Playboy. Casanova. Don Juan. These were all the names people no doubt called him. And they were all the names he had called himself at one time or another. Reality can rarely be reduced to a label though, and now he knew the truth.
It had started in college. In the summers Jake had worked for a catering company in the resort area south of his hometown. Several upscale resorts and big vacation homes dotted the lake there. The same lake his family had spent so many camping trips at, as a kid. Now it was the home of the rich and beautiful people. But rather than despise them, he wanted to know them, live like them. He figured if he got a job as a caterer, he could be around them and learn their secrets.
His first couple of jobs with the catering company was hosting private events at the resorts. He only got to mingle with the rich, well-to-do guests intermittently though. Then he was offered a weekend job, which a lot of the young staffers were not inclined to accept. That first job changed everything.
It was a birthday bash for an older, but still active widow by the name of Candice Parker. She lived in a magnificent house right on the lake. Her friends had organized the party for her and she had gone along with it to appease them more than anything. All the faces were familiar and somewhat boring to her by now. She spent most of the night talking with the staff, paying special attention to Jake. He was a server and good at his job. His flirting among the women at the party was always subdued, but unmistakable and well received. He figured his natural charm and good looks (on more than several occasions people said he reminded them of Johnny Depp) would land him a date with one of the younger women. If they were married, it didn't make much difference to him. He was just after a good time after all.
By the end of the night, he had three phone numbers, all from married women. It didn't surprise him. What did surprise him was that Candice, the guest of honor, had asked him to stay and he had accepted. She made a flimsy excuse about wanting tea being served to the few remaining guests, but he could sense otherwise.
When the other guests and staff had all gone, he and Candice started to talk and didn't stop until late into the night. It turns they both loved literature, and he actually had an opportunity to use what he had learned in those two literature courses that his Dad had scoffed at. She had been a creative writing teacher before she got married. Her late husband felt a woman's place was in the home, so she had quit and regretted it ever since.
Jake had other jobs in the other big houses around the lake. He knew if he could get the woman of the house alone during these private parties, even for a few moments, that she would want to see him again and spend money on him. This took the form of lunches at the big resorts or even shopping trips in the nearby city while their husbands were doing business. Sex never came up primarily because he never brought it up. For these married women, they wanted companionship and good conversation, which they weren't getting at home. And this was worth much more to them than what they spent on Jake.
He kept thinking back to Candice though. She hadn't pushed him to come back as she wasn't totally blind to the desires of a young, good looking man such as him. But she had miscalculated the desires of this particular young man. He did call her again, only to be told she was about to leave for Europe on an extended stay. Then in a moment of boldness, she asked him to go with her to be her traveling companion. And for the next six weeks, they toured all of southern Europe, including Greece, the western coast of Italy, Rome, and the south of France. He received a better education of the Old World civilizations in just those six weeks than he ever could have in school.
Returning home, he quit the catering job and moved into her big, beautiful house on the lake. His favorite thing was to smoke a pipe out on the shore of the lake, imagining himself in another era. Her favorite thing was parading him around the lake at different events, letting the imaginations of the other guests run wild.