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Betting On A Sure Thing

Category: Mature
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I had just finished my freshman year of college, having somehow existed through months of frustration. My grades were excellent but my sex life was a failure. With hormones pumping throughout my body at breakneck speed, and a goodly amount of attractive girls running around campus suffering with the same condition, one would have thought that I would have connected with at least one member of the opposite sex. Alas, it did not come to pass. I was heading home without any good stories to tell to my old high school buddies and especially my best friend, George Simmons.

Before leaving for college, we had made a bet, wagering one hundred dollars on the best sexual encounter we would have before seeing each other again. George had always been lucky with the girls in high school, and I was sure that he would have one hell of a story ready for me when I saw him. I had had a few backseat car adventures with a rubber covering my cock at high school too, but this was college. This was different and I had nothing to tell him. Honor being utmost to our story, I had resigned myself to loosing this bet. That was until Mrs. Simmons called and talked to my mom.

Mrs. Simmons and my mom go way back. They had been best friends when they were young and had somehow ended up living very close to each other, one block to be exact, after marriage. Pregnancies seemed to have been planned also, leading to my friendship with George. Naturally, living so close and parents knowing each other had made frequent visits to each other’s house the norm. Mrs. Simmons had always treated me well, never minding my presence. George’s father had a good job with an investment firm, so his mom didn’t have to work. Instead, she had devoted her life to pleasing the kids of the neighborhood. Having spent so much time with the area kids had seemed to stop the aging process for Mrs. Simmons.

While my mom and the rest of the mothers of the surrounding homes got older in their actions and appearance, George’s mom stayed as fresh and as young as my first clear memories of her. She would play baseball and football with the boys, getting dirtier than most of us. She even took a bunch of us camping once and did a better job than any of the fathers ever did. She was voted “Best Mom in Town” by all of the boys we hung around with. She had also won a vote that George never knew about. The rest of the boys in the neighborhood had unofficially elected her in a secret ballot, “Prettiest Mom in the World.” Mrs. Simmons blew all of the other moms away in that vote. You know, it’s hard to vote against your own mother in a beauty contest, but no other mother even got one vote. Thinking back, she reminded me of that physical fitness guru Denise Austin. She was blond, beautiful, fit and trim, and bubbly. A little while after Mrs. Simmons and my mom had finished their chat, I learned how blond, and how beautiful, and how bubbly she remained.

My mother talked with Mrs. Simmons for quite a few minutes and then relayed the expected message from George to me. He had arrived home a couple of days earlier and couldn’t wait to see me. Seeing me wasn’t what he wanted. Money was. I had known George all of my life and he couldn’t wait to brag about himself. It was a quality his mom had always hated but had no control over. She blamed it on her husband, saying that it was a fault that almost drove them apart. She would always say, “Why can’t you be like your friend Paul. He doesn’t need to brag.” She warned him that, “bragging would get him in trouble some day or lead to something that no one would be able to control.” I’d get embarrassed as she put her arm around my shoulders as she said this, but I also liked the soft touch and smell of her skin when it happened.

Unfortunately, due to my lack of sexual activity at college, I was now in store for another round of boasting from George. Mrs. Simmons had told my mom that George would be leaving for the day quite soon, and that I should come over as soon as possible. I left as soon as I could, wanting to get this entire episode of my life over with. Little did I know that Mrs. Simmons would make me want this day in my life to never end while she helped me win my bet with George.

Summer had taken hold with a vengeance this year, with heat and humidity reigning and showing no signs of abdication. I put on a pair of cut-offs and tank-top and headed for George’s house. Memories of my youth flooded my mind as I walked; fun and worriless summers seemingly so far away now. I didn’t have a job lined up and I was going over my friends’ house to lose one hundred bucks. As I walked around to the back door, which was my old and familiar entrance to the Simmons’ house, a slight feeling of depression began to fill my body. I knew that I would have to endure the usual spouting off by George, as he would wallow in his own self-proclaimed glory. Most of his other shortcomings were easy to overlook, but I just could not take his arrogance, just as his mother couldn’t. At that moment, I would have done anything to change the outcome of our bet. I would have sold my soul to the devil for just one wild incident with a girl. I walked through the unlocked door, just as I had done thousands of times before. The familiar aromas that one becomes accustomed to with frequent exposure eased the tension I felt throughout my entire body. I quickly recognized the smells of their kitchen, the fresh linen in the laundry room, and the soft perfume that Mrs. Simmons always wore. I called out as I seated myself at the kitchen table.

“Hello,” I said. “It’s me, Paul.”

I waited for George’s piercing voice to fill my ears, but it never came. Instead, the pleasant voice of Mrs. Simmons chimed from somewhere down the hall. I heard her light footsteps before I saw her.

“Hi Paul,” she said happily. “It’s just me. You missed George. He just left.”

“Oh,” I said with little enthusiasm. “I came as soon as I could.”

“Well,” she answered as she approached the table. “You don’t have to sound so disappointed that it’s only me here to greet you. I thought you might be a little more pleased to hear my voice instead of George’s.”

“I’m sorry,” I said as I got up from the table. “It’s nice to see you again Mrs. Simmons. It’s been a long year. How are you doing?”

“Well,” she said as she came over to give me a hug and quick kiss on the cheek. “That’s a little better. I’m doing just fine. It looks as if college life suits you just fine Paul. Seems that you’ve grown a bit more from last time I saw you.”

She stood back and took a good, long look at me. It was as if she were sizing me up, preparing to buy me and take me home. I took the opportunity to evaluate Mrs. Simmons too. As usual, she had not changed one bit, still resembling a vibrant Denise Austin. She still looked as young as when we played our games together with the rest of the kids some ten years ago. She was wearing a pair of shorts that came to the middle of her thighs. Even though she was a year or two older than my mother, she was probably sixty pounds lighter. Had my mom been wearing those shorts, flesh would have been exploding from beneath the hem. On Mrs. Simmons however, there was more than enough space to put a hand up inside between the material and her skin. Her legs were tanned and trim, muscles still as visible as they had always been when she ran the bases during our backyard baseball games. She wore a loose fitting shirt, the top two buttons undone in a vain attempt to stem the heat of the day. Mrs. Simmons must have been working pretty hard around the house because her sweat had stained a good portion of her shirt. Beads of moisture that had probably collected on the inside surface of her tits had succumbed to gravity and rolled down the middle of her chest. A large dark area of wetness discolored the stomach area of her shirt. Patches of darkness also marked the underside of her tits, allowing her bra to be quite visible through her shirt.

“Would you like a glass of iced tea Paul?” she asked as she made her way towards the refrigerator. “I’ve been doing some work around the house and I’ve been sweating my ass off.”

“Sure Mrs. Simmons,” I answered as I watched her walk away.

A dark stain of wetness had created a thick line of discoloration right down the middle of the back of her shorts. Material had gathered into the crack of her ass, defining the round and firm shape of her cheeks. As she opened the door and bent down to get the container of tea, her shorts fought to ride up. Friction, caused by the heat of the day and her body, was finally overcome. Her shorts sprung up as if launched from a catapult, sticking to the alluring underside of her ass. When she stood up, her shorts stayed where they were. Automatically, she reached around with her arm, pushing the index finger of her right hand under the legs of her shorts and pulling them down. Maybe she had forgotten that I was sitting there, but when she turned around she didn’t seem to realize what she had done. She continued to talk to me as if nothing out of the ordinary had happened. We sat and sipped on the cold drinks as we informed each other about of lives over the past year. Even though we were only sitting, sweat soon began to spill out of our pores. Mrs. Simmons didn’t have the air-conditioning on in the house. She said that it was her way of keeping her weight down. She’d put the air on before her husband came home. She said that she had grown accustomed to the heat and that she didn’t mind sweating.

“In fact,” she said leaning over and talking softly, as if someone else might hear, “now that George is away at college and his father is at work, I can walk around with little or no clothes on. I just have to make sure that the curtains are pulled.”

She gave me a little wink when she told me this and the thought of seeing Mrs. Simmons walking around, wearing only a bra and panties, or maybe nothing at all, entered my mind. Sure, I had seen her in bikini bathing suits when they had thrown pool parties, but that was different. Dressing like that was expected. Undressing in order to stay cool, when someone might unexpectedly visit or see, was exciting, adventuress. The more I thought of it, the more normal it seemed that Mrs. Simmons would be the type of woman to do something like that. She was different from all of the other moms around. And, she had a body that really didn’t need clothes. During those pool parties, she was the only mother that would dare wear a bikini.

“I’ll be sure to visit unannounced during our next heat wave,” I said jokingly.

“You be sure to do that Paul,” she said laughing. “The weatherman says that tomorrow is going to be even hotter.”

We both giggled at our little flirtatious banter, but I did feel somewhat strange that she played along so willingly. She refilled our glasses and we talked some more. I always felt comfortable with her, more comfortable than with girls my own age. I had no need to be someone I wasn’t. With her I was Paul, not some superman that someone else wanted me to be. As Mrs. Simmons finished her second glass of tea, she got up from the table fanning herself.

“Stay here, would you Paul?” she said. “I’ve been working all morning and I must look and smell horrible. I need to take a shower. I’ll only be a few minutes. Have some more tea and I’ll be right back.”

She turned quickly and made her way down the hall before I had a chance to answer. I heard doors opening and closing and then the soft footfalls of Mrs. Simmons’ bare feet on the hardwood floor of the hall as she made her way to the bathroom. I leaned over and thought I caught a quick glimpse of her naked leg glide into the bathroom.

“Did she still have her clothes on, or was she naked?” I wondered to myself. “Nah. Just your imagination.”

The thought of going up to the bathroom door, which was left slightly ajar by George’s mother to let the steam escape, and peeking inside entered my brain. I might be able to see Mrs. Simmons’ naked body through the frosted glass of the shower stall. Even with a distorted view, I was sure that she would look beautiful. Fear of getting caught kept my ass glued to my chair. That fear, however, didn’t stop my cock from getting hard. An uncomfortable bend soon formed in my shorts as the thought of Mrs. Simmons’ naked body, only a few steps away behind an unlocked door, filled my mind’s eye. The bet with George and the lost money were a million miles away. Finally, after about twenty minutes, which to me was quite a long shower, the water stopped. I crammed my mind with other thoughts, trying to deflate the rigid pole I had between my legs. I heard Mrs. Simmons humming to herself as I awaited her return. I turned my back to the hallway, not wanting her to think that I was trying to see her as she came out. Time seemed to drag as the sound of her hair dryer droned from within the bathroom. Finally, the dryer was turned off and I heard the bathroom door creak as it opened. I expected to hear her footsteps head towards her bedroom, but instead they came towards the kitchen. Her bare feet padded on the linoleum floor as she approached the table. As I turned, I saw Mrs. Simmons standing across the table from me with a wide smile across her face. She was only wearing a soft, pink-colored, satin robe. It came down to just above her knees, her smooth tanned legs and bare feet seemed to dangle from underneath, as if she were just floating there. A satin belt was tied around her waist, amplifying the curves of her torso. The cleavage of her soft breasts was only slightly visible. However, the round, full size of each tit was clearly defined, as the satin material of the robe seemed to adhere to each of them. I was only slightly aware of the sound I made as I gulped a large volume of hot, thick air into my lungs. I was totally unaware of the unhidden bulge that had quickly reappeared in my shorts. Even the uncomfortable bend in my cock couldn’t stir me from my shocked stupor.

Without saying a word, Mrs. Simmons made her way around the table to where I sat. In one easy, fluid motion, she easily lifted her body onto the table and sat right in front of me. Had I been more conscious, I would have watched intently as she mounted the table, hoping to get a very good look at what was between her legs. Unfortunately, blind shock had gripped my senses. She now sat in front of me with her legs closed, knees held tightly together. Even so, with the hem of the robe now located in the middle of her thighs, I could easily make out the soft blond hairs that sprouted between her legs. She leaned towards me, her tits pitching slightly forward. The top of her robe opened slightly and the soft, white, inner portions of her tits became visible. Had the muscles of my eyes been any weaker, I’m sure that they would have fallen out of their sockets and down the front of her robe. Finally, the pounding of my heart, and the exerted efforts of my lungs to bring oxygen to my numbed brain, woke me from my daze. As I looked up into Mrs. Simmons’ dark blue eyes, I heard her speak.

“Now what’s this I hear about a bet between you and George?” she asked.

“Huh?” was all that came out of my mouth.

“Wake up Paul,” she said, as she reached out all held my chin softly in her hand. “You and George made a bet. I overheard him talking…gloating to someone on the phone. He said that he was going to take you for a hundred bucks.” She let go of my chin and leaned back on the table, resting on her hands. The top of the skirt portion of her robe pulled up higher on her thighs, making the view to her pubic hairs even better. She showed no disquiet about her exposure and continued to talk as if nothing was wrong. “I heard him say something about making out with a girl. Best story wins. Am I close, or what? Tell me Paul. Does it have to do with having sex with a girl? Is he going to win? Tell me he isn’t Paul. Tell me you’ve got a better story. I don’t want to her him bragging about how he took you for a hundred bucks all summer. Tell me Paul. Tell me you’ll win.”

“Well,” I said, sounding very embarrassed about having to tell her that George would win. Here I was, sitting and looking up the robe of my friend’s mother, gazing at the pubic hairs between her legs, and I didn’t feel bad about that. However, having to tell her that her son would win a bet from me had me wanting to crawl under a rock.

She listened intently as I told her about the bet. A full range of expressions appeared on her face as she listened to all of my attempts and failures throughout my school year. She laughed frequently, even though I didn’t think that all of my efforts were that funny. Her tits were jostled by her expressed amusement and I watched her nipples harden as they rubbed against the satin material of her robe. I could tell, however, that her mind was working, thought processes setting sights on a solution to my dilemma. I don’t know why, but I didn’t recognize that she considered the bet to be her problem as well. I forgot that she had to live with George, and his boasting could be relentless. When I had finished with my account, she sat back up and folded her hands on her lap. I found that I had relaxed too, not feeling as uncomfortable as I had been when she first came into view after her shower. Even my cock had relaxed, although I could still tell that a larger that normal amount of blood was being pumped through its arteries. Ultimately, a smile that conveyed a sense of triumph became visible on the face of Mrs. Simmons. She leaned towards me once again, and as she spoke, I noticed for the first time how large and full her lips were. Each word seemed to be erotically released for my visual enjoyment. I thought that I could watch her talk for hours; mesmerized by the shapes her lips would take on with every word she spoke.

“Tell me Paul,” she began. “What would you say if I told you that I might know a girl that may be willing to help you win this bet?”

“Huh?” was my response once again.

“I’m sure I know someone that would enjoy seeing you beat George at his own game,” she continued, excitement building in her voice. “She’d love to see George have to eat his words. You should have heard him talking to his friend over the phone Paul. He already had your money in his pocket. Said there was no way he could lose this bet with you. That’s why he made it. Listen Paul. If there’s a way to beat him, you’ve got to take it. Believe me, I wouldn’t suggest this if I didn’t think it would work. I have a picture of the girl and I’m sure she’ll be more than willing to help. All you have to do is agree. Let me get the picture. Once you see her picture, you won’t be able to say no. Wait here. I’ll be right back.”

In an instant, she was down off of the table. Any attempts at refusal would have fallen on deaf ears. The slapping sound of her feet rapidly hitting the oak floor of the hall quickly faded as she made her way into her bedroom. I turned my stare to where she had been sitting on the table. A distinct image of the round shape of her ass was visible on the thick sheet of glass that covered the table. A representation, created by moisture from her damp body, was displayed in front of me. Slowly, regrettably, the image disappeared. I leaned towards it, wishing that it would remain, when I noticed a small pool of water in the middle of the image. Undeniably, it had dripped out of her cunt, from somewhere within that hidden hole where her most desirable essence lay. Closer examination revealed the presence of two pubic hairs. I reached out with both hands, picking one hair up with each. I brought them close to my eyes, fascinated by their coiled shape and soft blond color; the same color of the hair on Mrs. Simmons’ head. I put them both into my pocket, praying that I would be able to find them later when I went home.

The sound of a drawer closing loudly and the echo of Mrs. Simmons’ bare feet once more alighting on the floor made my heart skip a beat. Her unbridled enthusiasm radiated hope, curtailing even my thoughts of certain defeat. She came over to me carrying a large book that I recognized as my high school yearbook. She had her finger inside, marking the page that she wanted to open it to. As she moved, I noticed that her robe was not as tightly closed as it had once been. Her hurried movements had opened the front quite a bit. Below her satin belt, the flaps of her robe had spread apart and exposed a large portion of her upper thigh. Sure, I had seen more when she had worn her bikini, but this was different. Skin, which was supposed to be hidden was now uncovered for my eyes to see. When she leaned over to place the book in front of me, the upper portion of her robe hung loosely down. Her right tit, which was the furthest one away from me, was totally revealed. It was more pointed than I had expected, crowned by a very hard nipple. Unconcerned with what part of her body I might see next, she opened the book to the page she had found and pointed at a picture. It was an action snapshot of a cheerleader. A wide, enthusiastic smile graced her face as she seemed to be hanging in mid-air. Her attractive legs were spread wide apart as she held her pom-poms high above her head. Adequate breasts, which would still grow in size, distorted the name of our school. To say that I was pleasantly surprised by Mrs. Simmons’ choice was a great understatement.

“How would you like her to help you out Paul?” she asked with pride.

“You’re kidding. You mean to tell me that she might be willing to…you know…help me…I mean…” I stammered.

“Yes Paul,” she replied. “I’m sure that this girl would do anything to see George have to eat his words. It’s something she’s waited for all of her life.”

“Who is she?” I asked, not recognizing her. “She doesn’t look familiar, even though she went to school with me.”

“Look harder Paul,” she replied. “You’ve known her all of your life, but…she didn’t go to school with you.”

I looked at Mrs. Simmons with a puzzled stare and then focused on the girls picture once more. Suddenly I realized that her cheerleader uniform was outdated. I searched the page for the date of the yearbook, finding it at the top corner. As my eyes focused on the date, I blinked as 1977 came into view. The book was 24 years old, 5 years older than me. In fact, that was a year before my mother graduated from high school. I felt a tightening in my chest as I looked back at the girls’ picture. I noticed a blackness start to grow at my peripheral vision and I was soon looking through a black tunnel. I zoomed in on her image, concentrating on her face. Her blond hair and large lips took my breath away. I pulled my vision down to the bottom of the picture, looking for the printed caption. I quickly found it, just above Mrs. Simmons’ left hand, the hand that had a diamond and wedding band on its ring finger. I read what I dared not.

“Jennifer Dietz cheerfully shows her school spirit!”

Even in my debilitated state, my brain continued to work somewhat. Jennifer! That was Mrs. Simmons’ first name, but I couldn’t recall her maiden name. However, I knew that she was part German, and Dietz did have a European ring to it. I felt sweat rolling down my chest as I slowly turned my gaze up towards Mrs. Simmons’ face. A delighted smile greeted me as she realized that I knew it was her picture in the yearbook. I pushed my chair away from the table, trying to get as far away from the picture as I could. Even though Mrs. Simmons’ robe was barely covering her well-shaped body, I didn’t look at anything else but her eyes. A distinct expression of devilish bliss glittered within the dark blue pools that stared back at me.

“It’s you,” I said, pointing at the book and then at Mrs. Simmons, and then back at the book again.

“That’s right,” she said matter-of-factly. “Great idea, Huh?”

“No!” I said loudly. “No way!”

“Yes Paul,” she replied softly. “Yes.”

“You’re crazy,” I said, trying to laugh. “You on some drugs or something?”

“No Paul, I’m thinking very clearly. Who better than me?”

“No,” was all I could think of saying.

“Who else is going to help you?” she asked.


“You’ll never find anyone else in such short time.”


“I want to see you win more than anything.”


“Do you want to lose a hundred dollars?”

“No. I mean yes. I mean…I don’t know anything anymore.”

Mrs. Simmons took a step towards me. I pushed my seat back again, not realizing that I had been pushing it back with every no I had said. I slammed into the cabinets and waited until Mrs. Simmons finally reached me. As she squatted down next to me, the front of her robe draped over the outsides of her legs, revealing her entire crotch to me. She had her legs spread wide apart for balance, as she rested her ass on the heels of her feet. Although I was in a somewhat panicked state, the sight of the slit between her legs was in perfect focus. She repositioned herself, and the lips of her cunt spread ever so slightly. I felt my cock harden even more, pushing powerfully at my pants. Suddenly, I felt her hand softly land on the skin of my inner thigh. I quickly averted my stare from between her legs to her calm and understanding face.

“Listen very carefully to what I’m going to say to you Paul,” she said slowly. “Do you hear me Paul?”

I nodded yes.

“Good,” she continued. “When you see my son again, he’s going to think that he’s taken you for a hundred dollars. He’s going to let the whole world know about it. He’s going to brag so much that you’ll have to hide during the daytime, and only come out at night. And you know what Paul? I’m going to have to listen to it for the entire summer. He’ll never let a day go by without reminding me how my “favorite” neighborhood boy struck out with every girl on campus and had to cough up one hundred dollars. That’s right Paul. You were my favorite. Still are. That’s why you have to win this bet. You’re not going to be able to find someone to fuck today other than me. George will be back later this evening with his father. Right now they’re both in the city. I sent George with the car to pick up his dad. He took the train into work today and had planned to come home that way too. When I heard George talking to his friend over the phone about this bet, I had to think fast. George has to learn a lesson about bragging, and if I can have a hand in screwing him over, well then, I’m going to do it. You have to go through with this Paul, or there’ll be hell to pay for the both of us. So, what’ll it be? Do we work as a team and teach George a lesson, or do we suffer, listening to his arrogant, conceited bragging for the rest of our lives.”

I knew that everything Mrs. Simmons had just said was true. George would never let me live this down. Plus, knowing how she felt about me and how badly she wanted to teach her son a lesson, made refusing her offer that much harder. Nevertheless, I still couldn’t accept the thought of having sex with her. Screwing some girl at college is one thing. Fucking your best friends’ mother to win a bet from him is something else. Adding in to the equation the fact that the woman offering to let me shove my cock into her pussy has been my mother’s best friend for over thirty years was just mind-boggling. I didn’t want to say no, but I couldn’t say yes. I couldn’t say anything. I just sat there, staring at her eyes and listening to the deafening silence of the house.

Sensing my no-win situation, Mrs. Simmons took matters into her own hands, or maybe I should say, she took my cock into her own hands. With deliberate, thought-out movements, Mrs. Simmons easily undid the snap and zipper of my shorts. Without hesitating, she reached inside and easily pulled my hard throbbing cock out into the heat of the day. Unable to really believe what was happening, I sat motionless and watched as she held my cock in her hand. A soft smile that relayed the feeling that everything was all right beamed from her face. As she got down on her knees and positioned her body between my legs, I didn’t believe that she would do what I thought she was going to do next. I felt my left leg begin to shake as I watched Mrs. Simmons bring her face over my crotch. As the back of her head came into view, I felt the large soft lips of her mouth envelop my cock. Slowly, purposefully, she began to slide her mouth up and down over the shaft of my cock. Her warm saliva quickly began to drip down to my balls. Sweat and spit soaked my shorts in seconds. A rapid flick of her tongue to the underside of my cock was all it took to send the muscles around my balls into convulsions. I held onto the bottom of the chair as my hips lurched, and I felt the tip of my cock probe deeply into her throat as a salvo of cum flew out of my cock. Mrs. Simmons didn’t flinch. She continued to bob up and down on my cock as another round of cum traveled up and out of the shaft of my cock. I was soon aware of a hot fluid beginning to cover my balls as cum began to flow out of Mrs. Simmons’ mouth. Another flick of her tongue brought a final explosion of cum from my cock. A moan of accomplishment came from George’s mother as she lifted her head from my cock and swallowed whatever cum was left in her mouth. Thick, white fluid covered her chin as she smiled up at my face. As she spoke, I could see the white remnants and sticky tendrils of the fluid produced by my balls adhering to the inside of her mouth.

“Well Paul,” she began. “How was that?”

I gasped for a breath and said, “Wow.”

“Let’s see you find a college girl that’ll do that,” she said as she wiped the sticky mess from her chin. “I bet George didn’t get a blowjob like that.”

“I doubt it,” I replied.

As she sat back down on the kitchen floor, Mrs. Simmons untied the belt of her robe. She leaned back on her hands and spread her legs in a futile attempt to cool off. When I was younger, and we had played a hard game with the other kids of the neighborhood, Mrs. Simmons had always assumed this position to rest. Seeing her again like this made the whole situation easier to accept. We were on the same team once more, playing a game against her son and playing to win.

“Well I guess I’ll win this bet, right Mrs. Simmons?” I said.

“You’re not going to win anything with just a blowjob Paul,” she countered. “You and I are far from done. I don’t want there to be any doubt of you winning. This was just a preliminary round. We’ve got all day to make sure you win. I have plans for you Paul.”

She put her hands on her knees and then pushed on them until they touched the floor. The lips of her cunt spread farther apart than what I had seen earlier. She then shook her shoulders from side to side, making her tits swing back and forth. Even though I had just emptied more cum into her mouth than I had ever produced, my cock lurched with excitement at the site of my mother’s best friend sitting naked on the floor in front of me. A small drop of cum oozed out of the tip of my cock.

“Save that for later Paul,” she said with a smile. “Why don’t you get out of those dirty shorts and I’ll wash them. You can take a shower while a take care a few more things that I need to get done.”

As if in a trance, I did as she said. I struggled a little bit with the uncomfortable feeling between my legs as Mrs. Simmons scurried around her kitchen. She went to the back door and closed it. Anyone could have walked up to the back screen-door and watched as Mrs. Simmons “bobbed for apples” over my cock. She put some dishes away and then glided across the floor to reposition the chairs around the table. All the while, her untied robe tried unsuccessfully to keep up with her flowing movements. Her trim, naked body was always two steps ahead of the pink, satin material. Her pyramid-shaped tits pointed the way and her firm ass hardly shook with each step. That now familiar sound of her bare feet on the linoleum floor ushered her long legs past my view. It was the same stride she had when circling the bases after she hit a homerun for our team.

Completing my task, I stood naked holding my clothes, waiting for my next set of instructions. My cock had begun to hang, instead of pointing out and slightly towards the left, as it usually did when it was hard. It was still more than twice its normal size. It amazed me that Mrs. Simmons had no difficulty putting the entire hard shaft into her mouth. My cock pitched upwards as the vision of the back of her head rising up and down between my legs reentered my mind. Its motion must have caught Mrs. Simmons’ attention because she stopped what she was doing and spoke.

“All set Paul?” she asked, as if nothing was unusual about the situation occurring in her family’s kitchen.

She, her husband and son, and even my parents with me by their side, had gathered together and eaten meals here. Now, she had just given me a blowjob at the kitchen table as nonchalantly as she had probably eaten today’s breakfast. George’s mother walked over to me and took my dirty shorts in her hands. If she had touched the sticky mess that was contained somewhere within, she gave no sign that she had. She smiled as she held the bundle next to her body and then leaned over and gave me a soft kiss on the lips. I didn’t kiss back, although I don’t think that she expected me too. I’m sure she knew that I still needed time to feel relaxed with what was happening.

“Follow me,” she said, as she turned and headed off towards the hallway.

Obediently, with my cock swinging to the left and right, I trailed Mrs. Simmons like a puppy. I thought to myself, as I watched the motion of her ass beneath her robe, that none of this would be happening right now if it wasn’t for her son George. Had he not conned me into accepting this bet, his mother wouldn’t have just had my cock inside of her mouth, using it as a receptacle for the sizable amount of cum that by balls produced. I wouldn’t be in a predicament that I had no idea of how to get out, although, a few minutes ago, there was no way that I wanted to be anywhere else. If he had only been less obnoxious, his mother wouldn’t have been so determined to see him lose. Because of his actions, I was now following her, without a stitch of clothes on my body and her wearing little more than myself. She made a quick detour into the laundry room, placing my soiled shorts and shirt on top of the washer. I stood exposed like Michelangelo’s David, waiting for the appreciative stare of my audience. Mrs. Simmons turned with an admiring glance that was aimed in the direction of my cock.

“Be careful where you stick that thing Paul,” she said as she gave it a playful tap, having a little bit of cum stick to her fingers. “You could hurt a girl that isn’t as experienced as me. Time for your shower,” she continued, as she wiped the leftovers of my blowjob from her hands.

She led me inside her bathroom and began to run the water. I stood watching as she closed the door and proceeded to take her satin robe off to hang it on a hook that was on the wall. When she turned and saw my unbelieving stare, she giggled.

“No Paul,” she said. “I’m not joining you right now. Maybe later. You go clean yourself. I’ve got one more thing to take care of.”

I felt my cock begin to stiffen again as I stood next to her in the confined area of the bathroom. I still felt that I shouldn’t let anymore happen between us, but the physical reactions that were taking place inside of my body far outweighed the mental ones in my brain. If this was how fate had decided that my life and hers would proceed, then who was I to step in and demand changes. I didn’t start these events; I didn’t initiate what was happening between Mrs. Simmons and myself. Someone or something else had written the script to this day, and I was now determined to play my part as best as I could. As she tried to make her way around my body, she held onto my waist and allowed her tits to rub against my back. I felt the soft hairs that covered her cunt brush softly against my ass. We said nothing, but we were both aware that we liked very much what we felt. When she finally stood in front of me once more, my cock had hardened with its normal bend to the left. She brought her lips to mine and kissed me again. This time I kissed her back. It wasn’t a passionate kiss, but I felt the muscles of my crotch tighten and my cock expand with excitement. We kissed again and then once more. My heart was pounding rapidly and if I continued to breath as I was, I would soon hyperventilate and pass out. Mrs. Simmons was keenly aware of what was happening as she put her hands on my chest in order to separate our bodies. She took a step back, resting her body against the sink cabinet. Her funnel shaped tits pointed directly at me, her hard nipples beckoning me to suck on them. I leaned towards them, wanting to hold one of them in my mouth. She reached out and placed her hands on my shoulders, stopping my advance.

“It’s nice to see that you’re starting to accept what going on Paul,” she said softly. “You’ll have your way with me soon enough. Remember, we have to do this right so you win this bet. Like I said, I have one more thing to do before we go on. You take a long, cold shower and calm down. When you’re done, come to my bedroom. I’ll be waiting.”

She gently placed her hand on my face and left me alone. Even over the sound of the running water, I heard her feet pad back to the laundry room to wash my clothes. Again, I obediently followed Mrs. Simmons’ orders. I entered the shower, adjusting the temperature to the coldest temperature I could stand. Wanting to make sure that all of the cum was washed out of the hairs around my cock, I scrubbed my crotch more carefully than usual. I thought of anything but Mrs. Simmons. Slowly, my cock telescoped back to its normal size. The cold water drew my balls back into my body as my sac shrunk into a puckered pouch. I thought that I heard Mrs. Simmons make her way back through the hall to her bedroom. I wondered if she peeked into the bathroom to watch me wash. Finally, having felt that I had recovered from what had happened to me in the kitchen, I turned the water off and began to dry myself. Suddenly, I heard Mrs. Simmons talking to someone. I thought that my heart stopped for at least two beats, thinking that someone else was in the house, possibly Mr. Simmons and George. Not moving a muscle, I strained to hear another voice. Finally, I realized that Mrs. Simmons was talking to someone on the phone. I began to breath again, thinking that maybe I had made a mistake in accepting Mrs. Simmons’ scheme. Maybe I should end it all now and take my chances to win the bet with only the story of my blowjob. I made my way as quietly as I could back to the laundry room. To my dismay, my clothes were still in the wash. I was naked, inside my friends’ house with his mother waiting for me in her bedroom. I had no other option than to go to her room. I slowly padded my way to the end of the hall, following the sound of her pleasant voice.

As I stood naked in the doorway, I saw Mrs. Simmons standing with her back towards me. She was in front of the windows, pulling the shades down. She was wearing a threadbare t-shirt that scarcely covered the cheeks of her ass. She was conversing enjoyably over the phone, laughing at something the other person had said. As she pulled the last shade down, a sun-catcher that was on the window fell to the floor. She bent over to pick the object up, causing her t-shirt to ride up on her back. Her round, firm ass expanded into my view. The inviting sight of the soft mound of her pussy dropped down between her firm legs. All thoughts that being in her bedroom was a mistake vanished for that moment. Again, there was no other place in the world that I would have wanted to be. When she turned around and saw me, a wide smile enhanced her pretty face. With her next few words however, she stopped my heart from beating for a second time.

“He’s right here with me now Joan,” she said with a smile.

Joan was my mother’s name. Instinctively I put my hands over my crotch, trying to hide my cock and balls. Mrs. Simmons placed her hand over her mouth, stifling a laugh of amusement. I looked at her pleadingly, thinking that she was telling my mom about what was going on between the two of us. Not missing a beat, Mrs. Simmons continued to talk to my mom as she conveyed to me with hand gestures and facial expressions that everything was all right. She strolled over to her bed and jumped onto the mattress, waving her hand and inviting me to sit next to her, putting her finger over her lips, telling me to be quiet. Cautiously I joined her, for some reason thinking that my mother might be able to somehow see me through the phone lines. Mrs. Simmons held the receiver away from her ear, letting me listen in on their conversation.

“I really appreciate you making dinner for Paul,” my mom said happily. “You’re sure it won’t be any problem Jennifer?”

“Not at all Joan,” Mrs. Simmons said. “It’ll be nice to have some company. I feel terrible that he missed George. I feel that it was my fault, not calling him earlier.”

“Oh, he’ll have more than enough time to see George again,” my mom replied.

“He knows he can come over whenever he wants Joan,” Mrs. Simmons said smiling at me. “Do you want to talk to him?”

I shook my head no, not thinking that I would be able to get one word out of my mouth to save my life.

“No. That’s all right,” my mom answered. “Just be sure to send him home when he starts to bore you.”

“That may take quite a while Joan,” Mrs. Simmons said as she wrapped the fingers of her free hand around my cock. “Right now, your son is the most interesting thing I’ve seen in a year.”

I couldn’t believe how my mom and Mrs. Simmons laughed at her last comment. They went on talking for a few more minutes as I sat naked next to my mother’s best friend. They talked about the weather, the latest news, the new clothing store in town, and other menial things. They then set up a date for a bridge party with two other mothers they knew. I sat in amazement as Mrs. Simmons carried on, doing what she had to do, not to be sociable with my mother, but to be able to fuck her best friend’s son without any unscheduled interruptions. Finally, they said their good-byes and Mrs. Simmons turned the portable phone off.

“We’re all set Paul,” she said triumphantly. “Your with me until I’m sure you win this bet.”

“What about Mr. Simmons and George?” I asked. “They could come back at any time.”

“Not to worry,” she said as she got up to put the receiver back into its cradle and to take her t-shirt off. “I called them while you were in the shower. They won’t be home until after mid-night. So, what do you say? Let’s you and me start winning that bet.”

With that, she walked over and stood in front of me. She leaned down, putting her hands on either side of my legs, and kissed me. This kiss, however, was not like the others she had given to me today. This time, she pushed her tongue lovingly into my mouth. Slowly, she probed with her tongue, finding mine and playfully dancing with it. I soon forgot that the tongue I was playing with belonged to woman who wore a wedding band on her left hand. With my eyes closed, the uncomfortable feeling of having sex with my friend’s mother never entered my thoughts. Even though she had gone to high school with my mother, it did nothing to deter the excitement building between my legs. My cock was rock hard in seconds, throbbing as it rose up into the warm air of the day. Mrs. Simmons knew immediately when my cock was as hard as it going to get. She slowly withdrew her mouth from mine and bent down to put her face over my cock for a second time today. Once again, I gazed down at the back of her head, her blond hair shinning as a ray of sun found its way past the shades. For one more time, I watched as she let her large lips float up and down over the thick shaft of my cock. This time however, the rapid flick of her tongue didn’t send my cock into convulsions. Instead, I reached around her chest cautiously, my arms moving spasmodically until my hands arrived at her tits. Her tits were even more pointed now, the pull of the earth elongating their form until a perfect conical shape was achieved. I cupped her tits gently and pushed them back up towards her chest, flattening them against her warm body. I heard her moan with pleasure as she continued to suck on my hard cock. I fought the urge to cum in her mouth, doing my utmost to enjoy the sensations she was benevolent enough to bestow upon me. Finally, I leaned back on the bed, waiting for Mrs. Simmons to conclude her oral workout and wondering what George would say if he knew that his mother would do these things to me so that he would lose a bet.

At last, Mrs. Simmons took her mouth off of my cock. As she wiped her spittle from her lips, she smiled and got onto the bed with me. She put her fingers to her jaw and began to massage the muscles just below her ears as she knelt beside me.

“I’m not used to keeping my mouth open so wide for so long,” she said. “That cock of yours is a lot bigger than I thought Paul. Believe me, my husband just doesn’t match up to you. I can’t wait to start and feel you pushing that tool into my cunt. I’m sure that the only time I had anything that big inside of my pussy was when George was coming out.”

She laughed as she talked, crawling on her hands and knees to the head of the bed. I watched as she flipped over onto her back, resting her head in the palms of her hands and spreading her legs until she was comfortable. I made my way to the middle of the foot of the bed, far enough away from Mrs. Simmons so that neither one of us could touch the other. One would think that having sex with someone you knew since childhood would have made things easier, but when that someone was your mother’s age, and her best friend, hesitancy had to be expected. Was one hundred dollars that important? Did George’s boasting really bother me this much? I was constantly fluctuating from acceptance to rejection of the whole situation. Mrs. Simmons used this delay as an opportunity to remind me of the purpose of our actions.

“Don’t let any of this bother you Paul,” she said softly. “Remember, you wouldn’t be here if I didn’t want this to happen. My son needs to be taught a lesson that I should have taught him years ago. I failed to take steps back then that would have prevented all of this. Now I have to act. I can’t let you suffer for my mistakes. If having sex with you is the price I have to pay, I’d gladly do it a million times. Honest Paul, I don’t consider this to be horrible or repulsive. Right now, I can’t wait for you to be on top of me. I haven’t been this excited about the prospect of having sex in a long time. I’m as hot as I’ve ever been. Please, don’t make me wait any longer. Don’t torture me. Put that hard cock into my cunt and win this bet from George.”

Mrs. Simmons held her arms out towards me, wiggling her fingers, beckoning me to come to her. I looked down between my legs, my throbbing cock rocking back and forth with each beat of my heart. I saw a large drop of clear fluid welling up from the hole at its tip. I watched as it began to roll lazily down the shaft of my cock. I looked back towards Mrs. Simmons, her arms still extended out in my direction, waiting to hold me tightly against her warm, soft body. I don’t consciously remember willing myself to move, but I recall how her hands seemed to grow in size as I neared her. I do remember how her face beamed with delight as she gently cradled me in her arms. I remembered my childhood, when she hugged each of her team members after every hard-earned victory. We may have been celebrating our victory over George a bit early, but I think that we both knew that there was no way we were going to lose.

We kissed with more passion than I had ever known. Moans of pleasure and excitement came from both of us. Our hands gently caressed each other’s body and delighted in the soft, warm touch of our partners skin. We held each other tightly, not wanting our bodies to be separated despite the heat of the early afternoon. When our mouths finally parted, Mrs. Simmons whispered in my ear. She was showing me the way towards ecstasy without me realizing it.

“Suck on my nipples Paul,” she said quietly, the heat of her breath sending goose bumps down my neck.

Obediently, I lifted my body from hers, exposing her pointed tits to the cooler heat of the room. Although she was on her back, her tits still retained their conical shape. I grasped the left one gently in my hand and softly squeezed it. Mrs. Simmons moaned with satisfaction as the tip of her tit rose from the pressure of my fingers. Her nipple levitated, sitting at the top of her tit like the beacon of a lighthouse. I quickly placed my mouth over it, amazed at how hard it was. Mrs. Simmons let out a little squeal as millions of electrical pulses shot through her body. I let my tongue caress her nipple, intrigued by the reaction her entire body exhibited. She drew her feet up towards her ass and lifted her hips from the bed. Her upper body squirmed like a snake, moving from left to right as I tried to balance myself on top of her. When I began to suck on her nipple, she arched her back and grabbed the sheets of the bed. I think that even if my mother had walked in on us at that time, Mrs. Simmons would have begged me to continue. As I proceed to do the same to her right tit, I sensed her lift her legs from the bed and then felt her gently rest them on mine, her heels positioned on the insides of my thighs. I felt my body press further into her crotch, the soft hairs covering her pussy rubbing against my belly. As I continued to stimulate her nipple, she wiggled her crotch back and forth against my stomach. I felt the warmth and wetness of her cunt as the lips of her pussy stretched apart. A slippery, warm liquid soon coated my stomach. I knew that she would need to make more of that juice when she tried to take my cock inside of her body. Thankfully, she had decided that now was the time to try. She took my head in her hands and tenderly lifted it from her nipple. She looked into my eyes with a hungry stare, now wanting to fuck me more than she wanted to teach her son a lesson. My winning a bet was secondary to the uncontainable desire she had to have my cock inside of her cunt. Having me fill her cunt with cum was more important to Mrs. Simmons than me having a hundred dollars stay in my pocket. At that point in time, it was more important to me too. I didn’t care that she was George’s mom. I didn’t care that she was my mom’s best friend. I didn’t care that she was more than twenty years older than me. All I cared about was sticking my hard cock into her. She spoke, but I already knew what she was going to say, and she wouldn’t have to ask twice.

“Fuck me Paul,” she said desperately. “Shove that big cock of yours inside of me. Make me cum. Make me happy. We’ll show George how to win a bet over sex. He’ll think twice before he challenges you again. Come on Paul. Take me. I’m all yours. Do what you want to me. Fuck me Paul. Fuck me.”

With that, she took her legs off of mine and tucked the heels of her feet up against her ass, spreading her knees as far apart as she could. I got up from where I was and quickly positioned my cock at the opening of her cunt. I could see it shine as more of her fluids oozed out from within. With her fingers, she spread the lips of her cunt as wide as she could, setting in motion the fuck of a lifetime. I placed the tip of my cock at her hole and lowered my hips, forcing the head of my cock into cunt. The warmth from inside of her body somehow felt hotter than the heat of the sun. She moaned with delight, knowing that soon my entire cock would be throbbing inside of her. As I slowly began to push the shaft of my cock into Mrs. Jennifer Simmons, I saw her eyes begin to widen with unexpected surprise. She knew that my cock was big, but I guess she really didn’t appreciate its full size until she felt her cunt begin to expand in order to accept the shaft she had so easily taken in her mouth. Up until my freshman year of high school phys. ed., I wasn’t aware of my size until some of the guys commented on it. Even back then, I was bigger when I was soft than most of them were when they were hard. The discrepancy is size was quite apparent then, and another five years of life had done nothing to curtail my growth.

“Oh my God,” she said slowly, each word taking at least five seconds to exit her mouth, her eyes unblinking. “I don’t believe what I’m feeling. Oh my God Paul. Please take your time. I feel like I’m fucking a god damned horse.”

“Do you want me to take it out?” I asked, thinking that she didn’t like what she felt.

“Don’t you dare do such a thing,” she said as she held onto my ass tightly with her hands. “You’re not going to hurt me Paul. This is going to be the best fuck I’ve ever had, that is, as soon as my cunt stretches enough to take all of you in. Don’t worry. This is going to be fun. Just take your time. When you get that whole thing inside of me, then you can start pumping. I’m positive I’m really going to enjoy helping you win this bet now.”

With that, she let go of my ass and once again placed her hands under her head. She took a deep breath, her expanding lungs lifting her firm, pointed tits towards the ceiling. As she exhaled I sensed her body relax, the tight grip that she had around my cock lessened. I pulled back, taking the small length of my shaft out of her cunt, letting only the head of my cock remain inside of her. Now having a greater sense of responsibility for my actions, I prepared to do as Mrs. Simmons had asked. I looked at her face and saw her smile. She licked her lips and nodded, letting me know that she was ready. I took a deep breath and gently began to lower the shaft of my cock inside of her once again. Pushing my cock into her by only millimeters at a time, I hoped that I wouldn’t hurt her. I pulled my cock back as slowly as I had pushed it in, retreating until only the head of my cock still remained, and then slowly re-entered her lubricated hole, adding a few more millimeters each time. I continued this process until half of the length of my cock was inside of her. Mrs. Simmons had now closed her eyes, concentrating on what she was feeling between her legs, willing her cunt to expand. I turned my gaze to where our bodies were one, scrutinizing my cock, which was wedged tightly into her cunt. As I continued to pump, I noticed how stretched the flesh around her opening was. I was fascinated as to how the inner lips of her cunt followed my cock as I entered her, diving down inside of her as if glued to the shaft of my cock. When I pulled my cock back, they unfolded outwards, seemingly trying to stop my withdrawal. Further and further I pushed my cock into her, contemplating about the amount of suction that was being created by the tight seal around my cock. As the entire length of my thick cock finally fell deep inside of her, a rush of air was forced out of her cunt, the size of my cock leaving little room for such a needless substance. A victorious sigh of success was happily expelled from my mother’s best friend as she felt the end of my cock extend to the back walls of her cunt. She could be proud of the fact that her older age had no effect on the ability of her cunt to stretch to its limits and accept a cock larger than any other it had ever entertained. She could brag about it to anyone she cared to; I wouldn’t mind. As I started to pump my cock into her once more, again I thought of the suction building inside of her. I imagined the walls of her cunt fluctuating back and forth as a vacuum was created inside her cunt. A crazy thought, that if we continued long enough I wouldn’t be able to pull my cock out of her, entered my mind. I saw the two of us naked, attached at the hips, unable to break apart. Mr. Simmons and George would come home to find us butt naked, walking around the house like a pair of Siamese twins. I could just see the two of them trying to pull us apart as the vacuum inside her cunt fought to keep us together. Don’t get me wrong. To be in that situation for the rest of my life, my cock buried deep between Mrs. Simmons’ firm and muscular legs, would have been just fine with me. The only drawback would have been the awkward task of explaining to my mother how her best friend of thirty-or-so years ended up being happily perched on her son’s hard cock.

The movement of Mrs. Simmons’ legs quickly brought me back to the task at hand. Instinctively, I had been pumping my cock in and out of her cunt as I enjoyed my fantasy. She was now holding the backs of her thighs, tilting her hips higher into the air. Large amounts of fluid were now drenching her cunt; her body recognizing the problem created by the size of my cock and taking steps to remedy it. I was amazed at how easily my cock slid in and out of the pussy of George’s mother. She still had her eyes closed and she was now humming softly to herself, just as she had when she was drying herself after her shower. The volume of her song increased ever so slightly each time my cock bottomed out deep inside of her cunt. Finally I recognized the tune as the fight song of our high school. Being the cheerleader that she was, she was cheering us on to a victory over her son. I began to thrust my cock into her with more force, gradually building up speed. Mrs. Simmons easily stayed with me, now spreading her legs farther apart. I found myself plunging deeper into her cunt, even though I thought that this would be impossible. Suddenly, she began to hum louder as she opened her eyes. She looked straight at me, a determined look covering her face. And then, all of a sudden, she stopped humming and began to grunt as she rocked her hips forcefully into my crotch. With each downward plunge of my cock into her hole, she powerfully responded back to my action. At last, her grunts turned into a low moan that filled the heavy air of the room. I felt the muscles of her cunt tighten around my cock as her orgasm took control of her body. She brought her hands to my ass once more and held on to me as tightly as she could. I felt the nails of her fingers bury into my cheeks as she began to lose any control she had left. Immediately, the muscles of cock and balls sprung into action. I felt my balls tighten for the second time today, squeezing the hot, thick fluid produced within into the shaft of my cock. I sensed the muscles of my cock convulse, transporting my cum through the entire length of my cock in a heartbeat. The head of my cock expanded as the added volume of my erupting cum spewed into Mrs. Simmons’ cunt. My cock was buried as far as it could go into my mother’s friend, the hot liquid shooting out and hitting the back walls of her cunt instantly. Immediately, cum ricocheted off of the walls of her cunt and back towards my cock. Instantly, I felt the warm, sticky fluid cover the head of my cock. George’s mother shuddered beneath me as she sensed her cunt begin to fill with the fruits of her labor. A thrilled squeal quietly escaped from her tightly clenched lips, sending my balls and cock into another spasm of action. Another load of cum was instantly produced and deposited inside of my mom’s best friend, by the child she had given birth to. Mrs. Simmons reached up and grabbed her tits, squeezing her nipples as she pitched her legs back and forth though the air, rocking her hips purposefully against my crotch. She was rubbing her clit against my body, instantly transporting herself into another orgasmic seizure. Following her cue, I began to pump my cock in and out of her cunt once more. With every withdrawal, a warm, sticky goo made of cum and her lubricating juice exited from her cunt. I felt another load of cum being quickly manufactured in my balls. Muscles were working furiously in a vain attempt to launch the last shipment of hot, sticky cum into her. Consciously I held back, waiting until I couldn’t delay any longer. When I felt the pressure in my cock build to its highest limits, I plunged into her cunt as far as I could. I heard my mother’s friend gasp as my final payload of rapture inducing cum rocketed into her cunt. It flew out of my cock as if powered by a rocket. Mrs. Simmons’ eyes expressed her surprise and pleasure as she felt my projectile explode inside of her. Her mouth opened as a cry of delight left her lungs. Her hips continued to rock back and forth as she rode out the last waves of her own delirious inducing orgasm. She now had so much fluid inside of her cunt that the entire volume of the last deposit of cum wouldn’t fit. A white, warm, sticky solution oozed its way past the entire circumference of my cock, soaking the entire crotch and ass of my friend’s mother. Despite the obvious mess, I pressed my body as forcefully as I could onto Mrs. Simmons. I loved her for what she had just done, and I loved her for being the friend she was to all of the boys of the neighborhood when we grew up. All of them would have wanted to thank her for being who she was in some way. I could only hope that the way I had just thanked her would be sufficient.

As Mrs. Simmons finally descended from her physically induced high, she wrapped her legs around my body, pressing me even harder between her legs. I felt my cock convulse inside of her stretched-out cunt with every beat of my heart. I wondered if her insides would ever revert back to their normal size, or had I stretched her out permanently? In spite of the heat created by ourselves, and the large, yellow orb in the sky, we remained locked in the same position. Every few minutes, I could sense a slight vibration pass through Mrs. Simmons’ body, producing a soft moan of satisfaction from her throat. She seemed quite content to have me stay on top of her. I felt the muscles of her cunt squeeze my cock forcefully, as if she were trying to wring out the last drops of cum which might still remain within the entire length of my cock.

Finally, the sounds of the newest batch of young children in the neighborhood filtered through the open windows. Their laughter made both of us stir and the feeling of the mess between our legs told both of us that it was time to clean up. As I lifted my body off of Mrs. Simmons, I knew that my cock was still as hard as when we had started. We both watched as I slowly began to pull my cock out of her cunt. In spite of the workout we had just put her cunt through, her hole was still tightly wrapped around my cock. I fully expected to hear the sound of a “pop” when it finally fell out of her. As the final inch of my shaft appeared and we both knew that the head of my cock was next, we both stared intently for the final show. Pulling my hips back, the head of my cock saw the light of day once more. The hole of her cunt remained open, as if an invisible cock was still inside of her. And then, as her cunt quickly began to return to its normal size, a flood of cum was expelled from her hole. A few seconds of calm was followed by another torrent of fluid. As relieved as I was that I hadn’t stretched her out of shape, I felt responsible for the changes her body was going through now.

“Sorry about that,” I said softly.

“Don’t be silly Paul,” she replied with a smile. “That was the most fascinating thing I ever saw my body do. Believe me. It sure beats giving birth.”

I smiled at her and leaned down to give her a kiss, thankful that she wasn’t upset. This time, as the cool water of the shower ran on and on, two bodies occupied the shower stall. Mrs. Simmons joined me now, enjoying the refreshing feeling of the soft spray and the grateful touch of my hands. I too enjoyed the attention she awarded to me, thankful that I hadn’t met anyone at school. Having no concern that her husband and son would return early, or that my mother would ever suspect that anything so unusual would occur between her son and her long time friend, we remained naked after our shower, eating leftovers at the kitchen table as my clothes dried in the dryer. We had sex one more time before I left, with Mrs. Simmons sitting on top of me. She rode me like a professional bull rider, her cunt glued onto my cock in spite of my bucking hips. Following another very quick shower, we put our clothes on and I prepared to leave out the back door. As I stood on the porch I searched for words to thank her.

“I really don’t know what to say Mrs. Simmons,” I said slowly. “I never thought that anything like this would ever happen to me…or you. I hope that you won’t be upset by any of this later. Its just that…”

“Paul,” she interrupted. “You don’t have to apologize for anything that happened today. It happened because of George and it happened because I wanted it to. I vowed to myself a long time ago that I would help you in anyway I could if you ever needed it. In order to win this bet you needed my help, and if the help that you needed required me to fuck you…well then, I was going to fuck you. And believe me Paul; I’d do it again…bet or no bet. You can’t begin to imagine how good it felt. Now you just go home and tell your mom that you had a nice dinner over here. Tell her anything that you want and I’ll back you up. You sleep well tonight, and then come over tomorrow to collect your hundred bucks.”

She leaned down from the doorstep and gave me a soft kiss on the cheek, just as she had when I first entered this same door earlier in the day. As I walked away, I wished that I could have stayed longer. I knew however that my mom would worry, not that her son might be fucking her best friend, but that her son was beginning to be a nuisance to Mrs. Simmons. I went straight to bed when I got home, sleeping as soundly as I had when I had exhausted myself playing outside as a child. Yes, Mrs. Simmons had probably tired me out back then too.

I woke the next morning, surprisingly quite refreshed. My friend George had already called, impatient to see me. The weatherman was predicting another scorcher. After a hearty breakfast, I made my way to the Simmons residence. Mr. Simmons had gone to work. George and his mother were in the kitchen eating their breakfast. I joined them at the table and Mrs. Simmons smiled as I sat in the same chair she had given me a blowjob in. I knew what she was smiling about but I hid my amusement. After a little polite chatter she left us, allowing her son and myself to settle our bet. Following our stories, it was obvious that I had won. The only thing I changed was the name and age of my partner. Other than that, I told George everything that his mother and I did to each other. Just recounting the events of the previous day produced a rock hard cock inside of my pants. I was positive that George had one too, and I wondered if he would still have gotten one if he knew that I had fucked his mother instead of some fictitious cheerleader from college. Despite my clear victory, George’s pride was evidently bruised. The boasting that he was prepared to churn out was now stuck in his craw. Defeat wasn’t as hard to accept, as was the inability to boast. As Mrs. Simmons re-entered the kitchen, and as George placed the last twenty-dollar bill in my hand, he unwittingly offered up his mother’s delectable body to me once again.

“How ’bout giving me a chance to get even ol’ pal,” he asked slyly. “I think you just got lucky this time. Why don’t we give it another go, okay? Same bet for this year too. Or are you afraid?”

I glanced at George’s mother as she stood behind him. Her eyebrows had lifted with delight and a wide smile adorned her youthful looking face. She was nodding her head rapidly, her hands clasped together in a prayerful plea. I decided to play hard to get, wondering who would be more upset.

“Gosh,” I said with an air of reservation. “I don’t know George. Can I think about it and let you know later?”

“What’s the matter Paul?” he asked with an irritated tone. I could tell that his arrogance had suffered little from losing the bet. “You know you can’t win again. That’s it. You know you were just lucky. I could win this bet nine out of ten times against you. How ’bout this? Double or nothing. You got the guts for that Paul?”

I looked at Mrs. Simmons once more, but this time she wasn’t looking at me. She was staring at the back of her son’s head, disappointment and disgust marring the beauty that should have been gracing her face. Her fists were clenched as if she were ready to pummel her son with a thousand blows. The hurt that she felt made my final decision more resolute.

“Okay George,” I said hiding my anger. “It’s your money. Two hundred bucks, winner takes all.”

“Great,” he responded. “Two hundred, winner takes all.”

We reached out to each other and shook hands to seal the bet. Mrs. Simmons beamed with excitement and silently applauded the outcome. I held onto her son’s hand tightly, not letting him pull his hand from mine as I added another stipulation to our bet.

“One more thing,” I added, as mother and son looked at me with anticipation. “Let’s not wait a year. How about making it for this upcoming semester?”

“Fine with me,” George replied confidently, gripping my hand even tighter. “Its your money.”

Squeezing in return even harder, I added, “We can do this until we graduate. How does that sound?”

“Done,” he said, sealing his and his mother’s fate.

“Done,” I replied.

As we emphasized the completion of the terms of our bet with a final shake, we both smiled at each other, but for different reasons. I glanced at Mrs. Simmons once again. She had a far away look in her eyes as I watched her bring her hand between her legs. She tugged at the seam of her pants between her legs. Juice had begun to flow from her cunt in anticipation of three more years of fun. George broke the strained air of the last few minutes with words that illustrated his lack of awareness about his attitude.

“Hey man,” he said happily. “Weatherman says it’s going to be hotter today than it was yesterday. I’m heading for the beach. Why don’t you come along? Maybe we can find some good lookin’ babes. What do ya’ say? I’m leaving right now.”

A negative headshake by Mrs. Simmons really wasn’t necessary, but the intensity of her movements told me that I would have a much better time if I stayed in the vicinity of her body, specifically her legs. With actions that showed disappointment, I told George that I couldn’t make it this time.

“I’d love to man,” I said, “but my parents had some errands they wanted me to tend to before they came home from work. Maybe next time.”

“Okay man,” George replied, not sounding too disappointed.

Suddenly, Mrs. Simmons, who hadn’t said a word since she had returned to the kitchen, spoke to me in a sexy voice that her son had no perception of.

“Would you like to stay and have some cold iced-tea before you leave Paul?” she asked with a knowing smile.

“I’d love to stay and have a drink Mrs. Simmons,” I replied, emphasizing the word stay.

“Great,” she said happily, as she made her way to the refrigerator.

As she bent over to get the container, taking more time than was necessary to find it, I appreciatively stared at her firm ass, understanding that the view was intentional. She shifted her weight, causing her shorts to ride up into the crack of her ass. With some additional help from a tug with her hands, the cheeks of her ass were lay bare for my eyes to see. George was totally oblivious to what was happening as he prepared to head off for the beach. Finally, his mother brought the iced tea to the table and poured me a drink.

“Thank you very, very much Mrs. Simmons,” I said, silently speaking the words “nice ass” to her.

“Your very welcome Paul,” she replied, as she silently spoke the words “fuck me” to her son’s best friend.

Finally, George was ready to leave. His mother and I walked him to the front door to see him off.

“You sure you don’t want to come man?” he asked as he walked down the steps.

“Positive,” I replied. “You have a good time.”

“Better time than you’ll have man,” he said, throwing in his last dig.

“I doubt it,” I said softly, as Mrs. Simmons closed the door, my hand sliding down the back of her shorts and taking a firm hold of the left cheek of her ass.

“I doubt it too,” his mother said, as she slid her hand down my shorts and squeezed my hard cock. “Practice makes perfect, right Paul?”

“You can bet on it,” I said, as we leaned towards each other and kissed.

We laughed as I placed my half empty glass of iced tea on a living room end table. I took my shoes off and walked with Mrs. Simmons back to her bedroom. The weatherman was right. Today was going to be much hotter than yesterday.

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