AlwaysOlder's Blog

David didn’t really want to bring his son, Billy, into his office today, but his boss was strangely insistent that he bring Billy in for “Bring Your Child To Work Day”. On the bright side, David didn’t have to worry about dropping his kid off at school. On the other hand, Billy had just turned 11 and had more energy than he knew what to do with. He thought his dad’s office was extremely boring and would honestly rather be at school. After watching his father work on a spreadsheet for an hour, Billy decided to sneak away while his dad was on a phone call. He initially just wanted to find a vending machine, but soon came across a dark wooden door with a golden nameplate that read “Bailey Whitner, CEO”.

Curious, Billy quietly turned the handle and peaked into the executive’s office. It was empty. He slipped past the door and quietly closed it behind him. He walked up to the desk that looked more expensive than his dad’s car and jumped into the plush, leather chair that probably cost more than his father’s yearly salary. He noticed a photograph of Mrs. Whitner with her family on the desk. She was beautiful, mature yet youthful for her age, and she was standing above her two daughters with her athletic husband’s arm around her shoulder. Billy began to look around the rest of the office as he spun in the chair, taking in the massive library of business books that adorned the bookshelves lining the office walls. He spun faster and smiled, happy to be looking at anything other than a spreadsheet, until he felt a wave of dizziness suddenly wash over him.

He grabbed the desk to stop himself, waiting to catch his balance before jumping out of the chair. As he did, he noticed his fingernails beginning to grow longer and polished before his very eyes. Before he could react, he felt a tickling sensation creep across his skin as his clothes began to morph. His t-shirt began to stretch and warp into a white suit jacket, but not one like he’d ever seen his dad wear. His entire torso was nearly exposed as the sleeves grew longer than his arms, cutting deep with ample room in the upper chest. His cargo shorts underwent a similar change, growing long past his legs while matching the silky texture of his new top. He was shocked, but thought he looked pretty funny in clothes that were obviously too big for him. He was about to run to his dad to tell him what happened when he suddenly felt a snap on his back. He looked down at his chest and saw a large velvet bra materialize around his pecs.

“Wait, isn’t this what mommy wears?” he thought to himself worriedly. Another tingle came from his crotch as his boxers began to tighten, morphing into a tight silk thong. His confusion was briefly put on hold as an intense pressure rapidly began to build in every bone in his body. He moaned in pain as he rapidly began to age, his bones stretching and rearranging themselves as his skin was stretched into a smooth, creamy texture. He winced with every popping joint and cracking bone, leaving him on the verge of tears as his growing body began to settle. He wiped his eyes and looked down at his rapidly changing body, realizing that his new clothes fit him nearly perfectly now. His feet tingled as his childhood sneakers morphed into a pair of black high-heels, relieving the pressure on his mature new appendages. He felt the tingling run up his legs as his thighs began to thicken, filling out the loose fabric of his pants. He let out a feminine gasp as his inflating ass pushed him upwards in his seat, fitting perfectly into his new tailored pants.

His expanding behind caused his new underwear to be pulled even closer to his crotch, forcing his boyhood between a new fleshy opening between his legs as he began to quiver in pleasure. He couldn’t help but moan in a deep, seductive voice as every fiber of his being was seized with pleasure. It was like a lifetime of orgasms happening at once to a boy who had yet to experience his first. He didn’t want to be changing like this, and he was still terrified of what was happening to him, but it was getting harder for him to focus on anything as his mind was overcome with ecstasy. He slipped a slender new hand down his pants to feel his new sex and was shocked with how wet it was between his legs. Simply touching his new clit sent more waves of pleasure coursing through him. His moans finally began to subside as a flash of clarity reminded him that he was just a kid visiting the office with his dad. None of this should be happening.

Billy wanted to scream, but before he could call for anyone, his new diaphragm forced him to inhale as his chest began to grow. He looked down at the massive bra wrapped around his chest and dreaded what was coming next. His adolescent mind was still filled with thoughts of boobs being gross and girls having cooties, so realizing that he was about to have his own pair of breasts sent shivers down his spine.

“Nooo- OOOH!” He moaned as he felt his sensitive new nipples brushing up against the silk undergarment. His breathing grew heavy as his massive new bosom rise and fall with each breath. He poked one and groaned, surprised by how good they felt to be touched. He ran a finger up his exposed cleavage, horrified by his own body, yet unable to ignore the new desires flooding his mind. This body wanted to do things that confused him. It wanted to wrap itself around the man in the family photo, it wanted to feel the pressure of the two daughter’s heads pressed against its breasts as it hugged them goodbye for school, but most disturbing of all, it wanted to dominate Billy’s father. Billy’s elbows hit the desk as he grabbed his head in horror.

“Why!? Why is this happening to me?!” He cried in his feminine new voice. “I’m just a kid! I don’t want to work in an office! I don’t wait to be my dad’s boss!” He winced and grabbed his face as he felt it shifting beneath his palms. His eyes grew wide and seductive while his nose grew sharp and petite. Makeup began to apply itself to his face as his lips grew slender and moist. His jaw cracked while his chin grew angular, like a feminine goddess. Shiny blond hair began to tumble down around his face before quickly styling itself into a professional look. He was an exact copy of the woman in the photo now. He was Bailey Whitney, CEO of TGAP Financial. In a panic, he suddenly reached into a random drawer of the desk and pulled out a sleek tobacco pipe, somehow knowing that this would relieve some stress. Working entirely off muscle memory, he quickly packed some pipe tobacco and lit it with a match, inhaling deeply and basking in the nicotine rush. He tried to think of his family, of his dad right outside this office, but could only think of the family in the photograph on the desk.

He wanted to fight the changes happening in his mind, knowing that the smoke was causing his memories to change, but he couldn’t help but take another long drag from the pipe. He exhaled as memories of playing with his friends in school turned into studying finance while all the other girls slept their way to good grades. He remembered all the elementary school boys who both teased him and had a crush on him…no, her. She remembered meeting her husband in college and using her inheritance to start her own investment firm. She remembered the day she became a mother to twins. She felt her nipples harden as memories of breastfeeding her children forced their way into her head. Her new sex began to moisten again as she remembered all the nights that her husband swept her off her feet and rode her well into the morning sun. Billy made one last feeble attempt to hold on to his old childhood by thinking about his…her dad, but as the name and face of David entered the new woman’s mind, she could only think of the surprisingly attractive lackey that she had hired six months ago. With a final, unwanted puff of the pipe, Billy gave in to his powerful new personality. She was Bailey Whitney, a self-made female millionaire who was admired by millions around the globe.

Bailey smirked as she embraced her new life. Sex, power, and money were what drove her, and she had decided it was about time for her to get a new boy-toy in the office. She loved her husband, but she wanted someone to control, someone younger than her who could please her at any time. She picked up her phone with a wicked grin and paged David into her office. He walked in nervously, having never been in that room before, and was immediately smitten by his own boss. She leaned in, presenting her massive cleavage to her young employee and watching the erection in his pants grow with excitement.

“Hello David. I’ve been admiring your work for some time, and I think it’s time you and I had a chat about…moving up in the company.”

“Wow, thank you Mrs. Whitney, but have you seen my son around here? Someone said they saw him sneaking into your office earlier…” he stammered, clearly turned on by the creature in front of him.

“Oh, don’t worry. I gave him a job to keep him busy for a while,” she said with a seductive grin. She took another puff of her pipe and blew a smoke ring towards David, making him dizzy and forgetful. All he could do now was focus on the beauty in front of him. She teased him over to her desk with the curl of a finger and grabbed his hand with a powerful tug. She shoved his hand into her bra, moaning at the sensations of being groped by a man. She smiled dominantly as she looked at her lustful new office pet. “Do as I say and I think we’ll both be very happy with the future of this company. Now, this next task required a hands on approach…”