Ji-yoon's Virginity
I thrust my hips with fierce determination. Perhaps moved by my efforts to raise her stats, Ji-yoon lay beneath me with a tearful face, letting out sweet, sobbing moans.
My waist moved at its absolute peak speed. The urge to climax surged through me, and I unleashed a thick, messy load straight into her pussy. An enormous volume of semen—fitting for an A-rank—completely filled Ji-yoon's womb. When I finally pulled my cock out, I got to admire the creamy waterfall of cum pouring from her cunt.
I took a moment to catch my breath and drank some water. The sun had set long ago, and midnight was approaching. After all that hip-pumping purely for stat gains, Ji-yoon's CON stat had finally broken past 100. With the goal achieved, there was no need to rush anymore. By dawn, Ji-su, Si-eun, and Juniel—who had gone out hunting—would return.
Ji-yoon lay there panting, cum still leaking steadily from her pussy. I spoke to her.
“Should we call it a night? We've hit the target, and the others will probably be back soon...”
At my words, Ji-yoon quickly sat up.
“U-um... Oppa.”
“Yeah?”
Ji-yoon called my name but couldn't continue. She fidgeted restlessly. What was going on? It looked like she had something to say.
I told her, “Didn't I say before? If you want something, just tell me. You can speak comfortably.”
“Ah...”
Ji-yoon stared at me quietly, then lowered her head and murmured, “C-could we... do it just one more time? P-please...”
Oh? I hadn't expected that kind of request. We'd already done it quite a lot. Was she still not satisfied? Well, to be fair, it hadn't really been sex for pleasure. It was mostly just me pounding and cumming to raise her stats... Yeah, it was pretty boring sex, honestly. No wonder she felt unsatisfied.
We weren't short on time, and since this would be the last round, I should make it feel really good for her.
“Why wouldn't I? If you want it, of course I'll give it to you.”
As I moved closer, Ji-yoon hurriedly spoke again.
“Um... Oppa.”
“Yeah?”
“.....”
She couldn't speak again. I'd have to wait a little. As expected, after a brief pause, Ji-yoon seemed to steel herself and opened her mouth once more.
“I... I've been thinking about something.”
“Go ahead. Speak freely.”
When I looked at her with warm eyes, Ji-yoon bowed her head deeply and began.
“Ji-su... and Si-eun unnie... and even... Juniel... They all gave their first time to you, Oppa.”
Hmm. So this was what it was about. Ji-yoon had been subtly watching everyone else for a while now. She seemed to feel incredibly guilty that she was the only one who hadn't offered her virginity to me. But I was fine with it. No one took care of me as meticulously as she did, understanding even the smallest details of my heart and acting on them. Still, it seemed that wasn't enough for her.
With a guilty expression, Ji-yoon continued.
“I felt so sorry toward you... Everyone else experienced their first time with you, but I couldn't...”
“You don't need to think like that. I don't mind at all.”
“But... my heart just won't feel at ease...”
Hmm... What should I do? Even I couldn't regenerate a hymen that was already gone.
As I looked at her with slight awkwardness, Ji-yoon said to me, “So... I want to give you the first I can offer.”
“Huh? What do you mean...”
When I asked in confusion, Ji-yoon silently got on all fours in front of me. It looked like she was preparing for doggy style, but something was different. She grabbed both cheeks of her ass with her hands and slowly spread them wide open for me to see. With her face buried in the floor, she spoke in a voice that sounded like it was crawling from her throat.
“Th-this side... has never been used by anyone... I couldn't give you my front virginity, but... I want to give you my back... virginity. I-is that okay...?”
I stared blankly at Ji-yoon's fully spread asshole—her anus. Anal sex. Was I really about to do the kind of anal sex I'd only seen in porn? No, the whole situation itself was straight out of a porn video. Since she couldn't give me her front virginity, she'd give me her back one instead. Was she an angel?
As I continued staring at her in a daze, Ji-yoon spoke shyly.
“I-if you don't want to—”
“No. I want it. I really want it.”
My cock was already rock-hard from anticipating what was to come, pressed firmly against my lower abdomen. The thick, bulging veins stood out more than usual, showing just how excited I was right now.
Ji-yoon continued in that tiny, crawling voice.
“N-normally you'd need a lot of preparation for this... but since our bodies don't require that kind of prep... you can just do whatever you want, Oppa.”
She was right. Normally, anal sex required extensive foreplay because you were putting something in a hole not meant for it. But as Ji-yoon said, my thralls didn't need any of that preparation.
Wait a second. Come to think of it, didn't that mean my thralls were perfectly optimized for anal sex? Not just Ji-yoon, but the other girls too...
“O-oppa? I'm getting really embarrassed... C-could you do it quickly, please?”
Ah, I'd gotten too lost in my fantasies. Ji-yoon's current position was definitely something to be extremely embarrassed about—lying face-down while using both hands to spread her asshole wide open. If we had time, I'd want to stare at it forever. I'd have to make the other girls do this later too.
I approached Ji-yoon. When I sat beside her, she flinched visibly. Even though we'd mixed our bodies so many times, she still looked quite nervous. I gently stroked her body to help her relax.
I slowly ran my hand down her smoothly curved back, moving toward her ass. Ji-yoon began breathing in short, quick gasps. As my fingers gently explored the area and brushed against her anus—
“Kyaa!”
She let out an adorable squeak and twitched hard. Ah, her reactions were too cute.
I began properly touching her back hole, caressing it slowly.
“Hngh... O-oppa. A little gentler...”
“How does it feel?”
At my question, Ji-yoon shook her head and answered, “I-I don't know. It just feels... a little strange...”
“Really?”
I opened the cap of the lube sitting nearby and squeezed a generous amount directly onto her ass.
“Hiiiik!!”
The cold gel made her shiver all over, goosebumps rising across her skin. I slowly massaged the lube into her ass until my hand was completely covered in it too. Then I used my slick fingers to gently tease and tickle her asshole. Ji-yoon trembled and bit her lip.
“Are you okay? Should I stop?”
At my concerned question, Ji-yoon shook her head vigorously.
“No, Oppa. You have to do it. I... I want to give you my first time too...”
What a sweet girl. She really was an angel.
I continued massaging her asshole, applying plenty of lube. Leaning close to her ear while she remained on all fours, I whispered, “I'll start with one finger. Okay?”
“...Yes, Oppa. I'm ready.”
“Good. Relax... Here I go?”
“Y-yes... Hngh.....!!???”
A moan that sounded almost like a scream escaped her as my middle finger was sucked inside. It went in more easily than I'd expected. But Ji-yoon was trembling all over, so it clearly wasn't easy for her.
“You okay?”
She forced an awkward smile. “I-I'm fine. Really, I'm okay, Oppa. So... you can keep going comfortably...”
Hmm. Stopping here wouldn't be doing her any favors. And honestly, I didn't want to stop either.
I slowly added more fingers, stretching her gradually. My cock was much thicker than my fingers, after all—I needed to loosen her up at least a little. Once I had three fingers inside, I began slowly thrusting them in and out.
“Hngh... Hiiik... Hngh... Haaang....”
Ji-yoon let out strained, whimpering moans. After moving my hand for a while, the tight muscles of her anus that had been gripping my fingers began to relax and soften.
It seemed like she was ready enough. I pulled my fingers out and pressed the head of my cock against her asshole. My dick had been twitching and leaking precum for a while now. I rubbed it along her ass crack, coating it thoroughly with lube. Then, with the tip pressed against her entrance, I asked, “Ji-yoon. I'm going to put it in for real now. You good?”
She answered in a tense voice, “Yes... I'm okay, Oppa. Don't worry about me... Just do whatever feels good for you.”
She buried her face forward again and added in the tiniest whisper, “Please... accept my... first time...”
God, could any woman be better than this? Just for the emotion she was giving me, I had to do my absolute best.
I slowly pushed my cock into Ji-yoon's asshole.
“Ughh.... Uuugh...... Hngh.....”
Her reaction was completely different from when I entered her pussy. She clearly looked like she was struggling, but I didn't have the mental capacity to focus on that. The fact that this was my first anal sex, combined with how insanely tight Ji-yoon's asshole was gripping me—it was enough to drive me crazy.
I already felt the urge to cum while I was still pushing in. Her anal muscles squeezed with unbelievable force. Among all the girls, Juniel had the strongest pussy grip. But Ji-yoon's asshole far surpassed even that.
“Hoo... Hoo... Khngh.... Ahhng......”
Ji-yoon let out rough, labored moans. But I was struggling too. If I let my mind wander even a little, I'd blow my load instantly. Slowly... slowly... deeper... deeper. Her asshole seemed to suck my cock in like it was devouring it. Finally, I managed to bury myself to the hilt inside her ass.
Ji-yoon was breathing hard. Goosebumps covered her shoulders and back.
“Haa... Haa... O-oppa...”
“Ji-yoon, it's all the way in. You okay?”
“Yes... I'm fine... How about you, Oppa...? D-does it feel good...?”
“I'm about to lose my mind. If I relax even a little, I'll cum right away.”
“Th-that's good then... Enjoy it a lot, Oppa...”
With my cock fully buried in her ass, I slowly stroked her back. She probably needed a moment to adjust. Even though I wasn't moving, the inside of her ass kept writhing and squeezing my cock in the most insane ways.
While she adjusted to me, I focused hard on getting used to her incredible tightness. Eventually, her insides seemed to soften a bit.
I spoke against her back. “I'm going to start moving now. I'll go slow, so don't worry too much.”
“Yes, Oppa.”
Every time she spoke, her ass clenched down hard. The sensation was unreal.
I began slowly pulling out. No—pulling wasn't the right word. It felt more like I was being dragged out. Her asshole clung so tightly to my cock that it came out with me.
“Hiiak... Hngh..”
I pushed back in, fighting that incredible tightness. And so the thrusting began.
“Hngh.. Haaang... Hiiak.... Haak...”
As I watched her back while she moaned, a different kind of conquest than regular doggy style surged through me. I grabbed her ass with both hands and gradually increased my pace.
“Ahk... Haang... Haak.. Haak...”
Her pitiful moans were driving me insane. The pleasure at the tip of my cock was already threatening to explode. I grabbed both her hands and pulled her upper body upright. Since my cock was in her ass instead of her pussy, it was surprisingly easy to lift her. I kept thrusting while grabbing her breasts, and Ji-yoon turned her head to kiss me, panting heavily.
“O-oppa... Ahang... D-does it feel good? The feeling... Haak...”
“It feels amazing... Really, it's the best...”
Breathing hard as I slammed into her ass, the urge to cum rose again. Not yet. I couldn't end my first anal experience this quickly. I pulled my hips back and withdrew completely.
“...Oppa?”
Ji-yoon looked at me with half-lidded eyes. I laid her down properly on the mattress.
“Y-you want to do it in this position?”
“Yeah. I wanted to try it like this.”
I laid her flat and placed a pillow under her hips. When I spread her slightly raised legs, her asshole lined up perfectly with my cock. I pushed back inside her.
“Haak..!”
I resumed my piston movements. The sound of my thighs slapping against her ass began to echo.
“Oppa.. Haaang... Oppa... Oppaaa...”
Slap slap slap slap slap. The wet sounds of flesh meeting flesh filled the room as I stared intently at her pussy. From the look of her, she didn't seem to be feeling that good. Feeling pleasure from anal sex on your first try was probably only something that happened in porn. She was clearly enduring the strange sensation for my sake. Because she was such a good girl.
But I couldn't accept only myself feeling good. We had to feel good together.
I sped up my hips and slipped my fingers into her empty pussy.
“Hiiyaak! O-oppa?!”
Ji-yoon let out a strange cry and stared at me with wide eyes. I inserted two fingers and gently scraped the front wall of her vagina.
“Ahang! O-oppa. Aaaang! Aaaang! Oppa aaah..!!”
Her moans completely changed. And... she was squeezing incredibly hard. Both her pussy around my fingers and her ass around my cock. Ji-yoon began clamping down on both with tremendous force. I fought through the pressure and kept moving my hips and hand.
“Oppa! Haaang!! Oppaaa!! T-too! Aaaang! It feels too good!! Ahaang Oppa!! Haaang! What do I do... What do I do...”
It didn't take long after I started fingering her for her to start saying “What do I do?” That was proof she was approaching orgasm. I wasn't far behind either. I'd been desperately holding back the load that was ready to burst from the tip of my cock. I planned to cum the moment she reached her peak.
I thrust hard with my hips, fingered her pussy vigorously, and used my thumb to rub her clit. Ji-yoon's moans grew higher and higher, and I could feel her body starting to tremble.
Finally—
“Oppaaa!! Haaang!!! Kyaaaaaaaang!!!”
With a high-pitched scream, Ji-yoon's body went rigid. Her dark pupils rolled back completely. Confirming she'd reached her climax, I gave one final powerful thrust and buried my cock deep in her ass, unleashing everything I had.
“Krrrrrrraaaaagh...!!!!”
An orgasm so intense it felt like my cock might explode, accompanied by a massive eruption of cum. Spurt! Splurt!! Spurt!!! It felt like I was releasing more semen than in any sex session before. The flow just wouldn't stop. Ji-yoon trembled as she received my load and whispered weakly.
“My belly... my belly feels... so full... Haaaaang...”
I'd cum a lot. Really, a ridiculous amount. When I pulled my spent cock from her loosened asshole, the cum that had pooled inside came gushing out with a wet psshht. From her pussy, the pressure forced out the earlier load, which began flowing out in thick streams. A double cum waterfall poured from both her holes. It was truly a spectacular sight.
Ji-yoon lay there completely spent, twitching weakly. I collapsed on top of her, exhausted from pouring out every ounce of my strength.
Ah, that really was an incredible first time from Ji-yoon.