The Best Friend

I hate it when girls call me a good guy. When girls say I’m nice, and easy going, when they say I have a good sense of humour, that I’m easy to talk to, when they call me a catch, I fucking hate them. Every guy does when it happens to him. Anyone who’s ever been asked, “How is it possible that a guy like you is still single?” hates the girl who’s asking him. And the reason is simple: because whenever a girl asks you that question, inevitably a single response pops into your head, “If I’m really so great, why aren’t we dating?”

When I was in high school, my best friend was a girl named Ash. In high school, talking to girls is awkward. It’s full of um’s and ah’s and trying to sound witty and cool when you’re neither. It involves trying to hide that crack in your voice, of trying to keep her facing the side of you with less acne, and of trying not to sound like a total loser. But not with Ash.

Ash was my best friend in high school. Ash was the kind of girl I could relax with. I could stop worrying about what to say and just be myself. She was the type of girl you took on bike rides through the woods just cause you were bored. The type of girl who would sneak into R-rated sci-fi movies with you or laugh at your dick jokes. Ash was the type of girl who would beat you at videogames, then shove it in your face and do an annoying victory dance while you sat there emasculated and without retort. Ash was the type of girl who would regularly call you a loser and a bum, while giving you a playful shove and big grin.

She was the girl next door. She was tall and had long black hair which she always wore in a pony tail under a baseball cap. She dressed like she should’ve been your brother, and for some strange reason, seeing this cute, B-cup girl dressed like a boy was an unusual turn on.

Ash was the girl that you get a crush on because you click.

High school was an era of awkwardly timed erections, of wet dreams and constant fantasizing. It was a time when you sometimes walked your bike home because you couldn’t ride a bike with a boner. It was a time when you developed crushes on your teachers based more on their breast size, and less on their attractiveness. High school was the time when you learned how to put on a condom by practicing on a cucumber during the Sex Ed section of Gym class.

Maybe it was the fact that Ash and I fit so well together, that we clicked on some level that I can’t describe, that we were best friends, or then again, maybe it was just the constant hard-ons, but it was around this time of sexual awakening that I started to fantasize about Ash. I started to wonder what would happen if we started dating, if I kissed her, if I married her, but mostly, if I put my penis in her. It was around that point that I got my crush on her.

You see when it comes to teenage boys, there isn’t much difference between having fantasies and feelings for a girl. Mmmm, I would really love to stick my penis in her while she’s wearing a maid’s uniform and bent over my bed. I guess I love her.

So I decided to act.


The night I decided to act, was perhaps the most romantic type of evening one engages in during high school: a sleepover. Sleepovers weren’t too uncommon for Ash and I. I’d often spend the night at her place if we stayed up too late watching movies. And it certainly wasn’t uncommon for us to cuddle up in our pajamas as the night went on.

This particular night, Ash and I were in her basement watching television. We were cuddled up together, my arm around her, her head on my shoulder, blanket over top of us. She was gently rubbing my chest with her hand. I was trying to keep the blankets angled properly to hide my slowly growing woody.

Same ol’ story. Boy meets girl. Girl in short shorts cuddles with boy. Girl gives boy raging hard-on which boy hides under blankets. Boy attempts to fuck girl in parents’ basement.

Lounging on the sofa with her, it feels so right. She’s told me a thousand times how relaxing she finds our time together, how she could just fall asleep in my arms sometimes. And like a barometer reading the sexual tension in the air, my fully erect penis was telling me it was time to stop being a pussy and kiss this girl.

On TV we’re watching some lame, made for TV movie that I haven’t even been paying attention to. Instead, I’ve been working up my courage.

To work up courage the easiest thing a guy can do is literally turn off his brain. My head is running through a thousand scenarios of what will happen when I try to kiss her. She could be disgusted, enthralled, ecstatic, mortified, confused... the list goes on. In the worst scenarios, I’m physically assaulted before she throws me back out onto the street, and in the best scenarios, well... a lot of the same physical acts are occurring, but in passion instead of anger.

I’ve practiced what I’m going to say and do. I’ve thought it all through. All the signs are there, she’s got to like me. Just kiss her and the rest will take care of itself.

I know what to say, what to do, the time is right, perfect even... so stop postponing and just do it!

I take a deep breath, push out any thoughts I have, good or bad, because I know they’ll fuck me up, and I just stare at her for a moment until she finally looks back at me.

Ash looks at me with her soft brown eyes and smiles. “What, loser?”

I smirk at her flirt. “You,” I say.

“Me?” she scoffs.

“Are you staring at me?”

“Maybe,” she jokes.

“Well,” I say coyly. “You’re not allowed to look at me like that without kissing me.”

She laughs and pats my chest then turns back to the TV.

Heart’s beating faster. More blood to south, less to the brain. It’s okay, I don’t need it. Don’t think, just follow through.

“No,” I interrupt her. I reach my free hand over to her cheek and turn her face towards mine, “I’m serious.” I lean forward. Lips pursued, our eyes locked. Closer and closer to the first kiss.

And then... she laughs.

She kisses me on the cheek and turns back to the TV again.

“You’re such a kidder I love it,” she tells me, gaze fixed on the TV. “Could you imagine? Us?” She turns to me and laughs again. “I love that we’re so comfortable that we can even joke about it.”

Just the response I was going for...

I laugh it off, “Yeah that would be crazy...” But on the inside, I’m not laughing. What... the... fuck? I run through the events that have just transpired quickly in my head. Wait, should I still make a move? What does she mean, “Can you imagine? Us?” Man... she liked me though… didn’t she?

In the midst of the confusion, my erection dies.

At least I can stand up again.

She laughs again and tickles me a bit. She starts talking about how we’re both so lucky to have such good friends. Then she retracts a bit and says she doesn’t want to get all mushy. She asks if I have a crush on anyone. I say no. I’m still not really paying attention. She acts surprised, and tells me that she doesn’t understand how I’m still single, how I haven’t met someone yet. I just shrug. I kind of hate her right now, but I’m pretending not to.


One of the unfortunate things about having great female friends is falling for them.

I spend the rest of the night stewing a bit in my own head, trying to figure out what, if anything, I can do. But the conclusion is simple: there’s nothing to be done. She doesn’t like me. She just wants to be my friend.

We talk a bit more, just about fluff, nothing in particular, then it’s time for bed. I brush my teeth and crawl in to the basement bed. She comes out after brushing her teeth and crawls into bed with me.

“I’ll sleep with you here tonight,” she tells me.

“Okay,” I reply on auto-pilot.

“Cuddle with me,” she says. “It’s cold.”

She cuddles into me and we begin to spoon. She pulls my arm around her and holds on to it.

She purrs, “You’re a good friend.”

Just what I wanted...

And then she starts to drift off to sleep.

I on the other hand, lay there, unable to sleep, just thinking. Thinking about us, about, well, not just us. If it’s never going to happen with Ash, well, then I have to move on. I start thinking about other girls in my school. Maybe I should ask one of them to the dance. Kara is cute. Anne’s got a great ass. Oh and Ms. Porter has that naughty librarian thing going on. Ok well not so much but her jugs are huge. Mixed in all of this I’m still thinking about Ash. I mean how can I not?

Fuck! Why just friends? Why doesn’t she like me like that? Ash is cuter than Kara. Ash has a tighter ass than Anne. And so what if she doesn’t have the librarian thing going on, she’s more fun than any other girl I know. I can talk with Ash, I can have fun with her, I can relax with her.

She’s so cute and adorable the way she laughs. And she’s laying beside me in her PJs. She’s laying beside me, in only booty shorts and a t-shirt, my cock pressed... oh shit...

It starts to happen.

Oh fuck... ok, math... what’s 12 X 28?

10 X 28 is 280. Plus 2 X 28 which is 56, so 280 plus 56 gives me... 336... fuck! Too easy! 144 X 513!

I start running through equation after equation.

I start trying to think of dying grandparents and old pets. I think of war and death and dying and anything I possibly can. What do I have to do tomorrow? Saddest movie I’ve ever seen? What homework do I have?

Then images of big tittied teachers and bare naked co-eds start popping into my head.

Fuck, fuck, fuck!

Bigger and bigger it grows. Usually not a problem, but I feel it digging into Ash’s ass already. And that thought makes matters thoroughly worse!

I try to pull back, lean my pelvis back as far as I can, but Ash stirs in her sleep as she feels my arm pulling away.

“No,” she murmurs, “cuddle.” She’s half asleep and doesn’t realize what’s going on. She pulls me back towards her and my dick goes fully erect, it slides out of the scantily buttoned fly on my boxers and right in between her legs, just under her ass.

Her legs tighten a bit, and I realize... I’ve just been trapped!


As I lay there, trapped in some strange sexual wrestling hold, I hear Ash begin to snore. She only does this when she’s really sleeping. And she’s such a heavy sleeper.

I contemplate waking her, but I really don’t know how I’d justify having my cock out and between her legs if I did.

“I just kind of tripped and slipped into your vag.” Yeah… she'd never buy it…

I take deep calming breaths, trying my best to relax myself, and maybe deflate my little soldier enough to free him from his thigh-gated prison. But I’m fighting a losing battle. For every unsexy thought I conjure up, the act of her gently squeezing my member between her naked thighs is enough to keep him fully erect and ready for action.

I wonder for a moment how far away I am from her pussy.

Ok, thoughts like that... NOT HELPING!

We’re cuddling so close I can smell her. My arm is wrapped around her. My dick is jammed between her legs. I couldn’t get away if I wanted to, and I can’t think of anything but sex.

It figures... horniest time of my life and I’m trapped next to the only girl who doesn’t want me.

“Maybe you should put it in her... that would wake her up!”


Why don’t useful thoughts ever pop into my head like that?

Try as I might... there is nothing I can do. All I can do is lay there. Dick in a trap, horny as hell. I lay there for hours with my eyes closed, trying my best to think of unsexy thoughts, at first, but eventually I just give up and let my mind wander to whatever perverse thought it wants.

I figure, I’ll never fall asleep unless I calm down, but I’m wrong.

I end up falling asleep, thank god. But asleep, I dream of nothing but fucking. Fucking missionary, doggy style, cowgirl, reverse cowgirl, wheel barrel, in the shower, on the floor, in the kitchen... I dream... about fucking.

I drift in and out of being half asleep and awake.

Like some strange mix of reality and fantasy. In the real world I’m physically with the girl I want, and in the dream world, well, I’m with a lot of girls.

At some point in the night we shift around and my member is freed.

But my dreams keep going.

In my dream we’re making out and she’s not wearing shorts or panties. I’m grabbing her bare-naked ass and she’s gripping my cock. In my dream my little sergeant is making his way in past her thighs. In my dream she wants me, and I give it to her.

Around this time of dream induced fantasy fucking I drift into consciousness and realize that I’m rubbing my dick on something.

I open my eyes slightly, still in a daze. I’m laying on my back, Ash is cuddled into me, with her head resting on my chest, and her hand laying on my dick which I am vigorously pumping up and down.

“Holy shit!” I exclaim.

I stop moving immediately. I’m fully awake now. I look over to her.

“Ash?” I whisper.

She doesn’t respond.

“Ash?” I repeat.


I take a deep breath and push her ever so slightly off of me, but she stirs a bit, moves a bit, pulls herself a bit closer, and her hand grips my dick.

I almost jizz right there.

She’s gripping me like a kid playing with a joystick. Ironically, this is what I’d always wanted her to do, but I just kind of hoped she’d be awake when she did it.


I look down and realize that my penis is still jetting out of my PJs, and she’s fully gripping it. It’s not a tight grip. It’s the kind of grip a sleeping person has on their pillow or the person next to them. But fuck, for a virgin high school kid, having a girl touch you like this, even if she is unconscious, is almost too much.

I wonder for a moment, who is raping who.

Ash’s grip lightens a bit, but my cock is still not going anywhere.

I always imagined that the first time a girl had her hand around my dick I would be in an awe inspired paradise. I mean, as a teenage boy, I would literally sit up at night and try to think of ways to get girls to touch my penis. Yet here I am, laying in bed next to a beautiful girl—next to an amazing girl, next to a girl I fucking want to date and marry—she’s got her hand around my cock, and I’m trying to think of ways to not jizz all over myself.

It’s an interesting exercise. Usually when my penis gets touched I look forward to cumming. I even try and make it happen quickly, if I’m in a rush or if I think my parents or brother might come knocking on the bathroom door and kill the mood. I’ve never tried not to cum. And it’s fucking hard! (Mind the pun.)

I decide to try and move her again.

I push her gently, trying to move her without waking her up. I really don’t want to wake her up right now. If I thought explaining why my dick was between her legs would be awkward, I couldn’t even fathom how I would explain away this.

I push her again, and she does get off me, but she pulls my dick wish her as she goes.

I’m caught between pain and ecstasy. If I don’t move with her, her sliding hand is going to jack me off and I might cum right there. So I turn with her hand, and now we’re both laying on our sides, facing one another, with one big elephant in the room, laying directly between us, cocked and ready to fire at any second.

Perhaps worst of all, as I look at her, I notice that one of the spaghetti straps on her top has fallen down, and her naked breast is now hanging out, staring at me.

I try to look away but it has some strange power over me. Like a booby trap. A real booby trap. My gaze remains fixed. Even if I didn’t want to think about sex right now, I no longer have that ability.

As I stare into her orb of sexual doom, I feel my dick pulsating a bit, and it rubs in her hand each time it does. Which of course, only makes it pulsate more and more and well... I’m fucked!

I slam my eyes shut and tell myself not to look, not to think. I run through all the possible outcomes of this night in my head, and I start to wonder, if I did just ejaculate all over myself, all over her and she woke up to cum spraying everywhere, would it really be my fault? I mean, yes I know she literally just told me that she wants us to be friends and only friends, but hell, my penis doesn’t know that. I could just say, “I’m sorry but you gave me a hand job in your sleep, what was I supposed to do?”

I try harder and harder to not think about sex, to block out the knowledge that my best friend is jacking me off in her sleep. But the more I try not to think about it, the more I have to think about it.

She moves again.


I start to try and pull my dick out of her hand, but the pulling sensation feels too good. I can’t... if I pull it out I’m going to cum!

Double fuck!

The tit looks at me!


She gives a sigh in her sleep.

Fuck why is that sexy?!

Then, she jerks in her sleep for just a second, her hand clamps down then releases, and it’s all just too much. I feel it coming. Like a beaver’s dam trying to block a tidal wave, there’s no holding back here. I’m going to fucking cum. My dick starts to pulsate more and more. Fuck!

And then it happens. After hours of trying not to, of trying to hold it in, of burying my dick in her thighs and dreaming about fucking, of her groping me in her sleep, I cum. My instinct is to shout out but I gasp repeatedly instead, trying desperately not to scream aloud. I cum. And I don’t just mean that I cum, I mean, I cum!

Squirt after squirt flies out of my penis, and with each squirt, the angle and direction of my dick shifts. I hit her eye, my stomach, her belly. I shoot jizz all over her naked tit, all over her hand, and all over our pillows and sheets. I even have to lean my head back during the worst of it, so I don’t get it all over my own face, although I do hit my nose. Hours of being fully turned on leads to a huge buildup of cum, and I shoot it all over the both of us.

And there, at the height of my ecstasy, what a perfect time for her to wake up.


She yawns lazily and stretches. There’s jizz on her lips. She pulls her hands to her face to rub her eyes, but as soon as she does the abundance of semen all over her eyes and hands becomes dead obvious.

“Oh what the fuck?!” she exclaims and she jerks her hands back from her face. She starts to use her arm to try and rub whatever it is in her eyes, off her face. But I got her arm too, and so she just smears more of it across herself.

“What... the… FUCK?!” she repeats louder this time. She starts spitting, trying to get the cum away from her mouth. She shoves her head in the blankets, looking for a dry spot, to wipe her face off. It takes her a minute to find an unsoiled piece of cloth, but she eventually finds some.

She’s standing up now, wiping cum off her face.

Her boob is still hanging out of her shirt. My horny teenage self is still looking between her and her damned teasing tit. The situation is fucked.

I stand up to try and reassure her or explain myself. In the confusion, I forget to tuck my penis back into my pants.

She drops the blanket and opens her eyes, “What the hell was... oh my god, why is your dick out?”

I don’t know the polite way to say that I jizzed all over you from a nocturnal hand job.

She gives me a grossed out look and leans back a bit.

“Uh... your... thingy is out!” she repeats.

I look down and see my cock is still peaking out of my boxers. Still erect. Like an eager little turtle peaking out of his shell, aching for more.

That’s when she notices her breast is showing. She throws a hand up over it out of embarrassment. But quickly the look of embarrassment turns to that of realization, anger, and disgust.

“Oh my god!” she exclaims.

The hand hiding her tit feels the cum on her boob. She looks down at herself and realizes what it is that’s covering us both. We look like we’ve both been slimed by a horny ghost.

“OH... MY... GOD!” she yells. “How could you?!”

“I uh...”

“No really! Physically, how could you?! This much?! THIS MUCH?!”

What could I say?

“I’m a teenage boy,” I shrug.

“OH MY GOOOOOD!” she yells again as she turns and runs upstairs.

I can hear her screaming and gasping as she runs. I’m left downstairs, alone, covered in my own juice. I look down at my still erect penis and all I can think is, “How in the hell am I still ready to go again?”

God, high school is awkward times...

The true test of a friendship is whether you’re still friends after you cum all over her. Believe it or not, I actually stayed friends with Ash after we finally got a chance to talk. After I finally got a chance to explain to her what happened. Well, the censored version. I left out all that stuff about my dick going between her legs and the hand job. In the version she got, I just had a wet dream about a girl in our class.

I think it was an eye-opening experience for Ash. And that eye was covered in cum when it opened. It made us both realize why guys and girls need a bit space, even if they are best friends.

Guys and girls can be friends. They can be good friends. They can be close friends. They can have connections and share, and enjoy time together and open up to one another. They can be physically and emotionally comfortable and connected. But everyone needs to remember that no matter how aware a guy is of the fact that a girl is a friend and only a friend, his penis will never learn. No matter how platonic a relationship with a girl is, if they get too close us, eventually, we’ll just cum all over them.

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