Fifth Wheel - Cover

Fifth Wheel

by Ann Douglas

Copyright© 2022 by Ann Douglas

Erotica Sex Story: Harold wasn't having fun on spring break. His buddies seemed to use him for transportation. The last day he got lucky when he met a busty older woman.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Consensual   Fiction   Oral Sex   .

Harold Carter sat alone at one of the smaller tables set against the back wall of Captain Jack’s, nursing the still half full glass of beer he’d ordered a half hour before. Up on the stage at the other end of the bar, a singer was performing Gilbert O’Sullivan’s hit from last year, ‘Alone Again, Naturally,’ a song that accurately described how his night was going. In fact, it pretty much described how his entire week had gone. Spring Break in Fort Lauderdale was supposed to be about cutting loose and getting lucky, or so all the magazine articles said. From the sandy haired nineteen year old’s perspective, he had as much of a chance of scoring tonight as Senator McGovern had of beating President Nixon last November.

Five nine, with an average build and equally average looks, Harold had enjoyed mixed success with girls back in high school. He’d dated a few girls his first few years, but none of those relationships lasted long enough to get serious. Senior year, however, he thought he’d hit the jackpot when Susan Adams not only made it clear early on that she wanted to go steady, but before the year was out had gone all the way with him — twice.

It wasn’t until he’d gone home to Blue Ridge Falls for the Christmas holidays that Harold realized his success with Susan had been due more to her desire to have a boyfriend — any boyfriend — than his charms. In the few months he’d been away, he’d been replaced both in Sue’s affections and undoubtedly in her bed. Tony Hamilton, who worked at Mitchell’s Hardware, might not have gotten a scholarship to some fancy out of state college, but he was there every Friday night. And as far as Susan was concerned, that was what mattered most.

In the seven months since he’d started at Northern Georgia State, Harold hadn’t so much as been on a coffee date. A small college, at least compared to its more well known neighbors, the school had a male to female ratio more than two to one. A fact that elevated girls who might have only been a five elsewhere to an eight or nine, along with the expectation that they could be more choosy in deciding who to grace with their company. It was a situation that seemed to have followed him down to Florida.

“How come you’re not sitting up front there with your friends?” a soft but unfamiliar voice to Harold’s left asked.

It took a moment for Harold to realize the question had been addressed to him. Turning in the direction of the voice, he found a woman in the black slacks and white pirate blouse that served as the costume for all of Captain Jack’s Buccaneers. What set the curly haired brunette apart from the other waitresses, at least to him, was that she was clearly older than the rest. Taking a guess, he thought her in her late thirties, or perhaps even as old as forty — which to him was pretty old. After all, his mother was forty-two.

She had a pleasant smile and bright blue eyes, but for the most part, the word that came to mind in describing her looks was ordinary. Not that he meant it in a bad way, but simply that if he’d passed her in the street she’d hardly draw his attention — at least not for her facial features.

The view a bit lower, however, was a different story. Filling out the low cut blouse was a bust that had to be at least thirty-eight inches, barely contained by the tight fitting top. None of the other servers came anywhere close; in fact, Harold couldn’t remember ever meeting a girl who did.

“Excuse me?” Harold asked.

“I asked why you weren’t sitting up front with your friends,” she repeated, motioning with her head to a table only a dozen feet from the stage where four other young men sat, accompanied by an equal number of attractive young women, sat. “They are your friends, aren’t they? I saw you all come in together.”

“Well yes, sorta,” Harold replied.

The quizzical look on the waitress’s face said that needed a bit of explanation.

“It’s just simple math, really,” Harold offered, only answering the first half of her inquiry. “Five guys, four girls, who needs a fifth wheel?”

“That’s just awful,” the waitress, whose name Harold now noticed from her tag was June, said. “What kind of friends do that?”

“Well, they’re not really my friends,” Harold said, now explaining the second half, “at least not close ones. We just all live in the same dorm back at school. I was sort of a last minute addition to the road trip.”

“How was that?” June asked.

There really was no reason for Harold to share the story, but then again, there wasn’t any reason not to.

“Well, originally Steve Burke was supposed to be the fifth guy,” he said. “They were using his car for the trip down. But he had to cancel the day before they were supposed to leave due to a family emergency.”

“And if you all weren’t, as you said, really friends,” June asked, “what made them ask you?”

“I guess I was the only one still at the dorm that had a car,” he explained, realizing as he did how much like a loser that made him sound.

“I see,” June said, glancing back to the table in front where the four couples seemed to be having a pretty good time. “Just out of curiosity, who decides who has to leave if you meet an odd number of girls?”

“We draw lots,” Harold replied. “Short straw leaves.”.

“And how many times have you had to do that?” she further asked.

“Four,” he replied.

“And you’ve been here how many nights?”

“Six,” Harold said. “This is our last night; we’re heading back north tomorrow.”

“Why do I have the feeling that I wouldn’t be going too far out on a limb if I were to guess that you’ve come up with the short straw more than anyone else?” June commented.

Harold didn’t have to confirm her observation, the way he just glanced down at the glass in front of him did that well enough. By the third drawing he’d realized that he should’ve avoided the short straw, if only by random chance. His fourth loss seemed statistically impossible.

“You know you’ve been faked out, right?” June asked, pointing out the obvious.

“Yeah, I finally figured that,” Harold admitted, realizing now that the drawings had been rigged.

“These guys let you drive them five hundred miles and...”

“Actually it was closer to six,” Harold automatically corrected her, realizing as he did that the added distance made no difference. “But we took turns driving and they paid for gas,” he added, as if that made it all right.

“You’re too nice, kid,” June finally said. “Me, I’d have skipped out on them midweek and let ‘em take Greyhound back to school.”

Then, to his surprise, June reached down and picked up his now warm glass, replacing it with a full one from her tray. When he looked up, he was met with a broad smile.

“On the house, kid,” June said.

“Harold,” he said, figuring giving her his name was the least he should do.

“Do they call you Harry or Hal?” June asked.

“No, they don’t,” Harold replied, the inflection in his tone making it clear that he disliked either diminutive.

“Somehow I didn’t think so,” she said before making a half turn in the direction of the table that had originally ordered the drinks on her tray.

She paused a moment and turned back to Harold, leaning down so that only he could hear what she said.

“Let me share a little of the skinny that goes on around here,” she whispered. “It might make you feel a little better. Those plastic friends of yours might see themselves as a bunch of Casanovas, but those girls they’ve been buying drinks for all night are townies, not horny coeds looking to party. The chances of any of them getting into their panties are, well, let’s just say I have a better chance of waking up tomorrow and finding Rock Hudson in my bed.”

Then with a soft chuckle, she was gone.


After finishing his drink, Harold decided that just sitting here watching everyone else have fun was hardly the best way to spend his last night in Fort Lauderdale. He left a tip next to the glass that was more than what the beer would’ve cost, then got up and headed for the exit.

It was a cool, clear night and since they’d all slept in that morning, Harold wasn’t the least bit tired. Noticing the entrance across the road to the boardwalk that ran the length of the beach, he decided to take a little stroll. As he climbed the stairs, he saw that a number of other people had the same idea, but once he’d reached the boardwalk itself, he was disheartened to discover that most were couples. Still, it was a nice night, so he mentally flipped a coin and set off in a southerly direction.

After about a half mile, he wondered if he had subconsciously picked the direction opposite of most of the other walkers. The spot where he now stood was practically deserted and leaning on the railing overlooking the beach, he studied the bright full moon in the sky.

It was an activity he’d greatly enjoyed as a kid, having spent many a night out in the yard with the telescope he’d gotten for his thirteenth birthday. The gift had given him a brief surge in popularity among his classmates, at least until they discovered that he actually was more interested in looking at heavenly bodies than those that might be glimpsed if you pointed it towards the right window.

Eventually, he’d learned the topography of the lunar surface so well that now, even without his telescope, he could find the landing sites of the six lunar missions. Tranquility Base was easy, but the Taurus-Littrow valley, the site of the final Apollo flight last December, took a little more doing. As he remembered watching the last moon walkers on television, Harold also recalled where he’d originally planned to be this week.

“Well, hello stranger,” said a now familiar voice from behind Harold, interrupting his thought. “We have to stop meeting like this or people are going to begin to talk.”

Turning around, Harold confirmed the voice, finding June, now wrapped in a light sweater, standing there.

“What brings you this far off the beaten path?” June asked, adding that most of the tourist attractions were back the other way. Her own presence was explained by her sharing that she lived just down the road.

“Just enjoying the night air and appreciating the scenery,” Harold replied, adding that he normally didn’t get as good a view of the moon back at school.

“You did seem a bit lost in thought when I came up behind you,” June observed. “I wasn’t sure if I should disturb you.”

“Oh, it was nothing important,” Harold smiled. “I was just thinking that they’re going to launch Skylab tomorrow, and if I’d stuck with my original plans for this week, I’d have been there to see it go up.”

“That’s a rocket, right?” June asked, having seen something in the newspaper about it.

“Well, actually it’s a space station,” Harold corrected her, “the first American one. The Russians put up the first one, Salyut, last year. But they do launch it into space on a rocket, a Saturn V.”

Harold chided himself for his response, knowing he had that idiot grin on his face that he got when he talked about the space program. Both back home and even at school, he was always reminding himself that not everyone was a space geek like him, interested in every little detail.

June didn’t seem to have taken offense at the correction, asking instead if that was what he was studying in school.

“Well, I’m a general science major,” Harold replied, “although if I could work for NASA, that would be bitchin.”

“Can you see the launch from here?” June inquired, sounding genuinely interested.

“I’m afraid Cape Kennedy is too far north for us to see it,” Harold replied, “almost two hundred miles.”

“I guess I’m just showing my ignorance,” the older woman said. “I really don’t know much about the space program other than they launch rockets from here in Florida. You’d think that after living here for almost a decade I’d have learned more about it.”

She went on to add that she’d moved to Florida from Chicago after her divorce, wanting to make a fresh start. She couldn’t remember exactly when, but it had been soon after President Kennedy had been killed.

Harold had only been eight back then and only vaguely remembered the assassination.

“You know, there’s a much nicer view about a quarter mile or so down,” June mentioned as she changed the subject. “That is, if you were still planning to walk some more.”

“Might as well,” Harold mused.

“Great, then I’ll walk with you,” June said, “seeing as I’m going that way anyway. If you don’t mind the company?”

“Nah, not at all,” Harold replied. “Actually glad for it.”

They continued talking as they walked, with June asking more about what his life was like back in school, as well as what kind of television and movies he liked.

In a funny coincidence, both of their most recent favorite movies starred the same actor — Marlon Brando. In Harold’s case, it had been ‘The Godfather,’ a film he had seen with his father, and for her it had been ‘Last Tango in Paris,’ a film Harold had only heard about as none of the theatres back home showed films like that.

As far as television went, June liked shows like Columbo and McMillan and Wife. Harold’s favorite show, when he had the time to see it, was the TV version of the movie M*A*S*H.

“I saw that once or twice, but wasn’t that impressed,” June offered. “I think most television shows based on movies don’t last too long. After all, they don’t have the stars that made the original film such a hit. Plus, there are some things that you can say or do in movies that you certainly can’t do on TV.”

“I have a feeling that this one might be the exception to the rule,” Harold suggested, knowing that he was speaking from the heart and not his head. What June had pointed out was true, and in the end M*A*S*H would probably soon be canceled and forgotten.

She asked a bit about his hometown and his family, and if he had a girlfriend back home.

“I used to, but not anymore,” Harold answered.

“What happened?” June asked.

“What I guess usually happens to a lot of couples after high school, especially when one of you goes off to college,” Harold replied. “She wanted a boyfriend that was there, and not a four hour drive away.”

“That’s too bad,” June said, trying to sound sympathetic, “but I can understand where she was coming from. Some parts of a relationship can’t be phoned in.”

It was probably too dark to see that the last comment had made him blush, at least Harold hoped it was. If it wasn’t, June didn’t seem to take notice of it.

“No new girl at the college?” she inquired instead.

Harold gave a much more general recitation of his observation that with guys outnumbering girls at school, they were usually looking for more than average.

“I don’t think I’d call you average,” June remarked after a momentary pause. “In fact, I think you’re rather cute.”

Before Harold could reply to the compliment, June turned in the other direction, looking at something in the distance. Then she turned back to Harold.

“Well, here’s the spot I was talking about,” June said, stepping past him over to the edge of the railing to look out on the horizon.

Following in her steps, Harold stepped up alongside her and followed her gaze out to where the full moon was reflected on the ocean. In his opinion, the view really didn’t seem any better than it had back at his original observation point — in fact it probably wasn’t as good. Still, if only to be polite, he agreed how nice the view was.

They stood there watching the waves break along the shoreline for a minute or so, then June unexpectedly said that it was time for her to say goodnight.

“That’s me in that red and white building just over there,” she said, turning around and pointing out the small two story apartment complex just beyond the road.

“Oh, okay,” Harold said, a noticeable regret in his voice. The nocturnal stroll along the beach had been the most enjoyable part of his day. After thinking about that for a few seconds, he repeated it aloud.

“Oh, that’s sweet,” June replied, impulsively leaning inward and kissing him on the cheek. “I enjoyed it too.”

She started to walk away, the boardwalk at this point being level with the road, then paused after going about thirty feet. Looking back over her shoulder, she confirmed what she already knew — that Harold was still watching her.

“You said you were headed back to school tomorrow, right?” she called out just loud enough to heard.

“Yes,” Harold confirmed, wondering why she asked. “We’re supposed to head out about noon.”

She seemed to digest the confirmation for a few long moments, making no effort to continue on her way.

“You know,” June said in the same tone, pausing a second to glance right and left, as if to check whether anyone else was around, “this is probably pretty far out there as ideas go, but as they say, life is short and nothing ventured, nothing gained.”

Harold was confused and the look on his face confirmed that he had no idea what she was talking about.

“So I was just thinking,” June went on, “that, if you don’t find the idea too absurd, you might stop by my apartment when you finish your walk, it’s 1C by the way, and we could continue our chat.” She paused a breath then added, “Or perhaps find something a bit more interesting to do.”

With that, she abruptly turned her head and continued walking, going another ten feet before again looking back.

“And just so you don’t let yourself think you’re just letting your imagination run away with you,” she said, now loud enough for anyone who might have been within earshot to hear, “I am offering you the chance to get lucky tonight. The choice is yours, but just give me at least twenty minutes to take care of a few things.”


As June receded into the darkness, Harold stood there stunned, unable to believe what he’d just heard. It was like something out of those blue movies the fraternities sometimes had private showings of. One of his cousins, who was a brother, had invited him to a screening when he’d first arrived on campus. It had been an eye opener, as they certainly hadn’t anything like that that back in Blue Ridge Falls. Well, at least not that he’d known of. His Dad was a lodge member, and it wasn’t inconceivable that things like that happened there too.

Just on the other side of the road, Harold saw June reappear for a moment as she passed under a streetlight by the edge of her building. Then, just as quickly, she again passed from view as she moved out from under the cone of illumination, presumably entering the structure.

‘So what do I do now?’ he asked himself, feeling a bit asinine to have even asked himself the question.

After all, he’d come down to Fort Lauderdale to sow some wild oats, and here he was being presented with an opportunity to do so on a silver platter.

Back in high school, Harold had read an illicit copy of “The Graduate” that was being passed around. Illicit only in the respect that neither the school or town lobby would carry the book. In reading the best seller, he’d been enthralled by the character of Mrs. Robinson, a woman who by her own admission was twice the age of the recent college graduate she seduces. The imagery of the book — he’d been too young to see the movie when it first came out — had stayed with him for months, especially during some of his private nighttime exertions.

No, the question really didn’t need to have been asked.


Even though it was already after midnight, Harold found three men sitting outside the building when he’d finished following June’s path. Two of them were playing a game of chess on a small folding table, while the third alternated between watching the game and listening to a distant baseball game on a transistor radio. The spectator, older than the participants, looked up at Harold’s approach and, since he didn’t recognize him, gave him a look that seemed to challenge his right to be there.

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?”

 
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