Rebecca is a 40-year-old financial-services manager who lives on the Danforth. She describes her look as “nerdy librarian” and herself as“smart, interested in ideas and politics, and a feminist.” She enjoys watching movies at home, going to pubs for drinks, and traveling, and met Gregory online.
Since my last relationship ended, I’ve discovered that I’m a bit kinky and submissive in the bedroom—I like to be tied up, dominated, and, occasionally, spanked. Dominance and submission is a fantasy of mine, and I’ve had some really positive initial exploratory experiences, mostly because I had very firm boundaries with partners.
Gregory and I talked online for about two months, and our chats slowly started to heat up. I liked that he was smart, from the same part of town, and dominant, but gentlemanly. I was ready for a relationship, and he was open to having one. He also had a nice smile and warm eyes.
We arranged the date via instant messenger, and decided on a tapas place. I tend to be guarded in the beginning, but I felt at ease right away with Gregory. He was very good looking, funny, and a bit older than me. It was a friendly, instant connection; we had lots of ideas and tastes in common. We talked about design, food, neighbourhoods, family, exes, and books.
It started to get quite flirty and hot when we talked about sex. For a couple of hours, we shared stories, our interests, and kinks, and it sounded like we would be very compatible. I could tell he was strong and confident enough to take control, but that he wouldn’t rush either of us. He told me later that he thought I had played our date very cool, watching and observing. When we left the restaurant after a few hours, he walked me to my car and gave me a hug. He didn’t even move in for a kiss. His reticence just made me more interested.
Our next date was pretty impromptu. I liked him, but I wanted to find out how much before I brought him home. After another three hours of great conversation, flirting, and holding hands across the table, I dragged him to my place. No blindfolds, no restraints, and no anal were the rules that first time. He spanked me, called me bad names, made me serve him on my knees, and then smothered me with warmth and affection afterwards.
We’re still together. We have kinky sex, we support each other, and we have long, smart conversations with lots of flirting and handholding. The spanking remains damn hot, but now, occasionally, I spank him too.
Rebecca rates her date (out of 10): 8
Want to be a dating diarist? Email datingdiaries@thegridto.com