It wasn't too long after we started experimenting with adding other people into our sex life that I was asked to go to New York City with a client to look for condos in Manhattan. Usually I wouldn't do such a thing: one, I do not hold a NY real estate license and two, I don't know the market, but this particular client is both a celebrity who has brought me a lot of business over the years - buying 4 houses through me in LA - and also recommended me to many of his friends and that has led to a lot of money for me over the years. So I agreed to accompany him for three days to the East Coast and help him make a decision.
We were greeted at JFK by his NY realtor. I was a little surprised by the fact he was only 25 years old. This is high dollar real estate we were looking at for a high profile client. I was not as surprised that Stephen was incredibly attractive and dressed in a $3,000 suit. Since I was not officially working, I was dressed in what I call "sexy conservative" - this day was red 5" patent pumps, black leather skinny pants, a red satin cami and a black cashmere cardigan over top to maintain the professionalism.
Our first day was not very successful as we found nothing that remotely interested the client, but Stephen got to figure out a little better what he was looking for and Stephen and I had a little bit of fun lightly flirting and getting to know each other. We went to dinner at Le Bernadin and Stephen promised to do some homework tonight and we'd have a much more successful day tomorrow.
The second day was a lot better. Stephen had really listened and although we did not find "the" place, he was close and I knew he would get there day three. I could also tell Stephen was paying more attention to me. That day I was dressed in 5" black patent pumps, black satin capri pants, a green satin blouse and a black leather blazer.
Day 3 my mind was wandering. I was starting to think about Stephen and what might be hiding underneath those designer suits. I was dressed straight up sexy this day - those same black pumps, tight black leather pencil skirt that came just above the knees (no slit, no give and you couldn't fit paper between my ass and that skirt), white satin blouse opened to show just a little bra if your view was right and my strand of pearls and my black leather blazer on top. After looking at 8 places, our client decided to put an offer in on the the first place of the day. He'd given me instructions on how to structure the offer and so he left to party with friends on the last night while Stephen met me at the hotel for dinner and to go over the offer.
I don't remember when I got the idea, but I decided I was going to fuck Stephen. I stayed professional and we finished the offer over cocktails and then decided to have dinner together anyhow. We quickly got personal, he asked about LA, I asked about NYC. He talked about an endless string of girlfriends and I talked about my husband.
Somewhere near the end of the entree I started flirting pretty heavily. I kept touching him more, playing with my hair, all the usual girl tricks. He asked about dessert and I suggested that we head to the hotel bar for a drink instead and he agreed. The check came and as he took care of the check, I slipped off to the little girls room.
Once in the bathroom, I quickly dialed my husband's cell phone. He answered and was happy to hear from me. I asked him where he was and he said he was still at the office (7:30 in LA) and that he was the last one there. This made me happy. I told him to stay put, close the office door and in one hour, log into Skype - I had a surprise for him. He was excited and promised to be logged in at 8:30.
I met Stephen at the table and we walked to the hotel bar - he ordered an Old Fashioned and I ordered a Chopin martini. Now, as we were standing at the bar, I started getting more physical. I reached around and touched the small of his back, slid my hand down to his ass and gave it a little squeeze. He was a little surprised - I think he figured me being married I was just having a little flirty fun out of town but I straight up said to him, "Why don't we finish our drinks and head up to my room?"
"Uh, um, but you're married."
"About that.." I said, "My husband actually approves of me sleeping with other men. He's discerning, he doesn't want me sleeping with just anyone, but if they're sexy, fit, handsome and preferably have a large cock, he gets off on watching me."
"Uh, is he upstairs?" He asked me nervously.
"No, but I was going to call him on Skype. He's in his office in LA."
"I don't know."
I moved my hand down and grabbed his cock, which I was happy to find thick and hard as a rock. "You know you want to, I can feel it."
"Well, you're very sexy, but this is kind of weird to me. I've never done anything remotely kinky."
"Why don't you come upstairs, let me make you comfortable and you can leave at anytime?"
He looked at me for a long time, my hand rubbing his bulging hard on and finally he said, "Okay, but I'm going to need another drink."
I smiled and gave that cock a good squeeze and said, "I have a bottle of 21 Year Old Glenlivet upstairs, will that do?"
"All I need is an ice cube" he said.
With that we went up to the room. No words were said the entire time and he didn't even try to touch me in the elevator. He was nervous as all hell. Honestly, it was a little bit of a turn on. He obviously found me attractive and the fact he was nervous about it was cute.
