Betting On A Sure Thing

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.