Jacob and Craig were saggers. They wore their jeans as loose as they could get away with and let them ride very low on their hips. This meant that much of the time, their underwear was showing above their jeans.
This was not uncommon at Ocean High School. Lots of guys liked dressing this way, so Jacob (his friends called him Jake) and Craig fit right in. Most of the guys at the school didn’t really give sagging too much thought. They grabbed whatever underwear was sitting on top in their underwear drawer and that’s what they showed for the rest of the day.
What Jacob and Craig didn’t know about each other, even though they had been friends since grade school, was that each boy really put a lot of thought into how their underwear showed, and what kind of underwear they wore. Both wore very traditional, full-cut boxer shorts, typically stripes or plaid, which is mostly what was sold in the local department stores. They wore certain colors under jeans, others under khakis or cargo pants. So while they wanted to look like their fashions were careless and even sloppy, their clothes were carefully chosen and arranged to get just the effect they wanted.
They even practiced sagging in the privacy of their own bedrooms. They would stand in front of their full-length mirrors and pull their jeans down, then up, examine how their loose boxers billowed over the tops of their pants, then try it a different way. They’d bend over in front of the mirror to see how much of their boxers showed in back. (Jacob even had several T-shirts that were too short to reach all the way down to his jeans waistband, so he knew that at least a little of his underwear was showing at all times.) When sitting in class, their jeans wrapped almost completely under their butts, exposing 6, 8, or 10 inches of their boxers. They and the other saggers at school thought this was really cool.
But there was more -- one more little twist that would lead to an encounter that neither boy could have imagined.
While Jacob had no idea that Craig paid the same amount of attention to underwear that he did, he had often admired Craig’s sagging. He admired Craig in general because he was a cool, good-looking and popular boy. He often found himself emulating what Craig did.
One day, Craig, Jake, and several other guys went to the beach. Nearly all of them were showing their underwear waistbands over their shorts. Craig was wearing some nylon board shorts that he’d had for over a year. They fit well, but were too small for serious sagging. But what caught Jacob’s eye was Craig’s boxers. They had a regular pattern of small, red and gold diamonds on a white background. He had never seen Craig wearing patterns before. To Jacob, something about these shorts made them the sexiest boxers he’d ever seen. They demanded to be looked at. Jacob knew he had to get some like these.
Later that week, Jacob was getting frustrated as hell. All through the mall, all he could find were stripes, plaids, and boxers with logo waistbands, which he really didn’t like at all. Finally, at a big discount store, he found what he was looking for. They were white with a blue and black pattern of alternating small squares and larger diamonds. He felt a stirring in his crotch as he picked up the package. The other shorts in the package were nothing special, so he rummaged through all the packages in his size (actually a size too big – he liked them baggy) and struck pay dirt. Three patterned boxers in one package. There were the blue and black ones, the same pattern in red and black, and a pair with small fancy round dots.
By now, his cock was fully hard and straining against his jeans. Fortunately for him, his jeans hung so low that the result was just a gentle bulge behind his fly, so the chances of anyone noticing it were small. Still, he was blushing bright red when he went through the checkout stand. He couldn’t wait to get home with his new patterned shorts.
That night, he spent nearly an hour in his room trying on each pair of shorts with just about every pair of pants he owned. He wanted to figure just the best way to show off his new boxers. His cock didn’t go soft the whole time.
By the end of an hour with a non-stop hard-on, Jacob was more than ready to jack off. His cock had already dripped pre-cum into the shorts he was wearing. That kind of worried him, though. He used to have some plain white boxers that he accidentally came in while looking at porn on the Internet. He was horrified to see that there was a stain on the fabric even after they were washed, and immediately threw them away. He definitely didn’t want to stain his new best boxers.
Still, looking at his patterns turned him on so much, he didn’t want to stop. So he kept adjusting his clothes in front of the mirror. He pulled his jeans down and back up again, watching how the stiff fabric puffed out over the waistband of his favorite jeans. Thinking about how Craig would react when he saw these shorts, he pulled up on his boxers waistband until they were almost all the way to his navel. This caused the fabric to rub against his cock. At that same moment, the vision of Craig showing his cool patterns at the beach popped into his head.
Suddenly the need to cum became overwhelming. ‘Not in my patterns,’ Jacob thought to himself. He moved quickly to his nightstand and pulled out a handful of Kleenex, then frantically unzipped and tried to work his dripping cock out of his jeans and boxers. He could feel his cum rising, and held back as hard as he could. Finally he got his cock free, and it instantly spewed a huge shot of semen that arched completely over the waiting wad of tissue and onto his bed. He managed to catch the rest of his copious load, and was just amazed at how much cum his balls were ejecting. When it was finally over, he couldn’t help giggling at his complete release without even jacking off!
Jacob decided to save his patterned boxers for special days when showing off really cool boxers would be the most important.
That day came two weeks later. Jake, Craig, and his buddy Jim had agreed to meet at the mall to hang out. Jacob wore his favorite sagger jeans, short T-shirt, and the red and black patterned shorts. Modeling his outfit in the mirror, Jacob felt his cock stiffening once more. He hadn’t worn any of these shorts since buying them and giving them their first washing. He was surprised at how soft they felt when he first put them on. Now the soft fabric was rubbing his boner with every movement. He hoped it didn’t stay like that all day.
By the time he finished the short bike ride to the mall, his cock was soft enough that he didn’t have to worry about it. He saw Craig sitting on a concrete bench near the entrance. Jacob’s heart skipped a beat when he saw that Craig’s jeans were halfway down his ass, and a whole bunch of his boxers were showing. They were patterned!
Jacob locked up his bike, making sure to bend over a lot so his jeans would fall and his boxers would ride up. In a well-practiced move as he stood up, he pulled up his jeans just enough to make his boxers billow out so his T-shirt would rest on top of them.
As he approached Craig, Craig turned and saw him – and his boxers. Craig’s face just lit up.
"Hey Jake, wassup?" Craig said.
"Na’ much," Jacob responded, grinning broadly. "Where’s Jim?"
"Aw, Jim couldn’t come after all. He had to go visit his relatives," Craig said.
"Too bad," Jacob said, even though he didn’t mean it. He really just wanted to spend time with Craig, with both of them sagging and showing off their patterned boxers.
What Jacob didn’t know was that Craig felt the same way about patterned boxers. He bought his first pair almost a year earlier after he saw Jim wearing some. Unlike Jacob, though, Craig had no problem with shooting off inside his new boxers. Ever since the first time he tried them on, he’d regularly soak certain pairs of his patterned boxers with hot juice while picturing Jim showing his shorts. It was weeks before he could show his patterns in public – every time he caught a glimpse of himself in a window or mirror, or if he saw someone checking out his sag, he’d pop a rod.
Now the boys were standing outside the mall entrance making small talk. They hardly ever made eye contact, but each would check out the other’s boxers whenever they had the chance. They adjusted their pants a lot. As they stood and fidgeted, their pants would drop down, down, down. Then they’d lift them up a little, causing their boxers to ride up more and more. To show as much of his pattern as he could, Craig would casually run his hand up under his T-shirt and over his stomach. Jacob didn’t have to do this because of his short shirt. They were displaying their patterned boxers for all to see, but mostly for each other.
Finally, they went into the mall. At one point, Jacob found himself behind Craig on an escalator. The back of Craig’s T-shirt was caught on his boxers, so Jacob was able to study the pattern close up. There were rows of small medallion shapes in blue and gold with black outlines. Jacob once again felt his cock stirring. He shoved his hands in his pockets.
After hanging around the mall for half an hour or so, Craig suggested they just go back to his place and maybe play video games. Jacob eagerly agreed.
When they got into the house, Craig told Jacob to go up to his room while he got them some Cokes to drink. When Jacob got there, he desperately wanted to peek inside Craig’s underwear drawer, but he didn’t know which drawer it was, and he definitely didn’t want to get caught trying to find it. So he just pulled his jeans down so they were halfway down his ass and sat on the edge of the bed and waited.
Craig came in with the drinks and handed one to Jacob.
"Hey man, I gotta tell you," Craig said, "those are really cool boxers."
Jacob could scarcely believe he was hearing this. "Thanks," he managed to say. "Yours are really cool, too."
Then Craig took the next step. "Yeah, I really like patterns like this. What about you?"
"Yeah, they’re totally hot," Jacob said, his heart pounding and his cock growing.
Craig set his drink down and lifted the bottom of his T-shirt. With his other hand he adjusted the waistband of his boxers. "It’s like, they’re so cool for showing off when you’re sagging and everything."
"Definitely," Jacob said, mesmerized by Craig’s display. He thought for a moment he saw a bulge in Craig’s jeans, but he couldn’t be sure.
"I gotta get some short T-shirts like yours though. That’s such a hot way to sag," Craig said.
Now Jacob stood up to show off. "Yeah, it’s really hot if you wear boxers that are too big for you, cuz they hang all out the sides and stuff." He demonstrated by lifting his jeans. So much of his boxers were sticking out of his pants that the fabric actually fell over the top of his jeans waistband.
"Oh man, that’s so hot!" Craig said. Both boys were now fully hard, but they were so interested in each other’s shorts that they barely noticed the bulges.
Jacob pulled his jeans down so that the belt was now resting on his cock stem. He slid his hand over his belly, lifting his T-shirt. There were at least 8 inches of patterned boxers showing. "Can you imagine walking around school and shit like this?" he asked.
"Fuckin’ hot!" Craig said. "That’d be so hot, man. So how many patterns you got?"
"I dunno, five or six," Jacob lied.
"I got a bunch," Craig said. "You wanna see ‘em?"
Jacob thought he’d died and gone to heaven. Maintaining his composure, though, he just said, "Sure."
Craig went over to his dresser and pulled out the bottom drawer. Jacob thought this was odd – the bottom drawer was the deepest, largest one. How many boxers could Craig have?
That question was answered quickly – a lot. The drawer was completely filled, mostly with the normal plaid and stripes. But Craig reached over to one side and pulled out a whole stack that were nothing but patterns.
Jacob’s eye’s widened. "Cooool."
"Yeah, and you should see Jim’s boxers. His are totally the best patterns," Craig said enthusiastically.
"Jim likes patterns, too?" Jacob asked.
"Oh fuck yeah," Craig said. "He doesn’t sag as much as you do, and he wears long T-shirts, so you don’t get to see them, but that’s about all he wears."
This may or may not have been true. Craig had only glimpsed Jim’s shorts a few times. He’d only seen Jim’s patterns twice, but over the last year, they became the seed for a whole series of obsessive fantasies that Craig had invented for Jim and his patterned boxers.
Jacob’s cock bulge was now impossible to ignore. Craig wanted to call attention to it but wasn’t quite sure how to do it. His own cock was like an iron pipe in his pants, its poking blunt end making a tent in his loose jeans.
"Um… do you get, like, turned on by these patterns?" Craig asked quietly.
"Uh, a little, I guess," Jacob responded, clearly embarrassed but realizing he couldn’t deny that he had a stiff cock.
"Yeah, me too," Craig said. Jacob now took his eyes off Craig’s underwear and checked out the bulge in his jeans. Jacob felt relieved and excited at the same time.
"You should see how turned on Jim gets," Craig said. "I saw him cream his boxers once."
This was a complete fabrication, but Jacob had no way of knowing that. His eyes flew open. "No shit?" he asked incredulously.
"Yeah, we were out in the yard and we both had our shirts off and I was wearing these boxers here," he said, picking up a pair with small red and blue octagon designs, "and he was wearing these blue patterns, and he goes, ‘These patterned boxers really get me hot." And I go, ‘What do you mean?’ And he goes, ’It’s like they’re so cool, they make me all hard.’ So I go, "Yeah, me too.’ Jim goes, "No way.’ So I pulled my boxers up real high, and I’m totally showing like 10 inches of boxers, and I go, "Yeah, these are way cool.’"
Jacob glanced back down at the octagon patterned shorts as he imagined his friend showing them off that much.
Seeing that Jacob was believing every word, Craig continued to describe his favorite erotic daydream. "Then Jim’s all, ‘That’s so fuckin’ hot. Oh fuck, I can’t hold it!’ I go, ‘What do you mean?’ and he’s all, ‘Uh! Uh! I’m shooting in my patterns!’"
"Wow," Jacob breathed.
Craig was really getting into sharing his jack-off fantasy. His cock was dripping big globs of juice into his medallion patterned boxers. "And he’s not even touching it! There’s this wet spot going all down his leg cuz his cream was soaking right through his boxers."
Jacob’s poor cock was about to burst. The head, sliding against the soft, patterned material, was angry, shiny red. The shaft was straining to break free of his jeans.
"So, um, have you ever shot off in your patterned boxers?" Jacob asked in a shaky voice. Even though he was afraid that the answer might just send him over the edge, he had to know.
"Oh man, I try not to, you know?" Craig lied again. "Like, I haven’t creamed the ones I got on now cuz they’re brand new. But some of these patterns are so hot, it’s like I can’t help it when I wear them. These ones here…?" He reached down and picked up a pair with bold, red and blue diamonds. "I can’t wear these without shooting off. They’re totally my favorite patterns."
"Don’t they get, like, stains on them?" Jacob asked, his voice quavering with excitement.
"Yeah," Craig admitted. He spread the diamond patterned shorts on the bed. Sure enough, there was a slight discoloration alongside the fly. "There’s something hot about showing off my cum-stained boxers, though," he said.
Jacob felt faint. There were Craig’s hot patterned boxers and you could see right where he had been shooting his sperm into them. And he sagged in them, too!
"Um… Did you ever do it?" Craig asked.
"No," Jacob said. "I’m afraid to get my best boxers all stained up. My mom might see."
Craig was disappointed with Jake’s answer, but he was intrigued by one thing. "Your best boxers, huh?"
"Yeah, I mean, it’s like, you know, these boxers are so cool, but maybe it would be kinda hot to sag with cum stains on the front."
Both boys were more aroused than they’d ever been. Their breathing was fast and shallow. Their cheeks were flushed, their ears bright red. Their cocks throbbed mercilessly inside their patterned boxers.
"Show me your patterns like you did before," Craig said.
Obediently, Jacob pulled his jeans down low on his hips and lifted his T-shirt.
"Ohh, your patterns are sooo hot," Craig said, taking in every detail of the pattern and how the boxers billowed out over Jake’s jeans.
Jacob didn’t know how much more of this he could take, but he still managed to ask, "Why don’t you do it, too?"
Craig quickly pulled his jeans down to his cock stem and lifted his shirt, too. For several minutes the two boys stood there, displaying their favorite patterned shorts to each other. They both kept continuously adjusting their shorts and jeans using their well-practiced, mirror-honed techniques, but this time they knew it was really turning on another sagger. Jacob even turned around and bent over like he did in front of the mirror. When he stood up, Craig did the same. The only sound in the room was the rustling of clothes and the boys’ heavy breathing.
"I don’t think I’m gonna be able to hold it much longer," Jacob croaked as he watched Craig pull the billowing fabric of his boxers out over his pants.
"Oh man, you don’t want to mess up your good patterned shorts," Craig urged, even as he pulled up on his boxers waistband.
"Unh, it’s so hot," Jacob murmured. "We’re both showing off our best boxers… and I got cool patterns just like you. I can’t believe you’re getting totally hot watching me show off my patterns." With pre-orgasmic contractions shaking his body, Jacob began fingering his waistband and used both hands to pull his boxers up as high as he could. The soft fabric slid even more on his tender, aching teen boner as he displayed what seemed like yards of patterns.
"Oh shit, you shouldn’t have done that. I don’t know how long I can hold it looking at your cool patterns show like that," Craig said.
Suddenly Jacob’s face scrunched into a look of intense pleasure/pain. "Oh shit, it’s coming out! I’m creaming my best patterns!"
"Hold it back, dude!" Craig urged.
"Mmph! Can’t!" Jacob grunted. He hung onto a nearby chair for support as he stood in front of his friend, helplessly ejaculating into his boxers and jeans. Even as spurt after spurt of hot cum filled his shorts, Jacob’s eyes darted between the medallion patterned boxers his friend was displaying, and the cum stained diamond patterns still laying on the bed.
Craig was really turned on by showing off his boxers while Jacob was cumming inside his.. He pulled his jeans down some more. Then some more. With his jeans all buttoned, zipped and belted, Craig pulled them down until his throbbing boner sprang over his jeans and into the freedom of his baggy boxers.
"UNH!" Jacob yelled when he saw this, his whole body racked with a huge spasm.
"Fuck man, your jeans are getting all wet, just like Jim’s," Craig said. Jim’s climax was pure fiction, but here it was happening to Jake right in front of his eyes. It was too much. Craig’s untouched cock began releasing a hot flow of semen into his own boxers.
"You’re makin’ me do it, Jake. I’m creaming in my boxers, too," Craig said. Jacob already knew. He saw the wet stain spreading. Even more cream spurted into Jacob’s saturated shorts.
Craig was able to maintain his composure better than Jacob. He described his ejaculation for his friend’s benefit. "I can’t stop it either. It’s all coming out… right in my boxers. Fuck! I’m getting stains on my new patterns."
It was worse than that. With his cock head poking right into the thin fabric of his boxers, globs of white semen were bubbling through and dripping over his belt and down the front of his jeans.
Even though his balls were nearly drained, Jacob’s orgasm continued as Craig stood there sperming his cool shorts and talking about his patterns. Finally, there was nothing left. The tension left Jacob’s body, and he sat down heavily on the bed.
Craig couldn’t help reaching down and milking the last few squirts of sperm into his boxers. Four strokes, with his hand making squishy wet noises over his drenched boxers, and it was over for him, too.
Jacob looked up at him with a wan smile. Craig smiled back.
"What do you say we go shopping for boxers when your pants dry?" Craig asked.
Jacob simply replied, "Cool."
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