Strange Relationship

"See, this is what I was talking about last night. Everything you wear is smart, and pretty, but never sexy. What I have in mind for you to wear will make you look sexier, and if you look sexy you'll feel sexy. Then other people will come to regard you that way, and you'll be fighting them off, you'll see." She smiled as he continued. "You have a fantastic figure, women half your age should be jealous."

"Look at this tummy. Flat as a pancake, and mmm, skin so soft..." he started stroking her tummy, first with the tips of his fingers, then with his whole hand, slowly backwards and forwards across it. His fingers touched upon the waistband of her knickers and for a moment he seemed to be massaging the area of her tummy and inch or so below the waistband. Then he was talking again.

"I like your shoulders and neck too..." he leaned further into her so that when he spoke, she could feel his lips on her neck, and she instinctively tilted her head sideways so he had unhindered access to her neck. He used his hands to gently massage her shoulders and the tops of her arms. "I love kissing a woman's neck, they always seem to respond to it. How about you Caitlin, do you like it?" She murmured her agreement, but by now her eyes were half-closed as if in a daze. She was content with the touch of his lips, and the sight of his hands all over as she watched in the mirror.

"I'll tell you what else I like Caitlin. I think you have the most fantastic breasts too..." Her eyes snapped wide open as she felt the clasp of her bra undone, and with a feather light touch he'd dragged the straps down her arms, allowing the bra to drop to the floor. Then his hand were on her tummy again, just inches below her breasts. "Look at them, so firm." Unbearably slowly, his hand moved up her body until he was cupping them gently with his hands. She allowed her head to lean back against his chest and she watched in the mirror as he held them. He wasn't doing anything with them, just taking their weight gently in his hand. "Hmm," he said, "I think I've guessed just about right" and with that his hands were gone.

He lifted up the black basque, and disentangled the straps and the g-string from their hanger. As she held it in her hands, it seemed so petite, she thought she would never get into it. "Oh, I didn't realise it came with its own g-string. Let's try that on too." He looked up and caught her gaze in the mirror and she realised with dread that he meant for her to take her own knickers off in front of him. She gulped, and paused, but then she was doing it, allowing them to rest on the floor with the rest of her clothes. She stood naked before him for the very first time. She stood still, allowing his eyes to roam over her reflection. He snaked his right arm around her until it was resting on her groin, just millimetres above the top of her pubic hair. He started to rub his hand slowly in a small circle.

"Very nice, very nice. One day, do you know what we'll do? We'll trim this a little, make it nice and short, and tidy." And with that he was rubbing his hands in the soft down of her pubic hair, allowing his fingers to become entangled in the tight black curls but never allowing himself to come into contact with her sex. She held her breath for what seemed like hours, before his hand was removed and he patted her ass. "Let's get a move on then, they'll be sending a search party for us."

She dressed slowly and deliberately, pulling the tiny black g-string on first, then the basque. He presumed to fasten it for her while she stood with her head inclined, holding her hair up. She rolled the stockings up and fastened the clips one by one, and then slipped back into her shoes. Finally she looked up and stood in front of him in the lacy black basque. His eyes feasted on her, and right at that moment she could not ever remember feel as aroused as she did at that moment. Ben swallowed hard. "Well, if that doesn't make a man want you, nothing will. Let's get these bought."
They drove home and discussed the plans for that night. Dean revealed that he'd arranged to meet someone he knew. She was to be waiting in the bedroom from eleven onwards in her new lingerie - whichever set she wanted from today's expensive new acquisitions. He would send her a text when they were on their way back, after which she was to wait in the bedroom, in the dark.

As arranged, Ben went to meet his friend. Over the next couple of hours, Ben was careful to make sure that his friend had more to drink when he did. He didn't want him to have too much to drink, but he certainly needed him to be more open to suggestion. But Ben had selected his target well. He asked his friend about his love life, knowing full well that his girlfriend had walked out on him a couple of months before, and since then the man had not even had so much as a one night stand.

"Well, to be honest Ben, I don't seem to have had a lot of luck with the girls since I became single. I just don't seem to have the confidence to approach girls anymore. I've even thought about joining one of those online dating agencies."

"That seems a bit desperate!" Ben laughed.

"That's how it is mate. If nothing else, I'm absolutely desperate for a shag!" He laughed. "I'm going to get another round in, do you fancy one?"

Ben drained his glass and waved it at his friend to signal his agreement. Once he was alone at the table, he produced his mobile phone and began to tap in a text message.

With a couple of hours to go, Caitlin bathed and pampered herself, before selecting the black basque. She applied her make-up carefully and then dressed slowly, enjoying the feel of the material on her skin. She could feel herself getting wet, and as she lay on the bed in the darkness, she began to wonder how she would keep her hands off herself. She was helped in that quest by the beep of her mobile phone with a text message:

Everything going okay. Back about half eleven. Be ready. Ben

She shivered with anticipation as she snapped her mobile shut. She still couldn't believe that she was going through with it, but the thrills that she felt merely from choosing underwear made her think that she was right. There was no way that she should, or even could, turn her back on her sexuality. She lay back in the darkness.

She had no way of telling whether she'd been waiting minutes or hours. The thick curtains precluded almost all light from the streetlamps and it took some time before her eyes became adjusted to the dark. She'd gone with the basque in the end, and once her eyes became adjusted to the dark, she could make out the contrasting black panels of material against her china white skin. The thought of what was to come was torture, both arousing and daunting and the same time.

Some time later, she heard the key turn in the front door. Lost in her reverie she had heard neither car door nor footsteps. The front door click quietly shut and she could hear someone moving about, but could not discern whether there were one or two people downstairs. After another almost intolerable wait, her ears picked up the soft pad-pad of feet on the staircase carpet.

Someone eased the bedroom door open, and a shape appeared in the doorway. There was yet another wait until the newcomer's eyes acclimatised to the gloom, then he made straight for the bed, sitting on Caitlin's right with his back partly turned to her. He reached over with his right hand and slowly ran a hand up and down her stocking-clad leg, stopping before her made contact with her tingling flesh at the top. Long, sensuous strokes, designed to make him as well as her feel at ease with his presence. Caitlin watched him while he did it, trying to work out his features, but there was far too little light to attempt identification. Eventually he stood up, pulling a t-shirt over his head. Her heartbeat quickened as he knelt on the bed by the side of her, kissing up and down her legs. She parted them everso slightly and he took the hint, running the tip of his tongue around the elasticated band of her stockings.

He kissed his way up to the quickly dampening crotch of her panties. She was acutely aware that he must be able to smell her becoming aroused, something she'd always been embarrassed of even with her husband. If so, he didn't appear to care. He kissed her through the flimsy material of her panties, and then began to lap at where he approximated her pussy lips would be. He wasn't quite right, but his attention served its purpose. He adjusted himself so he was between her legs with his bum up in the air. With a free hand he drew aside the gusset of her panties. The air felt like electricity to her exposed sex. Hungrily and without finesse, he started to lap away at her, his tongue and lips frequently coming into contact with her straining clitoris but with no rhythm or method. She bucked her groin up at him, trying to produce the friction that would take her on to the next plateau.

He knelt up unexpectedly, and for a brief moment she wondered whether he had had a sudden attack of nerves. But she needn't have worried. All he wanted to do was gently raise her bum from the bed so that he could slide her panties down, which he did with gentle ease. He sat still, and nervously she began to wonder what he was doing. She took matters into her own hands, inserting one finger into her own pussy and gently flicking it in and out. He must have appreciated what he saw, because the next moment she heard the zip of his trousers go down. From his silhouette she deduced he must have been masturbating himself slowly as he enjoyed the view.

Emboldened by this new turn, she stopped masturbating and reached over to the top drawer of her bedside cabinet. She'd always been far too nervous to buy her own sex toy, but what she had retained was a hairbrush with a pink, ribbed rubber handle. This brush never left the drawer save for those precious times like this when she used the long handle to masturbate with.

She licked the handle up and down, savouring the lingering remains of her own juices. When it was nicely lubricated - not that she would need much help in that department - she quickly rolled over and presented him with her bum. She lay with her bum right up in the air, him between her ankles, and her face pressed against the cotton quilt cover. She manoeuvred herself so that the hand with the hairbrush had plenty of free play, then she began in usual fashion by rubbing the tip of the brush against her clitoris for a few moments. She could see that he was still masturbating to a slow and consistent rhythm.

When she couldn't wait any longer, she eased the hairbrush handle inside her pussy an inch at a time, until she had the full six inches of the handle inside her. She sighed as she felt the juices flowing around it, and for a few moments she just left it there. Then with practiced ease she started to work it in and out of her sex, at a steady, never varying pace. She heard her partner's breathing start to quicken, and he put one hand onto her butt cheek as he masturbated. She loved the though of putting on a show for him, even if it might be a little too dark to make everything out. Stealing her other hand between her legs, she used her index and middle fingers to spread her pussy lips wide apart.

He was massaging her butt now with his free hand, and before long the ball of his thumb started to come into regular contact with her anus. He seemed unsure of what to do next, as though he wanted to penetrate her with it but was unsure whether to proceed. Caitlin didn't really care one way or another, the consistent rhythm of her favourite toy was bringing her closer to her first orgasm, and combined with the erotic situation she found herself in - living out one of her favourite fantasies - she was on a sure-fire winner, no matter what he did right now.

He leaned over to plant big, slobbering kisses all over her butt, being surprisingly considerate and avoiding doing anything that might spoil the rhythm of Caitlin's masturbating. Slowly but surely, his attentions edged closer towards Caitlin's anus until he was licking it up and down, trying to penetrate it with his tongue. When he used his thumb on it again he found success, piercing her tight bum hole until his thumb was inserted as far as the first knuckle. He seemed content to leave it there, just waggling and twisting it in random fashion as they both continued masturbating.

She felt the headrush associated with her first orgasm seconds later, muscles clenching on the hairbrush handle inside her. She sighed luxuriously and withdrew the hairbrush, concentrating on the feelings her partner was producing in her anus. She felt invigorated from her first orgasm and wanted to seize the initiative. She took his hand by the rest and pulled it gently away, the soft plop as his thumb left her bum hole making a hole in the silence. She spun round and buried her head in his lap, using a hand on his chest to force him to lean back. She took his erection in her left hand. It was a good size, not the biggest she'd ever had, but thick and smooth. She flicked her tongue over the head a few times before gorging on it, deliberately slurping and sloshing it around in her mouth for effect.

She felt the salty pre-cum, and silently cursed him for paying too much attention to himself whilst masturbating over her. She'd smelt the alcohol on his breath and wondered whether he'd had a drink too many, and whether he would last long once he was inside her. She worked on the head of his penis for several minutes, slowing down once or twice when she thought she detected an involuntary thrust of his hips.

She stopped and lay back, legs wide apart and knees in the air. She wanted him inside her sooner rather than later if there were any questions about his staying power. He took a moment to cotton on to that but was soon on top of her, guiding his erection into her wet sex. It slid in easily, and in one movement he pushed it to the hilt, where he lay still for a moment. It produced a wonderfully light-headed sensation inside her and she smiled in the darkness. Then, he began thrusting into her, gently at first with long, slow strokes to the full extent of his length. She thought he would slip out of her if he kept drawing back that far, but he always seemed to know exactly when to stop. Then he was inside her again, his hot shaft filling her up.

He began to speed up, slowly at first, then accelerating and shortening the outward stroke. Their pelvises began to bang together, and she closed her eyes and bit on her bottom lip as her unknown lover pounded away at her. This was the first man other than her husband that she'd had in over twenty years, and she was by now loving every single minute over it. She allowed to him to hammer away at her, almost using her for his own means. She had her nails digging into his butt cheeks, which only served to spur him on.

She felt the familiar spasmodic thrusts from his hips, a sign that he was not far from his orgasm. She was not going to orgasm from penetration, and she'd wanted it to last a little longer, but the main thing was that she had had sex at long last. So she drew him closer, squeezing his shaft with her vaginal muscles. He grunted, and with that final thrust, loosed his sperm into her. He paused to catch his breath for a minute, his quickly shrinking cock still inside her. She made no effort to move him. Eventually he clambered off her and stood up, ferreted around on the floor for his shirt and left without looking back.