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One Night, Hopefully More - @JoeLechene

I never did stand a chance, did I? I sat on the couch and watched him make out with some random chick through the open patio doors. Every time his hand groped her side, it made me regret coming to this party more than I already did. This entire thing was his idea and I only came to it because he was my best friend. If only he knew that I wanted to take our friendship to an entirely different level. Of course, I would never do such a thing for the fear of losing him. I would forever be his wingman, destined to be stuck watching him. Wishing that it was me that he was making out with instead of some random chick. I knew that I could never be with him that way and it tore me apart every time that I looked at him.

...

Cooper and I had been best friends for as long as I could remember. Our fathers both practiced together at the same law firm, which meant we spent a lot of time together while they frequently worked late. We practically did everything together growing up. We watched cartoons, ate meals, and eventually played sports together. Fuck, we even lost our virginities on the same night. Unfortunately, it was to two different girls and not the way that I really wanted to lose it. Cooper always had my back growing up and I had his. Regardless of whatever stupid thing he talked me into doing.


...


I watched as he left her to refill his red plastic cup with more booze. Cooper had become quite the drinker during our high school years. I guess that being the Captain of a state championship winning basketball team can have that effect on a man. Lots of winning game parties meant lots of drinking. Tonight though, he seemed to be guzzling way more beer than usual. Normally I wouldn't worry about the amount that he drank. Tonight though, he was starting to worry me.

Cooper had five more drinks to my two before he started to sway while talking to the same chick. I could tell just by looking at her that she was getting annoyed. As the party was quickly dying down, she left him on the patio. Without even giving him a kiss goodnight, she walked away from him. Leaving him behind in a drunken stupor.

Not wanting to leave my best friend hanging any longer than I should have, I got up from my seat on the couch and walked out onto the patio. Cooper drank what remained in his red cup as I wrapped my arm around his waist and guided him back into the house. Getting him up the stairs to the second floor was no easy feat since he was beyond wasted. He stumbled every other step on the way up the stairs.

I held onto him by the back of the belt while I fumbled with the keys, trying to unlock his room. He always kept it locked on party nights, so he didn't walk into some random couple fucking on his bed. After unlocking his door, I led Cooper inside still holding him up by the back of his belt. As soon as the door was shut and locked behind us, I laid Cooper down on the bed. My oldest friend laid incoherent as I pulled his shoes and socks off his size thirteen feet. I was able to pull his t-shirt off over his head, but that was as far as I was willing to go. I managed to lift his still jean clad legs onto the king-sized mattress and pulled the covers up over his naked mocha torso. After changing into my pajama pants, I joined him on the opposite side of the bed. This wasn't the first time that we had shared the same bed and I doubted that it would be the last.

...


It was still dark when I woke back up. The moonlight was shining through the windows and I felt a pressure on my body that wasn't there before I went to bed. At some point during the past few hours, Cooper had moved over right against my side. This kind of contact wasn't something that happened before, despite the number of times that we've slept in the same bed. I remained completely still beside him for fear that I would wake him up. After what seemed like an eternity, I felt a hand brush over my thigh. I had to hold my breath when it stopped directly on top of my junk. At this point, I was trying to just pan it off to him being in a drunken unconscious state. That all ended when his hand started groping me.

I would be lying if I said that this whole ordeal wasn't turning me on. I could feel myself very quickly hardening in his grip. Only the thin fabric of my boxers and pajama pants separated my hard-on from my friend's hand. His hand remained in the same place, palming me through the thin fabric for a few more minutes. I tried not to freak out the entire time that this was happening. Cooper's hand started to move upward, this time stopping on top of my happy trail on my bare stomach. When it started moving again it started south, this time with his fingers working under my pj's and boxers. I felt his fingers pass under the waist band and immediately come into contact with the head. Cooper didn't stop there, he kept going until his hand was covering my shaft. I remained calm this entire time, that was until he wrapped his hand around my swollen member. I let out an involuntary gasp and instantly regretted it. Cooper started to pull his hand out of my pants, but I quickly grabbed his wrist and held it in place.

I turned my head and looked at my friend laying against my side. "You don't have to stop."

He replied, "Jay, I'm so fucked up right now. This is something that I've thought about, but never had the balls to try sober. And, that bitch left me blue balled."

"Then don't stop."

Still holding onto his wrist, I pushed his hand back to where it was previously residing. He grabbed a hold of me again and started gently stroking. I reached over and ran my hand down his chiseled torso. When I reached the top of his jeans, I didn't stop until I found the monster underneath the fabric. Of course, I had seen Cooper naked before, but never fully aroused. He was packing some serious heat in his pants. It had to be at least ten inches and thick. Not wanting to miss this opportunity, I reached over with my other hand and undid the button and zipper on his jeans. I slid my hand back down, this time going under his boxer briefs. After my fingers ran through his coarse black pubes, they found the silky skin encompassing his hard shaft. I ran my fingers up his length until they brushed over the plump head which was already dripping. My fingers swirled around the head, smearing his juices all over it.

That was it, the final moment that meant there was no going back. I rolled over on top of him leaving our bare torso's barely inches apart. Moving my body down towards his feet, I grabbed onto the waist of his jeans and underwear, pulling them both down in one swift move. His now nude mid-section laid before me in all its true glory. I took him in my hand, pulling it away from his stomach and looked at the glistening head. It was now or never, and I didn't know if this opportunity would ever present itself again. Without thinking anymore about it, I bent down and took as much of him into my mouth as I could. My hand worked the rest while my mouth engulfed at least half of his meat.

As my tongue licked his shaft, I used my other hand to take off my pj's and boxers. Cooper followed suit and used his legs and feet to kick off his jeans and underwear. The object of years of obsession was now naked with me hovering nude over top of him. At this moment I wanted him so badly and he wasn't objecting to anything that I was doing. I released my oral hold on him and reached over to the nightstand. After turning on the small light, I retrieved the bottle of lube that I knew he kept in the drawer for lonely nights alone. I pumped a generous amount onto my palm and used it grease up his mammoth rod and my hole. I straddled him and lined Cooper up before very slowly sliding myself down on him. Cooper just laid there with his hands on my thighs as I worked him into me.

This was the first time that I had a man in me and he wasn't exactly normal sized. It took me a while to get use to his length and girth. If it wasn't for the couple drinks that I had tonight, I'm not sure that I could have handled him at all. Once the pain had subsided, I grabbed onto the sides of his chest and slowly started riding him. I slid my ass all the way up to the tip before lowering myself back down to the base. Cooper tightened his grip on my thigh with one hand and placed the other on my throbbing cock. He stroked me while I rode him, going faster as time went on. I could feel his chest heaving as he started bucking into me, matching my movements. My best friend was fucking me and enjoying every minute of it.

As the sun started peeking through the windows, Cooper grabbed onto my waist with both hands and rolled us over. He was now on top of me, between my legs and pounding me hard. I pushed my head back into the pillow and gave myself to him. Cooper resumed stroking me only this time with lube on his hand. I didn't even notice him squirt the slick liquid into his palm and I quite frankly didn't care. His thick cock was hitting my spot dead on and it was about to send me over the edge.

The morning sun glistened over his milk chocolate skin as he pounded my poor ass. When the time finally came, it hit me like a tidal wave. I started squirting all over my pale white stomach as my hole clenched around the fuck stick buried inside me. Cooper arched his back and bit his bottom lip as he thrust into me one last time before I felt him spasm inside me. He collapsed on my stomach, letting my juices mingle with his sweaty torso. After he pulled out of my used hole, I grabbed my shirt off the floor and wiped both of us off. I laid back down beside him and he put his arm around me, pulling my back against his chest.

...


When I woke up later that morning, we were still in the same position that we fell asleep in. I rolled over and looked into his groggy morning eyes.

He smiled at me and said, "I love you, Jay."

"I love you too, Cooper."

His head closed the distance between us and our lips met in the middle. It wasn't a wet or sloppy kiss, it was more sensual than that. The kiss was very slow and passionate, like we had been lovers for years. As his hand grabbed my back and pulled me into him, I knew that our friendship had just transformed. I knew that I was home the minute my lips touched his.

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