I recently met up with a guy who was staying in an airport hotel near us.
Jack and I had been chatting online for a few weeks as he was planning his business trip to town. It started out innocently enough with my giving him some restaurant and sightseeing suggestions. But as I got to know him better, we got to talking more and I found out that his home situation was a little sad.
Jack was in his late 30s, a few years younger than me, married for a short time with small kids and a stay at home wife too tired for any sex by the time he gets home from work. Sadly, it's a story I hear far too often. It opened the door for us to starting to flirt a little and ultimately deciding to actually meet up in person when he came to town.
We had arranged to meet up at his hotel when he got to town. I made it clear to him that I would be with hubby as he always goes with me for safety reasons and also because he loves to watch if things go in that direction! Jack was nervous but OK with it.
Before i meet someone, hubby and I have a ritual we go through. He will pick out the dress and shoes and underthings he wants to see me get taken out of. He then likes to watch me as I work on my hair and makeup. I like to tailor my look to the type of guy I'm meeting. For Jack, I went for the sexy girl next door look but added a little extra eye makeup and teased the newly blonde hair a little to give me a bit more of an edgy naughty look. Hubby says I act naughtier as a blonde, but I think it's just that the guys are more into it.
Hubby likes to take a picture of me all dressed up. He calls it the before picture. I struck a prim and proper next door pose in the driveway before we drove to Jack's hotel and met for dinner and drinks in the lobby restaurant. He was waiting for us and we had a fun time at dinner with a healthy dose of flirting with each other. With hubby in tow, I like to take the time to meet a guy for dinner and give both guys a chance to get to know and relax around each other so there's none of that competitive alpha male weirdness going on. A few drinks usually helps with that and it helps me relax some too, but sometimes its not enough and the date has to end. This time, however, everyone seemed to be getting along quite well. The bill came and our new friend paid, carefully and nervously in cash, I noticed. We discreetly took separate elevators up to his room so that none of his colleagues would see that we were going up together.