In the Park

I guess I couldn't have been dating Mandy too long at that point. Maybe only a week or two. Prom definitely hadn't happened yet. We for sure hadn't lost our virginities to each other yet.

In fact I know we hadn't been dating long, because when Kaylee invited me to hang out it didn't even cross my mind that I should probably say no. Kaylee and I had been friends since junior high. She was the girl that I always complained about my girl problems to, or in some very rare cases, shared my triumphs with. Still though hindsight is 20/20 and although I know better now, I definitely didn't back then. The truth is though she didn't even register as a threat. We had just never been interested in each other in that way. She had told me that she was into me when we had first met, but by our senior year she had completely gotten over it.

Kaylee was... well, she came from a lower class family - she was never quite put together. I wouldn't necessarily call her "trailer trash" but she was trailer trash adjacent. Looking back, it shouldn't have been surprising that of all my friends, she was the one that managed to get pregnant in high school.

Anyway she must have been having some problems with Tommy or Dereck. Honestly can't remember. She kind of jumped from guy to guy. Whoever it was in that week was unimportant, but she had called me up - as she always did - and suggested that we meet up at the pond in the park. Like I said, I didn't give it a second thought. I left a note telling my parents where I'd gone and walked out the door.

It was only about a mile, so I decided walking would give me an excuse to at least move a bit - and besides, it would take Kaylee a solid 30 minutes to get there anyway. It was the second mistake I made that day.

We lived in a small town. Well, kinda. It was a small town connected to a big city. I guess you'd call it a suburb? But it felt so insulated from anything hip. It was basically a churchy farmland masquerading as suburban sprawl. Anyway, despite being a pretty populated place in our corner of it, everyone knew everyone. If anything scandalous happened, it was guaranteed to be discussed in hushed tones amongst the folding chairs on Wednesday nights, or in the parking lots on Sunday. Word traveled quickly.

Fortunately there weren't too many people at the park that day. It wasn't empty, but there were fewer than I would expect for such a nice sunny day in the spring. I spotted Kaylee first - she was seated on a concrete bench by the pond, but by the time I was 50 yards away she caught sight of me and popped up to walk towards me.

She walked a bit awkwardly at first, tugging at the legs of her - rather short - jeans shorts to fix how they had ridden up her hips while she was sitting. They were high enough that they made a shallow "v" on her. It struck me as a little funny that she would wear something so revealing and then have to work so hard to make them more modest. She eventually got them situated as she walked, and with her waistband lowered a sliver of tummy showed beneath her band tee.

"About time!" She called out when she was within earshot.

I just shrugged her off. She had to know I was going to walk.

"What took you so long?" She pressed.

"I walked, Kaylee.." I replied, a little annoyed by her accusatory tone.

She tossed her curly red hair and fell into stride next to me. "Ohmigod. Did you start the calc homework yet?"

"No. I literally had just got home from wrestling practice when you called. Why? That's due tomorrow right?"

"I think Ms. Jean hates us. There's like 50 problems."

"Oof." I replied. "Well there goes my night."

"For real. Did you have big plans? Seeing Mandy tonight?" She elbowed me playfully in the ribs.

"Not really." I stepped off the walking path under the nearest tree. It wasn't too hot out but the sun was a little harsh. "I think she's buried in some report or something. But I'd definitely rather not be spending my night doing math."

She leaned up against the tree next to me and we both lowered ourselves until we were sitting with our backs against the trunk. "What about you? Any big plans this fine evening?"

"You're looking at them." She shrugged dismayed. "Allie is with Ben, and Rachel didn't pick up when I called."

"Oh so I'm the backup?"

"Well yeah." She teased as she gave me a playful shove. I should have expected it. Kaylee was always trying to find little ways to knock me off balance. Ever since we first met. Still, it caught me off guard and I had to brace myself with my opposite hand to keep from falling over.

"You trying to start some shit?" I shot back at her.

She didn't respond, she just struck - while I was righting myself her hands shot toward my side and got me in the ribs. My body bent sideways into it as my muscles spasmed at her tickling.

Tickle fights weren't really uncommon between us, but I don't think we had one since what had come to be known as "the incident" among our friends. Kaylee had been quick to start shit that day but I had pinned her and Allie relentlessly tickled her. It was all in good fun, but apparently Allie was a bit too relentless. It took us a little too long to realize that between Kaylee's uncontrollable giggles she was gasping out "I'm peeing! I'm peeing!" It was hilarious, but it still took like an hour to clean up Allie's carpet.

I wasn't about to let her provocation go unanswered though. If I did, who knows what sort of garbage she'd think she was allowed to get away with?

I squared up and lunged toward her. Her arms shot out in front of her as she dodged her torso backwards away from my grasp. Her wavy red hair fell into her face. I had been going for her sides - eye for an eye and all that - but with both of her legs shot out in front of her I changed my strategy: her legs were incredibly ticklish above her kneecaps so I went for those instead.

It happened too quickly for her to react. She squealed at me as I gripped onto her thigh. Her knees shot up out of my grip and she fell onto her side away from me in the grass, giggling all the way.

I let her fall and didn't pursue. I had proven my point. As she collected herself and started to sit upright, I got a decent eyeful of her butt. Her shorts were already pretty short, but when she curled up it caused them to ride up a bit. I hadn't ever noticed before, but it wasn't half bad! Not that I would ever act on it or anything, but you know.. good for her. Good for Tommy or Dereck or whoever.

I expected it to end there. She would have no chance overpowering me by herself. Even when she, Allie and Mandy had all ganged up on me I was able to hold my own, and Kaylee was far and away the smallest of them.

My overconfidence left me wide open though. As she calmly hoisted herself upright again I let my guard down. It was then that she struck. What really caught me off guard was that she didn't go for my sides at all - she straight up lunged at me and tackled me. The contact immediately toppled me over into the grass, with her landing on top of me. I reflexively twisted so that I was laying on my back and grabbed at her wrists so that she couldn't just immediately commence with tickling me.

We froze that way for a moment. I was on my back in the grass. She was kneeling astride my chest, leaning over me supporting her weight on her wrists where I held her. Once we reached a sort of equilibrium she sat down, still astride my chest. It was a little rough and nearly knocked the wind out of me.

"What's your plan now?" I asked. "You know I could get out of this any time, and then you're in for it."

She blew her hair out of her face and twisted her wrists in my grip to try to break free. I held tight. The struggle didn't last long and eventually I felt her body begin to relax. I knew I shouldn't but I couldn't help but look down at the way her legs were spread astride me. I know she was my friend and all, but she was just so close and her denim shorts were so short and so tight. I did my best to not look, but at the end of the day she is a girl and I couldn't help but to keep glancing at the space between her legs. Her shorts looked painted on; her seam was riding up just right. It was a bit too much for me. I felt a familiar tightness growing between my legs and could feel my cheeks turning slightly pink as well.

I mean, I knew it was completely normal for a guy like me to have that sort of physical reaction to a girl sitting astride him, but it felt a little wrong since it was Kaylee. I never really looked at her like that. For the briefest moment the thought occurred to me that she was doing this on purpose, and that she had orchestrated our compromising position. It just didn't make any sense to me. There wasn't any chemistry between us - we had never been a "thing," and she knew I was dating Mandy. Still it wasn't like we didn't talk about sexual things every once in a great while.

Like there was that time we were talking on the phone and we somehow got on the topic about the time she had walked in on Ally humping the corner of her bed. I had probably asked her a hundred questions while feigning disinterest. She had dutifully relayed every minute detail to me - she described how she had walked quietly into Ally's room to find her straddling the bottom corner of her bed rhythmically thrusting her hips. She painted a perfect picture for me - from the little gasps she was making to how her PJ bottoms had ridden up her crack a little bit, to how she had squeeked out a half gasp and how red her face turned when Kaylee had finally made her presence known.

And yeah I admit I had definitely been masturbating that time while she told me her story, but it isn't like I told her told her that; it isn't like she knew right? But it definitely wasn't because I was into her - it was just hot to think about Ally getting caught like that.

But even worse with her astride me and blocking my line of sight, I had no way of knowing if the growing problem between my legs was properly hidden. It was bad enough that I was laying in the grass with this girl straddling me. The last thing I needed was a boner sticking straight up in my shorts or worse wiggling out of the top of my waistband. I caught an older couple out of the corner of my eye walking around the pond about 20 yards away, and knew I had to act.

"Truce?" I finally offered her hoping to get out of my predicament. I should have been smarter about it. In hindsight I guess she never actually agreed to a truce. She just relaxed her arms a bit causing me to let go.

To my surprise she didn't get up right away. She just put her hands high on her thighs to brace herself.

"Enjoying yourself?" I asked when it became apparent she had no intention of moving. I put my hands behind my head to brace my neck.

"Hell yeah. This is the first time I've ever actually pinned you." She replied with a small head tilt.

"Well get up already, people are starting to look." That was a lie. The couple had turned and walked off paying us no mind and there was nobody else around. I knew it, she knew it.

I saw the spark of mischief flash behind her eyes a split second before she snapped into action directly attacking my armpits with her fingertips. Reflexively my elbows snapped down to my sides and my hips bridged to try to buck her off. If we were on the mats I wouldn't have any trouble getting out from under someone so much smaller than me, but typically my opponents didn't resort to such unsportsmanlike tactics such as tickling.

After a brief struggle I once again had her wrists in my hands, but as I had come down from my bridge I had shoved her pretty hard. She was no longer kneeling astride my chest - had landed directly astride my lap.

It took me a moment to catch my breath before I was really able to assess the damage. If our position was compromising before, it was straight up scandalous now. I mean, it was still fine. It was just Kaylee. If it were anybody else I imagine I would have thought twice and stopped things right there.

I was holding her wrists tightly and keeping her assault contained but I knew I had to keep my eyes fixed on her face to see if she was going to glance down. The pressure she was exerting on me as she sat astride my lap felt nice - as shameful as that was - but I didn't dare look down to see if my erection was obvious. If I had her eyes would have been sure to follow mine and then I would be in a world of embarrassment.

So instead our eyes remained locked and we stayed frozen like that for what seemed like minutes. It was taking every ounce of my willpower to not squeeze my glutes and push back into the pressure she was exerting on my lap. I was fighting against a raw instinctual urge and wouldn't be able to hold out for long. I had to wonder if she was fighting the same urge. There was no way she couldn't feel the rock she was sitting on in the middle of my lap. Her face didn't betray any understanding of the situation though, so we just remained frozen in place, waiting to see who was going to move first. Maybe that's what made it ok. Neither of us wanted to acknowledge what was obviously happening.

She was the first to break our standoff. I saw her begin to glance down so as quickly as I could I made a move to try to get out from under her. In hindsight I probably should have tried a little harder. She rolled her hips slightly and leaned on her wrists over my chest to keep me pinned. As she rolled forward, her pubic mound rolled up my shaft. Between the half-assedness of my escape move and her leverage over my body I didn't make any progress towards breaking free, but as much as I hated to admit it to myself the struggle itself felt pretty good. As part of my escape (or maybe, whether or not I was willing to admit it to myself, just because it felt good) I had flexed my glutes up towards her. No matter my reasoning behind it, the move had left me in quite the predicament.

If I had relaxed once we settled into our stable position, she would have known that I had been flexed. She would definitely feel me move between her legs, and it might bring to her focus the stiffness separating us. Still, as we were her mound was smashed up against me and I could feel every small movement she made. Every breath, every little movement she made to stabilize herself on top of me was varying the pressure ever so slightly. Her tiny movements on top of me felt so good. A little too good if I was being honest with myself. I got caught up in that feeling for one second too long, and I heard her giggle.

I refocused on her face. Her eyes were cast downward between her legs. My cheeks immediately burned hot. I knew I was busted.

Her eyes came back up to meet mine and she bit her lip and let out a tiny voiceless grunt as she thrust her hips forward sharply. It was raw. It was primal. But mostly it just felt amazing.

It wasn't like I was completely inexperienced. I had made out with girls before. And of course I had jerked off countless times. But this was my first time with a girl on top of me grinding like that. It caught me off guard how much better it felt. Something about the pressure between those parts of our bodies, even through our clothes, felt exponentially better than my hand or any pillow ever had.

I knew I had to look down at myself to assess the damage. The cat was out of the bag anyway, so I just went for it. Luckily I found I was still completely contained within my shorts. My waistband had settled behind the head of my dick, which was causing me to strain hard against the fabric on the front of my shorts.

Kaylee slowly sat up. Neither of us said one word about truces or bothered to acknowledge what was happening between our legs but the entire energy of the moment had changed. I released her wrists and her hands went to her knees.

She sat there still for a moment perched on her knees straddling my lap. Her back was arched more than could have possibly been comfortable, but it served its purpose in increasing the pressure between her mound and me. The outline of my hard shaft was unmistakable through my tan shorts. I was hot-dogged perfectly in the crease that the seam of her too-tight jeans shorts made.

It all just felt so unreal. I had a hard time believing it was happening. It felt like she just happened to be sitting there coincidentally, and that I was somehow to blame for being inappropriate by being so turned on by it. Meanwhile my instincts were yelling at me to thrust forward and up. They were yelling at me to drive my dick into her. A narrow two-inch patch of frayed denim was all that was standing between us. Her shorts were so short I could see where her bare inner thighs turned concave as they approached her sex. I could just loop a finger in there, pull everything aside and take a peek...

That wouldn't be right though. It would definitely cross the line into cheating on Mandy. Besides - it wouldn't work. Her shorts were so tight they looked like they were painted on. It also just felt wrong - naughty or something. I would love to say it was because I was thinking about Mandy, but it was more because it was Kaylee. We didn't have that kind of relationship. We were just two friends wrestling in the park.

Despite the strictly platonic nature of my predicament when I thought about how close I was to seeing everything, about how tight her shorts were and about the remote possibility that she might be getting some pleasure by rubbing up against me it started to become too much to handle. It took a while for that last thought to fully form but once it did, an all too familiar warmth beginning to radiate at the tip of my cock.

While it felt amazing it was a wholly unwelcome feeling. I knew I couldn't give in to that here. Not only would I would die of embarrassment, I knew that something about the act of actually cumming would push me from the realm of incidental contact among friends to straight out cheating. I knew I had to stop daydreaming or I was going to lose control. I looked at the tree next to us to try to think about something, anything else. Once I got control of my urges and the warmth started to recede I looked up at Kaylee.

My eyes followed from her hands on her thighs up her arms. Her shoulders were slightly shrugged from how she was bracing herself on her thighs, causing her small perky tits to press together under her thin rock band shirt. Her chest was rising and falling quickly, but I knew I couldn't let my eyes linger on her chest for too long or I would undo all of my hard tree-staring work.

It was like she was waiting for me to look up at her and meet her gaze. When our eyes finally met she was staring down at me with a look of surprise and amusement. Her lips were slightly parted with the faintest hint of a smile.

Her emerald eyes remained drilled into mine as she slowly reached out with her right hand and touched my stomach. She raised her eyebrows at me ever so slightly as if she were asking for permission. I didn't react. I probably should have. She made a tickling motion with her fingertips. It wasn't malicious and it certainly didn't tickle, but I acted as though it did.

I lifted my hips into her making a show like I was trying to get away from the "relentless onslaught." I twisted and writhed my hips back and forth to really drive the point home. Her mouth opened wider as she went along for the ride as if I was a bucking mechanical bull; she locked down onto me matching my movements. With each movement, each little wiggle rubbed our parts together giving me delightful pressure that I was reluctant to admit I was enjoying. My feigned escape attempt only lasted for thirty seconds or so when once again I felt the electric warm early warning signs of an impending orgasm building in the tip of my dick. My balls were screaming at me to let them empty. I knew I was getting frightfully close to the edge. I knew I had to stop. I often balled up a pillow or occasionally just humped my hand into my mattress to get myself off at home, but I was always careful to have some tissue nearby or strategically placed as a barrier for the impending explosion. This was happening so much faster than when I did it at home though. I knew if I kept it up any longer I was about to have a mess to deal with so I lowered my hips back to the grass.