New Experiences with my Best Friend [M/M] | 2016

Note: Everything in this story actually happened. Embellishment in the writing is done just to make it flow and sound better when read. Quotes are as I remember them, most aren't exact.

So let me preface the story just a little bit. James and I (Robert) have known each other since we were in 3rd grade. We would hang out at one anothers houses all the time, play video games and watch sports. I moved to a new state at the beginning of 7th grade though. I was still close enough where one of us could hitch a ride and hangout for a weekend or sometimes longer during the summer. We spent long nights playing games and talking about a bunch of stuff. He was probably my best friend for most of my adolescent life.

We both were straight. We'd had multiple girlfriends, some more serious than others and never thought about the possibility of being gay. He was an athlete and at times exuded the jock persona but did a good job of mixing up his personality though and we always had fun. I was still a virgin in the conventional sense (Just messed around with a few girls, mostly foreplay) and he'd been with one or two women.

Fast forward to 11th grade. He's up for a visit to my house. We're both 17 years old, he's standing at about 6'3", slim build, short dirty, darkish blonde hair with pale blue eyes. I'm 5'11" in decent shape myself, dark brown hair and eyes. I'd never looked at James with any sort of desire (I was really unaware of my sexuality at that point) and that changed this night. I'm hanging out in the room he'll be sleeping in waiting for him to get done brushing his teeth. He comes in and I show him how to set the sleep timer on the new TV we have.

"Press this button and then type in the number afterwards." I explained.

Right then he takes his shirt and shorts off leaving only his tight boxer briefs on. Apparently this is what he wanted to sleep in. I glanced at the slight definition of abs and trimmed hair on his chest. I quickly finished explaining the TV, being flustered by his body. I said goodnight, and went to my room where I proceeded to jerk off, confused at my own hormones.

For awhile after that I had thought about James in a very different light, jerking to the thought of him many times. The next summer rolls around and things begin to get interesting. A year of build up made me really sexually flustered on his visit. We'd watch a movie in his bedroom every night and I'd make subtle "accidental" touches. He didn't seem to care and it drove me wild. His last night there, we get done with the movie and I head to my room. I started to jerk off to relieve some of my tension, still under the covers because it's kind of cold. I'm getting close but I hear his door open. I stop moving as he walks in, sitting under a blanket with my dick out.

"I can't sleep" he says plopping beside me on my bed.

He starts to examine the bookshelf next to my bed and ask me questions about what some of the things are, completely unaware what was less than a foot away from him. He lays down next to me to get a better look at a particular picture on the shelf. I shimmied closer and felt the head of my dick brush against his ass. At this point we lock eyes for a second. I'm rock hard and I put my hand on his waist.

"I should go to bed" he quickly says.

"Oh... Ya, you probably should."

Looking back I think he wanted it as bad as I did at that point, but was too nervous. I doubt he came into the room to look at that bookshelf and he had been dosing on and off toward the end of the movie so I don't buy him not being able to sleep. Regardless we both woke up the next day and acted like nothing happened. When he was packing up his stuff, I was cleaning the room he'd stayed in. I emptied the garbage and noticed several used tissues that hadn't been there when we'd watched the movie.

My mom drove James back to his house that day and I tagged along for the ride. On the way my mom stopped to see an old friend and said she be about 15 minutes. After about 60 seconds of awkward silence he says,

"I think I hurt my knee yesterday playing basketball"

"Really? Where?"

He motions toward his knee cap. I reach my hand over to find where and poke his knee in a couple spots.

"Ya it's right about there"

I continue to feel around his knee before he says,

"Quit, that's annoying!"

I keep poking just to irritate him, and he rolls his eyes. He's trying to ignore be as I slowly start to work my hand to the upper part of his leg. After moving consistently up his thigh I reach the fleshy part of his pelvis.

"You're, uh, getting kind of close to my special area" laughing as he spoke

I lock eyes and say "Oops", continuing to poke.

I switch from a prod to a rub. My hearts in my throat at this point, as I slide my hand down his inner thigh. My pinky brushes his soft cock which quickly jumps to attention. I glance up to see his face and he's in amazement, not taking his eyes of his dick. I slowly start to jerk him off through his basketball shorts.

"You should..." he breathed heavily, as I quickened my pace.

"You should sto...", he sighed as he laid his head back and closed his eyes.

Out of the corner of my eye I notice my mom heading towards the car. I whip my hand away and James realizes what's happening and starts to look at his phone nonchalantly. We finished taking him home and that trip ended, both of us filled with sexual tension.

Fast forward a couple months, to the summer after our Senior year. By then I'd lost most sexual tendencies for James as I'd found a couple girls that peaked my interest. We had talked about a road trip for years and decided to finally do it. We booked the hotel for three nights and were on our way. Being stuck in the car for several hours, we got to catch up on almost everything. The first day was relaxing, fun and really enjoyable. It was great just hanging with my friend again. That is, until our last afternoon away from home.

James wanted to take a nap but I was pretty bored and insisted otherwise. I suggested giving him a massage instead of going to sleep (This wasn't uncommon, I give good back rubs, he'd be completely clothes and I did it pretty often to a bunch of my friends). He agreed and flipped over onto his stomach. I sat down on the bed next to him so I could be comfortable as well, repositioning when I need to work different areas. Everything started as normal; shoulders and upper back, moving down to his waist. I worked his calfs a little and moved to his thighs next. As my fingers slipped under his shorts for a brief second, the desire I hadn't had in quite some time came rushing back.

"Why don't you, uh, flip over so I can do your front?" I said.

I was expecting some questioning from him since that wasn't part of the normal routine but he did it without hesitation. As he rolled over I immediately took notice of his bulge. He wasn't hard, just seemed to be ready at any moment. I started at the pecs, moved to the abs, switched to legs and moved back to the torso. I sat myself next to his shoulder to work his lower abdomen and thighs. I could tell he'd been working out because of the increase in definition on his abs. Now it was less of a massage and I was just running my hands along his upper legs, ever so slightly grazing his groin area.

It was decision time now; go for it or let the massage end. In one quick move I glided my hand along his leg, grabbed his package and started jerking him through his shorts. My heart pace quickened and he stayed silent. I continued to slowly move my hand up and down his clothed shaft as he began to squirm. I couldn't stand it anymore and thrust my hand down his pants to feel his warm cock. It was probably 5", but felt so perfect. I jerked him like that for a couple seconds until I pulled it out, revealing it from his shorts. Anxiously wanting to move this along I started to pull his shorts all the way down. That's when he finally said something.

"Robert wait."

I stopped. Looked at him and we shared a second just looking at each other's eyes.

"We probably shouldn't do this. It might make things weird."

"I'm willing to risk it" I asserted.

I rounded up all the courage I had at that moment and plunged my mouth onto his cock. I heard him gasp and moan as my tongue made contact with his tip. I was now rock hard, hidden in my pants as I was sucking my longtime friends dick. I moved slowly but deliberately up and down his shaft. He kept his pubes nice and short. His balls were so well groomed too I couldn't resist popping one in my mouth. Every movement I made seemed to have him on cloud nine. I wrapped my lips on his head and jerked him off into my mouth. His moans were getting considerably louder when he did something that caught me off guard.

James ran his had down my side, reaching down grabbing onto my hard cock. I gasped, dropping his dick out of my mouth momentarily. He continued to rub my cock through my shorts and I went to town on him again, with even more fervor this time. I could taste the precum starting to leak so I knew he was close. I picked up my pace. He stopped jerking me and ran his hand through my hair.

"Oh my god, I'm gonna fucking cum!"

I pulled my mouth away just in time for him to shoot up his stomach and all over his shirt. I jerked off his pulsing dick as ropes and ropes of jizz came out. I slowed down as he finally stopped and sat breathless. I laid next to him, side by side, and started to undo my pants, figuring I'd finish myself off (which I knew wouldn't take long) while he was still in bliss. Suddenly he grabbed my arm, stopping me. He undid my button and zipper, popping my 6" cock out. He took it in his hand and jerked it so tenderly and passionately. He grazed my head, held with such a nice grip. I couldn't resist the urge anymore to cum. No warning, I just jizzed all over my clean shaven stomach.

We both sat there for a couple minutes, thinking about what we had just done. Eventually he got up to clean himself off and I did the same. We continued our day as normal and didn't really mention it. For a year and a half it stayed that way, until one time things got hot and heavy again. That's a story for another day though. Hope you liked it :)