Serendipity

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Unexpected sequence of events creates greater opportunity.
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Ann Douglas
Ann Douglas
3,178 Followers

Cutting the engine while still coming down the street, Jeff McKnight quietly guided the AMC Spirit into the driveway, careful not to put so much as even a scratch on the brand new car as he gently applied the brakes and brought it to a stop. If someone had seen him perform the unorthodox park, he'd have said he coasted in so as not to wake anyone at this hour -- it was three in the morning after all -- but that would've been a bold-faced lie.

Even if he didn't want to admit it to himself, the truth was that he didn't want anyone to know he'd come home this early. Early of course being a relative term. On a normal night, three hours past midnight would certainly be considered quite late, but tonight had been the Senior Prom for Mooreland High's Class of '86, and walking through the door any time before dawn would inevitably draw attention and unwanted questions. Especially since he'd made no secret of his post-Prom plans, plans which, despite nearly two months of planning, hadn't quite turned out as he expected.

Taking the key out of the ignition, Jeff took a deep breath and dropped his head back against the headrest, closing his eyes for a long moment as he again reviewed events. Officially, the school year had ended Friday, with everyone but the senior class being dismissed for the summer. Tonight, or more specifically last night since it was already Sunday morning, had been the Prom, and come Monday morning, they would all get their diplomas and move on to the next phase of their lives. In Jeff's case, that meant leaving Glendale California for Fort Sill in Oklahoma to start basic training.

This weekend was going to be the last big blowout, a chance to party, say goodbye to his friends, and most importantly, leave his virginity behind. The last had been a prom night tradition even before his parents' time, and one that Jeff and his best friend, Carl Warren, had pooled their resources to make it as memorable as possible.

Jeff and Carl lived across the street from each other and had been best friends almost from the day the Warrens had moved in, ten years before. Looking back, Jeff always found it funny that his mother had to literally drag him and his older sister over to meet the new neighbors. The house had previously belonged to old lady Winters, and one of the first things every kid in the neighborhood learned was to stay well clear of it and her. He couldn't have imagined back then that the once forbidden house would become almost a second home, and the people moving into it practically family.

Over time, the two boys became as close as brothers, delighting in telling unwitting strangers that they were fraternal twins. This despite Jeff having a pale complexion and light blond hair, while Carl's skin was closer to dark mahogany and he wore his curly black hair in a tight afro.

The Cardinal Red Spirit that Jeff was driving actually belonged to Carl, a graduation gift from his father so that he'd have something to get around with when he went away to college come the Fall. The car had only been delivered two days ago and tonight was the first time they'd used it, picking up their girlfriends, Emily Greene and Penny Singleton, and driving to the Holiday Beach Country Club where the Prom was being held. After the dance, they'd gone on to the Lafayette Cove Resort for a different type of celebration.

Carl had been dating Emily since the beginning of the school year and Jeff had been going out with Penny only a few months less. Both couples' relationships had become progressively physical, although neither had gone all the way yet. They knew, however, that that was only a matter of time, and what better time could there be than the night of the Prom? Especially since the last of them would turn eighteen two days before.

Prom had indeed been spectacular and everyone had a great time, dancing and snacking the night way while keeping a watchful eye on the clock and the approaching midnight hour. That was the time they'd make their exit and head over to the Cove. The clock had finally chimed and as one day gave way to the next, the two couples slipped out to the parking lot. As they did, they discovered that they were far from the only graduates who'd planned to take the party to more private settings.

To save time, Carl and Jeff had checked into the Resort earlier that afternoon and already had the key. The suite they'd booked had been far from cheap, but they figured it was worth the expense so that each couple could have their own bedroom. A coin toss had determined who got which, with Jeff winning the larger room and better view. As he watched Carl and Emily practically race to their room, Jeff doubted either of them was going to spend any time admiring the view, and the bed in either room was the same size anyway.

In fact, Jeff barely gave the view in his room a brief glance before his attention was absorbed by the more enticing sight of Penny coming out of the bathroom in a translucent, light blue baby doll negligee, An outfit she had secretly borrowed from her older sister, who had worn it on her wedding night. Penny's bright pink nipples were clearly visible in the see-through gown, as was the thick patch of red hair that the matching panties did little to conceal.

"Wow!" was all Jeff could think to say as she strolled across the room to the side of the bed.

Jeff never undressed so fast in his life, stripping down to his boxer shorts as he left the rest of his clothing in a rumpled pile on the floor. Penny had already slid onto the bed and Jeff eagerly followed her from the other side. They started to make out, mouths colliding as excited hands rolled across willing bodies. It was a path they'd gone down before, but this time there'd be no stop sign to hold them in check.

Jeff had one hand under the flimsy material of Penny's top, pressing tightly against her breast, even as the fingers of his other hand found their way down into her panties, there to rub against her pussy. All the while their tongues intertwined within each other's mouths.

Penny's hands were both inside Jeff's shorts, one wrapped tightly around his cock, the other cupping his balls. The warmth and excitement of her touch had brought the short haired teen to a hardness he'd never experienced before. In only a few more minutes, his life would forever change. Or so he thought.

Jeff kissed her once more, a feverish anticipation fueling his desire as he slowly lowered her down onto the mattress and began to slide down her panties. Somewhere deep inside, a small aspect of his mind noted that this was the furthest that they'd ever gone. A small notation, that would be soon be wiped away by what was to follow.

As Jeff began to slide the thin underwear down across the cheeks of her ass, Penny lifted it just a bit off the bed, the bare minimum amount of space needed to allow him to take them totally off. He'd gotten them more than two-thirds there, when the redheaded teenager unexpectedly dropped her bottom back onto the mattress, impeding their passage.

"Jeff, stop," she said.

His attention more on the sudden resistance of movement than her words, the meaning of them didn't initially register on Jeff.

"Jeff, please stop," Penny repeated, her words now accompanied by action as she replaced his hands on her panties with her own and pulled them back up.

This time, the words had come through clearly, especially since they were followed by the motion of her body as she pulled away from him.

"Is something wrong?" Jeff asked, not really sure what was happening.

"I'm sorry, Jeff, I really am," Penny said as she slid back even further, pulling her loosened top closed as she did, "but I can't do this. I thought I could, I really did, but now that we're here I... I just can't."

"I don't understand," Jeff said, confusion in his voice.

More than half the bed now separated the two of them and Jeff made no attempt to close the gap. Instead he sat silent, giving her a chance to explain just what the hell was going on.

"I like you, Jeff, I really do," Penny said, "in fact, I think I might even love you. I couldn't have come here with you if I didn't."

"But...?" Jeff interjected, knowing that there was a but in there somewhere.

"But, as much as part of me wants to do this, another part says I shouldn't," she said. "Your first time should be something special, something that you can look back on and feel good about."

"This isn't special?" Jeff asked as he indicated the room around him with an outstretched wave of his hand, thinking how many of their classmates were either down at the cheap motel by the beach or worse, in the back seat of their cars.

"I'm not talking about the room," Penny replied. "The room is awesome. I don't think we could've found a better place."

"I still don't understand, then," Jeff repeated.

"A week from now, where will the two of us be?" Penny asked.

"Penny, you know where I'll be," Jeff answered. "You've known for months that I was going into the Army after graduation. You even helped me fill out a lot of the paperwork."

"And I probably should've said something months ago," Penny added, "but I didn't. I didn't because I thought that we could make a long-distance relationship work, a lot of people do. But now, I'm not so sure any more."

"Carl is going away to State in a few weeks and Emily is staying here," Jeff pointed out.

"Carl is only going to be a couple of hours' drive away," Penny countered. "He'll be home just about every weekend and during school breaks. How often are you going to be home, Jeff? You can't answer that, not when you don't even know where you're going to be six months from now. Didn't the sergeant down at the recruiting office say that there was a high probability you'd be stationed overseas?"

He had indeed, which at the time Jeff had found exciting. Now he was realizing some of the price he'd have to pay for that opportunity.

"My Dad was drafted into the Army, Jeff, and my Mom waited for him to come back from Vietnam," Penny said. "She once told me that they were the longest, loneliest two years of her life. You enlisted, and that means that you're going to be gone for twice that long. Thankfully there's no war now, but I don't think our relationship can survive that."

"Penny, you know that I want to marry you eventually," Jeff said.

"That's the key word, isn't it -- eventually," Penny said. "What does that mean? When you finish basic training, after your first overseas deployment, or when you finish your enlistment? Even if you put a ring on my finger before you go, what kind of people will we be two years from now if we're not together during that time? Will we even care about, much less love each other?"

She paused and took a deep breath before going on.

"I know this is a lot to drop on you at the last minute like this, and I really should've expressed my doubts about what we were doing when I first started having them, but..."

"But you're expressing them now and that's what matters," Jeff said, realizing that he really hadn't spent much time thinking about what the future would hold for Penny and him, other than expecting she would wait for him to come back. Now, listening to her concerns, that seemed like such a naïve belief.

"I thought about it for a long while, and kept telling myself that at least we'd have tonight together," Penny added, "but the more I thought about it, the more I realized that wasn't going to be enough."

The actual words hadn't been said, but they didn't need to be. Jeff knew their relationship had just come to an end. Deciding that perhaps they both needed to hear that, he said it out loud.

"You're not angry, are you?" Penny asked after Jeff had done just that.

"Angry, no, of course not," Jeff said, not adding that disappointed was another matter.

He didn't say it, but Penny could tell that he was from his tone and body language. Then there was the matter of the quite visible erection straining against his boxers.

"Would you like me to give you a blow job?" Penny asked, her eyes clearly focusing on his hardness.

Jeff wouldn't have been human if he didn't consider it, even if only for a few moments. Over the course of their relationship, Penny had gotten him off with her hand a number of times, as he had with her, but could never bring herself to take him in her mouth. For her to offer to do so now, Jeff knew, was a major concession. No, not a concession, he corrected himself, a consolation -- as in consolation prize.

"No, you don't have to do that," he said, well aware what he was turning down.

"Okay," Penny replied with a clear sense of relief. She would've done it, but was thankful she didn't have to.

"Maybe we should just get some sleep," Jeff suggested, thinking they should just put this night behind them.

"Actually, I think it might be better if you took me home," Penny replied.

"You mean now?" Jeff asked.

The look on her face said just that.

"If we spent the night, then everyone would assume that we did it," Penny pointed out, "even if we didn't."

'A lot of people are going to think that anyway,' Jeff thought, recalling how many people saw them get into Carl's car in the Country Club's parking lot, a few of whom had to have heard them say where they were headed.

Before he could point that out, Penny expanded on her desire to cut the night short.

"It really doesn't feel right staying here with Carl and Emily doing it just down the hall," she said. "I'd rather just go home."

What she didn't say, and Jeff had no way of knowing, was that she feared that if they spent the night, she might brush aside her rational decision and act precipitously. And if she did have sex with him, it would make it that much harder to put the relationship behind her.

Jeff shrugged his shoulders in surrender and slid off the bed. As he did, he realized that he had to let Carl know they were leaving, otherwise he'd be looking for the two of them come morning.

"I have to let Carl know we're going," Jeff said as he headed for the door. "Give me a couple of minutes and I'll be right back."

-=-=-=-

"Carl?" Jeff said softly as he knocked on the door of the other bedroom, repeating it twice before hearing muffled voices replaced by the sounds of footsteps.

The door opened a third of the way and an understandably upset face appeared in the opening.

"Jeff, I love you like a brother, but you'd better be telling me that the hotel is on fire," Carl said.

Whatever Jeff had planned to say was lost once he glanced past his friend into the room beyond. There, illuminated in the light of the table lamp, and only partially covered by a sheet, laid Emily Greene. One of her large caramel breasts was exposed, the dark nimbus surrounding its nipple clear even at a distance. It proved a distraction strong enough to cause Jeff to go momentarily blank.

"Jeff?" Carl said in a louder, more impatient tone, snapping Jeff out of his stupor.

"Oh yeah," Jeff replied in a voice almost too low to hear before switching back to a more conversational tone.

Quickly, he explained what had happened.

"Man, that sucks," Carl said once Jeff had finished. "So, what are you going to do?"

"I'm going to take her home," Jeff said matter of factly. "What else can I do? I just wanted to let you know where I'd gone."

"How are you going to get home, it's almost two in the morning?" Carl asked.

Until this moment, Jeff hadn't thought about how he was going to get Penny home.

"They have to have cabs downstairs," Jeff replied after a few seconds' thought. "I mean it's a hotel, right?"

"No, don't do that," Carl said. "Take my car. You can come back for us in the morning."

"Are you sure?" Jeff asked, grateful but hesitant.

"Yeah, I'm sure," Carl smiled. "Just don't make it too early; we're probably going to want to sleep in. Just let me get the keys."

As Carl stepped away from the door, leaving it partially open, Jeff saw that his friend had been standing there stark naked. When he opened the door further to hand him the keys, Jeff got a second look at the girl in the bed -- this time both of her breasts were visible.

'Well, at least one of us is going to have a good night,' Jeff thought as he turned and headed back to his own room.

Penny was fully dressed by the time he returned, the Prom gown she had worn no longer looking as inviting. He excused himself for a few minutes, figuring it was best to get dressed in the bathroom.

Once out of the hotel, it took less than twenty minutes to see Penny home, then another ten to do the same for himself. Or at least put him across the street from home.

-=-=-=-

Locking the car, Jeff was about to head home when the driveway light on the side of the house unexpectedly came on. Reflexively, the teenager looked up at the window by the side door, just as a familiar voice called out.

"Is someone there?" it asked.

"Well, so much for being quiet," Jeff said under his breath before raising his voice to say, "It's just me, Mrs. Warren."

"Jeff?" Felicia said, surprise clear in her tone.

There was a blur of motion away from the window as the figure in it moved to the side door.

"Is something wrong?" she asked as she opened the door and stepped onto the small landing. "Where's Carl?"

Despite being dressed in a robe and having her hair tousled, Felicia Warren didn't give the impression of having just gotten out of bed. For whatever reason, Jeff got the impression that she'd been up for some time.

"Carl's still at the hotel," Jeff said, trying to formulate an explanation as to why he wasn't. "I... I had a small change of plans for the evening."

"A change of plans?" Felicia, well aware of where they'd gone after Prom and why, asked.

Jeff's expression told her that he wasn't eager to elaborate.

"But Carl is okay, right?" she asked further.

"I'd say he's more than okay," Jeff replied, realizing as soon as he did that it might not have been the best answer, considering who he was talking to.

"I think I'd like to know a little more about this change of plans," Felicia said. "Why don't you come in and have some coffee while you tell me about them? I'll even give you a little time to come up with a convincing lie if you think that the truth isn't going to suffice."

Glancing across the street at the dark windows of his own house, Jeff decided that waking up one household in the middle of the night was enough. He climbed the two steps leading up to the side door and accepted Felicia's offer.

True to her word, Felicia waited until Jeff had gotten a good start on his coffee before asking once more for an explanation, reminding him that if he was going to make one up, it had better be a persuasive one.

But the idea of lying to the woman sitting across from him never entered Jeff's head; he had too much respect for her for that. Just about everyone in the neighborhood knew that Jeff and Carl were best friends, but few would imagine that Jeff also had a very close friendship with Felicia Warren as well. And not for the reason that a casual onlooker might think.

Five four and a hundred and thirty pounds, the forty-five-year-old housewife had a figure that drew the attention of nearly every man in the neighborhood. With soft coffee skin and neck length curly auburn hair, Felicia had looks that made her appear a decade younger than her years. Once, during his earlier teens, Jeff had read the tag on her bra in a laundry basket, finding it an impressive 38DD. Of course, that wasn't the sort of thing you were supposed to note about your best friend's mom, but few guys his age could've resisted the temptation.

But again, it wasn't her bodacious boobs, as Jeff had heard them called by others, that had been the foundation of their friendship. No, it was the number of late nights he'd sat on a stool in her kitchen sharing, at first a hot chocolate and later coffee, while they discussed his life and the world around them. Most times, Carl was right there with them, other times not, especially as they neared young manhood and his interests grew to include the company of more unrelated women. Jeff had a good relationship with his parents, better than most of his friends, but sometimes it was good to have someone older to talk to that wasn't a blood relative.

Ann Douglas
Ann Douglas
3,178 Followers