You Write the Caption! - New Job, New Clothes, New Life (Patreon)

I was so enthralled by the stories you sent in last month, I want to keep going!

This one is from Jason. Thank you, Jason!

I had a lot of fun with this transformation, and I think "Jessica" turned out lovely! 😃

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Two years ago, Jeff responded to the ad looking for an executive assistant. He had been unemployed for 10 months, and as his bills stacked up, he would do anything for a paycheck. Luckily, the boss (Mr. Gordon) was willing to overlook his lack of experience and hired Jeff to start immediately.

He showed up the first day in his best suit. Other than the office coffee tasting very strange, he had no difficulties adjusting to the new job. He answered calls, planned meetings, and did anything possible to impress Mr. Gordon.

After a few weeks on the job, Jeff noticed changes to his body. His hair and nails were growing out of control, and his dress pants and shirts no longer fit correctly. He didn’t have the money for a new wardrobe, but he couldn’t show up to the job looking like a slob! Jeff went to Mr. Gordon to ask for a salary advance. After finding out about Jeff’s predicament, Mr. Gordon said he would take care of everything by the end of the week.

Friday rolled around, and Mr. Gordon said they would be taking care of the wardrobe issue that afternoon. Jeff worked feverishly throughout the morning to get things in order, chugging coffee along the way. Around lunchtime, he felt woozy. Soon after, he fainted as everything went black.

Jeff awoke in a hospital bed. There were beeping machines everywhere, and new sensations across his body. Mr. Gordon greeted him from the foot of the bed: “Hello, Jessica, welcome to your new life.” Jeff’s mind raced as he finally put the pieces together.

Jeff had been out for 3 months. The surgeons had done a lot: Breast implants, facial feminization surgery, voice feminization surgery, and a cute little slit between her legs.

Once Jessica was released from the hospital, she discovered Mr. Gordon already delivered her new wardrobe. It was only fitting for an executive assistant: Skirts, blouses, and heels!

After some practice time at home, Jessica was ready for her first day of work. As her heels clicked across the office parking lot, she realized her life would never be the same.