A Rewarding Evening

It's Friday evening, and we are in our suite at the Beekman Hotel on the edge of the Wall Street area in lower Manhattan. We have decided to take a long weekend in the city, visit some galleries, walk Central Park, have a couple of good meals, and use the opportunity to live out another of the erotic fantasies we have been writing about. This time it's what has occupied our thoughts quite a bit recently - high class prostitution. Ever since you told me that you have harboured thoughts of being a prostitute for quite a long time, we've been eager to see how it might work out.

As always, the question is just how well reality will live up to our erotic imaginings. So, far, we have yet to be disappointed, but this one could be a little more hit and miss.

I'm enjoying helping you dress for the evening. The green silk corset has been laced up, and then I help you slide into the sheer stockings and attach them to your garter straps.

Somehow, as I am doing this, my fingers manage to slide all the way to your delicious pussy, and gently caress your moist lips. Then my tongue finds its way into that sweet tasting slit, arousing you still further. You tolerate it for a moment or two before punishing me for my impudence with a couples stinging blows from the flat of your hand across my face.

Now I sit back on the bed, nursing my gin and tonic, and watch as you wriggle into the tight black leather skirt, which just comes below your knees, and then as you put on the matching jacket, leaving the top button open so that just a glimpse of the green silk corset can be seen. This is one of my favourite outfits, the leather is so soft, and I can smell its scent from where I am on the bed. Then on go the five inch black leather pumps from Louboutan. I love the contrast of the red soles, very sexy. I think to myself that it will be very hard for any man to resist you in this outfit.

I continue to watch as you sit down at the dressing table and start to put on your lipstick. First the red, scarlet really, chosen to match the colour on your shoes. Then, carefully applied, a thin line of black ombre around the red. I don't know why, but this always looks very dominant to me. Task completed, you stand up and turn around to face me.

"What do you think?"

"Perfect. Any man who would not want to take you to bed and fuck you to death, must have a serious problem."

"Yes, but will a good looking black businessman be willing to pay for his pleasure?"

"Well, given what I am looking at, I would certainly think so."

"Shall we go down?"

"Yes, it's just past seven, so things should be moving along quite nicely by now."

"You are going first?"

"Yes as we discussed, I'll get myself a comfortable seat in one of those cosy corner booths, if I can."

You give me a light kiss as I pass you towards the door, "See you down there."

The bar is already quite busy as I squeeze myself into a corner table. The clientele is largely executives from the business district with a sprinkling of couples thrown in, much the same as we had seen the previous evening when we came down for a drink before dinner to scope out the scene. There are still a few seats left at the bar, and I note with interest that tonight it's all men there, mostly in groups, but a few on their own, including three black men, two of whom are quite good looking.

I'm still studying them when I see their attention shift from their current focus to the entrance to the bar. It's almost comical, watching all these heads swivel at once. Of course, I know the reason why, without even having to look for myself, although I do. They are all smitten by this vision of loveliness that has just arrived; a beautiful, elegant forty-somethingish woman in a stunning black leather suit, impossibly high heels, but with a reserved, unaffected air about her that is sexy in an understated way. You know that they are all asking themselves one question - is she alone?

You take a seat at one of the vacant spaces at the bar. Not, I note next to any of the black guys, but between two younger white males. We have always wondered what happens now. Do you buy your own drink, or does someone immediately offer you one? You have only been there a moment when a man in his mid-thirties detaches himself from the other two men he is standing with, walks over to you, and says something to which you nod. He calls to the barman, and then both of you walk back to the group he is with.

You stand and chat with the group for maybe twenty minutes, obviously enjoying their company. I wonder what the conversation is all about. Are they interested in you? Are you interested in them? They are all quite good looking, fit, and they seem to have a good sense of humour judging by all the laughter.

I am watching you intently, wondering just what will happen here. Then, I see your head swivel towards the entrance, and I follow your gaze, and I understand why your attention was distracted. He's just walked in, hasn't he? The tall, lean powerful black man we always thought might turn up in the bar. He appears not to notice you, and walks over to the bar, taking a seat by himself. He calls the barman over and orders a drink. Then he turns to the room and his eyes settle on you. After that, they never leave you, not for an instant. He doesn't even look at his drink as he picks it up.

You continue chatting with the group for another few minutes, but then with a shake of your head, you politely wish them good evening and head back to the bar, drawn by his gaze to the empty seat next to him. Now my gut is churning. I'm excited, aroused, and I know that you are as well, probably even moreso. The game is on.

From the cut of his well-tailored dark blue suit, I guess that he is in the financial industry, and either in town on business, or stopping off for a drink before heading home. From his build, broad shoulders, tight waist, he definitely looks like he works out. He could even have been an athlete. I'd put him in his early forties.

He calls the barman over again and orders you a glass of champagne. The two of you are quickly into an animated conversation. I am sure that he is finding out what you are doing here, whether you are alone, maybe what are your plans for the evening? I watch as your knees come closer together, as his fingers lightly brush your arm occasionally, and then his hand comes to rest on your thigh. There is already an easy intimacy between the two of you. You appear to be totally absorbed by him, sparing me not even a glance for maybe half an hour, until you finally appear to take a look around the room, and giving me the briefest of smiles as you do so, but not sufficient to cause him to look in my direction.

He orders another round of drinks for the two of you, and you continue chatting for another twenty minutes or so. All the while I am watching the two of you intently. I don't want to miss any of the little intimacies; the knee contact, his hand gently caressing your thigh, your hand resting on his arm. You could be two lovers out for a drink. But this is a man you encountered not even an hour ago. I wonder how excited you are, whether you are getting very moist between your legs? Whether you can't wait to crush your lips to his, and feel his big hands running over your breasts.

Yes, this is why we selected the Beekman. The bar is a known haunt for wealthy financial executives looking for company for an evening, and maybe willing to pay for the pleasure, and, being on the edge of Little Jamaica, with a mixed black and white clientele. Our fantasy was indeed coming to life here. The elegant businesswoman on her own at the bar. The husband tucked away in the corner, relegated to the role of voyeur. The good looking black executive looking for some companionship.

I wondered what you had told him about yourself. Whether you had decided to stick with the business woman in town for the weekend, looking for a wild evening, or whether, as we had sometimes thought, decided to play the role of the bored housewife, moonlighting as a high class escort, looking for a new client? Either way, it looked like you were enjoying each other's company.

After an hour or so, the conversation looks like it is winding down. You stand up, pick up your purse, give him a friendly smile and a nod, and turn to leave. You don't even glance in my direction. I notice that he is watching you all the way to the entrance. At first, he shows no sign of leaving, and I wonder if the two of you had decided to go your separate ways, but after a few minutes he calls the barman over and settles his tab. Then he walks towards the entrance. I get up and follow him out towards the elevator. I know that this is not in the script, but I have to know whether he's otherwise engaged for the remainder of the evening, or whether you have decided to be very discrete.

We both stand waiting for the elevator. I find it quite wild that he has no clue that he is standing next to your husband. Is he also staying at the hotel? If he is, it's on the ninth floor, the same floor as us. I nod at him as he asks what floor I want, "Same floor please". We exit the elevator. I go left, he goes right, towards our room. I walk slowly, looking back over my shoulder. My stomach gives a big lurch as I hear him knock on one of the doors. I quickly look back again. Our door! Your arm reaching out for him! He steps inside and as the door shuts, I think I can hear laughter.

I retrace my steps until I stand outside our door. Then, again not in the script, I put my ear very close to it and try to catch any sounds coming from within the room. I can hear voices, but very indistinct. Then there's a silence, quite a long one, then more voices. I am torturing myself now. Has he just kissed you? Is he already undressing you? My mind is racing as I turn away and take the elevator back down to the bar.

I am alone in the bar with my thoughts, my very wild thoughts, for over two hours. All the time I am wondering what is happening right at this moment in our room. I think of you doing all the things that we had imagined in our fantasies and more besides. I imagine him kissing you, undressing you, caressing you, making you shudder as you cum. I imagine you sucking his cock, looking up into his eyes. I wonder if you are playing dominant or submissive with him.

I am broken out of my reverie by the phone ringing. I hear your voice on the other end of the call, "Hello, it's me. I excused myself to go to the bathroom, so I could call you. We are heading out together. He wants to take me to a club that he knows. It's called the Negril Village Lounge. It's not far from here, near Eighth Street, I believe. So if you want to you can come back to the room in ten minutes or so, we'll be gone by then, or if you want to play the voyeur some more, you can take a cab to the Negril, and maybe I will see you there. I have to go now."

"Yes, I'll be at the Negril, but before you go, tell me quickly, so I can sit and imagine what you have been doing, how is he? I assume not bad if you are heading out to the club with him."

"His name is Lebron, and he is a very good lover. A very good kisser, and he has a nice long, thick black cock that has kept me very satisfied for the last two hours. And I think he really likes my cocksucking skills. After we got to our room, I gave him a really good, slow blowjob, and then he was all over me."

"What did you tell him? What we agreed?

"Yes, he thinks that I am here on business and have to stay over for the weekend. But I also told him that I am very dominant, that I like all my men to worship me. Actually, he's already had a taste of the whip, which I think was a new experience for him. Listen, I have to go now. I'll look for you in the lounge. Bye!"

As soon as you put the phone down, I walk quickly outside and hail a cab. The ride to the Negril Village takes only five or six minutes. Once inside, I am faced with a choice, the upstairs or downstairs lounge? I take a look in both rooms. The downstairs lounge is darker and more intimate. Both rooms are about two thirds full, mainly occupied by couples and small groups, mostly black, a few white and a few more interracial. A few couples were dancing in the downstairs lounge.

I decide that downstairs will be the place, and I find myself a table towards the back of the room from where I can see almost everyone. A black waiter takes my order for a double gin and tonic. He is obviously a bit surprised to see me, a white guy, there alone, but he says nothing. Maybe he thinks I might be there to pick up one of the good looking black girls I notice dotted around the room.

My drink arrives quickly. I look around the room, I am the only white guy on my own, but there are a few single black males. Mostly it's black couples and groups, but there are several white couples with black male companions. I amuse myself by wondering how many white cuckolds there are in the lounge. A few of them become obvious when their wives head for the floor to dance very closely with their black companions.

It's half an hour after I arrive, when I am just about to check upstairs, that you and Lebron walk into the lounge. I notice immediately that you are holding hands, and that you look like you have been very well fucked. You've also changed into one of your rather daring, low cut little black dresses, which shows off your figure and your legs very well.

Luckily, Lebron spots an empty booth just across from where I am sitting, and heads towards it, so I will have a clear view of the two of you. But then you pull him back and point out a different table, a bit further away and more secluded. I know that you have seen me because as you turn away, you glance quickly over your shoulder at me, your expression as if to say you don't want to make it easy for me to be the voyeur.

However, I can still see the two of you, although not as directly, and you aren't sat facing me, but I can see that as you sit down, he draws you towards him, and you exchange quite a lengthy kiss. As always, that immediately raises my arousal level.

Lebron orders drinks, and then it goes even higher as I watch him take you onto the dance floor. The way you dance together, closely, hands all over each other's body, it must be obvious to everyone in the room that the two of you are lovers.

After a couple of dances, you head back to your table, and I can see the two of you thoroughly enjoying each other's company. I am sure that there is a lot of caressing taking place under the table. I idly wonder if you are wearing any panties, in fact if you are wearing any underwear at all. Maybe a garter belt?

I look at my watch, and see that it is eleven-fifteen. You've been at the lounge for just over half an hour, and the two of you are back on the dance floor, his hands blatantly caressing you as you move together. It's almost like simulated sex.

I become aware of a group of four newly arrived black guys, all big and good looking. They are stood on the edge of the floor watching you with Lebron. Then I see Lebron catch sight of them as well, and he gives them a big grin and a wave as he points them to your table.

You finish up your dance and head back to the booth. Two of the men stand up and let you slide along into the middle of the group. This is also not part of the script. I wonder if Lebron has told you that he has asked four of his friends to join you both. And what are you thinking, as you sit among these five good looking black men.

I really can't see you very well now that you are in the middle of the group. I can catch sight of you every now and again, but it's more the men that I can see, and they all appear to be enjoying your company. It's not long though, before you to take to the dance floor with one of the new arrivals. It's wonderful to watch you dancing very close to him, his face close to yours, his hands holding your body even closer. The guys left at the table are also watching the two of you, and I can see them occasionally pointing at you as they talk. I'd love to be listening in on their conversation.

Over the next hour, each of the men takes it in turn to dance with you, and there is one spectacular dance when two of them take you onto the floor. Watching you dance with one close up in front of you and the other close behind you is simply an erotic tableau with clothes on.

Finally, you appear to excuse yourself and head for the washroom. I wonder if I should follow you, but I don't want anyone to realize that we are together. I shouldn't have worried because it's not two minutes before my phone rings. "Are you enjoying the evening?" you ask.

"It's simply amazing. Five good looking black guys? That was definitely not in the script. But I have to say that you look very much as if you belong with them."

"I feel like I belong with them. They are actually all very nice men, and they are all very good to dance with. I am enjoying their company."

" So have you any idea what happens next?"

"Oh yes, I am just taking a quick break so that I can call you before the five of us head out. They have made me an interesting proposition, which I just can't refuse, so I will be heading out with them, and probably won't be back at the hotel until Sunday afternoon. So, you are going to be on left on your own with your thoughts and imagination for the rest of the weekend."

"That was very fast of them. Are you sure that this is what you want to do?"

"Absolutely, we are going back to Lebron's home for some fun. It seems like he has never yet met a woman quite like me. He's fascinated by me being dominant, and as I said he loved the whipping. So the five of them have invited me back to have some fun, but with me playing a very dominant role. I think I will end up whipping them all. And it goes without saying that they will all end up fucking me. By the way, don't go back to our room yet, as I am popping back in to pick up the toys on the way back to Lebron's place. Oh, and one more thing, I decided to get into the role a bit more, so I made it clear to Lebron that, as a very astute businesswoman, he should know that before he invited his friends along that I don't do things like this for free, so they have agreed to pay a thousand dollars each for the weekend. How about that?"

"Now that's a first. Being paid for your pleasures. You seem to be totally into this new role. Five thousand dollars. That will pay for the weekend and leave a lot left over for a shopping spree maybe."

"Yes, it will won't it? So, I must go now, but I will try and phone you along the way when I can and tell you what is happening, so you can lay back and fill your mind with all kinds of deliciously depraved images of me. And for sure, if we head out tomorrow evening, I'll let you know so that you can come along and watch."

"Have fun, don't do anything I wouldn't. I'll miss you all weekend."

"I'll miss you too, but think of all the things I am going to have to describe to you when I get back. This could be a whole chapter in the new book. Bye!"

A minute later I watch as you make your way back to the group. My stomach is absolutely churning, my whole being filled with lust, as I see the five men get up and submissively follow you out of the lounge. I think back to how much it took for me to persuade you to try out this adventure. And now you are leaving in the company of five good looking black guys for a weekend. And they are paying you for your time. Then it starts to sink in, you really are becoming a black cock whore, aren't you, albeit a dominant one, and loving every minute of it. What have we started here?