[M4M] Desperate femboy crossdresses for his new job

NSFW

I fidget with the hem of my pencil skirt feeling the unfamiliar breeze on my inner thighs. My low cut blouse hugs my petite frame tight showing the small bit of cleavage I was able to create by wearing a lift up bra. I pulled out my phone and double checked my hair and makeup to make sure I looked presentable. It had taken days of practice to get this look right. Finally, the silence was interrupted by a door opening.

"Miss Jasmine? He's ready for your interview."

I nodded and got up following the secretary down the hallway. My heels clicked on the tile floor as I focused on making sure not to trip. I still couldn't believe I was doing this. Sure, I was desperate for a job, but dressing up as and pretending to be a woman just for a job is insane! The secretary led me to an office where I stepped inside and saw you sitting there. With a deep breath, I smiled wide, held a manicured hand out to you, and spoke in the bubbly girly voice I'd been practicing.

"It's a pleasure to meet you sir!"

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I'm looking for a partner to play out this silly little idea of mine. The basis of the story is that my character is down on his luck and desperate for a job. He found a personal assistant position that pays well, but they mentioned they're only hiring women for the position. Instead of finding a different job, my character desides to pretend to be a woman and reapply again. To my shock, I actually get the job.

The story progression I'm thinking is we do the interview then my first day on the job where you are being very flirty and handsy with your new personal assistant and I realize why it is you insisted on only hiring women. Eventually, you make me give you a BJ threatening to fire me if I don't comply. This escalates to you bending me over your desk and lifting my skirt up to fuck me. I'd love if either you somehow don't notice my cock and fuck my ass thinking I'm still a girl or you do notice it and don't care because a slut is a slut. Eventually, the story can progress to you taking me to dinner and such as well.

As for my character, I will play as Josh (or Jasmine as he goes by in female form). I will be about 5'5 with shoulder length blonde hair, a cute soft round face, blue eyes, and pale skin. I'll have a thin frame with a surprisingly thick ass and thighs for a guy that adds to my ability to fit in as a girl.

I am open to suggestions for the roleplay. Please just send me a chat with any ideas you may have for the story or our characters if you are interested. Thank you for reading!

Posted Jun 2, 2026, 1:03 PM UTC

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