After my 30-minute swim, I was relaxing in a lounge chair. Although it was a typical Denver spring, with a stiff wind lowering the 60-degree temperature outside to a wind-chill of 40, the infrared panels in the ceiling kept the whole pool house cozy enough for me to stretch out on a pool chair and relax, wearing nothing but my Speedo. The Olympic-sized pool was in a separate, heated building about a hundred yards from the main house.
There was an outdoor pool closer to the house, but it was for entertaining and letting little kids splash around and shit like that, and it was still covered for the winter. The “regulation” pool was for me to exercise in. I was captain of the swim team at The Wyndover-Grantham School, a private college-prep on the outskirts of Denver.
I was just about to fall asleep, hoping to dream of a hot guy with a big cock, when I heard the pool house door open and close. If my timing was right, it would be Tony, the pool man, come to do the weekly maintenance and cleaning.
I had the hots for Tony. He was built like a brick shithouse, with strong, muscular arms, shoulders, and legs, and washboard abs. I knew this because all summer long, he wore only a pair of sandals and cut-offs when he came to work on our pool. Now, of course, he’d be dressed a lot more warmly, given the distance between where he parked his van and our pool house. Nevertheless, he was ideal eye-candy for a horny boy like me.
Lazily, I opened one eye, hoping against hope that he was wearing something revealing today, despite the cold. I shot up in the chair, both eyes wide open, staring at a total stranger.
He walked up to me with a big smile. “Hi, there. I’m Alan, your new pool guy.” He extended a hand for me to shake.
Suddenly feeling exposed, I grabbed my towel and spread it over my legs and waist. “Hi. I’m Bruce, uh… Bruce Hobson.”
He was no Tony, but he was not in the least hard on the eyes. About six feet tall, sandy blond hair, green eyes, and a three-day light brown beard, he would definitely do as a replacement for Tony in my masturbatory reveries.
“What happened to Tony?” I asked, trying to hide the disappointment in my voice.
“Oh, we traded routes. He wanted something on the east side.”
“Really? What’s over there?”
Alan grinned slyly and got a conspiratorial look on his face. “Well, there’s a certain lady who’s alone all day, and her pool needs a lot of attention. And Tony like to give the ladies a lot of attention!”
There went my fantasies about sex with Tony!
“Aren’t you sorry to lose that route?” I said, responding to his hidden meaning. “If the lady is that much in need of attention, couldn’t you provide it?”
He hesitated and then winked at me. “That’s why we traded. Tony likes the ladies, but I’m more interested in the guys – especially studs like you! With this trade-off, we both get what we want most.”
With that, he reached down and lifted my towel off me, revealing the hard-on in my tight bathing suit. I blushed a deep shade of red but didn’t move.
As he carefully folded the towel and set it aside, he said, “As Mae West said, ‘is that a banana in your trunks, or are you just happy to see me’?”
He held out a hand to help me get up, and smoothly brought me into his arms. He leaned toward me, his lips parted, and brought my face to his. Our tongues met and then began to explore each other’s mouths. I was still so surprised by everything that I was as limp as a rag doll.
He leaned back, breaking our kiss and looked at me, surprised. “Aren’t you the dude who is always undressing Tony in your mind? He told me he always tried to get a hard-on in his shorts every time he came here, just to fuck with your head!”
“Um, yeah, I guess so,” I stammered. I couldn’t believe this was really happening.
With that, I returned his kiss enthusiastically. Our tongues dueled. I sucked on his lips while he ran his fingers through my damp hair. He sucked my tongue deep into his mouth and then squeezed it back out. Our chests pressed together and I could tell that he was hard, too.
Pausing to take a breath, he asked warily, “So, are you parents home?”
“Nope. Dad’s at work and Mom is at her bridge club. They won’t be home for another couple of hours.”
“Anybody else here?”
With that, he quickly knelt in front of me and pulled my Speedo down to my ankles. My hard dick popped up and almost hit him in the face. He opened his mouth and quickly took the head in, sliding his tongue down the underside.
“Oh, shit! That’s so fuckin’ good!” was all I could muster, as I involuntarily bent my neck back and closed my eyes. I couldn’t believe it: I was getting a blowjob from a complete stranger, right in my own pool house!
Alan took my whole erection into his throat, pausing at the base with his nose in my closely-shaved pubes. He put both hands on my ass and began to pull me into his face, then gently pushed me backward. Basically, he was fucking his own face with my cock!
As he pulled my ass toward him, one of his hands began to massage my crack. Then he used both hands to pull it apart, spreading my glutes open. I soon felt a finger tracing up and down and stopping every time it found my asshole.
“Mmm,” I moaned. “Fuckin keep doin’ that!”
“You like it?” Alan asked, as he put a little more pressure on my hole.
“I fuckin love it!” I groaned, pressing my ass backward and helping his finger enter me.
Alan didn’t need any more invitation than that. He pushed his finger deep inside me and then began to rotate it all around my rectum.
“Man, if you don’t stop that shit, I’m gonna cum!” I squeaked.
Taking my cock out of his mouth, Alan just said, “I’m ready for it. Lemme have it!” He eagerly resumed his deep-throating.
With that, I exploded, shooting five or six hefty gobs of splooge into his willing mouth. As quickly as I shot, he swallowed each dose. I felt my anus muscles contracting as I came, squeezing tight against his finger, deep inside me.
“Fuck! Oh shit! That’s so fuckin good!” Breathless, that was all I could say.
After he had drunk every drop of my love-juice, Alan said, “That was some load, Bruce. How long’s it been since you came?”
“Actually, I jack off two or three times a day. This is the third load for today.”
“Impressive!” Alan exclaimed as he withdrew his finger from my butt, “You sure can shoot a big one!”
I took a wobbly step back and my dick slurped out of his mouth. I was breathing so hard I could barely speak. I looked down at the man kneeling in front of me.
“Where the hell did you come from? And why haven’t you been here before?”
“Like I said, it was Tony’s route until he got the hots for the lady over on the east side.”
Standing up, Alan gave me another deep kiss. I thought I tasted my own cum in his mouth. As the kiss ended, I collapsed onto my beach chair, my Speedos still down around my ankles.
“I’ve never done anything like this before…” I began.
“No problem. You’re a quick learner!”
With that, I reached over and began to fumble with Alan’s belt. He reached down and quickly undid it, unzipped his pants and dropped them to the floor. He wasn’t wearing any underwear.
“Commando!” I exclaimed.
“Always — at least when there’s a chance I’ll need to get ‘Little Alan’ out in a hurry.”
With that, I took his semi-hard prick into my mouth and began sucking it rapidly.
“Whoa, Bruce buddy. Slow the fuck down. I want to enjoy this!”
I did as he said and began a slow up-and-down on his cock. It was a lot bigger than mine, but I soon figured out how to relax my throat and take it all the way in.
“Mmm. That’s the way, Bruce. You’re gettin’ the hang of it.”
In response, I quickened my pace again.
“Hold your horses, buddy-boy. I don’t want to shoot yet.” With that, Alan, lifted me to my feet again and gently turned me around. He stuck his finger into my asshole again, and in a moment, I felt a second one enter me, then a third. He began finger-fucking my virgin ass, and I answered by pushing back as he penetrated me.
“Bend over,” Alan said hoarsely, and I bent at the waist and put my hands on the back of the chair in front of me.
I heard him spit on his cock a couple of times and then I felt it rubbing up and down my ass-crack. I had never been fucked, but I was SO ready for it to happen.
And Alan was ready to make it happen. I felt his cock-head press on my tight hole.
“Just relax,” he told me, as I felt it pop inside me, past the first ring of muscles. I froze. The pain was unexpected.
“Breathe, Bruce! Push back out like you’re taking a shit.”
As I followed his direction, I felt his cock slowly press through the second muscle-ring, and it was suddenly deep inside me. He stood perfectly still, allowing me to get accustomed to the intrusion. Then he slowly began to move it in and out. The feeling was indescribable.
A gorgeous hunk of a man was fucking me, and I was loving every minute of it! I had seen a shitload of porno magazines with pictures of this, but nothing had prepared me for the actual feeling. As much as I was living in the moment, giving up my cherry asshole to a gorgeous hunk, I was excitedly thinking about how I would tell my best friend Craig about this.
Alan had both hands on my hips, and he was increasing the speed and force of his thrusting inside me. I heard his breathing get deeper and faster, and I knew he was getting close to cumming. I braced myself against the chair, doing my best not to get knocked over by his pounding of my ass.
Suddenly, he shouted, “Fuck! Shit! I’m cumming!” and I felt something hot fill my insides. He kept on thrusting and I pictured my cavity being filled with his boiling cream. Finally, he pushed deep inside me and stopped, his cock completely filling my man-pussy. Breathing hard, he leaned forward and rested his chest on my back. Then he gripped me in a hug and lifted both of us upward, so that we were standing straight.
This changed the angle of his erection inside me, and I felt a sudden jolt of electricity somewhere inside my ass. Without warning, my balls contracted again and I shot another load onto the chair. Alan pinched my nipples and chewed on my earlobe as my cum spewed all over the floor in front of me. He held me tight for what seemed like minutes, then relaxed, took a step back and withdrew his now-flaccid penis from my butthole.
I turned to face him, gave him a quick kiss on the lips, and said, “Well, Alan, you just took my ass-cherry. I hope you enjoyed it.”
With a wide grin, he replied, “Best fuckin cherry I ever had! I hope you enjoyed it, too.”
I answered by kissing him deeply again, but it didn’t last long. Alan pulled away, bent over and pulled up his pants, and took a couple of steps back.
“Well, kid. I’m glad you’re on my route now. I better get the job done here before I’m late for all my other customers.” He gave me a sexy wink, a kiss on the cheek, and walked over to pick up his pool-cleaning tools.
Stunned, I stood silently for a minute. Then I picked up my Speedo and quickly exited into the bathroom. Under a hot shower, I considered what had just happened to me.
In all my eighteen years, I had never had sex with another person. Oh, sure, I jacked off with Craig and a few other guys from time to time, but we never touched each other.
I wasn’t sure what to think. I knew that what we had done was perfectly legal, since we were both over eighteen. And I knew that I did it willingly – eagerly, in fact.
But somehow it didn’t quite feel right. Sure, we kissed and hugged and cuddled each other, like lovers would do. But there was something else, something was missing. I just couldn’t name it. I peeked out the bathroom door to check on Alan, and he was gone. I found myself wondering if I would make a point to be home next week when he arrived. I kind of thought I might not.