Most of the women in this thread have made a very distinct distinction between "random women" and "my friends" and I'm not sure why there's a distinction between them.
I'm not picking on you MM, you're just the last one to make the line explicit:
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I like pornography. I give my boyfriend pornography. I encourage masturbation and fantasy. But I would be offended if I found that he was masturbating to pictures he had secretly copied off of my friends' web sites. Sorry, it's just wrong. Not only would be it be disrespectful to me, to our relationship and to my friends, but I think it would betray a lack of judgment and character that I would find to be very dismaying.
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So you like pictures of random naked men and women. You give your boyfriend pictures of random naked women. You encourage him to masturbate to said pictures of random naked women. But you'd be offended if you found he was masturbating to pictures of a SPECIFIC naked woman that you know?
Why the divide?
A naked woman is a naked woman, whether you know them or not. I really don't see why you need to differentiate.
My hypothesis is that anyone freaked out by naked friend instead of naked random person is (in reality) insecure about their appearance and afraid that their SO will leave them for their friends. The reason it is "freaky" with friends and not random strangers is their proximity; the 'threat' of them leaving you for the other person is presumably higher, because they actually have geographical access to the person?
The only problem with that presumption is that it's a stupid one. If someone is going to cheat on you, they're going to do it regardless of physical distance. Sure, their proximity might increase the likelihood - but if you're really worried by that increase of probability, then you have other issues to deal with (like that either (a) you don't really trust your SO or (b) your SO is a cheater).
To further add; if I'm going to be downloading pictures of naked women, there isn't a hesitation in my mind - "oh, I know this person. it'd be weird for me to do this." Why is there for you (or women, in a generalized sense)?