I am 45, a professional, married 2x, with a great sex life. However, at this stage in life I enjoy a good jackoff session. My fetish is legs and high heels and it all started when I was 16 years old. I have told this to no one, but feel comfortable to write about it now.
When I was 16 I had a girlfriend who would give me handjobs, but go no further. Her older sister, 18, was known to be somewhat of a 'slut'. I could have gotten what I wanted from her but I was too shy. So I enjoyed the handjobs and enjoyed more jacking off and dreaming about her older sister. We lived in a beach community and the girls had a pool in the back yard. One day I realized I could watch the girls walk past my house coming from the beach. So rather then locking myself in the bathroom with a copy of Playboy I stole, I planned to wait for them and from the basement window get of good view of the girls on the sidewalk. After what seemed hours I spotted my girl and her sister walking up the street. I ran into the house. Of course no one was home. Into the basement, dropped my shorts and started to pound my meat. And what a view! My girl, blonde, tan, with knockout thighs. (remember I was born a leg man) She had over her swimsuit a yellow rain jacket. Her thighs drove me wild and I thought of her hand stroking me. Her older sister had a bikini. Just as they passed the window I let go my load all over the wall. Wow!!
I cleaned up the mess and made this jackoff a regular thing.
A few weeks after that, I told my girlfriend how much I love to look at her thighs as she jacked me off. I eventually got the guts to convince her to wear that raincoat and a pair of her mother's high heels. Then one day after she was ready to give up on me after 15 mins of jerking, I was shocked as she took my hand and said, 'you do it. I don't mind.' We went out for a year after that and sex was her posing for me in those spike heels, in shorts or a swimsuit. Then things really got crazy when her mother caught me in their bathroom, looking out the window at the girls by the pool and stroking my cock.
To be continued!