WHO YOU DATING
INTERNET DATING AT ITS BEST/WORST
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(2009/09/09)
 
I don’t know why, but the title of this post sounds like a Sylvester Stallone movie. If I was as smart as Stallone, I could get eight or nine posts out of this one theme. I could call each post like, "Rocky Sex," I through VIII. That's right, the first sex can be rocky and we'll get to that.

Anyway, as noted in the kissing post, we are all pretty much no longer virgins, so sex should not be quite as hard as it was when we were sixteen in the days before free love.

Many people today are products of the free love generation and have a healthy, modern attitude about sex allowing them to hop into bed with you relatively soon and without all the hoopla that used to proceed sex in our prudish past.

Sex is no longer a taboo that results in condemnation to hell and an eternity of shoveling hot coals, unless, of course, you contract some STD that causes your private parts to feel like they have been shoveling hot coals for an eternity.

There is really no schedule or rules about having sex for the first time. Much of the decision is all about common sense. If you are the shy type or if sex is painful, or if you are not looking for a sexual relationship, it may not happen so fast or at all. It is not proper to force anyone unless you are an invader, plunderer, or rapist.

If sex is important to your relationship and the feelings are mutual, it's going to happen and there are some guidelines for those of you who need them.

As a rule of thumb, or shall we say a rule of penis, after three to four dates, you can reasonably expect to have connected sexually.

If you engaged in sex on the first date, that may be considered inappropriate for an online Internet date. It's just not classy, though it is fun.

First date sex is more common when you meet someone at a bar and get sloshed prior to the actual sex.

Second date sex on your iDate is not unheard of, and is generally related to chemistry (a good thing) or how horney you are (not always so good to let your hormones dictate your behavior) or desperation (not such a good thing).

Holding off sex for too long is a way to lose out on this person. We are grownups, and as such, it shouldn’t take you ten dates to figure out if you want to sleep with this person.

I can see holding off sex for up to five dates, but after that, there may be something wrong, unless it’s a morality question and you, or they, don’t believe in premarital sex.

This, of course, tells us that you, or they, want marriage as the outcome, and that’s okay as long as both parties agree.

There are those women (I think you know this isn’t generally a guy thing) who will not sleep with a guy without a commitment and that doesn’t have to mean marriage. It could just mean a commitment to an exclusive dating arrangement, a.k.a - a committed relationship, also known as a monogamous relationship, and if you are really old and still have any memory left it used to be called “going steady.”


This “no sex” without commitment is more “old school,” often times has religious overtones, and it is actually very noble and probably safer both physically and emotionally. You have to respect that in a woman, and if you really like her, you will. And if it’s the guy who feels like this, wow, he’s a keeper; or a nut case; or has something wrong with his penis.

In either case, there should come a time for the first sex. So how do you go about this often times awkward first sex?

It is best to set the stage. Rather than making an attempt to do this at a movie theater, or restaurant, wait until you get back to your place and try luring the person into your bedroom by suggesting that you watch a cable movie or cable special using the great line, “I only get cable on the TV in my bedroom.”

This offers the opportunity to lay in bed and watch "the movie."

Now if you are clever, this movie should be so bad that you start talking and pretty soon you lean in for the kiss. This should not be the "first kiss" as discussed in The First Kiss post. By now you have kissed this person goodnight at least once or twice.

You take it from there. It’s kind of natural, like riding a bike. No it's more like climbing a tree. That doesn't explain it well either. It's more like doing the mambo in a horizontal position. Oh, just "do it."

Since you are over the first kiss thing. It should be smooth sailing, unless there are issues to address, like, “before we do this, I wanted to mention my penile implant” or “I think you should know about my colostomy bag", or the fact that you had a sex change operation. These are all issues that could hinder the normal progress of first sex.

Assuming everything is okay, you can expect either a very receptive partner or perhaps some coy, hard-to-get protestations like, “What kind of a guy do you think I am.” Oops, it will more likely be, “What kind of a girl do you think I am?”

By the way, the answer to that question is, “The kind of girl I’ve always dreamed about.”

Realize that first sex is not always ideal sex. You may be so excited by the newness factor, the forbidden fruit factor, or the performance anxiety factor that you guys may become impotent or ejaculate prematurely. The women, for the same reasons, may become frigid, dry, or start crying.

If you are a caring person, you have to show compassion and understanding. It is best to joke about it and try again later now that the ice has been broken.

Just a note of trivia: Alaskan ice fishermen never have these problems with breaking the ice.

Since the first sex may not be ideal because of the essence of first sex, you have to be open to see the potential that it could get better, or you may miss something that becomes really good.

It is very likely that if it’s not great the first time, it will get much better as the comfort level matures.

There is also the possibility that it will be the best sex you’ve had in the past year; partly because you haven’t had any sex in the past year, or because the chemistry is there and there is nothing hotter than first sex with a new partner if you can get over your inhibitions.

Of course, it could also be terrible because you or your partner are just not very good at sex. The good thing about dating versus the old time practice of planned marriages is that if you are not compatible, you move on.

Second and third sex should be better and better. It only starts going downhill after you've been together for a while, especially if you got married, and you've had time to take each other for granted. Don't let that happen or you will be on Internet dating sites as a divorcee in no time at all!


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