This story is based on fact, with a few slight modifications to make it more interesting. I have changed the names to conseal both my and the other person involved's identities.
It was a hot summer day after my freshmen year in highschool. School had ended only a week previous. My brother and I had made plans to go to Six Flags the next day and both decided to bring friends. I called up my friend Matt so that he could sleep over and then we could go bright and early the next day.
Matt is tall for his age. He was about 6' 1", blonde hair, blue eyes, and an average build, nothing too spectacular, but nothing to be ignored. He showed up at my house with his duffelbag and pillow. I told my parents that we should set up down stairs, because we didn't want to be too loud while talking that night (my brother's room is right next to mine.)
After we had setup and had dinner, we played playstation until around 10:30 and then we decided to go settle down. Matt and I went downstairs, and pulled out the sofa, and placed our sleeping bags ontop.
"It's okay if we share a bed, right" I said, "We'll be in seperate sleeping bags, so we won't do anything 'gay' now."
Matt chuckled, "ha, ya, that's ok. But if I wake up with a sore asshole, it's your fault." He said jokingly.
"Ha, ha, ok."
Still bashful, I changed in the room, and Matt changed in the bathroom. I was wearing a pair of sleeping boxers over my regular boxers, and a grey tank top. Matt came out dressed in a pair of long pajama bottoms, and a tight teeshirt.
"Dude, you're gunna be boiling in that." I said. He just shrugged and came into bed. We layed there, our faces only inches away, and talked for around an hour. After a long pause, Matt said, "hey, i'm bored. Wanna play truth or dare?" I was shocked.
"I guess" I responded.
"Ok, it can actually be kinda fun without any girls sometimes."
"Ya, ok. But here are the rules: 1. No daring the other person to do anything you wouldn't do yourself. 2. Nothing with lasting effects. It has to be done and over with tonight. 3. Nothing that will directly get you into trouble. 4. No repeating dares. 5. No turning down dares, or you will lose one piece of clothing and have to sleep without it."
"ya, ok. That's a good idea, that way neither of us will pussy out."
So with that, the game started.
"You choose who goes first, since you suggested the game" I said.
"Okay, fine. You dare me first, I choose dare."
"All right, let me think for a minute... I know, I dare you to moon the window." Matt quickly stood up. There was some light coming in the room from the street lamp. I could clearly make out what he was doing. I watched his pants go down a little in the back. I wished I was outside then, to see his white bottom. "Is this good." He asked me. I nodded my head and he returned to his spot.
"Truth or dare" Matt said.
"wanna just get rid of the truths? They kinda suck. They're pointless." He he asked. I replied with a nod of my head. "Okay then... I dare you to take this pillow, and go into the next room, take all your clothes off, and use this pillow to hide yourself in until your next turn." I got hard just hearing him say that. Good thing I had his pillow to cover my dick with. I didn't want him to see that I was hard. I left my clothes there and came back. I saw him look at me in surprise. I guess he didn't think I was as built as I was.
"Okay, Now I dare you to go out there and..." everything was going so fast. I was laying there next to him all but naked, and I didn't know if he was ready for my dare. I didn't know if he was straight, but just wanted to be funny, or what. I decided to shoot for it, because he wouldnt tell anyone because of what he dared me to do. "go out there and strip, and come back here with just my boxers on." Damn! I knew that it was too much. I was just waiting for his sarcastic comment, and for him to run home scared.
"Sure, why not." He said! The second he walked through the doorway, I got the boner of a lifetime. He was wearing my underwear! I couldn't believe it! When he got closer, I could see that he was getting semi hard as well.
"Okay, if that's how you're gunna play. Fine, go and put on my underwear, and then go outside, and run down your drivway in it. Then come back here and give them to me. Then you can go get your clothes, except for these." He said, pointing to my boxers that he was wearing.
I stood up, walked out and put down his pillow. I looked around for his underwear. Then I spotted them. In gym at school, he always wore boxers, but I was shocked to find a pair of blue Hanes boxer briefs, with a grey band around the top. It was the first time I had ever worn boxer briefs. They were very comfortable. I had a boner, and they did an okay job at consealing it. With jeans, it would be completly invisible to the spectator. I walked back through the room where Matt was, and opened up the door to go outside. Matt got up and watched me from the window. I sprinted out and back, hoping noone could see me. I came back in, took off the boxer briefs, and put back on my sleeping boxers, leaving my tank in the next room.
"That was a good one. I hope noone saw me."
"I think I was the only one" he said.
"Good. Now, it's my turn. I dare you to put my boxers in your mouth, then go outside, on your hands and knees, and piss in the bushes, just like a dog." The bushes at my house were right at the edge of the property line, so it would mean he would be naked for a while.
Matt stood up, with a look of surprise on his face, and slowly pulled down my boxers. When the waist band slid below his dick, it sprung up into action. His dick was a little larger than mine. It was around 8", mine was 7 1/2". He stepped out of them, blushing, and then put them in his mouth, winking at me as he did it. An evid grin went to his face, as he turned around, opened the door, and went outside. He crawled quickly, his perfect butt in the air. He lifted his right leg, and had to wait for a while before the piss started to flow. When it did, he lost his balance and fell, leaving the urine to fly everywhere, including on my boxers. This was the most amazing thing I had ever seen! No porno video could beat this. I felt like my rod was ready to break through my sleeping boxers and rip them a new fly.
Matt came back in, stood up, and let my wet boxers fall to the floor. His nippels were hard, because it was a little cold outside. "Wow" was all I could mutter. He looked at me, grinning happily.
"Now what do I do" he said, "can I put my clothes back on?"
"Yeah, I guess." I said as I picked up my boxers. "actually, just your underwear." I changed my mind.
"Okay, you like these?" he said, putting them back on
"Yeah, I want a pair!"
"You can wear them tomorrow if you want."
"All right!" I couldn't believe what he had just offered me. "then next time I see you, we can swap back."
"Nice!" he said, "can I wear a pair of your boxers"
"Sure"
"Okay, Now I dare you to strip, and stand in the corner, with your eyes closed until I say you can leave" Matt said. I whipped my sleeping boxers off, and sprinted to the corner, thinking I knew what he had in mind. I closed my eyes, and waited. I knew he was checking me out. Suddenly, I felt his hand on my butt. One finger reached into my hole. The other hand grabbed my rod. He spun me around, using it as a lever. I felt his tongue touch my balls, then move up my dick. I felt like I could spew right then. I flinched, and he stopped, and told me to open my eyes. I looked down at him and smiled. We both went back to the bed and layed down. I was naked, he was still in his boxer briefs. I dared him to go limp, and let me do to him, whatever I wanted until he came. Matt liked this idea and just relaxed.
I put my mouth up to his bulge. I covered it, through the tight pouch. I used my hands to pull his dick out. As I did, a strand of precum stretched from his circumsized head to his boxer briefs. I put my mouth back over it and started to suck. I pumped his dick for only a few seconds before it spewed all in my mouth. I went up to kiss him, and shared his treasure. Then he moved his hand over my throbbing dick and started to jerk it.
"Wait" I said. I stripped him of his boxer briefs and moved him to the edge of the bed. I spread his legs and licked his ass, lubing my way in. I inserted my dick and started to hump him. Before long, My juice was inside of him. We cleaned up, and went to sleep, wearing eachothers underwear for the next day, until our next adventure.