AlwaysOlder's Blog

“You sure your mom isn’t going to notice some of her wine missing?” Derrick asked as he swirled the red liquid around his cup.

“Yeah, it’ll be fine. She bought this wine years ago from some exotic country and probably already forgot about it.” Phil responded, pouring himself another glass.

“Well then, cheers!” Derrick exclaimed, holding his cup up for a toast. The young boys laughed, enjoying their first drunken buzz at Phil’s house while his parents were away on business. The two were nearly halfway through the bottle and already having a hard time handling their liquor, with Derrick rocking back and forth in his chair and giggling uncontrollably. It didn’t take long for an accident to happen, with Phil knocking over his glass and spilling it all over his friend. 

“Aw man, I’m sorry. Maybe we should slow down a bit.” He said, grabbing his friend some napkins.

“No worries, this was a cheap shirt anyway. I’m just gonna go wash up then we can finish the bottle.” Derrick stood up and looked at the expensive wine dripping down his face, thinking about what a waste of good wine this was. He made his way to the bathroom and began to wipe the stains out with little success.

“Ah man, I guess this shirt is done for…” he grumbled, looking down at the red splotches dotting his chest. He was so preoccupied with his shirt that he didn’t even notice his hair beginning to grow. It wasn’t until the stains on his shirt began to spread that he realized something was wrong. He wiped his eyes, thinking that he was just too drunk, but no matter what he did, he still saw his white shirt turning a pinkish color as the stains melded into the fabric. What scared him more, though, was the fact that his chest was beginning to protrude through his tightening shirt, nipples hardening as they rubbed against the shifting fabric. He tugged at his shirt in confusion, watching his chest grow more quickly by the second. It wasn’t long before he swore he’d grown a pair of…boobs?

The changes began to accelerate, causing his already woozy head to spin even more. He groaned as he felt himself grow taller, the surrounding bathroom seemingly shrinking as he gained height. He grunted as his frame began to crack, his limbs elongating as his spine curved inwards. His tightened shirt began to tear as his chest widened, revealing sharp collar bones and cleavage from his inflating breasts. He cried out to his friend for help as his hair lightened into a brown shade, but Phil had already begun playing music on the stereo and couldn’t hear his friend’s desperate cries from the bathroom. 

The terrified boy was about to make his way back to the dining room when he felt more pressure building in his lower half. He turned around just as his hips exploded outwards, tearing his pants at the seams and revealing the soft, supple skin of his growing ass beneath. He watched his expanding posterior in the mirror, his mouth agape in shock at what he saw. Just as his pants finished ripping open, he had a sudden realization. His reflection looked more like Phil’s mom than he wanted to admit.

Derrick’s hair continued to tumble down his neck as his tattered clothes began to restitch themselves into a form-fitting dress. He watched his transformation unfold in shock, holding back tears as the image in the mirror looked more and more like his friend’s MILF of a mother with each passing second. Everything had become so sensitive, and even his voice was changing into her’s. He heard his breathy whimpers grow mature and sultry as he continued to age, his feminine curves growing more extreme with every passing moment. He ran a hand through his silky new hair and smelled the familiar scent of his friend’s mother’s shampoo. He was about to scream for help when he felt strange sensations building in his chest and crotch. 

With a sudden spasm of his body, his sizeable chest burst forward, exposing his hardened new nipples to the cool air. He cupped his breasts and cooed in pleasure, reluctantly acknowledging how good they felt to be touched. He watched the cloth turn a deep red as it stitched itself back across his chest, shaping itself to accommodate his massive new bosom. The tingles of pleasure ran down his torso and began to focus on his crotch, causing him to lift the tattered dress and watch in horror. His dick began to twitch as two fleshy lips formed around it, swallowing his shaft and balls and pushing out any liquid left inside. He began to blush and moan as his sex inverted, reaching down to his tight new orifice just as it closed around his manhood. He quivered in unexpected pleasure as more juices ran down his milky thighs, the bundle of nerves from his dick becoming a sensitive new clit at the top of his pussy. His mind began to go blank as he pushed his slender fingers in and out of his new sex, unable to resist the urges coming from between his legs. With a final motion, he came as a woman for the first time and squirted all over the floor, his breath growing so hot it began to fog the mirror. 

Regaining himself after the wave of pleasure, he pulled the dress down and covered his quivering new sex. He began to cry in shame, reluctant to believe he’d just masturbated with his friend’s mother’s body. It was his body, though, and his mental fog was making it tougher to remember who he really was. The alcohol in his system was blending with the estrogen flooding his bloodstream, allowing his ego to slip further and further away. All he could think to do right now was to call his son…no, his friend for help, but what would he say now? He was only minutes away from fully becoming the real owner of the wine they’d recklessly consumed. 

He grabbed his head as new memories began to populate it. He remembered birthdays as his body gained a slight layer of fat, the tight dress only accentuating his feminine curves. He remembered going to college and getting a job. He remembered working his way up the corporate ladder and enjoying all the business trips the company paid for. He remembered different types of wine and where they came from. Tears began to roll down his eyes as his sprouting memories became more personal…familial. 

His hair tumbled down to his lower back as he winced, trying to fight the memories he was having of his best friend as a baby. He remembered how happy he was when Phil’s first word was “mama” and when his baby boy took his first steps. He remembered meeting Phil’s dad…his husband…on a work trip. He blushed as he thought of the night after their wedding, the tropical smell of the beach, the soft silk sheets, the passionate lovemaking. He felt himself growing wet again at the thought of being penetrated by Phil’s father. It felt like he was reliving all of his sexual encounters all at once, and the pleasure was simply too much for the once young boy. 

Derrick screamed in a mix of confusion and ecstasy as the wealth of sexual knowledge flooded his mind. He began to revel in the sensations he never could’ve felt as a boy. The sensitivity of his new body, the desire that men felt when looking at him, the envy women had when he walked in a room. More than any of those things, though, was the maternal instinct taking over his brain. His sultry, drooling mouth curled into a satisfied smile as he felt the joys of being a mother cross his maturing synapses. He loved breastfeeding his baby, Phil, and watching him grow into a handsome young man. He felt joy at the remembrance of Phil’s report cards and academic performance. He knew his son would grow up into a fine young man, and he couldn’t be prouder. With a final sigh of acceptance, Derrick embraced his new life as the MILF of his best friend. He was Derrick no more. She was Diana, avid wine connoisseur, loving mother, and the object of desire for everyone in her neighborhood. 

The sultry woman walked out of the bathroom, filled with confidence and smirking at how good she looked in her favorite red dress. She grabbed her wine glass off the shelf and made her way to the dining room where her teenage son was dancing around to some music. She paused and sipped her wine, waiting for her son to notice her presence.

“You get those stains ou- MOM?!” He stuttered, shocked by her sudden appearance. “I thought you were traveling!”

“Oh, I made the quick trip home, sweetie. I just couldn’t wait to try this wine any longer,” She said as she slowly sipped her glass. “Aren’t you a little young to be drinking? And did I say you could open this bottle?”

“Uhhh…sorry, I’ll buy you a new one. Please don’t be mad…”

“Don’t worry, I won’t tell anyone. Just, ask next time, okay? There’s a reason I was saving this bottle…”

“Okay, mom. Say, did you see Derrick? He might’ve had a little too much to drink.”

“Oh, I think he enjoyed the wine more than anyone.”