Believe me, I'm Gay E7 | My straight best friend helps me understand how to bottom (Patreon)

Everyone is over the age of 18

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I feel like bottoming is really the ultimate test of whether one is gay or not, you know? Like anyone can enjoy sucking dick… ok, now that I’ve said that out loud, perhaps not. I mean to say, getting fucked feels like the final boss of finding out what I like as a gay man.  The idea has been sitting in the back of my mind since, well, forever. I have pictured myself on my back or on all fours with someone inside me, but a fantasy is a fantasy. I haven’t even put a finger up there yet. Don’t judge me! I just feel like I wouldn’t be able to figure out the positioning of how to make it all work. 

Before, my only option was to find a stranger to do it for me, and that thought absolutely terrified me. I mean, I can barely make small talk with someone that I’m not familiar with. So, I’m light years away from being comfortable enough to let them stick something up my butt. 

But now…there’s Kai. Kai, my best friend, who would rather see me experiment safely with him than with randoms. It’s stupid, because I’ve sucked him off twice now, but I still felt silly asking for more.

I mean, he did cum both times, so… he doesn’t hate doing it. Just cause he’s straight doesn’t mean he’ll say no to anal right away.

I bring it up to Kai the next afternoon while we are hanging out in my room after swim practice. He really is the only person I can say this kind of stuff to. “I have been thinking about trying to bottom. Like, actually um … going further than just sucking.” 

Kai, laying flat on his back on the bed and massaging his shoulder, puckers his lips. “That’s getting fucked in the ass, right?”

I nod and rub the back of my neck because the words feel big coming out. “Yeah, but I don’t want to try it for the first time with some Grindr stranger.”

“Yeah, I get that, dude. I wouldn’t do that. Wait, how many fingers do you have to practice with?” He holds up his hand and puts his index and middle finger together. “Hold up, how many fingers is my dick?”

“3.” I say without hesitation.

“Three?!” Kai adds his ring finger. “You telling me you shoved this in your ass?” He turns his body towards mine.

“No!” I know he’s going to tease me for blushing. “Actually, I have never put any fingers in. Not yet anyway.”

He tilts his head and studies my face for a second. “How do you know you’ll like it then?

“I don’t.” Help me? I say in my head.

Kai leans back on his back and crosses his arm. “You want me to put my hand up you? Is that what you're asking?”

“Not a hand!! Just a finger!” 

“I'm kidding, dude. Chill.” He turns back to the side to face me. “If your ass gets as red as your face, you're going to be really popular.” His fingers brush my bangs off my forehead. “Does it?” 

I shrug. How would I know? 

Kai stands up from the bed. “You know how Coach takes videos of us so that we can see our form and change it?”

“Yeah?” I sit up on the bed, and watch him look for his phone. 

“Let's start with doggy.”  He looks more focused on his phone than me.

“I don't get it.” But I trust my friend. I crawl onto the mattress and kneel there feeling exposed even with my shorts still on.

“Arch your back a bit so your ass pops. Yeahh, the creeps are going to love this.” He laughs. 

“What are we doing?” I look over my shoulder at him and see him taking his job as a photographer seriously. 

“I learned in marketing class… that first impressions are everything,” Kai mutters in between snaps. “Okay, take it off. Then, on all fours with the knees wider.”

My hands tremble as I pull my shorts down, and his hands take over to pull them off my ankle. 

“Chest down a little.”

I drop to my elbows and spread my knees until the position feels ridiculous and hot at the same time. Like, my asshole feels totally visible, and I don't think I've felt that before. 

Kai kneels behind me on the bed and angles the phone close. “Cheeks are a little red.”

The phone was on silent, and I don't know how many photos he took. It did feel like it took forever before Kai flopped on the bed next to me.

He shows me the screen after. The close-up is sharp… and embarrassing. My hole looks small and pink, mostly smooth with some dusting of hair lining the sides.

I stare at the photo for a long moment, and can't believe I've never met that part of my body. “Is that… good? 

Kai zooms in and out of the photo. “Oh yeah, this is a nice hole. You can tell it hasn't had much use. I'm surprised. Thought you'd be gaping after you told me you're gay.” 

I shove him in the shoulder, but his sturdy frame doesn't budge at all. He gives me a toothy grin, and I feel my cheeks burn up again. 

“All your cheeks are red now,” he says. I can feel the heat on my ass too as he says it. Kai gets up and checks again. “Yup. Like a tomato.” 

I feel the mattress dip as he settles behind me again. My cock, visibly hard probably, twitches as I feel his presence close to my most vulnerable part. 

“It looks nice and tight.”

His finger pushes on the ring and I flinch. 

“You good, dude?” 

“Yeah.” I settle back in and put my chest down, feeling my cheeks spread wider for him. 

“I don't know about gay dudes, but I'm pretty sure every guy loves something tight.” 

Kai spits into his hand then presses one wet finger against my hole. The pressure is gentle at first, just circling the rim.

“Oh!” Something slips into the relaxed muscle. 

“You okay, Miles?”  He pushes in one knuckle deep then pauses.

I gasp and rock forward without meaning to. My body jerks on the sheets every time he moves. “Fuck. Is that two fingers?”

Kai chuckles low in his throat. “It's one fingertip” I feel him wiggle it in my bum. “You're so tight, dude. It's not going in any further.”

“Ah! Ah!” I twist at the strange feeling in my ass. As much as I want to try, I feel my body resisting the gentle penetration. 

“Alright, this isn't working. You need to stay still for me to get deeper. Lay down?” His finger exits me. 

I flip over and lie flat with my legs spread. Kai climbs up and straddles my chest so his weight pins me down against the mattress. He is undoubtedly heavier than me and the pressure feels grounding.

“Okay, hold your legs. Yup.” 

His ass smells great. 

“Oh… Kai…” The wet finger slips in me again. Any involuntary movement from my upper half is stifled by his weight. 

“Oh yeah, this is better.” His finger pushes along. 

“Oh!” I grip the back of my knees tightly for comfort. 

What is that?

The feeling gets further away as he moves his finger out, but comes back as he pushes it back in. 

“You're hard as a rock.” 

There. Again. “Oh…oh….”

“Going to put another finger in.” My hole cedes to the additional pressure. 

“Oh…” I lift my head and look straight into the back of his shorts. “Oh!” 

“How's that?” I feel him wiggle his fingers independently, and I crunch so far up that my nose touches his lower back. “Yeah? Oh damn, your cock is leaking.” 

Yes! I kiss the exposed skin just under his shirt. Yes! 

“Dude, you're leaking so much.” I feel his hand pick my cock up, and I imagine his face as he studies the precum drool. 

I need something in my mouth.

“Can I suck you?” I ask, caught in a horny daze. I kiss his back again, silently begging for my finger fucking. 

Kai lifted his hips just enough to shove his shorts and briefs down. It was a storm of his fabric and legs as he shuffled them off, and I was lost in the wind of his scent. The next thing I felt was his balls on my nose, and his hard cock tip at my lips. 

I open wide and take him in, and give the first suck as he gets back into fingering me. The dual sensation makes my hips buck up off the bed. His finger curls inside me and finds that spot that sends sparks up my spine. I moan around his cock and feel the vibration of my friend’s moans back at me. 

“Dude…” His fingers pause, and his hips move, thrusting himself deep into my willing mouth. “Fuck, Miles.” 

It was a miracle that I didn't gag, but it felt like another mode had switched in my brain. A sort of … face-hole mode. I held onto my legs as he explored the back of my throat easily. 

I felt it when he relaxed into it. It was a signal of him feeling like he's not going to hurt me. His thrusts became more smooth, and they became for him and not for me. 

Kai picks up speed with his hand while pumping into my mouth. His breathing turns rough and uneven, contrary to his thrusts. “Fuck, that feels good. Your throat is so wet today.” His fingers lose their gentle touch, and every couple pokes is laced with a hint of pain. 

I love it. 

Fuck, I love it. 

Kai tenses above me. “Oh fuck, gotta cum. In your mouth?”

“Mmm!” I confirm, feeling his cock inflate further and dying at the excitement of the upcoming taste. 

“You sure? Oh!” 

“GUH!” The spurt of liquid activates my gag reflex. He pulls out and I chase him, not wanting to lose any cum. 

“Fuck, Miles!” He holds steady as I milk his thick cock. His fingers go back to fucking me, and I go crazy on his dick. “Ah! Ah!” 

“MMMM!” His finger hits this one spot that makes me feel like I'm going to explode.

And I do!

“AhHHH!!!”

I shoot hard, bucking my hips. The feeling of cumming handsfree is so unique and unfamiliar that my body doesn't know how to react. I want to fuck something but there’s nothing to fuck. It’s just coming out of me in jets.

“Fuck! Dude! Ah!” I feel him pull his face back. His gooey dick is pushed deeper inside my mouth and then lifts off me as he sits back on his knees. “Fuck, man. You didn’t have to do all that.” 

Oh… he's covered. One of his eyes is closed with my cum on it, and some of my jizz hangs off his chin. 

“I need something. Fuck, that's burns. Miles!” 

I could barely move. I just laid there shivering as he wiped his face with his shirt. 

“God, I’m never giving a girl a facial again.”