Hello. My name is Carl. I am a middle-aged man, with what I've been told is quite a past. As I was lying in bed one evening with a current ... fuck-buddy? FWB? ... we started talking about our sexual history. While hers is very limited, she was fascinated listening to mine. She told me about Literotica and suggested that I sign up and start writing some of this down. After thinking about it for a while, I decided, why the hell not?
The following stories are all true, to the best of my memory. Names have been changed to protect the not-so-innocent. (If anybody reading these stories thinks that they know who I am, please send me a message through the feedback link.)
I was, and maybe still am, probably what would now be called a man-slut. I realized a long time ago that I am simply not good at long-term relationships. I have truly tried, but after a while, they just tend to fall apart, especially as I got older. Even my marriage fell apart, but that was honestly just as much her fault as mine. I make no apologies or excuses. I am merely telling my story.
I hope you enjoy reading them as much as I did living them. I will do my best to tell you all of this in chronological order, but I make no guarantees that they will come out that way...
This first chapter is rather long, but it covers a two week period, so I hope you will enjoy the lead up to what is still one of the most memorable and important encounters of my life.
*****
The earliest memories that I can tell you about, and stay within the legal limits of Literotica, would be from my High School years.
I was a jock all through high school. My freshman year, because of football and wrestling, I went from a short, chubby kid that was picked on by other boys and ignored by most girls, into a slimmed down, solid, muscular young man. By my junior year I stood 5' 9" and weighed in at a solid 160 lbs. during wrestling.
While I was in high school, both from walking around the locker rooms and from dating, I learned that I was better hung that most of the other guys. A couple may have been a little longer, but I was definitely thicker. Some guys gave me grief for that, but the few girls that I dated either loved it or seemed a little freaked out.
I went to an all-boys Catholic school in Chicago and was a three sport athlete, having helped take our football and wrestling teams to the state finals. I lost my virginity my sophomore year to a cheerleader from our "sister school", Our Lady of Perpetual Motion, who had heard through the grapevine (I think that meant her sister's boyfriend, who was also on the football and wrestling teams) that I was bigger than most of the other guys in the locker room. She was determined to find out for herself, and find out she did at one of her school dances.
The summer before my senior year, my parents decided that our family was going to take one last family vacation. My mother's logic was that I would be going away to college next year, and we may never have a chance like this again.
Usually, our family vacations included my mother's brother and his family. My aunt and uncle had a daughter, Debbie, who was just a month younger than me, and a son who was a year younger than my brother, who was 12.
One of the poorly kept family secrets, poorly kept mainly because my mother couldn't keep her mouth shut when she drank, was that Debbie wasn't a "blood" cousin. Her mother, my aunt Eileen, had an affair just before she and my uncle got married, and Debbie was a result of that affair. My uncle Bob, to his credit, never acted like he knew, or cared, and raised Debbie like a good father.
We had both just turned 18, had grown up together, our family houses being only a couple of blocks away from each other. She was like the sister that I never had, and I was the brother that she never had. We were like best friends. We were always there to critique each other's love interests, and to console each other after our relationships failed. We both had pretty active social lives, and this being our last summer before college, neither of us was looking forward to this trip.
When our parents started planning this final vacation, Eileen and Bob announced that they would not be going because Eileen was pregnant again, but they convinced my parents to take Debbie and her brother Bob Jr. along with us.
It was decided that this trip would be two weeks long, leaving in early July so that we could be back in time for me to make the beginning of football practice. We would start by spending a few days at Six Flags in St. Louis, and then head west for some camping. As a budding photographer, one of the biggest upsides to me was a chance to try my hand at some nature shots, something hard to do living in Chicago.
We left Chicago early Saturday morning after my father and I strategically packed up our station wagon. Debbie and I had already convinced my parents to let us sit in the fold-down back seat, facing the back, and put the younger two in the seat behind them with all of our the camping gear in the cargo space between the back seat and our far back seat, and the suitcases on the luggage rack.
It was hot when we left, and we knew that it was going to be even hotter in St. Louis when we got there, so everybody was dressed lightly, in shorts and t-shirts. Debbie was wearing a tank top and Daisy Dukes, a style very popular in the mid-late 70's.
Debbie stood about 5' 2" and might have weighed 100 lbs. With her long blonde hair, toned body, and pretty face, Debbie was, as we said in those days, a 'fox'. Knowing that she was my cousin in name only made her even more attractive to me. More than once as we walked around the neighborhood together, older people would tell us that we made a very cute couple.
The fold-down seats in the backs of station wagons was just wide enough for us to sit comfortably, and we soon settled in for the three-hour long drive.
"I'm glad you were able to convince your parents to let us sit back here," Debbie told me as we hit the expressway. "At least back here, we can talk."
"I just wanted to be away from them, and the boys," I laughed. "Being able to talk to you is an added bonus."
"Oh, thanks," she said, smacking me on the shoulder. "I'm just an 'added bonus'? I would think that your favorite cousin would be the main attraction!"
"You are always a main attraction," I assured her, laughing as I put my arm around her shoulder and holding her.
I swore that I heard her sigh as we sat like that for a minute, and I then moved my arm.
"Too bad we can't do anything about the sleeping arrangements," she said softly.
"I know," I replied.
That was going to be the biggest pain about this trip. My parents had decided that we were getting three rooms, and that Debbie and I would both room with our respective brothers.
"Junior snores and talks in his sleep," she moaned.
"I'll trade you. Davey not only snores, he farts ... a lot."
"Ewwww!" she exclaimed, laughing.
The whole drive we talked about everything possible. We teased each other for a while about how both of us were single over the summer, both agreeing that after our last relationships, that was probably not a bad thing.
The only down side to sitting in the fold down seat was that it wasn't quite as wide as the other seats, so Debbie and I couldn't help our legs from bumping and rubbing, not that I minded. Debbie didn't seem to mind, either, because she never pulled away.
At one point, about three hours into the drive, we pulled off the main highway for gas and lunch. As soon as my father turned off the car, Debbie started to climb out the rolled down the back window, not waiting for me to open the tailgate. The way that she was turned as she climbed out, her ass was right in my face, and I stopped, staring at the firm globes.
Before I could climb out myself, Debbie stopped and turned around, catching me looking at her. I saw a small smile appear on her face, and she turned back around and walked in to the restaurant.
Every time that Debbie looked at me while we ate, I noticed that she had that same smile.
As soon as we were back on the highway, Debbie leaned in to me. "Were you looking at my butt before?" she asked.
"I couldn't help it," I told her. "You practically stuck it in my face as you climbed out of the car."
"I'm sorry," I added after a couple of seconds of silence.
"That's ok," she said softly. "I don't mind."
A couple of hours later, we were at the motel in St. Louis. The first thing that we all decided to do after we settled in to our rooms was to go to the pool.
After spending a couple of hours soaking in the cool water, we all went out to dinner. My father said that he was tired from the long drive, so my parents went to bed early while the rest of us went to our rooms.
Fortunately for me, my brother nodded off early, so I rolled a joint, put my swim suit back on, and went back out.
The humid air must have made the door to the room swell, because I had to pull it hard to shut it. A couple of seconds later, Debbie's door opened and she peeked out.
Seeing me outside, she quickly slipped out and walked over to me.
"Where are you going?" she asked softly.
"I'm going for a smoke and a soak," I told her, showing her the joint.
"Wait here, I'll join you. I could use a dip in the pool, too," she told me, slipping back into her room.
A couple of minutes later, she came back out and I led us around the far corner of the building. I lit up the joint and took a hit, and then passed it over to Debbie.
"I don't know," she said, "I don't smoke that much."
"I don't really smoke that much either," I said, "but we're on vacation, and I don't start football practice for another month."
"It's up to you," I told her. "It'll make floating in the pool even better, and I guarantee that you'll be able to sleep through the night with your brother snoring."
"Good point," she replied, taking a hit.
A couple of minutes later, we walked to the pool together as the buzz from the pot swept over us. By her uncontrollable giggling, it was obvious that Debbie really didn't smoke pot that much.
When we were in the pool earlier, I realized that for one corner of the deep end, we could float and soak up the cool water and no one could see us from the hotel, so that's where we stayed, hanging on the wall, talking and enjoying the relative quiet.
We had been in there for about a half hour, when Debbie spoke up after a couple of minutes of quiet.
"Can I ask you something, without you laughing at me?" she asked softly.
"Of course," I replied. "I would never laugh at you."
"Yeah, you say that now," she said.
"C'mon, ask," I told her.
After a couple of seconds of silence, Debbie looked at me. "If we weren't cousins, would you ever think about asking me out?" she asked.
I didn't know how to respond. I knew that she had to know that we weren't really related by blood. I had always thought that she was one of the nicest, and most beautiful, girls that I had ever known.
Before I could say anything, she spoke up. "I know we're not really blood," she told me, "but if we were just neighbors, or if our parents were just friends..."
"I wouldn't think twice," I told her. "I would have done everything I could to make you my girlfriend."
Even in the low light of the pool, I could see her blush. "Cool," she replied quietly.
"I've always thought what it would be like, having you as my boyfriend," she said a couple of seconds later.
"Really?" I asked, surprised to hear that she felt the same way that I did.
"Yeah."
"I've got an idea," I told her after thinking about all of that. "Why don't we pretend that we are, while we're on vacation?"
"What do you mean?" she asked.
"We're going to have a lot of time away from my parents and the brats while we're on vacation," I told her. "When we're alone, let's be boyfriend and girlfriend?"
