Date Night

She was gonna get fucked tonight. This wasn't confidence or arrogance. It was need. It had been too long since her divorce and the father of her children had moved out to start a new family with a much younger woman. Claire had waited long enough for love. Something was going to happen tonight.

Her friends had suggested a dating app, and she didn't even realize how easy it was to sift through profile after profile of some seemingly decent men, swiping left and right and blocking any suspicious-looking messages.

She had briefly entertained going out with some of the younger men because of their shirtless pics with their chiseled abs, but her son was 23 and it would have been awkward to look him in the eye, or heaven forbid have to explain what she was doing with someone his age. No, she'd stick to other men who looked like they'd been around the block and maybe were even divorcees themselves. They surely weren't old enough to need Viagra quite yet. Though some were likely getting there earlier than others. She just had to choose wisely, like the smart woman she was.

She ended up choosing a handsome man with grayed tips because she was pleasantly surprised to find him amicable and a man who really seemed to love his own children. That was the selling point for Claire. She knew a man who truly loved children was a kind, gentle soul, and even if he was too gentle to rock her world, she at least knew she'd be safe with him.

They'd set the date for 7:30 p.m. tonight, and Claire was just getting ready. She was going to put decent effort into this, and not half-ass it like the end of her last relationship. While many things were important for the date, like the way she wore her hair, the look she went after with her makeup, and the scent of her perfume, those choices were simple enough. What Claire really took her time getting ready with was picking an outfit.

It had been years since she'd bought anything truly special, as is usually the case when your husband has a mistress. But she still occasionally indulged in shopping when the mood hit her right. Usually nothing more than the bargain bin panties at Victoria's Secret, but at least it was something she could wear.

She found a nice pair with matching garter belts and was just putting a skirt and a blouse to go with it when she decided to try on the skirt. She knew she must've put on a few pounds since her husband left her, enough to make her want to make sure it wasn't too snug, though she knew she definitely hadn't hit the next size up yet.

She left the rest of the outfit on the bed and pulled on the skirt. It was snug, but she was able to get it over her hips. She smoothed it over and was standing there assessing herself when she heard her son Gabriel's voice right behind her.

"Are you headed out tonight?"

She turned around, her nude flesh exposed except for the little that the skirt covered, and began an explanation. "Yeah, I got invited out by a friend, so you're gonna have to get dinner for yourself."

"Alright. Anything you need while you're gone?"

"If you find time try to get some laundry done."

He continued standing there for a moment, and she suddenly realized he was ogling her exposed flesh, starting to make her feel a little uncomfortable. "Gabriel," she implored, "I need to take a shower."

He shook the haze from his head. "Sorry I thought you were gonna ask for an opinion on your outfit," he said with a sheepish grin.

She reeled at her hasty response and remembered the bare semblance of her outfit. "I guess you're right." Relieved, she held up the blouse centrally and made sure it covered one of her tits as her arm strategically covered the other. She tried to pull down her skirt and close her legs shut while she posed for him in place, but his gaze was locked well below the fabric. "How well does this go together?"

"Mom..." Gabriel trailed off.

"Gabriel?"

"You don't want my opinion."

"What?! Don't let me leave here looking foolish!"

"You don't look foolish at all. Mom, this skirt is going to get you," he paused, "...fucked."

She felt the ache between her legs. "Gabe!"

"What? It's true! I'm just glad my friends don't come over anymore," he said as his eyes were still on the bush poking out from underneath her skirt.

"What's that supposed to mean? Does your poor mom embarrass you?"

"No, I just wouldn't want 'em seeing anything."

"Ha! Seeing this old lady? They wouldn't even..." her thoughts went back to similar young men on the dating app and she began to blush profusely. "Gabe, thank you baby, but I really need to get myself ready now." She watched him slink away then shimmied out of the skirt and set it with the blouse and the matching bra on the bed.

As the water ran over her skin, she sighed and her mind began to wonder what Gabriel had meant about his friends. What would a bunch of young men want with an old lady while she was getting dressed? Oh. My. God. He meant they'd want to fuck me. Those naughty college boys with their raging hormones and insatiable sex drives, their spontaneous erections...

She closed her eyes and began to caress her body as thoughts of Gabe's friends took over her mind. Her hands were now their hands in her mind's eye, and they were growing increasingly bold. Her fingers became tongues as she flicked her nipples, gradually moving her hands down between her legs. The fantasy grew more intense as she imagined them taking over.

She couldn't even see Gabe there watching her silhouette as her ass pushed against the glass of the shower door. He snatched a panty off the floor just as she began to moan, and high-tailed his way out of there.

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He'd tossed the panty in the laundry basket on his way to go make dinner. He'd already cooked up the simple meal and was cleaning dishes when his mother bid him farewell on the way to her date. After watching a little TV, he was on his way back to his room when he remembered the laundry basket. On top of some khakis and shirts was the panty he'd picked up earlier while his mother was showering. Since the fabric was a little more delicate, he set it aside and began to cycle the rest of the load.

When he came back again later to switch out the clothes, it was still laying there almost forgotten. It triggered the memory of his mother in her skirt, and he found himself wondering what she actually had worn with it. He knew it was wrong, but it had been so long since he'd had a girlfriend. He was unable to control his wandering thoughts.

His heart began to thump as he slowly picked up the panty. His curiosity took over and he unfolded it and brought to his face to search for her aroma. But it a fresh laundry scent. She hadn't even worn them. But they were quite soft, something like silk but not exactly. He continued to inhale, then made his way back to his room with her panty in tow. He pushed the door behind him for more privacy as he continued to breathe in the fresh panty on his face. He had the urge to taste vagina, and imagined this was a woman's scent.

He turned to sit on the edge of the bed, pulling out his cock to stroke it and edge closer to orgasm. He lowered the panty between his legs, rubbing his dick with the soft fabric. The thrill was about to make his heart explode.

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Meanwhile, Claire's date had not ended as she had expected. The date itself went fine, but when it came time to head home, her invitations may have been just a little too zealous. Her date declined, insisting that sex on the first date would ruin any relationship potential that they might have had. While Claire admitted she probably would've echoed that same sentiment years ago, that was not her plan for the night. But as she started to sound more and more desperate, she spooked the kind gentleman and both ended up heading home, all alone.

When she arrived home, she could see a light was still on in Gabe's bedroom. She wouldn't burden him with her drama, but instead just wanted to find some comfort in reverting back to her role as Mom. As she knocked lightly on the door and pushed it open more, she could see him hunched over on the foot of his bed, muscling something furiously right in front of him.

Her eyes must've been getting worse, because she caught a glimpse of a color matching her own skirt and it slowly dawned on her what he was doing. He eventually started to shoot, ropes of thick cum landing right on top of the colorful fabric, which caught most of it.

"Son, have you seen my..." she interrupted as she watched the white liquid pooling onto her garment. "Panty? I must've forgot to put it on."

She adjusted her mini-skirt as she walked toward him, smoothing it along her hips and revealing her unshaven muff.

He looked up with his eyes wide, caught in the act with her intimate parts right in front of him.

"Oh, it seems you're using it. Well I guess it's better than pumping it inside some young girl."

He looked stunned and hurt at the same time.

She turned around and made her way to the doorway, stopping short to fix a painting on the wall that must've been knocked out of place when she barged in his room.

As he watched her on her tiptoes, he begged her, "Mom, please don't go."

"Honey you already decided to take care of your business by yourself. What do you need me here for? Clean up your mess and bring me back my laundry."

"Can't... Can't you... help me?" he stammered.

She stared for a moment at her cum-covered panty and then at his flaccid, shriveling cock and felt bad for him all of a sudden. She'd left her baby all alone, and once again was being cruel because of the things that were beyond their control. Horny boys all masturbate, she told herself. Nothing to get worked up over. She shuddered.

"No Gabe, that's not what moms do. You're a grown man and need to take care of yourself."

He watched the curve of her bottom as she walked away with her real-world femininity on display in her impossibly short skirt. At least she didn't seem too mad at him. But she did let him off way too easily for the panty.

Back in her room, Claire had already taken off her makeup and undone her blouse. She let out an exasperated sigh as she plopped down exhaustedly onto her bed. She laid there for a moment, arms spread out wide, before rolling over and reaching toward her bedside table with one arm.

She fumbled around, patting the top of the table until her hand wrapped around the smooth silicone of the object she had been seeking. Her fingers wrapped around the realistic toy that she normally would've hidden from view. It was there because she'd wanted to display sex positivity after her date that didn't end as she had anticipated. And now that she was alone, her needs, among other things, demanded fulfillment. She slowly dragged her arm back across the bed toward her and brought the recently washed sex toy to her lips.

Oh honey, what's this? she thought, imagining her invisible lover. You're so naughty!

She inhaled the artificial scent and pursed her lips before slapping it lightly against her breast. She then rolled over onto her back and reached her fingers down into her bush, applying light pressure as she squeezed the girth of the dildo the same way. She drooled spit onto the tip still pointed up at her between her breasts. She slid her hand down her stomach slowly with the toy tight in her grip.

You naughty boy, pulling out that hard cock right next to me in my bed. Did seeing me dress like this turn you on, dear? Is that why you stole my panties?

She knew she was wet even before she found her swollen clit and started to rub it. Her artificial lover plunged into her soaking pussy simultaneously.

Is this what you wanted to do? Fuck mommy's juicy pussy with that big cock of yours? TAKE IT, BABY. FUCK ME GOOD.

As she thrust the toy deeper inside her longing body, she knew she was on the verge of provoking a mind-blowing orgasm. She imagined the unexpected scene from earlier, her son's cock sputtering his sticky liquid all over her clean panties. Then her body tensed as she imagined it squirting inside as he pounded her womb, filling her with every inch. She clenched down as the orgasm surged throughout her trembling body.

"Fuck Mommy!" she demanded aloud as she was now double-fisting control over the dildo that she was plunging into her sopping snatch without ceasing, until she came down.

"Whew!" she exhaled deeply.

She finished cleaning up, placing the toy back inside its drawer, still stark naked when she heard soft footsteps and a familiar deep voice.

"Mom, are you done? I wanted to apologize to you for earlier. Didn't mean to ruin the end of your night like that," he said with his head hung low.

"Oh, you didn't ruin it all," she said as she struggled to contain a huge smile.

"I brought back your, umm, er, your laundry," he confessed.

"I sure hope you didn't steal it on purpose."

"No, Mom, I was just doing laundry like you asked me to and found them lying around. Honestly." But he didn't mention he'd found them while she was showering.

"Alright then. And is this the first time you've done this with my undergarments?" she continued.

"Yes, I swear!"

"Good. And it'd better be the last." She winced, but he didn't seem to notice at all.

"Mom, I'm sorry. I don't know what came over me, but it won't happen again."

"Your horny cock came all over. I understand," she added quickly.

He raised eyebrows at her language, but sought to change the subject. "How did your date night go?"

"Oh, honey, kinda similar to yours."

"I wish I could make it up to you."

"Maybe you can." She stood up and made her way to a bedside drawer, pulling it open and then leaning over to go through its contents. Not finding what she was looking for, she made her way around the room and got on her hands and knees to look for something on the closet floor, near the shelves of shoes. She got back on her feet and went to the headboard of the bed. All while completely naked.

"Mom, what are you looking for?"

She was still rifling through the contents of the headboard and replied, "Here they are! Found 'em!"

"Found what?" he asked reflexively.

She turned around and showed him a pair of furry handcuffs with a wide grin on her face. But he wasn't looking at her face now. He was unabashedly taking in the striking contours of her mature body, as he must've been doing during her entire search.

"What are... those... for?" he finally stammered.

"Son, I watched you shoot your load in my panties earlier."

"Mom, I said I'm sorry."

"Then you've been standing there watching me and it looks like you've got an erection again."

She didn't even know about the shower, or she would've mentioned that, too.

"I'm just returning your... things," he said, offering up the panty still in his hand. "I wasn't trying to..." She couldn't tell if he was in denial or just thought she was oblivious to his roving eyes.

"You weren't trying to what? Look at this?"

She turned around and arched her back, then looked back and saw him examining her posterior.

"No. I wasn't." He replied matter-of-factly, leaving alone that he'd obviously been ogling her naked body since he had entered her room.

"And you came into my room when you knew I was still getting dressed. I bet you if we took off your pants, you'd prove my point about easily getting it up again."

"I came to apologize. And it's actually not that hard," he said cryptically.

"No? Not even if I said you should handcuff me because Mommy's been naughty, too?"

She tossed the handcuffs and he barely caught them.

"That's not what I meant."

She placed her hands behind her back.

"Mom, I don't think this is a good idea."

"Baby, Mommy's been naughty. After you left, she lubed up and fucked one of her toys thinking about you."

His eyes widened, but he didn't reply.

"But it's just not the same as the real thing. You'd better cuff me before I do something I might regret later. Do it now."

He hesitated for a moment, then she felt the cuff as it clicked around one of her wrists, dangling in place. "Mom, what are you up to?"

"You're gonna stop Mommy from being bad. But at least take off your pants and let me see it."

He unzipped his jeans, and sure enough, stuffed inside at an awkward angle was a rigid boner. It bounced out when the zipper reached the bottom.

"See, I told you I was right. What are you gonna do with that thing now that you don't have my panties?" She snatched it away with her free hand, then watched his cock twitch.

"When I was playing with my toy, I bounced back against it like this to cum. Maybe that'd work for you too."

She bounced her ass against him a couple of times to demonstrate.

"Mom, stop. This isn't appropriate." He clicked the other cuff onto her wrist and she played along, pursing her lips as her eyes drew down. "I'm just trying to help. I told you Mommy's feeling naughty."

"Yeah, but you're trying to make me hard again. You seem to keep forgetting that we're mother and son."

"Did I though? Maybe that's what makes it naughty. The same reason you wanted to cum in my panties."

"How do you know that I wasn't just imagining some other woman?"

"Because you keep coming back to see me. And your cock is hard right now."

They both looked down at his cock as it lightly brushed her ass, verifying her claim.

"Or do you just wanna imagine another woman?" she asked innocently.

She bounced her ass up and down and it slapped against his cock, bouncing it as well.

"You mean another woman with a fat ass?"

She paused briefly at his language, then continued to play along.

"Does this fat ass turn you on, player?"

He looked down at the round shape in front of him and his heart began to beat even faster now.

"If you want, you can feel it."

He reached a hand down and squeezed a cheek, then pulled on it and watched as it jiggled back into place.

"Damn, that thing really moves, doesn't it?"

"Is that all you want? Just to watch it jiggle a little?"

"No, I wanna squeeze your breasts too. Make sure you've got a complete package."

"Well what are you waiting for? Don't be shy!"

With that she felt him lean against her, the heat of his cock burning against her backside. He reached around to squeeze her breasts, and nuzzled his face into her shoulder. "Wow," he gasped, "they're so pliable!"

"Did you think they were fake?" she chuckled. "They've only gotten a little bigger since you were just a..."

She stopped herself.

"Mom? I mean, lady?" he said, keeping up their role-play. "Ma'am, can you show me again how you moved your ass?"

"You mean when I was fucking my dildo and imagining naughty things?"

"Yes. Show me again. Was it like this?"

He leaned back and jerked on the handcuffs. His cock slid into the small of her back as her ass moved back.

"Sort of. A little bit harder. But I don't want to hurt you. Why don't you grab my hips so I can show you?"

She felt his strong hands on her waist, and they both worked their hips as his cock grinded her backside.

"Oh that ass feels amazing. But I suppose it doesn't feel as good for you on the outside."

"That's true. If you were my son, I'd just let you cum. But since you're another man, I want you inside of me."

"And if I do that, then you'll show me how your ass bounced on your toy when I wasn't around?"

"Yes, I promise. But you have to agree to stick it inside."

"Didn't you say earlier that you had to lube up your toy?"

"That's also true. Let's try something."

"What's that?"

"You said this feels good, right? Why don't you keep rubbing against me until you're lubricated."

"You mean like pre-cum? Isn't that dangerous? And I won't be able to pound as hard when I'm so close."