A Mother's Dilemma - Cover

A Mother's Dilemma

by James_Steele

Copyright© 2023 by James_Steele

Incest Sex Story: Busty single mom, Barbara makes a bad choice all because she wants her son.

Caution: This Incest Sex Story contains strong sexual content, including Ma/Fa   Fiction   Incest   Mother   Son   Analingus   Masturbation   Oral Sex   Big Breasts   Size   .

Barbara couldn’t wait to get out of there and get back home. The whole reason she was lying naked on a bed in a five-star hotel room with her boss’s cock between her wide-open legs was because of her son, Levi. It was completely his fault.

It was also Levi’s fault that it was all but impossible for the busty, raven-haired beauty to concentrate on what she was doing. She had finally decided to let Lymon, her married boss, fuck her and yet the only cock she could think about was Levi’s. Her son’s cock was both longer and thicker than her boss’s by a wide margin. Beyond that, his body was also so much firmer and more trim, with the fluid muscularity of a younger, more active man. And while she didn’t exactly dislike Lymon, he was a man she would otherwise never notice in a crowd if she didn’t happen to work for him. But for Levi, the stacked and statuesque beauty harbored a deep love that could never be mentioned outside the quiet privacy of her tumultuous mind.

Lymon was now very excitedly pumping his aroused tool into the snug slit between Barbara’s long, toned, and wide open thighs.

“God damn, you’re so hot, mmmmmm, so good,” the somewhat portly fifty-year-old moaned as he gazed at the heaving wobble of his office manager’s perfect, melon sized tits. The man’s belly was jiggling almost as heavily as Barbara’s luscious orbs while he jerked his awkward body harder and faster between her model quality legs.

It was nice to have an eager cock in her pussy again after going without for much too long. The slippery friction felt better than her fingers, but the rapid, jerky thrusts of her excited boss were doing very little to drive the woman’s spectacular body toward the heights of pleasure she could only remember from her sexually adventurous past. If not for the fleeting memory of the sight of her son’s impressively virile cock, Barbara probably would’ve needed the little bottle of lube she’d tucked in her purse before leaving her house to meet her boss in a three star hotel two cities away from where she lived.

Being married, Lymon wanted to hold their tryst out of town where there were lower chances of being recognized. That was fine with Barbara. Even though she’d been single for the past ten years, the last thing she needed was to be recognized going into a hotel with her boss. She had actually been relieved when he didn’t want to bother with having dinner or drinks in the hotel lounge and preferred to meet at the room and get right down to the business at hand.

Barbara had been working at Lymon’s real estate office for the past six years, and as his office manager for the past two. He’d shown a lot of interest in her from the beginning, but only over the past several months had he begun dropping hints about sexual liaisons outside the office. Barbara rebuffed him as politely as she could, but right about the time she started to think about contacting a lawyer and filing a sexual harassment suit, she suddenly decided to take him up on his offer. He seemed just as surprised as she when she said yes. And if it hadn’t been for an unsettling incident at home just a few days before, she would’ve been shopping around for lawyer by now.

Until the previous Monday morning, Barbara had thought she’d achieved a state of mind that was free of the baser desires that had plagued her luscious flesh for most of her life. Not that she didn’t get horny or indulge in erotically charged private time. It was just that she’d given up on sex or dating in order to focus her attention on her son and career, in that order. And now, Lymon was reminding her why. It did feel good to have a cock pumping her pussy, but instead of concentrating on her pleasure, her mind was already fast-forwarding to how awkward things were going to be afterward.

On top of that, she was surprised to realize she was bored. Her boss’s arousal had little effect on her. And he was so consumed with his own pleasure it was almost as if he was jerking off in her pussy. He probably even thought she was wet all because of him, but nothing could be farther from the truth. It was Levi she was wet for, her son who had no idea his mother was off in another city in a hotel room with a married man’s excited cock jamming relentlessly into her warm, slick pussy.

Meanwhile, Lymon was grinding his forgettable dick into Barbara’s exquisite body like a man possessed. He would’ve been crazy not to. But he was oblivious to the distracted mood of the stellar beauty beneath him. As long as her bulbous tits kept heaving and shaking to the jerky force of his thrusts, he could keep on assuming he was fucking her like a stud. He had no clue she was actually thinking about her own son and the ripe, hard, virile, young cock that made her stop in her tracks just a few days before.

Levi had been out that night with Brynn, the girl who’d grown up right next door. Barbara didn’t know how the two could grow up being such good friends without becoming a couple considering how good looking and popular they both were. They were as close as siblings, but without the traditional rivalry.

Barbara had been in bed when Levi came home and went directly to his room. Before another ten minutes had passed, she could hear the telltale sounds of her son giving himself that special pleasure a young man often does in the privacy of his own room. Barbara lay in her bed and smiled as she listened to sounds she was sure her son didn’t mean her to hear. But there was something so sweet about it, and being a woman who had never gotten as much sex as she’d always craved, she couldn’t control the wet warmth spreading through her pussy. She actually deigned to touch herself as she eavesdropped on her cock-stroking boy.

The aroused mother then became aware of Levi’s voice. He was muttering something to himself while he jerked off. She assumed his feelings for Brynn must be changing and that he was jerking off to thoughts of the pretty, young blonde he’d spent the evening with. Was her grownup boy falling in love? The thought actually made Barbara’s pussy even hotter, but driven by curiosity to hear what he was saying, she got out of bed and tip toed out of her room to Levi’s door.

Wearing her long, oversized T shirt and nothing else, Barbara leaned closer to the door and discovered it wasn’t completely shut. There was an inch gap between the edge of the door and the frame. This made it so much easier to hear her son’s feverish groans of pleasure. The sounds he was making were much louder and clearer here, making his mother’s unexpected arousal spread deeper through her core. If she’d been wearing panties they would’ve been soaked by now.

Brynn must’ve gotten him very sexually frustrated to make him jerk off so forcefully right after their night out. But Levi wasn’t the only member of their household that was frustrated. Barbara felt her pussy drip molten honey down her upper thighs as she listened to his animalistic grunts and groans. Against her better judgement, not that she was showing any kind of judgement at all at the moment, she reached under her sleep shirt and started rubbing her badly neglected pussy. At the same time, she put her eye to the crack in the door and peered into the room, finding that she had a good view of her son standing naked beside his bed.

Levi looked amazing! His twenty year old body looked so young and defined, and his cock was like a beautiful piece of sculpture. He looked big and hard as a marble column, his flesh glistening with a thick coating of precum his hand was spreading along his shaft as he stroked it. Barbara gasped quietly as she saw her boy’s cock for the first time since he’d become a man. It was so beautiful, so manly and virile. His mother instantly knew it was a cock that would send any woman into ecstatic delirium.

This was when Barbara also caught the words her horny man-boy had been muttering.

“Oh, fuck, yes, suck it,” he moaned, working to keep his voice down but arching his body as he jacked his shaft harder. He was breathing so hard he couldn’t get the words out too clearly, but his mother distinctly made out: “Fuck, ohhhhhhhhhhh fuck, you’re so hot. So. Fucking. Hot. I – I – I love you even more when you suck my hard, fucking cock!”

Barbara could tell that last remark came out louder than he wanted to. She went on to assume that he and Brynn weren’t doing anything sexual together, as she’d previously thought. Otherwise, why would he bother jerking off to her right after they’d been out together?

Yet Levi’s gorgeous body and cock, not to mention his amazingly erotic excitement, had his mother’s pussy leaking like a broken faucet. She’d always loved hearing a man talk dirty to her, and hearing her son spew that horny filth made her excitement even harder to bear. She spread her feet further apart to give herself better access to her clit. With her gaze transfixed on her son’s cock and rapidly pounding fist, she furiously rubbed her aching clit as she raced toward the edge of her peak.

“Oh fuck, I’m gonna cum, Mom,” Levi moaned. “Gonna cum in that hot, sexy mouth!”

Barbara was barely aware of what she was hearing as her own orgasm erupted in concert with her son’s. She felt the sparks of intense pleasure rippling through her as she watched Levi spank out a plentiful load of spurting cum, knowing he was imagining his juice going straight into his own mother’s mouth. She was shocked by his sordid desire, and even more shocked to find herself cumming as hard as she could remember.

When it was done, she tip toed back to her own room, vowing to keep this forbidden secret to herself. The fact that she’d frigged herself to a climax while spying on her masturbating son was just as scandalous as his fantasy desire for her. Those were the kinds of things no one ever needed to talk about.

But it was only another day or two before the constant ache Levi had unknowingly put between his mother’s long, shapely thighs led her to take her boss up on his offer. She’d thought Lymon’s cock could give her enough relief to stop seeing Levi’s luscious rod in her mind day after day. But she’d been wrong. With the sweaty businessman now straining between her wide open legs, Barbara could think of her son’s cock and his cock only.

It was only the memory of Levi’s swollen man stalk that inspired his mother to begin rocking and grinding the slender curves of her hips, squeezing her pussy into the spastic thrusts of her excited boss.

“Ohhh, yeah, what a hot fuck!” Lymon growled, assuming it was his own prowess inspiring the dark haired beauty to finally come alive and fuck him back.

Barbara’s pussy quivered with arousal as she relived those torrid moments spying on her naked and highly aroused son. Remembering the way the young stud had called out for his beautiful mother at the moment of his climax excited her even more now that she had a living cock pumping into her juicy depths. She did her best to imagine it was Levi’s cock inside her even though Lymon’s couldn’t match the size or strength of the younger man’s organ. But this was the closest the horny mother would ever get to enjoying the succulent man flesh she’d seen her boy fist pumping just a few nights ago.

Barbara knew it had been a mistake to finally take her boss up on his offer. Things would end up changing around the office and not for the better. Yet she’d been completely at a loss to think of another way to release the incredible tension her son had unwittingly put in her body. She was finally getting close. With her eyes closed and visions of Levi in her lust-fogged mind, Barbara ground her pussy even harder into her boss’s thrusting cock, well on her way to a shame filled climax.

Lymon, however, was already so much closer to his own climax that he couldn’t last long enough for Barbara’s.

“Yeah! Oh yeahhhh, fuck!” he cried out as he spurted without warning into the brunette’s velvety fuck hole.

The pudgy, pasty businessman spent himself into his exquisite companion’s tight nest until he flopped breathlessly onto the mattress beside her. Barbara’s head was spinning with frustration. She was even a bit disgusted with her boss for leaving such a mess between her thighs without giving her the pleasure to make it worthwhile.

“That was so good,” Lymon crooned, proud himself. “I always knew it would be. Aren’t you glad you finally gave in?”

At least he didn’t wait for an answer, but he made a move to kiss her. Barbara smoothly slid away from the naked slob and glided out of the bed. “Oh, ummm, after a workout like that I need a shower,” she claimed, rolling her eyes as she turned to go into the bathroom.

Barbara locked the bathroom door. The last thing she needed now was for Lymon to think he could join her in the shower. She turned the water on hotter than she usually liked it and spent a long time scrubbing away the sweat and cum. She took as much time as she could get away with to shower and dry her long, black hair. Unfortunately, she couldn’t hide in the bathroom all night. But then, she was relieved when she finally went back into the room to find Lymon snoring away in a sound sleep.

Careful not to wake him, Barbara got dressed and slipped out of the room, leaving her boss to wake up alone, whenever that would be. She made her way to the parking garage to retrieve her car and started driving home at midnight. She’d told Levi not to expect her back until the next day, but she couldn’t fathom spending the rest of the night in that room with Lymon. Even without traffic, it would take her nearly an hour to get back, and that was plenty of time to come up with an excuse for coming home unexpectedly at such an odd hour.

Fortunately, it was Friday, so Barbara wouldn’t have to go in to the office and face a triumphant Lymon until Monday. She fully expected him to start asking for a repeat performance, and she could use the weekend to think of a good way to put him off. She didn’t want to end up quitting her job after having worked her way to a managerial position. She started to feel better when she realized she now had something to hold over Lymon’s head. If the going got tough, she could easily threaten to tell his wife about their one night stand.

Barbara felt better to think her job standing was secure, but there was still the problem that Lymon hadn’t come close to satisfying her needs. To make matters worse, thoughts of her son’s unforgettable cock refused to leave her in peace. Her pussy was still wet, a condition that was aggravated by the load of cum Lymon had so recently let loose inside her. She ended up driving most of the way with one hand while the other was under her dress rubbing her unsatisfied slit.

By the time she got home she was in a rare state of arousal. She went into the house quietly, knowing Levi was most likely sound asleep. She took off her heels and padded quietly upstairs where she opened the door to her son’s room. As expected, he was sleeping peacefully, but with the sheet only covering his feet. The rest of his body was fully exposed except for the white boxer briefs he’d worn to bed. Even from the doorway, Barbara could see the nicely defined bulge in the crotch of her son’s briefs. After seeing how big he got when he was aroused, she could tell his impressive cock was now at rest but still making a prominent bulge in the fabric.

Still holding her heels in her left hand, Barbara quietly padded into the room and stood beside Levi’s bed. She was sorely tempted to wake him up just so he could see her in the little black party dress she’d put on for her tryst with the boss. It showed more of her impressive, E cup tits than anything else she owned, and she now knew her son admired them more than he was supposed to. But she was admiring the bulge in his briefs and nearly forgot everything except the empty ache deep in her pussy.

Her son’s thighs were strong and muscular, which made the hefty bulge in his briefs look that much more appetizing. She was dying to see him hard again, like the last time, but that didn’t seem to be in the cards tonight. Yet her mind was easily able to fill in the blanks as she imagined how the size of his aroused pole would be stretching those briefs if it were hard.

Barbara pulled the top of her dress down to expose her fleshy tits. Her nipples were fully erect, and the soft mounds felt heavy in her hands as she fondled herself beside her sleeping son.

“You’re not the only one with perverted fantasies, mister,” she whispered as softly as she could, her fingers pulling and twisting at her sensitive nipples. Then she pulled the hem of her short dress up around her hips and pushed her fingers into her panties from the side. Her mound was freshly waxed and felt as smooth as silk as she rubbed closer and closer to her aroused slit.

“Is this how you think of your mother?” she whispered, squeezing a finger down along the lips of her pussy. She rubbed her slit and continued kneading her tits with the other hand. Her eyes roamed her son’s nearly naked body while she wished he was anyone except her own flesh and blood. Her entire night with Lymon now seemed like an embarrassment.

But there was something more to it than that. Savoring every inch of Levi’s fit, perfect body, his mother realized her love for him was behind every other feeling she had, even the ones she wasn’t supposed to be having. And she knew he loved her back just as much. It showed in the way he treated her like a queen. It hardly seemed right that she could go out and let Lymon ram his cock into her pussy when she barely even liked him, but Levi, whom she loved more than anyone else alive, could never be close to her that way.

“Mommy wants it too, baby,” she whispered as she squatted enough to allow her finger to penetrate her sodden pussy.

Keeping her other hand in constant motion over her big, exposed tits, she slipped a second finger into her hole and pumped her slick channel while she ground the pad of her thumb into her clit. She felt like she’d lost her mind to be standing right next to her son’s bed with her tits out and her fingers pumping in and out of her juiced up pussy, but it was like there was a force driving her that was more powerful than her senses. Her breath started to go ragged while she pulled and twisted more roughly on her swollen nipples. At the same time, her fingers were pumping strong and steady into her pussy and driving her rapidly toward a dizzying climax.

“Oh, oh, ohhhhhhhhh,” she moaned, fighting to keep it quiet. “Mommy’s gonna cum. Gonna cum just for you, baby, just like you cum for Mommy.”

Barbara’s voice was cut off by her ragged gulps for air while her body shivered and then tensed with the flowing currents of pleasure rushing through her. It seemed like forever before the shivers of pleasure stopped rolling though her luscious body. Then she caught her breath and realized what she was doing. Thankfully, her son kept sleeping through her entire indulgence, but she was now standing by his bed with her melon sized tits fully exposed and the hem of her short dress bunched around her hips.

“Oh god, what have I done?” she whispered hoarsely. “Forgive me, baby. Mommy couldn’t help it. I promise it won’t happen again.”

Barbara pulled her dress back down over her ass and pussy but left her juddering tits exposed as she turned to sneak out of the room. She was relieved she’d gotten through this lapse of judgement without waking Levi, but she felt like a guilt-ridden pervert nonetheless.

The statuesque brunette made it to the bathroom adjacent to her own room and stripped off her dress and ruined panties. She got into the shower and scrubbed herself all over again, as if she were trying to wash away her filthy sins. Afterward, she took a few minutes to dry her hair. She then went to bed naked and slept until late the next morning.

When she woke up, Barbara had all but forgotten she went to sleep naked. She usually wore panties and a big T shirt or nightie. Feeling foolish for all of her bad judgement lately, she quickly pulled a satin robe over her buxom body and went downstairs to make coffee.

“Oh, I didn’t realize you’re already up,” she said when she discovered her son was already there and already had a hot cup of coffee in his hand.

Levi was leaning back against the counter. He was only wearing the same boxer briefs he’d slept in. His mother couldn’t help letting her eyes roam up and down his nearly naked body. His cock was partially swollen and jutting at a sideways angle. It would’ve looked impressive just as it was, but Barbara had already seen it in its fully impressive glory. The sight served as a reminder of her regrettable night with Lymon, and also of her senseless masturbation standing over Levi’s bed.

“It’s already ten, Mom,” her son replied. “And I thought you weren’t coming back ‘til this morning. Is everything okay?”

Barbara was painfully aware of Levi’s glances at the deep valley of creamy cleavage exposed at the top of her robe, not to mention her long, fit legs. The robe didn’t make it to the middle of her thighs, and her son’s searching look made her blood feel warm and her nipples swell with sensation.

“Oh, right, ummm, there was a booking SNAFU at the conference,” she sputtered off the cuff. “So I decided to make the drive back last night.”

Levi nodded. He looked skeptical. He put his coffee cup on the counter and then poured another one for his mother, setting it down on the table. She thanked him and sat down in front of it. He picked his cup back up and resumed his position against the counter with his semi-swollen cock making a conspicuous impression in his snug briefs. Barbara wished he’d sit down because the sight of his succulent bulge was threatening to make her pussy leak.

She started to think of something to say about the fictional conference she’d told him she went out for last night, but it was Levi who broke the guilty silence.

“Mom, I know you weren’t at a conference last night,” he said. “I don’t know why you think you had to tell me some story. I thought you trusted me more than that. I know you went out to meet some guy.”

Barbara went speechless for a moment or two, feeling like she’d been busted doing something wrong. She pretty much had been, but the only reason she bothered was because of that man flesh making a bulge in her son’s briefs.

“Of course I trust you, Honey,” she said, almost stammering. “I just, umm, didn’t want to say anything in case it didn’t work out.”

He still looked skeptical. “Well, you came home at a weird hour last night after saying you’d be gone overnight, so I’m guessing it didn’t go too well.”

As Barbara sighed, her immense tits pushed outward and spread her robe a little bit wider. Levi was staring at them and his mother could swear she noticed an increase in the size of the bulge in his briefs. He didn’t seem to care that his meat was slowly swelling in front of her. Maybe he wanted her to see it. Otherwise, he could have easily taken a seat where his most prized physical attribute would be hidden from view.

“I’m afraid you’re right, Sweetie,” she admitted. “It was a really dumb idea. You can be sure your silly mom won’t be going on any dates anytime soon.”

“I’m sorry, Mom,” he said. “For you, anyway. Not so much for me.”

Barbara reminded herself he didn’t know she’d seen him jerking off and calling out to her as his pleasure peaked in an explosion of young, spurting cum. Her nipples were so hard now and aching with need, but she certainly couldn’t encourage his forbidden attraction. Could she?

“Why not for you?” she asked curiously.

“Because I like it better when you’re here instead of out with some guy who probably doesn’t deserve you.”

Despite what she’d already seen and overheard, Barbara was taken aback at her son’s remark. Between the tone of his voice and the serious frown on his face, Levi seemed downright upset. It was one thing for a younger man to have unmentionable fantasies about his mother – as a single mother, Barbara was keenly aware of the classic Oedipal Complex – but his attitude came off as jealous.

“And how would you know if that’s the case?” she asked with sincere curiosity.

Levi shrugged, trying unsuccessfully to look indifferent. “I just do. Why else would you come home when you did?”

He had a good point, but his mother wasn’t about to reveal any details about the night before. She then realized she was just as guilty of jealousy as he. She never approved of the occasional girls he went out with, even Brynn, and even though she tried not to let it show she always found a way to express her irritation. There was always a moment where she’d let it drop that she thought the girls were never pretty or nice enough for him, even when they were.

But now, as she sat at her kitchen table absently gazing at the semi-erect impression of his cock in his briefs, she realized the girls her son went out with always looked like her in some way. That seemed to put a whole new perspective on the masturbation session she’d spied on just a few days ago. And now that her pussy was warming up more than she was comfortable with she wanted to escape. With her half-erect son staring at her like a piece of meat to be devoured while casting judgement on her unidentified choice of men, she felt like she was getting the third degree.

“Okay. You’re right,” she admitted with a heaving sigh. “I was trying to have a nice time, but, uhh, then I realized I’d made a mistake. Happy now?”

Barbara flashed back on Lymon thrusting excitedly into her pussy while she’d been thinking of the very same cock now visible in Levi’s boxer briefs. Then she flashed on the day she saw him stroking it and calling her name. She flashed on the shameless way she’d finger fucked her pussy standing right next to his bed the night before. All of which Levi never needed to know.

“Mom, I’d never be happy about something like that. I just,” he hesitated and thought, “I just don’t know why you wouldn’t rather stay home with me. I’m pretty sure you don’t mind my company, right?”

Barbara couldn’t help smiling. “I love your company, and you damn well know it. It’s just ... well, you know, even mothers who love their sons more than anything get lonely sometimes.”

Levi shrugged, feigning total cluelessness which irritated his mother.

“No one knows as well you that I haven’t been on a date in ages,” she snapped, surprising herself as much as Levi. “Unlike you, for example, who hardly ever dates the same girl twice. I suppose you just get what you want and then move on.”

Levi was clearly surprised by his mother’s reaction. He actually looked a bit angry now, and his cock was getting bigger in his briefs. He still wasn’t fully erect, but with an organ his size it didn’t take too much to look conspicuous in a tight pair of underwear.

“Think whatever you want.” His tone sounded as irritated as hers. “But it’s not like that at all. I can pretty much guarantee that I’ll never get what I want.”

Barbara felt her face go hot. She was visibly flushed and her eyes welled up. A week ago, she never would’ve suspected what it was her son really wanted, but now she knew. It was knowledge she couldn’t get out of her mind no matter how hard she tried. And now she just felt sad for both herself and Levi. For him, because she knew he was right that he would never be able to have what he really wanted. And for her, because she could never give it to him even if she wanted to be able to more than anything. How did their previously normal lives ever become so twisted?

“A lot of us want things we can never have,” she admitted, her voice softening as she leveled a serious look at him. When the blush started to creep across her son’s guilty face, Barbara realized she said more than she should. She never wanted him to realize she knew of his forbidden desire, but she’d suggested just enough to give it away. At least in his shame he barely noticed she was also suggesting the same thing about herself.

It wasn’t fair to let her son feel all the shame over something they both felt, but she could hardly bear knowing how frustrated he must’ve been just then.

“Sweetie,” she said, trying to lighten the mood. “There’s nothing wrong with wanting things we can’t have. It happens to lots of people. It’s only wrong if we act on those feelings.”

She didn’t mean to, but she couldn’t stop her eyes from dropping to the bulge of his youthful cock. She didn’t want to gaze so obviously but she couldn’t help it. Besides, it seemed like a better way to confess her feelings to her son without saying the actual words. A swarm of heat flushed through her pussy as she realized her son now knew as much about his mother’s lewd desires as she knew about his.

Levi’s cock quickly grew to its full size. He put his hand over it as if he was trying to cover it up, but all he really did was grip and squeeze it in front of her.

“I don’t see why that would be so bad,” he said suggestively. “If it’s what both people want, why shouldn’t they?”

“Because it’s so wrong, baby. So very wrong.” She kept her eyes on his throbbing bulge even as she denied the hot love they both wanted. He squeezed his rod and moved his hand along his throbbing shaft. Barbara’s nipples felt like they were burning and her pussy felt even hotter. It was shameful, yet no one ever made her feel the way Levi did. She lost herself for a moment or two as she grew mesmerized by the sight of his hand moving over his cock. It should’ve been her hand. It should’ve been his cock avidly pumping her wet pussy the night before. But what kind of woman did things like that with her own son? What kind of woman even thought about it?

 
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