X-Rated Romp Through Life

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Bill's sex life from 18 on with many, many women.
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Prologue

The imaginary ramblings of this aging but still very sexually active man sometimes wander to his partially true but mostly imagined past. This is the tale of that mostly imagined life. I leave it to the reader to distinguish fact from fantasy. The names and places have been changed or most likely invented so that the reader is left with the thought that it might be he or she who is a part of this ramble.

Along the way, we have done one of two things with our limited years where sex is concerned: we have denied our capacity to excel in our sexuality and, at times, even denied its existence, thereby reaching the end with the nagging question, "Why?" Alternatively, we took full advantage of what we received at birth. Whether male or female, we have experienced the delights that sex alone offers. Experiencing orgasm with another human is understood only if indulged in frequently and with as much creativity as possible and with a willing partner who shares the quest for the most intense orgasm.

I cannot imagine the man or woman who, on his or her deathbed, has to wonder what sex with people who were available would have been like and how it would have changed his or her view of the world if prudishness was let go. They must wonder why they gave in to the dictates of fear, family, society or religion and sacrificed a huge part of whom and what they were: primarily sexual beings. This caution is directed primarily at the female reader since I have found in my travels that the female of the species is much more sensitive to their sexual nature than are men. It has been rare that I have found a woman who wasn't willing to initiate sex and then follow through with some of the most erotic techniques imaginable.

Just know that I will not been one of those who will leave this earth with any questions about sex unanswered. When I am breathing my last, it will be with the memory of the many woman with whom I have shared that which is at our core as humans: sex, or just plain fucking.

This story explores the sex life of Bill, an imaginary character who had the luxury of growing up in a family that did not adhere to the sexual mores of "normal" society. His mother died when Bill was very young, and his father remarried. His stepmother came into the marriage with a child who was several years older than Bill. By the time Bill became a slave to his overactive libido, his stepbrother was in the military. On the rare occasion that he returned with his wife for short visits, Bill was talking to a stranger. I guess one could say that Bill was an only child. His stepmother guided his trip through childhood, adolescence and early adulthood. He would thank her right to the grave.  

Chapter One

"It's about time," she said as she walked slowly toward me with the towel covering the critical parts of her body, parts that I had seen only in glossy magazines. She was naked under the towel that did not do such a great job of hiding any of those critical parts. I sat on the edge of my chair with an increasing bulge showing under the towel covering my now raging hard on. When it no longer served any purpose to attempt to hide the obvious, I pulled the towel from my lap and from under my ass, letting it fall to the floor, something I would never have dreamed of doing until that moment.

She continued to walk toward me, stopping just long enough to direct her attention to my cock and to lick her lips. She then lifted one leg over mine and straddled my legs, sliding her body down my front while pressing her breasts to my chest. The towel covering them did little to mask the sensation of her breasts as they pressed against me. Her towel had ridden up to her waist, leaving her vagina exposed and open to my cock which was now poised at its entrance. Slowly and deliberately, she slid down onto my cock, all the time looking into my eyes. She said nothing as she impaled herself with the help of one hand.

It took all of my concentration to keep from coming. This was the sexiest thing that I had ever experienced, although my experience was limited; I had never actually had my cock inside a woman, although my prom date had her hand around it. She sensed this and sat still while I settled into the sensation.

She began to move her breasts in a slow circle on my chest. Her nipples grew even more rigid, if that was possible. I took hold of the bottom of her towel and pulled it up. It caught for a second when it reached the underside of her breasts. They were firm and bigger than I was used to; my prom date had let me feel her breasts, but I had to reach under her dress to do it. I pulled harder and the towel slid over them. They bounced once then settled into their natural state, which gave no indication of sagging. Given her age, I found this unusual but very appealing. They looked a lot like some of those I had seen in glossy magazines that made the rounds of guys my age. When her towel was on the floor and her breasts completely exposed, I cupped them with both hands then lowered my head and played my tongue over her nipples. She finally gave out a low moan and began to move herself up and down on my cock, which was beyond anything I had experienced in my somewhat abbreviated sex life.

Eighteen years was not long enough to have formed the sort of experiences that would allow comparison with what was happening. She had sex down to an art form, and she was not reluctant to satisfy her needs.

Betty was my stepmother's best friend. She was younger than my stepmother by about ten years which made her about 38, but they seemed to have a lot in common. Her body was the stuff of a boy's wet dreams. She was about my height: 5'9". She must have weighed about 130 pounds. Her hair was short; it came to the bottom of her neckline. As I said, she was everything a young man could dream of in a woman. Naked, she was beyond the dream state. Now I know that she had the same sexual appetite as my stepmother.

As I look back on those times from the perspective of a middle-aged man, I view them with new appreciation for what Betty and my parents did for me. Some may have seen what we did and what I learned and from whom as perverted. I view it as nothing of the kind. It was an education that led me to a fulfilling life, a life that I might have missed without the early education offered by Betty, my parents and some other very significant and willing teachers.

My education began at Betty's house on the lake on one particularly memorable day. Betty asked my stepmother if I could help with some things that she needed done. I guess, in retrospect, me fucking her was high on her list of this she needed help with. We were going to take her boat out of the water and pull it into the boathouse where she would scrape it and put on a fresh coat of paint. As I left the house that morning, my stepmother reminded me to take my swimsuit and told me to have a great day.

When I arrived, Betty was in the yard raking leaves. She was wearing shorter shorts than I recalled seeing her in, not that I was complaining. A tight white T-shirt covered her breasts. I noticed that she was not wearing a bra, or maybe the bra she was wearing did not hide much. Whichever the case, her breasts caught my attention. I think she noticed that I was in a tit trance and asked if there was anything I would like before we started. I assumed, being the naïve kid that I was, that she meant a soft drink. I declined anything and managed to focus on her face in an attempt to get my over active cock under control.

Betty put the rake away and told me to follow her down to the lake where the boat bobbed in the water. She suggested that I wear shorts or a swim suit today because I would be in the water. I wore a loose pair of tan shorts and a pull over shirt. I followed Betty to the lake, all the while trying desperately to watch the trail and not her ass.

Betty lived on a lake near us. She had a cabin that her father had built many years before. It was right out of a book of beautiful cabins of the north. It was rustic and modern at the same time. It was made of logs but had all the modern conveniences. At the lakeshore were a sauna and a boathouse. A dock with diving platform and ladder extended out about fifty feet from the shore. There was a small gazebo up from the beach and slightly hidden among some trees. I always loved her place.

When we reached the lake, Betty suggested that I get in the water behind the boat and push it up onto the beach as far as possible while she pulled on the mooring line. The boat was heavy; it was made of wood and had been in the water all summer. As we began to work together to move the boat up the beach, the mooring line that Betty was pulling on broke and she fell backward onto the sand. Her shorts rode up on her legs and I got an even better view of her crotch. A slight flash of panty came into view for a second or two before she recovered and stood up. She brushed herself off and smiled. After a short discussion about how we should proceed, we decide that we should both get behind the boat and push. We stood very close together behind the boat, our hands on the transom, and began to push.

When we reached the sand, the boat came to an abrupt stop and our feet went out from under us at the same time. It was turning into a comedy act. The plunge into the water had a beneficial consequence, however. The thin T-shirt that Betty was wearing became semi-transparent. My earlier question was answered; she was not wearing a bra.

Betty sputtered as she stood up, brushing her chest. She looked down and saw that she appeared almost nude from the waist up and simply shrugged as though this was an everyday occurrence. It may have been for her, but it definitely was not for me. She suggested that we try a different approach.

We took opposite sides of the boat, pulled and lifted at the same time. This was a fortunate choice because I had developed a serious hard on that was making the job no less difficult. Directly across from me was a now semi-nude Betty, a woman I had previously thought of as someone who visited my stepmother on a regular basis and someone who fed my over active fantasy life when masturbating. Now, here she was showing me her breasts and her panties because her shorts had become translucent as well.

"Bill, should we give this up and get a tractor and try again another day?" Betty asked. As she spoke, I noticed that she was looking at the formation in my shorts.

"That sounds like a good idea. If we keep this up, we'll end up hurting ourselves," I replied.

This, however, left me with no place to hide my little problem, even though the "cat" was now out of the bag.

"Since we're already wet, how about if we take a swim then go up and have lunch," Betty said.

"Great idea," I replied, hoping that her top might become even more transparent.

We both waded back into deeper water where we were still touching bottom but the water, still warm for late August, came to our chests. Betty ducked down and began to swim out further. I followed close behind. She suddenly stopped, at least as sudden as one could stop in water, but I didn't notice and swam into her from the rear.

I grabbed her around the middle to keep from pushing her under and in doing so, I grabbed her breasts; they were soft and warm. The nipples were hard and long. My cock was jammed against her ass. After holding her longer than was necessary, I let go and began to tread water a few feet from her. She looked at me with a slight smile and said nothing about what had happened. She then turned and began swimming back toward the dock with me close behind.

My cock was in a state that made it difficult to swim, but I managed to get to the dock as she climbed out using the ladder. Then it was my turn, my telltale hard on almost out of control. Luckily, or maybe by design, Betty continued to walk away from the ladder, giving me a chance to get onto the dock with minimal embarrassment.

As we walked up the hill toward her cabin, Betty turned and told me to hurry, that the first one to the cabin had dibs on the shower and dry clothes. She must have known that I did not have any dry clothes with me. We both began to run up the hill. She was in her late thirties, but she could run as fast as I.

By the time we reached the cabin door, my hard on had reduced to a manageable state and I was able to face her. Her T-shirt was still semi-transparent, however, and the effect began to work on my cock once more.

Betty glanced down toward my cock for a second as she turned and walked toward the shower. I noticed a swing to her hips that was not there before. Maybe she was anticipating what was going to happen.

"I'll get a towel, and you can dry off. Take your shorts and shirt off if you want and put them in the drier. They should not take long to dry. You can use the towel to wrap around you. I'll be right out."

With that, Betty walked into her bathroom. I heard the shower begin to run a short time later. I also noticed that she had left the door partially open. As I slid my shorts down and took off my soaked underwear and T-shirt, I glanced into the bath. I could just make out Betty through the smoked glass shower door. She had to know what she was doing and that I was doing my best to sneak a peek at her.

Before I heard the shower stop, I had wrapped the towel around my hips and sat on a kitchen chair. I thought that I could stay there and not have to get up and show my predicament; that's how naïve I was at eighteen.

I was unable to get a good view through the open door as she got out of the shower, but my imagination completed the picture. After a few minutes, Betty came out of the bath, a towel wrapped around her body in the most sexually exciting way I could ever have imagined. The magazines that the horny boys in the community passed around were no match. She had dried off for the most part, but water still glistened on her chest above her breasts.

"About time," she said. I was not sure what that meant, but my cock seemed to have an idea. Betty almost danced toward me, never taking her eyes from mine except for the quick glance at where my cock was now trying to escape the confines of the towel. I thought that if it got any bigger, it would burst. Even when I got a hand job from my senior prom date, it did not get this big. Since the cat was now out of the bag, so to speak, I pulled the towel from around my waist and exposed my cock to Betty.

"I've been waiting for this for a long time, Bill," Betty said. "Ever since you were about sixteen and began to show signs of what you were going to become. I was just waiting until you graduated and were legal. You can call this your graduation gift from me, a gift that will keep on giving if you want."

With that, Betty walked toward me, straddled my legs and settled at the head of my cock. She reached down, took my cock in her right hand, and guided it to her vagina. I could feel the slippery entrance as she flicked the head of my cock from the front to the back until she was moaning. She then settled herself onto my cock, which slid its full length into her. I thought that I would come right then if she moved at all.

"Did you know that your stepmother and I talked about this and thought it would be a great way to train you in the ways of the female anatomy and satisfying a woman?" Betty said as she sat on my cock.

I was surprised by what she said, but not surprised enough to stop what was happening. If anything, it made the experience even sexier. Imagine, an older woman showing me what sex was all about, and the older woman was Betty whose body was beyond sexy; It was the perfect place to practice the most exciting thing a young man could do with a woman. Yes, I had my cock inside a woman. Being jacked off by a female's hand just didn't compare.

As Betty started to lick my ears and neck, I had an orgasm that must have shot like a water cannon into her. I felt like I was never going to stop coming. Betty yelped like a puppy as I shot semen into her. She continued to bounce then put both her legs around the back of the chair and pulled me into her. We sat like that for a minute while we recovered enough to get up.

Betty slid slowly off me and stood up, my sperm glistening on her pubic hair, some starting to run down her legs. This was my first view of a real vagina, or pussy, as my pals and I called it. She picked up her towel and wiped her vagina and legs. As she did so, she bent down and kissed me on the lips. The kiss was unlike any I'd felt. Even the ones that my prom date applied fell short, and she was a great kisser. Maybe it was because my prom date had not sat on my cock.

The kiss lasted at least a minute. Betty then stood up and took my hand. She led me into the bathroom where she turned on the shower. She got in then pulled me in by my reinvigorated cock. The shower was roomy enough for one person, but two people made it a forced sexual exercise. We had to rub together as we let the water run over us. Betty took a bar of soap and began to soap me where she could reach. Her hands ended up on my cock, which had found new life.

"My, aren't you the horny guy," Betty said with a big smile. She worked her hand back and forth on my cock in a skilled way that led me to think that she had practiced the art of the hand job. I found her vagina and soaped it up and down. I slid first one then two fingers into her and jacked them back and forth. This was something of which I had only dreamt.

"Bill, if you feel toward the top of the opening you'll find a little bump; that's my clitoris. Rubbing and sucking on that is what makes me come."

Betty took the middle finger of my right hand and guided it to the spot. Slowly and gently, she moved my finger around her clitoris. When she was satisfied that I had learned enough for the moment, she let me take over. It took about two minutes of what I thought was a decent technique for Betty to start breathing hard and tell me not to stop. Then she came. As she did, I slid two fingers into her vagina. I reached in as far as I could reach then withdrew them. As she continued to come, she still jacked my cock with all her might. The hand job worked its magic and I came, shooting more semen on her hand, legs and shower wall.

We both hung on to each other as we came down from the sex-induced high that we had both experienced. It was amazing that we did not injure ourselves in the close confines of the shower.

With my semen washed from the shower wall and Betty's hand and legs, we got out of the shower and dried each other. She gave special attention to my cock, which seemed to have developed a mind of its own. I paid close attention to drying her breasts. I was in love with them. They stood out proudly from her body in a way that made them impossible to ignore.

"I don't want to get too personal, Betty, but how do you manage to have such great breasts?"

"Do you mean for a woman of my age? And you can call them tits if you want to. I know that's what guys your age call them."

"Well, yes, I guess that's what I mean. And I'd like to call them tits. They're beautiful."

"Thank you. I had help from a plastic surgeon who gave them new life about a year ago."

"I thought that I saw something different about you about a year ago."

"So, you've been keeping track of my body, have you?"

""Yes, I have. Your body has always been great, but it got better."

"Did you masturbate thinking about my body?"

"All the time; I used to think about what you must look like without clothes while I jacked off."

"Now you won't have to wonder, will you? We can even take some pictures today, so you have something to remind you when I am not available. How would you like that?"

"That would be great, but I'm afraid my stepmother might find them."