A Complicated Relationship

Editor's note: this story contains scenes of non-consensual or reluctant sex.

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This started out as a short, straightforward cuckold story. However, the main characters, Jack and Diane, seemed to take control of the storyline, making the sex broader and darker, and Diane's cuckolding of Jack turned into ...

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A complicated relationship

I don't think I every really expected to get married, let alone to a woman with supermodel looks, who turned out to be a nymphomaniac who tried to turn me into a cuckold, then dragged me into incest with her family. After all that, I couldn't have imagined I'd still love her, but I do, though our relationship is, well, at best, complicated and few would surely ever understand it. I know I don't.

But I guess I should start back at the beginning. My name is Jack. Most people would call probably me a nerd, or a geek. I'm a lean six foot, but my arms and legs seem bigger than my body deserved, so I always look gangly, rather than athletic. My parents both died in a car accident when I was three, and I was brought up by my mother's older sister, whose children had already grown.

I was always hopeless at sports, even basketball, which otherwise I seemed to have the build for, so I never got any attention from girls at school, who always followed the sports jocks, it seemed. At home, it was like being an only child, in a family which never really wanted to have to look after any more children, and certainly not a nephew.

Perhaps it wasn't surprising, then, that I became a loner, but this suited me just fine, because I discovered I had a thing for computers, first with games, then rapidly moving on to teaching myself low-level programming. What I love about computers is that they are so ruthlessly logical, totally predictable and totally stupid, but yet can do a few simple things so unbelievably fast that most people think they are smart.

Did you know that all a computer processor can do is really to add, subtract, and to compare whether one numeric code is the same as a different one? To even to get them to do something as simple as multiplication, a human has had to work out a set of instructions to string together multiple additions to get the answer.

That's the whole challenge: to find ways of programming them to do clever things. When people say 'it's just a computer error', it's wrong. It's always the human who made the mistake, or failed to anticipate a special set of circumstances where the ruthlessly logical computer would just do what it was told, and deliver a perfectly wrong answer.

By the time I was a teenager, I could write code in many computer languages, and I could hack into no end of systems which were supposed to be private. I got a real buzz from being able to do it, though I never tried to do any harm, and looking back, I guess it just substituted for the excitement that normal kids seemed to get from sex. To start with the prospect of it, and then the first actual steps. So me, I never took any steps into sex, even when I was way past eighteen.

No, I just shrugged off the names I knew people were calling me, finished my education in computing science, and with funding from my surrogate parents, who were glad to be rid of me, I moved to Silicon Valley, and set up my own computer company, focusing on security.

It was hard at first. When I pointed out the holes in a company's system, their IT folk were defensive, and when I got past them, their bosses first reaction was that I was trying to hold them to ransom, like a Russian hacker. In the end, though, I broke through, becoming trusted and well rewarded. I took on staff, and expanded into image manipulation, you know, the sort that can create what is now called 'deep fake', where an individual's appearance can be convincingly grafted on to someone else's body in a totally different context.

And that's where this story really begins. I was twenty-four, still a virgin, though that wasn't something I thought about much, when a big, world-famous fashion house gave me a contract to create them a new app. What I was offering was a way for a customer to photograph or video themselves in a standard way, then they could select an item from the company's sales range, and the app would show them dressed in it. Perfectly.

The customer could change sizes, colours, patterns: everything. Then they could order it, confident that it would be a perfect fit when it arrived. Of course, the company also learned a lot about customer preferences as they tried things out, and ended up with an anonymised dataset of their customers' measurements, so they could avoid making styles, colors and sizes that no one wanted. That in itself must have been more than worth what they paid me.

This was how I first met Diane, when I was called to a meeting of a world-famous fashion house in Burbank. I suppose I was expecting that the meeting would be with IT guys: men and women, geeks a bit like me, so I when I'd signed in at the reception of the glitzy glass and steel lobby of the company, I was stunned when a smartly-dressed woman came to get me.

And she was not just a woman, but the most beautiful woman I had ever seen. Well, she must have been for me even to have noticed.

"Hi, you must be Jack," she said, smiling, and offering her hand for me to shake.

"Um ... yes ... I guess so," I stammered back, as I took her hand.

Her grip was firm, not one of those awful dead fish handshakes I hated. Her hair was pale brown, her eyes emerald green with shards of brown, and her face was beautifully symmetrical. I knew she must be wearing make-up - I mean, surely no one had lips quite that color - but it was so subtly applied I couldn't spot it.

She led me to a glass-fronted elevator, and as we rose through the huge atrium, she was telling me things about the company and the building. Or at least, I think she was, because my brain was busy checking out her elegant curves: firm breasts, perfect for her size, and balanced beautifully below a slim waist by the hips that had wiggled so delightfully as I followed her, and a lovely, rounded butt.

I told myself that I was just checking her out to work out how well the app would handle her, though for the first time in my life, I knew I was lying to myself. Just a bit.

She took me into a light and airy office, furnished with a large desk in pale wood, matched by a filing system in the same material, with a large-sized iMac computer on the desk, and a coffee table in the same wood, surrounded by four, obviously designer chairs.

"Please, take a seat. I just need you to sign our NDA before we get started. We already signed yours electronically, didn't we, but we're still a bit more traditional."

I sat in one of the chairs, and watched as she took some papers from the files, then walked back over to the coffee table. I'd expected her to sit, but instead, she bent over and slid the paperwork towards me.

It was a long way down to bend, and there was no way I could have avoided seeing what I saw, as the loose scoop-neck of her dress fell forward, revealing her cleavage. Well, more than cleavage, because I could see almost all of her breasts hanging in front of me, and I couldn't help trying to work out whether those were her nipples, or just the material of what could only have been the tiniest bra.

"Well, do they look acceptable, Jack?" she asked.

"Um ... well ..." I mumbled, as I hastily started to turn the pages of the agreement.

"No, not the papers, silly. My tits. I don't think I've ever known anyone stare at them quite like that, not since they first grew, anyway. Girls have them, you know. Surely you've seen some before?"

I felt a blush start as I looked up to her smiling face, then I got hotter and hotter as it spread, until I'm sure I looked like a red balloon.

"Um ... yes ... nice ..." I muttered, not wanting to admit that I really hadn't seen many this close, and desperate not to insult the woman who I guessed would finally decide if we got the contract.

"You know, Jack, you're a refreshing treat from the guys around here. I think maybe we'll get along fine - as long as you sign, of course."

She was giggling now, and rather than standing back up, she jiggled her shoulders, making her breasts dance around inside the dress, causing me to go even redder.

In the end, the agreement looked fine, and after I'd signed, she took me to a meeting room, where I was to give a presentation, followed by a demonstration of the beta version of the app. The room was full of fashionably-dressed women, none older than thirty, I guessed, and a slightly smaller number of men.

I knew that some of the women would be thought attractive, perhaps even beautiful, but none quite matched Diane, who flirted outrageously with all the men. I noticed hands touching her ass, before she pushed them away, and arms brushing across her breasts.

"Everyone - this is Jack, who, as you can see is more of a geek than a fashionista, but he's here to tell us about his new software, which, if it works, could really give us an edge over our competitors."

I did the talk, demonstrating the app by photographing Diane, and two of the other women, showing how it was then possible to see how they would look in the example dresses I had on the system. Of course, there were lots of questions, but most of them I was able to deal with easily.

"Don't the clothes in the photograph get in the way, though?" someone asked.

"Well, it would be better if the pictures were taken with just underclothes, but as long as what the person is wearing is a good fit, it still works," I replied, to a question I'd had myself in the beginning.

"Ah. Are you sure you're not just trying to collect pictures of women in their undies?" Diane asked, smiling.

Of course, this was another one of the first things we had to deal with, making sure that the photographs were never transmitted.

"No, not at all? Didn't your IT guys check it out? Anyway, what would I want with images of women in their underclothes?"

"Oh Jack! With a name like yours, as well! You'd be able to jack off to them, wouldn't you? And the way you were looking at my tits earlier, and some of the women we have as clients, I bet you'd come easily even with their bits covered."

I don't think I'd ever been so embarrassed since I let out a fart trying to do gymnastics in junior school, and my face went even redder than before. That's it, I thought: that's the end of the deal.

"Seriously, though, Jack, yes we have looked at it carefully, and we would be happy to guarantee our customers' privacy."

It turned out I was wrong. Diane agreed to work towards a big launch at a fashion show in Vegas in just a few weeks' time.

"Thank you so much," I said after Diane gave me the signed contract back in her office, and I was so pleased, I totally lost it and gave her a hug.

"Oh, I'm so sorry," I mumbled, as I realised I'd just crushed her tits against me, and whether she noticed it or not, I felt something unusual happening between my legs, and realised I'd just pressed my hardening cock into her belly.

"Don't worry, I was beginning to think I'd lost it, darling," she smiled back, brushing her hand across the front of my pants, sending my face red again. "I'll send the meeting invitations for the follow-up electronically."

I flew back home elated, but deeply disturbed. Elated because the contract would really put my little company on the map. Disturbed, because of the effect Diane had had on me. I'd never let girls trouble me, and I knew that there was no way a nerd like me could get anywhere with a beauty like her. At best, she'd flirt with me, the way she had with her team, but nothing good could come from it. She'd get what amusement she could from me, then spit me back out.

The trouble was, I just couldn't get the image of her tits out of my mind, the feel of them squashed against my chest, nor her touch against my traitor of a cock. And she'd planted the idea of jacking off in my mind, so after tossing and turning in bed thinking about her, that was what I did, imagining what those breasts were like.

Over the next few weeks, I had numerous visits back to the Company. Diane's behaviour was even more outrageous, though her team seemed to take it in their stride.

"You know, Jack, I really think we should do a proper comparison between a fully clothed woman, and one in just underclothes. You said it was better, and I'd like to know just how much. I'm game, who else is up for it?" Diane said at the third meeting, taking me by surprise.

It wasn't just her words that took me by surprise, but the way she was undoing her blouse, which she threw on the conference table, then undid her skirt, and let it drop to the floor, leaving her stood in a white lacy bra and panties. I groaned to myself as I noticed the dark circles of her nipples showing through her bra, and what looked like a patch of hair through her panties.

While I groaned, the rest of the team cheered, and even more so when one of the other women, Julie, did the same. Her tits might have been bigger, but it was Diane whose body mesmerised me.

"Hey, Jack-off Jack! Wake up! This isn't just for your enjoyment, let's run some tests," Diane said, looking me straight in the eye and smiling, making me blush again, and hope that the bulge in my pants wasn't too obvious.

It wasn't just the sight of her almost naked body that turned me on, but the way she still kept flirting with everyone, brushing against them, and letting them touch her as they joked about how, if they recommended this, potentially hundreds of women would be photographing themselves, and what a shame it was they wouldn't be able to see.

Then it hit me. From the way most of the men were looking at Diane: they'd fucked her! Once I'd seen it, I knew from the look in their eyes that they knew exactly what was under Diane's skimpy underwear. The strange thing was that some of the women seemed to have the same look as well, Julie certainly. I'd been pretty sure a couple of the men were gay, though, and I couldn't quite work that out.

Of course, it was no real surprise when the images from the app, and the fittings it suggested, were just that bit better when in the original photograph the woman was wearing only their underwear, but I could see that with a few tweaks to the program, I could make it even better, making full use of the additional body information that had been hidden.

When I got home that night, my mind was full of images of Diane's body, and of her being fucked by the men who worked for her. I wanted to be one of them, of course, but what baffled me was that I also wanted just to watch her being violated by the others. And, once more, I lived up to Diane's name for me as I jacked off, imagining her fucking.

I made the adjustments, and customised the look and feel of the app to meet the needs of the fashion house, and then the time came for a final demonstration to senior management, who would then decide whether to launch the product.

It went fabulously. Diane took the lead, dressed only in a different set of underwear, seeming to have no embarrassment at being that way in front of her bosses. I thought I saw that look again from one or two, which probably explained it. The biggest surprise, though, was when one of the vice presidents stripped down to her underclothes and tested the system for herself.

They signed the deal, and against my better judgement, Diane persuaded me to join the whole team in going to a bar to celebrate. I didn't drink much, and I hated the sort of idiotic small talk that goes on at parties and bars, so I just sat in a corner and tried to keep to myself, just watching Diane flirting.

The more I watched, the more confused my feelings became. Part of me despised her, the same way I had the airhead cheerleaders at college, whose only interest seemed to be getting fucked by the best players on the team, and clearly Diana had been fucked by most of the men. That was even clearer to me now.

The trouble was that part of me wanted to break my virginity by fucking her myself, but even more disturbing was the fact that I was equally keen to watch her get fucked by her work colleagues. She was laughing and joking with the team, touching their arms or putting hers around their shoulders, and there were arms going around her as well, usually straying down to run over her gorgeous ass.

Given her show in underwear, I now knew exactly how gorgeous that ass was, and part of me wanted one of the guys to lift her skirt to reveal it. Worst of all, I wanted them all to tear her clothes off, bend her over one of the tables, and fuck her, one after the other.

Lost in my own, shocking mental images, I hadn't noticed that most of the team had drifted off, until Diane sat down opposite me.

"Finished flirting, then? I'm surprised you haven't gone off with one of the guys; or perhaps several of them."

"That's what I like about you, Jack. I can see that you're attracted to me, but unlike all of the others, you aren't constantly pawing me, trying to get in my panties."

"They have been in them, though, haven't they? I've been sat here thinking up my new app: 'have they fucked yet?'. It just needs a picture of the two people's faces, and it will give you an answer. From the look on your faces, I know you've fucked most of the men in your team. I've just got to perfect it, as I was sure a couple of the guys were gay."

"Oh, they've fucked me as well, Jack. I let them use the back door so they felt right at home." Diane replied, smiling, and bending forward to let me see down the front of her blouse.

"Back door? I don't know what you mean."

"Up the ass, darling, up the ass."

Whilst Diane was now laughing out loud, I was going red again.

"I love the way you're so innocent, Jack. Don't tell me you've never used a woman's asshole?"

"Um ... no," I muttered, getting redder and more embarrassed.

"Oh shit, I didn't mean to embarrass you. And you're wrong about the women as well - I've fucked most of them one time or another."

Oh God, a picture of Diane and Julie, licking each other's pussies sprang into my mind, making my cock get stiffer, even as it disgusted me.

"Wouldn't you have liked to watch? Isn't watching two women together every man's fantasy?"

As she spoke, she moved her hand under the table, and I gasped in shock as I felt her touch my cock through my pants, and I knew she'd take its hardness as confirmation of what she'd said.

"Leave me alone! You're just a fucking slut, Diane. I'm going to catch my flight. Just email me details of the launch. I suppose I'll have to see you then."

I stormed out of the bar, leaving Diane speechless, her mouth open. I guessed that no one had ever turned down her advances before. I had time to remember why on the flight home, as I kept thinking about her perfect body, her prefect tits barely hidden under the different bras I'd seen her in, her curvaceous body, and the promise of even greater delights between her legs. More than anything, though, I couldn't stop thinking about her with a guy's cock up her ass, or rolling around on a bed with another woman.

Damn it, I lived up to her nickname for me again, as soon as I got home and in bed.

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And it just got worse each day over the couple of weeks until the Las Vegas launch. I'd never cared much about sex before, but now it totally obsessed me. I didn't get it, nor the confusing emotions churning around inside me. I despised Diane for being such a slut, yet I wanted to fuck her myself. Was it just to punish myself for lusting after her, because I burned to watch her fucking, men and women, in every depraved combination that my twisted brain came up with?