By: MrCreamJeans
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.
"No, why?"
"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.