If you want her to include anal into your regular sexual menu, you have to repeat the above procedure many times until she gets used to it.
If she has a strap on dildo up his anus at the time he comes, it's certainly going to be a new experience for him!
Ir you will tear and that hurts bad.
If you're a man, you can see how it adds to sexual pleasure if you stimulate your own anus with a well-lubed finger when you masturbate.
Description: You or she can stimulate her clit at the same time. The combined finger play of the vagina and anus in this way, whether or not accompanying cunnilingus, is graphically termed "the Bowling-Hold" in American slang, from the similar position of the thumb and middle finger in holding a common bowling-ball.