My first time

The first time I ever played with a guy I found him to be rather understanding and willing to help me along my journey to finding the inner goddess in me. He came out from the western suburbs where he was staying for the evening, cabbed all the way into the city, then took me out toy shopping.

We had a great evening at Leather Sport checking out all the cuffs, collars, whips, and canes. He asked me to pick out anything I wanted, didn't matter how much it cost, and he would buy it for me. I picked out my very first pair of leather cuffs for both the ankles and the wrists. I had also picked out a rather long riding crop that was rather thin on the end.

When we got home from shopping, I made him strip down. He was a thin man, maybe 5'7", and a decent size cock. He looked wonderful in the cuffs with his ass in the air awaiting what I would do to him.

He was married at the time, so I resisted leaving marks, but that did not deter me from some ass play and leaving a nice mark from the riding crop that was gone before the session was over. He told me it was a marriage of convenience more than for love. Amazed me that couples still got married politically rather then for family or love.

As he was kneeling there with his ass in the air, I could not help but play with his ass. It was one of the first things I learned to do with a boy. He loved my vibrator going in and out as it was covered in veins, but the best was taking some old glow slicks from the freezer and playing with his sense of touch. I would blindfold him, place one of the glow sticks in his ass and then use a couple and lightly rub them on his skin.

I loved watching the goosebumps appear on his flesh and playing connect the dots with a marker. I would draw out all kinds of designs on his back and make him try to figure out what I was doing. Sometimes I would run my nails along his sides, he would squirm, but in the end his skin would be covered in goosebumps that I would start singing the song from Pee-wee's Playhouse "La-la-la, connect the dots, la-la-la."

He liked when I had control of his body from his ass, nipples and cock. Loved when I would work his ass with my dildo and stroking his cock at the same time. I would edge him so close to cumming that when I stopped it would be dripping onto the hardwood floor. Pushing his face down into the puddle that his cock just drooled would seem cruel to some of you, but he loved the humiliation of it.

I would make him lick his cum from everywhere it might fall, from the leather of my boots, to the dirty wood floor. He loved it all. He was even surprised when I would stuff ice cubes in his ass and then make him try to answer complex questions while trying to keep the water in as the ice melted.

Thought we did not see much of each other after a few brief encounters, I sometimes wonder if he comes to chicago on business or pleasure with another Mistress.

I miss playing with my first, but I have since moved on to bigger and better things. This weekend I will use sounds on a boys cock and he will not know what hit him.

Stay Kinky Chicago!

Mistress Julie

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