Author's Note: I wanted to try my hand at some more one-off stuff instead of long stories, so hope you enjoy. Looking forward to hearing what everyone thinks at oliver.day.149@gmail.com
There's A First Time for Everything
Hi. My name is Tom, and this is a story about an event that happened with my friend Will when we were seniors in high school. We had been going to school together since we were very little, but we didn't really know each other well until high school when we got introduced through a mutual friend and started playing video games a lot together.
One Friday, Will had invited me over for a night of gaming, so I had brought an overnight bag to school, so we could go straight to his house after school was over. After we got to his house, we played games for a few hours until it was time for dinner. We ordered some pizza and ate. I expected that we would just go back to gaming after we finished eating, but Will surprised me instead.
He had a mini-fridge in his room that usually just held sodas, but he moved over and opened it and pulled out a 6-pack of beer! I had never drank before, and he admitted that he hadn't either, but that his older brother got it for him when he was in town last week and he wanted to try it together. So we decided to slip the beers in a backpack, and head over to the nearby park. It was just getting dark, so it should be empty.
The two of us got to the park finally, found a nice spot to crash, and cracked open our first beers. I didn't love the first sip, and I could tell from his face that he didn't either. Will wanted to keep drinking, since his brother warned him that he might not like it immediately, but that he should try to finish his first one. So, we both tried and sipped down our first cans until they were done. I still didn't love it by the end of the first can, but I understood it a bit more, so I was willing to go for a second can, but go a bit slower. I picked up a second can, and a few minutes later, Will followed suit. We had been mostly focused on the beer before, but for the second, we drank slower and chatted.
We chatted for a bit about some upcoming games that we were excited to play, and about some random stuff going on in our lives, but I could tell his inhibitions had gone down some when he started telling a story about his cousin. We had been friends long enough that the topics of porn and jerking off had come up once or twice, and so I wasn't surprised that Will had done those things, in fact, I assumed he did it quite often considering my frequency, but it was surprising to hear him talk so openly about it.
///"So anyways... My whole extended family rents out this group of cabins by a river each summer, and we spend a few days there. Usually a few days like that isn't too bad to go without jerkin', but for some reason, by the second day, I couldn't stand it! And with so many people up there, it's hard to get any private time to deal with it... Luckily, my older cousin Dave had just broken up with his girlfriend, and was used to having all his needs met, so he had the same issue as me, and since we shared a room in the cabin, we were able to go there without worry of being barged in on and take care of ourselves... You ever done that with anyone?"
"No, can't say I have... did you guys..." I started to ask, curiosity getting the better of me.
///"We didn't like... DO anything together... we just jerked off, and since we didn't have service or wifi, he shared some porn he had downloaded on his phone to help."
"Damn... sounds like an interesting experience." I responded.
///"Yeah... fuck, even talking about that is giving me a bit of a stiffy... maybe it's the beer... I don't know..."
"Well I bet jumping in the cold water would calm that right now," I suggested.
///"Very true... do you dare me? I don't think I would do it normally, but with that beer who knows?"
"Fine, I dare you to strip down and jump in the lake!"
///"Damn Tommy... I'll take that dare... if you'll do it after me!"
"Deal"
Will immediately stood up and started stripping, first losing his shirt, and then shorts to reveal a pair of tight blue briefs, and an obvious boner starting underneath. I was surprised to see his briefs and found myself unable to look away from them and everything they were trying to cover. He moved toward the lake and got in - slowly at first and then eventually jumping all the way in. Once he took the plunge, he beckoned me over toward him.
I swallowed the last of my third beer that I had opened during his story about his cousin, and stripped down to my red boxer briefs, only to find that I was also hiding a growing boner. Luckily, Will was probably too far away to see, and I quickly got into the cold water to hide and try to get rid of the boner. The water was freezing, so I could feel my boner subside by the time I reached Will in the water.
"So," I started. "Did the water help with your situation?"
///"It sure did, it's fucking cold in here. How about yours? I saw you had the same issue I did when you were stripping," he teased.
I got a bit red in the face, but nodded.
"///"Well, I need to move around, since it's so cold in here," he said as he started to splash me and start moving around.
We splashed around for a bit, and then started to lightly wrestle and just play around in the water. Unknown to me, as we started playing around, all the physical contact with Will was quickly resurrecting the boner inside my underwear. Will and I had never had a lot of physical contact other than the odd high-five or hug, especially with this little clothing on, and since we were in the water I didn't realize what was happening.
We kept playing around for a while until we started to get tired and cold, so Will suggested we get out and dry off so we could head back to his house. He helped me stand up in the water and put his arm over me as we walked out toward our clothes. Once our torsos and then our underwear was out of the water, it immediately became apparent that both of us had rock hard boners that were sticking straight out. The soaking wet underwear we both had on also didn't help since the way the wet underwear stuck to us left very little to the imagination. (Especially for Will in his briefs!) I turned red again as I noticed, but Will seemed unbothered, and just said "Nice cock" in a joking way. My dick noticeably twitched when he said that, but I tried to just ignore it as we made our way to a patch of grass to lay down and dry off.
We laid down next to each other to start drying off, and just sat in silence for a while. I was pretty unsure of what to say, and still embarrassed of my boner, so I just tried to think of other things and have it go down by itself. I was not successful. 15 minutes later, my body was mostly dry but my underwear was still wet and still tenting my hard boner. I looked over at Will and was surprised to see him in the same situation still. He seemed to notice my movement and moved to sit up, and so I joined him.
///"Damn... both of us are still bricked up..." he said.
"Yeah... I don't know what to say..." I admitted.
///"Don't worry about it bro... we're both hormonal teenagers, so it's not too strange... but I was serious before... that thing is impressive," he said as he tapped my exposed thigh, which again made my dick twitch and my face go red again.
"Thanks... yours is too, it barely fits in those briefs..." I said and noticed his dick twitch in the same way mine did at the complement. Without even knowing what I was doing, I had scooted closer to him so our knees were almost touching.
///"Yeah... if I knew I was going to strip down and have a huge boner tonight, I would have worn something a bit more modest... but I normally like how briefs fit me..." he said as he leaned his knee over to touch mine.
The alcohol and my arousal had taken over, and without thinking, I said "No, I'm glad you wore them..."
"Oh... so you like seeing my wet briefs with a hard boner underneath?" he teased back, and I looked away when I realized what I just said out loud. I felt his hand lay gently on my thigh, so I looked back over to see Will's face very close to mine. Somehow, my hand made it to Will's thigh, and suddenly Will moved in and pressed his lips to my cheek. Instinctually, I started to do the same back, but instead ended up going straight for his lips and placed my lips right on his.
We quickly both pulled back, but as I felt my hand moving slowly up his leg, I suddenly knew what I wanted, and pulled Will back in for a kiss. At the same moment we both seemed to break through whatever had been restraining us and quickly intensified the kiss. Will pulled me closer so that our legs intertwined and I could feel my dick getting pressed against his legs as I felt his dick get pressed into me in the same way. It only took a few moments before our mouths opened into the kiss and we were fully exploring each other's mouths. Our hands were also both exploring each other's bodies, and I found myself drawn lower and I started playing with the still wet waistband of his briefs, and that was somehow the part of this whole thing that turned me on the most.
Just as we were getting going, Will broke the kiss, and I felt a rush of worry fall over me - was he changing his mind, was this a mistake? He obviously saw the worry on my face, and quickly assured me I didn't need to worry.
///"No no, don't worry... I was just thinking... maybe we should head back to my place to continue this? I'd rather not get caught doing this here..."
I realized he was right, and, so reluctantly, I found my clothes and got dressed so we could walk back to his house. We had mostly dried off by that point, but our underwear had still been pretty wet, so in addition to still having visible boners, the wet from our underwear was seeping into our shorts. Seeing the brief-shaped wet spot on Will's shorts didn't help with my boner, but it was dark enough outside so it didn't matter much. The 20 minute walk which normally wasn't a problem was agony this time, and we tried to restrain ourselves as we walked, but we kept taking turns moving in and planting kisses on each other. I had so much to say to Will, and this seemed like a good time to do it, but I couldn't seem to find any words, and maybe he was the same.
As we kept walking, the occasional kisses got more frequent, and when I would move in to kiss him, my hands would wander a bit and touch any part of him that I could. He followed suit and was the first to grab at my hard dick through my shorts. I yelped a bit when he did that, but returned the favor, and he yelped back before kissing me again. It took all I had to not throw him into one of the lawns we walked by and rip all his clothes off, but I restrained myself. We approached his house, and he pulled away from me.
///"Just until we get inside, okay? Let's... take the back door..." he said gesturing to my still-visible hard-on.
I nodded and followed his lead. We walked into the backyard and took the stairs to the basement door, where Will's room was, and got inside.
After making sure the doors were locked, Will came over, smiled at me, picked me up, and walked me over to his bed while we made out. He laid me on the bed and stripped me back down to my boxer briefs, which were finally dry by this point. He admired my tented underwear for a moment before giving me a little dance as he stripped back down to his briefs and joined me in the bed.
///"So uh..." he said as he broke another kiss. "Is there any specific way you wanted to do this?... I'm... kinda new to this..." he said.
"Uh yeah... same here... but I did have a thought..."
///"By all means... lead the way!" he said with a kiss.
I scooted back in his bed to give Will some room in front of me, and laid back as I brought Will on top of me. I spread my legs and pushed my crotch forward as I guided Will to push his hard dick toward mine. Our hard dicks made contact with just the fabric of our underwear in the way, and I let out a very guttural moan when I felt the contact. I started to thrust forward a bit and grabbed his ass and pulled him toward me to do the same.
"Is this... okay?" I asked.
///"Fuck yeah... this is incredible!" Will said as he started to grind into me.
I pulled him in to kiss some more as we ground our dicks together, and it was a good thing we were kissing, or I would have made some noises that would have been heard upstairs. Will kept kissing me and started to thrust harder and longer into me. Feeling the shape of his hard cock against mine was almost too much, and I started to get close to the edge. I was sad that it was almost finished, but I wanted to cum so bad. But right on cue, Will broke our kiss to say something.
///"Hey... I'm gonna... cum really soon. Do you wanna keep these on right now, or can I..." he asked as light tugged at the top of my underwear.
"Yes please," I responded.
Will smiled and pulled my underwear off of me, leaving me completely naked in front of him. He then pulled down his own briefs and gave me my first view of his dick. Even though we had been friends a while, we mostly gamed together, so there had never been a reason to be naked together. Maybe if there had, I would have realized some stuff about myself sooner.
Will got back on the bed and moved close so our cocks were together. He lined them up and grabbed them both together before he started jerking them together.
"Fuck Will... I'm not going to last long with that..."
///"Me... me neith..."
But he couldn't finish that thought because we both started cumming. I started to yell, but Will moved down and covered my mouth with his own to stop both of us from making too much noise. Will collapsed on top of me and we kept kissing for a few minutes.
Eventually, the mix of cum on my stomach started to get gross, and we could both tell. Luckily, there was a shower in the basement, and Will again picked me up and brought me to the bathroom. We got inside together and cleaned up, but as was the theme of the night, we couldn't stop kissing and our hands found their way to each other's dicks, and we each made each other cum one more time. Once we had finally finished in there, we made our way back to Will's room and bed.
///"Do you uh... want to put something on for bed... or...." he asked.
"I'm good just like this."
Will smiled, pulled me into bed, and got our naked bodies under the covers. He pulled me close and even though I had never slept together in a bed like this with anyone (especially naked), I quickly drifted off to sleep.
The next morning, I woke up with Will in my arms, and suddenly the memories of the night before came flooding back to me. Along with the memories, a lot of disparate thoughts also flooded my mind. How did I go from never really questioning my sexuality before, to... this?