My Sisters Pt. 01: Claire

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Three sisters to fuck, a million dollars to win.
5.6k words
4.3
95.8k
112

Part 1 of the 4 part series

Updated 09/22/2022
Created 07/18/2014
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I am looking at three photographs.

In the first one there is a beautiful young woman sitting on a carpeted floor leaning against a sofa. She has shiny long black hair which is falling around her right shoulder. She has her head tilted slightly forward, and there is just the faintest hint of a smile on her lipsticked mouth. She is wearing a long woollen cardigan which looks almost like a drape wrapped around her shoulders. It reaches the floor but would be hip length if she were standing up. She has her legs drawn up and her arms are grasping her knees. Between her legs there is just visible the white material of a pair of knickers.

The second photograph is just a face. A close up of a face. It is a pretty face, young, pink skinned, there is a made-up eye looking straight at me, its colour a grey-green. It is an inquisitive eye. The other eye is not visible, hidden behind the loose brown hair that falls across the face. The nose is perfect, shaped just above the two full lips that are slightly apart as if the girl has just spoken. The lips look a little dry. Just visible in the background is a shoulder, bare except for the blurred impression of a single black strap.

The third photograph is a head and shoulders image of an attractive woman. It is a little more than a head and shoulders, it would be more accurately described as a head and breasts image. The woman is extremely attractive, more in the realms of beautiful than the first two, she has long brown hair that is tied back on top of her head, and her two deep brown eyes are looking intently at the camera. She is wearing a dress which is black with white shapes and flecks through it. The dress is low cut and affords a wonderful sight of cleavage of what would appear to be two perfectly formed breasts. The woman has her right arm raised to allow her fingers to play with her hair. It also displays the uncovered skin of her right underarm and allows a view of the bra strap running around her body. Like the second photograph this image suggests the woman has recently spoken, as her lips are slightly apart, more so that the second photograph because her white teeth are visible.

You might be wondering why I am looking at these photographs. Is it just porn I have downloaded from the internet? Am I going to masturbate looking at them? Are these photographs just random women who have taken my fancy? Well, the answer is no to these questions. These three women are my sisters, and the photographs were all taken on the same day three months ago, the day I fucked them all. These are the 'before' shots. That is, before I fucked them. I have 'during' and 'after' shots too, but these 'before' shots show my sisters at their most gorgeous, before I accomplished the 'trifecta' - on the same day I fucked one in the mouth, one in the cunt, and one in the ass. I then managed to persuade them to fuck each other, but that is another story. This story is about how I fucked all three of my older sisters on the same day, something I think I have always wanted to do.

I am the fourth child in my family and the only boy. I grew up surrounded by females as my father left us when we were barely old enough to remember him. My mother brought us up with the help of her sister, my Aunt Grace. She never married so we really had two mothers. Like most children we didn't know any different and we just accepted things in our family and just got on with it. As we grew older and became more aware of the world, something became apparent to all of us - by some quirk of nature, the members of my family are exceptionally good looking.

All of us. Myself included. Some have even said myself above all, but I couldn't possibly comment. What I can say is that my sisters all developed a natural beauty from quite a young age, they were head-turners from as early as I can remember. Tall, slim, dark haired, all have dark brown eyes, and they all have that undefinable something which sets them apart from others. They can wear any clothes and they look like models. No matter what they do with their hair, they shine. They have a natural grace in the way they move, it is a silky elegance that is entirely unselfconscious and unaffected. They all excel at sports and have developed beautiful athletic bodies that are a pleasure to watch. They all worked hard at their studies and all achieved highly in the academic world. And on top of all that, they are all lovely human beings who make friends easily and make other people feel special. It's a rare gift but all three of my sisters have it.

As do I. I don't want to beat my own drum here but I am very much my sisters' brother, cut from the same cloth you might say. I can't claim any credit for any of this because it all came naturally without my having to do anything, but I have a fabulous muscular body that is admired equally by men and women, I am top of my class at college in every subject I am taking, I am adored by everyone I am involved with, and, to be brutally frank, I am the most delightful, helpful, capable, and giving person I know! You might be feeling nauseous reading this right now, but as I say, I claim no credit for any of this, it all just landed in my lap and I just get on with it. I should also say here that I have one other characteristic that will feature prominently, as it were, in this story... I have a simply stupendously gorgeous cock. Now I'm no expert in cocks, all I know is that everyone who has come in contact with my member has said the same thing... it is big, it is beautiful, and for those who have experienced it, it is as hard as a rock. And can remain so for hours. I can even cum and retain a serviceable level of hardness. How I don't know, it just happens that way.

So how come I got to fuck my three sisters in the one day? Well, I am ashamed to admit it was all rather tacky. It was the result of a bet. Yep, that's right, money money money. But not just any old bet - this was a whopper. This was the big one. This was the life changing bet that never comes your way unless the Gods are smiling with a full set of teeth and beautiful shiny lips. This bet was worth one million dollars! One million. One million to fuck three women in the one day. I promised not to divulge the source of this bet, and I won't, but suffice it to say that the individual in question is a very wealthy businessman of my acquaintance who has a warped sense of humour. He's also my part-time lover, and the man responsible for more cock in my ass than any other person in the world. He thought it would be highly amusing to see if his gay lover boy could get it up enough to fuck three women on the one day.

We haggled over the conditions - he insisted they had to be 'real women' as he called it - that is, not hookers or lady boys or anything like that. I insisted I got to select the women. He made the condition that each had to be fucked by my cock in a different way, and that I had to cum inside the women fully through the mechanism of intercourse. We came up with the mouth-cunt-ass criteria together. He insisted that I gather photographic evidence of the acts. I insisted that it would be acceptable for me to tell the women about the bet and offer them a cut of the money if I wanted to. He wasn't happy about that initially, so we had a competition to decide the winner. We stripped off and got into a 69...whoever made the other cum first would have it their own way. I won easily. I am, I have to say, an expert cock sucker, I can bring a man to orgasm in under 30 seconds from flaccid, and that is some skill.

So the bet was laid, all that remained was for me to organise to get myself laid. The decision to go for my sisters was an easy one. First, I have easy access to them. Second, I know them well. Third, they are very sexy and I thought I wouldn't have any difficulty getting it up for them. Four, it's something I have always dreamed about, even in my recently converted gay state. And five, I had a sneaky feeling they rather fancied me in 'that' way.

So, decision made, I arranged to visit my sisters on a particular day each in turn starting with the oldest. I allowed three hours per visit. Game on!

My eldest sister is Claire. She's the one sitting by the sofa in the photo. She's twenty eight and is married with two kids. She works as a sports physiotherapist for a big football club. She is sexy and sassy and won't put up with nonsense from anyone. I know her body very well even though I've never had sex with her because she used to let me stay in her room when I was younger, so I've watched her get dressed and undressed a hundred times over the years. She only kicked me out when she found me wanking under the table holding a pair of her used knickers wrapped round my cock. She laughed at the time.

I went to her flat at nine in the morning. I told her I wanted to see her about something, and suggested we have breakfast together. Amongst all my other talents I am a very good cook. Breakfast is my speciality. Her husband and kids would be long gone by nine, so we'd have the morning to ourselves. We've always got on well so I knew she would be looking forward to my visit. I rang the bell. She buzzed the outside door and I went on up.

"Hi," she said breezily, opening the door. We hugged. She was wearing a tight-fitting white blouse and a blue skirt. Her long black hair was tied back. She was gorgeous, as usual.

"Hello sexy," I said. "Did you get any this morning?"

Claire was used to my suggestive comments, and duly ignored this one.

"I hope you've got something nice for breakfast, I'm really hungry."

"Hungry is good," I said. "I can work with hungry."

"Have you put on weight?" said Claire, looking me up and down. "You're podgy round the middle."

"Podgy my ass," I said. I put down the bag I was carrying and whipped off my shirt. "Where?" I said.

Claire looked me up and down, shaking her head.

"God, Danny boy, how do you do it?" She put her hand on my chest, and ran it, palm down, around my stomach, around my back, and up to my shoulders. "Not an ounce of fat anywhere. That's one hell of a torso you have there, little bro."

I smiled. "Not just the torso, sis. My other parts are pretty spectacular too."

"Yeah yeah," she said, smiling.

"So I've been told," I said.

"By yourself no doubt." She picked up the bag I had brought in as I put my shirt back on. She looked inside and started taking things out of the bag.

"Eggs. Cream. Onion. What's this? Corn bread?" She stopped and looked at me.

"Dan?"

"Claire," I said. She smiled.

"You know how I'm your sister and everything?"

"Um," I said, "not sure what the 'and everything' is but the sister part I recognise."

"Smarty. I'm your sister, but if I wasn't your sister..."

She paused. She had a tin of chopped tomatoes in her hand and was toying with it, turning it over and over as if she were reading all the writing on the label in minute detail.

"I mean you're a gorgeous man with a fabulous body..."

"And other parts," I added. She smiled, looking right at me.

"And other parts, so you've been told..."

"What's up, Claire?" I said. I knew something wasn't right.

The smile disappeared from her face.

"If I wasn't your sister, would you fancy me? As a man. I mean, me as a woman, not your sister, and you as a man, not my brother." She stopped, and looked at me, tears welling up in her eyes.

"Claire," I said, "you are the sexiest woman on earth and any man, even a gay brother, would fancy the pants off you. If John has done something to you just tell me and I'll bash his fucking brains out."

Claire's eyes twinkled, and she smiled.

"No, it's nothing, nothing's happened. I just wanted to check."

"Check?" I said.

"It's a woman thing. You wouldn't understand." She giggled. "Now how about some breakfast little bro? What did you want to see me about anyway?"

It was my turn to smile. I looked my sister in the eye.

"Well, as it happens, it's what you just said, really."

"What did I just say?"

"About fancying you."

"What about it?" she asked.

"Well, the thing is Claire, not only do I fancy you, as only a gay man brother figure can, but I want to fuck you. Today. In fact, I need to. Sis."

Claire had been sitting silently for a good five minutes.

"Fuck," she finally said.

"Precisely," I said quietly. I wished I hadn't. This was not the moment for flippant comments.

"Fuck."

She had hardly moved in the five minutes since I had told her about the bet, she just sat motionless. I sat down opposite her and kept my council. I thought it would be best to let her work it through. Her skirt was quite short, coming to only half way down her thighs, so I had an uninterrupted view of the white knickers between her legs. I thought looking there might help me get into the zone.

"Fuck," she said again. "That's a lot of money."

"Indeed," I said. What was wrong with me? A simple 'yes' would suffice.

"I..." she started. "We..." She looked me in the eyes. "You know I love you, don't you?"

I studied her eyes.

"There's a 'but' coming, isn't there?" I said.

"But," she said, then she stopped. "Fuck that's a lot of money!"

"It's nothing if you won't, if we don't, you know, fuck," I said. "That's the deal."

Claire stood up.

"Take your pants off," she said briskly.

I was taken aback. "What?" I said weakly.

"Take your pants off and show me your cock, Danny boy. I can't decide without seeing the merchandise. You know me." She smiled. It was a genuine smile. I sensed she had 'worked it through', and like the sister I knew oh so well, once she had come to a decision, there was no time to waste, and no going back.

I stood up. She watched me closely. "Shirt first," she said. I pulled the shirt over my head for a second time. She smiled. "Fabulous, Dan. That's a turn on by itself. Speaking as a woman, not a sister you understand?"

"Goes without saying," I said. I then unbuckled my belt and slipped my jeans off. Claire's white knickers had had some effect, but my days of being fully turned on by women's underwear were past me, so my rod was not exactly iron-hard.

Claire stepped towards me and looked me in the eye.

"Little brother," she said, smiling. She squatted down in front of me and laid her hand on my cock which was making a valiant effort to raise the material of my boxers.

"Let's see," she said, and without further ado she pulled my boxers down. My cock sprang out, and managed a half-mast salute. It was still quite a sight, even though I say so myself.

Claire was smiling. "My little brother's cock," she said. She wrapped her hand around the shaft and gave it a little squeeze. Then she opened her hand and began stroking, gently up and down, she cupped my balls in her hand and used her finger nails to tickle and scratch. Clearly my sister had had a lot of experience in the cock department, in no time she had my member throbbing away like it did in my partner's mouth.

"Very nice," she said. Then she suddenly stood up. She grabbed my cock in one hand and squeezed it tight. I smiled - that was my favourite thing, a tightly squeezed cock.

"I'll tell you what, brother," she said. "As much as I am in thrall to your amazing body, which I have to say is bloody amazing, I'm sure I'm wet just thinking about it, as a woman you understand, but I can't let you fuck me properly, fully. That's John's privilege and duty. But I can let you have my mouth. How about I suck you off, that can be my contribution to your get-rich-quick scheme? You said you have to have all the sisters in different ways, I'm the only married one so perhaps we can persuade Jilly and Beth to let you have them the other ways? I don't think Beth will mind but Jilly might object. Might I suggest mouth for me, ass for Beth and cunt for Jilly? God what am I saying?! But that's what I think."

She stopped talking, but continued to squeeze my cock. This had gone better that I had any right to imagine. Not only was I to get my cock into my big sister's mouth, but she was going to help me persuade the sisters to let me fuck them too! One million dollars here I come!

"Are you a big comer?" was the next thing Claire said.

"I... yep," I said.

"Do I have to swallow?" she asked next.

I hadn't thought of that detail.

"Er, no, I don't think so." I said. "Unless you want to."

"Not really," she said. "The eggy breakfast you will make me after will be quite enough sustenance for me."

"I'm going to change," Claire said, and she dropped my cock and turned away. "Don't go anywhere, I'll be right back."

So I was left there in the kitchen, stark naked, with a fast withering cock and a half unloaded bag of food. What should I do?

Nothing as it turned out, Claire was only gone for two minutes, she returned wearing the woollen knit mini dress she has on in the photo. She strode over to me and put one hand flat on my chest, and one hand around my cock. She gave my cock little gentle squeezes as she spoke.

"I want to get things clear, Dan. As far as I am concerned this is a one-off, I'm happy to help you get your money but we're not going to make this the start of some crass incesty affair thing which is bound to go wrong mainly because you appear to be a gay man with three sisters, so how's that going to work? Furthermore, I am happily married..."

I put my hand over Claire's mouth.

"Shut the fuck up, sister," I said. "Any more furthermores and I'm going to put your head down the toilet. Now let's do this. I want to, you want to, don't you?" I looked at her and raised my eyebrows. She nodded.

"So get yourself over there by the couch, sit down in a provocative pose so I can take a photo, and prepare your mouth for a good fucking. It's time my cock visited the inside of your body. Despite the fact you are a slightly distasteful female, I'm rather looking forward to it." Claire mumbled something. I took my hand off her mouth.

"Me too," she said. She looked me in the eye and bent forward and kissed me on the lips. "I know this is all wrong but I don't care. Let's take it slowly and really enjoy it," she said. "Brother."

"Sister," I replied with a smile.

Claire moved across the room in that easy, loose limbed way she has, she really was a delight of a woman. I could feel my cock stiffening. Wow! Not many women have that effect on me. She reached the sofa and turned to face me.

"If I sit on the floor I'll be about the right height for you to stand, if you get what I mean. Your cock my mouth same height is what I meant to say!" She was grinning hugely.

"Perfect," I said.

She pushed a small coffee table aside and sat down on the floor with her back to the sofa. She lay her legs out straight on the floor. "How's that?" she said.

I walked around in front of her.

"Not sexy enough," I said.

"Oh thanks," she said.

"Not you," I said, "the pose. Try lifting your knees, so I can see under your skirt."

"Not your sort of thing usually?"

"This is not usually! Just lift up...more...bit more...there! Perfect." Her feet were now only a foot or two from her bottom, so her knees were up in the air. I had a lovely sight of her knickers just peeping out from between her legs, lovely and white and smooth.

"Nice knickers," I said, smiling.

"Thanks," said Claire. She reached back and undid her hair, letting it cascade around her shoulders.

I took a photo. Then another. And another just to be sure.

"He'll love these," I said. "I'll take some more of you with my cum on your mouth, or face, or wherever it goes."

"Lovely," Claire said. "Anything to oblige." She smiled.

I put the camera down and looked at Claire. She was ravishing.

"Dan?" she said.

"Second thoughts?" I asked.

"No," she said, "not at all. I, er, I want it now."

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