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I'd also suggest going to the bathroom at least an hour or two before. And if you ever get to the point of wanting to try rough anal sex - an at-home enema beforehand is a good idea. :thumb:
also as for it hurting, yes it does hurt if too ruff and it goes really far up. gulp. i remember my first time i was drunk thank god. it went straight up and it really really hurt. the best thing is to lay on your belly, make yourself comfortable and relaxed plenty of lube and take it easy. you got all night afterall. dont rush it please, you could cause both yourselfs harm. do it at your own pace and im sure you will learn to enjoy it.
as for anal sex being classed as the "gay way" this is not the case. many straight couple have tried it at least once within a relationship.