Problem with a One Night Stand Ch. 04

"Fuck." I groaned out, lost in the sensation again. "You're killing me."

"Or maybe you want me to fuck you?" He continued, releasing my shaft and letting his fingers drift down to my balls. He played with them for a moment, rolling them gently between his fingers before sliding one finger to the sensitive area behind them. He was dangerously close to my hole and my cock was gladly on board for round two. "I've been watching your ass for weeks. I can't wait to be inside you." All the dirty talk was doing wonders for my libido. "I bet you're so hot and tight."

"God, you're dirty." I laughed, breathless as his fingertip began to massage my hole. Part of my brain was warning me that this was yet another horrible decision, but my cock was definitely going to win this fight. "Let me get you wet. I want to suck your cock again." He didn't comply with my demands, but rather, pressed his fingertip inside me. I let out a groan as he paused, letting the tight ring of muscle adjust around the intrusion. He leaned down and kissed my chest, making his way between my nipples and nuzzling his face into the skin there. His breath was hot and fast, and I loved that he was barely containing himself. I winced as his finger began to move inside my ass, pushing ever so slightly into my canal. "Lube." I murmured. "Night stand." Barry took the hint and nodded, pulling his finger out and reaching over me to the nightstand behind my head. I tried not to laugh as things went crashing to the ground, not sure if it was drunken clumsiness or a desire to fuck something.

He finally got the drawer open and pulled out the small bottle of lube I kept in there. "Well, well, well, what is this?" He laughed.

"What?" I asked, angling my head back to see what he was looking at. The realization hit me seconds too late. In his hand, Barry was holding one of my toys that I forgot were in there when I sent him in for supplies. Andrew usually had his own stuff in his pocket, and I never had to worry about him going in my personal stuff. In his hand, Barry had a nice vibrating butt plug that I had bought over the summer when I realized I was going to be alone for the months before school started. "Oh." I muttered, the tips of my ears warming. I'm sure my face was a bright shade of red to match. "Yeah."

"I'm so torn right now." He laughed, reaching in for another dildo. This one was mildly more embarrassing. It was pretty large, but I honestly just didn't use it. Jason and I had bought it one day last year when during an adventure into Georgetown. But now, Barry was sitting there on my bed, airing out all my dirty laundry, and probably making all kinds of assumptions about what a dirty little slut I was. Awkward. "I don't know if I want to play with one of these guys or just get in you myself. The options are endless. I never would have pictured you as so adventurous!" He grinned down at me. At least he found it entertaining.

I sat up and gave him a glare before pulling the vibrator and dildo from his hands. He grinned impishly at me as I tossed them back in the drawer, pulled out a condom, and handed it to him. He looked down at the condom in his hand, and burst out laughing again. "Now what?" I groaned. This was getting disastrous fast. People laughing at you when you are trying to get them in bed is not usually a good thing.

"Please tell me you got this from the campus health center and didn't spend money on it." He laughed, holding up the condom for me to see. It was indeed one I had gotten from the free basket at a school fair, but I hadn't paid attention to the package. It had a basket of laundry on it, with the words "drop a load" in big, neon pink letters.

"Oh god." I laughed. "Where do they get these things?"

"This is hilarious." He continued. "I'm pretty sure this is the best one I have seen."

"There's one in there with a Pokémon ball on it." I offered. "It says 'gotta catch em all' on it."

Barry's eyes went wide and he dropped the current condom on the bed before digging around for that one. He proudly held it up when he found it and grinned. "Which should we use? Do you want me to drop a load or catch all my spunk? I'll leave it up to you."

"Such a gentleman." I rolled my eyes before grabbing the one from his hand and dropped it back in the drawer before slamming it shut. I grabbed the laundry basket one and ripped it open with my teeth. "Get over here and let me get this on you, or you'll be fucking yourself later."

"You're feisty." He grinned, but moved closer to me and watched as I rolled the condom over his thick, hard length and gave him a few strokes with my hand. His head tipped back as I continued to massage him. "Get on your back." He demanded, although his tone was gentle as he pushed me down by the shoulder. I complied with his request and laid myself down, letting him crawl over me. We moved the rest of the way in an effortless transition, his body sliding over mine as if he was designed to fit between my legs. I spread wide and drew my knees up to my chest as he slathered some lube on his shaft and my hole. He may not have finished prepping me, but I wasn't going to wait any longer. My desire was met with the pressure of his cock head on my hole. I relaxed against him and welcomed the thick, pulsing intrusion into my body. "Fuck." He groaned out. "You're so tight, Josh."

I could only moan in response as his cock slid into my ass, stretching the muscles with a delicious sting that made me want to cry out. Barry stilled inside me once he was an inch in, his hard head nestled just inside me. "More." I begged, and he complied, slowly inching himself all the way in. For a straight guy, he sure had a lot of confidence in gay sex. It was more arousing than I ever could have imagined. "Oh god, yes." I moaned out as he bottomed out inside me, his hips pressed against the backs of my thighs.

"God, Josh. You feel so good around me." He grunted. "Can't wait to drop a load."

I couldn't hold back the laugh that erupted from me. "Oh my god." I moaned out. "You are just the worst."

"Best condom ever." He grinned. The grin stayed plastered on his face as he began to rock his hips back and forth, sliding his shaft in and out of my tight canal in smooth motions. He had a strong control over his motions, and I found myself getting lost in the pleasure. The pressure of him inside me gave way quickly, evolving into a satisfying thrum of contentment as he pressed in and out of me in a slow, steady rhythm. Barry adjusted my legs so they were wrapped around his waist and leaned over me, propping himself up on his elbows so he could kiss me as he thrust inside me.

"Oh god." I moaned out as his thick head bumped against my prostate. My head rolled back on the bed and I felt like I was going to explode again already. "Right there." I told him. He took my request seriously and angled his hips so he could thrust harder into me, repeatedly hitting my prostate over and over again. The pressure of his cock on my gland was enough to drive me wild, and my balls tightened as he continuously pounded into me. "Fuck, that's good. Harder."

Barry increased his speed again, thrusting into me harder and harder, his breath rapid against my face as he focused on pounding me as hard as he could. His eyes caught mine, and I found myself breathless as he stared right into my eyes. I couldn't break the connection, no matter how hard I wanted to just throw my head back and cry out in joy. There was something more here than just a casual fuck. Barry wasn't looking at me the way you look at a one night stand. Was it possible that this was more than just a drunken adventure between two friends after too many beers and buckets of booze? It was hard to imagine anyone wanting me as more than that, so I pushed those thoughts aside and squeezed my eyes shut, enjoying the pleasure Barry was giving me. His thrusts were getting more erratic, and I could only guess that he was getting close to finishing. "Cum for me." I told him, my eyes still squeezed shut in an attempt to disassociate myself from the connection I felt between us.

Barry slowed his thrusts, coming to a complete stop inside me. I felt his face nuzzling my neck. "Hey." He murmured softly against my skin. I opened my eyes and angled my head so I could actually see him. He looked concerned, and I felt terrible for shutting this all out in an instant. "You okay?"

"I'm fine." I told him, gulping as I attempted to keep eye contact. "Just a little...yeah."

He gave me a smile, completely different from any one I had seen from him before. It wasn't one of his usual impish grins, but something softer. "I feel it too." He told me, kissing my mouth gently. Gone was the hurried rush to the finish line, and he had shifted into something more sweet and sensual. "But I want you to cum for me." He told me. "And I want to see how much you love it." I swallowed, instantly turned back on at his suggestive words. He began to rock his hips again, never taking his eyes off me. I wasn't imagining it, there was definitely something real there, and Barry was obviously just as impacted as I was. I have had a lot of sex before, but this just felt like more. I felt cherished, cared for...these were not things that any guy had ever given me before. Barry was pounding me now, the bedframe squeaking in protest as we rocked back and forth. He pulled back slightly and worked his way between us, taking my shaft in his hand and stroking me tight and fast in time with his thrusts into my ass. My moans had evolved into incomprehensible babble, and his pupils were dark with lust. "Cum for me." He moaned out, his words striking a cord within me, as I exploded for the second time that evening, white ropes of thick cum spraying across my chest. Barry let out a long moan as he gave a final thrust inside me before I could feel his thick cock pulsing inside me as he let out his own release. He stilled for a second before collapsing back onto his elbows. He was breathing fast and hard, but he never broke our connection. I panted beneath him, watching in awe as he licked up some of my cum from my chest before shooting me one of his grins and leaning down to kiss me. I could taste myself on his lips and tongue, but I didn't care at this point. I felt like a bowl of jelly, he could do anything he wanted.

Barry scooted up off of me, before pulling out of my ass. I watched in silence as he got up and tossed the condom in the trash before picking up his original t-shirt from where we had spread it out to dry. It was still damp, so he used it to wipe the rest of my cum from my chest in a tender gesture I greatly appreciated. He cleaned himself off once I was clean, and then settled beside me on the bed, his naked form pressed against me. I fit against him perfectly, so I snuggled against him and enjoyed the closeness while I could before the inevitable freak out came. "That was amazing." He murmured before pressing a soft kiss to my bare shoulder.

"Mmm." I agreed, too tired to attempt more communication. Between all the booze and the multiple orgasms, I was completely spent.

I don't know how long we laid there in silence, but I eventually drifted off, lulled into sleep by the sound of his gentle breathing beside me. I didn't even realize I had fallen asleep until I awoke a couple hours later when Barry moved beside me. I sat up instantly, freaked out that he was about to realize what he had done.

"You okay?" He asked. "You look like you've seen a ghost."

"I'm fine." I told him. "You heading out?"

"Just cold." He shrugged, and moved so he could pull my comforter over us. I watched in silence as he snuggled back down, patting the bed beside him for me to lay back down. I did, too tired and borderline hungover to care. Barry wrapped himself around me, and covered us both the blanket before immediately passing out again. I let the anxiety dissipate and closed my eyes, ready to sleep myself. I could deal with the fall out in the morning.

I have to admit, one of my favorite things in the world is waking up in the morning with someone in bed with me. For pretty much my entire life, I had always been kind of an after thought for people. My parents were often out of town, whether it was for business or just for fun, and I was usually left behind. Both of them preferred early morning flights, so they often took off without telling me. It was how I ended up in boarding school for middle school and high school, but even in 1^st or 2^nd grade, I often woke up to an empty house. You get pretty used to being alone when it happens often enough, but it takes a toll on you after a while. I feel like I have spent the majority of my teenage years seeking approval from people who will finally prove to me that I am someone worth loving. I thought Adam loved me, but I think he just loved the idea of me being at his beck and call. The way he used me to destroy so many relationships and hurt so many people at school, I don't think there was any way that I could ever feel that way about him anymore either. Andrew could have been promising, but at this point, I think he just wants to get in my pants. Seems like he's far more interested in that Greg guy than in me. Was I so undesirable that people felt the need to run away from me as fast as their legs could carry them?

Needless to say, waking up to find Barry still in my bed was like waking up on Christmas day to find the shiny new bike I wanted under the tree. I woke to the sound of my phone buzzing on my night stand, so I grabbed it before it could bother him and checked the text. It was only 5 am, but this was the time we usually got up for crew practice anyway so my body was not too alarmed. I was happy to see that it was a group text from the other captain of the crew team, informing us all that practice was cancelled due to more rain and thunderstorm warnings. He encouraged us all to go to the gym in the afternoon for a group work out but would otherwise see us the next day. Satisfied I could get some more rest since I didn't have class until 10, I plopped back down on my stomach and turned my head to face Barry. He had slept through the vibration somehow, which was pretty impressive since it sounded like a steam engine to me, but he managed to look perfectly content just snoozing away. He was on his side, with one arm draped over my naked waist under the comforter, and I couldn't help but grin as I realized that he had not only stayed the night, but had also snuggled with me. I knew there had been a deeper connection last night. Not to mention, Barry was way too good in bed to be 100% straight, so maybe he could possibly be into me too. Maybe he would break up with his girlfriend and start dating guys, specifically me. The day before had been a ton of fun, I'm sure we could have a lot more fun in the future as well.

"Why are you up so early?" He asked me, not even opening his eyes. How did he know I was already up?! He opened his eyes and smiled at me. "Hey." He murmured.

"Hi." I returned. "Practice was cancelled."

"Oh, thank god." He rolled over onto his back and stretched out with a giant yawn. I trailed the length of his solid abs as he did so, my mouth watering as I took in the wall of smooth abs. "There is no way I could handle being on a boat right now."

"Apparently it's raining still."

"Are we working out later?"

"This afternoon."

He smiled and rolled back onto his side so he was facing me. "My head is killing me." He pointed out as he reached out and began to rub my shoulder gently. "How are you feeling?"

"Actually, I feel pretty fine. I guess two monstrous orgasms will have that effect on you." He grinned at my response. "Want some ibuprofen? I think I have some around here somewhere."

"I'm good." He pressed closer to me and let his hand trail down my side to my bare waist. "Must be nice to be 18, no hangovers for you, huh?"

"Just lucky, I guess." I scooted myself so I was a little closer and able to feel the heat radiating off his body.

"Feel like getting lucky again?" He grinned, wiggling his eyebrows at me. I stifled a laugh. "I'm just kidding." He moved even closer, and leaned in until his lips were pressed against mine. It was nothing more than a gentle peck, but it was enough to get my heart pounding and some blood flow to my dick.

"I'm surprised you're still here." I told him, ducking my head slightly.

"Why wouldn't I be?"

I gulped, afraid to answer but also knowing that he would never let it go. "Well, I mean, most guys don't stick around for the morning after."

"You've been hanging out with the wrong guys." He tilted my chin up before he kissed me again, this time a little more deeply. "You're a great guy, Josh, and any guy would be lucky to have you. Stop wasting time on placeholder relationships, and find the guy who appreciates everything about you. You don't have time for scrubs. You deserve someone who likes you just the way you are."

His lips found mine once more, and I was smitten. He was basically telling me that he wanted me, and there was no way I was going to give that up. I had never even considered Barry as a potential partner, but now, it was so obvious that he would be perfect for me. We had a lot in common, we got along, he was cute as hell, and he seemed to like having sex with me. And it was really fun sex! This could be the start of something new and wonderful. With my excitement renewed by the realization that he wanted to be with me, I let myself get lost in his touch again. His kisses were deep and sensual, and spoke to me of something more than just a casual night of experimentation.

We must have been kissing for what seemed like hours when his phone started to ring on the other side of the room. I pulled back so he could answer it, but he just lowered his head so he could start kissing down my neck. "Your phone." I laughed.

"I'll call them back." He told me, rolling me onto my back and attacking my chest with his lips, letting them roam from one nipple to the other. I let my fingers tangle in his short hair, letting out a gasp as his teeth nibbled at my nipple. I had always loved having my nipples played with, and this time was no exception. Tiny moans escaped me as he worked his way over them, alternating between sucks, licks, and nibbles. Each scrape of his teeth was a straight shot to my dick. Anxious to get my hands on him, I gently pulled his head back up to meet mine before letting my mouth crash into his. I worked my hand between us until I got a good grip on his dick, happy to see that it was already hard and the head was slick with precum. Barry let out a moan into my mouth as his kisses became sloppier with every stroke of my hand. Finally, he broke his mouth away and pushed back, watching my hand work over his shaft. "God, you're so good." He moaned. Preening under his compliment, I began to work my mouth down his chest until I was settled between his legs with my mouth next to his cock. His head was glistening with his juices, his shaft hard as steel in my hand, the dark red of it contrasting with the light tan skin of his stomach. With a tentative touch, I flicked my tongue along the underside of his shaft, teasing the ridge of his head with every tiny movement. He lay still beneath me, eyes on me as I took in the site of the gorgeous piece of meat he had between his legs. I watched in awe as a bead of precum formed on his tip, so I pressed my tongue against his slit and lapped it up. I decided to make up for his short BJ last night and went at him with full enthusiasm, pulling out all my best tricks. As I worked my mouth up and down his shaft, his hips bucked beneath me, his fingers tangled in my hair, and his moans echoed around my room. We ignored the sound of his ringtone going off for a second time, and then again for a third time, because I was too busy swallowing as much of his dick as possible and he was too busy getting his dick sucked to even care. Judging by the lack of control he usually possessed, I would say Barry was enjoying his dick in my mouth too much to even care that someone was trying to reach him.