Guys, When should I tell him I’m a virgin?

I met a guy online and we’re kind of hitting it off. Not to put the cart before the horse, but if things keep going well- when should I tell him I’m a virgin? Guys- would you want to know before you officially started dating a girl or is it something you wouldn’t mind finding out after a few months?
Updates:
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Update with another question: what’s a good way to tell him/say it? Something along the lines of “I feel like this is going somewhere, so I wanted to tell you before we get to far that I’m a virgin...” I just want to be able to take things slower/get comfortable with baby steps, not waiting forever just until I find a guy that’s cool with that
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Superb Opinion

  • There are many possible reasons why you might want to tell your partner you're a virgin: You intend to stay that way until marriage. You want to be intimate but you're afraid you won't know what to do, or won't be any good. You want to share your sexual histories since you will likely be intimate at some point. It depends on your reason dear Pink Anonymous.

    • It’s definitely that I want to be, but I’m afraid of not knowing what to do/needing to stop/not being good or able to handle him... so I’m that case, any advice?

    • First, let’s get started with an important reminder: you get to decide which sexual activities are and are not on the table for you. Your body, your rules.

    • If penetration is the thing that feels most triggering to you, you can try taking baby steps towards getting more comfortable with it on your own. Masturbation is one of the best ways to practice. The next time you masturbate, take plenty of time to unwind before doing anything. Take slow deep breaths, counting to five on the inhale, holding for five, then counting to five on the exhale. Start off your masturbation by focusing on your clitoris, so you can get even more relaxed and start feeling pleasure. Then, hold a finger against your vaginal canal. Keep taking slow, measured breaths, and see how your body responds. If you feel any tension or panic, move your finger away and take a few more breaths. If you feel up for it, bring your finger back and try again.

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Most Helpful Guy

  • Before you start having sex, definitely. I don't know if there's a single right time, you may have to play it by ear. You'll want to take it slowly at first (and that's likely how you're feeling, anyway), and remember that the first time is usually rough and awkward, and sometimes painful. Stick with it; it gets better.

    • Any ways I can make it less rough/awkward? Lol I’m super eager, but obviously that eagerness isn’t matched with experience haha so I won’t actually know what to do

    • Take advantage of what you've learned through masturbating. Everyone's a little different in what they like, and the gap tends to be wider in women. This means that even if he's had a lot of experience, you'll need to help him through what you enjoy. Experimenting is fun, don't get me wrong, but it will likely take a few tries before you fall into a rhythm. Communication is key, and don't take it so seriously that you forget how to laugh if something funny happens- that goes for both of you! If you leapt ahead too fast or too far into dildos and vibrators, you'll need to remember that a natural penis can't match them in terms of the sensations it can give (if you haven't, don't be scared of them, just remember that they're there to supplement, not supplant). You'll both learn with time. The key is to keep talking and take it as slowly as you need to, without being afraid to move forward.

    • This is really helpful, thank you... possibly a dumb question but going along with what you’ve said... When it comes to showing him what I like/ what I do to myself (example: clit rubbing), is it best to just do it myself and hope he takes over, put his hand there and ask him that way or like somehow actually ask him for it? If that makes sense... like I don't know how much of that is vocal versus me showing him/guiding him (and vice versa)

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What Guys Said

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  • I wouldn't mind finding out after a few months. It'll be a pleasant surprise, but ultimately, it wouldn't matter to me much one way or the other.

    • Is there a good way to say it? Like do I just say it Casually when I feel things escalating? Do you normally have a sexual conversation with a girl that would be a good opportunity for it to come out?

    • If it comes up organically, I guess. If you ever have the conversation of "Well what kind of stuff do you like?" that's a pretty good time to slip in "Well, I'm a virgin, so..." Or it may never come up. You might just have a passionate moment all of a sudden. You'll know when you get there. Just do what feels natural.

    • Does it change things/ruin the passionate moment for you? Like if a girl were to tell you when you were really getting into things, would you stop and talk about it, wait for another time, etc? Or keep going?

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  • Depends do u want the question awkward or normal

    • What do you mean? Can you explain?

    • Dont make it that he questions it just tell him when it comes up but after read wtf he says guys there are always creeps

  • I love virgins, as I'm virgin too lol