In my years as a libertine, I’ve learned through trial and error that some basic, flexible guidelines help me to make the most of the lifestyle I’ve chosen, with as few hassles as possible.
The most important rule is that anyone I have sex with for whatever reason must be a fully consenting legal adult, needless to say. This is to protect myself and make my life easier. The fact that teenagers tend to get on my nerves makes this rule easy to keep.
Condoms are important for one night stands, though I do tend to dispense with them fairly early on in an ongoing relationship. I also do not get into relationships with active alcoholics, drug users, or those with major mental illnesses. And I am strictly heterosexual.
Another strict rule is to never make a promise I have no intention of keeping, because it will bite me in the ass every time. This goes for both one-time deals and for ongoing relationships.
For a one night stand encounter, I make it quite clear at the outset, that I’m not interested in anything more than the one time. It’s important to me that anyone I have sex with be doing so fully informed and of their own free will. I’ve been turned down many times, but it’s no big deal. For every one who is offended by the idea of casual sex simply for it’s own sake, there are others who are turned on by it. At the end of such an encounter, I tell them I’ve enjoyed it and say goodbye, with none of this "I’ll call you" bullshit.
For ongoing relationships, both casual and of the more emotional variety, explicit honesty is even more essential. At the beginnings of such relationships, I tell them upfront that I am a libertine, and just what that entails. I stress that I will never be faithful to them -- even if I come to love them in the course of the relationship and that I do not believe in legal marriage. (I was married once, very briefly, in the early 80s, but I’ll not do that again). I also tell them that I don’t expect them to be faithful to me. I am not attracted by clingy women with no life of their own. If they can deal with that, we give it a try and see how it works out; if not, then no harm done.
I tend to prefer married women, or those in long term "marriage clone" relationships, as they usually have other things in their lives important to them and don’t need me to "take care of them" or are looking for a husband. I will not get involved in any kind of ongoing relationship with a married woman in any kind of abusive situation, however, as I have no desire to get involved in the middle of shit like that, nor do I want to possibly make things worse for her.
When I do get involved in a satisfactory ongoing relationship with a married woman, I am discreet, doing nothing to call attention to our relationship in public. Nor do I have any interest in getting between her and her husband. Their marriage is their private business and I have absolutely no interest in it, whatsoever.
I also have had ongoing relationships with unattached women, though these can sometimes be more complicated than with those in other ongoing relationships. One common problem that occurs is that the woman might be able to accept non monogamy intellectually, but as the relationship progresses, she finds she can’t quite accept it emotionally. Several times, either consciously or unconsciously, the woman has hoped that once love has entered the picture, that I’ll suddenly decide I want to be monogamous, after all, and want to get married, just as it happens in romance novels. Unfortunately, I’ve had a few relationships to end because this issue could not be resolved between us. The most successful relationships I’ve had with unattached women have all been with those who are very independent and who are usually libertines as well.
Nothing is hassle-free in life, but this has worked well for me in 30+ years of being sexually active.
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