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Finelooking ladyboy assnailed in bathroom. NHS 'Is sex painful the first time? We are not able to acknowledge receipt of emails. Use lots of lubricant! This is because you could transfer small amounts of faeces to the vagina which can cause urinary tract infections such as cystitis. Please let us know any comments you have about the content on this page. For penetrative sex, make sure you use a condom and lots of lube — some people feel safer using extra-thick condoms for anal sex.