Brief Encounters Ch. 03

****All characters are fictional and are over the age of 18*****

Chapter 03 of the Brief Encounters Anthology:

Best Friends

It was a few weeks before the end of senior year when I had a sleepover with my two best friends, Dylan and Nick. The three of us had been friends since elementary school since we lived in the same neighborhood. We went through middle school and high school together. Some of us had it easy, while some of us didn't. I didn't have a good time. I was gay so that led to a lot of guys picking on me. But thankfully, I have friends like Dylan and Nick to come and defend me. Specially Nick. He was ready to throw hands if needed.

Dylan was tall and thin, he stood at six feet two inches. He was on the basketball team naturally. He was the jokester of the trio. Always cracking a joke even in the darkest of moments. Nick was the shortest of the trio, he was five feet and six inches tall but he worked out a lot. The man boxed and was on the school soccer team. He was a bit more serious but he had a soft side to him. He and Dylan would get into fights from time to time, however.

And then there was me. Well, I'm gay obviously and they both know it. Unfortunately, I have never had sex with either of them even though I've dreamt about it a few times. I was the middle of the trio, I was six feet even and thin. My muscles were located on my lower body as I played tennis a lot.

The school day had ended and so was the school week. Like I said previously, senior year was due to end and thus the end of high school for me. Me, Dylan, and Nick were some of the few who were over 18 due to when our birthdays landed. I had no plans for the weekend.

Dylan bumped into me with a smile on his face, "Hey, Myles, what are you doing after school?" He had his blue and orange basketball uniform on.

I shrugged, "I have nothing in mind. How about you?"

"Nothing. I was thinking why don't we go to my house and play some games."

"Like a sleepover? Aren't we a little old for that?"

"I mean if you don't want to that's fine."

It didn't bother me at all. It's just been a long time since we had a sleepover. "Sure, I'm down. You wanna go ask Nick?"

"Of course, let's go ask that shrimp taco."

The two of us laughed and walked to the soccer field.

When we got to the field Nick was still in practice. So Dylan and I sat on the bleachers and waited for practice to end.

The practice had finally ended. Nick noticed us right away and grabbed his bag, then walked to us. "What's up losers?" Nick said covered in sweat.

"Nothing much," I bent forward, "We were wondering if you wanted to have a sleepover at Dylan's?"

A confused look was on his face, "Sleepover? What are we twelve?"

"Oh come on? We only have a few weeks left before we all depart high school. I figured it would be cool to have a sleepover."

"It's a little gay, don't you think? No offense, Myles."

"A lot is taken," I said sarcastically.

Dylan's phone vibrated. He looked at the text message and cursed, "Never mind, my mom is having her boyfriend over tonight. The two will probably be fucking. I definitely don't want to be home for that."

"Fine, we can have the sleepover at my house," Nick said, "My mom is working a double and my dad is still on his business trip."

"Perfect!" I added, "We can try that new pizza place by your house."

"Good point!" Nick said, "Let me hit the showers and I'll be right out."

Nick left the locker room and showered.

A few minutes later, he reunited with us and we walked to his house. Nick had swapped his soccer team uniform to black shorts that ended just above his knee and a white tank top. As we walked we talked about what pizza topping we were going to get. We got to the pizza place and ordered the pizza. When it was done, we went straight to Nick's house.

We each made a plate and went to his room to play video games.

For the next few hours, the three of us played Mario Kart, Street Fighter, and some Call of Duty. It was now 8 pm at night and Nick suggested we watch the new Chris Hemsworth movie. Which we unanimously agreed to watch.

When the movie had ended it was almost 11 pm. Nick got off his bed and stretched, "Fuck, I'm still energized. What do you guys want to do next?"

"Fuck if, I know," said Dylan.

"We can play some more games?" I suggested.

"Nah, Nick has lost too much today."

"Fuck off!" Nick replied angrily.

Dylan brushed off the comment, "Quick to anger," he teased.

The thing with Nick was that he was quick to anger. And Dylan knew this. This often led to an argument. Nick grunted and walked to the door but while doing so he kicked Dylan's leg. Dylan's reaction was to pull on Nick's shorts, exposing his red and blue checkered boxers. Nick laughed and removed his hand. "Pizza face," Nick said. Referring to the time Dylan had an acne problem.

This aggravated Dylan. From the floor, he sprung up to his feet and wrapped his arm around Nick, "What you say, Shrimp taco?"

The two then began to fight. However, it was clear they were playfully doing it as they were both laughing. They always insulted each other. I stood up and rested my butt on the desk next to his bed as I already knew what was going to happen. Nick pushed Dylan away from him and the two locked arms once again. The two began to wrestle and I was the referee.

I stood there as my two best friends wrestled one another. Dylan had pushed Nick against the bed which allowed him to springboard himself onto Dylan. The two wrestled on the ground for a bit before both of them stood up. Once again, they locked arms Nick got the upper hand on Dylan and got him in a headlock. But it seemed that he was holding the head too tight as Dylan started to yell to let go. Nick wasn't letting go he was waiting for the tap, but Dylan wasn't giving it to him. Instead, Dylan did something else. He reached for Nick's boxers and grabbed them pulling them down.

My eyes widened and my jaw dropped in shock. I was expecting to see Nick's privates but I didn't. Instead, I saw he had underwear under his boxers. Not just any underwear. He had on a pair of white briefs under his boxers.

Embarrassed, Nick released Dylan and quickly pulled up his shorts and boxers.

Dylan looked at me in shock and then we turned to Nick. "Shut up!" Nick said.

"You wear tighty whities?" I said.

Dylan and I both started to laugh.

"I said 'Shut up!'"

Dylan sat down on the desk chair with his hand on his face. His face was turning red from laughter. Nick's face was turning red but for a different reason. "Stop laughing you two! Myles wears briefs too!"

"Yeah, but I'm gay. It kind of comes with the territory. Plus, I don't wear tighty-whities. I haven't worn those since elementary school."

Dylan calmed down, "It's cool dude. It's just funny. I mean why even wear them under your boxers?"

Nick sat down on the edge of the bed, "I like them okay? The support and they give me a lot of good flexibility. Some of the guys on the team wear them too."

"I bet they do, but I doubt it's tighty-whities!" I said between laughs.

"Fuck you guys!"

"So why tighty-whities?" Dylan said holding back a laugh.

"They're cheap. You can get a lot for the price. I use them for practice"

"Okay, he has a point. They are usually cheaper and you get a lot," I said. Dylan burst into laughter which caused me to do the same.

"You know what? Fuck you guys! I don't want to have a sleepover anymore. Go home!"

The laughing stopped and that's when Dylan stood up to apologize, "I'm sorry, bro,"

But Nick wasn't having it, "Nah, I'm good. Go home. Fuck you two," He then lay down on his bed and began looking at his phone, "You know where the door is."

Dylan looked at me and we shrugged. "I really wanted us to have a good night and I am sorry for laughing."

"Go away!" Nick said.

Dylan sighed. Then it looked like a lightbulb turned on over his head. He opened Nick's drawers until he found the underwear. He pulled out a pair of his white briefs and disappeared into the bathroom. A moment later he came out wearing a pair of Nick's white briefs, "Look, Nick!"

Dylan looked absolutely sexy in the underwear, to be honest. They hung a bit loose on him due to him being skinnier than Nick. But they looked good on him.

"Go away!" Nick repeated.

"Come on, Nick" I urged.

Nick reluctantly turned around and saw Dylan in a pair of underwear, "You really wearing a pair of my briefs?"

"Yeah! And to be honest, they are comfy."

"Don't patronize me," Nick said without emotion.

"I'm serious," Dylan said, "What you think Myles?"

"I mean, I already wear briefs so I know the comfort very well,"

"Then remove your shorts, let us all be in briefs in solidarity."

My eyes widened. I was nervous to even remove my shorts as I was growing down there with the sight of Dylan in briefs. "Come on, Myles," he urged.

"Alright," I removed my shorts and stood in my baby blue Calvin Klein briefs.

"Ooh those are nice," Dylan said.

"Thanks," I said. It was the first time he ever complimented me on my underwear. It honestly felt odd.

"See, we're doing it to support you," Dylan said, "Now come on, remove those shorts and boxers."

Nick rolled over on the bed and stood up, "What the fuck is wrong with you?"

"What?"

"Why are you doing this?"

"Come on, what's the issue? Remove them and overcome your embarrassment."

Nick looked at me then looked down at my briefs, then turned to Dylan and did the same. "Fine."

Nick pulled down his shorts and boxers and stood in his white Fruit of the Loom briefs. The underwear looked so good on him. They hugged his big body well. The waistband was just above hip bone and his bulge looked like it held a tennis ball inside. The mere sight got me more aroused. I lowered my shirt to cover my growing erection and said, "So can we put our clothes back on?"

Dylan turned to me and said, "Why?" his eyes moved south to my groin and noticed me covering my bulge. He walked over and lifted my shirt, "What you hiding?" he saw my growing erection and said, "Oh? You getting aroused?"

"A bit, yeah," I mumbled out.

The two then laughed.

"Cut it out, you two."

Nick pulled his boxers and shorts back up.

"I have a question," I said to Nick, "When you change in the locker rooms before showering, how do you avoid anyone seeing your briefs?"

"I go to the bathroom first and remove the briefs."

"Ah I see. Well, I know we're best friends but you look really good in those briefs."

Nick blushed, "Thanks, bro."

I turned to Dylan and said, "You too."

Dylan smiled and approached me, "Oh yeah? You think I should start wearing them?"

"I mean, if you want to. It's entirely up to you."

"Nick over here is a great underwear model, ain't he?" Dylan teased.

"Oh suck my dick, Nick!" he said with a hint of anger.

"I doubt I'd even be good. But Myles over here is a good cocksucker, from what I was told."

"Excuse me?" I said with a confused look on my face.

"Yeah, I heard from a little birdy you give good head," he pointed his finger to Nick. Whom I had never sucked. So I was even more confused.

Nick said nothing.

"Nick, you wanna tell him," Dylan pushed.

Nick looked at Dylan and then back at me. He saw I was confused. I was eager for his answer. It was almost dreadful to hear his response. Nick chewed on his lip for a bit and then answered, "Tim told me how good of a cocksucker you are."

Rage flashed across my face as Tim had told me he would never tell anyone about the blowjob. But it seemed he did and it just happened to be my best friend. "That shithead! He swore me to secrecy."

"Relax," Dylan said, "It ain't no biggy. The school year is almost over. When Nick told me, I was curious to see how good you were. We both were."

"Really?" I said, turning to Nick.

Nick turned away, reluctant to answer.

"He's being a shy baby. Why don't you suck me off first? I bet he'll join right after."

I looked at Nick who said nothing, then I looked back at Dylan. I had a dream about sucking them off but I just never wanted to make things weird between us. It was out of nowhere that Dylan was suggesting this. But I couldn't complain.

I lowered myself to my knees before Dylan. My hand reached for his bulge and I began to massage it with my fingers. Dylan's cock grew in size and I pulled it out of the fly of the underwear. His cock was long and thin. I peeled back the foreskin and saw a bead of precum resting at the entrance of the urethra. I brought my lips to the tip and parted them. My tongue slid under the shaft as the cock moved deeper into my mouth. I closed my lips around the base of the shaft and moved my head back and forth. I used my tongue to lick the tip of his cock.

Immediately, Dylan began letting out moans. My hands slid up his hairy long legs until they met his butt cheeks. I took both cheeks into my hands and groped them. Dylan had placed his hand on the back of my head and began to thrust. Slowly at first, then he sped up.

A big thrust came from Dylan as he shoved the tip of his cock into my throat. I held it hostage in my throat, allowing the throat muscles to enclose on it. Sending more pleasure through his body. A satisfied moan left his mouth as his cock left my throat. He pulled out his cock and turned to Nick, "He's really good. You should give it a try."

Nick said nothing.

"You scared you'll like it?" Dylan teased. He then pointed to the tent in Nick's underwear.

Nick grunted.

He rose from the bed and stood next to Dylan. I pulled down his shorts and boxers. I loved staring at his package in those briefs. The underwear was so snug on him. I pulled out his cock through the fly and immediately began to suck on it. His cock was as long as Dylan's but it had a bigger girth. The foreskin naturally peeled back when it was aroused. I wrapped my hand around the brown shaft as I sucked on the pink tip. Nick moaned as Dylan stroked himself.

I removed my hand from the shaft and brought both hands to Nick's well-toned ass. His cock entered my throat. I gagged due to the girth. Nick moaned while my hands tightened on his ass cheeks.

Nick's cock left my mouth and I turned back to Dylan's. For the next several minutes, I alternated between both men's cocks. It truly was a fantasy come true.

Dylan wanted to take it to the next step, however. He told me to stand up. Which I did. I felt his hands on my ass cheeks for a brief moment, then he opened my briefs and pulled down just below my cheeks. I felt him part my cheeks, "I've been curious about how tight you are."

Without protest, I said, "Go find out," at this point, I was fully invested and glad that he wanted to take things further.

Nick was about to protest when I bent over and sucked on his cock.

I felt the tip of Dylan's cock against my hole then he pushed. The cock slid inside me, "Ooh that's tight," he said.

With his feet, he parted my legs almost to a V-shape. I felt Dylan's hands on my hips as he began to move his hips. He started slow but then quickly sped up as soon as he found a groove. "Nick, his hole is tight and it feels good."

Nick said nothing. Instead, he sat there on the bed enjoying my blowjob.

Nick's cock entered my throat once more. This time he released a loud moan. A moan that urged Dylan. I felt a slap on my cheek as he was now fucking me at full speed. His cock constantly rubbed against my prostate sending rapid waves of pleasure. I moaned but it was muffled by the cock in my mouth.

As Dylan fucked me, he let out a flurry of moans. I knew he was close. He tried to speak but couldn't. His body began to slow. He lurched forward as the first shot of his cock entered my rectum. He came to a complete stop as he released the rest of his load. I felt his cock twitch inside as he filled my hole.

A long grunt came to Dylan as he finished. He pulled out his cock and said to Nick, "Your turn."

Nick took out his cock from my mouth and said, "No, I think I'm good."

Dylan placed a hand on his shoulder and said, "Trust me, you'll like it. Come on, don't be a party pooper. Do it and we'll take your tighty-whities secret to the grave. Heck, I'll even wear them for a week."

Nick looked at me then back at Dylan, "Alright, fine."

The two swap places. Dylan sat on the bed before me, with his cock tucked back into the briefs. Nick pressed the tip of his cock against my hole which was leaking cum. Which acted as lubricate. The thick cock entered my hole causing me to wince. It slithered inside me filling any gap inside me. It felt amazing. Nick held onto my waist and began to move his pelvis back and forth.

Unlike Dylan, Nick moved with force. His pelvis collided with my cheeks causing a slapping sound. It was painful at first but as soon as he found a rhythm, the pleasure came pouring in.

I held onto Dylan's waist as Nick fucked my tight hole. He was aggressive. Which was something I loved. The sheer amount of pleasure that washed over my body caused me to moan. Dylan reached for my cock and used the movements from Nick's thrusting to jerk me off.

The sounds of slapping skin could be heard throughout the entire room. My knees were starting to get weak but I held on for Nick. His left hand slapped my cheek while his right hand was planted on my lower back. His breathing was deep and I knew he was sweating.

I lowered my head as the movement had drawn me close to climax. I tried to warn Dylan but failed to do so. A moan left my mouth as I fired my load onto his forearm. It was so much that it had dripped onto his legs. Even one shot had made to his stomach.

Dylan removed his hand from my cock and said, "Wow, that was a hefty load."

I was about to reply when Nick's body jolted. The first shot of cum flew into my rectum. The thrusting slowed and Nick poured the rest of his gooey liquid inside me. His knees had bent and he was hunched over. Moaning through his teeth.

When the final shot came. He released a final moan and said, "Fuck!"

His cock left my hole and I fell to the ground. My legs were like jelly, "Are you okay?" Nick said.

I rolled on the floor with a smile, "Fuck yeah, I am okay. That was so fucking hot."

Dylan grinned, "I'm glad you enjoyed it."

I got up off the floor and cleaned myself. The two boys cleaned themselves and tucked their deflated cocks back into their respective underwear. Nick and Dylan were sitting next to one another in their white briefs. The image was something I wish I could print out of my mind.

"I wish we did this more often," I said.

Nick was the first to speak, "I have to admit, I wouldn't mind that."

The rest of the night we spent it in our underwear reminiscing about the years we spent together. I brought about the many times I had dreamt about doing something with them. I truly was happy to have friends like them. I would miss them when the school year came and we would all depart our own ways. But we did have summer to see each other. Who knows what would happen during those summer times? I just knew this wouldn't be the last time we did this.