Resort Tales #5
These ‘resort tales’ are one off recollections of a boy lover’s adventures at various beach resorts around the Caribbean. The stories, other than being written in first person by ‘Craig’, have no link to each other.
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Chapter 1 – My new underwear
A few weeks before a recent trip, I had ordered some new underwear for myself. I am a bit of an underwear geek, so this is hardly a rare occurrence. My overflowing underwear drawer is filled with lots of brands – 2xist, Andrew Christian, American Eagle, etc. Most are trunks or boxer briefs, but some are briefs and a few are old boxers.
I had seen an advertisement for a new brand and had been curious about them. Their webpage described underwear that had special compartments for one’s dick and balls that held both snuggly and comfortably but apart from each other to avoid sticking. I read a few reviews. Many reviewers touted they were like wearing nothing at all! I was intrigued.
Although they were a bit pricey, I couldn’t resist trying them. When they arrived, I immediately fell in love with them. The first time I pulled them on and my dick slid into the hole designed just for it, I was hooked. Not only were my boys nicely supported, my cock also had a home to call its own. Everything was held in the positions they would be if allowed to hang free. Not only that, they provided super easy access ‘the equipment’ for pit stops.
Long story short, I loved these underwear and I planned to order more once we were back from our trip. I wore one pair on the way to Mexico (our destination), and I packed another to wear home. (In between I wore athletic style / quick drying trunks under my swimmers).
Why am I telling you about new underwear? Because little did I know that the pair I packed to wear home would eventually help me get my hands on some hot teen dick.
Chapter 2 - Rodrigo
It was 3-4 days into our stay when I met Rodrigo. He joined in a water polo game. He was clearly Hispanic, though he spoke perfect English. I guessed he was probably 15, perhaps 16. He was about 5’9” and 175 pounds (yes a little pudgy). He wore glasses and sported a stylish haircut, short on the sides with a longer hair on top.
As I always do, I mixed in some conversation during the water polo game. I was shocked when Rodrigo told me he was only 13. He was very tall for 13. As I looked him over again, I noticed that his arm pits were still smooth and the fact that his face was still just a tiny bit ‘boyish’. Ok, I thought, he does kind of look 13 also.
In the course of an hour long game of water polo I learned quite a few things about Rodrigo. He was from Texas (San Antonio), both his parents were Mexican, and he speaks Spanish at home. (He was amused I am sure at my feeble attempts of Spanish with the staff). He was very proud of his heritage and freely talked about all the idiotic stereotypes people have about Mexicans. “Let’s get some things straight,” he told everyone. “No, I didn’t sneak across the border, I am not a drug dealer and no I don’t have a low rider.” I loved that he was so brazenly making fun of all the stupid stereotypes. He did admit to liking tacos.
“Tacos? Everyone likes tacos Rodrigo!” I told him. “You left out a couple other stereotypes. Your family probably works really hard to give you things they didn’t have and your family is probably very close, right?” (I loathe the stereotypes of Mexicans that some Americans hold. The immigrant families I have known are all fantastic very hard working people who will do anything for each other).
He looked at me and smiled and gave me a small salute. I had earned his respect.
As the game began to die out, conversations increased. I learned a few more things about him. He doesn’t play many video games. He even hates Fortnite. He takes his schoolwork seriously. He struck me as a young man with very strong convictions and a strong sense of right and wrong. Even in the game I noticed he played very fairly and tried to include little kids (something I did myself). I was quite impressed with him as person.
That is until the subject of relationships and such came up. I don’t remember how it came to the subject of same sex relationships, but Rodrigo clearly had a homophobic streak that I wasn’t expecting given everything else I already knew. He used the term ‘faggot’ and talked about gays being ‘not normal’. I was disappointed. I know there is a machismo anti-gay sentiment common in Hispanic culture, but the rest of his positions seemed so just, this just didn’t fit. Was it based on religious convictions perhaps? I left the pool puzzled about him.
Chapter 3 – Getting to know Rodrigo a bit more
A few days after meeting Rodrigo, we found ourselves sharing a lounger on the sidelines of a pretty competitive volleyball game. We were making small talk and it lead to a much longer conversation.
We started talking about music and found we actually liked a lot of the same artists. He was shocked to hear I actually liked the rapper Eminem and we talked a lot about our favorite songs of his and how much emotion he packs into his songs. Our conversation was going so well we both declined to move on to volleyball whenever spots opened up.
Our conversation moved on from music. “Do you like Anime?” he asked.
“Nah, not really.”
“I love it. It’s cool. Did you know there’s a kind of Anime that is like pornographic?”
Now of course I knew that, though it was not something I’m really into. “Yeah, I’ve run across it a time or two I think. I forget what it’s called though.”
“Hentai,” he answered quickly.
“Yeah! That’s it. I knew I would recognize it if I heard it,” I answered. “So, what are you doing looking at porn son?” I teased him.
He gave me a shy grin. “I think you KNOW what I’m doing Craig. You’re not that stupid.”
I laughed. “No worries. If the internet existed when I was 13, oh boy, I would have been doing all kinds of things.”
“You wouldn’t believe the things that are out there. On the dark web especially.”
Now THAT intrigued me. I don’t explore the dark web, wouldn’t even know how to – but I am pretty sure the stuff out there wouldn’t be your typical legal porn. Maybe my new friend wasn’t so pure after all. As curious as I was to know what else he had found, I decided it was safer not to get the topic too close to my own attractions. “Yeah, I hear there is crazy shit out there.” I let the topic drop.
He changed topics for me. “Have you ever heard of Inimissimi? It’s like a Victoria Secrets in Italy, but they sell men’s stuff too. My mom went to Italy and bought me some underwear there and it’s like the best ever. So soft.”
OK now this was a very unique topic for a 13 year old to bring up out of nowhere!! I was kind of shocked, but hey, underwear is definitely of keen interest. “What kind are they?”
“What do you mean?”
“Like what style? Boxers, boxer briefs, briefs? Maybe trunks if they are from Europe?”
“I don’t know what you call them,” he answered. “They are like speedos,” he added, drawing lines with his hands from inner thighs up to his hips, demonstrating the cut.
“Those would be briefs Rodrigo. I didn’t know kids your age wore those. I thought everyone had moved on to boxer briefs and trunks these days.”
“Not me. These are so comfortable. My mom ordered me more online. It’s like all I wear now.”
“Nice. I have a ton of different types. It’s nice to change things up. But my favorites are one’s I just got. They have like a special pouch to put your dick in.”
He looked at me puzzled. I tried my best to explain but it’s difficult without pictures. “Just google it when you can, it will make more sense.”
At that point we got coaxed back into playing volleyball, so our conversation came to an abrupt end.
As I was showering that evening, I replayed our revealing conversation. He likes porn – not a surprise at all, but the dark web? And discussing underwear? Then it suddenly hit me – Rodrigo likes guys! All his “faggot” pool talk was just to put on a façade, or maybe to deal with his own self-doubt!
We were in another water polo game the next day. Rodrigo was being his normal outgoing self. I had been in a struggle for the ball and had just come back from under the water near him.
“Oh my god, Sorry! I said the F word,” Rodrigo said and then paused. I assumed he meant “Fuck” of course as I hadn’t heard what he said since I was under water.
“Faggot,” he said after a pause.
As I moved past him, I slapped him on the back and said quietly so only he could hear, “Aw, don’t be so hard on yourself amigo.” I didn’t wait for his reaction but moved back into the game.
A few moments later when I turned, he was still glaring at me. It wasn’t a glare of anger. It was more of a quizzical look. I knew right then I had guessed right about him. I had pierced his façade of machoness and figured out his secret. I smiled at him and nodded.
The game ended soon after and I dried off and started walking down the beach towards the grill to grab a burger. I was surprised when he suddenly came running up beside me. Before I could even say hello he drilled me with a question “How the fuck did you know?”
As we walked, we talked. “I didn’t KNOW for sure, but I had a hunch. I mean we did talk about underwear yesterday ya know?” He chuckled. “Let’s grab a bite and sit down and we can talk. It’s ok Rodrigo. Really.”
I intentionally chose a table far from other guests. He had just sat down with his tray of food and taken a bite when he asked me. “So are you…um…you know? Too?”
“I’m have numerous attractions Rodrigo. And yes, sometimes they include guys. But it’s complicated.”
“Yeah me too,” he said.
“Yeah I remember. Hentai? We talked about it yesterday.”
He looked around to make sure nobody was near and then leaned in. “I look at a lot more stuff sometimes,” he responded with a guilty look on his face.
I assumed he meant gay porn obviously. “Yeah, ok, so lots of people like gay porn. I’ve watched it too. No big deal.”
He was silent for several seconds, pensive.
“I…um….found other stuff too. On the dark web. Stuff with boys my age,” he answered, looking down. Before I could respond, he cursed himself. “Shit, I shouldn’t have told you that. Now you think I’m a perv probably.”
I reached under the table and gave his leg a friendly squeeze. “Relax man. It’s fine. If they are your age that seems normal to me. If I was looking up that stuff, I’d be a perv, but not you. But damn dude! Be careful. You can get in trouble with that stuff.”
He looked down, solemn. “I know, I tried to stop but it’s hard. I mean boys my age are cuter than hair men.” He looked at me. “Sorry no offense.”
“I understand, completely!” I whispered and gave him a wink as I got up and went to refill my drink. He gave me a puzzled look as I walked away. I have no idea if he really understood what I was trying to insinuate.
I returned with my drink and we ate our last few bites in silence. The discussion was apparently done. He knew that I knew he was gay or bi – I never really asked which – and he seemed to want to leave it at that.
As we were almost ready to leave, he spoke up. “Any chance you’d show me those underwear? I googled that shit and I couldn’t quite figure out how they work?”
Chapter 4 - Score
Rodrigo followed me back to our room and followed me inside. He looked around briefly at our well kept domicile. “Just like your room,” I asked?
“Yeah, but ours is just opposite… and a little messier.”
I went to the closet and slid open the door. I had all of my underwear and socks stored in a pullout drawer. I opened it and retrieved the pair of underwear I had packed along to wear home. They were black with a navy blue waistband and navy blue stripes on the side.
I held them up. “Here they are,” I said.
Rodrigo reached out and felt the material. “Wow, they are really soft. Just like the briefs my mom got me in Italy. But they just look like boxer briefs. What’s so special?”
“Yeah, but they aren’t,” I replied. I turned them inside out. “See the hole here? You’re dick slides in there when you put them on and it keeps it separated from your balls. And they have a special support pouch for your balls too.” I could see him trying to work out in his mind exactly how it all worked. “It’s hard to explain. I really didn’t get it either until I put them on for the first time. And then I was like WOW.”
He continued to hold and stare at the round 2” hole made for one’s penis. “I know this is kind of weird,” I began, “but we’re kind of the same size I think. What size is your waist? You could try them on if you wanted?”
“36, but um…that’s ok. That WOULD be weird.”
“Yeah I get it. But honestly, they are practically new and I am not even sure I’ve worn that pairyet.” Rodrigo thought for a minute. I could tell curiosity was getting the best of him. “Really, don’t sweat it. I have others I can wear if I need them. And I could really rinse them out too or whatever.” Truth was I would have gladly worn them, knowing my dick was housed in a pair of underwear that had held his previously.
“You…you…sure you wouldn’t mind?” he stammered.
“Dude, just try them on. I promise you you’re gonna fucking love them.”
“All right,” he sighed. “I’ll just go in here,” he said, going into the bathroom and pulling the sliding doors shut. (The bathroom had two sliding doors with slats that separated it from the rest of the room.)
I stood outside the door and watched through the slats. I heard him strip off his swim trunks and saw them hit the floor through the door slats. “When I pull them up my dick just slides into that hole all by itself. You don’t really have to work at it or anything.”
“Ok,” he answered as I saw him stepping into my trunks. “It does just kind of pop in,” he commented as I heard the waistband snap. “Holy shit, these feel awesome!” he exclaimed.
“See! I told you!” I answered.
I was shocked when he actually opened the door and was a little embarrassed at being caught waiting just outside the door. “They fit me really well too,” he said, turning from side to side. I could see the dick pouch nicely filled as well as his ass filling the backside of the trunks.
“Yeah, it looks like they do Rodrigo. I told you that you would like them huh? Did you figure out how the fly thing works?” In this underwear, you dick rests in a J-shaped piece of fabric and to access it you just reach slightly under and pull out wards. It’s very easy. Then to put it back after pissing you simply fold the material back over the end of your cock.
Rodrigo reached down to the fly and was at first puzzled. Then a gentle pull of the fabric released his cock and suddenly there it was! A gorgeous 13 ½ year old uncut piece of Mexican meat dangled just before me. It was probably almost 4” soft and rather thick. I couldn’t help but to stare. In fact, not only did I stare, but my hand instinctively began reaching for it before I caught myself.
But not before he noticed. “Were you going to grab my dick?” he asked accusingly, backing away into the bathroom.
“No, not really. I mean it’s a really nice dick, especially for a 13 year old. I guess my first reaction was just to touch it, but I caught myself. Sorry Rodrigo, I didn’t mean to frighten you. You should probably get changed so we can head back down to the beach,” I said as I slid the door shut so he could change.
After I closed the door, I walked over to the desk to plug my phone in. I was shocked when I turned around and Rodrigo was standing just outside the bathroom door looking at me, his dick still hanging out of my trunks. It was clearly fuller than it was a few minutes ago.
“It’d be ok….you know… if you….um….wanted to…you know…. touch it.” I couldn’t believe my ears.
I walked to him, looking him in the eye. “Are you sure Rodrigo?” I asked as I got up to him, his gaze still locked on mine. He totally seemed like the type of kid who was going to have post-orgasmic guilt and I wanted to make sure he was really ok with it. “No regretting this?” I asked. He shook his head.
I reached out and took his hefty cock into my palm and gave it a gentle squeeze. He gasped. I pulled gently, giving it a couple soft strokes. I could feel it growing and stiffening quickly in my palm, beginning to point slightly upwards. Looking down, I could see his pink glans extending past his quickly withdrawing foreskin as I gently kneaded his gorgeous cock. His foreskin was tight, peeling away slowly but remaining taut against his cock head, which is a huge turn-on for me.
I rubbed my thumb over the top of his head, flicking his piss hole and feeling a few drops of pre-cum under my thumb. I rubbed it over the whole of his now exposed and apparently super sensitive cock head. “Oh god,” he moaned as I continued the motion.
“You sure you don’t want me to stop Rodrigo? This is ok amigo?” I asked as I continued to fondle his hardness.
“Don’t you fucking dare stop Craig,” he answered opening his eyes and staring at me briefly before closing them again and moaning as I slowly stroked the length of his full erection, which was now easily 6” long.
I grabbed his dick and pulled. “Let’s move to the bed and get comfortable,” I said as I guided him around the corner to the first bed, leading him by his hard cock. When he reached the bed he flopped down on his back. I propped a couple pillows under his head. “Get comfortable Rodrigo. I want to play with this hot dick for a LONG time.”
“Oh fuck, I don’t think I can take much more…but…I’ll try,” he whimpered.
I pulled my underwear off him in a quick motion. I didn’t want him to jizz all over them. I already planned to give them to him. I took in his boy beauty. His plump erection rested on his soft belly, almost reaching his belly button. It rested on a small bush of dark black pubes. His balls hung low, and not surprisingly, were still smooth (just how I like them). “Be right back,” I said. I realized I hadn’t latched the safety lock and didn’t think this a scene my family would like walking into.
When I returned I softly stroked the length of his dick with my finger, using the softest of touches while my other hand cupped his super soft balls. “This is one fine cock Rodrigo. Thanks for letting me get to know it a little better. I switched to a firm grip and watched his skin work up and down his plump pink head. Soon Rodrigo was issuing a string of expletives in Spanish, most of which I did not understand.
But I do know some Spanish slang. And in the midst of his stream of profanity, I clearly picked out chupa mi verga (suck my dick). I looked up at him, his eyes were plastered shut as his mouth continued to move. “Yes, sir,” I said coyly before lowering my mouth to his cockhead and engulfing the tip in my mouth.
I had positioned myself such that I could watch his reaction. When my mouth hit his cock, his eye’s shot open. “Oh fuccccccccccccck,” he said as he arched his hips, seeking deeper warmth for his teen cock.
I took more of his cock into my mouth and sucked gently, causing him to yelp loudly and buck even more. I knew he wouldn’t last long and as much as I wished the playtime with his teen cock would last forever, I also knew I couldn’t take too long and risk someone coming back to the room. So I pulled back his foreskin and plunged deep, taking his cock into my throat and sucking. He responded by thrusting like mad. I knew my mouth would soon be flooded with whatever load he was capable of producing.
As it turns out, his load was more substantial than I expected. It was thick and creamy and much more copious than I would have imagined. I let it gather in my mouth as his orgasm subsided and then swallowed his creamy goodness, before letting his wet cock slip from my mouth. I looked up at Rodrigo and there were two small streaks of tears running from his still closed eyes. I wiped them away. “You ok amigo?” I asked softly.
He nodded. “I’ve just never cum so hard before. Not even after jerking off all night. I wasn’t sure what actually being with another guy might be like, but that was …was….awesome.”
“No regrets then?” I was fearful he was going to have remorse now that the act was complete.
“NO!” he answered. “No way. That was amazing.”
“Good to hear,” I said. “Stay here.” I went and got a towel and his swimsuit and came back and wiped his soft dick clean of my saliva and his jizz. “We better get going amigo before we’re missed.”
“Yeah,” he answered, pulling on his trunks from the edge of the bed. “Craig? Thanks!”
“You’re welcome,” I answered, pulling him to his feet and giving him an embrace.
I offered to let him take my underwear home, but he refused and said he would order some himself.
We left the next day, but I did see Rodrigo eating alone at the breakfast buffet. We said goodbye there, next to the donut bar. “Thanks so much,” he told me.
“Be yourself Rodrigo and don’t be hard on yourself either,” I reminded him.