The first time I was pegged was with an old girlfriend. Asked her if we should get a strap on and she couldn't have raced to the sex shop fast enough. She bent me over her bed that night and ass fucked me. While I still like the feeling, I much prefer the raw flesh of a man up my ass compared to a toy. They're so stiff, in a not "hot cock" way. I was still insecure back then, so I regret a few things, mostly that she was very fun and kinky and today me would have had a threesome with her and another guy. Too bad.