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This story is a fantasy involving two teenage boys in High School. You can see a list of all my stories on the authors page under the author, Playtime69. All comments are appreciated and can be emailed to ShortStories@PlayTime69.e4ward.com. Please identify what story you are talking about when you send me a message.
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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