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Alexandra and the Pensioners

"Size matters but not as much as knowing where the money is."

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Author's Notes

"As a sequel to “Money Talks,” Alex writes about her life after leaving Hank."

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.

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“He was very strong and pounded into me for what seemed forever. I guess he liked it because he kept grunting and groaning the whole time. When he finished, I was dazed but for some reason, happy. I had done it. I had finally become a woman and was no longer a virgin." The thing is," I told Nolan, “he made me never tell anyone, or else he would start rumors that I was a slut who sleeps around. He would make sure my parents would be the first to find out.

"Of course, my dad's friend took advantage of the situation and picked me up at high school, parked in a forested area close to home, and fucked me in the back seat of his Volvo station wagon. This went on until I graduated a month later.

"After that, having a boy get hard and ooze precum fascinated me. I loved touching their erect pole and teasing it with my lips and tongue. From then on, I was sexually active all through college loving the excitement of hearing them talk dirty when cumming inside me. There is something about feeling squirt after squirt of semen shooting inside me that a man just can’t understand. You know, Nolan, the strange thing is, I can’t remember my dad’s friend’s name but that must be why I like older men."

Nolan asked why I become an escort.

“It’s a long story but to start with, I love sex as you know.” I took another sip of my martini then said, “I met a young wealthy guy while I was doing my dissertation on ancient sexual perversions. We lived together and we enjoyed a lot of hot sex until he left for Paris to enroll in a culinary school. He was gone a year. By then I found a job teaching at a junior college.

“One of my students was a hunk who was hard to resist. We lived together for a short time until he graduated. Before leaving school, he hooked me up with some friends who paid for my company. It was his idea to leave teaching and be an escort.”

After a month together, Nolan asked me to marry him. I told him that I loved his company and that he was the best pussy licker I’d ever had. But I said I wasn’t the marrying type. That’s when he gave my name to his friends at the club. After that, I was busy three or four times a week, usually in the afternoon when the men were “golfing.” It amazed me how virile men in their sixties, even seventies, can be. Most wanted anal. It was something that had been on their bucket lists for a long time. I charged double for accommodating their fantasy.

George, who I had met for a two-thirty appointment, asked me if I would entertain some friends at a bachelor party. His son was getting married and George wanted to give him a special send-off to a life of matrimony.

"What exactly do you mean, George? How do you want me to entertain your son?

“Oh, you could do a strip for the guys and maybe something more.”

“You mean you want me to fuck your son.”

“That’s right and maybe some of his guests. I’ll pay you a flat rate for the whole evening.”

“How much?”

“I was thinking four figures.”

“Give me two grand and I’ll do it.”

"Agreed," and he wrote me a check right then.

The party was an orgy, reminding me of the Ides of March celebration I had enjoyed with Hank, my old boyfriend. Unlike the Ides of March party where a friend of mine was the girl of attention, I was the centerpiece at the bachelor party. The groom was to do me in front of his friends. So, I was to fuck him on the pool table.

Two men picked me up and gently laid me naked on the green felt. It was showtime. By popular request, I was told to spread my pussy lips and pleasure myself. I wasn’t alone because after a few minutes of giving them a show, my audience had their pants down with stiff pricks being rubbed and firmed for the main event. To watch almost a dozen guys jerking off together gave me an added incentive to show off.

By that time, the group had gotten a little rowdy, but the show must go on. The best man’s job was to be like a male fluffer to prepare me with his mouth for the groom. He was a marvelous pussy eater, and I came twice during the preliminaries. Finally, I got a look at the groom’s donkey size cock. I could only imagine how happy he was going to make his bride. I was desperate to get him inside me.

Despite his size, he slipped in without hesitation. I let him use me as he wished. His buddies had plenty of suggestions and he tried most of them on me. Being the center of attention with all the smartphones clicking away added to the excitement making me feel like the queen at the ball or in this case, the queen of the balling. He finished fucking me on my hands and knees while his friends mocked us with howls and barks.

By that time, two guys couldn’t hold it any longer and sprayed gobs of cum on my tits and face. Another one straddled my face sticking his nicely proportioned dick down my throat. It wasn’t long before he reached a powerful climax with cum dripping down my chin.

I was so hungry for more cock, I yelled out, “Who’s next?” Right away a guy climbed on top of me slamming his dick in my steamy pussy and didn’t seem to mind getting sloppy seconds. Neither did the guys that followed. I didn’t keep score but there was probably a half dozen players that I “entertained” before the party ended. There aren’t words to describe my satisfaction of having hard cocks streaming warm cum after warm cum into my pussy.

There was only the pool cue incident that made things a little kinky. One of the drunk party guests picked up a pool cue. He decided that it would be a nice fit in my well-lubricated hole. Yes, it fit fine. I was happy that he fucked me with the fat end of the stick. I left the party leaving a badly cum stained billiards table.

I had been on the escort circuit in Florida for about a year when I found out about ‘OnlyFans.’ It is an online, mostly pornographic service, from England. I decided to create a similar website where I could model and entertain users like at the bachelor party and maybe have live online sex. Of course, they would pay for a membership. I called my website, “Who’s Next?”

Sergei was the son of Dimitri, a Russian who offered me a job as one of his “hostesses” at his Sweat and Lovely “boarding house” that was next to the Sweat and Lovely strip club and adjacent to the Sweat and Lovely adult bookstore. The Happy Ending Massage Parlor wasn’t far away and owned and operated by Dimitri’s Asian wife. I told Dimitri I was doing fine as an independent although in summer when business was slow, I stripped at his club to lure more clients. In the back of the bookstore, there was an adult film studio where I did some modeling and appeared in several of their videos.

Anyway, Dimitri’s son, Sergei, was the technician and sometimes actor at the film studio. He was a genius with computers, and we got along well. For the price of a couple of free ones on his dad's yacht, Sergei set me up with a secure website and cameras. One of the first performances online was giving Sergei a blowjob. Later, after the website got more clicks and members, I fucked him which was a membership special available for viewing by those with premium accounts. That was what made the viewership explode.

The only problem was that I needed girls, so I hired some of the strippers from the Sweet and Lovely strip club that doubled as prostitutes. I had a team of women with the help of porn actors from the film studio.

"Do Your Own Porn" became a hugely popular feature where members posted their pictures and videos. It surprised me what folks will do to be performers and exhibit themselves publicly. I called it a swinger’s club without leaving home. Eventually I had to impose an age limit of eighteen when kids of questionable ages tried to post iPhone videos of their girlfriends.

I was making real money with my escort service and website, the kind I dreamed about after leaving college. All that was left to decide was what kind of sports car to buy and whether or not to marry Sergei who said he wanted to make me an honest woman. "It’s the right thing to do, Alex,” he said.

“But Sergei, I love my work and I’m not giving it up just because I’m married.” He said he didn’t care as long as he was my first fuck in the morning and the last at night. Cum to think of it, maybe I’m the marrying type after all.

 

 

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Written by xhardx13
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