I've played with anal toys throughout much of my life and dabbled briefly in anal sex (me being penetrated) with a girlfriend a few times. I believe early on I experienced a very slight amount of tearing as I had a burning sensation and a very small amount of bleeding after bowel movements for about 2-4 days after. But then everything is fine. I can use fairly small anal toys (1-1/4" or less in circumference) without any problems (no bleeding) as long as I'm very careful with insertion. My wife is open to using a strap-on so I'm going to propose we begin experimenting. We've found a dildo that is 1-1/4" in circumference and I read reviews on anal lubes and find a highly rated one that is a lot thicker than your typical water based lubed. I have several questions: 1) Is there any way to strengthen my anal tissue to make it more resilient from tearing. I suspect I have some minor scaring which is sensitive to tearing. Would rubbing or injecting some Vitamin E oil or cream in my anus every day for a few weeks possible improve things making me a little more resilient or some other treatment? 2) My wife is a clean freak. Until now I take care of the insertion of the anal toy and clean-up. Most times it comes out clean although some times it can be a little dirty. If her strap on gets visibly dirty - it's going to be a major turn-off probably to the point she won't want to continue strap-on play. I know my cycle in that almost every morning I have a bowel movement so I know that is not a good time for strap-on play. However, I've noticed that as I've grown older (now in my early 40's) my bowel movements take much longer and I find that I am sometimes impatient and end up sometimes ending my bowel movement prematurely only to have to have another one an hour or too later (just haven't got accustom to having to sit on the pot longer.) I suspect an anal douche before anal sex would remedy any possibility of things getting messy, but that could be a major mood killer. I'm wondering if possibly taking a small dose of a gentle laxative at the right time would insure that I have more complete bowel movements in the morning so that I'm cleaned out all the way until I go to bed? I just would not want something like that to backfire on me though.
I recommend douching first. It can be done a little while before, privately as not to kill the mood. I have a friend who tried it and said it worked wonders.