My best masturbation memory I use in a solo capacity.
When I was younger (a little over 13 and in middle school), my parents worked a lot and many times were not home when I went to sleep. They both worked at a warehouse center and had to receive and catalog shipments after regular business hours and prepare for the next day orders. There was a girl named Tara, a junior or senior in high school, who lived a few houses down and was not much older than me. From what I remember at the time, she was average height (brownish hair, dark eyes, and moderately tan skin for a Caucasian female). My parents would have her stay over at our house on the nights they had to stay at work late. This arrangement was frequent and I thought nothing of it at the time.
One evening, my mom had to go back into the the warehouse during Christmas season to help my dad manage the increase in packages. Tara came over a little early before my mom left. My mom mentioned to me as she was leaving, "Make sure to take a bath or shower tonight because you won't have time tomorrow morning since we are leaving early to run errands before your cousins come to visit. Oh, and don't forget to wash under your foreskin." And then to make things more awkward for me my mom quickly said, "Tara, please make sure he remembers to shower or he won't do it. And check if he's clean. I'll be home before midnight." My face must have turned bright red. I can still remember the intense embarrassment as my mom closed the door and I faced Tara. Usually Tara came over and I had already bathed. This was not something Tara really did for me and to this day I don't really know what my mom was thinking, as I was already very independent and was probably old enough not to need someone over.
Tara and I hung out like we always did when my parents were gone. We watched TV, ate dinner, and then I got ready for bed. I got up and took a quick shower and was headed in my room when Tara came around the corner and asked if I cleaned myself and then, to my horror, asked, "Did you clean under your foreskin like your mom asked? I guess I should check since she asked me, if that is okay." I said, "Sure," sheepishly. To make things worse, I was cold walking from the bathroom to my bedroom and was covered with nothing but a towel. Tara followed me into the bedroom and I sat on the bed. She asked me to remove the towel. I distinctly remember experiencing shrinkage because I was cold, so I must have looked less than impressive to her. She reached out, and with her thumb and index finger, slowly retracted my foreskin to examine my gland. Then she said, "I guess it looks clean," as she manipulated my foreskin between her fingers and then proceeded to pull my prepuce back over my head. I didn't know it at the time, but my penis leaked a little precum (as it does when my foreskin gets fully retracted). Tara wiped away the precum at the tip of my foreskin with my towel and said, "well, I will tell your mom you bathed. Have a good night." And left the room.
I wish I would have cherished that moment, because it became one of the best memories I had growing up (and I still masturbate thinking about her and that one and only "check" she ever performed on me). Tara was so clinical and mature about examining my uncircumcised penis. She confidently retracted my foreskin, made an assessment of my cleanliness, and then pulled my skin back over my head. What really turns me on is that she knew to wipe the tip of my foreskin with the towel when I had some precum built up. At the time, I was so nervous and anxiety-stricken to understand that what was happening could have been so much more amazing. I live out of state now (after I graduated college and got full-time employment). Tara got married and has a family that live pretty close to my parents I believe. Occasionally, I will see her visiting my parents when I come home for a holiday. I secretly hope she remembers that one time she had to "check my foreskin." But sadly, I doubt it even crosses her mind.
With that memory I always imagine that she continued slowly masturbating my penis by retracting my foreskin, looking at my exposed head, and then returning my prepuce into its natural resting state. I turn my hand and simulate the movement her fingers did and pretend it is her massaging my uncut penis. Another really interesting thing I find is that at the time Tara examined me, I was in a state of shrinkage. It is a huge turn on to me to be totally exposed to a female in my most small and vulnerable state. I have not had many (hardly any) sexual experiences. I think it might be that I am nervous of the still "taboo" view of uncircumcised males in American society. So masturbating to the thought of a female being okay with my foreskin is so amazing.
Thanks for letting me share.