The Bozo the Clown Show
I never met a breast I did not want to fondle and play with, and a nipple I did not want to suckle.
Hormones kicked in and jump started my libido in seventh grade: I attended a parochial grammar school in Chicago. In eighth grade we had an out of uniform event for eighth graders only, uniforms hid everything. Margie showed up wearing a tight fitting bright pink sweater; she was showing off her chest which was far and away more developed than any other girl in eighth grade; in fact she could have given Annette from Mickey Mouse Club a run for her money and what boy at that time did not have naughty thoughts about Annette???
I was horny and had erections a lot, almost to the point of being embarrassed. Because I attended an all boys high school, I had almost no contact with girls day to day. I feel that set me back socially and emotionally. I also had a secret crush on my mother's best friend who came over regularly. Her friend was almost a head taller than me and she also had a very abundant chest. I think that is where I got hooked on older women and fantasizing about them teaching me all about how to please and pleasure them.
All men (guys) are NOT created equal; I made that discovery the first week of high school, in the gym locker room. The guy whose locker was next to mine, and mind you we were the same age, around 14, the guy could have gotten a lead in any adult film he wanted. He was of Italian descent; he could have given John Holmes a run for his money, he was that hung. Seeing him hanging out next to me twice a week was ego deflating for; how can I even begin to "compete"...??? I spent my high school and early college years trying to build up the courage just to ask a girl out. In the meantime it was Playboy and either hand.
My grandfather owned a four flat; we lived on the second floor. He rented out the two smaller apartments, mostly by word of mouth. The summer of my junior year in college he had rented an apartment to a couple in their twenties. I presume they were married??? Her name was Jeanne, she was a natural redhead and she had a more than abundantly developed chest! OH MY! The first time I saw her I was looking down from the porch railing upstairs as she was walking below; all I saw was red hair and her chest. I presume she knew I was the landlord's grandson?
Over winter break I was beyond bored, getting more frustrated socially and almost desperate. Jeanne had gotten a puppy, so I made up an excuse to see it. Of course I was more interested in getting as close as I could to her chest! We chatted while seated at her kitchen table, she was home by herself; I did give some attention to the puppy. As I was leaving we stood close, I reached out and squeezed her breasts and asked her if they were real. I do not recall everything she said but I do recall her telling me to come back around noon the next day or the day after.
Next day I knocked quietly on her door, I did not want to bring attention to myself. She opened the door slightly; when she saw me she opened it just enough so I could enter then shut and locked the door. Jeanne was barefoot; she was wearing a sheer yellow thigh length teddy and matching yellow panties. I followed her to the smaller bedroom where the TV set was on, and I remember like it happened yesterday, the Bozo the Clown show on WGN-TV was just starting. I sat next to her on the bed and after a couple of moments she took off her teddy and asked me if this is what I wanted to see? Understand, until then I had never seen real bare breasts, only pictures in Playboy. All I wanted was Jeanne's breasts; I had my hands full, both hands. Had things stopped there I would have left with a huge smile.
Jeanne had other ideas and I was so completely unprepared for what happened next. She asked if I wanted to see more; well there wasn't a whole lot more to see except for what was in her sheer yellow panties. Off they came, she laid on her back, pulled up her knees, spread her thighs apart and invited me to get as close as I wanted. I forgot about her breasts. I took my time touching and exploring her. Had this happened when I was older, for sure I would have buried my face between her thighs and given her oral pleasure.
Jeanne was not done; after letting me explore for a while, she raised herself up on her elbows and softly said "Would you like to try putting it in me?" In a moment my clothes were in a pile on the floor. She shifted positions; now she was fully on the bed and I made my way between her thighs; we were in the missionary position. "Was this a dream; was this really happening?" In the meantime the Grand Prize Game was on the Bozo Show!
I wish I could say that this was the best day of my life up until that point. She was ready and willing to claim my virginity; it was going to be all natural, no protection. She told me not to worry, she was pregnant with their first child. Jeanne would be my first and it would be memorable. But that did not happen. I was OK playing with her breasts. When she took off her panties, I was not anticipating that at all. I was sooooo nervous. When she had told me to come back, I cannot remember how many times I pleasured myself just thinking of her breasts in the twenty four hours between yesterday and the next day. She reached between my thighs and began to work on me; she did a lot to get me hard. All I could manage was to dribble some in her hand. It was over; so was the Bozo Show. Her womanly scent on my fingers lingered a couple of days. When I got home next time from college I found out she and her man had moved.
To this day I wonder what she was thinking when I originally squeezed her breasts before she asked me to come back. She certainly could have rejected me completely, even threatened to tell my grandfather and my parents, after all, she was married. Did she say anything to her man; was he in on all this? A comment she made had me thinking she was doing this on her own??? Her outfit when she greeted me at the door when I came back caught me completely off guard; she had to have given thought to what she had in mind to do with me; how far she was willing to go. I wondered also...."what if...", what if she had taken my virginity, what if she had liked it, would we have done it again?