Chapter Text
It’s nine pm on a Friday night, and the house is empty.
Garrett called me thirty minutes ago to tell me that he’d be spending the night in Hannah’s dorm room, and Logan is out with Grace. Dinner with her and her dad, he said. Tucker isn’t here either, but he’s been MIA these past few weeks. At this point I don’t even bother to try to guess what he’s doing.
It’s… weird. A year ago, the place would have been full to the brim with hockey players. Garrett and Logan demolishing a round of ice pro on the TV. Fitzy and the gang in the kitchen, slamming back shitty beer or a round of vodka. And me, laid back on the couch with some puck bunny on my lap, wondering how long it would take the team to notice I was fingering her through her shorts. Everything has changed, and I didn’t even notice.
Maxwell invited me over to Malone’s to grab drinks when I got out of practice, but I told him I was swamped. ECON final.
Well, that’s not totally true. I do have an ECON final, but I would’ve put it off for one more day if it meant I could see Allie again. I pull out my phone and text her.
ME: house empty 2nite. down for a repeat of last week? ;)
ALLIE: UGH
ALLIE: im stuck in rehearsals. director wants 2 stage the big confrontation scene n it’s taken us HOURS. probs b here until midnight :(((
ALLIE: i’ll b thinking abt ur dick the whole time tho
ALLIE: splitting me open…
Fuck. Her words go straight to my cock, as does the memory of last week. Both of us in the bathtub. The spray of the shower hitting my back as I buried my tongue between her legs. Her thighs clamping around my head while I sucked on her clit. Driving the dildo into her, her pussy swallowing it whole, hungry, she was so wet.
Suddenly I’m hard, and I can’t concentrate on whatever my notes say about liquid assets or income tax. Whenever my eyes try to scan the page — and I don’t even know why I try — all I can see is the swell of Allie’s breasts, her nipples impossibly pink and swollen… fuck
I do what I’ve done every time I’ve found myself in this situation. I get up from my desk chair and walk towards my bed, grabbing my waistband on the way. Once I’ve crashed against my pillows, I pull down my sweatpants.
My cock springs free from its confines.
Better to spend five minutes jerking off than three hours trying to work in agony.
I take myself in hand, biting down a groan. Every stroke sends tendrils of pleasure through my body, from the top of my head to the tips of my toes. At first, I work myself slowly, cautiously, sweeping my thumb under the head of my penis just how I know I like it, but soon enough, my hand has picked up the pace. I touch myself in quick, hard strokes which leave me throwing my head back against the pillow and scrunching my eyes.
I’m imagining Allie’s sinful mouth. Some of the girls I’ve been with treat blowjobs like an obligation, sucking me off just because I’ve eaten them out. A quid pro quo. I think it’s a shame that so many guys won’t go down on girls that they feel the need to do that, because you can always tell. Not Allie, though. She sucks dick like she wants it more than you do. Quite the statement, because I really do want it every time.
I think about her tongue running along the underside of my dick, and a moan can’t help wrenching itself out of my chest. In a vain attempt at replicating the heat of her mouth, I rub my hands together and spit on my palms, even though at this point I’m already wet with precum.
My free hand reaches down to cup my balls, and I squeeze around them as I stroke. I move my hand down to my taint, pressing down like some of my hookups have done, and white blooms around the edges of my vision. In my mind, Allie is still bobbing up and down on my cock, little mewls slipping out from her lips. God, Dean, you have the most perfect dick in the whole fucking universe.
At this point I’m almost thrusting up into my hand, I’m so close. Then, my free hand moves even lower...
Let me stick one finger up there and see what happens.
Allie’s voice rings crystal clear, almost like we’re back in that bathtub. My right hand stills. I snatch my left hand away from my butt cheeks like it’s been branded.
I wasn’t lying when I told her I’d never experimented with ass play. Despite my extensive sexual history, I’ve never tried it. Some girls have genuinely offered to do it, but I’ve always told them no. Others have brought up the possibility with a smirk. They sigh in relief when I swat their hands away, and they say, “Oh, thank god you’re not one of those guys.” Whatever that means.
Then, there are the boys, like Logan and his jug of pink lemonade. Every day after he found me in the bathtub with Winston the dildo perched on the porcelain edge, he drinks a glass of it slowly like he’s in some sort of bizarre porno, looking me right in the eye, almost like he’s telling me, “I know what you are.”
I’m not a homophobe, but I don’t want them assuming those things about me. It’s like, there’s always been something degrading about butt play, you know? It’s just never appealed to me. Plus, I like knowing that, despite all the rumors about me — which, by the way, are spread by jealous losers who aren’t up to their knees in pussy like I am — there’s still a line that I won’t cross.
Are you not the least bit curious to know what it feels like?
My mind returns to our conversation last week. One part of me remembers the shame that sprung up inside me when Allie said that, especially when she offered to hook me up with one of her male theater buddies in the same breath. But another part thinks about how good it felt the night when we first hooked up, when I was immobilized on my bed, completely at her mercy. A part of me thinks… that I might go wherever she wants to take me.
And that scares the fuck out of me.
Out of curiosity, I drag my ass back to my desk chair and wake up my iMac. I pull up a familiar website. Scrolling through various pages of thumbnails that set off my Nope!-o-meter, I find out that looks semi-normal and click on it.
In the video, a pale man and a woman are in a living room with a teal blue couch. The woman is a brunette with heavy tits that remind me of Allie’s. The man is sitting on the couch, and I watch as the woman blows him for a minute, her brown hair splayed over the sofa. He lays back with his cock and balls out in the open. I can’t look at him directly — I focus on the actress. Then, her index finger slowly disappears into his asshole.
The actors fade away, and I can only think of me and Allie. What if it was her, sinking her finger into me inch by inch, smoothing her palm over my thigh and encouraging me to take it, just a bit more? What if I was the one who was spread-eagled, taking her as a girl takes a dick? Part of me says no fucking way, but almost without willing it, my asshole clenches at the thought. And I realize the fact of my neglected cock, weeping uselessly onto my thigh.
I grip myself once more, give one stroke, then two, until I’ve got a steady rhythm.
Absent-mindedly I open the top drawer on my desk. Among packs of condoms and Q-Tips I find it: a bottle of lube. Not long ago Garrett had left one just like it on my bed with a note that read, “For your ass.” He didn’t count on the fact that I keep one in my bedroom already just in case. Although I can proudly say that most girls I’ve been with don’t need it.
The lube is cold when I squeeze it onto my fingers. I try to get in a good position on the desk chair, parting my legs slightly while I trail my left hand down my lower back. I cautiously slip my hand between my butt cheeks, getting used to the shock of the lube.
And then I push the very tip of my finger into my asshole.
It feels hot and cold and painful at the same time. My breath cuts out in a sharp inhale. I work my dick with my right hand while I keep my finger in place, knowing fuck-all-what to do with it. After a minute or so, the pain has subsided, but it doesn’t feel pleasurable either.
I try to relax while my finger goes deeper. I remember how the few adventurous girls I’ve tried anal with liked to go slow, and, after a few minutes, with a lot of effort, I’ve got both my index and my middle finger pumping in and out of my asshole. It’s not doing much for me, but the hand working over my dick and the thought of Allie’s slender fingers inside me keep me just interested enough to not give up completely.
The woman on my computer screen is fucking the man with her fingers now, crooking them in a way that makes him erupt in open-mouthed gasps. I figure that’s what I should do, too.
I sweep my finger experimentally, seeking out the bundle of nerves that Allie talked about so lovingly, but the feeling remains the same. Yeah, right. I’m already proving the boys right about my unconventional proclivities, and on top of that, it doesn’t even feel that good.
I’m about to close the porn video in shame when my fingertip rubs against a small bump on the walls of my anus.
The first time I had sex, it had felt like I had discovered an ancient secret or the cure for cancer. It was so unfair that people were walking around and going on with their lives knowing that this kind of pleasure was possible. That those bastards hadn’t even told me.
When I touch that spot in my asshole, a thrill of pleasure races up my spine and a groan erupts from my mouth before I can stop it. My legs kick out from under me and I have to put out my right hand to stabilize myself before I fall off the chair. My dick is throbbing harder than ever. I bear down on my hand, chasing the high that a few seconds ago became an exciting possibility, my finger moving faster and harder.
I imagine myself face-down on my bed. Allie is thrusting into me with her hot pink dildo as her hand reaches around to stroke my dick. I can feel her tits crushed against my back. I can hear her breathy moans against my ear and the occasional praise of her sexed-up voice: You’re so fucking sexy, Dean, so good for me.
My head falls back against the headrest, my mouth forming incoherent words while my mind can only repeat feels good like a fucking mantra. There’s a delicious pressure building somewhere deep in my core as I rub myself. Feels good, feels good, feels good.
Before I know it, the pressure builds and I’m spilling into my hand with a strangled moan. I come for what feels like five minutes, a whole hour for all I care. My eyes are scrunched tight; I’m here and not here and on the ice and in outer space.
Finally, I open my eyes to face reality. I’m in my room. The video is still playing — the woman has moved to fucking the man from behind at a punishing pace that has my asshole stinging in solidarity. My notes are neatly stacked at the edge of the desk, away from the spray of come that has otherwise marred the surface. And I’ve just had the first prostate orgasm of my life.
I clean myself with the box of tissues I keep in my room for that very purpose and slide on my sweatpants. Well, I think, back to studying for ECON. Hope this doesn’t awaken anything in me.
Except my mind is still wandering. And without thinking much about it, I type a few words into a search engine and click on the first article that comes up:
A Beginner’s Guide to Pegging.