Date: Thu, 15 Jun 2023 22:42:47 -0600
From: Oliver Day <oliver.day.149@gmail.com>
Subject: There's A First Time for Everything

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?