Message: How to Prepare for Anal?
Anonymous: How do you prepare for anal? It frightens me to think that something big would force in there.
You don’t force anything in, to begin with. You start with something small and lubricated (always lubricated) that you can fit in comfortably (like a finger), and you combine gently inserting that with rubbing your clit or using a vibrator. You masturbate like that often, trying to orgasm while something is in your ass. As you become more comfortable with that, you try something a little larger (maybe two fingers) and repeat. After you can fit around the size of three fingers in without difficulty, buy a small/medium buttplug (something around the size of the Tantus Ryder) and work towards being able to insert that easily and wear it during masturbation or sex and even other times as well.
Continue gradually increasing in size until you feel comfortable trying with a trusted partner who will take care to go slowly at first and let you adjust and get used to his size. If anything hurts, take a break and do more warmup with something smaller.