This story is about me finally finding a best friend that I'll remember for the rest of my life.
I had moved around a lot as a kid and up until 16 years old, keeping friends was hard. Then 3 weeks ago we moved to this new school in upstate New York. A fancy looking campus with multiple academic buildings and perfectly manicured sports fields.
4th period was ending -- gym class. I was almost done changing and pulling my ratty t-shirt over my head when HE walked up.
"Nice foot work, dude." Jared said. He was tall, a good half a foot bigger than me. Slim build from swimming with great pecs and a model's hair which he constantly pushed back in an effort to make everyone's hormones go wild. Skin gorgeously dark tan and eyes that sparkled. His chest had just a little hair right on his pecs - enough to make every boy around him feel less manly. When he spoke I got hard instantly. Luckily I already finished putting my jeans on cause it helped hide my bulge.
"Uh thanks." I said tripping over my words like an idiot.
I don't know why I got hard talking to him. I don't think I'm gay. I certainly don't want people to think I'm gay, but for some reason being around this dude made my cock go haywire. Who am I kidding?
"You play?" Jared asked.
"Nah. Just gym class."
"Too bad -- you've got good legs." Jared said. I almost leapt out of my skin. I looked around but only Jared and I were left in the locker room. The others had cleared out apparently.
"Uh..."
"For soccer, dude. Lighten up."
"Oh! Yeah, well thanks." I said, relieved.
"Hope we'll play again soon on the same side. Unless you always bat for the other team?"
He flashed his perfect smile.
"Jared," he said, extending his hand.
"Rae, " I replied, shaking hands with him. I felt like he was towering over me.
"Well got the girlfriend waiting. Keep in shape."
Jared let go of my hand and used his now free hand to slap my ass. It seemed like a normal macho guy thing; except he did linger long enough to feel up my ass. Or maybe I imagined that.
We hung out at school over the next several weeks. There were many times we'd be in class goofing off together. Or hanging out behind the cafeteria when he was avoiding his obnoxious friends as he sometimes called them. Turned out, his girlfriend had quite the posse whom he was belabored into also being friends with. And sometimes Jared just needed a break from all that. Apparently, I was easy going enough to give him that. Me!
We played footie and told dirty jokes and talked about hot girls in our grade. Occasionally, we'd even study together. It was bliss. Except it was also torture because every time he laughed, or smiled at me, blinked -- I'd get super horny. This guy did things to me that were more than hetero.
Most of the time, there was nowhere to jack off at school so I was forced to wait until I got home to get off. I'd shoot one or two loads in the morning before running to the bus. Then agony for the 8-hour school day. My nuts were always bursting by the time I got home. Most of the time, I'd find a sea of pre-cum in my boxer briefs from the course of the day. My underwear was straight up wet on the days Jared copped a good feel.
Oh yeah, the playful game of ass smack that started that first day in the locker room had escalated to Jared spanking my ass, then pausing to watch my bubble butt jiggle a bit. Or when no one else was around, he'd even grab it a bit and lightly run his finger a long my crack.
It never lasted long but he and I both seemed to have an understanding not to discuss what was happening. Or how many seconds he left his hand on my butt (6 seconds being the longest by my count). The game of grab ass was easy enough to explain away. Especially because he had a girlfriend.
One day, Jared and I finally decided we should hang outside of school. And so a sleepover was put into motion for that Friday night. Jared would come over to my place because my single dad always went out on dates on Fridays. This meant the two of us would have the whole house to ourselves.
Finally, it was Friday. Foolishly, I'd forgotten to set my alarm so no morning jack off session for me. To make matters worse, Jared came up to me at lunch to explain that he was just going to ride the bus home with me, so his parents didn't have to drive him to my place.
Once the two of us got on the bus for my place -- Jared started in on one of his rants about a biology lesson earlier that day. I was grateful because it made me forget how horny I was. At this point, it had been over 24 hours since my last jerk off session and I didn't dare to think about how much my balls were bursting to shoot a load.
It was my first sleepover with a friend so I'd over prepared the night before. I had cleaned up my room but not too much (had to look cool) and laid a bunch of snacks including my favorite candy -- cinnamon jelly beans.
Jared and I spent several hours or so talking about random topics: girls at school we liked, places we wanted to travel to, teachers we hated, etc. I showed him the house, we played video games, went for a hike in the woods out back and watched a little TV.
Around 12:40am, we both knew it was time to head to bed. I was intending to show him out to the couch he'd be sleeping on in the spare room. And asked him if he wanted extra blankets.
Jared got up and moved really close to my face. He locked eyes with me. I'm sure he could see in them how confused I was. Then he leaned in and grabbed my ass -- huge handful of it. His finger caressed my crack, breaking his six second record by a couple of seconds. His eyes flashed, saying "All I've got to sleep in is my gym clothes. You think I could do a load of laundry so I have something to wear tomorrow."
"Oh yeah of course. Or would you like to borrow some of mine."
Jared laughed. "Don't think you'll have anything big enough to fit me," he said, looking up and down my body. My eyes followed his. His attention on my ass had made me spring massive wood. I hoped it wasn't as obvious to him.
"I'm a bit bigger than you, my trim little buddy."
I blushed. Of course, he couldn't wear something of mine. He was a muscular swim god and I was a short, lean, average guy.
"You smell like cinnamon." Jared said and walked away, but not before giving my ass another playful smack. I trembled in front of him, unable to figure out how to respond. Jared interrupted my awkward silence: "You going to show me where the laundry is?"
"Yeah," I replied. My dick has grown to full mast in my pants. I tried to adjust it as subtly as possible hoping he couldn't see the bulge.
We walked across the house to the laundry room. I stood while Jared threw his gym clothes into the washer. He took off the shirt he was wearing, his socks and tossed them in as well. He leaned over to turn the dials and get the load going, showing off every inch of that Greek runner upper body in his remaining shorts.
"See something you like," Jared said, figuring out the right setting.
"What? No. Me? No. No, I'm not gay." I spat out, barely making them sound like words.
"No worries, dude." Jared said, then continued,
"I don't care either way. But it was just a joke."
Jared put his hands on my shoulders, I think hoping it would calm me down. Instead, I became very aware of the precum dripping from my dick and into my boxer briefs.
My phone buzzed. A text from dad: Sleeping at hers tonight.
"Oh shit. My dad's not coming home. Are your parents going to be pissed?" I asked.
"Nah. I just won't mention it. Besides, it's not like you and I are going to blow up the house."
"True." I was sweating a little which seemed to amuse Jared.
"You need to loosen up," said Jared. His hands were still on my shoulders, rubbing softly.
"Oh? How do you propose I do that?"
"Up for a dare?" Jared said, smiling.
"What kind of dare."
"You'll have to loosen up enough to ask me for it." Jared replied, cocky as ever. And leaned in close to me again. I became very aware of his scent all of a sudden and was even hornier than before.
"Uh, I guess."
Jared left his clothes to wash and headed back to my room. He plopped himself down on my bed. I came in after him and closed the door. Then opened it again, thinking that seemed weird.
"Ask me." Jared said while purposely letting his exposed upper body make contact with my pillows. I'll never wash my pillow cases again.
"What's my dare?" I asked.
"I dare you to do a striptease down to your underwear -- And it better be good underwear." Jared said, looking like a fox in a henhouse.
"What's good underwear?" I said and then immediately regretted not objecting to the idea of stripping.
Jared smiled at my willingness. "Something that shows the curves. No baggy boxers. Something risque."
"I don't know what I would have."
"I'll pick them then." And he jumped up without a word and started unapologetically rifling through my closet.
"Ok." I said. Standing there having an out of body experience while the hottest guy in my grade hunted through my personal stuff and then went rifling through my dresser. My dresser! The thing filled with the stuff kids don't want their parents to ever see. And here was my hot best friend, penetrating my secrets while I just stood there waiting for him to lead. In the back of mind, the growing embarrassing realization that I was going to strip for him.
I walked over to my closet and went inside. Jared said, "Good idea. See if you can find something in there while I keep looking. Slim pickings so far."
Jared found at least 12 pairs of boxers or boxer briefs. Sometimes he would take a moment to consider a pair the boxer briefs but ultimately they all went to the same place.
"Hey." I said, looking out from my closet, "That's a trash can."
Jared didn't stop what he was doing but he cocked his head sideways at me, saying, "Relax dude. You don't want these tired shorts. It's time a stud like me told you what you should wear."
"...told me?" I mumbled to myself. Jared cocked another smile at me, showed me a pair of my favorite Calvins and then threw them in the bin. He moved over to me -- a still stunned look on my face -- and said, "Relax dude. I got you. Now keep looking. Bring me everything you've got."
I turned around again to head back into the closet. Jared smacked my ass and then went back to trashing my undies. I gathered more discarded pairs of my shorts from the closet.
The ones that were old, or I'd grown out of, or the unopened package of 2(X)IST trunks, I'd hidden away after stealing from the mall. Too embarrassed to buy them.
I started at myself in the full-length mirror on the back of the door and then opened the front of my jeans and looked down. A full-on wet stain all over the front of my boxer briefs from my precum -- the front of them looked less like I'd wet myself and more like someone had squirted me with frosting. Won't be wearing these in front of Jared -- I'd need to change out. Mmmmm, I think I love the feeling of cum on me.
Since I started wacking it, I've always hated that slimy sensation on my skin. Once my orgasms subsided, I'd always run to the nearest thing to get the spunk off me.
But now, the thought of cum swimming all over me turned me on in a new way. My skin tingled and my dick twitched from the excitement of it.
I stripped off my clothes down to my skin and rifled through the pile of underwear on the floor. It was hard to tell what was clean or dirty, but that's the life of a teenage boy's closet. I found a few boxers that were from my younger days and some black briefs from middle school. Not sure, either of them would really fit without riding up my ass crack. But I set them aside and kept looking for something better.
At the bottom of the pile was my uniform from middle school Cross Country -- a pair of running shorts, a mesh T and a black, blue-lined jock strap. Then an old speedo from freshman year of high school -- why did I still have those? The school mascot was the Ram, so in the most unfortunate way, RAMS was printed across the butt part of the suit. I immediately stuffed these two items behind a box on the top shelf along with the wet-with-cum boxer briefs.
"How's it going there, little buddy?" Jared hollered.
"Still looking." I whimpered. I realized the very sound of his voice had gotten me hard again and I was leaking precum down the length of my 7-inch cock. Shit.
I grabbed the nearest thing to me -- the button up shirt hanging behind me. My one and only dress up shirt was used as a precum rag as I smeared the inside of it with pre fuck juice and used the collar to get the tip of my dick. Hoping Jared wouldn't come in. I hung it back up believing this was the best course of action.
"I'm almost decided," Jared said.
I went to my hamper -- I'd cleaned my room yes, done my laundry yes, but I'd gone for a run last night. In the mostly empty hamper were a pair of dark blue trunks that I'd worn during my run.
I turned and looked at myself in the mirror, holding the trunks and then sniffed them. They smelled like sweat with a little musk. Not too gross and what other choice did I have.
I saw myself for the first time. Yeah, I was skinny but I still had definition in my arms and legs. And then, maybe for the first time, I saw my ass. It was bigger than I remembered and wonderfully round like two firm cantaloupes. Maybe that's why Jared always grabbed my ass - anyone would be jealous, even a straight guy.
Slipping them on, I noticed my figure. I liked what I saw, but I also forgot why I always wore them to run. You see I've had them for 2 years and so they are a size smaller than my usual. Looking at myself - they indeed rode up my ass. At least 20% of my ass was showing, which was more than a bit of a stretch for me. Also, it was impossible to hide the size and outline of my package in the front. But what other choice did I have? I slipped my jeans back on.
"What's taking you so long?" Jared said, popping his head through the door.
"Just getting it all for you." I said, scooping up the pile of underwear off the floor.
Jared's eyes lit up and his smile brightened enough that I could see his pearly whites. "Let's see." Jared said.
"Yeah they are." I said, somehow seeking his approval for bringing them.
"Cool. Don't want to touch any of your dirty shorts." Jared said, beginning to rifle through the pile in my arms.
"Nope.. nope.. nope." He said, continuing to toss pair after pair unceremoniously in the direction of my trash bin. At the bottom of the pile was the package of unopened 2(X)IST. I blurted out, "Uh, those aren't mine... I mean my dad bought them for me."
Jared used his hand to ruffle my hair, saying,
"No worries dude -- it's okay if they're yours. Let's have a look."
He ripped open the package - his arm muscles flexing perfectly in the dim light of my bedroom. I found a spot on the wall, trying not to make myself any hornier than I already was.
Jared held up a pair. I know my face was bright red as he beheld the front pouched, white and red pairs before him. In my head, I knew it would be an 8 on the embarrassment scale if he made me wear them in front of him, but I knew there was worse tucked away in the closet behind me, so I told myself, IT COULD BE WORSE.
Famous last words.
"Nah. Maybe another time." He took the red pair and went over to his backpack pack, stuffing them in one of the pockets.
I opened my mouth to object, but what could I say. I couldn't claim these gay-ass underwear as mine. I certainly couldn't let this stud friend of mine know that I wanted them. So I said nothing.
"First step." Jared said, "Purging. All part of the dare. And the process."
"What process?"
"You getting comfortable being sexy. We're about to unleash what's inside of you."
For some reason this little voice inside me said I liked that idea. Getting girls (and maybe boys) because I was sexy. I could be that? Hell yes, sign me up.
He pointed to the pile of clean, some brand new underwear on the floor.
"Oh yeah, sorry" I said -- why did I just apologize? Whatever. I gathered all the underwear off the floor. A big heap in my arms.
Jared came up to me and grabbed my shoulders, rubbing them gently. "Alright dude. Time to show me that commitment." He pointed at my trash bin. Oh shit. All of these? I briefly looked down to see quite a lot of my go-to pairs in there. The ones he had removed from my dresser. But Jared was my friend and a nice guy. I'm sure he left me plenty of other pairs.
Jared came up behind me as I stood over the bin. He breathed with me, rubbing my shoulders and giving me encouraging pats on my ass. I took a deep breath and dropped a few, still more in my arms.
Jared replied, whispering next to my ear, "That's it buddy. You don't need those since we are friends now." He paused, then whispered, "I dare you to let go."
Jared backed off and surveyed me as I talked myself into it. Somehow everything he just said made sense to me, and I could not tell you why. All I needed was him to dare me and I knew I would do it.
Another deep breath and I bent over stuffing the bin full with the remaining shorts. Jared stared at me, or maybe my ass as I finished stuffing them down so they'd all fit. "High fives, dude" Jared said and we jumped to double high five -- making me feel like I had achieved greatness in his mind. Trying not to think about how few pairs of underwear I'd have to get through a week. But surely he'd left a bunch in my dresser.
"Yes!" I called out. And Jared turned me a little so he could slap my ass hard.
"Yeah dude. 1st step done! You are rocking it."
I felt like a millionaire getting praise from him. My only friend and a fucking stud. My cock twitched in my jeans and I felt a big glob of precum spreading in my trucks, making me wet again. Fuck! So embarrassing if Jared sees it.
Jared sat back down on my bed, his chest glistening with a bit of sweat. He sighed, then said, "Next step -- Trust. If you can't trust your bro, who can you?"
"Yeah. I trust you, Jared." I said, stumbling for his approval.
"I don't know. Did you bring me all of them?"
"Ugh..." Not knowing what to do and afraid to disappoint him.
"Don't make me ask again. And don't lie to me. Ever."
Fuck. I nodded at him and he joined in, nodding also. Then he looked at me like "well?" I turned and headed back into the closet. I reached up and grabbed the two things I'd hidden before. Holding the speedo in one hand and the jock strap in another, I shamefully, but obediently headed out of the closet to give them to Jared.
"Dudes don't lie to each other." Jared said, shaming me as I came out of the closet believing I was holding the two most embarrassing things anyone could have.
"I'm sorry. You're a friend just trying to help me -- I shouldn't lie to you." Jared brushed it off and looked at them in my hands like prizes in a game show. His eyes flashed with a look that scared me a little, then it went away.
"I didn't know you were a swimmer." He said, shifting my discomfort. "That explains why you have such great glutes."
"Thanks." I said grinning, feeling a little bit better or maybe just distracted from my situation. I spread my arms apart so he could see each of them.
Jared surveyed them for a minute then pointed saying, "Wear those. And put the others in my backpack."
To be continued