try approaching him from a different angle. Ask him if he knows how much he can take? turn it into a challenge, buy a dildo similar to your penis and have fun with it without alluding to the fact you want to have sex straight after. just have fun, and if all goes well, the both of you will be so turned on and prepared it should go easy. This is how I was broken in, anyway. Anything more than three or four fingers got a little uncomfortable, then my boyfriend got me a vibrating dildo as a challenge. Sex wasn't the immediate agenda, but after a good hour's play i could take the entire 8 inches. So there you go, and hope you have some fun!!!