I’m a younger guy, 21 now I was 20 at the time, and I have a thing for older women. Usually 28-35, this in part to my more recent revelations that I am more submissive, and a lot more to do with the fact that older women generally tend to know what they like so sex isn’t a guessing game.
I had met this woman on tinder a few weeks before, our messages were flirty at first, but grew to be highly erotic as time went on. She had an incredible imagination, and the words she used and descriptions she gave had me in ecstasy many a time.
This brings us to our first time actually meeting. I had invited her out for dinner, she said there was a Panera near her offices(she is a huge fan of Panera) and we decided to meet there after she got off work. It was a cold day, even just walking from my car to the door of the restaurant left me with a few shivers and rubbing my hand together. I had chosen my favorite outfit for the occasion, black jeans distressed on the thighs, a white button-down shirt with blue and purple floral print on it, and a black satin jacket that cut off high on my neck. She was wearing a short black skirt, enough to preserve modesty, but even so she had her legs crossed, a burnt orange sweater, with a thin silver necklace and matching earrings, along with her stockings and short black heels she was quite a sight. I could feel the eyes of every guy in the restaurant on me as I went to sit down. Feeling a little awkward I embraced her quickly before sitting down, trying to ignore all the onlookers. She was far more confident than I, head high and a light in her eyes as she looked me up and down. I’m on the shorter side 5’9 and thin, I played soccer and tennis most of my life so I never put on much weight, but still have an athletic build. I could tell from the curve of her hips and the definition of her arms that she took excellent care of herself. As we were talking and waiting for our order numbers to be called, I felt her heel grace the inside of my leg. At the time I thought nothing of it, until it happened again, and a third time. I could almost feel her wrapped around me as she gave me a playful smile with the most beautiful gleam in her hazel eyes.