Seducing My Married Coworker

Author's note: If you couldn't tell by the title, there is unfaithfulness present in this story, to a degree that would be infuriating to some. I would recommend against reading this if that's something that may bother you. This story is also a story in a traditional sense; it's not just a quick fantasy fuck. I almost categorized it under Literotica's 'Novel and Novellas' heading, but ultimately decided it was too tightly focused on sex and seduction to fit there. Still, set your expectations accordingly. The third act in particular gets a little heavy; stick to the first two parts if you want something less complicated.

Last warning--the main characters are not paragons of virtue. This story is not designed to illustrate any kind of ideal, but rather capture a more realistic view of two coworkers who become closer than they should. The characters aren't meant to be likeable, but they are critical to the story, flaws and all.

And the usual disclaimers: all characters are fictional, similarities to real-world people/events are purely coincidental, everyone involved is of legal consenting age, etc.

My name is Ian. This is the story of some of the hottest sex I've ever had. I don't say that lightly--I've been with over a hundred woman in my life. I know your first reaction is to be skeptical, but it's true. It helps that I follow the two classic internet rules of how to get girls: 1. Be attractive and 2. Don't be unattractive.

I've been told I look like a more approachable version of Ivan Drago from the old Rocky movies. I'm a big guy, at around 6'5" and at the risk of sounding immodest, I'm built. I'm not as beefy as Ivan--no man is without major steroids--but I'm a personal trainer (part-time, at least) and spend a lot of my time working out.

Good looks are extremely helpful in getting women, for the confidence boost if nothing else, but they're not enough on their own. At least, not for my numbers. You also need to be able to connect with women; show interest in their interests; anticipate their turn-ons and turn-offs, understand what they want from sex, and so on. Experience and willingness to be turned down is also critical. I've had at least as many failures as successes, but I've learned how to deal with rejection.

But the biggest secret to sleeping with lots of women is to broaden your standards. I'm thirty-two now, but when I was younger, I only wanted to sleep with 9s and 10s. That was fine for a while, but everything changed one night after I slept with a 6. I won't go into details now, but that night changed my life. At the time, it was the best sex I'd ever had. I couldn't believe how much this 6 had outshone the other objectively more attractive women. I thought maybe it was a one-off, but after a few more 6s, I realized it wasn't.

It took me a bit to figure out why 6-sex was so much better, but I've developed a few theories. First, 6s are more appreciative when a guy like me shows interest in them. 9s and 10s take it for granted, but for these 6s, I may be the only 10 who's ever approached them. Second, 6s generally know they're 6s, and they've developed in other ways to make themselves more attractive. 9s and 10s usually coast on their looks, but 6s tend to be more interesting. My last theory ties these two other theories together: because 6s don't usually get to be with 10s, and because they don't rely on their looks alone, they're usually better lovers. They realize that a 10 fucking them might be a once-in-a-lifetime event, and they show it.

Once I realized this, I expanded my range from exclusively 9s and 10s to 5s and up. And the amount of women I was sleeping with skyrocketed. I admit it's a bit reckless to sleep with so many women, (especially without condoms whenever possible), but I don't have any kids yet--at least as far as I know. I have had an infection or two, but nothing incurable. Well, besides herpes, but everyone has herpes these days. Most of the time you can't even tell.

But enough about me. Let me introduce you to the woman who would become my favorite partner: Cassi.

Cassi was a coworker of mine at the outpatient physical therapy clinic I work at. Well, technically, she's kind of my boss because she's a physical therapist, and I'm just a PTA (aka an assistant). But she usually worked at one of our sister locations, so when she did cover a shift at ours, she didn't pull rank on me.

When I first met Cassi, I thought she was a 5, and an uninteresting one at that. Cassi is a bit older than me, at 36. Physically, she's on the taller side (maybe 5'11") with long straight red hair that falls halfway down her back. But she looked very lanky, especially in her loose-fitting scrubs, and I prefered my women with a bit more meat on them. She also didn't wear any makeup, which didn't do her any favors. I know many guys say they prefer no makeup... but trust me, most of them prefer light makeup and just think it's no makeup. Still, I'd slept with other 5s before, but they usually had redeeming qualities.

I didn't see that in Cassi. She was a chatter, but it seemed like all she talked about was her family and her church. She was happily married to her high school sweetheart, Joseph, and they had two perfect angel sons who were now in middle school. They spent a lot of their free time volunteering and going on mission trips together. I died a little any time I was sucked into one of these conversations.

If things had gone differently, it was entirely possible I never even would have given Cassi a second thought. But then Casual Friday happened, and everything changed.

As I mentioned, Cassi didn't usually work at my clinic. She filled in once every month or two on average, when another physical therapist needed time off. This is how I'd gone a year knowing Cassi without ever seeing her in anything other than loose scrubs. But one Friday, she had a shift to cover, and instead of her usual scrubs, she came in wearing jeans and a T-shirt.

When I laid eyes on this new Cassi, I didn't even recognize her at first. Not to be overdramatic, but it was like she was a completely different person. Yes, Cassi was still skinnier than I normally preferred, but I could now see she had curves after all. Her ass wasn't large, but her frame made it seem bigger by comparison. Plus, her tight jeans emphasized how well-shaped it was. Cassi had breasts too. They were a B-cup at most, but again, on her frame, they were noticeable.

She also had put on some light makeup, and her slightly splotchy skin now looked smooth and flawless. Plus, she had done something with her eyeliner that made her blue eyes really stand out, in a piercingly attractive way. Ironic that the first time I'd seen her in makeup was on Casual Friday, but I wasn't complaining.

Seeing Cassi transform like this was an epiphany for me. If Cassi had been hiding herself physically like this, maybe there was more to her personality too than #faithandfamily. I decided to find out.

At lunch, I made sure to sit across from her, and unlike my usual strategy of avoiding chatting with her at all costs, I initiated a conversation. After some light small talk, I transitioned to my hidden purpose--digging for signs of a real person under Cassi's boring veneer.

"Hey Cassi, I just realized I've known you for about a year now, and I still don't know much about you. I mean, I know about your church and family, but I mean you personally. Do you have any hobbies?"

Cassi looked at me thoughtfully, putting her fork down from the salad she'd been eating. "Oh man. I have more hobbies than I have time for these days." She smiled wistfully as she turned her full attention to me. It was like she had just been waiting for someone to ask her that question.

"Let's see. I run quite a bit, and I like hiking too. Disc golf is a lot of fun, but I don't get to do that much anymore. I bake--I've been making our own bread for years now. I like to read..."

"Oh yeah? Any favorite authors or genres?" I interjected.

She looked around conspiratorially and leaned in towards me. In a low voice, she said, "Don't laugh, but I actually really like Stephen King."

I laughed. "Stephen King? The guy who wrote all those horror stories about killer clowns and killer dogs? You're pulling my leg, aren't you?"

Cassi shook her head at me, as if she was annoyed at my disbelief, but she kept smiling. "I told you not to laugh. But yes, that Stephen King."

I stared at her, still trying to decide if she was messing with me. "I'm sorry. I just can't picture Little-Miss-Innocent Cassi reading those kinds of stories. No offense, of course."

"See, you're not the first person who's told me that," Cassi said, jabbing her fork at me pointedly. "But what none of you understand is that Stephen King's not really a horror writer. I mean, he is, but he's a actually a character-author first and foremost. He just uses horror situations to bring out different sides of the people he's created."

"Uh huh..." I said, with a heavy undertone of skepticism.

"Listen, I know you're making fun of me now, Ian, but I know what I'm talking about. You know The Shawshank Redemption? Stephen King did that. Stand By Me? Stephen King. The Green Mile? You guessed it. Mr. King himself."

"Wait, Stephen King wrote The Shawshank Redemption?"

Cassi smirked triumphantly. "He sure did. Bet you didn't see that coming did you? And even his horror stories spend a lot more time developing his characters than you think. That 'killer clown' you referenced? You're talking about the story 'It', and that book's over a thousand pages long. Yes, there is horror there, but it's more of a coming-of-age story about a group of friends."

"Okay, damn," I said holding up my hands in mock surrender. "I take it all back. Maybe I'll have to give him a chance sometime."

"You should. He's amazing. But what about you, Ian? What hobbies do you have?"

***

We talked through the rest of our lunch. I was surprised by how much I enjoyed our conversation. It was a far cry from the usual meaningless small talk I'd grown to expect from Cassi. Like I'd begun to suspect, it turned out there was a real person inside Cassi after all. I had to admit, I was becoming interested in her.

But would I be able to do anything about it? The biggest problem was the fact that Cassi was happily married. I'd slept with married women before, but they had all been unhappy with their husbands. You never knew what someone's marriage was really like behind closed doors, and it was technically possible that Cassi and Joseph were having problems... but I doubted it.

The fact that Cassi and I worked together--at least occasionally--also complicated things. As a rule, I tried to stay away from sleeping with coworkers, at least in jobs I liked. Several years ago, I'd had a bad experience after a fling with a coworker turned sour. I had to quit that job ultimately, and I swore to myself that I'd be much more careful in the future.

And yet, for the rest of the shift, I couldn't stop thinking about Cassi. I wondered how she'd react if she decided to give herself over to me; how her thin body would feel under mine; how she'd react to the pleasure I could give her...

I made up my mind. I was going to try to seduce Cassi. My chances may not have been great, but I knew if I didn't try, I'd always wonder about what might have been.

Despite what pick-up-artists would have you believe, there's no surefire way of seducing a woman. But I have learned a few tricks over the years.

My first step was to hint to Cassi that I found her attractive. This can take some finesse, but if you can put the idea in a woman's head that you've noticed her--without seeming creepy--often times she'll begin to think about you in the same way. In fact, for many of my conquests, this was pretty much all it took for them to offer themselves to me. To be fair, my looks helped a lot here, but I think even a less attractive man could use this as a solid starting point.

And so, when Cassi and I were between patients, I casually quipped to her. "I know this is random, but I wanted to tell you that I almost didn't recognize you this morning. Being outside of your normal scrubs, I was like, who is this red-haired woman coming in like she belongs here?"

Cassi laughed. "Yeah, this is my first time doing Casual Friday. But the only clean scrubs I had left aren't my favorite. So, I decided--jeans it is!"

"Makes sense. For whatever it's worth, you look great in them. If you don't mind me asking, where did you get them from?"

"Why? You looking to buy some for yourself?" Cassi arched an eyebrow at me.

"Hey now, don't judge. So what if I am?" I shot back, before smiling. "But no, I just want to know so I can recommend them to my future girlfriend."

"They're Levi's. But really? Your future girlfriend?"

Cassi wasn't buying it. I sensed it was too early to be overly forward just yet. Time to let my finesse work. "It's not as crazy as it sounds. There is a specific girl I'm pursuing; she's not just hypothetical. And she's a sucker for new clothes--I figured I might surprise her with some."

"Ah, a romantic then. I wouldn't have pegged you as the type," Cassi teased me gently.

"I just like making my women happy," I shrugged, hoping Cassi caught my subtle undertone. "I appreciate your help."

"No problem," Cassi said. "Let's get this next patient--another runner's knee. Fantastic."

***

The rest of the day was uneventful, but I hoped the seed I planted in Cassi's mind was growing. I knew Cassi was going to be at the clinic with me all next week too, so I was in no hurry. Besides, I knew that if I were going to have a chance at Cassi, I'd need time to work on her first.

Over the weekend, I developed a plan. I thought it was pretty good, but time would tell.

On Monday, I was disappointed to discover that Cassi was back in her loose scrubs and no-makeup look. Still, there was no backing off for me now that I knew what lay underneath her plain exterior. I did some very light, subtle flirting to keep her mind-seed growing, but I was careful to never cross any boundaries.

At lunch, I sat near her again. After some more small talk, I sprung my plan into action.

"So, Cassi, you mentioned that you run and hike. Do you go to the gym too?"

Cassi shook her head. "Not anymore. I used to, but between work and my family, I found it was easier to just workout from home. We're signed up for a streaming exercise platform, so I just use that now."

"Oh yeah? How do you like it?" I said, keeping it casual.

"I mean, it's fine. Hard to beat the convenience factor."

"I get that. Have you ever used a personal trainer before? I mean obviously, you're a physical therapist so you don't need the exercise-planning help. But for motivation and coaching?"

"No. I never saw the need, to be honest. Especially if I have to pay for one."

Hm, this might be a harder sell than I'd hoped.

I leaned forward towards Cassi. "I don't know if you know this about me, but I do personal-training on the side. Been doing it for about ten years now. I do a session here at the clinic before opening hours with some other people from work at a discounted rate. If you want, I can give you a free trial just to see if it's something you like?"

"I mean, I dunno. I'd hate to leave home early and leave Joseph alone to get the kids ready for school. Plus, I'm used to working out at night."

"It's totally your call, no hard feelings either way. But think what you could do with the extra time in the afternoon. Don't worry about deciding now, but I'll be here all week if you want to give it a shot. Class starts at 6am and lasts 45 to 60 minutes, including warmups and cooldowns. We'll be done with enough time to shower and get ready for the day."

"I'll think about it," Cassi said, but I couldn't tell if she meant it or not. Still, I knew there was only so much I could do. The rest would be up to her.

The next morning, I woke up early to arrive at the clinic at my promised time. Even as a PTA I had been working there long enough (and was seen as reliable enough) to have my own set of keys and alarm codes. My adrenaline was pumping as I waited eagerly to see if Cassi would show.

Unfortunately, 6am came and went, with no sign of Cassi. It looked like I'd swung and missed. I went ahead and worked out alone to vent my frustration. Once finished, I used the clinic showers to clean up. I couldn't resist masturbating as I imagined revealing my cock to Cassi, her eyes going wide at the sight of it...

The workday itself was nothing special. Cassi and I worked together some more and ate lunch together again. I hadn't planned on saying anything to her about missing the morning workout, but frustration and curiosity got the better of me.

"I noticed you weren't at the workout session this morning. Decide to pass on my offer? No worries, like I said before. I was just wondering."

Cassi eyes widened and she held her hand up to her mouth. "Oh, Ian. I'm so sorry. I completely forgot about it. I got busy last night helping Dan and Michael out with their homework, and it just slipped my mind. I do want to give it a try though. Here, I'm gonna set an alarm so I don't forget this time."

"It's fine! Like I said, I was just curious. By the way, you inspired me. I picked up a Stephen King book to read--The Shining. The movie was pretty good, so I figured I'd give it a shot." I said, downplaying my excitement about Cassi's commitment.

Cassi nodded at me with a mix of approval and respect. "The Shining is great. Fair warning though, it's quite a bit different from the movie. But I think you'll like it."

"Can't wait to get into it!" I said enthusiastically, but it wasn't the book I was looking forward to.

***

Early Wednesday morning I was back at the clinic, hoping that my luck would change. I decided that if Cassi didn't show again today (and didn't have a good excuse as to why) that was probably a sign that my seduction attempt was a dud. Two misses in a row is usually pretty final.

But I needn't have worried. Just before six, a car pulled into the parking lot and Cassi emerged. She was wearing a singlet with a sports bra underneath and loose-fitting shorts; her red hair was pulled back into a pony tail. Objectively, it wasn't a sexy look at all, but it was the first time I'd seen Cassi's bare shoulders and upper chest. It made it easier for me to imagine the rest of her body.

As Cassi entered the building, I made a show of greeting her.

"Good morning sunshine! I hope you're as excited for this workout as I am!" I cheered.

"Wooo!" Cassi cheered back, before she noticed the empty room around her. "Where is everyone else?"

"They must have decided to sleep in this morning," I lied. "So, it's just you and me. But don't you worry, I'll have you so focused on the workout you won't even notice."

"I hope you don't have anything too hard planned. I'm not used to morning workouts, remember?" Cassi said, setting down her bag.

"Don't worry. I won't give you more than you can handle," I said with a devilish smile. "But let's get started. I figured we'd work on lower-body today if that sounds good? Let's go ahead with the warmup. Get into a lunge position for me," I said, as I slipped into trainer-mode.

The workout itself was over before I knew it. I kept it professional and didn't touch Cassi once, despite my overwhelming urge to do so. She took to the workout quickly, pressing her body harder with each exercise. I was legitimately impressed with how in-shape she seemed to be, despite her looking like a strong gust might blow her over. She wasn't muscular, but clearly she made good use of what little she had. I did allow myself to admire her body as it twisted and strained in the different exercises. Still not my preferred body type, but damn if she wasn't winning me over.