Intervention

That stunned Shirley even more. Never had she imagined that Dean might be interested in her that way.

"Dean, I don't know what to say," she finally responded.

"Then I'll say something," he offered, "even if it makes me out to be more of an idiot than I've already done. Shirley, I've been having fantasies about you ever since high school, I think you're the perfect woman, and I couldn't want anything more than to have you be my first."

"Oh Dean," Shirley said, reaching to stroke the side of his face.

"I knew it was never going to happen, but now," he started to say, only to have his words cut off as Shirley leaned forward and kissed him.

They'd shared friendly kisses before, but this one, even though just as brief as those, carried an intimacy they had lacked.

"That was nice," Dean said as he took a step back.

"Yes, it was," Shirley admitted, "but it might also have been a mistake."

"Why?" Dean countered.

"A number of reasons," she offered.

"Like?" he asked.

She opened her mouth to give one, but none seemed forthcoming.

Shirley had never been as promiscuous as, say, Joy, but neither did she lead a monastic life. Sex to her was a human need, separate from love and one she enjoyed when the opportunity presented itself. And as much as she hated to admit it, it had been a bit of time since it had.

She reminded herself that, only a handful of minutes ago, she was willing to see Dean in Sylvia Myer's bed. Was there a reason why hers wouldn't be just as good a destination? He was no longer the fourteen-year-old who had first come to work at Gilhooley's, back in high school. It would've been a lot simpler to dismiss his interest if he were. No, he was by any definition a grown man, old enough to make his own decisions. Why shouldn't she let nature take its course?

"Dean, are you really sure about this?" she asked with her last bit of conscience.

"Absolutely," he replied, "more than I can say."

'I hope I don't regret this later,' Shirley told herself as, abandoning any further prudence, she took Dean by the hand and led him back to the couch in the living room.

-=-=-=-

Despite Shirley's kiss in the kitchen, Dean was still a bit hesitant as to what to do next. With Melanie, he'd had to practically ask permission before so much as kissing her. Thankfully, Shirley quickly made it clear that wasn't the case here -- not by a long shot.

As soon as they'd sat down, Shirley laid her left hand on his thigh, sliding it up his leg until it came to rest against the noticeable bulge in his shorts. Dean let out a loud sigh as he felt her fingers press against his cock, a satisfaction reflected in the smile on her face. She continued to rub her hand back and forth against his hardness, causing it to grow even more.

"You can touch me too, you know," Shirley said in a soft voice, "anywhere you want to."

Tentatively, Dean reached out with his right hand and placed the palm of it on Shirley's breast, squeezing it softly. He could feel the hardness of her nipple even through the dual layers of her bra and the dress over it.

"Oh, you can squeeze it harder than that," Shirley laughed. "I'm a big girl, I won't break."

Dean quickly followed her instruction, becoming quite pleased with himself as he reached out with his other hand and followed suit on its twin. Shirley let him play with her breasts for a minute or so, then told him to just sit back and relax.

Undoing the top button of his shorts, Shirley pulled open the top of his pants and slipped her hand down them. The outline of his cock was much more visible in just his underwear and she grasped it firmly, pleased with both its length and girth. It wasn't the largest cock she'd ever felt, but it was certainly nothing to complain about. Up and down her hand moved, bringing his manhood to its full length, with the uppermost tip now peaking above his waistband.

Leaning over, she kissed the exposed tip, running the length of her tongue across it before wrapping her lips around the head. At the same time, she dropped her hand to just below his balls, cupping both softly.

"Fuck!" Dean exclaimed, unable to believe how good it felt.

"No, that comes later," Shirley chucked as she let his cock slide out of her mouth. "First I want to enjoy this a bit, and I'm sure you will too."

With that, she put her mouth against the cloth covered protrusion and kissed it, rubbing her hand against his balls at the same time. Dean found himself laying his hand against the back of her head, running his fingers through her hair as he both arched his head backward and closed his eyes to better enjoy the incredible sensations.

Dean then slid a hand across her back and around her side, again placing it against her breast. This time, he didn't even consider that he might be doing it too hard. Shirley continued to rub his cock through the thin cotton, massaging it with both her mouth and hands. Then she slid her hand under the right leg of his shorts until finally making flesh to flesh contact, the warmth of her hand matching that of his cock.

"Oh God!" Dean gasped as, with her fingers firmly wrapped around its length, Shirley began to pump his cock.

"Did it feel this good when Melanie played with it?" she asked as she looked up at him.

"No, nowhere near," Dean managed to reply, thinking as he did that the blonde's motions had been stiff and mechanical in comparison.

"Good," Shirley simply said as she tightened her hold even more.

She continued to play with his cock and, as she did so, Shirley couldn't help but think what a stupid idiot Melanie had been. Even as just a boytoy, Dean certainly had the tools to get the job done, plus it was also obvious that he'd have done anything to please her. Yet she had tossed it all away, preferring to play him for a fool instead.

Taking hold of the waistband of his shorts, Shirley dismissed the foolish girl from her mind and focused instead on making Dean forget she ever existed. A quick tug brought them down along his thighs, exposing his hardness to the open air. Again, it was hardly the biggest cock she'd ever seen, but it was more than satisfactory and now it was hers to do with what she willed -- and right now, she had an abundance of will.

She guided Dean to his feet, sliding her hand up along his inner thigh until, after stroking his balls with her fingertips, she wrapped her fingers around his thickness. Quickly she brought the head of his cock to her waiting mouth, sliding it past her lips and deep within her. A loud moan erupted from him as he felt her warmth engulf him.

"Oh, dear God!' Dean gasped as he realized that everything anyone had ever told him about how great a blowjob was had been true.

As much as she liked to fuck, Shirley had always liked giving head more, even back in high school -- a rarity in the late fifties when few girls were willing to do so. It gave her a sense of control, even power, as she swallowed a man's hardness, drawing it deep into her throat. At the same time, one hand caressed Dean's balls while the other continued to pump his length in and out of her mouth.

Shirley's tongue washed over the head of Dean's cock, then slid down his length, bringing with it a delightful thrill that resonated throughout his body. In less time than he'd thought it possible, a small but familiar feeling began to grow deep inside of him, one that slowly but steadily rose to a crescendo as the fire in his loins reached volcanic dimensions.

Something that didn't fail to catch Shirley's notice as she increased her efforts, taking him deeper into her mouth, even as the motion of her head became a blur. Dean tried to hold back the rising tide, but had little success as, only brief moments later, he exploded into Shirley's mouth, filling it with the fruits of her labors.

Dean had been unsure if he was supposed to warn Shirley about what was about to happen, and then it did so with such unexpected force that he didn't have time to decide. He needn't have worried, as her response to the eruption was to slam his cock all the way to the back of her throat, allowing her to effortlessly swallow every drop of the white cream spilling out of him. In fact, she continued to do so long after he was spent.

-=-=-=-

"See what you've been missing?" Shirley said as she let his now deflated cock slip out of her mouth.

"I never imagined ..." Dean started to say, not quite sure how to complete the thought.

"Well, now you don't have to," Shirley smiled as she looked up at him before rising to her feet.

"I don't know how to thank you..." Dean again started, this time to be interrupted by Shirley.

"Oh, don't worry, I'm going to show you how," she practically purred. "We're far from done."

With that, she took hold of his left hand and slid it under the bottom of her dress, pressing it against the now very wet panties she wore under it. Her fingers over his, she rubbed them against her pussy, sighing heavily as they produced their desired effect.

"Hands are good," Shirley said, "but a nimble tongue is even better. I'm going to show you how to use both."

With that, she directed him to finish what she'd started with his pants, followed by the rest of his clothes, all of which quickly piled up beside the couch. While they did, Shirley took the opportunity to admire his youthful body as never seen parts of it came into view. As she watched, she gently ran one hand across her breasts and the other between her legs, picking up where Dean had left off.

"Well, I guess it's only fair that I get naked too," Shirley said once Dean had finished. "I hope you won't be too disappointed.

Having already slipped out of her shoes, Shirley reached under the hem of her dress and pulled down her panties, dropping the damp garment onto the bare floor. Then she turned around and, drawing attention to the zipper running down the back of her dress, invited Dean to undo it. She could have done it herself, of course, but she knew from what other men had told her, that one of the things a man always remembers is the first time he unzipped a woman's dress.

As the dress grew loose around her, Shirly pressed her body back against Dean, taking his hands and closing them around her bountiful breasts. He instinctively squeezed them, feeling again the mix of soft flesh and hard nipples as his fingers moved across both. With her back exposed, she further invited him to undo the clasp of her bra, something he'd often practiced doing on his sister's when it was his turn to do the laundry.

The bra likewise undone, Shirley again took control of his hands and slipped them under the cups, pressing the palms against her bare flesh. She directed his attention to her thick, stubby nipples, as well as the large areolae that surrounded them. She let him play with them for a bit, then gently removed both hands as she stepped forward a few steps before turning around.

Her bra and dress dropped to the floor, leaving her with nothing left to preserve her modesty. Although modesty didn't seem to be much of a concern as, with her hands on her hips, she struck a pose to allow Dean a good look at her, her body gently swaying first to the right, then the left, to give him a better view.

"Well, what do you think?" she asked.

Even though the woman before him had just introduced him to oral sex, not to mention the promise of more to come, Dean did try to answer the question as honestly as he could. Yes, Shirley was older than the women he'd seen in Playboy or the occasional R rated movie, and yes, it was also true that she weighed more than was considered to be sexy by most standards; yet despite that, or perhaps because of it, he found her highly desirable. She was real, that was the only way he could explain it.

On a body almost a half-foot shorter, her large, full breasts were the size of volleyballs, and while they were hardly as firm as Melanie's, Shirley hadn't hesitated to give him full access to them, which made all the difference in the world. He had no idea what his now ex-girlfriend looked like between her legs, but the waitress' mound was covered by a thick thatch bush of hair, its color a mix of brown, grey and just about everything between. The sight fascinated him, especially since he knew he was about to have the opportunity to examine closer. In fact, since again, unlike Melanie, she was giving herself to him freely rather than making him earn every little bit of access, how could he think she was anything but beautiful. And he said so.

"I think you are beautiful," Dean said with a broad smile.

"And I think we need to get your eyes examined," Shirley laughed, "but not right now. Now I have something else I need for you to do."

Moving back over to the couch, Shirley sat down and, lifting her legs onto the cushion, spread them far apart, displaying her dark mound and creating a space for him to approach it. She gave him a sort of 'you know what to do' look and without hesitation, Dean proceeded to give it his best effort.

Guys always talked about going down on a girl, but Dean didn't know anyone who had really done it. Oh, he knew all the jokes about the smell and such, but really had no practical knowledge of where to start. Thankfully, Shirley seemed to have anticipated that and took the lead there as well. She reached down with a free hand and parted the folds of her mound, revealing a rich pinkness within. Again, following her instruction, Dean got down on his knees and, bringing his face right up against that pinkness, he kissed the center of it. Then he reached out with his tongue and using the tip, began to caress it from top to bottom. He wasn't sure exactly how to describe the smell or the taste, but he did know that there certainly was nothing fishy about either, despite the stories he'd heard.

Eager to please, it didn't take long for him to really get into it, and the soft moans of appreciation that Shirley began to offer were like music to his ears. Admittedly, he had only a general sense of what he was doing, but it did seem to be enough as not only was the robust woman spread before him not complaining about his efforts, as Melanie was sometimes wont to do, she was actively encouraging him.

"Yes, just a little higher," Shirley said with shortened breaths, "and just a little harder now. You're doing fine."

He also noted that she'd said that with her eyes closed, as if she wanted no distractions from to her enjoyment. Again, following her direction, he slipped first one, then two fingers deep inside of her and began to gently slide them in and out, his pace quickening once he saw how she was reacting to his thrusts. There was a clock on the wall but, absorbed in what he was doing, Dean had no idea how long he'd been trying to please her, only that at some point the older woman brought it to a close with a simple, "that was good."

Reaching down between his legs, Shirley closed her fingers around his cock and was pleased to find it hard again. Not that she hadn't expected it to be -- after all, youth had its advantages. She slowly stroked it for a minute or so, then invited Dean to climb up onto the couch behind her. Once he did, she wrapped her left leg over his and placed his cock against her pussy, pressed it against her mound just enough to part her folds.

"Ready?" she said, drawing attention to the fact that he was about to lose his virginity.

"Oh yeah," Dean enthusiastically replied.

For some inexplicable reason, a stupid conversation he'd once had with a couple of buddies popped into his head. The topic had been, just what qualified as losing your virginity? Was it enough to just get your cock inside a woman's vagina, or did you have to climax it it as well? One of his friends thought it didn't count unless the girl also climaxed, but the rest of them all agreed that couldn't be right. Whatever the standard was, Dean was sure of one thing; he was about to satisfy all of them.

"Okay, slide it in me, as far as you can," Shirley said releasing her hold on his manhood in favor of his own.

Holding the base of his cock tightly, Dean slipped the head of it deep inside her. He could feel the warm embrace of her sensitive flesh as it wrapped around his own, sending a thrill of excitement through his body. Finally, before he'd even realized he had done it, he was as far inside of her as it was possible for him to go.

"Congratulations, you are no longer a virgin," Shirley grinned.

"That was it?" Dean replied, disappointment evident in his voice.

"Well, technically yes," Shirley replied, "but don't worry, it gets better. Now just start to slide it back and forth, start slow, then pick it up once you get comfortable."

Sure enough, it did get better as Shirley had promised, since within a few minutes Dean was fucking the woman pressed against him as if his life depended on it. He had one hand on the underside of her left leg, giving him more leverage as he slipped in and out, while his other arm rested under her body, allowing his open hand to tightly hold onto her heaving breast.

"That's it, baby, give it to me," Shirley called out as she slammed her body back against his, pulling him further inside of her, "give me that hard cock!"

Moving his hand from her leg to Shirley's free breast, Dean took hold of it as well, allowing him to grip both as he pulled her down on him. An act the larger woman loudly encouraged.

"Yes, play with my tits while you fuck me," she cried between moans. "Squeeze them as hard as you can."

Eventually, Shirley replaced his hands with her own, allowing him to concentrate his attention on simply fucking while she rubbed her nipples.

"Am I doing this right?" Dean asked at one point where it seemed like she was momentarily distracted.

"You're doing great," Shirley insisted.

Nevertheless, only a few minutes later, she urged him to change positions so that he was now laying down with her perched over him. Now, with his cock deep inside of her and his hands again encompassing her breasts, Shirley began to ride him like a cowgirl on a prized stallion.

"Oh yeah, that's better," Shirley said as she again ground her body down against his.

Dean had to admit, it was better, proving that he had a lot to learn. Hopefully Shirley was going to be willing to teach him. But that was a worry for tomorrow; right now his main concern had to be the reappearance of that familiar feeling from before.

Both of their bodies had become blurs of motion as, with shared cries of delight, both reached for the summit. A goal that seemed closer with each passing breath. He was sure they were almost there, when Shirley again suggested they change potions.

Now she was on her knees with him behind her, tightly holding onto her hips as she pressed his cock into her with ever increasing intensity. Her large breast swung every which way as her body rocked under him, even as he drove ever onward.

"I'm almost there," Shirley said from beneath him, echoing the voice in his own head.

He could feel the last vestiges of control slipping from him, causing Dean to fear that he might climax without her. Then, at what seemed the last moment, he felt her body beginning to shiver and quake beneath him, the muscles of her sex contracting around his.

"Fuck!" Dean cried out as he came with an intensity that made his earlier climax seem like the aftermath of a wet dream.

Every bit of energy drained from his body as he felt a sense of peace and accomplishment unlike any he'd experienced before. Shirley also felt wrapped in the joy of orgasm, her own body alive with excitement. Together they skirted the boundaries of heaven, sharing the gift that only joining could bring.

-=-=-=-

Monday found them both back at the diner, Shirley behind the counter and Dean at his usual table, no less than three books opened in front of him. He didn't even have to look up to know that Melanie had just come in the front door; the reaction of the men sitting at the counter off to his left had been enough to tell him that she had.