Betting On A Sure Thing

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 Suddenly I realized that her cheerleader uniform was outdated.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.

"No."

"You'll never find anyone else in such short time."

"No."

"I want to see you win more than anything."

"No."

"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.