The First Time
I’m telling the story of how I broke my crush’s anal virginity. She lay on the bed with her hips at the very edge, a towel-wrapped pillow propped beneath her waist. She pulled her knees together and lifted them toward the sky, clasping her hands around them to keep them from splaying apart.
"For now... please, start by loosening me up with your fingers..."
Her reaction was different from when we had vaginal sex. Back then, she would be soaking wet even without foreplay, but now she was on the verge of tears, her neck twisting this way and that from the pain. To be honest, I think I have a bit of a sadistic streak. The more Yerim cried, the more she complained of pain, the more aroused I became. Suppressing my surging excitement, I raised my middle finger and slowly pushed it into her pink anus.
"Haa-hk, ah, ah..."
Intermittent screams escaped her lips. Even getting past the first knuckle was a struggle. She was clenching so tightly even now; I couldn't even imagine how it would feel once I put my cock inside.
"Yerim, relax a little. It won't go in."
"Augh, okay."
Yerim gasped for air, trying her best to let go of the tension. She reached one hand down to her crotch to fiddle with her clitoris, but I didn't like that.
"Yerim, don't touch your clit. Don't be cheeky. You should be able to feel good with just your ass, right?"
"Yes, yes, you're right. You're right, Oppa..."
Like a girl caught stealing, she pulled her hand away and grabbed her knees again. But it seemed the tension wouldn't fade so easily. When I pulled my finger out, her sphincter gripped it so tightly it was sticky. The skin around her anus stretched and pulled every time I withdrew. I decided to show a little mercy and applied more love gel to my fingertips.
Squish, squelch. The sound of my fingers stirring her rear became stickier. At the same time, Yerim’s screams grew a little sweeter. Once I had slowly worked my way up to the second knuckle, I added a back-and-forth motion and began massaging the inside, causing Yerim to bite her lip in pleasure. Before I knew it, sticky nectar was leaking from the center of her pink pussy.
"Why is your pussy leaking when I'm only poking your ass?"
"Ah, ah. Yerim is... ah, I'm a pervert who gets off on anal, that's why. Thank you for playing with meee."
About ten minutes after I started poking her, I pulled my finger out. Her anus didn't snap shut; it seemed properly loosened. It pulsed, opening and closing, revealing the bright red flesh inside. It looked ready for insertion. But there was something I had to do first. I pulled out my phone and hit record. It was Yerim’s anal debut, after all—shouldn't I keep it as a video? I pointed the camera toward her face.
"Yerim. You're about to lose your anal virginity today. How do you feel?"
Her face, flushed from the intense anal foreplay, was bright red. Even if it was her first time having anal sex, she was a succubus at her core. She might cry from the pain at first, but eventually, she would burn with pleasure. Anticipating the insertion to come, Yerim gulped and opened her mouth.
"Kangmin Oppa, thank you. My pussy and my ass are both yours. Please use them however you want. I'll clench down tight with my virgin ass for you. Please, use me as much as you want."
I had expected her to say she hated anal sex but was doing it because it was my request, but this was pretty good in its own way. Then again, would a succubus ever say she hated it? I swallowed hard and began the entry once more. I spread her feet apart and changed her position so her thighs were pressed firmly together. Standing in front of the bed, I aimed my massive member at her opening. Holding the camera in one hand and my cock in the other, I slowly inserted myself into Yerim’s anus.
The camera clearly captured my thick shaft slowly sliding in. Leaving her wet, light-pink pussy behind, I dug deep into a hole that a normal woman would never use in her entire life. Yerim’s mournful screams were being recorded clearly.
"Aughhh—Oppa, it's all the way in, right...?"
"No, it's only halfway."
Yerim’s face turned pale. I zoomed in on her face as she stared at the point of insertion. The way she gritted her teeth in extreme pain was insanely sexy. Her hips were glistening with a mixture of sweat and love gel. I put more weight into it. Yerim twisted her thighs and begged.
"Oppa, Oppa, Oppa, it hurts, it hurts! Please, just stop moving for a second!"
But I didn't listen. I kept pushing until my entire length was buried deep inside her. My massive, thick rod was buried to the hilt in Yerim’s rear. It was a different kind of tightness than her pussy. Because I had applied plenty of love gel, which was much more viscous than her natural fluids, it felt much slicker and tighter. I moved my hips slowly. I propped the phone up on a stand nearby and grabbed Yerim’s thighs with both hands. Enjoying the folds inside her, I ground my hips like a millstone.
"Augh, ahhhhh!"
Yerim gave up on trying to stop me and tried not to tense her glutes to minimize the pain. Her anus stretched wide, struggling to accept my size.
"Yerim, doesn't it feel good to be fucked in the ass?"
Unlike the very beginning, she was quite relaxed. It was still tight, but not enough to make her scream and cry. Yerim shook her head back and forth. Her black, silk-like hair whipped from side to side.
"Augh, augh, Oppa. Anal sex, it feels good... ah, what do I do..."
Before long, the screams coming from Yerim’s mouth were mixed with sexy moans. The sharp pain that felt like it was tearing her sphincter apart was turning into a pleasure that seemed to caress every nerve in her body.
"You said this was your first time having sex through your asshole, so why are you enjoying it so much? You little slut."
Every time I scolded her, her anus would clench down noticeably tighter. She seemed to enjoy the dirty talk, too. As I began to thrust in and out in earnest, the obscene, squelching sounds echoed through the room. I pulled out until just the head remained, then slammed it back in to the hilt, drawing out gasping moans.
"Aughhh, it feels good. Augh, ah..."
"You're about to cum, aren't you, Yerim?"
"Yes, yesss—"
I picked up the pace. My wicked, fleshy pillar hammered in and out between her cheeks. "Haa, haa, haa." Moans escaped my own lips. Her sphincter was clenching down hard. She was on the verge of climax.
"Yerim, I'm cumming, clench tighter!"
"Augh, yes—yes!"
At my command, Yerim tensed her glutes so hard that dimples formed. Her hips trembled as she reached her peak. At the same time, I pushed harder and pumped my semen deep into her anus.
"Haa..."
When I pulled my cock out, the bright red flesh of her insides was exposed. Mixed with the white, milky fluid, it looked incredibly obscene. Her anus didn't close, but kept pulsing. Yerim panted, saying in a faint, dying voice,
"This is why I don't really like anal sex... it just leaks out..."
"But it felt good, didn't it?"
When I asked, she blushed and nodded. Then, she shifted her position and brought her mouth to my cock.
"Thank you for stuffing your cock into my dirty hole. I'll clean it up for you."
She opened her mouth to swallow my member, then looked toward the camera and flashed a V-sign.
"Show me the video later, too. I think it'll turn me on so much."
Wow, that was some seriously intense sex... We had been at it so hard since morning and lunch that she didn't even flinch while cleaning my member. Once the love gel and semen had all disappeared into her mouth, I lay back on the bed. We were both covered in sweat from how intense it had been.
"I think you were more excited during this session than any other time, Oppa."
"Hmm, really? I guess... I do have a thing for that."
"...I'll do it whenever you want, Oppa, but I don't want to do it too often... I think I'm bleeding a little... and it hurts..."
"Oh, is that so?"
Yerim burrowed into my arms, acting spoiled. Seeing her look up at me and plead, I felt like I wanted to put my own sexual preferences aside and do whatever she wanted. I mean, it wasn't exactly a place designed for insertion. But if I could make her feel pleasure there, wasn't it meant to be used? To be precise, the nerves in the vagina were connected to the anus, so it was designed to feel sexual pleasure there, too. So, it was meant to be used together from the start. Wouldn't I be missing out on half of life if I didn't use it?
"Later, if I ever go to the Akashic Records, I'll look for some magic to keep you from getting hurt. Until then... I'll be gentle. I won't be as rough as I was today."
"...Okay."
Yerim replied with a pout. It didn't seem like she was all that fond of anal sex. "Oppa... by any chance. Could you do it one more time..."
"Oh, right, the phone!"
I pretended not to hear her, got up, grabbed the phone, and hit the stop button. Our tryst had been recorded properly. I checked the time after a quick glance. Hmm, an hour and a half until my part-time job... I should sleep a little, wash up, and head out... Doing it again right now is impossible! We've already done it twice today!
"Ah, come to think of it, Oppa. This 'phone' thing. Could you buy me one, too?"
Yerim asked, her eyes sparkling. Oh, come to think of it, does she need a phone?