As a rideshare driver, Saturday nights are a lot of fun. You get to meet many interesting people from all walks of life. St. Patty’s Day weekend was extra festive, the green beer flowed, and business was non-stop.

I picked up a beautiful solo woman rider in her early to mid 30’s from a bar in the Wrigleyville neighborhood on her way home in the West Loop. As I ask how her night was, she says, “It could be better.” She enjoyed a night out on the town but was disappointed with how her date turned out. As a result, she was on her way home alone.

As she talks about her disappointing evening, I notice her breathing change, each breath a little shallower. I look in the rearview mirror; our eyes connect as she shows a playful grin that invites trouble. I hear that very light and distinct wet sound of foreplay as she starts to bite her bottom lip. There is no way that what I think is happening is happening. Do I dare turn?

If you know me, you know that there is no way that I would let this moment pass without knowing for sure. Temptation overcomes my good sense as I turn to confirm what I suspected. She had her skirt hiked up, and knees spread enough apart to give me a glimpse of her fingers pleasuring her very wet kitty. I can’t believe this was happening in my vehicle.

She would achieve an orgasm tonight regardless of how her date turned out. I don’t know who her date was, but I have him to thank for the fantastic experience that ensued in my car. No, we did not have sex; I did not even touch her. It took every ounce of restraint not to touch her. I simply can’t assume the risk that this was a trap to later allege assault while on the Rideshare’s clock. But I drove slowly and eventually arrived at her destination and sat in the car, watching until she was done.

She regained her composure, smiled, and hurried inside the house as she looked back, smiling. I would not indulge while on the rideshare’s clock, but it created a new RP kink that I’m dying to replay while off the clock.

So if you are ever in Chicago and need a ride while enjoying a night on the town, be sure to contact me. There’s a lot of fun to have while off the clock.