[MF] Emily, the uptight account girl that loosened up

This happened a couple years ago, at my previous job, when I was just short of 40. This was a big ad agency, and since we ran a lot of global business, we didn’t just have creative types there but also lots of more admin type staff. I was not in a management position at this time, but was more of a “make things happen” type guy, the kind that took up a lot of space in discussions about work.

There were two fairly distinct groups at the agency, those who made, and those who forwarded emails. Among those who forwarded emails there was a particularly annoying girl, Emily. She’d been hired straight out of business school, and looked after accounting with one of our bigger clients. As I think back, “uptight” is the best word I can think of to describe her. A daddy’s girl through and through, he’d coached her through elite level gymnastics her entire life, and had bought and renovated her and her boyfriend’s last three apartments (since uni), so that she now lived the perfect middle class life at 27. Thick blonde hair in a tight, strict bob, often tied in a ponytail, and oh-so-boring clothes, maybe a blouse and a pair of jeans, at most a funny color on an accessory like a pair of earrings. We made fun of her, called her “applecheeks”, because of her aggressively healthy, always-happy-but-not-too-much, look. And yeah, she had high and full cheekbones, always rosy.

We met at Friday beers and such, but never really connected. As soon as I’d bring up anything outside of work (or her workout routines, which she loved talking about), she’d glaze over, still smiling, but obviously disconnected. Then we ended up in a project together. The big client she was hired for was doing badly and she didn’t have enough to do, so she was put on this chaotic thing that I was in charge of. In the first few weeks, she was equal parts irritating and helpful. She actually brought a sense of badly needed order to the project, and the client was very happy to have her on board, so when we were going out to an event that was part of it, in Amsterdam, she came along and we all stayed at the same hotel – Emily and I, the team of four more people, and about the same amount of people from the client.

Of course running the event was intense, and maybe that combined with the distance from home, made her lose her footing a bit. The second morning in Amsterdam she showed up in a white tight t-shirt and leggings, unthinkable at the office, but holy hell did it show something new. Emily’s days as a gymnast had given her an impeccably toned body, on top of which there was a tight layer of feminine wellbeing. A thin neck under that thick hair, small but perfectly shaped tits, an impossibly narrow waist that flowed into wide round hips and onwards into thick muscular thighs and tiny calves. She looked like a fitness queen, with a dreamy layer of thickness on top. It was almost like I could feel my pupils widen as she stepped into the breakfast room. We said our good mornings, and then she headed for the buffet.

I can still remember when she turned around as if it was right here, in front of me. It was the moment I went from liking tits, to becoming an all-in ass man (nothing wrong with tits, but those who know, know). I feel like I could write a novel about Emily’s ass. Perfectly round from any angle, just an extension of the shape of her hips, accentuated by that narrow waist, it flowed into her wondrous thick thighs, firm and smooth with a tiny triangular gap opening right at the top showing off the outline of her pussy (of course there was zero hint of cameltoe, this girl is a perfectionist). The crease underneath each buttcheek was distinct, because her ass was so full, but the fabric of those tight leggings never folded. As she walked toward the trays with coffee cups, seeing it move, the only thing I could do was stare.

I think she noticed, because she made a comment about not bringing enough clothes on the trip, as an opening into a passive aggressive tirade about the problems with the project and how it had been set up, and how she would have done things. Throughout the day, she kept whining, and both I and the rest of our team had a very hard time handling the negativity and questioning, as we were scrambling to patch this event together. We all worked late, and then went straight to bed, anxious for the big day after.

The actual event ended up going really well, with thousands of people participating, and press coverage to boot. So as we wrapped up, we were all happy and exhausted. Except Emily, of course. Over dinner with the clients, she kept nagging, almost complaining even though this really wasn’t the time or place. I felt I had to give things a steer, so I asked her quite sternly to come with me to get drinks for everyone. On the way to the bar, I put my hand on the small of her back and said “Hey, you really need to play nice now, Emily”. “What?” she said, feigning ignorance, but the way she blushed made it clear she knew she was out of line.

During the rest of dinner, she kept looking at me as if she was looking for approval, which was irritating, but also made me feel in charge. The day had been a success, and even Emily knew it. We were all getting tipsy, and the group split up with some people going to the dancefloor, while I stayed with the senior client chatting along. When our drinks ran out, I waved at Emily (she had the corporate card), and we went to the bar to get refills. Here’s where things took a turn, when she turned back from the bar, looked me in the eye and said, “You did really well today” or something to that effect. Someone bumped into me pushing me toward her just then, and as I was standing right behind her, that made my groin and her ass connect, and I felt her push back against me, with a slight smile.

“Oh yeah?” I said, to which she just looked down, still smiling, and turned back to look for the bartender. The rest of the night there she kept having some part of her against me, her feet or legs under the table, or touching my arm to get my attention. Her big, dark brown eyes looked into mine as i felt her finger scraping the side of my thigh under the table. We were probably a bit drunk by then, because I responded by leaning close to her and whispered “You want me to fuck you, don’t you?”. She nodded.

The hotel was just next door, and it was time to go to bed anyway, so I finished my drink and said goodbye to those still there. Emily stood up as well, and moved toward the door. Catching up with her, I put my hand on her waist, and let it slide down over her ass. It felt even better than I had imagined, and hearing her ask “You like that?” made me suddenly aware that I was hard, my jeans stretching tightly against my cock. I wanted her to feel it, so as we were making our way through the cramped doorway, I grabbed her waist from behind and pressed myself against her. “I do”, I replied.

She was weirdly quiet on our way back, for someone who was always talking. As we went through the lobby of the tiny hotel we were in, she just followed me, into the elevator. “So you want me to fuck you?” I asked when the doors closed, and slid a hand around her waist, underneath her sweater, feeling her smooth skin as my hand continued down her pants, until I could grab her ass, pulling her firmly against the bulge in my jeans. “I think I do” she said, kind of meekly, “but please don’t tell anyone?” She looked at me pleadingly, as I said “Sure”, pushing my hand further down her pants, until my fingers found her pussy from behind. Feeling the warm wetness made me groan in anticipation, and she pushed her face into my chest and let out a whimper. As the elevator slowed down, I grabbed her hair with my other hand and pulled her head back, so that she was looking up at me as I put the finger that had just been in her pussy into my mouth.

She tasted fresh and sweet, just what I expected, but better. I felt how the pent up stress and frustration from the last few days rose up inside me, how my cock felt like it was going to burst right through the zipper, and how I just wanted to grab Emily and shove myself inside her. The alcohol probably also helped with lowering my inhibitions. I almost pushed her by the waist toward my room, and quickly got us inside. Even before the lights had come on from me putting the keycard into the master switch, I was pushing her face first up against the wall, holding her by the hair as I bit and licked her neck, wildly grinding my cock against her ass. I reached round and unbuttoned her pants, pulled both them and her panties off down to her ankles, squatting down. I took a good long look at without contest the most perfect ass I’ve ever seen, before I gave it a hard smack. She let out a surprised “AH!”, and then I slapped her ass again, harder this time. “Stand still” I told her, grabbing her buttocks and pulling them apart, so I could see her completely smooth pink asshole, and her pussy, lips parting and showing her wetness as I gripped her ass even harder.

I was completely taken over by aggressive desire now, I just wanted to consume her body, and punish her for being such a bitch. I held her with all my force, as I pushed my face in between her asscheeks, and pushed my tongue against her asshole, and then toward her pussy. I reached between her legs with one arm, so I could push on her mound, forcing her ass and pussy to grind on my face. I could hear her incoherently going “Haaaaaa” as I pushed my tongue against her silky, puckered little asshole, again and again, straining it so I could start pushing my tongue inside her. My thumb found her clit, and this made her relax a little, and suddenly my tongue could enter her ass, little by little I pushed deeper, wiggling it inside her, feeling how it was starting to ache from the strain. This had all happened really fast between the elevator and my tongue in her ass, so when I let my lips close, sliding them over her asshole as I leaned back until we weren’t touching, she seemed to become aware and said “What the fuck?!”.

I just gave her a really hard smack on the ass, before I stood up, and quickly undressed. I was in such a state of flow, hard as a rock, my cock pulsating with my heartbeat. I grabbed Emily by the neck with one hand, while my other put her hand on it. As I kissed her, she rubbed my cock hesitatingly, and I really wasn’t in the mood for that, so I put my hand on hers and gripped hard, squeezing her hand around my cock, bucking my hips so I was fucking her grip. This felt good, but I wanted more, so with my other hand I started pulling her hair, downward, slowly disengaging from our kiss and forcing her down on her knees just by the bed. Since I was controlling her grip on my cock, I could easily steer it into her mouth, as she groaned. I fucked her mouth slowly, watching as my glans disappeared into her, stretching her lips as it pushed inside. She was leaning back against the bed, and her muffled moans vibrating through me brought me way too close to orgasm, we were just a few minutes in after all.

“Get on the bed” I told her as my glistening cock slid out of her mouth. She slid up, lying on her back, legs wide apart, panting. It was an awesome sight, her slightly frightened gaze, the red patches on her neck, stiff nipples, flat belly and completely smooth pussy, swelling with wetness. I got on top of her and pushed myself inside, all the way, as I leaned on my elbows and grabbed her hair, pulling her hard down on my cock until our pubic bones were grinding against each other. I could feel her stifled moans and heavy breathing in my ear, as I pounded with all my force, short deep strokes, feeling her pussy stretch, and my glans being gripped from bottoming out. Every time I pushed in, she let out a sharp shriek.

After a while I was getting warm, so I slowed down and slid in and out of her with long strokes, as I raised my head above hers, and looked her in the eyes. “You like this, don’t you?” I asked her, and she just closed her eyes and nodded. The feeling of control was total, and made me swell up again. I sat up and grabbed her hip, flipped her over and gave that impossibly sexy bubble of an ass a hard slap. She was lying flat on her belly, and sitting between her legs I got a perfect view of her gaping wet pussy, and I could see how her juices had leaked down over her asshole, making it glisten. I got on top of her thighs, and held her asscheecks hard apart, as I slid my cock down her buttcrack, pushing it against her with my thumbs. I wanted her to feel it pulse, how much I wanted to fuck her there and then.

She was moaning, so I kept sliding my cock against her asshole for a while, before I let it slide down, and back into her pussy. I was so turned on from looking at her thin waist and thick ass, that I had to go slow, watching my cock stretch her pussy open, slowly sliding in and out of her. My thumb was pushing on her asshole, increasing the pressure on my cock, and I wanted more, so I pushed even harder, until slowly her asshole gave way, and my thumb slid inside her. Suddenly her moans were deeper, more uncontrolled, and she was bucking back on me. Feeling my hard cock sliding in and out of her pussy against my finger inside her ass was so dirty, and I caught myself smiling at how this uptight girl was behaving. I started fucking her ass with my thumb, sliding it slowly in and out in the opposite rhythm to my cock in her pussy. Seeing that tiny asshole gripping my thumb was so hot, so I wanted more.

I put my hand up to my mouth, and spat on my index and middle finger, and then put them against her without losing pace fucking. I slowly pushed them inside, feeling the stretch of her little sphincter hugging them, slowing down as the pitch of her moans increased, but never pulling back. I could feel her relax as my fingers finally went inside, her smooth insides and the head of my cock pushing against them. She was slippery and wet, and fucking her ass with two fingers was soon easy, her bucking intensifying as i spread my fingers inside her, stretching her even further.

There was only one thing in my mind, her asshole and how I wanted it. So I slid out, held her open with both hands, and pushed my glans against it. I could hear her panting as the head of my cock slowly pushed her ass open. This was much more than the two fingers that had just left her. I leaned forward and put one hand on her neck, while the other held my cock in place against her asshole. Slowly, slowly, breathing into her ear, I pushed my cock inside her ass. As I felt the glans going inside, she let out a long, loud “uuuuuuuuugh”, that didn’t end until my cock was completely inside her, and I felt her firm buttocks pressing hard against my stomach.

Holding her still, the feeling of her silky smooth, warm asshole around my cock was exhilarating. I reached down with my now free hand, and grabbed her pussy. She was so wet I couldn’t believe it. Rubbing her and pushing my fingers inside made wet, slobbery noises over her deep moaning. Without really sliding out, I started moving my cock inside her ass, pushing her down on my hand. When I felt her relaxing a little, I started pumping my cock, slowly, enjoying the feeling of how her asshole gripped the base. We slowly picked up pace, both my cock in her ass, and my hand rubbing her dripping pussy. After a while, I was losing control again, and just wanted to fuck her, hard.

I sat up, and put my dripping hand on her face, pushing my glistening fingers into her mouth, two at a time, grabbing her chin and her neck, fucking her harder. She was licking my fingers, breathing frantically. Then I sat up and leaned on her back, pressing her into the bed, pounding her ass harder and harder, feeling the full length of my cock slamming into her, her ass smacking against my sweaty stomach with every stroke. I was balancing on the edge of orgasm, my cock rock hard, swelling inside her. As I looked down, it was veiny and purple, and I wanted to see more, but now I became aware of the loud, rhythmic, deep moans that Emily was making. Every time my cock bottomed out, she’d grunt, a little more desperately. I kept the pace, but hearing her so out of control made me want to go deeper, harder and heavier.

After just a few strokes with my full weight behind them, her grunts turned into a long wail, and I could feel her pussy pulsing, hard, on my cock in her ass. Her orgasm just kept going for what felt like forever, and I kept fucking her, but as her moaning dampened, I sat up to watch my cock sliding into her. Seeing her ass, with my cock in her asshole, how tight it gripped, the juices leaking out of her, and the incredible shape of her body sent me over the edge, and I came. As I felt it I shoved myself deep into her, and just let it flow, pulsing into her warm body. It was hypnotic. When I came to, I realized she was still moaning slow guttural sounds, “Huuuuuh”, “Huuuh”, with her breathing. Her body was vibrating, and she was holding my arm in a tight grip, pulling me against her. We were soaked in sweat, and the sheets were dark in patches from all kinds of bodily fluids.

Feeling her against me was nice, but I could feel my dick sliding slowly out of her. As I pulled out, she let out a louder moan, and I gave her a playful slap on the ass. Seeing her from behind as I was standing up was a beautiful, sexy mess, flat on her belly, sweaty and shaky, eyes closed and moaning into the bedsheets, legs spread apart, her ass all red and swollen, with cum leaking out of her. When I got back from cleaning up, she was sitting on the bedside, looking into the carpet.

“Fuck you”, she said, before gathering her stuff and going to the bathroom. We slept separately that night, and the next day was awkward. But less than a week later she texted me, and we ended up fucking on and off for the next year, until her boyfriend found out. He even called me and told me what an asshole I am. Anyway, they’re married now, and I heard from Emily last week, which is why I ended up writing this.

Source: reddit.com/r/gonewildstories/comments/9m8e4e/mf_emily_the_uptight_account_girl_that_loosened_up