Chapter 3: Flirting on the Trail

Looking at the brochures and stuff in the room, Kristen and quickly tried to figure out what to do. The beach area was closed to swimming back in 2006 and the lodge didn’t have a pool either so swimming, or at least flirting while pretending to go swimming, was out of the question. Then I noticed a hand-out showing the various trails at the park. There was one, called Woodland Trail, which was supposed to be an easy hike with just a few hills to start while you’re still fresh and then passing through what once was a farm. The trail was advertised as being 1-1/2 miles long with a typical time of thirty minutes to complete. I figured it was just the thing to work out the stiffness from the trip without getting too carried away physically. Plus, if it DID start to rain, we wouldn’t be that far out from the middle of nowhere where we would get too badly soaked or chilled.

After discussing our plans with my dad and aunt, my dad drove Kristen and me to the Park Office where the trail started. My Aunt Linda stayed back and I could tell from the way she was looking at my dad that she would getting herself ready for his return as soon as we were out the door. Dad said that he would pick us up in an hour or so at the other end but as horny as he was we knew we could take our time and he wouldn’t mind a bit. Besides, we had our cell phones so if anything did come up, we could always call him.

Neither Kristen or I changed clothes except to replace our sandals with sneakers. The sandals would have been a pain, literally, on the trail. As for the rest of our outfits, we could have probably worn about anything as odds were we wouldn’t see anyone. In past years, I’d never seen anyone heading for or leaving from any of the trails as it seemed most people came here for the lake, not the trees. Heck, if it wasn’t for the fact I wanted to give my dad some time alone with Aunt Linda to start out the day, we wouldn’t be out here now. Looking at the first hill w would to climb at the start of the trail, I was starting to wonder if even this was such a good idea.

My dad left in a rush, not that I blamed him. As Kristen and I were about to get started, I saw three guys approaching the trail head and so we stopped to say hello. They all looked younger than us and I noticed none of them seemed to look above our necks at first - typical teenage boys! After I told them who we were, they introduced themselves as Darren (nineteen), Kyle (eighteen) and Drew who was Kyle’s fifteen year-old brother. At least that’s what he claimed to be although I was guessing he was more like fourteen, or even younger.

Darren was the one that immediately caught my eye while it was no surprise to me that Kristen had her eyes undressing Drew from the start. Drew was right in the middle of the age range that she preferred - thirteen to sixteen although sometimes she would do a seventeen year-old. The way she explained it (or should I say, rationalized it) was that age boys in that range were old enough to have some idea of what they were doing - maybe even having had sex already but typically not experienced. At the same time, even if they weren’t virgins the odds were they weren’t not veterans so it was fun for her to “teach” them. While I can’t say there wasn’t some physical attraction for me as well, I make it a pretty solid rule to avoid such temptations. In this day and age it doesn’t look good on your resume when applying for a teaching position to have a history of underage sex with a boy (or girl I guess for that matter).

Kristen, given her vocation, had no such concerns and so she indulged herself regularly. Although we never discussed it much, I also got the impression that her mom didn’t mind it when Kristen brought home a young stud either! Something told me the boys probably liked it just as much as the mother and daughter did. I wondered if any of their friends even believed them later when they tried to claim they’d had sex with a MILF and her daughter!

Although Darren looked the sharpest so far as I was concerned, it wasn’t like Kyle was a wimp either. Actually, I wouldn’t mind being laid by either of them, especially as horny as I’d been today. They were both wearing shorts that came to the tops of their knees with ribbed tank tops that showed off their physiques. Mmmmmmm, these boys certainly didn’t spend all day in front of a video game console, that was for sure. Later I would learn that they were wrestlers which accounted for their upper body strength and strong legs.

Drew was, well ... Drew was supposedly fifteen so what could you expect? He was sort of skinny and he didn’t seem to be nearly as athletic as the two older guys. He may not have LOOKED as hot, be he WAS certainly getting hot as he stared unabashedly at Kristen and me, mostly at Kristen I noticed which might have been because she was giving him the most attention as well.

I’m sure nobody would be surprised that we decided to do the trail together. The guys were staying in the campground along with their families for the weekend and were on their way back from just walking around I guess. I’m sure the road would have been easier and faster than the trail but somehow I don’t think that was a major concern for them, especially given who their traveling companions would be. From the way Kristen was unabashedly sizing up Drew, I had no doubt what was on her mind. I’m sure Drew was fantasizing about her as well, just as any boy his age did about every girl stranding on two legs. Still, I would have bet the farm that he had no inkling whatsoever of just how close he was to having his dreams fulfilled!

As for Darren and Kyle, they were also staring at Kristen but they had a few looks for me as well. What can I say? Anytime I’m with Kristen it was usually the same - they guys loved the perky little “teenager” more than the “old” college graduate. Somehow I’d never anticipated that turning 24 would ever make me so old. Still, I was pretty certain that they wouldn’t turn me down once they realized where Kristen’s tastes lay.

Once we got on the trail it was like the rest of the world disappeared. My perceptions about the popularity of hiking seemed to be confirmed as there were no signs of anyone else, not even any trash or footprints to show that anyone had been by recently. I have to say, shorts like Kristen and I were wearing may be entertaining to wear around the house and such, but when it came to walking any significant distance their shortcomings became apparent pretty quick. Being as tight as they were in the crotch, they had this annoying tendency to pull up against me. Normally that wasn’t a bad thing, such as when I was sitting down or driving as it can be quite stimulating. In this situation, though, it quickly became irritating.

Several times I noticed Kristen reaching down and pulling at hers, evidently having the same issue as me. If we’d been wearing bikini bottoms underneath, at least ones that could be worn in public, I’m sure we would’ve ditched the shorts after the first 100 yards or so but walking bottomless through a public park wasn’t necessarily such a good idea, no matter how appealing it may seem at the moment.

As we walked we let the boys do most of the talking. It was an old trick that my dad had taught me early on about boys. I can remember him telling me that if I really wanted boys to have a conversation that they would always remember with me, just let them do all the talking! It still amazes me at times how much men will tell me when I keep my mouth closed. Actually, my dad told me he used the same technique with clients in that if he just sat at his desk quietly they would sooner or later start telling him things they maybe had no intention of saying when they started.

So before we reached the top of the first hill - taking several breaks along the way, I knew where they lived, what schools they went to, what jobs they had, and even the fact that not one of them had a steady girlfriend. There’s something about boys that to prove how cool they are, they like to see how bad they can make their buddies look in comparison.

So with the three of them trying to one-up each other and show off, I soon learned that Drew was a virgin (no surprise there), Kyle had done it once with a girl at school that never saw her again afterwards, and then there was Darren who claimed to be a stud but Kyle countered by accusing him of exaggerating his “conquests” significantly. Interestingly, most of what I learned about each one didn’t come from them but was offered up by one of the other two and it became a bit of contest between them as to who could spill the beans more on the other.

While they were bragging about themselves and cutting each other down - apparently thinking that somehow this would somehow impress the older girls they were with. meanwhile, Kristen and I remained quiet, grinning at each other now and then when something particularly ridiculous or embarrassing was revealed. While they were spilling their guts, so far they really knew nothing about us and in my book, in such situations that’s best, at least for me. Really, what DID they need to know about my personal life? It’s not like either of us was interested in becoming their girlfriends or even having anything to do with them after today. They knew our first names and that we were from the general Pittsburgh area, and that was about it. Oh, they also knew we were cousins and our ages, although they seemed surprised at Kristen’s while nothing was said about mine.

Grrrrrr ... So far we’d mentioned nothing about our sexual histories or experiences and if I had my way, it would stay that way. The more naive and inexperienced they thought we were, the better. Boys have such fragile egos! Being older than them, I think had they known the true extent of our past, especially Kristen’s, they would’ve been totally intimidated.