I lost your e address so hopefully you will find my reply here. Yes, bananas make a good beginning toy for use with your fella. Several advantages, you can pick most any size you might feel comfortable with. Just be sure they are fairly green and stiff! You mentioned that he might be a little hesitant at first so I would suggest that the next time he is going down on you that you use one on yourself. You will want to be quite vocal about how much you are enjoying the banana and he will probably get the idea the next time you begin to play with him. The lubes I use are fairly simple, mineral oil or Crisco. They have the advantage of being edible as well as being cheap to use. You will want to take a tiny slice off the rough end and you can always cover it with a ribbed, lubed, condom. I also use a homemade lube that is really really slick but we can cover that later. Good luck with your anal play and hopefully he will cum around for you.