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This was one of my favorite experiences ever, and I figured it was about time to share. During my senior year of high school, I worked at a fast food place with a few other students, and being in a fairly small-ish town, we saw friends and people we knew quite a bit. In particular, I have this friend named Natalie. At the time of this story, she had shoulder length brown hair parted on the right side, very pretty full lips, absolutely stunning long legs, and, honestly the most amazing ass I’ve ever seen to this day. Natalie and I have an odd sort of dynamic in that we flirt quite a bit, but we tried having a relationship thing once and it didn’t work. There’s still some weird chemistry there, like sometimes we push each other around and call each other names, but it’s all in good fun. Anyways, one day while I was working, Natalie came in, and she was wearing this white dress with small blue stripes that was pretty in all the conventional ways, just like she was. She came up to the register where I was waiting intently for her to order the same thing she always ordered, I think it was a turkey sandwich featuring avocado. Anyways, we converse a bit like we normally do, and I retrieve and deliver her sandwich. She says "Thanks a lot, asshat!" and leaves. Like I said, it’s just some normal friendly banter, but, as she’s leaving, I look directly at her ass. The dress is just tight enough that I can make out her butt well enough to get thoroughly reminded how hot she is. I let out an involuntary sigh as I gaze unabashed at her ass, but, unbeknownst to me, a mutual friend of ours, Allison, saw that whole ordeal, stare and all. We make eye contact and I stutter out some joke, she laughs a bit and says it’s ok before we go back to work the rest of our day. Later that week, I get a text from Natalie, asking whether or not I’d like to hang out. Not terribly outlandish, so I agree to. We meet up at the school parking lot, and she’s wearing this tight pink sweater, accentuating her lovely average breasts, (never got the actual size, my guess is about b or something), and tight, dark blue jeans that accentuate my favorite part. We agree to cruise around in her car since it has better gas mileage than mine. We went around town for a few hours, having a good time, and I’m taking in a lot of great views of her general beauty, especially because she smoked cigarettes and that’s one of the hottest things I‘ve ever seen. By the end of the day I’m pretty horny, definitely waiting to jerk off when I got home. However, she asks if I want to come over to her place and play some card games, one of our favorite activities. I say yes because, other than my libido, I have no reason to say no. Her family was generally very strict Christian, aside from her. Their house was fairly sizable and new, sort of modern and blocky, like rich people in California (probably). We get there and most of her family is watching a movie, I’m pretty sure it was Sin City. We say hi, before heading upstairs to her room. Her family thought nothing of it because of our long friendly history together. We decide to play Uno, a go-to game for our friend group, but, the thing is, we’re both very competitive and real good at Uno. I think we start playing at about : and we don’t finish up until maybe nine o’clock. One game, an hour and a half. During the game though, we’re talking. "So," she starts, looking at her cards. "Allison texted me the other day." "Oh yeah? This sounds interesting." Sarcastic, I was. "She said you really liked my dress," she stated nonchalantly, almost like she didn’t care honestly. I sort of knew where she was going. "A conventionally cute dress for a conventionally cute girl," I said, trying to use the word ‘conventional’ as an insult. "She said, and I quote: ‘he looked like he was drooling a bit after you said goodbye.’ I don’t think I quite understood what she meant." Oh, she did. We made eye contact and I was a touch flustered, honestly, so I changed the subject. "We’ve been playing this game for a while now, why don’t we make it more interesting?" I asked. I didn’t really have an idea, my mind at the time was thinking maybe money or something to that effect. "I think I have a good one," she said. We both had a great deal of cards in our hands at this point, so it all seemed far off and inconsequential. "The winner gets to order the other around all night." Immediately, my mind went to sexual places, something both of us had experience with, but she didn’t even seem phased so I agreed. Seeing the possibilities and finally having a real reason to care about the game, I stepped it up. We continued the game until nine-ish, the rest of our conversation continuing normally. Finally, I saw an endgame. The way we play Uno, I had basically a + card in my hand altogether (one being a wild draw ), and a red # probably. The bottom line: the game was mine. It all happened really quickly, maybe within thirty seconds, I went from five cards to none and the game was mine. A second later she swore in frustration and threw her cards down, but I’m pretty sure she was smiling. It was quiet for a second until I spoke. "Oh, where to begin?" I said slyly, she threw me some mad stink eye. "How about you go grab us both some water?" I wanted to start off slowly, I had an idea of where to go, but I didn’t know if she wanted to go so far and I didn’t want to make her uncomfortable. She came back and we discussed the game a little bit, and she faked contempt towards me. "So what do you think of that dress?" I asked eventually. "I like it, but probably a bit less than you do," she said, and it reminded me of tsundere girls. "But I think I can tell where this is going." "Maybe just a brief little fashion show. No harm in that," I said as I sat on her bed. She sighed and went to her closet, rummaging until she found the dress, and went to her bathroom to change, since it was just across the hall from her room. My heart was racing so fast, we’d never done something this intensely intimate before, and she was basically about to just flaunt her body in front of me. I’d jacked off to imaginary scenarios that weren’t nearly as hot as this! I waited there for a while, but it probably just felt longer to me, before I heard her call across the hall. "Ready?" she asked as I heard the bathroom door open. ""I’m ready if you are," I called back, blood racing. She stepped into the room wearing the dress, as expected, but something was different. She obviously had applied some makeup while she was in the restroom, but the difference wasn’t in her beautiful lips, or her picturesque hair. She was walking slowly, deliberately, every step holding my attention with no mercy. She looked up and caught me staring, probably slack jawed, at her whole appearance. I looked quickly back at her. "A deal’s a deal," she said as she walked towards me. My pants were substantially more uncomfortable than they were during Uno. As she finally reached me, she bent over and grabbed my shoulders, arching her back and thrusting her body upward, making sure to leave less than an inch of space between my face and her breasts. She shook her chest slightly, teasing me, before turning around sharply, and grabbing her ankles quickly. It took every fiber of my being to not grab her ass or just cum right there. She slid her chest back up to standing position, shaking her ass as she did so. The dress wasn’t incredibly short, but it wasn’t a full length dress either. She walked towards the wall and lifted the back of her dress just enough for me to catch a glimpse of her underwear. Good god, it’s getting hard to focus on writing this. She stood flush against the wall before pushing it so her body formed a right angle, her ass, once again front and center. I ventured a sentence into the electric silence. "Wow," I said, at first, the words almost failing me. "Either you’ve done this before, or you’re enjoying this as much as I am." She looked back at me smiling, half stink eye half smile. "I think I’ll let you determine the answer to that," she said walking back to me. "I think I more than accomplished what you wanted me to with this whole thing. What do you wanna do now?" "Are you sure you wanna know?" I asked, laughing. "It doesn’t get any less… provocative." She sighed once more, "A deal’s a deal!" She winked. It was game time. I stood and grabbed her shoulders and positioned her quickly but gently, she was now bent over her bed, elbows holding her up. I stood behind her and just basked for a moment. I put my hand on her lower back and slowly moved it lower, before adding my other hand. The dress was soft, but definitely was not my goal. I lifted up her dress and got my first unabashed look at her ass and underwear. She was wearing a simple blue pair of briefs but they were still absolutely incredible. She laughed as I started to really play with her ass. I was in another world, practically heaven. I snuck my fingers into her underwear, ready to pull them off when she spoke. "Hold on," she said, standing up. I thought maybe I had gone too far and I was terrified. She walked over to her door and closed the door, even going so far as too lock it. Reassured, I watched as she walked back over, and assumed the position on the bed once more. I chuckled and pinched her ass, earning a breathy gasp from her. Wasting no time, I yanked her underwear down. I couldn’t breathe at the sight of her pussy and ass, things I once thought I would never get to see. I decided to start the real foreplay. I kissed her ass softly, enjoying the faint but distinct smell of her sex. I squeezed both cheeks and just enjoyed myself a bit before I spanked her. It wasn’t hard but it was definitely unexpected. She yelped and covered her mouth and I laughed. She joined in my laughter and I went back at it. After a bit, she spoke. "Hey, loser, I’m waiting over here." Always the banter. I unzipped my pants. "I’m the one in charge here, loser," I said, relishing that last word. I pressed my underwear tent into her ass and she breathed. "Fine," she said. I ground my dick into her for a few seconds before pulling down my underwear altogether, my cock springing up to vigorous attention. I pressed it against her ass crack, getting harder than I ever have before in my life. I just ran my dick up and down her crack, teasing her. "Are you ok without a condom?" I asked. She quickly nodded. I immediately obliged and thrust into her. If god had his way, I would’ve came right there, but I fought for it. We had both gasped at the realization of what was happening. Using her hips, I slowly started going at it, each thrust of mine seemed to invoke a breath in her, and so I sped up gradually. She was so tight, I would thrust for a while and then have to stop for a second to not cum, but I played with her clit in the meantime. Eventually I built up a rhythm we were both feeling and we both breathed heavily. She looked back at me with a face full of pleasure and said: "You’re still in charge, ya know…" I knew her implication. I grabbed her hips and thrust into her harder and faster, I was really feeling this and knew I couldn’t keep this up for too long. I smacked her ass hard and she moaned. I went a step further and leaned into her, pushing her body down, and pulling her arms back towards me. Her face buried in the sheets allowed more vocalized pleasure, so her muted moans just increased. I went as hard as I could into her and she started showing signs of climax. She started wiggling around and grabbing the sheets and such, I knew she was close. I continued thrusting as her moans built in speed and brevity, before she arched her back and tensed up. I could feel myself inching closer also, so I knew what I had to do. "Bring me your face," I said quickly, and she obliged as best she could. She had just enough time to push the hair out of her face before I practically exploded all over her face, shooting one of the biggest and most intense loads of my life. We just stayed in that position for a while before I leaned in and told her to suck me for a bit. I was spent so it was only a few seconds, then I told her to clean herself up. "Asshole," she smiled and started to wipe all of the cum off of her face and lick it up in her mouth. So that was basically the end of the night for this sub. We didn’t start dating since we were both close to graduating and were going to very different places for college, but we ended up hooking up a bunch more as the year went on. I might tell some of those stories if there is interest. imadethisforpornkt