I (34/M) fucked my (45/F) boss while traveling on business last week

I travel a lot for work. From time to time my boss will accompany me on some VIP type meetings. Last week was one of those times. We were in San Fran and, to make really long story short, the hotel screwed up our booking and had us booked in one room rather than two separate rooms. After some protesting and some escalation, nothing could be done as they were 100% sold out. So we had no choice but to stay in the same room. A little awkward but we’ve worked together for several years and have been on several business trips together so not TERRIBLY weird.

So my boss is a total milf. Remember Desirae Spencer? She looks very similar to her, except the tits aren’t quite as big. When I first started working for her I totally wanted to fuck her. She dresses well – always wearing tight skirts and nice button up, with the occasional dress. And she’s really smart, which is a big turn on. Anyways…

We check into our room and she says she’s going to take a bath. This is what she does on every business trip, I later learned – check into a hotel and then take a long, relaxing bath. After just a few minutes I hear her yell out for me with a “I forgot my shampoo, can you get it out my bag for me? It’s on the blah blah blah pocket.” I get it for her, and while doing so I notice a dildo and some lube in the bag. A BIG dildo, mind you. Like, a “how does that fit in” type big. My mind starts realllllly wandering. I knock on the door and she says “just toss it in, thanks!” Not wanting to be a total perv (it’s my boss, remember) I do so and don’t try to see anything even though I SO want to.

Fast forward 20 minutes and she’s done and comes out, fully dressed in shorts and a sleeveless shirt. She puts her shampoo bag in the pocket and must’ve realized that her dildo was there because she stopped and her face got bright red. I smiled and said “if you want me to leave for awhile so you can use that, just say the words. No worries.” I can tell she feels super embarrassed so I said “hey it’s okay, we all masturbate.” She gives a little fake laugh, clearly still feeling embarrassed. We have a pretty jovial working relationship, so I don’t feel the least bit weird about joking with her. She said “I don’t know how that got in there” and then shifted the conversation elsewhere.

Fast forward a couple hours and we’re out getting a dinner as we have no plans til the meeting the following afternoon. Again, this is typical for us when we travel. We’re eating dinner, a couple glasses of wine in and she says “I cannot believe you saw that in my bag.” Don’t worry, I tell her, I didn’t think anything of it. Then it gets good… she said, “come on don’t lie… you didn’t imagine me with it?” I was really surprised so I was silent for a few seconds, but then said… “well, my mind may have wandered” with a smile. Our waiter walked over right at that moment so the conversation ended. Damn him. We’re leaving and heading back to the hotel and as we’re walking in the lobby I jokingly say “so you need some time to yourself with your friend in the bag?” She gave me a little smirk and said “no, let’s go to our room funny guy.”

As soon as we get in the room she says to me “why would I want to play with a dildo when I can play with you?” and she starts to unzip my pants. I stop her and say… wait, you’re married and you’re my boss. “Stop,” she says, “my husband hasn’t fucked me in months and I’ve been thinking about this for awhile.” Boom, that’s all I need to hear.

We start kissing, she has pulled my cock out of my jeans and starts stroking it. I’m on the big side and she said “mmm, you’re bigger in person than you are in my fantasies.” I go “what do I do to you in your fantasies” and she said “you don’t do anything – I do everything to you.” She leads me over to the bed and pushes me down on it. I pull my pants off and she proceeds to give me the best blowjob I’ve ever had. No joke. Deep throating my cock while playing with my balls for what seemed like forever. Then she’d suck on my balls while jerking me until I said “come here, let me taste you.” She sat on my face and I went to town on that pussy. She was perfectly waxed, not a hair in sight. She tasted really good. I licked her for awhile while fingering her soaking wet pussy and then she flipped around and she sucked my dick for awhile as I ate her out.

Then she said “I need this dick inside of me” and sat on it and slowly worked it in until it was all the way inside of her. I’m not gonna lie, I didn’t last long – she was riding my cock really, really hard and moaning really loudly. I loved watching her tits bounce around as she was bouncing up and down. She’s screaming and moaning pretty loudly and then says “my God your dick feels so good!” I eventually said to her “I’m gonna cum soon” and she said “fill me up, I want it inside of me” and I let loose as she was still bouncing on me really hard. She was doing that thing where she clenched her pussy as I was cumming. Oh my GOD did that feel good.

Afterwards she leaned over me, my dick still in her, and I wrapped my arms around her as she whispered in my ear “not a word of this to anyone.” I said, “don’t worry, this will be our little secret… as long as we can do it again in the morning.” She leaned up and looked at me and laughed as she said “oh, we’re doing it again before we go to sleep. We’re doing it again in the morning and we’re doing it again before we leave tomorrow. I haven’t cum like that in a long, long time. I’m going to enjoy your dick as often as I can!” And she was right. We fucked four more times between that night and the following afternoon when we checked out. Three times in the bed, one time in the shower.

We’re going on another trip next week. Not sure what will happen but I have a feeling we’ll wind up in the same room somehow again!

Source: reddit.com/r/gonewildstories/comments/538sxu/i_34m_fucked_my_45f_boss_while_traveling_on