I find that with each new girl I start sleeping with then I have to go back to square one of only penetrating her to an extent (i.e. probably about 75% of my length at the start) and it takes a month or so of quite regular sex before I can get up to about 90% penetration. Now I'm not saying that sex is all about it being as deep as possible; it's more that the more of me that they can happily accomodate then the less likely I am to hurt them and hence the more enjoyable the encounter can be. So far I have found that the missionary position is good but lifting the legs up towards their head means that I have to be much more careful. Doggie style is good as it is easy to control the depth. Taking them vaginally from behind whilst they're lying down can be an excellent position as I can really go for it as I simply can't fully penetrate them and they enjoy it too because of the good rubbing that happens. Then there's there's taking her from behind whilst in the spoon position and this works well but quite a few girls always find it uncomfortable, which I've never understood. I've discussed having anal sex with only two of my partners and tried with both of them - but both said it was too painful. Any tips on how to help this? (We used lots of KY and were trying it doggy-style - any better "learner" position?) Any thoughts/tips/advice would be greatly appreciated.