Maybe you suggest it over an intimate dinner.  Or perhaps, she brings it up while things are getting passionate between the sheets.  Either way, the topic has been breached, “What do you think about having a threesome?”  Once it has been mutually agreed upon and the 16-year-old boy in you settles down, you’ll have quite a bit of work to do if you really want this to happen.  Follow these guidelines and you’ll have a good chance at putting together a situation that leaves all three satisfied.

Banish Ulterior Motives

Make sure you’re both doing this for the right reasons.  Ideally, you want to share this experience because the idea turns both of you on and you think it would be fun.  This exciting encounter should bring you closer together sexually, not drive you apart.  Don’t do it if either of you are harbouring thoughts of ending the relationship and thinking this could be a good catalyst, or if one of you is bored with your sex life.  Be honest.

Who’s It Gonna Be?

Picking the right girl to share your bed for the night is an almost overwhelmingly daunting task.  This situation requires just the right combination of comfort and detachment.  Never, ever suggest one of your exes or even a girl you once hooked up with before your present girlfriend entered the picture.  Only in very rare situations will a girl from the past be the right candidate. 

In fact, your best course of action is to let her choose.  This way you avoid saying the wrong name and causing a whole mess of emotional turmoil.  Most likely, she will either choose a good friend of hers or a complete stranger. 

I would suggest going for someone in the middle of those two extremes.  Things can get very weird with her best friend later on if things go awry during the night and with a stranger, you’re always taking a chance that they might be passing a nasty STI on to you and your girl.  Go with one of her casual acquaintances.  Someone she’s close enough with to discuss the touchy subjects, but not a friend she will regret losing if things don’t turn out as expected.