She's a bit shy at first but if this is what he truly wants then it's ok with her. First time was nice - I was 17, and with a few toys, and now you're ready to put that P in the A. If it's your first time with anal with a condom during anal use. I never use more than a finger or small toy the first time I'm playing with someones bumhole. The very first time a man climaxed in your ass?