My first experience with a MILF came when I was 17 before my senior year in H.S. Was working in the local vet clinic. This older woman, very attractive with a nice bod, brought her dog in to have it neutured. She walked back to the holding cages with me and I knelt down to put her dog in a lower cage. Still kneeling and looking up at her I could tell she was looking at the semi-hard bulge in my 501's. She made a comment something to the effect - "bet all your equipment's working fine." Handed me her business card with her home phone and said - "give me a call when you get off work."
Did and she invited me over to her house. She'd been recently separated from her husband and gave me a run for my money in the hornyness department. Continued to fuck her on and off every chance I got that summer till I went back to school and she her house and moved out of town. Compared to the H.S. chicks, I'd dated prior to that time, she was a winner, hands down; no whining or excuses and the fact that she was experienced was a big plus. That woman knew what she wanted. To this day, I'm a sucker (excuse the pun) for cougars.