Glad It Was a Good First Experience
Chae-ah had given me such a humiliating experience.
So this anal fingering now could be seen as fitting punishment for that.
But damn, I was in such an awkward spot.
I couldn't enjoy dishing out the punishment, yet I couldn't just let it slide without any either.
"Chae-ah, relax. It's okay."
"I-I know, but... hngut…♡"
It was just one finger. I hadn't even thrust it in roughly or quickly.
I'd inserted it as gently and slowly as possible, giving her time to adjust.
Yet her walls were clamping down on my finger so tight, it felt like the blood couldn't flow.
"Chae-ah, look at me."
"Y-Yes…?"
Chae-ah had her eyes squeezed shut and her fists clenched tight.
Anyone seeing this would think I was forcing myself on her.
This was just me helping my beloved girlfriend try something new.
"Does it hurt?"
"N-No...♡"
Her voice trembled with a hint of coquettishness—she was definitely feeling it.
"Then can you try relaxing a little?"
"I-I want to, but... I'm so tense…♡"
"Pfft, why are you tense? It's fine."
"B-Because... it's my first time…♡"
She emphasized it with shaking eyes and clenched fists, and a sharp pang hit my heart.
It felt like I was doing something I shouldn't to her.
Guilt gnawed at my conscience.
If she'd looked at me with her usual gaze, I could've laughed it off. But those wide, sparkling eyes just tortured me more.
"R-Right... first time... yeah, it is your first, isn't it…"
"Unni…?"
"Should we do it later? We can stop for today."
Back when she'd pissed all over the bathroom floor, I'd planned to pound her ass until she squirted and came.
But now everything had changed.
I decided this wasn't punishment anymore. I was just gently guiding her through her first time, step by step.
Those sparkling eyes and her expression had played a big part in shifting my mindset.
"I-I want to do it…♡"
"Hmm, that might be tough. You're clenching so hard, no blood's getting to my finger."
"Huh…? I-Is it that bad? When I put my finger in your ass, it was fine."
It was the difference between a used hole and a fresh one, I guess.
Thinking like that made me feel a bit gross, like some anal masturbation addict.
"Wanna try deep breaths?"
"Suuup... hoo... suuuup... hoooo…"
She followed my suggestion, breathing deeply and slowly. I kept eye contact, smiling to ease her nerves.
Gradually, the tight walls around my finger started to loosen.
Now I could probably wiggle the first and second knuckles, tapping lightly.
"I'm gonna start stimulating a bit now. Don't freak out, okay?"
"Y-Yes… Ah, unni... hold my hand…"
At her request, I offered my other hand. She grabbed it desperately with both of hers.
It was like she was psyching herself up for a bungee jump or something.
But to make her first anal experience a good one, I had no choice but to go along.
"Here I go?"
"Y-Yes…"
-Squuuish!
"Hnguuuuut…♡"
I just pressed the first and second knuckles against her walls.
As they tried to clamp down again, I spoke up to reassure her.
"It's okay, Chae-ah. Look, we're still facing each other. No need to tense up."
"Y-Yes… unni…♡"
The walls loosened once more.
"One more time."
-Squuuuish!
This time, I pressed harder, holding it longer.
"Huya aaaang♥"
As I pressed upward, her hips subtly bucked up then settled.
Her changing moans told me she was starting to feel it properly.
"You good?"
"Y-Yes, I'm good…♡"
"I'll count to three, then pull out a bit and push back in."
"O-Okay…♡"
"One, two... three."
-Squelch!
"Hihigiit…♡"
Pulling out slowly, I felt a deeper warmth and vivid texture.
It was like her walls were coming out with my finger.
"Still good?"
"Y-Yeah, good…♡"
"Pushing back in now."
-Squelch!
"Huhya aaaang♥"
I slid it back to the same depth.
Her anal entrance dimpled inward around my finger, and her body twitched upward.
"Hiiiit…♡"
"How's it feel?"
"G-Good…♡ N-Not painful…♡"
"Glad to hear it. Can I go a little faster now?"
"Y-Yes, but... n-not too fast…♡"
"Got it."
-Squelch! Squelch! Squuuuelch! Squelch!
I repeated the slow in-and-out, watching her every little reaction.
"Hng…♡ Huya aang…♡ Huguuut♥ U-Unni…♡"
Her calling me "Ungni" was lethally cute every time.
That kind of cuteness only deepened my guilt, making me feel like I was doing something wrong.
"Yeah, Chae-ah. Unni's right here."
"Hueuk…♡ G-Good…♡"
"Wanna speed up a bit more?"
"H-Hug me…♡"
Before quickening the finger prowling inside her ass, I let go of her hand and pulled her into a tight embrace.
She wrapped her arms around my neck, pressing so close not even a sheet of paper could slip between us.
-Squelch! Squish-squish! Squelch!
"Huhiya aang♥ G-Good…♡ U-Unni's finger feels so good…♡"
"Being this cute is against the rules."
She looked scared yet was trying so hard to accept it—it was just too adorable.
I'd completely abandoned any thought of punishment now.
I was just helping her have a great first time.
"U-Unni… I-I'm gonna cum…♡"
"Yeah, go ahead. It's okay."
"Ungnii… Hiya aang♥ Hugut…♡"
Figuring she'd need stronger stimulation to finish, I pressed hard against the wall.
"Hya aaa ung♥"
She hugged me even tighter, her legs squeezing my hips.
With rough moans, her body shuddered violently, then she collapsed, letting her arms and legs flop onto the bed after pouring everything out.
"I-I came…♡"
"Good girl, Chae-ah. You did great. I'm taking my finger out now."
"O-Okay…♡"
-Squelch! Pop!
She'd clenched so hard that pulling out made a clear, crisp sound.
Whether from embarrassment, she covered her mouth with both fists, peeking at me.
Mentioning the sound would ruin the moment, so I just stroked her bangs.
I peeled off the used finger condom, tossed it in the trash, and planted a soft kiss on her forehead.
-Mwah!
"Hehe… Unni gave me a kiss."
Just an forehead kiss had her beaming innocently. I lay beside her, gently caressing her cheek.
"I was planning to punish you, you know."
"It wasn't punishment?"
"Wasn't it too gentle for that?"
"Come to think of it... you were like a doctor, unni."
"Pfft, an anal specialist?"
"Yes! Heehee."
Today's mischief could be forgiven as cute aegyo.
Thinking back, she probably hadn't expected that situation either.
"Just get past tomorrow, and it'll be my birthday."
"Yeah, true. Your birthday's coming up soon."
"I'm excited for your gift, unni. Can't you give me a hint?"
"If I did, you'd guess it right away."
We pulled the blanket up to our shoulders and lay facing each other.
She wrapped her arm around me like a hug, then her hands naturally slid down to grope my ass.
"Natural, huh?"
"Can't I touch?"
"No, go ahead. Touch."
"Hehe, okaaaay."
With that bright smile, she got even more bold.
"Unni, I wanna go on a trip with you sometime."
"A trip sounds great. Where to?"
"Huh? You really mean it?"
She seemed genuinely shocked at my positive response to her casual suggestion.
This was the girl who'd pretended not to know my feelings despite knowing them, pushing me away countless times.
Now that we were dating, she wasn't oblivious enough to brush it off.
"Yeah, of course."
"A-A week! No, that's too long. The store can't close that much... umm…"
"Pffft! Take your time thinking."
I could see her already planning in her head—it was obvious, so of course I laughed.
"Unni, let's go early July!"
"Early July? Why then?"
She narrowed her eyes and glared at my question.
Was that the wrong thing to ask?
"Chae-ah…?"
"Right now, your girlfriend is wondering how you fell for a girl like me."
"H-Huh…? Did I do something wrong?"
"That's our 100th day!"
Hearing why she'd picked early July made my mind go blank.
We'd barely started dating—just a day in.
Yet she'd already calculated our 100th day?
The very idea of marking 100 days hadn't even crossed my mind.
"Oh, right. 100 days. Yeah, that's our 100th day."
My response felt like sitting on a bed of nails.
"Then let's do it then."
"I see you brushing it off."
"S-Sorry, unni's sorry. I love you, Chae-ah."
"I know that's half-hearted too, but I hate myself for smiling anyway. Pffht."
I reflected on when I'd last bothered with 100-day anniversaries.
Not even in my early twenties.
Not since high school or after twenty. Never.
"Guess I need to put in a lot of effort."
"What effort?"
"Effort to keep our Chae-ah smiling."
I couldn't just blame the age gap.
I'd lived a life so far from the romance she craved.
Time to slowly walk back toward that romance.
Only then could I make her truly happy.