2-2. Helena takes his virginity

Alright, sorry to keep you waiting. I brought the lube that was provided in the room. Mmm, you're being such a good boy, staying in the exact position I told you to. Then I'll kneel right behind your ass. Ufufu, your little pussy is completely exposed. Hmm, let me see... Oh wow, this is quite something. Hehe... So, before I put it in, I'm going to check how much your anus can stretch. If it's too tight, sometimes penetration isn't possible. But in your case, I don't think we have to worry about that. First, I'll drip some lube on your hole... Ahaha, it was cold and you jumped? Sorry. I'll put lube on my fingers too. Okay, all set. Now, I'll start with my index finger. Here we go—pressing the tip right against your entrance. Ufufu, your ass just twitched. Here comes this thin little finger, about to violate your hole. Are you embarrassed? Or excited? So cute. Now I'm going to spread your tight little hole and push all the way in. Squish, squish, squish... Wow! It slid right in to the base. Hey, even with lube, normal people don't take it this easily on their first time. You've definitely played with your ass before—fingers or toys, right? Someone as experienced as me can tell at a glance. This ass has already been played with. So? Time to come clean and tell the truth. Ufufu, I knew it. You've been dreaming about getting your ass fucked for a long time. And while playing with yourself, you ended up making it this loose. Ahaha, no need to be embarrassed. I've seen plenty of boys like you. If anything, it feels almost fated—like you prepared it especially for me to fuck. It's making my heart race. Let me see... looks like there's room for another. This time my middle finger... Squish, squish, squish... There we go—second one went in so easily. At this rate, a third will be no problem. Here comes the ring finger... Squish, squish, squish... Perfect—third one in without any trouble. Getting this stretched with just fingers is pretty hard. So you've definitely used some pretty thick anal toys, haven't you? But... you probably never actually came from anal play, did you? Ufufu, thought so. It's common for beginners. You read somewhere that anal orgasms feel way better than regular ejaculation, so your expectations got huge. You figured "bigger is better," ordered the thickest thing you thought you could take, but in the end you never reached climax—just ended up with a stretched hole. If you'd kept at it patiently for days, you might have eventually gotten there... But it takes time and effort, and if you live with family it's hard to hide. Plus, the first few disappointing tries crush your motivation—so most people give up. But don't worry. Since you're this loose, my cock will fit perfectly, and today I'll definitely make you have your first anal orgasm. Even if you never came, you probably found your prostate while playing, right? Of course you know it. The prostate—the "female orgasm switch" deep in a boy's ass. Like a boy's version of the portio. Hmm, your prostate is... right here, isn't it? Right... here. Ufufu, you just let out the cutest little moan. It's okay—moan more like a girl. The more you let yourself moan and get into it, the higher your sensitivity will climb naturally. So don't hold back—convince yourself you're a girl getting her pussy fucked, and let me hear those adorable moans. Here, rub rub rub rub rub rub rub... Good boy. I can't hold back anymore. I've confirmed you can take it, and that you can feel pleasure from your prostate. Time to get to the real thing. I'm pulling my fingers all the way out. Here we go. Ufufu, it feels good coming out too, doesn't it? Now I'm going to fuck you deep and hard with my cock. You'll feel the pleasure of being filled and the pleasure of being pulled out—over and over. Just imagining it is already driving you wild, isn't it? Now I'll pour plenty of lube on my cock... Spread it all over... Okay, ready! Grabbing your hips tight with both hands—no escaping now. A boy on all fours, trembling and panting, waiting to be penetrated... so pathetic and adorable. This is your big first time... Do you want it slow? Or all at once? Hm? Ufufu, as I thought—you want it hard and fast. Got it. Then I'll make this a night you'll never forget. First, I'll give your hole a little kiss. Mmm, smooch. Ufufu, you twitched again. Your ass is quivering right before getting claimed by a superior cock. Or... is it welcoming me with hot, eager kisses? That just makes me even more excited. Ahh, I can't wait anymore. Here we go. Get your pussy fucked by my cock and become my girl. Ready—go! Congratulations on losing your virginity. I'm all the way in—buried to the hilt. Ufufu, your ass-pussy is squeezing my cock so hard. I suddenly spread your virgin hole wide and crushed your prostate—it must be panicking and trying to push me out. Too bad. You're not moving me an inch. I'll pin you down and keep ravaging your most sensitive, shameful spot. This grip is incredible. You're trembling and breathing so hard. Even though you've stretched it, having something this thick this deep is a first—so you're scared? Then maybe I'll pull out for a second. Here—slowly... Ahaha, even coming out feels amazing—your walls getting scraped by my ridge, making you writhe. Almost all the way out... and then slam—deep again. You weren't ready for that, were you? You let out the most pathetic sound I've ever heard. I'm going so slow, and you're already this much of a mess—if I go faster, you won't last. Slowly out... slam! Out... slam! Hehe, how's that? Getting used to it? Then shall we start for real? No matter how good it feels, this slow pace isn't real sex. Don't worry. Earlier I went all in at once so you'd never forget losing your virginity, but from now on I'll be gentle. Ready for me to start thrusting continuously? Ufufu, you nodded so eagerly—so cute. Then here comes real sex. Here we go—slam, slam, slam. How is it? Not too much? You like this? Getting excited from my cock sliding in and out? You're doing great moaning like I told you to. Japanese boys really do make the cutest crying sounds. Hm? Asking if I've had sex with other Japanese people? You're so pure and adorable. Yes, of course. Whenever I see a cute Japanese girl while studying here, I hit on her. Actually, every girl in our seminar is already my sex friend. Surprised? You really hadn't noticed? Didn't you think the girls in the seminar were acting a little distant around me? I'm a futanari, but my legal gender is female, so even intense physical contact gets laughed off, and it's easy to get close. Then, once trust is built, I pick the right moment alone to reveal I'm a futanari. Everyone's shocked at first, but in the end they accept it with a smile. Just like you did. Thanks to futanari becoming widely known around the world. After that, every girl who learns I'm futa always begs, "Can I see your cock?" Some are just curious, others are shy but interested in sex and find it easier to ask a "girl" like me. I happily agree and show them my rock-hard cock. Then the rest is pretty much the same as with you. Their eyes lock on my huge cock, breathing gets heavy, and they make that sloppy, fully aroused female face. Once that happens, they're conquered—addicted to my cock. Japanese girls are said to be modest, but once they trust you, they become obedient like pets, moaning sweetly and shamelessly every time I pound them. So cute. After just one time, their bodies can't live without my cock anymore. Even though there are plenty of people with cocks besides me. Maybe because the only boys around them have tiny cute dicks like yours—all the Japanese girls are sexually frustrated. Oops, did I hurt your pride again? Sorry. But I do love boys like you with cute little cocks. You can't possibly beat someone with a real cock like mine, yet you get desperately hard anyway. Then you naturally lose, obediently offer your ass-pussy to the superior cock, and now you're moaning cutely, writhing, leaking pre-cum from your pathetic losing dick as it flops around helplessly... That miserable, ridiculous sight is just too adorable. Here, I'll keep thrusting while leaning over your back. Nnh, nnh, there. Yes—hugging you tight from behind. Keep holding us up on all fours, okay? Ufufu, in this position my big breasts press against your back—it must feel exciting. Boys really do love boobs, after all. But you also love getting your ass pounded from behind like this. Those moans aren't acting anymore—they're coming naturally from deep in your throat every time I thrust. Your prostate sensitivity is climbing fast. Part of it is me hitting your sweet spot perfectly with my huge cock... But the biggest reason is that you're genuinely excited and loving this situation. Hey, you're a masochist, aren't you? In a normal situation, you'd be the one grabbing a girl's hips and pounding her from behind like a man, making her moan. Don't you feel pathetic having your male role stolen by a girl like me? Everything happening now is because you love losing to a girl and being dominated—you're a total masochist. Normally, no guy would get on all fours and offer his ass just because he lost a dick-measuring contest. The moment you realized you were inferior, a strong sense of defeat flipped your masochist switch. You didn't care what happened anymore—you wanted me to pound you deep, to expose your most humiliating side as a man. You know what? Once a futanari girl fucks a boy's ass even once, he can never defy her again. He fully accepts his defeat as a male, and it gets etched into his mind and body: "I can never beat her." You instinctively knew that would happen, surrendered completely, and offered your ass, didn't you? You're such an incurable pervert. ...And I love it. I adore perverted boys who throw away all male pride just for depraved pleasure and offer their holes. Ufufu... As you wished, I'll make you my cute sex friend who can't live without my cock. Ufufufu... To make a masochist like you even more excited, let me push you a little further. If I cum deep inside your ass-pussy right now, what do you think will happen? When a boy gets creampied by a futanari girl, his cock gradually gets smaller and stops getting hard. Hm? Can't believe it? But ever since futanari became more common and recognized, there have been studies showing exactly that. I couldn't believe it at first either, but I've seen several guys whose cocks stopped working and shrank, so I'm sure it's true. When a boy gets creampied by a futanari, his body realizes "I've been turned into a female—I'm disqualified as a male" and completely gives up its male functions. Scared? Don't want to live with that pathetic loser cock? Or... does it excite you? Imagining getting creampied by me, turned into a complete female-fallen masochist who can never have normal sex again—does that send shivers down your spine? Ah, your moans just got louder. Hearing that made you even more excited? You're such a pervert who gets off on being reduced to a pathetic state. ...Go ahead, try to run if you want. If you keep giving in to this temporary pleasure and shaking your hips, you'll end up with an irreversible male body. Thanks to you servicing me so eagerly, clenching your ass-pussy around my cock, I'm about to actually cum. Every girl I've fucked, when I ask "I'm about to cum—what do you want?" begs in the sweetest, most desperate voice, "Please cum inside!" Are you the same...? Come on, what do you want? I'm pinning you down—you can't escape unless you clearly say "stop." If you really hate it, I can forgive you and not cum inside. ...But I desperately want to creampie you right now. Please? I love pumping my cum deep inside a pussy and impregnating a girl—it feels amazing. Your cock might never work again. But in exchange, I'll make you my sex slave and keep fucking you with my cock forever, just like this. You'd be much happier living as my sex slave—turned into a slutty anal girl who can take any toy—rather than as a weak boy with a tiny dick, right? So please—take all my cum in your pussy. Say it cutely: "Please breed my pussy with Helena's seed." ............Ufufu... Ahhh, you said it? You're sure? Okay then—no holding back. I'll shoot every drop I've saved up for you these past few days deep inside and completely turn you into a girl. Hm? What's wrong? Something coming? A feeling you've never had before is building? Hehe... Looks like your first female orgasm is finally here. Good. I'm about to cum too. I'll crush your prostate hard the moment I shoot—so we'll cum together. On top of the pleasure of anal climax, you'll feel the ecstasy of being bred—etching female joy into your mind and body. Here it comes? You're cumming? Your whole body is shaking. Good—I'll count down, and at zero I'll finish you off on your prostate. Show me your shameful orgasm face and become my girl. 3, 2, 1, 0! Nngh... Here it comes. I'm pumping all my cum into you—breeding you... Ufufu, what an amazing voice. The pleasure explodes from deep in your ass and floods your whole body—you're shaking uncontrollably. It's okay—collapse onto the bed if you can't hold yourself up. That's it, good boy. Here, I'll keep grinding your prostate with my cock. Grind, grind. Ufufu, you're stuck in continuous orgasm, can't come down. Getting bred by me, becoming my girl—your whole body is trembling with joy. Hm? Too much pleasure it's scary? It's okay. Here. I'll hold your hand. Cum more—keep cumming. Get addicted to my cock. Make it so you can't live without my cock. Grind, grind, grind. Ahaha, the moment you came you arched your back hard. Now roll over onto your back. You have the happiest face I've ever seen. I'm so glad you enjoyed sex with me this much. Your little cock is dripping pre-cum everywhere—such a mess. How was it? Getting fucked and forced to female orgasm felt incredible, didn't it? Now you understand firsthand why all the girls in the seminar became addicted to my cock. Your face says you don't need normal sex or even ejaculation anymore—as long as you have my cock. You're happy to be my sex slave, aren't you? No visible change in your cock yet, but after I creampie you many more times, the changes will start appearing—so look forward to it. Now that you've officially joined my sex friends, I have a present for you. Here—this. Know what it is? That's right—a chastity cage. A device to stop a boy from touching his cock or cumming or having sex without permission. Ever heard of orgasm control? It's a long-term play where a masochistic boy hands the key to a woman and lets her control his ejaculation. A boy locked in chastity will do anything for permission to cum—he becomes an absolutely obedient slave. For a man, losing the right to cum freely is unbearable torment. I get it—I'm a futanari too. Anyway, I want you to wear this from now on. Because you're my girl now. Girls don't need to ejaculate. Getting fucked by my cock feels way better than cumming. Your tiny cock is going to become useless anyway. Forget about the cock between your legs and become a complete female-fallen masochist who only thinks about being more feminine. If that makes you even more obsessed with my cock, I'll be thrilled. Please? I did sleep with every girl in the seminar, but you're the first Japanese boy I've ever approached. So you're special to me. I want to be much, much closer with you. Please wear the chastity cage, completely forget about your cock, and turn into a slutty girl who only thinks about getting her pussy fucked by me. Nnnn... yes... haa... you’ll wear it? I'm so happy. I really do love you. Okay, spread your legs a bit. Yes, perfect. First the ring around the base, then the cage over your cock, lock it to the ring, and finally—click. All locked. Mmm, it suits you perfectly. I brought different sizes since I didn't know yours yet, but bringing the smaller ones was the right call. Does it hurt? No? Good. Look—this is the key to the cage on your crotch. As long as I have it, you can't masturbate or have normal sex. Ufufu, only now realizing what a huge promise you made? Just thinking about me controlling your cock is turning you on? For a masochist like you, even the ultimate male humiliation—having a girl lock your cock—turns into pleasure. So cute. As your cock gets smaller, I'll switch to even tinier cages—so look forward to that. Oh, but when your lust builds up too much, you can do as much anal masturbation as you want. Fingers, toys—anything. Go ahead and relieve yourself as much as you like. Though no matter what you use, it'll never be enough, and you'll soon be craving my cock again. Ufufu. Now then—ready for round two? Hm? You thought we were done? One orgasm isn't nearly enough for me. I'm not letting you sleep tonight—get ready.