Fantasy Fulfilled Work Trip

I had an upcoming work trip scheduled. I was stoked for it. Not the work part. but because the office manager was also going on this trip. Not just any office manager. For this story we will call her Kelly. This person is like Donna from the show Suits, if you watched it.. you catch my drift. All seeing and all knowing. She knows the perfect things to say in every scenario. Aside from the innate ability to do her job, she is a show stopper. Sometimes she will wear this low cut white top... one of those shirts that you have to remind yourself time and time again to look her in her eyes or you might get caught with hard on in the office imagining what she may look like without the barrier of a shirt and that would be embarrassing. Sometimes I get caught daydreaming about seeing those huge breasts wrapped around my... well we will get there.

A little about myself - I'm 38 years old with an average build. I try and work out to stay in shape. I'm currently caught in fantasies involving the the office manager and now we're going on this trip... well it hasn't done anything to help stop the rush of blood making my dick hard as a rock.

I'm telling you.. some days when I get ready to leave the office I have to wait around for all the other agents to leave for the day and satisfy my needs. I imagine she is right there under my desk bobbing up and down on my hard cock. She is looking me straight in the eyes and enjoying every second. While she is doing this she is moaning and humming which makes me unable to hold back. I dream she is capable of taking me all the way down her throat. She can go from the tip of my dick all the way to the base and as I get ready to shoot my load, after the first spurt in her mouth, she takes me all the way down into her throat and stays there while I cum down her throat. She swallows it all and pulls off. As she catches her breath, she goes back to make sure that I'm entirely cleaned off. She goes all the way down and takes the tip of her tongue and presses up on the underside of my hard cock while backing off to get all of my load to satisfy her desire.

But what am I thinking? There's no way someone like her would give me the time of day to satiate my wants and desires. Besides what if something happened and she told someone? That would be the end of my career and my life. I have to maintain control on this trip. I know it will be difficult but I'm sure she won't wear that top and that everything will remain professional.

The days leading up to this trip were very busy. It was arranged that we would fly into the airport and we would be each getting our own rental cars when we landed. I was excited and nervous at the same time.

The days before the trip were a blur between work, the gym and other preparations. By the time I got to the airport and met up with Kelly, she was her normal beautiful self. Except for the fact she was wearing that one shirt she couldn't have worn. My golly. Did she look ever sexy in the white low cut top. This is off to a rough start for me trying to remain in control.Since I had been so busy this week I never got the chance to satisfy my own needs and already felt blood flowing down to my dick. Not off to a great start.

I walked up to her and said, Good morning! She turned around and gave me a hug and returned the sentiment. When we separated she was blushed. She apologized for hugging me, saying she's never been on a work trip, and that she's a hugger in her personal life and she shouldn't have done that.

Gosh this trip is going to be a long one. That hug really didn't help me. It's the first time I really got to feel her chest up close. Thoughts are starting to go no where good. It didn't help that I was wearing my gym jogger pants. Why did I do this to myself.

We sat down as we waited for our flight to begin boarding. I tried to take my mind out of the gutter. These joggers won't help hide anything. We made small talk and discussed the trip. We talked about places to eat and sights to see in the area. We talked about how we have both been going to the gym lately. I shared that I had done leg day earlier this morning and I was super sore. She is extremely easy to talk to.

The next couple of hours weren't interesting much at all. We boarded the long flight and were sitting next to each other. Since she hadn't flown before, I let her have the window seat. After we were in the air for a little while, she decided to take a nap and I turned on a movie on my iPad.

As she laid up against the window I couldn't help but notice how her top had gotten pulled tighter and downwards. Fuck. I was staring and imagining being able to grab and caress her chest. I felt the blood start rushing to my dick. I was getting harder and harder until I was fully erect. Again, why did I wear these jogger pants. They leave little to the imagination. My dick print is crystal clear.

As I reach down to adjust myself I stroked my hard cock a few times and push it down to try and hide it. I look over at Kelly laying there and she appears to be asleep. Her face is as blushed as it was after our hug earlier. No way she caught me? Did she? Immediately I stress out. I go back to my movie and hope that she didn't see me staring at her or grabbing my hard dick in my pants.

She kind of rolls over and is now leaning kind of up against me. This view of her chest does not disappoint. I can only imagine grabbing and squeezing her breasts. As she was changing her position, her arms are now on my side instead of the windows. Her hand lands on my thigh. Great. With this view my rock hard cock is going down my right leg and her hand is terribly close to touching it. Half of me wants to grab her hand and place it in my cock. I can't do that. I sit there for a few minutes when she begins to rustle around a little bit more and it's like the gods are reading my mind. Her hand lands. Right. On. Top. Of my hard on in my pants. Gawd was I in heaven. This view, her hand on my dick. I didn't know what to do.

Suddenly the stewardess is walking down the aisle with a tray of some drinks when we hit turbulence. Yep. It spills. Right on top of my lap. Instantly Kelly "wakes" up if she was ever asleep. Was she I wonder? My hard on immediately goes down, And the stewardess begins apologizing and grabs us some towels.

We wipe ourselves up and thankfully it was just waters. We go on about the flight when Kelly looks at me and asks if I liked the view. I was flabbergasted. Did I get caught? I answer with yes it is quite the view And how much I enjoyed it. Unsure if she was talking about out the window or her quite visible chest when she was asleep. Was that a smirk on her face?

When we landed at the airport, we began looking for the rental car check in booths. When we finally found it, there was quite the line. As we get in line we hear arguing and everyone seemed on edge. The worker puts out a sign that says they are out of cars at the moment. Most people walk away.

I know we already had reservations for our vehicles, so I walk up to the desk and ask if the sign included reservations. The attendant stated that it didn't, just no extra cars for folks without reservations. I was relieved. We start the check in process when Kelly asks me if we were supposed to reserve the cars or if someone else did that. I was shocked and found it kind of funny. We are responsible for booking our own hotels and rentals! She looked upset and stated she had no clue. I look at the attendant and stated we only had one reserved car. As she begins the check in process I tell Kelly there is no reason we couldn't share a vehicle. I'm sure the hotel will have extra rooms and we can reserve one when we get there. The attendant hands us the keys and tells us to have a fun trip!

As we are walking to the lot I look at the keys and it's a ford. I start pushing the button to hear the horn and find that for our vehicle we had a newer ford f-150. Man this sucker was nice! It was all black, with a chocolate interior. It had all the bells and whistles. As we threw our bags in the back seat and hopped into the front we both were amazed with how spacious it was. It had the center console on the seat. The ones that flipped back and made it into one large bench seat. It had driving features and even would maintain its own lane.

We were getting ready to leave when Kelly said she was going to go inside and change before we left. It's warmer here and after the water spilled, she put a hoodie on. I said I'd wait in the car and dig into all these features. When she came back out she had on a zip up jacket and looked comfortable! We had about an hour drive from here to the new offices. As she got closer and started to get into the truck, I'm sure my mouth was hanging open. She had the zipper about about 3/4 zipped. I swear she had no shirt on the way she was moving around in the jacket. As she hopped up into the truck the view confirmed my suspicion. Bam. Hard as a rock. Tell me again why I didn't wear different pants.

As we start on the road we get on the highway and it's not very busy. We are talking about life and talking about our workouts at the gym. I was telling her about the leg day I just did on this 4 week program, and how intense it is. I described it and told her to be careful it will make you very sore! As I'm describing the soreness, she asks specific questions about where I'm sore at and what would help. I told her Id like to book a massage and get all the knots out of my legs and thighs. She flips up the middle console and asks if she can try and help as she always was intrigued by massages. I don't have any time to react when she starts kneading my left thigh. She keeps asking if it feels good and if it's helping. I can barely speak. There is no possible way she can't see my rock hard cock going down my right leg. She is so sexy next to me and her jacket is slightly unzipping. As she continues to work on my left leg with her hands, it feels so good. I'm speechless and at a loss of words. It's not possible for her to not see my hard cock on the other side. I set the auto drive feature on the truck and lean back a little bit terrified to say anything.

She continued to massage my thighs in silence. She reaches over and starts on my other leg closer to her. As she does I start letting out some heavy sighs. She says this side appears to be worse that the other. As she says this she grabs my cock through my joggers. She says this appears to be a hard spot that she will have to work extra, and I just moan. She starts rubbing through the pants, and if I couldn't get harder at this point I certainly did. She asks me if I want her to continue in this spot. I respond by raising my hips up slightly and begging for more. As I raise my hips up she slightly lowers my pants and my cock flys straight up. Still unable to speak. She starts stroking me and asks if this is helping my soreness. I moan, yesssss.

Kelly sits back slightly and unzips her jacket over halfway spilling out those amazing tits. She says I have been dreaming about this moment since the trip was booked and I didn't want to waste any time over the next couple days. I'm glad you enjoyed the view in the airplane, I hope this is a bit better. With that, she leans down and wraps her lips around the head of my hard cock.

I let out a deep moan. It feels so good and the visual was great. She starts to move up and down on my shaft. She reaches up with her hand and is playing with my balls. She continues up and down on my shaft and I can feel her tongue. This is amazing. I place my hand on the back of her head and she moans. I take this as being ok to direct, which can be iffy sometimes. I push her head down further and further until I'm in her throat.

This is surreal. She starts bobbing from head to base and I can't last much longer. She can feel me getting close. She moves her hand from my balls and slides a finger down close to my ass and presses. I've never felt this sensation before and she starts moaning while bobbing up and down.

I can't last any longer and start moaning and letting her know I'm going to cum. I know it's going to be a lot not having taken care of myself before the trip. She keeps going. I start shooting my load, and when I do, she moves my dick as deep as it can go and I'm shooting straight down her throat spurt after spurt. She swallows it all. When I finish, she comes off my cock and takes a breath. She goes back down to clean me up.

Afterwards she raises up, full tits on display. I said oh my god Kelly, that was amazing. She said that she hoped I liked it, and that's she loves giving head. She hopes that this could kick off a long trip filled with fun and a crazy fantasy filled trip...

I can't wait to see what happens next.