Woulda Coulda Shoulda
by Ann Douglas
Copyright© 2026 by Ann Douglas
Erotica Sex Story: At forty-five, divorced bookkeeper Julie Wilkes has settled into a predictable life. Then she accidentally overhears nineteen-year-old Chris Cassidy confessing his secret attraction to her. With his summer job ending, Julie faces a delicious dilemma: play it safe or seize one unforgettable opportunity before it's too late?
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Age Gap Consensual Fiction Workplace Analingus Masturbation Oral Sex Petting Slow .
August 1975
Julie Wilkes sat at her desk in one of the tiny offices in the basement of Sutherland’s Emporium. The forty-five-year-old bookkeeper should’ve gone home two hours ago when her workday officially ended, but with nothing but an empty apartment to go home to, the dark-haired redhead would rather catch up on some work. She’d worked at the Brooklyn department store for nearly thirty years — first as a part-time sales girl during her last year of high school, then as a full-time sales associate while she went to the local community college at night, and finally in her present job after she’d gotten her degree.
Sutherland’s itself first opened its doors back when her grandfather had been a child, quickly becoming a neighborhood institution where you could get everything from houseware to pets, auto parts to children’s toys. The last became even more important years later when they began converting part of the top floor every holiday season into a winter wonderland, where parents could bring their kids to not only meet Santa but, from the late forties on, get a picture with him as well. Even more recently, they’d rebuilt part of that same space to hold a couple of full-sized AFX slot car tracks, where players could either rent cars and controllers, or bring their own, and compete for prizes.
Almost from the beginning, the store’s slogan had been “You can find everything at Sutherland’s,” and most people firmly believed that. Julie certainly had, given that she’d even found her husband there, a truck driver in the delivery department. But unlike many things found at the Emporium, her marriage hadn’t come with an extended warranty, much less a lifetime one, and had crumbled three years ago, just short of their fifteenth anniversary. Following their divorce, Carl Wilkes, who had always been a marginal employee, sought employment elsewhere, finding it at a similar store up in the Bronx — along with someone new to share his bed.
They hadn’t had children, and, with Julie having always earned her own keep, their separation produced few changes in her life other than an empty space on the other side of the bed. One which had been filled only irregularly in the years since, as the newly single woman discovered far too many men viewed being divorced as being synonymous with being an easy lay. Having been sexually active even before her marriage, Julie didn’t have a problem with doing the deed; she just didn’t like the assumption that it was a given, preferring sex to be on her terms.
An unexpected voice abruptly interrupted Julie’s concentration, causing her to look up and confirm that she was indeed alone. There had been a time when such an occurrence caused her to wonder if the halls of the century-old building were haunted, but now she knew it was merely the result of a poorly designed HVAC system. One which sometimes created a cross-talk effect, conveying distant sounds with such clarity that you’d think they originated in the same room. It didn’t happen that often and usually only lasted a short time.
Curious and a bit bored, Julie got up and moved over to the wall-mounted air vent that the sound had originated from. After listening intently for a minute, she realized that it wasn’t just one voice, but three, all male. As they became more distinct, she was able to recognize one as that of Danny Wray, a delivery driver who had once worked with her ex-husband. The second voice also belonged to another driver, Henry Warren, who had only been with the company about two years.
The last voice, however, was harder to place, but it was definitely younger than the other two. It was only when it grew stronger, indicating that the speaker had moved closer to the vent on his side, that Julie finally identified it as that of Chris Cassidy, one of the college students hired as summer help. The sandy-haired nineteen-year-old had no set job assignment, but was moved around to fill in for people on vacation. Evidently, this week that was shipping.
Seeing as delivery drivers knocked off even earlier than most other employees, having started well before the store opened, Julie was confused as to what they were all still doing here. A memo that Wayne Bennett, the general manager, had sent out last week drawing attention to some unexplained inventory discrepancies abruptly came to mind, and while she hated to think they were stealing merchandise, she felt obligated to be sure.
Julie didn’t have to listen long, however, to realize they weren’t here after hours for any nefarious reason. They were simply taking advantage of an empty locker room to hang out and have a few beers. Technically, drinking on company property was a violation of the rules; but it wasn’t like she hadn’t broken a few of them herself over the years. Besides, their being slightly inebriated made the conversation more interesting.
“So, come on, Chris, you still haven’t answered the question,” Danny Wray said. “If you could fuck anyone that works here, who would it be?”
“I know who I’d pick,” Henry Warren interrupted, his slight slurring of his words suggesting he’d had more to drink than the others. “Jenny Lane, hands down.”
“Yeah, like she’d want to screw a decrepit old asshole like you,” Danny responded, turning his attention from the teenager to his thirty-eight-year-old partner.
“Why not, she’s fucked just about everyone else, from what I hear,” Henry laughed.
Jenny Lane, Julie knew, was a vivacious blonde who worked the cosmetics counter up in the lobby. Twenty-five years old with a scandalous reputation, it was rumored that she’d slept with half the sales staff, including a few of the married men. Julie thought that was an exaggeration, but not by much.
Danny, it seemed, had already announced his pick before Julie had come in on the conversation. She idly wondered who it had been.
“There’s no one here at the store that really interests me,” Chris finally replied.
“Bullshit!” Danny echoed. “I know for a fact that you got a thing for someone that works here. Pete Cameron told me.”
Pete Cameron was one of the salesmen in the Sports Department, Julie recalled.
“He said that you told him that night he and Billy Taylor took you out to O’Malley’s,” Danny continued.
“They got me drunk the night they took me to O’Malley’s,” Chris stated with conviction. “Things you say when you’re drunk don’t count.”
“In vino veritas,” Danny countered, causing both of the other men to stare at him.
“What the hell does that mean?” Henry asked.
“It’s Latin,” Danny explained. “It means ‘in wine, there is truth’. In simple terms, it means that the things you say when you’re drunk usually prove to be true.”
“Where the hell did you learn Latin?” Henry said, his slurring causing him to have enough problems with English.
“I read a lot,” the older man replied.
Henry knew that was true, not being able to recall a time when his partner didn’t have some book stuck in his back pocket. Still, that didn’t answer the question of who it was that Chris had said he found attractive, and he said so.
But Chris still sat silent.
“Wait a second, Pete Cameron is one of those guys who, well, you know...” Henry abruptly said, bending his wrist forward as he attributed the younger man’s silence to a totally wrong conclusion. “Are you saying that Chris is...”
“No, not at all,” Danny said, quickly cutting Henry off in a sharp rebuke. Pete’s sexual preference wasn’t really common knowledge and he was surprised that Henry knew of it. “Chris likes girls, he just likes a particular sort of girl.”
Again, Henry was confused as to what the hell that meant.
“Alright, I said that I thought Julie Wilkes was really sexy, okay,” Chris said, a bit angry in his tone. “Are you satisfied now?”
“What?” Julie said in a voice just as loud, her own surprise enough to cause her to forget that the cross-talk effect could work in the opposite direction as well.
“Who?” Henry asked, not recognizing the name.
“The old lady from accounting,” Danny replied, “the skinny redhead with the small tits.”
Glancing down at her breasts, which measured 32B, Julie had to admit that someone else might consider them small. Not her of course, as she had always thought they were the perfect size for her five-foot-eight and a hundred and ten-pound frame.
‘And I’m not old,’ she thought to herself, even though she was older than either of the senior drivers.
“I still don’t know who you’re talking about,” Henry said as he tried to put the name and description together but again came up empty.
“The one that looks like the mom in that Fifties sitcom on ABC,” Danny finally said. “I can’t remember her real name, but on the show she’s Mrs. C...”
“Oh wait, now I know who you’re talking about,” Henry interrupted, rattling off both the character’s name and that of the actress who played her.
Meanwhile, Chris had gotten up from his folding chair and tossed his now empty beer bottle into the brown paper bag it had come in. He hadn’t said another word since he’d blown up at Danny and was grabbing his own stuff in an indication that he was leaving.
“Oh come on, Chris, we were just having a little fun,” Danny pointed out.
“Yeah, fun,” the teenager replied.
“Look, I wasn’t trying to embarrass you, I mean, it’s just us guys here,” Danny went on. “It’s not like one of us is going to say something to anyone else.”
Chris seemed unconvinced, but at least he wasn’t still headed for the door.
“Look, some people speak the truth when they have too much to drink; some just make assholes of themselves,” Danny offered, a concession that did seem to mollify the younger man.
“Alright, as long as it doesn’t go beyond this room,” Chris finally said as he dropped back into his chair.
“Scout’s honor,” Danny grinned, holding up three fingers, even though he had never been one.
Henry also raised his hand, although the gesture he made with his fingers more resembled that made in a popular margarine commercial than the one used by the youth organization.
A few moments of silence followed, during which Danny offered Chris another bottle from the brown bag, an offer that he declined, saying he’d had enough.
“So, what is it about Mrs. Wilkes that attracts you?” Danny inquired, his curiosity prompting him to risk setting Chris off again.
“I don’t know exactly, I just get ... oh, I can’t explain it,” he said, his previous anger no longer evident.
“She really gets you hot and bothered, doesn’t she?” Danny offered.
No answer came through the vent, but Julie took the silence as acknowledgement.
“Well, maybe you should do something about it,” she heard Danny suggest.
“What do you mean?” Chris asked.
“Well, some women like younger guys,” Danny said. “You know, I used to work with her old man; he walked out on her a few years back. So I gotta figure she might be a bit desperate for companionship these days, if you know what I mean.”
“I am not desperate,” Julie said under her breath in a voice too low to carry, the declaration sounding a bit hollow as none of her dates since her divorce had been much to crow about.
“And it’s also been my experience that some of those moms next door types are really hellcats in bed,” the older man added, “especially if it’s been a while.”
Again, Julie heard no comment from Chris, leading her to wonder if he agreed or disagreed with Danny’s statement.
“So, if you made a pass at her, what’s the worst that could happen?” Danny asked. “She says no and you move on, but at least you’d have tried. I mean, you’re back at school in two weeks, so what have you got to lose?”
“If you think she’s that hard up, why don’t you give her a go?” Chris retorted.
“Not my type,” Danny laughed, “I like a woman with big boobs. Besides, I already got a girlfriend, and she takes really good care of me. I’m not about to screw that up.”
Chris thought for a moment about the photo Danny had shown him and Henry the first time he’d been assigned to shipping at the beginning of the summer. The dark-haired Latina in it, who looked to be only a few years older than Chris, certainly had big boobs. The older man had described them as being 42DD in size.
“Hey, you think that maybe she’d be...” Henry interrupted, popping out of the beer-induced haze he had drifted off in, only to be just as quickly shot down by Danny.
“I think you need to set your sights a bit lower, pal,” he said before again turning back to Chris. “Just think about it, kid.”
Just then, whatever caused the cross-talk effect changed and the voices faded until they were gone. If Chris had given a final response to Danny’s comment, it had been too indistinguishable to be understood.
Dropping back into her chair once she accepted that there wasn’t going to be anything more, Julie slowly shook her head in disbelief at what she’d heard. It was absurd, she thought, the very idea of her and a kid like that. Well, maybe not a kid because, after all, he was almost twenty — but still.
Closing her eyes, Julie tried to recall her interactions with Chris over the summer. Most had been of the friendly greetings as they passed in the hall variety, but there had also been the week he’d filled in for their vacationing clerk. She remembered him as being extremely eager to please, going above and beyond what was normally expected of summer help.
Sure, they’d had a few conversations, mostly about general things like, what he was studying in school, did he have a girlfriend, how did he like working at Sutherland’s? The answers to which she’d mostly forgotten. Yet there had been a compliment he’d paid her one day that had stuck in her memory. About how nice she looked in the dark green dress she’d been wearing that day, the color going so well with her hair. It seemed such an unusual thing for a young man to say, which was why she probably still remembered it.
It was only as she thought of that that she also recalled a comment that Alicia Ortega, the assistant bookkeeper, had made the next day. She’d said it was a good thing Chris being there was only temporary, because she got the impression that the kid had a bit of a crush on the older redhead. Julie had told her that was absurd; she was old enough to be his mother. Alicia, however, had been adamant.
“I could’ve been mistaken,” the Hispanic woman had said, “but I’m fairly certain that he had a hard-on when he was talking to you yesterday. At least that was the way it looked from across the room.”
Somehow, despite having been much closer, Julie had missed that observation.
Over the next two days, despite the absurdity of the idea, Julie found it near impossible to get the overheard conversation out of her head. It became a constant distraction, so much so that, when Bill Riley, the head of maintenance, called her on Friday morning, the shrill echo of the phone interrupted yet another replaying of the incident.
“What can I do for you, Bill?” Julie asked, shifting her thoughts back into work-mode.
“Just calling to see what time you want me to have someone pick up those records that need to be sent to the warehouse for storage?” he said.
“I still have a few files to go through before I pack them away,” Julie said. “Would five o’clock be too late?”
“Well, most of my guys are looking to be out the door by then, it being Friday and all,” he replied, “but give me a moment to check the schedule. I might be able to grab one of those summer kids to take care of it. I doubt any of them are going to that party at O’Malley’s.”
Not planning to go herself, Julie had forgotten about the Last Call Party that had been announced in a flier on the bulletin board. A party celebrating the retirement of Charlie Nelson, who, also having started as a teenager, had been at the store almost fifty years.
“God, I hope I’m not still doing this when I’m sixty-five,” Julie thought as she could hear the sound of pages being turned on a clipboard as Bill flipped through the day’s work roster.
Finally, Bill came back on the phone, saying that he had Tony Moore scheduled until six, so five wouldn’t be any problem at all. In fact, he’d make sure that he was down there with a hand truck by a quarter to.
“That would be great,” Julie said before hanging up the phone.
When Bill had mentioned the summer kids, Julie had a moment of trepidation, worried that it might be Chris that he sent down for the box. After what she’d heard the other night, she had felt a little self-conscious being around the teenager and had deliberately gone out of her way to avoid him. Which was silly really, she told herself, because nothing was ever going to happen.
“Hey girl, ready to head out to lunch?” Kathy Howell asked as the full-figured brunette stuck her head into the open doorway of Julie’s office.
“Just a minute,” the bookkeeper replied as she finished the column of figures she’d been checking. “Okay, done.”
Gathering up the scattered papers, Julie organized them into orderly piles, then wrapped a rubber band around each before dropping them into the large wooden completed box on the corner of the desk. She suddenly paused for a long moment, a look of concentration filling her face. Then it faded and, pushing her chair back toward the wall, she rose to her feet, adjusting her long-sleeved button-down blouse and gray skirt, both having been wrinkled from sitting too long.
“Something on your mind?” Kathy inquired as Julie stepped into the hall with her.
“No, why?” Julie asked in turn.
“You had that look on your face that you usually do, when you can’t get something out of your head,” Kathy explained.
“I guess it’s just that I have a lot to do today,” Julie answered. “In fact, maybe I should skip lunch and...”
“Oh no, we’re going to lunch,” the older woman insisted. “Anything you need to do will still be here when you get back.”
Thinking she was right, Julie locked the door behind her.
Even though cafeteria service had been done away with years ago, people still brought their lunch, be it brown bag or something from the local eateries, to the old lunchroom to eat, if only because it gave them the opportunity to run into people from other departments that they hadn’t seen for a while.
Kathy and Julie grabbed a small table at the far end of the rectangular room, laying out the lunch specials they had picked up from Burger Barn. As they ate, Kathy noticed Julie constantly looking past the brunette’s shoulder at something. Curious, she turned her head to see what it was?
She didn’t see anything out of the ordinary, just people enjoying lunch and conversation. The table off to their left was filled with some of the girls from Kitchenware, and the one behind them had some of the summer help. Just past both, however, sat Jenny Lane with Mark Goldstein from Home Appliances. The blonde was facing toward them and Kathy could see that she was wearing a blouse that looked to be at least a size too small.
“Looks like Jenny’s going for one last goal before the weekend whistle blows,” Kathy said in a low tone as she turned back to Julie.
“What?” the redhead asked.
“Jenny,” the older woman repeated. “If she opens one more button on that blouse, I think it might burst.”
“I hadn’t noticed,” Julie replied as she glanced first in the counter girl’s direction, then back down at her food.
“Then what were you looking at?” Kathy asked.
Before Julie could answer, the sound of shuffling chairs behind them filled the air as the table’s occupants got up to leave. A movement that caused the redhead to look up as the foursome pushed the seats back before walking away.
“Ah, I see now,” Kathy grinned as she took in the group of younger men. “I guess it can’t hurt to look now and then, if just to remind yourself that you were that age once too.”
Julie forced a small smile, as if trying to say that was what it was.
“Which one were you fancying?” Kathy asked, leaning in closer to her friend as not to be heard.
“None!” said in a response that came much too quickly.
The volume of her response also caused two of the girls from Kitchenware to turn and look. A hostile stare from Kathy, however, was enough to convince them to turn back around and mind their own business. Once they did, the brunette turned back to Julie.
The momentary disturbance had also drawn the attention of one of the employees who had just vacated the adjourning table. Taking note of Julie, he’d left his associates behind and walked toward her instead.
“Mrs. Wilkes,” Chris said in a soft tone, causing Julie, who had turned her attention back to her food, to again abruptly look up.
“Chris!” she said, her face becoming flustered.
“I don’t mean to disturb your lunch,” he said, “but I just wanted to let you know that I’ll be down at a quarter to five to pick up those records for the warehouse.”
“You’ll be down?” she replied, her voice a little shaky, “I thought Bill Riley was sending Tony Moore to get them.”
“Tony felt sick and went home early,” Chris said, “so I said I’d stay around and take care of it.”
A long moment passed as Julie sat silent, until finally she simply said, “Oh, okay.”
Chris then flashed a broad smile before walking away, picking up his pace after a few feet in order to catch up to his companions.
“And what the hell was that about?” Kathy, who had been watching the interaction with a keen interest, asked once Chris was far enough away.
“What was what about?” Julie asked, feigning ignorance.
“Oh, don’t try and play dumb with me,” Kathy said with a grin. “You were practically quivering when that boy came over to you.”
“It’s nothing,” Julie insisted.
“Nothing my ass,” Kathy replied. “I’ve known you far too long not to know when something’s bothering you. You know you can tell me anything.”
A long moment passed as Julie sat silently. Finally, she decided she had to tell someone; if only to get a dispassionate opinion.
“Okay, but you can’t tell anyone else,” Julie replied after a moment’s reflection.
Using her index finger, Kathy made a cross her heart motion, then leaned in so that Julie could keep her voice low.
After looking around them to be sure no one was paying them any more notice, Julie told Kathy about the conversation she’d overheard the other night.
“And that’s what you’re upset about?” Kathy said, trying hard not to laugh.
“Are you saying I shouldn’t be?” Julie replied. “I’m not used to having someone talk about me like that.”
“Like you were a woman instead of a walking adding machine?” Kathy asked.
“I’m more than twice his age,” Julie stated. “I could be his mother.”
“Actually more than twice,” Kathy smiled, “but so what? And you’re not his mother.”
“It still doesn’t seem right,” Julie added.
“Why not?” Kathy asked. “You know, they say most women don’t reach their sexual peak until their thirties or forties, while most men hit the mark by their twenties. Sounds like a win-win to me.”
Kathy paused a breath, then added that she’d also heard that some younger guys like older women.
Julie couldn’t help but recall Danny saying much the same thing through the air vent.
“Are you seriously going to tell me that you didn’t go home that night and at least wonder what it might be like to be in bed with him?” Kathy asked.
Julie didn’t answer, at least not directly, but the expression on her face said she had. In fact, she had done more than simply thought about it, that same night, she had masturbated herself to sleep doing so.
“He’s definitely cute; maybe a bit shorter than I like,” Kathy added, making reference to the fact that Chris was a couple of inches shorter than either of them, “but that’s not reason enough to toss him back in the pond.”
“Are you saying that I should...” Julie said, hesitating mid-sentence for a long moment, “that I should act on what I heard?”
“I’m saying you should at least test the waters,” Kathy replied. “How many women our age get an opportunity like this, to take a bite out of the forbidden apple, so to speak? Far too few not to let it pass unsampled.”
“Would you do it in my place?” Julie inquired.
Now it was Kathy who turned to see if anyone was listening and was pleased to see that the girls at the next table were getting up to go. She waited a few moments until they had, then turned back to Julie.
“Sweetie, being totally honest, if a young guy like that was interested in me that way,” she said, still maintaining a low voice, “I’d probably take him home and ride him like a pony without even a second thought.”
“I can’t believe that you mean that,” Julie replied, sure that her friend was kidding.
“You know Tony, right?” Kathy asked rhetorically, referring to her husband of nearly thirty years whom Julie had met on a number of occasions. “Well, as much as I love the big lug, the last time he rang my bell, Kennedy was in the White House.”
That, Julie thought, was more than she really needed to know. Still, it did drive home Kathy’s point. Her own track record in bed hadn’t been all that spectacular, even before her marriage had turned sour.
“Look, Julie, it’s your decision, but you really should think about it and not just dismiss the thought because some people might think it inappropriate. In the end, it’s none of their fucking business,” Kathy concluded. “I’d hate for you to look back on this a few weeks from now and say ‘woulda coulda shoulda?’”
That, Julie had to admit, was a phrase that applied to far too many things in her life.
The wall clock read four thirty as Julie closed the last file folder and dropped it into the cardboard box next to her desk. The cover followed, slipping securely in place as the July invoices and payment vouchers were ready to send off to the storage warehouse. There to probably sit undisturbed for years until IRS rules said it was okay to destroy them.
Thinking about her tongue-tied behavior earlier, Julie wondered if she should simply leave the records box out in the hall for Chris to find and get a small jump on the trip home. An idea that was good in theory, but quickly proved impractical as she unsuccessfully tried to lift the heavy case. How could paper, she asked herself as she felt the strain on her back, weigh so much?
She was going to have to wait for Chris after all.
A wait that didn’t last long, as only a minute later, a knock on the door frame stirred Julie from her thoughts. Looking up to see Chris, who had changed from the coveralls he’d been wearing earlier to a t-shirt and a pair of shorts, standing in the open doorway, she felt her heart skip a beat.
“I hope I’m not too early,” he said as he stepped inside the small office, wheeling a hand truck ahead of him.
“No, not at all,” Julie said, trying not to react at how much better he looked out of the drab work outfit. “I only finished packing everything up a few minutes ago.”
“Great,” Chris replied as, reaching the center of the room, he looked down at the large box next to Julie’s desk. Then, noting that Julie was staring at his unprofessional attire, he explained that since it was the end of the day, he’d already cleaned up and changed to save time later.
Swinging the hand truck around the desk, Chris maneuvered its nose plate under the box and slipped the heavy case into place. Then he unhooked the bungee cord from its back and used that to tie the carton down. The whole process took less than a minute.
“I feel bad that you had to stay late to wait for this,” Julie said, suddenly wanting to extend their brief interaction.
“I volunteered, remember?” Chris said as he shook the hand truck slightly to make sure that its load was secure.
“Oh yeah, you did say that in the lunchroom,” Julie replied.
“Also, seeing as it’s my last day, I’m really not in a hurry to leave,” Chris unexpectedly added.
“Last day?” Julie repeated, a slight confusion in her tone. “I don’t understand. Don’t the summer hires work until Labor Day?”
And Labor Day, she knew, was still ten days away.
“Usually,” Chris confirmed, “but something came up and I’m going to have to head back to school earlier than I originally planned.”
He went on to explain that he and two of his classmates had pooled their resources and secured off-campus housing for the new semester. It had been a last-minute thing, the rooms only just becoming available; so they needed the extra time to move in and get things set up. The roommate who had found the place was up there already, but he and the other co-tenant were planning to drive up together on Sunday.
“Your own apartment,” Julie said, “that’s a big step. You must be excited.”
“Well, a third of an apartment,” Chris laughed, “but yeah, I’m pretty excited to be getting out of the dorms.”
“You didn’t like living in the dorms?” Julie asked.
“They’re okay, but there are too many distractions,” Chris said.
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