I met a woman online who was nearby and (through reading my posts on this very website) interested in trying this very fantasy out with me. Well... we got to know each other online/over the phone before she came out and said it... but she made it pretty clear once the idea of meeting came up that she wanted to try this specific thing out.
I'd never 'been fucked' before, and made that very clear to her (but I was totally into trying it!). She told me she had used a strap-on before, but only with other females.
Long story short, we met in person, things clicked between us, and after a few more meetings we set aside a weekend to get a hotel and 'share all of our wildest fantasies' :biggrin1:
We didn't try this until Saturday evening, after spending the better part of 24 hours getting to know each other's bodies in a more standard sexual sense. Honestly, 'pegging' was okay, but we were both kinda let down by the experience. Watching this beautiful woman get that dominant look in her eye was hot as hell but for some strange reason I had a hard time climaxing... and I think that with the amount of time I took in that regard, she got kinda 'tired out' after a while. The feeling of being penetrated left me kinda let down to be honest - not bad, but not great.
Afterwards we switched places, and put ourselves in the exact positions the other was just a few moments before... we both had a lot more fun like that :biggrin1:
Her and I have met a few more times since then, and probably will again soon (she's probably gonna end up reading this too lol). We haven't done this since, and honestly this is just something we joke about now.
I'd be more than willing to try it again, but I can live without it. I think that about sums up how she feels as well.