Problem with a One Night Stand Ch. 05

I could hardly get my words out. "I never have." I admitted. "I've just always been with bigger guys who always took my smaller size as an invitation to top me. I love it though so I'm not complaining, but... yeah."

"I've never bottomed, if that helps." He told me, stopping his distracting exploration of my chest and propping up so he could face me. "I've only ever been with Casey, and he never wanted to mix things up."

"So what are you saying?" I asked, a burst of insecurity flushing through me. "The sex wasn't good the way we did it? You want to change it?"

"Oh, god, no." Barry laughed. "Josh, seriously? You think I don't enjoy what we have?"

"I don't get where you are going with this."

"Where I'm going? Josh, hopefully wherever I go, you'll be going too. I want us to be happy, and if we need to have these awkward conversations, so be it. I was just letting you know that eventually, I want you to fuck me. It has nothing to do with you being bad in bed or not being satisfied with you. It's that I want to try something with you because you are so good. I have never experienced anything like what you and I have. If you don't want to change it, that is absolutely fine with me."

I flushed, embarrassed that I was already letting my insecurity show already. "Okay, sorry." I mumbled.

"Don't be sorry." He smiled warmly. "Let's just have some fun, okay? You are being far too serious right now, and I think I know how to put a smile back on your face."

"Oh really? How so?" I grinned back at him, regretting my words as he sat back and flipped me over until I was on my stomach. "Hey!" I laughed out. "You can't just toss me around like a rag doll!"

Barry pulled me up onto my hands and knees, holding me in place with one hand on my hip while he reached over with the other to get to the other condom and lube bottle. I tried to look back to watch him, but he moved way too fast for me. In no time flat, I heard the crinkle of the condom wrapper as he opened it, and a second later watched it fly across the room. I gasped as the cold lube hit my entrance and his fingers gently wiped it around my hole. "I think you like it." He whispered in my ear as his thumb gently breached me. I moaned out in pleasure as he held it there, desperate for more.

"I do." I panted out. "Don't tease me, Barry. Fuck me."

"Think we can compete with them?" He gestured towards our headboard, which was probably directly opposite Matt and Jason's. I could barely hear anything from them now that the blood flow was going straight to my cock as a result of Barry's subtle maneuvering of his thumb and fingers on my ass.

"Oh my god, yes." I moaned out. "Fuck me. Please."

I felt Barry position himself behind me, and moaned out as he popped his thumb out from my tight hole. The emptiness was quickly remedied with the press of his fat cockhead pressed against my tight ring. He ran a hand down my spine as he eased into me slowly, drawing out a long moan from me as he took his time pressing inside me. "Oh, fuck, Josh, you're so tight." Barry moaned out as his thighs bumped into the back of me. His palms smoothed over my ass as he withdrew in a single slow motion and then rammed back in. I wasn't ready for it and let out a yelp as the pleasure coursed through me. The thump of the headboard with his rough thrust made us both laugh, and before I knew it, we were both moaning out as he pounded into me with a ferocity I hadn't expected. Barry gripped my hips tight enough to bruise as he slammed into me over and over again, making me moan like a porn star with each slap of his balls against me. My elbows buckled and I lost my balance after a particularly rough thrust that hit my prostate, and I found myself face down in a pillow, my hips still up in the air where Barry kept his tight grip on me.

"Oh fuck, oh fuck, oh fuck." I moaned out. "Fuck me harder."

Barry groaned out a response that I didn't quite understand, but he did do as I asked and began to pound into me harder than I had ever experienced in my whole life. I couldn't even appreciate the fact that the headboard was crashing into the wall with a force that threatened to break it. Once Barry reached beneath me and gripped my cock, I didn't stand a chance, shooting my load all over the comforter beneath me while Barry's thrusts got more erratic right before he pulled out of me. I felt his load land on my skin, marking me as his, right before he landed on top of me. His lips traced along the backs of my shoulders before he rolled off to his side, bringing me down with him.

"Fuck, Josh." He laughed out, panting as he stared at me. "Still think I have any complaints about sex with you?"

"I think you made your point." I agreed. "That was...wow. Just, wow."

He ran his hand along my side. "I agree." He smiled at me before tapping me gently on the ass. "Come on, let's go shower so we can go to breakfast. I'm starving. That was way too much exertion for a Sunday morning."

I laughed but followed him to the shower, allowing him to gently wash me with the washcloth. He was soft and kind as he cleaned my well-used ass. Once we were both scrubbed down, we spent the rest of the time making out under the warm stream until the water ran cold. I was addicted to everything Barry gave me, and part of me was worried about that fact. I tended to go in all in with relationships, and I didn't want to do it again. I still had a lot of scars from the whole disaster with Adam, and I didn't want to chance losing myself in a guy who would mess with my head all over. It took all summer to build myself back up, and damn it, I was going to stay up.

The five of us enjoyed a nice brunch before we made our way back to the train station, but we were all more than ready to head home. The limited amount of sleep I got the night before caught up with me, and once the train was steadily making its way back to Connecticut, I let my head fall onto Barry's shoulder and slept the entire way home. He walked with all of us back to our dorm, but when I invited him in, he said he had to go home and unpack some stuff. I hadn't even realized just how big his duffle bag was, considering he was only going away for the weekend. He must have had to take a ton of stuff home from Casey's, and now I was the jerk who didn't even really acknowledge that it was probably tough for him to end a six-year relationship.

By the time I made it to bed, I was beyond exhausted and knew it would be a struggle to get out of bed for crew in the morning, so I decided to skip my weekly hang out with some friends and went right to bed. I had just snuggled under the covers when my phone vibrated across my night stand. A thrill went through me when I saw it was Barry telling me to sleep tight. He was so damn nice, I felt like the luckiest guy in the world. I shot off a quick text back, wishing him a good night, before I put my phone back on the counter and snuggled back under the covers. Now that Barry was single, I would have to remind myself to ask him to go to the election night party with me. I should also probably get back to my father and mentally prepare him that I would be bringing a date. He didn't really care about my sexuality, as far as I knew, but he was not always open to surprises, and dropping into a nationally televised event with a guy three years older than me might set him off, especially since Barry didn't have political connections like all my other exes I have ever had. I discovered long ago that just being honest with my father usually limited the nonsense that he would typically spew out at me. We didn't have a bad relationship per se, but it wasn't the best either.

Shoving thoughts of my father aside, I snuggled into bed and let dreams of Barry in a three-piece suit waiting for me at the bottom of a flight of stairs like Leonardo DiCaprio in Titanic fill my mind instead. It made for a much pleasant end to the night, and I couldn't wait to ask him to come with me the next week. It would be the perfect night out to celebrate our new relationship, and with that, I was able to fall into a peaceful slumber for the first time in a long time.