[MF] Vegas this weekend with my [40M] boss’ daughter [22F]

Let’s try this again, since it looks like it got removed. I’m not sure where to best post, since nothing has happened just yet….but here goes.

My firm is sending three employees to a seminar this weekend in Las Vegas. Me and two other employees, a male and a female, leave tomorrow afternoon. However, since he owns the company, my boss is using the trip as part of a family vacation as well. He and his wife fly to Vegas Sunday, and they will be there through 4th of July and fly home the afternoon of the 5th. Fine.

The boss, however, has a daughter – Shelby, who was also going. She is 22, has one year of college left, and she works as a courier in our office part time, then has an internship at a local TV station as well, where she hopes to get a job as a local reporter next summer. Shelby is a nice mix of girlish and womanly, sweet and dangerous, innocent and…not, or so it seems to me. She has a cute, little build, with maybe 32b breasts and a nice ass and legs. I know she runs, but I suspect she works out too. She has a bit of a Ronda Rousey build and vibe going on, but with brown hair. We had flirted before, but it was more silliness than anything, and she would typically talk to me like she might talk to an older brother – casual and comfortable, but not really suggesting anything. Anyway, today I went into the copy room and she was there, wearing a sort of tan, tartan skirt and a white blouse, her hair in a ponytail….so business dressed, but looking fun…and cute.

“Ready for Vegas?” I asked.

“Yeah we are,” she said. “How about you?” I told her I was and asked if she’d ever been. She said she hadn’t, and neither had her friend, Madison, who was going with her. “Have you been?” She asked. I told her I’d been about ten times. “Big baller!” She said, teasing me. “I hope you don’t mind us tagging along,” she said. The girls are flying out on our flight, staying the full length of the trip, and of course, her father was paying for it. He and his wife are then flying out Sunday morning. Being that just hanging around hot girls is currency with other hot girls, I certainly did not mind. “You’ll have to show us around,” she said.

“Deal” I said, still checking her out while she continued to work at whatever she was doing for her dad. About that time he came around the corner.

“You ready to leave tomorrow?” He asked me. I again said I was. “How about you?” He asked his daughter.

“Yeah,” she nodded.

“Are you all riding together?” He asked. I didn’t know that was an option and probably just looked at him like I was dumb.

“Madison and I are taking an Uber,” Shelby said. “But James is getting us a limo from the airport to the hotel.” My boss laughed a bit at that.

“Good,” he said. “Keep those two out of jail and if they cost you any money, make them work it off.” I think it was an innocuous comment, and he said it as he grabbed some things off the copier and walked out. But I saw her grin and raise her eyebrows at me.

“That sounds fun,” she then said, still with a smirk.

“You’re trouble,” I said, taking what I had come for and leaving to my own office.

“Uh huh,” she said, smiling as I left. I thought little more of it. A few hours later, Shelby came in my office to drop off some transcripts she had picked up across the city. She dropped them on my desk, then sat on the couch in my office and began looking through a magazine.

“You want to meet us at the airport bar before we leave tomorrow?” She asked. I told her that sounded good. “What are we going to do tomorrow night?” She asked. I sort of shrugged.

“I don’t know. What do you want to do?” I said. She put the magazine down and smirked again.

“Something I have to work off,” she replied, winking at me as she broke into a grin. She stood up and continued to smile at me as she walked out of my office. I won’t lie….I was instantly hard when she said that. I did not see her the rest of the day, but I did get online and book a limo from the airport to the hotel, figuring I would surprise everyone when we landed, and show off a bit, since she had mentioned that earlier. I finished the day and went home. While packing this evening I got a text from Shelby – she has all of our numbers in case she has to find us or get us a message, etc.

“We’ll be at the airport bar around noon,” it said.

“I’ll see you there,” I said, still wary of jumping full steam ahead at my boss’ daughter. My phone warbled again.

“What happens in Vegas stays in Vegas, right?” Her next text read. I didn’t know immediately how to respond. “Yes” seemed too forward. “No” seemed like I was rejecting her.

“Why?” I replied. “What is going to happen in Vegas?” She just sent back a winking smiley, with nothing more. “See you tomorrow,” I texted.

I won’t lie. I’m interested in the possibilities here and at the same time excited that it could be super dangerous, at least to my job. At the same time, I’ll be there three days without my boss present and the girls clearly want to hang out some, so I’m down. Sorry if this wasn’t slutty enough yet, but I’ve never gone to Vegas and not hooked up with someone there, or a date I was with, so I’m sure there will be some follow up of some sort. Bear with me.

To be continued….

Source: reddit.com/r/gonewildstories/comments/6k5t6s/mf_vegas_this_weekend_with_my_40m_boss_daughter

22 comments on “[MF] Vegas this weekend with my [40M] boss’ daughter [22F]

  1. -_- stop being a whore for karma. At least include something not just background.

  2. Which do you want more your job or to get in her pants? If her dad who is your boss finds out what will he do that could effect your job?

  3. Love the setup, nothing wrong with a good teasing story. Hopefully we will get to hear about the payoff this weekend!

  4. So our plane is delayed and we are still at the airport bar. As girls will do, they have gone to the restroom together (I never get it), so I’m here with my two coworkers in this sort of loungey area in the bar. I got there a bit before noon and checked in, got through security, and made my way to here to find it was just me and the other guy going on the trip. I ordered a Crown Black and Coke and settled in. A bit later, I sort of jolt as I feel some hands on my shoulders from behind, sort of trying to shake me.

    “Vegas!!!!!!” Shouts Shelby, clearly eager to go, as she continues to try to shake me.

    “Hey!” I say, turning around. I saw her friend trailing behind her…Shelby had apparently skipped ahead when she saw us, so Madison was still approaching. And let me say….DAMN. Madison is wearing some white jean shorts over a NICE, thick, firm-looking ass, and an Ohio State tee shirt that’s fitted, gray with red print and white stripes around the sleeves, and her hair in a loose ponytail. Honestly, Madison might be SUPER fun to play with – she has a cool personality and seems down for anything. Anyway, Shelby is wearing a CUTE white romper with some blue print design on it, looking nice herself, and she proceeds to introduce Madison to me and Morgan (the other guy from work). The girls sat down on a lounger/couch to my right and I wave the waiter over.

    “Four shots of Jameson (my name is James and that’s my drink), and whatever drinks these two want. Morgan hates fun, so nothing for him,” I say.

    “Shots and a drink?” Shelby asks. “Are we starting this already?”

    “Starting?” I say. “You’re both way behind.” The girls order some sort of girl-tini, and we are ready to go. When the drinks arrive, we all take our shot (even Morgan), and I raise them up. “To Vegas honeymoons without any weddings, and to Morgan who gets neither!” Morgan sort of smirks and rolls his eyes and the girls giggle. Madison almost can’t take the shot without gagging and Shelby is ready for another one.

    The girls mention they want to go dancing tonight and asked where we should all go to dinner. Morgan says he’s going to play poker and will just grab a sandwich or something. I don’t think he’s big on “going out” per se. And he’s married, so….there’s that. Shelby called him a fun-hater and proceeded to sip her drink. I told them where I AM going, as if I didn’t care whether or not they were going with me or somewhere else. Shelby asked where it was, I told her. She asked what kind of place it was, and I just said, it’s the kind of place I like. Then, she goes, “I’m asking what I need to wear.” Funny….I hadn’t actually invited her to join me. But it’s a casual place, so I told her I was wearing shorts and a t-shirt. It’s a million degrees out there, and my shirt is from American Eagle….it will be fine. She says “cool,” and doesn’t bring it up again.

    Also, I got to chat with Madison a bit. I find out that the two met in college, but she’s actually a year older and already graduated, and works in medical sales. She mentioned a boyfriend, but Shelby sort of winced at her and goes, “Whatever….he’s a piece of shit.” Wow. But Madison laughs and says that he kind of is and she’s probably breaking up with him, but didn’t want to go through all the shit that comes with that just yet. We order another round of drinks, but no shots this time, and continue to hang out, just sort of talking about the trip and miscellaneous crap. The female co-worker showed up and so I kind of cut the flirting a bit, and we’ve been sitting here now about 2.5 hours, and we are delayed for another 30 minutes. So far, so good, I suppose.

  5. I’m going to post updates here until something wild or slutty actually happens – no need to create a new post unless it does. But we just got in and got checked in. When we got on the plane, the seats had pretty well been taken so the best we could do is get the girls the two outside seats on one row, then I got the middle seat in the row behind them. I was a bit bummed by that, but after the drink cart came by, Shelby turned around and spoke to the woman in the outside seat by me. Next thing I know, she has gotten the woman to switch seats with Madison, let Madison take Shelby’s seat, and then Shelby moved beside me.

    “Are you causing disruptions?” I ask.

    “No, I wanted to sit by you,” she says. “Now we can all talk.” We really couldn’t….she could talk to Madison, or to me, but not really all of us chat….but whatever. Morgan was in the row ahead of Madison and pretty well in his own world, while our other coworker was across the aisle from him in the middle seat. The attendant brought our drinks and the girls both had screwdrivers.

    “This is good, try it,” Shelby said. It was just a screwdriver….nothing great, but okay, so I took a sip.

    “That’s pretty weak,” I said, smirking. Shelby rolled her eyes. At one point, she got restless on the plane ride and as I was looking at a magazine, she sorta tilted her head over and laid against my arm. “I’m not that kind of guy,” I said, giving her a skeptical look. She sat up and looked back at me like she was fake-offended and goes, “You should be,” and put her head on me again, this time wrapping my right arm in a tight hug, clinging to me a few seconds before letting go and just sort of relaxing there.
    She started talking about work and asked me what kind of boss her dad was. I wasn’t about to have that conversation for a couple of reasons. So I sort of looked at her like she was a child and go, “Are you flying to Vegas with me or your dad?” She broke into a nice smile and goes, “Fair point,” and crossed her legs, leaning onto me once more. She and Madison chatted for a while and then she asked what I was doing when I got checked in. I told her I’d probably hit a bar for a while then get ready to go to dinner. She said she thought they would check out the pool. Not a lot else happened on the flight, but eventually we landed and As the girls waited for their bags, I wandered outside to the transport station and gave them the ticket for the limo and they told me it would be about ten minutes. I go back in and the girls are still waiting. Shelby says she sees her bag and pointed out this bright blue monster of a bag. Before it gets to her, I I put my hand on her waist, step close to the belt and around her, and grab it for her.

    “That was sweet,” Madison cooed. Shelby said thanks and I told them both, with Morgan and Michelle (coworker #2) let’s go. I wandered outside and everyone asks if we have a shuttle or want to get an Uber or what. The guy from the service waves us over as this giant, white, stretch escapade limo pulls up. “Oh my god!!” Madison says and the girls shriek. Morgan grins and shakes his head at me, then leans over and goes, “If you’re doing what I think you’re doing, you’d better stick with Madison.” I just sort of give him the chin up nod and tell him to just get in. We pile in and even though there is plenty of room for us all, Shelby climbs across where I am sitting, balances with one hand squarely on my things, then pivots to sit right next to me on a side seat. She was so close our thighs were touching. We carried on with small talk since the other coworkers were there, and the ride to the hotel was only 10-15 minutes. We stood in line and the girls checked in at a different station than I did, so they went upstairs first. Also, Shelby’s dad got them a suite, and I got a regular room, so we are in different parts of the hotel. Unfortunately, Morgan, Michelle, and I are in a row, while the girls are on a different floor altogether. I got checked in and a while ago my phone went off and Shelby had texted that they were going to the pool. Then it went off again:

    “If you’re not coming down here, let us know when you’re ready to go eat.” I texted back that I’d come down for a couple of drinks and we could go to dinner afterward. So here I am….made it to Vegas….heading down to grab a drink with a college girl before we all go to dinner and see where the night goes. If I have any more updates today, they’ll be brief, and probably nothing will happen tonight. We’ll see. But I’m pretty excited and hoping for the best!

  6. Cant you post the entire story at one go? I dont want to be looking through the comments for updates.

  7. Just got in and have to be awake in five hours. Will update tomorrow. No sex yet, but she’s asleep in my room and I can see her hot pink panties in the floor. Full story tomorrow.

  8. Nice! A developing story with a lot of potential!
    Hope you get to have sex with both of the college girls…

  9. Alright, guys, I can’t do a long post because I’m at meetings all morning but I promise I’ll do one this afternoon. As we speak the girls are at the pool and I’m heading there after these meetings end, but I don’t know where they will be. Last night was a great time at dinner, some gambling, a stop at two clubs, and eventually Madison getting super drunk and having to go to bed early. Shelby and I went back out and then I told her I had to get something from my room. We ended up making out in the elevator and then she fell asleep in my room. There’s a lot of detail that I have to leave out and will get to later….but I also have a dozen messages asking for updates, so this will have to do for the moment. I promise to get the longer version to you later this afternoon before we head out to dinner this evening.

  10. Hey guys. Leaving the pool now, going to my room. I’ll have an update about everything in the next hour.

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