The First Time I Slept With My Boss

The First Time I Slept With My Boss

Working late took on a whole new meaning.

Blonde woman behind a bar with beer taps.Photo by Matthieu Comoy on Unsplash

Getting along with your boss has its benefits. Your work environment is more relaxed, you enjoy coming to work, and you don?t mind doing your job. When you?re happy in your place of business you?re more productive.

There?s getting along with your boss, then there?s really getting along with your boss.

When I was in my late teens, I was a waitress at a local tavern. When I started there, I wasn?t quite 18, so I wasn?t allowed to tend bar, but I could wait tables on the restaurant side. The bar and the restaurant were separated by a hallway to block the noise and rowdiness that ensued from the bar side.

If one of my tables ordered a beer, someone from the bar side had to run it to my table.

It was one of my favorite jobs I ever had. I made decent money in tips, especially once I turned 18 and could finally work the bar. We only served beer, so I didn?t have to be 21 to serve.

Image for postPhoto by Evan Dvorkin on Unsplash

The owners were an older couple and their son. The son was in his late 20s and what you would call a party guy. He was the type of dude you see in movies based on a college campus, where there?s always that one guy who never seems to graduate and is a good 5 years older than everyone else.

David was fun and outgoing, the perfect person to own and run a bar.

When the bar closed, those of us who worked there would hang out and watch movies and eat. This was back in the day when not everyone had access to satellite television, so it was a treat to be able to watch movies on-demand or pay-per-view.

David and I worked together a lot and got to be pretty good friends. He didn?t live far from the bar and oftentimes, would just have someone drop him off when he was working so he could have a few beers during and after his shift. Whoever he closed with would just drive him home.

Image for postPhoto by Alexandra Luniel on Unsplash

Vee, his mom, kept a bottle of Jack in the kitchen for cooking. One night after we closed, David and I decided we would take shots while watching horror movies.

It?s a good thing I?d seen Children of the Corn multiple times before because I would not have been able to tell you the plot that night.

Before that evening, we had flirted here and there, but nothing serious. Being honest, David was a flirt in general. It was part of his personality, so when he flirted with me, I didn?t take it seriously. I flirted back, it?s just who I am.

David is a good looking guy, in the cute, stoner guy kind of way. He?s not someone whose looks would stop you on the street, but once you?re around him and talk to him, you see it.

After we had a couple of shots, he put his arm around my shoulder and leaned in. Like a side hug.

?Hey. You know I like you, right??

?Well, yeah. I like you too, David. You?re being weird.?

?I don?t want to be weird. I just wanted you to know I like you.?

?Okay, David. I get it.?

?I don?t think you do. I?m not saying I like you as a friend. I mean, I do. But I mean, I like you more than that.?

?You?re drunk.?

?No, I?m not drunk. I?m tipsy. I just have enough courage to tell you what I?m thinking. But I know what I?m saying.?

?So, are you saying you want to do something about this, or are you just making a declaration??

He leaned in and put his hand on my face. I pressed into his hand and told him to kiss me.

Boy howdy, did he.

Image for postPhoto by Pablo Heimplatz on Unsplash

I love kissing, especially when it?s good kissing. Until then, my experiences had been fairly limited to boys who enjoyed shoving their tongues down my throat or just pecking on the lips. I believe I may have been thoroughly kissed once at that point.

This was a thorough kissing.

Every one of my senses was fired up. He pulled me into his lap, straddling him, and never broke the kiss. His hands were in my hair, rubbing my neck, down my arms, on my waist.

He slid his hands under my ass and squeezed.

Oh, man.

I could feel his length under me, growing harder by the second. Grinding my hips in circles, we were both coming undone.

I stood up long enough for him to undo his pants and to remove mine.

In what seemed to be one fluid movement, I slid back down on top of him and took every inch. Moving in tandem with our heartbeats, which felt like they were flying out of our chests, I rode him hard.

?I want you from behind, stand up.?

I got up and walked over to the pool table and bent over. Grabbing the sides of the table for support, I felt him lift my ass higher and push himself inside. I?m surprised we didn?t move the damn table.

I figured out I loved having my hair pulled.

With his hand wrapped in my hair, he came roaring soon after.

Cuddled together in a booth moments later, sleep threatened us both. I finally sat up and began getting dressed.

?I guess I should take you home before morning, huh??

?Yeah, probably a good idea. Are you good??

?Oh yeah. I?m better than good. We should definitely do this again.?

?Yes, we should. And I think you deserve a raise.?

If you liked this story, you may enjoy these other tales of first times!

The First Time I Squirted

Female ejaculation isn?t a myth, but you have to find the g-spot

The First Time I Gave A Blow Job

Summertime, best friends, and dirty dares.

Demeter DeLune is a writer forged from the fires of desire. You can join her mailing list here.


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