First times can be tricky things sometimes.
Sometimes they can be pretty straightforward; the drunken, random, don’t ask their name, don’t tell them yours one-nighter. Yes, I’ll admit that I’ve had my share of these. In this situation, it’s basically just a fuck, it’s what both parties want. There’s no “getting to know you”, there’s not even the slightest consideration that this might become a “thing”; it’s simply just fucking as an elaborate form of masturbation, with little or no consideration for the other party. To be honest, in the grand scheme of things, they don’t really even qualify as “first times” as there’s very little chance of them ever being repeated.
No, the first times I mean are the “date” types.
There’s the whole fuck on the first date, or wait dilemma. If I fuck him on the first date, will he think I’m cheap/easy/a slut? If I wait until the second or third date before fucking him, only for the sex to be crap, have I wasted my time when I could have fucked him on the first date and moved on?
There are no right or wrong answers to this.
Yes, I have fucked on the first date and yes, sometimes I have waited. There have been good and bad experiences in both situations.
In the case of Master C and me, it’s fair to say that we didn’t date until after the fourth or fifth fuck.
The sexual politics and double-standards can be a bit of a minefield though.
Sometimes, you just know, even on the first date, sometimes right at the point of meeting them, that the night is going to end up in bed. The chemistry is there, the spark, the lust, it just all clicks into place and by the time the meal/drink/film/welcoming kiss is over, all both of you want to do is tear each other’s clothes off and get down to it. If that happens, great. If the sex is even half way good and the guy isn’t a total out-for-himself bastard, there’s a pretty good chance you’ll do it again. If it later transpires that despite the quality of the fucking, the rest of the relationship is non-existent, you can move on and at least you’ve had some fun along the way.
Similarly, sometimes it pays to go a bit more slowly. You may like him but he doesn’t quite excite you. You try a few more times and you either decide to fuck him or fuck off. I will admit to the fact that there have been occasions when I’ve fucked him and that has been what has finally decided me to fuck off, but that’s a different issue.
The truth is though, there is no “right” time to fuck somebody for the first time other than, possibly, if it feels right, then do it.
The other dilemma, having had that first fuck, is do you want to have a second? That is one that only you can decide. First fucks are rarely mind-blowingly great, but there is usually enough indication as to whether or not repeated practice would make it worthwhile. If you’ve unleashed your world class blow-job skills on him, and he’s reciprocated by giving your clit a perfunctory and obligatory flick of his tongue before climbing aboard and giving your cunt a two minute pounding before rolling off and starting to snore, then the chances are, you’re probably not going to give him another chance; but what if the reason he came so quickly was that you were just a little too enthusiastic with your sucking, leaving him no hope of lasting? Maybe a second try once he’s got his breath back?
Your instinct is probably your only real guide; only you can decide how much pleasure giving potential he has. Ultimately though, sometimes a girl just has to move on and prepare herself for her next first time.