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Ashley Always Wins

Category: Anal Sex
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I want to tell you all a little story about a former fuck buddy of mine. I’m using the term “fuck buddy” here relatively because we never technically fucked per se. Suffice to say that I met a crazy girl who did some crazy things with me. OK, I’m being too vague now, and I’m probably confusing you. Here’s how it all happened:

A few years ago, I got on a big health kick. I started buying all organic food, I got a pedometer, and I started running my ass off. I wasn’t living on campus at my college anymore, but I had an apartment right next to the school’s recreation complex. Just outside my front door were the intramural football fields, a rugby field, a lacrosse field, a baseball diamond, tennis courts, an indoor pool, a small gym, a track and a bike/running path. It was a massive area and very well taken care of. I didn’t actually use half of the facilities. In fact, I mostly just used the running path. The path wound in between all of the fields and buildings. I always ran at night because I had class during the day, but I didn’t mind. I liked to run at night. The path was lined with trees and bushes, which gave it a sense of privacy, but the entire area was fairly well lit up so you weren’t running through the dark.

It was a great area and many people used it at night just as I did. One night, I was stretching beside the running path, getting ready for a long run. A girl was jogging down the path and stopped a few yards from me. I didn’t think anything of it at first. But, after several moments, I realized that she wasn’t moving on. I looked over at her to see what she was doing, and, to my surprise, she was looking at me. I don’t mean that our eyes met and we fell in love. She wasn’t looking anywhere near my eyes. She was checking me out. What’s more, she was making it very obvious. She didn’t even care if I saw. I was getting eye-fucked right out in public.

So, seeing as how she was staring at me, I gave her body a once over of its own. She had a petite, athletic body; short, but she had a round, juicy ass. She was wearing black short shorts that just barely covered her up and a black tank top with a sports bra underneath. All of her clothing was very tight and I could tell she had a nice pair of perky tits, probably c-cups. She started to walk over, her blue eyes locked onto me like a lioness tracking her prey. As she approached, I finally got a good look at her pretty face and noticed that she had her dirty-blonde hair tied back in a ponytail just the way I like.

“Hey,” she said.

“Uhh, hey there,” I said. I tried to play it cool, but I was nervous by nature. I had never been approached by a girl like this before. She was so forward and confident. She smiled when she saw how nervous I was getting.

“What’s your name?” she said.

“I’m Matt,” I said, awkwardly sticking out my arm for a handshake. “What’s yours?”

“Call me Ashley.” That was a strange thing for her to say. Did she mean that her name really was Ashley? Or, was her name something else and she just wanted me to call her Ashley? Holy shit, did she not want to tell me her name because I was in for some anonymous sex? Was this going to be my first one night stand? Was she going to–

“Want somebody to run with?” she asked.

“Uhh…. Umm…. Sure?” Ok. Maybe I was getting a little ahead of myself before. Hot girls don’t just walk up to random guys and ask if they want to have sex. She didn’t even know me after all. So, I finished stretching and we started jogging together at an easy pace. After a couple of minutes of me trying to think of what to say, Ashley said,

“So, you live around here?”

“Yeah, just over there,” I said and pointed in a direction that I was pretty sure was right. The path was winding and the trees made it hard to tell directions.

“Do you go to school here then?”

“Yeah,” I said.

“What do you study?”

“Engineering. Do you go to….”

“I’ve got a proposition for you,” said Ashley, interrupting me.

“Umm, alright. What is it?”

“A race.”

“A race?”

“There’s a boulder about half a mile ahead of us. First one there wins.”

I thought about it for a few seconds. Fuck it. Why not? Happens all the time, right? Nothing strange about this.

“Ok,” I laughed. The whole situation seemed pretty bizarre to me. Some tight-bodied girl had eye-fucked me and then challenged me to a race. “You’re on. What do I win when I beat you?” I was feeling a little more confident now and decided to tease her a little.

“If you win, I’ll suck your dick,” said Ashley in the absolute calmest manner I’ve ever heard. I almost choked on the air I was breathing. Was she serious? I looked at her face and saw that she wasn’t kidding. “But,” she continued, “if I win, you eat my pussy.” This was a fucking dream. No way was this really happening. I couldn’t lose. If I beat her, I got a blowjob. If I lost, I got to eat her out. I love eating pussy. I would have done that for free.

“That sounds… uhh… fair. Ok, should we do a ‘ready, set, go’ or something?”

Ashley turned her head towards me. She had a big smile on her face like she knew something I didn’t. “Ready, set, go,” she said, and we were off. I quickly learned that the reason Ashley was smiling was because she was a very fast runner. She was out in front of me immediately and stayed there for the rest of our race. I was sprinting as fast as I could, trying to catch her, but I wasn’t making any progress. I don’t even think she was running as fast as she could herself. It was like she was toying with me, running just fast enough to stay in front of me, but slow enough so that she could watch me try to catch up.

Soon, I could see the finish line and gave up entirely. I slowed to a comfortable pace and decided to give in to my complete and utter defeat. The sight of Ashley’s ass bouncing with each step in front of me was my consolation prize. I crossed the finish line gasping for air. Ashley didn’t even seem winded in the slightest.

“You lose,” she said. Then, without even giving me a chance to catch my breath, she dragged me off the path and into the bushes. No more than five yards off the path, she found a tree and put her back up against it. She quickly slid her shorts off, tossing them aside. Then she pulled her panties down, leaving them around an ankle. She roughly pushed me down to my knees. I was still gasping for air, but she placed a hand on the back of my head and shoved my face into her hot pussy.

Her warm thighs were on either side of my face and it was so hot between her legs I thought I might melt right then and there. I opened my mouth and started to lap at her with my tongue, moving my lips over hers. Ashley instantly began moaning. She was suddenly incredibly turned on. I wondered if running was like an aphrodisiac to her. Maybe she got off on winning. Either way, she was thoroughly enjoying my tongue between her thighs.

She pulled my head away every once in a while so that I could get a few breaths in, but she would always shove me back down for more. My nose was nestled into a soft patch of hair directly above her pussy. She kept herself nice and trimmed, but maintained a traditional patch of pubic hair.

Her pussy was soaking wet and continued to gush juices which I happily lapped up. Ashley continued to moan despite the very public area that we were in. Luckily, no one happened to be near us, otherwise they would have heard her no problem.

“Yes, yes, yes!” said Ashley. “Eat my pussy. Make me cum.” I worked my tongue as best I could. I flicked it over her clit, lapped along her inner lips, and even prodded into her hole a ways, penetrating her. Her moans grew quicker and more frantic as I worked. She let me up for air and I saw that she had one arm holding onto the tree behind her and her eyes were shut tight. She shoved me back between her legs one last time and I worked my tongue directly on her clit.

“Oh yes! I’m… I’m… I’m cumming,” she said in a hushed, strained voice. Her legs tightened around my head like a vice and the hand on the back of my head was pushing hard, smashing my face deep into her hot snatch. I felt her legs shake as her orgasm swept through her body, draining her of energy and expelling shear joy.

Finally, she released my head from between her powerful legs. I slumped down, gasping for air. Talk about a fucking workout. My heart was racing, my lungs were burning, and I had an erection that could have cut diamonds. After I got enough air to ensure I wouldn’t pass out, I looked up and saw Ashley sliding her shorts up over her beautiful curves. She looked down at me, kneeling in the grass. She gave me a satisfied smile.

“Thanks,” she said. “Bye.” Then she just turned around and ran off. I sat there in the silence that followed, wondering if she was maybe just fucking with me. She wasn’t. I was left in the bushes, worn out with a raging erection in my shorts.

I decided to skip the rest of my run and walked back to my apartment. I hopped in the coldest shower of my life, but it did little to cool me off. I took care of my unceasing arousal, had something to eat, and went to bed, all the while thinking of the crazy night I had just had.

I thought I probably would never see Ashley again, but I was wrong. One week later, I was running down the path again and there was Ashley, leaning against the boulder we had raced to.

“Look who it is,” she said. “Wanna race?” And, just like that, I had a fuck-buddy of sorts. We started meeting every week at the same time and place. She would make a bet with me, always with the same stakes. If I won, I got a blowjob. If she won, she got eaten out. We didn’t just race though. Clearly, I was at a disadvantage in that field. She always won races. So, we started doing other things. As it turns out, I was at a disadvantage in most other things as well. We played soccer, and I ate her out. We had a jump rope contest, and I ate her out. We even played basketball, and I ate her out. She was short, but she played dirty. Every week, I ended up on my knees in the bushes with my face between Ashley’s legs getting covered in pussy juice.

Ashley was absolutely dominating me in every contest we had. Once, I suggested horse shoes. Guess who one. I did win once when we had a sit-up contest. But, I suspected that she was on her period that week and just let me win. I didn’t care though, because I was too thrilled that I was finally going to get a blowjob. I took full advantage of the situation as well. We went off into the bushes like always and I used that ponytail of hers as a handle as I roughly thrust into her mouth. She took it all, never so much as gagging. Eventually, I came in her mouth and she swallowed it in a few big gulps. Then she stood up, wiped her mouth with the back of her hand, and said, “See you next week.”

I had never met a girl so fit. You wouldn’t even think it to look at her. She wasn’t overly muscular or anything. Still, it was pretty emasculating getting my ass kicked by a girl. And, it was incredibly frustrating eating her out almost every week and then having to walk home to jack off. We had been having our little competitions every week for two months, but we had never actually fucked. Not even back in high school had I eaten a girl out so many times and not gotten to fuck her. So, one day when she said she wanted to change the stakes a little, I was all ears.

By this time, she knew where my apartment was and usually met me at my front door. Of course, I still didn’t have a clue where she lived. In fact, I still didn’t know if Ashley was even her real name. Anyways, on one particularly warm night, I walked out my front door and she was standing there waiting for me. She had on a sexy little black tennis skirt and held two racquets. She held one out to me and told me we were going to play a set of tennis. I smiled as she turned to walk towards the courts, her tiny skirt swaying back and forth with each step.

She knew that I loved to watch her ass as she walked and usually made a point to walk a few steps ahead of me so that I could stare. She wore a small pair of tights underneath the skirt that were basically panties. They clung to her round cheeks and outlined her shapely ass.

“How does my butt look tonight?” Ashley suddenly said. I was a bit surprised because she rarely acknowledged when I stared.

“Delicious,” I said, salivating.

“Really?” she said. “Good enough to eat?”

“Oh, you have no idea.” I could feel myself already growing hard. I had become conditioned to get extra horny almost an hour ahead of time whenever I was going to work out with Ashley.

“Oh yeah?” Ashley stopped walking and pulled up the tiny skirt to give me a full view of her ass in her tights. “Would you say it’s… good enough to lick?”

“I…. Wait, what?” What did she mean by that? Where was this going?

“I want to change the stakes of tonight’s bet,” said Ashley. Something in her tone suggested that she wasn’t really asking.

“Ok. What do you want to wager?” I was curious, but also nervous about what I thought she was about to suggest.

“If I win, I want you to lick my ass.”

“You mean, like… lick it how exactly?”

“Thoroughly. If I beat you, you have to give me a full-on rimjob.” I was a little shocked at the request. I didn’t think girls were into that sort of thing. On one hand, I had never licked a girl’s ass before, and the idea was a little scary to me. But, on the other, I did worship Ashley’s ass, so that would probably make it a lot easier.

“Well, what do I get if I win?” I asked.

“If you win? Hmm…. What do you want?” I had never been asked to alter the wager before. So, I just thought, ‘Fuck it. Might as well ask for something crazy from her in return.’

“If you win, I eat your ass? OK. If I win, I fuck your ass.” I smiled mischievously. I expected her to make me pick something else. But, without so much as a pause to consider it Ashley said,

“Deal.” Then she continued to walk to the tennis courts. I would like to go back in time and take a picture of my face at that exact moment. The mixture of shock and arousal that rendered me speechless must have made quite the sight.

After a few moments of not moving, I hurried after Ashley. The prospect of finally getting to fuck her, nonetheless getting to stick it to that luscious butt of hers, was more motivation than I ever needed. I was picturing all the different positions I could put her in, when a thought occurred to me. She had agreed to the terms of our wager very easily. This could mean a few things. First, she could just be a huge slut and anal wasn’t even a big deal to her. That was wishful thinking mostly. Secondly, she could just really want her ass licked badly enough to allow anal to be put on the table. Or, and this one made the most sense, she could just be really fucking good at tennis.

After four games of getting my ass handed to me, I decided it was probably that last one. I had only managed to score three or four times and was getting my ass beaten up and down the court. After she slammed in the last point of the fifth game, Ashley turned around and pulled her pants down, mooning me.

“Just want to give you a preview of what you’re in for,” she said and gave her big ass a slap. “Your tongue is going to be going right around here.” She slid her index finger into her crack and moved it up and down the length of her ass. I was getting nervous, knowing that my tongue would soon be lapping at her asshole. What had I gotten myself into? Ashley drew out the final game, prolonging my inevitable defeat. After she scored the final point, she slowly walked up to the net with a smug look on her face. I walked up to the net to meet her, a look of shame on my own face.

“Wow, this must be really embarrassing for you,” she said, still smiling.

“Alright. Alright,” I said.

“What was it that you wanted to win again? If you won, you were going to fuck my ass?” She was merciless when it came to teasing. “Did you really think that was going to happen?”

“Yeah, yeah. I get it. Ok, where do you want to go?”

“What do you mean?”

“I mean, should we go to that spot by the boulder, or is there a hidden spot nearby?” Ashley smiled wickedly.

“Who said we were going anywhere?” she said. I looked around. Ashley and I were the only people at the tennis courts, but we were by no means hidden. The huge lights illuminating the courts left no room for us to hide like we usually did. There was a tarp of sorts along the fence, but it was still pretty easy to see through. Surely she didn’t mean to do it right here on the court.

“What are you up to now?” I said. This prompted Ashley to hop over the net to my side of the court. Then she slid off her tights and her skirt in a slow, sensual motion. She turned back towards the net and bent herself over it, holding onto the top with her hands. There she was in front of me, completely exposed in the middle of a tennis court. Her big ass looked absolutely superb as she gently swayed it back and forth, beckoning me forwards. I felt my cock pressing out against my shorts and I wanted nothing more than to grab her firmly by the hips and slide myself into her. However, I had different things to attend to. A bet’s a bet.

So, I positioned myself behind her and got down on my knees. I gave one firm cheek a slap because, honestly, how could I not spank her in that position? Then I placed one hand on either side of her and spread her out. Her pussy was already glistening wet. Right above, her tight little asshole stared back at me, waiting. I have to admit, it actually looked pretty cute. It’s not like she was asking me to do some scat porn or anything, so I was already warming up to the idea of this rimjob.

I decided to take it slow though, and started licking her butt cheeks. With long, slow licks, I worked my tongue all over her big, curvy ass. Despite having just played a set of tennis, Ashley had barely broken a sweat. It’s like she hadn’t even tried and still destroyed me. I slowly worked my way towards the center with my tongue, licking the crack of her ass. I was still warming up to the idea of actually licking a butthole. However, Ashley had other plans. I felt her hand on the back of my head as I had so many other times before.

“Don’t be shy,” she said and shoved my face deep into her ass. Whether I was ready or not, my face was smashed up against her puckered hole. I stuck out my tongue and gave a tentative lick. I was pleasantly surprised by the taste. I don’t know what I had expected, but I found that I actually enjoyed the taste of her ass. It wasn’t as sweet as her pussy, but it was still rather nice in its own way.

Ashley removed her hand from the back of my head, but I kept my face buried in her backside. I was licking wantonly and really began to enjoy myself. Ashley started to moan and encourage me on.

“Yeah, that’s right. Lick my ass. You filthy boy, lick that dirty asshole,” she said. The way she was talking to me was turning me on even more and I lapped at her pucker vigorously. I couldn’t get enough as I continued to worship her ass. I grabbed her round cheeks and squeezed, savoring the feeling as I worked that firm butt. From time to time, I would slip my tongue down to her pussy to tease it a little, but Ashley seemed to respond more to my tongue in her rear, so I concentrated my efforts there.

She was working her clit with one hand, but she would occasionally move to one of her tits which were hanging just over the other side of the net. Ashley was really getting caught up in the pleasure which was now surrounding her body. She didn’t care that she was in the middle of a well-lit tennis court for anyone to see. In fact, I actually forgot about that too for a while, getting caught up a little myself. The idea that somebody could be watching us engage in such a perverted act from the darkness was a bit of a turn on and only added to our arousal.

“Take your cock out,” said Ashley. “Stroke it while you eat my ass.” I obediently pulled down my shorts and began stroking my massive hard-on. With my head comfortably being smothered by Ashley’s butt and my cock in my hand, I was in bliss. I couldn’t believe how much I was enjoying myself. I stiffened my tongue and worked the tip inside of Ashley’s tight pucker. She gasped and furiously began working her clit. I worked my tongue in a small circular motion.

“Cum,” said Ashley. Her words were hushed and strained. She could barely manage to get a full sentence out. “Cum…. Cum with me.” Her body tensed up and then began to shake. I continued to lick her while her orgasm grew and grew. She squealed as her climax took over her senses. She bucked her hips and rocked herself back against my mouth.

Only when I was completely sure that her orgasm had gained complete control of her did I stand up. With my cock in hand, I stroked myself as fast as I could. I watched Ashley writhing in ecstasy in front of me and I quickly felt my own orgasm begin. I placed a hand on the small of her back to steady myself as I felt a familiar tightness in my balls. Just as Ashley’s orgasm was winding down, I began shooting my hot cum onto her ass. She had grown limp with exhaustion as stream after stream of my cum splattered across her ass.

After my orgasm finished, we remained motionless, barely able to keep from collapsing from the aftereffects of our powerful orgasms. Ashley was quite the sight, bent over the net with her pants off, her ass covered with cum. She reached behind her and began rubbing my jizz all over her butt, working it into the soft skin as if it were lotion. She licked her hand clean and found her clothes. She stepped back into her tights and skirt and made sure she had everything on straight. Then she looked at me, smiled and said,

“See you next week.”

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