This became the new pattern of her life over the next few weeks. She felt so alive! She no longer had to worry about how she looked or behaved; she had given over that part of her life to James. She found it so liberating! She found she could tease him by opening her legs, giving him little glimpses up her skirt, knowing that he probably couldn't actually see her pussy, of casually running a finger between her breasts, tweaking her nipples while he wasn't looking and pretending not to notice how his eyes devoured the sight of her turgid nubs poking through the gossamer thin material. It always ended up with him taking her and fucking her hard, to their mutual satisfaction. It was after an excellent session with him taking her from behind, on her knees, doggy style, with them both relaxing in a warm post-coital afterglow that James made his play.
"Elaine, I'd like you to do me a big favour."
"Yes, of course, James, what is it?"
"You know my nephew, Simon?"
"Well, I've never met him, but you have talked of him a few times. You are very fond of him, aren't you?
"I am. I think of him like my own son, sometimes and I'm worried about him."
"Why, what's wrong, did something happen to him?
"No, nothing's happened, but he's going through a difficult time." James hesitated before going on. "He's eighteen...and still a virgin!"
"Is there...something wrong with him?" an image of a fat, spotty teenager with greasy hair and bad breath went through her mind.
"No, not really, it's just that he's very shy, he has no confidence with girls and it's getting worse as he's getting older. Other than being a little underdeveloped for his age, he is a fine, handsome and intelligent young man, but I'm worried that if he doesn't get over this, it will affect him for the rest of his life. Time was, a worldly uncle would arrange for a courtesan to take a boy into manhood, but I don't think that that would work in Simon's case; a single tumble with an escort wouldn't give him the confidence he needs. He needs a warm-hearted woman to take the time to teach him to be a man."
"I'd like that woman to be you, Elaine."
Elaine was shocked to her core! While they'd touched on this subject before, that James had intimated that he might give her to another man to further his business, she had thought it a remote prospect, and that if it ever happened, she would see herself as some sort of modern-day Mata Hari, a femme fatale, using her feminine wiles to give the man she loved an edge over his rivals. Not be used to give a mercy fuck to some no-hoper of a nephew!
James looked at Elaine. She was looking around the room as if trying to find a way to physically escape. She was wringing her hands and the expression on her face was one of despair. Then all of a sudden, she stopped and visibly relaxed and looked him in the eye.
The thoughts that ran around Elaine's head were those of confusion and worry. What would James think of her if she said yes? Was this some sort of test, and would she pass if she said yes or no? Did he still want a relationship with her? And how would he deal with his nephew once the boy had had her? Was she to be discarded after she had done this 'favour'? But then...She had made a commitment, and she was a woman of her word. If James asked this of her, she must do it. If he finished with her afterwards, then he wasn't the man she thought he was and didn't deserve her. She would have to trust him to deal with the consequences. She did trust him.
"What must I do, James?"
And so it was, a little more than a week later, that Elaine found herself standing on the step of a well-appointed house in the suburbs, with a small case in her hand. James had told her that he'd arranged for her to house-sit for his brother while he and his wife were away for the week. He'd promised his brother he'd do it himself, but now Elaine was here in his stead. Simon had kicked up saying he was too old to have a babysitter, even though he looked forward to James's visit. Only that morning had James phoned to say he couldn't make it, but that a friend needed a place to stay for a week, and it would kill two birds with one stone. Simon had groaned with despair, though James had hastened to add that his friend was a young woman, and he was sure that they'd get along famously. Simon's curiosity was piqued, but he was half sure she'd be some crusty old dragon. For her part Elaine had been well briefed by James. He'd shown her a photograph, probably taken a couple of years previously; he looked to be about 15 or 16 in the photo, and not bad looking for a teenager. She'd been told to be gentle with him, to nurture his budding manhood, teach him the ways of women: but not to come on too strong or too sophisticated - that would scare him off. No, she was to play the fresh, wholesome girl next door, gentle and caring but so, so hot! In short, she was to use whatever skills she had to get the job done. She was to be given the boy and she had to return the man! "Easier said than done", she thought to herself. Throughout her short life, with her exceptional beauty, she had always been the pursued, not the pursuer. She didn't really know how to take the lead, but she would try her best; she had promised James. She would make it impossible to resist her!
She'd thought hard about her wardrobe for the week, and she wanted to create a strong first impression. For their first meeting, she'd worn a thin knitted top over a gossamer-light bra that allowed her nipples to protrude very noticeably. She was wearing a short little flared denim skirt and a light cotton petticoat underneath, projecting slightly from under the skirt. She wore flat casual shoes with little ankle socks and it felt very strange after wearing nothing but stiletto sandals for weeks She had wondered about wearing panties, but James had said nothing and since she was neither at work or having her period she felt she shouldn't wear any, even if she wasn't with James. Well, that was going to be her excuse. At any rate; she secretly licked being a little slutty, going around naked under her skirts. Actually, she was really looking forward to the time when Simon first discovered her bare pussy underneath her skirt; he'd be so turned on!
She had rung the bell and as she was waiting, she heard muffled footsteps coming towards the door.
"This is it, Girl! Over the top, once more unto the breach, stiffen the sinews and summon up the blood! and all that!", she thought as she pulled her shoulders back and pushed her breasts out.
The door opened and to a casual observer, it would present a comical sight. Both the woman and the boy looked at each other, with their mouths open and without saying anything for what seemed like ages.
Elaine's first thought was, "HE LOOKS LIKE A 16 YEAR OLD BOY! That wasn't an old photo that James showed me! It was recent!"
Simon's first thought was, "Fucking Hell! She is absolutely gorgeous!" He didn't know whether to look at her face, her breasts or her legs, and tried to scan everything at once, and he didn't know if it was that that was making him dizzy, or the loss of blood from his head as it rushed down to his cock.
Elaine was the first to recover and she painted on a bright smile. "Hello, I'm Elaine, James's friend," holding out her hand.
Simon took her hand in his. It was so soft and warm. It gripped his lightly and he took his eyes away from her spectacular breasts long enough to gaze into her deep blue eyes. "Hi, er...I'm...er Simon". He kept hold of her hand, not being able to move a muscle, only to become lost in her warm gaze.
After a while, Elaine was forced to say, "Well, are you going to ask me in or what?"
Simon jumped, letting go of her hand and stumbled backwards, saying, "Sorry, Sorry! Please come in, yes, James did mention you'd be coming, said you'd be staying a week, my parents are away, thought I needed a baby sitter, worried that I might have wild parties while they were away, advertise on the internet or something, I really.." he finally had to stop babbling because he'd ran out of breath.
Elaine stepped into the house and laid her warm hand on his arm, "Well, this is also doing me a favour, I'm stuck for a place to stay while my apartment is getting decorated. Don't worry, I won't cramp your style, and if you want to bring your girlfriend back, I'll beat a hasty retreat to my room."