Dean's Summer Ch. 1

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.

“What are you doing?” she asked when she had regained her composure.

“You told me to find a job,” I said. “And I found this one.”

“As an escort? How could you?”

“Mom, you’re the one who wants an escort.”

“Yes, but that’s… Oh my…” She lowered and shook her head.

As we sat there, I gazed over her. The dress fit snugly around her body. It accentuated her chest, hips and waist. My eyes were drawn to her exposed chest, there was a plunging V-shaped neckline that ended just above the area between her breasts. I raised my head slightly to get a better view and realized that she wasn’t wearing a bra. I gasped.

She looked at me. “What are we going to do now?”

“Erm, it’s your night, what do you think?”

She looked me over and sighed. “Let’s go home, I don’t want to think about this any more.”

She got up and walked towards the park’s exit. I followed behind her. I realized that her back was even more exposed that her front. There was a similar plunging V-shape cut-out that ended at her belt. As we walked, I admired her slender back and noticed the way her hips swayed. Wow, mom really was gorgeous. At that moment, I felt my pants getting tight. I had a hard-on! My mom was turning me on. I knew I couldn’t let it happen, but as I looked at her from behind, I couldn’t help it. I pretended that I was just looking at another attractive woman.

We arrived at our parked car at the exit. Without a word, mom unlocked the door and got in. I sat in the passenger seat next to her. She started the car and drove off. It was maddeningly quiet during the entire journey. I leaned back and wondered where it had all gone wrong. As we drove, I glanced over at mom. With her arms slightly raised, it lifted the top of her dress slightly and I could see the side of her breast. My eyes widened and my cock hardened. Mom was too intent on watching the road that she didn’t see my gaze sweep over her entire body. It ended at her stockinged legs. The edge of the skirt had moved up slightly as she manipulated the pedals, exposing half of her thighs. For the first time, I knew what my friends saw in mom. And it frightened me.

It didn’t take long for us to reach home. Mom got out of the car quickly and entered the house. I followed her as quickly as I could. The house was empty, meaning that Rebecca and Amy were partying and wouldn’t be home till well past two. I looked at the wall clock, it was only 10:30 p.m. I started to dread being alone with mom.

Mom walked through the living room, heading for the kitchen. I made my way to the staircase. Then mom stopped. Without turning around, she said, “I was really looking forward to a nice quiet night.”

“I know,” I said, “and I’m sorry.”

She turned her head. “No, you don’t understand. I’ve been feeling so lonely that I just wanted to be with a man. And not just any man, but one who could make me feel young again.”

That got my attention. Mom needed to feel loved, not as a mother, but as a young, beautiful woman. She had been alone most of her life, sacrificing her personal and social life to care for three children for almost 18 years. And now, when she had the chance to be with a man again, I had screwed it up by answering her ad.

I felt sorry for her. I walked up and wrapped my arms around her waist. As I leaned forward, I said, “I’m sorry, mom.”

“That’s ok, son, you didn’t know.”

“I wish there was some way I could make it better.”

“Just hold me for a while, dear.”

So I did. But the close contact with her coupled with her sweet-smelling perfume made it hard for me to maintain my focus and I felt my cock hardening again. I didn’t move in case I gave myself away, but if I didn’t, then my cock would be pressing against mom’s ass, and she would know. I was in a dilemma and decided that I should distract her.

I placed my hands on her shoulders and squeezed lightly. Mom sighed. She was really tense from tonight’s encounter and a massage would do her good. I continued kneading her neck and shoulders, careful not to accidentally move her dress. Mom dropped her head and sighed again.

“Move lower, dear,” she said softly. My hands moved down her back, massaging her tight muscles along her backbone, until they reached the end of the exposed portion. My mind had already given up control and now my cock was doing the thinking. My fingers slipped under the edges of her dress and massaged her sides. When she didn’t do anything to stop me, I moved my hands up.

Then I touched the sides of her breasts. She let out a soft gasp. I stopped. When she didn’t offer any other resistance, I continued massaging her sides. Soon, my hands were at the edge of her shoulders. The dress rested precariously on the tops of my hands. A slight move and it would fall off.

I leaned forward. “Mom,” I said.

“Yes, dear,” she responded.

And I kissed the back of her neck. She purred. I kissed her again, then down her back. I came up and moved closer to her, pressing my hardness against her bum. She gasped.

“Dean?”

I lifted my hands and moved off her shoulders. The dress fell off, hanging from her belt and baring her top. Before she could block herself, I cupped her breasts and squeezed tenderly. She cooed and groaned. I kissed her shoulders.

“Mom,” I said, “take off your belt.”

Slowly, she worked at her belt buckle, then pulled it off and tossed it aside. Her dress fell all the way down to her feet. I moved a hand from her breast down her abdomen until it touched the edge of her panties. She moaned. I slipped it underneath and cupped her mound. She was wet.

I lowered myself until I was at eye-level with her bum. I placed a tender kiss on one cheek. In a smooth stroke, I pulled her panties down. Without being told, she stepped out of them. I tossed them aside, then turned her around. Her hands went through my hair, drawing me closer to her shaved pussy. I leaned forward and kissed it. She groaned. I kissed again. She groaned again. Then I gave a long lick along its entire length.

Mom trembled and nearly collapsed. I looked up at her as she looked down. “My god, Dean,” she said, “I just came.”

I stood up and started unbuttoning my shirt. She unbuckled my pants and pulled the zipper down. Before long, I had taken off my shirt and my pants were in a pile at my feet. Mom pulled my briefs down and let my cock spring up. She grasped it. I groaned.

“It’s so beautiful,” she said. “Like your dad’s.” Then she knelt down. I knew what was going to happen next, but I didn’t expect how it was going to feel. Mom swallowed the entire length of my cock and sucked it. I groaned and nearly came, but somehow I managed to hold it in. Mom continued sucking while her fingers traced the sensitive area between my balls and ass. It was fantastic, better than any I had ever received from the school girls.

I placed my hands at the sides of mom’s face and pulled her up. I planted a passionate, desperate kiss on her lips. She responded by opening her mouth and letting her tongue surge forward. As we kissed, she wrapped her arms around my waist and pulled me closer. My dick was pressed against her pussy and I started humping. She giggled and broke off the kiss.

“What are you trying to do?” she laughed.

“I, err…”

She made her way to the stairs and started walking up. I looked at her, unsure of what was happening. She stopped and looked at me. “Coming?” Then she continued walking up.

It took me a while to realize that she wanted me to follow her. I ran up the stairs and headed straight for her room. She was already lying on the bed, her legs spread apart, her pussy exposed. She turned and looked at me. Without a word, I approached her and got onto the bed. As we gazed into each other’s eyes, I positioned myself between her and slowly lowered myself.

Her hand found my dick and guided it into her pussy. She gasped when the head went in. I held my breath as I entered her. The feeling was fantastic! Mom’s pussy was as tight as any teen’s even after having three kids. My dick felt like it had entered a hole too small for it. I gasped when my entire length was inside her.

I looked at her again. She wrapped her arms around my chest and her legs around my waist. “Fuck me,” she said softly.

I didn’t need to be told twice. I drew out slowly, then plunged back in. She groaned and squeezed her eyes shut. I continued moving in and out, increasing my pace. Mom was groaning and screaming. “Oh, fuck, fuck!”

“Aah, mom, ooh…” I placed a hand on her breast and squeezed She squealed.

“Oh, Dean, fuck me, oh fuck me…”

I was fucking her faster than I had ever fucked anyone before. Mom’s pussy was simply incredible, she was squeezing on me, making her hole even tighter, but it felt doubly as exciting. Mom really knew what to do.

“I’m going to cum, mom,” I said.

“Oh fuck…fuck me, Dean,” was all she said.

I wanted to pull out, I had never cum inside a girl before for fear of getting her pregnant. But as I pulled out, mom would force me back in. I felt the pressure growing and knew I couldn’t stop it. I was going to cum inside mom!

Then I shot out. I shouted as my cum flooded her womb. Mom moaned, her legs squeezing me tighter, pressing me firmly against her body. My dick jerked within her, shooting more cum. Even when I felt that I had no more cum, mom’s pussy continued kneading at me, making me shoot more.

Finally my dick started to go limp. Mom unclamped her legs from around me, letting me get off her. I pulled out slowly and mom yelped when my head popped out. She looked at my glistening dick, then at my perspiring face.

“Mom, I…”

She placed a finger on my lips. “No, Dean, it’s ok,” she said. “There’s no need to explain.”

“No, mom, that’s not what I meant…”

But she cut me off again. “I know what we did was wrong, it’s incest, and we should never have let it happen again. But I needed it, you know, I just had to have a dick up my pussy, and you were there, so…”

I chuckled and shook my head.

“What’s so funny?” she asked.

“Mom, all I was going to say was: are you going to pay me?”

She looked at me in a strange way, then a smile spread across her face. “Let me think about it. If you’re really good, I may give you something better than money.”

I stopped and looked at her. “You know, you were a great fuck.”

“Thank you, hon.”

“So I was wondering, do you think it’s genetic?”