I agree with Confused. There's no rush. The more comfortable you are, the better. Work towards getting comfortable doing what you're doing now, and gradually crank it up (if you so chose). When the time is right, you'll know.

As far as your hypothetical scenarios go, it's hard to answer if it would count, given that what people consider "still a virgin" varies from person to person, sometimes wildly. Honestly, in regard to that question, I think if it happened and someone asked each of you, he'd probably say "Oh yeah it counted" whereas you'd probably decline. I wouldn't worry so much about that, as it's hard (if not impossible) to get a definitive answer.

If for whatever reason (mentally or physically uncomfortable, too much, you want a snack, whatever)at any time you want him to stop, tell him in no uncertain terms to stop. Immediately. If he has even an iota of respect for you, he'll comply. There are no exceptions to that.

Preparation on an emotional and mental standpoint is getting comfortable with him. Don't rush into this. Take things slow, and get more comfortable with intimate settings. It's like easing your way into a swimming pool, going from the kiddie section to the deep end. Allow yourself to get comfortable with one depth before moving on (and no, diving is not an option for the sake of this analogy )

Physically, it's all about the foreplay and respect to your wishes. The more aroused you are, it's infinitely for the better (more lubrication, more...what's the word...open? ). Arousal with also help with the mental state a bit. He should know this is new to you, and respect your wish to be gentle. It'll take a bit for you to adjust to him, and it'll (as I'm told) gradually feel better, with subsequent times being less and less of an issue. I don't know too much with certainty about what to expect as far as the hymen (if that's even an issue...some people aren't even born with one . Just covering all the bases here), as I've heard varying accounts from "painless" to "slight pinch" to "unbearable agony" (to be fair, the third one only popped up once in sarcasm, but you get the point ), and it will bleed a bit the first few times, but nothing extensive, as I'm told. It might be beneficial to ask the women's section if you're concerned about that particular point.

Lastly, try to relax a little. The more apprehensive you are, the more difficult. Just make sure you are comfortable with this guy before you go further, and make sure he respects you enough to treat you the way you deserve through this.

And of course, be safe*, and have fun.

Hugs,
Harley

*PS: In the event it does happen (in which case, congrats! rofl Among my friends at the same age, I'm doing a really poor job if this were to be considered a race ), you -may- want to mention the IUD you mentioned in your other topic. I've heard they can...lol well, poke back, if they're inserted too low. I dunno how much of a poke that could be, but he should probably know, if nothing more than for a courtesy.