Oh man. This monthly contest is my jam.
First off, I am begging you PLEASE do not fuck your intern. Please do not date your subordinate at all. It’s all fun and games until someone gets heartbroken, harassed, and/or sued. Really. Do not do it.
However, when I was an intern, I did indeed fuck my boss. We ended up hating each other, but there was a magical window of time when we were fucking each other while I worked for him. Our office became a far more interesting place.
He understandably had some reservations about this relationship. If we had met under different circumstances we absolutely would have dated in a second because we had sexual chemistry, but the realities of dating my boss who was over a decade older than me didn’t quite hit me when I was in my early 20s.
It took us FOREVER to fuck and when we finally did he made it clear we would NEVER fool around in the office.
*Lolololol.*
I used this rule to play… and for a while that’s all it was.
Once we were in a meeting and he texted me, “I want you on this table” I responded by telling him I desperately needed his dick in my mouth and that I would let him put me to my knees and fuck my mouth so hard I cry.
That was a fun one to watch him receive. He shuddered in the middle of the meeting and had to close his eyes. He started to compose himself so I sent another.
I told him I was so wet I was going to ruin my underwear and I was craving him inside of me. He looked over and I sucked on one of my fingers while he stared like he was in pain.
*He was. I look good in a suit.*
When the meeting ended he asked me to stay behind so we can go over how we would divide up the legal research left on this brief. After everyone trickled out I turned and smiled at him. “Are we actually going to discuss this brief?”
“Hell no, I just couldn’t stand up.”
I laughed. “Are you taking me to dinner tonight?”
“That depends, are you going to let me fuck you before or after?”
I unbuttoned my top slightly and leaned back as I smiled. He put both his palms on the table and looked at me like he was about to die. “Oh my god, V. You’re going to kill me.”
“I can suck you off in your office.”
“We can’t.”
“Alright then I’m going to go get myself off in the bathroom.”
“Holy shit. You do that?”
I stood up and leaned over to put my hands on the desk. “The first time I did it was after you marked up my brief and leaned over my desk. I thought about what it would have been like to bend over that desk and let you spank me for every mistake I made. The second time I did it was when we were in the elevator and you touched my blazer and told me you liked it. I thought about you fucking me in ONLY that blazer. Finally, this morning I thought about you fucking me in your office. When I was being too loud you stuffed my underwear in my mouth and told me you’d spank me if I didn’t shut up… So yeah, I do *that.*”
“Mother fucker,” he whispered as he put his head to the desk in agony. “I’ve never met a girl who talks like you.”
“You’ve never met a girl who fucks like me. We’ve barely hit the surface.”
He groaned. “I haven’t gotten randomly hard like this since I was a teenager. I have to fuck you. Let’s go to lunch.”
“It’s 10:30.”
“It’s an early lunch.”
“You have to be in court in an hour.”
“I can’t go like this.”
“Then go jerk off in the bathroom.”
“Go to my office.”
“Is that an order?”
“Yes, because if you continue to stand there I can’t even walk down the hall. Now go and wait for me.”
I did. I sat in his chair and waited for him as I unbuttoned my shirt. When he entered his eyes got wide as he slammed the door behind him quickly. “Jesus V! What if someone else had walked in?”
“Lucky them? Besides, I’m about to get on my knees and suck your dick. I think my shirt is the least of your concern.”
He sank onto his couch. “This is a horrible, horrible idea.”
“Want me to leave?”
“God no, but you have to. I’m sorry.”
I buttoned my shirt and got up to leave. “It’s cool. I’m going to go think of you while I get off in my office.” I stood over him and put a hand to his cheek. “You buying me dinner?”
“Slap me.”
*He’s one of THOSE.*
I slapped him and he nodded his head.
This went on for some time. I’d mess with him, he’d mess with me, we’d hang out after work, fuck each other silly, and then we’d drink wine and listen to Pink Floyd. It was a fun time.
Once we had a big win on a case we had worked really hard on. We weren’t even out of the building we were visiting before he grabbed my ass. That subway ride back was torture. We started making out and became that couple half the car hated.
*Side note: all lawyers fuck after a big win, right? This is a universal truth.*
“You were fucking sexy earlier, by the way,” he said as he broke away to kiss my neck.
“You’re brilliant,” I moaned.
“Say that again.”
I laughed and put my mouth to his ear and whispered, “You’re fucking brilliant.”
*Alright. I’m stopping this story because even though we are immensely happy in this scene, he was an ass. He was a brilliant ass, but my ass is not only better but I am more brilliant than him. We would later hate each other over it and engage in behavior that would ensure mutual destruction.*
*In this moment though? Holy shit, we were electric. It’s actually been pretty rare I’ve had this much raw passion with someone.*
We stood up and he pushed me against the door to kiss me. I almost fell back when they swung open at our stop. He pressed me against the station wall and we kept making out.
“We have to stop,” he finally said as I bit his lip. “Someone might see. Let’s go to my place.”
“You have a meeting in an hour,” I breathed.
“Why do you know my schedule. Are you stalking me around the office?”
“No asshole, you’re just my boss.”
He stopped then and stepped back. “I am, aren’t I?”
“Don’t get weird.”
“It’s work hours. We have to stop until the day ends.”
I whined and gave him a pleading look but conceded. “Fine.”
We got back to the office and acted relatively normal as we walked through the halls. When we got to his office door I smiled and told him I’d see him later.
He nodded and was about to leave but mumbled, “Fuck it,” before grabbing my hand and pulling me in.
*His door did not have a lock. We were idiots.*
He immediately shut the door and pulled me into him. He put his hands on my face when we started kissing. It was sweet for a couple of seconds until he steered me to his desk and then pushed me back so I was sitting on it. He wrapped my legs around him.
*Holy shit.*
He pushed my skirt up as I reached to unbuckle his belt.
“I have to take these off,” I whispered as I reached for my underwear.
This dude shakes his head, reaches both hands between my legs, and rips my underwear in half.
*Good God.*
I unzipped his pants and started pushing his pants down. He put his arm around me and pushed me to the edge of the desk before he reached to push himself inside of me.
I moaned at first, but he threw a hand over my mouth and shook his head. “We have to be quiet,” he whispered.
“Fuck,” I squeaked.
I was hella tight to the point it was almost painful but also so, so hot.
The first time he thrust into me he pulled me into him and I bit his neck to keep from screaming. He did as also having a very difficult time.
*There is no reason for me to add this part but I’m going to anyway…*
He asked me to be his fucking girlfriend at this point. I hadn’t actually been someone’s girlfriend in years. Perhaps it was his dick inside of me, but I agreed.
“Really?” He breathed as he stared into my eyes .
“Yes! But please fuck me right now.”
He went hard then. He wrapped my hair around his hand and pulled me toward him as he slammed into me over and over again. He went so hard I started shaking and he put his hand back over my mouth as I moaned.
“You can turn me around,” I whispered.
“Fuck no,” he moaned.
*He was also one of THOSE.*
“Ok, but I’m about to come,” I cried. I was literally crying because sex is actually really hard when you’re naturally loud and have to stay quiet.
“Good because I am too.”
I clawed at his back through his blazer and pulled him close one more time as I came around him.
I could barely speak but I threw my head back and quietly gasped as I erupted. He came then too and kissed my neck as he whispered my name and then pushed me back on the desk.
Friends, that’s how I became my boss’s fucking girlfriend. There were absolutely no complications at all.
Source: reddit.com/r/gonewildstories/comments/v8xuhl/the_first_time_my_boss_fucked_me_in_his_office_fm
Oh golly. Office stories. My favourite.
>The first time he thrust into me he pulled me into him and I bit his neck to keep from screaming. He did as also having a very difficult time.
Holy fuck that is steamy. I have a wicked mental image in my mind of you two. The suits…. oh lordy. How am I gonna sleep after that story V. Thanks for that lol.
>Friends, that’s how I became my boss’s fucking girlfriend. There were absolutely no complications at all.
Also somewhat amusing knowing the context of this relationship since I’ve read all of your stories. lol.
“There were absolutely no complications at all.”
Reader, there were many complications.
> First off, I am begging you PLEASE do not fuck your intern.
“Challenge accepted”
> Really. Do not do it.
“Challenge forfeited”
> It took us FOREVER to fuck and when we finally did he made it clear we would NEVER fool around in the office.
“It’s gonna be legen….wait for it…dary!”
> He was. I look good in a suit.
“Nothing suits me like a suit”
> “You’ve never met a girl who fucks like me. We’ve barely hit the surface.”
*High five* like an actual high five cause this was *chefs kiss*
> Once we had a big win on a case we had worked really hard on.
“Lawyered!”
> I whined and gave him a pleading look but conceded. “Fine.”
“Whenever I’m sad, I stop being sad and be awesome instead.”
> He asked me to be his fucking girlfriend at this point.
“Classic Schmosby”
> I could barely speak but I threw my head back and quietly gasped as I erupted. He came then too and kissed my neck as he whispered my name and then pushed me back on the desk.
“I said a bang bang, bangity bang. I said bang bang, bangity bang (bang bang bang)”
> Friends, that’s how I became my boss’s fucking girlfriend.
So HIBMBFG, it’s a bit cumbersome but ok….
And the best part is that the ending of this “series” is quite bad too!
Good luck on the monthly contest! Cheers Ms. V!
Ahhh I’ve been waiting for this story for so long.
This must have been super hard to write up considering how much you hate him now?
For me, it’s the way you describe yourself in this one and any other stories about him. Unbuttoning your work shirt while waiting in his chair, the texts, the dirty talk and the confidence of yourself. Naughty, confident lawyer V (and of course chess V) > all the other roles you’ve described.
As an owner of a company, I can’t lie, I want this kinda spice just once. It sounds too fun. (Maybe I just powerful women in office wear?)
When your book is published (yes when, not if) will these stories appear in chronological order or in some other order?
Also if eventually you come out of the closet as an author how obvious is it going to be who this former boss boyfriend is?
Winner winner chicken dinner 🥇
!updateme