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.