Author's note: This story involves remorseless cheating, attempted homewrecking and impregnation coercion. If you're not into that, you're probably not going to enjoy this. Otherwise, hope you do enjoy.
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Ok so I accept cheating with your boss is both cliche and, well let's be honest, not exactly challenging. Fish in a barrel kind of thing for sure.
But that doesn't mean with a bit of creative forethought it can't be exciting and very, very satisfying. You just have to put a bit of effort into the details and build up the anticipation.
The second part was already shot for me with one of my previous bosses, James.
Within the first week of working at the agency, I had found myself, quite by design, staying late one night just with him. And sure enough, by 8:30pm, with everyone else gone, I was bent over his desk in his corner office getting my proper company induction. My small frame was getting the executive management treatment as my skirt was hiked up over my hips, my bra pulled down so it was also around my waist, my lace panties pulled to the side, and my top lying on the floor.
James was married, young by senior management standards, handsome and in good shape. Also, well endowed. So ticked my boxes. All of those attributes meant he was more than a little self-assured. Arrogant really. And I had no doubt he played around a fair bit. So being bent over his desk didn't give me much of a sense of achievement. For that I needed to be more creative. And after a few weeks, my inspiration hit me.
His wife had this routine of coming into the office and taking him out for lunch once or twice a week. It was adorable, sickeningly so. But I kinda enjoyed it. Her and I would chat when she came in. I think she liked talking to me. Helped her feel young again as I would tell her the PG version of my weekends and trips away. That life had now totally escaped her, especially as she was six months pregnant with their first kid.
On one particular visit, my evil mind crafted what would make this affair a bit more unique and satisfying, if not a bit evil.
James was running late from a meeting and Sarah, the wife, was happy enough chatting away with me. I happily indulged her slightly annoying run down on everything involved in getting ready for a kid. A nodded away as my mind went back to the prior week when her husband was eating me out on his desk late one night.
Sarah was good looking enough. Like they made a good pair. She just seemed a bit uptight and a bit posh. And you could tell she was starting to lose what would have been a reasonable figure due to the kid and all the supporting infrastructure mom bods develop.
James finally showed up and I gave him a fun little smirk that Sarah didn't notice as I kept talking to her. And that's when she told me how James' sister and her best friend had organised some baby shower this coming weekend. It was starting off at the most famous day spa in the city and carrying on with some high tea event at one of the most exclusive hotels, and then some surprise that they weren't telling her about.
The thought of her being out for the day doing baby stuff and James stuck at home, probably bored, needing something to do, made my evil mind go into overdrive. As I said goodbye to Sarah with a sickly sweet and totally fake little kiss, I had already put the bones of my scheme together.
See, while James and I had managed to have some fun over the last few weeks, we had never got to fuck outside of the office and already that had started to get a bit boring for me. It definitely seems James had a work side, a party side and then a home side. It was time to help him shake that up.
I had to be careful. You don't get to be in James's situation and living that kind of life without taking precautions. Like how he would never cum inside me. He either insisted on wearing protection or pulling out. I think he knew what kind of girl I am and how badly organised I can be, which means often forgetting to take the pill. So, I couldn't just say I should meet him at his house for fun on Sunday. No, this would have to be subtle and well crafted.
But I could still tease him about what he was going to do while his wife was out for the day. Over the next few days that's exactly what I did. First saying that he should join them, and it sounded like just his thing to him then saying how he would probably play golf first thing to a few jokes about how the guy version of a baby shower would be at a strip club. It was all laughed off with fleeting acknowledgements of the innuendo.
Casually, I slipped in that I was actually having brunch with a friend around his part of the city on the Sunday. She lived nearby and it was easy for me to get to. Like what a coincidence. Like a typical self-absorbed male, he didn't think anything of it except to say that the place we chose was pretty good and he goes there with Sarah fairly often. Perfect.
Helpfully, while he does like to keep things separate, he does allow for some overlap. This is in the form of him and I texting each other. He obviously keeps a pretty close guard on his phone under the guise of his important job.
So, it wouldn't have been a shock that I texted him Sunday morning as I noted the time. Sarah and her friends would just be getting to the day spa. He probably wasn't expecting me to ask him what he was up to or telling him my friend had had to rush off for some family emergency and I was left with two brunch meals on the way. I wasn't surprised when the speech bubble dots hung there as he thought about what to do and what to say and how dangerous this was. So, I interrupted his hesitation and texted him that it would be quick. I had plans on the other side of town.
After a few more hanging dots, I finally got a seemingly reluctant, 'oh yea sure. I guess.' Don't worry, I wasn't offended or disheartened. I also didn't have plans across town. What I did have was one of my go-to man pleasing outfits on. The kind that you could get away wearing during the day, if you had the body for it, but if you wore to the office you'd be straight over to an awkward conversation with HR.
It consisted of a tight top with a deep v neck. The full shape of my breasts were visible with my sheer bra doing its job of being subtle. The top finished well before my tight designer jeans started with their very revealing rips and tears showing the skin of my shapely, but toned legs all over. Some of the rips were tantilisingly close to some of the action parts, like you hand to be mindful with underwear choices to avoid a clash. To complete it, I was wearing my favourite and very expensive high heels. A nice gift from a former lover. But I was careful not to go overboard. It was definitely head-turning but on someone like me, who could humbly pull it off, not outrageously slutty.
About 10 minutes after we finished the texts, I spotted James before he saw me. He was wearing shorts and a light dress shirt. I did appreciate how he could make himself look hot and well-groomed effortlessly without falling into the trap of going overboard. He did, however, look uncharacteristically flustered. His eyes looking around in a slightly nervous motion. I think I had spooked him. I was on his turf.
I stood up right as he spotted me and a smile that seemed a little forced came onto his face. I wanted to give him a good look at me as he came over and I forced a hug and a kiss on the cheek. I wanted to make sure he knew what was on offer.
Then we sat down right as the waiter brought over two Bloody Mary's that I had ordered before - asking for an extra shot. "Oh sorry. I hope you don't mind a stiff drink in the morning. My friend has to start off the day with something strong." I lied with effortless ease.
