Progression Ch. 01

His thumbs then flew across the virtual keyboard without his brain's permission, tapping, sliding, deleting, rewording, typo-ing, then finally hitting send.

Don't be shy mom it's just me, move your hand away and take another

She didn't respond, giving Rory ample time to take it back. He didn't. He waited, his eyes riveted, his body tense if she would actually follow through.

She did.

"Christ," he murmured, drinking in the sight of her heavy tits freely hanging, her dark nipples pointing straight at the camera.

Rory set his phone on the counter, and without looking away from it, unfastened his pants and lowered them down enough to free his hard cock. Over the past few months, he had saved a multitude of her pictures, but he never once actually went through with masturbating to them, more than happy to get his kicks with women looking for a one-night stand.

Well not anymore.

He wrapped a hand securely around himself, paused as if questioning what he was doing with his life, then began stroking it. This wasn't what he had in mind when he made the suggestion, but... fuck it. He knew a great pair when he saw them.

U look incredible he typed single-handedly, How do u feel??

Exposed was her immediate response, giving him pause, but then she added, kinda sexy 2 I guess

U r sexy

She sent a blushing emoji, then as if they were doing a business transaction, told him it was his turn to finish the trade.

Fair's fair.

He yanked off his tank top and stepped back into the living room for better lighting, his dick bobbing along. Ignoring it for the moment, he started angling his phone to get a good angle of his pecs and flat stomach. He snapped a pic, and while it looked decent enough, he couldn't help but feel like it was missing something.

He glanced down.

Ah.

There was the missing piece.

He held his phone out again, getting a similar shot, then using his free hand, nudged his dick into frame. He only captured the tip so as to not be too obvious, then shut his brain off and hit send. Her response was immediate.

Oh honey you look so handsome / Strong 2 / Im proud of you, Rory <3

Rory smiled at her praise. He began typing a response back when she sent more.

Wait / Whats that?

He chewed on his tongue, not sure if she was being serious or not. While it wasn't a straight-up dick pic, anyone who'd ever seen a penis would recognize the rounded shape of the head and piss hole. Maybe she was giving him the benefit of a doubt. Who in their right mind would send their own mother such a picture, right?

Rory teased his bottom lip with his teeth for a moment before deciding to be truthful about it. He wasn't a kid anymore, he couldn't feign stupidity. He'd own up to it, just as a man should.

It's my penis / Sorry but / I just find u so incredibly beautiful / Ur pic gave me a boner

He didn't know how he expected her to respond to that, so when she sent him an army of blushing emojis, he let out a little laugh. When she didn't add anything else, he figured their chat was over and made his way to his bedroom.

When he sat at his computer, he plugged in his phone, and a few minutes later, he had her topless pic downloaded and expanded on his screen in glorious 4K.

"I am so going to hell," he chuckled, drinking in the details of her pores and the slight bump of a pimple.

He grabbed the little bottle of lube he kept next to his computer for when he watched porn, wet his palm with it, and flicked his eyes up to her face. She looked so embarrassed, her blush spreading from cheek to cheek and across her nose as if a painter had swished his paintbrush with an extra flourish. He could almost trick himself into believing that she looked as if she knew he'd get off to it, and had been flattered or maybe even a little turned on by the prospect.

Moaning at the very idea, Rory got to work.

Very quickly, he lost himself to the rhythm of masturbating, his slick hand rapidly jerking his shaft as he mindlessly stared at the screen. He'd known that his mom had fantastic breasts, but seeing them like this, he would dare say that they were perfect. They weren't as firm as the ones he was used to when sleeping with women his age and drooped a little without support, but they filled up the entire screen without much effort, her nipples not aroused in the slightest but looking utterly chewable like pieces of soft candy. Rory licked his teeth, suddenly itching with the desire to give them a little nibble and suck until they expanded inside his wet mouth.

Rory gripped the armrest of his chair with his nails, imagining her soft flesh pressing up against his face, smothering him, and he wouldn't even care. He'd happily pass out on those pillows in a heartbeat, and get possibly the best sleep of his life. He began panting, wanting to be with her, and forced himself to slow down, needing this to last a little longer before shame followed him all the way to the grave.

His concentration broke when his phone abruptly chimed with text messages. He thought about ignoring it, but curiosity got the better of him, especially when he saw that they were from his mother.

I don't believe u rory / Are u really hard because of me?

"Sure am," he muttered, unplugging his phone with his clean hand. His computer chimed at him for disconnecting, but his mother's tits remained on the screen, forever safe in a private folder with all the rest.

He leaned his torso back as he aimed his phone's camera in a certain way that captured not only the top few inches of his slick, red cock and a dribble of cloudy precum leaking out of the slit, but also her topless pic in the background, so that she knew he was currently getting off to it.

She messaged him back immediately.

Oh my / Look at you being so naughty / Naughty boy...

Rory's nostrils flared. She never once in her life called him that. He'd always been so good for her, but now here he was, masturbating to his own mother's tits, sending her pictures of his hard, aching cock, wishing he could fondle them in person, lick them, fuck them, all the while calling her all the things he thought about her: beautiful, sexy, hot, amazing, riveting, alluring.

Mommy's naughty little boy

Rory moaned, his eyes slitting as he read the words over and over, his hand on his cock slipping completely off of it as he increased the pace, the squelching of the lube intense. His balls drew up, and he knew he was a goner.

"M-mommy," he eked out, his face heating up in both embarrassment and arousal, but the moment he jumped that first hurdle, his tongue loosened and he gasped, his head leaning back as his cock pulsed in his grip, shooting ropes of semen up his bare chest. "Ah, shit- mom- fuck- m-mom!"

By the time Rory could catch his breath, he had no wherewithal of how much time had passed. He sat slouched in his chair, his toned chest heaving and streaked with an impressive amount of cum, some of which had splattered his chin. He looked down at it and at his spent penis, flaccid but still dribbling out white fluid, his skin glistening with lube.

Without giving it much thought, he raised his phone and took a picture of the aftermath, taking care to include his tired but sedated face, and sent it. He gave it a few seconds thought before quickly adding a message.

Still don't think your hot enough?

Minutes passed. Rory became a little worried. He hadn't gone too far, had he? He sat up, feeling a little gross, and was all too prepared to delete the pic from his computer and drink enough alcohol to give himself poisoning, when his phone happily blipped. Cautiously, he picked it up.

I might need a little more convincing

His mood dropped but promptly flew back into space when a pic pushed through right after, showing a close up of her dainty hand and what could only be lady-cum webbing between her fingers, thick and gooey.

But ur on the right track honey <3