A Gentleman for Lynn Ch. 01

This is a true story, or about to be when we meet. We've been chatting for a couple of months and have become good friends, if only on-line. I told her I'd be writing this for her, so there is an intended audience of one, but other readers can look in! I'm sure our actual first meeting will be different, but this is my nirvana. Don't look for sex here in the first chapter; seduction takes time.

I was seated at a corner table in the Punch Room bar on the fifteenth floor of the Ritz-Carlton hotel in Charlotte waiting for her, a little bit before our 4 o'clock meeting time. I wanted to get there early because I wanted to ensure everything was right. It was to be her first time with a man.

"What'll you have, sir?" asked the bartender, an older gentleman in black pants, white shirt, and black bow tie.

"Zubrowka Martini, up, twist." I replied and after looking at the well-stocked bar, "and when my partner arrives, a Glenmorangie 25-year neat, water on the side."

"Yes sir. And for a vodka drinker, you know something about whiskeys, too" he smiled and left to make the drinks.

I chose the Ritz-Carlton for a couple of reasons. First, it had a dark, quiet lounge off the main lobby away from the hotel foot traffic, and second, the Ritz always had bathrobes in its rooms. Lynn would be arriving at the hotel in her outward, male clothes, wearing her gurl clothes underneath. "It'll be our secret, just for us two" she had told me. The bathrobe was important because not only was it her first time with a man, it was also the first time she was revealing her true feminine nature to anyone, and I thought it would be more comfortable for her to get out of her street clothes and put on a robe over her lacy feminine undergarments before coming out into the room, if only to undress in front of me.

We met online in a gay chat site that specializes in older gentleman a few months earlier and we took an immediate liking to each other. Soon we were chatting exclusively with each other almost every day. Often when we had time, I would bring her to orgasm from our explicit chatting. "What about you?" she'd chat back after a long pause that signaled to me that she had cum. "Being an older gentleman lover means you always bring your woman to climax first" I'd told her. I'd heard that before in my thirties, and now that I was sixty-four, I have to say it is true- I really care about her needs before my own.

Unlike a chatroom, there was no guarantee she'd show up. It was a huge step for her, or any person for that matter, to embark on an affair, let alone a gay one and a cross-dressing one at that, and I'd been stood up before. But the timing seemed to be perfect. My wife was out of town on a business trip, which meant I could drive to Charlotte from our house on the North Carolina coast. Lynn's wife worked, so Lynn could get away during the day for a "business meeting."

At four o'clock, however a very pretty, younger man walked through the door of the Punch Room, and I knew it was my date. Close-shaven with very soft features in his face and hair with just a hint of eyeliner, Lynn was the epitome of gender-neutral.

I immediately stood to greet him. He may have been younger, but there was a woman underneath, and good manners dictated that I rise to greet her.

"Lynn?" I asked, although I needn't have. "Jim?" he replied.

"Finally, we meet! Please, sit with me. I hope you don't mind; I took the liberty of ordering us drinks."

I could tell Lynn was nervous. She had to have been! It was a big first step, and I had ordered her the Scotch to try and settle her.

"Your drinks, sir" the bartender said as he laid the vodka Martini in front of me, and her Scotch in a leaded glass cut highball glass opposite mine along with a small pitcher of mineral water and left as quickly and quietly as he had come. I'd be tipping him heavily.

"How did you know?" Lynn asked as we sat down opposite each other as men are apt to do.

"Remember? You told me once, Silly, 'on rare occasions single-malt Scotch' when I asked you what you like to drink." I poured a few drops of water from the small pitcher of water into her drink to release the Scotch's smokey flavor.

"Oh, I did, didn't I?" she smiled and said, "You really are attentive, aren't you?"

She reached over and touched my hand with her delicate fingers. Her nails had a soft clear polish on them, quite unlike mine which were cut very short, my fingers with still-healing scratches from working in the garage at home. Lynn's fingers were a little chilled too, betraying her nervousness.

"What did you do?" she asked when she saw the small, wrapped package in front of her on the table between us.

"Oh, just a little something" I told her, "Go ahead, open it!"

She undid the red ribbon and unwrapped the package and after peeking under the tissue looked around the room to ensure no one would see a man take out a white silk camisole offered as a present from a would-be lover.

"It's perfect! Oh, I'm just so happy, I'm about to cry."

"Now, no you don't" I reassured her, "It's just nerves Lynn, have a sip of your drink."

"It's just perfect. I can't wait to try it on. Thank you so much, sir, but I don't have anything for you!"

"Oh, but you do" I said as I spied something she was wearing. I wonder...

"I do?" she asked.

"Around your neck is a gold chain... is the key to your chastity device attached to it?"

Her face turned three shades of red as she looked at me, coyly nodded and silently reached over her head and pulled off the thin gold chain, which did indeed have the key attached. She handed me the chain and key, which I placed in the side pocket of the blue-checked Canali sport coat I was wearing, all the while never breaking eye contact with her.

This, of course, made her blush even more, as the skin of her neckline down to her shirt flushed a similar color red as her beautiful face. It was clear we were already establishing the nature of our relationship during those first few minutes. I was the man and even though he was wearing a loose-fitting golf shirt and slacks in the Punch Room of the Ritz Carlton, she was the woman.