Date: Thu, 24 May 2018 22:25:46 +0000
From: Jack Stories <storiesbyjack@hotmail.com>
Subject: I Dare You - Chapter one

Hey!

This is my first time writing something for the site but I've been a reader
for a very long time. I'd be really grateful for any feedback that you
could send my way. My email is storiesbyjack@hotmail.com and I've set up a
tumblr storiesbyjack.tumblr.com where I'm going to put updates and
different things I find hot.

The stories are mine and any similarity to anyone, living or dead, or real
life events is just a coincidence. These stories are about sex between guys
so, if you are offended by that, you shouldn't carry on reading this. It is
set in England and the main character is in his final year of sixth form at
the local high school. Part of this chapter does have to be the set up for
future chapters so please bear with me.

**********************

Chapter 1 of "I Dare You"

If you'd have told me that, by the end of the day, I'd be doing this in
front of an entire audience, I'd never have believed you.

I've always been quite a reserved person - growing up, my teachers had
always described me as 'the quiet one'. "Jack needs to be more outgoing,"
they would say. "He needs to stop being so shy." I guess that descriptor
had fit me pretty well. I'd never really been in trouble but also never
stood out for positive reasons either: I had friends but not that many; I
achieved well but not overly well. I just... existed.

That had never bothered me but it is the reason that I had reached my 18th
birthday without having come out to anyone or even had any sexual
experiences beyond wanking myself every so often. That's why what I was
doing now was so strange for me, so against my normal character.


Today was a special day. It was the day I was finally turning 18! In
reality, that didn't come with the freedoms you might expect - I was one of
the oldest in my year group which meant that I had nearly a full year to go
before I'd get to go off to uni and spread my wings. I'd known I was gay
for a few years but had decided that I didn't want to come out until I got
to uni. I didn't know how my parents were going to react and, to be honest,
I just didn't want to deal with all that drama.

The majority of the day passed pretty normally. I went to school and spent
most of my time with my best friend, Will. With a few exceptions, we were
in pretty much the same classes for every subject. That was great for me
because my circle of friends only really consisted of Will and a couple of
other lads I'd known since primary school. Now, I know what you're
thinking: "this will be one of those typical stories where the author falls
for his best friend, how predictable and sweet." You're wrong and on
several counts. First, let me clear that this isn't some sort of love story
and, second, I couldn't possible fall for Will because I'd already spent
most of my teenage years lusting over the sexy fucker and shooting nearly
daily loads while imagining what the look on his face would be when he
fucked me for the first time. My feelings towards him are definitely, and
firmly, locked in the lust camp. Besides, I'm pretty sure he's straight. I
mean, he's never actually dated a girl but I think that's more because
we're both social losers than because he isn't interested in them.

I do feel a little bit bad for Will. He was definitely good looking enough
to be in the popular crowd but he'd never quite managed to migrate over to
them. Hell, I'd say he was one of the best looking guys in the year! He
dwarfed my 5ft6, standing at 6ft1. His styled blond hair always seemed to
look better than my messy dark locks. We were both pretty slim though I
think he had a little more definition coming in than I did. There is one
area that I had him beat though! No! Get your head out of the gutter - I've
not seen his dick for years! No, my eyes: I have those bright blue eyes
that you sometimes see on dark haired people. You know the type that seem
to pierce and pop in every photo? They were definitely my best
feature. Well... that and my 6.5 inch uncut cock.

Anyway, school wasn't that interesting but it was a Friday - thank fuck -
so at least my birthday was at the start of a weekend. Will and I were
going to hang out but my mum had messaged me during the day to tell me that
I had to be home for a family birthday dinner. I didn't mind as my parents
are pretty good to me - they'd saved up and bought me a load of driving
lessons for my birthday even though we didn't really have any money so the
least I can do for them is turn up to a birthday dinner.

I'm not going to bore you with the trival details of our family
chatter. Save it to say that my mum and dad both gushed over me a little
and my 16 year old brother was his usual annoying self. It's what happened
after the dinner which was important and the reason we are writing this
story.

It turns out that my grandma has been debating what to get me for my
birthday and had ended up setting on a brand new smartphone. Now, that
might not seem like something for an 18 year old but, actually, it was my
first smartphone. Like I said, we never really had a lot of money and so I
was incredible grateful to her for doing this for me. I was especially
grateful when I realised that I'd now have constant access to a wide
collection of hot and horny porn when I was up alone in my room.

That's where we start getting interesting. I'd headed off to bed early,
stripped off completely and was now laid completely naked on my bed with my
hardening cock in one hand and my new phone in the other. I was in the
middle of watching an xtube video with a cute little twink, who looked
quite a lot like me, being pounded by a big rough older guy when I
accidently clicked on one of the banner ads. A series of windows opened on
my device offering me everything from more porn to cures for erectile
dysfunction - not a problem I have, believe me. If anything, my cock has a
mind of his own and is hard more often than not! Anyway, I started closing
them to get back to the video when something caught my eye.

"We dare you!" it said - red letters on a plain black background. I don't
know why but I felt drawn to it so I clicked on the text and it brought me
to a signing in page. I looked around for some clue as to what it was but
the only thing I could find was the text that had now appear at the top of
the page: "For kinky, dirty and hot fun, sign up now. You won't regret
it. Go on, we dare you!"

I was intrigued. If I had known what was going to happen in the coming
days, weeks and months, I wonder if I'd have made a different decision but,
either way, I signed up.

Once I was inside the site, it appeared as if I had some kind of profile
and it was asking me to fill in all these different details. It started off
easy - age, height, build, etc. but quickly turned very sexual and asked
about all the different experiences you'd had and what your kinks were. To
be honest, I just skipped out that whole section because I'd never done
anything with one before.

After filling in the profile details, several buttons appeared. I could add
to my profile, check my 'dares' or join the chatroom. Given that I'd just
filled out my profile and just joined the site, I opted to enter the
chatroom.

Instantly, messages quickly filled my screen and rolled by at an
exceptional pace - this was obviously a busy site and the posters all
appeared to be guys and very horny ones at that. They all had pictures of
themselves next to their messages but when I typed in 'Hi,' my message
didn't even come up. Suddenly my phone beeped and a new window opened.

"Hey there," a message read, "You're new to the site, aren't you?"  "Yes,
I've just joined," I typed back, "What is this?"  The reply was instant:
"Don't worry, I'm a moderator so I'm here to explain everything to you and
get you set up properly. I take it that you're gay, yes?"  My heart started
to beat faster in my chest. I'd never really talked to anyone - online or
not - about this but decided to bite the bullet.  "Yes, but I'm not out." I
said.  "That's ok. This site is for gay guys who are looking for some horny
and kinky fun. Basically, it works like this. Other guys on the site can
set you dares and challenges to complete. The more you complete, the more
points you earn. The points can be exchanged for different things -
vouchers, gifts, even money - and you can earn bonus points for doing the
challenges in interesting or unusual ways."  Well, as soon as the word
'money' appeared on the screen, I knew I was in. Uni was less than a year
away and I wanted to have enough saved up so that I could live
comfortably. My parents had been on at me about getting a part time job for
a while now so maybe this would fit the bill.

"So, what are the dares like then?" I asked, curious as to what I'd have to
do.  "It varies," the moderator explained, "They can be quite tame or can
get quite wild - it completely depends on who sets you some dares and which
one you pick to do. Most of the time, they are quite sexual but, let's be
honest, we're all just a bunch of horny guys here so that's to be
expected."

I did debate whether this was the right thing to do. On the one hand, I was
an inexperienced closeted gay guy and I wasn't sure I was quite ready for
something like that but, on the other, I needed cash badly and there was a
huge part of me that actually wanted to have some real fun rather than just
imagining it all the time.

"I'm in," I typed after a few moments of deliberation.  "Great! Do you want
me to set you up with your first dare?"  "Sure!"

The chat window closed and I was returned to the main chatroom. The
moderator had already posted a message explaining that I was new to the
site and looking for my first dare. He told the room it had to be a mild
one so if they wanted to submit a few, he'd select one.

After a few minutes, I saw him directly address me in the room.  "Jack," he
wrote, "a dare has been selected. I can see from our system that you are on
a phone at the moment - does it have a camera?"  "Yes," I replied, my
message appearing in the main chatroom for the first time.  "Brilliant!
Your first dare comes from user 'xwatcher'. He wants to see you naked on
cam for the whole room to see and wants you to wank until you've
shot. There are 50 points attached - what do you want to do?"

Well, in for a penny, in for a pound, I reckoned. "Ok, sure," I typed,
"I've never done that before though."  A message came into the room from
'xwatcher': "Even better! We get to see your first time cumming on cam."

The moderator explained how to set it all up and, as soon as my camera was
active, the messages of support and encouragement came flooding in. I moved
my phone so that you could see the underside of my uncut cock and then up
my body towards my face.

I was looking down, reading the messages, as I started to stroke my
cock. It was the hardest it had ever been and I wouldn't have been
surprised if it had stretched up to 7 inches of uncut teen meat. I was so
turned on. As I worked my foreskin back and forth over my throbbing cock,
the guy's watching seemed to be loving it.  "Yeah, wank that big teen
cock," one said.  "Fuck! He's so cute! Looks so fucking innocent," another
had added.  "Damn - look at that precum - show us some of that!"

I ran my fingers over the top, coating them in the copious amounts of
precum that had now started to leak from my cock and showed it to the
camera. My cock slapped back against my smooth abs as I let go of it.

"That's so sexy," one of the commenters wrote, "Don't waste it - lick it
off!"  I was really getting into the moment so I didn't even think about
whether to do that or not, I just obeyed and brought my fingers to my lips
with the camera following it. I wrapped my tongue around my middle finger
and sucked the sweet precum right off it. It wasn't the first time I'd
tasted my own and, over time, I'd grown to love the slightly salty nature
of warm spunk.

I returned to stroking my cock. My hand sliding quicker and quicker, the
sounds of my foreskin sliding against the wet head of my cock filled the
air around me. I could feel it pulsing against my palm and I knew that it
wasn't going to take me long to shoot a load all over myself. The guys
watching seemed to know that too because they started posting requests to
tell me where to shoot.

"Oh your abs," one suggested.  "No, over the sole of your foot!" another
offered.  But it was the suggestion from the original poster of the dare,
xwatcher, that caught my eye: "Lift your legs up over your head and shot on
your face."  I'd never done that but the idea alone had me nearly losing my
load. Sliding down the bed, I lifted my legs into the air and rested the
soles of my feet against the wall at the head of my bed, I walked them down
slightly until my cock was directly above my face. It was difficult to
angle the phone in this position but I managed to get it pointing at my
face as the urge to cum reached its peak.

Spunk rained down onto me. I shot far more than I had ever done before: jet
after jet of thick, creamy teen cum coated my face and hair. Glancing over
at the comments coming in on my phone, the audience were loving it and
calling me all sorts of dirty names like a nasty slut or filthy
faggot. That just turned me on so much more and was definitely responsible
for the last two ropes of jizz I managed to work out of my cock.

Letting my legs fall, I lay there, panting and reading through the comments
being posted. After a few moments, the moderator told me to close the
camera and explained how. He told me that it was common practice to take a
photo of a completed dare and upload it to your profile as proof and as a
history of what you had done. I started to say that I hadn't even thought
about taking a picture and now it was done but, luckily, it turns out that
he had and, within seconds, he'd uploaded a photo of my face, coated in
spunk as the main picture on my profile. He welcomed me to the site once
again as he transfered the 50 points over onto my account and told me that
he'd sent me an email with a link to an app that I could use instead of
having to log onto the site every time.

After thanking him, I closed the chat and forced myself to get up and into
the shower so that I didn't wake up with dried cum all over my face. My
final thoughts, as I drifted off to sleep, were all focused on what other
possible challenges and dares I might be confronted with the next time I
logged in.

**********************

Thank for reading this! I hope you enjoyed it - I certainly enjoyed writing
it. I'm hoping to get a lot of the dares and challenges from your
suggestions so if you have any ideas as to what you'd want Jack to get upto
then please email me at storiesbyjack@hotmail.com and check out the tumblr
at storiesbyjack.tumblr.com