[MF] Perks of Business Travel – Chicago

I am an attractive professional, 46yo, MWM, 6 feet 1 inches tall and fairly fit. I am an avid runner and like to stay in shape. I also have a job that requires a fair amount of travel all over the globe. It sounds fun, but can get old after a while. Typically, I am only in a city for one night at a time so it is a lot of airports, conference rooms, and hotels. Fortunately, I typically stay in very nice hotels, Four Seasons, St Regis and Peninsula Hotels are my favorite. While I have been traveling for many many years, I stumbled onto Craigslist Casual Encountes a few years back and my life on the road became a little more exciting.

This was not my first success story from Craigslist, but one of the first and I thought I would share it with the group. Hope you like it.

I had meetings in Chicago on Friday morning and decided to fly in from NY a little early and enjoy the evening in Chicago. The afternoon before I was set to fly out, I decided to post an ad on CL stating; Attractive Professional visiting on Business. Within the add, I indicated that I was staying at the Peninsula Hotel and wanted to meet for dinner, drinks, or more!

After getting a number of spam emails and solicitations to sign up for verification services, Monica sent me a reply (not her real name, but the one she used). In her first email, she enclosed a picture of herself taken in wearing a bikini in a lounge chair showing only her body and legs, no face. I replied back with a picture and we started chatttjng. After a few emails, I realized she might be a real person, Craigslist does work once in a while. After we both became comfortable, we agreed agreed to meet once I got into town and she said to call her when I landed.

In the taxi from O’hare, I gave her a call we we decided to meet at the bar in my hotel. She lived in the suburbs and was driving into the city leaving me plenty of time to get some work done and get cleaned up for dinner, hopefully more.

At the appointed time, I walked down and met her in the bar at the Peninsula, which is one of my favorite bars, small, dark, lots of overstuffed leather chairs, just a great hotel bar.

Now about Monica, she was 48 yo, divorced, about 5’1″, but had heels on, brunette hair down past her shoulder and literally about 105lbs soaking wet. She looked incredible. She was wearing a nice top and designer jeans which contrasted my suit and tie. I greeted her with a quick kiss on the cheek and then we sat down on had a couple of drinks. Scotch for me and white wine for her. The conversation flowed smoothly and we were both happy and relaxed.

I was starving and we agreed to walk to a great restaurant a couple of blocks away for a light dinner. However, she suggested that inchange into something more casual before we left. Not to be rude, I invited her up to my room as I changed which led to some passionate kissing to break the ice. Not sure why, but we decided to continue with dinner so anquick change and we were off. However, we both knew what the evening held.

We had a quick dinner st the bar at the China Grill and then back to the hotel for me. In fact, during the dinner, I offered her another glass of wine and she accepted by staying after this, I am definitely spending the night with you (not wanting to drive). Can you say, check please.

Once back in my room, we begin making out on the couch like a couple of teenagers. I loved her tiny little body. At one point she straddled me, faced me and was grinding into my cock. I still remeber this, she leaned back, unbuckled her wide leather held and pulls it off throwing it on the floor. The undressing cam fast and furious after that. First I removed her shirt exposing her small a/b cup breasts. I happen to love tiny breasts and hers were perfect, top with lovely dark nipples which were responsive to the touch. After playing with her breasts and pushing my hands down the back of her jeans to feel her ass, I moved her to the bed sliding her jeans off in the process.

I had to take a moment to take in the sight. Here was the beautiful lady, with a perfect body for her age, that I met the first time a few hours before, laying on my bed wearing in a sexy black satin thong. I was in heaven. I quickly undressed and begin to worship her body, kissing her lips, her breasts, her flat stomach, and her soft inner thighs, before finally kissing her wet pussy covered only in the satin material. I slowly removed her thong leveling her completely naked, open and exposed. The. I began to lick her perfectly shaved pussy, slowly at first then building in intensity until she was grinding on my face. I was able to bring her to an orgasm in a matter of minutes and then I found out what she really liked to do.

It turns out, that she absolutely loved giving head. I mean she spent most of the night literally with my cock in her mouth, soft, hard, she did not care. In fact, when she was not sucking my cock, her hand would be playing with it casually as we talked. I have never been with a lady that enjoy cock, and in particular, cock in her mouth as much as her.

While we did have sex three times that night and in the morning, I always came in her mouth. And she seemed to always be playing with my cock. Even the couple of hours, we slept, her hand was on my cock as she curled up beside me. She was amazing.

In the morning, we each jumped in the shower and got ready for the day. I kissed her goodbye at the door to my room after signing over her valet slip to my tab.

Fortunately, I got to spend another evening with Monica on another trip to Chicago, but that is another story.

I have had a number of great experience during my travels. Happy to share if there is interest.

Source: reddit.com/r/gonewildstories/comments/6ww1y0/mf_perks_of_business_travel_chicago