I first met Christy about five years ago as I was about to separate from my then-wife. We had mutual friends and had met one evening at a wine bar in our small downtown. While I did not know her back in high school, I did know her older sister as she was my age. Ironically, she and I worked for the same large manufacturing company in town. I was in Sales and Marketing, and she was in Payroll.
Christy had been separated for almost two years and was finalizing her divorce from her Ex. It was a long, painful, and expensive divorce. They seemed to argue over everything, often spending more on lawyer fees than what said item might be worth.
She gave me some very good advice as I moved out and my wife and I started the divorce procedure. I learned that she was also a man-hater, as she no longer trusted anyone with a penis. Yes, her husband had been cheating on her for about two years when she finally caught him.
After about six months I had several friends tell me I should date Christy. We seemed like a good match, they said. There was one big problem, I did not find Christy attractive. She had a typical fifty-plus-year-old woman BBW figure with big tits, but I simply did not find her attractive. She had thin lips, deep-set eyes, a bad at-home golden blonde hair dye job and did not know how to dress her curvy body.
Over the years we hung out regularly both with our group of friends or just the two of us. We had much in common, including our lack of success with online dating. There were two of our friends who used to always tell me I should just hook up with her. It was well known that she had hooked up with other men in a FWB situation.
Fast forward to October 2022 when Christy and I were both off work as our company had closed for two weeks for plant maintenance. We were simply trading a few texts one day asking what the other was doing. We were both bored. We made plans for me to pick up dinner at an Italian deli.
After arriving she opened a bottle of vino and we started catching up about our vacations the week prior. She had gone to Nashville and New Orleans while I went to an all-inclusive resort near Cabo San Lucas. We soon made a salad and went out to her pool to eat dinner. And we had a second bottle of wine.
It was very warm for the second week of October and Christy joked about us going swimming.
“I love that idea! Let’s jump in,” I said.
Christy laughed, “You don’t have a suit.”
“I’ll skinny dip,” I joked, thanks to the wine.
“I dare you,” Christy said rather loudly.
I stood up, pulled off my t-shirt, kicked off my flip-flops, and started to unbuckle my belt. I looked at Christy and she was laughing.
“Ok, very funny,” she said.
My khaki shorts fell to the concrete, and I stood there in just my black Under Armor boxer briefs.
“I’ll put my suit on if you swim in your undies,” Christy said as she stood up.
Without saying a word, I stepped out of my undies, turned towards her giving her a full view of manhood, and took a few steps down into her tanning ledge.
“Oh my God!” she stammered.
“Come on, get naked,” I told her with a laugh. I turned back toward her, “Get a good look at my cock because once I jump in the water it will be total shrinkage,” referencing one of the classic Seinfeld episodes.