I was chatting online this weekend, and started flirting with a guy who will be known as the Cool Kid, as his screen name implied just how cool he was. After a short little conversation, late on a Saturday night, I made the conscious decision that, you know, masturbation is losing its fun, I’m fucking breaking, if not broken, and when he asked if I would like to head over to his place to "watch a movie" I threw all caution to the wind and agreed. "Watch a movie" being the "Wanna come up to my place for a cup of coffee" for the college crowd. Sure, he had roommates, and didn’t have a TV in his bedroom yet (he’s subletting and just moved in a few days earlier) but what’s a few details?
I walked over to his place, conveniently located across the street from our favorite liquor store. I called when I was across the street, and he met me in the lobby to let me in. A little shorter than his picture led me to believe (I often don’t really realize my own height, and so I didn’t think much of my 6'2" to his 5'9") but still cute and weight proportionate. He’s half-Hawaiian, tan skin, dark hair, perpetual 5 o’clock shadow, dark eyes, and comes up to my shoulder.
His building is this massive, oppressive apartment building; with security that beats anything I’d ever seen. Not only were there cameras everywhere, on the porch, in the lobby, in the hallways, in the elevator, but channels 100-120 allowed anyone in the building to see who was around, who was drunk and passing out, who was bringing up a boy he met online up to his room for a late-night bout of hootchi-cootchi.
Up the elevator to his apartment. Pretty standard chit-chat, mostly about how it was drizzling out and he felt bad that I had to walk the few blocks to his place, and me shrugging it off, saying that bumping into random, festively drunk people on a Saturday night amused me enough to make up for it. Then explaining why I was home alone and online on a Saturday (one of my best friends had some friends from home visiting for the weekend, and I didn’t get along with them, so I politely excused myself from hitting the bars with them) and then why he was home alone (he got home from a long day of waiting on tables and wasn’t in the mood to hit the bars). My lips feel dry but I think it would feel too weird and forward of me to be putting on chapstick.
In his room, same room number as mine (first coincidence of the night). A pretty nice place, lots of foliage for a place with one straight-acting gay guy and three straight guys. A fair amount of cardboard boxes around, mostly empty. Pretty swanky place, overall. To the left, down the hall, last door. An awkwardly shaped room, lots of angles, only one 90*. Three alcoves, if such a thing is possible. Double bed, with a body pillow (have I told you how much I love body pillows?), an empty tv stand, a boombox on the dressers, lightly playing the local college station, a desk with books piled on top, with a desk light on and facing the wall, two candles lit (possibly vanilla), and a butterfly chair with some clothing piled haphazardly.
Continuing with the small talk. I take off my jacket and throw it on the butterfly chair, take off my ring and watch and stick them in my jeans pocket, and kick off my shoes. CoolKid sits on the bed, and I follow. He's an accounting major, all right brain. He doesn’t like going to the gay clubs either. He grew up in the small town where I went to school my freshman year before I transferred, and moved to a suburb of my hometown, working at my mall throughout high school. He’s a transfer student too, 24 years old, and graduating in a few months. He’s taken a few semesters off due to a family emergency and to make money. I brag about how I don’t have classes on Wednesdays and Fridays, mostly because I try and bring it up in every conversation and rub it into everyone else’s face. We’re sitting on the bed, and I scoot back on the bed, and we lie down together, on our sides, continuing our conversation. We still haven’t touched.
We have a few friends in common. Acquaintances, really, including one who just found out he was HIV+ the day earlier. We both felt kinda awkward since neither of us liked him, but still. Silence, and the specter of AIDS. Some crappy song came on the radio, and we talked about that. I lean towards him more, and let my knee rest against his. He mentions how he still feels kind of grimy, even though he took a shower after work. I reach over and run my fingers through his hair, saying he looked fine. He leans in, I lean in, mouths touch, tongues explore, except that explore is a dumb word to use in this situation. Soft lips, tasting of chapstick.
He rolls on top, the body pillow buffering us from the wall. We roll again, still kissing, deeply but not forcefully. His hands up my shirt, the small of my back. My hand still at his head, the other around this back. My hand reaches around, and up his shirt to his somewhat defined, hairless chest. He runs his hands on my jeans, tracing my outer then inner thighs. We’re still kissing. He reaches his hands up, and starts to lift up my shirt. Our kiss breaks for the first time, and I pull off my shirt while he helps somewhat, or at least tries to help. I throw my gray sweatshirt off the foot of the bed, then start to pull his red tshirt over his head, making him sit up in order to get it off. We kiss some more, my chesthair probably feeling scratchy against his chest.
Our hands explore downward. We unbutton buttons, we unzip flies. CoolKid tugs on my jeans, and I get up, stand at the foot of the bed, and let my jeans fall to my ankles, and step out of them as I grab his denim and start to pull, making his hips up to let the denim pass. He’s wearing grey boxers, I’m wearing grey trunks. As I pull off his jeans, I grab one of his socks and rip it off his foot, then take off his other sock, while I do that cool little thing taking off my socks without using my hands, sliding my toe between the elastic band and my hairy calves, sliding off one sock, then the other. I run my hands up his legs, under his boxers slightly but never touching his cock, climbing back onto the bed, on top of him. Dry humping, thrusting, kissing more. My right hand on his nipple, twiddling. I don’t really think he particularly likes this, but whatever. CoolKid grabs my ass as we frot, grinding our cocks together though the thin fabrics. He takes off my underwear first, and then I his. I don’t really take a look at his cock yet. We’re still dry humping, now cock to cock directly, stomach to stomach, chest to chest, legs somewhat intertwined.
I kiss my way down his body, spending more time on his nipple than I probably should, to his shaved cock. I prefer body hair, in all honesty. Too much attention to that sort of stuff just makes me feel uncomfortable. Trimming is fine, encouraged, even, but a shaved pubic reason always feels weird.
And his cock. Thick, uncut, or possibly cut with a bit left over. CoolKid’s is the first guy I’ve slept with with a cock as thick as mine, if not maybe a bit thicker. Not much foreskin, to the point where even now I’m not really sure if it was a sloppy circumcision or what. Big curve to it. We’re talking banana, 120* angle, give or take. (Later, he’ll tell me how he’s never been able to top a guy successfully, he’s either too thick, or can only slip it in an inch or two before the anal cavity doesn’t bend in ways to let his cock fully in.) Incredibly awkward to suck, but I manage. Not quite deep-throating, but I do my best.
I kiss my way up, and let him taste his precum on my lips and tongue. I roll off him, he slightly pushing me, as he makes his way down to reciprocate. Very nice. He comes back up, and we kiss, letting me taste my own precum. I get one of my pubic hairs in my mouth. I pull off of him, fish it out with my tongue, and protract it with my fingers. I show him, he’s only able to see it barely in the dimmed bedroom, and we giggle.
I kiss my way down again, this time putting my body at a t, hoping that this position will make sucking his cock easier. It doesn’t; the curve is still too awkward, too sharp an angle to glide down the throat easily. He runs his hands on my thighs, but is unable to grab my cock. After a minute or two, I get on all fours over him, my knees and calves somewhat cramped against the wall as my cock dangles over his mouth. We sixty-nine for a bit. I’m a bit too tall for this to work successfully, so I play with his taint and balls. (I think rimming is kind of gross.)
CoolKid’s got skills, he’s able to deepthroat and more, his lips extending over, grabbing some pubes, his nose pushing deep into my balls. It’s amazing. I give up on his cock, and just watch him go to town, grabbing more and more of mine. I lean up and straddle his face, amazed at his abilities. He starts to gag, taps my thigh a few times and I pull up. My cock never leaves his mouth, though, just a few seconds on the head before he pushes his head up and forward for more. Damn he’s good.
I lean down again, playing with his cock more, slipping my fingers down, tracing his ring, pushing gently against it. He’s really into it, letting my cock escape from his lips and starts grunting in a high-pitch. I climb off him, and start stroking his cock and playing with his taint. I align ourselves missionary again, and we dry-hump, this time my cock between his legs, poking at his scrotum as we hump (I am about 6 inches taller than him, after all.)
He whispers "One sec" and rolls over, scrounging under the bed. He can’t find his lube. He sits up and grabs his boxers. "I think my roommate has some in his bathroom. He’s asleep, let me go check." And he does, boxerclad, leaving the door slightly ajar as he leaves.
I try and position myself sexily, but in the end all I can think of is how much fun I’m having, and how... comfortable this all is. I don’t want to say that this feels ‘safe’ or like ‘home’ or anything dumb like that but it definitely feels...comfortable.
He returns, and I squirt some on my hands, and finger him for a while. One finger in, and he’s contorting. Gasps, little uh-huhs, little ohs. It’s been a while since I’ve had sex so I can’t be sure how accurate my gage is, but it feels tight. I try slipping in a second finger, and fail. I twist my hand around, feeling his ring expand and contract around my finger. I slip in my middle finger, and this time it works. I wish I would have cut my fingernails beforehand, but he doesn’t say anything, so I’m hoping it wasn’t a problem.
I remove my fingers, and squirt more lube in my hand, and stroke my cock, mixing the precum with the lube, which has a slight warming sensation.
“Do you want to wear something?”
“Huh? Oh yeah—I just usually put lube on first. Feels better.”
He rolls over and searches under his bed again. He pulls up a condom.
“I don’t think I have any extra-larges. Is just a regular ok?”
I say I’ve never tried an extra-large, so it should be no problem. I’m grinning like a motherfucker, because, well, it’s awesome that he thought I needed to use extra-larges.
I hate putting on condoms, if only because my hands are usually all lubey, but I’m able to rip it open with my teeth and slide on the condom. I squirt more lube in my hands, and apply liberally to my condomed cock. I rub the rest on his cock, stroking gently, getting him ready.
I lift his legs, and ready myself, only to find that I’m starting to go soft. Not completely soft, but after pressing against his hole I’m not rigid enough to get inside him. Fuck fuck fuck fuck fuck panic mode sets in. Sure, it may happen to all men, but it doesn’t happen to me goddamnit motherfuck.
With his legs on my shoulders I start stroking, thinking of anything, of CoolKid, of Jake Gyllenhaal, of the videoclip of a really hot facial I downloaded the day earlier, anything, anything. This is not the way hookups are supposed to go, especially my first one. I’m a good boy. I am owed. This should be a scene right out of the Great Cock Hunt, not a commercial for Cialis. Fuck fuck.
I’m pretty sure he notices. I mean, how could he not? I’m not going to dignify this with words. He clears his throat.
"Maybe we should try a different position." If anything, his voice is warmer.
"Um, how about with me standing?"
"Like I’m standing on the edge of the bed, and you’re at the edge, you know?"
He gets onto his hands and knees, his shins dangling off the side of the bed.
I get up, and stand at the ready. Even though it’s pretty dark in his room, lit only by a few candles and a lamp that’s pointed directly at the wall, I can still tell that this is a wonderful sight.
I’m standing, stroking my cock, starting to worry about the condom sliding off. No response. Jake Gyllenhaal, that hot video of a facial, former sex partners, nothing. I say, "You can get on your back. That’ll work too." I don't want him to get uncomfortable. I think I’m hard enough, and I push between his cheeks, but it keeps sliding around and not able to push through.
I sigh, exasperated, and climb onto the bed, on my back.
"I should’ve looked harder and found an extra large."
"No, I don’t think that’s it. I’ve never used an extra large." I don’t mention how I haven’t fucked a guy in almost 18 months, and how the male penis can keep growing until the age of 25, and I’ve always been somewhat thick, but that’s not relevant. "I don’t know what." I think about saying This has never happened to me before but I don’t. It’s just too dumb-sounding. I don’t want to be that guy.
I’m stroking, I grab more lube, hoping that will work. He straddles my thighs, one of his hands on my balls, the other on one of my nipples. I’m slapping my cock against his legs, gripping the base for a makeshift cock-ring, anything. The condom’s still on, I’ve never gone completely soft, but I’ve never been a good sturdy rock since we started trying.
I’m somewhat hard, and he climbs up and on. No luck. He starts to, I guess dry-hump, letting my cock slide between his legs, pumping at his scrotum, but to no avail. I half-heartedly play with his cock, which has grown flaccid. I sigh, and push him off of me, so that he lies next to me.
"I’m sorry. I just don’t… It just feels..."
"Are you sure it’s not the condom?"
"I’m pretty sure that’s not it. It’s like, I don’t know."
I roll the condom up and crumple it into a small ball and shove it back into its original wrapper, which is lying next to one of his pillows.
"Let’s just worry about you, ok?"
I sit up a bit, and reach my hand over to CoolKid’s groin, slipping past his balls and down to his hole. I tap my finger against his ring, and he doesn’t gasp this time.
I cock my head, and sit up more. I start pushing my finger in, but he’s still just lying there, not really responding. He motions for me to pull out, so I do and lie next to him, both of us staring at his ceiling.
"I’m feeling kind of... numb, I guess, down there." He says after a few seconds of breathing.
"Yeah, me too! That’s the word I was looking for. Something just wasn’t feeling right."
He grabs the lube, stands up, and makes his way to the lamp. He adjusts it, letting more light permeate the room.
"Maintain Desensitizing Lubricant. Blah blah …slightly deadens the nerve endings to give you staying power for all night long."
"Slightly deadens nerve endings?" I sit up as I ask the question.
"Slightly deadens the nerve endings." He sets the lube down on the desk, readjusts the lamp, and comes back to bed. I’m running my hand through my hair, trying to regain some composure, and he lies down, his head on my shoulder, turning his body towards mine. I extend my arm out, and wrap it around him. The nook.
He’s in the nook. He’s in my nook. He’s in my nook! I fucking love the nook. His head is dangerously close to my heart, we’re breathing in rhythm, his head is floating up and down as I breathe in and out.
I lean my head down, resting my face against the crown of his head. This definitely feels... comfortable. More than it probably should.
I break the silence. "Well, I guess that explains it."
"I’m still kinda embarrassed, though."
"Why should you feel embarrassed? I feel embarrassed. I mean it was my stuff."
"No, it was your roommates. And I still feel dumb." I mean, after all, it was my flaccid cock. I didn’t say that, but I was thinking it pretty audibly.
He yawns. "So what are you doing tomorrow?"
"I dunno. I’ve got some homework I should be doing. A couple hour’s worth."
"Um... I work from 7-3, and then I should probably do some homework too, but nothing that important."
"You have to be at work at 7 AM tomorrow?" I looked over at his alarm clock and it’s almost 3. "I’ll leave and let you get some sleep." I’m pretty embarrassed, but not very tired. I’ve never been the kind of person who has sex and then turns over and falls asleep. I always get a second wind, which more than one former boyfriend has found annoying.
We get out of bed, and try to determine our clothing situation. He finds my socks, and throws them to me. I put on my underwear, and am trying to figure out which pair were my jeans when I realize that he’s getting dressed too.
"Why are you getting dressed? You should go to bed."
"I’ll walk you out."
"Aww… You don’t have to do that." I still grin, though.
"Nah, it’s no problem." Still grinning, and he is too.
I'm dressed before he is, and I make sure that the bathroom is the door right outside his room, to the right. "I just want to wash my hands. They’re still kind of lubey."
I’m washing my hands, looking at myself in the mirror. I’m not crushing on this guy. That’s not the way hookups work. I’m just trying to project a sense of connection to quell any sort of guilt I’m feeling about sleeping with a guy
He walks me out, and I’m still all apologies. I mean, what else can you say when your troops weren’t ready for battle? Sure, it may not be entirely my fault, but still: I saw, but I didn't conquer, and I certainly didn't come. He’s shrugging it off, a perfect gentleman, telling me not to worry about it. I’m suddenly super self-conscious, walking into the elevator and reminded of the cameras, and how everyone in the building could be watching us at that very moment.
We step off the elevator, and walking toward the lobby.
"I’ve got a fair amount of homework to do tomorrow, but if you call me and hang out or something, that'd be cool." I like the way CoolKid thinks. I’ll get a chance to redeem myself, but what’s more, I’ll get to see CoolKid again.
"Yeah, or I’m just doing homework tomorrow. Feel free to call me if you get bored or whatever."
We’re in the front lobby, right outside the doors. I fumble around, and can see three security cameras. I want to kiss him goodbye, and I’m pretty sure he wanted to kiss me goodbye too, but it just felt too weird.
Fortunately, two drunks, a girl in a dress and heels and a fairly unattractive black guy in a suit and corsage, bumped into the front door, the girl trying desperately to fit her key into the lock. She’s failing, miserably. They’re both laughing loudly.
We’re smiling, both smiling, and glad that they broke the tension. He says he’ll see me later, I say sweet dreams. I then open the door for the inebriated couple, and make my way home.
(NB--All artwork by the incomprable Steve Walker
Also, this post is almost 15 pages, double-spaced, in a word document. If you made it all the way through, good for you.)