Summer had arrived. The sun shone brightly, the air was dry and seething, and plants and animals were alive with the beauty of the world. It was the summer of the new millenium, but nothing seemed different. In our small town, time seemed to stand still while the rest of the world moved on.
School was out and I was looking for a job. Given a choice, I would rather have lazed away my whole summer at home, doing nothing but watching TV. And maybe shooting some hoops, after all, I had to make sure that I kept my physique, it was the one thing, the only thing that attracted any girl’s immediate attention. Ever since I first realized what sex was, I had been teasing and turning on many girls, especially those in my school. It had benefitted me somewhat, after all, I’d found out what was written in every stall in every girl’s bathroom while fucking the brains out of some young tart.
But the job thing was my mom’s idea. Her usual preaching was that she had worked during all of her school holidays so that she could pay herself through college. That’s how she got her law degree and went on to become a successful family lawyer. It was ironic, though. She was helping these families sort through their legal troubles when she herself was screaming bloody murder at my dad.
I’d never known my dad. I was only 2 years old when my mom packed up my two sisters and me and left my dad. Dad never bothered to keep in contact. According to what mom said, he had hooked up with some young thing somewhere on the opposite side of the world. I didn’t care, as long as there was food on the table, shelter over my head, and no questions asked about my life. Mom understood that pretty much, she was persistent only about that I do well in school and find a job for the entire summer, like my sisters.
That’s one thing I really hated, being compared to my sisters. Rebecca at 20 years old was in college, so of course she needed the money. She had found a job as a secretary at some office and earned pretty good money. Amy, 18, was still young and optimistic, so she had become a part-time nursery school teacher. The money wasn’t that great, but she said she found joy being surrounded by screaming kids, and who was I to argue with her.
That left me, the middle child at 19 years old. Mom named me Dean, apparently after an old boyfriend. I guess I was the only realist in the family. I was in the prime of my youth, with three free months ahead of me, and now I had to be cooped up in some office or storeroom or somewhere. But what could I do? It was either I get a job or mom would make me pay rent. My choice was clear.
So there I was, in our backyard, my legs in the pool and the classifieds in my hands. The water felt really refreshing around my legs and I was tempted to jump in for a swim. But I knew that if I did that, then I’d forget about job-hunting, and mom would scream at me during dinner. I scanned through the columns and columns of job listings. It was amazing how our small town could generate so many jobs. A few ads caught my eye, particularly those that were well paid.
It was too hot to wear anything, but for decency’s sake, I decided to keep my boxers on. I didn’t need to since a privation fence went around our backyard. It was so high that even I, the tallest in the family, couldn’t peek over it on tip-toe. Mom valued her privacy and I didn’t blame her. At 38, she still had a killer body. She was a slender waist, long legs and well-shaped 38D breasts. She kept her curly brown hair at shoulder-length, which didn’t look too bad on her. She was a health nut, so she kept in shape by exercising regularly. My friends had often remarked about how they were turned on just by looking at her. And then they’d tease me about living with a goddess.
No, three goddesses, since my sisters were also rather good-looking. Rebecca, a school volleyball player, had a nice firm body complimented by long slender legs. The only thing that stood out, and I meant this is the nicest possible way, were her 40DD breasts. Amy, on the other hand, had breasts that were a respectable 34C. She was naturally slim. She could eat a whole cow and still be light enough to be blown away. But that made her look cute enough to be swept off her feet, if the guy didn’t do it literally.
When they swam, I’d steal glances at them. I told myself that it was just a hormonal, primal thing. If a man saw three beautiful women in wet swimsuits, of course he’d want to check them out. On the other hand, I had often wondered whether mom or my sisters had looked at me when I swam. After all, I had read that women are attracted to well-built men, as evidenced by the number of girls who swarmed to me, so could the women in my family be any different?
Anyway, that was the furthest thing from my mind at that moment. I needed to find a job, like now. And just then, I spotted an ad in the personals section.
“Wanted: SWM in late teens to escort lonely SWF, 38 this Friday night. One time only, will pay in hundreds. Interested, leave voice message on XXX-XXXX.”
“Hmm, that looks interesting,” I thought. It was only for one night, but if the pay were really as stated, then he wouldn’t have to look for another job for the rest of summer. But then, he would have to accompany a 38-year-old woman. “That’s as old as mom,” he thought. She could be some old, dumpy woman with crease lines all over her body and saggy breasts. He was repulsed at that image. Then again, his mom was proof that women in their late thirties could look stunning.
He decided to take the risk and picked up his mobile phone. His mom didn’t know that he had one. She’d kill him if she found out because it would be a sign that he didn’t trust her with his private calls. The truth was, he didn’t. How else could he talk dirty to a young slut from school? He dialled the number quickly. After a few rings, he heard a recorded message from a sultry feminine voice. He knew that it could be a cover for a really ugly old hag, but he crossed his fingers, then spoke into the phone, “Hi, my name is Dean and I read your ad for an escort. I’m 16 years old, have a great athletic body and lots of experience. I’d really love to hear from you, call me at this number.” I left my phone number and hung up. Then I threw the newspapers aside and dived into the water.
During dinner, mom asked if I had found a job. I said, “Maybe, I’m waiting for a return call.”
“Oh, that’s good,” she said. “Hope that works out.”
“What job is it?” Rebecca asked.
“Just some manual stuff,” I replied as seriously as I could.
“Cool,” Amy said. “You should be able to manage just fine.”
I made a face at her, then left the table. I hurried up to my room and picked up my phone. I had turned it off and listened to my voice messages. Then, I heard the one I wanted: “Hi, my name is Lisa, I got your message. I think you sound really nice and I’d like to see you. Meet me in Greener’s Park at the bench near the stone bridge this Friday at 10 p.m. Don’t be late.”
My heart jumped. I had a job! And if this woman sounded as determined and sexy as she sounded, then I was in for the time of my life. This was the first time I had ever done this sort of thing and my heart beat faster than a locomotive. Needless to say, I couldn’t sleep that night, nor any other nights until Friday arrived.
Since it was the weekend, everyone had plans. Rebecca and Amy were going to hang out with their friends and mom said that she had a dinner date. I said I was going to catch a movie after dinner. However, as soon as everyone had left, I started preparing for the night. I put on a fresh shirt and nice pants. I thought about wearing a tie but decided that it would be too formal. I wore dark socks and matching leather shoes. Then, at 9:30 p.m., I sprayed some cologne on and left the house.
I arrived at Greener’s Park at 9:50 p.m. and headed straight for the designated bench. There was hardly anybody there at that time, no couples ever made out there ever since the authorities realized what had been going on and installed more lights. I guess that’s why it made sense to meet there, we could get to know each other better before we did whatever we did.
The bench was empty when I found it. I sat down and inspected myself. I smoothed out my shirt and pants and swept back my hair. I was determined to make the best of the night. Then I remembered that I hadn’t brought any condoms. I panicked. Weren’t escorts supposed to ensure that they had protection? I cringed as I saw my entire night go up in smoke.
Just then, a woman appeared from under the bridge. She was wearing a long black dress and large hat. Her black high-heels made a tocking noise on the pavement as she walked towards me. I swallowed as I watched her approach me. My heart beat faster and faster.
Then she looked up. “Dean?” she said.
That voice sounded strikingly familiar, but I chose not to pursue that line of thought. “Yes, I’m Dean,” I replied. “Are you Lisa?”
She gasped. “Oh my god,” she mumbled. With one smooth move, she took off her hat.
Now, in the brightness of the lights, I looked at the face and nearly died. Lisa was mom! “Mom, it’s you!” I yelled.
She trembled and her legs looked like they would fail her. I quickly got up and helped her sit down. All this time, she was looking at me as if it was the first time she had seen me. I was looking at her in the same way and wondered what the repercussions were going to be when we arrived home.
