May 072014
 

I have recently started a new relationship, and we have been getting to know each other including experimenting a little with different sexual things. The topic of anal sex came up and she is turned on by it, but so far her rule is “two fingers max.” She’s a very small person all around, and that includes her asshole. She wants to stretch her ass to accommodate my cock, so we want to know how to do it and how long it will take.

–Patient in Palo Alto

Her small stature does not necessarily have anything to do with how much cock she can take in her ass. Haven’t you seen those tiny porn starlets take huge dicks up their butts? It is absolutely possible. Her objective should not be to stretch her ass, but rather to learn to relax the sphincter muscles to make penetration comfortable and pleasurable. I suggest you begin slowly. Try one finger in her ass, your tongue or fingers or a vibrator on her clit, and a rousing orgasm. From there, let her set the pace as you work your way up from one finger to two, and so on. You can also work your way up with dildos or butt plugs in graduated sizes. You shouldn’t move on to the next step until everything feels great. How long it takes to get used to this new sensation, be comfortable with anal play, and work up to a cock in her ass will totally depend on her. Don’t be so focused on how long it will take, just enjoy all the fun you’ll have getting there!

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