You can lose your virginity however you like . I am someone who doesn ' t think your first time needs to be ' special ' or even with someone you love if you just don ' t care about that stuff . In fact , when I read your title I assumed with was a a female asking and my first thought was go for it ! However , there are a few practical reasons I think that , as a guy , a gangbang may not be your best bet . Gangbangs are kind of difficult for the guy . Often you ' re standing around with a bunch of other dudes watching a chick have sex and then when it ' s your turn you need to get in there , fuck and get out . Staying hard under these circumstances can be surprisingly difficult . You ' re basically responsible for getting hard and staying hard and then you have to perform on demand . As well , there ' s some expectation of stamina . You ' ll stand and wait , then maybe getting oral for a bit , then stand and wait and maybe get PIV for a bit , then stand and wait , then maybe some more PIV , etc . So you ' ll want some idea of how long you last especially during PIV and you don ' t have a basis for that comparison . So if you have an issues around performance anxiety OR if you ' d be really messed up if this goes badly , I ' d take a pass . Also , if this is a regularly occur event , talk to the organizer and see if you can go once just to watch though as a single guy they are less likely to allow that . Why not just find random 1 on 1 sex online ? That sounds a whole lot easier for your first time . Okcupid , Plenty of Fish and Fetlife are all great ways to find casual encounters .