Memories of Judy, my first Affair.

My first affair was in early 2010. I don’t know what led me to cheat, but I have an addictive personality. I was married with children, and we were like many couples, happy at times, but not all the time. Couple this with the easy access to married women on AOL, and I wouldn’t have gone down this rabbit hole.

Remember AOL? It was like Craigslist years later for bisexual hook-ups. There was a married affair channel on AOL, and it was well attended. Strike up a conversation, go to a private online room, and you are halfway to having an affair. I found it easy to talk to women; I am a good listener.

The married cheating sites today are full of scams, and the platforms are designed for income, not your pleasure. AOL was full of real people who were curious and desiring an affair.
I met Judy online, a married woman on Long Island. She was easy to talk to, and we shared some pleasant conversations. I was in New Jersey, but my job allowed me some travel. I had a vendor in a nearby town, so we began to discuss a meeting. She was married to a church elder and part-time minister, and she was religious, an unlikely candidate for an affair. Yet, she felt she wanted to experience something more, having dated only one man, her husband.

I was going to Long Island, and we arranged to meet. This seemed too easy, and I felt like I was being followed, maybe a scam or worse. Yet, I arrived at a meeting place, and she was there. I did not date much before being married. Most of my girlfriends were long-term, so this was a real adventure.

Our conversation flowed as we walked through town. We held hands and kissed often. We were like two teenagers, so refreshing. We had lunch in a small restaurant, sitting close, snuggling up, and kissing. The owners were an elderly couple. I think the lady knew there was something untoward going on; she often gave us disapproving looks. We both had wedding rings on, and I wondered, didn't she ever see a happy married couple before?

Her husband, an old-world Italian man, looked at us with a smile; his thoughts were obvious: “ahhhh Amor.”

This was the extent of our first rendezvous. I drove home happy with thoughts of Judy. I could not wait for our second meeting, and she felt the same.

Our next meeting was at a pancake house, which became our meeting place for future rendezvous. We always met in the morning. Afterward, we went to a clean yet cheap motel with day rates. The sex was awesome, and we cuddled in bed for an hour after, pillow-talking. There were so many memorable moments.

One time in the heat of passion, she didn't want me to wear a condom, saying she wanted to feel me naturally. We always used condoms, but this time our lovemaking was beyond belief. We took a calculated risk.

At our love hotel once, I noticed a car with a man reading a paper. Once again, I feared I was going to be blackmailed, but apparently, he was watching another liaison. I wonder what ever happened.
We used to walk through a boat dock/park, and one time we didn't have time for a room. Right there in the car, in public, she gave me a wonderful front seat BJ. Afterwards, we walked around the dock, kissing and holding hands, then came back to the car, and she gave me another wonderful BJ.

We knew we would never take this relationship further, yet we expressed our love for each other. Love is a special word and feeling. This was real; it felt great knowing someone loved me, and I loved her.

I am not sure why it ended, but the memory was forever. Even now, decades later, on my birthday or hers, we send a greeting and always sign it, "With True Love". It was as if she were my first true love, and in a way, she was. My first lover. Beautiful memory!

This sparked other affairs, which at the time were easy to arrange. Great and interesting memories of these other lovers, but none as strong as the rendezvous with Judy.

PostNote 12/23/25 : Today is her birthday, and we exchanged loving messages today and recalled the time in the coffee shop. I will never be with her again, but the feelings and memory continue.. happy birthday my love...