The Secretary(Road Trip) by Red Tempest

It was June and the weather was great, the boss comes into my office and tells me that in 2 weeks, him and I are going on a trip to Chicago for a seminar. I thought fuck the last thing I wanted was to be stuck with him in a seminar. I told the wife about having to go away in a couple of weeks with the boss to Chicago, just so she knew what was going on. A week later he stops back in and tells me he is not going, they are sending him to New York, for a meeting with the corporate bosses. He told that all the arrangements have been made for me to go to Chicago alone. I immediately though of Stacey, wonder if she could go with me, what a fun couple days that would be.I called her at her office, and explained what was going on, and asked if she could join me on this road trip. She was excited, and said let me check some things out, and get back to you. I said ok, sure hope that you can go. Few hours later she called me back all bubbly saying that she could go, got the time off from work, and her husband will be gone that week up in Canada on a fishing trip. She also said that she has a cousin in Chicago that she could use as an excuse to go visit. We chatted some more on the planning of the trip, I told her next Tuesday morning be at the office at 7 am and she could park her car out back in a shed where it will safe, and we would head out to Chicago. It would take 6-7 hours to get there from here.

Tuesday morning right around 7 am in rolls Stacey. She gets out of the car and gives me a hug and a kiss. I grab her bags, and put them in my car. She gives me the keys to her car and I put it in the shed, and close the shed door and lock it. We jump into my car and away we go. She is all excited about this trip, and seeing her cousin. She described her cousin as in her early 40’s, with auburn hair, green eyes, very pretty. She is married with 2 kids, and works as an office manager for a small company. Her husband is a salesman, and he is gone a lot on calls. They have a nice house in one the Chicago suburbs. She ask what hotel we are staying at. I replied the seminar is held at the Silversmith, so we are staying there. She said I heard that was a real nice place. I have never been to Chicago, so I would not know.

She chatted all the way there, and wanted to know if I needed her to spell me on the driving. I said nope I was good. I enjoyed the trip with her, and she looked great. We arrived at the hotel around 3 pm, and got checked-in and the bellboy took us up to the room. It was a spacious room with a queen size bed in it. Stacey looked at me kind of quizzically, and I said that I changed the room from double beds to a queen, after the boss changed plans. We unpacked our clothes, and got things squared around. She came out of the bathroom and I was look out of the window at the view. She walked up behind me and put her arms around, and gave me a hug and put her head on the back of my shoulders. I turned around and wrapped my arms around her and gave her a big passionate kiss. I broke the kiss and we moved over to the bed and we stripped our clothes off, laid on the bed and made mad passionate love. We both fell asleep afterwards, and slept for a couple of hours. We were both pooped from the drive and the sex.

It was around 5 or so when we got up. We took a shower together, and had fun washing each others body. Her cousin told her of a couple of real good restaurant, to try that were first class.
We went to the Chicago Prime Steakhouse, and had a simple fabulous meal. The food and service were great, and well Stacey she looked simple ravishing, but then she was going to be dessert. Seeing how this was a business trip, and was paid for by the company, we took a cab to dinner, and then on the way back I had the cab driver show us some of the downtown sites. When we got back to the hotel, we went into the 14 karat lounge for a couple drinks and to unwind a bit. We discussed Wednesday agenda. She said that her cousin was picking her up at noon and they were going to have lunch and then go shopping, and to a beauty spa for the full treatment. She then had dinner reservation for us at 7, at a very up scale restaurant. Sounded like fun for her, as I would be stuck from 8 to 5 at the seminar.

We got back to the room around 11 or so, and got ready for bed. I was standing in front of the window in my boxers and tee shirt, while she was in the bathroom. She came out wearing a robe, and as she got near me she dropped it on the floor and stood in front of me naked giving me a kiss. She turned around and I ran my hands up and down her body, squeezing her tits and nipples. I bet we were giving all the window peepers a good show. She turned back into me and pulled my boxers to the floor and kneeled down and start to suck my cock. I said Stacey there could be watchers out there, and she replied let them look I don’t care, and she sucked away. Finally I pull her up to me for a passionate french kiss, with our tongues dancing around with each other.

We made our way over to the bed, kissing passionately, and grouping each other, both of us full of booze influenced lust. She started to work her way down on me, kissing and sucking my nipples, as she stroked my cock. She then moved on down to my shaved penis, and plant kiss all over it and my balls. The effect was sending me into escalating pleasures. She looked at me and said I just can’t wait anymore I am so wet, that I need you in me right now. She got up and straddled me guiding my cock right into her steaming wet pussy. It felt like I just entered a furnace, she was so hot. She rode me like there was no tomorrow, just pounded on top of me as fast as she could. I thought for a minute we would wake up the whole hotel. She threw her head back and cried I am going to cum, and she had a very intense orgasm, bathing my cock, balls, and thighs with her cream. For some reason she did not crash into my arms or stop fucking me, she kept right on going. She had this wild crazy look on her face and in her eyes. She yelled I am coming again, and she let loose with another wet orgasm, and then she collapsed on my chest.

I let her calm down for a few minutes and then rolled her over, never letting my cock out of her pussy. I started to stroke slow and deep, hoping that I could last all night. She started to wiggle and squirm, and I picked up the pace. Soon I could feel that tell tale sign of my nuts tightening up and my cum start to race up my shaft, and I shot a load that lifted us both right off the bed. We both laid there exhausted, our hearts were just pounding from all that sexual excitement. Finally with her in my arms we fell asleep. All of a sudden the fucking phone rang, and I though what the hell, who would be calling this late at night, till I realized it was morning and, that was my 7 am wake up call. She said who is that, and I replied it was your husband. She popped up in the bed wide eye looking at me, I was grinning like the cat that swallowed the canary. She said it is not, and threw the pillow at me. I laughed and answered no it was my wake up call, and I tossed the pillow back at her

.

I went into the bathroom and shit, shave, and showered, came out and got dressed for the seminar. I told her they were serving a continental breakfast at the seminar. When you get up and ready, just order room service and charge it to the room, for your breakfast. She replied ok, and said I am going back to sleep, and pulled the covers up over her head. I leaned over and pull the covers down a bit to give her a kiss goodbye, and told her I would call around noon. She just pulled the covers back up, and mumbled something from under the covers. I left her $400 to spend on her self today.

The seminar was very interesting, but it was hard to keep my mind on what was going on, when all that I could think about was Stacey. Finally noon came and it was break time for lunch. They had a buffet table setup with soup, salad, and sandwiches on it. It was ok, it did fill up a hollow spot for a while. When I finished, I stepped out of the room to give Stacey a call. She answer, and said the she and her cousin were sitting down to have their lunch. We chatted for a bit and then her food came so we said our goodbyes. I went back to the seminar and she to her lunch.

The girls had a great time together, they shopped till they dropped, and then went to the beauty spa. The owner was real good friend of her cousin. They both had a massage(I wish I could have done Stacey’s), mud facial, toe nails and finger nails painted. A relaxing soak in the spa, a shower to clean up. Finally their hair all fixed up, and make-up applied by the beautician.

She called and said that they were on their way back and should be there around 6 or so, I said see you then. I went into the bathroom and shaved and showered, and got dressed in my suit and tie. There was a knock on the door, so I open it up and there they were with their hands full of bags. Both of them looking simply gorgeous. I grabbed their bags for them as they both came into the room. She introduced me to her cousin Mandy. Mandy is very pretty, in her early 40’s, with auburn hair and sparkling jade green eyes. She is a slender gal with nice tits, may be 34 C, and a killer ass. If you forgot I will refresh you on what Stacey looks like. She is a doll, in her upper 40’s with a hour glass figure, blonde hair, soft brown eyes. Her assets were perfect 36 C breast, slim waist, perfect ass and legs.

They shooed me out of the room and told to go down to the bar and wait for them. It should not take them long to get ready. Yea right where have I heard that before. So down to the bar I merrily went to have a cocktail, and to wait.

Within 20 minutes in came the ladies, and WOW I almost spilled my drink as I gawked at them, and so did the rest of the guys in the bar. Stacey had on a low cut silver dress with a silver crown like thing in her hair. That dress fit her like a glove, leaving not much to your imagination, as all of her assets were on full display. Mandy had a emerald green dress on that sort of matched her eyes, and some sort of green decoration in her hair. Her dress also fit like a glove, with low cut at the top and long slits on the sides. They walked up to the table and Stacey giggled telling me that I could now close my mouth. I tried to work my mouth for what seemed like 30 seconds, but I could not get any words to come out. Finally I took a long pull at my drink to wet my whistle, and I was able to speak, and said, wow you two look fabulous. I quickly helped both ladies sit down and we order a round of drinks for us.