23.Sex with A Straight Friend

Sex with A Straight Friend
Fred's and a straight friend: I am gay and my best friend is not, but I think he is bi curious. By the way he is happily married. We have talked about gay sex before and although he says he has more enjoyed seeing lesbian sex than gay sex he has insinuated that he might strongly consider experiencing gay sex. I tell him all my gay sex adventures and he seems very interested in them, although I haven´t been able to tell if he was aroused or not. Sometimes I feel he wants to ask me, or lead me to having sex, but I do not know if I should make the first move or not, and I know he won´t make the first move. He is probably expecting me to go first as I am the out gay guy. I figure if he wants to experience gay sex it might as well be with his best gay friend rather than with a stranger, although with a stranger he might not need to see him again if he didn´t enjoy it. In the past we have had a threesome (M-W-M) and we were all comfortable and I caressed his penis (shaft) while he was having sex and he didn´t say anything. What shall I do ?
Advisor says: Well I think the issue here is do you want to have sex with such a good friend if it may complicate things between you? In situations like this where it is difficult to talk openly about something, most people will give hints and ideas as to what they want or how they are feeling. Often if they don't then it is something they are not willing to consider at the current time.
Maybe he does feel attracted to men as a lot of married men do. There is a natural bonding between men and this can lead to intimate experiences between men even if they are not gay. Maybe this is what your friend is feeling? You may find that the best answer here is not to push the situation as it could turn unfavourable. Maybe he is happy to listen to you when you talk about gay sex and maybe he does like the idea but it is something that he would never actually be able to contemplate as he is married.
At the end of the day the decision to pursue this is going to have to be made carefully and you will have to try and judge the situation as it unfolds. You wouldn't want to ruin your friendship although if you have already had a 3-some with another women and you talk about gay sex then it would seem that he is someone who is already pretty open minded!
You could always try going out for a few drinks with him one night and just be a little bit more flirtatious with him or make a few remarks about having sex with him and see his reaction. You can word this in a very neutral way just to judge reactions as this will help you decide what he is thinking and what it is he wants!