Since I was eighteen, I always had a thing for elder women. Though I never had crushes on my school teachers or even in college, but mature women always fascinated me.
I have had my fair share of elder women, in fact, as a 19 year old, I lost my virginity to a 32 year old neighbor, Nikki. It had started with her catching me staring at her since I was 18, a bit of childish flirting followed. I used to make any excuse to be at her place, even babysit-ted her 2 yr. old kid, just to be around her. Her elder sister, about 35, knew what was in my mind and even she used to openly flirt with me - whenever on weekends she used to come over at her place. A couple of times, we ended up kissing and I had seen her naked, while changing or while using a shower a couple of times. She never discouraged me or stopped my advances, but it was lack of confidence or waiting for the right time, that it took a long time since we finally fucked! Since then I have had 4-5 relationships with women who are about 10 year elder than me. Growing confidence and better understanding of women emotions and the ability to have a good conversation has helped me a lot.
But this story, is about my encounter with a 42 yr. old lady. I am 32, working as a financial consultant. I joined my new firm about 2 years ago, and am doing very good in terms of my career. Have a good rapport with my boss and also my team.
About three months in my job, I had to travel to Japan for a week and in this context I met Carol. Carol was the secretary of the Admin Head of our office and she was the one who used to arrange the tickets, stay, visas and Forex. On my first look, she came across as very very desirable - she looked around 35, high cheek bones, just a hint of cleavage in a white shirt and a grey skirt up to her knees. The things that impressed me the most - were her shapely legs, perfectly accentuated by the black high heels and her ass. For a short woman, she is about 5'4 - I am 5'10 - she had great legs and the tight skirt made her ass looked delicious.
She was the prototype of my kind of women, and I immediately wanted to make a move, but being relatively new in the job and her being the secy of a very senior member of the company, I kept things professional. Even she was a thorough professional, she ensured that all my travel requirement were met and she even suggested a few clubs and decent dinner options.
On my return, just to have a window of interactions and possibly more, I got her a bottle of wine, just as a token of appreciation. I got it delivered to her desk with a simple note of thanks. She called me a few hours later thanking for the wine.
I didn't see much of her in the next few weeks, but met her once at the cafeteria. I had a long evening ahead of me and even she was going to be late. We chatted for about 30 minutes while we had our coffee and some light snacks. She was married, had a 10 yr. old daughter, and lived near to my apartment and loved running and swimming. I swam few times a week, but played tennis regularly. Her daughter had started playing tennis recently and she asked me if I could coach her a bit for her school tournament, by then, I had really got a liking for this lady and happily agreed. I would get a chance to meet her on weekends and the possibilities were endless! We parted ways, finalizing to meet at my club on Saturday morning. I invited her to swim at my club before the tennis lessons, hoping to see her in a swim suit!
