Me and my Boyfriend (15 and 16) have tried Oral sex several times now and he can penetrate me perfectly fine without problems. But when i try to penetrate him he moans that it hurts. He says as I'm entering him that they're generally isn't enough space lol sorry had to laugh at him there. His Penis is 7.5 Inches and mine is 5 Inches. We don't use Condoms as we have both gone for Doctors checks to see if we have any stds etc... And they told us we're both fine. We use Lube tho. Would using a Condom help in anyway? Not sure what questions to ask because I'm not sure what the problem is.seeming as his Penis is bigger and he can Penetrate me perfectly fine. I guess what i need is any tips on how to make it more comfortable and less painful for Him?