Stretching Out My Gal Childhood Friend's Ass with Anal Play
It had been about three days since I'd laid a kiss on Seo Narae at the university.
And here I was, visiting her house once again—this time in pursuit of pussy.
Just like always, I stripped off every stitch of clothing, rolled a condom onto my cock, and lined it up against her pussy, only to be met with—
“Haaah, honestly…”
“Why the death glare this early in the morning? Don't feel like having sex?”
I asked, watching Narae sigh irritably for what felt like the hundredth time.
Could her period have started? If so, then I was the one who'd been insensitive.
“Sorry. I never figured today would be that day…”
“What are you talking about? I'm tired because I had to explain you and all this nonsense to the girls, thanks to you.”
Apparently not her period, then. Good—no reason we couldn't get right to it.
It had been three days since I hauled the assignment Narae had left behind all the way to campus and handed it over.
And apparently word had spread like wildfire around the university in the meantime.
Something about it reaching not just students in our department but people in entirely unrelated majors.
Then again, upperclassmen had been sniffing around her constantly since her first year, so it wasn't exactly surprising.
“I've been wanting to ask—why did you suddenly start playing boyfriend out of nowhere?”
“No particular reason. I figured if you got a real boyfriend, I wouldn't be able to ask you for dirty stuff anymore.”
“For such a vulgar reason… I can't believe I got my hopes up, honestly.”
That's what I said, but it drifted pretty far from my true feelings.
Yes, Seo Narae cutting off my access to pussy would have been a full-blown emergency—but the truth was, the feeling that I simply didn't want anyone else taking her from me was far, far bigger.
Even coming by every day demanding sex carried that cheap ulterior motive: make her so addicted to my cock she couldn't even think about another man.
She might like me now, but I can't let her lose interest in an unemployed bum like me.
If my only selling point is this cock, then I have to use it to keep her attention. I planned on doing the same with the other three childhood friends, too.
“Anyway, you've made my life exhausting in every possible way, so if you want sex, you're the one who's going to have to work for it.”
“Well, at least no guys will bother you for the rest of your time there. I'd say that's a win.”
“I'm graduating soon anyway, so what does it…”
“You've still got a year and a half left. You took that leave of absence, so you're only a junior.”
“Hmph. That's not something I want to hear from a dropout.”
After our brief spat, we ended up having sex like always, and wrapped the whole affair up in under ten minutes.
One good pounding and even the pettiest argument evaporates—sex really is a wondrous thing.
“Hey. You remember how you said you wanted to… you know.”
“Huh?”
I was pulling the used condom off and tossing it in the trash when she suddenly hit me with a sentence that dropped its object entirely, leaving me utterly confused.
“…Ugh! Last time! You said you wanted to do it in my ass, remember!”
“Ohhh… that.”
Blushing a little, she dredged up the conversation we'd had at the university.
Apparently she'd taken my request—let me use your ass in exchange for delivering your assignment—straight at face value.
“Well, honestly, half of that was a joke.”
“Heh. I guess you weren't as desperate about it as I thought?”
She said that while crossing her arms and looking down at me.
My bluster had backfired spectacularly, and now the whole thing felt like she might not let me do it at all.
“I deeply apologize for my insolence. Please, grant me your back door.”
“…Oh. Fine, then.”
Anal sex ranked solidly in the TOP 3 of the fifty sexual acts I'd sworn to complete before I died.
If bending my head meant burying it in her ass, I'd bow as deep as she wanted. It was practically the dream I'd been chasing since childhood.
“Honestly, what's even so great about doing it in the butt?”
“Because it's hot, obviously.”
“At least you're honest. I don't really get it, myself.”
A woman's ass is a far more secret place than even her chest—something most people rarely get to see.
The anus, revealed only when you spread those usually-hidden cheeks wide open, could honestly be considered on par with the pussy itself.
And on top of that, there's the unbearable decadence of taking a hole meant for waste disposal and using it for sexual relief.
Not that I'm into scat, mind you…
Either way, anal is magnificent. Anal, back door, anus, butthole, asshole—the sheer variety of names for it means you never get bored.
“So? Want to do it right now?”
“Hold on. Even for you, right this second is a bit…”
Her sheer ignorance caught me so off guard that I waved my hands in panic.
Setting hygiene aside, her ass hadn't been trained at all yet—there was no way Narae's back door could take this monstrous cock of mine.
My cock, with a proven track record of clearing the 25cm mark with ease—if that went into an untrained anus, there was no telling what irreversible disaster might follow.
If I force it in and she ends up… unable to close… how the hell do I take responsibility for that?
A scene I didn't even want to imagine. It might turn me on, but this was still the body of a precious childhood friend.
“I'll go do some research, so you just wait here. Want me to whip up a PowerPoint by tomorrow while I'm at it?”
“You're being ridiculous… Fine, whatever. I don't want it to hurt either.”
And so I began my studies in earnest, all in service of training Seo Narae's ass.
Forcing my cock in cold turkey would deliver nothing but pain—pleasure would be lucky to get a word in edgewise.
Worse, like some microscopic onahole, there was a real chance it simply wouldn't go in at all. Which meant I had no choice but to learn how to loosen her back door properly and keep the pain to an absolute minimum.
First, I turned to that familiar wiki to learn about the risks of anal intercourse.
“Infection's the biggest danger, just like I figured.”
Because the anus connects directly to the rectum, apparently bacteria like E. coli can travel up the urethra if you go in without a condom.
So condoms are essential after all.
I'd always dreamed of someday going raw in a back door, but no matter how much I wanted it, it was far too risky—so that particular dream would have to stay locked away in my heart.
Unlike the pussy, the anus doesn't secrete its own fluids, so lube was a must, too.
I can just use what I already bought, right?
I'm the type who stockpiles lube for smooth onahole sessions, and since the ingredients are basically the same as commercial lubricant, there'd be no problem slathering it on her back door.
Beyond that, I dug through a number of firsthand accounts and absorbed meticulous knowledge on everything—how to do an enema, tricks for getting a cock in, and even aftercare once the sex was over.
Exactly twenty-four hours later, I found myself back at Seo Narae's house, where…
“…You want me to put this thing where?”
She stared at the anal plug I'd handed her with an expression of pure disbelief.
“I even brought lube to make it easier.”
“That's not the point… it's just, this is my first time seeing one in person, okay? I'm a little thrown.”
“Don't worry. It's my first time seeing one with my own eyes too.”
If it weren't my first time, that would be a whole different problem.
“I'll put it in for you, so bend over and show me that ass.”
“Uuuu~! This is so embarrassing! Can't I do it myself?”
“Doing it alone is rough. Knowing you, you'd have a crisis of confidence halfway through and quit—so let me handle it.”
“…You have to be gentle, okay?”
Muttering those words like she was on the verge of tears, she slowly began to peel off her bottoms.
Out came that sturdy, easy-birth ass of hers, the same as every time I saw it—and when I spread her cheeks apart with my hands, today's target came into full view: that chrysanthemum-shaped butthole.
“Get on the bed in cat pose… wait, do you stand? Whatever. Stick that ass up and hold it.”
“L-like this?”
“Okay. Now spread your cheeks with both hands, just like that.”
Shhaaap—
Holy. Shit.
A sight that pulls a gasp out of you all on its own.
She wasn't just spreading her ass—she was flattening the exact spot where her back door lived, stretching every last wrinkle of that asshole taut in full, glorious display.
The utterly vulgar sight of my childhood friend, trusting me enough to bare her back door without a shred of defense, was almost too much to bear.
I want to just slam it in right now… but no. I have to hold back.
Fighting down my erection for dear life, I slathered the lube thickly around her back door.
Squelch— squelch—
“Ah, mmm… that feels weird…”
A small moan escaped her as the cold liquid trickled down over her butthole.
I'd applied plenty around the entrance, so now it was time to go after the long-awaited interior.
I first tried slipping my index finger into that cute little pucker clenched shut in a perfect O—
“NyaAAAH?!”
“?! What the hell, did it hurt that much?”
“Nnngh, no… it doesn't hurt… hyaAAAH!”
Startled by Narae's scream, I reflexively yanked my finger right back out of her asshole. I hadn't even gotten a proper feel for it yet.
Don't tell me…
She was face-down in the bed, panting hard, chest heaving with ragged breaths.
Apparently this girl was absurdly sensitive back there.
Come to think of it, she really did have the face of someone weak to anal. Even the way she acted screamed tsundere.
I have no idea what a “face built for anal” would even look like, but at least in Seo Narae's case, it seemed she'd been born with a constitution that felt everything through her butthole.
…Maybe I should tease her a little.
She'd turned her head away so fast I couldn't get a proper look, but I had a feeling that when her ass got teased, humiliation and pleasure hit her at the same time—and it made for an unbearably cute expression.
I wanted to see that face. The one she showed no one else in the world—a face she showed only me.