Fifth Wheel

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Ann Douglas
Ann Douglas
3,175 Followers

Flashing a smile, Harold walked right past them, wishing them a good evening as he stepped up to the row of bells and confidently pressed 1C. What seemed a long wait followed and during that pause, the young man wondered if perhaps he was the victim of a practical joke. For all he knew, June could've walked right past the small apartment complex and gone elsewhere. He didn't need to turn around to know the older man was boring holes in the back of his head.

"Hello?" a quiet voice said over the intercom, a voice too tinny to recognize.

"It's Harold," he simply said, wondering what to do if the next words were "Harold who?"

Instead what he got was a loud click as the solenoid in the door lock disengaged and now he was able to now turn the knob. With a soft sigh of relief, Harold pushed the door inward and stepped inside. The man behind him had already lost interest, turning his attention back to both his games.

Once inside, Harold found there were five apartments on the first floor, with 1C being at the far end of the hallway. When he reached it, he saw that unlike the outer door, the one to the apartment was unlocked and already open a crack. He took a deep breath and gently pushed it open further, giving himself a moment for his eyes to adjust to what he could see was a semi-darkness beyond.

While the light was off in the small vestibule, it was still possible to find your way beyond the threshold by the dim light of an open room on the left of the short walkway. Taking a tentative step inward, he softly called out her name.

"June?" he said, a slight tremor reflecting a still felt hesitancy.

"Close the door," he heard her say from the direction of the light.

Now satisfied that he was in the right place, Harold did so, making sure he heard the lock click into place before moving any further forward. That done, he turned back around, expecting to find a still empty hall. Instead, he found a sight that took his breath away as a second hall light suddenly came on.

There, bathed in the soft glow, stood June wearing a short sky blue nightgown that revealed more than it concealed. The top of her pirate outfit had certainly put her breasts on display, but it might as well have been a nun's habit in comparison with the see-though properties of the nightwear she'd replaced it with. Large thick nipples pressed through the thin lacy material and, as he shifted his gaze downward, Harold could see a thick dark bush through equally transparent panties.

Time seemed to stand still as Harold stood transfixed, oblivious even to the sound of his own heartbeat – which had sped up considerably.

"Well, are you going to just stand there and stare," June finally asked, once it was obvious that Harold had been awestruck into immobility, "or are you going to come in?"

-=-=-=-

As he passed June into the room from where the original light had come, he found unsurprisingly that it was her bedroom. In the few seconds it took for her to turn off the hall light and follow him, Harold took in his surroundings.

The bed was the first thing that caught his attention of course. Simple in design, it had plenty of room for two, he was glad to see. Not willing to go to a motel, Susan had screwed him on her own twin sized bed, one with a mattress barely wide enough for one and a frame that he was worried at the time might collapse under the weight of both of them – especially in light of what they were doing on it. This bed, however, looked more than sturdy enough for the task.

The rest of the furniture in the room followed the same pattern as the bed, a mixture of styles that seemed more functional than decorative. The room wasn't exceptionally tidy, but neither was it exceptionally messy, 'lived in' came to him as the best way to describe it. There were a few articles of clothing tossed about, most notably the waitress outfit from Captain Jack's, draped over an old wooden chair off to the side.

It was only when he took a moment to look at the chair that Harold noticed the built in closet behind it, the one with what appeared to be, on a second look, two cloth shower curtains hanging on a rod. One of the curtains was partially open, revealing a different sort of clothing than the ones haphazardly tossed about. Clothing that almost instantly replaced the exhilaration he'd been feeling with trepidation.

"You don't live alone, do you?" Harold asked, the focus of his gaze leaving no doubt that he was referring to the unmistakably male clothing hanging in the closet.

"No, I have a roommate," June said as if it had no more importance than the fact that the sun would be coming up in a few hours. "But if you're worried about being interrupted, don't be. He's not home, nor is he likely to be in the next few days, much less the next few hours. So we're quite alone here."

"Boyfriend?" Harold asked, not having seen a ring on June's finger.

"No, not really," June replied.

The look on Harold's face said that this time he was the one who needed more of an explanation.

"His name is Sean, and he's a trucker," June replied to the silent inquiry, "one of those guys you see on the Interstate, driving those big eighteen wheelers. In fact, that's where he is right now, up in Georgia making a run. And what the two of us are doing is, well, I guess you could call it cohabiting, that's as good a description as any. We share rent, utilities, and other expenses – and yes, we also sometimes share more than a bed when the mood strikes. But that's the extent of it. I don't ask where or with who he sleeps while he's out on the road, and he gives me the same courtesy. So now, if that's a problem for you..."

"No, it's not a problem," Harold said. His sudden concern that a boyfriend, possibly a jealous one, might show up at a most inopportune moment, in which he would quite literally have his pants down, now seemed a bit silly.

"Good," June smiled as she moved a few steps closer to Harold. "Now that we've got that straight, and since you've already pretty much seen what I have to offer, don't you think it's time to show me what you bring to the table, or bed as the case may be?"

With that, June reached out and undid his belt buckle as well as the clip and zipper of his tan slacks. Before he could even fully react, she had her left hand down in his underwear, closing her fingers around his cock.

"Very, very nice," she said, sliding her fingers up and down its length, gauging its size. "You know, I would've been a bit hurt if I didn't find it already hard," she added with a soft laugh, "but this will do just fine."

Withdrawing her hand, she moved it and her other hand to the sides of his pants, sliding her thumbs under the waistbands of both his slacks and the boxers beneath. In a quick motion, she dropped down on bended knees and pulled both all the way down to his ankles. Freed from any restraint, his engaged manhood sprang to attention.

"Very nice indeed," she repeated as she rose back to her feet, taking a step back let him step out of his pants and also remove his shoes and socks.

Her hands again moved to his sides, this time grabbing the edges of his dark t-shirt. With equal ease, it too was gone, leaving him as naked as a newborn – that is, if a newborn had a lightly haired body and a raging hard-on.

Placing the outstretched fingers of both hands on Harold's chest, June ran them across it and then down along his stomach. From there she dropped her left hand to cup his balls, causing Harold to let out a soft moan as she glided her hand up along the underside of his cock to the edge of its crown.

"I bet that ex-girlfriend of yours misses going down on this beauty," June commented as she ran her hand down it in the opposite direction.

"She never ... I mean," Harold started to say reflexively, then remembered too late that he didn't have to reply to everything June said.

The look on his face said what his hesitant response hadn't.

"No way," June said in disbelief, certain she was reading his expression wrong. "Are you telling me she never went down on you?"

Embarrassed, Harold just slightly shook his head no, a reluctant reply that caused June to jump to an extreme if wrong conclusion.

"Oh my God, you're not a virgin, are you?" she asked.

"No, I'm not a virgin," Harold replied, quickly finding his voice again.

"Not that I would've minded," June responded with a predatory grin. "I've never popped a young man's cherry before. I've heard it can be a lot of fun."

"I'm not a virgin," Harold repeated, knowing that his face was again a bright red and this time there was no darkness to hide it.

"Okay, I believe you," June said. "I guess you were just unlucky enough to have a girlfriend who didn't like giving head," she added as her eyes again surveyed his manhood. "Me, I love giving blow jobs."

Harold's reaction to that caused another question to fill June's head.

"You have had a blow job before, haven't you?" she asked. "I mean, you did date other girls before, what was her name again, oh yeah, Susan?"

Again Harold replied with silence.

"Seriously?" June asked skeptically. "You're nineteen years old and you've never had a blow job?"

Again, Harold just slightly shook his head no.

He was being honest in that he wasn't a virgin, but behind that truth was that both times he'd been laid it had been with a girl who knew as little about what they were doing as he did. Which was basically what went where.

And as far as the girls he'd dated before Susan, well, he'd never gotten past second base with any of them. Well, maybe shortstop might be more accurate, because Janet Price had once given him a hand job, and, even if she'd used a handkerchief to hold it, it still counted.

"Well, my young friend," June said with mirth in her voice, "it seems you are in desperate need of an education. So let's get to it."

With that, she led Harold over to the edge of the bed and pushed him down onto the mattress. Then, standing over him, she reached up and one at a time, slid the spaghetti straps of her nightgown off her shoulders, causing the thin garment to slide down the length of her body – leaving her with only the equally thin panties by way of concealment.

"Sweet Jesus!" Harold exclaimed loudly as her breasts came into full view.

Full and rounded, the mammoth mounds were capped by thick nipples that stood erect in the center of dark circles almost the size of his palms. Discounting brief, accidental glimpses of his sister growing up, they were only the third set of boobs he'd ever seen. And while at the time he'd been highly impressed by the two high school girls who had let him examine theirs intimately, neither set could compare to the bounty now before him.

"I see you're taken by the girls," June laughed softly as she the massaged both breasts, rubbing her thumbs against the stiff nipples. "Not bad for an old lady of forty-five, don't you think?"

That June was a half decade older than he'd earlier imagined went right past Harold's head, but would come back to him much later when it no longer mattered. Right now, it wasn't the head on his shoulders that was in charge.

But even if it had been, logic and reason would've been tossed aside a few beats later as, without further preamble, June dropped onto the open space on the edge of the bed and leaning over the nineteen year old, took hold of his cock and slipped it deep into her mouth.

-=-=-=-

'Oh my God!' Harold's inner voice thundered in his mind as he felt the warm wetness of her mouth engulf his manhood.

He'd heard guys brag about having their girlfriends suck them, about how incredible it felt. Yet, up until this moment, he'd always felt they'd been exaggerating. Now, if anything, he felt like their claims had been vastly understated.

The sensation of June's lips sliding up and down the sensitive skin of his cock produced a thrill he was having trouble finding the words to describe. Add to it the delightful sensation of the tip of her tongue rolling along his length, and the task became impossible.

Harold watched in fascination as her head rose up and down on his cock, her heavy breasts hanging free and bouncing against his body on the downward strokes. He'd never felt so hard before, or imagined that a woman could take so much of him into her mouth.

Not that he thought he was huge by any means, but Harold knew where he stood in the size department. He'd made enough surreptitious comparisons in the high school showers and locker rooms to know he had nothing to feel anything less than confident about.

June let his cock fall free of her mouth, but not the hand she had wrapped around its base. She ran her tongue along the underside of his shaft, rolling it across his balls before taking them in her mouth, one at a time.

"Oh yeah!" Harold moaned loudly, a spark racing across his body as the tip of her tongue now danced across the underside of his scrotum.

She took his length back in her mouth, sucking it deep for what seemed like forever. Her tongue seemed everywhere, producing unimagined delights, causing a familiar pressure to build within him, one that he doubted he could long hold back – not that he really had any desire to.

June again let his cock fall from her mouth, and this time she made no move to reacquire it – at least not initially. Instead she slid off the bed and stood back up, causing Harold to fear something was wrong. He needn't have worried as, after sliding off her panties, she turned her full attention right back to him, in a way he didn't expect.

June took his cock in hand and pivoted her body over his, dropping down until the head was positioned right at the entrance of her pussy. Then, with a broad smile on her face, she slid down his pole until all of him was buried deep inside her.

"Hell's Bells!" Harold cried out, echoing a phase his grandfather had taught him when he was young, much to the annoyance of his mother.

If June's mouth around his cock had been a bit of bliss, the feel of her pussy was pure paradise. In the small amount of time he had allowed himself to consider the question during his slow walk from the boardwalk to the apartment house, Harold wondered how different being with the older woman would feel as compared with his previous experience with Susan. After all, while he suspected he hadn't been her first, Susan was just beginning her way down that road, whereas June obviously had a good number of miles behind her.

As she rode his cock with increasing speed, the answer to his question turned out to be not the one he'd expected. Susan, while pleasant, had admittedly been an uninspiring lay – pretty much having done little more than spread her legs apart and let him climb on top of her and slide it in. June, on the other hand, was proving a sexual dynamo full of seemingly boundless energy.

She shifted position so that she was actually rotating around his cock, even as she continued to ride it back and forth. She'd had him place both hands on her upper legs, allowing her to use one of her own to reach back to brace herself against the mattress. Her other hand played with her breasts, squeezing the soft flesh and hard tips.

After what seemed a long time later, she again shifted position so that now both hands braced her, allowing Harold to add the thrusts of his cock to those of her body, nearly doubling the pleasures he had been enjoying.

"That's it, baby," June said between breaths, "fuck me, fuck me good."

Experience told her that Harold was on the edge, and she still had a bit of a way to go. Bringing one hand back between her legs, she began feverishly rubbing her pussy, quickly narrowing the gap between them. By the time the younger man cried out in delight at his climax, June was there to share in it.

It was a small celebration, one that lasted less than a minute, but a celebration nevertheless.

Drained, June collapsed into the empty half of the bed, reaching up to cup the back of his head and pull it close enough for his lips to reach hers. It was a pleasant kiss, Harold thought, but at the same time bittersweet, as everything had happened so fast.

"I hope you enjoyed that as much as I did," June finally said a long pause later.

"Absolutely," Harold replied, trying hard to not show any disappointment in his tone. "It was incredible. "

"Good," June smiled, "and I'm sorry I got a little carried away. I can't remember the last time I did that."

"I didn't mind," he answered, this time failing to hide his mixed emotions.

"But you're a little disappointed," June said.

"No, not at all," Harold insisted.

"Honey, don't lie to me," she countered. "I hate it when men do that. I can tell you're a bit let down and I don't blame you. I promised you a night to remember and that's what you're going to have."

"We're not done?" he asked hesitantly.

"Certainly not," June laughed. "Baby, any idiot can fuck; all that takes is a hard cock and a bit of stamina. But now that we've gotten that out of the way, I'm going to show you how to really please a woman. That is unless you'd rather just pack up and go, now that you've gotten your rocks off."

"Absolutely not," Harold said firmly.

"Good, I knew you were a smart kid when I first saw you back in the bar," she smiled.

Looking at that smile, Harold wondered if she had been planning this back when she'd left him that free beer. He proved himself as smart as June suggested he was by not asking if she had. Sometimes it was better to just go with the flow and see where it took you.

-=-=-=-

June suggested that they take a few minutes to clean up and catch their breaths. She offered him first crack at the tin framed shower in the small bathroom, a courtesy he greatly appreciated once he felt the hot water wash over his body. When she had first mentioned the shower, Harold had thought she intended for the two of them to share one, a particular fantasy of his, but once he saw the size of it, he realized that would've been impossible. There was more room in a phone booth than in the cheaply made enclosure.

It wasn't until he was just about finished washing himself off that Harold realized that June was watching him from the doorway. He'd only pulled the shower curtain halfway closed, just enough to keep the spray from splashing out onto the floor, which had left just enough of a view for her to see him. The idea that she was watching him bathe gave him an unexpected thrill.

As they changed places, their bodies brushing against each other in the small room, Harold wondered if June expected him to watch her as well. He didn't want to ask because he felt, regardless of the answer, just voicing the question would make him look like an idiot. So he was greatly relieved when, after turning the water back on, the barmaid made no attempt to close the curtain at all. If that wasn't a sign, Harold didn't know what was. Figuring he might as well get comfortable, he sat down on the toilet seat, only a few feet away from the shower. June flashed him a quick smile, acknowledging the correctness of his choice, then turned and reached for the washcloth and a bar of soap.

Harold watched fascinated as, after first wetting herself down, June soaped up her entire body, spreading a thick lather all over her breasts and then down between her legs. She tightly squeezed her mounds, arching her head back with closed eyes, pinching her nipples between her fingers. From there, both hands ran down her stomach, converging between her legs to wash out the thick bush which had become matted with the juices of both. She then turned her back to the teenager, spreading her ass cheeks and cleaning there as well. Finally, satisfied that she was fresh as she could be, she turned the shower knobs from their halfway positions to full and rinsed away all of the soap.

Ann Douglas
Ann Douglas
3,175 Followers