If At First You Dont Succeed

Chapter 1: Pat and Rick and Jane and Don.

Jane was nervous from the git go. She'd been with the company only a month. Pat was her boss. Jane still had not made up her mind whether she liked or disliked her. She could be curt, also affable. You never quite knew what to expect. But she was always fair, so much Jane had to admit.

She'd agonized over what to wear. Silly really, but she always did. In the end, she went for the plain pink dress, longish, though not too long, which fastened tight across the top, leaving arms and shoulders bare.

"What d'you think?" she'd asked Don, twirling before him, bare-footed on the carpet.

"Looks great," Don said, trying to be enthusiastic.

If he'd been honest, he would have told Jane that the tie that held the dress in place was pulled too tight, giving her a 'prom-like' appearance. Jane was five years past 18. A moderate amount of latitude in the tie would have been more appropriate. Don, older than Jane by a few years, enjoyed the odd glimpse of pure white breasts down the top of a dress and would not mind at all if other guys got a titillating view of Jane's. He'd watch, thinking 'Eat your heart out, buddy. Mine, all mine.'

They'd been a couple for only three months, but Don knew already that asking Jane to loosen the tie would result in an impatient gesture, her running upstairs, and a complete change of outfit. The tie was tight so her breasts would not be visible at all, even when she bent forward. Neither would they budge one centimeter, held firmly in place between the tie and the demi-bra.

Don thought to himself 'Isn't the whole point of a demi-bra to give the guys an occasional look?' But he said nothing.

"Shoes?" Jane was saying.

"How about the black strap-ons?" Don said, looking at his watch. They were already late.

"A bit risqué, don't you think?"

"I don't think so," Don replied.

The strap-ons highlighted Jane's elegant feet and slender ankles. What was the point in having such attributes if you didn't show them off once in a while? Jane was truly a stunner and her habit of 'hiding her light under a bushel' had begun to annoy Don. He said nothing because he sensed his desire to 'show her off' was basically sexist. He was a bit ashamed of this, but it did not make him feel any different.

"Mmmm!" Jane pondered. "I think I'll stick with flat. Better be on the safe side."

She slipped into a pair of black shoes with flat heels, and looked at herself in the mirror, from all angles.

'Now she really does look prom-esque, Don was thinking. But he said nothing. He was dressed as usual, jeans, a sports shirt, open at the neck. And the amulet. He always wore the amulet, even though Jane often made negative comments about it. He had told her the necklace was an heirloom, but in fact it had been given him by a college buddy, Rivera, a Brazilian and inveterate rake. He scored with every girl who caught his eye --- at least by his own account. The amulet was engraved with an 'ancient Indio fertility symbol', he'd said, soberly.

'Help you with the ladies, my friend' he'd added, significantly.

Shy by nature and overawed by his ebullient and gregarious friend, Don had not believed this nonsense, of course, but accepted the gift in the spirit in which it was intended -- and by implication, admitting that he could do with all the help 'with the ladies' he could get. To his amazement, he'd scored the very first time he'd dared to wear it. And though this remained very much a one-off – he had, in college parlance, gotten lucky – the amulet became his good-luck charm.

They arrived twenty minutes late. Don was irritated. He liked to be punctual.

"Don't be silly," Jane had said. "It's fashionable to be a bit late. It's expected."

Pat did not appear to disagree. Her greeting was warm.

"I do hope you don't mind," Pat said, "but I've had dinner catered. Just no time. Anyway," she continued, taking Jane by the elbow, "the caterers do a much better job than I ever could. You really wouldn't want to try my cooking."

Don was not thinking at all of Pat's cooking. He'd never set eyes on her before, but even as he shook Rick's hand, he now could scarcely keep his eyes off her. What a contrast. Prim little Jane, her attributes all safely hidden away. And hot Pat, everything on show. Long, slender, bare legs – black strap-ons set them off to perfection --- a skirt revealing enough to whet the appetite for more, and a white blouse that was as close to transparent as it could be without actually being it. The contours of Pat's breasts showed through unashamedly, and those points had to be .... her nipples!

Don caught the look on Rick's face and read his mind. 'Sexy, ain't she?' He almost answered the unasked question!

He was caught unawares. Pat was Jane's boss. He'd expected a bit stern, perhaps, even prim. Business-like at the very least. It was why he had been a mite grumpy. Expectations for the evening had fallen under duty rather than pleasure.

It took Don a while to reconcile his expectation of Pat with what turned out to be the reality. Well, to be honest, he never did quite adjust.

He joined in the small talk over drinks, then dinner, but his mind was focused on a single question that arose as the two couples sat across from each other sipping cocktails. Pat had crossed and re-crossed her legs. Her movement was swift, and it remained merely a suspicion......?

Rick was older than Pat, possibly already into his forties, and Pat was older than Don and Jane. Low thirties, maybe. Who cared? Her body was well preserved and she displayed it with unabashed assurance. Everything about her oozed sensuality.

Don ate and drank mechanically, trying manfully to keep his eyes from Pat's breasts as their form and contour adjusted naturally to her movements.

During after dinner drinks, Don's kept Pat's thighs in the corner of his field of view. He followed the talk vaguely. This skirted current events and fastened somehow on the two couples who'd made a top news story out of 're-vitalizing their relationships' by having sex every day.

"Can't imagine what all the fuss is about,' Pat had said. "Hell, once a day! What's so special about that?"

She'd glanced at Rick, who nodded solemnly in acquiescence.

"And writing books about it, too" he'd said in that deep voice with a slight southern twang.

"Hell," he turned his head to eye Don and Jane, sitting together opposite, "if all she got was once a day....?"

He'd nodded at Pat, leaving to the imagination the diabolical consequences this would have.

Don knew that Jane would not like this kind of talk. She'd probably not even noticed the news item. He had. It was all over the web.

"Boasting about 'doing it' on the edge of the bed, for the first time," Pat continued blithely. "I mean, gimme a break."

She'd eyed Don so directly then, he was sure he'd blushed.

"All that talk about 'varying it'. I mean, so primitive, don't you think?" Pat was saying.

"We found a great way to keep things spicy," she continued, eyeing Rick seductively.

Rick grinned.

"Pat's idea," he said, eyeing Jane.

"You tell," Pat said.

"Maybe our guests aren't interested, Pat," Rick said, his gaze roaming from Jane to Don and back again.

Don found his voice. Hell, one of them had to say something.

"Er..No! Not at all," he said, clearing his throat. "Every couple needs ..er.. something."

"You're so right, Don," Pat said, rewarding him with a brief parting of her thighs.

A thrill ran through Don's body that was utterly disproportionate to the brevity of the glimpse --- OhmiGod! Was it obvious that his dick was straining against the tight denim of his jeans?

"If you don't work on it, you so easily get in a rut. Been there, done that," Pat was saying.

Rick was chuckling. Pat elbowed him, playfully.

"Third time lucky," he said, lightly.

Pat threw him a look, possibly suggesting a fourth time might be even luckier, though only possibly.

"We have this roulette wheel, y'see," Rick hurried on. "A toy, really. But it serves its purpose. If it comes up red, it's Pat's turn, black it's my turn."

"Er... For what?" Don said, interrupting the brief silence.

Jane had her stone face on. He hoped Pat and Rick did not notice.

"Whoever's turn it is makes the rules. You know. If it's Pat's turn I have to do what she says, and vice versa. No exceptions."

"That's how we find out what turns us on," Pat said.

"Number below 16, it's for two hours, above it's four hours," Rick said.

"Then we spin again," Pat interposed, "If he's got any gas left!"

Which drew a belly laugh from Rick.

"I hafta admit it," he said. "She outlasts me every time – well, nearly every time."

"That's interesting," Don said, struggling. Four hours? What could you say?

"Works for us," Rick and Pat said, in unison.

"But, hey," Rick continued, "chacun a son gout. What works for one couple doesn't necessarily work for the other."

Don steeled himself for the question – what 'trick' did he and Jane use -- which never came.

"Well now, how about another round of drinks?" Rick said, jovially.

Jane consulted her watch.

"It's getting late, Rick," she said. "I think we'd better be getting along."

"Work tomorrow, eh," Rick said. "An' I'll bet she's a real martinet!"

He said it playfully, but drew nevertheless a sharp dig in the ribs from Pat.

"Not at all, Rick," Jane said, far too seriously. "She's a great boss. It's a pleasure to work in her department."

"And you're great at your job, Jane," Pat said, fulsomely.

"See. You!" another playful dig at Rick. "We get along fine, don't we Jane."

.......................................................................................

Don knew it was coming. Jane drove.

"You drank too much, as usual," she'd said, sharply.

There was a long silence, during which Don failed to keep a mental image of Pat out of his mind. The pollen was up in no uncertain way. But Don knew that the evening would not end as he fervently wished it would.

"Disgusting," Jane spat out, eventually.

Don remained silent.

"You, too," Jane continued.

"'Every couple needs something'", she mocked.

"I hadda say something, Jane. What was I supposed to say?"

Silence.

"And don't think I didn't notice," Jane said, after a long pause.

"What? Notice what?"

"You ogling her. Dressed like a cheap whore. Ugh! Disgusting."

Don considered several responses. He was not in any sense drunk, but had imbibed sufficiently to mull over the pros and cons of suggesting that Jane lighten up some – even that Rick and Pat's 'game' may be healthy for their own relationship.

But the timing was not right. Jane's frigid attitude had damped the pollen all too effectively. Don's dick no longer tested the zipper of his jeans.

"D'you know what," Jane said, with an air of incredulity. "I think she didn't even have panties on!"

"Really?" Don said, feigning innocence.

.........................................................................................

When their guests left, Pat and Rick relaxed on the sofa, enjoying martinis, three fifths ice-cold vodka, two fifths Vermouth and an olive.

"What d'you think?" Pat said.

"Him, for sure. He couldn't keep his eyes off you."

"I noticed. Not bad looking, either. I could go for him."

She looked at Rick interrogatively. He shrugged.

"How can you tell?" he said. "Pretty little thing? I'll bet she's got one hell of a body under all that armor."

"Very uptight, though."

"God, Yes! You think she actually screws him?"

"I expect so. The way I used to, with my first. Bless his heart. He was nice enough, but he had no idea how to get me going."

"You think young Don can get her going?"

Pat considered.

"Nope!" she said. "But he'd sure like to."

"Which means?"

"We agreed. Whichever. She's a definite 'notatall', he's a 'maybe'."

"My bad luck," Rick replied.

"No," said Pat emphatically. "My good luck!"

Pat and Rick had talked about it enough. Each emerging from a series of stultifying relationships, they had 'found sex' with each other. It was exhilarating, fulfilling, exhausting. Could anything be better? Neither knew, but they were ready to push the envelope to find out. Occasionally, if one or the other was not in the mood, they'd use a porn movie, sometimes 'his', sometimes 'hers' to get them going. It always worked, and gave them not a few ideas. But there's a limited number of techniques a man and a woman can use to extract mutual pleasure from 'the finest thing in life'. They'd been through them all, many, many times.

The obvious next step, though, a swinger club, was a total failure. Fat, ugly or both, some cute young things dragged along by their partners, to whom they clung like limpets. Single guys on the prowl, some of them attractive in an animalistic way. Pat was not averse to an FMM threesome but the guys on the prowl did not cut it for her. Anyway, the ambience was all wrong.

They'd decided. Private, or not at all. Jane and Don were 'trial couple number three'. One and two had drawn four 'notatalls'.

Chapter 2: Jane and Don.

A week had passed since 'the dinner', and Jane still had not loosened up. Don tried everything – well, everything he knew. But as the nights passed by, with Jane retiring to the bathroom, closing the door, emerging encased in a flannel nightgown, undoubtedly panties underneath, slipping into their king-size and turning her back to Don and her light demonstratively off, Don began to get frustrated. And not a little mad.

What was the point of having a relationship with a woman if you did not have sex? He might as well room with a guy. At least they'd have some fun. Sex was the force that drew men and women together, and kept them together, was it not? The withdrawal of sex by one party was asking for trouble.

Sure, many had been the times previously when Don wanted sex and Jane did not. But she had been tender.

"Not tonight, Don. Just hold me, cuddle me."

Don really liked Jane. He was a nice guy. She was a very nice girl. He'd done what she'd asked – held her, cuddled her, soothed the wrinkles left behind by her day in the office, stroked her neck, kissed her softly.

She'd sighed.

"You're such a wonderful guy," she'd said. "I'm so fortunate."

Then she'd fallen asleep.

Don had hung in there, confident things would change. Inside Jane was a butterfly. He had just to figure out how to coax it out of its chrysalis. Now, he was not so sure. Not even cuddles. Maybe the chrysalis was all there was?

Since leaving college, Don had dated, if infrequently. Some of his dates had ended with a kiss and a cuddle in the doorway. But not all. Sheena, for example. They'd met one afternoon when she sauntered into his cubicle carrying an armful of folders. He'd seen her around, but not taken much notice.

"You have nice hands," she'd said, seductively.

"Er...Thank you," Don had stammered.

"Would you like to slide one up my skirt?" Sheena said, as though asking if he'd like a coffee.

Don looked up sharply. Was she serious? She was! 'Come on, get on with it', her expression said.

"Someone will ..er.. see," Don stammered.

"No they won't. I'll keep my back turned. It'll just look like we're chatting."

Don remembered still how his body had tingled all over as tentative fingers slid up soft inner thigh, met naked pussy lips, which parted soooo readily. 'I'm pretty wet. You can start with two, first slow, then three, fast and hard.' It had taken half an hour and his arm was about to fall off when Sheena celebrated her orgasm with a faint 'Oh!'. Then, 'That was nice. Come by tonight and I'll do something nice for you'. She scribbled her address on the scratch pad.

'Something nice' turned out to be a full-throated blow job. Don lasted five minutes, the only five of the evening that one part of him or another was not stimulating Sheena's cunt. She was truly insatiable. Thereafter, she'd stop by his cubicle mid-morning to be finger-fucked, and again mid-afternoon, and she'd pout sulkily if he made an excuse for the evening.

Small wonder that he hadn't survived the Sunday of the second weekend. They had been at it since Saturday noon. Break for a pizza, a few hours sleep here and there, otherwise raw sex in tooth and claw. Don had woken around Sunday noon to the feel of Sheena's teeth on his dick, which remained stubbornly limp. It was worn out. And once it became apparent this was a semi-permanent condition, Don was peremptorily thrown out.

Still, Don had learned some things about himself that he previously did not suspect. He could get it up night after night, for many hours at a time: he could survive a vicious fellatio for thirty minutes, and still have enough gas in the tank to fuck for a another half hour before coming: he could come inside her and keep it stiff through a second round, and sometimes even a third. If his dick had eventually gone on strike, it was after a workout the like of which many a porn actor would have been justly proud. He concluded it was not he, it was Sheena. She didn't need a man, she needed a football team!

'What the hell do women want?' he'd often asked himself, realizing only gradually that this was a ridiculous question. Each 'date' was different from all her predecessors. Don worked in the IT sector, so he was familiar with the term 'bandwidth'. He'd just never thought of this in the context of female sexual appetite.

Jane was Don's first live-in. He'd not shaken off his innate shyness. Jane had made him feel good about himself. She was a truly nice girl, pretty and what a body! This had been very much on view during their courtship. They'd sat on his couch, undressed each other garment by garment until both were naked. Then a long, tender kiss as his hand explored every inch of her, the so soft breasts, long slender neck and back, the silk of her inner thighs, the heavenly warmth when he finally dared to explore the holy of holies. Their sex was the antithesis of the wild, interminable sessions with Sheena. Sensual, gentle and brief. Once Don came, that was that. When she returned from the bathroom, they'd kiss and cuddle for a while, but there would be no resumption of 'proceedings', even if Don tried to initiate this.

But Don did not mind. He was in love.

When Jane moved in, the sessions on the couch tapered off. They shared a bed, after all. If Don started something on the couch, Jane would take him by the hand and lead him to the bedroom. Where the light went out too soon. Her peerless torso met his eyes less and less frequently.

Sure, there was lots of touching, feeling, kissing, stroking. But when she was ready, strictly missionary, under the sheets. Don tried to draw it out, but after all the stroking and kissing, five, ten minutes was as long as he could restrain himself.

Jane gave every impression of enjoying their couplings, even though they ended long before she was even close to orgasm. She did not seem to mind. A tissue was at hand, and when she returned from the bathroom, the nightgown was on. A quick last kiss, and she'd snuggle close to him and fall asleep.

At first Don was content with this. Jane was no longer his 'date'. They had a 'relationship'. Naturally, the bloom of their initial encounter, of being 'in love' wore off. At least he was 'getting it' regularly. No longer the torture of 'dating' and 'will she, won't she'.

But as time went by he had gotten frustrated. Sex as routine? Was this the way it was going to be? When he thought about it, he realized that he had never managed to bring Jane to orgasm. Was there something wrong with her? Or with him?

He'd tried to talk to her about sex, tried also to mix it up. But Jane didn't like to talk. It embarrassed her, she said. And when he tried to interest her in new things, she gently steered him back into the routine. He yearned to caress her pussy with his tongue and lips, but every time he'd made a move in that direction, two hands grasped his head and returned it to her breasts.