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Depending on your personal views from sex, but I'd just say that like anything else there is a 50-50 chance of things going smoothly, at best. Find out if either of you are jealous types, with histories of strong posessiveness, then verbally and respectfully lay your rules and boundries. You can't know how either of you will react for certain, but if the act under the specified circumstances isn't going to cause either of you undo grief or guilt you should be fine. Always be clear before and after of where you two stand with eachother, respectfully. This all goes for him of course too. Without boundaries though, its just far more likely to end up an emotional mess. One problem you may have judging from your post is the difference between being attracted (emotionally? physically? both?) is if its just a fear of commitment and emotional attraction exists, then it is almost guaranteed to get messy or into a relationship. If its purely physical on both parts, you might be ok. Generally only really mellow people or very flighty people can get away without too much emotional entanglement, as long as there aren't any mixed signals of course.
"The Greatest Enemy of Knowledge is Not Ignorance, It is the ILLUSION of Knowledge. Stephen Hawking"
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