Lisa And The Bet

This is one of the more significant events of my teen years. Not just the sexual aspect, but all the drama it caused. In a couple of previous stories of sexual exploits, I have changed the names of the people to protect their innocence, so to speak. I will engage in no such noble behavior for this story. Everyone got what they deserved in the end.

I was eighteen years old and in alot of trouble. I had been caught with two sheets of LSD. I was a month away from sentencing and scared myself into leaving town. As it turns out, I probably wouldn't have ended up in jail after all, but that is an entirely different story.

I packed up a backpack full of essentials and stuck out my thumb. Twenty-four hours later, with no sleep, I found myself in a truck stop in Fair Play, South Carolina. It was about an eight hour drive from where I had started. That was about par for the course. I usually averaged twenty-five to thirty miles an hour when hitching.

The waitresses in the place had taken an interest in me. Well, everyone had. It was just the waitresses who approached me. I was a sight to see, I'm sure. I was the quintessential hippy by appearance. Suede jacket with long fringe, matching boots, a paisley headband and cobalt blue, John Lennon type specs.

I was lavishing in the attention, but I had a ride to New Orleans that was leavin soon. One of the waitresses approached me and pointed to the counter at a man sitting with one of the other waitresses. He motioned for me to approach. I did.

His name was Olin Daniel Partain Junior. Try to imagine the name spoken in a strong, southern accent. He went by Danny.

"How you doin? My name's Danny, and this is my wife Lisa."

"Pleased to make your acquaintance."

"Whoo boy, you sure do talk like a yankee. So, where're you headed, or aint that my business?"

"Well, I'm about to catch a ride to Louisiana. Then...I don't know- south into Florida, or maybe west. I've never been to Mexico."

Lisa went to punch her timecard, as her shift was over. I couldn't help but notice the way her ass twitched when she walked. It wasn't an unusual thing for me to notice, but it wos far from the kast look I would take at her ass.

Danny continued, "What would you say if I could get you a job and a place to stay?"

"I'd say that would depend on the job and where I'd be staying."

Well, it turns out that he could get me a job as a brickmason's assistant. I stayed in the camper on their property the first night. The next night, after they decided I was safe, they set me up in a room in their trailer. In short time, I was an integral part of the household, from chores to finances.

One day, a few weeks after I had arrived, we were talking about sex. It wasn't anything suggestive, just talk of a primarily 'joking around' tone.

I made some comment referring to my sexual skills and Lisa said, "Boy, I'd make you cry for your momma!".

I though it an odd statement in it's context and company, but not nearly as odd as Danny's response.

He turned to her and said, "I bet you fifty bucks you can't."

A moment of silence weighted the air. I wasn't sure exactly how serious he was being. It turns out, he was dead serious. Suddenly, her bravado vanished, and she was the quintessential bashful schoolgirl. What a bet anyway. As if I would lose control of my mouth and brain and cry out for my mother? It seemed as if he was just arranging for me to fuck his wife. Why? I didn't care.

The next few moments of conversation served to crysallize the seriousness of his proposition. Lisa requested that I shave (which I never did). Danny explained that he would lock himself into the room at the end of the trailer and give us as much time as we needed. I couldn't believe it. I was going to fuck this man's wife... with his permission!

So, that night I showered and came out into the living room. Lisa went to the bathroom to get ready. She called out for Danny and he went back to the bathroom. I could see him but not her.

"Whoowee! Maybe he will cry for his momma after all!" Then to me, "Whitey, you better come through for me, I don't wanna give her fifty dollars of my pay just for her to spend it on woman type shit!"

With this, he entered the room at the back of the trailer and closed the door.

Lisa called out to me, "Turn out the lights and light the candles on the table and the TV!"

I did. When I told her it was done, I heard the door open. I still doubted the reality of this. Was it going to be a big hoax at my expense? Then she emerged.

She had her hair down for the first time I had seen. Her brown curls just passed her shoulder. She was wearing a baby blue teddy. Her thighs looked exquisite. She walked over to the couch and sat by me. She faced straight forward, not looking at me. I turned her head with a light touch of my fingers to her cheek. We kissed. She came out of her shell almost instantly. I kissed her cheeks and pulled her lips lightly with mine. We touched the tips of our tongues together playfully and then I sucked it as she pulled it back into her mouth.

The hand that had turned her cheek had slowly slid down her neck, over her shoulder, down her arm and settled on her hip. I squeezed the flesh of her hip. There is nothing else that feels quite like the way a woman's soft flesh gives way under the pressure of a firm grip. I slid my hand under her ass just as my other hand found the shoulder strap of her teddy.

I pulled back from kissing her so I could see as I exposed her breast. It was the first time I'd seen a woman's flesh under candle light. The effect is one to behold. I didn't touch her there just yet. I brought my other hand up to move the other shoulder strap and pulled the teddy down to the point where her hips stopped my progress. She was perfect.

I got off the couch and kneeled in front of her. We kissed again. As we did, I brought my hand to her left breast and grazed my palm over her nipple. It stiffened immediately. I kissed her chin and along her jawline, as I squeezed her tit. She moaned. It was all the encouragement I needed. I continued to kiss down her neck and onto her shoulder as my hands began exploring that of her body that was now exposed. I held both breasts and she told me to push them upward. I did, and she pushed her hips forward to make the first contact below our waists.

Part of me wanted to push her on the floor and fuck her furiously, but I knew things might end too quickly. I held tough. I pulled my hands back down, sinking my fingers into the flesh of her tits and slid my hands around to her sides. As my hands slid down toward her hips, she ground her pussy up against the bulge in my jeans. I was delirious. I forced myself to take note of the way she felt for fear I would race past parts of the experience and not enjoy them fully.

My hands came down to where her torso narrowed. At her waist, I could almost lock my fingers behind her back and still press my thumbs into her tummy. It was so overwhelmingly the feeling of a woman. At twenty-three, she was by far the oldest woman I had been with. I lost my will. Each of my hands grabbed an opposite hip. Fingers on her ass and palms on her thighs, I pulled her into me hard.

I sucked on her tit, taking the as much of her breast into my mouth as possible then releasing it to flick at her nipple with my tongue and pinch it with my lips. I pulled her off the couch and began kissing her stomach. My hand went between her legs. The lips of her pussy felt swollen and fleshy. Her teddy was wet.

I traced her belly button with my tongue as i rubbed her pussy through the teddy. I kissed and licked my way to the edge of her teddy and pulled it off her hips with a swift motion. I rubbed my face, my lips, my nose over her tummy and down into her soft hair. I pulled back for a second to look. I wondered if she shaved any. The hair on her pussy was just a small oval. The lips of her pussy were already open and the moisture on them gleamed in the candle light.

I took one long lick up the whole length of her slit and lingered on the clit. She was only the fourth girl I'd been with. I wasn't very experienced, but I knew what I was supposed to be doing. It didn't matter. I was hungry for her pussy. If only I could fuck her and lick her at the same time.

Her clit swelled. I pushed it up with my tongue and then down again, pushing it back under its hood as well as is swollen size would allow. I did that until I ached for the rest of her pussy. I sucked on the lips and pushed my tongue as deep into her as I could. I tongue fucked her until it felt as if my jaw would lock up. I started rubbing her clit with my bottom lip.

"Suck on my clit!" she cried.

I did. It was my first time discovering the technique. I have used it ever since. I pulled her clit between my lips and sucked it into my mouth as if I were drawing an over frozen milkshake through a straw. Then I pulled my head back, still sucking but pulling her clit almost back out with my motion... then back in. This didn't last long because she clamped my head between her thighs. I couldn't move my head at all. I could barely breathe but the flesh of her thighs against my face and the subtle smell of her womanhood had me ensnared. I kept sucking as best as I could, and she bagan to thrash. It occurred to me that this might be dangerous, but i continued. Then she bucked hard and let out a scream that brought the thought of Danny back into my head.

But just for an instant.

As she slowed down her motion and eased her grip, I was dizzied by the atmosphere. I sucked the fluids from her. She was considerably wetter from her orgasm. I literally drank from her and swallowed her fluids as the nectar they were.

I dragged my lips back up her flat tummy and onto her tits again. I was still clothed. She told me to stand up. She stood with me. She pulled my shirt up over my head and pulled her body flush with mine using the waist of my jeans as a handle.

"Ooh, who's excited!?", she said coyly as her thumb rubbed the pre-cum over the head of my dick. I was protruding over the waist of my jeans by this point. She undid them and gripped my dick tightly. Her hand was cold, which felt amazing. She stroked it two or three times and then dropped to her knees and pulled my jeans to the floor. I stumbled a little stepping out of them, and my dick bounced a little, bumping against her cheek.

She pushed my dick against my stomach and put her tongue under my balls. It tickled and titillated at the same time. She made little circles on them with her tongue and then lifted them with her free hand and ran her tongue up the back of my balls, almost from between my leg until they fell from her tongue.

She looked up at me with big eyes and asked, "Am I doing it right?".

"Oh God, yes."

She sucked them into her mouth in their entirety. When she pulled them out, she began to rub the head of my dick on her lips as if applying lip balm.

"Do you want to cum in my mouth, or in my pussy?"

I didnt' know if I'd ever get this opportunity again, so I dropped to my knees and pushed her down to the floor. She raised her legs high and spread them wide. I took her legs and put them on my shoulders and pushed into her. Her cry out as I did excited me. I slid slowly in and out of her, so she would feel every inch fully. I thrusted a little harder at the end of each in stroke. I felt cum boiling inside me. I began to fuck her hard. She cried out with every thrust. Her eyes were closed tight and her head was thrashing left with one push and right with the next. She was going to cum again. She pushed up to me again and again until her body stiffened with her pussy pushed down over my dick all the way to the base. I could actually feel the muscles inside her twitch. I still wasn't cumming.

As I pulled back, her pussy was noticably tighter. A few more thrusts and her body relaxed. I told her to turn over. I pulled out and she did. I looked down at myself. I don't think I'd ever seen myself that hard. I felt the manhood in my soul. When she turned over, she was on her knees and elbows. I pushed her down so her head was resting on the floor. I watched as my dick spread her back out. It was only a matter of seconds. I came so hard that I could see my cum pushing out of her as I pushed in. I collapsed forward, pushing her the rest of the way to the floor.

I was breathing hard as if I'd run five miles. She asked if I'd cum. I asked her what if I said no.

"I would say keep fucking."

My dick had yet to soften, and those words and the feel of the flesh of her ass made me feel ready to cum again. I didn't think I 'd ever feel the inside of her again, so I began moving. She didn't feel as tight now, but the feel of her ass as I pushed excited me enough to make up for it. Each thrust was accompanied by a popping sound as the air was trapped between my loins and her ass. I came again in a minute.

I rolled off her and we kissed. I said we'd better get dressed. We did. We turned on the lights. She went and put on a pair of jeans. I put on mine and Lisa told Danny he could come out. He did.

"She got nice tits, don't she."he said because she was still topless. "Lemme see you squeeze one."

"Danny!" she said in an admonishing tone. Then she added quietly, "Well, one quick squeeze!" and thrust her tits out toward me. I squeezed them like I wanted it to hurt. She grabbed a shirt and slid it on. She gave him an odd look and me a very sexual one.

Our sexual activity continued without his knowledge. I was told that they hadn't had sex in months. I was told he hit her and that he'd tried to get her to do a dog. She had kicked it so it would run away. Our affair got pretty serious and Danny found out. He moved out and came back. We continued. Eventually, he used his knowledge of my legal stauts and had me arrested.

I never saw Lisa again. I talked to her on the phone a couple of times. Last I heard, their house was demolished in a hurricane. I have also come to the conclusion that he told her what he was going to do. Oh well, live and learn.

A few good memories persist. His wife will always be part of my memory.