A few years ago, my childhood friend and I (both about 14) were hanging out. My friend had just gotten her first “sexy” bra and thong set, and decided to strip down and show it to me. I obviously got horny and touched her body, but it never got any further. We’ve both dated guys, but I’ve caught her watching lesbian porn before (I do as well). Now that the years have gone by (we’re both 18), I’ve always thought about that day, and if she’d be interested in having a lesbian experience. Do you think it’s worth a shot, and how should I approach it?

Are you looking for a sex buddy, or moving to the next level of an already established relationship? Your approach depends on your intentions, so talk about it with your longtime friend. What are your intentions, since sex among long time friends muddies the waters of what you have established so far.

Actions have consequences, you should know that from your other dating experiences. So approach this VERY honestly and honestly look deeply into your intentions. Going from friends to sex buddies, or friends with benefits, is a very big deal, and should be treated as such. Honestly, and THOUGHTFULLY.

That's what females have always told me so that's what I will tell you. Yeah I'm a guy! An old school type of guy.