Over the past year me and my girlfriend have gone from analingus to fingers to small anal vibe. Just the other night she asked me to use her Lelo Liv on/in her anus and later on that night she thought she would was ready for me to have anal intercourse with her. As soon as my tip touched her she changed her mind . I'm pretty average sized, but even average sized is bigger then the Liv. She's tiny (5 feet, 90 lbs) and is very afraid that us having anal sex will cause her a lot of pain.

Can somebody recommend a plug for her? One that we could leave in while we fool around and that will get her "ready" for me. Not too big, but at least as wide as the Liv.

For that matter, can somebody recommend a book or website for the both of us to read. She's very afraid of my hurting her, and that's the last thing I want to do. less

Two goodies: The Ultimate Guide to Anal Sex for Women by Tristan Taormino and/or Jack Morin's Anal Pleasure and Health for the books.

Have her start with the more serious exploration on her own. She's right - after the first time playing around with a small toy you're almost guaranteed not to be ready for penis-anal intercourse. Think about it yourself - if you played around a bit with a finger or the Liv once would you feel comfortable with her using a dildo of your size on you? Probably not.

You're on the right track with silicone toys. I'd say keep playing with the Liv, both on her own and with you (she needs to get comfortable enough to relax both on her own and with you in order for partner anal to be successful). You might want to get a mid-sized plug of about 1-1/2 inch (provided she's comfortable taking the Liv) and perhaps down the road a wider dildo, but for now work on relaxing with the Liv, fingers and maybe another toy. She has to be 100% comfortable with anal play being safe and pleasurable. less