Jill's house stood in a large garden in a leafy part of town. Jill had her own business, and at 24 she was considered a bright young thing in the business world. Great things were expected of her, and as far as I knew, it was so far so good. She had a lovely big house, brought with the proceeds of her manufacturing companies. She did something in steel and something in fibre glass and something in lingerie -- an odd mix but she seemed on top of it all. She wasn't married and as far as I know had never had a serious relationship. This was a concern for The Parents, apparently, they went on about it all the time. What is it with Parents and daughters? They never hassled me about my unmarried and childless state, so why put all that on Jill? She seemed happy enough, although her relationship with The Parents had become rather tetchy of late.
To be honest my relationship with Jill was not the best either. Despite being her stupendously gorgeous and talented brother Jill never made any effort to contact me, or showed any desire to spend time with me. She was the youngest of the sisters, and therefore closest in age to me, but that didn't seem to count for much. I'm not saying we didn't get on or we have fallen out or anything like that, just that we don't have the easy communication I have with Claire and Beth. As I swept down the long gravelled driveway towards Jill's house I wondered how I was going to complete my plan..... fucking one sister, problematic. Fucking two sisters, a miracle. Fucking three sisters, an impossible ask? Especially when the third sister is likely to be the most resistant to even the suggestion of a brotherly fuck.
As I always do I parked my car around the back of her house, next to the kitchen. Jill said she would be home around two, so it was no surprise to see her red sports car parked there too. I pulled up next to it, climbed out of my car, and went through the gate towards the back door. I was feeling nervous! Me, Mr Confidence himself. My cock was unusually quiet.....nothing was stirring down there. Not a good sign, although not an unexpected one in the circumstances. As I approached the door I began to wonder how this day would end. Would I fulfil my mission, or end up in frustration in more ways than one? What if Jill did not want to....do it? It would be pointless offering her a cut of the money, she had more than enough of that already. Money, or at least a little bit extra, would mean next to nothing to her. Even the whole lot would barely turn her head. Would I have time to find another woman? I could buy one easily enough, but that would be against the rules. Nope, I'd just have to do my best, use my whole arsenal of winning charms, and hope against hope that my sister would relent and let me fuck her. Just the once. No long term commitment, just in, out, shoot my load, one million dollars thank you very much. Surely a sister would indulge her little brother, just the once?
The back door was open, so I went through and into the house. Jill was there, in the lounge room, standing looking about her. She looked at me over the rim of her glasses.
"Hello Dan," she said. I smiled and gave her a little wave. "Samples," she said, opening her arms and indicating around her. On all available surfaces were sets of underwear, knickers, bras, camisoles, slips, corsets, all colours and patterns and styles. "Summer collection time again, I've got to choose." She looked at me as I stood there. "Coffee?" she said.
Jill is a very pretty, happy looking woman. She has similar features to the other two but she just carries it off in a more, I don't know, sexy and feminine way. She has a natural confidence about her, verging on arrogance, but she has the sweetest smile which disarms and invites at the same time. Men and women go weak at the limbs in her presence which is not a good career move for them because she is quite ruthless in her business dealings, and she will exploit any weakness to her own advantage. Drooling men are putty in her hands. Whimpering women seeking her approval have no chance. I am somewhat impervious to her charms, and usually it really doesn't matter to me, but on this occasion I had a mission and a purpose and my task was to break through that force field and get my cock into her knickers.
"Do you have anything stronger?" I asked. "Beer?"
She looked at me. "Of course," she said. "Hard day at the office?" She smiled.
Now, that got me wondering. Her magic was working on me already! Did she know anything? Had Claire or Bethany talked to her? Was this just chit-chat, or was she maneuvering for position? She was so good at finding a chink, which she would then unceremoniously drive a bus through.
She opened the fridge and took out a beer, which she waved at me. I shrugged and nodded.
"Claire called," she said, slipping her finger under the ring-pull of the can. As she looked at me, she ripped the ring off with a pssst, and handed me the can.
"Glass?" she said.
"Did she?" I said, shaking my head at the offer of the glass. I took a pull from the can. Ah, lovely and cold, just what I needed. Too cold to taste, but that's the only way to drink that sort of beer.
"She did," said Jill. She pointed to a chair and slipped herself onto one in one elegant movement. Jill was wearing a lovely tight fitting dress, typical of the sort of clothes she wore. It hugged her beautiful figure without being suggestive, and displayed just the right amount of cleavage to leave you in no doubt that this was a woman in full control of herself, and a strong, assertive woman, do or say anything about her body at your peril! The dress was black, and it had flecks of white and red and other colours all over it as if a painter had loaded his brush and flicked the material from afar. It was lovely. And when she lifted her arm to play with her hair I could see under it, which revealed she was wearing a deep red-coloured lacy bra. Again, suggestive without being slutty, and definitely a challenge to the viewer to know what to do with that information. In the right hands that is powerful stuff indeed, and Jill's hands were crafted from the right stuff!
"It seems," she said, "that you have caused quite a, what shall we say, stir...amongst the sisters?" She took a sip from the glass of water she had poured herself. She kept her eyes on me as she did so. I took a swig from the beer.
"It would seem so," I said slowly, my eyes not moving from hers. "Stir is probably a good word," I said.
"Hmm," she said, slowly putting her glass down. She raised her arm and pulled a strand of hair back behind her ear. "Claire was......" she started, then she stopped and quietly drummed her finger nails on the wooden table top. "Claire was......Claire was remarkably....obliging, wasn't she?" She smiled, but her eyes didn't smile with her lips.
"Obliging?" I said. "Sounds rather....contractual. I'd have said more like...involved." I smiled back. "Enthusiastic, even."
"Hmm," said Jill. "Claire is never enthusiastic, she's too....cautious."
"Not this time," I said. "Guarded yet deliberate, I'd say." I took another drink from the beer, which drained the can, so I scrunched it up in my hand and placed it, in a tight ball, on the table. Jill watched me in silence.
"Bethy, on the other hand," she said, "sounded quite overcome." I smiled at her choice of words.
"You could say that," I said.
Jill looked at me for what seemed like a long time. Then she stood up, went to the fridge, took out another beer, pulled the ring top off and threw it into the sink, and then returned to her seat, sliding the can across the table with a perfect weighted push which had the can sliding to a stop an inch from my hand.
"When a potential client wants to do a deal with me, I expect them to do a great sales pitch," she said, smiling again. That smile of the assassin. She raised her eyebrows.
I looked at her for a moment. Then I put the can down on the table with a thump. I stood up.
"Fuck it, Jill. I'm not playing your fucking game," I said. She sat back and folded her arms. "I need to fuck you to win one million dollars from Thomas, I know that's, well that's, it's well, it's what it is, I know that's not a lot of money to you but it's the whole world to me and I've....done two thirds of the task and as bizarre as this may sound I'm asking you to let me fuck you in the traditional way, nothing weird, just a normal...." I shook my head, " a normal boy-girl thing, boy-girl fuck, you know, missionary and all that, just the once, you can shut your eyes and wear a head set playing any music you like, or radio, radio's fine too, and once it's done we can just forget about it and go back to normal, maybe we can't but we might be able to just forget it ever happened and I can get the money and you can, well, you can be happy you helped me get ahead. You're good at that, Jill, it's an endearing quality you have. Amongst lots of other endearing qualities." There was silence. I couldn't cope with silence, I needed noise. "Claire quite enjoyed it actually. So did Beth."
I stopped. Jill sat for a moment, arms crossed, looking at me intently.
"Isn't there a photograph involved?" she said.
