When I was in my late teens, I couldn't let a minute pass by without thinking about sex or a day without jerking off. I was obsessed with my penis. Even for a kid, I built up a pretty decent collection of hardcore magazines and a couple of videotapes to masturbate to. Both my parents worked full time, so I had free run of the house to totally strip down, lie on my bed and beat my meat while watching the hotties on the TV screen have everything done to them that I wish I was doing. You see, the girls my age only wanted to kiss, and never seemed to want to fool around any further than that. For that matter, I didn't want to respect them, I just wanted to fuck them and have them blow me with no strings attached. And as for the girls that would go all the way? Well, my parents and their friends would hardly approve of their social standing so it was a no win situation.
As with anything a kid does repeatedly, over and over, I began to get comfortable with jerking off, so much so that I had set aside times to do it. For instance, if I jerked off early in the morning, then I could jerk off again after school and be ready again for that night before I went to bed. But by doing it so much, I started to get sloppy about my clean up. Instead of flushing the incriminating Kleenexes full of my wad, I started to let them build up in my trashcan. I always wondered if our maid knew what she was emptying, but I didn't think too much about it. I figured she had no clue what a 18 year-old boy was doing in his room alone all the time. But I would soon find out just how much she knew. When I ran out of tissues, I started using gym socks to drop my load into and then I would put them in the hamper and they would come back as good as new. That's when Lisa, our maid, comes into the picture.
She used to come by every Friday for a few hours and do her work. Well, on one Friday afternoon I was busy stroking my cock to a Club Magazine when I heard a knock at my bedroom door. I immediately froze, realizing that my clothes were piled on the floor out of reach and there was an incriminating bottle of moisturizer lying next to me on my bed. I knew my parents weren't home yet, so I figured whomever it was would figure I was asleep and would go away. Not the case, the doorknob turned and in walked Lisa. After she realized what I was doing she quickly looked at the floor, made a noise of disgust and rushed out into the hallway. I got all embarrassed and started to put my clothes on apologizing for what she had seen. After I got dressed, I asked her what she needed as if nothing had happened. She then informed me that she realizes I have certain needs and urges to act on those needs, but she would appreciate it if I would either stop masturbating into my socks or stop putting them in the laundry. I felt like a kid getting his hand caught in the cookie jar. She stressed she wanted to tell me directly and not go to my parents and embarrass me. My mother would have been horrified thinking that my sperm was swimming with all of her expensive clothes and my father would have thought I was a bigger freak and disappointment than I already was. I thanked Lisa, and strangely enough, from that point on we had sort of a bond with each other. Like we were sharing a secret or something.
One day, Lisa made a joke about how light the laundry seemed without all my socks in it. My face turned red and we both laughed it off. Then to my surprise, she told me how she thought it was cute. I was thinking, how cute is a 18 year old who can't keep his hand off his dick? But I decided to go with it anyway. I never really thought of Lisa as particularly attractive, I guess I always thought of her as just the maid and not a person. But on this day, I realized that she was quite attractive. Her hair was pulled back and she had beautiful olive skin. She had a nice round ass and a beautiful set of breasts. A solid C cup if I had to guess, and they seemed to defy gravity. Then she caught me off guard by opening up personally. She asked me why I didn't have a girlfriend that could take care of my needs. And I answered that at my all male school, there wasn't much of a chance to meet girls. She then told me that her ex used to watch a ton of porn and that it always bothered her. I told her I had no choice, that fantasizing could only take you so far. She still expressed disappointment that I watched it and stated that she felt it was degrading to women. I then jumped on the opportunity and invited her to judge for herself with what was in my collection. Surprisingly, she agreed and said it couldn't be that bad if I spent all my time watching it.