Anonymous encounter: The boy was half my age

The boy was half my age

‘Hi, I’m Aaron’ he said.

‘Jeremy’ I replied. ‘Glad to finally meet you. I have been looking forward to this moment’.

He smiled and just said ‘me too’.

‘Come on in!’ I said, as I invited him into my hotel room and closed the door behind him.

We were in Fargo, North Dakota. This is where I’d be staying for the next two weeks. Although I travel a lot for work, most of the time, it is to large cities, like New York, San Francisco, or Atlanta. I don’t particularly look forward to travelling to smaller places, like Fargo. First of all, smaller cities usually don’t have proper hotels, like a Hilton or a Marriott. Instead, I have to settle for a Holiday Inn Express, while having to dine at the Olive Garden; Applebee’s if I’m lucky. But more importantly, the gay scene in small Midwestern towns is often microscopic and the pool of guys looking for anonymous sex is limited. Most nights, it ends up being me and my trusted right hand, trying not to soil my computer screen while watching porn.

That’s why I was so excited to see Aaron. It’s not often I can land a piece of a 19-year-old’s ass, and of all places, in Fargo, North Dakota. I’m 42, although my online profile says I’m 36, and it’s been a while since I fooled around with a guy who technically is still a teenager. I’m not quite sure what fuels younger guys’ daddy issues, but I don’t tick any of the daddy boxes they are probably looking for. I don’t have a hairy chest. I can’t even grow a fucking beard. And I don’t have a 9-inch cock either.

Aaron must have been 5’11” or 6’0”, just a couple of inches shorter than me. He wasn’t a model or anything, but there was a freshness and innocence about him that I found very attractive. ‘Cute’ is really the only word I could think of to describe him. He was wearing round glasses that made him look a little nerdy. He was probably the kind who liked to spend hours studying at the library of his university, something I never really did when I was his age. He was wearing navy Bermuda shorts and a white tank top with a large blue horizontal stripe in the middle. If I were to measure his arms, I’m sure their size would come back bigger than mine. But if I could analyze what they were made of, I’m not convinced all of it would be pure muscle.

Although we were meeting for the first time, it felt like we had known each other for a while. Anticipating it was going to be a challenge to find guys in Fargo, I had started my hunt a couple of weeks prior to coming here. To my surprise, I had managed to secure a couple of promising swipes, Aaron being the top contender. I guess the demand for anonymous gay sex in a small Midwestern town might not be all that high, but the supply is proportionally just as low. And there is probably not that much fresh meat roaming through that part of the plains. I must have felt exotic to the locals.

Because we had connected ahead of time, Aaron and I had been messaging for a while by the time we met in person. I do enjoy messaging future hookups. I have no particular issue with hotel sex, when the guy comes in, drops his pants, I pound him, he walks away, and we never see each other again. But I also enjoy knowing a little something about the guys I fuck. Messaging beforehand builds up the excitement and contributes to making the encounter almost feel like a proper date. Through our messaging I grew fond of Aaron. I liked his sense of humor. I believe he liked mine too. I especially enjoyed the naiveness of some of his comments.

Extracts of our messaging:

Him: ‘Are you a top of a bottom?’

Me: ‘I’m a top’

Him: ‘I’m normally a top too, but I’m due for some dicking’

Me: ‘Don’t worry. My dick is not that big. It’s not going to hurt’

Him: ‘Lol’

Him: ‘At what time should we meet?’

Me: ‘Let’s plan on 8pm. That way, even if I have a late night, I should be done with work and dinner’

Him: ‘Is it OK if I shower in your room beforehand? Nobody likes a sweaty dick’

Me: ‘I completely disagree. Tons of guys crave for sweaty dicks’

Him: ‘Lol’

Me: ‘Your comment reminded me of this guy who ranted on an online message board because someone had stolen his jockstraps while he was showering at the gym. And his clueless ass asked: Why would anybody steal my sweaty jockstraps? Who does that? Well, a lot of guys want to jack off while sniffing a frat boy’s sweaty jockstrap!’

Me: ‘But to answer your question: Yes, you can shower in my room if you want’

Him: ‘OK. See you tomorrow at 8’

And 7:59pm it was, when I heard a knock on my door.

Aaron was a college student. He had just finished his freshman year at the University of North Dakota. He could have gone to North Dakota State University, in Fargo proper, but he convinced his parents to let him go to Grand Forks instead, an hour north of Fargo. Close enough for comfort for his mom, but far enough to allow him to live his life. I don’t blame him. I can only imagine that being gay in high school in Fargo, North Dakota is probably not conducive to having lots of sex. It’s fair that he wanted to explore his sexuality away from home. He happened to be back in Fargo for the summer, staying at his parents, but a lot freer to come and go no question asked, since he had been away from home for a year now.

While we were messaging for the last couple of weeks, I couldn’t help but trying to read in-between the lines of his every message. Even though he came out during his senior year in high school, I can’t imagine that he had a zillion opportunities to experiment in high school. And, unless he had turned into a complete slut in his first year in college, he couldn’t have been with more than a handful of guys, at 19 years of age. What did he mean by ‘I’m due for some dicking’? Did he mean that he had experimented once or twice, but it had been a while? Or did it mean he was due for having a dick up his ass for the very first time? I’ll never know if he had a virgin hole or not, since I was too much of a gentleman to ask and risk putting him in an awkward situation. But regardless, there couldn’t have been a lot of traffic down his tunnel. His boy cunt would probably be tight.

Aaron was treating our hotel room hookup like a romantic date and had been planning this encounter the way a girl plans her wedding to the last detail. His tank top, his shorts, his haircut, his glasses, everything had been carefully selected. And I’m sure his entire day had revolved around getting ready for the evening.

Since we had already been messaging for a while, I didn’t feel any additional introduction was necessary. I was just eager to get down to business with that college kid. I wrapped my left arm around his waist, pulled him toward me and started kissing him. A gentle kiss at first, but quickly, I stuck my tongue into his mouth, and his tongue followed suit. After a minute of kissing, I started lifting his tank top. He raised his arms to help me out. He now stood shirtless in front of me. He was completely smooth, just like me: no chest hair, no treasure trail, not even hairs around his nipples. His abs were not defined, but his stomach was still flat. ‘Still’ was probably the right word because I could sense his stomach would not remain flat forever. He had mentioned being in the swimming team in high school. And I’m sure his abs were probably more defined a year ago. But just like I was unconvinced his arms were pure muscle, I suspected that a deadly combination of Mc Donald’s, Taco Bell, and university cafeteria food was slowly washing his swimmer’s body away. But who cares what his body would look like in ten years? Only this evening mattered. And his 19-year-old body was fuckable enough for me tonight.

Since I didn’t want to make him feel uncomfortable by being half naked in front of me while I was still fully dressed, I took my shirt off as well. And I’m proud to say that my 42-year-old stomach was just as flat as his. Hehe!

While we were kissing shirtless, my hands started unbuttoning his shorts and lowering his zipper as he did the same. Both our shorts dropped down to our ankles. Since I was coming from work, I was wearing random boxers, which happened to be red that day. But the boy was wearing a pair of leopard print briefs. No randomness in that choice of outfit. I could picture him scouting all the undies in his closet, hesitating when looking at the leopard print ones, and going for it anyway. Although I was smiling inside, I couldn’t help but find him cuter by the minute.

My right hand started wandering around his bulge while my left hand grabbed his waist again, pulling him towards me in a manly move. His downward pointing cock was desperately trying to get hard but was constricted by the tight briefs. Both his hands were holding my neck as we were kissing. He was on his toes, trying to make up the 2-inch difference between my height and his. Since my dick was a lot freer to move inside my lose boxers, it was already rock hard and pointing upward.

I got down on my knees and my mouth started tracing his shaft through the fabric of his tight leopard briefs while my right hand was massaging his balls and my left hand was exploring his ass crack. I could feel his cock throbbing between my lips. Although I like foreplay as much as the next guy, I was getting horny and impatient to see how much the boy was packing. I was also feeling pity for his poor throbbing cock that desperately wanted to be set free. I couldn’t resist anymore. I lowered the waist band of his briefs and his pulsating pole sprung out.

The first thing I noticed was that he was completely shaved, which came as a bit of a disappointment. I don’t mind some trimming. My bush is trimmed too. But completely shaved is a bit extreme. I felt like some of the testosterone that I crave for in a man had evaporated along with his shaved pubes. Not that I would have any clue what sex between a man and a woman feels like. Never been there myself! But it feels to me like a man and a woman are somewhat complementary. With man-on-man sex however, there is an inherent rivalry between two equally hungry males; one eventually submitting to the other. Who’s the tallest? Who’s the most muscular? Who’s got the biggest schlong? Who’s got the biggest pair of balls? And who’s the hairiest? Those are all masculinity traits that two men can use to size each other up. The fact he was completely shaved curbed the intensity of the rivalry between the two of us. Would he have had a hairy bush otherwise? What about his treasure trail? Those are all attributes I would have loved to study in detail. And because, at 19, he was barely legal, his shaved pubes made him look like a pre-pubescent boy, which kind of felt wrong. I’m into men, not into boys!

The second thing I noticed was a tiny little tattoo, slightly to the left of his shaft. It was some kind of symbol that I didn’t recognize. I’m not quite sure how much tattoos cost these days, but I know they can get pricey when they cover a lot of real estate. Aaron was clearly on a student budget when he got his. It was so close to the base of his shaft that he could only have been laying naked in front of the tattoo artist; and shaved too. Did he get hard while he was being worked on? I certainly would have in that situation.

Having now a sense of how thoughtful Aaron was before making any decision, big or small, I couldn’t help but retrace the internal struggle he must have gone through before his tattoo ended up at the base of his dick. I’m sure he had craving for ink for a while, hoping to look badass. But he also knew his mom would likely disapprove. So, he got one right at the base on his dick, where strangers or family could never tell. And even when naked, the tiny tattoo was only visible if he had his pubes shaved. I wondered how many other guys had seen it before me.

Shit! Why does my mind always wander around like this? Why can’t I just focus on servicing his cock instead?

His cock was nice. Probably the same length as mine, 5 ½ or 6 inches erect, but a bit thicker. It was thinner at the base, thicker in the middle, and thinner again toward the tip. It had a pointy cut head, shaped like an arrowhead. I took the arrowhead in my mouth, while stroking his shaft with my right hand. My mouth gradually edged its way along the shaft, eventually engulfing the whole length, as my nose pressed against his non-existent pubes. My hands moved on to grab his bubble butt, pulling his body toward my mouth. I made it a point to take his whole length in, which I’m thankfully capable of doing with a 6-incher. This is a rivalry after all, and I wanted to show off my skills to the boy.

As I was working his cock, sliding my lips up and down his shaft, he started moaning. But not a deep manly moan. More like a high pitch girly moan. The one a soprano virgin would make the day an expert tongue reached her cunt for the first time. I was thinking to myself: ‘If this is the sound you make while my mouth is working your pole, I can’t wait to hear what sound you’ll make when my cock is pounding your hole!’ I sucked him a little bit longer and eventually got back up to give him a kiss.

‘Do you like my dick?’ he asked

‘Of course, I do’ I responded

‘I’m sorry it’s not bigger’ he said ‘I’m below average. I’m only 5 ½.’

‘You’re not below average at all’ I said. ‘I’m average. And I think yours is a bit bigger than mine.’

‘Let’s compare’ I added.

I dropped my boxers and positioned my dick right next to his.

‘See, we’re exactly the same length’ I said. ‘But yours is pretty thick’.

‘You think so?’ he asked, kind of surprised by my statement.

‘Well, thicker than mine’ I added, while pointing at our two cocks side-by-side.

What is wrong with kids these days? They watch so much porn at such a young age that their perception of normalcy is completely distorted. They come of age thinking that 6 inches is ridiculously small, 8 inches is average, and 10 inches is the goal. Aaron had a perfectly normal sized dick but still had insecurities about his manhood. This was yet another cue that he hadn’t seen many dicks in real life.

Then, it was his turn to get down on his knees. By that time, my dick had been precuming for a while. With my finger, I collected the precum build-up on the tip of my dick and moved my finger to his mouth for him to lick.

‘Do you like it?’ I asked.

‘Yes, it’s sweet’ he replied.

‘That’s good because there is a lot more where it came from’ I said.

He started working my cock. His thumb, index, and middle finger jerking the base of my shaft, his lips around the top half, and his tongue working my dickhead. At least, I could tell it wasn’t his first-time sucking dick. But it was a little bit too sensual for me. I was craving for something rougher.

‘Take it all the way’ I ordered.

While I said that, I put both my hands on the back of his head and pressed his head toward me, forcing him to take more of my dick in. When I felt my dickhead reach his pharynx, I released to let him breath, and then shoved my dick deeper into his mouth, applying more pressure than the first time.

‘Come on Boy! Take it all the way. It’s not that big!’ I said. ‘It’s about time you learn how to take a whole dick in your mouth’

My cock was about three quarters of the way in, but not quite fully. I pulled out again and pulled him right back in.

‘Come on Boy! I won’t let go until I feel your nose buried into my pubes’. I said ‘Show me what you can do’.

This time, I could feel his nose in my pubes. I held the pressure on his head, as I could hear him struggle. But I thought to myself that a former swimmer should be able to hold his breath for a few seconds.

‘Come on, five more seconds! Four, three, two, one, zero. Good Boy!’

I let go of his mouth and, before he was able to catch his breath, I made him stand up, grabbed his head with both my hands, and gave him a passionate kiss, my tongue invading his mouth, the same way my cock did a moment ago.

‘I hope my dick wasn’t too rough on your mouth’ I said.

‘Don’t worry, I’m up to the challenge’ he replied.

‘Good, ‘cause it’ll be a lot rougher where it’s going next’ I joked.

‘I can handle it’ he said.

I threw him on the bed and jumped on top of him, kissing him some more. I was enjoying the tension of me pretending to play rough, although it was more for show than anything else. He was a sweet boy and I wanted to push him outside his comfort zone, but not in a freaky way.

We eventually started 69ing. I was sucking his dick in a voracious way, while he was sucking mine in a much more sensual way. Since I wasn’t sure how long a 19-year-old could last, I would stop occasionally, to ease the pressure mounting in his dick. And then, I would go right back at it.

While I was enjoying the appetizer, I couldn’t stop thinking about the entrée. All I cared about was stuffing my hard cock in his little boy cunt. I still wasn’t sure if it was a virgin hole or not, but I didn’t really matter to me. Just the thought that it was even a possibility was enough to drive me crazy. I couldn’t wait any longer.

‘I really want to finish you off’ I said. ‘Right here, right now’.

He slid off the bed and went on to grab the backpack he had left at the front door. From the front pocket, he pulled out a bottle of lube and a plastic bag with at least a dozen condoms. It was an assortment of brands I recognized, like Trojan, mixed in with no-name ones, of all different colors. They were probably free giveaways he had collected at safe sex awareness events on campus. How organized he was and prepared for everything never ceased to amaze me. He was so damn cute!

He got up on four on the bed, exposing his pinkish hole. It looked awfully inviting. Even though it was my dick, more so than my mouth, that I wanted to shove up in there, I still went on to rim his hole, just light sensual touches at the very edge of his rosebud, kind like light brush strokes. This probably caught him by surprise as his whole body tensed up at the first touch of my tongue. But he relaxed shortly after. He seemed to be enjoying this feeling, based on the whimpering sounds coming out of his mouth. I then took the bottle of lube and dropped a couple of squirts on his rosebud. I rubbed it a little bit and inserted a first finger, and then a second one. His hole was tight, as to be expected, but he took my fingers without any complaint. He started moaning again, as I stroked my fingers in and out of his hole. After he was loosened up, I turned him around to have him lay on his back, made him spread his legs, and got on the bed, my rock hard cock facing his hole about to be violated. I put a condom on and lubed up my dick.

The odds of this 19-year-old cumming faster than me were pretty good, but I didn’t want to leave anything to chance. I would die of embarrassment if I wasn’t able to last longer than him. I positioned myself in such a way that my knees were bent, and my thighs were spread on each side of his ass, with his thighs spread over mine. My ass was touching the sole of my feet. And I extended my arms behind me, for stability, with the palm of my hands touching the bed cover. I seem to remember that this position is called ‘arch’. But I’m not very good at theory. Everything I know about sex, I learned through practical training. Lol. I know there is a college level course called human sexuality, where you probably learn these kinds of things. But if human sexuality is not a class specifically designed to allow football players to get passing grades, then I don’t know what is. I never was a football player anyway. I never took that class.

This arch position had two benefits. First, my bent knees felt somewhat uncomfortable, which would distract me from cumming too quickly. Second, my dick would penetrate his hole at such an angle that I could pound harder on his G-spot. I don’t have the girth to tear his ring apart. I don’t have the length to explore deep inside his guts. So, I have to focus on the what my 6-incher can do best: Hammer his G-spot and beat it to submission.

I pulled him toward the tip of my dick, put a pillow under his lower back, and started probing his hole. Initially just teasing it with the head and pulling out. Then getting back in, a little bit deeper this time, and pulling out again. The third time, I shoved my tool halfway in. Next thing you know, I was balls deep into his boy cunt. Balls deep sounds like I’m bragging, but when you only have a 6-incher, it’s kind of a given that you’ll get balls deep. Lol. I worked his hole very slowly at first, to give his ring a chance to adjust to the invasion. And little-by-little, I started picking up the pace, his moaning increasing in unison.

His right hand attempted to grab his pulsing dick, but I pushed him away.

‘Hands off, Boy!’, I instructed. ‘You’re not allowed to touch yourself. You’re mine and, from now on, I’m the one in charge’.

He went on to stretch both his arms and grabbed the headboard behind him. I could see the little patches of light reddish-brown hair in his armpits. At least one area that had survived his razor blade and reassured me I wasn’t fucking a 12-year-old.

‘Keep your hands over there’ I continued ‘You’ll only be allowed to cum when I decide it’s time. But once I let you, you’ll cum like you’ve never cum before. And I want you to keep eye contact with me’.

‘I’ll try’ He smiled.

My cock relentlessly hammering his G spot, just at the right angle, made him squirm like a little bitch. Boy, was he a screamer! I could only think of how poor the sound proofing of these prefab hotels was. If I could hear my neighbors watching TV. If I could hear them flush the toilet. If I could hear them slam the door. Certainly, they could hear the boy’s screams. The guests on the 5th floor could hear him. The ladies at the receptions could hear him. He was out of control. My neighbors would be giving me an interesting look tomorrow morning, if we ever came out of our rooms at the same time.

I couldn’t help but wonder if Aaron would have kept the volume down, had we been doing it at his parents’ house rather than in my hotel room. I once had a neighbor in my apartment building who was having loud sex with his girlfriend. I don’t know what he was doing to her, but the bitch liked it. And she always made sure the whole building knew. I was joking about it with my colleagues, one day over lunch. This was 20 years ago, a different era, when casual conversations were still allowed in the workplace, and you didn’t have to watch your every word by fear of offending someone. I was asking their opinion on whether my neighbor was the guy or the girl. They all agreed it had to be the guy. If it had been the girl hosting and the guy visiting, there is no way she would ever have been screaming like that. Aaron clearly didn’t care how loud he was. And I didn’t care about what my neighbors would think!

Even though he couldn’t jerk his cock and I wasn’t jerking it either, I could tell he was getting close. Now that I knew for sure he would be cumming before me, it was time to try a new position that was more comfortable for me but just as pleasuring for him. I pulled my dick out of his hole and pulled his body towards the edge of the bed. I stood up on the side of the bed, put his knees on my shoulders, and shoved my cock right back into his boy cunt. I started fucking him while standing up. And he went right back into screaming mode.

‘I’m a hunter, Boy! And today, you’re my prey. I’ll finish you off’. As I was saying this, I accelerated the rhythm and started hammering his G spot at 120 BPM. I eventually grabbed his cock to start jerking it. Within less than ten strokes, his cock erupted and discharged a creamy load on his bare chest. Although I had instructed him to keep eye contact with me, his head shook from left to right as the ecstasy was more than he could handle. And he let out an even louder scream, if that was even possible. Then a second load splashed on his stomach, followed by a third one and a fourth one.

After he was done cumming, I continued pounding his hole and jerking his cock, making sure to rub his sensitive head with my thumb. He kept screaming, but a different scream this time. He was begging me to let go of his abused cock. They say good sex is 50% pleasure and 50% pain. I made sure I was keeping things in balance. I eventually released his poor battered cock and pulled out of him in one thrust. The suddenness of my exit made him gasp. I ripped the condom out and started jerking my rod on top of his. So much pressure had been building up that my cock exploded right away. My first load landed in his right eye. This caught him by surprise, and he brought his finger to his eye, as if he was trying to get rid of a fly. That poor boy just couldn’t catch a break from all the abuse I was giving him. As he was trying to clean my cum off his eye, I think I sensed a bit of fear. He was now blinded, unable to see where the abuse would be coming from next. My second load landed on his lower lip. ‘Fuck! I just missed his mouth by a millimeter’ I thought to myself. The following loads landed on his chest and stomach, which were already covered with his own cum.

I collected some of our man juice medley with my finger and brought it to his mouth for him to lick. He turned his head in disgust. I didn’t even try to force feed him. The boy had endured enough abuse for the night. Instead, I brought the finger to my own mouth and licked it lusciously, as if it was ice cream dripping out of a cone. I made sure he saw the movement of my Adam’s apple as I swallowed. I did it while giving him a ‘You still have a lot of learning to do, Boy!’ kind of look. I didn’t have to say it out loud. We understood each other. Man sex is not just unicorns and butterflies. They call it ‘the dirty’ for a reason.

My body collapsed on his. The sweat on my forehead running down my nose and dripping on his nose. We smiled at each other, and I started kissing him again. The look of fulfillment on his face filled me up with both pleasure and pride. Once again, my average sized dick had managed to get the job done. His dick was now soft, but mine was still rock hard and pulsating.

We showered together, washing the cum off each other’s body. He got dressed and I kissed him goodbye, still naked, still at half-mast, still content. That night, I had the most restful sleep I’ve had in a while.

We started messaging the next day.

Me: ‘I had fun last night’

Him: ‘Me too. It was amazing’

Me: ‘We should do this again. I’m in Fargo for another week’

Him: ‘That would be great’

Me: ‘I feel it’s my turn to return the favor. I’m due for some dicking too’

Him: ‘I can take care of that’

Me: ‘Can I ask you a favor though?’

Him: ‘Sure. What is it?’

Me: ‘Can you not shave your pubes until next week? I want to be fucked by a real man, not a little boy’

Him: ‘OK. We’ll see how much I’m able to grow back in just one week’

Me: ‘I can’t wait to feel your dick up my ass’

Him: ‘Be ready for it. I won’t be holding back, lol’

To be continued.