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My Naive Little Coworker

Category: Mature
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Ever had a co-worker you wanted to fuck so badly it almost hurt? I think that’s fairly common, especially for men of my age and experience. But to have that coworker admit they feel the same makes it much more interesting. Add to that a 20plus age gap and endless creativity, and going to work can be almost dangerous.

A few months before I turned 50, I confronted a coworker about her ogling my crotch. I don’t know if she was aware of how often she did it. She said she wasn’t, and I believe her based on her deep blush. I’m the only man where I work, so I do catch coworkers on occasion, but with her it was a bit different as she was the youngest woman there.

Anyway, what I thought I knew was that she was a somewhat awkward young woman with perhaps a subconscious crush on an older man. We’d worked together for a while, so I knew she didn’t have a father, and thought maybe it stemmed from that? She even came to me with homework on occasion as she worked through college. It was unsettling at first but still flattering. She’d lost 40plus pounds a few months before this started, leaving her with a pretty nice body, so despite her being a mouthy redhead with a feminist bent, having her blush when I caught her eye was hardly an insult. I figured at my age I could adjust my standards some for compliments right?

I suppose I should describe us a bit more in detail here. She’s about 5’8, maybe 140 pounds? She’s got one of those figures that’s sort of thin and lanky on top, but a full ass? She was self-conscious about how the size of her breasts, but I would place them at maybe a B cup? Definitely enough to work my mouth around I thought. She also has this thick, sort of curly red hair and big eyes that I suspect on occasion she tries to work to her advantage (think calf eyes). I’m 6’4, a little bulkier with shoulders she called broad and an ass I thought was decent and she confirmed.

When I first confronted her and made her admit she “liked” me (I had no idea!), we behaved as people do with a newfound affection. I still don’t know why her. Mouthy, stubborn, a little standoffish, occasionally cursing like a sailor, she was hardly my ideal. I ended up by her desk more often than usual, and she in my cubicle alarmingly often. It was harmless at first. She was actually sort of re-assuring to my slipping self-esteem, I was horny, and it was springtime.

Then we started to play truth or dare via text message. This is when she revealed a few things I did not know and the trouble in my pants started. My little coworker, who I thought was naïve, had had more sexual partners than I had. She also posted nude pics online after blocking out her face and tattoos (yep, she was an aspiring businesswoman with tattoos, surplus earrings and blue mascara- what a cliché right?).

She wouldn’t tell me where those pics were, but within a couple months I was able to “dare” her into a pic via text. It took forever, daring, coaxing and nudging, but the first time I opened that text message and saw her pussy, I felt my stomach clench and my dick harden in a way it hadn’t in many moons. My type or not, I really, really wanted in that.

Then came the dare that started the physical part of it. She actually dared me to grope her breast in the same room with another coworker! I had groped her a bit in the break room but over her clothes and in passing. With this dare though, I upped the ante and standing behind her at her desk, shoved my hand down the open neck of her peasant blouse and gently squeezed that firm, small breast. Her reaction was a deep blush and clapping her hand over her mouth. Our other coworker never even noticed.

From there, it just got more heated. This woman was cautious in deference of her career, but still liked a good dare. She even started going without underwear at my nudging. The first time I stood behind her at her desk, and she lifted her skirt to show that sweet little pussy without any fabric over it it took several hours for the image to fade.

I mean, can you imagine? This barely 27 year old woman sliding her skirt up, with her thighs apart just enough to see the slit? All I wanted was to lean forward to slide my hand into her lap and into that slit. I also wanted to pound that all day, and it was 15 feet away, with nothing to hold me back but a thin skirt. A couple times I snuck up behind her and did reach into her lap. The jerk and gasp I got in reaction was rather flattering. She was always so warm there too.

That was the other thing- she tended to wear skirts, those clingy fabric kind. When she stood at the right angle beside me at my desk, I could almost see the outline of her pubic mound. I doubt anyone else could see it but I could hardly see anything else. Like I said she was thin enough, there was actually a mound there. I imagined it would feel great when slamming into it… Sort of soft but firm.

She brought me back to my younger years, which is largely how this all got out of hand. The first time I came up behind her at her desk and pulled my dick out before she even looked up was memorable. That blushing gaping look was sort of a balm to my lagging self-esteem. Maybe it sounds sick, but it never hurts to be made to feel desirable and well, like a man. After a while I coaxed her to reach up and touch, even stroke me, while standing at her desk with my back to the others.

A couple times when we were alone after work, I tugged her into my lap or against me. She had this way of running her hands over my chest and shoulders that made me feel…different. She was exploring me, eagerly. She sometimes would drop her head onto my chest, and just stand there with me, quietly exploring. It was rare, as she rambled when she got nervous but those moments made me question a lot about myself. Just a few months after I confronted her, we were a little too comfortable with each other.

Early on we established there was no chance of a relationship working out, and neither of us was going to pursue it, and there would be no sex between us. As far as a relationship went, she had a young child I had no interest in raising, and I was comfortable with my life. She actually got pissed when I accused her of being in love with me. Like I said, she was sort of unusual but perfect for this type of thing.

Oddly we would occasionally fight and then almost make up like a couple. She was pretty hot-tempered. The first time she yelled at me, she apologized via text, and then came into my cube after hours when all but a few people were gone. As she stood there talking to me, I slid my hand up her firm inner thigh to feel her quiver.

I thought it was rejection or nerves as we could hear the next person over typing until she quietly giggled sheepishly, put my hand back, and quietly revealed she was ticklish even there (really, who’s ticklish at 27?!). I had to try again to work around that, but when I cupped her pussy through the silk thong, I very nearly came in my pants- she was soaked. A couple slow strokes through that silk, my fingers were wet.

When I took them away and slowly rubbed them together to test the moisture, she blushed deeper and stammered. Apparently she didn’t realize it was that noticeable. That was the great thing about her- she was knowledgeable enough I didn’t feel guilty or like I was leading her astray, but she was in a little over her head with someone my age.

I kept pushing her to give me details on her fantasies about me. Eventually she revealed she thought about me while “flying solo.” I liked that idea… But when she wrote out her fantasies, which included a detailed blowjob chapter, the boundaries all fell apart. We sort of avoided staying late together as most times when we did we fooled around a bit and it worried me. After I read that fantasy though, I felt my interest in her, and more specifically her pussy, peak as it hadn’t since the first time I touched her (at that point I was touching her daily).

My birthday was also coming up. I did not want to turn 50. I knew I was still attractive, but the new aches and pains I felt in the last few years were depressing. In her way, she re-assured me, telling me if I could make her blush like I could, I couldn’t possibly be that old. Still though, at her age, she couldn’t understand this type of thing.

A week or so before my birthday, and a couple weeks after she let me read her fantasy, we were the last two in the building. I knew she was there as I could hear her typing. I wasn’t sure if she knew I was there, as she tended to blare this awful head-banger music in her headphones while she worked. About 5:30, when she normally punched out, I heard her putting things away and so on. Then she came out of her cubicle, stopped in mine on her way out, and stood as she had so many times before, leaning against the partition that formed the door.

I bantered with her, teasing her about the construction workers in the building that she had told me she’d caught checking her out earlier in the day. She found it sort of flattering. She tended to move around a lot when she spoke (I think she drank 2 pots of coffee every day) and ended up a bit closer to me.

Slowly, so she knew damned well what I was doing and had a chance to bail, I reached out and grabbed that clingy skirt and tugged her into my lap. I liked the way she didn’t resist, and the way she relaxed, trusting my arm around her. I got the feeling she’d been treated badly in the past by the way she seemed flattered by those little things. With that soft blushing smile I recognized as the companion to a wet pussy, she leaned into me and kissed my neck. Murmuring she asked how I was doing today. I had to clear my throat before making a flippant reply that I had something heavy in my lap and there was this redhead that wouldn’t leave me alone. She chuckled and bit my ear.

By this time, as you can imagine, I was rock hard under her soft ass. The way she was arching into me did not help. She was rubbing my chest again in the way I liked, that gentle but urgent exploration. I unbuttoned her sweater and slid my hand into it to fondle her breast. She sighed and moved her mouth to mine.

That should have been my red alert. Neither of us had made any move to kiss each other before. I could feel a fine sheen of sweat on her skin as I wrestled with her bra and I was a little warm myself. Eventually she broke her mouth away from mine and leaning back, reached her arms behind her and unhooked it herself, under her sweater.

Another red alert. We tended to work around clothes but not take them off and had never unhooked her bra.

This was the ultimate taboo for me really. A coworker, young enough to be my daughter, in the office. I have to say though that just made me hotter… I don’t think it hurt her any either.

Once free of the tight confines of the bra, she leaned into me and gave me an open-mouthed kiss, smiling. We might have been okay, but she shifted her hip slightly (she was sort of side-saddle with her side to my chest) and was suddenly putting additional pressure on my groin. She pulled back and nuzzling my neck, whispered in my ear she was afraid there was something wrong with my lap… I chuckled and squeezed her ass with one hand and her breast with the other and advised that she be a good “team player” and investigate the issue.

We both sort of giggled there. I don’t think I’d come that close to teenaged giggling in decades. Like I said, I think young pussy has a weird effect on men my age. I asked her if she’d like to turn to face me. I knew she had fantasized about me helping her to finger herself to orgasm, in my lap. I wasn’t sure of the details but that was plenty. She nodded and immediately moved to stand.

Maybe that should have been the biggest red flag of all. This mouthy little feminist never, and I mean never, came even close to taking direction from a man in her life on principle, so to see her move that fast at my suggestion… But then she put her hands on my shoulders, lifting one leg then the other, and guiding them under the arm rests of my chair, settled directly on my cock. I was not worried about red flags. I was more concerned with red haired pussy.

Settling down she ran her hands over my shoulders and kissed my forehead. Sliding my hand up her thigh, I came to her hip… Then nearly stroked out realizing that today of all days she was minus panties. I stopped cold, making her jerk back and stare at me. She asked if I was okay, looking concerned. I nodded, then shifted my weight, realizing perhaps for the first time how risky this was. Huskily I told her I hadn’t realized she was without underwear and suggested maybe we should stop now.

Lifting my chin, she made eye contact and nodded with those big eyes staring into mine. Kissing my forehead again, she started to rise, telling me it was fine and probably for the best. As she started to stand, her pussy came forward and brushed against my hand. I realized she was just as wet as she had been the day she had yelled at me when her moisture soaked her silk thong.

I took my hand off her breast and put it on her shoulder, pushing her down into my lap again. She started to bitch, exasperated, and told me to stop being so fickle. I yanked her hair hard enough to jerk her down to my mouth and slid my fingers close enough to her pussy to feel that short hair against my fingertips as my tongue went into her mouth.

She went completely still and seemed to be waiting for something… And I obliged, sliding one finger deep into her. Damn, she was tight. She joked a lot about having a big baby and the resulting damage but I can’t say I had a complaint. Her pussy wasn’t completely smooth on the inside, but instead had all these little ridges, sort of like a head of lettuce or a flower has folds? I’m not great with poetic descriptions but I somehow knew those were the kind of ridges that would act as great friction as I pounded her.

She slowly moved her hips forward, sort of riding my finger, as her tongue moved against mine. I curved my finger a bit, and felt her moan vibrate in my mouth. Now that my finger was a little deeper, the cum was really coming down. It was thick and hot and almost dripping down my finger.

Pulling my mouth from hers, I murmured in her ear to start working herself. I can’t recall the terms I used, but she suddenly looked up and smiled and asked “Really?” like I had just done her such a favor. I got the feeling again that maybe she hadn’t always been accommodated sexually in the past and appreciated little touches.

I almost felt kind of bad, like she might be vulnerable in a way I didn’t know of, but that warm, sensual smile just did me in. She wanted me to do exactly what I was doing. I knew part of her arousal was likely because I was just as off-limits to her as she was to me, but still, I was flattered.

Anyway, she tucked her head into my neck and reached down between us. I saw her shoulder moving since she was facing me and felt her hand brush against mine. She ran her fingers over my hand, seeming to note where my finger disappeared into her. That hot, thick fluid was all over her hand and mine. Every so often her knuckle or finger would brush against mine and slip around… It just emphasized how wet she was for me.

Within a couple minutes she was rocking back and forth on my finger, more or less riding my hand. As bad as I wanted her to do the same to my dick, I really wanted to see her work herself to orgasm. I whispered this interest in her ear and she pulled back, slowing, and breathlessly asked me what I needed. I yanked her skirt up so her pelvis was completely exposed to my gaze.

Blushing slightly (really, she actually blushed with my finger in her and halfway to cumming in my hand) she tucked her skirt down under her ass and whispered to keep it down to avoid staining my pants. Returning to moving her hand, she moved to sit at sort of an angle so I could look down and see her lap. Her hand was somewhat in the way but I could still that bright red, almost orange hair, barely covering that sweet little mound. She kept it short, but didn’t shave it all off.

That reminds me, I had asked her months before not to shave because it made her seem so young it weirded me out. She actually agreed with my reasoning. I preferred it long, sort of retro, actually, and sometimes she would grow it out and then do a before and after trim picture for me. She was damned accommodating at times for all the sass…

She was climbing, I could tell. Those tight walls were starting to clench around my finger and she was whimpering into my neck. Her free hand was clenching my shoulder and I was lost in the smell of her arousal, sort of musky and sweet, when I heard her whisper in my ear she’d like another. Sort of lost in thought I muttered another what? She sighed and jerked her hips forward in response.

I had teased her for months about how many fingers she would need from me. Realizing that was what she’d meant, I gently pulled the one out, then slid in the pair, pointer and middle. I noted her sigh when they slid in. It sort of made me wonder if she would sigh like that for my dick sliding deep in her, or if she would moan.

That must have been what she needed, because her hand started to work faster and her hips jerked with it. Whimpering steadily, sort of breathy soft noises, she was climbing . Her ass was tense against my thigh and she was straining against my hand. Looking down I noticed my fingers were wet past the last knuckle with her cum…

Then she started to orgasm. It had only been a few minutes but felt so much longer, watching that tight little mound on my hand. I had wondered before if she would be loud and but she kept a lid on it as anyone could enter the suite from just down the hall. She started to moan, tucking into my shoulder to try to muffle the noise. As she spasmed and jerked, she moaned my name and whispered the most sincere thanks I have ever heard, both before or since.

I rode out the whole thing with her. I couldn’t see her face but felt the tension and the heat radiating off her, the sweat forming on her skin. Looking down again, I could see those firm thighs tensing as she moved and had a good idea that she would look much the same on me.

Eventually, she slowed and stopped, still tucked into my shoulder. I should have let her get off my lap as she likely would have. I could have asked her for a blowjob or something to make us even. She seemed always concerned about physically teasing me and leaving me hanging, so she likely would have done it without protest.

But somehow I ended up unzipped. I think I meant to just tuck my erection against her stomach as I had in the past, to feel that warm skin against me. I don’t know who unzipped me. Our hands were tangled in our laps. She was just far enough back on my legs either of us could have done it really. I just realized my dick was throbbing against her thigh, apparently about the same time she did…

Looking up with those big blue-green eyes (and by now, enormous pupils) and asked me shakily what I was doing. I think she meant more what did I want, like the blowjob I mentioned earlier. I just shook my head and I think stuttered something about not being sure. She started to tuck her skirt down and brushed against my dick.

At this point I was starting to leak pre-cum. I whispered into her hair to please just touch it, just hold it against her. She shifted slightly away from me, letting me rub against her thigh, and sighed, caressing her free hand down the back of my neck. Her other hand grasped my dick and gently squeezed. She had touched me enough that she knew what I liked, and gently ran her fingers up and down my length.

She stopped when she reached the moisture at the head though. Again moving back to look into my eyes, she whispered one of us needed to move… I nodded, and dug one hand into her hip. The other hand had somehow gotten tangled in those long red curls and tugged her close to my mouth. As she leaned in to kiss me she slid forward, I was against her pubic mound, then…

Her damp heat enveloped the head of my dick. I felt her jerk slightly. She seemed startled. I wasn’t in all the way but could tell how much I would enjoy if it if I was.

She was holding perfectly still. I don’t know when I closed my eyes but opened them to find her still staring at me. She looked torn, sort of stuck. She hadn’t pulled away though, so I knew she wanted more of me in her. She seemed afraid to make a move though. Her hair was still in my hand, so I tugged her back to my mouth. She managed to lean in this time without moving her lower body. I whispered against her mouth she didn’t have to continue if she didn’t want. She nodded then said something barely audible ending with “don’t know.”

When she looked down, or maybe just away from my gaze, her hips moved just a fraction, pushing me in to that slick heat just a little more. Suddenly the hand resting on her hip moved to the small of her back and nudged her forward. I didn’t have to push her very far before she took the rest of me in on her own with a gasp.

Both her hands were clenched on my shoulders. She was so warm… I had felt the heat radiating off her crotch, even inner thigh, for months and knew it would be but it still floored me. There was also that wetness. If those firm walls clenched around me weren’t enough, that thick, smooth moisture would likely have done it. I could feel some more sliding down her as her walls flexed and hugged me.

I realized either one, she was not used to my size, or two, she had not had any dick in a while, by the way the walls clenched and relaxed. I didn’t think I was particularly huge (I have some modesty) so I assumed it’d been a while for her. I knew she masturbated regularly but wasn’t sure about actual sex frequency.

Moving my hand to her thigh, I gently stroked her leg and asked if she needed a moment. She nodded, then started to ride me ever so gently. This was not the boisterous, reckless sex I had expected. She seemed to be testing, waiting for something. After a few of those back and forth moments, I was completely covered with her fluid, and she had worked me all the way in and out several times. I was dying to thrust but sensed she wasn’t ready somehow.

Just as I was about to ask, she suddenly pulled back, almost to a withdrawal, with just my head still inside that slippery haven, then thrust her hips forward. I felt something rounded and firm bump my head, and realized it was her cervix… She must have been waiting to open up enough for me to do that. I didn’t know or care because then she finally started to ride my dick as she had my hand.

She had a way of rocking with just her hips, so she didn’t push too hard on my chest or sprawl on me like women occasionally do. After a couple of these more aggressive thrusts she put my hands on her hips, biting my ear gently, and whispered “Guide me.” I didn’t need further instructions.

I spread my hands open so my thumbs rested on her hips and my fingers reached to her lower back. I urged her into a harder rhythm, and soon she was grinding into me. This was what I had expected, and feared, all these months. There seemed to be no limit to her cum, slipping everywhere. I somewhat expected it to soak through her skirt and into my pants at any moment.

She was panting in my ear when she slipped off me. With a gasp she grabbed me and guided me home, then moved her legs in a bit closer. I could hear her high heels click slightly on the floor as she sought traction. I was climbing pretty steadily at that point. Those walls… The “flower” folds I felt earlier had the exact effect I thought they would, hugging me tight as they clenched, and giving me friction enough to counteract all the lube she was producing.

I realized her open sweater had slipped off one shoulder. I nudged it down a little further, pushed down the laces of her camisole and bra and took her nipple into my mouth. There was a whimper… Then I bit down just enough to count. That earned a moan and a particularly deep thrust, her cervix almost caressing my head.

The chair was creaking as she surrounded me. Her curly hair was in my face, her large, hard nipple in my mouth and her legs tensed up and squeezing me though they were forced apart by the chair, when I felt myself go over that first hill approaching orgasm. I let go of her nipple long enough to choke out a question about whether she was ready. I have no idea how I worded it and doubt it was suave in any way but she got the idea. She mumbled something about “can’t” and I swore at her (like I said, not suave) and told her to use her hand.

She nodded and for the second time since I’d known her, did as I told her. I felt her get warmer around me and figured she was catching up. The way she went back to tucking her head into my shoulder confirmed it. She was riding me with long strokes, taking the full length into her and then back out. As the speed of her hand increased, so did the heat, then she started to moan my name again.

She wasn’t able to stay tucked into me so tightly this time due to the pace, and her moans were almost deeper, more urgent. I didn’t expect to hear myself do the same when that orgasm hit me in the back of the knees out of nowhere. I think it was the way, as her body tensed again and I felt that rhythmic clenching start, she whimpered “please” in my ear. I still don’t know what she was asking for as she was doing the work, but I went over that hill and the waves were incredible. It was one of those cums that grabs your whole body in its clench/ release pattern from your toes up to the back of your neck.

I think she started to cum right after I started, and I felt yet another gush flow over my dick as I started to fill her. She was struggling to stay on as were both sweating and our groins soaked in fluids, but didn’t miss a beat, riding my dick til her legs gave out.

She told me later I nearly yelled in her ear; I maintain it was just a moan. I don’t recall much from the time I started climbing to when I slowly caught my breath, except for the huge waves rolling over me. That I’ve never forgotten. When I did finally come down, I found my little coworker curled into me, but without the tension in her body. The sweat showed on her face and chest. Her camisole had come back up to cover her breast, but above it I could see the shine. I even felt it through our clothes.

I reluctantly gave up her heat, largely because I feared I might lose my hard-on soon and didn’t want her to see, and nudged her down further in my lap. When she stood, she grasped my shoulders, and I could see the tremble in her legs as she lowered her skirt. It’d been a long time since I’d felt that, what’s the word… Proud, or maybe satisfied, in kind of a Neanderthal way. Helping her stand and untangle her shaky legs from my chair, noting the cum slip down her thigh and that lush musky scent, just increased the feeling.

To this day, every time my “naïve” little coworker gives me that knowing half smile, my dick and my pride both swell with remembering that feeling. The thing about forbidden fruit, or more bluntly, pussy, is it never loses its taste. I may be half a century old, but I’ve never enjoyed and dreaded going to work so much in all my life.

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