I've had anal sex before with my ex who was average and so the anal sex was comfortable. Recently I started talking to an old fwb again who is above average. His thickness is a major turn on and I'm really excited to start having fwb with him again but he wants to try anal for the first time. I'm almost hesitate due to do it because it's hard to give him a bj due to it being so thick that I have to really widen my mouth and jaw. Due to his size, how can I prepare myself to do anal? Mind you I'm not used to using lube or anal play or fingering. I'm not one to give up so easily, I really want to try for him because he has told me that the women he has already slept with refuse to give him head and to do anal. Any advice or suggestions would help. UPDATE: On Saturday, I finally met up with him and I told him that I really wanted to try anal for him but he was more concerned with hurting me (very sweet, I know) so he wanted to wait to try anal. So I was able to give him head and deepthroat him first even with his thickness which then caused him to cum too soon after we started to have sex afterwards. He felt so bad, but I was happy to satisfy him with head because I really did want to try for him. Within a few minutes he was able to get hard again and continue having sex, and when he finished he said I was too tight for him. LATEST UPDATE: we did it! No lube necessary just used my natural pussy juices like expected and it was very enjoyable and so he too enjoyed it. Unfortunately a few hours later I ended bleeding which is normal. So at the moment I'm healing and am not going to tell him because I don't want him to feel bad.