I was planning to post a question along these lines when I found this thread. As always, I turn to my friends in the forum for advice and input (no pun intended).

My little sub has expressed a willingness to experiment with anal for some time. We haven't gotten around to it yet but we have a free weekend coming up. I recently came into a little windfall of $$$ so I'm planning a trip to the "toy store" later today to pick up some nipple clamps, a HUGE dildoe and a butt plug. I want to break her into anal in such a way that it can become a normal part of our sex. Over the years I've been around a bit (I'm 15 years older than she) and I've had women that tried and hated anal, most that will tolerate it...and one or two that actually liked it. This one likes a certain amount of pain and I think she would really like it if broken in correctly. My idea is this...

I thought about buying a moderately sized butt plug and a topical anesthetic. I figured that after she is tied, whipped and I'm working her with her dildoe...when she is really excited, I could insert the plug to get her relaxed and loosened for later. I was thinking that the anesthetic might minimize the pain of her first experience and make her more available in the future. This is just a personal "brainstorm" and nothing I have tried before. Any thoughts or ideas from those of you with more experience would be welcome.

If she wasn't special I'd just do it...but this one is a keeper and I want to go carefully. She has enjoyed every form of bdsm I've introduced her to so far and I'd reall like to add anal to the repertoire. I'm looking forward to your responses. She is usually tied "spread eagle", but I can change that if it will work better.