Woulda Coulda Shoulda

"You are really good at this," Julie offered even as she enjoyed the waves of pleasure.

He was good at it, Julie honestly believed, although not good enough to bring her to orgasm in this manner. Still, give him time to become a bit more experienced, she thought, then he's going to be really something.

But that was the future, and it would be some other woman that enjoyed his later talents. Now at least, it was time for Julie to return some of the pleasures this young man had been bringing her.

If a bit reluctantly, she eased his face out from between her legs, then directed him to stand up. No sooner had Chris done so, Julie gripped the bottom of his shirt and pulled it up and over his head, tossing it aside. There was little hair on his chest, and what there was of it was lightly colored enough to be almost transparent. Still, Julie ran outstretched fingers across what there was of it, leaning inward far enough to run her tongue across his own sensitive nipples.

'I'll bet those college girls don't think to do that,' Julie thought, recalling how little she had known about pleasing a man at the same age.

If she took the time to inquire, she might've been greatly surprised by what some of those college girls knew. She herself had come of age as one of the first wave of baby boomers, a good decade before the start of the sexual revolution. But then again, some things only got better with practice, something she'd had decades of.

Reaching down into his shorts, Julie closed her fingers around Chris' cock, pleased to find it rock hard. It was only of average length and girth, but so had been that of her ex-husband. It would've been nice if he was larger, she thought, but then again, average had always gotten the job done before and she didn't see a reason to doubt it would now.

With one hand still wrapped around his cock, Julie used the other to slide down Chris's shorts, tugging first on one side, then the other. His boxer shorts followed, their looseness making their removal even easier. His sneakers and tube socks could remain, she decided, not wanting to take the time to undo the laces in order to remove them.

"This is a really nice cock," she said to Chris as she continued to stroke her fingers along the sensitive flesh, knowing that was something that every man, regardless of his age, wanted to hear.

With that, she dropped to her knees and guided it into her mouth, wrapping her lips tightly around it as her tongue washed over the head, covering it with the wetness of her mouth. Relaxing her throat muscles, a benefit of the experience she'd noted earlier, Julie took his full length inside her, her chin bumping up against his balls as she did.

"Oh God, Mrs. Wilkes," Chris gasped loudly.

Abruptly, and unexpectedly, Julie stopped what she was doing and let his cock slide back out of her mouth. Once it had, she looked up at Chris and said, "Honey, you've got your cock in my mouth. I really think you can stop calling me Mrs. Wilkes."

"Okay... Julie," Chris said after a second's hesitation.

"That's better," Julie smiled, "now, where was I, oh yes."

Bringing her mouth back to within half an inch of his cockhead, the redhead reached out with her tongue and ran the tip of it under the underside, rolling down the length of his shaft until she reached his balls. Then she took each of them, in turn, into her mouth, sucking on them gently before working her way back to the top. There to again take him deep into her mouth, sliding her head back and forth with ever increasing vigor.

A pleasing warmth spread across Chris' body as she continued, an excitement that only grew as not only did she slide one hand back to his balls, massaging them as she sucked on his hardness, but she guided the other around to his backside, slipping it first between his cheeks, and then into his ass, two fingers burying themselves inside up until their second knuckle.

Chris' reaction was instantaneous and he let out a soft cry at the unexpected penetration. As with most men, any sort of ass play reeked of homosexuality and he didn't know how to react to it. But, after a few moments as the surprise wore off, he actually began to like it, especially since Julie was still enthusiastically sucking his cock. Part of his mind rationalized that it couldn't be gay if it was a woman doing it. And after all, it was just a couple of fingers. Of course that led to the question, would he feel the same way if it were something larger -- but that wasn't something he wanted to think about.

Between the suction of Julie's mouth and the press of her fingers in and out of his ass, Chris could feel a rising tide building up deep inside of him. One that he knew would soon enough lead to orgasm. And as much as the idea of climaxing in the older woman's mouth excited him, he really wanted to fuck her before that happened. It wasn't that he didn't think that he could get it up a second time, but he worried that she might not be interested in a second round.

Julie must've been reading his mind, he later thought, because after only another minute or so, she again let his cock drop from her mouth and withdrew her fingers from his ass.

"Time to fuck," she quipped as she got back on her feet.

Glancing around the small office, Chris noted that it didn't have so much as a couch, much less anything that might be used as a bed. He wasn't looking hard enough, he realized a few moments later, as Julie stepped over to her desk and, with a swipe of her arm, brushed everything on it onto the floor. Then, plopping her ass up into the side of it, she leaned back across the flat surface, arching her legs as she did so in order to create a space for him between them.

Following her lead, Chris moved to the side of the desk and, holding his cock in his hand, brought the head of it to the center of her pussy where, applying a bit of pressure, he parted the folds and eased himself forward, slowly at first, but then with quicker and longer thrusts as he buried his full length inside her.

"Oh that's so, so good," Julie moaned loudly.

Chris was surprised at how nice his cock felt inside of her. While he hadn't really dwelled on the idea, part of him had sort of assumed that the older woman's pussy would be, well, worn was the word that came to mind. After all, she'd been fucking since before he was born. Yet the press of her pussy walls against his cock felt pretty good, and while it wasn't as tight as some of the college girls he'd screwed, it wasn't bad either.

"Fuck me, baby," Julie echoed as her body bounced back and forth on the desk, her small breasts quivering as she moved, "give me that hard cock."

His hands pressed against the inseam of her outstretched thighs, Chris gave her all he had, ramming his cock deep inside her again and again, his body dripping sweat as he did so. A condition that Julie mirrored. As Chris lifted her legs higher to allow him to go even deeper, the redhead grasped her breasts with her hands, stroking their nipples as she savored the simmering fires within her.

They went on for a while longer, until Julie told him she wanted to change positions. Once he'd pulled out of her, the lithe redhead lifted herself off the flat of the desk and rotated her body until she was facing away from Chris on all fours. Stepping back to her, the sandy haired teen again eased his cock into her. But this time there was no need to go slow and he immediately picked up where he'd left off. Holding her tightly around her waist, Chris' motions soon became a blur as his own internal inferno neared critical mass, causing him to fear that he might finish before Julie did.

A worry that resolved itself a few frantic breaths later when the forty-five year old's body suddenly convulsed as waves of ecstasy ripped through her slender form. An eruption of passion that had been long absent from her life, evoking a silent promise that it wouldn't do so again.

Chris also climaxed short moments later as, pulling out at the last second, his cock splattered droplets of white all over Julie's back and ass. Then, totally drained he slid onto the desk, falling into a space that Julie created next to her. She leaned over and kissed him softy, telling him that had been the best fuck she'd had in the last ten years.

-=-=-=-

As Julie restored the office to a semblance of normalcy, Chris made his way down to the driver's locker room down at the end of the hall to make use of the showers there. When he returned ten minutes later, fully dressed, the redhead was sitting on the edge of her desk -- also dressed. The office didn't have a shower, but it did share a small bathroom in which she'd been able to wash up in.

"This is our little secret, right?" Julie said as she stepped up to him and softly kissed him on the lips.

"Of course," he assured her. "Besides, who'd ever believe me?"

'You might be surprised,' Juliet thought but didn't say, recalling how quickly many people tended to accept a rumor as fact, especially if it was salacious.

"I guess I should get going," Chris said, realizing that the fires of only a short time before had now grown cold. "I still have to bring the box up to the loading dock."

"Oh yeah, I'd totally forgotten about that," Julie laughed.

A quiet moment passed, during which she looked at the young man who had just transformed her world, wondering as she did if it really had to end here.

"You said you're leaving Sunday, right?" she asked.

"Yeah, we should be on the road by six," Chris replied.

'Still a day in between,' she thought as she recalled how he had felt inside of her; wondering if perhaps an encore performance might be in the cards.

But, instead of suggesting just that, Julie found herself wishing him a safe trip instead, as the real world outside the confines of her office reimposed itself on her thinking. She didn't regret what she'd done, but realized it would be better to take a step back and sort out what she wanted before going further.

Staring at Chris' ass as he took hold of the hand truck and steered it out into the hallway, Julie wondered if, once he was back at school, the young man would regale his roommates with the story of the horny old lady that he'd screwed on his last night on the job. It would be a pity if he didn't, she thought, because she was certainly going to share it with Kathy.

"In fact," she said to the now empty room as she glanced at the clock and saw that it was still relatively early, "I think I'm going to call her right now."

END