A night with my boss (26m)


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After working such long hours most weeks, it was all the time nice when I was able to take a company trip and have the business provide me with some R&R at the hotel spa. Most meetings we had a group of us go to present ideas to fellow colleagues out of state and we would all the time try to make it as enjoyable as efficient after hours to make up for the amount of time spent preparing for these meetings. One of my coworkers, we’ll call her Carly 32F, was the manager on this particular trip and she wasn’t a regular on these trips because she had 2 kids and was either pregnant or babysitting and wasn’t able to come. Well, her husband was taking care of the kids and she was loving every second of it. The minute those meetings ended, she told the entire group, which was 3 of us and her made 4, that we were heading out for drinks. One of our colleagues had to back out cause they weren’t feeling great, but myself, Carly, and another school Jim (28 m) were game, and we headed out.

We all got shots to begin out with and we were having a great time. Carly was really loving it up, she had multiple shots and did some karaoke and bombed incredibly, but it was fun to watch. Jim and I congratulated her and said maybe she should take it easy cause we have meetings tomorrow still. She laughed and said they were in the afternoon and ordered another shot. She explained how for the last 2 years her kids and husband made it hard to go out and have drinks and dance like this and while the business was paying for it, she was going to take benefit. Jim was feeling the effects and said he was going to take a cab back and that I should make sure she gets back in one piece.

Carly came back and noticed that Jim was gone and said fuck Jim let’s do another shot. So we did and then we got to talking. Carly wanted to know what we did while we were ok these trips cause everyone all the time talked glowingly around the water cooler, but when she came around, the talk was all the time how wonderful the meetings were and she knew that was bullshit. With the alcohol and the fact we were alone, I just kinda blurted out, well the guys and I we usually talk about the girls we hookup with while we’re out here. She looks intrigued and asks if that’s why you’re all the time so willing to go. I don’t hesitate, as maybe I should’ve, but I go yeah, there’s some crazy horny girls who love hooking up with businessmen on the road. She asks what type of girls I hook up with and I responded that many of them were school girls usually. She looks at me and I’m feeling like maybe I shared too much and says, well you have any plans with anyone yet. I’m taken a back but reply no I don’t. The silence between responses was deafening, but then she utters I’m glad to hear that, cause I don’t like to distribute. I was stunned, but at this point my cock took over and I blurted out, why don’t we get a cab.

We call a cab and begin to take the 10 ride back to our hotel. The minute we get in the cab, she grabs me in close and starts to kiss me. I was a little shocked, but I wasn’t gonna pass this up. She was wearing a pencil skirt and my hands flew up her thigh and I rubbed her pussy through her panties and I could already feel she was dripping. She told me how her and her husband haven’t fucked much since the kids were born and she was soo horny always. I slide her panties over a little and slide 2 fingers in with little to no resistance. She’s so wet and still tight. I can’t believe her husband wouldn’t want to fuck this tight pussy. She but my lip as I thrusted my fingers in her. She felt my stiff cock through my pants and that her husband hadn’t gotten this hard for her in 4 years. I whispered in her ear that she was going to feel what a real man does inside her. Her pussy tightened and she came all over my fingers. The cab had arrived at our hotel. I took my fingers out and she grabbed them and stuck them all the way down her throat and thrusted my hand back and forth. She got out of the cab and adjuster her skirt. I threw a $50 at the cabbie and he told me to catch up to her before she finds someone else to fuck. I push through the revolving doors, I think to myself, should I really be doing this?

To be continued..

NSFW: yes


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