So if you haven’t already, you can read pt 1 of this story [here](https://old.reddit.com/r/Erotica/comments/g7jtpx/how_my_best_friend_and_i_became_more_than_that_mm/).
After that first time, fooling around became a semi regular thing between me and my best friend, Chris. That first encounter was particularly intense, but after that things were a little more tame… For awhile. We’d wait for times when we’d be alone, we’d hang out normally for a bit as if we weren’t getting ready to mess around and then one of us, usually him, would propose we “relax” or something.
We’d throw porn on, pull our dicks out and comment on the scene like film critics and casually start jerking off. Sometimes he’d just ask “you wanna…?” and suddenly we’d be stroking each other. Most of the time we’d finish ourselves off, comment how great that felt and then go back to hanging out like normal.
The more intimate stuff, we didn’t mention. We weren’t using the toy together, we didn’t kiss or grind on each other like we did the first time. Just good old fashioned jerking off.
One time he took things a step further though. We were doing our thing and I found the scene particularly arousing. I commented to him that I wasn’t going to last long.
He smiled in response, “You can’t control it?”
“Sure I can”
“Nah, I don’t think I believe you” he teased.
“Watch me, I’ll last the whole thing”
“Yeah right, bet you finish before I do”
“You’re on” I said, emboldened by his taunting.
Now that we were betting, I was determined to wait. I started going more slowly and trying to chill out. Chris, of course, noticed this and said, “Oh hell no”
He took this as an opporunity to reach over and start stroking me. I hesitated but he pointed out it was more fair this way. Now, I don’t know if that actually made any sense or if we were just looking for an excuse. But it sounded pretty good to me. So now it was a normal mutual jerk session with the caveat both of us were trying to resist cumming… And therefore both of us were trying very hard to make the other one cum. In the past it had felt simply transactional… We were “bonding” or whatever. But now we were both trying to do what the other one liked. Somehow a bet had turned into pretext to pleasure each other.
But no one was complaining. We both rose to the challenge.
His dick felt amazing, as usual, but he was impressively hard this time. He was shaved, which I liked, and had an absolutely beautiful cock. His hands, however, were kinda slender, not quite feminine but still really gentle. I had always liked the feeling of them moving over my skin, the image his fingers gripping me tightly.
Following the video, Chris had decided to try to stimulate my cock like the guy on the screen. So as the chick gave the dude head and worked the end of his dick, my friend focused on the same spot as mine. Which I found interesting and exciting. But apparently it wasn’t as effective as my strategy. I was jerking his dick like it was my own, going the full length, feeling the shape of it hard beneath my hand, sliding my fingers a bit with evryy stroke so they passed over the best feeling parts, I had this down to a science. And finally having an excuse to go for it, trying to make him finish? I hadn’t realized how much I wanted this.
It was working. He had started with smirking and taunting but had gone quiet. His eyes were closing as he let in and out airy breathes. I was enjoying myself but honestly was far more engaged with making Chris cum. I wasn’t at all focused on getting myself off.
I could tell he was close but he wasn’t going to give up the bet easily. But he always initiated this shit and was clearly enjoying himself. I knew I could get him over the edge.
So, turning away from the screen and toward him, I reached over with my other hand. We hadn’t established any rules, so why not go all out? As one hand continued stroking him, the other landed on his stomach where I felt his tightened abs. It wandered down, momentarily joining my other hand as it moved up and down. Then, based on my own experience, I went in for the kill. I reached down and started playing with his balls, rubbing them gently and pushing my hand against them.
He hadn’t been expecting that. His dick throbbed strongly in my hand and his eyes flew open, “Whoa, what the hell”
“Oh my bad”
I almost stopped, but he reached down and grabbed my wrist, holding it in place. I smiled, looked him dead in the eye and continued. He returned the smile before his face changed as he moaned. But he held eye contact. I loved this. I was still smiling, my face unchanging as I stared him down and played with him. His hand rose to my neck and I could feel him swell up in my hands. His breathing quickened. He gripped my shoulder as he suddenly spasmed and begun pumping cum out over my hands while his balls tightened and twitched. I slowed down but didn’t stop as he continued to pulse in my hands. He fell back, depleted.
“I win” I declared simply as I reached for a towel to clean my hands.
“You win” Chris admitted, still breathing heavily.
After he recovered, we grabbed a few more beers and threw our shorts on before we headed out back with a packed bowl. His house was pretty secluded and it was the middle of the night. We went out and sat on the waters edge with our feet hanging off the dock. I was teasing him that I’d won our bet. At first he just joked that he had won, really, but eventually pointed out “Hey I could have made you cum easily dude”
“Are you sure cause that was the whole bet and you failed.”
“I thought the bet was to stroke each other off like normal, I didn’t know we could do extra stuff like you did”
“Well I wouldn’t have stopped you” I reassured him.
“You might have” he laughed.
“Oh? What’d you have in mind?”
He wouldn’t direct at first just saying, “Trust me, I could get a guy there no problem, with or without porn. Getting a guy hard is no problem. I just didn’t know we could go all out.”
“You’re only making me more curious, honestly”
Given how close we are, I guess what he said next shouldn’t have surprised me “ever wonder what blow jobs are like?”
“Uhhh” I was taken off guard nonetheless “Receiving, I guess it depends on who’s giving. Giving, I don’t know anything about.”
“I kinda wanna try it”
“You haven’t had a chick do it?”
“I have” he said “I mean I want to give one.”
That one hung in the air for a minute. It was clear now what he was getting at. After the awkward silence, I didn’t want him to feel bad so I tried to respond casually, “I don’t know dude, don’t think it’d do it for me. Was that your secret weapon? Think if you had blown me you’d have won?”
He laughed nervously “Maybe”
“Nah we swap handjobs but that’s different, we get ourselves going and just go back and forth. But a blowjob from a dude, I don’t think I could even get hard.”
He waited a moment before responding “Sounds like a bet”
I waited a moment before nodding and saying “Yeah. Bet ya can’t”
Without a word, we started grabbing at my pants. I pushed him away and wagged a finger saying “cheating”
He smiled, seeming to enjoy the new challenge. I looked around nervously but knew no one could see us. I pulled my shorts down enough to let my now soft dick flop out as well as my balls. Once it was exposed I nodded and said “Mouth only. Telling ya, I’m straight, won’t do anything”
Yeah, I was just talking shit. I wasn’t sure how it would feel but it seemed like the only way to justify everything we were doing was to act overly macho about this stuff. Really, it was just fun to experiment with someone I trusted this much and who was this game.
After a final nervous pause, he adjusted himself, looked my direction and lowered his head. Once there, he didn’t hesitate. Something told me he’d been waiting for this. His lips met the tip of my dick as he tongue pushed out past them. Right away I knew I had been wrong. It felt just as good as any chick but even more so because we were pushing boundries together. Despite that I was really nervous and didn’t get hard right away. So he borrowed a page out of my playbook and started using his hands to play with me while exploring my dick with his mouth, touching the base of my dick and my balls. I twitched as his touch sent wonderful little shocks through my body.
I was slowly growing in size and I moved from nervous to transfixed. As I started to chub up, he pulled away and laughed “what’s going on down here?”
“You stole my move” I joked in response.
He went back to work. For some reason stopping for those few seconds really helped. As soon as I felt the warmth of his mouth again I was committed. I felt my dick start to get harder as I placed a hand on the back of my best friends head. Chris changed angles as he adjusted to my growing hard on. Eventually things progressed to a full blowjob at which point he stopped again.
“So much for not getting hard from a guy”
“Yeah yeah” I still felt shy about it and so my banter had suffered.
“I won this time” he observed.
“I guess you did” I responded, trying to ignore how horny I still was “so what do you want for winning?”
His response spoke for itself. He dove back down on my dick and went all in, pushing himself as deep as he could. At this point I found it hard to imagine he hadn’t been practicing because he was a bit too good at this. He had gone from “trying to make you hard to prove a point” to “I am your whore” pretty quickly. He was licking all over my dick, balls, and plunging down taking the full length from time to time. He seemed to like my hands on his head but I tried to be gentle and let him set the pace. I was entirely lost in the moment and couldn’t tell you if it was 5 minutes or 45. All I could think about was the softness of his lips as they ran along me, his tongue as it moved across every part of my dick, and how good it felt every time he pressed down onto me.
Then I could feel it. I panicked momentarily as I said “Dude I’m close should you…”
He didn’t stop but got more aggressive moving up and down and taking me as deep as he could.
I moaned out louder than expected, gripped his head tight, and he went down as far. as. he. could. I then began pumping out the biggest load I had ever felt and could feel as he swallowed over and over taking it down his throat. I couldn’t believe what was happening. Every muscle was tensed and finally I shot the last bit out and began to relax. He sucked for a few more seconds before sliding off my dick and inhaling. He was surprisingly clean, seeming to have taken every last drop.
I fell back on my onto the dock, laying flight under the starlight breathing heavily and still in disbelief. He leaned back on his arms and said with self satisfaction “Yeah I win.”
—
Thanks for reading! Let me know if you liked it and if you have any interest in commissioning a story of your own.
Source: reddit.com/r/eroticliterature/comments/g7k32h/how_my_best_friend_and_i_started_fooling_around
That was really awesome.
The 1st part has been removed.