When dating your boss gets complicated [MF]

When I was an intern I dated my boss. I would humbly suggest not doing this. All ethical implications aside about power dynamics and consent, shit simply gets messy.

Especially considering that, at the end of the day, he was still my boss. That didn’t magically go away just because his dick had been inside of me.

So he once gave me an assignment I worked all fucking weekend on. I wasn’t allowed to bill by the hour but if I was it would have cost our client a small fortune they wouldn’t have even blinked an eye at because they have more money than God.

*BTW, I’m about to be VERY vague on what happens next for obvious legal reasons. Stay with me through this non-specific retelling and I apologize for the obvious gaps.*

Anyway, come Monday morning I was sitting on his desk. I had barely seen him all weekend because of this project but I had spent the night with him and we had fucked in his shower less than an hour ago. We had also gotten breakfast and walked in together.

My point is: He had plenty of chances to talk to me.

“Should I go ahead and format that argument?” I asked. “[My other boss] approved it.”

“Yeah, we’re actually not submitting that. We’re going with a different argument and ignore this issue.”

My mouth literally hung open. “Since when?”

“Since I made the decision.”

“…When did you make that decision?”

He stopped and sighed. “Last week. I didn’t want to tell you. I think it opens up more liabilities.”

“You let me work all night Friday and twelve hours on Sat for an argument you’re not going to use?”

*I’d like to elaborate more on why this was a complete dick move, but I can’t without being more specific about the nature of this case.*

“Viola, I’m sorry. You weren’t supposed to know until this morning. It would have been obvious we were socializing.”

“It’s a stupid decision not to include it! I’ve listened to 15 hours of audio from this arbitrator. He is going to bring it up.”

“He won’t.”

“He will.”

“Stop taking this personally and be professional.”

“It is my professional opinion that we’re going to look like idiots if we don’t bring this up. It looks like we’re hiding something.”

“I’ve done this before, V. Please relax. It won’t be a big deal.”

It was brought up and we looked like idiots. It was, in fact, brought up within the first ten minutes and I watched my boyfriend stumble over himself as he tried to explain why he had not submitted this fucking document.

All I’m saying is, I was right.

I didn’t have to say that at the time because he got his ass handed to him like a fucking child. I actually didn’t even care I had worked late anymore, I just felt bad for him. As we were walking out his boss turned to him and said, “Well done, you just lost this fucking case.”

We didn’t. It was all ok. At the time things seemed bleak though.

We were on the subway after and he couldn’t even look at me. I tried to take his hand and he pulled it away.

“Do you want to walk around the park for a little to cool down?” I asked. He was clearly too upset to work.

“No, Viola. I don’t want to walk around the fucking park. I want to go back to work because that’s what some of us have to do.”

*I had worked all weekend but thanks for the condescending rant about work ethic.*

*This was the beginning of a very, very shitty downturn.*

“How the fuck could you possibly be mad with me about this?”

He glared at me. “Don’t act like you’re not validated right now.”

I sighed. “I’d rather not be validated and have you in a good mood.”

*This was partially true, anyway.*

He lightened up a little after that but retreated into his office for the rest of the afternoon. Apart from a single email telling me I needed to double check precedent on a document, he didn’t contact me at all.

*This was rare for us. We had spent the past two months flirting nonstop in the office.*

Finally, when my day ended I walked by his office door which had been closed all day and knocked. He told me to come in but didn’t look up from his desk.

I finally lost it. “You can be mad at the situation but you can’t treat me like shit.”

“Am I not allowed to be in a bad mood?”

“Yes but sulk WITH me. Don’t shut me out. It’s my case too.”

“Hardly.”

“Jesus. What is going on?”

He finally looked up and shrugged. “I feel stupid.”

“You’re not stupid. It was a fair call.”

“No, I mean, I feel stupid for getting involved with you. It’s clouding my judgment.”

*Okie dokie, asshole.*

I turned around and left. I was so pissed off I walked 15 blocks home, stole my roommate’s wine, and collapsed into bed. He tried to call me three times. I sent one tipsy text that said, “Figure your shit out,” and then turned my phone off.

He showed up at my door an hour later.

I didn’t even say anything I just let him in and walked to pour myself more wine.

“Are you drunk?” He asked.

“A little.”

“Why?”

“Oh my boss is kind of an ass, actually. He made me work all weekend on research he was going to throw out and inexplicably got mad at me about his decision that cost us credibility.”

“Wow, he sounds like an ass.”

“You have no idea.”

“Maybe he had his reasons and feels really bad.”

“You think that’s the case?”

He nodded as he poured himself a drink. “I’ve been struggling a bit, V.”

“With me?”

“Yes but it’s not your fault.”

“What’s wrong with you?”

“I think the correct word is obsession. The first thing I thought today when I fucked up wasn’t about our client or my boss, but what you would think.”

“Oh.”

“And I can’t tell if you’re really WITH me. You’re constantly talking to other people and you seem so uninvested.”

“I’m your girlfriend…. Although today made me question that a little.”

“I’m sorry I’m not perfect and live in the real world with consequences.”

“That’s not a real apology, bro!”

We got into a fight then. He accused me of not caring and I accused him of being immature.

*He was over a decade older than me. He should have learned basic decency by this point.*

He got so mad he threw my glass against the wall.

“Either fuck me with that energy or get out!” I screamed.

“Who the hell says that?” He yelled back.

*Fair point. There is something wrong with me, but definitely more wrong with him.*

He pushed me against the wall and tore my shirt off. I started unbuttoning his but he stopped me and pinned my hands to the wall. “You don’t get that,” he said.

*I should pause here. We had fucked and fucked really hard but we had never really had angry sex before. After this, I’m pretty sure we’d just pick fights with each other so we could have angry sex like this. I’d also like to point out that we did indeed have safe words at this point.*

“Try to slap me,” he whispered.

*TBF, this was kind of his thing, so it’s a little less weird than it sounds.*

I did for a while but he kept my hands pinned to the wall. Finally I got a hand free and managed to slap him once across his face. He smiled then, grabbed my hand and dragged me to my bedroom. He threw me onto my bed and got on top.

“I’m going to fuck you,” he growled into my ear.

“Good. Use me. Take all your frustration out on me.”

“Who the actual fuck just says shit like that, Viola?” He yelled as he tore my underwear off.

*Yeah… He loved and hated my sexual experience. On one hand he’d ask for it and think it was hot but then he’d get self conscious every time I did something new in bed.*

“That’s not even that fucking weird!” I yelled back.

He stopped and looked at me then. “If you want to talk like we’re in a porn then fine, but then I’m going to fuck you like we’re in one.”

I slapped him again. “If you even can.”

*Lol, he could. This was the only thing we really got right. Our sex was insatiably good.*

He flipped me on my stomach, put his hand around my throat, and told me not to move. He went all the way inside me quickly and told me to shut up when I cried out. I clawed at the sheets and told him to go harder.

“I don’t want to hurt you,” he whispered, breaking character.

I snorted. “Oh please, don’t be a fucking bitch. I’ve been fucked harder than this.”

*Ill file that under ‘things I would not say to people today,’ but I was immature and angry at the time.*

“Fine,” he gasped as he tore the fuck into me. He spanked me once and then thrust so hard my bed hit the back wall and left a dent. “If I tell you to work all weekend, you fucking work all weekend.”

*^See this line above? This line right here? This is why you don’t fuck your subordinate. Even though sex is an absolutely wonderful release, do you see how easy it is to blur lines? Like, are we role playing or is he actually taking out his professional issues on my vagina? I think we often walked right up to that line and it got confusing.*

*And I realize this might sound like an odd rant from this account, hypocritical even, considering the shit I’ve let people do to me in bed. Hell, the shit I’ve begged people to do to me in bed. However, that dynamic has never really bled into real life power positions before and I don’t think either of us knew how to handle it.*

*I didn’t say any of that. You know what I said?*

“Fine, I’ll work whenever you want. I’ll do whatever you want.”

*Yep. That’s what I fucking said.*

“Tell me what you’d let me do.”

“I’d let you come on my face. Or better yet I’d let you come on my suit and wear it all day. Then I’d let you throw it on the floor and make me lick it off.”

He stopped only for a moment before he kept pounding into me. “Again. Who. The. Fuck. Says. That?”

*I do, asshole. Don’t ask if you don’t want dirty talk.*

“Do you want my cum inside of you?” He asked as he thrust harder and made me moan.

“I want your cum on every inch of me.”

“Fuck,” he yelled as he came. He rolled over and laid beside me. It took a few beats to catch his breath. “I’m so sorry.”

“For what?”

“You didn’t come. Just give me a minute.”

“…Anything else you want to apologize for?”

“Nope.”

On the bright side, we did fuck a lot that night, but he never really apologized.

And thus began the toxic turn of our relationship.

Source: reddit.com/r/gonewildstories/comments/vblobg/when_dating_your_boss_gets_complicated_mf

9 comments

  1. Enjoyable and your writing was great, you handled how and what info could be shared in a clear manner

  2. > I turned around and left. I was so pissed off I walked 15 blocks home, stole my roommate’s wine, and collapsed into bed.

    My apologies but after this part, all I could think about was what if the whole time you and ex-boss were arguing, your roomie was just there sitting on the couch like nothing was happening. To you and your ex-boss it was the start of “the end,” but to her “it was Tuesday.”

    Btw I still don’t like him for how he treated *future husband*, but hey you still kinda got way more from that relationship than him and a lot of sex, so in a way you “won.” Cheers to “lessons learned” and to you Ms. V!

  3. Lol, Holy fuck Viola. I gotta say that’s one of your best works so far. That is quite possibly one of the hottest and most toxic office relationships I’ve ever read about/heard/seen. I work in a similar corporate setting and I have never read such crazy tales before. Also I gotta say your dirty talk is fucking next level. I aspire to be that creative.

    >I’d let you throw it on the floor and make me lick it off.”

    Brilliant lol. I love the italic rants/lectures/advice juxtaposed with the events lol.

    I will admit I have had a somewhat toxic office corporate relationship, but not quite on the level of yours. I had an office tryst with the office bitch, who used to nitpick me constantly. Eventually…we got together somehow and it was a actually really harmonious relationship that went on for a long time. Somehow we made it work, it was one of the best relationships of my life lol. Our relationship was a lot easier for us girls due to the fact that the office was like “Oh, I’m so glad they made up now. “They’re such besties now”” Heh. Just gals being pals.

    Eagerly awaiting more office content o.o

    I work from home now for the most part now so I don’t get access to all the juicy gossip anymore.

  4. I know you’ve written extensively about this relationship. I can’t fathom sex being that good to make it worth overlooking the toxicity. You really ARE good at sex 😁

  5. Yeah. This is a hot mess, and he’s way too big of a dick, regardless if he gives good dick or not. He’s a moron.

  6. Oh well yeah… when this happens… :(

    My owner of the company / employee work fantasy doesn’t seem to hot anymore.

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