Max’s Freudian Slip #24
Author’s notes:
Apologies for such a long gap between chapters. A new chapter of Max’s Awakening was recently uploaded in the young friends section, for those of you following both stories.
I hope Covid-19 hasn’t caused too much trouble in your lives!
This chapter picks up the morning after Craig and Max’s big fight (after Max was caught on the beach with Eduardo’s cock in his mouth and Craig admonishes him for being too impulsive and careless.)
Please remember to support Nifty so the platform for these stories can continue.
Chapter 24 – Diving Deep
It was difficult to sleep after the blow-up with Max. I tossed and turned all night thinking about what had happened. I concluded at some point in the wee hours that I had been too harsh on him, and for that, I felt guilty. But there was also no question that Max needed to figure out how to curb his impulsiveness. I heard Max shifting a lot as well. I don’t think he slept any better than I did.
I must have eventually crashed hard, because the alarm gave me a rude wake up when it sounded. Max and I were both groggy, but we managed to drag ourselves out of bed and make it to the dive boat without being too annoyingly late. We were both unusually quiet through breakfast, but I tried my best to be pleasant. I wanted to start the day with a clean slate, so I didn’t make any mention of the previous night’s events.
Diving was much more fun than our first two days had been. That was partially because we were finished with Max’s instructional dives. Max had passed his tests and was now a full-fledged PADI scuba diver, so we were able to enjoy the dives without being interrupted by skills testing. Our company on the boat was a lot better as well. Charlie and his prick of a father were replaced by two really fun middle aged women. At first I assumed they were just good friends, but after talking a bit, they informed us they were married.
They were very outgoing and took an interest in Max right away. They were impressed with him being a young diver. They told us they had a son themselves, younger than Max, but that he wasn’t the type to try scuba diving. As I watched Max interact with them, it reminded me of Max’s qualities that made him special. He was affable, engaging, and completely charming. By the time we were gearing up for our first dive, I could tell the two ladies already adored him. It only served to remind me that I was probably too severe on him last night. Thankfully, he didn’t seem to be showing many ill effects of our argument. But, maybe these two women were just what he needed as an alternative to talking to me.
***
The diving was superb and Max spent a lot of time with our new dive partners when we took a break between dives. I let him wander off to the beach with them while I stayed on the boat and visited with Adrian, our dive master. Adrian said the Charlie and his dad had been just as much a pain the prior two days on another boat. I wasn’t surprised.
As the boat returned us to the resort at the end of our morning, I was alarmed to see Eduardo sitting on the end of the pier, waiting for us. My heart sunk. I was fearful that something had happened in relation to last night (such as the security guard having found his parents). But, thankfully he was just bored and couldn’t wait for Max to return. As our boat approached he stood and started waving. You could tell he was very pleased to see us. He had a huge smile on his face, completely opposite of his demeanor from late last night.
He grabbed lunch with us and told us about his morning. He’d said he’d been keeping to himself, just to avoid potentially being seen by the guard with his family. But he reported he hadn’t even seen the guy. I surmised that he probably works nights, so day time was not likely to be an issue. But in relaying that to the boys, they were suddenly scared about being around the hotel that evening. They both begged me to go into town again for dinner again and to hang out. How could I say no?
As we were finishing our lunch, Eduardo asked Max if they could go up to our room. “I’ve got something I want to show you,” he said. But he said it with a smirk and a certain look in his eye. I had a feeling the “something to show” was a big hunk of Mexican teen cock. I told the boys I was going to relax by the pool and do some reading. I grabbed Max’s arm and pulled him to me just as they started to head off. “Make sure you lock the door ok, if…well, you know.” The last thing they needed was a maid walking in on them.
“Got it,” he replied with a smirk.
***
Full from lunch and tired from diving, I headed back to the main pool area. This resort has extensive greenery around the large central pool. It’s like a miniature tropical jungle. In the middle of the shaded forest they strung a couple of hammocks, reachable by stepping stones. The hammocks, and the stones to get to them for that matter, are so well hidden that a lot of people don’t even notice them. It seemed like a perfect place to go relax.
I was pleased to find both hammocks empty and climbed into the shadiest of them. I closed my eyes and tried to catch some sleep to make up for last night’s restlessness. Unfortunately, I was close enough to the pool that the noise of playing children and Latin music kept me from being able to really fall into a deep sleep.
Which - turned out to be a rather good thing. I had probably been lying there about 20 minutes when I heard an unusual language being spoken from the direction of the pool. It was either Dutch or German, neither of which I’ve heard spoken much on Cozumel. (Lots of Dutch and German people do visit the Riviera Maya but they tend to stay on the mainland). I opened my eyes just in time to spy a blonde boy of about 12 through the foliage. He was pulling on a pair of red boxer briefs and I focused in on him just in time to get a brief glimpse of his pale butt!
Wow! What an unexpected surprise! He walked a bit to the left and turned. I could see he was wearing a German national team football (soccer) jersey. He was absolutely gorgeous. My mouth dropped at his stunning beauty. He had an adorable face with a perfect complexion, topped with a wavy mop of thick blonde hair. I wasn’t close enough to see his eyes, but I’m sure they were a perfect shade of blue. His mother, the voice I heard, was waving him to come along. It appeared they were headed to lunch and that he had wanted to change into dry clothes first. He carefully hung his wet trunks across the back of a lounger and off they went. There was a mom, dad, this boy Adonis and a smaller version of him that I presumed was his little brother.
I know German’s have a much more casual attitude about nudity than the rest of the world. They are the originators of the whole FKK (Frei-körper-kultur) nudist culture after all. I’ve seen many a German family change their small kids pool side, but I’ve never seen a boy quite this old willing to be so daring. He had ducked behind a cabana, so he was partially hidden from view, but I am sure there are several angles where he could still be seen. Including of course, my perch amongst the trees. I guess he just didn’t really care. (An attitude I find quite liberating actually).
Needless to say, that little surprise glimpse of hotness had me quite alert. There was no way I could doze off now and perhaps miss him changing back into his swim suit after they had lunched. I grabbed my phone from my bag and thumbed through some emails and then, inspired by my young German friend, decided to head off to nifty to read a selection from the adult youth section.
There was a story by one of my favorite authors (Pink Panther) that I had been meaning to read more of. It was a story about a teacher at an all-boys school in England in the early 1960’s seducing his students. I had gotten a few chapters read a couple weeks before and wanted to pick it up again on this trip, but hadn’t found the time yet. It was a good story, setup with an interesting array of characters. He’d managed to bed a boy or two in the first few chapters. I had just begun the 7th chapter when the German family returned. I lowered my shades, cocked my head, and placed my hat over part of my face. I would appear to be sleeping should anyone happen to look this way through the leaves. Then I watched.
The show was not a disappointment! German boy, and his little brother, who appeared to be maybe six or seven years old, grabbed their trunks off the back of the chair and ducked behind the cabana. The little brother wasted no time undressing, tossing his shirt off and pushing down his shorts. He seemed to enjoy being nude and bounced around, almost dancing as he gathered his trunks off the cement. I could see his long foreskin dangle in front of him, jiggling as he moved. His trunks must have been wet still, because they got stuck around his thighs as he tried to pull them up. His brother came to the rescue and helped pull them up the rest of the way. The little guy started to run off before his brother yelled to him. He came back, grabbed his clothes, tossed them on the chair and ran off towards the pool, leaving his brother alone. It was really quite an adorable scene to watch. The little brother was way too young to be an object of any lust (at least for me). He was at an age where I find boy’s to be very cute, but not arousing, if that makes any sense. I would describe seeing the younger boy naked as just ‘interesting’. Big brother, of course, was a different story.
The older blond gave a glance in many directions and then peeled off his shirt. He either didn’t see me or plainly didn’t care. I was only 15’ away at most, but amidst the trees. He pulled down his shorts and underwear all in one swift motion. With his back towards the cabana, I had a perfect view of his boyhood, which was divine. While he appeared hairless, it appeared the boy was clearly at least close to the onset of puberty. His balls hung low and above them arched a thick tube of boy cock that had to be at nearly 4” long with another good inch of loose foreskin hanging beyond it. He must have a thick cock head, because even at my distance, I swear I could make out the ridge of his head beneath his skin. My heart raced and I had to swallow to keep from gasping. The boy was stunning in every way. He was perfection. What luck!
I couldn’t help but think that he could be a slightly younger version of Max. They both had similar hair and similar builds. The German boy wasn’t as muscular as Max, but he still had a very lean, athletic body. I would guess that he played a lot of soccer. And just like Max, he was a bit of nudist it seems. Watching the boy made me a bit remorseful that I never knew Max, at least not intimately, when he was the age of this boy. It’s the perfect age in my opinion, when puberty is just beginning to change a boy’s body. Their balls have dropped and their cock is growing, but they are still completely smooth (or close to it) and perhaps beginning to experience wet orgasms. Is there not a more perfect time in a boy’s life?
By the time he pulled on his trunks and headed off towards the pool, my cock was rock hard. I placed my towel over my legs and gave it a few tugs before returning to my nifty story. Needless to say, the more I read, the hornier I got. As Alex, the teacher in the story, made his way through more horny students, my cock was oozed a copious amount of precum into my Speedo, which I still had on from diving.
The one interesting aspect of this nifty story, at least sexually, was the position that Alex and his boy-loving mentor preferred when fucking their students. Alex, the protagonist, liked to have his boy’s lay face down on the bed with a pillow under their hips to prop their ass in the air. He liked lying atop them and “giving them what they need” (which means he liked to fuck them really hard until they creamed the pillow with their boy juice – if they were old enough to cum that is). According to the author, an already tight boy hole was even tighter in that position. I must say the thought of topping someone, or getting topped, in that position intrigued me. I’ve topped a few guys, and been fucked many a time, but never had I done it in that position. On my hands and knees (doggie style) had been my most commonly used approach. Though, I had also ridden a few guys from the top and been fucked on my back.
Alex’s mentor had an even more peculiar preference. Gordon, the teacher who showed Alex the ropes when Alex was just a boy, liked to sit on a chair with his rather large 8” prong pointing in the air. The boy would face away from Gordon, spread his legs, and lower himself down onto the teacher’s cock. Once impaled, the boy would put his feet on the something in front of him so that gravity would bring the full length of Gordon’s massive cock to rest inside the boy. Gordon would then grab the boy by the hips and fuck him silly.
Beyond being intriguing, I couldn’t help but to apply these images to my own desires with Max. Last night, before the incident with the guard and our fight, we were on a path that I anticipated would end the night with my cock inside him – FINALLY getting to fuck a boy for the first time. In my head, I had planned to do it with Max on his back, so I could watch his face as a man-sized cock invaded his tight hole for the first time. I thought that would allow me to monitor his reactions for any misgivings or signs of pain. But now, having read this story, I began to ponder the idea of doing it like Alex prefers – with Max face down on the bed and a pillow propping his ass up, like a gift for my taking.
At that point of course, I wasn’t sure if Max would even still be willing. Yesterday he told me he wanted it. But I wasn’t sure if the fight might have changed his attitude. Maybe he wasn’t horny any longer? Or if he was, would he still be after Eduardo ‘showed him’ whatever it was he had to present?
After my afternoon of erotica reading and German boy watching, I knew one thing for sure: I had thoroughly dismissed any reservations about taking it further with Max. I was sure as hell hoping Max had retained his interest because I desperately wanted to make passionate love to him. But, I knew it would not feel right, and as special as I longed for it to be, unless Max truly wanted it as well.
***
I had to hunt down Eduardo and Max to have them get ready to go into town for dinner. They weren’t in any of their usual spots. They weren’t playing water polo or hanging out near the pool bar or at the pool tables. I ended up finding them on the small beach cove, building sand castles with Marcelo. The idea that the two teenagers had gone up to our room to mess around earlier (at least I presumed they did) and were now on the beach playing with Eduardo’s little brother struck me as kind of funny. It was also cute and reminded me that even at 14, there was a little innocence left in Max yet.
As we went to our room and got ready, Max seemed unusually quiet. I wondered if the events of last night were weighing on him still or if something had happened with him and Eduardo. I surmised that the latter seemed unlikely with them having been hanging out happily on the beach. But before I could ask him about it, he had retrieved his phone and was in the midst of a text conversation, or three. I decided to just let it go for now. I didn’t want to put a damper on a good day. We could always talk at bedtime. Though, there is something else I’d much rather do than talk.
***
We met Eduardo in the lobby and caught a cab to El Moro. Max continued to be subdued on the cab ride, choosing to stare out the window instead of engaging with Eduardo or I. Maybe he was just intrigued by the array of shops and homes that dot the back streets, but it sure seemed like something was on his mind. It made for a somewhat awkward ride, filled with silence.
El Moro is one of my favorite restaurants on the island. It’s far from the main drag where tourists typically go. It’s a pretty good size restaurant though, considering it takes up the front patio of the owner’s house. Ray, the man that runs the place, makes it seem like you are visiting your favorite uncle’s house for Sunday dinner.
We were just walking in the door when I heard someone calling out Max’s name. It was the ladies from the boat! They had just sat down with their son at the end of a long table. They immediately invited us to join them. You could tell they were thrilled to see Max again (even though we were to be on the boat together tomorrow as well). Their son, Joshua, was 12 but didn’t look it at all. He kind of reminded me of the kid Lucas in that movie with Charlie Sheen and Corey Haim (Lucas). Joshua had thick, medium length black hair that was rather unkempt. He wore glasses that were framed by some freckles. If I had to describe the look, I’d call it ‘band geek’. Not that I was judging him, I like boys of all shapes and size and interests. I was just trying to give you a feel for what he looked like.
The moms kept trying to get Joshua to engage in our conversations, but he resisted. It was obvious that he was horribly shy. It didn’t help that Max and Eduardo were both being quiet too. Finally, somehow in the course of talk about vacations, we got to discussing New York City and started talking about various Broadway shows. The kid suddenly came to life. He wasn’t a band geek - he was a theater geek! He knew a ton about Broadway. We had seen several of the same shows and got to compare notes on who was starring in them and what our favorite parts were.
He followed Max to the restroom just before our food came and returned even more talkative. He suddenly seemed very interested in Max’s sexuality. He was asking all about how he knew, when he knew, when he planned to tell the world, etc. I am not sure what they talked about away from the table, but clearly returned knowing that Max was gay. Max might have told the moms while on the beach between dives and perhaps Joshua had heard about Max from them? Or did he actually find out from Max when they were in the restroom? Could they have actually messes around in the bathroom? No way.
Joshua’s litany of questions brought Max out of his quiet mood as well. With someone so interested in him, he was talking a lot again and seemed more like his usual self. It was good to see. Maybe I was concerned over nothing?
Watching Josh interact with Max, it became obvious the younger boy was completely enamored with Max. I’m not sure if he was crushing on him, or just in awe of how bold Max was with being ‘different’. Joshua was certainly a unique, so maybe Max was a role model of sorts for being different and confident? Either way, it was a pleasure to watch Max help bring this shy kid out of his shell. The mom’s were watching the entire time and smiling at each other and at me. It made me a proud ‘dad’.
***
When our food came, Max wolfed down his steak and rice. But, I was very glad to see he abstained from the refried beans. (For obvious reasons).
***
It was rather late by the time we got back to the resort. After dinner we went to the square and listened to some live music, did a little dancing (my first time dancing with a lesbian - I think) while the boys played tag and hide-and-seek with a group of local kids. It was fun to watch them interact and even Joshua seemed to be enjoying himself. Max seemed out of whatever funk he had been in (if he had been in one at all). He was smiling and laughing as the group played. It struck me a little funny that Max could be so mature at times. He was begging for me to fuck him yesterday, but yet today he was still playing like a little kid on the beach and now here in the square. It made me pause. Should I really be thinking about fucking him?
My hesitance didn’t last very long. As we danced and drank under the moonlight, sex permeated my thoughts. I had done nothing to alleviate the tension built up during the German boy display and erotica reading. I didn’t have time to jerk off in the shower. I was still mulling the idea of topping someone, ok – namely, MAX, with him lying face down on the bed with a pillow under his hips. I was just hoping he would be in the mood for it. So far the day had gone reasonably well – Max was enjoying himself and it seemed last night’s follies were past us. How to bring it up though? He hadn’t mentioned it since yesterday afternoon. Would he be interested still?
***
We had delivered Eduardo to his parents and made plans to meet them in the lobby before they left the next afternoon. We were alone on the elevator riding up to our room. “Are you ok?” I asked him.
“Sure. Why?” he replied, looking at me as if it were a strange question.
“I don’t know. You just seemed awfully quiet at the start of the night. That’s all.”
“Um, um….I was just a little tired I guess,” he replied.
That actually made sense. He hadn’t slept well and didn’t have a nap like I had. I was probably making something out of nothing. “So everything is fine with you and Eduardo?” I knew they were fine, but I really wanted to segue the conversation into finding out what they did in our room after we got back from diving.
“Oh, we’re good,” he replied, emphasizing the word good. “REAL good.”
“So I take it you guys got to finish what you started last night on the beach?”
Max confirmed what I suspected. “Yeah, no interruptions this time. He loved it.”
“Did he return the favor?”
“We 69-ed for a while. But once I made him cum he didn’t want to do anything else,” he explained.
Perfect! That meant Max has to be a bit horny, right? The elevator opened and we walked off. “Oh you poor poor boy,” I said overly dramatically as I patted him on the shoulder. “Max, you know all is forgiven about last night. I’m so over it. Hopefully you are too.” And hopefully you’re willing to let me fuck you still, I thought to myself.
“Yeah,” he muttered and wrapped an arm around my waist and gave me a side hug as we walked down the hallway. “Thanks.”
***
I was hot and sticky from being out in the humidity all night and felt like a shower. Plus, if we were going to maybe fool around, I wanted to be clean for Max. I hoped he would want a shower as well so that he too would be clean. Especially his back end. “You want a shower?” I casually asked as we entered the room. “It’s your turn to go first.”
“I need to talk to Cam first, so you go ahead,” he replied and he took his phone to the balcony.
I stripped off my shirt and then remembered I had told my wife I would call her when we got back to the hotel. I sat on the bed and dialed her number……..
***
I had just hung up and plugged my phone in when Max came in from the patio having finished his conversation with Cam. “I thought you were going to shower?” he asked.
“Sorry dude,” I said. “Got stuck on the phone with home. You can go ahead if you want.” Then I had an idea. “OR we could just shower together real fast. It IS late and we have to get up early you know.” Many a fuck session begins with a harmless shower, right?
“Sure,” he shrugged and headed for the bathroom. As soon as he rounded the corner I jumped up and did a little dance of excitement as I kicked off my shoes.
I stripped down and looked to make sure I wasn’t boned up already. It might be creepy for him if I walked into the shower already hard. I wanted anything that eventually occurred to have seemingly happened spontaneously. My cock had plumped some, but it was still soft enough to dangle and sway as I walked. I headed around the corner and into the bathroom. Max was standing just outside the shower, naked and beautiful, with his hand testing the water, waiting for it to warm. He took one sight of me and laughed out loud. I guess he didn’t expect me to come marching into the bathroom naked.
“Don’t laugh at my dick!” I told him. “It’s not that big!” My stupid dad joke made him laugh even more. “And it’s not THAT small either.” He was giggling as he stepped into the shower. I briefly admired his perfect body from behind. His perfect round ass set atop muscular legs and a below a smooth heavily tanned back. The tan lines from wearing Speedo in the sun were unbelievably sexy. His body is already off-the-scale hot, but with the addition of the deep tan outlining his sexiest parts, he was unresistable.
I couldn’t help but to compare Max’s rear to the similar butt of the German boy. Max’s was more muscular, but just as pale and smooth - and inviting. Could there be a more perfect barely 14 year old ass to sink one’s cock into? I couldn’t imagine anything could compare.
As he turned to the side, his 3” soft dick came into view highlighted by his short bush of blond hairs. God! He was even more perfect than the German lad! I decided I better get into the shower before I got too aroused.
We took turns soaping and rinsing off. Max had just finished rinsing his hair was letting the spray wash over the front him. I put my hands on his shoulders and leaned into him. “Max, I’m really sorry about being so angry last night,” I said softly as I gently massaged his shoulders.
“It’s ok. I was pretty stupid too,” he replied. I grabbed the bar of soap and ran it over his back and across the top of his ass and briefly into the top of his crevice. His body was silky smooth. It was firm and muscular, yet still soft to the touch. Hair takes away so much from a guy’s attractiveness. It’s evil. Feeling his velvety smooth body was making me so horny. It’s a wonder I didn’t bend him over and fuck him right there in the shower. The image of doing exactly that certainly flashed in my mind.
I put the soap on the tray and wrapped my arms around him from behind. “I don’t know if you realize it, but you’re very special to me Max. Honest. I love you dude.” I was never good at sweet talking. I’m always too direct, but hey, I had tried. I relaxed my hug and stepped back slightly. I ran my finger over his soapy back and down onto the top of his ass. “Any chance you still want to put one of those condoms to use?” I asked.
His response surprised me. He flinched and twisted away from me! It was a silent but clear rejection that I did not expect. It wouldn’t have surprised me if had said no, but his reaction seemed to say he was almost disgusted by the idea. “Sorry,” I said immediately, aware that I had clearly approached this wrong. “I didn’t mean to….” I said, but couldn’t quite finish my thought. I was angry with myself for turning him off like that. I should have waited for him to bring it up again!
“No, it’s….um….okay,” he stammered. But his body language was saying something else. “You just surprised me and um… your finger tickled. That’s all.”
I wasn’t really buying it. I backed off. “Nah, it’s okay dude. I shouldn’t have brought it up. I told you I would leave it to you to initiate things and then I didn’t even follow my own rule. We don’t have to do anything.”
“No!” he responded sharply, which caught me off guard. “I…uh…wouldn’t mind a blow job if you wanna do that. You know, since I didn’t get to cum when I was with Eduardo.”
It wasn’t what I had hoped for. But, alas, beggars can’t be choosy, right?. And the truth was I could dine on his awesome cock all day, every day. “As you wish,” I told him.
***
I grabbed a towel and dried him off. I was trying to pamper him and make him feel special. I thought it would be cute to carry him from the bathroom and that almost ended in disaster as my foot slipped a bit on the wet tile and I almost dropped him.
I took him to the bed and lay him on the pillows. We looked at each other and smiled. For all we’ve done so far, we still hadn’t really made out. I knew he and Cam kissed, but I wasn’t sure what Max would think of doing it with a man. I gently lowered my lips to his and gave him a soft, non-aggressive kiss to test the waters. He reached behind me and pulled my head tighter and immediately pushed his tongue into my mouth. I guess that question was answered. We made out for a couple minutes before I broke free and moved south.
I went to work plying his chest with moist, airy kisses. I gently sucked and licked both of his nipples while my hand stroked his chiseled abs, intentionally avoiding his cock. I gave his nipple the gentlest of bites with my teeth causing him to moan. They stiffened to my touch. His smallish nubs firmed into hard little pellets upon his chest, surrounded by small circles of slightly darker flesh. For all his progress through puberty, Max still had small, little boy teats. I’ve always enjoyed nipple play, but I much preferred Max’s smallish nipples and smooth chest to the bigger nipples of hairy-chested men. I slowly shifted downward, my pointed tongue tracing its way to his belly button. I glanced down and saw his cock was almost fully erect and coming upwards to meet me. It was a beautiful sight, with the piss hole looking at me like an inviting, seductive eye.
I swirled my tongue into his belly button and then worked lower until his hard cock poked me in the cheek. I turned my head and took it into my mouth and swirled my tongue across the flared head. His hips arched instinctively as he gasped. I felt his hardness against the entrance to my throat. I sucked and bobbed before letting his 5” of teen dick slide from my mouth. He let out small complaining whine at the loss of the warmth my mouth had provided. I kissed his cock from top to bottom and bathed his hairless balls, before taking him back into my mouth.
I continued for several minutes, stopping the full on sucking frequently to make sure he wasn’t getting too close. I squeezed his cock at the base as well to quell any impending orgasm. I wanted to make this last.
I decided after another few minutes of taking his cock deep to change things up. He was shower clean, so it was a perfect time to sample his boy pussy. I climbed over his left thigh to position myself between his legs. I used my nose to lift his hairless balls and licked at his taint. I listened for an objection, but none were voiced. Rather, only soft moans came from the head of the king size bed. I ground my hard cock into the mattress as I licked closer and closer to my target.
I took my hands and ran them up and down his smooth thighs several times and then slid them under and lifted gently. His hips rolled just enough that my tongue slipped down onto his pucker. I’d fantasized often about what the anus of a boy would taste like. It exceeded my expectations. It was clean and oh so smooth. Not having hair around the orifice to contend with was wonderful. It seemed cleaner and more pristine, like picking fresh fruit from the vine.
I lapped at his tight hole as he whimpered subtle moans. He must have liked what I was doing, because he grabbed his knees and pulled his legs towards him, spreading his ass and giving me even better access to my prize. Whatever reservations Max might have had in the shower had now clearly vanished.
I pressed harder against his opening. I curled my tongue and pushed. The tight ring barely gave. Oh my god how tight it would be if I actually got to fuck him! “God you’re one sexy boy,” I whispered seductively before resuming a more aggressive attack on his wrinkled pucker. It tasted perfect. No funk at all. It was heavenly.
I pushed harder with my pointed tongue and this time it slipped inside of him. “Oh fuck,” he moaned. I loved making him feel good like this.
I poked it in and out a few times. “Oh shit Craig,” he moaned. “Pleaaaaaase fuck me,” he begged in his sweet operatic voice. I’d had guys beg me to fuck them a few times, but to hear it in a softer, boyish tone was so much more arousing.
I laughed inside at how much Max and I are alike. Having a skilled tongue work my ass has always been a sure fire way to get me in the mood to be fucked. Max was apparently constructed with the similar wiring. “As you wish,” I told him.
“I’ll get the stuff,” he offered. I got up to allow him to go to his backpack. I stroked my aching cock as he rummaged around in it. He came back with the lube and a strip of three rubbers. “How do you want to do it?” he asked.
“Right now I want to eat you some more so just get on your hands and knees,” I ordered him. He climbed in front of me, his ass looking back at me. “That’s it. Now put your head down.” I pushed his muscular cheeks apart and went back to work tonguing him. He moaned in delight and pushed back towards me as I kissed, licked and tongued his pink hole. I reached between his legs to give his cock a squeeze. It was rock hard and when I squeezed it, I was rewarded with a huge smear of teenage precum on my fingers.
I smeared the slick juice directly onto his hole. My finger was covered in enough of it that it slid right inside, the ring clamping tight against my digit. The tightness and warmth was incredible. He pushed back towards me, pushing my finger deeper. There was no doubt now that he wanted what I was about to give him.
I withdrew my finger and licked at him some more, enjoying the added taste of his delicious precum. As I enjoyed the flavor, my hand reached behind me for the lube. I coated two fingers with lube and gently pressed them inside. Max let out a slight whimper as the added thickness stretched him. I slowly worked them in and out, spreading them a bit to open him up. He moaned and began to rock his body to fuck himself onto my invading fingers.
I could feel his ring begin to loosen. It was still tight, but not nearly as tight as when it was just one finger in him. I grabbed the lube and squirted more onto his opening. I reinserted two fingers and then added a third. I very slowly worked them in and out as I grabbed the strip of condoms with my free hand. I thought about how incredible it would be to fuck him bare, but dismissed the idea quickly before I let it take hold. It was simply too risky.
I tore open the foil with my teeth as I continued kneading his boy cunt. I surprised myself with my retained skill of applying condom one handed. Back when I was fucking girls in college, I had learned to do it one handed while my other hand was busy fingering their smelly cunts. I guess it’s kind of like riding a bike, you never forget how.
“Are you ready for this big dick Max?” I asked him, pulling my fingers free.
“Yes daddy,” he moaned. “Fuck me.” Oh man. Him calling me daddy almost made me cum into the rubber. I’d known for a while that Max had a submissive side based on the details he had shared about some of his sexual encounters with Cam. It was quite clear this submissive side was coming out now. If he wanted me to be his daddy and in control, I was going to do my best to give him just what he wanted.
“Hand me a pillow, BOY,” I directed and slapped his ass lightly.
“Yes, sir,” he replied and pushed one back to me. He was really getting into his role, clearly.
I placed it on the bed in front of his knees. “Ok then, lie on that,” I instructed.
He must have never considered getting fucked while lying on his stomach either, because he started to roll over onto his back. “No, not like that, face down,” I commanded in a firm authoritarian voice.
He flipped back over and lowered himself onto the pillow. “That’s a good boy,” I praised him. The pillow raised his ass perfectly. Those round globes of flesh were perfectly displayed. I was so glad we left a light on. None of this would be as thrilling in the dark. His ass was there just for ME, positioned to be penetrated by my throbbing cock. I rubbed my hands over each pale mound and moaned. Damn! What a perfect ass! I pulled the hemispheres apart, revealing his well oiled boy cunt. It was slightly open from the prior work of my fingers. I couldn’t wait to get my hard cock in there. My manhood was as stiff as I could ever remember it ever being, and it was already twitching in anticipation of what was to come. I’ve dreamed about sex with boys for the past thirty years. How many times had I jerked off imagining my cock sliding into a boy’s ass? And finally, I was about to have my fantasy come true. I took a deep breath to calm myself. I didn’t want to cum as soon as I entered him.
I spread his legs wide and leaned forward and lowered my cock into his crack. Just the warmth of his mounds surrounding my hardness felt amazing. I slid it up and down a few times, just enjoying the friction. I pulled back and pointed my steeled rod downward with my hand so that it was pressed squarely against his loosened hole. Even with all the prep work, it was still tight against my flared head. I leaned forward and got nothing but resistance. I lowered myself further, letting more of my weight fall against him and suddenly his ring gave way, and my cock pushing deep inside him.
He grumbled and sucked air in through his clinched teeth, like one does when they are trying to keep from crying out. I hadn’t intended to penetrate him so quickly. It just happened. Perhaps, this wasn’t the best position after all for a teen to take his first adult cock. “You ok bud,” I whispered.
“Yeah,” he replied between heavy breaths. I could tell he was trying to fight off the discomfort of my thick cock buried in his ass. “Just…give….me…a …. second… to…get ….used to….it,” he managed to say between grunts and breaths. I lifted my hips to take some of the pressure off, resting my weight on my forearms which I had planted on either side of him. I lowered my face and nibbled at his earlobe and kissed his cheek.
“Take your time Max. Just let me know when you are ready,” I said before I gave him some breathy kisses across his neck. “Then,” I said and paused, “then I’m gonna fuck you hard. Real hard. It’s what you want right?”
“God yes!” he moaned. “Thank you, sir,” he added. He actually pushed up with his hips, bringing more of my cock into him. I let my hips drop and just like that, my entire cock was buried inside him. My pubes pressed against his smooth teen ass. My chest lay against him, sharing the heat of our bodies. Alex from my story was right! This was a very nice way to fuck a boy. I’d never felt anything as tight or warm on my cock. “Just go slow Craig,” he pleaded.
“Don’t worry Max,” I replied. “I can guarantee you I won’t be rushing this.” I started slowly moving inside him, pulling out barely an inch before pushing back in. My head was against his, so I as detected his breathing return to normal, I started elongating my thrusts and pushing in deeper. I must have hit that magic spot inside him, because with each deep push he began to let out a soft whimper. He was clearly starting to enjoy this.
It was such a different feeling topping a young teenager like Max. His body is so much smaller than a man and thus, there was an enhanced feeling of dominance and control that I never noticed the few times I’ve fucked another man. I usually preferred bottoming with men, but I realized there was just a different dynamic with a boy. Being able to wrap my arms around a smaller, smooth body and be in total control as my invading dick elicited boyish squeals of pleasure was a completely different experience. And I loved it.
“This is amazing,” I told him as I begin to pick up the speed of my thrusts. I ran my hands along his arms, feeling the soft downy hair that covered them. I reached his hands and clasped them from above, weaving my fingers with his. He returned the grip, molding our hands together. The feeling of bonding was almost surreal. I’ve never been one to be a ‘dom’, but there was something about being on top a smaller boy, holding him in place while I fucked his tight hole that was incredibly erotic. He must have felt it as well, because after closing his fingers around mine, he hooked his feet around my ankles, further squeezing us together into one form.
I started pumping him hard, flexing my hips forward and pushing into him as deep as my 6” cock would go. With each thrust, Max began to purr. Little high pitched boy moans of delight poured out of his mouth. I was so glad his voice hadn’t changed yet, because these high pitched yelps were hot as fuck. I kept pounding away and his moaning and whimpering kept getting louder and louder. I was lost in the moment enough that I didn’t recognize right away exactly how loud he had become. I don’t think he had either.
“Shhh,” I whispered to him as I stopped pumping with my cock fully buried in his tight ass. “You’re going to have the neighbors know what we’re doing.” I pushed my arm against his mouth to keep him quiet and resumed fucking him.
As I worked my cock in and out of his ass a new feeling came over me. You know how people describe making love to their soul mate as some sort of Nirvana? As some incredibly deep, almost religious experience, full of euphoria? Well, I had never experienced such a thing. I’d always assumed it was because I was just too practical and not sappy enough.
Turns out I was wrong. I just needed to be having intimate sex with the right person. A boy. Max. Taking Max’s ass was on a several planes higher than any other I’d encountered during sex. It was definitely not just a good fuck. It was so much more. I loved this boy. Max surrendering his ass to me like this meant something special. I only hoped he felt some of the same emotions.
Another feeling soon erupted inside me. This one was more familiar. It was the oncoming feeling of an intense orgasm. “Oh shit Max,” I moaned, “here it comes baby.” My thrusting transitioned into a series of short quick jabs as the intensity quickly built and I could feel a huge load of cum rise through my piss tube and erupt from my cock. I let out as a series of short yelps as my body twitched and my cock throbbed, pulsing more and more of my hot seed into the confines of the Trojan. I collapsed onto Max, our sweat covered bodies sliding against each other. I had to gasp to regain my breath.
I rolled off of Max and onto the mattress, my softening cock slipping from his behind with a slight pop in the process. The moving air felt good against my sweat covered chest. I became aware that my hair was soaked in sweat as well. It was quite a work out.
“Did you enjoy that as much as I did?” I asked my boy.
He caught me by surprise by leaping into my arms and hugging me. “I love you Craig,” he blurted out. “That was amazing,” he added as he pushed into me. So apparently Max had felt some of the same emotional feelings that I had. At least I hoped that was it and that he wasn’t just reacting to being pleasured physically.
His sudden professing of love for me had caught me a little off guard. “Ok,” I replied. “I love you too Max. Did you cum though?” I asked. I reached for his dick to see if it was covered in cum or if I needed to finish him off.
I got confirmation both from Max and his cock. “For like two straight minutes I think,” he replied proudly as my hand took hold of his cum covered penis. He gave me a kiss on the cheek. It was sweet. I looked at him and a tear was falling from his eye.
I wiped his cheek. “Hey! It’s ok. Are you sure I didn’t hurt you?” I asked, suddenly concerned something was wrong.
“Nah. It did at first, but then it was fine. I’m crying just because I’m so happy,” he said as he buried his head into my chest.
“Me too Max. Me too. You made quite a mess,” I quipped as I squeezed him tight. “Look at your cum all over my hand,” I said, holding my hand up to show him before licking it clean. “Let’s get you cleaned up.”
***
I went to the bathroom and pulled the condom off my soft cock. I don’t think I’ve ever filled a condom so full. It looked like three loads in that thing. I flushed it and soaked two washcloths in hot water, using one to wipe the traces of cum from me.
I returned to the bed with the other. After licking what traces of sweet boy juice I could find on his cock, I gingerly cleaned up my boy. His cum was the best! The idea that I would have the flavor of it in my mouth as I went to sleep was very gratifying. I picked up the pillow which was soaked in Max jizz and even licked a couple of the bigger drops of cum from it before tossing it to the floor. Looks like we’d be tipping the maid extra tomorrow I thought. Next time I should have put a towel on it before I have him lay down.
I pulled the blankets back over us and Max curled up against me. I kissed him on the forehead and pulled him tight.
“Thanks again for everything Craig,” he said. “This trip’s been lit.”
“Max, even with last night’s little argument and stuff, I’ve never had a better vacation than this. Honest. And this, tonight, well that was just icing on the cake.”
“Yeah. I could definitely do THAT again,” he replied. “Are you still thinking we have to stop doing this when we get home?”
“I don’t know Max,” I answered. “It would probably be for the best, but we can talk it about it more tomorrow. Okay? It’s late and we have an early alarm to dive.” I knew what Max was feeling. I didn’t want to stop this either. That was the most incredible sexual experience of my life. I was born attracted to boys, so naturally this was pinnacle. But, post orgasm, my logical side was also starting to reestablish itself. It really would be difficult to continue. And risky, oh so risky.
“Okay,” he surrendered and lay against me quietly.
I thought of one more thing I’d been meaning to tell him. “Max?” I whispered many minutes later.
“Yeah.”
“I meant to tell you how impressed I was with the way you were around Joshua tonight. He really seemed to come out of his shell. His mom’s were looking at you and smiling all night once you started answering his questions.”
“Thanks. No big deal. He’s cool. Big time different, but nice. Do you think he’s gay? I do.”
“Well, if I had to bet, I’d say yes. I mean he does like musicals, right? He seemed mighty keen on asking you about your gayness too. But who knows, he could just be a curious kid. I thought maybe he had confided in you while you guys alone at some point.”
“Nah, he didn’t. I shoulda got his insta or something to keep in touch with him.”
“Well were diving with the moms tomorrow. Maybe you can ask them.”
“Sweet idea. Maybe we could meet for dinner again even.”
“Good idea. One more thing. This is our secret, remember? You can’t tell anyone. Not even Cam, right?”
“I know.”
“Great. Goodnight Max.”
“Goodnight daddy.”
“Goodnight sweet boy.”
Goodnight daddy. Those two words were music to my ears.
** End of Chapter 24 **
Author’s notes:
How many more times do you think Max and Craig will fuck before they go home. They have two full days left on the island before catching a noon flight on the third day. Will Max even be able to walk onto the plane by Tuesday when they leave?
Continued feedback appreciated – craigpnifty@protonmail.com. Really though!!! Us writers are attention whores, so if you are enjoying this saga, please drop me a note.
A reference was made in this chapter to a nifty story. The nifty story I referenced is real. It’s called The Hunting Season (by Pink Panther). I like his writing, and parts of this story were very good, though the sex became redundant. Other stories of his I liked much more, but there was some good nuggets from this one that stuck in my head, obviously.