Brother and Sister

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She's an escort, and he becomes her client.
7k words
4.57
76.1k
164

Part 1 of the 6 part series

Updated 06/10/2023
Created 06/27/2018
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chris99999
chris99999
3,974 Followers

"I'm sorry, Rebecca isn't available. But we have a new girl, Angelina, and I am sure that you will find her a suitable replacement. Would you like to meet her?"

I didn't say yes to Grace straightaway, because I didn't want to appear desperate. But if truth be told, I was. It had been a tense day, and I needed to unwind. And the best way for me to do that, was to have good sex with an attractive woman.

By the time the call had ended, all the arrangements had been made. In fifty minutes, Angelina would be here, and she would be a beauty. I knew the precise time that she would arrive, because Grace had told me, and her ladies were always punctual. And, I knew, without having to ask for details, that she would be pleasing on the eye, because you didn't get to work for Grace, unless you were at least a nine out of ten, for both looks and personality.

While showering, I found myself thinking about the first time. It was nine months ago. I had just signed a lucrative contract, and Bill, the client, had insisted that we have a few drinks to celebrate. I didn't want to, but I couldn't get out of it without appearing rude. My signature on the document had made me, at only twenty five, a millionaire. You would think that I would want to go out and have a good time, but what I really wanted to do, was to go home and work on my next patent, that would earn me another million.

Bill suggested that we go back to his hotel. Apparently, the bartender there made a mean cocktail. I was happy to do that, but his hotel was on the other side of town, forty minutes away. It would be a late night, and I wasn't looking forward to the journey home, especially after consuming a lot of alcohol. Then I had to smile. Problem solved, I would book a room. There was no point in having money, if I didn't use it to make my life easier.

Traffic was a bitch, and forty minutes ended up being fifty five. However, it was worth it, because, as promised, the cocktail was divine.

I was on my second Singapore Sling, when he asked, "I know that you aren't married, but do you have a girlfriend?"

"No," then I quickly added, "But I have had girlfriends before."

That got a polite smile from him, but I could tell that he really wanted to laugh. It was a stupid thing to say. I had just confirmed his opinion of me, that I was a nerd. But I wasn't upset about it, because it was true. However, I now wasn't just a nerd, I was a very rich one!

I thought that he was just making polite conversation, but his next question made it clear that he had asked for a reason.

"Would you like some female company?"

Before I could give him an answer, he said, "Of course you do. After making both of us a lot of money, why wouldn't you?"

He was now making a call. I would probably have said yes, but he hadn't given me the opportunity to do that. An hour later, there was a woman in my hotel room. She was very attractive. I wasn't an expert on women's clothes, but even to my untrained eye, it was obvious that what she was wearing was expensive.

"I'm Rebecca, and you must be David. It's nice to meet you."

She then gave me a smile, so radiant, that it took my breath away.

When, after two hours, she left, I was in love. The sex hadn't just been good, it had been out of this world. However, I couldn't believe how stupid I was. Before leaving, she had given me a business card.

"If you want to see me again, and I hope that you do, then please call this number."

It was a plain white card, with just a phone number on it, and the following words, in bright red ink.

'Grace's Girls'

I had naively thought that she was one of Bill's friends, but she wasn't, she was really an Escort!

After showering, I made myself a drink. A double of my favourite malt whisky. It was to relax me. I was excited, but I was also nervous. Very soon, Angelina would be here. I have always been awkward in the company of women. I'm better now than when I was a teenager, age and wealth have improved my confidence, but I still find it daunting when I meet a woman for the first time, especially when it's one, that soon after, I will be having sex with.

Why am I like that? It's not that I'm ugly, or that I have a small cock, that I'm embarrassed about. My looks are at least average, and my cock, at six and a half inches, is better than that. It's just the way that I am. I can't complain. I didn't get as much self-confidence as I would like, but I got way more than my fair share of intelligence. And that high IQ, coupled with a fierce determination to succeed, had made me, at a young age, very wealthy.

As expected, Angelina was on time. And, as with all Grace's Girls, her effortless charm soon put me at ease. We were now sharing a very expensive bottle of champagne. While we made small talk, I was taking the opportunity to check her out.

She was late twenties, possibly older, but I would be surprised if she was over thirty. Despite her pretty face, that was framed by a stylish hairstyle, a lot of men that were younger than me, would not find her attractive, because she wasn't curvy. Her tits weren't melon size, that teenagers always drool over. She was slim, with subtle curves, and her breasts were not much more than a handful. However, as far as I was concerned, she was perfectly formed, and her body would more than satisfy all of my needs. Grace knew my taste in women, and she couldn't have selected a better one for me than Angelina. Next time I speak to her, I must remember to thank her.

As soon as she emptied her glass, I offered to refill it, but she said no. Then she took hold of my hand. The meaning was clear, it was time for us to go to the bedroom. When we got there, she turned to look at me. She was smiling.

In an authoritative voice, she said, "Undress me."

It was a command, rather than a request, but it was one that I was happy to obey.

I started with her blouse. As I slowly unbuttoned it, I gazed into her large chocolate brown eyes. You could get lost in them. When the last button was popped, I parted it, and then I slipped it off her shoulders. It fell onto the floor.

When I looked down, I could see her breasts, covered by a red bra. They were small, but they were enough to make my heart beat faster, and for my cock to rapidly expand. I could never understand why most men preferred them large.

When I reached behind her, to unhook her bra, she said, in a low voice, that was almost a whisper, "It opens at the front."

I mumbled, "Sorry," and my embarrassment amused her, because she giggled. I didn't mind, because it was my fault, and it was worth it to hear her giggle in such a girly way.

Her bra was now off, and I was staring at her tits. Two little mounds, topped with pink rosebud nipples. They were perfect. But should I touch them now, or wait until she was naked?

"What about my skirt and panties?"

Good, she had made the decision for me. Her skirt was pale blue, the same colour as her blouse. Would her bra and panties also be matching? I would bet big money that they were. It was time to find out if I was right.

After I had unzipped her skirt, I tried to pull it down, but it was difficult, because it was tight on her. She helped me by wiggling her hips. Watching her do that, sent a surge of excitement through my body. And, as I thought that they would be, her panties were indeed red. I didn't have any problem getting them off. When they were down to her ankles, she stepped out of them. Then she kicked her shoes off.

She was now standing in front of me, completely naked, but I was still fully clothed. She then giggled, and even though it was nice to hear it again, I didn't understand why she had done it.

"Is that a gun in your pocket, or are you pleased to see me?"

That made me laugh. She had giggled because she had seen the bulge in my trousers, caused by my cock straining to get out. What she had said wasn't original, but nevertheless, I had still found it funny.

Then she surprised me, by quickly putting both her hands onto my chest, and pushing me onto the bed. I landed heavily, but before I could complain, she was straddling me. Her cute bottom grinding down onto my throbbing cock. When I reached for her tits, she brushed my hands away.

"No touching," then, after giving me a wicked smile, she added, "Do you want me to fuck you?"

Before I could say yes, she was unzipping me. She had asked, but she knew that I was never going to say no, so she hadn't waited for an answer. She got my cock out, with a speed and efficiency, that confirmed that she had done this lots of times before. This was no shy virgin, this was a woman that was used to handling a cock.

As she slowly lowered herself onto my cock, she gave a low moan, that turned into a gasp, when I was fully in her and she was sitting down on me.

It took her a minute or so, to get used to my cock, then she got into a nice rhythm. She was now raising herself high, making sure to use my full length.

"My little pussy loves your big cock."

I wouldn't call mine big, but her pussy was definitely small. It was very tight. This was good, but unfortunately, it wasn't going to last long. Very soon, her sweet pussy would make me come.

It only lasted five minutes at the most, with the last one being frantic. It ended with her moving so violently, that each time she sat down, it winded me. Ideally, I would have liked to have fucked for longer, but my climax was a long satisfying one, so I wasn't complaining. While I was flooding her pussy, she had made all the right noises, so it was possible that she had reached it as well, but it was more likely that she had faked it.

Half an hour later, after we had finished the champagne, I was alone, sipping a steaming mug of coffee. If anybody had seen Angelina leave my apartment, they wouldn't have thought anything of it. Her appearance, and manner, said business woman, or professional, rather than an Escort. However, if they had realized why she had been visiting me, it wouldn't be a worry. I was single, and more than able to pay the very high price that Grace charged for her girls. I wasn't ashamed about paying for sex, but it was something that I have kept hidden from my family. My parents have traditional views, and knowing what their beloved Son was doing, would shock them.

On Sunday, as usual, it was lunch at my parent's place. A roast and the full trimmings. Today it was beef.

"How's your business. Still making you obscene amounts of money?"

That was from my Father, and it wasn't because he was jealous. He was a Dentist, with a lucrative private practice.

"Yes, but it will be next year before my new patent is approved. When that happens we can all retire."

"But between us, we already have enough money to do that now."

Mother was right, but like me, my Father enjoyed his work.

Then, after sighing, Mother spoke again.

"It's never going to happen. Are you going to work until you drop?"

The question was for both of us, but neither of us answered her, because we didn't need to. She already knew what we would say. It was yes.

My Sister arrived late, just in time to eat with us.

"Sorry, the traffic was horrendous."

Then she laughed. It was Susan's usual excuse for not being on time. But it was a joke, because she only lived a five minute car ride away.

"Tell me little Brother, how's your sex life?"

After getting a stern look from Mother, she rephrased the question.

"I meant to say, how's your love life?"

"It's none of your business."

"So it's that bad."

I just ignored her. If I was to reply, then it would just encourage her to taunt me even more. My sex life was good, no, it was even better than that. But there was no way that I could tell her who I was having sex with.

On Monday, I woke up with a raging boner. I was tempted to swiftly deal with it, but I had a better idea. I would call Grace, and book Rebecca for this evening. Shooting my load into her sweet pussy, was a lot more enjoyable than jerking myself off.

At midday, I called Grace's Girls.

"So what about Angelina?"

"That's a no as well."

I gave a heavy sigh, both of my top two choices were unavailable. This could take all day. There was an easier way of doing this.

"Grace, please just tell me who I can have."

"Kelly, Jasmine, or Sabrina."

I had seen Kelly before, and she had been good, but the other two were new to me. I could go with Kelly, the safe option, or I could be adventurous. I decided to take a risk.

"I'll have Jasmine or Sabrina. Who do you recommend?"

"You can have both if you want, and I'll give you a thirty percent discount."

As much as I would like to, a threesome would be too much for me.

"Thanks, but I only want one."

"Then it has to be Sabrina. She has only been working for me for two months, but she's already very popular. You're lucky that she is free tonight."

"OK, I'll have her."

"Good choice. She'll be at your place at nine o'clock tonight."

"No, I'm staying at the Palace Hotel, the Queen Anne Suite."

I was meeting a client there at five o'clock, but we would be finished at seven, eight at the very latest.

But as they say, the best-laid plans of mice and men...

The meeting turned out to be a long one, only ending at eight thirty, and without a satisfactory outcome. We parted on friendly terms, but only just. He wanted what I had, but he wasn't prepared to pay the market price for it. In a week's time, we would do it all over again, but I wasn't confident that the outcome would be any different.

While I quickly showered, I tried not to think about it. It had been a long tiring day, and I was tense. What I needed to relax me, was a stiff drink, followed by the company of a beautiful woman, who was willing to satisfy all my sexual needs. And that was what I was going to get!

She was late, but only by two minutes. As I opened the door, I decided that I was going to tease her about it, but I needed to be careful. I didn't want her thinking that I was being serious.

With a smile, so that she knew that I wasn't really annoyed, I said, "You're..."

I didn't get to finish what I was going to say, because I was shocked. And from the look on her face, it was obvious that she was as well, perhaps even more than I was.

She was calling herself Sabrina, but her real name was Susan. I knew that, because she was my Sister!

We just stood there, staring at each other, for what seemed like a long time, but was probably only a few seconds, before she broke the silence.

"We should go inside, before somebody sees us."

We were now in my room, and the door was closed. My mind was whirling, trying to work out what to say, and what to do. A drink might help.

"I'm having some champagne, would you like some?"

"Yes, and pour me a large one. I need it."

Then I laughed, not because what she had said was funny, but because I needed to do something to relieve the tension between us. And it worked, because she joined in.

When she'd finished laughing, her face became serious, and then she said, "There's two ways we can do this. Pretend that it's some misunderstanding, or say it as it really is."

I was clever, but not clever enough to come up with an innocent explanation. It was best to just tell the truth.

After taking a deep breath, I said, "I paid Grace for Sabrina to come to my hotel room, to have sex with me."

I had confessed. It was now her turn.

"And I work for Grace as an Escort. Sabrina is my working name."

For the next fifteen minutes, we told our stories. I, telling her about my meeting with Bill, that had ended with Rebecca coming to my room, and she, telling me about how she had started working for Grace's Girls. She was in a bar, waiting to be served, so she started up a conversation with the woman next to her. It was Kelly, and they ended up drinking together. Her new friend was happy to talk about her part-time job as an Escort for Grace. My Sister was intrigued, and when Kelly suggested that she should give it a try, that's what she'd done. And, as they say, the rest is history.

"So what do we do now?"

"We finish the champagne. You then leave, and I go to bed and jerk off."

"Thanks for sharing that with me. I now have an image in my mind, of you playing with yourself, that I'll never be able to forget."

Then she laughed, and I joined in.

Half an hour later, she was gone. Even though nothing had been said, we had an understanding. We would not talk about this to anybody. Neither of us wanted our guilty secret to be revealed.

I waited another week before calling Grace again. I had been working sixteen hours a day, and when I wasn't working, all I wanted to do was have a quick meal, then go to sleep. But it had been worth it. I had hit my deadline, and now I could relax. However, before I could do that, I needed to meet with a client at the Palace Hotel.

I got to the hotel at five, and surprisingly, by six, we had struck a deal. I had expected it to be a long meeting, but it wasn't. I was happy about that, but it now meant that I had a long wait before Rebecca was due to arrive. A leisurely shower, followed by a room service meal, ate up some of the time, but despite that, the time still dragged, especially the last half an hour. When, at exactly nine o'clock, the doorbell chimed, I jumped up from my chair. Finally, she was here.

When I saw her, I thought that my eyes were playing tricks on me. I rubbed them, but when I removed my hands, nothing had changed. She wasn't Rebecca, she was my Sister, and she looked angry. Why was she here?

"What do you think you're playing at?"

"I don't know what you mean, but you'd better come inside."

She did, and she made it clear that she was indeed angry, by slamming the door.

It took five minutes, before we understood what had happened. She had thought that I had deliberately asked for her, and that was why she was angry. But now that she realized that I hadn't, she was calm, even finding it funny. Apparently, Rebecca wasn't feeling well. My Sister knew that, but what she didn't know, was that she had been sent here as her replacement. She had just assumed that she was seeing somebody that had asked for Sabrina. I now wasn't happy. If Grace had told me about the swap, I would have been able to say no, and I could have asked for another lady. I was going to ring her up and give her a piece of my mind.

Fortunately, before I made the call, I noticed that Grace had left a voicemail, and a text. I hadn't been alerted to them at the time, because I had silenced my iPhone before my meeting, so that I wouldn't be disturbed, but I had forgotten to set it back to normal afterwards. It was my fault that I had missed them.

"So what do we do now?"

It was what she had asked last time, and I was going to give her the same answer as before.

"We finish the champagne. You then leave, and I..."

I didn't get to say the rest, because before I could, she jumped in with, "That's enough."

We were on our second glass of bubbly, when she suddenly declared, "I'm going to give you a massage."

That was a surprise. She had never offered to do that to me before.

"Why?"

"You've paid out all that money, and you're not getting anything in return. And it's the second time that it's happened. It doesn't seem fair."

I couldn't argue with her logic, but did I want my Sister touching my body? Wouldn't that be weird? No, it was just a massage. Then I noticed that she was rubbing her calf.

"What's wrong with your leg?"

"It's OK, just some stiffness. I went for a run this morning, longer than I normally do."

"It looks like you're the one that's in need of a massage."

For some reason, that got a big smile from her.

"I think you're right. But be gentle with me."

It had just been an observation, but she had taken it as me offering to give her a massage. And she was now starting to undress, so it was too late to say no.

chris99999
chris99999
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