Betting On A Sure Thing

"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.