I thought I was sneaky, I really did. Apparently, I was wrong. But I should start from the beginning. My name is Alex, and I am the star quarterback of my school. Basically all the students look up to me in some way, the teachers love to point to me as an example, and even around town I get friendship discounts at shops and all sorts of perks. Ever since I led our small team to the state title, I've been the town hero, more popular than pretty much anyone else. What can I say, I live in a pretty conservative town that just loves its football—the straight-laced sports hero plays perfectly here, and I'd be lying if I said that I didn't occasionally take advantage of that status to get myself out of situations I rather wouldn't be in. Occasionally! It's not like I'm going around banging the mayor's daughter and getting out of it with nothing but a winning smile and a shrug. Besides... I haven't banged anything yet. Yeah, I know, the big jock of the city is a virgin, whatever. I'm getting to that.
You see, I have a problem. I'm gay. I don't exactly know how it started... maybe hanging out in the locker room with all those other muscular, good-looking guys just had an effect on me, maybe it's something deeper in my past, I don't know, and I don't care. And normally, that wouldn't be a problem, but in this town? I'm pretty sure it is. These people here are definitely way too much into machismo and all that, practically obsessed with being manly. And, well, it's not just that I'm gay, but I'm also into crossdressing. So far, I haven't tried anything outrageous, but I do have a pair of lingerie panties—I got them off some girl that I told I wanted them to "remember her by", she ate that up like nothing—that I occasionally wear under my regular clothes when I go to school. I just really like the feeling of the lace against my skin... it's something special that makes me feel soft and comfortable, rather than the hard, manly exterior I'm expected to show all the time.
So this puts me into a conundrum. While there is a chance that this town might suddenly become OK with homosexuality and crossdressing if their hometown hero were to reveal that he's into that, the more likely option to me is that I'd get dropped like a hot potato and become persona non grata before I could even say "hut hut hike", and that would absolutely ruin me. And therefore, I keep that secret locked up real tight. While I can wear my lingerie under my clothes during regular classes just fine, I obviously cannot wear them when it comes to going to football practice, but I have a solution for that. I used a bit of my clout to get the janitor of the school to give me a key for an old storage room he doesn't use anymore—I gave him a story about how I need a cool, dark place where I can be alone before games to focus, and of course the janitor is a fan of the team just like the rest of the town, and giving him an opportunity to claim that he helped with getting the team a win could've gotten him to do anything.
I've been using that room to change out of the lingerie and into more regular underwear, stashing the lingerie in a lockbox before heading out to the practice, game or whatever. Then, afterwards, I would return there again to change back into the lingerie and head back home, leaving everybody none the wiser. Or so it had been. Because, well, I thought I was sneaky, but evidently, I was wrong. For you see, right now, I'm standing in that room, suddenly realizing that I forgot to lock the door, wearing nothing but a shirt and panties, and staring at the other person that is now standing in the room with me. Honestly, it's pretty much a worst case scenario to me—not only was I caught, but I was caught pretty much entirely in the act, and this guy could just take a picture of me with his phone and ruin me entirely.
But to my surprise, he doesn't do that. As my mind races to catch up with what is happening, I start getting a better picture of who it is that just caught me. It's a nerd, quite clearly. Diminutive stature, glasses, long black hair, orderly clothes... this guy is absolutely a nerd, and that might be what actually saves me. While the other jocks at this school take great glee in bullying nerds, I don't do that, and in fact often make efforts to stop some of the other jocks from bullying nerds. It's not something I do for altruistic reasons, obviously—in fact, I've been doing it for pretty much precisely this situation. I wanted to make sure that I'm nobody's enemy, so that nobody would actually want to ruin me. And as I try to stammer out an explanation, the guy just smiles and says "It's OK... you don't have to worry." before pulling out a pad and pencil, writing something on a piece of paper, laying it on a nearby table and leaving the room again before I even have a chance to speak a fully formed sentence.
And so while the very first thing I do after he leaves is locking the fucking door so this doesn't happen again, I then take a look at the piece of paper he laid down. To my surprise, it's an address. An address, an instruction to come at midnight and "come the way I'm most comfortable", and a name... "Simon". The note even has a little heart next to the name. There's no doubt in my mind what's going on... this guy just all but propositioned me for a gay hookup of sorts. And the thing is, I'm pretty sure I could just stand him up and nobody would be the wiser. Even if he tried to reveal my secrets, nobody would believe him. He took no photo evidence or anything. But then again... he seemed like he had no ulterior motives in this. Maybe I should just hear him out.
Eventually, it became clear to me that I had to at least talk with this Simon. With about five minutes to midnight, there I am, standing in front of the door of the house at the address on the piece of paper, wearing my normal clothes with the lingerie underneath, because after all, that is the way I feel most comfortable, and I'm pretty sure that's what the note was getting at. After a few moments, I manage to build up the courage to knock, and after only a few seconds, the door opens and there he is again. Simon. The only one that knows my secret. But if he's going to be blackmailing me over it, he's doing a great job at hiding it, because his expression is nothing if not friendly and open. With a gentle wave of his hand and a cheerful "Come on in!", he motions for me to come inside, and thinking nothing of it, I simply follow.
As he leads me up the stairs and towards his bedroom, he begins to talk. "So, Alex... the big sports hero of the town, and a secret crossdresser. You live quite the life, don't you? I... I just have a single question for you before we continue. Are you gay?"
It's such a blunt question I never expected to answer honestly, but at this point, there's no point in denying it, he's already caught me red handed. So I nod. "Yeah, I am."
We enter his bedroom and he hops onto the bed, sitting down and facing me. "Well, as you might have gathered by now... so am I. We're pretty similar, aren't we? Both of us hiding our deepest desires because we think the rest would never understand..."
While I had expected that, the way this conversation is progressing has me a bit surprised. Might I have actually found a soulmate? Someone I could finally confide my desires in? Someone that wouldn't judge me? The thought seems too good to be true, but here I am, and when I look into Simon's eyes... I can see nothing but sincerity there. He's genuinely wanting to help me. But before I can reply, something strange happens. Emotions start bubbling up inside of me, and before I know it, tears are starting to form in my eyes. It's like all the pent up fear over being exposed has come back all at once now that I feel free.
I choke back a sob or two, but then he takes me by the hand, pulling me closer to the bed. "Hey, hey, it's OK, Alex. Just let it out. You're safe now... I'll listen to everything you have to say, OK?"
And it's like his voice is unlocking thoughts I had locked away so long ago. I practically collapse onto the bed, all my energy leaving me at once, and then the tears finally flow, leaving me sobbing openly with my face pressed into a pillow. And Simon doesn't pressure me at all. He just lays down on the bed next to me, gently patting my back and whispering soft reassurances in my ear. After a few minutes, the tears start to dry up, and I manage to lift myself off of the pillow and look into his eyes. There's such a loving look in his eyes, the kind of look that tells me that finally, I've found the one. The one I can rely on. It might be incredibly stupid to fully confide into someone about ten minutes after you first met him, but... it feels so right.
With a gentle smile, he asks "Do you feel better now?", and he's right. I do feel better.
The next half hour or so is spent entirely on telling him all my experiences, all my fears and desires, everything. I'm an open book to him now, and it feels so good to finally let go of all these secrets. Simon, for his part, just listens intently, occasionally chiming in supportively when he feels like I'm getting worked up again. Eventually, I've said everything I could say, I've completely poured myself out in front of this little nerd, and I feel better than I've ever felt in my life.
"But, um... I think that's enough about me. What about you, Simon? What's your story?" I ask, wondering about his background.
He smiles again, that smile that just makes my worries fly away. "Oh, there's nothing much to me. I've always had a certain desire for boys, and just buried it deep inside of me, knowing that this town wouldn't look nicely upon a gay nerd like me. But, now that you're here... I can be a bit more open. In fact, um... I have something I want to ask you. You're wearing those panties, right? Could you show me?" he replies, a blush spreading on his cheeks as he looks away shyly.
Thinking about it, I see absolutely no reason to not give him what he wants. He's been nothing but open and friendly towards me... and hell, he's already seen me like that before, so it's not like it's anything he hasn't seen before. So with a bit of trepidation—I'm obviously still not used to stripping down in such an intimate setting, after all—I take off my regular clothes. My shirt, my shoes, my socks and my pants all hit the floor one after the other, and now I'm wearing nothing but those lace lingerie panties. I'm starting to get hard just from the sheer thrill of intentionally exposing myself like this, and the bulge is becoming quite noticeable.
"You're beautiful, Alex, you know that?" Simon mutters, staring at my bare chest. His hand slowly moves forwards, reaching towards my abs, and his eyes rise to meet mine, silently asking for permission. After giving him a short nod, his fingers brush against my muscles ever so slightly, moving up and down with timid, yet deeply intimate movements. "Feels so nice..." he whispers under his breath. After a few moments of him silently caressing my six-pack, he suddenly snaps out of it and blushes more heavily, clearly embarrassed he's gotten caught gawking.
Simon clears his throat before talking again. "Um... so... sorry about that. I lost myself a little..."
I hold his hand gently, caressing it a bit to reassure him. "It's OK. Nobody's ever looked at me like that before, and to be honest, it was kinda exciting..."
"Um, well, if it's something exciting you want... I have something else you could try. It's in the walk-in closet over there, on the stool. Take... take a look and see if you want to give it a try." he mutters, almost like he's ashamed to even suggest it to me, causing me to wonder just what it is he's got in there. Well, he's got me curious, so I get off the bed and walk into the closet. I take a look down at the stool, and now I see why he was so embarrassed to ask... this is a Playboy bunny outfit. Bunny ears, a leotard, cuffs, a white collar with a bow tie, and a little apron that'd probably make me look like a dirty maid. As I stare at the outfit, emotions are battling inside me. On the one hand, yes, I did wear and in fact am still wearing lingerie panties, but that's not open and visible most of the time, and this is a full slutty outfit. But on the other hand... I want to make Simon happy, and it seemed like this means a lot to him, especially given that the outfit seems to be my size and he must've gotten it especially for me. And not to mention... the idea of letting Simon take control and order me around a bit is turning me on. What could be the harm in letting go a bit? Simon's nice, there's no way he would ever hurt me in any way. He's been nothing but welcoming towards me and my desires... so why not give in to some of his?
After a few moments of thinking, I make my decision, and put on the bunny outfit. The leotard fits very snugly around my crotch, and seems to make my bulge all the more noticeable, which is probably the intent. I'm not sure how much more of this I can take before my erection is going to be standing at full mast, because this is really turning me on. After putting on all the accessories, I turn around and step back into the bedroom, where Simon is waiting. When he sees me in that bunny outfit,