Hawaii

The first day after the last day of high school (and three days after my 18th birthday) I stepped onto a plane headed for Hawaii. The Big Island. Kona side. Not that I wanted to go to that particular island, but I wasn't exactly rich and my parents' friends had a timeshare they let me rent cheap for two weeks.

It was going to be two weeks, from all I knew about the Big Island, of slow living and boredom, but at least it was Hawaii and not Cabo or some of the other seedy places some of my friends were going to that summer. Plus, it was my first vacation away from my parents, all alone. No one would know me, no one would have a say in anything I did. I left the Pacific Northwest a boy to become a free man going to Hawaii.

As the plane took off from Seattle-Tacoma Airport, I thought about the end of my high school years - all the pain and wonderfulness that was high school. In high school I was two different people. I was the star quarterback who dated Stephanie Moore (the prettiest cheerleader), the best shooting swing guard on the basketball team, the fastest hurdler the school had seen. Like, literally, I had broken the 100 and 300 records. I was that tall, handsome guy with the muscles and athletic prowess. Top that off with my stellar academic achievements, the fact that I was Homecoming King, and that I wasn't a fucking bully, and I was the most popular guy in school. I knew this.

I also knew that I was gay. Or maybe bi.

I couldn't decide, to be honest. Steph had been a willing teacher of the ways of the sexually active, and I had been a willing student. From the moment we had first made out to the moment she first slipped a rubber over my prick, I had enjoyed every minute of it. And Steph wasn't a missionary only type of girl. No, eventually I stuck my hard dick in just about every spot I could in her and enjoyed every second of it. What made Steph special was, she was happy to stick a hard dick into my every spot, as well. Her particular kink was pegging, and nothing turned her on more than dressing me up in her clothes, complete with makeup, and hammering me from behind.

It certainly developed a dick fetish of sorts, and seemed perfectly wonderful to me.

But, then, even before Steph had initiated me, I held a fascination for dudes. Naked dudes. Naked dudes with big dicks. Especially older, manly naked dudes with big dicks and big muscles. Sears catalog men's underwear ads? Hell yeah. Men's work out magazines? Definitely. The first time I saw a picture of a naked dude with a big dick in a porn magazine my buddy Freddy had somehow acquired I nearly burst. It was a pic of a guy standing over a crouching blonde, his dick pressed against her red lips, his balls hanging down low.

"Look at those tits," Freddy breathed. I nodded, staring at that dick. That was a hell of a night, too, because it was the first time I had ever touched another guy's dick. I had gone to spend the night at Freddy's our sophomore year and he whipped that mag out. We went through the pages, lying in his bed, looking at the wildly posed photos, both of us sporting boners.

"Dude," Freddy said, "I have to jack off or I'm going to have blue balls for a month."

"Okay," I said, not sure what was going to happen next. Without ceremony, Freddy whipped his pants down and started stroking his prick. I followed suit, of course. We held the magazine in one hand each, while stroking our meat with the other. I was looking more at his dick than the pages, though. Now, Freddy was no Adonis. In fact, he was, at best, nondescript. But seeing a hard cock in the flesh was an eye opener. His dick was smaller than mine, just like he was, and the head was a light pink while mine was a deep red.

"Let's do a buddy tug," he said. He dropped the magazine and got up on his knees. I again followed suit, not sure what was going on. Once on our knees, we faced each other and he pulled his t-shirt up, pinning it under his chin, as did I. He reached out and grabbed my dick and began tugging. I grabbed him and started tugging as well. He was hot and hard in my hand and I could feel the precum juices seeping from the tip onto my palm. The pungent scent of two horny erections about to explode wafted up and I wanted nothing more than to bend down and see what he tasted like. Within seconds he jerked and his cum shot onto my forearm. I gasped, watching his belly clench and feeling his cock throb, then my own prick exploded, shooting a fat stream of a load that splashed against his bare belly.

We fell down in a well-separated heap and never spoke of it again...

The flight to Hawaii was uneventful other than the flight attendant, an older woman, who flirted with me outrageously. I knew I could have probably had a place to stay that night if I didn't have access to the timeshare. I can honestly say, at that age I was like candy to older ladies. They just loved me. Too bad I didn't love them as much.

The timeshare itself was pretty nice and I was pleasantly surprised as I got out of the taxi from the airport. It was up the hill a bit from Kona, a small house with a nice private backyard with a view of the ocean below. It was like a little oasis, with trees all around keeping the neighbors' eyes out and a pool. The first thing I did was rip all my clothes off and skinnydip for the first time in my life. I was in heaven.

Luckily enough the timeshare was an easy walk (for me) away from Kahalu'u Beach. The next morning I threw on my swimsuit and t-shirt, some tennis shoes and grabbed a towel and some snorkel gear, and walked the mile or so down to the beach from the house. It was still pretty early, so there weren't that many people there yet, and I had the black sand beach almost all to myself. I spread my towel out and headed into the water. The water was warm, the snorkeling amazing, and I stayed out there probably longer than I should. When I came back up out of the water I could see that the beach was filling up. Luckily enough my towel (and shoes and shirt) were still there. I picked my way through the early beach goers wading in the shallows and immediately stopped just as I left the water. Walking toward me along the beach with a bag, an umbrella and a towel was a big, tall, muscular guy, and I recognized him immediately.

"Coach Blane," I said.

He stopped for a second and blinked at me then a smile lit up his face. "Holy shit, if it isn't Sam the Man!"

I laughed. He had been calling me Sam the Man since I was a freshman. I put my hand out and he grabbed it then, surprisingly, pulled me in for a "bro hug." I didn't know what to do as he patted my back so I did the same to him. He was about 6'4" and everything about him was broad. Even at 6' tall I felt small next to him and, certainly, small pressed up against him in a hug.

"What the hell are you doing here?" he asked.

I told him about the timeshare and how I had been saving up for this all through high school. The whole time I was trying not to stare. I had never seen Coach Blane without a shirt on and he was, to say the least, impressive. Big deep chest, trim belly with a hint of a six pack, long muscular legs and broad shoulders and huge arms. I was confused. After a bit of small talk I told him where my stuff was and invited him to join me. He followed me to my towel and, so we could share the umbrella, he put his towel right next to mine and settled down.

Coach Blane had always been one of my favorites. Unlike some of the other coaches he seemed genuinely nice. It helped that he was really handsome, too. He had the strong good looks of a rugged leading man - square jaw, full lips on a mouth that always seemed ready to smile, piercing light blue eyes and thick brown curls with just a hint of grey at the temples. All the girls in school had a crush on him. I never considered having a crush on him because having a crush on a guy who is so obviously straight was kind of weird, in a way. Plus, he was my coach and that all was just weird to me. If anything it was a father-son relationship. You just don't crush on your mentors...or I don't, at least.

But there I was, laying back next to him, trying not to stare at his thighs, or his shockingly slender ankles, or those calves, or the obvious lump in his shorts, or his belly, or his chest...the list of things to not look at was a long one, so I just stared out over the water as we talkd.

I had never actually talked to Coach Blane much beyond the typical coach/player conversations. He was our offensive coordinator/coach and had pretty much made me the quarterback that I was, but we had never talked about personal stuff. As we hung out there he asked me lots of questions about where I was going to school (Stanford), what my plans were (pre-med) and if sports were going to be a part of those plans (nope). The whole time I was curious about where his wife was but was afraid to ask. It was actually he who brought it up when I asked him if he came to Hawaii often on vacation.

"No, no, this is the first time," he said. "My wife and I divorced this year and I had entered this drawing the state put on to give teachers some spiffs. An all-expenses paid trip to Hawaii was one and...here I am."

"Sorry to hear that," I said, not sure what else to say.

"That I won the drawing? Jeeze." He laughed.

I blushed. "No, I mean the divorce."

"Ah, you know," he said, brushing it off. "I mean, it was meant to be. I'm not really traditional marriage material."

I nodded as if I knew what he was talking about but I had no idea what that meant. He seemed like completely traditional marriage material to me. Handsome, nice, incredible body for a guy in his 40s. Perfect. He laughed, as if he understood my obvious confusion, then he gestured to the water. "I'm going to go for a quick dip. You mind hanging out here and watch my stuff? My wallet's in my bag and the thieves love tourists at this beach."I nodded and he hopped up and did a quick stretch, arching his back. His shorts rode low on his ass, just showing the tops of the firm globes of his ass. After a moment jogged down to the water. I watched him wade out for a bit then plunge in. Something inside me was kind of breaking up a bit and I tried to banish the bad thoughts from my brain. Coach Blane was hot. From the front or back, he looked damn good. That ass he was rocking in those shorts was to die for. And that smile. And those eyes. Jesus Christ.

After a few minutes I saw him coming out of the water. Every woman on the beach, young and old, paused to watch with me as he strode up, water streaming down his body, his swim trunks plastered to his body, his prick an obvious, and very fat, lump, down one thigh. I think I muttered something to myself and willed my own dick to stay down as he sauntered up toward me, looking pretty pleased.

"That water is awesome," he said, grinning. He sat down next to me and I averted my eyes as he laid back. Don't stare at his dick bulge, I said to myself. Don't do it. How embarrassing would it be to be caught drooling over your hyper-hetero coach's dick bulge? Horrifying.

"So how's Stephanie Moore? You guys still dating?"

"Steph? Uh...well, not really. I dunno, to be honest. She's going to school in Scotland."

"I thought somebody on the faculty had said that. St. Andrews, right?"

"Yeah," I said.

"I mean, you guys could probably stay in touch, right?"

I shrugged. "We talked about it. I think we both know that wasn't going to happen. The long distance romance."

"That's probably wise," he said.

To clear my head I decided to go for a quick dip myself. After a few moments in the soft warm water I came back up, wiping water out of my face. I was conscious of how my swimsuit clung to my body like it had Coach Blane's and was startled to realize that my prick was at half erection after that swim. Trying to look perfectly confident I walked up through the gawking ladies and sat down next to Coach Blane.

"Well, it appears you gave the ladies a show there," he said.

I blushed. "I think they're all lonely."

He laughed then bit his lip, looking away from me. "I just realized that I'm probably an old stick in the mud for you here, I should probably leave you alone."

"Why?"

"Oh, you know, I don't want to cock block. You know, having a middle-aged wing man is probably not best if you want to meet someone new."

I laughed. "Nah coach, that's not...it's cool. I mean, I'll be honest, I'm not looking to get laid. Besides, you were my favorite coach and...it's cool hanging out with you."

He laughed a little and I could see him blushing. "Thanks...that actually means a lot to me...and please, call me Denny. I'm not your coach anymore."

"Okay, Denny," I said and I felt myself blush a little. Jesus, I thought, don't make this weird. For a moment I thought of agreeing to his offer to leave me alone, just to ensure I didn't make a fool out of myself, but then I decided against it. I can keep myself together, I told myself. I've been keeping secrets for years.

By the time lunch rolled around Denny and I had gotten to know each other pretty well. I told him all about my dreams of joining Doctors Without Borders and he told me about his strict Christian upbringing and how it had made him want to be a teacher ("I am horrified by the ignorance I endured and, in some ways, perpetuated until very recently," he said). We hopped into his rental car and got some lunch at a restaurant in Kona and, sitting across from him, I was regretting my decision to not push him away. He was handsome, smart, funny, kind. He was pretty much the perfect man and, frankly, I was not sure why his wife divorced him. So I asked him.

"Why did your wife divorce you?"

I just came out as a blurt, said right after he had told me a funny story about one of the other coaches who was a renowned asshole. The way I said it came across as a gushing compliment, I might as well as said "I can't believe your wife divorced you, is she stupid?" and I blushed immediately afterward.

He immediately got quiet, but he didn't seem angry or upset by the question. "It was the other way around. I divorced her."

"I'm sorry," I said. "I shouldn't...that's none of my business..."

He smiled and actually reached out across the table and put his hand on mine to comfort me. It was a big, strong hand that covered mine easily and I thought of that hand on my body and nearly shivered. He pulled back. "Nah, that's okay. I don't mind talking about it. The bottom line is, she started going elsewhere in the end. You know...she was a roamer."

"She screwed around on you?" I blurted and immediately blushed again. "Jesus, I'm...sorry, I'm just being a dumbass."

He nodded. "She did. I don't blame her. I wasn't really there for her, I guess."

I tried to remember his wife. Hot blonde, in great shape, big tits. Just the woman you would think the hottest teacher/coach in school would be married to.

I nodded. "Well...her loss."

He smiled. "Thanks, but she'd probably disagree. Anyway, that's water under the bridge. What are you up to this afternoon?"

I shrugged. "I dunno. Did, uh, you have any plans?"

"To be honest, probably a shower and a nap. I'm staying at a B&B. If they had a pool I'd lounge in that all afternoon. It's getting a little sunburny for the beach."

"My place has a pool," I said. "It's nice. Private. I skinnydipped for the first time ever last night because the neighbors can't see."

Denny was taking a sip of water and he snorted a bit then coughed. "Is that an invite?"

"Sure," I said, swallowing. "I mean, that's what I was going to do this afternoon. Skinnydip, shower, nap."

Denny paused for a bit. He looked down at his wrist watch, as if thinking about the time. After a moment he shrugged and nodded. "Sounds like a plan to me."

We drove in Denny's rental up the hill to the timeshare and I showed him in.

"Nice place," he said.

We walked through the house to the back yard. There was a back porch with an awning for shade, a couple of comfy reclining beach chairs with thick cushions, a table and the pool. All around were trees and straight ahead was the expanse of the ocean beyond Kona.

"Wow," Denny said. He looked at the pool and then at me. "So...skinny dipping, huh? I haven't in years."

I decided at that moment to not think anymore, to just do. So I pulled my shirt up over my head without saying anything and then shoved my shorts down my legs and stepped out of them. I took a deep breath, avoiding looking in Denny's direction, knowing full well that my cock was already at half-staff. Without a word I walked into the shallow end of the pool, then dove underwater, letting the sun warmed water flow over me. When I came to the surface I saw Denny undressing as I did. When he shoved his shorts down his pricked swung out, maybe a bit more than half-staff and my eyes widened. He was thick and uncut, springing from a thick black bush of lightly trimmed pubic hair.

Denny stepped forward and into the pool, then dove in like I had. When he came to surface he smiled. "Goddam, this feels good," he breathed.

I swallowed and nodded. "Yeah, I stayed in a bit too long last night."

We swam around for a few minutes, barely exchanging a word, then finally Denny stopped and tread water in the middle. I went to the side of the pool and turned around to face him, putting my arms up on the pool edge to hold myself up. I caught his eye and felt my heart stop. We must have stared at each other without speaking for a full minute. I felt my mouth open slightly and his eyes darted down then looked away.

"This is wrong," he said suddenly. "I should leave. I should've left when I said I should've earlier."

"I don't want you to," I said. "I like having you here."

"But you...I'm your coach."

"Not anymore," I said. "You said it."

He suddenly swam over to me. I took a deep breath as he came near, putting his hands up on the edge of the pool and pulling himself in close. With a shock I felt his hard, hot, thick member touch my thigh. His face came near mine, our lips nearly touching.

"You're so beautiful," he said.

"So are you," I said. I instinctively pushed my hips forward, pressing myself against his belly and he groaned. Our lips met, and his tongue thrust into my mouth. Holding himself up with one hand he slid his other down my back to my ass and pulled me tighter to him. I could feel his cock pressed hard against my thigh and I let go of the pool edge, bringing my arms around his waist and holding on as we kissed.

To be honest, it was WAY better than kissing Steph Moore.

When our kiss broke off he slid his mouth down my neck, then to my chest. Suddenly he pulled back and looked at me, gritting his teeth.

"You're 18, right?"

I nodded. "Yes...and I'm a willing participant. And I'm not your student."

He laughed a little. "That doesn't make it right," he said. He took a deep breath and let it out then pulled me by my hand toward the shallow end of the pool. "Come on," he said.

We walked out of the pool, his hand still holding mine. Once on the dry patio he turned around. My eyes widened as I stared down at his thick cock arching up away from his body. I took a deep breath and reached out, grabbing it with both hands. It was so thick I could barely get my hands around it. I slid one hand down to cup his balls, which hung down like two walnuts in a loose sack. The skin was soft, silky, warm and enticing. So much better than Steph's strapon. I licked my lips and looked up at him. He was watching me, his eyes intense. Keeping our eyes locked I knelt down and brought that fat cock to my lips, giving it a kiss. A pearl of precum squeezed out and I tasted it with my tongue, enjoying the bitter, creaminess of it. His scent was intoxicating, the feel of his balls jerking in time to his pulsating cock was overpowering. I needed more.

I pressed my lips against the head, feeling the shaft swell in my one hand in response while his balls jumped in my other hand. Opening my mouth I slid him in, over my tongue. He swelled even more, the cock head spreading like a cobra, filling my mouth. More precum creamed inside my mouth, coating my tongue and I moaned at the pleasure of it. By now my eyes were closed and I felt his hand cup the back of my head gently, pulling me in as his hips thrust forward slightly. His cock slid in deeper and I opened my jaw wide to let it in until it pressed against the soft palate. Almost without thinking, I opened my throat and he pressed in further. After a moment I gagged and had to pull back. A rope of spit hung between my lips and the tip of his cock as I looked up at him.

"You okay?" he groaned.

I nodded, grinning. "You so fucking big. Like as big as..." I stopped right there and blushed. There I was, kneeling in front of this guy holding his cock that I had just had in my mouth and I was embarrassed to say that his dick was as big as my girlfriend's strapon.

His eyebrows went up. "As big as who?" He asked it gently, a twinkle in his eye, but I could also see the confusion.

"A-as big as Steph's...Steph's strapon," I said. I started to laugh, maybe a bit wildly, as he stared down at me in shock.

"She..her...wait, what?"

I took a deep breath. I still held his prick, which was softening, so I stroked it, trying to recapture the erection. "She had a strapon," I said. I gave his cock a quick suck then pulled back, satisfied as it hardened in my hand. "And she, uh...she used to fuck me with it."

He groaned again and reached down, pulling me up to my feet. I wrapped my arms around his neck and he reached down, grabbing my ass with both hands and lifting me up as we kissed. I wrapped my legs around his waist, feeling his cock spring free to poke against my ass. I felt his fingers slide in between my ass cheeks and pull them apart, letting his cock head poke against my pulsing anus. He broke off the kiss and looked around, still holding me up by my ass.

"Is that a shower over there?"

I followed his gaze and nodded. He carried me over to it and, still easily holding me with one hand clutching my ass, he turned the water on. A cold blast of water hit us and we both gasped and laughed, then he slid me down and I lowered my feet down to the ground. I slid my hands down to his chest, feeling the muscles twitch under my palms. Denny grabbed some soap and lathered me up. When he slid his soapy fingers between my ass cheeks I arched my back and moaned as he slid a fat finger in.

"Tight," he groaned. I pushed back against his finger, feeling it slide deeper into me. Denny turned me around suddenly and knelt down behind me. He bent me over at the waist and I felt his face push against my ass. I gasped as his tongue found my hole, swirling around, then pushing into me. He reached up and tugged at my cock, which throbbed between my thighs. It was too much.

"I'm going to cum," I gasped. Denny turned me around and sucked my throbbing cock into his warm, wet mouth just as I exploded in a knees buckling orgasm. I could feel my cum streaming into his throat and he held my hips tight as he swallowed every drop of it. Finally, after I had nearly fallen down, he stood up, holding me steady.

"You okay?" he asked, his voice thick with desire. I nodded.

"That was incredible," I said, my voice shaky. I reached down and felt his still raging hard-on. It was my turn. Taking the soap, I lathered him up, following my hands with my lips, suckling his nipples, licking his armpits, taking in his scent. I knelt down and cleaned and kissed up and down his legs. At this balls, I eagerly opened wide, taking each on in for a suckle while he groaned and threw his head back. The combination of soap and man scent easily brought me back to erection. I turned him around and lathered his ass up, sliding my fingers between his round, muscular ass cheeks. I pulled them apart and dove in, running my tongue over his soapy anus, feeling it contract as he moaned. He reached back and held my head against his ass as I rimmed him until finally he stepped away and quickly rinsed himself off.

Denny stepped in and kissed me again, then slid his rough cheek over mine to whisper in my ear. "Do you want me inside you?"

I nodded, my cock throbbing at the thought of it. To say I was a bit nervous, though, was an understatement. Having your kinky girlfriend peg you was one thing, but having a hung stud like Denny fuck you was another thing altogether.

We dried off and went inside to the bedroom. I climbed into bed as Denny rummaged around in his bag and pulled a rubber and some lube out. "Always ready," he said, smiling. He got into bed with me, looming over me, thrusting his still hard cock against my thigh as we kissed. After a moment he gently turned me over, onto my stomach and lifted my ass up.

"You have such a sweet ass," he said. He pulled my ass cheeks apart and spit, then rubbed the spit against my anus with his thumb as I moaned. Denny leaned in and licked my ass again, swirling his tongue around it, coating it with spit. After a moment I felt a warm, lube slick finger press against my ass. I arched my back as he slid into me. He started slow at first, finger fucking me little by little until his finger was in all the way to the hilt. After a few minutes of him fucking me and me moaning, I felt another finger join the first. I gasped as my anus stretched wide. Again, he slowly fucked me until the pain subsided and it was nothing but pure joy of being fucked.

After a few more minutes of that pleasure he pulled his fingers out and I felt him position himself behind me. I arched my back, scared and excited as I felt the tip of that fat cock press against my hole. He pushed against me slowly, letting it enter me gently, or as gently as it could be considering the girth. I gritted my teeth against the stinging pain, trying to relax myself and let him inside.

"You okay?" he asked, for what seemed like the 100th time that day. I nodded, burying my face in a pillow. "Should I stop?" he said. I shook my head.

"No," I gasped. "I want that big cock."

I heard him take a big breath and then slowly push deeper. The head popped in past the sphincter and I sighed as the stinging lessened. I actually pushed back against him, feeling him slide into me deeper. Halfway down the shaft I could feel it widening and I stopped, whimpering. He pulled back slowly until only the head was inside, then slid forward again. Over and over he pumped my ass, slowly, gently, getting deeper and deeper. I could almost feel the self control he was exerting to not just fuck me silly right then and there. After a while I wanted to feel him press against me, to fill me entirely. I began to push back, getting him deeper and deeper until, sure enough, I felt his pelvis press against my ass. Soon enough he was speeding up and I was gyrating my hips.

There were times when I had had fantasies about being forcibly taken by some well hung stud, about being a sex slave or harem slut for some big dicked hunk. That's what I felt like right then. I wanted him to fuck me wildly, to take me hard and long and violently. I was his to be used as he wanted in that moment.

Suddenly he stopped and slowly pulled himself out. I looked over my shoulder and he grinned at me. "We need to change things up," he said.

Denny lay on his back and had me straddle him. I reached behind me and grabbed his rubber-covered cock, still hard as a rock, and positioned it upright against my eager hole. Without ceremony I slid down that pole, skewering myself on his throbbing meat. He thrust up into me, lifting his hips up from the bed and I fell forward, stopping myself with my hands on his chest. I bent down and kissed his chest, licking and biting his nipples as he thrust up into me. The feeling of his belly contracting against my hard cock as he pumped was sending me over the edge. He pulled my face up and we kissed, our tongues dancing wildly in time to his pistoning cock.

It wasn't long before I felt him begin to stiffen and swell even more. His already fat cock stretched me to the limit and I moaned with pleasure as he jerked and pumped, I felt the rush again, felt my toes tingle and I moaned into his mouth that I was cumming. When I did I felt my sphincter tighten around him and he threw his head back, thrusting hard up into me, his body arching high above the bed. He held that for a moment as my prick pumped cum onto his chest then I felt him jerk as he cried out. His prick pulsed on the walls of my tight, throbbing hole as he came deep inside me.

We fell into the bed and lay there, exhausted. He held me tight. I could feel his cock shrink inside me and begin to slip out. I reached down and touched the sticky wet goo on his belly then held my cum covered hand up.

"I came on your stomach," I whispered hoarsely, laughing a little. "Which is a good thing. I wouldn't want to get the sheets all gross for our nap."

Denny grabbed my hand and ran his tongue over my palm, licking my cum up. When he was done I pulled his head in and kissed his cum drenched lips.

"I have a feeling," Denny said, "we won't see much of Hawaii beyond that pool outside and this bedroom inside."

I grinned. "Sounds like a plan," I said. "Sounds like a great plan."