Chapter 13
My hips squirm under him as he finally presses his finger in, unsure if I should move towards or away from the intrusion. Eventually, he works himself up to the knuckle, pressing his finger against my walls as if testing the stretch.
It doesn’t seem very stretchy to me, honestly. How was this supposed to work? Isn’t there supposed to be stuff you need to do before anal?
I remember reading somewhere that two raccoons can fit up a person’s ass, and Colten’s dick didn’t seem to be as big as two raccoons, so it’s probably fine?
I try to think, but nothing else really sticks past the feeling of Colten’s finger in me. It's pressed against me, working inside of a very vulnerable spot I’ve never thought much about.
Currently, it’s all I can think about.
“Dry…” Colten mutters before taking his hand out of that space between my legs. I have a moment to catch my breath before he’s scooping up the cum on my twitching dick and going back in, his finger now slick and sliding in deep with ease.
Yeah, that’s, hm! He’s so smart! I knew I could trust him.
Especially when his finger slides in further, much further than before, the path slick with my own spend, before curling and—
“Aaaahhh!” I let out a breathy moan, my dick quickly filling back up even as it spasms from over-sensitivity.
“That,” Colten starts, watching me as his finger continues to rub against that spot, clear excitement in his eyes as he makes me writhe, my hips bucking just from one finger, “is your prostate.”
“Gaahh,” I reply with my whole heart.
There’s some drool dripping down my chin, but I can’t bring myself to care, not when Colten keeps pressing that darn prostate thing! Some pre-cum dribbles from me even though my dick isn’t even fully hard yet.
Jesus Christ, why did no one warn me about the prostate? That’s amazing!
“Feels good?” Colten asks smugly, finally letting me breathe as he pulls his finger away from that one spot, instead working deeper.
I’m still twitching, my body sparkling with fissures of pleasure at each twitch.
I finally open my eyes, though I don’t remember closing them, and notice just how bright it is around us.
I’m breathing hard, too hard, and my eyes are stinging from how bright it is.
Reaching up, I finally tear off the blanket around us. Sweet, fresh air rushes in and cools down the sweat covering my body.
I fling the blanket aside and suck in a deep breath. The glow between us immediately floods the room, casting long shadows that shift and stretch with every movement.
I wiggle my foot, fascinated as its glow sends a nearby table's shadow dancing across the floor.
Colten also breathes in deep, his finger pausing as he takes a moment to enjoy not breathing in hot, recycled air.
“Good idea,” Colten murmurs before dipping down and capturing my lips. His finger also resumes moving, pushing further into me while avoiding my prostate.
As my body heats up again, he pulls his finger back before squeezing in another alongside it. It’s a lot, more than it should be with just two fingers, or at least more than I think it should be.
Colten doesn't rush me. He keeps his movements slow and deliberate, waiting until my body adjusts before adding another. By then, I'm so focused on the steady pressure that I barely notice the change.
As good as it feels, though, I quickly realize he's not actually trying to make me feel good. He’s preparing me, which is apparently different.
I squirm under him, trying to get his fingers to brush against that spot again, but his free arm settles firmly across my hips, pinning me in place with effortless strength. Darn it.
“Behave,” Colten warns. I roll my eyes and let out the most dramatic sigh I can manage.
In retaliation, the asshole bites my pec.
“OW!” I yelp, trying to escape his sharp teeth, but he still has that steel bar of an arm on my hips.
“You know what Coach says,” Colten says when he finally releases me and shoots me a cocky grin. “There’s no place for attitude on the field.”
Then he licks my pec, right over where he bit me, as if that will make up for it. It kind of does.
“Why are you talking about Coach right now?” I groan before realizing that, hey, my hands are finally free, and then proceed to tackle Colten.
Colten is not prepared for that at all, so I have the element of surprise on my side. I roll Colten over, his fingers sadly falling out, but more importantly—I finally have a chance at beating Colten!
My hands wrap around his arms, pinning them to his sides as I press my body weight against him, reversing our positions.
I grin, victory singing in my veins, as Colten struggles unsuccessfully in my hold. I weigh quite a bit more than him, and the soft mattress doesn’t give him much leverage.
“Your winning streak ends now, Freeman!” I laugh, holding him down as I shoot him a smug, cocky, and victorious grin. Colten looks half annoyed and half impressed, his mouth twitching as if holding himself back from laughing with me.
“Proud of yourself, Farmboy?” he asks, finally giving up his struggle beneath me.
I preen at him before nodding. “I knew I would get you one day. Now, you just need to admit I won—”
Somehow, while he was struggling, he'd worked one of his legs between mine without me even noticing.
At least, not until it presses right up against where my cock is still hard and heavy.
My body folds instinctively toward his, chasing the pressure before I can stop myself. Every coherent thought evaporates, replaced by the overwhelming need for more friction.
Colten doesn’t waste his opening.
While I'm distracted, grinding shamelessly against his leg, his other leg snakes between mine. Before I realize what's happening, he's slipped free of my hold and rolled us over.
A second later, my face is buried in the mattress with Colten stretched over my back.
My hips instinctively rock against the sheets, the rough drag of the fabric teasing rather than satisfying.
That familiar swoop I feel whenever Colten pins me during our wrestling crashes through me so hard I can’t hold back a moan as I arch my back under him. He has my arms held behind my back, forcing my face against the bedsheets.
“Looks like I get to keep my streak,” Colten says, the smug asshole.
Before I can retort, he pushes his hips up against my ass, and oh—my mind fills with static as I feel his bare dick rub between my cheeks, the hot, swollen head dragging right up and down against my twitching, empty hole.
A dizzying wave of need crashes over me so suddenly I have to squeeze my eyes shut just to keep from cumming right there and then.
He isn’t even inside of me yet, but just feeling him rub against me, the weight and heat of his dick searing into my own skin, so close to just slipping in…
"Please," I breathe, pushing back against him before the word tumbles out again. "Please, Colten."
“Please, what?” Colten, the absolute asshole, asks.
He drags his dick extra slow right over the opening, before grinding his head against my hole, but never hard enough to actually enter. He just keeps pushing against it, slipping past it over and over again in a taunting, frustrating rhythm.
“Please fuck me!” I beg, straining against his hold as I push back against him, trying to get him to finally slip inside me and fill me up.
“Well, since you asked so nicely,” he drawls, leaning forward, his dick tightly tucked between my cheeks, before pulling back and raising my hips up to place a pillow underneath.
Despite my dick being hard enough to score from the halfway line, my face still burns at having my ass presented, propped up and open for Colten.
Embarrassing…but not embarrassing enough to stop.
Until he leaves the bed entirely.
“What are you doing?” I ask, holding myself back from tackling him and forcing him back into bed with me.
He squats over his luggage, rummaging through it. “Cum isn’t a real substitute for lube, especially not for a virgin.”
“You have lube?” I ask, curious. He brought lube with him? Did he expect we would go this far?
“I have an extensive first aid kit,” he says, standing up and holding up a packet of lube.
“...Why is that even in a first aid kit? That’s weird.”
“I’ve always stocked some in there since freshman year to make sure everyone stays safe,” Colten says before climbing back on the bed and behind me. “You’ll thank me in about thirty seconds.”
That makes a shiver go down my back, especially as I hear the sound of paper ripping. His hand then pulls my ass cheek open, exposing my stretched out hole.
I can hear him hiss, and I look back to see him slather the lube over his dick. I think about laughing at his annoyed expression, as he’s clearly not enjoying how cold the lube is, but manfully resist.
I forget all about his silly expression when he pushes forward just enough for the head of his lube-covered dick to finally slip in.
We both groan as he stretches me even wider than his fingers, my body shaking as I both want to push closer to him, or press away from what I begged for.
I end up staying where I am, shaking as Colten slowly pushes himself in, bit by bit, slowly filling me with the heavy heat of his dick.
I feel like I’m coming apart at the seams, experiencing the most strangely arousing feeling of my life while also questioning if this is really happening.
Colten, my best friend, the man I have depended on again and again for the last three years, is grunting next to my ear as he feeds his hard dick into me, forcing my body to accommodate him in every way.
It’s too much. It’s everything. It’s suddenly hitting me that this is a line we haven’t crossed yet, but one that will never be uncrossed.
We’ve been friends and roommates for years. We’ve learned how to exist around each other, patiently figuring out how to fit into each other’s lives until it became second nature.
Until my life didn't feel right without him beside me.
But this is different, bigger. Too much and not enough all at once. My thoughts won’t settle, and my chest is too tight, like I can’t quite contain everything I’m feeling.