Betting On A Sure Thing

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.