>>6831221Dick size actually does matter. A long one may be too long and won't go all the way in because of your internal anatomy - there's only so much space.
If it's short, but thicc, it will feel like you're being STUFFED with a dicc, and if you've not done much with your butthole, it will hurt quite a bit with some bleeding if he goes in raw (no lube) and just jams it in.
>does it feel better than masturbationDepends on the person. Some people can achieve prostate orgasm which feels SO MUCH BETTER than standard orgasm for men, but others can't, no matter how much they try.
If you're wanting to experiment, I suggest you buy a medium-size dildo and lube it up before going in; insert slowly and gently, don't just ram it in there.