Jon arrived home from his friend Kenny's house and realized that he was getting quite a collection of other guys' boxers. He had Rod's shorts, which Rod had just royally creamed during their no-hands jack-off contest. And he also had two pair of Kenny's - one that Kenny gave him after he wet his pants with cum while they were walking home, plus the ones he was wearing, which he was given after the one-on-one contest with Rod.
Jon had long had a "thing" for boxers. During the summer, he was always walking around shirtless with several inches of boxers showing above the waistband of his pants or shorts. He loved seeing other guys dressed the same. He liked looking at what kind of shorts the other guys wore: the prints, the brand names, the fabric, and everything about them. And what he told Kenny was true, he did jack off thinking of girls, but he also jacked off thinking of his buddies in their boxers, especially the ones in the J.O.C.K. club.
Now in the privacy of his room, Jon pulled his shirt off and stood in front of the mirror. He carefully arranged the underwear so it showed over his jeans, and felt himself getting hard as he imagined Kenny in this outfit. The jeans were a little tighter than the ones he usually wore, so his cock couldn't poke straight out. Instead, it crawled down his thigh. As it became fully hard it looked like a thick pipe under the worn denim. Jon reached down and gave it a squeeze. The tightness of the jeans felt good, and even though he'd had a massive orgasm less than an hour ago, he was horny again, and his cock wanted to squirt, and Jon contemplated jacking off inside Kenny's boxers.
Then he had an idea. Quickly he stripped down and put on Kenny's faded and well-worn shorts first - the ones he picked up on Tuesday. They were the softest, and they were so old that Jon was certain Kenny had shot off in them before. Then he pulled Rod's shorts, still damp from his previous ejaculation, over them. Finally, he put on the boxers Kenny gave him today. He arranged the waistbands so all three shorts were showing. His cock was throbbing like crazy at the thought of what he was about to do. Now he squeezed back into his jeans, which were much tighter with the three layers of shorts underneath them, so tight, in fact, that he couldn't button the top button.
Jon looked at his reflection in the mirror. He was wearing all these other guys' boxers! And they were all showing! And he had a big boner in them, right where the other guys got their boners! And he was wearing two pairs of Kenny's, the same guy he'd just jerked off!
Jon's head was swimming with all these thoughts. His hand covered the straining lump of his hard-on and began rubbing. As he expected, Kenny's worn shorts felt very soft and smooth against his tender prick. He could also feel a little of the cold wetness in Rod's boxers. The room reeked of cum.
Jon's eyes were riveted on the reflection of his waist where three pairs of boxers showed above his pants. The first ones were his favorites - Kenny had worn them the most, they had the coolest pattern, and they were the ones his dick was now rubbing against and getting wet with pre-cum. With his free hand he fingered the three elastic waistbands, re-arranging them to show even more. The crotch seam of the inside pair pressed into his balls. Far from being uncomfortable, it just heightened the erotic feelings.
Incredibly, he was just moments away from another orgasm. His hand was rubbing frantically over the bulge that pointed down his thigh. If he rubbed any harder he'd have to worry more about the fabric giving way than any stains he might leave. But he didn't have to worry about that. His balls were ready to eject another load.
"Gonna cream them," Jon mumbled. "Gonna cream where they cream, cream right in their boxers. Awwwwwwwwwwwwwww!"
Hot wetness shot down his leg. His cock pushed angrily at the confining layers of cloth as it splattered hot cum all over Kenny's old boxers. Despite his earlier orgasm, there was so much cum that it began soaking through all three boxers, making a small wet spot on the denim. He couldn't help rubbing his spurting cock even more, milking the last of his load through the cloth. A couple of last squirts and it was over.
Jon stood up straight and examined the damage in the mirror. His boner had softened only slightly, so it still made an obvious bulge. There was about a two inch wet spot showing through at the end, and a little of the creamy white stuff had even come through the denim. Jon couldn't help giggling. He'd just jacked off in these other guys' underpants, and it felt great. He knew he'd be doing more of it, but for now it was time to throw Kenny's shorts in the wash so Kenny wouldn't know. Rod's, however, he'd leave cum-stained for future enjoyment!
On Monday Jon saw Kenny walking to class. He glanced at Kenny's pants and saw an unmistakable bulge there. Kenny was walking around with a boner for all to see! Jon's own cock tingled as he caught up with his friend.
"Du-u-u-ude," Jon chortled, looking straight at Kenny's jeans. "What's up?"
"Ha-ha," Kenny replied sarcastically. "Shit! I don't know what I'm going to do until tomorrow, man. It's been like this all day."
"Now you know what I went through last week," Jon said.
"Hey listen, I had an idea. You still got Rod's boxers?" Kenny asked.
"Yeah, of course I do."
"Cool. I think I want to borrow those for tomorrow," Kenny said with a diabolical smirk.
Jon laughed out loud. "Oh, man! I can just see Rod's face when he realizes your jacking off in his shorts!"
"I'm not going to jack off inside them," Kenny explained. "I'm gonna wear some really soft pants and do it with my dick sticking out the fly."
"Of your pants?" Jon cried.
"No, dummy, I mean out the fly of the boxers. Kinda like freeballing, but Rod will think I creamed inside his shorts."
Jon laughed out loud. "That's great! Yeah, come by my house after school and I'll let you have them."
"Hold on. When you took them home Rod had creamed in them. Have you washed them?" Kenny asked.
"Dude, I'm not gonna put on his shorts after he's worn them… especially after he shot off in them."
Jon blushed. "Uh, yeah, sure, of course not."
"So, any chance you could wash them when you get home from school?" Kenny asked.
"Uh, yeah, I can get them washed. No one will be home until five or six anyway. Gives me plenty of time," Jon replied.
"That's great, man," Kenny said. "I'll meet you after last period."
After school he met up with Jon, and they headed to his house.
The two immediately went up to Jon's bedroom. "Here are Rod's boxers," Jon said as he stuck them out at Kenny.
"Great," Kenny smirked as he took them. Then, as he noticed Jon was just standing there, he said, "What about the two pair of mine that I lent you. Can I get those back?"
"Oh, yeah, right," Jon said as he went over to retrieve Kenny's boxer shorts. He'd been hoping Kenny would forget he had them, at least for a while longer.
"Dude, you better not have creamed in my boxers," Kenny said after Jon handed them over and he immediately started to examine them. He saw the look on Jon's face and knew that he had. "D-u-u-u-u-d-e, both pairs?"
"I'm sorry," Jon said sheepishly as he looked at the floor, and then he looked up with a sly smile and said, "But you really should have figured it would happen when you lent them to me. You know I can't help myself."
"Yeah, I probably should've known," Kenny chuckled.
"But don't worry, I washed them," Jon assured.
"Well that's good news. But if I ever lend you another pair, no more cumming in my boxers, ok?"
"Ok," Jon said meekly and then perked up. "Hey, tomorrow's the big day. You finally get to cum!"
"Tell me about it, I can't wait!"
A few minutes later he was on his way home.
On Tuesday morning Kenny pulled on Rod's boxers and his softest pair of khakis. They were a little dressier than he liked, so he usually didn't wear them to school, but they were the softest pants he had, and he also figured they'd show a good wet spot. He then put on an oversized t-shirt. He knew he was going to make quite a stain with his dick outside of the boxers, and he didn't want to have to rely on his books to hide it. The t-shirt went down well below his crotch, solving that problem.
Kenny's boner didn't go down all through first period. As he walked to his second class he moved his books and quickly glanced down to see how obvious things were down there. Even with his loose oversized t-shirt he could tell there was a pole poking straight out from his crotch. When he got to class he sat down quickly. Jon walked into class, looked at Kenny and gave him a thumbs-up sign to encourage him.
With about fifteen minutes to go in the class, Kenny stealthily reached into his pants pocket to begin masturbating, looking forward to a release he had denied himself for days. To his horror, he suddenly realized that this was not going to work! The outside seam of the pants pocket was sewn to the leg seam. He couldn't reach his cock!
Jon noticed the seemingly frantic activity in Kenny's lap as Kenny tried to find a way to reach his boner under the cover of his khakis. Jon couldn't quite figure out what was going on, but assumed that Kenny was really going for it so he could win the contest. He began his own concealed stroking, shifting his attention back and forth between the teacher and his jack-off buddy in the next row.
Kenny had managed to get his cock through the fly of Rod's boxers, and he even got it to bend over enough to allow him to wrap his pocket-covered fist over the head. But he really doubted he could get off like that. Finally, with only about five minutes to go, he thought about Rod's technique for a hands-free orgasm. He pulled his hand out of his pocket, sat up a little and crossed his legs like he'd seen Rod do. His cock was immediately enveloped in a fold of the soft khaki material. He began moving his hips as subtly as he could.
Jon was amazed to see this. He had figured out that Kenny was trying Rod's technique but couldn't understand why, especially since Kenny had told him that he was never able to cum without stroking it. But Jon had his own ejaculation to worry about. He quietly jiggled his boner, ready at any time to squirt some juice into his shorts - just enough to make a spot that would keep him from having to do it in front of all the guys.
Kenny was getting worried. His hip-thrusting against the khakis felt good, but the fabric was kind of thin and didn't provide any pressure on his cock. He didn't think it would be enough to make him shoot his load. Once again he shoved his hand in his pocket in an effort to give his cock some additional stimulation. He found that he could pull the fabric of his pants and make it slide against his throbbing hard-on. He put his other hand in his other pocket and began a tug of war, making the cloth slide back and forth. This he thought might work. But it was too late. The bell rang signaling the end of class. The students all stood up and quickly made their way out of the room.
Jon walked over to the still-seated Kenny. "Dude, what happened?" he asked, seeing Kenny's crotch was totally dry.
Kenny was desperately pulling his pants around and staring at the small cum stain on Jon's jeans. It wasn't going to work. He sighed and the tension left his body. "Let's go," was all he said.
As the boys walked to the meeting Kenny explained about the pocket seam.
"But if you show up at the meeting without a cum spot they're gonna make you jack off right there," Jon reminded him.
"Yeah, I know," Kenny replied. "But I gotta get rid of this load anyway. Damn!"
They turned the corner to the least-traveled section of the school where the J.O.C.K. members met. Rod had not yet arrived, but the rest of the guys were comparing their wet spots.
One of the guys looked up and called out to Kenny, "Hey Kenny, you gonna win this week?" Then he looked down at where Kenny's t-shirt covered his crotch. "Hey, Kenny's got a boner!" he shouted.
"Oooh..." several guys intoned, and then somebody called out, "C'mon Kenny, lift up your shirt."
Kenny lifted the bottom of his shirt up over his stomach. There were his almost dry pants (with just a tiny pre-cum spot), his big hard-on… and Rod's boxers sticking up a couple of inches.
It was at that moment that Rod came walking around the corner, books over his crotch. He stopped in his tracks. He realized that Kenny hadn't cum in class, but was about to… in his boxers!
Without another sound the group closed in a circle around Kenny. "Come on, dude," someone said solemnly, "You gotta cream 'em."
Kenny was glad that Rod had seen he was wearing his boxers. Even though his cock was still sticking out the fly of the shorts, he knew that Rod couldn't know that. Now Rod was standing right in front of him and had to watch as he jerked off through his pants. Standing inside the protective circle of cum stained guys, Kenny wrapped his hand around his bulge and began stroking.
After the rough time he'd had in the classroom, and the days of abstinence, Kenny's soft khakis felt wickedly good against his tender cock shaft. In less than a minute of stroking he was ready to let go, but he wanted to give the guys, and especially Rod, a good show.
"Go for it, Kenny!" he heard one guy say.
Other guys in the group quietly called out similar encouragement:
"Cream your pants, man!"
"Let it out!"
Kenny felt the cum working its way into his cock shaft. He kept stroking. He looked at Rod, who was staring intently at his jack off session. But Kenny was amazed to see that Rod's free hand was buried behind his books, and it was clear he was rubbing his cock as he watched. Rod was obviously turned on by the fact that Kenny was about to cream in his shorts. Kenny looked around and saw several of the guys were surreptitiously rubbing their cocks through their pants, too.
Kenny decided to give them a real show. He was bent over a little at the waist as he gave his ready-to-spurt cock the few additional strokes that would take it over the edge. As he felt the cream rise he suddenly released his throbbing cock, stood straight up and pulled his t-shirt up over his chest, exposing his crotch, his tight stomach and, of course, several inches of Rod's boxers. Staring straight at Rod he stood stoically as his untouched prick began ejaculating in his pants. Since it wasn't restrained by any underwear the wet spot appeared immediately.
"Check it out!"
"Cool!" the guys in the group murmured.
Everyone could see each time Kenny's cock throbbed, and each time it did the wet spot grew bigger and shinier. What was amazing was how many times it jumped, each one representing another spurt of creamy juice in his khaki pants. Throughout his orgasm Kenny did his best to maintain his calm facial expression and to control his breathing as he watched Rod watching him cream.
It was Rod's face that betrayed excitement. With his hand extremely busy under his books, Rod suddenly got this pained look. Could he be cumming in his pants a second time? Or did he miss creaming in class and this was his first?
Kenny's cock began softening even before all the jizz was drained from his balls. Cum continued to dribble out as he looked down to inspect the damage.
"Oh shit!" he said quietly.
The group all laughed and broke the circle, exposing Kenny to view. The stain was like an elongated ice cream cone, with a bulbous top alongside his fly tapering to a point a few inches above his knee. Even his long t-shirt wasn't going to hide this! The other guys were pointing and laughing at the embarrassing wet patch.
Jon had watched all this, feeling sorry in a way for his cool buddy. But he knew that Rod had been watching and thought his boxers just got royally creamed, so it was worth it.
Since Jon was last week's winner (thanks to Kenny's classroom display), he called the meeting to order. "Ok, who's the winner this week?"
"Larry's got a pretty big one," someone said.
Attention turned to Larry who must have had a great orgasm in his last class.
"Anyone else?" Jon asked. "What about you, Rod?"
Reluctantly, Rod pulled his books away. The wet spot alongside his fly appeared to be the same size as Larry's. But there was something else - another set of wet spots. They were below the first, and consisted of several blobs and a couple of streamers going down the front of his thigh, all shinier than the big stain. It was obvious they had just been made in the last couple of minutes.
"He creamed his pants watching Kenny!" Larry called out.
Now, all hell broke loose. There began a raucous debate on whether Rod's jack-off session at the meeting disqualified him from possibly winning. One group thought that since he creamed in class it didn't matter what happened afterwards. But several guys viewed jerking off at the club meeting as something only losers did. As president for the week it became Jon's call. He was ready.
"I'm willing to ignore the second jack-off," Jon said solemnly, causing several guys to groan. "But his class stain and Larry's are about the same." With a smug expression he continued, "So I think it comes down to whether either of them was freeballing."
Everyone knew that Rod often didn't wear underwear so he could have the biggest stain. So everyone began clamoring to see whether the two contenders were wearing underwear.
Kenny wasn't at all sure about this strategy. He was sure Rod was wearing his boxers, and now the rest of the guys were about to see the same pair of underwear three weeks in a row. Somebody was going to notice! What Kenny didn't know was that Jon was counting on it.
Larry pulled his shirt out of his pants and revealed the waistband of his white briefs. Rod slowly lifted his shirt to reveal Kenny's shorts.
Sure enough, someone noticed. "Hey! Those are the same boxers Jon wore last week!" someone shouted.
"No, those are Kenny's shorts," someone else said.
All eyes turned to Kenny and Jon.
Jon grinned at Kenny and turned toward the group. "No way," he claimed. "Check it out." And with that he pulled his own shirt up, revealing... Kenny's boxers? Jon's boxers had the exact same print as the ones he creamed in last week!
For a moment Kenny was speechless. Recovering quickly, he stammered, "I, uh, my shorts like that are at home."
Rod didn't know what to think. He didn't want to tell the guys that he'd borrowed Kenny's boxers to wear for the contest, and now Jon and Kenny were bailing him out. He jumped on the bandwagon.
"Yeah... these are mine," he said.
There was some murmuring in the group as the guys tried to figure out the "coincidence."
Jon regained control. "Ok, since both guys are wearing underwear I think Rod should win, because he actually came twice!"
It was obvious some guys disagreed, but since Jon was presiding it was his call. No one congratulated Rod, though. Rod set the next meeting to suit his schedule, Wednesday at lunch, and the group dispersed except for Rod, Jon and Kenny.
"Uh, thanks guys," Rod said sheepishly.
There was a moment of awkward silence.
"Where'd you get those boxers, Jon?" Kenny asked.
Jon grinned broadly. "Well, I remembered what brand they were, so I went to a few stores until I found ones with the same pattern," he explained. "They're really cool," he added enthusiastically.
Smiling, Kenny just shook his head in disbelief.
"We got some real problems here," Rod said to Kenny. "What are you going to do about that stain?"
"Hmm, yeah..." Kenny said, looking down at the mess down his leg. He also looked at Rod's pants. The wet patch wasn't as long, but neither was his shirt. It was pretty obvious.
"You wanna ditch with me?" Rod asked. "We could go behind the janitor's shed for a couple of hours."
Kenny thought it over. He almost never ditched class, but he figured this was a pretty good reason. "Sure," he said. "Jon, you want to come?"
"I already did, dude," Jon said with a silly grin.
The other guys groaned.
"Nah, this'll be dry pretty soon. I'll see you guys later." And with that Jon took off toward the snack bar.
"Come on," Rod said. "I know a way where no one will see us."
Rod led Kenny through some access roads around the back of the school, and they eventually found themselves behind the shed. Although the small space was deserted, the ground was littered with cigarette butts, a sure sign that this clandestine hangout was well used. Rod sat down on the ground with his back leaning against the shed wall. Kenny joined him.
"I can't believe Jon went out and bought those boxers," Rod said. "He sure covered our asses."
"Man, I was freaking when he started talking about having you guys show if you were freeballing," Kenny said. "I pretty much knew you were wearing my shorts, and I figured somebody was going to notice."
"Well, Jon was right about one thing," Rod said, lifting his shirt again. "They are cool boxers."
Kenny laughed. "I'm not sure I want them back now, now that you and Jon have both creamed them!"
"Hey, I'd say you did a pretty good number on mine," Rod countered.
"I guess so," Kenny said, deciding to keep up the appearance that he actually squirted through Rod's shorts.
After a short pause Rod said, "That was pretty hot the way you came today. Your face didn't even look like you were shooting. That's the sign of a real J.O.C.K. member. You can't let the teachers know what you're up to."
"It felt pretty weird," Kenny said. "I mean, it was sticking out there all hard and doing its thing and I wasn't even stroking it." He looked down at his wet pants. "I didn't think there'd be so much, though."
"What did you think about having to jerk off in front of the guys?" Rod asked somewhat tentatively.
"Oh, it was ok I guess. I've been jacking off in class for a few weeks, usually with Jon watching me, so it wasn't so bad. But I guess you really got off on me doing it in your boxers like that," Kenny grinned.
Rod had a funny look in his eyes. His gaze shifted quickly between Kenny's eyes and his lips. Kenny stopped grinning. Rod mumbled, "It was totally hot." Then he leaned over and planted his lips firmly on Kenny's!
Kenny was so shocked, it took him a few seconds to react. He started to pull away, but the larger boy held his head and continued kissing him. Finally Kenny managed to break free and push Rod away.
"Dude!" Kenny said loudly. "I'm not gay, man!"
Rod was immediately apologetic. "I'm sorry! I'm so sorry, man! Jeez, I fucked up. Oh fuck, I'm so sorry!"
"Ok! Ok, dude! Calm down," Kenny said, wiping his lips.
"Oh fuck! Oh fuck! Don't tell anyone ok?" Rod implored, looking like he was on the verge of tears.
"I won't tell anyone. Chill, man," Kenny reassured. After a moment, he asked, "Are you gay, dude?"
"Fuck, I don't know. I've never done anything like that before," Rod said, sounding as confused and upset as he looked.
"So why now?" Kenny asked quietly.
Rod looked into Kenny's eyes for the first time since the kiss. "You're a hot dude, Kenny," he said. "I mean you're really good looking, and you jack off in class, so I know you're horny, and then you totally creamed my boxers right in front of me, and... and..." he paused for a moment and then continued, "…you're really nice, you know? I just felt like... like... kissing you."
Kenny was almost as confused as Rod. In the last week or so he'd jerked off with his cock out in front of another guy, let that same guy jack him off the next time they were alone together in his room, he'd shot off in front of a whole group of guys while wearing another guy's underwear, and now that guy was kissing him. He was pretty sure he didn't feel "romantic" about other guys, but now these guys were coming on to him.
"Are the other guys in the J.O.C.K. club gay?" he asked Rod.
"Fuck, I don't know," Rod replied. "I mean, I've heard a couple of rumors about a couple of the guys, but nothing for sure. And that's not what the club's about, you know? It's like, well, it's just about gettin' away with shit and shooting your load and laughing about it."
"Yeah, it's pretty fun getting off in class like that. But that day Jon caught me was really the first time I'd ever done it," Kenny confessed.
"No shit? Man, I've been jacking off in class since before I could even cum. Maybe that's why I got held back - I wasn't paying attention to anything but my cock," Rod laughed.
Kenny laughed, too. Then there was an awkward silence.
Kenny finally broke it by saying, "Hey, uh, we're gonna have to get our boxers back. How do you want to do that?"
"You mean I can't keep these?" Rod asked, grinning.
"No," Kenny said. Even though he never planned to wear them again after what they had been through, Kenny figured if anyone should get to keep them it should be Jon.
"Ok, how about I come by your house on Saturday. We can trade back then. Is that cool?"
"Yeah, that'll be ok," Kenny agreed.
By this time the sun had done its work. Kenny's pants were mostly dry, although the light colored fabric showed a tell-tale track which was obvious if you looked for it. Rod's pants were also dry enough to be presentable.
Kenny looked at his watch. "Hey, we can still make fourth period."
They both got up to leave.
Rod put his hand on Kenny's shoulder. "Hey, uh, thanks for understanding."
"No problem, man."
And with that the two boys went off to resume their day at school.
TO BE CONTINUED…
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