[Handsome Creepy Eel]

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anal

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straight answer

Not making fun of you, it's just a funny combination

Ok, on a more serious note you need to give us more details. What kind of lubrication did you use, when and in what amount? Was a condom involved or not? What position? Did you do any foreplay, including playing with her pussy and first slipping a finger or two into her ass? She needs to be very relaxed.

If you don't do this, then lots of pain is expected. If you do, then pain will be more on the hurts-but-feels-good level for her.

p.s. Samseau has written a great guide to anal sex somewhere in the Game section, but I can't find it right now. Maybe someone else can help.