I [F] Blew My Boss for a Vacation

Hi! My name is Sarah, I’ve been a lurker here for a long time and decided that I should contribute as well! This is a story that happened a few years ago, but it seemed like a good one to start with.

For reference, I’m 5’2, 135 lbs. I have shoulder length blonde hair, with straight-across bangs and blue eyes. I’m 25 years old, but 22 at the time of this story.

I was about two weeks back from a vacation, and it had cost all my vacation leave for the year. My friends parents had offered to pay for all of us to stay at their rental in Florida. I really wanted to go, but had no leave left, and honestly couldn’t afford to take live without pay.

My boss at the time was an easy going, charming, pretty attractive man. He was twelve years older than me, but we got along great. We would have causal conversations, talk about life, share dirty jokes, and were sometimes a little flirty. Flirty enough for me to know that he found me attractive as well.

One afternoon, while in his office and chatting, I mentioned the vacation dilemma. The conversation had been good, and I knew I could get away with it, so at the end I added,
“Whose dick do I have to suck to get vacation around here, huh?” In an exaggerated voice and while laughing.

He laughed, and said, “I tell you what… I’ll see what I can do..”, while laughing and playing it off.

“I hope that’s a promise!”, I said, smiling as I left.

I wasn’t confident he would actually take me up on that, but it felt hot to have had the confidence to put that on the table.

Later that same day, shortly before end of day, he called me into his office. He was sat behind his desk.

“So, Sarah, about that vacation.. I may have made some arrangements.”

I smiled, and moved over to his side of the desk. “Oh.. really?” I moved close to him, and saw he already had a bulge.

He saw that I had saw, his hand brushed against it slightly.

“Well, Chris… I’m a woman of my word!”, I grinned and got on my knees, I started to pull down his pants. He realized I was serious, and with my help his dick was out.

I blew this man more enthusiastically than I had in my life. It felt dirty, naughty, and I felt powerful. I sucked him dry right there in his office.

When I was done and his load was swallowed, he told me to enjoy my vacation. I laughed and we chatted a bit, while he tidied himself up.

“Let’s do this again sometime, I think this is a good arrangement” I smiled and joked, as I left his office.

“We’ll see about that.” He grinned at me as I walked out.

And that’s the end! I hope you enjoyed – there’s more to this tale, but that was the first chapter. I hope you enjoyed! Feel free to message or chat, I’m always open to meeting new people :)

Source: reddit.com/r/gonewildstories/comments/lad6q9/i_f_blew_my_boss_for_a_vacation

19 comments

  1. As a boss… I’m half horny and half mortified. ??

    *Damn workplace harassment training jingling around in my brain… hahaha*

  2. Blowing (and fucking) my boss was such a thrill. I hope we can do it again because he’s got some grade A dick game.

  3. It’s a great story. It’s also a tragic the pitiful number of vacation days American workers get.

  4. Get a sign for his door that says “Cash, Grass, or Ass, nobody rides for free” :)

  5. As a Boss, I’d like to hear more Boss adventures!! Well written, good work! ?

  6. ? me reading this as I sit in my office. ?

    Such a great line “whose dick do I have to suck…” Another author had a great story that took a turn for the better with that exact same line. ?

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