Jul 4, - Should I try it? Be careful with whom you do it. Could be very risky. This is very graphic, but you should know this before you do anything like that. One of the Double penetration with boyfriend and toy. If you need to post a picture, you should be going to a doctor. • All posts here . To this day, this is one of the best orgasms I have ever had. Anyway I tried DV once but they couldn't both fit in there and one of them gave up.