this is real cute but you're making a lot of assumptions there bud. how do you know i was dry, etc.
in answer to your question which i think was related to me losing my virginity...hmm..i guess pain that you can't control (ie period pain, or rape) is always worse because you can't prepare for it mentally. in that case, period pain is generally worse but there's the one time in losing my virginity he didn't stop in time, that fucking killed lol.