if that meant helping him out as long as I could rub my dick on his ass.

“Well that will make me cum,” my buddy said.

“Perfect,” I told him and thrust upward and kissed him again.

I gripped his dick and our tongues went in and out of each other’s mouths. His ass was working up and down the length of my cock and god it felt good. Why did my buddy’s mouth taste so good and why was kissing him making me do things I didn’t think I wanted to do.

I jacked him off the best I could through his shorts. Making sure he stayed as horny as I was so I could get off, I really needed it. He got really tender with his kissing, thoughtful and almost caring. It was driving me wild, I was on the edge as he broke his lips from mine and looked down at me for a second. His hot breath on my face, I took a deep breath, breathing him in. We looked intently into each other’s eyes. My hand was still moving up and down his cock. He was still rubbing his ass on my dick.

“You’re gonna make me nut,” he almost whispered.

“Me too,” I told him as I watched his face.

I saw his expression change, our eyes were locked. My best friend was cumming and my hand felt his dick expand in his shorts. I was doing it for him, I was making him cum. It was a fucking trip and I thrust up against him a few times and felt my own load building to the end.

I wanted to kiss him again, taste his lips and tongue as I blew. I leaned up and pushed my mouth on his and I let it go. The passion was crazy between us and I felt it from my head to my toes. I felt the warm cum jet out of me, making a mess in my shorts as I gave him deep kisses that I had only showed past girlfriends. He moaned in my mouth. I could still feel his cock jumping in my hand, still unloading in his underwear just like I was doing in mine.

I didn’t want it to stop. I didn’t want to face what we had just done without the horniness to cloud our brains. We kissed some more, slowly coming out of our fog. Enjoying the afterglows of our orgasms.

“That was intense,” he said as I moved my hand.

“To say the least,” I laughed nervously.

He looked down at me, like he could tell exactly what I was thinking. I blushed, I felt like he saw a part of me I didn’t know I had in me or that he’d judge me for doing it, even though he did it too. But instead of making it strange or saying something childish he leaned down and gave me one last kiss.

“You’re an amazing friend,” he told me.

My heart warmed, his words gave me comfort and I felt the same way about him.