Femboy chronicles

I looked at my dad with horror in my face, i stood frozen as he looked straight at me from the doorway. “Caleb what the fuck are you wearing!?” He says angrily clearly holding back from yelling “it’s not what it looks like daddy!” I normally don’t call him

That but felt like i needed to start begging and be on his good side. “I lost some stupid bet so this is what I had to do “ I say with tears starting to form in my eyes, you have to remember that my dad was old school military man, nonsense kind of man, he was extremely homophobic as well. “Stop it!” He says waving his hand around as if he doesn’t want to hear it. “You’ve got make up on!? A maids outfit? You look like a girl!!” He says as he approaches me and starts to circle around me inspecting me. I try my best to cover up with my hands and try to pull the skirt down. “Dad please, this isn’t what you think I promise!” I say in complete hysteria

“If this is a lost bet, then maybe I can see past this, but I do believe that you are lying to me, you don’t like sports, you down show interest i girls, and you don’t even look like a real man. So if this is a bet then I won’t find any more fruity stuff in your room then would i?” He says looking at me. “Wait dad you don’t have to “ he stops me mid sentence as he walks to my drawer and by luck pulls my pantie drawer first. “What the Fuck Caleb!?” He says angrily as he grabs a fist full of them, all different colors and styles, he picks one out with his free hand and it is my pink thong “what this last of the bet also?” He asks rhetorically. “Look soon, I know exactly what this is, you’re living a secret life and one I cannot support, I’m gonna make this very clear and I’m only going to say it once”

I had gotten down to my knees in disappointment and dreaded to hear what he was going to say, my dad is not the kind to joke around or play games. “You have until the end of the day tomorrow to move out, if you don’t we will kick you out” he says very much matter of factly. “But dad, I don’t have enough money to move into my own place!” I plead with tears in my eyes “tough shit” he says in a low voice as he heads towards the doorway “you’re no son of mine” he says as he leaves the room.

My mom is completely submissive to my dad and she can’t protect me, this is really how it’s gonna end living with my parents I think to myself. I muster up the energy to get up and close the door and I start to slowly take my maid off outfit off as I didn’t feel like wearing it anymore. I was on and off crying the rest of the evening thinking about what to do. All of the small group of friends I had in high school have moved out for college so I really don’t have anyone or anywhere to move to.I was laying down on my bed just contemplating all options I had which really the only realistic way out was to live out of my crappy car until I gathered enough money to get my own place. Just then I get a text from my boss Chris “hey Caleb, can you come in early tomorrow, Shawn has something and forgot to schedule him later, so you can come in at 7 and he’ll take your shift” I figured this is better to give me time in the afternoon to take everything can with me before I’m forced out of my own home

“Yeah Chris that works, see you then “ I text him back “great, thanks man!” He says back.

I try to get whatever sleep I can. I end up getting ready to work my folks are dead asleep and I don’t really want to see them anyway, I make it to work right on time, Chris was on his work computer doing something when he sees me walk in. I was visible troubled as I had my head down and looked like I hadn’t slept at all “yo Caleb thanks for coming in” he says as I walked near him, I mustered a low “yeah” and walked past him “hey man you alright?” I stop and close to a break down and I knew I couldn’t really talk so I just shake my head “no” he looks at me confused “what’s up man, what’s wrong?” Yeah Chris can be a jerk sometimes especially when he makes fun of me, but he’s not the worse manager so I do think he’s being genuine when he asks.

“I …. I uhm” I say trying to fight off tears “I just got kicked out of my house man” I say still looking down not being able to look into his eyes.

“What!? Why man? You got anywhere to go?” He asks, without answering the first piece of his question  again shake my head no as there’s a single tear that runs down my cheek. “Oh shit” says Chris as he looks at me, it was early in the store so there really wasn’t anyone there yet in terms of other employees. “I gotta be out by today” I say as my voice is crackling “damn man that’s sucks, I - I’m sorry dude” he says putting a hand on my shoulder as this is the first time anyone has tried to comfort me it did feel nice I think to myself.

After a pause he says “look man, my roommate moved out last month and I was going to use the spare room for my music, but if you need a place to stay while you get back on your feet you can move in” he says in a nice comforting voice. “R-Really? Chris, you don’t have to…. Are you sure?” I ask not knowing what to say and in awe that he’d offer something like this to me, someone who isn’t really close to him at all, actually someone he constantly torments, maybe he’s actually a better guy than I thought? “Yes man I’m sure, I get out at 3, so gena your stuff and meet me at my place whenever you’re ready” he says casually as he goes back to working on his computer

My mood had completely changed after that, I had a pep in my step and seemed like I was going to be ok. I was going to go home as and grab as much stuff as I could and run away from that place, if my dad didn’t want anything to do with me, then I wouldn’t ever want to see him again anyways I think to myself.

The shift goes on without anything else out of the happening, I was a bit more receptive to Chris’s jokes and let him poke at me a bit more since I knew he was doing be a huge favor so I didn’t mind it as much. I normally would be a bit upset, especially when I couldn’t get a bag of dog food up on the shelf he said something to the effect of “maybe you should stick to stocking the tissue paper where all the women are at!” While the other guys had a laugh and I exhaustively dropped the dog food as it was my third attempt to get it on the shelves. I just laughed and let him have his moment humiliating me.

The end of my shift arrives and I grab a couple of boxes from work and head home, once I get there my folks are not home, I’m sure they did not want to see me when I left, better for me I thought. I ran into my room grabbed everything I could, and of course I grabbed all of my femboy outfits, clothing, makeup, and the two toys I had, which was a small butt plug with a gem at the end, that I had only tried about 2 times, and a smaller sized dildo with a suction cup at the end, that I have used maybe once a week, not always in me, but to practice blowjobs.

I am an actual virgin though, so the dildo and plug are the only real experience I have. Nonetheless I put them in a box covered them up with regulars clothes and started to pack my car up as much as I could, I only wanted to make one trip.

I made it to Chris’s house around 5:30 or so, I texted him that I was at his townhome as I didnt know exactly which one it was. He texted me the building number and it was nudged in the corner so I found it and went in and knocked on his door, box in hand. “Hey Caleb, need help with anything?” He asks as he was wearing casual shorts and loose fitted shirt, dressed down from work. “Yeah only have a few boxes “ I say grunting with the one I have “ha this one is already heavy for you ain’t it?” He jokes as I give a sigh and roll my eyes “so it begins huh?” I ask as I step in. He walks me to the spare bedroom, to my surprised it’s mostly furnished, bed, dresser small tv etc. “wow Chris is this awesome!” I say excitedly “I can’t thank you enough man, I swear I’ll only be here a short time before I get out of your hair” I say in a thankful voice.

Once we finish taking down all the boxes and I’m in a spot to get things organized Chris comes into the room “hey man before you unpack everything I think we should talk first” he says. I was a bit surprised but it is his place so his rules apply I think to myself “look you didn’t answer why you go kicked out, and I didn’t want to press you, I only know you from work, so I need to know why you got kicked out and I need to look through your stuff. It’s not that I want to be nosy, but it really is for my safety, I need to make sure you’re not bringing any drugs or any weapons you know”

My heart starts to go crazy, I can’t tell him the real reason! And if he goes through my stuff he’ll know my secret, maybe this isn’t a. Good idea? Maybe I should jus go…… but go where? My mind was going crazy too!! I sigh “I don’t know if I’m ready to tell you why I got kicked out Chris” I say in a sad tone “look I understand that it may be private, but I do have to go through your stuff, does that make sense or seem fair?” He asks i knod my head agreeing to what he said. Maybe he won’t find anything, or he’ll think the panties are just regular clothes, he won’t be thorough enough to figure me out I think to myself hopefully.

The first box he opens is already a bit questionable as I had a few of those squish-mellows “what the heck dude, i thought only girls used these?” I said as he tossed them to the side that box had my normal clothes and work clothes, but to my horror he was taking everything out piece by piece and even unfolding garments to make sure there wasn’t anything hiding within them, he was being extremely thorough!

“Look Chris “ I chime in as he completes the first box and moved on to the second one, this one had my panties and make up and girl clothes, the maid outfit was In the third and final box

“Yeah?” He says opening the box and looking up at me “I - i uhm” I stutter not knowing what to say “I don’t think you should look into that box” I say turning red in the face, he pauses to look at me “really and why is that?” He asks defensively, he must of thought he was right in regards to it being weapons or drugs “it’s personal stuff” I say in a low crackling voice as I know it’s pretty much a weak objection. “Well let’s have a look then shall we!” He says as he opens it quickly

Right on top is my panties collection, different colors and styles, from g-string, thong, Lacey, cheeky, pink, black, white panties. He looks at them looks at me and is confused “why do you have these?” He asks not being able to put the dots together . I turn red again not being able to answer, in the silence Chris puts it together “ohhhhhh, wait a second, these are yours?” He says quickly dropping them back Into the box as if he’s grossed out by it “you wear these?” He asks as I look at the ground “yes Chris, but don’t tell anyone please!!” I manage to blurt out knowing that he knows my secret “do you wear them to work?” He asks as he dives back into the box “I-I’m not gonna answer that!” I say as i and tomato red from embarrassment “well I’m gonna assume yes then” he says as her goes back into the box and finds my makeup stuff “hold up!!” He says shocked “you wear makeup too!? Who are you!?!?” He says not angrily but almost sarcastically

“Chris please, c’mon that’s enough “ I say reaching. Over to grab the box “no no no!” He says slapping my hand away “there’s still one box after this and I think we already know why you been kicked out, so this next box is just for fun he says smugly. He grabs the last box and this is the one with my two toys and my maid outfit along with toiletries and other misc. he quickly opens the box and right on top is my maid outfit in all its glory “oh shitttttt this is better than I thought “ he says all to excitedly “dude you’re like full on femboy aren’t you, does anyone know about this?” I am mad and red in the face but the jig is up I cannot deny it “yes Chris, I do it in private, and no, only you and my dad , that’s why I got kicked out, can I have my stuff back now?”

He digs through the bottom of the box and finds what I was hoping he wouldn’t he looks up smugly and lifts up the butt plug and dildo in the same hand “so your a gay femboy?” He asks smiling as he shows them to me “Chris please I’m begging you, that’s everything, look didn’t bring in my drugs or weapons ok, are we good?” I say dying of embarrassment

“Yeah we’re good” he says standing up “I just think that the is new roommate situation has turned out a lot more interesting than I thought it would be” he says smugly as he leaves the room. I sit on the bed all my stuff laid out a mess and think to myself, what the heck did I get myself into?