Strap-ons
I am, alas, an anal virgin. When I was in my late teens and early twenties I was exclusively gay and topped maybe a half dozen times. I've been married twice and have had sex with two women in addition to my wives. I have not had anal sex with a woman. To date I have had nothing larger than a fleet enemy in my rectum. However, largely as a result of reading the posts on this site, all this may be changing, at least in my mind. I find myself fantasizing about both fucking shemales and getting fucked by them. Whether I'll actually do it is another matter. Knowing how squeamish I am just at the mere thought of a rectal exam, I do have my doubts. However, I have read posts that suggest starting with small objects, eventually working up to cock-sized dildoes. Maybe this would be a way to go.
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