Brief Encounters

*****Everyone in this story is fictional and over the age of 18*****

Chapter 5: Detention

The lunch lady winked at me as she poured another scoop of corn onto my tray. She knew I loved corn. Her name was Linda a lovely lady in her 50s. I thanked her and went down the row to the cashier where I paid for my food. I sat at an empty table with my food. My friends, James and Franks whom I normally sat with were on a field trip, which was the reason why I was alone at lunch.

I was almost done eating my lunch. All I had left was a cherry tomato which had turned into a soccer ball in my mind. I played with it with my fork moving it from one side of the tray to the other. I couldn't wait to play soccer in college. I was a senior in high school and one of the very few who had turned 18 while still in school. The soccer season was over which is why I was playing soccer with my cherry tomato.

My cherry tomato soccer game to an end when I heard a commotion. I turned around towards the source of the noise and noticed it was Cillian and his group of friends playing around. They were a few feet away from me. Cillian was the quarterback for the school's football team. He also happened to be my crush. But I never acted on it due to him being straight.

Cillian was also 18 years old. He was tall and thin but had a muscular body. He had short brown hair with emerald-colored eyes. His skin was tan and he had an infectious smile. Despite other high school quarterbacks, Cillian wasn't a bully. He was a very friendly guy and he even spoke to me. I guess it was because we were both on sports teams so he didn't see me as the nerd that I truly was. 'The athletic nerd," is what my friend Frank would call me.

Cillian was surrounded by his friends, Nathaniel, Ricardo, and Elliot. From that trio of friends, only Ricardo I found attractive. The other two looked stupid. Ricardo was Puerto Rican and looked like a young Daddy Yankee. But I knew I never had a chance with him. The man was straight and had a girlfriend. I would have to cast a gay spell in order to even have a chance of having sex with him. Unfortunately, magic wasn't real. It was the same with Cillian, to be honest. The man was straight.

I ignored them and pressed my fork into the cherry tomato piercing the skin, and lifted it towards my mouth. It was about to enter my mouth when I heard yelling. Once again I turned to see Cillian and his friends get more rowdy. This time, Cillian had Ricardo's head locked under his arms. Ricardo pleaded with him to release his head but Cillian refused. That's when Nathaniel went behind Cillian and pulled on the waistband of his underwear. My jaw dropped open as I was Cillian get a wedgie. What was truly shocking was the fact that Cillian had a pair of gray briefs.

Cillian let go of Ricardo and stepped back. The trio then began to laugh at him as he tucked his underwear back into his pants. Cillian's face turned red. He was so embarrassed that he shoved Ricardo to stop laughing, but the Puerto Rican continued to laugh. They were laughing so hard they couldn't speak. But it seemed they were trying to point out that Cillian had on briefs.

Cillian shoved Ricardo once again. This time Ricardo stopped laughing and carried a serious look on his face. Ricardo shoved Cillian back getting a little too close to me. I was about to say something but Cillian pushed Ricardo back. Which resulted in Ricardo retaliating and pushing him back harder. Cillian's body collided with mine and both of us fell to the floor. It happened so fast that I wasn't able to react in time.

The cherry tomato rolled past my head. I turned to Cillian who got up and put his hand out, I slapped it away. I was so annoyed that he had knocked me off my bench. I got to my feet and dusted my clothes. Once again Cillian came to me and asked if I was okay, but I was too furious to hear him clearly. I pushed him back and he quickly got upset and pushed me back. This time I fell towards the table causing my lower back to hide the side of the metal table. I grimaced in pain and that's when a teacher came between us.

"Hey! Stop this!" the teacher looked at both of us.

I quickly calmed down but not for too long as the teacher then said, "Both of you, detention!"

"What? But I didn't do anything," I pleaded with him.

The teacher shook his head and said, "You shoved him back, escalating the situation. The both of you have detention," he then turned to the trio of guys who were laughing, "You three also have detention!"

The school bell rang. I marched myself to the detention class. Rarely did I have detention. I still couldn't believe that I got it and it wasn't even my fault. I entered the classroom where I saw Ricardo, Nathaniel, and Elliot sitting in the back. The classroom was full. I handed the teacher my detention slip and he shook his head, "Sorry, I'm full. You're going to have to go to the other detention class."

I groaned, "The one in the basement?"

He nodded.

"That one is literally a freezer."

The teacher simply shrugged.

I stood at the top of the steps of the main building. The basement was right at the end of the steps. I hated that room. I climbed down the long flight of stairs and entered through the basement door. There was Coach Cai, he was the coach for the school's basketball team. On the desk was a barely opened pack of cigarettes and a newspaper. He turned to me as I handed him the detention slip. He said nothing and just nodded to the empty desks in the room. No one else was in the room besides him.

I sat in the third row, third chair furthest from the left of the room. I placed my bag on the table and sighed. A few minutes later, Cillian appeared. I quickly turned away. Although I had a crush on him I was so mad at him. It was because of him that I was down in the freezer.

Cillian walked down the middle aisle passed me and sat at a desk across from me on the row behind me. I didn't want to turn around to see him.

No one talked. The only noise came from the coach when he coughed. He flipped through the newspaper and then coughed again. I looked at the clock and saw I still had 40 minutes to go. It was cold. And I hated it.

Coach Cai lowered his newspaper and looked at both of us. He grabbed his pack of cigarettes and rose from his chair. He then walked to the door and said, "Remain quiet...or don't. Fuck if I care," then coughed and walked up the stairs.

Not like I had any reason to talk. Especially to Cillian. Fucker got me in detention. I was so pissed at him. But the image of him getting wedgie stuck in my mind. I couldn't believe that he wore briefs. I wonder why he wore them. Did he have some fetish? Was he coerced by a girlfriend to wear them? Or did he just genuinely like them?

I felt a tap on my shoulder, I didn't know when it happened but Cillian had moved to the desk behind me. "Hey, I'm sorry for crashing into you."

At that moment all my anger towards him fled. I smiled, "Thanks, Cillian. I know you didn't mean to. I'm sorry for shoving you. And sorry for being mad at you."

"It's no problem, Mitch. I'll make it up to you somehow. I just got carried away at the moment."

"I don't blame you. You got wedgied by your friends and exposed your briefs."

His face flashed red, "You noticed the briefs, huh? It's a good thing I wasn't wearing one of my white pairs. The teasing would've been far worse because of the whitey tighties."

"Whitey-tighties," I corrected.

"Is that what they call it?" he laughed.

"Yeah. I have to ask though. It's not common for straight dudes like yourself to wear briefs. Why do you wear them?"

Cillian shrugged, "I've always liked wearing them. Boxers and boxer briefs ride up too much for my liking. My dad wears briefs too and calls them a man's underwear." He explained to me one day that they just get the job done, they give you the support and cover what's important. But you know nowadays, briefs are frowned upon and often a reason to bully someone. I do wear trunks though when I know I am going to have to change in the locker room."

"Well, I definitely agree with you on the part of the brief. As I wear them myself. But aside from comfort and support, I also find them very sexy on people. Especially, straight men like yourself."

Cillian grinned, "Is that so?"

I shook from the cold. Cillian noticed it and got up from his chair. He took off his letterman jacket and put it over my shoulders. Then he grabbed a chair and sat next to me. The gesture took me off guard. I wasn't expecting him to do such a nice thing to me.

"Thanks, Cillian. You didn't have to. What about you?"

He shrugged, "I work in a freeze at my dad's gas station, I'm used to the cold. Another reason to wear briefs, is they keep you warm down there."

"True that."

"So how long have you been wearing briefs?"

This is a conversation I never thought I would ever have with a straight man, let alone Cillian. But it was happening and I was happy.

"Honestly, I never changed my underwear. I tried boxers and boxer briefs, like yourself but also didn't like them. My mom kept buying me them but just could never get into them. When I got my own money, I would buy my own pairs of briefs. I started with Hanes and Fruit of the Loom, but then started buying higher quality briefs and never went back."

"Better quality? Like Calvin Klein?"

I nodded, "And a few other brands."

The sentence intrigued him, "Oh yeah? What other brands? I wouldn't mind trying out some new ones."

"Well, I own a few Boss pairs. A few Tommy Hilfiger, which I have on right now. There are also some lesser-known brands like Tani and Mack Weldon. I know a dude who wears exclusively 2(x)ist."

"Hey! I know that brand. I have a few pairs of those. A girlfriend's brother gave me a pair once out of nowhere."

"Wow, that's funny. Maybe he wanted you to model them for him."

He smiled, "Maybe. But it's too late now. I don't date her anymore."

"I just can't believe we're having this conversation."

"Why is that?"

"It's just not a conversation two men normally have."

He chuckled, "Yeah, I guess you're right. Especially with my friends. The thought of an underwear conversation would just cause them to laugh at you and call you gay."

I was glad that my legs were closed because I had a raging hard-on. I couldn't believe that he was casually talking about briefs with me. As if it were nothing. I could just imagine him walking out of the shower with just a towel on and opening his drawer full of briefs. Slipping on a pair and walking around the room in them.

He tapped me on the shoulder and broke me from my thoughts, "You okay there?"

"Yeah, it's just, I bet you look hot in those briefs."

His eyes widened, "I mean, I've not heard anything to the contrary," he sat up in the chair and said, "Hey! Why don't I show you?"

My eyebrows rose in shock, "Really? Here?"

"Yeah! Why not! I owe you anyways."

"What about Coach Cai?"

Cillian rose to his feet and began to undo his pants, "Don't worry about him, he'll finish his pack of cigarettes before he comes back down here. Heck, he'll probably end up leaving."

"Are you sure?"

Cillian didn't answer me, instead, he opened the flaps of his pants and pulled the pants down to his thighs. I gulped in amazement at his gray Calvin Klien briefs. I knew exactly what pair he had on too, as I had the same pair but in white. They were the Icon Micro briefs. They had a metallic silver waistband with the brand's name in giant letters. The underwear fit him so well and snugly. His bulge was shaped like a pear with his member pointing north. The sight alone was enough for me to want to ejaculate in my own briefs.

"So what do you think?" Cillian said.

I gulped, "My God, Cillian, those briefs look amazing on you. Can I see the backside?"

"Of course," he turned around.

Each butt cheek filled the underwear well. His cheeks were so round it reminded me so much of a peach. The urge to reach out and touch it was strong.

Cillian turned back around, "Not bad huh?"

"You could be a model for Calvin Klien."

"You really think so?" He said excitingly.

"Hell yeah!"

"Maybe I should apply," he paused and then said, "Let me see what you look like in yours?"

"You serious?"

"Yeah, I wanna compare."

I was reluctant to do it because I knew I had a stain from the precum and I knew he would notice it right away. Maybe it would even cause him to end this. But it was only fair to do it.

I rose from my seat and undid my pants. I peeled them off to expose my white Tommy Hilfiger briefs. The stain wasn't instantly noticeable but if he looked more carefully he would notice it.

"Not bad, not bad. I see playing soccer has paid off," Cillian said referring to my muscular thighs. "Uh, I see you didn't shake in the bathroom?"

My face went red, "Uh, it's not that, it's precum," my voice trailed off.

"Oh?" then the realization hit him, "Oh! I see. You got a little aroused, huh?"

I chuckled nervously, "Yeah, you look really hot in briefs."

"I'm very flattered, Mitch," Cillian then snapped his fingers, "I got an idea to pay you back, you wanna suck my dick?"

Once again my eyes widened in shock. It felt like I was in a wet dream or a porn. Where the jock has sex with the nerdy guy. I was actually stunned by everything.

"Uh...what? Sure...oh my god," I blurted out.

"Relax," he assured me, "it's genuine."

"What about the coach?"

"Like I told you before, he'll likely finish his pack and then walk away. Trust me, I know Coach Cai."

"Are you sure you want to do this?"

"Yeah, I've never gotten head from a guy before. I've been told they are better than women," he shrugged, "Plus, I too got a little aroused by our conversation."

I planted my butt cheeks onto the seat of the chair. My pants were around my knees. Cillian brought his crotch closer to my face. It was true he was aroused. I could see the tip of his cock poking out from underneath the waistband. Any fear of getting caught went away as I dug my fingers under the waistband and pulled it down.

Cillian's cock sprung out before me semi-erect. The foreskin covered the majority of the tip of his cock. I brought my lips to the tip and used them to push back the foreskin. My tongue slithered underneath the shaft as I took more of his cock into my mouth. The contact made Cillian moan. I began to move my head back and forth slowly. Feeling the cock grow inside my mouth. My hands moved up and down his hairy thighs for a bit before moving around to his toned butt cheeks.

Cillian lifted his shirt as I sucked on his cock. It was now fully grown. I removed it from my mouth to stare at it for a moment. It was about 8 inches in length with the girth of a carrot. The foreskin naturally retracted exposing the bright pink tip of his cock. The cock had a slight curve to it. It glimmered in the light due to the coating of saliva on it. I brought my mouth and tongue to the tip and began to pleasure Cillian's cock.

My hands were glued to his toned butt cheeks as I sucked on his cock. I moved back and forth at a steady rate, taking my time, and indulging in the once in the lifetime moment. Cillian didn't hold back any moans. He fired them out like a machine gun.

I swallowed his cock into my throat. The warm muscles of my throat tightened around the tip of his cock sending waves of pleasure throughout his body. I felt his brown pubic hairs inside my nostrils, tickling it. A moan combined with a grunt left Cillian's mouth.

I released the cock from my throat and went back to bobbing my head.

The moans and grunts grew more frequent. I couldn't believe I was sucking Cillian's cock. I could hear his breathing grow deeper. I knew he was close. Using my left hand, I stroked the base of his shaft as I moved my head back and forth in rhythm with my hand.

Cillian bent forward slightly and planted his hands on my shoulders. A drawn-out moan left his mouth as he fired the first shot of cum. It splattered against the entrance of my throat. The rest of his load soon followed forming a pool of translucent gooey cum on my tongue. Some of the cum dripped down into my throat.

When Cillian finished, I used my tongue to lick his urethra making sure I got every last drop of his load. The cock left my mouth and I swallowed his delicious load.

"Holy fuck! That was amazing, Mitch. It is true, guys suck better."

I grinned, "I'm glad to be the one to make you realize that."

"I'd love for you to fuck me," I blurted out.

"I can go another round," he said with a grin on his face.

"Let's do it!"

"But let me sit down, my legs are a bit like jelly."

Cillian pulled the bottom of his shirt over his neck and pulled his pants down to his ankles, then he sat down on the chair in just his briefs. I removed my pants and briefs and climbed over him. I rested my thighs on his thighs and brought his cock to the entrance of my hole. I grabbed onto his shoulders as he pushed his cock inside me.

A gasp left his mouth and he rolled his eyes, "Fuck that's tight."

The cock slid inside me and he held onto each of my butt cheeks. The letterman jacket held onto my shoulders as he moved me up and down. The cock rubbed against my prostate constantly sending waves of pleasure up my body. Cillian would constantly release a moan and roll his eyes back from the pleasure.

Together we moaned, gasped, grunted, and rolled our eyes back as he fucked my tight hole. I continued to bounce up and down while he held a tight grip on my cheeks. Cillian stared directly into my eyes with his mouth wide open. Deep breaths left his mouth as he continued to show a face of amazement. His eyes rolled back as did his head. I felt the second load of cum explode into my rectum. But he continued to bounce me up and down as he released his gooey load. The amount of pleasure I received from it caused me to come to a climax. I held onto my dick as I fired my own load. It splattered on Cillian's chest. It was a total of five powerful pumps.

Cillian stopped bouncing me and looked down at the load of cum on his chest, he laughed and looked at me, "I wasn't expecting that."

"Yeah, my bad."

"I didn't even know you could cum like that."

"A good fuck like that will do that to you," I licked off the cum from his chest and got off of him.

I helped him clean up and then we got dressed. Together we left the classroom 15 minutes early and at the top of the stairs, Coach Cai was gone. Then we departed our own way.

The next week, I ran into Cillian in the hallway after the last period. He flashed a smile and said, "Hey, Mitch, how are you doing?"

I grinned, "I'm doing great how about you?"

"I'm good. Listen, what are you doing after school?"

"Nothing, why do you have something in mind?"

He grinned, "A few things. How about we go buy some underwear?"

"I will gladly go underwear shopping with you, Cillian."

We smiled and left campus in his car.