ok well i've had my fair share of meaningless one night stands and have always found the sex enjoyable. I actually lost my virginity to a strange at a festival and have never had any regrets I think perhaps your getting to caught up in the detail and planning. And if your already having doubts etc then this probably isn't the way to go about losing your virginity. Let it happen naturally meet a girl and if it feels good and right for you both let the mood take you WHAT I'M GONNA SAY NEXT ISN'T MENT TO OFFEND YOU; your an adult now and yes it's good to have fantasies, but dismissing things because it isn't the "perfect" scenario is quite immature. Sex isn't paint by numbers and it's not a movie, things happen that are unexpected just like everything else we do in life Have fun, use condoms and relax !