First Time

Chapter 14 – Come to the island

La Isla de Aquinas – Chapter 14

“This is amazing!” I said as Glenn, Gloria, and I entered the apartment.

I immediately ran over to the balcony to enjoy the view we had of the ocean. As the soft, warm breeze touched my skin and the sunset colored the sky red, I felt a weird calmness flow through my body.

“This view is great. Isn’t it, honey?” Gloria asked as she stood beside me on the balcony.

“Thank you guys SO much for taking me here with you!” I said and hugged Gloria tightly.

But the moment I realized I was hugging her tightly, I let go and stepped back a bit. “Sorry! I don’t want to hurt the baby,” I said, afraid she would be mad.

“Haha! Don’t worry, honey! It’s safe inside my belly. No need to worry that you’re going to hurt it.”

“Oh… I thought I’d…” I stammered and hugged Gloria tightly again.

“Right. Let’s finish unpacking. We’re invited over at Thiago’s for dinner. And believe me, you don’t want to miss that!” Gloria smiled.

So after we unpacked and I made the bed in my small room, we went out to Thiago. Glenn had rented a car so he could visit his old friends. Since it was a convertible, I insisted on driving with the top down. Glenn just smiled when Gloria pressed the button, and the roof automatically opened.

This was precisely how I always pictured a vacation. Having fun and doing all sorts of stuff you wouldn’t do at home. And all that with a nice, warm breeze in a new environment.

When we arrived at Thiago, a man looking about the same as Glenn came running with his arms spread and called out his name. The moment his body collided with Glenn, they hugged each other firmly with loud pads on their backs and shoulders.

Next, he greeted Gloria, and a woman joined him. After Glenn introduced me and I got hugged too, I learned that Thiago was Glenn’s best friend when they grew up. Finally, his wife, Maria, invited us over to the table where we had one of the best meals I ever had.

Glenn and Thiago shared a lot of childhood stories about all the mischief they did and got away with. All of them were having a good time, and I had to laugh at a lot of the funny stories too. Sometime during all of this, the conversation became more serious.

“If those idiots think they can take our island, they’re in for a treat!” Thiago said sternly.

“I know, T. But don’t do anything stupid, okay? I’m sure they’ll find a diplomatic solution and push back these Nicaraguans,” Glenn replied, and he sounded all serious now too.

I later learned that they barely avoided a full-blown civil war at that time by sending US troops to keep the peace. One of the outcomes of the peace negotiations was that a part of the island became a permanent part of Nicaragua

At the time, this didn’t register with me. I only noticed a lot of soldiers in the lesser part of the town and the graffiti sprayed on the buildings with all sorts of images I couldn’t place and text I couldn’t read.

I was getting pretty tired, and when Gloria saw me yawn, she announced it was time to head back to the apartment.

The following day was all about revisiting old friends. Again. And although these were all very friendly people, I was starting to get bored. So when we were sitting at the breakfast table the following morning, Gloria asked, “How about you and I doing something fun today while Glenn visits some more friends?”

“That sounds great!” I said enthusiastically, glad to do something else than being the fifth wheel on the wagon.

“An excellent plan!” Glenn said and looked at Gloria, “But is it okay if Scott and I do some shots on the beach for about one or two hours first? The light is fantastic this time of day.”

“Sure! That gives me time to plan something for us. Back here at ten?” Gloria asked with a twinkle in her eyes.

“Let’s go, Bud! We’re heading to the beach,” Glenn said as he got up and grabbed his camera bag from the cabin in the corner.

“Don’t I need my swimming trunks or something?”

“Nah. We don’t need them. But bring a beach towel just in case,” Glenn smiled and winked at me.

When we reached the beach entrance, Glenn pointed to the left. So after I took off my shoes and felt the dry sand between my toes, we started walking in that direction. Despite the already lovely weather, there weren’t many people on the beach. Before we started walking, I could see a couple and a man with his dog walking in the distance to our right, but other than that, we were alone.

To the left of us, old cabins were overlooking the ocean. The location was incredible, but these cabins looked old and worn. As far as I could see, none of them were occupied, which was a bit of a shame considering the fantastic spot on this beach.

“What’s with these cabins?” I asked Glenn.

“They were put here about a decade ago. But no one took care of them, so now they’re old and shabby.”

“Pitty,” I said.

“There’s the spot I was thinking about,” Glenn said after we walked some more and pointed toward a lush bush of tropical plants on the end of the beach, where the ocean crashed with mild waves at the shore.

“That looks nice!” I exclaimed, impressed by the tropical look I only saw in magazines up until now.

“I think it’s the most beautiful spot on the island,” Glenn said as he put down his camera bag.

As I put down the bag with the towel next to it, I asked, “What do you wanna shoot today?”

“I wanna do another Pyntar shoot today. But a little different than usual. Where most of these are single-shot images, I want to tell a story here,” he said, looking expectantly at me.

“Okay… and?” I asked, completely clueless about where this was going.

“On the island,” Glenn continued, “all beaches are clothing optional. You can be naked if you want to, but you don’t have to. I’ve seen families having fun on the beach completely naked, sitting next to another fully clothed group. And everything in between. No one cares.”

I must’ve looked stupid because he started laughing when Glenn looked at me. But, it didn’t make me feel uncomfortable at all because I knew he’d explain everything.

“Sorry, Bud. I guess I don’t make a lot of sense. I want to tell a story with multiple pictures. The story is about a boy on a beach,” he said, theatrically waving his hand to accentuate the location, “who discovers the joys of being naked outdoors. Or just in his undies,” Glenn quickly added.

“Oh,” I simply said, envisioning the shoot in my head already.

“That’s up to you, of course,” Glenn said, trying to size me up about being naked.

“So I need to do some acting for this shoot?”

“Acting is a big word. I want to tell a story with pictures this time. It’ll be a first for me too.”

“Sounds like fun! How do we do this?” I asked, excited to get going.

Glenn talked me through his plan, and after a few minutes, I walked toward the bush in my short blue sweat shorts and white t-shirt, with the bath towel around my neck. Glenn was behind me, snapping away already.

“Stop there and look around,” Glenn said while I was facing the ocean.

After a few pictures like this, Glenn told me to place the towel on the sand and to take off my shirt. Next, he asked to walk knee-deep into the ocean.

“Look at your pants. Try to look worried they’ll get wet,” Glenn instructed me as he was standing in the water next to me in his underwear and shirt.

I did just that and felt the tension inside build. I knew what was coming next, and I felt pretty excited. When I was back at the towel, I waited a few moments for Glenn to catch up and waited for further instructions.

“Slowly drop your sweats, Bud. I need to shoot both the pants and your face, so please take it slow.”

“Okay,” I mumbled, surprised that my dick was still soft.

After I kicked away my sweats, Glenn took a few close-up shots of the bulge in my tighty-whities.

“Look around shyly to check if no one is looking and hook your thumbs in the waistband,” is all I heard.

I did just that, and I felt incredibly naughty for what I was about to do. I didn’t know why, but I was still completely soft despite all this tension.

“Slowly pull them down…” Glenn softly said as he was snapping away.

The moment my dick was free from its confinement, I felt the warm breeze on it and realized how awesome it is to be naked on this beach.

After Glenn was done with the closeup from my dick, balls, and ass, he asked, “Can you stretch your body? That way, it’ll look like you’re enjoying this freedom even more.”

I turned my body toward the ocean, put my arms in the air, and stretched. Then, I casually wiggled my midsection so my dick was flopping gently from left to right.

“That’s awesome,” Glenn said to me. “Can you run around and do some exploring near these bushes?”

After pretending to play and discover, Glenn directed me to the ocean again. I got in, and with the water ending just below my balls, I looked into the distance. Glenn took his shots again, and as I went for a swim, he tried to follow me as far as possible. Eventually, I swam back toward him and almost touched the camera as I got closer.

“Lie down on the towel to let the wind and the sun dry you,” Glenn said as we walked out of the ocean.

“Do you want me to make my dick hard?” I asked as I looked down toward my shriveled dick and balls.

“Dick, huh? What happened to willie?” he chuckled.

“Michelle said I shouldn’t call it a willie anymore after… you know…”

“Haha! She’s right. You’ve got a real dick now! You’ve jerked, you’ve fucked, and you can shoot cum. Yeah. That sure qualifies as a dick to me,” Glenn said, ruffled my hair, and patted me on my butt.

“But do I?”

“Uhm… It would make some nice pictures if you decide to spank it…” Glenn smiled after he looked around and saw nobody even remotely close to us.

“We’ll see,” I smiled mischievously and walked over to the towel.

“Go for it,” Glenn said as he put the camera in front of his face.

I stood by the towel with my back toward Glenn. I stretched again and pretended to look around carefully. I already saw that we were completely alone at this end of the beach and felt my dick chub up a bit from the anticipation of what I was about to do. After a few moments, I kneeled and laid down on the towel on my back with my legs spread slightly and my hands folded behind my back. As I looked at the passing clouds and listened to Glenn’s camera clicking away, I let my mind drift to my actions with Michelle. The images of Michelle’s body below me quickly morphed into Becky’s naked body in front of my eyes, and I realized I was getting hard.

I noticed Glenn being close by to shoot as many pictures as possible of my growing member, which excited me even more. By the time I was fully hard, I was so horny that I just had to jack it. So as I gripped my hard dick and started sliding my fist up and down, I heard Glenn moan a soft, “Oh yeah…” and decided to give him a good show.

My right hand was finding a nice rhythm, but I wanted more this time. So I spread my legs further and let my left hand slide down between them. As my index finger started searching for my butthole, I saw Glenn move in the corner of my eye, and he walked over, so he looked up at me from between my legs. He got to his knees and moved even lower to a point where his camera was almost touching the sand.

Doing such a naughty act in a public place was an even bigger turn-on for me than I expected, and I realized I was starting to get close already. I let my finger press on my butthole and relaxed my muscles down there. This immediately caused the tip of my finger to enter me, and a surge of pleasure shot through me as it happened. I pressed down and felt my finger go even deeper until I touched a spot that sent off fireworks in my brain.

“OOHHHH!!!” I moaned loudly.

I sped up the motion of my right hand and started moving my finger in and out of my hole. As I did this, I heard myself moan and felt movement on the towel, realizing Glenn was taking all sorts of close-ups of my body during this wild jack-off session. But I didn’t care. I was so engrossed in jacking off I only paid attention to the good feelings in my lower body, with only the sound of the crashing waves resonating in my ears. Even if a marching band walked by, I probably wouldn’t even notice.

My fist and finger movement increased even more, and I felt I was about to cum. I wasn’t sure how I did it, but I managed to open my eyes and look straight into the camera and moaned, “I’m cumming…. Ohhhh… Shoot my… ahh… dick!”

Glenn’s camera moved away from my face and immediately focused on my dick. Then, with a last, loud moan, I felt the now-familiar movement inside my dick, and a moment later, I felt two warm drops of liquid land on my belly after my dick spasmed wildly in my gripping fist.

I needed some time to recover, but I had to remove my finger from my butt to relax more comfortably. So, with a deep sigh and a squishy sound, I retracted my finger, and I felt my anus and lower-body muscles relax. The warm wind over my body, the sound of the waves in the background, and the screaming seagull in the distance were so relaxing that I almost drifted off.

“That was awesome, Bud!” Glenn said as he sat down next to me on the towel, looking at my face and smiling.

I opened my eyes and smiled back. Then I looked down at my belly, where my softening dick was lying on my thigh, and I saw the two clear drops of cum. I scooped them up with my right index finger and brought it to my face. It looked very watery and not at all like Glenn’s cum. But I was extremely curious about the taste, so I opened my mouth, and the moment they activated my tastebuds, I was surprised by its taste. Glenn’s cum was salty and musky. But this was sweet and light.

“This tastes good!” I exclaimed, causing Glenn to chuckle.

“Yeah. Your cum tastes amazing!” he said and quickly moved his head down to lap up the remains my fingers didn’t pick up.

“That tickles!” I giggled as his tongue moved over my belly.

We sat there for a few more moments when Glenn asked, “You really like anal stimulation, don’t you?”

“I like what?”I asked, vaguely aware of what he was talking about.

“Sticking things up your butt,” he said bluntly while looking at me.

This caused me to blush a bit, and after a few moments, I just nodded.

“I told you before. There’s nothing wrong with that. I just want to warn you about what you stick inside. Look out for things with sharp edges. This might damage your insides. But stuff like a hairbrush handle or banana is perfectly fine. Just make sure you lube up and be careful.”

“Lube up? You mean like using grease or something?”

“Yeah. Something like that. Just make sure it’s based on natural ingredients and doesn’t contain any alcohol or other aggressive substances.”

“How do I know which is right?”

“When we get back home, I’ll buy the good stuff and give it to you, okay?”

“That’ll be great! Thanks.” I said and suddenly felt even more grateful for having Glenn in my life.

“I’ll also buy you a small dildo that’s made for this, so it’s perfectly safe. Or you can find a boy who’s willing to put his dick up there. That’s even better than dildos or hairbrushes,” he smiled and winked.

“I think I’ve already found a guy that’s willing to do that,” I smiled and looked expectantly at Glenn.

“Haha! I’m willing, that’s for sure. But I think I’m too big for you and I might hurt you. Maybe in a few years, Bud.”

“I was afraid you’d say that,” I said, feeling a bit disappointed.

We went quiet after that and just stared at the ocean and the crashing waves. I looked over and wondered about the weird line of trees and bushes at the end of the beach. It almost felt like someone planted it there to prevent people from falling off the island or something.

The line ended at the ocean on both sides, and it looked like a lost piece of rainforest decided it liked the beach better.

“What’s with these trees?” I asked.

“Dunno. They’re here for as long as I can remember,” Glenn said as he looked at the tree line.

“Have you ever gone through to see where they end?”

“No. I went around the island with a boat once, and there’s no way to get there from the water. There’s sort of a ring of pointy rocks in the ocean after the tree line. I think it’s just rocks and stones over there.”

“Can we go and check it out?” I asked excitedly, already looking forward to an adventure with Glenn.

“I don’t see why. Like I said, probably nothing but rocks. And Gloria will be here soon. Maybe later, okay?”

I felt a bit disappointed, but Glenn did have a point. I was looking forward to spending the afternoon with Gloria, and we could always check it out later.

“Ready for a few more pics until Gloria gets here?” Glenn asked, holding up his camera and radically changing the subject.

“Sure!” I said, “What do we need?”

“I need just a few more to tell the story. Not everything I shot so far is suited for Pyntar,” he winked.

After he shot a few more with me lying on my back, some with my knee in the air to hide my dick, he asked me to roll over and lay on my stomach. After a few more of these, I heard, “There you are!” and I looked up to see Gloria walk toward us.

“Hi Gloria,” I said and waved.

“Just in time, Hon. We’re done here,” Glenn said and kissed his wife on her cheek.

“I’ll see you two later. I’m off to see Lucas,” Glenn said as he grabbed his camera bag.

“Any idea when you’ll be back?” Gloria asked.

“Not really. But knowing Lucas, it’ll be late. Or early,” Glenn smiled.

“Have fun!” both Gloria and I said as Glenn started walking toward the apartment.

When he rounded the corner, he waved at us. I got up from my sitting position and looked excitedly at Gloria, not feeling any need to cover up.

“You know you’re allowed to be naked out here?” I said, pointing toward both ends of the beach.

“Haha. Yeah, I know. And it’s just the thing for you, honey. Isn’t it?”

“Yeah. I really like it a lot!”

“Ready for the real fun then?” Gloria asked and handed me my swimming trunks.

“What are we going to do?” I asked as I took it and started pulling them up.

It turned out that Gloria had an excellent idea of fun. She rented a speedboat for us. There even was a parasail option on it, which I had to try out, of course.

We spent almost the entire day at sea. Every time I got behind the wheel of the speedboat, I felt like the king of the world. The sheer power of the boat, combined with the wind in my hair and the splashes of water in my face, was priceless.

After returning the boat, we went to the harbor, where Gloria had made reservations in a small restaurant. After getting our drinks, I raised my glass, and Gloria did the same.

“To an amazing day,” I said as our glasses touched.

“To an amazing day,” Gloria said in return and smiled.

We checked the menu, and after the waiter took our order, Gloria looked thoughtfully at me.

“The time in Africa is almost over for your parents,” she said, clearly trying to see how I’d react.

But I didn’t mind talking about it. I could tell Glenn and Gloria everything. So I shrugged and said, “I know. And according to mom, they’re going to live in Seattle for a year so that I can settle down even more. So I’m glad they’re thinking about me for once.”

I wasn’t angry or anything. It was just something I felt deep inside, something I could vent to Gloria about. She kept looking and just nodded.

“I get it. But it’s the life your dad chose, and you’ll have to deal with it. Sometimes things don’t feel fair, and I guess this is one of these things.”

“I guess. And with you and Glenn, I can do the things I like to do without the constant mocking from my dad. He wants me to play baseball or football. He just doesn’t get my interest in photography,” I glumly said.

“I wouldn’t worry about that too much, Honey. You just keep doing your thing, and he’ll see it isn’t a fluke or anything. It’s a very… uhm… manly world he’s in, and photography doesn’t have a very masculine image.”

“I know. And I don’t hate him for it or anything. And we do fun stuff together too. But I just wish… you know…”

“I do. But look at the bright side. When you’re staying in Seattle, you can come and visit us as much as you want!” she said smiling. “You’re funny, kind, helpful, and SO much more. We’re delighted you stayed with us this past year…”

“Almost a year,” I interrupted her with a smile.

“You’re right. Almost a year. But the guest room isn’t the guest room anymore. It’s YOUR room now,” Gloria said and pointed at me.

“I uhm…” I stammered, flabbergasted by her heartwarming words.

“So, please. Will you do us a favor and keep coming over, lighting up our days?”

“Yes. Yes! I’d love to!”

“I’ll drink to that,” and Gloria held up her glass of coke once again.

The dinner we had was excellent. The Colombian kitchen isn’t that well known across the world, but I didn’t eat anything that wasn’t tasteful during my time there. After Gloria paid the bill, we walked toward the exit and waited for the cab. Once it pulled up, I opened the door for Gloria to let her go in.

“Wow! Quite the gentleman,” she smiled.

I quickly walked around the car and got in on the other side. During the ride, I felt a warm feeling inside my stomach because of the love Gloria expressed for me.

“I really love you guys! And I can’t thank you enough for taking me in!” and I hugged Gloria tightly on the cab’s back seat.

“I love you too, Honey. And don’t worry about it! We’re so glad to have you over. You’re basically doing us a favor.”

When we entered the apartment, Glenn wasn’t home yet. But I felt tired, so I went to the bathroom to do my business and brush my teeth. Then, I walked back into the living room to give Gloria a goodnight hug and kiss, which she eagerly accepted.

“What’s the plan for tomorrow?” I asked before I left the room.

“I’m off early tomorrow. But Glenn will be home. I’m going to visit the other side of the island with Thiago to see how the situation is over there at first hand. I’m curious, and I might be able to use that in one of my lessons. I think Glenn only has one appointment tomorrow, and it’s late in the afternoon.”

“Cool. Goodnight!”

“Night, Honey.”

* * *

A honking car outside the apartment woke me up. I looked at the alarm clock and learned it was a little past nine. I idly toyed with my sparse pubes and with my balls hanging down in my loose sack as I thought about the great day I had with Gloria. My morning wood stuck up from my groin, and the urge to go peeing grew by the minute.

After doing my business in the bathroom, I wasn’t sure what to do. I felt a bit horny, but it was also almost time for Gloria to get up and start making breakfast, so a quick wank wasn’t an option. That’s when I realized Gloria was gone already and that it was just Glenn and me.

I figured Glenn would probably be in for some fooling around, so I quietly walked over to their room. As I approached it, I saw the door was open, and the light was streaming in from the window.

Glenn was lying on his back, legs spread, and one arm above his head. He snored loudly, and his face was looking toward the window, away from the door. The thin sheet was crumbled around his feet, and his dick lay softly on his thigh.

As I looked at his groin, I noticed how massive his balls looked compared to mine. They weren’t very hairy, so I could study them nicely from where I was standing. I wondered if I should wake him. He probably had a short night, but he’d already said he didn’t want to sleep this vacation away. So, after thinking about it for a few moments, I tip-toed over to the bed and got on the mattress between his legs as quietly as I could.

Judging by his snoring and the fact that he didn’t move a muscle, I figured I was still good. So I leaned forward a bit, took his soft dick in my hand, and sucked it into my mouth.

This was the first time I had his dick in my mouth while it was soft. I played with it by using my tongue and cheeks for a bit, and it started to grow before long.

After toying with it a bit longer and wrapping my lips around it, it was as hard as I remembered. The snoring above me had died down, but I saw Glenn was still asleep when I looked up.

Feeling Glenn’s hard dick in my mouth got me pretty worked up, so I decided to start sucking him for real now. I used my right hand to wrap around his shaft while my tongue worked his dickhead. I was getting into it when I felt Glenn move.

“Huh? What?” he mumbled, and moments later, I felt his hand on my head.

I let his dick slip from my mouth, looked up at Glenn, and smiled. “Morning,” I whispered and started lapping his dick from bottom to top like a popsicle while keeping my eyes locked with his.

“Ooohhh… that’s some way to wake up…” Glenn groaned.

Moments later, he rubbed me over my cheek and said, “Come here,” and he gently pulled me up to his body.

I crawled up to lay down on his muscular chest with my legs on each side of his body and my boner pressing in his stomach. He kissed me on my mouth and hugged me tightly.

“Why did you do that?” he asked.

“I like doing that. And I like doing this stuff with you.”

“We’ll… we’ve got all morning, so no need to rush,” Glenn said smiling.

Lying there on top of Glenn with his muscular body pressed against mine and with every now and then a warm breeze over my body, I felt safe, horny, and completely at ease. But when I shifted my body down slightly, I felt Glenn’s hardon press against my ass.

I looked at Glenn the moment this happened and firmly pressed my butt against it. Glenn just smiled and let me do my thing for a moment.

“I think I want to try it now. I think I can handle it,” I whispered, feeling a bit nervous because of his size but also excited as hell to try it.

Glenn looked at me and sized me up. I could see him struggling with what he should do, but after a few moments, he said, “First, we’re gonna try if it’s even an option. Your anus might be too tight for it, and I don’t want to hurt you.”

“Really!? Thanks!” I said excitedly and looked him deep into his eyes, “And I know you won’t hurt me! So how do we do this?”

“Haha! How can I say no to such eagerness?” Glenn laughed, “I’ll grab the lube, and we’ll try with my fingers how tight you are and let you get used to the feeling of more than just one finger.”

Glenn gently pushed me aside, where I landed on the mattress and lay on my back. My hand started toying with my boner as Glenn went to the bathroom. When he came back, he had a jar in his hand, and his bouncing boner led the way as he walked toward the bed.

“Get on all fours, Bud. It’ll be easier that way.

I quickly got on my hands and knees and asked, “Is that lube?”

“Yeah. It’s coconut oil. It’s one hundred percent natural and slippery as hell. People over here use it for all sorts of things. Here. Check it out,” he said, holding the jar in front of me.

I sniffed at it, and it didn’t smell like much. Just plain coconut. I dipped one finger in it and examined its texture. Glenn was right. This stuff was very slippery and looked a bit like thick water on my fingers.

“Cool. And now you put it on your willie, or what?”

“Not yet. First, I’m gonna use my fingers to lube up your hole. But more importantly, to check if it isn’t too tight down there. You ready?” Glenn asked as he took the jar, his boner wiggling in the corner of my eyes.

“I guess…” I said, still eager to try but a bit anxious about it.

I felt Glenn’s finger rub over my hole a few moments later. I was surprised about how warm the oil felt on his finger. I expected a cold rush like when someone squirts sunscreen on your back. But the opposite was true.

After rubbing around for a short while, Glenn said, “I’m going to press now and try to slide in. Don’t try to clamp your hole shut. Just try to push like you’re taking a dump. It’ll be way easier that way.”

I simply nodded and did what Glenn asked. And the moment Glenn’s finger started sliding in, I felt my boner twitch and couldn’t hold back a moan.

“You’re doing great, Bud,” Glenn softly said. “This was way easier than I anticipated.”

He started sliding his finger in and out, and each time he hit a particular spot, my boner twitched. Finally, after a minute or so, he slid out, stuck his finger in the oil, and said, “I’m lubing you up extra good to make sure it doesn’t hurt that much.”

I simply nodded again because I was enjoying this too much and didn’t trust my voice at that moment.

“I’m going to try using two fingers now. I think you’re loose enough for that. Is that okay?”

“Uh-huh,” I mumbled, pressing my ass against his hand and feeling all-new incredible sensations flowing through my body.

When Glenn’s fingers left me to scoop up some more oil, I felt empty but couldn’t wait for him to enter me again and rub against that weird spot inside me.

“Okay, Bud. Take a deep breath, try to relax, and push back a little, okay?”

“Yeah… just… I’m…” I stammered, trying to find the right words.

Glenn must’ve sensed I was ready for it because he started pressing with two fingers now. As the pressure grew, I remembered Glenn’s words, took a deep breath, and pushed back by using my muscles around my asshole. Moments later, I felt both fingers slide in slowly and moaned.

“Does it hurt?” Glenn asked worriedly and immediately stopped moving his fingers.

“No. It doesn’t hurt. I just… feel full. It feels good,” I said, still trying to relax as much as possible.

“So I just keep going?”

“Oh yes, please!”

After a few minutes, Glenn’s fingers were probing around and sliding in and out of my ass easily. Every time he touched my sensitive spot, I moaned loudly. My dick was rock hard, and I felt horny as hell by now.

“I didn’t expect it, Bud, but I think you’re ready,” Glenn whispered in my ear, his finger still sliding in and out.

I looked up, and a big smile spread across my face when I saw the look in Glenn’s eyes. Of course, I wasn’t very experienced yet, but I had seen this look before, and it was one of pure lust.

“I think it’s better if you lie down on your back. Just spread your legs, lift your knees, and place this pillow under your lower back,” he said and grabbed the oil.

I did just that and looked at Glenn while he lubed up his big, hard dick. As I looked at it and realized how much thicker his dick was, I suddenly felt a wave of nervousness wash over me. Glenn must’ve noticed because he asked, “Nervous?”

I just nodded and whispered, “Yeah. A bit.”

“Don’t worry. We’ll stop the second you want! Just say it, and we’ll find another cool thing to do,” Glenn said soothingly.

I was still horny as hell, so despite the anxiety, I nodded and said, “I want to do this, so just fuck me already.”

Both Glenn and I looked surprised as these words came out of my mouth, and I started giggling nervously while Glenn just smiled broadly.

“Alright, Bud. I’ll fuck you already!” He smiled and grabbed his hard dick in his hand.

Moments later, I felt the tip of his dick brushing against my slippery butt hole. He pressed firmly against it and softly said, “Remember. Deep breaths and press as if you’re going to the toilet.”

I nodded once more and felt my heart throbbing in my throat. I inhaled deeply, and the moment Glenn’s dick started sliding in, I exhaled and loosened my sphincter. I felt a popping sensation and a mild gust of pain. But the pain went away immediately, and I realized Glenn had entered me. The feeling was quite overwhelming, and I needed a moment to get used to being so full.

I looked at his face and noticed his worried expression. He was constantly looking at me to see if I was okay.

“I feel it,” I moaned softly.

“You okay?”

“Yes. Just give me one second to adjust.”

“Sure,” Glenn said and held his body perfectly still.

After a few seconds, I felt Glenn’s fingers wrap around my stiff dick, and he started playing with it. He wasn’t jacking me, just massaging it and making me feel good. This worked quite well, and after a few more moments, I said, “Can you go deeper?”

Now it was Glenn’s turn to nod, and with a soft push of his hips, I felt him entering me. It was a little uncomfortable, but the feeling of something entering me, the naughtiness of it, combined with his massaging hand, was way more powerful, and I started panting heavily.

When his dick rubbed against that particular spot inside me, I moaned loudly, and my dick started twitching furiously.

“Ooohhh. Yessss…”

Glenn just kept going. He slid in, retracted a bit, slid in further, and repeated this a few times. I was in heaven. The expected pain wasn’t there. Only the fantastic feeling of his hard dick inside of me and rubbing against something I didn’t know I had.

The moment I felt his pubes tickle against my hairless balls, I knew I would want this a lot more. Since his dick rubbed that spot the first time, I was on the verge of an orgasm.

“Oh, wow,” Glenn moaned, “you’re doing great! I’m all the way in.”

“Ooohhh. I know. Ahhh… I… hmmm…” was all that came out.

When Glenn slowly moved out, I felt like my orgasm hit me. But it lingered a bit, and when Glenn pushed back in, the same thing happened. With each fucking motion from Glenn, I felt like I almost came.

At that moment, I couldn’t speak anymore. Only low grunts escaped my throat, and all my attention was between my legs. Glenn was still massaging my dick, but he started jerking me in earnest after we fucked for a while.

The fucking wasn’t loud or obscene. Just slow, steady strokes from Glenn. But after he fucked me for a few minutes more, I noticed a change on his face. I knew by now that this meant he would be coming soon. At that moment, his inbound thrusts became more fierce, and when his groin slapped against my butt, this felt even better for me.

“AH! YES! AH! YES! AH! YES!!” I kept grunting.

“UH! UH! UH! UHH!” Glenn groaned.

The sound of loud slaps filled the room, and the feeling inside me intensified even more. I still don’t know if it was Glenn’s fat dick filling me up, the rubbing against ‘that’ spot, or the idea of being submissive to someone. But I don’t care now, and I certainly didn’t care back then.

“Ohhh… I’m cumming!” Glenn moaned and kept slamming into me.

The familiar tingle I usually felt when I came didn’t come this time. Instead, it was more like a whirlpool of soft cotton balls floating through my head and body. But when Glenn slapped at me with a final push, and his dick started kicking inside me, his hot cum coating my insides, all muscles between my belly button and knees began to contract.

Glenn and I came at the same time, and I felt so connected to him at that moment that I still remember that feeling vividly until today. My orgasm was very different from my usual orgasms. It usually focused on my dick, this time, it felt like it came from the inside behind my pubes. It’s hard to explain, and I still can’t put it into words. I did notice something splashing on my belly in the back of my head but was too engrossed with this different orgasm to notice or care.

Glenn stayed inside me for a few more moments but eventually, he had to pull out and lay down on his back beside me on the bed.

As we lay there side by side, regaining our breaths and letting the air cool us, I felt a bit of Glenn’s cum oozing out of my hole. I knew I couldn’t help it, and instead of feeling embarrassed by it, I felt a sense of pride for being able to give him this much pleasure and for being able to take his fat dick up my ass.

After a while, I felt something cold on my belly and looked down to see what it was. There, around my belly button, a long stripe of watery cum laid glistening in the morning light. I never came this much, and I wondered if this was even my cum.

Glenn saw me looking and said, “You came a lot, Bud! You’re becoming a man!”

He extended his fingers, scooped up a glob, and put it in his mouth. I did the same, and after two or three times, my belly was clean.

“How did I do?” I finally asked, curious how Glenn experienced it.

“Honestly?” he asked and looked at me.

I nodded shyly, a little bit afraid of what he’d say.

“I honestly didn’t think you could handle it and that you’d be too tight down there. But the opposite is true! You were amazing! It’s been a long time since I’ve had sex that was this good!”

I felt a blanket of pride covering me and realized we’d probably be doing this a lot more.

“And you?” Glenn asked, smiling.

“It was awesome! The moment your dickhead was in, I felt a bit of pain. But that was gone before I knew it. Your dick kept rubbing against a special spot inside me, and each time it did, it felt a bit better.”

“That’s your prostate. Most men like it a lot when it’s stimulated,” he said. And after a few seconds, “So do I.”

I felt a bit more oozing out and moved my hand down to assess the damage. Glenn noticed and said, “You’d better go to the bathroom and let it all out. After that, we’ll take a shower and clean ourselves up properly.”

And that’s precisely what we did. After showering, we ate breakfast together. And after breakfast, Glenn sucked me off at the kitchen table. Just like that. I wanted to return the favor, but he just said he wasn’t eighteen anymore and explained it took him a while to get going again.

It wasn’t even noon yet when we arrived at the beach. Glenn wasn’t much of a beach guy, but after a bit of whining from me, he decided we could go. Of course, we took the usual stuff like towels, sunscreen, and frisbee with us, but I insisted on leaving our trunks in the apartment. It took some convincing, but eventually, Glenn agreed.

Lounging naked on the beach with Glenn was absolutely amazing. We chatted a bit, swam in the ocean, threw the frisbee around, and generally had a good time. Being naked together in a public place added a whole new level to it for me, and it was simply fantastic.

I felt a bit odd down there for the rest of the day, but nothing substantial. Glenn assured me this would wear off. I didn’t care about it. I got fucked for the first time, and I loved it!

Copyright 2022 – Jason Crow
All rights reserved

Postica mea ridiculam sentit, sed eam amavi

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