Pegging My Boss after Catching Him Riding a Dildo

I fucked my boss with a 12″ strap-on.

Pegging my boss was a whole new experience for me, and it was so fucking hot! I had plenty of experience with kinky roleplay ideas; in fact, I’d even taken a co-worker on a sissy shopping spree! But I never dreamed I’d catch HIM doing something so naughty, much less joining in and pegging my boss. But one afternoon, I caught him in the act. I’d slipped into a meeting with him to look over a project with him. However, in the middle of it, I heard something interesting. His private office was rather quiet, so the only other sound should have been the fan he had blowing on the desk and the whirr of his computer. But in the midst of it, I heard a constant buzz. And now and then, it would fade to nothing, then grow in intensity again, almost like one of my vibrators.

After a few more minutes, I started looking at him funny. A little head tilt paired with a suspicious look. If he had a vibrator in his ass, I wanted him to really blush and squirm. So I started turning up the heat. “What is that? Do you hear that?” I mused, looking around the room as if searching for a cricket. He looked bewildered as I stood up and walked around the desk, looking blankly at the shelves… before settling my attention on him. Now, it was clear to me that the vibrating sound was coming directly from him; specifically, the buzzing was coming from his seat, muffled only by leather and black work slacks. With my naughty thoughts racing, I wondered if anyone was pegging my boss… He sure seemed to like things in his ass!

I wanted to be the one pegging my boss.

By this point, he looked mortified. I knew exactly where the buzzing was coming from but I acted confused as I walked back to my seat. He looked relieved for a second until I ruined it. “Is that a vibrator?” He was blushing in shock, but I just smiled. “Oh, it is…how big is it?” With my prying questions, my poor boss eventually caved in, admitting to all of it. He had an 8″ vibrating dildo in his ass, and he was barely managing to keep it in. He said his Mistress ordered him to keep it inside him for at least one meeting today, and she was controlling the vibrations through an app. She was the one pegging my boss! And now I wanted a turn.

So I stood up and walked over to his office door, shutting and locking it behind me. And as I turned to stroll back towards him, I finally noticed the growing bulge in his pants. “Drop them,” I ordered, pointing directly at his clothes. He stalled for a second, and then his impending orgasm won him over and he tossed off every piece of clothing. “Now bend over the desk, let me see what she’s fuckin you with.” I circled him, eagerly taking hold of the vibrator’s flared base as soon as he bent over. Now I was the one pegging my boss, pulling the big dildo out slowly, and pounding it back into him. He moaned like a whore as I did that, leaving me giggling with mischief. “Aw, do you like how I fuck your ass?”

I thrust it into him again, pegging my boss harder.

The vibrations had him on edge already, and they’d helped relax his tight little hole for nearly an hour. And here I was, finally taking control of him and pounding my cock into his ass. I pushed it further and stretched his little asshole, making him arch his back and whimper like a little bitch. “Who’s your Mistress now?” I asked him, the question leaving my lips as I pumped my cock into him several times in quick succession. I was pegging my boss so hard and the sensation drove him wild with ecstasy. It made him cream all over the desk in front of him as he called out my name.

There’s something sexy about turning a man into my little ass whore, I loved pegging my boss. Do you wanna be next? Call me.

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