In front of us stretched nothing but road and nature. Forever. Sometimes forest passed us by, sometimes cliffsides with nets protecting the road from landslides, sometimes even huge lakes in the distance. Other cars became less and less and less common. This would be scary, this idea would be idiotic, if circumstances were different.
I had resisted the urge to Yes an online stranger as I first introduced myself to the DTF world of the modern Internet. I had resisted the fans of my clumsy immaturish amateurish online profile. I had resisted "Come on, come downtown... =)" and "My friend and I would love to help you out, we'll all make each other cum a few times", and "Would you like to meet and play with my wife and I?" and all the classless to-the-point copy-and-paste offers. It was flattering, I guess, that I was desirable. I had never felt that way. But I needed to compliment myself too: I deserve a really good experience. My now-peaked libido was like an inpatient puppy with no chill and no caution, but if that puppy was too loud to be ignored then I would at least give it the best bone I could find it.
I was no celebrity. It was just that I was young, and my penis was a bigger than normal when it was hard, and there's something about "I'm shy but horny and I've never done this before and I want a man who can give me my first time" that just brings jackals as well as lions. I was, in principle, some sort of optimum demographic for the time being. And I was in some sort of sweet spot, where I was young enough to be endearingly innocent I guess? without being unethically young. And I could understand why inexperience was an arousing idea: that someone could "Aladdin"/"I could show you the world" me about gay sex. About sex at all. I liked that idea too. I imagined someone strong but gentle, someone powerful enough to be in control but who would use that power gently and for my pleasure. I knew that was a risky type to dogwhistle toward me.
There must be a responsible way to do this. My knees shook whenever I thought of a man touching my penis. my knees literally shook. I needed this badly, and I was aware that I was a cliche, some sort of archetype.
But as desirable as I might be to an older man, it was mutual: the idea of maybe a middle-aged regular-looking man touching - actually touching - my nakedness, and letting me touch a real erect penis - was just perfect. Nothing muscular, nothing young, just a Guy... taking off his clothes and showing me an inpatient penis for me to hold. A penis whose sensations I couldn't feel, not my own, but one that I learned to please by trial and error, by watching another man's pleasure and following his instructions.
Following his instructions... I had entered a phase where that sounded really nice, theoretically...
I had lost all illusions that this was average. I was unusually sexually charged, probably, unusually gay-curious, probably, unusually shy, trust me, and unusually brave to go to this length: to find a safe way to offer my body to a middle-aged stranger. Kind-of stranger; I made sure we would chat for months, and I subtly backchecked, and created situational safety-nets I won't go into.
I wasn't sure what sort of sexual being I'd turn out to be, but for now I found myself leaning into my innocence. For once, it was a good thing, because it aroused my friend in the driver's seat, apparently, and it gave me space to ask for guidance and be strangely honest. I'd never talked about any of these feelings and needs, it was always secret. It is utterly bizarre to say to another person that you are horny, much less describe your sexual fantasies and how your body cums. It was utterly weird answering the question about how my particular penis cums, that the orgasms don't squirt far. Imagine saying that to someone in conversation. But there's a perfectly reasonable context! Cum hitting a uvula must really suck. No pun intended.
For once, my nervousness felt nice. It was strange. My knees were shivering and shuddering again, like I was cold.
"Hey, you okay Kevin? We can go back if you like."
I grinned fondly, tossing my hair a little without intending to. "I'm a lot of things! I'm... terrified! But not of you. I'm just very, very shy. But I'm going to lean into this. I'm doing this. I like this. I'm here for this, and however nervous I look, I want this, unless I say I don't, okay?"
The man smiled and drove and nodded.
"Look, I've talked to you for a long time, and I trust you to get me through this." I paused and sighed and tightened my shoulders and released them again. "When we're back in Portland, I'm going to be a prude and too shy to kiss girls and sex will be something that happens when I'm alone at night, but for now..." I heaved another big sigh and made myself say what I'd been looking forward to saying to someone in those lonely moments just before cumming. "...My body belongs to you. It's yours. All of it. I want you to have it. It's yours right now."
It took all my bashful bravery to say that, I had no idea I had no idea how he'd react to that, what he'd do with that message, whether he'd pull over and take me or ask me to do something big or be weirded out by this directness I imagined in my fantasies what but I wanted to trust someone with the next step.
"Hey Kevin. It's okay, just relax. here, no one's around. Seriously, no one's around, no one will care. You sound like you need to be free. Wanna be naked?"
"...What, in the car seat?"
"Yeah. You'd like direction? Show yourself this is real, this is really happening. Take off your seatbelt, slip out of all those clothes, throw them in the back. Relax! Say No to anything you like, you know that, right? But if you're in Yes mode right now, go for it. Now's the time."
Well I had literally asked for something to happen, and the invitation was made. So I unbuckled. I looked at each horizon, for something that would make this tangibly hazardous, and had no excuses to tell myself. I had the willingness and lacked the reasons not to... so I was suddenly, for the first time in my life, out of reasons not to be naked in front of someone. So I went for it. And it felt so strange, to unbutton in front of a smiling man. I trembled, but I kept checking and it was not because I was cold, or scared of anything. I was shivering because I wanted a man to stare at me. I used every last bit of will shaking off this shy feeling and accepted that I was taking off my underwear and throwing them out of arm's reach.
My absurdly erect penis was touching outside air. My penis was being glanced at, so lingeringly that it was for the best that there were no incoming cars to watch out for. I was being watched. By this man in control. By Jack. A man named Jack is watching my erection. My penis knew it, it kept flexing and producing precum.
Before I ever heard it coming a car zoomed by us. Who knows what they saw.
I'm naked outside and driving. Well, being driven. Without clothes or seatbelt, without any security my body had gotten used to having, we drove on. My bare feet touched rubber. My bare bum touched old leather. My penis touched cool air. I smiled back at my driver. It was starting to become a little less Holy Shit.
The Holy Shit returned when Jack touched my face and neck, and then, I received my very, very first other-man's touch on my penis, a fleeting touch. My friend Jack spiraled one finger around the edge of my foreskin, gathered up a big bunch of precum, and tasted his finger. And kept driving, casually driving, leaving me gasping - literally gasping - for more. Jack enjoyed watching me squirm and listening to me pant, and he just drove.
It was Spring, thank god, so sunlight didn't hurt. I had no wish to nurse sunburns with no tan lines. I just felt warm and cool at the same time. And I believed Jack when he said I could change my mind. It's just that being naked in his passenger seat enhanced what was literally true: Jack was in the driver's seat. I've chosen this. It's good but weird, but I've chosen this. I do want this.
We chatted for a while about the milestones we passed, about how I used to come to these places when I was a kid, and they were gorgeous, and it made this trip feel like an adventure, this one an adventure I had chosen.
"Have you ever done something like this?" I asked him. I don't know why I hoped he's answer that he hadn't - I guess even though this was purely physical, I would feel less important if this was weekly for him or something. I wanted to be special too.
"Would you believe me if I said 'Hell No'? Kevin, talking to you online has been amazing. You're a lot of fun, you have one hell of an imagination, and this feeling of yours, this feeling inside you? There's something beautiful about it. It's not how most people feel about sex. Sure, I've met people and we've had all kinds of sex, and yeah, I've been in love... But it's like you're on some sort of pilgrimage about this giant horny feeling of yours! And I'm here for it. Let's find out where it leads. He smiled comfortingly at him.
I did believe him.
And looking down at his lap, too ample to conceal, jutting out to the right side and making an unambiguous impression of its shape, was yep, Jack's definitely erect penis. There was no mistaking it, no "just my keys" excuse - then again, Jack didn't seem like the type to have an erection and pretend he didn't have an erection. It's just... I'd never been in front of an erection before.
We chatted some more, and it became casual, but always with the flirty overtone of the fact that I was parading my body for him on his terms. Even so, it felt kind of powerful, both that I was breaking a law and that I was drawing the intrigued attention of a man in front of me.
Other cars went by. Sometimes I saw the people inside them, and sometimes I think they made eye contact with me. I trembled. But I trembled in the same way I trembled when I thought of giving my cum to someone else. That exact tremble, smiling shyly and moving my body a little flirtatiously, bashfully.
Before too long, we stopped by a cabin with huge windows, by a little creek. He pulled up to it. I wasn't expecting this. For some reason, I was expecting a hiding spot in nature somewhere. I don't know whether a real place felt weird because I didn't feel I deserved something nice like this, or because it didn't feel as illicit as I felt being here.
"Where's this?"
"I rented it. The owners live a way's up. It's used for cheap honeymoons and fishing trips sometimes, I think. So they don't come around when it's booked, they don't want to know or see that! Come on!"
He got out of the car. I spent a serious moment contemplating whether he wanted me, expected me, to get my clothes. I forced another moment of bravery and decided No.
So there I was, walking with Jack, naked. He led me with a gentle hand on my shoulder, smiling friendily. He sensed my thoughts rather well. "You're a grown man. You're allowed to do something about your desires. Heck we're pushing it with showing the sun your cock, but this is all natural!"
He didn't take me inside. Jack sat me down on some soft grass, and while I was somewhere between his knee-level and hip-level, he gradually took off his clothes. Holy shit. I don't know why I expected more prelude. Maybe because I didn't know how to transition into reality of Having Sex. But maybe he's Just A Guy, just like I hoped, and he needs this too? Kevin you're overthinking this, maybe he's just a nudist who wants to chat by a lake.