Date: Fri, 21 Jul 2023 22:51:49 -0400 (EDT)
From: ShortStories@PlayTime69.e4ward.com
Subject: I Dare You

	This story is 100% fiction and is for mature readers only. If you
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	This story is a fantasy involving two teenage boys in High
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                       I Dare You

                     by: Playtime69


	"I dare you." My best friend, Matt said.

	That was the worst sentence a teenage boy could hear. If you do not
take the dare you are picked on and made fun of, at the least. If you do
it, you then take a risk of getting into trouble and also being made fun
of. There is no good way out and each situation has to be weighed very
carefully.

	In this case, I had to think long and hard about my decision. I was
a 15 year old boy in high school band. It was an excellent band and we won
many awards. This put us in place to be invited to parades, competitions,
and even special events. It was at one of the events that this story took
place.

	The hotel arrangements for the band members was always the
same. The school would rent out an entire floor of a hotel and would put
two to four children per room. The girls always were on one end of the
floor and the boys on the other end. The chaperones would then be scattered
in separate rooms on the same floor. In this instance, the girls were on
the end of the floor with the ice maker and drink machines. This meant that
when the boys wanted ice or drinks or snacks they had to walk all the way
down the hall to the end requiring them to pass by all the girls'
rooms. Not too bad as we all stayed inside our rooms when we were in the
hotel anyway, so it was not like they would all be hanging out in the
halls. It just meant a longer walk.

	It was also a normal tradition for members of the band to pull
pranks on other members. Now the pranks could happen anywhere at any
time. They did not always happen on trips. They also did not happen very
often. But, when they did they were usually some pretty good pranks. The
band director told us that over the years he had seen just about
everything. Normally they were really stupid, non-damaging pranks. Every
once in a while they got out of control which led to disciplinary
results. One such prank one time was a guy was dared to jack off in the
elevator. Little did he know there was a camera in it and the security saw
what he had done and notified the band director. He was suspended from band
the rest of the year and was soon nicknamed, JO (Jack Off).

	Back to my dilemma. Matt and I had only been in our room a short
time from the long trip so we were each laying on our own bed
resting. Eventually Matt got up and began to take stuff out of his
suitcase. That was when I saw something that looked like a girl's skirt.

	"Wearing girl's clothes now?" I asked in a teasing manor.

	It was not that I had any objections to what he wore but we were
really good friends so if he was wearing girl's clothing and had not told
me then I was really going to be surprised. The band had some transgender
members and we thought nothing about it. They were really nice and we were
all friends. So my comment was not to be rude other than wondering why he
had not told me.

	Matt did not take offense but simply answered my
question. "No. This is not a skirt anyway, not really. It is a kilt."

	He then went into an explanation of what a kilt was and how his
Scottish grandfather had told him of such things. I had met his grandfather
so figured what he was saying was true. Plus, Matt was my friend. Why would
he tell me something that was not true.

	I had never seen a kilt and as best I could remember I had never
even seen a picture of one. This one was solid dark blue with red trim. If
fastened in the back with a button and a zipper down from the waist. It was
not very long but was long enough to cover my underwear even if I bent over
a little.

	Now back to where I was. "Come on...Well? Are you going to take the
dare?" Matt asked again.

	"All I have to do is put the kilt on and walk to the end of the
hall, fill up the ice bucket, get two soft drinks, and walk back?" I
checked.

	"That is all there is to it, Pat." Matt assured me.

	"What do I wear under the kilt?" I asked as I tried to get more
information.

	Laughing, Matt said, "Well you can go borrow some panties from your
girlfriend. If that would make you feel better."

	That was too much and I pushed him back onto his bed. He was
laughing hysterically as he tried to tell me just to wear my white
underwear. Then as a second thought and another way to pick on me he added,
"But...seeing you in her panties would be fun to see." He then collapsed to
the bed in a fit of extreme laughter. I really did not know if he was
saying that just to say it or if he really did want to see me in
panties. Either way, that was not going to happen.

	Finally, he sobered up and we were back into negotiations. "Ok. I
will sweeten the deal. Look at what I brought." He said as he pulled a
'Playboy' magazine from under his clothes. "When you get back we can...you
know with it." He told me as I looked over which one it was.

	We would use them quite often when I stayed at his house and when
he came to mine he always brought one or two for some nice viewing as we
jacked off. This did make me more interested. I figured though that I
really did not have to take the dare to get to look at it but if it made
him feel like he had won the dare then I was not going to make him think
otherwise.

	"Well?" Matt brutally wondered.

	I opened the door and looked down the hall. It was completely
empty. I figured that if I got ready and then checked to make sure the hall
was still empty then I would have a good chance in getting there and back
in one piece. I finally told him I would take the dare. I took my socks and
shoes off then my pants. I slipped the kilt up my legs and with the help of
Matt I got it buttoned and zipped. He had me tuck my shirt into the
waistband so the kilt was more visible. Looking in the mirror, I was
surprised at how cute I really was. It did not even go half way down
between my knees and underwear but covered everything it needed to.

	"Wow! You do look cute." Matt cooed.

	"Quit it." I yelped as I again pushed him to the bed.

	"No! I am serious this time. You really do look cute. It fits
perfectly." Matt said as he ogled the bottom half of my body. "If I saw you
in panties I would probably shoot my load right in my pants." He boldly
added.

	I was not sure if I should be mad, embarrassed, or excited. I am
sure I turned a little pink but in the dim hotel room lighting he probably
did not notice. I figured I had better get this over with. I opened the
door and looked out. No one in the hall, perfect.

	Just as I went to step outside the room, Matt called out, "Hey,
dipshit didn't you forget something? How were you planning on bringing the
ice back? Did you get money for dinks?"

	Because I was concentrating on one and only one objective I had
completely forgot about that part of the dare. I fumbled around and got
some money for drinks. I grabbed the ice bucket and soon was looking out
the door for the third time. Good. No one there. I stepped out and as soon
as I was outside the door, Matt slammed it shut. I had no choice now I had
to get the ice and drinks or he was not going to let me back into the room.

	I knew taking it slow would take longer and since I was barefoot
and on carpet I knew I was not going to make noise as I walked. I picked up
the pace but made sure I was not running. That would have got me in more
trouble than almost anything else. I had cleared the guys' rooms and was
now in the girls' section. Still feeling pretty safe I scampered on. Then I
heard it. The dreaded sound of a door opening. I looked back to see one of
the other guys coming out of his room. Our eyes locked. He then looked down
to see what I was wearing and whistled at me. It was the loudest whistle I
had ever hear. The sound bounced off the concrete walls in the hall making
it as loud as a fire alarm.

	Doors then began to open and the more doors that opened the more
heads that popped out. Most all of the girls' doors were open and some
stood looking and some stood in the hall as I made my way through the
gauntlet of band members. Remember these were all people I knew and
practiced band with. There was going to be no living this one down.

	I finally had enough and out of desperation I blurted out, "It is a
kilt! Guys wear them all the time in Scotland."

	Hearing lots of giggles and whispering, I made my way to the ice
machine to finish the dare. I filled the ice bucket with ice and then began
to try to get the drinks.

	Rachael, my 14 year old girlfriend came up to me and said, "Here
let me hold that while you get the drinks."

	"Thanks." I embarrassingly said.

	"Dare?" She probed.

	"Yeah." I gave the short response.

	"You do know that is not a kilt. It is a girl's skirt. I have one
just like it at home. I think you have been pranked." Rachael
sympathetically told me.

	"Great. I am going to kill Matt." I said as I could feel my face
turning beet red.

	Rachael being the calm one at that moment said, "Just keep in mind
about the prank you pulled on him a few months ago. It was the best I had
seen. I am sure he was just getting you back. Here let me carry the drinks
for you."

	"Thanks but I cannot let you do that. Part of the dare is that I
carry drinks and ice back by myself." I told her. "You can walk with me if
you want." I added.

	We took back off through the now entire band ensemble to my
room. "Do your panties match your skirt?" I heard a girl call out. "I have
a cute dress you might want to wear." Another girl yelled. As I got further
down the hall another girl said, "What you got under that cute skirt?" And
just at that time she lifted my skirt letting all behind me see my white
underwear. I swung around unintentionally flinging ice cubes
everywhere. The girls began to squeal and laugh as I finally made it back
to the boys' end of the hall. There were not as many boys out and they did
not seem to care too much. Most all of them had been pranked at one time or
another and most dealing with sex, nudity, clothes, or other personal
embarrassments. They knew what it was like and they either did not care or
thought I did look cute in the skirt.

	"Ok. Show is over. Everyone back to your own room." One of the
chaperones yelled out.

	He walked up to me and asked, "You ok?"

	"Yeah." I quietly said.

	"You got to admit. That was a pretty good prank." He then told me
as I made it safely inside my room.

	I made it inside the room, handed Matt his drink, and showed him
the half bucket of ice as I said, "Hope you choke on it. There I got
through the dare. Magazine please."

	Matt was rolling on his bed as he laughed uncontrollably. When he
finally could talk he said, "Now, we are even."

	"You wish. It is war now." I told him. Then as I looked at his
suitcase I said, "Magazine."

	With Matt finally down to a chuckle he said, "It is dinner
time. Then showers. After bed check, I will get it out."

	I knew that was best so I simply said, "Ok."

	Knowing he might have crossed the line he stuck out his hand to
shake as he asked, "Friends?"

	I took his hand and shook it telling him that it was a good prank
and that we were still friends. I was just worried as to what was going to
happen when I saw the others. I knew over time it would be ok. I just did
not know how long it would take.

	We went down and had dinner with everyone else. There were a lot of
giggles from the girls. Some asked if they could borrow my skirt. Some
asked if I wanted to swap clothes but overall it was bearable. We got back
to the room and showered. With about 30 minutes before bed check we watched
some TV.

	"Bam Bam Bam." We heard a pound on the door. Followed by it
opening. "Lights out in 10 minutes." The chaperone said.

	"Ok. We were just about to turn in. Good night." Matt said.

	A few minutes later I went and grabbed some towels. I threw them on
the floor in front of the door. This kept the light from shinning into the
hall so they would think we had turned out the lights. We now just had to
turn off the TV and keep pretty quiet. We could not moan too loud and we
could not make a lot of moving sounds. You would be surprised how easily it
is to hear what is going on inside a room from the hall. Waiting a few
minutes before he got the magazine gave us time to pull our underwear off
to be ready.

	"You really were cute, wearing the skirt. I was not joking about
that part. If you ever want to make me cum quick then all you would need to
do is put on the skirt and some panties and then lift your skirt up in
front of me. I would instantly blast a load." Matt admitted.

	I knew he was telling the truth because his cock had already
increased to 4" long. He only had another inch to go before he was full
sized and he still had not looked at the magazine yet. I, on the other
hand, was still at a mere 3". When I got fully hard though, I would surpass
his length by a good inch. Then again I was older than Matt, but not by
much.

	We sat side by side on a towel that was on his bed. The magazine
was in front of us so we both could look at it as we stroked. After what we
had both done and seen so far that night I figured this would not take too
long. We both began to stroke as we took turns flipping the pages. Some
pages were turned rather quickly and some were turned at a slower pace. It
just depended on what the girl looked like on the page. We were both hard
as a rock within five minutes of stroking. I was going to give it five more
before we exploded. That was until Matt stopped all of a sudden. I could
tell he had not cum and was wondering what he was waiting for.

	"Pat?" Matt slowly said.

	"Yeah, what?" I panted as I began to get close to blasting my load.

	"I got something to show you...but...I do not want you to think I
am weird or anything." He slowly said.

	"Dude. If I do not think you are weird after telling me you would
instantly cum if you saw me in a skirt and panties then I cannot think of
anything that would make me think of you as weird." I told him as I slowed
down on my stroking until I saw what he wanted to show me.

	Matt got up off the bed. His now hard 5" fairly thin cock bounced
up and down as he moved. He went to his suitcase and pulled out another
magazine. I tried to see the title as he returned to the bed but he had it
hidden.

	"Holding out on me?" I teased.

	"Kind a, but not really. Please do not think I am sick or
something." He begged as he plopped the magazine down in front of me.

	"Frotting Dicks? What kind of a magazine is that? What is
Frotting?" I began to question.

	Matt said very little but simply opened up the magazine. It was
just a bunch of dicks touching each other. Mostly two at a time. He pointed
to a list of steps required to Frott. I looked over them as my dick refused
to shrink any at all. Matt's dick was also staying rigid as we read it
together. Once we had been over the list and had looked at some of the
examples, Matt asked if I would like to try it. It did look interesting and
fun but I wanted to see if I could get a little something extra out of it
before giving in.

	"I tell you what. If you will put on the skirt and let me look at
you in it then I will give it a try." I told him.

	Something told me he had already tried it on when he did not even
try to get out of putting the skirt on so I could see him in it. He wasted
no time and jumped off the bed and in a matter of seconds he had slipped
the skirt on and turned around so I could see. His cock was sticking
straight out making a pointed rod effect in the front. In my opinion, he
just did not look as good in it as I did. Then I thought that when I had it
on my cock was limp so I looked more like a girl than a guy while wearing
it.

	Shove your dick between your legs and put on your underwear. That
will make you look more like a girl in a skirt than a boy in a skirt. He
did as I said and soon I was seeing something that was turning me on. Matt
did not have a shirt on and with his chest being hairless he looked like a
young girl in a cute little skirt. My dick began to bounce up and down as I
was enjoying the view. I told him to go look at himself in the mirror. He
did and came back telling me that he really looked cute. I agreed.

	"Where did you get this magazine?" I asked.

	"Same place I get the others, from my older brother." Matt
answered.

	"What about the skirt?" I wondered.

	"I told my sister what I wanted to do so she told me I could use
this one." He then explained.

	"Why not panties too?" I asked as my dick was begging for release.

	With a chuckle, Matt said, "My sister said she did not want any of
my friend's little dick, playing in her panties."

	I laughed myself at his answer. I then suggested he pull off his
underwear so we could try frotting while he wore the skirt. Matt then told
me that if we got cum on her skirt his sister would kill him so that we had
better not do that. I understood and told him to get it off so we could
frott before I exploded.

	With us both naked again, we got started. We sat in front of each
other, the magazines both now open, one on each side of us. My legs crossed
over the top of Matt's legs and our dicks touching each other. Following
the directions we began to rub them together. I never knew that my cock
rubbing another cock could feel so good. I grabbed both cocks and began to
stroke them together.

	"Oh fuck." Matt moaned.

	Matt began to hump me as I pumped our now pre-cum coated
cocks. Matt then wrapped his hands around mine as my hands were holding
both cocks as they both were about to explode. We both had lost control and
were bouncing, thrusting, pumping, and humping each other in no particular
pattern. We both were just trying to get off. When jacking yourself off you
can move and manipulated you dick so you can make yourself cum when you
want. This was like being teased to the max. We hit just the right spot for
a few seconds then off the spot just a little. Once back in the right place
the feeling or an orgasm would come back until we moved just a bit. This
bouncing around was driving us both into a frenzy.

	I lost control. I had to cum and I wanted my cum to spew all over
Matt's dick. I then wanted Matt to spew his cum all over mine. I pushed
Matt back on his bed with his legs going out straight. I jumped on top of
him, lining up our cocks so they were once again side by side. The heads
now touching each other. I began hump Matt's cock with mine. It was just
like when I fucked my girlfriends pussy only he did not have a pussy. He
had a cock so by rubbing my dick across his I found it similar but
different.

	I must have hit just the right spot for Matt because a few minutes
later I felt his cum spurting all over my dick and belly then it ran down
to my balls. The hot slippery layer of cum made my super-charged dick
explode. I blew more cum than I had ever blown before. My cum shot all the
way up to our chests as we continued to rub our bodies together. By the
time I was finished humping him we both were covered with cum from our neck
to our legs.

	We both were panting as we tried to keep quiet. There was no way we
could talk without grunting out too loudly due to the lack of
oxygen. Eventually we gained our composure and I got off of Matt. We both
sat up wondering what had just happened.

	"I am not telling anyone what we just did. Are you?" Matt quietly
asked.

	"No way, Dude. Never." I agreed.

	We decided we had better shower again because of the massive amount
of cum all over our bodies. We really wanted to sleep together in each
other's arms with the cum drying to our bodies overnight but we decided
that was not going to be safe. If something happened and we over slept the
chaperones would walk in on use and catch us in bed together. What we did
decide to do was as soon as we got home, we would spend the night together
doing the same thing only that time we would simply fall asleep
together. We wanted to know if this was just some adventure of if it was
something else.

	What about the skirt thing you might ask. Well, Matt 'borrowered'
some of his sister's panties and we took turns wearing them under the skirt
just for excitement before we frotted. It was a turn on but eventually the
fad faded away and we would just jack off together, on each other, or rub
each other until we exploded. We tried sucking each other once but neither
of us enjoyed that too much. The one thing we never tried was fucking each
other's ass. I had my girlfriend's pussy and Matt eventually got a
girlfriend so we did not need another hole to fuck. The frotting was
another story. That sensation lasted all through high school and beyond.

                           The End