Pegging

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.
 

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I also love it with role play too. After I split from my long term ex, I dated a Tanzanian woman for a short while. She would play boss/secretary role play where she would ...... me after finding I was looking at porn. She would release the strap on from under her business pencil skirt, make me suck it and then fuck me while telling me she was the boss now, I was to give her a pay rise, I was her little bitch and I would have to do what she said. (Sometimes she would make me wear lingerie, lipstick and heels). Honestly, it was heaven.