I want to have sex, but how can I get a shy guy into a situation where we might have sex? This is more of a relationship question—sorry. I’m a college student who loves being on top. Lately I’ve only been having sex with my papas, but I really want to do it with someone my own age, and I can’t stop masturbating. The other day, I hooked up with a new papa, and we had amazing chemistry and an incredible time, which made me want to do it with someone my own age even more. (Even though the physical chemistry was great, he was over 20 years older than me and wasn’t exactly handsome…)
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There’s a handsome guy five years older than me whom I’ve been going on dates with lately (we went out both yesterday and today), and I really want to have sex with him. On our date yesterday, he invited me to karaoke after dinner. I thought, “According to my statistics, fewer than 4% of men won’t make a move on you at karaoke. Well, he’s handsome, so why not?” But we spent two hours seriously maintaining social distance, each singing more than ten songs, and then called it a night.
He’s so handsome he looks like he could be in show business, but he’s extremely shy—so shy that he’s aware of it himself. Both of his last two girlfriends cheated on him, and he’s not very good at conversation, so he can be boring, but I really want to have sex with him. Until now, whenever I’ve been alone with a man in a private, dimly lit space, they’ve made a move on me 99% of the time, so I honestly don’t know how to make the first move myself. I have plenty of experience, but when things get heated and the flirting starts during sex, I’m usually the type to say, “Stopppp” while getting all worked up. I feel like if I make the first move, he’ll assume I’m used to doing that.
Obviously, having sex at karaoke is out of the question, so I really want to go to someone’s place or a hotel.
How can a girl naturally make the first move and invite a guy over?
I do want to date him properly, since sleeping with someone before becoming official usually ends with you becoming fuck buddies. If I really want to date him, should I avoid rushing into sex?
Even when I’m with my papas, I never initiate anything—I only do it when they invite me—so I have no idea how to break out of this situation.
👤Asked byGuest👩GenderFemale🎂20s👑Universe female member
Joe’s plan sounds good.
Still, I think it’d be better to go and take at least one lesson or trial session. I feel like you should make it look as authentic as possible, even if it’s just for appearances.
How to have her lie down, how much to undress her, where to start the massage—having seen those things firsthand makes a big difference compared with not having seen them at all.
That said, if you’ve experienced it yourself, I think you’ll probably be fine even without taking a lesson.
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Akki, a married woman I’ve recently become close with, also enjoys being on top, just like you do. I gave her a Womanizer as a gift, and she was delighted.
By the way, I once asked Akki, “What do you do when you want to get your husband in the mood?” Her answer was, “It’s easy—just give him a massage.” She’s quite the strategist, you know. Apparently, she actually went to a massage class to learn. At first, her go-to line was, “Will you be my practice model?” but she says she doesn’t need that anymore, so she quit the class（笑）。
So why not try a massage operation yourself? No, you don’t need to take lessons. Just say, “I’m studying massage so I can learn a useful skill. Would you be my practice model?” and start casually. Going straight for his private area would be too risky with a shy boyfriend. I recommend starting with the soles of his feet. In fact, foot massage was what Akki learned. According to her, it also gives you an excuse to have him lie on his back.
Don’t try to take things all the way on the first attempt. After you’ve tried a few times, say, “It’ll be easier to massage you this way,” and ask him to take off his pants. Then you’re in control. Move from his feet to his calves and then toward his inner thighs. Your handsome boyfriend’s package will probably be standing at attention.
Don’t climb on him right away. This is where you should take the straightforward approach and whisper, “I want to be with you.” If he gives you a firm nod, it’s time to bring out your specialty: being on top. What do you think?
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Start by telling him, “I’d like to be your cute girlfriend first,” and see how things go.
As for papa-katsu (compensated dating in Japan), you’ll probably have to either keep it completely hidden or quit.
Akari
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If I were to make a move in a karaoke booth, it would only be with a woman I was already intimate with.
If you genuinely want to date this handsome guy, don’t rush things.
If you’ve been going on dates regularly lately, I think he’ll eventually be the one to ask you to make things official.
The unfortunate part is that physical attraction and sexual chemistry don’t always match, haha.
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