Michael
was excited. He had a little extra spending money, so he decided to buy some new
boxer shorts. It’s what he usually did with his extra money. Michael was a "sagger"
– he liked to wear jeans and khaki pants that were too loose, so they would ride
very low on his hips. And when his shirt was off, the waistband and several inches
of his boxers showed above his pants. He loved showing off his underwear to anyone
who would look. Often when he was wearing a T-shirt, he’d casually lift the bottom
of the shirt up and rub his stomach, just to let whoever was in front of him see
his shorts.
He had particular tastes when it came to what were "cool boxers." He didn’t like boxer briefs, he preferred the full-cut traditional boxer shorts. And he liked patterns on his shorts. Plaids and stripes were cool, but small geometric patterns he thought were the best. When he knew he’d be somewhere where his shirt would come off – hanging out with his buddies, a party, or the skate park – he chose his coolest clean boxers.
There was a erotic side of showing his underwear for Michael. He’d frequently pop boners when he was sagging and his shorts were showing, especially when someone noticed them. It didn’t much matter whether it was a guy or a girl who was staring at the pattern on his boxers, he just thought it was totally sexy to be showing them off.
Recently,
when he was hanging out with his buddies, one of them, Nick, was wearing a pattern
that he thought was particularly cool. Just looking at Nick’s shorts had given
him a hard-on. He’d just spent the afternoon at the mall looking for that particular
pattern. He was really happy to have found it. And it was packaged with a cool
plaid and some stripes that he’d also seen Nick wearing, so he knew he’d enjoy
wearing all of them. He couldn’t wait to try them on.
On
his way home, his pants were sagging so low that some of his boxers showed between
his t-shirt and the top of his pants. When a hot guy noticed his shorts, Michael
couldn’t help but give him a show. He stopped in a doorway and "casually"
lifted the bottom of his shirt, showing five or six inches of his patterned
boxers. When the guy he was showing off to stopped and watched, Michael’s cock
began to stiffen, and he decided to go further with his display. He took his
t-shirt off altogether, and stood there "adjusting" his underwear
for the benefit of his audience. The other guy smiled, and wished he could hang
around and get to know this sexy sagger, but he was late to meet someone else
and had to leave.
The little show just invigorated Michael. Bounding up the stairs to his place, his semi-hard cock flopping around inside his loose clothes, he burst into the room, flung his back pack on the floor, and kicked off his shoes. He opened his pack and removed the package of brand-new boxer shorts. Taking it over to the couch, he tossed the package on the coffee table and sat back on the couch. Looking at the unopened package, he began fondling his still semi-erect cock through his loose khakis and boxers.
Michael
then picked up the package and, almost reverently, opened it. "Wow, I can’t
believe I have the same pair that Nick had," he said to himself. He opened
up the shorts and spread them out on the table in front of him. "Oh yeah,"
he said gleefully. "This is hot...yeah."
He
remembered how he had showed his boxers to the stranger on the street, and suddenly
wanted to see how he looked to the other guy. He had bought a full-length mirror
the day before, but hadn’t had time to hang it on a wall, so it was propped
up on a chair. He walked over to it and looked at his image. Grinning uncontrollably,
he began adjusting his boxers, and squeezing his trapped boner. This went on
for several minutes as he posed for himself, admiring how much of his underwear
showed over the top of his baggy khakis.
"Oh
yeah," he sighed. After a few minutes of rubbing, he went over to the couch
and once again looked at his new purchase. He quickly took off his pants and
boxers, revealing his stiff cock, and pulled on the striped pair. Pulling up
his pants, he walked over to the mirror and once again began adjusting his clothes
and playing with his boner. His pants were so low, the base of his cock was
just below the waistband, and the tumescent bulge of his throbbing cock could
be seen trying to push its way out.
As
much fun as he was having showing off these boxers, he really wanted to try
on the pair he’d seen his buddy Nick wearing recently. Going back to the coffee
table, he once again dropped his pants and shorts, and picked up the boxers
with the really hot pattern. "Yeah, these are just like Nick’s," he
said. He pulled on the shorts and admired them briefly, then he pulled on his
favorite sagging pants and zipped up.
"Yeah,
hot," he said when he saw his reflection. Now he really began playing with
his pants, his boxers, and his hard cock. He liked to play with the waistband
of the boxers, pulling them up higher, pulling the waistband out and letting
it snap against his tight stomach, pulling his khakis pants lower on his hips,
and throughout, rubbing his increasingly hot prick through the new fabric.
Suddenly
he took off his pants and stood in front of the mirror in just his boxers and
socks. These hot boxers were like a new toy to Michael. He rubbed his cock in
every imaginable position: through the fabric, sticking out the fly, sticking
over the top of the elastic, even sticking out of each leg hole. With his cock
back inside the boxers, he held the fabric around the bulge and admired it in
the mirror.
After a while of doing this, he suddenly stopped and said, "Oh! I better not cum on my new boxers. I wanna wear these to the party tonight." And with that, he once again pulled on his pants. He gave himself one last look in the mirror, going "Yeah!" as he saw his perfect sagging style. He snapped his waistband once more and sat back down on the couch.
He
picked up the plaid boxers and fondled them, saying to himself, "I can’t
wait to show these off at the party, especially if Nick’s gonna me there."
Then, picking up the striped pair, he mused, "I wonder which pair Nick
will wear."
Now he couldn’t help but reach down and stroke his cock through his pants again. With his free hand, he once again adjusted the waistband of his shorts. His breathing became heavier. "I just can’t cum in my new boxers," he told himself. "Oh, it’s so hot though, man, so fucking hot...Fuck yeah!" He didn’t stop his stroking, though, as he examined the boxers spread out on the table.
Finally he tore his hand away from his crotch. "No cum stains on these new boxers," he said with resolve.
Michael
picked up the plaid boxers again and felt the slightly stiff cotton fabric.
With a plaintive cry of "Oh man!" he flung them down and once again
began rubbing his twitching tool. He thrust his hand down inside his boxers
and began stroking the bare flesh of his cock. A look of intense pleasure came
over his face.
With his right hand buried in his pants, stroking the base of his cock, his left began teasing the head through the two layers of fabric. Then he once again pulled on the waistband of his shorts, making sure that even while jacking himself off, his boxers showed just right.
Wanting to see even more of his new boxers, he unzipped his khakis and peeled them back. A triangle of patterned fabric was revealed with his boner trapped underneath. He continued masturbating under and through the starchy-soft cotton.
"Damn, I’m making a wet spot," he moaned, although that didn’t stop him from continuing to stimulate his cock. After a couple more minutes though, he once again announced, "Damn, I got a wet spot on my new boxers." He’d had plenty of wet spots before, in fact he jacked off in his boxers regularly. But he wanted to save these new boxers for the party later. By reminding himself that they were new, he gained the resolve to once again close up his zipper.
His resolve didn’t last long. He once again adjusted the boxer shorts’ waist band. He gasped, "Oh God, so hot though," as his hand went back inside his pants, and once again began jacking his leaking hard-on.
The pre-cum he'd been leaking started smearing all over his cock head. The slippery sensations were incredible. Suddently he could feel a desperate pressure building. Part of him wanted to feel the sweet release of an orgasm. The part that wanted to keep from staining his new boxers spoke up, though. "Oh God. I shouldn’t be doing this!!!" he warned himself.
It
was in vain. Just seconds later, the first shot of molten cum began working
its way up his cock shaft. "Oh!" he exclaimed. "Awh! Awh! FUCK!"
Now Michael’s semen was firing right into the fabric of his new boxers and favorite khakis. His cock now coated in slimy cum, his hand began slipping and sliding over his cock flesh, causing a massive amount of cream to shoot from its tip. "Urgggh!" he grunted.
A
wet splotch appeared on the fabric of his khakis as his orgasm faded. With jizz
still leaking from his cock, Michael moaned, "Oh God! Fuck! I came in my
new boxers." But he wasn’t really that upset. In fact, he laughed with
the joy of the release, and grunted again as an "aftershock" sent
another glob of cream into his shorts.
When he finally finished cumming, he sat back and laughed again. "Yeah, I got the other two pair," he said, thinking that it probably wouldn’t be cool to wear cum soaked boxers to the party.
Wanting
to inspect the damage to his new boxers, Michael unzipped his khaki pants and
peeled them down to reveal his cum stain. "Oh man! My new boxers..."
he said. He put his hand back inside his boxers, and began feeling all the hot
juice on his cock and on the fabric. He was wondering if he should just go ahead
and wear these boxers to the party anyway...