Prom 2020: Mommy Helps Out

Summary: Mom serves as virgin son's prom date and....

Note this is A Love The One(s) You're With 2020 contest story.

Prom 2020: Mommy Helps Out

David wasn't the least bit surprised when this year's prom was cancelled, but he was nevertheless very disappointed. Truth being told, he originally had no intention even to go to prom... he hated everything about all the juvenile high school traditions, and he couldn't wait to leave his little backwater home town and attend college, where he would have the chance to hang with other academics... but his sweet girlfriend had really wanted them to go together, and she had even made it clear she wanted to do what everyone else (said they) did at prom... lose their virginities... and thus he had taken a complete about face, and had been really looking forward to it.

But alas, COVID-19 reared its ugly head.

And instead of her at least being available to do 'prom things' (hint hint) without the actual prom, Debbie had gone to the lake with her family, where the great outdoors gave them plenty of room for having fun even with social distancing, leaving David home alone with his mom. Not that that was entirely a bad thing. He loved his mom, it had only been the two of him since his dad died unexpectedly when he was a baby, so being stuck quarantined with her wasn't much different than the life he had already been living with her for as much of his life he could remember. Besides, he was mostly an introvert, and would rather be quietly at home, than out at a party or school event.

"So I have an idea," his mother Pamela... who felt she was way too young to be facing empty nest syndrome at her tender age of 37... said.

"What's that?" David asked, setting down a book from the upcoming fall's college syllabus: War and Peace, which was ridiculously long, and had a large cast of people, all with unpronounceable and quickly forgettable names.

"The two of us can have a home prom together," Pamela said, having found her husband's tux he had worn nineteen years ago when they had gotten married; it was classic black, and thus it never went out of style.

"How?" David asked, looking at his mom in her pantyhose (well, plus all her other clothes), and like he always did, his cock getting hard. Fortunately for him, she had continued wearing them every day, even when quarantine had required her to begin working at home. She was a psychiatrist, and she still cared for a full schedule of clients, although now she did it from home, using Skype or video calls, and emailing prescriptions to pharmacies. She still dressed up for work as if she was leaving the house, although she could have been naked below the waist and her clients would never know. (Although her grown son most definitely would, on the rare occasions he walked silently off-camera through their living room!) But of course she never would, for a multitude of reasons. One reason being that she refused to get complacent and lazily casual during these stressful times, but instead, attempted to live her life as if she weren't now living it almost entirely at home.

David's mom was a very pretty big-boned woman, which unfortunately in today's social media-obsessed, size-zero culture, meant many people considered her fat. She wasn't fat, just ask her son. Chubby perhaps, but truth was, she was a very attractive full-figured natural woman... with huge tits, a big ass, and great legs. She also had enticing blue eyes you could sink into and drown, and her smile could be sexy or sweet, depending on who she was aiming it towards.

"You want to know how? Come with me to my bedroom," Pamela said.

Those were, verbatim, the very words David had fantasized hearing many, many times, from various women and girls. He really liked Debbie of course, but he also had a secret crush on his English teacher Mrs. Walker. And he dreamed of fucking Beth, the blonde-haired, blue-eyed cheerleader... who oddly resembled his mother. But his greatest fantasy, just like many other boys (this next being something he had discovered through massive research in the form of reading endless online porn) was to bone his mother. He had been stunned when he realized that the stories about incest on Literotica were by far the most popular, that there were forums where people, mostly guys of course, but also more gals than one would expect, chatted about their fantasies or even realities of having sex with their mothers. (Yes, of course he assumed most of these so-called true life episodes were lies... but nevertheless, the idea really excited him, and his ad hoc surveying gave him a 0.01% chance (that's only one in ten thousand, but still more than zero) that he might one day sleep with his own mother.) And then he began watching and reading incest porn (most of it was step-mom, but some was staged or written as being authentic).

"Okay," he said curious to know what she intended, and needing a break from the endless book, that could also be used as a weapon for bludgeoning, it was so thick and heavy. He still hadn't decided whether he loved or hated the novel... he figured it would depend on whether the ending turned out to be worth the endless read.

Pam took her son's hand to lead him down the hallway. This was something she had always done, although now he was pretty much grown, not in public anymore. She did it not because she was some pervert, but because it was touch, which she missed greatly ever since her husband's passing, and it provided her with a natural, intimate connection between her and her son.

David far from minded holding his mother's hand... it had used to make him feel safe and secure, and now he simply enjoyed any opportunity to touch his mother... his cock rock hard, from admiring her cute feet and legs in their sheer pantyhose.

Reaching her room, Pam said, pointing to the tux laid out on her bed, "Try this on."

"You rented a tux?" David asked, surprised to see one in their house.

"No, it was your father's," she explained, pointing at the picture on her wall of their wedding day, where his dad was wearing the same exact tux.

"Wow," David said, as he looked at the tux.

"I think it will fit you," Pam said.

"Okay," David nodded, appeasing his mother.

"I'll give you a few minutes to try it on while I start getting dinner ready," Pam said. "Call me when you're ready to model it for me."

"Okay," David nodded. Once the door was closed, he got undressed and put it on. He didn't have a proper dress shirt on hand to go with it, but the pants and jacket fit him perfectly. He opened the door and called downstairs, "Mom!"

Pam returned a moment later and smiled warmly, her heart beating a bit faster as she gushed, "You look just like your father!"

"I do?" he asked, only having pictures to remember his father by.

"So much," she nodded, amazed at the resemblance.

David looked into the full mirror on his mother's bedroom wall. He couldn't believe how different he looked in this tux. Somehow it made him look more handsome, in the same way he always thought a pair of nylons made a girl look hotter.

"Your dad would be so proud of you," Pam said, admiring her son. She was so proud of him. He had worked hard in high school, and as a result had been offered scholarships to just about every major school in the country. He had also performed the man's work at home (he was great with tools just like his dad, and had become a great cook, preparing most of their dinners, because of his mom's erratic work schedule... which had become even more intensely erratic with this whole COVID-19 crap taking over the world).

"Think so?" David asked, this mother not talking about his dad very often.

"Oh honey," Pam said, coming over and giving him a tit-crushing hug. "You know he would be amazed at how well you've turned out."

"That's mainly because of you," David complimented back, loving the feel of her huge tits against his chest. His cock, that had deflated, was back up to full mast in a cock-beat. He knew his mom felt insecure about her parenting skills at times, and he also knew reassuring her was a good idea.

"Oh honey, I love you so much," she said, tears beginning to roll down her face upon remembering he'd be leaving home in a few months.

"I love you too, Mom," he replied, feeling a little guilty that he so loved feeling her big tits against his body, and because his cock was so fucking hard right now. He couldn't help it, but his cock flinched against her leg.

Pam was surprised to feel what was obviously her son's penis twitch against her leg. She wasn't sure how to react to that. Was he getting hard because of the hug? For some reason was he hard because of her? Was he simply hard because he was an eighteen-year-old boy?

She released her son, the hug having continued way longer than any she'd given him since he'd been a young boy, feeling very emotional because seeing him in his dad's tux made it obvious her son was turning into a man, and because in this tux he struck such a striking resemblance to the only man she'd ever loved. She couldn't explain it, but at this moment, for the first time ever, she was seeing her son as a man.

David didn't understand what he saw in her eyes, but he definitely saw something, so he asked, "Are you okay?"

Pam glanced down to see how obvious it was that her son did indeed have an erection, and the answer was very, as she answered, "It's just sometimes I still miss your dad, and I just remembered that you'll be gone pretty soon, too."

"Oh, Mom," David said, knowing it had been just the two of them for a long, long time. "Maybe I should find a school closer to home."

"No, no, no," Pam said, wiping her tears and feeling bad for making her son feel bad. "You've worked way too hard not to go to Harvard like you've always dreamed of ."

"You're not wrong, I have always had my sights set on going there, but I hate the idea of leaving you here all alone," David said, which was true. For his entire life, all he he'd known was living with just his mom, and conversely, that was all she had been doing for eighteen years, as well.

"To tell you the truth, I hate it too," Pam admitted. "But I'll figure it out." Changing the subject as she wiped a few tears from her eyes, "but let's not dwell on that; let's plan our Prom 2020."

"Okay," he agreed, not very excited about it, since there was no way their festivities would include what he had previously been planning... to lose his virginity with Debbie. But he knew his mom wanted to do this, so for her sake, he'd put on his big boy tux tomorrow evening and show his sweet mom the best time he could.

"Okay," she nodded. "Tomorrow is prom. We'll both get dolled up, dine on a delivered dinner from the best restaurant in town Le Chateaubriand, have a dance or two together, maybe even take some pictures, and do whatever else you want."

I'd love to lose my virginity to you, he thought to himself, but he just nodded, as he glanced down at her nylon-clad feet, "Sounds great."

"Sweet," she said, a word that had long fallen out of popularity, yet was still his mother's go-to word.

"Yes, Mom, saccharine sweet," he teased, something he did every time she said it.

"Teasing your old mother isn't very sweet," she objected mildly.

"You're not old, Mom," he pointed out the obvious. "There are women at your age who are just starting to have kids."

"Maybe that's true, but I still feel old," she sighed.

"Well, you're not," David said. "And I don't want to hear any more about it, unless you're fishing for compliments; in which case I have plenty to choose from."

"Fine," she smiled, She then posed playfully, "Then I'm a hot babe."

"You're joking, but I hope you know that every guy in my school, even the assholes, or rather especially the assholes, all think you're hot," David pointed out, having on many occasions seen guys checking out her big tits and ass.

"I can't imagine," Pam said, flattered to think so. Truth was, she had been oblivious to men ever since Sam's passing, focusing on just her work and her son. She had been in two rather brief and anti-climactic relationships over ten years ago, but both had failed; mostly because she couldn't help comparing the men to her deceased husband. Although at a medical conference a couple of months before COVID had hit, she had daringly tried out her first experience with a woman. A younger woman had hit on her at a bar where the conference was hosting a poker night. So tipsy, lonely and horny, she allowed herself to get fingered in a bathroom to orgasm, subsequent to which, curious, she went down on the girl, licking her to a rather loud orgasm while some other women were in the bathroom. It was exhilarating, even the walk of shame when she and her paramour emerged from the stall to be greeted by some playful applause, and the experience had made her feel sexually alive for the first time in years.

"Mom," David said, noticing his mom a bit distracted, decided to cross a line he likely shouldn't cross, yet felt the need to do something excessive to make his mother feel better, "please don't be offended by this, but if you weren't my mother, I'd be completely in lust with you."

"Really?" Pam asked, flattered by her son's words, and not interpreting them in the inappropriate way he'd meant them.

"Mom, you're incredibly sexy," David added, before figuring he may as well throw this next thought out there too, "plus, unlike all my classmates, even unlike most of my teachers other than Mrs. Walker, you wear pantyhose."

"You like pantyhose?" Pam asked, that having been his father's fetish. She had actually hated pantyhose as a teenager, until she met Sam. He revealed he liked them after a few dates, and thus she started wearing them all the time for him. He appreciated it, as he would massage her nylon-feet at school, in the car, and at their homes. She discovered there were various qualities of pantyhose. The kind she wore originally had been cheap and itchy; but the kind she wore in her senior year of high school and ever since, were sheer silk stockings... and once she could afford them, including many luxury brands from Europe, where hosiery was still fashionable, unlike here (although over there, they call pantyhose tights, and thigh high stockings are called hold-ups).

"Yeah, I do," he nodded, glancing down to her nylon-clad feet, and doing it quite obviously for the first time, and he added, "it's probably your fault."

She had long noticed her son checking out her feet in nylon, and this time she felt flattered. She knew as a psychiatrist that some sons become sexually aroused by their mothers (although she hadn't applied that thought to David until this very moment). She responded, "Actually it's your father's fault; his fetish was nylons, and I've worn them in memory of him ever since."

"So it's like father, like son, so if I check out your legs, I'm just honouring my dad's memory?" David joked, now not even pretending he wasn't staring at his mother's nylon-clad feet.

Pamela knew it was a little wrong, but she was enjoying the attention, so she wiggled her toes, as her husband had been particularly obsessed with her toes in sheer nylons... although she hadn't bothered to paint her toenails since the quarantine began. She would definitely make a point of doing so for tomorrow evening! As she recalled her husband's eight-inch cock, that used to bring her to multiple orgasms, she couldn't help but wonder if her son had also inherited that impressive gift, and with that thought secretly in mind, she said, "There is no one I'd rather you be like."

"And there is no one I'd rather have for a mother, not even some hot movie star," David said, his dick dying for attention.

"I'm going to finish making dinner, and then while we eat, let's watch Wheel," she said.

"Sounds good," David nodded, that being his favorite hour every night. Partly because he really enjoyed Wheel of Fortune and Jeopardy, partly because he loved how excited his mom got when she knew an answer, and partly because it usually meant an unbroken hour of his getting to stare at his mom's nylon-clad legs and feet.

Twenty-five minutes later they were eating dinner, guessing puzzles, and David was slyly admiring his mom's legs.

Pamela had never paid any attention to his fixation in the past; although she'd been vaguely aware of it, she had just focused on answering the puzzles, and then on answering the clues by forming questions. Yet tonight, she couldn't help but view her son in a different way. For one, she noticed he was constantly admiring her legs and feet, not just from time to time, like she had thought. For two, she now couldn't stop noticing the many similarities between her deceased husband and her son. The slightly crooked smile, the dimples, his constant glances at her, the affectionate (and even slightly horny, she now saw) look in his eyes. She couldn't explain it, but more than once she thought she was looking at her husband instead of her son.

Usually his mother was so focused on the puzzles and questions that she was completely oblivious to his constant glances and stares. But this evening, every time he admired her legs in the beige nylons she usually wore (4 days a week, black two days a week, and cream colour on Sundays... not that he kept track or anything, no, certainly not), she seemed to catch him looking... or sometimes instead, when he turned his head, she was already looking at him with what he could only describe as a perplexed look.

For them both, it became a strange game of cat and mouse, although neither quite realized they were playing it. David would get caught admiring his mom's feet, so he'd look away; Pamela would be looking at her son instead of watching the show, and then when his head began turning her way again, she would turn away.

Pamela, for a couple of reasons, decided to wiggle her toes and move her legs far more than she usually did. At first just to test her theory that he was checking out her legs and feet; and then once she had decided he definitely was, to tease him... she knew it was wrong, and she had no idea why she was enjoying her son's attention (other than because of her being physically isolated from the rest of the world, she was quite naturally starved for attention), but she was enjoying it... especially when she saw him adjust himself on more than one occasion; which brought her to the third reason: she was antsy herself, and a little horny.

David was confused by his mother's reactions, and by her slightly flushed cheeks.

Pamela was confused by her own reactions, and by the way that tonight she was constantly seeing her late husband in her son, who was very alive indeed.

That night David jerked off while reading erotic Mom and Son stories, while unbeknownst to him, his mother masturbated while imagining her husband was still alive, and he was fucking her like he had all those years ago: hard, rough, deep... although as she came, three fingers in her pussy while she spanked her clit with the other hand, it was her son's face that popped into her head!

David went to sleep, curious about what his mom would look like tomorrow, all dolled up... her very words.

Pamela went to sleep disgusted with herself. What kind of horrible mother has such twisted thoughts about her very own son?

.....

The next day, Pamela painted her fingernails and toenails red for the first time since the quarantine had begun. She applied her make-up with great care. She put on some glossy, bright red lipstick. She didn't know why she was going the extra mile with her undergarments, she certainly wasn't going to try and seduce her son, but she wore a fancy garter-belt and stockings for the first time in months. (She did wear the ensemble on occasion, just to feel sexy while she was out and about, even though no one else would know.) And tonight she even wore a thong (which she often wore, as she liked them... always had).