My First Time Pegging an Older Man

God, I just love how pathetic men can be for me

Especially the older guys. You know, the ones who front like they have their shit together then beg for my ten inch dildo when we’re all alone. I always thought dating an older man would look like something different. Like maybe I’d take a back seat for once and let someone else take control. Boy was I fucking wrong. My first time pegging an older man happened after hours and hours of him literally begging me to shove one of my cocks in his ass. So you know what I did? I made him suck it first.

Maybe there’s something about being a little older that makes men feel, I don’t know, rather shameless. Whatever it is, it took my relationship with this dude to a whole new level. And fuck, I loved being in control. My first time pegging an older man opened up this entirely new dynamic. When I say “suck” he says “how hard?” And on occasion, when I feel like getting some action, he loves the humiliation of having to put on one of my strap-ons so I can actually feel something inside me.

Things would only get more interesting after my first time pegging an older man.

Come to find out, actually, my new plaything happened to have a wife at home. I found out one day after a rough session. I was passed out on the bed and he was in the shower when his phone began to ring. Didn’t think much of it, I let it ring till it was finished. Then another call, and another, I swear there were at least five back to back calls before I finally picked up the damn thing to see who was blowing him up. Strange that he didn’t even bother to hide the fact that this woman was his wife. I almost thought about picking up and telling her all about my first time pegging an older man, and how it was her man at that…. was it possible he wanted me to find out? Either way, now I knew it.

This opened up a whole different kink for me: blackmail. We’d come so far from my first time pegging this older man. All I had to do was mention his wife’s name to get what I wanted. Reluctant to let me use my 12 incher on you? Well let’s see if Darlene thinks it’s a good idea. Too embarrassed to wear my heels and call yourself a sissy bitch for me? I bet Darlene would love to see that! That was my magic word. My ticket to every single thing I’d ever want from this man. I was on cloud nine and in complete control, more now than ever.

My newfound control over this dirty old man invigorated me in so many ways…

If he could have two women at the same time and still experience all the pleasure he could possibly want, who’s to say I couldn’t do the same? I didn’t just want blackmail, I wanted everything. Pegging, cuckold, blackmail, humiliation – the list goes on and on. My first time pegging an older man was long over. He needed to suffer for keeping secrets from the women in his life.

When I was done with him he’d have nothing but ultimate respect, and maybe a little fear, for every woman he’d ever come across. He wanted the best of both worlds? I’d make him entirely aware that I could, too. I’d tie him up and invite over the most large, masculine, big-cock men I could find to fuck me in front of him. Hell, I’d even invite some women to fuck me… just to let him know that he wasn’t special. And a woman could satisfy me more than his pathetic cock ever could.

We were so far away from my first time pegging an older man. Felt like centuries ago by the time I was done with him. He was a great learning experience, and a total ego boost when it came to practicing my control over pathetic, whiny, sissy older men. What can I say? I love men who love cocks. But my needs began to exceed what he was able to give me. He was still after the relationship side of things. I had outgrown any affection I felt towards him. Of course, he’d always be special to me. And I’m sure he’d see me again. I always remember my firsts.

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