Date: Tue, 29 May 2018 10:10:33 +0000
From: Jack Stories <storiesbyjack@hotmail.com>
Subject: I Dare You - Chapter 3

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.

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

Thank you for your emails so far. The dare for this chapter comes from the
suggestions from a couple of people and their kinks for underwear.

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

Chapter 3 of "I Dare You"

If you can believe it, after submitting the pictures, videos and story for
my 'being naked outside' dare, I closed the app and pretty much forgot
about it for a good few hours. I know that this site was a major discovery
for me and that I'd had two very horny experiences using it but I have a
life as well and I wasn't about to spent every moment of every day glued to
my phone. Well, not just for the dare app anyway.

I can't believe that I let my brother see me like that. At the time, I
didn't have a problem with it and it actually turned me on a little to see
him checking me out but, now that my horniness has been taken care of in
the shower, I actually felt a little embarassed. Not for me, my body is
getting pretty good now and I'm happy with my cock, but for him! There's no
way he looks as good as I do and I could totally tell that from the way he
was staring at me.

I was a little mean. After drying from the shower, I slipped on a tight
pair of CK boxers - the black material hugged my arse and the outline of my
soft cock was very visible. Then, acting like it was the most normal thing
in the world, I went downstairs to join my brother in the lounge. He was
sat in a chair and watching tv so I walked over to the couch and laid
myself down on it. He was behind me so I have no idea whether he was
looking at me; he certainly had a lot to see if he was. My torso was
completely exposed, with the outline of my abs standing out and the bulge
in my boxers wasn't hidden at all. I kept trying to do things that would
draw his eyes over to me as well: wiggling my toes so the movement would
bring his eyes; making quiet noises as I shuffled around so that he'd be
drawn to look and, of course, the most obvious of all, reaching into my
boxers to 'readjust' several times. If he was watching, I was definitely
giving him something to look at.

This was so unlike me and, honestly, I don't know why I was doing this. I
guess I wanted to give him hard time with how badly we'd been getting on
recently and, after seeing him staring at my naked body, I knew that this
was an easy way to get him. I didn't for one second believe that he was gay
or interested in me - Alex has had several girlfriends - but the fact my
body is developing was clearly irritating him and I was determined to play
on that.

However, my fun was cut short by the sound of my phone going off. No, it
wasn't the app - it does more than that you know! It was Will asking me
what time I was coming over. Shit! In all the excitement this morning, I'd
forgotten that I was supposed to be spending the day at my best friend's
house. He'd been stuck babysitting at all because his parents didn't think
his younger brother was old enough to spend the day alone in the
house. That was a bit ridiculous to be honest. At 13, Will and I had spent
loads of time at his or mine just the two of us but, for whatever reason,
his parents now didn't apply that same logic to their second-born son. I
messaged him to let him know that I was going to get ready and head over.

It didn't take long to dress. As I've said before, my style is fairly
simple so I can pretty much just grab several things from the waredrobe,
throw them on and they will match into an outfit. Today was a pair of black
shorts, a classic white t-shirt and a pair of red converses. I really
needed to get my other clothes back again - I know the vans were beat up
and nearly falling apart but they were my favourite pair. I didn't bother
with socks; I'm far more comfortable being barefoot and, at home or at
Will's place, I usually end up taking them off anyway.

The journey to Will's isn't far - to be honest, nothing is far from
anything in this village. I live right at one edge and it would take me
around 35-40 minutes to walk to the other side. Growing up here had been
nice once the rich snobs in the larger houses had accepted that we poor
folk were here to stay. Hell, my best friend was one of those rich lads
with one of the biggest houses in the area. That was one of the reasons
that we spent more time at Will's than at mine. At his place, you could be
there with the rest of the family and still not be on top of each
other. Well, that and the indoor heated swimming pool. There was no time
for swimming today though; Will had just bought a new game and the plan was
to spend the day on it.

As I was walking through the village, my phone beeped. My submissions had
been accepted and the author of the challenge had left some comments: "OMG!
I can't believe your brother saw you naked! And the fact you had to get
home completely in the buff as well is so hot. I've spunked hard watching
your video and your pics. I've asked that you be awarded double the points
for this one for going so far with it."

Fuck yes! I guess it turns out that pushing myself to go further than just
a quick flash in the garden really does pay off. I mean, I think it does. I
haven't actually fully checked out this points thing but, hey, earning more
of them can't be a bad thing, right? There were no comments from anyone
else yet but the pictures I'd taken outside, the video and the recount of
what had happened had all been uploaded onto my profile so everyone would
be able to see them. It was so hot to think of all the guys out there that
might be getting off reading about what I'd done or watching the video and
I was definitely inspired to do some more challenges. Unfortunately for me,
there weren't any waiting so I closed the app - I'm sure it would alert me
to a new dare when I got one.

"Mate!" Will greeted me as I reach his door, "I've been going off the
fucking walls - this kid is doing my head in."  "Aw come on, Chris can't be
that bad! I thought he was spending most of his time in his room now."
"Nah, all morning he's been bugging me. It's like he wanted to spend every
second with me!"  A pang of jealousy definitely hit when I heard him say
that. I'd genuinely do anything to get that sort of relationship back with
my brother. As it was, I played it off and agreed that Chris, Will's 13
year old brother, must be really annoying and that it was great that Alex
leaves me completely alone now.

So, Will's place is one of those houses that have dedicated rooms for
everything. There are several living rooms which are all called different
things. There's the lounge that his parents mainly use, the family room
where we spent most of our time when we were little, the dayroom which
isn't really used that much and, my favourite of all of them, the home
cinema. Now, it obviously isn't a full cinema - that would be ridiculous -
but it is a space used specifically for the massive TV and sound
system. That's where we were headed today to play on his new game.

We'd been playing for about 30 minutes, sat relaxed in the reclining sofa
seats, when his brother caught my eye from the edge of the room. Will
hadn't noticed but Chris was just stood there watching us play the game. It
was obvious that he wanted to come in and spend time playing with his
brother. If Will was going to just ignore his obvious pleas then I'd have
to take it upon myself to sort.

"Hey, do you want to play along, Chris?" I called out to him. Will shot me
a look as if to say 'What the hell are you doing?' but I just looked back
at him. He got the message. That's the benefit with having a friend you
have known for pretty much your entire life: sometimes words are needed.
"Are you sure?" came the quiet voice from the doorway.  There was a moment
of silence before Will rolled his eyes. "Yeah," he said to his brother,
"Come on, I'll show you how to play."

The next hour was full of laughter and banter as the three of us played
against each other in rotation. Will was the best by far which was to be
expected since he was used to playing on the console. I held my own against
Chris but he still beat me as often as he lost. I was about to start a game
when my phone went off. I recognised the beep and didn't want to check it
in front of my friends incase they saw what came up.  "I need to go to the
bathroom," I said, "Why don't you two play the next round?"  The brothers
agreed and I walked out of the room and upstairs, pulling my phone from my
pocket as I went.

There were a bunch of new comments on the new content I'd submitted for my
profile but I didn't have time to read those now. I knew what that sound
meant - a new dare had been made.

"I'm big into underwear," the dare read, "Wank that beautiful uncut cock
for me and spunk all over a pair of boxers and then wear them.

Fuck, just reading that made my cock start to harden. Initial plans started
to form in my mind and I hurried upstairs. I was intending to head to the
bathroom, have a quick wank, coat my boxers in my cum, slide them back on
and then join Will and Chris downstairs. That's exactly what I would have
continued to do if I hadn't walked passed Will's open door.

I paused. Just like with the being naked outdoors challenge, there was a
way to take this one even further. It would rely on Will being a bit of a
slob which, come on he's a teenage boy, I knew he was. Also, I'd have to be
very quick: I definitely didn't want my best friend coming up to catch me
doing what I was about to do.

Pushing his door open, the light from the corridor fell onto his
bed. There, next to it, in a pile was Will's latest washing. I rushed over
and started pulling through the clothes. It didn't take long to find
exactly what I was looking for - a pair of used black boxers. I quickly
pulled down my own shorts and boxers, leaving my t-shirt on, and laid down
on my best friend's bed.

My cock was already hard but it became like steel when I brought Will's
dirty boxers up to my face. His scent was all over them - I could tell that
before they reached me - but, when I breathed in his stink with the crotch
of his boxers pressed firmly into my face, it was like electricity to my
cock. With my right hand, I started to slide my foreskin over the head of
my cock. It was already leaking and dribbing down my hand. With my left, I
rubbed this dirty pair of boxers all over my face. His scent was
intoxicating. It was an incredibly strong burst of him as if someone had
bottled up every smell from his body and made it 10 times stronger.

I dropped my cock for a moment and reached for my phone. Opening the
camera, I took a series of pictures of my face with Will's boxers rubbed up
against me. Wanting to push it further, I opened my mouth and stuck part of
them in and it was then that I got a surprise.

As I posed for that picture, the smell of fresh spunk filled my noise. I
pulled his boxers from my mouth and turned them over. There, on the inside
of the cloth, was the evidence of Will's earlier wanking. My heart began to
pound and I wish I could tell you that I debated it but I didn't even do
that. No, I simply brought the boxers upto my mouth and my tongue darted
over Will's spunk.

This was the first time I had tasted someone's cum, other than my own of
course, and my tongue came alive! I know it wasn't from the source and, in
fact, it was probably about 2 or 3 hours old and had begun to sink into the
material but it was my first taste and I loved it. My cock was throbbing
without me even touching it as I took another picture of me with my tongue
touching the obvious spunk stains on Will's boxers.

I wasn't done with them but my cock had ideas of its own. It needed to cum
and it needed to cum now. I placed Will's boxers over my abs and lifted
them slightly as I returned to wanking my uncut teen cock. My balls started
to tighten and pull up against my boxer. It was time. In my hand, my dick
started to pulse and throb and I began to pant harder, trying desperately
not to cry out. Then, it happened. Rope after rope of my creamy teen spunk
shot out across his boxers. I managed to catch most of it as it flew up
into the air; the whiteness of my cum contrasting against the black of his
boxers. I bit my lip and moaned out as I teased the last few droplets out,
making sure to wipe those up with the boxers too.

I lay back for the second and admired my work. I had shot a lot! Much more
than Will had done earlier that day and the underwear was covered in teen
spunk. I snapped a series of pictures, capturing each side of them and then
remembered the last bit of the challenge. Standing up, I took his used
boxers and slipped them on, my teen arse and cock occupying the same spaces
that his had and the spunk still warm on them. My shorts went on over the
top. Unsure what to do with my own boxers, I simply folded them up and
placed them in Will's underwear drawer. The idea that, one day, he'll slip
my worn underwear on and wear them for the day without even knowing about
it was kinda hot and I was definitely chubbing up again as I took the final
few pictures for the dare app.

Before I left his room, I took a quick glance backwards to make sure I
hadn't disturbed anything and was really glad that I did! I thought I'd
been pretty good at catching all of my spunk but it turns out that my shots
were much harder than I anticipated. There, on Will's pillow, was a big
chunk of my spunk. I didn't know what to do but then I had a kinky
thought. Taking my hand, I rubbed it into the fabric until I just looked
like a slightly wet patch. If Will saw it, he would just think he'd been
drooling in his sleep. You and I would know that he'd lay his head down
there tonight with the smell of my spunk filling his nostrils.

Walking down the stairs, I submitted all the pictures and, again, a brief
summary of what I had done. Putting my phone away, I joined the two
brothers in the cinema room, desperately hoping they wouldn't smell the
teen spunk coated Will's boxers underneath my shorts. This dare app was
getting me into some interesting situations and I was loving every single
minute of it!


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

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