How do I deflower my boyfriend?

I've (F20) been dating this guy (M18) for four weeks and so far we've gotten to second base. I like him a lot but he's sort of the sweet nerdy type and a virgin. We connect emotionally really well. It doesn't have to be full PIV sex but I want to escalate things sexually - how do I know if he's ready? I don't want to overwhelm him, I don't even know how to make the conversation sexual!! What if he doesn't even masturbate?? What if he doesn't like something but he's too nervous to tell me? I have no clue how sexual he is. I feel sort of weird because I'm not a virgin and also two years older.

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Wonk.

If he's nervous, just be understanding and reassuring. It'll probably be fine as long as you don't make him feel inadequate for not knowing what to do.

>What if he doesn't even masturbate??

Ask him. If he does, tell him you want to watch him and show him how you do it.

If he doesn't, then just show him how you do it.

If he's not interested, then he's probably gay, and you should wish him luck before moving onto a straight dude.

Not necessarily, I didn't start doing that myself until I was out of high school. I dunno, I didn't even know how exactly I was supposed to do it. It wasn't until I went beyond the initial few jerks that I realized the pleasure it could bring. I couldn't go back after that. I just got hornier as I went into my 20's. Some guys can be pretty reserved at first.

I’ll tell you how to do that after you two are married

>Not necessarily
Not necessarily what?
The user quoted considered the scenario where OP's bf does masturbate, the scenario where the bf does not.
What else is left?

>It wasn't until I went beyond the initial few jerks that I realized the pleasure it could bring
man I can't imagine losing my virginity to a woman like this, it would feel demeaning.

Just because he's not interested now doesn't mean he's gay. A lot of my hs classmates thought I was because I never told them if I liked anyone and in the past would tell them I liked some random girl that didn't even exist. I wasn't gay, I just didn't feel the need to bang girls until I masturbated the whole way for the first time.

>It wasn't until I went beyond the initial few jerks that I realized the pleasure it could bring. I couldn't go back after that. I just got hornier as I went into my 20's. Some guys can be pretty reserved at first.


Well, I guess you win the "who did I misgender" contest, because I totally read you as a straight woman, probably based on the pic related.

If you're trying to take a dude's gay-cherry, though, then I will totally BTFO, because I have literally zero experience with it.

But, in general, if you're in an intimate moment with them, and you start jerking them off, and they're into it, then you're probably okay.

I bet he masturbates to you 3 times a day

oh no why would it be demeaning? Dont want to demean him just want to get in his pants

How did you first start?

I used to be like that with my ex gf. We never got to have sex.

oh just personal insecurities actually, he's probably more than okay with fucking you.

Just dominate him

Start kissing, guide him to be on top of you, if he start to stop tell him to keep going, make moans, if he try to run leg lock and cow girl.

What makes you fall in love with him? Please tell me. I’m gonna try to emulate him.

Not to be gay but he's super sweet and kind to me and he's really emotionally intelligent he reads all these books about emotions and when I get stuck with homework he helps me also he's funny as all hell he gives literally no shits what strangers think so he's always doing weird shit

Anyways thanks guys, will show him the magical world of sexy sex soon

he's a man, so getting him in the mood should be trivial. Getting naked should be enough.

He's going to be too nervous to tell you anything. Don't worry about it. The first time is never great for a man, he will be way too focused on looking cool and experienced and awesome. That's just the culture we live in, and that goes double for men.

Just be calm, tell him it feels good etc and that you're enjoying it. If he thinks he's doing great, he'll feel more relaxed.
Don't expect him to cum, he will probably be too nervous to enjoy it, and possibly too nervous to maintain the erection for any period of time.
Alternately, he might cum within 30 seconds. Some guys are like that.

Either way, the important thing is to tell him that you had fun and that you really liked it. You can give whatever reason you want, just make sure he thinks you enjoyed it.

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>Not to be gay but he's...
So he's normal, just had the confidence to talk to someone.

This.