Certified Sagger

Jake was a sagger. He liked to wear his boxers high and his jeans low. Nearly all of Jake’s friends were saggers, too. They’d hang out together at the park or the mall with their shirts off, each of them showing different amounts of boxer shorts waistbands above their baggy pants.

Sometimes they talked about sagging among themselves. They all agreed that chicks liked looking at their underwear and it was easier to start a conversation when the guy’s shorts were showing. One day, Chip said he thought the hottest girls – the ones who "put out" – seemed to go for the guys who were showing the most shorts. Even though these guys weren’t that experienced, there were nods all around, and several of them started to pull up their boxers and pull down their jeans.

Later that day, Chip’s idea got Jake thinking. One of the guys, Steve, was always showing the most boxers – sometimes the waist of his jeans hung down below his ass so about 8" of boxers would be showing. Sometimes he'd even walk around with his pants below his cock in front! Steve was also kind of a smart ass and Jake didn't really like him, but because he'd go for "extreme sagging," Steve got to talk to a lot of chicks. Jake wasn’t jealous or anything because he had a really hot girlfriend himself. But Jake knew something about Steve that the girls didn’t – Steve had a really quick trigger. He couldn’t hold his cum. (He heard this from one of Steve’s dates.) Jake was kind of pissed that Steve made this big show with his underwear but couldn’t really deliver the goods. He thought guys like Steve would give saggers a bad name.

An idea popped into his head. ‘How about some kind of test to see how long these dudes can hold their cum?’ he thought. ‘And then…and then … yeah, the guys who can hold out the longest could sag the most!’ He laughed out loud when the idea gelled into a name: "Certified Sagger."

But how would the test work? The guys couldn’t jack themselves off – they’d have too much control over how hot they were getting. And they sure couldn’t jack each other off! (No way!) Then he thought about his girlfriend, Tiffany.

Jake met her in the park when he and his sagging buddies ran into Tiffany and her friends. Jake was wearing his loudest patterned shorts and was showing several inches above his baggy jeans. He saw Tiffany looking at his shorts, and just about popped a boner when he saw her unconsciously lick her lips. In a bold move, he struck up a conversation with her, got her phone number, and even arranged a date! They’d been together now for four months.

Tiffany loved it when Jake would sag with his shirt off. She said it turned her on to see his underwear showing like that. She also loved to play with Jake’s cock. When they were alone together, she’d pull his cock out of the fly of his boxers and jeans and stroke him to orgasm while he felt her tits and pussy through her clothes. While this often resulted in splatters of cum all over Jake’s jeans and T-shirt, he didn’t really mind. He even got used to her giggling when his cock began squirting. When there were other people around, Tiffany would still try to rub his cock through his pants. Once, in a movie theater, she rubbed him so long and with such intensity that he ejaculated in his boxers. Of course, she giggled in the quiet of the theater when she felt his cock throb and the hot cum soak through the fabric. He was utterly humiliated at having to walk out of the theater with a big cum stain on the front of his khakis, and he vowed never to let her do that again.

But now Jake was thinking that if she could get him off like that, she’d be a great "tester" for his new "certification" scheme. She certainly knew how to get a guy off, and her giggle would be a perfect signal for timing the guy’s climax. The only snag would be convincing her to do it. He’d be seeing her that night, and he started thinking about how he would explain it to her.

Jake felt an unexpected pang of jealously when Tiffany enthusiastically agreed to perform the tests. "Ooo, that sounds like fun!" she exclaimed. "And I’d be doing all my friends a big service, too," she added with a mischievous twinkle in her eye. Her hand was already in Jake’s crotch, steadily rubbing his stiffening member. Testing was soon forgotten as they got down to business.

That Saturday, the guys were all at the park. Steve, as usual, was the most extreme sagger, showing diamond-patterned shorts below his ass in back and right down to his cock stem in front. Jake decided the time was right to propose his plan.

"Dudes, check this out," he said. "We know that chicks like it when we sag, right?" There were nods all around. Then Jake told a little white lie. "OK, so Tiffany had this idea: What if we could use sagging to let them know just how good we’d be in bed?"

"How would we do that?" one guy asked.

Jake grinned. He had them. "How would you guys like a free hand job from a hot chick?" Pandemonium.

"OK, OK, calm down!" Jake said, grinning from ear to ear. "The hand job is a test. To see how long you can hold it." Jake smirked when he saw Steve’s face change from joy to worry. In fact, several guys’ faces dropped a little when this was announced.

"Yeah? And then what?" Seth asked.

"The guys who hold it the longest get to sag the most, and the guys who cum the quickest only get to show a little waistband."

"Yeah, but how do the girls know what that means?" Chip asked.

"Check it out," Jake said. "Tiffany will to tell all her friends about it. And even the chicks that don’t know, well, they all like seeing lots of boxers, so it will work anyway."

"I don’t know, man…" Steve started.

Jake was ready for this. "Whatsa matter? You chicken?" he retorted. This challenge not only shut Steve up, but squelched all dissent.

"So who’s this hot chick?" Seth asked.

Once again, a pang of jealously went through Jake as he announced, "Tiffany."

"Woah!" "Awesome!" "Oh fuck!" The group of boys was clearly impressed, both with how hot the girl was going to be, and by Jake’s willingness to share her.

"OK, so here’s how it’s going to work. We all meet at my house next Saturday at noon – my parents will be gone for the day," Jake said. Then, in his firmest voice he added, "No jacking off after midnight Thursday! It’s gotta be fair to everyone." He grinned as he figured what each guy would be doing at 11:50 on Thursday night, including himself. "You’ll be alone with Tiffany in a bedroom, but no kissing her and no touching her! She’s gonna rub you through your pants for two minutes. Any guy who creams his pants only gets to show his waistband when he sags. As soon as she takes it out of your pants, you get to show another inch. For every minute you last, you get to show another inch. If you go 7 minutes total, you can show as much as you want."

"Seven minutes?" Seth snorted. "No problem!"

Jake grinned. "She’s pretty good, man. I wouldn’t be so confident."

Saturday morning, a few minutes before the guys were scheduled to arrive, Tiffany bounced up the steps to Jake’s front door. Jake saw her coming and was there to greet her.

"Hi Jake!" she bubbled as she came though the door and gave him a big hug and kiss. Jake hadn’t remembered seeing her so happy. They kissed again, and Tiffany began squirming against her boyfriend, causing his cock to harden almost instantly.

"Woah, babe! Slow down! I gotta take the test today, too." Jake said as he backed away. "You don’t want it to be over before it starts, do you?"

Tiffany gave Jake a mock pout, then smiled brightly. "So where do you want me?" she asked.

"In the spare bedroom next to the den," Jake said, guiding her to the location. When they arrived there, Tiffany once again latched onto him and began kissing and rubbing her firm body over his. Just then, the doorbell rang.

"Saved by the bell," Jake murmured as he broke away from his horny girlfriend. His cock was swollen and wagging in front of him under his loose jeans as he went to let in the first of his buddies. Within a couple minutes, they had all arrived, some already sporting half hard-ons in anticipation of what was to come.

"OK, Tiffany’s in there," he said, pointing to the spare bedroom. "I got each of your names on a piece of paper in this box and when your name gets drawn, you get to go in. You have a little while to get settled and then when I ring this bell, the time starts and so does Tiffany. Two minutes later, I ring the bell again, and Tiffany will take your cock out. She’ll signal when you pop your load." Jake knew what the signal would be – the delighted giggle she always did when he got off.

Jake drew the first name. It was confident Seth. He stood up and stripped off his T-shirt, wanting to show off his boxers to sexy Tiffany. He turned back to Jake and asked, "Is Tiffany really in there?" Jake nodded. Taking a deep breath, Seth opened the door to the bedroom and walked in. Jake heard him mutter, "Woah!" as he closed the door.

After a few moments, Jake picked up a bell from his mom’s prized glass bell collection, and gave it a little shake. Hearing nothing but some murmuring from the bedroom, two minutes later, he gave it another shake.

The wait was excruciating for all of them. Several guys tugged nervously at their hard-ons, trying to adjust them into more comfortable positions. Finally, a giggle came through the closed door. Jake clicked his stopwatch. "Four minutes, 38 seconds," he announced.

A few seconds later, Seth emerged from the bedroom, a sheepish grin on his face and wet splotches all over the front of his jeans.

"You get to show three inches of boxers," Jake said.

"Three? You said I went over four!" Seth argued.

"It’s one inch after the first two minutes, then an inch for every minute you complete after that," Jake explained. "But the three inches doesn’t include the waistband."

"Oh, OK," Seth said as he plopped, exhausted, into his chair.

"Hey, come here," Jake said. "You gotta pick the next name."

Seth got up reluctantly, suddenly self-conscious about all the spooge spots on his jeans. He quickly pulled out a piece of paper and handed it to Jake.

"Chip, you’re up," Jake announced.

When Chip stood up, it was obvious that he was fully hard in his cargo pants – they were tented out like crazy. A couple of the guys snickered as he made his way to the bedroom door. "Yeah, he's up all right!" one of them said.

When he opened the door, his reaction was similar to Seth’s. "Wow," he breathed, closing the door quickly behind him.

Jake was really beginning to wonder about this. What he didn’t know was that Tiffany had taken off all her clothes except for her frilliest bra and panties. The sight of her was enough to make any teen guy’s cock stiffen.

Inside the bedroom, Tiffany patted the edge of the bed, inviting Chip to sit next to her. He obliged and Tiffany waited for the sound of the bell to begin her task. It came a few seconds later, and she wrapped her small hand around the obvious bulge in Chip’s pants.

Jake didn’t know about Tiffany’s scanty attire, but he also didn’t know that her murmurs were from a devilish tease that he was performing on each of her subjects.

"Does your cock feel good sliding against your boxers?" said asked Chip softly. Chip just nodded. Her hand moved in a practiced rhythm as she continued her tease. "I love guys who show their boxers. Will you show me yours?" she asked sweetly.

Chip lifted the bottom of his sweatshirt, exposing a couple inches of his favorite boxers and his tight stomach.

"Oooo, I really like your shorts," Tiffany cooed. "I bet they’re your favorites." She knew darn well that each boy had worn his favorite boxers since they’d all (hopefully) be exposing them to Tiffany in the course of the test.

Chip didn’t think of this, and he nodded dumbly, amazed that this girl knew that guys had favorite underwear. Her assault on his trapped hard-on felt wonderful, and he could feel a drop of pre-cum escaping from his cock and soaking into his boxers. He was starting to worry that he wouldn’t make it to the two-minute mark.

"I wore my favorite underwear, too," Tiffany said, increasing the tempo of her relentless rubbing. "Do you like it?"

Chip realized that she was giving him permission to look at her boobs and her barely covered pussy! He gawked like the inexperienced teen he was, unable to respond to her question. His cock throbbed powerfully.

Tiffany felt the throb, and it excited her greatly. She really wanted to make as many guys as she could get off quickly, so her boyfriend would be able to sag more than any of them. "Ooo, you better be careful!" she purred. "You need to hold back now." The actions of her fingers belied her words. She was jacking Chip through his pants with the same stroke that made Jake cream in the movie theater.

Mercifully for Chip, the sound of the bell came pealing through the door. In a panic, Chip grappled with his pants’ button and zipper, then freed his cock from his pre-cum soaked boxers.

The wait on the other side of the door was brief. Just 15 seconds after the bell, Tiffany’s giggle announced the end of Chip’s test. Jake clicked the stopwatch as several guys laughed.

Even as they laughed, Chip was still squirting big globs of cream through Tiffany’s stroking hand. They mostly landed on his sweatshirt, with some of them wetting the front of his boxers. When he was through, Tiffany handed him a box of tissues to wipe up the mess.

When Chip emerged through the bedroom door, the spots on his faded red sweatshirt were really obvious. Several guys began laughing again, calling out things like, "Way to go, Chip!" and "You totally couldn’t hold it!"

Jake announced, "You can show one inch of boxers." Chip picked a name out of the box and sat down glumly.

Jake smiled when he read the name on the slip of paper. He knew it would be a short test. "Steve? Your turn."

Steve looked visibly shaken as he stood up. His T-shirt was a little tighter than the other guys’, and his pants sagged lower, so when he stood up, the shirt snagged on his billowing boxers so that the striped pattern showed all the way around. Since the top of his pants rested on his cock, there was a puffiness under the top of the fly that showed his state of arousal. He was really worried about this test, and when he opened the door and saw Tiffany in her bra and panties, all he could say was, "Oh my God!" This, of course, added to Jake’s curiosity.

Tiffany’s eyes lit up when she saw Steve’s boxers sticking out between his shirt and pants. As before, she patted the bed to show the nervous boy where to sit. The bell rang, and Tiffany began rubbing Steve’s pants with a vengeance. She had seen him sagging before and was really turned on by how much of his boxers were showing, but he was such a jerk most of the time that she really wanted to put him in his place.

"I love the way your boxers show like that," she whispered, stroking his member through his jeans. "They’re so cool. I hope you can hold back a long time so you can show off like that all the time."

Steve was in a total state of panic. He knew he wouldn’t be able to hold it a long time – he’d be lucky to get it out of his pants. He had to think quickly.

"Uh yeah…maybe you could slow down and help me out, OK?" he asked hopefully.

"Ohhh, I couldn’t do that," Tiffany responded. "We have to make the test fair for everyone." In fact, she was making the test unfair for poor Steve, using her best strokes early on and making his cock slide mercilessly against his soft boxers. Coyly she asked, "Can’t you hold back your cum?"

"Umm…I…I don’t know," he stammered, feeling his balls pulsing, ready to eject his load.

"Ohh, you can’t hold it back?" she teased. "A cool sagger like you? You know your shorts turn on all my friends, don’t you?"

On the other side of the door, Jake was straining to hear what was going on in the bedroom. He couldn’t make out anything, though, until he and everyone else in the room distinctly heard Steve’s desperate voice saying, "Please, Tiffany!" followed closely by, "Oh no! No! FUCK!" Tiffany’s laugh rang out and Jake clicked the stopwatch.

Hoots, hollers, and raucous laughter greeted Steve when he emerged from the bedroom with a huge wet spot covering the whole left side of his fly. Some of his sperm had even soaked up into the area of his boxers that showed above his pants. He looked completely miserable.

Jake relished announcing his time. "A minute, ten, dude! Waistband only for you! Pull ‘em up, dude! Ha ha ha ha ha!"

Steve angrily pulled up his pants to the prescribed height. Of course, being as baggy as they were, they didn’t stay there.

"You’re gonna have to wear a belt, man," Seth called out. "What a dude!"

One by one, each of the boys entered the test chamber, each emerging with cum spots on their clothes. Only one other guy came in his pants, and the longest duration was 6 minutes, 18 seconds. He got to show 5 inches plus his waistband. Purely by chance, Jake’s name was the last one remaining. When he went through the door, he was shocked and angry to see his girlfriend in just her bra and panties. That wasn’t part of the deal! She sat on the messed-up bed in a room that reeked of boy-cum, with one leg curled under her, her legs spread wide, and a few pussy hairs coming out of her panties.

"Jake," she whispered. "I’m sooo horny. Please don’t be mad. But I need you. NOW!" And with that, she jumped up and plastered herself onto her boyfriend, grabbing his face and kissing him passionately. The bell rang from the outer chamber, and Jake had a fleeting thought that he hoped those idiots didn’t break his mom’s bell. But that was soon replaced by a stirring in his loins as his overheated girlfriend rubbed herself against him.

"Fuck the contest," she breathed. "I want you to fuck me. Now."

Jake was astonished. Tiffany had never given any signals that said she wanted to go all the way. Now she was leading him to the bed and ripping open the button and zipper on his loose jeans. His cock sprang free, and Tiffany did something else she’d never done. She sat on the bed and wrapped her lips around Jake’s cock. She moved her head back a forth, swirling her tongue over the sensitive head.

As wonderful as this felt, Jake wasn’t about to give up the opportunity to dip his wick for just a blow job. Pulling out his wallet, he extracted a condom. Reluctantly, he pulled Tiffany off his cock so he could sheath his cock.

Tiffany smiled and laid back on the bed. Jake kicked off his shoes, whipped off his T-shirt, but left his boxers and jeans on. He knew they turned his girlfriend on. Then Jake partly laid down on top of her while using his hand to pull aside the crotch of her tiny panties. His fingers explored her sopping wet pussy until he found his target. Gently, he guided his cock into the hot, slippery hole. Slowly he pushed it in until it was completely inside her. He chuckled when he heard the second bell from outside, but then became serious, looking into the eyes of his beautiful girlfriend as he began stroking in and out of her. He couldn’t help but emit a low moan.

Outside, that moan was interpreted as the pleasure of Tiffany’s hand against Jake’s naked cock. "It won’t be long now," Seth predicted. Little did they know.

Tiffany was really getting excited. She had dreamt of what Jake’s hard cock would feel like inside her, and now it was happening – and it was better than she thought it would be.

Jake was starting out very slowly, thinking that’s what Tiffany would want. But he felt her hands over his lower back, pulling him toward her in an ever-increasing rhythm. So he increased the tempo of his thrusting, plunging his hard tool into her more forcefully.

She responded in kind, thrusting her hips up to meet him. Her hands wandered lower and encountered the waistband of his boxers. Jake had worn the boxers that Tiffany said she liked the best. Even though she couldn’t see them now, feeling them was giving a boost to her passion. She squealed quietly as she ran her hands over the billowing fabric.

The squeal made it through the bedroom door. Out in the den, the guys looked at each other quizzically. A few moments later, they heard grunts from Jake. "She’s really going at it," Chip said. "What’s the time, Seth?"

Seth had the stop watch. "Four minutes, ten seconds," he responded.

Tiffany was getting hotter by the moment. Keeping quiet was becoming more difficult. A particularly energetic thrust from her boyfriend caused another squeal to escape her lips.

Now Jake was building to his own orgasm. Fucking his girlfriend, even with a condom, was ten times more pleasurable than the hand jobs he usually got. "Oh! Oh! Unh!" he grunted.

The guys in the den grinned at each other. They were sure Tiffany’s hand job was about to get to Jake the way it had gotten to each of them. Then Tiffany’s voice emerged. "Yes! Oh, yes! OH!"

Now the guys were sure something else was going on. Steve, who was sitting closest to the door, grinned and stealthily approached the door.

"What are you doing?" Seth whispered.

"I’m just going to peek in and see what’s going on. It sounds hot!" Steve whispered back. Seth just shook his head. Steve carefully turned the doorknob, and silently cracked the door open. His jaw dropped. There was Jake on top of Tiffany, his jeans pulled down to the top of his thighs, and his boxer-covered ass working up and down.

"Well?" Seth whispered.

Trying to supress a giggle, Steve mouthed, "They’re fucking!" Instantly, every guy was on his feet, all trying to get a peek through the crack in the door.

Jake was oblivious to all this. He could only concentrate on the fantastic sensations of Tiffany’s spasming cunt around his tool. Tiffany, on the other hand, heard the commotion and looked toward the door. She saw several pairs of eyes peering in at different heights. She smiled to herself.

"Oh, you’re so good Jake," she said, just loud enough for the others to hear. "Fuck me, fuck me harder!"

Jake couldn’t believe it. Her words added fuel to the fire in his brain and in his groin. The best fuck of his short life would be over soon.

"Oh, baby! You’re so hot!" he murmured. "I can’t hold out much longer!"

"Oh yes!" she said. "Cum with me Jake! Cum with me….cummm…..Ahhh!"

"Oh! Oh! FUCK!’ Jake shouted, not caring who heard him. "I’m cumminnnnngggg!"

Tiffany wasn’t giggling this time. She joined Jake in abandoned thrusting and groaning, both teens enjoying their orgasms to the fullest.

Out in the den, the door had been opened several inches now, and a group of horny teen guys were standing there clutching their once again hard cocks through their cum stained pants. Steve was already having his second climax of the day, the results of which dripped out the bottom of his boxers and spread down the front of his pants.

Even with one hand rubbing his jeans-clad cock, Seth had the presence of mind to click the stopwatch when Jake announced his orgasm.

Now the boys carefully closed the door. Jake never knew they were watching. Steve stood there looking down at his hopelessly cum stained jeans and several guys took the opportunity to make fun of the hair triggered teen, telling him to pull up his cummy pants.

It was several minutes before Jake emerged from the bedroom. He knew he’d lasted longer than any other guy, and he thought he’d even broken the 7 minute barrier. He swaggered into the room with his shirt still off and the top of his jeans at the tops of his thighs, completely below his ass, cock and balls! A good 10 inches of his boxers were showing, and the bulge of his cock was clearly visible underneath his boxer shorts. He turned to Seth. "Well?" he asked.

"Seven minutes, one second," Seth said.

The room broke into applause. Jake enjoyed it, partly because he thought no one knew what really went on in there, partly because he could sag more than the other guys.

"You’re the man," Chip said.

The next day at the park, Jake was the only extreme sagger in the bunch, wearing the same jeans (with different boxers) in the same way as when he emerged from the bedroom. Each of the other guys sagged in proportion to their longevity in yesterday’s test.

Tiffany approached with several of her girlfriends. "Hi guys!" she chirped. "Hiii, Jake…" she cooed, sliding up next to her studly boyfriend.

The other girls studied the waistbands of the remaining guys and moved closer to the guys with several inches of boxers showing. Of course, poor Steve, with only the elastic of his waistband showing, was left out.

Tiffany ran her hand over Jakes tight stomach and whispered how much fun she had yesterday. Her touch and the memory of their fucking started Jake’s cock hardening. With only his flimsy boxers to restrain it, soon Jake had an obvious tent sticking out above his jeans waistband!

He quickly slid Tiffany in front of him, her back side toward him, and wrapped his arms around her. This hid his condition from the others. Tiffany felt the prod against her ass cheeks and pushed backwards. Jake winced. "Be nice," he whispered in her ear.

Tiffany had no such intentions. She subtly squirmed and wiggled until Jake’s cock was pronging right between her ass cheeks. She was wearing some lightweight cotton shorts, so it was easy for her to get a grip on his cock head. Now she started shifting her weight from one leg to the other, masturbating poor Jake’s cock head with every move.

Everybody was making small talk, and everyone was eyeing the guys’ boxer shorts waistbands. The guys, who habitually adjusted their jeans and boxers all the time anyway, were being extra careful about their adjustments. Plus, they wanted to make sure that none of the others was cheating and showing more than they were allowed to. The girls were just fascinated by the guys and how much of their underwear was showing.

Jake was oblivious to all this, but he was beginning to regret his extreme sagging. His boxers were already getting wet from Tiffany’s squirming, and he was in danger of ejaculating into his exposed boxers right in front of everyone!

Tiffany felt his cock throbbing and decided to put him out of his misery. She sneaked one hand behind her and grasped Jake’s boner, right through the material of his boxers! At the same time, she squeezed her ass cheeks together, clamping them against his throbbing cock head.

That did it for Jake. He briefly closed his eyes as his semen shot uncontrollably into this boxers. It soaked through immediately, wetting both his underwear and Tiffany’s shorts. The massive ejaculation ran down the front of his boxers and pooled at the top of his jeans, soaking the fabric there as well.

Tiffany couldn’t help herself. She giggled.

Every guy there knew that giggle. They all looked around to see Jake, red in the face, his front plastered against his girlfriend’s back side, and Tiffany removing her hand from around her back.

Steve would now get his revenge. "Hey Jake! You got a problem there, dude?"

The panicked look on Jake’s face answered the question. All the guys started laughing. "I…uh…No, no problem," Jake bluffed, holding Tiffany tighter than ever. Now the girls were starting to laugh. They had all felt their boyfriends hiding boners against them.

One of the girls spoke up. "C’mon Tiffany, we gotta get to the mall before it closes."

Tiffany hesitated briefly, then reluctantly pulled Jake’s arms apart. She spun around quickly and hugged him, whispering in his ear, "I’m sorry. I’ll make it up to you." She kissed him and backed away, leaving Jake with his ten inches of boxers exposed, five of them sopping wet with slippery cream, and clinging to the outline of his softening cock. He wasted no time pulling his jeans up to cover the mess, but it was too late. They’d all seen what happened. Some guys smirked, some laughed. Some of the girls giggled, but they all thought it was a hot sight.

After that, Jake decided that extreme sagging was OK only after he’d gotten off, preferably with Tiffany.