Femboy chronicles

Chris left me alone after he looked through all my stuff and I was able to organize everything the way I wanted. I hadn’t eaten dinner and I heard Chris cooking something up, I wondered if he was going to make me anything, but I think I needed more time to let the embarrassment pass. So I laid in my room just staring at the ceiling wondering if he’s gonna act normal or make a big deal out of it, I really hope he won’t make me talk about it, idk if I’m ready for that I think to myself. After enough time has passed I head out of my room into the living room where the kitchen and dining room are visible . “Hi Caly! Hope you’re hungry!” He says smiling and laughing to himself “caly!?” I say confused “yeah that’s your girl name now on” he says as he turns off the stove “for. Worry I’ll only call you that in private “

I roll my eyes “how about you don’t call

Me that at all?” I ask trying to sound assertive “no I think I will, don’t worry you’ll grow to love it!” He says so sure of himself. I ignore it for now since he is making us dinner, it was a simple chicken parm but definitely filling. We sat down to eat “so Caly” he says exemplifying the new name “I don’t really know you that well outside of being a weak employee and that you dress up as a girl” he says sarcastically “so what else is there to you?” He asks in a round about way of saying he wants to get to know me better “look man, that dressing up is a secret, I hope you can keep it that way?” I ask almost like I’m unsure “we’ll I think I can” he says with a half smile

“Dude c’mon, look I’ll be a good roommate, I’ll pay you rent and help around here” I say trying to earn him keeping it hush “yeah we’ll that was already expected” he says taking a bite of this food. “Look I’m not gonna be a total jerk to you, I just wanna have some fun with it” he pauses. “But in honesty, you said you did it in private, I’m assuming cause your parents didn’t approve…. Here in this house, I really don’t care” I pause to as I’m eating my food, what does he mean? Is he saying that I can wear it outside of my room? I never even considered this, the only person to see me dressed up was my dad and that went terribly. “W-what do you mean?”

I ask hoping he’d clarify.

“I’m saying that if you want to wear your femboy clothing outside of the room, I really don’t care, it’s your life you should be able to wear what you’d like” he says so casually as he’s finishing up his food.

“R-really? You don’t care if I’m dressed like a girl around here?” I ask knowing that’s exactly what he said “yes dude! I mean Caly! Wear whatever you’re comfortable with “ he says pushing his plate forward indicating he’s done.

I’m in shock that he’d be ok with this, I am pretty sure he’s straight, he’s good looking tall and medium build, he has nice well kept hair and probably around 6’2 190lbs, many would say a young Handsome man, he can’t be older than 25 either and he’s a manager looking to be in higher lever leadership at the store, he has a line of young girls that want to be with him! And here he’s ok with a femboy like me walking around in his house showing off some skin!?

“A-are you gay Chris?” I ask bluntly not knowing how else to ask. He chuckles and laughs a bit “no - no I’m not” he says motioning to get up, I don’t know why but I was a bit disappointed in the answer, maybe I was hoping he was, maybe I was beginning to get into that line of girls that wants to be with him, idk he felt like he rescued me and he’d been really nice since finding out I got kicked out so maybe I started to think of him as a bit of my knight and shinning armor. As he steps away from the table he says “I’m not gay, I’m bi”

He says as he heads to the living room.

“Are you gay?” He asks me, i pause and contemplate “I’m not sure” I say thinking in my own head “I haven’t had any experiences with either” I say a bit embarrassed but guess we’re letting everything out of the bag now. “Only with your dildo and plug huh?” He asks chuckling

“Dude shut up!” I say laughing back at him “I literally cannot believe you found those, I wanted to keep that a secret from you forever “ I say chuckling

“Look I’m gonna go for a run before i call it a night I know you’re off tomorrow so go ahead and clean this kitchen up and make yourself at home” Chris says as he heads to his room to change for his run. I found myself oddly satisfied knowing that I get to clean the place up while he goes on his run. I wanted to leave the place spotless for when he got back. I get a quick glance at Chris, he was wearing some short running shorts a tight fitted blue tank top and had a hat on. I never seen him out of work clothes so I found his style pretty sexy I thought to myself. Once he left I quickly cleaned up the kitchen, washed the dishes, wiped the countertops and got things nice in tidy. Once I was done I went back into my room and just kind of sat there for a bit, hoping this arrangement would work out, in a perfect world I’ll only be here 4-5 months I think to myself. Then I can get out of here. I decide it’s time to shower, so I grab the toiletries I have and I look into my drawers I see regular clothes and panties. I thin back at what Chris said, I’m conflicted, no one has willingly seen me in my fem clothes, I decide to not get any clothes for now and I would choose after my shower. So I head into the shower which has a jack and Jill type set up between my room and Chris’s room. I turn on the shower and finally have a chance to unwind and reflect on the last 24 hours and what a roller coaster it’s been.

As I’m finishing my shower I hear the front door open, I panic a bit because I have to walk a few steps in the hallway before getting to my room and all I have is my towel. Suddenly I hear a knock on the door “hey man you almost done in there, I gotta take a piss!” Says Chris

“Yes almost finished!” I say for some reason calling out in in a girly voice “

“Wow is that Caleb or caly!” He says chuckling. I laugh to myself at the embarrassment, nonetheless I stop the shower and dry off. I grab my towel and dry myself off, loosely wrap it around my waist. And unlock the door, as soon as I unlock the door Chris barges in while I’m still in there!

“Dude I been holding it I really have to go!” The toilet was nearby the door so he was standing in my way and i couldn’t get out without pushing past him. He had taken his shirt off and his back was all sweaty I looked away as he took a piss but he looked over his shoulder to me and I didn’t know how to react

“You’re a lot more feminine than I thought “ he said bluntly as he looked at me, I used one hand to hold the towel and the other to cover my chest and nipples almost like if I was a girl “dude you don’t have tits you don’t have to cover up there” and for some reason I found my hands moving away exposing my full top have naked body to him. After a solid minute of peeing he shook it off and stepped out “don’t forget what I said about what to wear Caly, it’s up to you, but feel comfortable in whatever” he says causally “you’re not gonna let the Caly thing go are you?” I say sarcastically as John walks away “nope! You’ll learn to love it!” He says as he goes to his room.

Once I’m in the clear I head to my room close the door and open my drawers, I decide to pull out from clothes just to get the feel of it, and I pull out some more conservative clothing. I extra large shirt a pair of non cheeky bottoms and short booty shorts, with the big shirt you can barely even see my bottoms, it was extremely comfortable, but I felt really weird Stepping into common area in this. I hear the shower head going as Chris is starting his shower, I decide since he’s in there I can at least sit in the living room to see how I feel, I sit down on the couch curled up and start scrolling my phone. I don’t notice the shower head stop until I look up and see Chris standing in the hallway with a towel around his waist looking at me

“You look really sexy Caly!” He says in a joking tone.

“Shut up Chris!” I say blushing a bit. I know he’s half joking but it feels good to receive a compliment and I feel a bit of butterflies in my tummy. I do take the opportunity to look up and see Chris drying his head with a hand towel and I see a light imprint of a six back and well defined chest. He looked like he definitely stayed active I thought to myself. Once he was done drying his head I looked away quickly maybe a bit too obvious “like what you see Caly?” I instantly turn red “I can ask you the same thing!” I say chuckling but defending my state “I already said you look sexy, so yes, I do like what I see!” He says

I blush and pause I just knod my head up and down with my hands up against my face trying to cover the smile and half blush “I’ve only seen you In work clothes so I didn’t know that you were even in shape!” I say trying to diffuse. “We’ll let me go change before you tackle me” he says laughing. I simply roll my eyes as he goes out of view. From his room

He hollers “I’m really glad you decided to dress in what you wanted to, you honestly do look good, I’m not lying to you!” He says as he turns the corner this time all he has is a pair of pajama bottoms and no shirt which I was not expecting “hey- uhm you’re not gonna put a shirt on?” I ask “should I?” He asks as he sits at the other end of the couch “well - I mean I guess you don’t have to, it’s your house” I say finding it hard to look away. “So how often do you used your toys?” He asks getting comfortable “we are not going to talk about that!” I say laughing and punching a pillow as a playful frustration. “As c’mon! I only ask so I know not to barge into a room to catch you!” He says as a lame excuse “look I only use them maybe a few times a month so not often” I say not being able to meet his eyes “we’ll use them as much as you want, this is a safe place, I’d be lying to you if I said I don’t have my own collection of toys” he says slyly

“What!?! you have toys too!?@ I asked Intrigued “I do, but they are a bit different from yours” he says “what do you mean?” I ask

“Well, from what I can gather even though you have not had experiences with boys or girls, you seem to be a bottom” he says, “I myself am a top and tend to me more dominant and like to control my partner”

So many questions were going through my head, why is my boss telling me these things, and what do they exactly mean, does that mean I’m more submissive? Too much information to process

“So my toys are really more aligned with that, I can show you if you’d like?” He asks. I was very intrigued and curious to see so I just knod yes without saying anything. He retreats to his room and I get a really good look at his body as he leaves and comes back with a decent size box.

“Theres quite a bit of stuff in here but don’t freak out” he says as he looks at me before opening it. He opens it slowly and I just gasp at all the different things I see.