So, let’s talk about an interesting time I had with my good friend Dan.
So, my name is Jack, and this story takes place over the summer when Dan
and I were both 16 years old. By this point, I was already sure that I
was gay. I had tried for a few years to like girls like all my other
friends, but it just wasn’t happening. At this point, I was still
partially in denial, but deep down I knew the truth. I had already
totally given up on trying to look at girls in porn, and was consistently
using gay porn or thoughts of guys when I jacked off, but I would have
never used the word `gay’ to describe myself at the time.
Part of the reason that I was in such denial was that I knew literally
nobody else who was gay. I mean I assume a few people I went to school
with might be gay due to just simple probability, but nobody was openly
gay and my group of friends were not just straight, they were all
extremely straight. All my guy friends had been dating girls since we
started middle school, and it didn’t take them long to start having sex
with their girlfriends, and even just having sex with other girls
randomly. I know this because they all were very open about their sex
life. A few guys even offered to show me pictures of them with girls to
prove it. I politely declined. I was not as open about my sex life. The
only experience I had before that summer was trying to make out with a
girl I knew. It was obvious that she liked me, and all our friends tried
to get us to get together. We were alone one evening, and we kissed. I
didn’t enjoy kissing her, but I tried to go farther because I still
wanted to be straight… but once her tongue went in my mouth, I freaked
out and had to stop. I didn’t tell her why I was freaking out, but she
seemed fine with it and promised not to tell anyone.
That was the only experience I had, that is, until my 16-year-old summer.
Most of my friends and I had gotten summer jobs to make some extra money
while we were off from school. None of our families had much money, so if
we wanted to do anything fun over the summer like go to the theme park,
we would all need to make that money. A few friends got jobs at fast food
places like McDonalds, which didn’t seem fun, but Dan and I were both
lucky to get jobs at the neighborhood convenience store. It was nice
since we didn’t have to dress in a uniform and deal with customers,
since it was our job to restock the store. We each had a few shifts over
the week where we would come in and restock shelves, and then we both
came in every Wednesday overnight to unload all the boxes of new stock
that had arrived. That was my favorite part of the job since the store
was closed so we didn’t have to worry about customers, and it was the
only shift Dan and I had together all week.
The first few weeks of the job were supervised by the owner. He came the
first week to show us how to unload the truck, how to organize all the
stuff, and how to restock. He was also there the next week to supervise
and make sure everything was fine, but after that, he gave us each a key
so we could do the unloading by ourselves and he could have the rest of
the summer off from that part of the job.
Even though Dan and I were in the same friend group, we had never been
particularly close, we just both were friends with all the same people,
but I was happy to get to know him better over the summer as we worked
together. But about half-way through the summer, I realized something.
The whole year of school prior, I had been crushing on this boy named
Luke who was a year older than me. But at the midpoint of the summer, I
realized that my affections had moved on and moved to Dan! I had
obviously realized he was attractive before, but I had never crushed on
him until the summer. He had gotten braces on during the last school year
and had buzzed his hair short over summer, but things I was finding
really attractive. As happy as I was that we were getting along and had
become good friends, I was really disappointed I had started crushing on
him. I didn’t want to ruin anything between us because of this stupid
crush. It really didn’t help when he told me about the hookups he had
with girls over the summer. It took all I had not to imagine the things
he was telling me and get a boner while he talked.
But other than the stupid crush, the summer went really well! I was
enjoying my time working with Dan, and I was able to go to the theme park
and the movies pretty regularly with my friends – something that we
hadn’t been able to do the summer prior because of money. That is, until
mid-August came around…
It was a Wednesday night and so Dan and I were unloading the truck at the
store. It was a super hot night. We would start unloading the truck at
10PM, so it was normally pretty cool when we started unloading, but this
night was particularly hot and it was still in the 90’s when we started
that night. We had unloaded everything from the truck, signed for the
delivery, and then had started bringing the boxes into the storage room.
After only a few boxes, Dan decided to strip out of his t-shirt because
of how hot it was, leaving him in just a pair of loose basketball shorts.
I was not super thrilled at this. It had been a busy few days and I
hadn’t jerked off in a while, so I hoped the sight of him shirtless
would not give me a boner as we unloaded.
We continued to unload for a while. I tried to distract myself from the
hot boy in front of me, but I was thwarted by the next thing that
happened. Dan’s shorts that he was wearing were a bit loose, and every
time he leaned over to pick up or put down another box, they would slip
down a little. At first, I tried to keep my eyes away, but it was
difficult and I don’t think I did a good job. As his pants started to
fall, the first thing I saw was a Calvin Klein waistband, but as they
fell further and further, I saw that the color of the actual underwear
was white, which was surprising, since white underwear was usually
considered `uncool.’ When I noticed this, my mind immediately filled
with pictures of Dan wearing nothing but a pair of tight, white briefs. I
knew he was probably wearing boxer-briefs like most everyone else our
age, but I couldn’t get the briefs image out of my head. I really liked
how briefs looked, so I had switched to them a few years before, but I
assumed I was the only one of our friends to wear them. Even so, the
sight of his white underwear was strongly affecting me. As we passed each
other, Dan kept making eye contact with me and smirking, which was odd.
It seemed like he knew I was checking him out, but wasn’t saying
anything.
My dick had been steadily growing all night since he took his shirt off,
but now it was a proper, full boner. I took a chance when Dan was turned
around to adjust myself and pin my dick upward into my own briefs. It
wasn’t ideal, but I hoped my baggy t-shirt would cover it until it went
away. Unfortunately, that was not to be. I also noticed that due to the
heat, I had been sweating a lot. Dan noticed this and told me I should
take my shirt off too, since it felt a lot better in the heat. Not
wanting to act weird or raise suspicion, I agreed. I just hoped that he
wouldn’t notice my boner.
Soon after, we finished bringing all the boxes into the back room, and
would need to start working on organization, since right now, everything
was just in a single pile. We started to move the boxes around into their
appropriate place in the storage area. Dan had pulled his shorts up a few
times when he noticed them falling, but by this point they were showing
his full waistband and almost an inch of the underwear below that. I was
starting to wonder if now he was doing this on purpose, since he was
still giving me weird smirks and he seemed to have stopped trying to pull
them back up. I really tried to stop looking, but it was really hard
whenever he leaned over to put a box down.
We continued for a while, and we got to the boxes of drinks for the
cooler. They all went into one corner of storage, so we had a system set
up where I would take him a box from the pile, and he would add it to the
pile in the corner. We got to the end of those, so I followed him with
the last box to put in the corner. He squatted in order to place the box
in the right spot, and I couldn’t help but stare at his underwear. And
then he finally said something
///”Like what you see?” He asked as he was placing the box.
I almost dropped the box. I was so surprised. He stood back up and
grabbed the last box from me. He placed the last box onto the pile and
turned back to me.
///”You didn’t answer my question… Do you like what you see? You’ve
been staring all night…” he said with a flirtatious tone as he grabbed
his exposed underwear waistband and gave them a quick snap.
All of a sudden my suspicions were confirmed. He had noticed me looking
and that’s why he was smirking. And he had started letting his shorts
fall more after he noticed. I wanted to deny it, but it was obvious that
he had noticed, and he seemed to like the fact that I was looking.
Somehow this gave me way more confidence than I had ever had before and I
decided to flirt back.
“Oh uh yeah… they look really good on you… I was just curious if they
were boxer-briefs or just briefs…” I said with a smirk.
Dan smiled at the question and surprised me again by pulling the front of
his shorts down to show off his tight, white briefs for a few seconds.
This also revealed that I was not the only one who was hard right now.
///”Briefs,” he said, followed by shining his metal smile at me again
before pulling his shorts back up.
I was very surprised, but also incredibly turned on by seeing him
actually wearing briefs. It took all my restraint not to move over him
and pull his shorts back down again, but I controlled myself and just
flirted back again.
“Fuck… you look really good in those…” I said under my breath.
///”Yeah? You like them?” he asked as he took another step closer so we
were only like a foot apart. “What about you… what are you hiding under
those shorts?” he asked.
“Briefs, same as you…” I said in a whisper.
///”You saw mine… it’s only fair I get to see you in yours…” he
said.
I smiled, and that was all the confirmation he needed. He fell to his
knees, grabbed my shorts, and yanked them to the floor exposing my red
briefs and my obvious boner to the world. He then stood up and smiled at
me again.
///”Nice… shows off that boner of yours nicely…” he said.
“Hey! You have one too! And why do I have to be the only one standing
here in my underwear?”
///”You don’t.” he said as he gave his shorts a little push and they
fell to the ground, showing off his tight white briefs in full. “So
what? Are we just going to stand here looking at each other?”
With that comment I lost control and smashed our lips together. I wanted
to hold it, but my nerves got the best of me. What if I misunderstood and
I just freaked him out. I pulled away, and I think he saw the panic on my
face, because he gave me another flash of those braces before pulling me
back toward him and joining our lips. This time I fully gave in and
quickly escalated the kiss. I poked my tongue at his mouth asking for
entrance, which he quickly granted. This was a new experience since I
hadn’t kissed a guy before, but when I felt his braces against my
tongue, I was reminded how hot he was and so my dick started to strain
even more against my briefs.
We continued to make out for a bit while we explored each other’s
bodies. He pulled me closer so that our boners were smashed together with
only the fabric of our underwear in between as we started to press into
each other. I felt him start to grope my ass through my briefs, and so I
moved my hand down as well. Instead of grabbing his ass though, I decided
to play with the waistband of his underwear. I rubbed my hands slightly
underneath them and pulled on the band a bit. Since my eyes were closed
while kissing him, it was a reminder of what he looked like in those hot
briefs. It was an amazing experience, but eventually Dan pulled away.
///”Uh, kissing you is great and all… but since we are already in our
underwear… I thought it might be fun to do a bit more… are you
interested?” he asked.
I didn’t even respond, I just smiled, gave him one last quick kiss, and
slowly sank down to my knees. Now I was face to face with Dan’s
extremely hard cock, only covered by those hot white briefs. I moved in
and started planting kisses on his hard dick through the fabric, and I
felt Dan’s hand move down and start pulling my face even closer to his
crotch. Eventually I was making out with the front of his underwear, and
as I did I could feel his dick getting even harder. As much as I would
have loved to see him cum straight into those briefs, I decided it was
finally time for them to go, since I wanted more before he came. I pulled
his briefs down to his ankles, fully revealing his dick for the first
time. I didn’t hesitate to swallow the entire thing. Even though this
was my first time giving a blow job, I had seen enough porn to get the
idea, and I think I did a good enough job for my first time.
I kept sucking his cock, and as I did he started squirming more and more.
His moans and swears also got louder and louder as I kept going. As he
was getting close to the edge, he was nice to warn me, but this was my
first time doing this, I wanted the full experience. I kept going until
he was shooting pulses of cum straight down my throat. I had tasted my
own cum before, so I knew I would like the taste, but I was surprised how
much better his tasted.
We took a minute as he recovered from his climax. He pulled me up so we
could kiss some more until he seemed to get his strength back. He told me
it was my turn, but I pointed to my crotch to show off the cum soaking
the front of my briefs. I was a little embarrassed, but he seemed to
enjoy that I was able to cum from giving head to someone else. (I wasn’t
surprised at all – I was so turned on while giving him head that it would
have been impossible for me NOT to cum… at least my first time doing
it.) He said he felt bad that he wasn’t able to return the favor,
especially since I had never had a blowjob before. I just smiled back and
kissed him again, and told him if he felt that bad, that we still had a
few hours of work to do, and I could cum again after we were done, and he
agreed.
He still felt bad that I had soiled my underwear, so he insisted that we
swap. We cleaned up our cum, and he gave me his white briefs to wear and
said he would take my cum-soaked ones home as payment and as a souvenir.
We both put clothes back on, with Dan going commando so we could finish
up our work.
Once we were done, Dan pulled me into another kiss and led me over to a
comfortable spot. He proceeded to strip us both naked and dropped down to
give me my first blowjob. It was just as incredible as I hoped it would
be. Even though it was my first time I could tell that Dan was
inexperienced in giving head, but he still did amazing. I made sure to
warn him when I was about to cum, and he swallowed my whole load just as
I did for him. As I was recovering from my orgasm, Dan jerked himself to
completion, which only took a few minutes since he had been jerking off
the whole time he gave me head, and he came all over me. We moved
together before making out for a few more minutes.
When we were done, we finally got up, cleaned up the cum, and got dressed
again. We locked up the store and headed to Dan’s car so he could drive
us home. Dan didn’t really act like anything was different as he drove
me home until we pulled up at my house. I started to say goodbye and
leave, but he pulled me into one last kiss before saying goodbye. I
smiled at his cute face as I left, and he flashed those braces at me one
last time before I went inside and went to bed.
You would think that after a night like that, things would happen a lot
more between us, but that wasn’t the case. The rest of the summer, I
never got that flirty vibe I got from him that night again, even when we
were alone for our night shifts. Like I said before, he and a lot of my
other friends hooked up with girls a lot, so I figured I must have just
caught him on a dry spell that night, but he didn’t make things weird at
all, which I appreciated. He even wasn’t scared to talk about it, making
jokes about some of the stuff that happened that night occasionally, he
just never seemed to want to do it again. I obviously did, but I didn’t
want to pursue him unless he seemed interested again.
Though the experience did give me the confidence to come out as gay to my
friends shortly after the next school year started, and I was so happy
that nobody had any issue with it. One of the girls in the group did tell
me she was disappointed since she had been crushing on me for a few
years, but she was still supportive and having both of those truths out
there allowed us to become much better friends. Dan was also super
supportive. He said he was so happy that I could be open about it and
also reciprocated by telling me that he was bisexual. He told me that
even though he liked having sex with both guys and girls, he really only
had the desire to date girls, and because of that, he would probably only
ever hook up with guys, and that he was going to keep his sexuality on
the DL because of that, but he wanted me to know since we had both been
each other’s first experience with another guy.
Dan and I did hook up a few more times over the next few years, once
during another dry spell he was having, and another after a girlfriend he
really liked broke up with him, but for the most part we just stayed best
friends, and luckily, even the additional hookups never ruined that
relationship. We hooked up one last time when we were both back home from
college over the summer, and that time he was the first guy to fuck me.
But after that, he found a girl and got engaged and eventually married,
so we haven’t done anything since. We are still great friends, and see
each other whenever we can, and I still appreciate that even though he is
married now, he isn’t afraid to acknowledge our experiences together
when we talk.
The End
