I'm sure there is a Freudian event that predates what I'm about to share. But my first experience as a cuckold goes back to my high school. I had fallen deeply in love with Jenny in my junior year. She was in my class and living with her grandmother in our small Ohio town, originally from Pasadena. She was blonde, beautiful, and so much fun to be with. I had started to hang with a slightly older group that drank, smoked pot, and partied kind of hard. Jenny was part of that crowd. She was dating Kevin who was an oil field worker with lots of money, attitude and weed. Jenny was really into him. I don’t think anyone noticed but I was really into her. I was smaller in frame and younger than Kevin. I wasn’t surprised that he attracted a beautiful girl like Jenny.

But sometime during that year Kevin dumped her, sending her back to Pasadena to live with her parents in a hurry. Quietly I was crushed. I had waited, and wanted her and finally she was through with Kevin. But instead of having the opportunity to make her mine, I lost her to the west coast. I was truly heart-broken.

Sometime during the following summer, she came back to Ohio. Having recovered from her own heart-break she moved back in with her grandmother. I wasted no time. I let her know immediately how I felt. She told me she thought that she might be in love with me too, and I was immediately past my point of no return. When we finally had sex felt like I was making love to a goddess. Her naturally blonde pussy, her large breasts, sweet smile and blue eyes made me insane love and lust. Her full (but fit) figure made me feel as though I was with a woman for the first time in my life. This was my first adult love affair.

When I wasnt working that summer, I was with Jenny. We made love often and went everywhere together. I had found my soul mate and I knew it.

We were both high school seniors that fall and everyone at our school knew that we were in love. I was on top of the world.

Then one Friday night, after getting off work at a local restaurant I went to Jenny’s grandmother’s house to pick her up. She wasn’t there. In retrospect, I see that her grandmother knew more than she was telling me. She knew that Kevin had stopped by to take Jenny out. She knew that I was being betrayed. But I was naive. I was only worried about her safety. The thought of her being a bad girl never entered my mind.

I spent the whole night driving around town. Going from hangout to hangout, looking for any clue to tell me where she was. Every hour or so I would return to her grandmother’s house only to not find her there.

At daybreak the following morning I caught up with her at the apartment of one of her friends. Immediately I knew something was up. Her eyes had never looked at me like that. Then she said it.

“I’m not going to lie to you. I was with Kevin last night. And yes, I slept with him.”

She was obviously embarrassed but not ashamed. She said she was sorry for making me worry about her but there was no apology for spreading her legs, for letting another guy - an older more masculine guy put his cock inside her. There was no apology for letting him cum inside her, as I later learned he did.

I remember very little dialogue after that point. I felt a blow to my gut. My head was spinning, and I was so angry! I wanted to smack her, or cry or something. But I don’t think I did anything really. I yelled. Big deal.
We continued dating for a few more weeks, maybe a month. But I no longer loved her. I was an ass to her for the remaining time we were together and even cheated on her in retaliation for the pain I felt. But in the end all the passion was gone and it was over. That was the autumn of my senior year of high school.

I didn’t know whom I was going to grow up to be then. I didn’t know then that I would one day actually want my wife to be unfaithful to me, even ask her to be. I couldn’t imagine back then that I would ask my wife someday to suck her boss’ cock. But I did. I didn’t know that I would someday spend hours talking my wife into spreading her legs for my best friend. But I did. I didn’t know enough when I was in high school to understand, and certainly didn’t know enough to enjoy the raw and deep sexuality that caused Jenny to spread her legs for Kevin that night, even though I know she loved me when she did it. I was too young.

About ten years later, standing at a window in the darkened kitchen of my own home, while stroking my stiff and aching cock, watching my wife give oral sex to her boss in our driveway I started to make the association. At that electric moment I remembered the agony and the euphoria that I experienced back in high school. I suddenly remembered the nights in my bed visualizing Jenny sitting atop Kevin’s cock, masturbating my own cock. Although she never really described anything they had done to me in any detail, in my mind’s eye I saw her slowly fucking him, her beautiful breasts in his hands. I imagined them cumming over and over again, together. Sometimes it is only vapor that separates our joys from our sorrows.