Well, it's the end of another day at the skate park with my buddy Taylor, and that means it's our obligatory attempt at taking a jump down the staircase, probably the toughest jump of the whole park. Sure, we've both done it before, but every attempt is an exciting moment, a thrill that the other spots here just don't bring. Of course, it's also more dangerous, so we only attempt it rarely. I've managed my try just a few moments ago, even if it was a close one, so now he's up. The smile on his face is confident as he rides his board up to the staircase. He takes the leap, soars through the air... and absolutely crashes and burns.
Rushing up to him, I can hear him cussing his heart out, and I help him back to his feet. Doesn't seem like a particularly bad crash, though I can see a bit of blood staining his jeans on the left knee and a slight rip. By no means something serious, it's just going to smart a bit for a few days, and I'm sure it'll heal quick. The two of us share some friendly banter over his failure, and eventually we part, as is usual. We've been doing this for quite some time now, after all, and we've been inseparable best friends for even longer. However, there are some things I don't share with him.
Indeed, after I get home, I take out my phone and check my social media, something I only do in private for, well, reasons relating to the people I follow there. In particular, there is an assortment of young men posting lewd photos of themselves... in girls' clothing. Yes, I'm into crossdressing guys. Guys in dresses, skirts, panties... I love it all, especially one of these guys. He's a new face that only recently popped up on the site, going by the handle "Sk8terBoi69", and he's a real beauty. Wearing a face mask to protect his identity by blocking most of his face apart from the eyes, and dressing in the most adorable, girly outfits, his photos are the hottest damn thing on the Internet. But there's one additional thing that sets him apart from the others—he lives in the same town that I do!
There truly is something special about a boy next door, even if I don't know which door around town hides him. It's like I could feasibly run into him out there, and that gives the fantasy that little extra kick. And, well, sometimes you do something when you get, er, excited that you wouldn't do otherwise. In this case, I shoot my shot, and directly message Sk8terBoi69, telling him how hot I found him and that we live in the same town, asking if we could maybe meet up. In response, he sends me a shot of his ass, which is just absolute perfection and gets me even more worked up. So... I send him a picture of my dick, which was of course rock hard, and ask again about the meetup, to which I don't get a response for a while. After this, I'm so pent up that I jerk off right then and there, and that gives me an opportunity, to, uh... come down again.
It's then that I realize that I was being a bit of an asshole. Just sending a picture of your dick isn't exactly good etiquette, and I was being real pushy. So with a sigh, I grab my phone once more and send him another message, this time an apology, and offering that we just forget about the whole thing. But what he sends back blows me away. The message reads simply "You know, it was stupid to send me a picture of your dick like that... you wanna show me it for real instead?" I'm stunned. Is he seriously saying what I think he's saying? Sure enough, another message comes in before I can even respond: "You know the park in the center of town, right? Be there at 9."
So "be there" is what I'm doing, rushing there as soon as I could, thinking largely only with my libido. Practically nobody visits the park at this late an hour, so it's dark and empty, and I'm really anxious that I messed up somewhere as I sit here on a park bench, illuminated by a nearby lamp, but then, I spot someone coming closer. It's him. Wearing a hoodie and fairly short skirt as well as cute striped kneesocks, I can tell it's him from his trademark facemask and long wig. This has to be Sk8terBoi69. "Hey... you must be Jacob, right?" he asks me as he gets closer, his voice immediately soft and sultry.
"Um, y-yeah," I stammer, still unable to believe this is actually happening. And when I stand up to meet him, he approaches me, grabbing my crotch, his eyes half-lidded with lascivious intent. Wow, he's forward... but then again, he's a crossdresser that posts dirty photos of himself online, so perhaps I should have expected this. "Ah, um... n-not here..." I mutter, slightly pushing him away, my face reddening rapidly. "I... I'll get a hotel room..." I then add, and he nods, most of his expression hidden by that mask, but with his eyes showing amusement, so at least it seems like he's not annoyed with me.
The trip to the local hotel goes by quickly, and of course, it would be my luck that all the cheap rooms are already booked, leaving only the expensive luxury suite, but fuck it, I can't let some money come between me and him, so the room is booked and we make our way there. In a way, this is probably for the better—if we really are about to do what I think we're going to do, a comfy bed is going to come in handy.
And so, there we are, the two of us standing in this quite luxurious looking hotel room, the stars visible outside through the window, the bed behind us as a not entirely unpleasant silence falls over us. "Am I everything you thought I'd be?" he asks me, wiggling his hips coyly, causing his skirt to sway and his socks to slouch a bit. Looking him over, God, he really is just as pretty as in his photos, maybe even more so. From his head to his... knees? Wait, on his right knee... that's a scab. Almost like he had some sort of injury there earlier today, right? And his handle... Sk8terBoi69. Assuming that's not just a handle, he's a skater. And thinking about it, his voice... he's putting a bit of a voice on, but it sounds familiar. Oh. Oh my God.
When the realization hits me, all I can do is stammer it out. "T-Taylor?!"