My First Time, Gay By The Beach

All characters are above the age of 18. Sean is 18, and Mason is 20.

*

Every summer, my family went to my mom's hometown in the south, a cute beach town. I got lots of quality time with family and friends, sun, sand, and exciting memories.

One of my mom's high school best friends still lived there and has 2 sons: Mason, two years older than me and who I got along with the most, and Blake, a year younger than me who was like a little brother to me. We essentially grew up together and spent most of our summers together. The parents would go out and have their own fun while we would sleep at each other's places and enjoyed summer to the fullest.

Many of my friends were in relationships and always talking about sex. Being gay in a smaller town, I hadn't had a lot of options. The only other gay guy at school, Tobias, was closeted. Tobias wasn't really my type, but he was eager, and without a lot of options, we had kissed and sort of done some petting over our clothes but that didn't really count. I hadn't even really gone past first base yet! I definitely wanted to try some things soon though...

Summer came around and while Mason and I kept in touch during the year, we texted way more often once I arrived back in town. I always looked forward to summers with him.

One morning a few days into the beginning of summer, my mom was hosting a bunch of women over and even though the house was already clean, she gave me a giant list of chores to do.

I texted Mason: SOS My mom is trying to make me clean and do other gross chores first thing of summer :(

Mason: Eat breakfast. I'm on my way.

Me: On your way where?

Me: To me?

Me: Hello?

I ate breakfast the slowest humanly possibly. Just as I was dragging my feet to get started on chores, the doorbell rang. My mom opened the door to find Mason with a bright boy next door smile, who said, "Hey Mandy! Some friends and I have plans and I thought Sean would like to join for the next two-"

I held up three fingers up behind my mom.

"Three days if that's alright with you."

My mom looked behind her at me while I gave my most innocent look I could. She didn't buy it but said okay since Mason was already here and offered him some snacks while he waited. He politely declined and said he had to wait in the car because he left it on for the AC since it was already so hot early in the morning.

I dressed in my brand new neon green booty short swim trunks I'd been excited to wear for months since I bought it and a see through tank. I raced to pack a bag, ran outside, and jumped in his car.

Mason is the best! Sometimes I thought he saw me as a little brother, because he's always looking out for and trying to protect me. I tried to knee over the center console to give a big hug but it was too wide so in my excitement I inched closer and ended up slipping over and straddling one of his legs. He pulled my right leg over is other leg so I was fully straddling him but closer towards his knees so it wasn't really indecent and we were able to hug.

"Thank you so much! You saved me!"

Mason laughed, "No problem. But what are you wearing?"

"I'm ready to go swimming in your pool!"

His hands landed on my hips and his fingers dug into the swim shorts that molded to my butt like a second skin, brushing the tips of his fingers back and forth. "You should've worn something over it."

Looking down, since he was wearing long dark jeans and a shirt, I suddenly felt a little underdressed but...

"I am! It's called a swimsuit duh. I'm wearing a shirt too."

"Barely," he laughed.

"Don't be pervy. Also why do you look way better this summer? Did you get even more muscles? That's unfair." Even though he's only 2 years older than me, I've always looked up to Mason. When I was a kid, I followed him around like a puppy. Now that we're both adults, I wonder if my infatuation is more than that...

"Maybe you think I'm more handsome because I'm your savior?"

"Yeah, you're my savior. You're my hero!" I ran my hand along his jawline from his ear to his chin, his slight stubble coarse against my soft skin, and he completely melted to my touch. Woah. It was also heady to see. I did it again. His hands moved from my hips to my thighs and tightened. He looked at me with those piercing eyes, and his lips parted. Just from my touch! I don't know what I was thinking, but I ran my finger tips over his bottom lip. He closed his eyes, tightened his hands on my thighs again, and let out a deep unsteady breath. When he opened his eyes, he seemed to be mostly back to his normal look.

Then he smiled mischievously and bit my finger! I always loved that he's so level headed and dependable, but I also loved his playful side. I giggled. He chased it with his mouth and bit it again.

"Ow, that one actually hurt!"

"Sorry, here," he said as he took my pointer finger in his mouth and sucked on it. I gasped. Omg electricity shot from my finger to my entire body. He looked pleasantly surprised and sucked harder. To my horror, I whimpered, and he twirled his tongue around it. I pulled my hand away, but he caught it and started sucking my middle finger. Ugh, I kept making more little sounds. I didn't know this could feel so good. This time, I pulled away then offered him my ring finger, which he gladly sucked too. This was so hot. I leaned forward, drawn in, his lips were really nice. What would it be like to kiss him? He let go of my finger and got closer.

"Your neighbors are coming this way."

"What?" I barely asked before he lifted me off his lap and gently threw me back into the passenger seat. Wow he'd definitely gotten stronger. I looked over and his muscled arms were tan and filled out.

A few moments later, a couple of old ladies knocked on the car window. I rolled it down and they said they're happy that I'm back for the summer and I should come over for tea etc.

When they left, I said, "Omg they were so close! They totally saw what happened! I mean, not that, um, anything did. But..." Seriously what just happened? I realized I'm half hard! I tried to cover myself.

"My front windows are tinted and it's pretty sunny out. I don't think they did." He put the car in drive.

I thought aren't front car windows not supposed to be tinted or something? Anyways, the conversation changed, and we drove to his place, catching up on the past year, talking about everything and nothing, laughing as usual.

When we got out of the car, he gave me a big bear hug. It felt like he just enveloped me. His body was hard and strong but also warm, though not too hot. He ran his nose up and down my neck. That was new. Was he smelling me? He stuck his nose in my hair behind my ear and definitely inhaled. He whispered with a growly voice, "I missed you so much." Aaaww. But it took me a moment to say me too, because his lips against my ear made me shiver. Another sensitive spot? I think he felt it, because he smiled then kissed my cheek but really close to the corner of my mouth.

"Damn, you're irresistible," he said. Had Mason always been so affectionate? I couldn't remember. I was feeling tickley.

He said, "Welcome back to the south!"

"Well, I've been here for a few days already."

"Well then, welcome to my neighborhood."

"Oookay," I rolled my eyes. We walked into the deserted building lobby of his family's condo and I joked, "Aren't you going to welcome me to your building too?"

"Yeah, welcome inside the building!" He pulled me against him and licked my ear! I made another embarrassing noise. "I love the sounds you make."

I said, "You're such a pervert..." He licked some more, his hands in my hair. "Uummm..."

He ran his lips down my neck and released me. My legs were feeling weaker. Wait, was he playing with me?

The elevator opened as soon as he pushed the button, and when he got in, he said, "And welcome to my elevator." Two can play this game. This time, I wrapped my arms around him and licked up his neck and sucked then bit his ear. Oohh he liked that a lot.

He pinned me against the elevator wall with his hard body, running his hands up and down my sides. Oops maybe he's not playing. That's when I truly felt underdressed. Like I was in my underwear as he had direct skin on skin contact with most of my body. His hand brushed my stomach.

"Seaaann," he drawled my name, almost sounding pained. "Who taught you to do that?" I was really liking his grumbly voice.

"I just did what you did." I started wiggling against him, needing some friction.

"I didn't bite you. Did your dumb jock Tanner teach you that?"

"You mean Tobias? How do you know about him?"

"Yeah, Tanner. I've seen him before, looking like he wants to eat you."

"No..."

"Did you date someone else this year? There's always so many guys around you wherever we go. Who taught you that? Tell me." He was all over me, making it hard to think.

"I, um, no. I just felt like it so I did."

"Good. That was so hot," he said as he pushed between my legs with one of his. Ah, sweet friction. He sucked and bit my ears. That did feel good! I could feel my orgasm building. Just a little more. The elevator door dinged and opened. Ugh.

He keyed into the condo, turned towards me, and started saying, "Welcome to-"

When his mom came up and said, "Hi Sean! So glad you're staying over! You looked flushed. It's already pretty warm outside. Wash up you two. I have some fresh juice on the table."

I was aching. Thankfully, I was behind Mason, so my hard on was hidden. I said thanks and rushed to the bathroom, locking the door behind me. I shoved my hand into my bottoms and rubbed. No more than 3 strokes later, I came with my legs shaking. I washed up and headed out.

In the dining room area, I sat next to Mason who waited until his mom and brother were up doing something else. He then grabbed my hand and licked my palm. His eyes flashed. He looked upset! He said, "Next time, don't wash your hands."

......

I had been at Mason's place for a few days now. There was a free concert being held by the boardwalk with carnival rides and stuff like that. I picked out jean shorts with a green shirt but realized I didn't have any clean underwear left. I quietly found Mason's mom and told her. She said there wasn't enough time before I had to leave for the concert to do laundry and that I should just go commando. That sounded like something my mom would say! No wonder they had been friends all these years. She also said she and her husband were meeting up with my parents and would be home late.

Mason, a group of his friends, and I had a blast at the boardwalk that night. Mason drove as usual. I sat in the back with some of the others. We ate and went on rides.

The sun went down, and I wanted to go to the concert. No one else wanted to, so Mason went with me. We were towards the front in the big crowd of people that seemed to get more and more crowded. People kept bumping into each other, and I was getting jostled around. Mason came up behind me and put his hands on my waist to steady me, which helped. I kept dancing but was bumping into the guy in front of me. Even if it was a little too close, I thought it's better to be too close to Mason rather than someone I don't know, so I backed up more.

Mason saw I couldn't really move forward anymore because of the crowd. He leaned in and said, "At least don't dance anymore." I said he's ridiculous and continued. After a bit, a song I wasn't as into started, and I realized Mason's erection was pressed against my butt. As I danced, I'd totally been grinding against him, too lost in the moment.

I froze, and Mason groaned, "Keep dancing." So I did. His hands roamed my arms, my shoulders, and my stomach. His hands went under my shirt and palmed my pecs. He asked, "Are you sensitive here?"

Yes, I loooved stimulating my nipples. I loved nipple play, but I wasn't going to say that!

He rubbed and my hips stuttered.

"Hmmm." He rubbed harder, and I undulated.

Everywhere he touched me felt like it was leaving a wake of fire. His touch was strong but cherishing. I was burning up.

His hands roamed down my sides and his left hand skimmed up my leg, to the hem of my tattered short jean shorts. He didn't get very high, but I panicked since that was when I remembered I wasn't wearing any underwear! What would he think? I was hard. What if my erection poked out of the small shorts? I really needed to start wearing longer bottoms.

I abruptly announced, "We should go back and catch up with your friends!"

"You go on. I'm going to need a minute."

We ate yummy, greasy snacks with the group and went on some rides. Except I was still half hard and these jean shorts rubbed against my sensitive head no matter how I adjusted. Every shake and rumble of the rides was only stimulating my poor cock. At this point, even walking was causing enough friction rub.

Then, everyone wanted to go on a thundering roller coaster. My dick could not handle that. Should I rub one out in the bathroom?

I said I would sit out on this one. Mason was trying to be encouraging saying he'd be there with me the whole time. "I know you're somewhat afraid of heights, but this ride is way less scary than all the ones we've been on so far."

He kept pushing and practically started dragging me to the ride, when I finally whisper-yelled at him as quietly as I could, "I can't go on the ride, because I'm not wearing any underwear and these shorts keep rubbing against me! I need a break." I was on edge.

"Why aren't you wearing underwear?"

"I ran out of clean ones and your mom told me to go commando!"

His eyes grew wide, "You know both our moms are crazy and we shouldn't listen to them about things like this!"

I thought he was going to continue on to chastise me for going on all the other rides or for dancing with him without anything on, but no. He ran his hand on the side of my hip and dipped his hand slightly under to find smooth skin only. He groaned, pulled me closer to him, and said, "You're not wearing any underwear, and you rode in my car." Bro dudes and their cars...

We sat that ride out together and I was able to calm down a bit. We had a good rest of the night. It was getting late and after swimming the whole day, we got tired faster than everyone else, so left early.

There was a shortcut we would take to his house from the beach but it was a bumpy ride, which caused the stimulations of my jeans against my cock again. I'd change positions or hold down my jeans from the side to decrease the movement against them. But as I got tired of holding or lost in the conversation, I'd stop and the relaxed shorts kept being loose enough to rub against me. The car bumps certainly didn't help. After a while, I gave up, whatever it's just Mason in the car. Who cares if I'm hard at this point, no one's going to care.

Turned out Mason did notice. He kept looking over, and I could feel his gaze on my legs. A part of me thought I was making up his attention, so I spread my legs a tiny bit, and his grip on the steering wheel tightened. He then reached over and pulled the side of my jeans and kept his hand on the edge of them, holding them in place.

"Holding it like this helps, right?"

"Yeah, a little."

As we talked about the night, his hand on my leg seemed to sear into me. I didn't know how to communicate that, so I told him the pressure of his hand was uncomfortable. He apologized and shifted his hand so it spread wider and now was gripping more of my inner thigh, which did the opposite of helping my situation. And was it just me or was his hand higher up now? I squirmed and spread my legs wider, which caused my shorts to slip from under his palm and definitely shifted his hand up even higher.

"Sean?"

"Just don't get closer."

"So this is okay?"

"Yeah, I think so."

He started caressing up and down. "You sure?"

"Mhm hmm." My head fell back on the headrest. He was definitely getting closer. I could feel the blood pulsating in cock.

"Your skin is so soft." He hands inches over my jeans.

"Uh, you're wet." I had leaked precome through my shorts!

He was so close to my cock head, millimeters away. "I'm not going to go any higher, promise." That was sort of gentlemanly and also very frustrating. I was embarrassed but mostly I was going slowly insane.

His hand stayed there and teased me for who knows how long. It could have been seconds or minutes or hours.

Then we hit a big bump in the road that jostled the car and his hand bumped against me.

"Oh fuck!" Mason said when his fingers pressed against me. Yesss, I ground my hips up against his hand. The perfect driver Mason swerved, he was losing focus.

I was already completely lost to the feeling and grabbed his forearm when he tried to withdraw.

"Sean, you'll hate me later for this."

"I'll hate you now if you stop. But stop the car. You're going to kill us," I panted out.

He started drumming my cock head through the shirts and I shouted. He parked on the side of the road. Benefits to the backroad shortcut- no lights and no other cars. He unbuckled and leaned over me as his experienced hands unzipped me and he pulled me out. Ah relief! His big hand grabbed my cock begging for attention and thumbed my head. He rubbed all around it in circles. My hips stuttered. He teased down to my balls and back up. He tightened his hand, and I started fucking up into his fist. Pleasure shot through my body.

My breaths seemed loud. It was too dark to see him clearly but his other hand was rubbing himself through his pants. He kissed my cheek then my lips just as he tightened and stroked me with a twist. I exploded and he swallowed my moans. My orgasm seemed to go on and on and he kept rubbing through it which prolonged it, until I was oversensitive and pushed his hand away. He kissed me again, long and hard. Then he tucked me back in my shorts.

As we got closer to his home, street lights started going by. I was awaking from my orgasm haze when I spotted a wet spot on his jeans. I softly poked it. "Is that... did you...?"

"Yeah, you made me come in my pants." I laughed and blushed. I hadn't even thought of helping him.

Maybe I should next time.

......

Mason, Blake, and I were going to rent a pedalo boat and spend the whole day just the three of us out at sea, under the sun. But, Blake bailed on us at the last minute. Some soccer club he was a part of was having a get together, so it was just me and Mason.

We took off from shore, and because we know the coastline so well, we went far out. The buildings were left tiny in the distance and we didn't see any other vessels around.

We packed bags full of food for the whole day and ate to our hearts content. He fed me fruit and I often ended up mouthing the tips of his fingers trying to fit each piece in my mouth.

I wore a Speedo. I thought it's a size too big so it wasn't outlining everything, you know. And I thought Mason might like it. He did. He totally did. I kept catching his eyes gliding down my body to get stuck on my Speedo.

We finished another round of swimming. We were at the back of the boat to get back on. Mason was next to me hanging onto the boat. To get enough purchase, I had to pull my legs forward and use all of upper body strength. I'm not unfit, but lean and a little shorter than guys my age, and I'm also not the strongest. While trying to pull myself up, I didn't make it on the first try and was kind of awkwardly hanging on with my chest almost on the boat, when I realized my Speedo being a size too big was bad because the force of pulling up quickly out of the water and the cloth being heavy with water caused them to slip down. Mason was right behind me! He was getting a good view of my crack right now!

I let go of one arm to try to pull them up, causing my body to start slipping off the boat. Mason reached up, grabbed my ass cheek, trying to push me up. I was caught off guard, so I tried to pull away. He must have thought I was falling again so tried to grab me but ended up grabbing my suit. When he pulled and I was trying to go up, he ended up pulling my Speedo off!