Trailhead Ch. 02

I'd been avoiding the trails in the afternoon for about a week now, not wanting to run into James but figured I couldn't let such things dictate my life. So there I was, cautiously scanning the parking area. I grabbed the dogs and made a beeline for one of the trails.

The walk was overall uneventful though the dogs had a blast, and I found myself back at the car, loading up the dogs. It felt good to be back out here. I missed it even.

"Hey Kris," I heard my name called. Shit, I knew exactly who it was. I turned around to see him.

"Hey James, how's it going?" He looked as nervous as I felt and, as last time, I softened a bit.

He responded, "I'm doing OK, how about you?"

"Good. Busy. A lot of work lately. I haven't even been able to get out much, trying to relax and prepare for the next days work in the evenings." This was basically all bullshit but it sounded good.

"Oh, good. I thought you may be avoiding me or something."

"Oh no, no, just been busy, in fact the dogs are loaded up, I should probably get..."

James interrupted. "Kris, can we talk about the other day? I've been pretty confused about things and I really don't know many people in town, especially none that I could talk to about that."

"Oh gees," I thought to myself. Reluctantly I agreed.

"Okay, I've got a few minutes, what's on your mind, James?" I could do this. Get it over with, quick and painless.

"Well, I thought we could meet up later, maybe grab a beer. I mean it seems like you need to go and, well, I don't know, I just need someone to talk to, somewhere mellow so we can talk. That's all."

I really wasn't into this idea but he seemed so sincere. How I end up in these predicaments I never understand. "Alright, that sounds cool. I know a place that has cheap beer and isn't exactly a hot spot. It's on Highway 62 just past the Gas N' Go, The Pinetop Inn."

"Yeah, just south of town, right? Does tonight work? They have food right? Do you want to grab some dinner later?'

It seemed like it wasn't a big deal. "Sure, that'll work. I just gotta get these dogs home and do a few things. How about 7 o'clock?"

"Cool, I'll see you there. Thanks, Kris."

"Alright, see you in a few hours."

I rolled into the parking lot at 7:05. James was already standing near the door, on the phone. There were only a few cars in the lot, which was good. I parked and went over. He had already hung up and we went inside.

The place was pretty empty, even for a Monday. A woman called out, "Sit anywhere guys, Molly will be right out." We sat down in a booth away from other patrons and waited.

James broke the ice. "I'm kind of nervous. I don't really know what to say."

I just nodded and began looking at the menu. Molly, our server came up and did the usual pleasantries, asking if we wanted anything to drink. "I got this James, can we have two Amber IPAs."

Molly acknowledged. "I'll be right back with 'em."

James started to continue but I interrupted. "How about if we make some small talk, get our food ordered and then talk about whatever it is we're gonna talk about once we're settled in here?"

"OK, yeah, I'm sorry. Like I said, I'm nervous."

"I think I'm going with the bacon cheeseburger and a salad. What about you?"

James had just started looking at the menu when our beers arrived. "Fancy meeting you two here."

I looked up to see one of the girls I had seen at the trail that day. The one with the tight, black shorts. She looked at me "I figured I'd see you guys around."

James looked startled. "What do you mean by that?" he sort of stammered.

"Don't you go to Hillsdale?" she asked. "I've seen you on campus. She then gestured towards me, "And him I saw out at the trails with his dogs." She smiled the whole time. "I told Molly I'd take care of you two tonight. She's lazy anyway. So here are your beers, do you know what you want to eat?"

I knew what I wanted to eat but we both ordered burgers.

"Okay, just yell if you need anything. My name's Steph, by the way."

I remembered that ass as she walked away. Tonight she wore white, denim shorts though, nearly as small and tight as the ones she wore that day. She had on a red halter top and you could see her black bra straps.

"There's one way to quit worrying about the other day" I said to James.

"What? Oh, her. Yeah, she's cute but I don't bother with girls too much. Not unless I know them."

"Well, I'd bother with her. You young guys waste too much time either worrying about the right girl or just being dicks to them. You'll be unhappy forever if you don't straighten out your issues with women, my friend."

This was my sage advice. Once I realized this a few years back, I wondered why the hell my father had never talked to me about these things.

"Look, I don't know what I want. Maybe I'm gay, or bi or something. I mean I like girls but sometimes I'm attracted to guys too. Then I feel guilty or dirty when I'm with a girl and thinking about some guy. So I've been focusing on school and trying to figure out what to do." James looked like he had the weight of the world on his shoulders. I just smiled and sipped my beer.

Steph popped up with a big smile, "You guys good? We nodded. She looked at James, "You alright?"

I stepped in, "Boy problems," I said with a grin, and winked at her.

She maintained her grin and replied, "I didn't know you boys ever had problems." Then she headed for the back.

James looked almost worse now. "Listen James. I'm a little confused too. But there's no use feeling guilty. That'll only cloud things for you. I'm just gonna roll with it. It happened and if it happens again, I mean, like with someone else or something I'll roll with it again. I'm not sure how much I liked it but it was pretty nice and I'm not gonna let confusion turn to guilt and keep me from enjoying life."

"That's easy for you to say, Kris. You're older and have had time to figure this stuff out. I still have to figure it out and it sucks."

"But that's what I mean. You don't have to figure it out. You try things and see how you feel about them. Quit trying to think through these things and just live. The answers will become apparent. Shit, I've done so many stupid and weird things in my life, most of which I never did very often, or for very long. I don't regret them and I definitely don't feel guilty about them."

"Here's your burgers! You guys want another beer?"

Perfect timing. Now James could mull over what I just said. Hopefully this was enough to chill him out. "Yeah, I'll have another. James, what about you?"

"No, I'll just finish this one, and could I have a glass of water?

"Sure thing. Still working on those boy problems, huh? I'll be right back."

I tried not to notice, but Steph had this fabulous bounce in her step, like she was light, happy.

James spoke up after a few bites. "I'm sure you're right. To be honest, I hadn't been worrying much until I saw you and started thinking about it more. I guess it'll just take some time. But where do we go from here?"

Steph brought our drinks but sat down in the booth next to me this time. She asked if we needed anything and James actually spoke up this time. "No, we're good."

She smiled. "That's good to hear. I don't like my customers leaving in a bad mood."

"Thanks, this is James, and my name's Kris, by the way."

She turned to me. "Haven't seen you out at the trail, Kris, you been hiding?"

I was a little surprised that she even feigned caring with our minimal interaction. "Oh, I've just been busy with work, and have been getting out earlier so I can get stuff done in the evenings."

We all made small talk while James and I ate. The usual, what kind of work I do, what their classes are, etc. Steph waited on her tables and came back in between like she was one of our pals. By the time we finished there was only one other table in Molly's section. Steph cleared our plates and asked if we wanted another beer. I

t wasn't even 9 o'clock yet, so I figured why not. Besides, here was a cute college girl giving us the time of day, which doesn't always happen to me. "I'll have another one, sure. James?"

James declined.

"Can you give us a couple minutes while I finish this one though?" And off she went to the back. She had other work to do anyway.

"So James, you gonna be alright?"

"Yeah, but, I was just wondering, about...us. How does this work?"

Okay, I knew he was confused, but I thought he didn't want anything more. Quickly I thought, be nice, be firm, be direct. "Like I said, I'm not sure how I feel about it either. So for now there's nothing to do. I'll see you around, we can talk if you need to but there's really not much else. Just let yourself settle down. You'll see, I bet you'll not think much of it in a few more days."

"Alright, I'm sorry Kris. You're probably right. Well, I should get going. I still have work to do tonight and I don't want to be tempted by your next beer. Thanks for the dinner. See you around." He yelled towards the back. "Bye Steph."

She came out with my beer. "Oh, you're leaving this guy to drink alone? That's not very nice."

I jumped in. "Don't worry, it's not the first time I've drank alone, I'm a big boy. Goodnight James. See you out at the trail."

With that, James left. Steph said she'd be back out and went into the back for a few minutes. I pondered things. I don't always get myself into these situations, but when I do I really have to work hard to straighten things out. I thought back to that day and kind of smiled. It was pretty fun. A handsome young guy catches me jerking off and we fuck in the woods near a trail where other people are a constant. I haven't even had sex that exciting with people I did know very often.

"You want some dessert tonight?" Steph jarred me from my daydream.

"No thanks. I love the apple pie here but that burger filled me up. I better focus on this beer."

Steph sat down across from me, "So what's wrong with your buddy?"

I took a slug of beer. "Oh, he's just new to town and doesn't have friends. And you know, he's a grad student so he's too mature to hang out with you underclass kids." I smiled, knowing that a young woman like this wouldn't stand for my alluding to her immaturity. I took solace in knowing that even if I was terrified of girls through my twenties, at least now I could feel comfortable and tease them and not worry about it.

She took the bait, of course, like many girls do when they sense a guy who doesn't necessarily want to get into their pants.

"I'm more mature than you know. I know most people my age are pretty stupid and immature still but some of us have grown up and learned a thing or two. I'll be right back." She stormed off towards the back. I watched her ass and legs as she walked. There's something about the way a woman walks when she's pissed. I sipped my beer.

She was gone for a few minutes. I was finishing my beer when she reappeared, standing over me at the table. She looked at me very seriously and said "Look, I'm getting off early, and since you were a jerk you can give me a ride home. In return I have a slice of our apple pie in this bag for you."

I almost laughed out loud from the look in her eye and the serious tone in her voice. But I knew that even though this wasn't a big deal she needed me to pay in some way. She probably also really needed a ride home, or my guess is she'd have to sit and wait for a co-worker for another hour or more.

"Wow, I'm sorry to have upset you so," was my half-sincere response. "Well, it's a deal. For a slice of apple pie, I'd do almost anything. Just don't think you're so tough, okay?"

"Fair enough. I've just got a couple things to do in the back. Do you want another beer or...?"

"No, no. Three is about my limit, especially if I'm driving." I know better these days, even if it means a chance to spend more time with an attractive woman. "I'll be ready when you are." I gave her my credit card for the bill and with that, she set the apple pie on the table and bounded off towards the back again. She came out a few minutes later and we headed out to my car.

"So where's your place?" I assumed it was near campus.

She replied, of course, "I live just east of campus, near 6th and Taylor."

We continued with some small talk on the way home. She told me that her roommate normally picks her up but she didn't want to wait around since she was getting off early.

"Besides," she said, "I always like meeting interesting people."

I kind of chuckled, "Well, I don't know how interesting I am but I'll take that as a compliment. These days, just about anything out of the ordinary seems interesting and exciting."

We pulled up to the house and sat for a minute. "Well Steph, it was a pleasure talking with you. Have fun at school tomorrow and maybe I'll see you on the trail."

"Well, I hope so, maybe tomorrow if you make it. Thanks for the ride, I really appreciate it. Hopefully that apple pie is worthy compensation. Goodnight."

With that, I watched her walk to the door. It was funny but I had that lingering feeling, like I was saying goodnight to a date that I should have been going inside with for a nightcap. But of course, it was really just wishful thinking. It did feel nice though, having the company of a young woman which consisted of more than a couple sentences or placing an order.

I drove home with a giddy feeling, thinking about the possibilities of how it could have gone. I could feel that stirring in my crotch. Hmmm, maybe I'll have to go home and jerk off to some of those possibilities tonight. Right after I eat that apple pie.

I got home and tended to the dogs, finished up some work and prepared for the next day. I didn't really have much to do and was glad I could settle down in front of the TV for a bit with the pie. I settled into my recliner and grabbed the remote. When I opened the bag, there were two dessert boxes in the bag.

"Two slices!" I thought to myself. Maybe she does like me hahaha. I pulled one box out, ready to dive in but noticed the other box had no weight in it. I curiously pulled out the second box and opened it. My eyes lit up and I instantly had a flock of butterflies darting around in my stomach. There in the box lay a bunched up pair of sheer, black, thong panties.

I set the slice of pie aside. I put the panties to my face with a big smile and inhaled. "Mmmm, it's been a while since I got to savor that sweet scent. My cock was instantly hard. This development certainly raised questions but my mind was beyond rational thought at the moment. There would be time to ponder this situation later. Right now, there was no stopping the inevitable...