My wife has always wanted to try anal but was also too afraid it would hurt. I told her to take her time and let me know when she was ready. So we asked some of the couples here at todp for some advice and many said to start with lots of lube and toys.
So these first pictures are of us doing that and she was in heaven. She kept it inside for over an hour and just let me rub her clit to a couple of orgasms during that time. Needless to say it was hot!
Next time we're going to try having anal sex. She told me she's ready and we will post those too.