I (41m) was 24 at the time. My best bud and I went out to a nice dinner to celebrate a promotion I had received. We went to a nice restaurant, which was on me as I got a good raise. It was an Italian joint and we were drinking lots of wine.
Our waitress was a tall blonde with an amazing ass and some perky C tits in her early 20’s. She was super cute and her and I started flirting almost immediately once we were sat. My friend and I talked about how hot she was and I told him I was going to take her home with me. He laughed and thought I was full of shit. After we ate my friend had to go and I told him I was going to stay for another glass of wine. When the waitress came back she asked where my friend went and I said he had to go. She said, “well I hope that doesn’t mean you’re leaving too” I told her I could use another glass of wine or two.