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CHARLIE - Part 1

Author: Dayvid Notellin (dnt_x-asstr@yahoo.com)

Title: Charlie

Part: Part 1

Summary: A mother observes her cross-dressing son, and discovers she's also a pervert.

Keywords: bF, inc (m/s), Ped, Mast, Voy, XDress, Oral

Date: 01/05/2016

Originally Posted At: https://www.reddit.com/r/Ageplaystories/

[Author's Note]

 

Another night, another asshole, another failure. Karen was getting almighty sick of first-dates. It wouldn't be so bad if she could at least bring herself to get laid, but she just wasn't that kind of girl. She had to at least like a guy before she could bring herself to put out for him, and it seemed like every guy she'd been out with for the past six months was a complete tool.

 

It shouldn't be this hard. At twenty-eight, Karen was an attractive young woman, if a bit on the petite side. Still, with her slim figure, clear blue eyes and long corn silk hair, even her modest bust line shouldn't be that much of a deterrent. And actually, she sighed to herself, it wasn't. Most of the guys she'd been out with weren't turned off by her killer body and firm ass - just the opposite. Many of them expressed too much interest - or rather, too much expectation. It seemed like they all felt that because of a dinner and a show, she should be obligated to put out, no matter how bad their manners or personality. Oh well, maybe next weekend.

 

Slipping quietly into the house, she expected, and found, the babysitter asleep on the sofa with the TV on. That was fine. Jaimie always took good enough care of her son Charlie, who was doubtless sound asleep upstairs. It was almost eleven, well past Charlie's bedtime even on a Saturday night. Gently she woke the girl, paid her, and sent her home.

 

Quietly she eased up the stairs. If she woke Charlie, she wouldn't be able to take care of her frustrated libido. That was the real bitch about being a single mother - the kid always seemed to interrupt her whenever she thought she was going to be able to get some "me time", which for her meant giving BOB a work-out. She smiled to herself. BOB was what she called her vibrator - B.O.B. Her battery-operated boyfriend. An old joke, still funny.

 

Immersed in her own thoughts of self-gratification, she was half-way through the doorway to her bedroom before she realized that the lights were on, the room occupied. At the far end danced a little girl - wearing her favorite teddy!

 

For a moment she froze in shock, rapidly replaced by fear (there was a stranger in her home) followed quickly by anger (the stranger was wearing her delicates!) followed immediately by even more shock - the girl wasn't a stranger after all! It took her a few seconds in the dim light and distance, but any mother will always recognize her son. Even when that son is wearing lingerie and makeup!

 

Quickly she moved back to the shadow of the hallway. She didn't want to freak Charlie out or cause irreparable emotional trauma. If it turned out that her son was transgendered - if that was the right word - she didn't want the discovery to be scarring for him. Her. Whatever. She loved her son more than life itself, and would do so whatever he, she, or it turned out to be. Taking a moment to settle herself, she peeked around the edge of the door frame.

 

Charlie was dancing in front of the full-length triple mirror, admiring his/herself, and as Karen's eyes adapted to the dim light and distance, she had to agree that he made a rather cute girl. His dark auburn hair was long enough to pass, and he'd apparently had some practice with makeup and had put on just enough to enhance without being gaudy. Pretty impressive actually, she thought, for an eleven-year-old boy! And the outfit he'd selected was one of her favorites. Light pink, translucent, and she was so petite and him sprouting like a weed - the darn thing actually fit him pretty well! If he'd had breasts, nobody would have suspected a thing. Heck, at his age, most girls didn't have tits anyway!

 

Even his dancing was somehow more feminine than masculine, the swaying motions graceful and somehow provocative. He'd always been interested in dance, but she'd only ever seen him dancing at school recitals and such. His dance now included much more hip-shifting and butt-jutting and other moves which the school board would not approve of, but which were common enough on dance shows and videos.

 

She found herself enjoying the show, her own body moving slightly to the tempo of the music - it'd been forever since a man had actually taken her dancing, and while she'd danced with her son a few times, it was always "proper" dances. Seeing him dance like this made her mind wander to pleasant dances she'd had in the past. There was something alluring and erotic about being pressed close to someone, bodies swaying together in tandem. It was like feeling each other up using one's entire body instead of just the hands, though the hands did their fair share. She loved having her butt cupped and fondled on the dance floor, and more than once, on a particularly dark dance floor, she'd let her partner do even more. One man in particular, Jim was his name, loved nothing better than slipping his hand under her hems to caress her privates while in public, and the dance floor was the best. More than once she'd left the floor with her thighs and calves coated with her desire, her feet wet where her juices had dribbled down into her shoes. Good times!

 

Karen shook her head. She was getting far too aroused, and was unsure of what to do. Perhaps since Charlie was busy, she could sneak back downstairs and rub one out in the laundry room. Not ideal, but her cunny was tingling something fierce, and she was long overdue.

 

It was while she was considering this that Charlie turned in his dancing, and for the first time she saw that the light pink panties were tented, stretching far out as his rock-hard boner fought for freedom. Her ears rang with the sudden rush of blood to her face. Doubtless she was blushing fiercely, her pulse hammering strongly in her ears. She ducked back behind the doorway's edge, praying that she hadn't gasped in shock, closing her eyes, trying to wipe the image from her mind.

 

It didn't work. The more she tried not to see it, the more deeply the image of those tented panties burned into her mind. The detail. The roundness of the tip pushing outward. The length - he had to have at least five inches. Was that normal for a boy of eleven? She didn't know. She only knew that the last time she'd seen it, it'd been about half that size. Of course, that had been a few years ago. She'd stopped bathing him when he was six because every time she did, he got an erection, and she didn't want to cause him any embarrassment.

 

But... wow. She hadn't been with a man in a long while, but that was no excuse for the rush of heat that she felt between her thighs! Okay, yes, she'd been remembering good times with Jim, and had obviously been predisposed to erotic thoughts because of yet another rotten date, but still. This was her son! She had to get herself under control.

 

Karen had never been one to shirk responsibility. Whenever there was an issue, she tackled it head-on, and this was no different. Taking a deep (quiet) breath to steady her nerves, she peeked around the edge of the doorway again. To her relief, Charlie had turned back toward the mirrors again, so his pecker wasn't in clear view. He was still dancing, his hands sliding over his body now like some sort of erotic dancer. Or so she imagined - she'd never been to a strip club, of course. She relaxed a bit - at least she hadn't interrupted him or betrayed her presence. She could still sneak downstairs, and now it was more critical than before that she do so. She could actually feel wetness down there.

 

And yet, watching his moves, the way he was caressing himself, it was mesmerizing in a way. She'd seen men beat off before, and it was always the same - they went straight to their cocks, jerking it till they came. Charlie's moves were far more like her own, and like she believed most women were. He was involving his whole body, all his skin. Caressing his shoulders, his arms, his tummy, his legs, his ass. Karen could almost feel those caresses, and she found herself touching her own arms, shoulders, tummy. Her breasts ached, and she kneaded them gently - they might be small, but they were very sensitive, and her yearning increased diametrically. Her nipples tightened, her breathing quickened, and when Charlie's hands moved to his thighs, so did hers. It wasn't a conscious thought, it was sympathetic arousal.

 

Charlie was obviously growing more aroused, his fingers moving between his thighs, and Karen realized the boy was caressing his balls - again, not like a typical man who'd be wanking like a ... like a wanker. The boy was enjoying the slow build-up, not going for the instant gratification, and the look on his face, innocence, pleasure, arousal - was a study of eroticism. The fine bone structure, lightly enhanced with artful makeup really did look feminine, and if it wasn't her son, she'd have been fooled. No man ever looked that erotically aroused! When men got aroused, their eyes opened, not closed, and their countenance became feral, not blissful.

 

She wasn't even aware of it when his movements brought his erection back into view, and Karen was staring at it almost a full minute before it occurred to her that she was looking at her son's penis (through her panties) while she was rubbing her own cunny. When had she started touching herself there? What fucking difference did it make? It felt good! She hadn't been this aroused in forever! She could feel a bead of juice trickling down her thigh, bringing back to mind the way Jim would rub her to climax on a crowded dance floor. She shivered at the memory.

 

Well, if she could get off on a dance floor with strangers pressed all around her, couldn't she get herself off without alerting her son to her presence? Hell yes she could! Besides, Charlie was immersed in his own pleasure. From the new angle, she could clearly see him rubbing the soft silky fabric of the panties along his balls. That was just fucking hot! She could totally relate to how that felt - she loved silky panties against her own nethers! Tonight she'd worn lacy unders, which didn't feel as nice but looked sweet. She frowned as she recalled her hopes for tonight - if only the guy hadn't been such a dickhead, he could have shared his dickhead with her! She slipped her fingers between the scratchy lace and her soft, smooth labes, feeling the warm wetness as her fingertips sought and found the groove, leaning against the doorframe to keep her balance as a powerful surge of pleasure coursed through her.

 

Charlie's dancing had all but stopped, so intent he was on the feeling of the silk on his balls. He moved the fabric, making it slide back and forth, and even in the dim light Karen could see the wetness at the tip darkening the fabric. She hadn't known if he was developed enough to produce cum yet, but apparently he was. She wondered why she'd never found evidence of nocturnal emissions - she'd heard that when boys got old enough, wet dreams were typically not uncommon, and she'd practiced "the talk" in her own head several times in preparation for that eventuality. But apparently her son was more cautious. Maybe he beat off every night before bed. That idea sent another surge through down her spine. She wouldn't want to walk in an interrupt him of course, but she'd always loved watching men jack off when she was with one who wasn't too shy to do it.

 

Apparently the boy was getting closer. He moved away from the mirror, pausing as he glanced at the clock. For a moment she was sure he was going to put a stop to his shenanigans, probably fearing she'd be home soon, but then he shrugged, apparently deciding she'd still be out a while. He walked over to the bed (even his walk was surprisingly graceful and feminine, even with his pecker tenting lewdly in her panties) and climbed up onto her bed. Her bed! Was he going to get off on her bed?

 

He was. The boy laid back on her pillows, rubbing cat-like against the silky fabric (not real silk but satin felt even silkier than silk did, which was why she had satin pillow slips and sheets). His lithe young body looked beautiful as he slid the bedcover down and rubbed against the slick fabric. It took her a moment to realize that he was dry-humping his hard pecker, through the panties, against the slick sheets.

 

Part of the delay was because as he was arching his back, face down, it showed his ass to amazing effect. The panties were purpose-designed to give the greatest effect of course, but even so, his ass was amazing! She wondered if she looked as sexy in that outfit as her son did. She hoped so!

 

As the boy's movements continued, her own fingers moved in sympathetic arousal. The boy was clearly getting off, and so was she. Trickles of juice traced down her thighs and legs, tickling their way down into her shoes, and her nipples ached so hard she had to rub them against the edge of the doorway though her top. Watching Charlie getting off was easily the most erotic thing she'd ever seen. Karen had never really thought about making out with women before, but knew now that she'd have to try it out. If a mock-girl could get her this horny, what could a real woman do with her body?

 

Carefully she let herself cum - only a little one... and another, just to ease the tension some. She damned sure was going to keep the big one to share with her son, even if he never knew about it! And the way his hips were moving, she thought he might be cumming pretty soon - at least she hoped so! She wondered what he'd do about the mess. Would he leave it in her bed? That would be hot! Her heart hammered. What if he'd done this before? Had she been sleeping with her boy's cum and just never knew? She knew she'd never be able to get into her own bed again without wondering - and without getting excited by the thought. Sure, until tonight, she might have found the idea distasteful. But now, tasteful - literally. She could totally see herself licking the sweet cum from the sheets. Oh God, she was going to hell, but fuck it!

 

Charlie rolled over on the bed, his cock distending the panties lewdly upward, and Karen's mouth felt dry. It was such a sexy sight, her panties wet with his juices, his young cock strong and hard, straining upward. She licked her lips unconsciously. She'd never been a huge lover of giving head, but her mouth watered at the sight and thought of taking her son's cock orally. She was beyond shame though, and merely accepted the thought as additional fuel for the fire that was burning between her thighs. So close, she thought. Come on darling boy, please hurry, I'm so ready!

 

As if hearing his mother's silent plea, Charlie grinned and playfully stripped the panties off, turning away from his mother in the process and giving her another wonderful view of his sweet round ass. Then when he turned back onto his back, his cock was in full view, standing stiffly upward like a rocket about to go off.

 

Karen covered her mouth quickly. She actually had gasped this time - more of a squeak actually, and was terrified that Charlie heard and would stop. She didn't actually even think about her own embarrassment at being caught watching him, she just wanted to see her little girlie-boy finish his sexy play! Fortunately, he was too wrapped up in his own play. He played with his cock - literally - as if he was a little girl who'd never seen one before. It was, bizarre and bizarrely cute, and bizarrely erotic. Powerfully erotic. It was in some strange way, like watching a young boy and girl the first time they play sexually together, and she was mesmerized as Charlie played both roles, the young girl exploring her first cock, and the young boy being touched by a young girl for the very first time. Karen thought she might explode any moment, and fought to wait until he did.

 

Fortunately, his build-up had been sufficiently arousing that he was more than ready to explode, as was made clear by the clear drops oozing out the tip of his cock. Every touch of "her" fingers seemed to draw another bead from "his" tip, which "she" then smeared around, making "him" gasp with the pleasure. Shortly "her" fingertips circled around "his" rock-hard member, making "her" coo with happiness and "him" groan with pleasure so intense it bordered on pain.

 

"Stroke it, you little bitch," he growled.

 

"She" giggled, and did so, making "his" body tense up.

 

"You like that, don't you," she asked.

 

"Oh fuck yes," he growled back. "I'm gonna spurt cum all over you!"

 

"Pwomise?" she said coyly in an even littler-girl voice, bordering on baby-talk.

 

Karen's head spun. She could actually "see" the "two" children, and she felt twice as voyeuristic as before. She wasn't just watching her son jack off, she was also watching her daughter play with her first cock! She was panting heavily, four fingers buried in her drooling, clenching pussy, trying hard to keep still, sure that the second her fingers moved, she'd begin cumming - and then the floodgates would be opened!

 

"I promise," Charlie said, his voice low, panting his barely-held-back lust. "I promise you'll be so covered with my cum that you may drown!

 

"Do it, I dare you!" Charlie taunted him. "I wanna see it spurt and feel it on me!"

 

"OH FUCK!" he cried out, his body beginning to jerk as "her" hand moved up and down. "I'm cumming! I'm cumming!" He shouted it out hoarsely, loudly, as if trying to announce it to the neighborhood. "I'm cumming nowww!" he howled out at last, and as foretold, a geyser of cum shot straight up, high into the air. Before it landed, "her" rapid stroking elicited another, and another. Rapidly the jets came out, flying up and arcing slightly to spatter down on "her" tummy, "her" chest, even "her" face. It seemed to go on forever.

 

Karen was right there with him, her own gush of pussy juices spraying out as his first spurt shot into the air, her hand slamming in and out of her spasming cunt rapidly as her own panting joined his. She was beyond caring about anything else, she needed to cum in the same way a man dying of thirst in the desert needs water. And cum she did - like never before, dousing the carpet in her bedroom doorway with her juices as they gushed out, hit her panties, then poured off her gusset thence onto the floor as she squatted there, hand-fucking herself with reckless abandon, watching her little boy - and her little girl - culminate their sexual play.

 

She was so spent by the time she was done cumming, that it took her several minutes to realize that she was actually fully in the doorway when she came, and was now sitting on her ass in carpet-puddle, leaning against the doorway for support, her body still shivering, cool with the sheen of sweat covering her, her throat hoarse. Had she screamed? Probably. She usually did when she came, and that one had been the most powerful climax she'd ever had.

 

She suddenly realized that they - no, he had to have heard her! No matter how engaged he was in his own sex-play, it'd be hard to ignore her own cries of passion. Bashfully she looked up at the bed, preparing for the worst.

 

"Mommy," Charlie said in a sweetly timid voice, more feminine than masculine, "I made a mess!" S/he looked about ready to cry, scared and nervous and hopeful all at the same time. "Could you get me a towel pweeese?" The baby-talk was back.

 

Karen smiled gently to let him/her know she wasn't mad, which brought a relieved smile to her child's face. With an effort, she struggled to her feet. "It's okay baby," she said softly. She walked slowly to the bed to give herself a moment to try to frame this revelation. If anything, she loved Charlie more than she ever had, but there was no denying that things had changed drastically. But Charlie more than anything else, needed to know that she still loved, supported, and cherished him. Her. Whatever.

 

By the time she reached the bed, she'd come to the inescapable conclusion that in a way, they were lovers now. They shared a secret. Several secrets. And it was up to her to guide her son/daughter. At the same time, she also had a new-found and intense desire to share even more with her kid, regardless of gender. She found both to be incredibly erotic, and she knew she had to experience more with Charlie.

 

Sliding onto the bed beside her baby, she leaned over and kissed those sweet lips. "Momma's here honey," she cooed. "You don't need a towel - if it's okay with you, I'll clean you up." Charlie looked at her quizzically, but nodded, accepting.

 

Knowing she was crossing yet another line, and yet thrilling at what promised to be a beautiful, enriching, and highly erotic experience, she began to lick the cum from Charlie's smooth, hairless balls.

 

From the first touch of her tongue on those smooth, hairless orbs, Karen knew that the adventure had only begun. As she scooped the sweet sauce, her ears ringing with Charlie's soft moans of pleasure, feeling Charlie's hands on her head, she had a glimpse of their future. She'd show "her" how to be a woman, and she'd make "him" into a man. The vistas of her newly-awakened pedophelic desires spread out before her, depravities she'd never even thought of springing full-formed into her mind. And she knew she was right when, as she climbed onto all fours to lick the cum from his thighs, she felt her son's hand cupping her soppy-wet pussy. Yes, he had a lot to learn, but they both did. And they'd explore this new life together, fully experiencing every pleasure and variation they desired.

 

FEEDBACK - Thank you for reading! If you'd like to leave feedback, please read the following:

If you leave feedback, please, please, PLEASE include the Name & Part / Chapter you're talking about. Thanks!

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Most writers appreciate feedback on their work. However most users would rather do so anonymously, especially for questionable subject matter such as that which I write about.

 

ASSTR used to have a feature to give anonymous feedback, but it now appears to be broken. So if you wish to leave feedback, you have two options:

 

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3. There are a number of free anonymous emailer services out there. If you use one of these, PLEASE include the subject "Feedback_Charlie1". A quick search found some examples:

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4. If you have another method to recommend, I'm all ears! Thanks!