My First Time Pegging a Man

The Opportunity for my First Time Pegging

One of my favorite and most powerful sexual experiences in life was my first time pegging my pandemic-era boyfriend. His name was Hunter. We met in the elevator of our shared apartment building exactly twice before the world shut down and quickly decided to lock things down together. He lived two floors above me, and on our second meeting, he helped me carry a large package into my place. One innocent “thank you” drink led to another, and the next thing you know, he’s got me pinned down to my bed and is absolutely devouring my pussy. Never have I had a man take such control over me during a fuck session. He turned me into an extremely flexible little fuck doll and had never been more turned on in my life.

A Man Like Him Could Make Me Do Anything

We were six months into our cocoon of lust, shaken up together between our two apartments. I learned Hunter had a lot of restless energy, not being able to play his passion of rugby anymore. I was more than happy to let him exert it all on me. For such a strong, masculine man, Hunter was an extremely open-minded lover. The two of us both had fun testing out different toys wrapped in the heat of a well executed roleplay. So when we exchanged sex confessions and I admitted I’ve always wanted to peg a man, he gave it about 30 seconds of thought before offering himself up. Never did I think my first time pegging a man would include such a domineering man like him.

The One Condition

Hunter had one condition for his first time pegging experience. He said it had to be a strap-on bigger than his cock. This was the true surprise for me, because that man was packing at least eight inches. We mutually explored a variety of butt plugs and he did love the occasional finger in the ass right before he came. However, going from that straight to a nine inch dildo, was a big leap. After a few days of intense internet research we ordered all the pegging components we needed. I had picked out a cute and naughty black leather harness with red devil horns on it. Hunter picked out a nine inch long and 3in wide black dildo and a large bottle of lube.

First Time Pegging Tools

The package finally arrived three days later and I swear Hunter looked more nervous seeing that box than he did during any rugby match he’d ever described to me. We spread everything across my bed like we were preparing for some filthy little ritual. The devilish harness alone made me feel powerful. Sliding the leather straps up my thighs and fastening that huge dildo into place completely shifted my mindset. Hunter just stared at me with this mixture of excitement and intimidation that made my entire body throb. I could not believe that for my first time pegging a man, it would be a physically dominant one and not some pathetic little cuck. I was about to make this rugby champion, my complete and absolute bitch. The focus of our next roleplay would be a dark and passionate blackmail affair.

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