hey about my 1st time.
we had been together for maybe 8 months.. i'd never had sex before, she had but a long time ago.
i asked her a recommendation for condom and bought what she suggested, when the time came it was difficult to keep it up, could penetrate, but any movement would cause me to slip out, i found the condom was very tight, but i thought it must be normal.
after the 2nd time without much luck she told me i was too big for that type (20cm long and 15cm circumference.) i went out got a large size and omg so much easier to get it over and doesnt strangle...
Unfortunately the large size is too short and it goes inside her and she pulls it off if were not careful, so i'm trying to find something longer..
but yeh, would recommend measuring urself before buying condoms for the 1st time, made my 1st experience rather terrible, but i guess 99% of 1st times go like that anyway :)