C, 29

Lubricated condoms are fine, but you're going to need more lube than that. Get yourself a nice water based lube No Vaseline!! Try Astroglide, or I prefer KY Silk. Anal-eze and lubes like that also contain a pain killer. It's going to hurt, and you gotta know when it does hurt so you can take it slower. If you are numb, you could go too fast and damage things. Take it slow and after the initial pain, relax and it will be enjoyable.