I stood just inside the lobby of the hotel where I had met James weeks before. As instructed, I stood just to the left of the revolving door, towards the concierge's desk. Nervously, I shifted my weight from one foot to the other -- the motion making me keenly aware of my skirt brushing against the bare skin of my ass.
I looked at my watch -- James's note said he would meet me here on Friday night at 6:30, and it was only 6:20. The note had arrived in a package earlier that week, along with a pair of incredibly luxurious grey silk stockings, a black garter belt and a lacy black silk bra and thong -- all now worn under my outwardly conservative black skirt, red silk blouse and black jacket. I gazed down at my right ankle, the gold anklet glistening atop my stockings, wondering what, exactly, the evening would hold for me.
Again, I checked my watch, 6:22, and glanced briefly at the wedding and engagement rings on my left hand.
Jack was supposed to have been home from a business trip this morning, but his flight was delayed, meaning I had had to prepare myself alone -- showering and shaving my legs and pussy, and -- as Dr. Fairchild had suggested -- giving myself an enema, in anticipation of being sodomized tonight.
I closed my eyes, wondering if my initiation would perhaps be James in a hotel room upstairs? But Dr. Fairchild had specifically mentioned "men" -- perhaps James and another man? Or perhaps she hadn't intended to imply multiple men.
My pussy -- having spent most of the day in moist tension -- squeezed in anticipation of the unknown. During my "affair" with Derek, I had always had some idea of what was going to happen, and of course I had known it was going to be happening with Derek -- or Derek and Jack. But as I stood here, watching the rush hour traffic move slowly past the hotel, I realized I had no idea what I would be doing tonight, or with whom.
My husband's unexpected absence this afternoon was at once a disappointment, and a turn on, as I was freer to imagine what naughty things might be done to me. My phone buzzed, and I checked the text message from hubby: "Just landed, will see you soon. Enjoy the start to your evening."
I smiled, and was about to type a reply, when I felt a hand on my shoulder. I turned to see James, smiling at me.
"Tammy, you look lovely as always," he said, giving me a gentlemanly peck on the cheek.
"Thβthank you," I stammered, as I realized that my evening's adventure was about to begin.
"I heard that Jack's flight was delayed?" James said with a wink. "Not to worry, I've told him where and when he will be able to meet up with you. I think we will be able to fill the time until his arrival," James added with a confident smile as he took my hand in his. My heart raced, as my mind ran through all of the scenarios I had imagined for tonight -- scenarios that had been enhanced during masturbation sessions the past few nights behind a locked bedroom door, with vibrators, nipple clamps and my leather collar all employed.
"Are you ready, Tammy?" James asked quietly, his ice blue eyes soft yet dominant, sparkling and incredibly sexy.
I gulped nervously, knowing that I would have to be "ready" for anything or everything.
"Yes, James," I answered softly. "I'm ready."
James' smile grew wider, and he squeezed my hand. I was expecting him to lead me across the lobby, to the elevators, to take me up to a room, and was surprised when he instead guided me through the revolving door, into the cool evening. He took my hand again, and we walked to a shiny, black Town Car parked in one of the ten minute parking spots just outside the hotel's circular drive. James opened the back passenger side door, and gestured for me to get inside.
After I was inside, he shut the door, walked around to the driver's door, got in, and started the engine. As we pulled into traffic, I noticed that the windows of the vehicle were heavily tinted.
"Tammy, if you will look inside the seat pocket in front of you, you'll find a black leather blindfold. If you would please put it over your eyes?" he said matter of factly as he slowly navigated between cars. I leaned forward, feeling my skirt against my ass, and found the blindfold, in between two chilled bottles of water. I put the blindfold over my eyes, and felt myself instantly become more aroused. I leaned back in the leather seat, desperately wishing I could slip my hand under my skirt to stroke my aching pussy.
After a moment, James spoke again, his voice firm, and just barely audible over the sound of rush hour traffic.
"Tammy, to begin this evening, we have a number of men waiting throughout downtown. One by one, each will join you in the back seat, and you will suck him off. After each man comes in your mouth -- and you will of course swallow -- we will drop him off, and go to pick up the next one. There are bottles of water in the seat pocket if you need a drink in between blowjobs."
I listened behind the blindfold, my heart racing. James continued.
"You will wear the blindfold until I tell you to take it off. Some of the men may join us later in the evening for the rest of your initiation, or not. This means that, after tonight, you will never again be sure of how many different men you have had sex with, nor will you know any of the specific men who will enjoy you tonight."
A nearby car honked, making me jump.
"So over the next few weeks and months, you will look at every man you meet, and wonder. Is the man standing in line behind you at the grocery store one of the men whose come you will swallow in the next hour? Or perhaps the shoe salesman at Nordstrom, kneeling before you, is a man you've knelt in front of, taking his cock in your mouth and pleasuring it?"
The car was silent for a long moment, as I tried to absorb what James was saying, and finding myself more and more turned on. Finally, James spoke again.
"I will tell you, Tammy, that at least one of the men you will pleasure tonight is a social acquaintance of you and Jack -- and that he is very, very much looking forward to helping with your initiation." My mouth was suddenly dry, wondering who it might be. I was about to reach for a bottle of water when I felt the car stop, and heard the back door opposite me open. I heard, and felt, someone sit down behind James' seat, and knew that the water would have to wait.
The car door slammed shut, and the vehicle started moving again.
I felt a large hand on my left thigh. "Good evening, Tammy," a deep, sexy voice said jovially. "I understand you've already had a little experience with a black man, so James thought perhaps you'd be most comfortable starting with your second black cock."