Readers Warning: The following fictional story contains elements of sexual activities between teenage boys. If the subject matter offends you, is not to your taste, is not legal in your area, or if you are not of legal age in your area; then you should not read any further.
This story is fiction, but is based on me and a friend who I messed around with when I was younger. We were both into sagging our pants and it's part of what led to us messing around, though it never developed like this story will. Again, the names, places, and events in this story are completely fictional.
I wrote a version of this story a few years ago but have made some major changes from what it was. The old story is in bisexual section under college stories. Please do not be confused since the titles are the same and I used a different email back then. This version is very different. The mention of girls is just to build the relationship between the two main characters, and will be limited to just this first chapter.
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Saggin' Together Chapter 1
It was a boring summer day and Jake and Steve were hanging out in Jake's room. It had been raining non-stop all day so the two friends were stuck inside. They were lying on Jake's bed playing video games and talking about the upcoming school year. They would both be turning 14 this summer and starting high school when the new school year started.
They were both looking forward to starting at a new school. Since their high school was regional, there would be all kinds of new people who the boys did not know. Plenty of new friends to make. The pair kept chatting about all the new possibilities the new school offered while they kept gaming.
"There's going to be so many new people. Four towns feed into the school so it'll be almost like a chance to reinvent yourself a bit!" exclaimed Steve.
"Yea, dude" replied Jake, getting some amusement out of his buddy's enthusiasm. "What exactly do you wanna change though?"
"I'm not really sure," answered Steve. "Like new style, new attitude, whatever I guess."
"Yea, that's not a bad idea. Maybe we should get more serious about exercising this summer. Hold each other to it and then we can build some more muscle to show off for the ladies," said Jake slyly.
"Good call bro!" replied Steve. "We're already in good shape from sports, so we can definitely do it!"
Steve was knocked out of the video game for a second and he turned to talk with Jake some more as he waited for his character to be revived. Jake was now lying on his back propped up on headboard. Steve noticed Jake had taken his shirt off so he could see the muscle Jake was talking about. Jake's chest was already nicely developed and his lean frame showed off the muscle he already had. A nicely developing six pack was below. Jake filled out his 5'5'' frame quite well and was clearly on his way to being a stud. His short blond hair and nice blue eyes complimented his tan complexion and lean features.
Steve had seen similar rewards from being on the same sports teams as Jake. But Steve had also been doing some extra exercises on his own at night so his chest and abs were more developed than Jake's. Jake had made a few joking comments recently about how "shredded" Steve was starting to look, and it nearly made Steve blush every time. Slightly less tan than Jake, Steve's brown hair and green eyes went well with his own lean and fit body standing 5'6'' tall.
Steve always thought Jake was really good-looking, but he wasn't really sure what those feelings meant yet. After all, they were both into girls as far as he knew. Earlier during the last school year, they'd made out with and gotten their first blowjobs together from two of their female classmates. It was awesome, but what Steve liked most was watching the look of pleasure on Jake's face as he got his dick sucked. Steve was surprised when he found himself wishing he was the one making his best friend feel that good. When Steve heard Jake moan in ecstasy as he shot his load in the girl's mouth, it sent Steve over the edge and he did the same. Steve wondered what Jake's load tasted like as his own was swallowed down.
Getting blowjobs had boosted the boys' confidence and popularity at school. Experiencing this first together also deepened their friendship. Steve was fortunate that they had managed to get blowjobs together a few more times from a few other girls in their class. And each time he was delighted by watching Jake get sucked off and wished he was the one who could please his buddy.
Just a few months ago, when Jake was spending the night at Steve's and the boys were engaging in the typical banter about girls. Thinking about the blowjobs they'd gotten earlier in the day had them both in need of relief. Jake shyly suggested watching some porn and jerking off, and Steve was quick to agree, hoping he didn't sound too excited. Steve barely focused on the porno as he watched Jake jerk off and shoot his load. The sight had Steve blasting his own load a few moments later. Jerking off together soon became a fairly regular thing.
Jake was engrossed in the game and did not notice Steve was staring at his shirtless torso. He answered Steve, "I'll talk to my dad, but I bet he'd let us use his gym in the basement if he thinks we're serious about it."
"That would be sick," said Steve. "Your dad has a ton of machines and weights down there, it'd be perfect."
"I'll talk with him this weekend about it and let you know what he says. You're about to come back dude, grab your controller," said Jake.
"Oh shit, thanks. Spaced out for a sec," answered Steve as he reached for his controller. The boys then resumed gaming and got lost in the virtual world. Their trance was only broken when Jake's mom knocked on the bedroom door.
Jake's mom opened the door and spoke to the boys, "Steve, it's still pouring out and there is lightning in the forecast. I talked with your mom and we agreed you can spend the night if you want so you don't have to bike home in the storm. Your mom can come pick you up but we figured you'd probably be ok with staying the night."
"Thanks Mrs. Matthews," answered Steve. "I'll spend the night if it's cool with you Jake?"
"Of course, man!" stated Jake. "We'll have more to game now since there's not much else we can do anyway with this weather."
"That settles that then," said Mrs. Matthews. "Let me know when you boys are hungry and I'll order you a pizza. Just try not to get to rowdy."
"Thanks, mom," said Jake as his mom closed the door and left the boys to their games.
The two friends went back to their game for another hour or so. Jake called down to his mom asking her to order a pizza, and it arrived about 45 minutes later. Jake turned off the game and put on a TV show they could watch while eating. He then ran downstairs to grab the pizza, soda, and some plates so they could eat in his room.
When Jake returned to his room, he put the food and other items on his desk and then turned towards his dresser.
"I'm going to get more comfortable," said Jake. He dropped his cargo shorts and stepped out of them as he rummaged through his dresser. Steve couldn't help but notice how firm Jake's ass looked in his red boxer briefs. Because his back was turned, Steve could not see Jake staring. Without turning around, Jake asked, "Want some shorts dude?"
Steve was almost entranced by the sight of Jake's ass, but he snapped out of it to answer, "Sure bro, thanks."
Jake tossed Steve a pair of gym shorts and found out a pair for himself. He pulled on his shorts and as he turned around, Jake watched as Steve changed into the gym shorts he'd thrown him. Steve also tossed off his shirt so both boys were now shirtless wearing just their gym shorts and boxer briefs. Steve thought he saw Jake staring at his body for a second, but before he could say anything Jake was walking towards the food.
"I'm starving, bro. This is gonna be so good," said Steve as he grabbed himself a slice and a drink.
"Yea, I'm starving too," said Steve as he got some pizza for himself. They got comfortable on Jake's bed and watched some TV while eating. It wasn't long before all the pizza was gone and the boys both laid back on Jake's bed while they watched TV. Lying next to shirtless Jake, Steve couldn't help but glance at his body a few times as they watched TV. Steve thought about those red boxer briefs Jake was wearing and then came up with an idea.
"So, dude, you were talking about doing new things to get some more girls, there's something else we could try," Steve told his friend.
"Yea?" queried Jake. "What is it?"
"Well, remember a few years ago when I went on that camping trip to Yellowstone for the week with a bunch of family?" asked Steve.
"Yea, what about it?" replied Jake.
"Well one of my older cousins there was hooking up with other girls at the campsite all week. It was almost ridiculous," Steve stated as he started his answer.
"He was really fit guy and pretty much always had his shirt off. But he also had this confident swagger about him. And he always wore his pants low so you could see his boxers," Steve continued.
"So, we need to have swagger?" asked Jake, a little confused as to what Steve was getting at.
"Well yea, but like I think the way he was dressed was part of it. You've seen how some celebrities and even guys in other towns wear their pants like that too," Steve tried to explain.
Jake interjected, "Yea, I actually noticed my brother was doing that when he came back from college. I asked him about it because I'd never seen someone dress like that before and he said it's called sagging. My brother said all the guys in his college do it to show off for the girls. I thought about it, but nobody in our school does it so I thought it might be weird."
"Well that makes it an easy call. If college girls like sagging we should try it too. We can get comfortable with it this summer so it's normal for us when school starts," said Steve trying to conceal his excitement.
Steve had always noticed older boys and some boys his age from other schools would `sag' their pants, as Steve now knew it was called, and he loved to look at the different underwear that was shown off. It was especially nice when there was a nice tight ass as well! Steve's thoughts like this confused him, and he still liked looking at girls too, but he liked looking at guys so much he didn't really want to stop. And now if he could convince Jake to go along with this idea, Steve would have a cute sagger to hang out with all summer.
"I guess," said Jake with some hesitation. "You really think it'll make a difference with the girls? I mean there will be other guys in high school doing it I'm sure, so it would probably seem normal to everyone but the kids we've known since kindergarten."
"Well, this along with working out, I think we'll be in a good place to hook up with some more girls," answered Steve with a smirk. He wasn't about to let his own sexual thoughts about sagging weird out Jake, so he focused on the idea of getting girls.
"It's real easy anyway," said Steve. "We just got pull our shorts down some so our boxers are exposed. Here I'll try it first."
With that Steve stood up from the bed and pulled the gym shorts he was wearing down an inch or two so that the waistband of his black boxer briefs was clearly visible. He walked around a bit and posed in front of the mirror in Jake's room before asking his friend what he thought.
"It looks cool," offered Jake with a somewhat forcibly subdued tone, "but my brother's pants were a little lower than that."
Jake then got up from his bed and pulled his own gym shorts down about 3-4 inches. His red boxer briefs were very visible, and he walked over to the mirror Steve was standing in front of. Steve lowered his shorts to match his friend and the two boys admired themselves, and each other, in the mirror for a bit.
Both boys had nicely developing v-lines trailing into their now visible boxer briefs and they spent the next minute or so looking over themselves while secretly stealing glances at each other.
"Should we try it with some different underwear?" asked Jake.
The level of curiosity surprised Steve and he retorted, "You can but I'd have to go home to get some more boxers. My folks would wonder why I'm running home for new underwear."
"I'll lend you some," offered Jake, "It's no biggie. I mean we've seen each other naked in the locker room and we've seen each other get head, so I don't see why it would be a big deal really. We're pretty close after all."
"Thanks Jake, I'm glad we're close like that you know. Let's really try it out then," replied Steve.
With that the two boys fishing went through Jake's underwear drawer to get a few pairs of underwear for each of them to try. Jake had a mix of boxer briefs and boxer shorts, so they grabbed a few of each.
Steve watched as Jake took off what he was wearing and his buddy's cock came into view. Steve had seen it before, but never got tired of the sight. Jake's cock had grown a bit and was now about 6 inches long. He knew because they'd measured recently to compare. Jake was slightly longer than Steve's 5.5 inches, but Steve`s cock was a little bit thicker. Both boys were circumcised and their cocks seemed to widen at the head.
Not noticing Steve looking at his dick, Jake put on some red plaid boxer shorts. He put on his gym shorts again and adjusted his sag to be about 3 inches. Steve followed Jake's lead and put on a pair of boxers with some cartoon characters. He adjusted his sag to match Jake and they both laughed at the cartoons on Steve's ass.
The two friends spent an hour or so trying different boxers and modelling their sags for each other. Steve tried on a pair of tight orange boxer briefs and thought about how hot it was to have his cock resting where Jake's had been. To Steve's surprise, he watched Jake pick up the pair of boxer briefs Steve had been wearing when they started and try them on. He adjusted his shorts so they were sagging about 4 inches.
"I think these look better on me," laughed Jake.
Steve laughed and said jokingly, "Maybe you should keep them."
"Mine now," laughed Jake.
"Well if those are yours, then these are mine" Steve joked back referring to the orange boxer briefs he was currently showing off.
As the two teens had been exposing themselves as they changed boxers, the sexual tension had really been building. Steve's cock would twitch each time he saw his friend remove his underwear and he got a clear look at his dick. Steve focused on the sagging for now.
Steve's focus was brought back to his stiffening dick when Jake exclaimed, "Man we look pretty good! We put on some more muscle and sag like this, we'll be gettin' girls all the time!"
The thought of getting with so many girls naturally made Steve start to stiffen up, and with how low his pants were sagging, it would not be hard for Jake to notice. But as exciting as girls were, Steve was even more excited at the idea of spending the summer sagging and working out with Jake. Jake's attitude about all this pleasantly surprised Steve.
Jake noticed Steve's bulge and since he was having a similar issue quipped, "Whatchya pitching down there?"
With a smile Steve replied, "All this sagging and thoughts about the girls are getting me hard. May have to take care of this soon."
"No time like the present," suggested Jake as he dropped his sagging shorts and shucked off Steve's boxer briefs. Steve followed suit and they each pulled a chair up to Jake's desk as Jake opened his computer.
Jake's dick was at full attention as he headed to his favorite porn site. As Jake browsed the web Steve admired his friend's lean body. The presence of his friend got Steve even more excited and his own cock was now completely erect. As Jake found a good video Steve turned his attention from his friend's body and towards the computer screen. The two guys leaned back in their chairs and started jerkin off in earnest. They ran their hands up and down the lengths of their cocks while watching a video of two guys banging one girl.
They sighed with pleasure as they stroked away and let the good feelings take over. They each had a hand firmly around their own dicks and got more and more into what they were doing.
"Fuck this is a hot scene," remarked Jake.
"Yea," replied Steve, "I bet it would be cool to double team a chick like that."
"For sure," agreed Jake. "We'll have to try it some time," he laughed.
The pair kept stroking their cocks while the porn continued. Steve was busy jerking his hard dick and he could hear soft moans coming from Jake as he was jerking himself off. Steve started to moan as well and the boys smiled at each other as the feelings of an orgasm started to build.
Steve looked back at the video and was surprised when he saw the two guys in the film were now kissing each other as they fucked the girl. The sight sent Steve over the edge.
"OhÉ.fuuuck" Steve moaned as his balls tightened and drew up into his body. "UhÉUhÉFuck," he felt his cum pulse through his dick until the first stream shot out and over his shoulder, the next one hit Steve's chest and another four of five shots of cum covered Steve's abs.
Seeing Steve cum so much pushed a button in Jake's loins, "oh shit, here it cumsÉfuck, I'm cumming!" And Jake's cock erupted. He fired a good six shots all over his chest and abs. Exhausted and satisfied the two boys slumped back in post-orgasmic bliss.
"Fuck, that was awesome!" declared Steve. "I don't think I've ever shot that far before. Not even sure where that first shot went," he laughed.
"Hahaha," laughed Jake, "It doesn't matter, that was fucking great. Let's grab a shower and clean up."
"Good call," said Steve.
The two boys then went to Jake's bathroom and since the shower was big enough for the two of them, they shared it to save time. When they got back to Jake's room, Jake pulled on the Steve's boxer briefs again. Steve looked at him a little curiously, which Jake noticed.
"I told you dude, these are mine," said Jake. "You said we should get comfortable with sagging so let's do it together whenever we can now." Jake pulled on his gym shorts but left them sagging a few inches and laid down on his stomach on the bed.
Steve was delighted to hear Jake was into the idea of sagging together. "Sounds good to me," said Steve. He grabbed Jake's orange boxer briefs he was wearing before off of the floor and put them on. Steve made sure his sag matched Jake's and then laid down next to him on the bed.
They spent the rest of the evening playing video games and watching TV, staying up as late as possible as boys tend to do. Eventually they started to get tired and got ready for bed. Their sags had gotten a little lower, but they decided to ditch the clothes for sleeping since it was so muggy out with the rain. They climbed into bed naked and quickly passed out into a peaceful sleep.
Jake was the first to awake in the morning. He looked to his right and saw Steve lying on his back. His hand was wrapped around his morning wood as he slept. Jake laughed at this sight but it made his own cock start to stir.
Jake felt strangely aroused by the sight of his friend and noticed he now had morning wood of his own. They'd always watched porn together when they jerked off before, but Jake didn't feel like watching anything right now. He reached down to grasp his hard cock. Jake started to rub himself and soon got into a nice rhythm as he found himself thinking about some of his sexual adventures he'd had with Steve.
The girls were ok. Jake had nothing against girls, but he just never felt very attracted to them. Getting his dick sucked was great and all, even if it was a girl, but the best part for Jake was that Steve was there. Steve was his best friend and it always felt right when they did things together and hung out. He was glad Steve was cool with jerking off together, but sometimes wished he would want to do more. Jake was realizing more and more that he was attracted to boys, and especially Steve. But Jake was afraid what Steve might not feel the same way and it could ruin their friendship. Jake had decided to try and discreetly see if Steve had any similar feelings.
The video Jake chose last night was part of the plan. He knew the two guys would kiss at one point and wanted to see how Steve would react. It wasn't lost on Jake that it was right when the guys kissed that Steve's cock exploded. It was definitely an encouraging sign!
Jake was still busy jerking himself off as he thought about Steve more and more. He looked over his friend's nearly nude body and felt his dick get even harder at the sight. Jake was loving the feeling he was giving himself and started to get really into it.
The sound of Jake's fapping was loud enough to rouse Steve from his sleep. As he opened his eyes, Steve saw Jake had his eyes closed and was furiously beating off. The image made Steve's morning wood pulse and he realized his hand was already on his cock. Steve decided to join his friend for a morning jerk session.
"Good idea, bro," said Steve as he quickly started stroking his cock to try and get some morning relief.
"Sorry dude, didn't mean to wake you," said Jake. "Just had to take care of this thing and didn't think you'd mind."
The two boys laid back on Jake's bed and kept stroking themselves. As they got more into it, their legs started to shift and soon were in contact with one another. They both leaned in a bit to enjoy the contact as they kept jerking off.
Jake's breathing quickened and he could feel he was about cum. Steve was not far behind and could sense what was coming.
"Are you close?" asked Steve
"Yea, I'm about to shoot," said Jake.
"Let's try and time it so we can cum at the same time, I'm close too," said Steve.
"That sounds awesome," said Jake with excitement. "I'm like real close though, are you?"
"Yea," answered Steve. "I'm gonna bust any second now."
He wasn't kidding. Just a few seconds later Steve's breathing picked up even more. "Oh damn, this is gonna be a big one again," he said as his cock felt ready to explode!
But Jake came first. "Fuck, I'm cumming dude, can't stop it!" exclaimed Jake and he closed his eyes as his orgasm began. The feelings in his dick were so intense that Jake couldn't help but arch his back and lean a little on his side. As a result, the first stream of cum shot from his dick landed on Steve.
Steve felt Jake's cum land on him and immediately started cumming, "Uh, fuck I'm cumming," he moaned as his load began to fire out his cock.
Steve threw his head back and his first shot hit the headboard of Jake's bed before the next one hit him square in his cheek. The rest of Steve's load landed all over his abs. Steve kept stroking himself as he came, completely lost in the feelings as his body stretched, his back arched, and his toes curled in pleasure.
Meanwhile, Jake was in the throes of his own orgasm as he finished shooting all over Steve. Jake opened his eyes and saw that he'd cum all over his friend. He was worried for a second, but from the look of ecstasy on Steve's face, it didn't seem to be a problem. A few more drops of cum dribbled out of Jake's cock and onto his body as he watched Steve's orgasm subside.
"Damn, that was even better than last night!" exclaimed Steve. "I hit myself in the face," he laughed as he felt the cum starting to drip down his cheek toward his mouth. Steve wiped it off but got a small taste and was surprised when he found himself thinking it tasted pretty good.
"That thing has got some range," joked Jake pointing at Steve's dick. "But at least we know where all your cum landed this time. Sorry I shot on you, it was so intense I didn't see where I was shooting."
"Clearly," laughed Steve, "It's all good man. I've never cum like this before now, but damn it feels good," said Steve. "Think I need a shower again, you mind?"
"Nah, I need one too," answered Jake. "I didn't shoot my whole load on you," he laughed pointing to the cum on his body.
The two friends hopped naked out of Jake's bed and headed to the shower again. When they were all cleaned up they headed back to Jake's room and cleaned up the food and everything else from the night before.
The rain let up overnight so Steve needed to be getting home. He went to get dressed into his clothes from yesterday but saw Jake had already put the boxer briefs Steve had been wearing on again.
"Well if you're keeping my boxers," joked Steve, "I'm keeping these."
Steve then put on the orange boxer briefs he slept in and pulled up his shorts. He decided he was going to leave them sagging for the ride home. He adjusted his shorts so that 2-3 inches of what were now his boxer briefs were showing. When Steve bent over or raised his t-shirt a little, his bright underwear was on display.
Jake saw this and couldn't help but feel a little excited. He put his gym shorts back on and left them sagging like Steve was. The boys admired each other's sags for a few seconds before Steve broke the silence.
"Alright dude, I'm gonna head out. Let me know what your dad says about using the gym."
"For sure. He gets back from his trip tomorrow, so I'll ask him them and let you know," replied Jake.
"Cool, well I'll see ya later then," said Steve as he walked out of Jake's room and outside to head home. Jake watched Steve ride away on his bike and the way he was seated, Jake could see the orange boxer briefs that now belonged to Steve. Steve's ass looked great in them. Jake looked down at his own prize, a pair of Steve's boxers that were now all his own.
Jake thought about how his cock was resting right where Steve's was. The thought excited him and soon his dick was hard again. Jake laid down on his bed and thought about Steve again, quickly stroking himself off to another powerful orgasm. "Next time maybe Steve and I can do some more stuffÉ" Jake thought to himself before grabbing a towel to clean himself off with.
Little did Jake know that the feeling of wearing Jake's boxer briefs left Steve with a raging hard-on as he biked home. As soon he got there, Steve ran to his room, stripped down, and played with his dick until he shot another big load all over himself. This time Steve ran his finger through his cum and brought it to his mouth.
"That tastes pretty good," Steve said to himself. "I wonder what Jake tastes likeÉ"
He hoped to soon find out.
Thanks for reading! Hope you enjoyed the story!
Comments, feedback, and ideas for future chapters are always appreciated. Stonerbro22@yahoo.com