Femboy chronicles

My name is Caleb, I am a 19 year old who really doesn’t have any direction in his life. I went to community college for one semester to get my old man off my back but turns out it really wasn’t for me. I work at the local grocery store stocking up shelves and looking to get my own place soon and figure it out from there. I’m on the smaller side I’m 5’2 130lbs, smooth white skin, dirty blonde messy hair and freckles I look pretty petite and fragile for a guy. Which suites me well because I am a secret femboy. Literally no one knows about this and there has been some suspicious of me being gay from friends and co workers, but luckily never confirmed. 

I play dress up on my own in my room, since I have my own card I’ll order my own things so my folks don’t catch wind of it, so far I’ve been able to order a few cute skirts, tube tops, makeup, and panties. I don’t have a large collection but I’m hoping to build on it once I get my own place. I’ve posted a few pictures of me dressed up with my face cut out and always get positive reviews, but always delete my posts getting scared that someone might recognize me! 

I was working a mid shift at groceries are us and it was a pretty mundane Wednesday, my boss Chris was a pretty easy going manager, treated us well and tried to help when he could. Only thing is that he would constantly pick on me, for being short or weaker than the rest of his staff, he’d constantly poke at me for having to use a step stool to reach the top shelves or when I would ask someone else with help for the heavier items. Other than that it was a half decent job. I wasn’t expecting to make a career out of it but rather hang out here until I figure out what I want to do with my life. 

after my shift I knew a new package had arrived for me and I was excited to try it on, this one took a bit to get as it was your classic femboy maid outfit, I was so excited to try it on and put on make up to see how I would look. I clocked out and headed home in my piece of crap car that was well over 20 years old in tv family. It barely drove and was a constant headache for me but it was what I had to work with.

Once I get home I grab the package from the kitchen table, my mom/dad would not open my package so I had no worries of them snooping around, “hey mom” I called to her as she watched the evening news “gonna shower and hang out in my room” I said as this was pretty normal. “Ok hun, there’s leftovers in the fridge in case you’re hungry” 

I quickly go to my room close the door and lock it and open up the package with excitement. It was perfect!! It looked like the fit was going to be great! I laid it out on the bed admiring it already thinking of poses to make. I take my shoes and socks off and my work shirt too leaving on only my khakis and white undershirt and before I fully commit I decide to go into the kitchen and grab a bite to eat. 

my dad was in there, my dad was old school. No nonsense kind of guy you know, military background. “Hey dad” I say casually “how was work?” He mumbled indicating it wasn’t to good today “when are you looking to get your own place son? I’d imagine you haven’t brought any girls over cause you don’t have your own place huh?” He asks a bit condescending. “I got maybe three- four months before I have enough saved up” I say. It was no secret I was trying to get my own place but I needed time.

I warm up my food and and head back to my room, now this was my first and last mistake. As I was carrying my plate of food and closed the door I completely blanked on locking my door as my hands were tied. I set my food down and turn on my tv to watch something mundane while I eat and think about the poses to do with my outfit. Between bites of my food I begin to apply my makeup, I was getting better at it. First foundation , blush, eyeshadow, lipstick. I truly would pass as a girl I keep telling myself. Once I was done with my food I set the plate to the side and strip down to my boxers “well these won’t work” I say looking my boxer briefs. I kick them off and go into a corner of my drawer and pull out a pair of black cheeky panties. “Much better!” I say as I give a bit of a bounce as I look at myself in the mirror.

I methodically put on the maid outfit making sure it’s on correctly and to be sure I don’t tear anything as I put it on. Once it is fully on I give a nice twirl be love the way it looks on me, black and white skirt above my knees, cute top, i look like I’m ready to serve!

I bend over pucker my lips which have red lipstick on them and snap a few pictures, that is when I notice a huge light enter my room, the only type of light that would be coming in if someone opened the door. I quickly panic stand up straight and turn around to see my dad at the doorway and me in my full outfit competed with makeup looking at him with comply shock

”what the fuck is this Caleb!?!?” He asked shocked