In the tenth grade I met Derek. Derek was a handsome, five foot ten inches tall guy with a great body at my school. We met in homeroom and hit it off due to our mutual taste in music. I noticed Derek on the first day of class. This was in 1990 and Umbros were popular. He was wearing white Umbros and a navy blue tshirt. The white briefs he wore under the Umbros were clearly visible. I was fixated on his briefs. I too wore white briefs under my Umbros, but I never had the courage to wear anything see through like those white Umbros. Mine were all dark colors. As he walked out of homeroom I walked behind him. I could clearly see every bit of his briefs. It was great. I introduced myself and we actually had our first two classes together. We sat beside each other and I kept looking at his briefs through the thin white material. I was hooked.
That night I fantasized about what I had seen. The next day I was anxious to see what he was wearing. I was in for a treat. He was wearing light grey Umbros and a white tshirt with what looked like colored briefs under his Umbros. I had never seen colored briefs before, so I wasn't sure if the material of his Umbros was making it look like he had on colored briefs. Lucky for me he turned in his desk to face me and the space between his leg and his Umbros opened up wide to reveal his crotch covered by the light blue briefs he wore. I got hard in my white briefs instantly. I was treated to more sightings that day as he walked, sat, and when his Umbros would open up.
The next day I saw his red briefs under his black Umbros. I wanted colored briefs for myself, but how? All of mine were white. I had just gotten a batch of new underwear for school so I knew my mom wouldn't buy me more.
On the fourth day he wore black spandex shorts with lime green stripes down both sides. Not only could I clearly make out the shape of his briefs, I could clearly see the outline of his dick. It was too much. Beneath my grey sweatpants, my dick was about to burst through my white briefs and I realized my boner was visible. I covered it as best I could with my books as we left homeroom. On the way to our first class, one of my other friends, Mike, came up to Derek.
"Man, you know everybody can see your dick in those shorts, right?" Mike said to Derek.
"Sounds like you're the only one looking" Derek responded.
"I can tell you're wearing underwear too!" Mike said. "Let's see what kind!"
Mike reached down, yanked Derek's white tshirt up with one hand, and pulled the front of Derek's spandex shorts away from Derek's body with the other.
"Hey! Stop it!" Derek yelled as the dark green briefs he was wearing were revealed.
Mike tugged down on Derek's spandex shorts when he saw the green briefs beneath. I felt bad for my new friend.
"Nice undies!" Mike laughed. He let go of Derek's shorts.
A small crowd had gathered and laughter came from all around as Derek pulled up the stretchy spandex material. He even adjusted his dick when his shorts were back in place. Nice!
"Very funny..." Derek told Mike.
Mike lifted the side of his shirt and yanked the side of the black sweatpants he wore down. He pointed to what, to me, looked like orange Speedos.
"Next time, get some nylon bikinis" Mike said. He released his sweats and his shirt. "Those are Underoos."
Mike walked away. Derek was pissed.
"What was that all about?" I asked.
"That guy sucks" Derek said. "I wear sexy underwear too."
"All I wear is regular white ones" I said.
"I have some nylon ones" he said.
"What? You wear Speedos?" I asked.
"No, I have some nylon bikini briefs like him."
I was lost. Only two days before had I seen colored briefs for the first time. Now, apparently, there were different kinds of briefs too. I wondered how many other guys wore colored briefs and bikini briefs and how many wore regular white briefs like me.
The next day was Friday. Derek wore red Umbros and I eventually got a glimpse of his briefs. They were burgundy. My favorite color! I wanted them badly.
Luckily enough Derek invited me to come hang out at his house after school. I eagerly accepted. I wanted to look through his underwear drawer to see what other colors he had.
I couldn't wait for school to end. Finally it was over. As we walked to Derek's house, Mike caught up with us.
"What do you want?" Derek asked him.
"What? Are you pissed about that yesterday?" Mike asked.
Mike looked at me and pulled the front of his navy blue Umbros away from his body. I could see his underwear. It was a skimpy pair of red bikinis with thin white horizontal stripes. The material was so thin that I could see every aspect of his dick.
"Dude, I got some sexy underwear this year! I got like twenty pairs of nylon bikinis! I'm gonna get laid for sure!" Mike boasted.
"Good for you" Derek said.
Derek and I started back on our way to his house. Once we were there we went to his room. There was a pile of laundry on his bed. There they were! The light blue briefs, the red briefs, and the green briefs. All folded and mixed in with several white briefs. I was in awe. Derek said he had to go take a shower. He walked over to his dresser, opened the second drawer, and pulled out a pair of light grey briefs. He left the drawer open and left the room.
I waited until I heard the water running and then I looked inside the drawer. It was full of his briefs. A few were regular white cotton briefs like mine. Most were regular cotton briefs in various colors with a plain white waistband. I picked up a navy blue pair and looked at the tag. They were Fruit of the Loom. So were my white ones. The bikini briefs were a mix of solid colors and patterns like leopard skin printed. The fabric was soft and sexy. I looked at the tags. The solids were made of stretch nylon and were Hang Ten brand. The animal print were polyester and Jockey brand.
I knew what I had to do. I saw that sexy red pair in his laundry pile. I had to have it. I kicked my shoes off and in one quick motion pulled my Umbros and white briefs off. I picked the red pair out of the laundry pile and pulled them on. I had precum wetting the front of the red cotton material as soon as they were in place.
Without warning Derek stepped into the room wearing only those burgundy briefs I had only glimpsed before.
"What are you doing with my underwear?" He asked.
"Um...I...just..." I stuttered, unable to say anything to explain myself.
Derek walked over to me and put his right hand on the red cotton fabric covering my boner.
"Take off the shirt" he said.
I pulled my shirt off. I was standing in front of him wearing only the red briefs I had just stolen from him.
"You like my underwear?" He asked.
"Yes. Yes I do. I love it" I answered.
He rubbed my dick from head to shaft over and over.
"What about the ones I'm wearing now?" He asked.
"My favorite" I said.
He took my hand and stuck it inside the front of his burgundy briefs. I wrapped my hand gently around his dick and began stroking it. As he got hard, I was impressed by the size. He was easily seven inches and cut. He put his hand down the front of the red briefs I wore and he slowly caressed my dick. My six and a half inches of cut dick tremored in his hand.
He knelt down and lightly pulled the red briefs down. He put his lips around my dick and proceeded to give me a blowjob. I felt my body shake slightly as his mouth engulfed every inch of me. I could tell he had done this before. He gripped my hips and I began to hump along to his rhythmic motion. He rubbed my hips, ass, and inner thighs as he took me to heaven in his mouth. I stepped out of the red briefs and guided him to the bed. I sat on the edge of the bed as he continued sucking me off.
I moaned as he sped up. I caught a sight of him still wearing those sexy burgundy briefs and I started to cum.
He pulled away and jacked me off with his left hand, sending cum flying all over my chest. He reached over and picked up a pair of his own white briefs from the laundry pile next to me. He wiped my cum off my chest and tossed the white briefs onto the floor.
"Mmm, that was good" he said as he laid beside me.
I reached over to touch his cotton encased dick. His sexy briefs were wet with cum.
"I couldn't help it" he said with a smile. "Oops!"
"That was amazing" I said.
"Looks like I better put on a new pair of underwear" he said. "You too. Those red ones have your precum all over them."
He stood up and walked over to the open drawer full of his briefs. He pulled out a pair of the Hang Ten nylon bikinis in black. He pulled them on. The stretchy material hugged the outline of his dick perfectly.
"I only wear my sexy bikinis on weekends" he said.
He reached into the drawer again and pulled out a pair of white cotton briefs.
"Can't believe you only wear this kind" he said.
He put them back in the drawer and tossed me a pair of light grey cotton briefs.
"We're gonna have to change that!" He told me.