Scott's New T-shirts

(Note: All photos are solely to suggest what a character might look like. They do not dopict any of these purely fictional characters.)

It was the first week of high school for Scott. There was so much to take in: the arrangement of the new campus, new teachers, new ways of doing things. But something else caught Scott’s attention. The older boys wore T-shirts – sometimes alone, sometimes under their regular open collar shirts, sometimes under V-neck sweaters – but their T-shirts were different from his.

Scott had always worn the tees his mom bought him. He had never really noticed any difference between the ones he wore and the ones his buddies wore. But the older boys’ T-shirts looked different somehow. They seemed to be made of heavier, whiter cotton than his, for a start. And the sleeves hung lower on their arms. But what really caught his attention, especially when they were worn under a regular shirt, was that the ribbed band around the neck stood up taller than his. The neck bands didn’t droop and sag the way his did after a couple hours’ wear.

Scott started feeling self-conscious about his T-shirts. He did what he could to make the neck show more underneath his button down shirts. But it still didn’t look right; it still didn’t look like the way the cool boys’ T-shirts looked.

The locker room was not a new experience for Scott; his junior high school had one, too, and all the boys would change clothes for P.E. But now he was thrown in with boys who were much more mature. Their dicks and balls were bigger and hairier. Their muscular development was greater. And when they took their shirts off, their T-shirts looked better.

 Scott’s locker was right next to a boy who was in 11th grade named Jim. He had the best looking T-shirts Scott had ever seen. One day, when the older boy had gone to take a shower, Scott decided to find out what brand of tee he was wearing. Taking a quick glance around to see if anyone was looking, and with his heart pounding, Scott deftly opened Jim’s unlocked locker and quickly examined the tag on his T-shirt. It said "Spartan." That definitely wasn’t the brand his mom bought, so now he knew why they looked different.

Scott spent the weekend at the mall, going from store to store, looking for this brand of T-shirt. Finally, in a department store called "Russell’s", he found what he was looking for. He picked up a package of small men’s tees and examined the contents through the cellophane wrapper. ‘Wow,’ he thought. ‘Look how wide that neck band is.’ He remembered how Jim looked in his Spartan T-shirt, imagined himself wearing one, and suddenly felt a familiar tingle in his crotch.

‘Oh no, I can’t get a boner!’ he thought. His desperation quickly gave way to resignation as his tender Freshman cock sprang almost instantly into complete rigidity in his pants. Now what was he supposed to do? He had brought enough cash to pay for a package of these T-shirts, but he didn’t want to go through the checkout line with a bump in his pants. So he decided to pretend to shop for some other things until it went down.

He was in the underwear section of the men’s department, and when he turned around, he was faced with a wall stocked with boxer shorts. He quickly scanned the huge variety of colors and patterns, when his eyes locked on something familiar. These boxers had the exact same pattern as Jim was wearing last Thursday. He noticed them because Jim let his jeans "sag" – they rode very low on his hips and exposed a lot of his boxer shorts over the waistband. He involuntarily let out a giggle when he thought about buying them so he could be wearing the same T-shirt and boxers as the cool older boy in the locker next door. He walked over and picked them up. His boner jumped. He couldn’t believe he was getting so aroused over underwear, but that didn’t stop him from rummaging through his wallet to see if he had enough money to buy the shorts, too. He did, and he took the package with him.

Just then, an older boy turned the corner on the aisle and headed for the T-shirts. Scott watched with fascination as this boy rummaged through the packages (rather than picking up the first package that matched his size). He was apparently examining the front shirt in each package. When he found what he was looking for, he put the rest of them back. Sensing he was being watched, the older boy turned and looked at Scott, who had a puzzled expression on his face.

"You gotta find the ones with the tight necks," the boy offered. He grinned when he saw the sudden look of understanding on Scott’s face, and headed off toward the checkout counter.

Scott looked down at the package in his hand. He couldn’t tell whether this neck was tighter than any of the others, so he went back to the T-shirts. He copied what he’d seen the other boy do, now paying attention to the circle formed by the neck band in the front of each package. Sure enough, there was quite a bit of variation. The one he had picked was pretty good, but he traded them when he found one that was even tighter.

Now he knew his boner wasn’t about to go soft any time soon, so he decided to go through the line anyway. The older boy he had seen earlier had just finished his transaction and was on his way to the door, and there was now only one housewife ahead of him. Scott held the packaged tees and boxers in front of his crotch, trying in vain to will his cock soft.

When it was his turn, he placed the items on the counter, then stood very close to it to try and hide his condition from the cashier. She was a cute young girl, probably still in high school herself. She smiled slightly as she scanned the two items and looked into the wide-eyed face of the young boy.

"That’ll be $18.62," she said. Scott handed over a wadded up 20-dollar bill. The cashier quickly made change. As she handed it to him, she said, with a knowing lilt in her voice, "Enjoy your purchases." Scott blushed 18 shades of red as she added in a soft voice, "They’re very cool."

Scott managed a wan smile, took his change and package, and hurried out of the store, his rock-hard boner bulge preceding him by a few inches.

On his bicycle on the way home, Scott’s cock never lost its hard. Pointing toward his navel, it slid back and forth against his belly every time he pedaled. When he thought about getting home and trying on his new purchases, the sensations in his groin increased. Several times he had to stop pedaling and coast for fear of ejaculating inside his jeans!

Once home, he made a beeline for his bedroom and closed the door behind him. He practically ripped open the package of tees, shaking out the top one and holding it up. Yep, the arms were longer, the neck band was taller, and the cotton was heavier. This was a cool T-shirt, he thought. He pulled off his own shirt and donned his new purchase.

"Wowww," he breathed out loud when he saw his reflection in the mirror. He couldn’t believe the difference between this shirt and the ones his mom bought. The neck band actually hugged his small neck, and the body of the shirt draped squarely off his shoulders. He ran his hand over the neck band, pressing it even tighter against his Adam’s apple.

In the reflection in the mirror, he saw the package of boxers on the bed. Once again, he giggled at the thought of wearing the same boxers as Jim. He went over and opened the package, pulling out the familiar shorts. Off came his pants and boxers, and up went the new shorts. His cock was still stiff as board, so it just poked out into the starchy new fabric of the boxers.

Despite the hardness of his cock, Scott wasn’t expecting what happened when he turned at looked at his reflection in the mirror. There was a new kid in a very cool T-shirt and boxers. He couldn’t believe the image. He also couldn’t believe it when his untouched boner started firing hot cum into his new boxers. He was so stunned that he just stared at himself in the mirror, watching the front of his new boxers get soaked with semen, and then watching even more semen leak out one of the leg holes. By the time he thought about grabbing his cock and stroking it, it was all over, and his boner began to wilt. He looked into his own eyes in the mirror and giggled once again. How cool was that? This new T-shirt was so cool, it made him cum all by itself!

He noticed some wetness was soaking into the bottom hem of the T-shirt, so he quickly took it off. The boxers were a hopeless mess, but a slight twinge went through his groin when he imagined Jim in cum soaked boxers like these.

But reality came back to him quickly when he realized these would have to go into the wash. What would his mom say about these foreign garments? As he pulled off the wet underwear, and pulled on his old clothes, he formulated a plan.

"Mom!" he called out as he exited his bedroom.

"In here, dear," she responded, sounding like she was in the living room. She was, and she was watching a tape of her favorite soap opera. This was a great time to ask her.

"Mom, I think I’m old enough to pick out some of my own clothes," Scott said, adding quickly, "I’ll pay for them from my allowance."

"OK, dear," his mother said, only half paying attention to the conversation.

"Great. Thanks!" And with that, Scott had permission to do what he’d already done.

At school on Monday, Scott wore one of his new T-shirts under a plaid, button-down shirt. He chose that shirt because with the top button unbuttoned, the collar spread wide to reveal lots of his new T-shirt. All day, he felt a new confidence that he’d never felt before. He felt unmistakably cool. He also found himself fingering the neck band of his T-shirt several times during class. Each time he felt his shirt, his cock would spring up in his pants. This one article of clothing was making him feel, well, sexy – something he’d never felt before.

But the most amazing thing happened in P.E. When he took his plaid shirt off in front of Jim, exposing his brand new Spartan tee, Jim, who had never said a word to the Freshman boy, said, "Cool T-shirt."

With an astonished look on his face, Scott turned to look at Jim. Jim was staring straight at Scott’s neck. Scott smiled and, as coolly as he could manage, said, "Thanks." Jim looked into his eyes and grinned, then wordlessly went back to changing into his gym uniform.

Scott was on cloud nine all through P.E. He also popped a boner several times during the period. A cool older boy had noticed him and his new T-shirt. Wow! At the end of the period, after his shower, Scott pulled on his underwear, and went to get into his new, sexy T-shirt. But just looking at it and handling it, Scott’s dick began to harden.

‘No, not now!’ Scott thought desperately. He quickly pulled the T-shirt on as his boner rose up, tenting the front of his boxers. When the T-shirt dropped down, it got caught on the tent, outlining it and making it very obvious. Before Scott could do anything about it, the draped prong caught the attention of Jim.

Scott heard Jim snicker quietly, and prayed it was about something else. As he pulled the bottom of the T-shirt over his boner bulge, he looked at Jim. ‘Oh shit," Scott thought in horror. ‘He saw it.’ There was no mistaking it, Jim was gazing directly at the now-concealed yet still obvious tent of Scott’s unruly boner. The smirk on his face said everything. Scott quickly turned his back to Jim and rummaged through his locker for his pants.

"Hey, don’t worry about it, man," Jim said, his deep voice oddly comforting. "It happens to all of us."

After he was safely in his pants, Scott turned, wide eyed, and faced the smiling Junior boy.

"You live on Hummingbird Lane, don’t you?" Jim asked.

"Yeah."

"Well, I’m just over on Blue Jay. Number 430. Why do you come over to my house after school?"

Despite being dumbstruck, Scott managed to say, "Yeah, sure."

For the one remaining period that day, Scott tried to figure out why Jim had asked him to his house. But he wasn’t going to turn down a chance to hang out with a cool older boy.

After school, Scott walked the extra block to find Jim’s house. Jim answered the door wearing a T-shirt and baggy jeans.

"Come on in," he said. "Let’s go in the den."

Scott followed Jim to the back of the house into a very comfortable room. Jim plopped down in an overstuffed chair and indicated for Scott to sit on the couch.

"So, you finally got some cool T-shirts, huh?" Jim started.

"Yeah!" Scott replied, a little too enthusiastically.

"You got Spartans, right?"

"Yeah, how’d you know?"

Jim smiled. "You can tell. They’re the only ones that fit like that, with that great collar."

"Yeah, they’re really cool, aren’t they?"

"But they give you a boner, too, don’t they?" Jim asked with a smirk on his face.

Scott blushed. "Yeah," he admitted.

"That’ll go away," Jim said nonchalantly. "But they are a turn-on."

Once again, Scott got that wide-eyed look that told Jim he was all ears.

"The cool chicks at our school won’t go out with a guy in a funky T-shirt. You gotta show that you got it together. You gotta show your cool tee."

"Wow," Scott breathed. He absent mindedly felt his neck again, causing his cock to begin hardening. It got even harder when Jim did the exact same thing,

smoothing the neck band of his T-shirt.

"Mm-Hmm. And you were showing your tee real good today," Jim said. Scott’s cock lurched. "But you got a boner again now, don’t you?"

Once again Scott blushed, nodding his head.

"Don’t sweat it. So do I," Jim admitted boldly. "Ever wonder why I sag my pants?"

"Cuz it’s cool?" Scott offered.

"Yeah, but check it out. They let me do something really great." And with that, Jim lifted the bottom of his T-shirt, exposing his washboard stomach and several inches of boxers.

At first, that’s all Scott noticed. But then he remembered that Jim had admitted having a boner. He scanned for evidence of it around Jim’s fly and didn’t see anything but a gentle swelling. But a moment later, he saw a bulbous bulge poking into the waistband of Jim’s boxers! His cock was sticking above his pants, with his boxers the only thing keeping it from view.

Jim laughed quietly when he saw the astonished look of recognition on Scott’s face. He dropped his tee and did some seemingly awkward maneuvering of his pants and underwear through the T-shirt. "Now check this," Jim said.

Scott looked at where Jim’s cock head was and could see a ridge under the soft cotton of his T-shirt. Suddenly the ridge jumped and became momentarily more prominent. Then a small spot of moisture appeared at the tip of the bulge. Scott suddenly realized that his cock was now sticking out of both his pants and boxers, and was now in contact with his tee!

"Uh huh," Jim said with a conspiratorial hush. "And now I can fuck my T-shirt." And as Scott watching in amazement, Jim began humping his hips, making his cock slide against his stomach, his boxers, and his T-shirt.

The room was silent except for the sound of fabric rustling as Jim continued to "fuck his T-shirt." He was actually getting the most stimulation from the friction of his cock against his stomach and the confining waistband of his boxers. But the sensitive underside of the head was sliding deliciously against the soft cotton jersey of his cool T-shirt. Soon, Jim’s breathing became more noticeable.

"Pretty cool, huh?" Jim asked. "I can do this anywhere, any time." Scott was incredibly aroused, but speechless at the display. "Just a few quick humps and I can completely sperm my cool T-shirt," he continued, his hot talk turning him on all the more. "I fuckin jizz my tee in class, at the movies, driving my car, any time I want. Course, if I’m somewhere people will see, I gotta be wearing another shirt over my tee, but I figured you’d like seeing this..."

Scott’s cock throbbed like crazy inside his pants, arching painfully against the restraining fabric. He reached down and adjusted his bulge.

"And you don’t have to use your hands," Jim continued, noticing Scott’s adjustment. "It’s cooler to do it this way than to beat off."

"But don’t you stain your T-shirt?"

The question caused Jim to increase his thrusting. "Oh fuck yeah!" he exclaimed excitedly. "I got tees that are so fuckin stained... so fuckin cool... aw fuck... fuck! Yeah... oh yeah... here it comes."

Scott watched intently as Jim made a couple of final thrusts, and wet streamers appeared on the T-shirt over his stomach. Jim gripped the arms of the chair as his concealed cock spewed wad after wad of hot cream, much of it soaking into his shirt. The movement of his hips caused the folds in the fabric of the T-shirt to move around, letting his cum fly in various directions. But soon the wet fabric was just clinging to Jim’s stomach, showing the color of his flesh through the saturated material.

Just like the day he first tried on his cool T-shirt, Scott, too, began squirting his cum without laying a hand on his crotch. He did his best to hide that fact from Jim by controlling his breathing. But he couldn’t help looking down at his crotch to see if his cum was soaking through. So far, nothing. Then he realized that the wetness was no doubt being absorbed by the tucked-in tail of his new T-shirt! That realization, that he was creaming into his tee at the same time as his new, older friend, caused a powerful contraction in his groin, one that he couldn’t hide from Jim.

Sure enough, Jim noticed. "All riiiiiight!" he said through clenched teeth, his own orgasm intensifying at the sight.

The sensations of the slippery, hot cream in his pants were too much for poor Scott. "I... I gotta grab it," he squeaked apologetically, as he gripped his fly.

"Go for it," Jim encouraged, his own orgasm waning.

Scott pumped a few times on his ejaculating cock, just enough to provide a satisfying finish to his climax. Both boys were sweaty and breathing heavily from their sexual release.

"Hey, you really are a cool little dude," Jim said. "We gotta do this some more, dontcha think?"

Scott smiled and said, "Yeah."

That night, Scott scoured his wardrobe for pants that would sag down low on his hips. There just weren’t any. He went through his wallet. There wasn’t enough for a new pair of jeans and lunch this week. He’d have to wait until next week. Then he remembered his sweat pants. They had an elastic waist, so he could wear them as low as he wanted. They weren’t the same as the jeans that Jim and the other boys wore, but they’d let him try out this new technique.

He actually had not changed clothes after coming home from Jim’s house. The cum never did soak through to his pants, and he really didn’t mind the dampness in his shorts. But now his clothes were all dry. He pulled off his pants and button down shirt, leaving him in just his tee and boxers. His cock was already bone hard in anticipation of what he was about to try. He then pulled on his sweat pants, deliberately leaving them quite low on his hips. He giggled again at the new sensation. Sitting in his chair, he adjusted the waistband of his boxers so that his cock head stuck out the top. Not being as well endowed as the older boy, he had to get everything very low to make it work. He noticed a stiff area on his T-shirt where his earlier load had been absorbed. His cock head was now pressing into the shirt just above the old stain.

He began thrusting his hips the way he’d seen Jim do it. It was certainly a new sensation. The top of his penis was sliding on his smooth tummy, while the bottom was being held by the elastic of both his boxers and sweats. The underside of the head was being tickled by the light fabric of his cool T-shirt. It didn’t take long for him to get a rhythm going, and it wasn’t much longer before he recognized that this was really going to work. He was going to cum into his cool tee!

The thought of the stain he was about to make didn’t enter his mind until it was too late. Remembering Jim’s huge ejaculation into his own cool T-shirt that afternoon gave Scott the stimulation he needed to bring himself off. When the first spurt wet his tee was when he suddenly realized that he really didn’t want stains all over his brand new, super cool T-shirt. Another spurt streamed up under a fold in the material, and he could feel his semen running back down his stomach and into his sparse pubes. He was about to lift his shirt and finish his orgasm by jacking off when he remembered Jim’s admonition that cumming this way was cooler than beating off.

‘It’s cool to squirt in your cool T-shirt,’ Scott thought as even more hot wetness spurted from his boner, further drenching his shirt. He let the rest of his cream out right into the T-shirt, all the while thinking about the cool Junior who showed him how to do it.

Scott slept very well that night.

The next day, he was looking forward to seeing Jim and telling him what he did. He had also decided to wear just a T-shirt today with no shirt over it. Now he was showing off his cool tee completely. He noticed several guys doing the same, but none had shirts as white and with as tight fitting necks as he did. Of course, every time he became aware of walking around in the coolest T-shirt in the school, he’d pop a boner, but the shirt was long enough to cover the bulge.

When Jim saw Scott come into the locker room, he laughed out loud. "You’re really going for it, aren’t you?" he asked.

"Yep," Scott said with pride in his voice.

"Had a boner all day, too?" Jim asked quietly. Scott just gave him a sheepish grin. "I thought so," Jim said. "Hey, come over again after school. There’s something I want to try. Oh, and check this out."

With that, Jim unbuttoned his shirt to reveal his Spartan tee underneath. Scott didn’t really think much of it until he took a close look. The whole bottom half of the front was covered with yellowish stains! Scott’s eyes opened wide.

"I told you I had some really stained tees," Jim said. "I’ve jizzed this one hundreds of times."

Scott really wished Jim hadn’t shown him that. Now he was getting his umpteenth boner of the day and he still had to change into his gym clothes.

Jim knew this. "Just leave your T-shirt on ‘til you get into your jock and gym shorts," he said calmly. Scott followed his advice, but when he dropped his pants, his new boxers, the ones that matched Jim’s – were exposed.

Jim laughed again, but all he said was, "Cool boxers."

Scott grinned, and quickly changed into the confining security of his jock.

Later that afternoon, Scott made his way to Jim’s. Wearing his cool tee and knowing that Jim would want to do something sexual had his cock standing tall. Jim came to the door wearing the stained T-shirt he showed off earlier.

"Man, that is one messed up T-shirt," Scott said once they got into the den.

"Yeah," Jim said, looking down at the stain. "This is my favorite one for creaming. Check out how this collar fits."

Scott looked. It was as high and tight as you could want. Definitely a great tee.

"Hey Jim, I got off like you showed me last night," Scott said, eager to share his experience.

"Cool. And you didn’t use your hands?"

"Nope," Scott replied proudly.

"Excellent!" Jim said, already adjusting his boxers so his cock poked out the top. "What were you wearing?"

"Well, I didn’t have any jeans that sagged like yours, so I wore sweatpants over my boxers," Scott explained.

"Were those the same boxers you wore today?" Jim asked, beginning to hump against his clothes.

Scott blushed. "No. But I did cream these the same day I bought them," he admitted.

Jim laughed again, but his humping intensified. "That’s cool. I cum in them, too."

That comment caused Scott’s boner to release a drop of pre-cum into his shorts.

"Hey, uh, can I ask you to do something for me?" Jim asked hesitantly, still working his hips.

"Yeah, sure," Scott replied. He’d do just about anything for his cool new buddy.

"Well, you know, one place I’ve always wanted to get cum stains on this T-shirt is the neck band." His humping was getting more intense. "It’s so fucking high and tight, it looks so cool under a shirt, it’d be just hot to see a bunch of jizz all over it."

Scott wasn’t sure where this was leading.

"It’s just that, well, I can’t squirt far enough to do that, you know? So I thought, well, maybe you could, like, you know, jack off on it for me," Jim finally managed to say.

Scott was shocked. The sort of spontaneous orgasms they’d shared was one thing, but this was a whole new level.

When Scott didn’t say anything, Jim got kind of scared. "Hey, it would be just between us, man. I just... I just want to feel cum on the collar... it’d be so hot, man."

Scott’s cock was throbbing and leaking as he thought about what he was going to do. It didn’t take him as long as Jim thought to make up his mind to do it. In fact, he wasn’t at all sure he’d be able to get his cock out of his pants in time! But he decided to play with the cool Junior.

He leaned back into the couch and smirked, "You want me to cream on your coolest T-shirt, man? You want me to squirt cum all over the neck? All over the part of the shirt that everybody’s going to see under your button down?"

Jim had a painful, almost desperate look on his face. He wanted this more than anything. And now he had to endure the taunting of a Freshman boy to get it. "Yeah Scott, come on, cum on my T-shirt."

Wordlessly, Scott stood up and walked over to the chair where Jim was squirming uncontrollably. Scott could see a big pre-cum spot amid the yellow stains on Jim’s shirt. He unzipped his pants, and worked his boner out through the opening in his boxers.

"Oh fuck," Jim intoned when he realized his fantasy was about to come true. He stopped his thrusting and stared at Scott’s cock. "You gonna do it? You gonna cum on my coolest T-shirt?"

Scott wrapped his hand around his boner. "Yeah," he said. "I’m gonna squirt my load right on your coolest tee."

Jim was a coil of sexual tension ready at a moment’s notice to release all his pent-up energy. "Fuck, oh fuck," he intoned repeatedly under his breath.

As Scott began stroking, he looked at his over-aroused friend and decided to give him everything he wanted. "Yeah, I’m gonna jizz your Spartan T-shirt, the T-shirt that makes you think you’re so cool, the T-shirt that all the girls like to see you wearing, that all the guys want to own. I’m gonna get it all stained up so you can’t wear it in public any more."

Jim’s quiet intonation changed to "No, oh no, not my cool Spartan. No, please." Scott noticed that Jim was still not thrusting his hips, but Scott didn’t know this was because he was desperately trying to hold back his load until Scott unleashed his.

He wouldn’t have to wait much longer. Scott was really getting into this. His stroking and his breathing became quicker as he said, "Such a cool T-shirt. Gonna sperm right on it, right... on... it. Aagghh!"

Even in the throes of the most intense orgasm of his life, Scott managed to carefully point his cock right at Jim’s neck band. The first shot was kind of small, landing on the seam at the base of the ribbed material. The second shot, however, was huge, completely splattering all over the neckband, Jim’s neck, and running down over his collarbone.

That triggered Jim’s cock to release its heavy load. The area around his cock head, already saturated with pre-cum, became dark and shiny as he squirted sperm under the cover of his favorite jack-off T-shirt.

Now Scott really lost control and began jacking his load all over Jim’s face, neck and chest. Several more shots landed on the target, Jim’s ultra-cool Spartan neck band, but the cum was flying hard and fast, and it was going everywhere.

The cool Junior boy now lost his facade and gripped his cock through the soaking wet fabric of his T-shirt. He began jacking it for all it’s worth, making sloshing, slurping wet noises as he filled his T-shirt with hot cum. White slime bubbled through to his hand.

Scott had finally drained the entire day’s worth of boners and frustration all over his T-shirt friend. He watched as Jim finished his own orgasm and marveled at how utterly soaked his T-shirt was. It now had two fresh loads – Jim’s had made a single, large wet patch at the bottom, and Scott’s had resulted in a variety of streams and splatters all around the neck of Jim’s shirt.

For almost a minute, the only sound in the room was the boy’s heavy breathing as they came down from their intense climaxes. Then, at the same moment, they looked at each other – Jim covered in cum, and Scott still holding his wilted cock in his hand. There was only one thing to do. Both boys sputtered and began laughing hysterically.

When the laughter ebbed, Scott asked, "So, you gonna wear that T-shirt tomorrow?"

"Fuck yeah," Jim said defiantly. "I think I’ll wear it under my V-neck sweater. Really show it off."

This started another round of laughter. The boys knew there’d be more fun in T-shirts to come.

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