I am a middle aged man who still loves to masturbate at least once a day. I was a late bloomer in this regard. I did not start masturbating until I was 16. I was a virgin until the age of 19.
Most of my early masturbating sessions involved imagining sex with women I knew in my life. Most frequent image was of my Mother's cousin Allison. Ally was about 10 years younger than my mom and was like a little sister to her. She had short blond hair, a beautiful face, a little on the heavy size with huge breasts. She lived in the neighborhood and would visit frequently. As I grew up and became more 'aware' of her, I would often sneak upstairs to jerk off during her visits. She had a flirtatious personality and would often tease me with little off color remarks or long hugs where she would push her tits against me. This went on until I went away to school. I only saw her once again before I turned 20 and that was at her wedding when I was almost 18. She married an asshole who thought he was God's gift to women.
The next time I saw Ally was at my parent's surprise anniversary party. We lived across the street from a playground and everybody parked there. It was a wild party. During the party I danced with Ally. I hadn't seen or talked to her in almost 2 years but still jerked to her quite a bit. As we danced it was obvious to anyone who looked at my crotch that Ally still had the same effect on me. At one point she pulled me close. She had to feel how hard I was. She asked if I would help her get the present for my parents out of the car which was pared across the street at the dark playground. Her husband was to drunk and to busy hittting on my Dad's secretary to help her.
As we walked she took my arm pressed it against her breast as she held my hand. She started asking me about my love life and shared with me that she and her husband didn't have sex so she masturbated a lot. She sensed my nervousness with this discussion and when we got to the car made me promise not to tell anyone else. She told me she knew she turned me on. She asked me what turned me on the most about her and I said everything. She then kissed me with her tongue and started rubbing my cock through my pants. She stepped away from me then just when I was about to come. She unzipped her dress, let it drop to the street, and removed her bra. This was my dream coming true. She let me play and suck on her tits. I asked if we could get in the car screw around. She said we couldn't have sex because we were related but she wanted to stroke me and taste me. She took my hand first and showed me where and how she wanted to be touched. She almost immediately started to moan and within a couple of minutes was having an orgasm. Now it was my turn. She started stroking me and within seconds I had a violent orgasm, shooting many feet out. She said I was naughty for not waiting and started to give me a blowjob. Within a few minutes I was bucking against her face coming again.
Ally and I have only been together 2 times since. She still wouldn't screw but oral was OK. I still to this day masturbate thinking about her