It might have started out light, but It hadn’t taken long at all before their kissing had developed into something more. It had begun as just a quick little kiss, not their first but sweet all the same, but before he had known it, he had had her shirt up over her head, her bra soon joining it in tandem on the floor, his small delicate hands guided by hers, both of them eager for him to start exploring the sensuous curves of her body.
It had been euphoric, the warmth and softness spreading under his fingertips as he had groped and squeezed her, needing to feel her in his hand, his confidence building as he wanted more and more, cupping and freely playing with the swell of her breasts, much to her delight.
As they kissed, his hand firmly pressing against her chest he felt her hand move down the front of his pants, tracing the smooth line of his feminine figure until it had come to his cock.
He had moaned into the kiss, eager as he had felt her fingers close around his cock, her hand finding it hard and giving it a few small quick strokes.
She had broken the kiss then, sitting up, Alex had looked across at her, a soft blush on his feminine features as their eyes met, hers searching for a moment before she spoke, her voice sounding a little cold.
“Did you hear that?” She asked, but he shook his head, he hadn’t heard anything.
He bit his lip, concerned and a little disappointed when her hand left the tightness of his pants and she stood, stepping away towards the drawers on top of which she had placed her phone.
“What is it?” Alex asked softly, his eyes looking at her with concern as she picked up her phone, unlocking it and scrolling through its contents.
“I swore I heard it buzz…” She said, hesitating for a few long moments, her gaze flickering from the screen to him.
“I-is everything…” he started, but she cut him off, hurrying over to collect her bra.
“It’s my parents… They texted me to let me know they have to come back, you can’t be here when they get back.” She said hurriedly and, without any reason to doubt the love of his life, he nodded, eyes wide as he sprung to his feet.
Still dressed it had taken him virtually no time at all to get himself ready, shuffling his coat on over his narrow shoulders and pulling on his shoes.
She had seemed keen to get him out of the house as soon as possible and he hadn’t resisted, finding himself torn from the warmth of her almost nude embrace into the bracing cold of the night air in less than five minutes.
He had been hurried out so quickly that when he turned to the door to kiss her goodbye, he had only been met by the approaching swing of the heavy door which swung shut with an air of finality.
He had sighed and, head down against the biting chill of the night air, had made his way home walking through the familiar streets illuminated only by the occasional street light.
When he returned home, feeling more than a little dejected, he had stripped himself of his coat and shoes, leaving both by the door before moving through to the sitting room, giving the room and attached kitchen a sparing glance to check for his mom before settling down on the sofa with a little sigh, curling his legs up under him.
A night alone at home wasn’t quite what he had been expecting and was a far cry from where he had been just a short while ago, in the soft enticing embrace on his beloved girlfriend, about to, he hoped, if not lose his virginity, at least go down on a girl and maybe get something in return too.
Nevertheless desperate to talk to her he pulled his smartphone from his pocket, putting in the little pattern he used to unlock it before checking for messages.
Alex smiled a little, his longbow lips drawing up in a gorgeous little line as he saw a notification from her already, and without knowing the path it was about to set him down, he opened and read the message.
“Alex, you’re really really sweet and I’m sure you’re going to meet someone perfect for you sometime, but you’re really just way too small for me. I knew you were a little girly and I thought that was super cute but a relationship needs to be more than that, I need a physical connection and I just don’t think I can have that with you, you’re just too pathetically small. Bye Alex.”
He hadn’t responded, he hadn’t needed to. The little ‘seen’ icon that would pop up the message for her would be all the response she would need from him to know he knew it was over.
He’d sat stunned for minutes, the phone dimming then locking in his hand, left completely shocked by what he had read. He wanted to unlock his phone, to read it again to be sure he hadn’t misunderstood, but his fingers wouldn’t move.
The phone clattered to the floor and Alex scooped up a cushion, bringing his knees high up to his chest and sandwiching the plush fabriced cushion between his face and his knees, his chest rising and falling erratically as, with no other way to react, he began to cry.
Jenna had been upstairs enjoying the peace and quiet of a house without her effeminate darling son with a luxurious hot bath, scented candles and more than one glass of white wine when she had, to her surprise, heard the door.
With no one else in the picture for her it could only have been Alex returning and, a little annoyed, she had let out a little bit of a sigh. While she adored her son to no end, she had been looking forward to a little bit of a break from having to control herself around him.
She had continued to relax in the bath, assuring herself that she wouldn’t be needed at least until the water ran tepid and was content to enjoy this little slice of peace, but the unmistakable sound of his crying reached her, even through the bathroom door and the pillow she knew he was doubtless clutching.
Biting her lip and with a little grunt of effort she lifted herself from the bath, her arms tired and heavy from what had been the penetrating heat of the scented waters, whose comfort she now left behind to be greeted by the steamy air of the bathroom, pleasant, but not nearly as pleasant as her bath had been.
Stepping carefully as not to slip she moved to switch the bathroom light on, the sudden iridescent light permeating every nook and cranny of the room serving to sweep away the last remnants of the warm relaxing atmosphere she had created with the candles low flickering light.
She caught a general outline of her figure in the steamed up mirror, unable to make out any detail as she picked up a thick white towel, patting down her fair skin in a hurried way, not being as thorough as she often would be, wanting instead to find out what had upset her son, though she had a pretty good idea.
After drying herself she glanced down at her body, twisting her wide hips this way and that to see if there were any glistening beads of water she might have missed on her impressive curves and swinging cock, but seeing none she set the towel down, scooping up instead a comfortable robe which she pulled on over her shoulders, feeling the fabric wrap around her like a well-deserved hug.
Her breasts, full and soft, felt uncomfortable without the support of a bra, but not wanting to go through the bother of finding and putting one on she opted instead to tie the bathrobes cord a little a higher under her bust, pushing it up and presenting a few inches of cleavage. Not that she was trying to look alluring, but with a bust as impressive as Jenna’s, there are few things you can wear without displaying your gifts just a little bit.
Blowing out her candles and finishing her wine she padded from the bathroom, opting to clear away the clutter later. She moved to the stairs and with one hand on the railing glided quietly downstairs, the carpet muting her approach.
“Alex sweetie?” She asked lightly, scanning the room as she entered with her hazel eyes, her gaze quickly settling on the small curled up figure of her son, wrapped up in his own arms on the sofa, his phone beside him on the couch, left ignored.
She hesitated, leaning on the doorway briefly and tilting her head, but he didn’t respond to her arrival, didn’t even acknowledge she was there, if he had even actually noticed.
Jenna took in the scene, piecing together the simple clues. He was supposed to be spending the night with his girlfriend, their first night together and, given how flustered he had seemed before going around, likely their first time doing a lot of things. But given his current disposition…
“Oh sweetie…” she said softly as she stepped over, sitting down gently on the couch beside him and slinking an arm around his slender waist.
It took a little persuading, but she was able to divert his curled up form from being wrapped around his cushion to be embracing her instead, his arm draped over her stomach, his head resting on the warm swell of her heavy chest.
She held him gently, consoling him with soft shushes as she gently caressed his long silken hair, waiting for him to calm down a little before she asked the question they both knew was going to come.
It took a little while, but his sobs and shakes slowly ebbed away, leaving him sniffing, breath still ragged as he leaned his head on her, staring off at nothing.
Glancing down at him, her face one of concern she reached down, one delicate finger wiping away one his tears, her touch drawing his attention, his doe-like eyes looking to meet her own.
“What happened, love?” She asked, the question inevitably making his lip quiver, his gaze quickly shifting away from hers once more, his hand clutching at the soft fabric of her robe.
He opened his mouth to speak, but after a moment closed it again, swallowing, “S-she… She…” he whimpered softly and she gave him a gentle reassuring squeeze, “She broke up with me…” he finally managed, though his tone weirdly, seemed a little defensive.
“Oh, honey… I’m sorry,” she said, holding him a little tighter, “I know how badly it hurts.” Which was true, she had had her own fair share of bad breakups back in her youth, before Alex. “Did something happen?”
He swallowed a little and looked away and she knew him well enough to read the flood of embarrassment on his features.
“Hmm?” she said softly, pushing just a little in her curiosity.
He looked up at her for a moment, taking in the soft smile on her full lips, noting how dark her usually vibrant naturally orange hair was, likely still wet from her bath. After a moment he sighed a little, relenting, though his voice remained soft, a little distant.
“She… Well…” he bit his lip, “Okay, so we were just… You know… Just…”
“Fooling around?” she offered helpfully and he blushed before nodding, almost imperceptibly.
“Y-yeah, but, I… She told me to go and I did… Then she just… She texted me and… And she… And it…”
His string of words trailed off showed no signs of picking up where it left off. After a moment she reached across and collected his forgotten phone, pressing it into his hands.
“Why don’t you just show me hm?” She asked gently.
Uncertainty he turned the phone over in his hands a couple of times until, at last, he relented, thumbing in the pattern that unlocked his phone and handing it to her.
She gently held it in her hand, away from his face so she could browse through his phone without having to reveal whatever the text had been to him again.
She knew her way around a smartphone and was soon inside the messenger she knew he used and found the most recent conversation.
She tapped it open and read through the message, feeling him curl up a little tighter against her as she did.
“Ooh honey…” she said softly, her voice consoling as she let out a little sigh of faux disappointment directed at his now ex.
After rereading it and, hiding a smirk, locked the phone and set it down once more, pulling him just a little tighter to her.
“What am I supposed to do now…” he said quietly, not framing it as a question, it coming across more of just a statement of how truly lost he felt in the moment.
She paused for a moment, seeing the conversation he probably expected play out before her, reassuring him he’d find someone, that she had just been shallow, that he was beautiful and kind and funny and any girl would be lucky to have him. But inside she knew that wasn’t true.
“Give up…” she said softly and he looked up at her a little sharply, his eyebrows furrowing a little and he looked at her in confusion.
She shrugged a little, “I said you should give up.”
“On what, her?” He asked, uncertainty.
She nodded a little, but continued, “and pretty much on girls in general, in a way… I mean… Oh, Alex, I knew I’d have to have this talk with you eventually but, there’s really no nice way to go about this.”
He moved to sit up a little, which she let him, but kept her arm snuggly around his waist, noting how as he sat up, she remained looking down at him, his body so slight as to be shorter than her.
“What… What talk?” he asked, concern in his voice.
“I mean… I’m sorry, but every natural born woman is going to have the same reaction as she is… All of them.” She paused, letting her words sink in, knowing that sometimes delivering the truth was like ripping off a band-aid. “You’re never going to really be able to satisfy them, you’re not really all that much of a man, you must know that?”
He looked like he’d been slapped and she couldn’t really blame him, but she kept her voice steady, her demeanour gentle. She watched as his eyes teared up once more, the boy feeling a second dagger in his back, this one from an even less likely source.
“Why… Why are you saying this?” He said, voice quavering, very much on the verge of crying again and, she gathered from his body language, very close to leaving her and storming off upstairs.
She thought for a moment… Because he had to know at some point? Because in this state, broken and vulnerable she sensed an opportunity? She had been looking to relax and unwind with a hot bath, but she had watched her son grow up into a hot piece of ass and maybe it was finally time to teach him that?
“Because I love you,” she smiled sweetly and squeezed him, “and I want you to be happy.” Not untrue, she thought.
“By saying I’ve failed as a man?” He asked, his accusation coming out in a soft shaky voice.
She paused for a second, reaching up to brush a strand of her almost dry orange hair back into place, their natural curls becoming more apparent as the weight of the water faded from it.
“Alex… To say you failed as a man isn’t really fair.”
He swallowed a little and seemed a little placated by that, indicating he hadn’t exactly understood what she had meant.
“I mean, you never ever really had any sort of a chance at being a man, I always hoped for your sake that puberty would be generous to you, and it was, just… Not in the ways most young boys hope it would.”
He scoffed a little, but tears were now once more running freely down his cheeks, “Oh, then how exactly was it generous?”
“Sweetie you’re so beautiful! I don’t know how you don’t see that… You keep comparing yourself to what you think a man should be, but have you ever just stopped to compare yourself to just about any woman? You’re gorgeous honey, I mean I would’ve killed to have skin as perfect as yours at your age, smooth as anything, curves and hips and an ass like you spend half the day doing squats…” she giggled a little, but he didn’t laugh, he merely looked dejected.
“So what, no woman will ever want me, you said so yourself! I’m just a-”
“Hey,” Jenna interjected, poking him gently in the arm, “I never said that.”
“I said you’d never satisfy any natural-born woman,” she clarified.
“Okay so I’ll never satisfy any woman, that’s the same as them not wanting me isn’t it?” He said, sounding more than a little exasperated.
She shook her head, “Alex you aren’t listening, I said any ‘natural born’ woman,” she said, emphasizing the words.
“What do you mean?” He said, hands folded on his lap.
She pursed her lips a little, “Well, sweetie, you know about mommy and her, you know, thing?”
She raised her eyebrows and after a moment his eyes went wide.
“Y-you don’t really think…”
She smiled softly and tilted her head, “You’ll never succeed as a man honey, but as a cute little girly boy? Sweetie if you wanted you could have women like me fawning all over you.”
He looked down and she smiled a bit, pushing the point, “Imagine that, walking into a room and being the centre of attention, everyone’s eyes on you, wanting you, absolutely desperate to get in your pants, to kiss you, to feel you up, to fuck you…”
He blushed brightly as his mom’s words, looking up at her sharply, “M-mom!”
She laughed and eyed him with a sly smile, “What? I might be your mom but I’m still hot-blooded, in my youth if a boy like you walked into my life I’d have had you stripped down and pushed up against the nearest wall in a heartbeat.”
His cheeks burned with a crimson and she couldn’t help but admit she was enjoying the reaction, so she continued, “Not that I haven’t thought about doing that to you anyway, of course.”
“D-don’t be gross…” he whimpered adorably, before looking away embarrassed.
“I’m being honest sweetie… Do you know how many times I’ve jerked off thinking of you? Mm…”
Biting his lip he made to stand, to leave, too conflicted to even look at her, but as he raised himself he felt her hand at his wrist, tight like a vice, pulling him back down to the sofa with a whimpering gasp, “L-let me go…”
“Alex, honey, this for your own good? You’ll never be happy until you accept who you really are…” She pressed, holding him still.
“I-I’m a man!” He protested, trying to pull his slender wrist free from her grip and failing utterly, Jenna not having to make any sort of effort to keep him in place.
“Really? Then show me.”
She smirked at his adorably pathetic attempts at breaking free from her, “Calm down sweetie, look, how about we make a deal?”
He pulled against her for a few moments longer before pouting up at her, noting her single raised eyebrow and patient expression. He swallowed anxiously, “W-what kind of deal?”
She smiled, “We do a size comparison and-”
“That’s not fair! I-I know you’re bigger than-”
She shushed him, frowning a little sternly, “Let me finish…” She paused, eying him for a moment but he remained quiet this time, “Good boy, now, we do a size comparison and, if I’m no less than three times bigger than you, you concede your rightful place…”
He opened his mouth to object, then hesitated, he was three and a half inches when hard, that would mean to lose, she would have to be packing more than ten and while he knew she was bigger, having seen her soft once or twice growing up wandering into her bedroom, he didn’t recall it being that incredibly big.
“…And what if I win? What if it’s not that much bigger than mine?” He asked, tentatively.
“Well, if that is the case, I’ve got a friend… A brunette, in her mid-thirties but she’s drop-dead gorgeous, owes me a few favours. If you win, I’ll have her pay you a visit hm? Make a real ‘man’ of you.”
Alex bit his lip, looking down for a moment, “What… Whats her name?”
“Jane.” Last name Doe, Jenna thought.
He looked at her, biting his lip, trying to picture this Jane in his mind, then finally, he nodded slowly, “O-okay…”
She smiled, “Good choice…” She purred low, as if he had had any kind of a choice in the matter, “Do you want to whip yours out first, or shall I?”
Alex hesitated, then nodded to her, his cheeks coloured, shy to reveal himself to her in such a brazen way, reservations that Jenna didn’t hold.
Smirking she reached down, twitching her bathrobe aside revealing her pale soft thighs and, as the fluffy fabric pulled further back, the pale soft length of her cock.
She didn’t look down as she revealed herself to him, in fact, she kept her eyes firmly on him, watching his expression, the widening of his eyes, the parting of his lips in surprise, the way the colour drained from his cheeks, his pallor becoming more like her own fair skin.
She reached down and caught the base of her cock, pointing it upwards though it flopped to the side, bowing mid-shaft as she was still soft. Her length and girth were impressive and she could tell by the stunned expression on his face and the slight blush at his cheeks that while he had been expecting something, he hadn’t been expecting all that.
“Want to concede, honey?” She smirked, unable to hide the smugness from her voice as she held her nine inch cock, “I know I’ve won and so do you.”
He looked up at her and swallowed, realising, perhaps for the first time, the full extent of his comparable feminine nature, “N-no.” he bit his lip, as it was he knew she was so much bigger, but if he was hard, and if, when hard, hers wasn’t any bigger, just thicker, he might just be safe.
“If I’m hard and you’re that big… I’d win…” He said, softly, a desperate edge to his voice.
She grinned and reached across, stroking the back of his head affectionately, though he grimaced slightly, “So you want to compare them both hard hm? Well then, you’ll have to help me get mine hard…”
“Or concede.” She finished, brightly.
He looked away, cheeks flushed, eyes searching at nothing as he thought, “…Fine…” he finally said.
“Good boy,” she cooed, “hold out your hand, you don’t need to look if you don’t want to…” She really didn’t care if he watched, she just wanted to feel him.
After another moment of hesitation he held his arm towards her which she took greedily, guiding it down towards her cock. Using both her hands to guide his hands and fingers to her soft length.
His cheeks glowed as she wrapped his hand around her length, letting him feel the foreign size and softness between his fingers and she wrapped her hand around his, making sure he couldn’t pull it away if he wanted to.
“Ahh, there we go…” She purred softly as she started to shift her hand up and down, jerking off with his small delicate hand, “that feels so good… Do you like that? Do you like stroking mommy’s cock?” She grinned.
He didn’t respond, but his cheeks were flushed crimson as she continued, his hand warm around her cock, she squeezed his hand, forcing him to grip her growing length tighter. She might have been a shower instead of a grower, but the few inches she would gain as well as the straighter poise of her cock, she knew, would easily bring her victory.
She bit a full lip, raising a hand to tuck a few stray strands of hair behind one ear, her hips moving slowly in rhythm with her hand as she grew hard.
Alex swallowed, feeling the heat emanating from the cheeks and the growing steeliness of her cock under his fingers. He felt the odd firm sponginess of her length and knew that she was fully hard. She didn’t stop though, obviously eager to continue as long as he let her.
“H-hey,” he said, pulling his hand away and turning towards her, noting the knowing smirk on her lips as she let his hand go, his gaze drawn inevitably towards her cock.
She was sat relaxing back in the chair, her hips pushed forward almost to the edge of the seat, her cock pointing straight up towards the ceiling, the pale length twitching eagerly, her balls drawn up tight underneath.
“You like what you see?” She teased and he looked, feeling a sinking feeling in his chest, knowing the outcome, “Come on now, this is your chance to win the bet, let’s see what you’ve got sweety.”
“I… I don’t want to…” He murmured softly, his thighs tucked tightly together as she looked on, admiring his reserved cuteness, one of her hands idly stroking her cock, keeping it hard as she watched. In her youth, before the wonders of motherhood it would’ve stayed hard on its own, but now it needed some gentle persuasion.
“I don’t care what you want Alex love… You either take it out and show me, or we go upstairs to my bedroom and I-”
“Okay, okay!” He said hurriedly and she grinned, he was clearly taking her threats legitimately now they’d come this far.
She waited patiently, enjoying the conflict that played across his face with every small movement, his cheeks bright as, for the second time this night he started to open his pants, reaching down and within.
She chuckled softly as he exposed himself, raising her hand to cover her mouth, though the laughter line around her eyes still showed her mirth, “Oh darling!”
They had both known she would win, but, to his shame and her glee, she hadn’t expected to find his cock, three and a half inches long, as hard as a rock as he presented it.
“I’m glad to see you’re conceding your place so easily…” She grinned, reaching a hand across to caress her fingertips through his hair.
“I-it’s not like that…” He said defensively, the humiliation plain to see on his face.
“It doesn’t matter what it’s like,” she smirked, “you know that I’m right, you’re not a man, you never will be. So, please… Let me teach you how to be the best woman you can be?”
He swallowed and looked distant for a few long moments, his cock twitching slightly before he turned and looked to her, his eyes wet, uncertain and broken.
“How…?” was all he said.
“It’s actually really really easy love. You just have to not be afraid of this.” She glanced down towards her own cock, giving it a few pointed strokes.
He swallowed, his eyes flickering down to look at it, “I-I’m not afraid of it…”
“Oooh? Then suck it.” She said, her voice sultry. He opened his mouth to speak but she cut him, “Ah ah, no back talk.”
Her fingers, which until now had been caressing his hair tightened slightly, exerting a pressure to push him down, an action that he resisted but not nearly enough to actually stop him.
“There, go on, it’s not going to bite, and you better not either…” She said with an edge of warning in her voice, though she didn’t think it would be a problem.
Alex whimpered a little, his hands moving to rest on her thighs to support himself as she urged him further down and down, the thick veined length of her hard monster approaching his lips, “I-I can’t…”
She bit her lip, so close now she could feel the warmth of his breath against her sensitive tip, “How about just a kiss then hm? Can you do that sweetie?”
He chewed his lip for a moment, feeling the pressure of her hand on the back of his head urging him onwards, “J-just a kiss?” he asked, voice a little shakey.
“Just a kiss.” She promised.
Closing his eyes he leaned down her hand midshaft guiding the tip of her cock to his approaching lips.
He felt something hot, silky and spongy bump against his lips which he puckered in a kiss, but as he did he felt her hips shift, her grip tightening and felt his head being forced down.
He whimpered in surprise as the tip forced its way between his lips, his jaw relaxing so he didn’t accidentally bite her as she slid her length into its new home, her son’s mouth.
“Ahhh fuck Alex, just like that, oh that feels so fucking good…” She commented, the pleasure obvious in her rich voice as he found himself with a mouthful of her long pale cock.
Jenna tilted her head back in bliss and held his head firmly in place with two hands, relying on her son’s submissiveness as she roughly began to move his head up and down, using his pretty pink lips and hot wet mouth like she would a fleshlight.
“Suck it, or I’ll have to use your throat instead…” She urged, feeling his lips, rolling up and down her length tighten to a seal around her, a sudden tingling pressure tickling the sensitive tip of her cock as he began to suck.
“A-aaah.. Yeah, see? Not so bad is it, aaah, oh fuck I wish I knew my son would make such a good cocksucker, come on, harder…”
He complied and she moaned, his tense muscles relaxing to let her do what she wanted.
Though he could feel a couple of tears on his cheeks, it wasn’t because of what she was forcing him to do, suck her meaty cock, but because he knew there was no turning back, no last-minute reprieve for his masculinity. She might have been forcing him, but it had only taken the barest amount of effort on her past, his resistance had been token at best, like he’d wanted it almost, or at the very least that he’d recognised it was inevitable.
As he relaxed she moved one hand from his head to slip it inside her bathrobe, cupping and squeezing one of her heavy soft breasts. Pinching the hardened nipple between her thumb and forefinger to draw as much pleasure as possible from her body.
“Play with my balls sweetie…”
He barely hesitated, one hand moving from her thigh down between her thighs, moving under the heavy orbs in their smooth sack to lift and cup them, giving them soft squeezes and rolling them between his fingers.
“Good boy…” She purred and he felt a little spark of pleasure inside of him, his cock twitching, a single shameful line of pre trickling down his cock, not that Jenna noticed or cared.
She lay there, cupping herself and guiding his head as he massaged her balls, feeling pleasure she hadn’t felt in years surge through her, the thrill of a special victory. She’d had sex over the years, sure, specifically, everytime her son had shown interest in one of his barely legal friends Jenna had gotten involved, turning the girls out and away from her precious son, at least until the right one came around. Jenna had recognised his now ex as the shallow bitch she was and knew, if she let their relationship blossom her finding out his size and subsequently ditching him would be inevitable. It had played out exactly as she planned, her son falling into her arms, broken and ready for her.
“Mmm…” She moaned low, rolling her hips in rhythm with the up and down motions of his head, “Use your tongue more, come on, if you want my cum you’re going to have to work for it…”
He whimpered, the only protest it seemed he was capable of but before long was obeying her, his tongue pressing tighter against and swirling occasionally around her. He was amateur she thought, not her best blowjob by a longshot, lacking conviction, skill or the ability to deepthroat, but still her pleasure raged, none of that mattered, he was her son and finally, finally he was going down on her.
She chewed on her lip, pinching and pulling on her nipples so hard it hurt so good, her nipples pulled away from her body, caught between her fingernails until they bounced back hard and throbbing.
“That’s so good baby, you’re going to make me cum soon, you want that, I know you do, you want to swallow mommy’s cum…” She panted low, her lips parted slightly as she watched the back of his head bob up and down on her length.
He did, gods he hated it but he did want her to cum. In the conflicted maelstrom of his mind he tried to reason it was because the sooner she came the sooner it was over, but even to himself that felt like a weak argument.
Her pace quickened and became more erratic, the movements of his head and her hips falling out of sync as she drew close, occasionally pressing too deep and drawing a gag from him, not that she slowed when he did.
Spit rolled down her cock to be massaged into her balls by his delicate hand and she knew she was close.
He felt her balls tense in his hand, but so distracted by the sensations pervading his mouth he didn’t piece together what it meant until the first blast of cum struck the back of his throat, she held him tight with her hand, keeping him pushed down as she fucked her cock up into his mouth, panting and gasping aloud, repeating the same instruction over and over again.
He did the best he could, his lips forming a tight seal as her cum pooled in his mouth around his lips making it difficult to gulp down, though he could taste it, for the first of many times he thought.
Jenna felt a line of thick cum ooze down her cock and squeezed his hair painfully tight, “I said swallow!!” She spoke louder, her voice shakey though her pace slowed, allowing him to swallow with more ease, his slender throat bobbing as he emptied his mouth of her contents down into his stomach.
She panted hard and long, sank deep back into the chair, her hand falling from his head.
He sat up slowly, his lips remaining tight so no more cum dribbled free from his lips and, once he was sat up he tilted his head back, finding it much easier to swallow.
“Mm… You missed a bit…” She said, her voice critical.
“I-I’m sorry…” he said, voice hoarse and she smirked a little.
“I’ll have to punish you…” She said, voice sultry and he looked at her, his face red, his cheeks wet and his lips puffy, “Mm, go to bed. I’ll be up in a few minutes…”
He looked at her, afraid to ask what his punishment would be but clearly not eager to stick around and anger her further. Standing and pulling his pants back up he stepped quickly from the room heading for the stairs.
“Oh and don’t forget to brush your teeth first! It’ll help with the taste.” She called after him, grinning to herself.
He blushed furiously as he made his way upstairs, but did as she suggested. He looked around the bathroom as he brushed his teeth, noting the empty wine bottle, the discarded clothes and scented candles but didn’t stop to clear up.
A few minutes later after he had brushed his teeth and washed his face he was in his room, undressing for bed when he heard his door swing open and his blood ran cold.
He turned to face her, but with relief, found she was standing with her bathrobe on, though the smirk on her beautiful face was disconcerting.
She had wanted to fuck him, of course, but she wasn’t as young as she used to be and would need at least a little while to recover.
“Here.” She said, smirking, tossing him something which he struggled to catch, fumbling but holding it, albeit awkwardly.
He stared down at the object, a thick black buttplug with something weird on the bottom, though he wasn’t sure what. He looked up at her, unsure but she tossed him something else, a little blue sachet.
“Lube.” She explained, “You’re going to sleep with that inside you. If you don’t I’ll know and then you’ll be in real trouble…” She paused for a moment, considering watching him try to get it in, but she wanted to feel the comfort of her own bed, “Oh and leave your bedroom door open tonight…” With a wink she turned and stepped from the room, leaving him alone with his new object.
Jenna walked back to her room and turned off the lights, slipping her robe off to land on the floor before climbing into her bed, sighing softly. It took a little while, as she thought it might, but before long she heard the soft whimpering sighs and gasps of her son, trying to work the doubtless incredibly well-lubed buttplug into his virgin hole.
It had been the kindest thing for him really, allowing him to go at his own pace while stretching his ass overnight, making sure it was nice and prepared for what she had in store tomorrow.
It took twenty minutes or so she reckoned until, after a very distinctive squeak, he went silent. She waited a few more minutes laying in her bed, listening out for any other telltale noises until she was sure he had either given up or had succeeded.
She smirked playfully and reached across to her nightstand, picking up a little plastic object. After a moment’s hesitation, she flipped the switch.
She heard a surprised yelp from across the hall followed by a series of whimpers and moans, her son caught off guard as the buttplug sealed in his ass began to vibrate.
Grinning she set the switch down and leaned back down, falling asleep to the sounds of her son moaning and whimpering like a bitch in heat. She wondered if he would cum, if he would touch himself, but she didn’t care.
For Alex it was the best worst two hours of his life, until, mercifully, the battery ran out. The vibrations had torn down walls and forced him to cum three times, his little cock shooting into his hands, leaving a sticky less that he wiped off on some discarded clothes. By the end of it, to his humiliation, he found himself disappointed when the battery ran out and he was finally allowed to slip into sleep.
He’d slept on his stomach, finding it to be the most comfortable way to sleep and and awoken to the alien sensation of a sharp tugging then a sudden void within him, he’d whimpered softly, putting his arms under himself to push himself up, eyes flickering open to see the dim light of morning bleeding in through his curtains, but before he had pushed himself up, he’d felt softness on his back.
“Shh…” Jenna whispered as she settled her weight down atop her son, her heavy breasts resting then pressing into his back.
“M-mom?” he whimpered softly, “w-what’re you doing?”
She let out a soft little laugh, kissing him on the back of the head before whispering, “taking care of my morning wood…”
He had opened his mouth to gasp but she had pushed his face down into his pillow as she slid herself forward. She had lubed her erect cock before entering his room and his ass, stretched and lubed from the buttplug couldn’t have been anymore ready for her if she tried.
He wriggled, hands gripping the sheets and feet kicking helplessly as she sank every single inch into his virgin ass in a single long slow stroke, her huge replenished balls pressing eclipsing his own smaller ones.
“Aahh…” she moaned low, pinning him with her body, her hips working in slow circles as she got used to having the tight ring of her sons ass gripped around the base of her cock, every inch being hugged by his new fuckhole, “this is what you’re for sweetie, every morning and every night you’re mommy’s new fucktoy, don’t worry baby, you’ll love it and hate yourself for loving it… But that’ll change…” she whispered, biting his earlobe gently, “you’ll see how right I am and before you know it you’ll be begging to meet my friends…”
With that the admittedly short acclimatization period was over, she was impatient and desperate to relive that first thrust into him. Biting her lip she closed her eyes and began to fuck him.
His ass was tight but accommodating, able to take the huge length she pounded into him, his moans coming out quick with his breath, the soft cheeks of his ass bouncing each time she slammed herself down into him.
Each thrust ground his hard little cock into the bedsheets, the friction pleasuring him, getting him off even as he hated himself for it, as she had said.
She wasn’t gentle, she wasn’t making love, she was just relieving herself with his body, jerking herself off with her newest toy.
Their bodies had grown slick, her breasts sliding over his back, her heavy balls slapping into his time and time again, reminding him of his inferiority.
The sensation of her huge cock driving in and out of his slender body, bumping into his G-spot time and time again had, to her amusement, made him cum twice in the time it took her to reach the finish line, each time his ass rippled and milked her cock like a sleeve, a sensation she relished as he made a sticky mess of his bedsheets, his toes curling, his pillow wet with spit and sweat.
Finally she had finished within him, pumping a thick hot load of her girl cum up into his butt, marking him as a bitch and she had lain with him, letting his ass-pussy milk every last drop she had to give deep inside him until she was soft.
She had stood, slapping his ass hard enough to draw a yelp and to leave a red handprint on the jiggling softness of his cheek as she smirked, leaving him to recover from his morning session.
Freshly broken and eager he hadn’t gotten off light. Later that morning they had showered together and she had made him suck her cock. In the afternoon after lunch they had watched TV together, him bouncing on her cock, in the evening she taken him to bed with a few more of her toys for a longer session, one that left him an exhausted cumfilled mess.
His only solace was that he knew she couldn’t keep up that tempo, and that given how much she had exerted herself would likely be sore the next day. But as they had fallen asleep in her bed, her caressing his hair, another buttplug stuffed up his ass, forcing him to hold her cum deep within him she had whispered softly that she was expecting a visit from family tomorrow…
Her two sisters, to be specific.
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