(no) regrets

on some level I guess I should be grateful that the first thing that comes to mind when thinking about bad decisions I made in high school is “asking out a particular straight guy.” he was in my advisory group — blond hair that at the time I might have poetically described as “windswept”, kind of a stoner-surfer thing despite the fact that this was New England and not California. also he was a libertarian — that really should have been the deal-breaker. but I thought he was cute (I stand by this assessment, frankly), and I liked his smile, and I thought he was funny — and he seemed to think I was funny, too. (I am funny, but my humor was underappreciated in high school. wrong audience.)

anyway, long story short I spent most of senior year crushing on this stoner libertarian, despite the fact that I still don’t even drink alcohol ten years later. (what did I think we were going to do on dates? for his senior project he rebuilt an old truck engine; I translated part of a Spanish novel.) I dreamed about him. I daydreamed about him. finally I worked up the courage to ask him out; I caught him outside on his way to his car. I’m too embarrassed to report the conversation in full but he turned me down, obviously, with the immortal words: “I’m not gay, dude — but it’s cool.”

I actually really appreciated, and still do, that he took it so easily in stride. I’ve been extremely lucky on that front, and I’m grateful to him for setting the tone early in my experience coming out to people and asking guys out.

I moved on — thankfully — to a series of college crushes, inducing varying levels of embarrassment, and then I graduated and moved to a city and got way sluttier. but, ten years later, my subconscious still regularly brings me very involved dreams to remind me of my terrible high school crush on Eric Brennan.

you may have guessed at this point where this is going. it’s been ten years since we graduated from our artsy little suburban private high school (there’s another difference: I was able to attend because my mom taught there; he was paying full tuition and wasting most of the experience doing things like getting extremely high behind the school at 11am on a Tuesday, such that he had to be shuffled around between handlers for the next few hours — a story I only found out about later).

it’s time for our ten-year reunion, and of course all I can think is: what’s going to happen if, or when, I see him?

I’ve been thinking about it so much that I’ve had two separate dreams about him this week. neither was particularly salacious, but both did involve me still having...feelings for him.

I’m sitting in my dad’s car in the parking lot, staring out the front window at the trees in front of me. what if I see him and he makes it weird? what if I see him and I make it weird? what if I see him and he’s ugly now? what if I see him and I fall for him all over again?

“no,” I say aloud. “it’s going to be fine. whatever happens, you’re over it. and besides, he probably won’t even show up. it’s not like he ever had much school spirit, or even that many close friends here.”

I get out of the car and walk up the driveway towards the main entrance, and, of course, the first person I see, about fifty feet ahead of me, is Eric.

granted, I haven’t seen him in ten years, except occasionally on social media, but it has to be him: no-one else in our class ever had that windswept — fuck it, that’s the only word for it — blond hair.

“well,” I say to myself, “here we go.”

I slow down, hoping maybe he won’t notice me at all, but he stops in front of the doors and turns around to look around. and spots me. he stares at me for a few seconds, trying to place me, then — smiles? oh, fuck.

“hey, Henry!”

“hey, Eric.” I can’t stop, or run away — which is basically what I did after I asked him out — so I have to just... keep walking towards him. I manage to smile back; my heart is pounding. well, at least I’ll get it out of the way early...

“long time no see,” he says when I get closer. to my surprise, once I’m close enough he reaches out and pulls me into a bro hug, giving me a hearty thump on the back. I’m too surprised to respond in kind. when he lets me go he asks, “how’ve you been, man?”

“uh. okay.” how am I supposed to react in this situation? “just busy with work.”

“ha, yeah.” he grins. “I know the feeling. it’s good to see you, man. glad you could make it this time around.”

for a second I’m not sure what he means, then I figure it out: I missed our five-year reunion because I was traveling. “ah, yeah; I wish I could have made it, but...”

“well, you’re here now,” he says. he pulls open the door and gestures for me to go inside first. then we turn right, following the WELCOME ALMUMNI! signs towards the arts center lobby, where the reception is — by the sound of it — already underway.

fortunately once we get there we’re both immediately pulled in different directions by other friends, but before we separate he flashes me another grin and says, “we’ll catch up later.”

what the fuck is that supposed to mean? I heard reunions are weird but this is a totally different level from what I expected.

still, the reception goes on, and as it does I relax a bit. it’s nice to see people again, although repeating my post-high school life story twenty times gets old pretty fast.

it’s also nice to see how people have grown into themselves — a bunch of the guys I thought were hot in high school are even more so, and even some guys I thought were ordinary-looking ten years ago are really working for me now. it was too bad my best friend couldn’t make it — it would have been nice to admire the eye candy with my one gay friend from high school. oh, well.

after a while I excuse myself from a conversation with some friends from Model UN and head to the bathroom. as I turn the corner around the wall separating the men’s room door from the stall and urinals I stop abruptly: Eric is standing at the left urinal, and I can hear a stream of piss hitting the ceramic basin.

he glances over his shoulder at the sound of the door and grins when he sees me standing there. “hey!”

“...hey.” I hesitate. there are only two urinals, with no divider between them; I’m not sure I can handle being so close to him in such an... intimate context.

my confusion must be showing on my face, because when he looks at me again — probably to figure out why I’m not moving — he says, “everything okay?”

“what? oh. yeah, I’m fine,” I say. “just...need to...”

“well, the other one’s all yours,” he says, jerking his chin at it. “don’t let me stop you.”

I don’t have a choice now, so I step up to the urinal on the right, pull my zipper down, and rich in to pull my dick out. I really do have to pee — I was so frazzled after running into him that I drank a glass of ginger ale and two glasses of water. but while he’s standing right there...

I’m trying not to look at him, or think about the fact that his cock is about three feet to my left, within easy reach, or look down at my own cock, which I can feel growing just from thinking about all of this. but staring directly ahead isn’t helping, and neither is the fact that Eric is still standing there, even though — by the sound of it — he’s done pissing.

I shift awkwardly on my feet, hoping he’ll just leave, but he still doesn’t. finally I dare a glance over at him. it’s supposed to be just a quick one, out of the corner of my eye, but it turns into a stare instead. he’s taken half a step back from the urinal now, but instead of tucking himself back into his underwear and leaving he’s...stroking himself, slowly, languidly. my eyes are instantly glued to his hard cock.

and, of course, he notices: “ha, I knew it. like what you see?”

I turn away quickly but I can feel my cheeks burning.

“it’s okay, man,” he says. “I don’t mind if you look.” I glance back over at him and he’s looking directly back at me. I meet his eyes and he smiles. “you can even do more than look, if you want.”

my mouth is suddenly dry. “w-what?”

“dude,” he says, “did you think I forgot about what happened senior year? it’s cool. I told you I don’t mind.”

cautiously, I look down, away from his face, down towards his dick, which he’s still casually stroking. it’s thick — really thick. longer than mine, although not the longest I’ve ever seen. cut, with a nice slightly flared head. neatly trimmed blond fuzz around the base. I swallow. I want it in my mouth. or more...

“touch it,” he says. he lets his hand drop away; his cock jumps, and I can see a drop of something — probably piss, but who knows? maybe precum — gathering at the tip. “I can tell you want to.” he nods down at my dick, which is most of the way hard now. then he adds: “I want you to.”

with difficulty I manage to tear my eyes away from it so I can look up at his face. he’s got that same cocky, relaxed smile that I loved in high school.

“...a-are you...sure?” thank god I’m twenty-eight now, because if I were still eighteen I’m sure my voice would have cracked on the question. instead I just sound like what I am: excited and terrified.

he laughs. “dude. do you want it or not?”

“...I do.”

“go on, then.”

I swallow again and reach slowly over to wrap my hand around his dick. obviously I can see how thick it is, but it’s still different to feel the heft of it in my hand. “...holy shit.”

he laughs again. “I get that a lot.”

“it’s huge!”

“yup.” he says it without conceit — just a simple statement of fact. still, I look down at myself: being so close to his cock really drives home just how average my own is. I shake my head.

“wow.”

“it’s not even hard yet, really,” he says, and this time he sounds a little smug. “play with it a bit and you’ll see — or better yet...” he leans over, causing my breath to hitch and my heart so skip a beat, and then he whispers seductively — not a word I thought I’d ever apply to Eric Brennan — in my ear: “why don’t we go somewhere a little more private and you can see exactly what I’ve got.”

I swallow again and my dick jumps. “yes, please.”

louder, he says, “good.” he reaches over and pats me on the back, then — with a moment’s difficulty — tucks himself back into his pants and zips up. “meet you in the foyer in ten minutes.” and then, softer again, he adds, “so you’ve got time to calm down and piss.” he nods down at me. “looks like it may take a few minutes.”

“o-okay,” I say.

then he turns and leaves, stopping only for a few seconds at the sink to quickly rinse his hands and dry them.

“what the fuck,” I whisper aloud to myself.

it does, in fact, take me a few minutes to calm down enough that I can actually empty my bladder, but finally I manage it. thankfully nobody else comes in. when I go back out into the arts center lobby I scan the room quickly and don’t see him.

I could rejoin my friends for a few minutes, but then I just have to think of another excuse to leave, so...

I head down the hall, back towards the foyer by the main entrance, although it looks totally different than it did when we were students. my heart is racing and my stomach is fluttering, and part of me thinks maybe I hallucinated the whole thing and he won’t be there. I’ve never been cruised like that before, and for it to be a guy as hot as he is...?

but there he is, leaning on one of the support columns because the benches the popular kids — of which neither of us was one — used to hang out on have been removed. he smiles when he sees me; somehow it’s even more charming every time.

“hey,” he says.

“hey.”

“come on,” he says. “follow me.”

“where to?” I ask, but I follow him even before he answers, down the hall towards the stairwell.

“wrestling locker room,” he says, turning to grin quickly at me over his shoulder. “no lock and nobody ever goes in there in the off-season.”

“unless they added a lock in the last ten years,” I say.

“nope!” he grins again. “I checked earlier — as soon as I saw you I figured I might need it.”

what does that mean? is he bi now, or just horny, or what?

“I used to jack off in there all the time back in the day,” he says, leading me down the stairwell to the basement, and then down another hall and through the swinging door — which, sure enough, has no lock — into a dark room. he flicks on the light and reveals a small locker room.

“I’ve never actually been in here,” I say. “sounds like maybe I should have stopped by sometimes when we were still in high school.”

he laughs. “you’d have gotten an eyeful, for sure.”

“and maybe more?” I ask, raising an eyebrow.

“eh, probably not back then,” he says. “although, maybe if I was high...” he shrugs. “anyway.” he cups his — now that I’m looking at it — very obvious bulge through the khaki shorts he’s wearing. “better start making up for lost time.”

I don’t need to be told twice. I step closer to him and kneel; I hesitate for a moment and look up at him, and when he nods I lean forward and press my nose against his bulge.

“there you go.”

he undoes his belt as I nuzzle his bulge, following the line of his cock with my mouth; as he tries to open the fly the metal buckle knocks me on the forehead, and I pull away for a second. “ow.”

“oops, sorry, man.”

“it’s okay.” and I really don’t mind, because he’s undone the button and unzipped his fly and is stepping out of his shoes and then his shorts. he reaches for the waistband of his boxers (of course), which are beautifully tented, but I stop him. “wait a second.”

I reach up to grab his cock, stroking it a few times through the fabric, then lean forward to take the tip in my mouth, enjoying the musky smell of sweat and skin and marveling, still, at the size of his shaft — and the head.

“mm, fuck,” he says. “never would have thought you’d be such a tease.”

I look up at him and wink. “just wait till I get going.”

he’s right, though — I’ve waited ten years for this, and I think I deserve it. I could pull it out through the fly, but I want full access, and I really want to see his balls. so, grinning up at him, I tug on the waistband and pull his boxers down. his cock springs up and whacks me on the cheek.

“sorry,” he says, although he doesn’t sound it.

“don’t be,” I say, glancing up at him. “I like that.”

“oh, yeah?” he was already smiling, but his grin definitely widens. “you like getting cockslapped?” he grabs the base of his cock and obligingly slaps it against my cheek again. “like that?”

“yes, please.”

he does it again, and then I turn and try to catch the tip in my mouth. I miss on the first try, of course, but he gets the message and helpfully guides it in. I run my tongue around the head and then over the slit, then start to bob my head on it, slowly — I have to go slowly to make sure I can keep my teeth out of the way — taking a little more in my mouth each time.

“shit, yeah.” he thrust forward a bit, the head brushing against the roof of my mouth and then sliding further in — and then further, as he puts his hands on either side of my head and pulls me down further, making me gag and swallow frantically. “fu-u-uck, yes, that’s good.”

I make a kind of strangled gulping noise and he laughs and lets me go.

“fuck,” I say, gasping. “that was hot.”

“yeah, it was,” he agrees. “I had a feeling you’d be good at sucking dick.” I look up at him and grin; he grins back.

“I like getting facefucked,” I say. “if you want to...”

“hell, yeah, man,” he says. “just let me know when you’re ready.”

I take another few deep breaths to steady myself, close my eyes for a second, then say, “I’m ready.”

“then open wide!”

I do, and a second later he’s sliding his cock into my mouth again, his hand on the back of my head again as he starts to fuck in and out of my mouth. he’s pulling far enough back that I can breathe in little spurts, in-in-in-in-in, out-out-out-out-out...

“that’s so good, man; fuck!”

“mghml!”

finally I have to pull away so I can take a real breath; I fall back a bit, gasping, and he immediately starts to stroke himself as he looks down at me in what I think I can fairly call “awe”.

“shit, dude,” he says. “you’re amazing at that.”

“thanks,” I say, still panting. I don’t want to waste even a second of this, though — I lean forward and he takes his hand away, but instead I aim lower, first pressing my nose against his balls and inhaling deeply, enjoying his musky, sweaty scent. then I open my mouth and take his balls in my mouth, first one at a time and then both at once, rolling them on my tongue and tugging gently at them.

“you like that, huh?” he laughs again.

“mhm!”

“feels good.” he starts stroking his cock again; when I open my eyes I see him looking intently down at me. I release his balls for a second and grin up at him; he smiles back. then I get back to it.

once I’ve caught my breath I let his balls go and get back to work on his cock, but slower now, alternating between focusing on the head and doing my best to deepthroat him. he seems content to let me work, occasionally thrusting his hips forward to help with the deepthroating, but otherwise just letting me go at my own pace, offering an occasional “yeah” and “fuck, that’s good” by way of encouragement.

as much as I’m really enjoying his cock, I’m conscious of the fact that eventually I — we — will need to get back to the reception, so I start to speed up a bit. he seems to like this, because he puts his hand on the back of my head, urging me to go faster.

“I’m getting close,” he says after a while, his voice now almost a growl.

I pull back for a moment, jacking him off quickly while I look up at him. “want to cum on my face?”

he looks down at me in surprise. “yeah?”

“please?”

he grins. “alright. suck it a little more, then — I’ll tell you when.”

I’m happy to obey, wrapping my hand around his shaft and stroking him while I focus on the head with my mouth and tongue. I’m getting sloppy, my hand and his cock slick with spit, and by the sounds he’s making it seems like this is working for him. it’s not long before he says: “fuck, here it comes!”

I pull away quickly and position myself appropriately, looking up at him, mouth open, waiting; he grabs the shaft with his own hand, gives it a few last strokes, and then his hips buck forward and the first spurt of cum lands on my left cheek. I close my eyes quickly, but fortunately the rest of his load ends up either on my forehead, on my cheek, or in my mouth, not in my eye. once I think I’m safe I open my eyes again, lean forward and take him in my mouth, working my way slowly up the shaft to make sure I get every last drop. finally he shudders one last time and then pulls away. his cock is glistening. I look up at him and very carefully lick my lips, but he’s got his head thrown back and is staring up at the ceiling, breathing hard.

“thanks, man,” he says, when his breathing has calmed down a bit. he tucks himself back into his pants, pats his bulge, satisfied, then — finally — looks back down at me and flashes that smile again, and I can’t help but smile back; I feel a drop of his cum dripping down my cheek. “I needed that.”

“a-any time,” I say, still a little dazed.

“see you in five years, I hope,” he says. he walks towards the door, then stops and turns back. “actually. how long are you in town for?”

“um.” I blink. “till Wednesday.”

“cool,” he says. “I head back on Tuesday. I’m staying at a hotel downtown — maybe you can stop by sometime.”

“I’d like that.” I give him my number and feel my phone buzz in my pocket.

“hope to see you before I leave,” he says. “you probably should clean up before you go back upstairs, by the way.” he laughs, and then he’s gone, the door swinging shut behind him.

belatedly I look around for something to clean the cum off my face. once I’ve checked myself in the mirror and made sure there’s no sign of anything, I head back upstairs. I pass him talking to a few of our classmates at the front of the reception and he turns to the side to grin at me for a moment, then gets back to his conversation.

it took a while to get to the payoff, I think, but maybe my high school regrets were worth it after all.