Trailhead Ch. 01

It was another afternoon walking the dogs, early fall when it's still warm enough to wear shorts and a light jacket while out in the weather. The area I go to is mixed-use with a nice, wide separated running and bicycling path. There are also dirt trails that wind around through the brush and trees.

Everything does a big loop back to the parking lot. I normally take Archie and Lulu (the dogs) out on the dirt trails so I can let them run free while avoiding as many of the uptight people as possible. Trails meander between shade and sun and this time of year is perfect for getting a little exercise without getting overheated.

Like most trips out I wore my trail sneakers, a pair of blue basketball shorts, white t-shirt and a black lightweight pullover, now that it would be cooling down by the time I got back to the car. I also wore panties today. I don't usually wear panties but lately I get more and more turned on by wearing them out in public. It's been about a week so I felt especially excited. I decided to wear my satin thong with a blue and purple floral print. The thing about them is that between the satin and the basketball shorts, if I start rubbing my cock it feels incredible. Smooth to the touch inside and out.

It's pretty much the same old routine. Pick one of a few trails that all go in the same direction and start walking. The trails criss-cross so I just sort of wander along, making it a point to try and change things up. The dogs tear off through the brush chasing each other and squirrels, jays and whatever else is out there. It's mostly quiet for me and it gives me time to think about the day, upcoming work projects, etc.

At times the trails also merge or come close to the exercise paths. And now and then I get to catch a glimpse of "the beautiful people." The ones driven to keep their bodies in tip-top condition. Nothing against them, I just don't have it in me these days. Sometimes I get to take some really good looks, a nice, tight ass in running shorts or yoga pants. Some jog so slow they barely get ahead of me. That's when my mind drifts away from the daily bullshit and into fantasy.

Sometimes I take a joint to smoke with me. I have a cozy spot about twenty minutes into the hike, well away from the exercise path and a little off of the hiking trail. There are a couple of boulders and a fallen tree to sit on. It's obviously a spot that the dregs like. There's always some fresh beer cans around and other evidence of nefarious activities.

My timing was good today. I got to the parking lot just as a couple of young women were getting out of their car. They were probably fresh college students as this is a college town and every fall this area gets flooded with a new batch of young, beautiful hard-bodies trying to stay in shape. I always welcome them when I can, half sincere and half sarcastic.

One of the girls had on a pair of the really short black spandex shorts, like volleyball shorts or something, and a thin, white t-shirt that showed her sport bra underneath. The other was wearing looser fitting nylon shorts. Not my favorite but she had a big ass that was at least hugged nicely in the rear. She wore a tank-top that showed her big tits.

As I parked and got the dogs out I was treated to watching them stretch out. My cock had already begun twitching and was half-hard, barely constrained as I moved towards them with the dogs.

"Easy boys" I said as we approached, the dogs getting more and more riled as we neared the trail-head, where they knew they'd be released. The two girls stopped and turned.

"Don't let us interrupt your workout. These two won't bother you." They had the typical reaction that college girls often have when spoken to by a non-peer, non-authority type...utter silence.

"Welcome to Hillsdale, I assume you're new here for school, right?"

One nodded her head while the other nervously responded "Uh, yeah, yes sir."

"Please don't call me sir, I'm barely thirty-six. It's a great town, I'm sure you'll both like it. There's a lot of outdoor activities, too. Well, have a nice run."

The other responded this time, "Oh, okay thanks, you too."

They often seem surprised when I just have a half-assed normal conversation and don't start picking up on them. Not that my cock wasn't about to burst out the side of my panties since the more it twitched and the more I looked at them the hornier I was getting. I just know how to control it a little bit. I released the dogs and off we went.

By the time I got to my smoke spot it was already getting to warm for the jacket so I took it off and sat on a boulder with it cushioning my ass. I called the dogs over so they'd know I was stopped and not keep going. I took a drink of water and put some in the cloth travel bowl that I carry for the dogs. They took a few drinks and darted into the brush.

I sat for a minute, taking in the sights and sounds of the woods. My mind wandered. I started thinking about the two girls back at the parking lot. Those asses, those nice tits, barely covered. I took a look around checking for any signs of people. First just a little rub of my prick. Scan the woods again. Then I grabbed myself and started really playing it.

"Just for a minute" I thought. "I gotta smoke this joint and get going." I thought back to the girls again, about coming up from behind them while they did their toe touches, rubbing their tight butts in those shorts.

Now furiously rubbing my cock through my shorts, it was too big to be constrained by the little panties I had on. It pushed out the side and I could feel everything.

"OK, I gotta stop." But I didn't want to. Then I heard something. It was rustling in the brush and heading towards me.

Just as Archie and Lulu popped out another dog ran through the brush into the clearing from the other way. The three dogs barked for a few seconds then began sniffing each other, tails wagging.

"Marley! Come here." The guy seemed worried so I told him not to.

"Dogs will be dogs. I haven't ever run into anybody out here that cares about dogs running loose." "Oh yeah, I just don't want him running off or bothering people. He's not very good and I'm new around here so I don't know the area well."

"Oh, you're new to town? Let me guess, moved here for school?"

"Yeah, I'm a grad student so I work at the college and am studying for my masters in health care. I'm going into physical therapy."

That made sense, he definitely had the college guy feel but seemed a little older. He also had a bit of the jock feel to him but a little more hip. He stood there with the sun creeping down behind him with some community college baseball hat, sunglasses, blue t-shirt, khakis and sneakers.

I stood up and walked over, extending my hand. "My name's Kris. Welcome to Hillsdale".

"James. Thanks. It seems like a pretty cool town."

"Well, everything you could want, bars, pretty girls and lots of outdoor activities. That's all I wanted when I was your age anyway. Oh yeah, and school." I smiled.

The dogs came tearing through and seemed to be having a blast. He seemed nice but I had other things to think about. Namely I really wanted to smoke that joint. I try to be cautious these days, but thought I'd feel out where he stood. I had a great opener.

"So, your dog's name is Marley, huh?"

"Yeah, my ex named him after that stupid movie, Marley and Me, but I usually tell people it's for Bob Marley."

This was a good sign. "Oh, so you must smoke then?"

"Well, yeah, sometimes, not very often. I used to more."

"Cool, well I was about to light up a joint when you two came bounding through. Care to join me?"

He looked nervous but said that he'd be down for a couple puffs. Music to my ears. Now I could smoke, finish the walk and get back before too late.

I enjoyed the long, quiet walks. Most people I meet on the trails are nice enough but I'm usually ready to go on my way after a few minutes of chit-chat. I lit up the joint, took a couple puffs and passed it to him.

During our smoke session we continued talking about the usual things; dogs, school, jobs. The dogs came bounding into the clearing again. This time Lulu was covered in something. I passed him the joint and knelt down to see what it was. It was just some leaves all caught up in a thick cobweb she had apparently run through. The dogs were staring off now and sniffing the air. Off they went again.

I sat back down on the boulder, ready to finish this joint and get going.

"Dude, you're wearing panties? I saw a whale tail when you knelt down," James said as he passed back the joint.

My heart sunk. In my head I exclaimed, "Fuck, shit, what the fuck!" But as I said, I've learned to keep my cool for the most part. I started to stammer a little, "Well, um, I just, this woman left them at my house and I kind of figured I'd see what they were like. I totally forgot I had them on even until you said something." That was pretty good, sounded innocent enough.

"Really? But you were playing with yourself when I came up. I could see you were still kind of hard when you stood up. And there was totally a wet spot on your shorts."

He was looking at my cock but he had those sunglasses on. He never would have had he not been wearing them. I fucking hate sunglasses. What could I say to him. The last thing I needed was some jock dude in town knowing I wear panties. I still had to respond.

"Look, what do you want? I'm wearing panties, okay. I tried them on. I got horny out here and was messing around. Alright. What the fuck?" I figured getting a little aggression might help kill the questioning so I could get those damn dogs and get the fuck out of there. "Look, I gotta get this walk done."

"Yeah, sorry, don't freak out. I was just surprised."

My aggressiveness seemed to work. I was now listening for the dogs hoping they were close. I was about to call them when James said "Kris, can I at least see them? I know you have to go but can I see them?"

Holy shit! Now this fucking kid wants to see them. This really took me by surprise. "What do you mean can you see them? Why would you ask me that?"

"Well, I don't know. I'm intrigued I guess. I don't know, never mind. It's weird anyway." His head lowered and he looked dejected.

Now I felt weird or bad or something. I thought he was gonna be a jerk at first but now he seemed sincere. But what the hell, it's not like I do this every day and everyone knows. Why does he want to see them? It's embarrassing, doesn't he get it. "I just don't understand why you want to see, that's all. You want to mock me?"

"No, not at all. I swear. I just wanted to see."

Fuck, I'm about to do this. "Aughh, okay. You can see."

I nervously looked around. The expression on his face seemed sort of sad now and didn't change when I affirmed that I would show him. I had butterflies in my stomach as I reached down to my waistband and my cock started twitching.

"Oh no," I thought to myself. I slowly pulled my shorts down to mid-thigh. There we were, some kid I just met, and me leaned against a boulder showing him my panties. He took his sunglasses off. My cock had started to grow and I hoped it would be over before it got too embarrassing.

"Can I see the back?" James asked. I couldn't go through that conversation again, and besides I could conceal my stiffening prick. I turned around and stared into the trees.

Then I felt his hand on my ass. I quickly turned and stared into his eyes.

"I'm sorry, I. Believe me I'm not gay. I never had sex with a guy. It, it's, you have a nice butt." His head dropped again.

My cock became rock hard immediately. He looked up, and then down. The panties straining against my cock to stay in place. He reached out and pressed his hand against it. His hand was warm in the cooling air and felt really nice. I looked around again scanning towards the trail.

"They're really...sexy" he said. I said nothing, confused as all hell and excited at the same time. I had no idea what I was doing. I hadn't had sex with another guy since I was a kid. He just held his hand there. "Your dick feels nice too."

"Thanks. Uhh..."

"Oh jeez, I'm sorry." And he jerked his hand away.

"No, uh, I mean, your hand, it feels good there. I just, I don't know." This was the most awkward shit, especially to be happening here in public, where people were jogging and cycling by just a few feet away.

"It felt good?" James asked.

"Um, yeah," I responded, trying not to sound very enthused. But I was so horny at this point that even though I felt apprehensive I wanted his hand back on my cock. He reached out and grabbed it this time. My cock pointed upwards and the strength and warmth of his hand pressed against the underside of my shaft. I closed my eyes. With one finger he pulled the top of my panties down over the head of my dick and exposed half its length.

"It's pierced! Whoa, that's awesome." He rubbed it and my cock jumped.

"Does that hurt?"

"No, the opposite. It feels really good."

He smiled and reached again rubbing his index finger in little circles just below where the shaft meets the head, where my frenum piercing is. I sipped in some air.

"You really do like that, huh?"

I nodded. Then he bent over and licked it with the tip of his tongue. He looked up and smiled. It was official now. There was no way I could stop whatever would happen next. I wanted relief for my aching cock and would have done anything to get it. And James seemed intent on continuing to take this further.

"That's nice," I muttered. He leaned back down again and took the head of my cock into his mouth. Fuck it felt good. He took it out and put it back in a few times, looking at it each time as if inspecting it. Then he pushed it against his lips with his mouth closed and rubbed it around, slowly opening his mouth and sliding my dick in about three inches. His tongue flicked and maneuvered around my piercing and head.

My cock was throbbing and I wanted this kid to suck it for real. I thought some positive encouragement might help. "That feels so good, James. Suck it. Your mouth feels so good."

With that, he took me all the way in, with a little trouble, but he did it. I could feel his tongue flicking the base of my penis as his warm, wet mouth engulfed all of me. He came up for air.

"I'm gonna suck you Kris. I'm gonna suck you hard. I love it." He practically dove back down and began sucking, taking it out and rubbing it on his lips, and I could feel him pull it to the tip sucking up pre-cum and then going all the way down on me. His hands were on the back of my legs. He slid them up to my ass and pulled my panties down to where my shorts rested. I stood up straight and he pulled my ass cheeks apart a little.

One of his hands moved from my ass and I could tell he was fiddling with his shorts now. To maintain leverage he moved the one hand on my ass closer to my crack. The whole time he never stopped sucking on my prick.

I looked down and could see he was playing with his own cock. Jerking it and smearing the pre-cum around the head. We were both buckling at random intervals. I could hear noises in the brush but didn't care anymore. This felt magnificent and I would be finishing with an orgasm even if ten people walked up.

He stopped and looked up at me smiling, and said, "This is awesome."

"Yeah, awesome," was all I could respond with between heavy breaths.

Before putting me back in his mouth he switched hands and began rubbing his own prick again. He grabbed my ass then swirled his tongue around the girth of my shaft as he methodically swallowed my cock to the hilt. As his mouth reached the base, I felt a wet finger begin pressing into my asshole.

"Shit, this kid is good," I thought to myself. He knows a finger in the ass feels good. He slid his lips back up the length of me and focused on the tip. He also started working that finger around in my ass.

At the same time he continued playing with his own cock. His coordination was amazing and I was getting the full benefit of it. Watching him furiously rubbing his cock, knowing he was so turned on by this began to put me over the edge. I knew it was time.

"Suck it, James. Suck me and fuck my ass. I'm gonna cum so hard. Finger my ass." I could feel him pick up the pace, everything became more intensified. He was like a machine.

"Where do you want me to cum, James? In your mouth?"

"Mm-hm". He brought his own hand up from his prick and began jerking my cock as he worked over my engorged head paying special attention to my piercing. Then, he pushed a second finger into my ass and I couldn't take it any longer.

I'm...gonna...cum." As I shot the first load he stuffed my prick back into his mouth. He then took my cock out and aimed it at his face, cum shooting on his cheeks and lips. I was about to collapse and as the cum slowed down he stood up, rubbing his cock.

He grabbed me with both hands and turned me around. I felt the tip of his cock press against my asshole while he jerked off. I was nervous but too spent to do anything. I took a deep breath and rested on the boulder. Any minute I figured he would cum.

Then he pushed his cock into my ass. This I wasn't expecting. But he started fucking me without hesitation. His cock was slick with pre-cum and after the initial shock it began to feel good. He was groaning and whimpering behind me. I knew he'd never felt this good before. I don't know that I had either.

"Fuck me with that hard cock, James. Fuck my ass. That sweet cock feels so good in my ass. Do it." And that was all it took.

A couple minutes and some dirty talk and he just started unloading his cum in my ass, which again I didn't expect. I could feel spurt after spurt shooting into my ass with force. He slowed down to a stop and leaned against me, panting in my ear.

He whispered, "Sorry, Kris. I didn't mean to."

"It's okay, James. I didn't expect it but I have to admit that you cumming in my ass was really hot. I don't mind."

"Kris, can I have those panties?" I smiled, looked around, pulled my shorts and panties down and handed them to him.

All three dogs came running up, looking at us kind of strange.

"James, that was great and all but I have to go. I don't know what else to say but I'm sure I'll see you around."

"Thanks," was all he said as he got himself together. I grabbed my jacket and headed back to the car. I was glad that at least the dogs spent the whole time running around with Marley.

As I got back to the car the two girls were doing some warm-down exercises and stretches. As me and the dogs walked by I asked, "Well, what did you think of our little jogging path? Beautiful right?'"

"Oh, yes si..I mean, yeah mister. It was amazing. We really like jogging here. How were your outdoor activities today?"

"Oh, real good, I haven't gotten a workout like that in too long." I kind of giggled and smiled. If they only knew. "Well ladies, see you next time."

"Yeah, we'll see you again."

I got into the car and started it up. A smile came to my face. After all that, I think those girls were even flirting a little. It's gotta be me, just because I got my dick sucked I'm feeling all studly. And then I felt cum running down the back of my leg and squishing into my shorts...