Like I told my friend Hank, I moved to Florida after teaching for two years in North Carolina. Hank and I had been close friends. I guess it would be more accurate to say we were lovers for a year before he enrolled at a culinary school in Paris. Soon after he returned, Hank hooked up with his high school sweetheart and married her. I had moved on too.
Hank and I had some great times together. We both loved sex and made the most of our many hours in bed. He was wealthy and I imagined being his wife. It didn’t work out. With him in France and me finalizing my dissertation, we lost touch with each other. Then I took a teaching job that wasn’t what I expected. I taught at a college where the students were interested in taking easy courses and having sex. The only thing we had in common was the latter.
It wasn’t the right thing to do but Herold was too much for me to resist. He was a student in my Sociality 105 class. I just couldn’t resist the boy. When we met at a seminar for “Social Interaction of Generations". We went out for a drink and flirted for a while before he invited me to his apartment. It should have been a one-night stand. Our affair continued until the semester ended and he graduated.
I introduced Herold to the same ancient perversions that Hank and I had enjoyed. Before Herold left to take a job in the family business, he suggested I take it one step further. He said, “You can make a lot of money engaging guys in your kinky eroticism.”
“What are you getting at, Herold?”
“How much do you make at the college?”
“About four grand per semester.”
“I think you could make much more as an escort.”
“An escort? You are kidding, of course.”
“You are sexy with a great body and know how to turn a guy into a fucking savage. I know a few guys that wouldn't think twice about paying you for sex. Their dads send them a generous allowance every month. You wouldn't want them to waste it on beer and inexperienced college girls, right?”
I laughed. “Of course not.”
He asked if I knew his friend Roger. I didn’t know Roger. “Roger has a job and is making good money in addition to his generous allowance," Herold said. "How about if I tell him about you? If he likes the idea, the two of you can get together.”
I agreed to meet Roger the following week. He liked the idea. Roger took me to his apartment and fucked me the same afternoon we met. Before he left for work, Roger gave me a hundred-dollar bill for a blowjob and finishing with a huge load inside me. It was fun and exciting. I wanted more. Anyway, the price was right. It was the first time I got paid for what I love to do.
As Harold said, college boys had more than pocket change to fulfill their desires. Herold did his best to hook me up with college friends and an occasional acquaintance from the Athletic Club where he caddied.
The second guy who paid me for sex was Will. He was young and it was Will's first time. He lasted about as long as it takes to wash your hands. It turned out that most of the college guys had little self-control like Will. None favored delayed gratification. They hadn't learned that a girl needs some gratification too.
However, I enjoyed showing the mostly inexperienced guys that fucking was more than the missionary position and the variety of cocks was stimulating. They say that size matters and it does, but the diversity of shapes has erotic charms of their own.
A guy by the name of Bill, although I knew it wasn’t his real name because Herold called him Taylor, came to me right after I had finished with a handsome black guy who called himself Vic. The reason for mentioning Bill was because he had an oversized, curved cock in the shape of a banana. He was more than thrilled to be fucking a girl that was so wet and slippery. Apparently, he didn't realize he was getting slippery seconds, but he loved it and I was rewarded when he pounded into me with his curved dick hitting all the right places.
There was another Bill, a common name after John in my job, who brought along a friend whose name wasn’t Bill. In fact, he never said his name, but I’d remember him again because of his pencil-thin cock. It went right up my ass while Bill fucked my pussy. Both exploded like fireworks on the Fourth of July. I got paid for overtime!
I was getting by but not in the way I had hoped. My income was barely covering expenses, although I loved the excitement of meeting young horny guys. It was like having nightly one-night stands with total strangers. Their youthful exuberance turned me on.
One of my tricks was a golfer that Herold knew from the Athletic Club. Bernie wined and dined me before fucking me at a motel. He was a great lover despite his age. Bernie was sixty-two with four grandkids. It was the first time I had more than one orgasm with a client, and he gave me a generous tip.
Bernie and I met twice more at different motels. He didn't want to be known as a regular at any of them. Bernie liked to talk about his grandkids and said he and his wife were moving to Florida where he could play golf year-round. That's when it occurred to me that Florida was where the money is.
I discovered a place where wealthy retired men liked golf and younger women. I moved to a Florida town on the Gulf side that included an upscale retirement village and was popular with snowbirds from the North. The beaches were an added perk.
Although prostitution is technically illegal in Florida, so is recreational pot and driving over the speed limit. So “technically,” I was dating or meeting an old friend. I had developed a sixth sense in North Carolina to keep out of view of the law that never seemed to be looking too hard.
At first, I lived and worked out of a trailer park. I thought it would be easy to find available men. It was, but not right away. To begin I went online to sex sites offering my company to local men. It turned out that their wives monitored what the men were watching. So, I thought of picking up men at bars. Older men drink but usually after golf at the club or social events with their wives.
Again, I struck out and was getting nowhere until I hooked up with a man during Happy Hour at the Pendulum Bar and Grill. Drinks were half price from four until six. I was there at five-fifteen when I met Nolan. He was a sixty-three-year-old widower who had lost his wife a month earlier. It didn’t take long for him to invite me to his home where I stayed the night. He was an amazing lover and like Bernie, had the staying power that I had missed with the college kids. He was a kind man and treated me like a queen.
I came back several more times. Before Nolan took me to bed, he liked to talk about the stock market and his late wife over cocktails. I listened to his stories and enjoyed hearing about his deep love for her. Nolan was also a good listener. I told him about myself and how my body had developed early attracting the attention of the boys in high school. "So, I dated a lot in high school," I said.
He asked me about my first time. I told him how my dad’s friend kept telling me how beautiful and sexy I was. "Every time he came over to have a few beers and watch baseball with my dad, he would hit on me. I was flattered but didn’t know what to do or say and dad didn't seem to care."
“Well, Nolan,” I continued, “you can imagine the rest. One time, the beer caught up with this guy on a hot afternoon when my dad had left for a dental appointment. I was wearing summer clothes that were nothing more than a bikini and sandals.
"My dad's friend asked me to move next to him while we watched the game. Before long he had his hands on my tits. It felt good so I let him do it just like with my boyfriends. It didn’t seem like we were doing anything wrong until his fingers began to explore my pussy. I didn’t know what to do. He was my dad's age and I hadn't learned how to say no to an adult. The thing is, it made me wet inside and felt wonderful.
"When he unzipped his pants and pulled my head down, I figured a blowjob was all he wanted. That wasn't new to me since I had done it with the boys at school. But that wasn't all he wanted. The guy pulled down my bikini bottom and turned me over on the couch. That was the first time I had felt a cock somewhere other than in my hand and or in my mouth.