As previously shared, I met Brady back in April and we had a fun first date. We bonded over cocktails, which led to an intense (and inappropriate) make-out session at an uptown lounge. When he expressed his desire to go out again, he indicated that he would prefer to go somewhere with more privacy (so as not to shock fellow patrons again) and shared that he wanted to spend more time with my sexy persona. I readily agreed and we picked a date for the following month given our mutually busy schedules.
We arranged to meet at an upscale bar (initially the Roosevelt Hotel rooftop lounge, which turned out to be closed for renovations), to give us the opportunity to reconnect after the four-week hiatus. I had been more casually dressed for our first date, so I made up for my error with an overtly sexy, black and nude, lace cocktail dress, which very much met with Brady’s approval.
Over drinks, Brady brought up the topic of a safe-word and stated that it would be… safe-word. I knew from our first date that he was into spanking, but we hadn’t discussed much else in the way of D/s play, so I wasn’t sure what to expect. Plus, this was only our second time meeting each other, so I was both excited and nervous at the same time, not knowing precisely what was in store.
We finished our drinks and headed over to the Roosevelt Hotel lobby bar where Brady ordered us a second round. As we sipped our cocktails, Brady handed me a room key and told me there was something on the bed that he wanted me to have. I headed upstairs, opened the door and was greeted with a note and a leather collar. I gingerly fingered the leather on the collar and then reached for, and read, the note.
“There’s only one decision you have to make this evening: to put on this collar or not. If you do, it means you belong to me tonight. You’re my courtesan, and the only thing you have to worry about is my pleasure.
You will do as you’re told, and if you make me happy you will be rewarded. If you don’t, you’ll be punished. It all depends on what I decide. If that’s what you want, have the courage to put this on and come back to me in the bar.”
It was a very titillating invitation. I put away the note, took a deep breath and fastened the collar around my neck. Then I grabbed the key, shut the door and returned to the bar. I don’t know if anyone else noticed my new “necklace,” but Brady was pleased to see me wearing it.
We finished up in the bar and went back up to the room together. I was to call him “Sir” and he would address me as his “Little Pet.” His first request was for me to take off my dress. I unzipped it and let it fall to the floor. I was then asked to sit on his lap, which I dutifully obeyed. Next, he wanted me to place my face against his hard cock so I could see how my obedience turned him on. Eventually I was asked to remove his clothing and then kiss (not lick or suck) his penis.
We then walked over to the bed to continue our mutual seduction. The outercourse was intense and orgasmic as he repeatedly tasted me, teased by nipples and otherwise brought me to climax. After several hours of play, we fell asleep, waking up with the first rays of sunlight. In the early morning hours, we resumed our exploration of one another.
Admittedly, I wasn’t sure if the scene continued from one day to the next, so I continued to request permission as needed and refer to him as Sir. Also, interestingly, there had been no impact play. Perhaps I had been too obedient and hadn’t warranted a spanking? I’m not sure, but I’m hoping for a debrief at some point.
By 7:30 AM, I was dressed and ready to head home to walk the dog. Before I left, Brady unfastened the collar and then presented it to me, saying that he wanted me to keep it and that it should serve as a reminder, whether or not I had it on, that I belonged to him during future encounters.
He accompanied me downstairs and outside as we said goodbye and I returned to real life. On the subway home, there was a text from Brady expressing his pleasure with me and the evening and his desire to meet up again soon.