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.

Sometimes I have baller moments [FM]

There is no reason to write this story other than the fact that it was one of the few moments in my life I was actually cool.

*I promise I am pretty awkward in real life.*

I had a crush on a dude I went to law school with, but he had a girlfriend so I didn’t think about it much. We’d very casually flirt but we’re both careful not to cross any lines and never said anything I appropriate.

One night we were out and I met his girlfriend and she was FUCKING HORRIBLE. She straight up slut shamed me in a group of people.

I was like, “Hi, I’m V.”

She looks me up and down, glares at me, and then says, “I know who you are.”

*Bitch, what? She had no reason to dislike me.*

NGL, I am an adult who didn’t exactly have a desire to unpack whatever insecurity she was harboring so I steered clear of her for most of the evening.

At one point we unfortunately all landed at the same table and she stares at me with undeniable hatred. I’m almost impressed by her commitment to this glare.

The first time my boss fucked me in his office [FM]

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.

My girlfriend had a very weird branding kink [FF]

*I should note the person in this story is no longer the 19 year old agent of chaos I dated. However, our relationship was toxic and sometimes our fights are worth including.*

Yes, I had a girlfriend who was very into degradation. She was weirdly obsessed with “branding” which scared the hell out of me… SHE scared the hell out of me. After this story she got pretty creative with temporary ways of writing on me.

*Once she put her underwear in my mouth and spelled her name on my back with hot wax. That’s not really relevant to THIS story but I wanted y’all to have that visual.*

Anyway, it started small. She would write in pen and draw temporary tattoos on my arm. Sometimes she’d add her name to them, which was complicated because I wasn’t “out” and would have to cover them up to avoid questions.

Things escalated once because we got into a fight. I remember this fight because it was so fucking absurd.

She walked in and asked what I was doing. When I responded I was applying for the Peace Corps she flipped fucking shit, even though I had been very upfront about my plans after graduation since I met her.

It’s always the ones you don’t expect [MF]

One of my best guy friends is a precious soul. Objectively he’s attractive but I’m just not attracted to him. For what it’s worth, I think he’d say the same thing about me. We once slept in the same bed when we were both single and there was absolutely no tension at all. My husband almost laughed when someone asked if he got jealous of how close I am with this person because the chemistry is not there.

*I know movies tell you that’s not the case and one person is always secretly pining, but sometimes there is simply nothing there. We’ve known each other for over a decade and have never even cuddled.*

Anyway, he’s such a precious spirit that when we were single I always worried about his lack of game. He hated dating apps and never seemed to put much effort into meeting people when we went out. He made plenty of friends though. Like we didn’t have to pay to drink at one of the bars we frequented because the owner found him so charming and just wanted us to hang with her.

When WE got offered $ for sex [MF]

This story is fucking weird. Keep in mind we were in a very interesting place with a slightly weird culture. Certain things got lost in translation, but I swear I just often got into fucking weird situations with this person. We were both reckless so we did things that often put us in the line of fire, but I swear he just attracted trouble.

Anyway, I was once at a hotel bar with this guy I was dating. We were flirting pretty openly and kept making each other laugh. We were actually being so goofy it was almost a scene.

We were celebrating this article I wrote so I was pretty dolled up. It wasn’t anything too crazy but I was in a black dress and heels. It may or may not have been low cut. He was in a suit.

*I’m not sure if this is relevant, but it is possibly worth noting because shit gets weird.*

Also, my date was hella hot. Women openly hit on him in front of me and we often got stared at. It’s a fun reality of being with a super hot person- it makes people weird.

You’ve heard of roadhead, but have you ever jerked off a pilot in the air? [FM]

Because I have.

I had a dear friend who was a pilot. Tbh, most of our friendship was platonic except this one moment.

We knew each other for years. I never really saw him sexually because when I met him he was dating my best friend.

*Then she fucked my boyfriend so we stopped being best friends and he stopped dating her. That’s another story.*

The Pilot and I continued to hang out after they broke up. He lived in my hometown so I only saw him a few times a year when I was at college, but we always saw each other when I came home. Weirdly enough, he was actually friends with my dad (even with the 30 year age difference) so he was at my house a lot.

Once the three of us were having dinner and my dad was like, “Why don’t you just date him?” when my pilot friend was in the next room.

*My dad was constantly begging me to date folks in my hometown.*

“I am DEFINITELY not going to date him.”

“Why?” My dad asked.

When I dressed up as a cheerleader and it was an epic fail [FM]

Writing this was very cringe. I still turn red when I think about it.

Sometimes I’m bad at sex, y’all.

I’m not very good at role play. Theoretically I guess rough sex is role play in a way, but I have a hard time playing actual characters.

For someone who is epically bad at this, I’ve had a weird amount of role play sex. It always seems like a good idea at the time.

So a guy once asked to fuck me in cheerleader uniform for his birthday and I agreed to try. I had to order one from Amazon because I was too embarrassed to ask my roommate who was an actual cheerleader to borrow her uniform.

So if I’m going to do this, I’m going to do it right. I wear pigtails, get knee high socks, and put on the sluttiest uniform I could find online. Physically, I have nailed this.

The problem? I don’t really know how to act like a cheerleader. You’re reading the words of a woman who was once an emo chess nerd.

My simple friend [F]

I had a friend in college who was not the brightest. She was sweet, but very simple and a tad slutty.

For example one day we were all chilling and I made some joke about how I swallow. She looks at me with complete sincerity and says, “Well, that’s good for health reasons, right?”

I wait for her to elaborate and finally announce I need a judge’s ruling.

“Well, because semen is really good for your health. It makes you skinny and cures hangovers.”

“Really?” I ask.

“Yeah and it helps prevent wrinkles if it’s on your face.”

“Hey honey… Who told you this?”

*We all know who told her though, don’t we?*

She had an asshole boyfriend who was also fucking dumb as dirt. He was a flat earther who didn’t know who the vice president was.

Anyway, I kindly explain I think there might be an element of manipulation here and she does not get it. She stares at me blankly and tries to explain that the reason her skin is so soft and wrinkle free is because her boyfriend is nice enough to smear his cum on it. She is dead serious about this.

My best friend indirectly got me laid [FM]

My best friend is one of the few souls on earth who knows my username so she’ll read this. I obviously had to change details, but y’all should get the gist.

I’ve talked about my best friend before, but it’s hard to adequately capture the depths of our relationship. She is tragically very straight, but we love each other like sisters.

She is my person.

Weirdly enough, we actually met because we were both casually hooking up with the same guy. He was once like, “I know this is weird but I’m also seeing this girl who reminds me a lot of you and I just think y’all would get along.”

We did. I’ve never clicked with ANYONE as quickly as I did with her. We moved in together within a month of meeting each other and have been inseparable ever since.

*Yes we have made out many times but I promise there is nothing else there. She is so straight she doesn’t like her own vagina.*

There was a magical time in life when we lived together when we were both single and we SLAYED! Before I had GWS, I had her. Every time we fucked we’d tell each other every single detail. She was my muse.