The first time I was pegged was back in the 1970s, long before the term pegging came into common use. We called it role reversal then. Luckily the woman who topped me was very experienced (and larger and stronger than I was at the time).
I was dressed up (wig, collar with leash, makeup, bra, garters, stockings, heels), spanked, and bound with my wrists secured behind my back. After I gave her some fellatio, she bent me over doggy style and gave me a pounding I will never forget.
I had no idea what to expect and thought I was being ripped apart, and cried and howled like a little girl. But once I realized that the louder I cried, the more aggressive she got, I realized that she had done this before, so I placed my trust in her skill. It is a shame that chastity devices weren't available then.
When she was satisfied, she spun me around and gave me a glowing, smirking, approving look. I then melted completely and cried like a baby. She held me tightly and I thought that I never wanted anything more than to be her little
****. I thanked her profusely when she was done with me, and saw her several times after that.
Unfortunately we lost touch, but if I found her today, I couldn't thank her enough for being her wonderful self. She had the strength to be her true self, but sadly I listened to everyone but myself, and paid the price many times over.