John understood the logic of checking out of his room by 11 am and saving a day of room charges by moving into my room. And the logic of using only one room for the rest of the week, since it seemed obvious that we intended to spend a good deal of time together now that we had realized our mutual sexual attraction. And moving into my room would be easier than me moving up to his room, he just has less 'stuff'.
But I could tell something was nagging at him. He insisted that he pay for half the cost of our shared room, rather than allow me to cover the cost of his remaining stay. He'd be saving several hundred dollars a night in room charges. That would make him feel like a 'kept man', a gigolo.
At first, I just laughed at his concern. Don't most men like the idea of being the 'boy toy' of a mature woman? He explained that maybe a younger guy would jump at the chance to be in that sort of relationship, but for him, it carried a negative connotation. A mature, financially secure professional person of equal stature, experience, and age doesn't want to be regarded as a plaything of someone else, no matter how great the sexual reward.
I admit I didn't see that one coming, and I should have. I told him that if it would make him feel better, he could Venmo me the difference when we checked out. That seemed to eliminate that hang-up. When you move into things a bit fast, it's easy to miss some of the subtle but important nuances in a relationship.
He brought up another concern. A basic inequality in our relationship. I'm married, he's not, and he's not in any serious relationship that would be jeopardized by our affair. I alone would bear the potential burden of infidelity rupturing my life if our relationship were revealed. He couldn't escape worrying that I would be the only one suffering any consequence for our actions.
This guy really is a sensitive and caring individual, I thought. He's worrying about stuff that hasn't even happened, and isn't likely to happen. And besides, that's for me to worry about, not him. And I'd already taken that possibility into account in thinking this through. He seemed to accept my reasoning. Another roadblock to great sex was removed.
John moved his belongings into my room, I got an extra card key from the front desk, and to see if there would be a change in my room charges for double occupancy. Thankfully, they charge by the room, not the number of occupants, so there would be no sudden, unexplained increase on my credit card bill. Not that my husband is that detail-oriented in the first place, or if he would even bother to look at my bill. But it doesn't hurt to check.
We went through the usual hassle of organizing our things in my room. Naturally, there were not enough hangers for all our clothes that normally require hangers, and I had used all the dresser drawers because there hadn't been a need to save space when I unpacked.
So we went through a round of my freeing up hangers for him, while I carefully folded clothes that had been on hangers to move them into drawers. Which meant consolidating my clothes to free up some drawer space for him. And then the task of organizing our stuff in the bathroom, another round of moving things and finding space for everything. By the time we were finished, the idea that we were doing all this for an enhanced sex life for a few days was not on the radar.
Pro tip #1 for having an out of town afair: Stay in separate but adjoining rooms.
Unfortunately, the hotel didn't have any of those available for those days. So yes, it was another hassle. We somehow managed the process without biting each other’s heads off.
I had to get moving after all that in order to get to my sister's place on time, since we were taking her kids to lunch and then an "Escape Room" experience. They're totally into those games, but it would be my first try at that genre.
John and I planned to meet later in the afternoon at the Whitney with his group. Apparently, even the women of the group were now a bit more accepting of my presence after our outing yesterday evening at the Met. And the men were glad to have 'Madame X' to talk to and look at. So I was more than welcome.
This was to be more of a 'dress up' affair because of a reception with cocktails and appetizers after touring some galleries, plus a much larger group of people, not just his CAA colleagues. Definitely not a jeans event, even John had to admit. He said to dress in something more formal, if I had something like that.
I did bring a long black satin gown that I thought might look good: it has a high slit up one thigh, and a plunging neckline with spaghetti straps. Even a strapless bra wouldn't work with the gown due to the sharply plunging neckline. It was meant to be worn without a bra. Or more accurately, it was meant to be worn by a younger woman with firmer breasts, this would be one of the last times my physique would likely make this dress work.
My black panyhose also wouldn't work with the dress, they would make for very visible panty lines beneath the fabric, so I substituted a pair of nice black thigh-high stockings instead. So basically naked underneath tonight.

The Escape Room was actually fun, though I'm not sure I contributed a great deal to the solutions. It basically involved solving the disappearance of a diabolical scientist working on a deadly virus and preventing a deadly epidemic in the process. It was very immersive and convincing with sound and visual effects, including fog, flashing lights, alarms, as well as various puzzles and riddles to solve in order to receive clues from an unseen 'game master' who monitored our progress.
I have to confess that in the mood I was in this week, my mind conjured up the possibility of a somewhat more risque genre of escape room. The adult-only participants have to answer various 'truth or dare' questions revealing their various kinks, past sexual experiences and fantasies in order to be rewarded with additional clues. And possibly rewarded by also discarding articles of clothing along the way, aided by periods of complete darkness or the requirement to don masks to prevent participants from knowing exactly who they're next to at certain intervals. The possibilities are endless. Of course, if I'm thinking of it, someone else probably has already.
I made it back to the hotel in plenty of time to change into my gown and get to The Whitney. The moment I stepped into the hotel lobby, I knew I had made the right decision on what to wear. All eyes turned my way, men and women. And the Uber driver's tongue hit the sidewalk when he opened the door for me. There was no way to step in and out of a car with a thigh slit like this without revealing something.
I realized when I got to The Whitney, I looked very much like John Singer Sargent's Madame X than anything else. Even John had to put his eyeballs back in his head when he saw me in the gown. I breathed a sigh of relief that my appearance may have washed away the doubts and conflict from earlier in the day.
The rest of the men in attendance were obviously envious of John's escort for the evening, and the women seemed a bit surprised at the change in appearance from the previous evening. I even let one shoulder strap occasionally and casually fall to mimic Madame X to complete the transformation and stir the imagination. Another vigorous shrug or a sneeze and there would be quite a display for everyone to enjoy. My erect nipples were bearing a good share of the burden in holding up my dress.
I took a selfie and sent it to David to excite him. Letting him see how I looked in this very public setting would turn him on completely. Much like our previous 'games' in less glamorous settings with fewer strangers than this. This was another level altogether as there were photographers, including one from the NY Times, taking pictures, some of which would end up in their paper, online and in print since this was a high-profile event with a number of VIPs in attendance.
It had the desired effect, especially when I texted that I was naked underneath the dress.
**Wow, I wish I could fuck you right now!**
I couldn't help taking a selfie with John, his arm around my waist and looking at me with obvious desire. I sent it to David.
**Who's that?** He texted back.
**One of my art history friends who desperately wants to fuck me** I knew that would get his attention.
**How do you know that?**
**Probably from the way he had his hand up my dress last night, and he said he wanted to fuck the daylights out of me**
The next text from David was a picture of his hand holding his very erect cock! I had his attention.
**We need a phone sex session when you get back to your room tonight!**
**That's a date, darling. I'll call later tonight after I get back to my room**
I didn’t say anything to John. I was thinking of how he would react watching me pleasure myself while David and I acted out our sex over the phone. Or maybe he would like to help out by acting as a proxy for my husband in our role-playing game? Or more? Two nights ago, David had been unaware that John was silently fucking me while we were on the phone, but I ended the call before John really fucked me full force. This would be a bit trickier to pull off.
I was getting wet thinking of the possibilities. I discreetly moved closer to John, so my ass could make contact with his pelvis, without anyone in the gathering noticing. His cock was like a piece of carved granite. Good thing this dress is black. John said he wanted to go outside to one of the dark corners of one of the garden terraces in the dark and fuck me like crazy. I told him I had something much better in mind once we got back to our room. My husband will be joining us again.
