Can two anal virgins learn on their own instead of outside help? Family tells me I have to have a guy show me how to know my body... .-. Which pisses me off. Who knows your body better than yourself? So do me and my boyfriend need outside help for how to do anal. The anal key points, when to push when not to? Someone told me he can only go so far before he pauses. Only I will experience the pain to know that right? Weird question I know. But please help.