So, I would like to consult the hivemind on sex with small penises and condom-haters.

For the first time in my life, it seems I might be entering into some sort of a fuck-buddy-esque situation. While I can see the thing going wrong in about a million ways, I would at least like to get some good sex out of it. Our first time together was nice but a bit underwhelming and, to be honest, confusing at times. I'm sure a lot of it had to do with him being nervous, but I would appreciate any tips on the following:

1) Small penises. Through coincidence rather than any conscious planning, I've only ever slept with guys with large-ish (but not freakishly so) members. My new fuck-buddy is less well-endowed. While I am not one to judge a guy by his tool, it did cause some surprising problems.

I like pressure on my clit while having intercourse, and thus like the missionary with my legs down or leaning over when I'm on top. Now, he insisted on putting my legs up high (even after I made it clear it's not my favourite thing) and I still don't know if it's because, ahem, he could reach me better that way or something completely different. And when I was on top, I had very little leeway to move before he slipped out. Any suggestions for positions that would give me some friction without requiring too much reach from him?

2) Condom-hating. Safe sex is super-important to me and I have zero intention of going without a condom with this guy. He, however, has issues with condoms to the point where he finds it extremely difficult to maintain an erection while wearing one. Have any of you encountered this problem or have any suggestions? I don't think he's doing it out of petulance or assholishness, and I'd really like to figure out a way around the problem. Cockrings? Some sort of super-human lube that will fool his penis into not feeling the condom? Viagra? I have no idea.

Thanks in advance, hivemind!