1st Meeting with Mistress Ch 04

Chapter 4 - Dinner, signing and becoming hers

In the early evening, as darkness was falling, I arrive at the hotel dinning room. I am afraid that she would not like me, I wouldn't be what she wanted, and send me on my way. The online Mistress I had been working with had been the sort that would take anyone and use them for whatever her goal was. I am now meeting with a real live Mistress, one who had been doing this longer than I've been alive.

I screwed my courage to it's sticking place, walk in and say to the host, "I'm here to meet a lady, named Victoria. She said that she would leave a notice with the head waiter."

"Are you Fred?" He asks, quietly.

"Yes" I answer.

"This way, please." He says, as he leads me to a small semicircle booth, near the windows. As we approach, a lovely lady stands up and greets me with an outstretched hand.

"Fred, welcome. I hope you are still interested." She says as we shake and slide into the rounded booth, sitting side by side.

"Oh, yes, I'm still interested. I've been worried that you would change your mind." I answer, with a worried tone in my voice.

A smile creases her face and she answers with "Not a chance, you are the best candidate I've interviewed in years. I've been looking forward to this the last week."

I answer with a "Yes, thank you ma'am." As I see a small smile, sneak onto her face and then disappear again.

A waiter and a waitress both appear opposite the two of us. "Something to drink?"

"Yes, a nice house red wine for the two of us, bring the bottle. While I read the menu."

"Yes, ma'am" the waitress answers, causing both of us to smile, as she turns and walks away.

I watch her walk away and think, nice ass. Mistress leans over to me and says "Nice ass on her isn't it."

I'm startled by Mistress voicing what I'm thinking. I look over at her and see her smiling at me.

"I think we will fit together quite well." She says, voicing what I was thinking again.

"What would you like for dinner?" Asks the waiter.

"A Caesar Salad for each of us, Chateaubriand for two, Au Gratin potatoes, and what ever this evening's vegetables are." I hear Mistress order for both of us.

The waitress returns with the wine selection. Sitting back, we watch as she opens to wine, hands the cork to Mistress and then, after a nod, pours the wine. She then stands back with a bowed head and hands crossed behind her.

"Anything else needed for right now, Mistress Victoria." Asks the waiter, with a twinkle in his eye and a smile for the lady next to me.

"Is she yours, William?"

"Oh, yes Mistress. Still in training, but coming along nicely. Is this one a new trainee?"

"Just finished the negotiations and in the final phases of acceptance. You remember that weekend, don't you?"

"Oh, do I, it is one of my fondest memories. That and the year that followed. It was in that year we discovered I was a switch, hence the young lady here as mine, among others."

"Any questions for my ex-submissive?" Asks my Mistress to me.

"Well, do you have any advice for someone like me starting out with Mistress Victoria?" I ask, hoping for some good guidance.

"My only advice, from a year of being hers is, listen to her, mind her, and most importantly enjoy her, for she is one of the best at this."

"Thanks, I will try." I answer truthfully.

"I'll head in and deliver your order, while I'm at it, I'll gift you two with an appetizer, on me."

"Thank you William that is a nice gesture to a plain old lady like me."

"You are not old and one of the more sexier women I know."

"Again, thank you for those kind words. Now off with you, I have a lot to discuss with this young man."

"Yes, ma'am" is the answer and they both disappear.

An appetizer of Oysters Rockefeller is delivered with a tongue in cheek comment "You may need these over this weekend."

"You cheeky boy, you know damn well that he will only need some Viagra."

"Yes, ma'am, but it pays to be prepared." Is the answer with a smile.

We chat as we eat dinner, and I discover that she usually has 1 to 2 new submissives per year. The more fun they are, the longer they last. Our situation is not discussed, for it seems we are waiting until after the meal, to talk about my admission into her harem.

As dinner is cleared from the table, Mistress brings out the contract. "Please read it over and note any changes you want. If no changes and you are satisfied, then sign and hand it back to me to sign."

I read it over, nothing changed, no additions, just the way I've seen it before. Taking up a pen, I sign away my right to make decisions for the next two days.

My possible Mistress now, by her signature, becomes my short term Mistress. I am now hers until Sunday noon. My stomach does a flip flop and I realize that I don't know what's next.

Mistress looks over at me and asks, "Are you wearing any underwear?"

"Yes, Mistress" for the first time and I know not the last time.

"Go to the bathroom, remove your underwear and bring them to me. You will not be needing them until Sunday afternoon and maybe not even then." Commands my Mistress, giving me my first command of the weekend, and definitely not the last. My stomach is doing another flip flop, a little worry and this was only the start.

I say "Yes ma'am" as I get up and head to the restroom. In there, I take over the handicapped stall and undress to the point I can get my jockey underwear off. Dressing again and keeping my cock out of the way, zip up. I now put the underwear in my pocket and head back to the table.

"Here you are, Mistress." I say, as I hand her the crumpled, handful of my underwear.

She takes it, spreads to out and examines it. "Ah, these are nice; I have always liked Jockey because of the pocket for your cock and balls." Holding them to her face, she says "and they are still warm. Good boy, sit down and we'll discuss what happens next."

I sit down on the bench seat next to her, where I have been for the evening. As I sit there, I feel her hand slide up my pants leg and cup my balls at the crotch. I spread my legs, giving her more access and hear a soft voice from her "Good boy, that is the correct response."

I feel the hand move a little higher and caress my semi-hard cock. As she leans over to look me in my face, I feel the hand grasp my dick, through my pants. As she moves her hand along my dick, both her and myself feel it grow longer and harder. "Very good, I like to feel it grow under my handling. Keep it up."

I smile and scoot forward to allow more access for her. She grips my cock and jacks it by holding my pants against my cock. I close my eyes, as the wonderful feelings I have been missing for the last month or so, are brought to the surface.

After getting the check and paying it (we split the check), we get up and walk out to her car, while I'm trying to hide my hard-on. The waiter sees us and with a knowing smile says "Good night and enjoy what's going to happen."

Mistress Victoria answers, "I have a feeling that I will enjoy anything that rises tonight."

The valet brings her two seat car, with the top down, around and she climbs into the driver's seat. I set my small bag behind the seat and climb in next to her. She looks over at me and guns the car out of the parking lot, laughing as we head toward the highway.

Up on the highway, she looks over at me and says, "Drop your pants onto the floor. I want to see your cock."

"Yes, ma'am" and undo my pants and drop them down around my ankles. My cock is now hard and standing straight up from the pubic hair at the base.

Mistress reaches over, grasps my cock and starts to run her hand up and down it. I close my eyes and lay back to enjoy her ministrations. She looks over at me and says "Do not cum. Remember you have agreed to have an orgasm only when I tell you to and right now, you are not to cum. Hear me, my toy, do not cum." As she is saying that, her hand moves harder and faster. I find myself fighting to keep from cuming, I've been turned on for a long time now, I feel my hands clinch and the mussels in my crotch clamp down.

"Mistress, please either stop beating me off or let me cum. I don't know how long I can hold off, please Mistress." With that begging, she stops her hand but continues to hold on.

"You did very well; we'll continue this in the hotel room, pull your pants up and settle down." As she exits the highway and heads back to the hotel, still holding my cock. She only removes her hand as I pull my pants up. After buckling my belt and zipping my fly, she pats the spot where my dick is hiding and says "Good boy."

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