Femboy chronicles

If it’s a date I decide to dress back in my boy clothes, I didn’t want to be in public so I put a graphic t and a plaid shirt blue jeans and tennis shoes, a bit casual but I didn’t want to be too formal. I go out in the living room when Chris comes out and he is dressed similar to me which I was excited about that we had the same kind of idea. When he sees me he has a bit of a puzzled look on his face “hey Caleb, what happened to Caly?” He asks. I chuckle knowing he’s talking. About my femboy clothing “oh yeah, well If we’re gonna be in public I thought I’d change back to boy clothes” I say looking at my plaid shirt. “Oh, well I’d really prefer for you to go out as Caly” he says as he approaches me “y-you would?” I ask a bit unsure of it all “we’ll yeah, if it’s a date then I want to go out with Caly, I think she’s hot, and again I’m here to help you really figure out who you are. And I need to nudge you in the right direction, going out in public as a girl I think would be a big step for you” he says as he’s standing at the hallway pointing to my room indicating for me to go back and change “but I never been out in public like that, I don’t know if I can” I say as I stand up and head towards my bedroom, Chris close behind me”

“Look it’s ok, put on some makeup, something sexy and I bet you’ll feel great about it!” He says to me as I sit on my bed “I-I don’t know Chris” I say ina soft defeated voice as I felt that I’d disappoint him if I didn’t do it “look Caly, do you want to go out on this date or no?” He says not angrily but more playfully like he’s poking fun at me. He knows I want to, idk why but I am starting want to be with him and of course I want to go out with him, idk what it means idk if it means I want to be together I just know I want to spend time with Chris. So when he asks the question I say “yes Chris! I do want to go on a date with you” I say as I stand up from my bed. “Ok we’ll let’s get Caly out” he says as he stands in my doorway almost indicating that he won’t step out while I change. “A-are you going to watch me change?” I ask unsure about it “yeah I can help you pick your first outfit you’ll be wearing in public!” He says all way too excitedly. I was beginning to get nervous, was I really going to do this was I really going to go out as a girl for the first time. It was happening all too fast, but I was excited  and nervous, and the sound of going out with Chris sounds comforting for some reason. I love the way he has been making. Me feel, even though it’s mostly submissive, I can’t help but the need to make him happy, the need to not disappoint him I think to myself. “I don’t have a lot of femboy clothing so we’ll have just a bit to work with” I say as I take some stuff out of my closet, as far as tops the best options where a black skin tight spaghetti strap shirt at showed of my smooth sexy shoulders and my slim figure, when it got cold my nipples would leave noticeable indentions on the fabric, along with blue Jean booty shorts that barely made it past my plum ass. I showed it to Chris almost seeking approval “wow you’re gonna look sexy in that, let’s go ahead and see you in it” he says still standing in the doorway. I hesitate “are you going to watch me change?” I ask a bit in a shaky voice as this excited me a bit too much but Also made me nervous “sure unless you want me to step out?” He asks, I find myself conflicted as I want him to make the decision but also giving him an answer would show my cards a bit. As I contemplate I think to myself he just saw me fuck myself with the dildo, I don’t think changing in front of him is a big deal. I think to myself. I casually take my plaid shirt and graphic tee off along with my jeans. I am standing In front of him with some boxer briefs. Which I notice won’t go with this, so I go to my panty drawer and I see Chris lean over to see what I got “it’s the first date, I think you should wear something special” he says. I immediately blush, why am I blushing? Why does that excite me, I don’t even really know what he means. But I gravitate to a thong I have that does nothing to cover my backside and barely holds my small member in the front. Again I find myself showing it to him seeking approval. I find myself saying without thinking “is this one ok ?” I say as I blush can’t believe my mouth just asked him that I think to myself. He smiled as he saw the thong, it was black, and the string was thin, he smiled and said “yes Caly, I’d like to see that on you” he says very seductively.

God why am I blushing and my cock twitched when he said that, fuck! He’s my boss and he knows more about me than anyone else even though I haven’t lived with him more than 2 nights!! And now I’m about to get naked in front of him for the second time within hours only for him to see me put a thong on. I put the thong on my bed as I try to make it seem normal for me to get naked in front of him, so I pull my boxer briefs off trying to not mention my half staff. And I grab my thong and slip it on, I go grab my shorts but Chris says “stop!” I freeze with the shorts in my hands “stay like this while you put on your makeup” he says. “You want me to stay in my thong?” I ask “yes, you look to damn sexy right now and I want to document our first date appropriately “ he says “oh-uh I don’t have any make up “ I say trying to get out of this and hope he’ll just let me put clothes on. “It’s ok I have some that a previous girl left behind one time” he says as he heads to his room quickly and brings out a decent amount of things to include lipstick, foundation/ blush/ and eyeliner. “This should work I think” he says to me as he hands it to me, and what does he mean by documenting it? God so many thoughts going through my head but I find myself reaching for the makeup, it had been a while since I put makeup on last time was when my folks went out of town and had to use my moms. I head towards the restroom where there is good lighting and a mirror. Chris close behind me no doubt he’s staring at my ass I think, I go into the rest room and set it down on the counter. “Ok I’ll try my best on this”‘I say as I begin to work on it. After about 15 minutes and him staring intently I was all dolled up, lipstick, blush and eyeliner, I literally could pass as a girl.

Chris took several pictures of me in different angles as I put the makeup on, idk why I let him or even object to it, but it felt exciting to have him look at me like that. Once I was done he even started to direct me in different poses at which I didn’t protest as I was gaining more confidence

“Have your back to me and look back and pucker your lips” he wanted to get my face and ass in the same shot, so did just that. I felt naughty, I felt a bit degraded, but I liked it? I kind of forgot that all I’m wearing is a thong and I’m in full blown makeup. But it felt safe with him. I thought to myself. After what felt like 100 pictures he then said “ok time to get dressed” he said as he motioned to my room, as I walked past him he lightly spanked my ass, i jolted up not expecting it but I kinda chuckled not protesting it. I got dressed quickly and put on some black vans with my outfit since I did t have actual girl shoes. My heart was beating out of my chest as I was nervous but excited “tonight Caly makes her first public appearance!!” Chris said excitedly, and I actually don’t even mind the nickname at this point, super weird I thought since I was so against it early on “thank you Chris” I say blushing as I come out of my room literally could pass as a girl “damn you look hot!!” He says as he looks me up and down “ready baby?” He says as he opens the door for me. The baby piece sent shivers down my spine and i had a nice bounce as i excited our place knowing tbh so was the first time ide ever been dressed like this in public. “Where are we going?” I ask Chris “Caly, don’t worry about that, this is our first date, should be a surprise shouldn’t it?” He asks. I simply jump into his car and we start to drive.

We got a medium scale restaurant not too fancy, we aren’t rich! The one thing that got me nervous is that it was close to where we both worked.

Once we get seated Chris and I start talking mostly casual things nothing too serious, if you were a guest here you’d think that we are your average couple, I am a passable girl and it looked like we were dating. My heart had stopped pounding once we got seated, I had a few nervous moments as we walked to the restaurant and waited for our table, I wanted to try and not be noticeable so I tried staying close to walls or objects that would hide me. But I started to notice that a lot of men were looking at me, checking me out, and as I saw more and more do this I gained more confidence. So once we sat to the table my nerves were a bit more calm. So by the time we sat down it felt like we were having a normal conversation, just as we were getting our food Chris interrupted the conversation mid sentence to holler out “hey Sam how are you, what the heck are you doing here!?!?” He says playfully. Oh fuck fuck fuck!!! It’s Sam from work! He was the lead in our dept, big body builder type guy, and i often relied on him to help with the heavy stuff and here I am dressed as a girl with our boss!! “Hey Chris! Didn’t know you were gonna be here, hey inventory numbers came back, we killed it man!” He say also excitedly before he turned and saw me sitting with him. “Oh shit, got a date with you huh?”

He asks, “I won’t interrupt, have a good night Chris” he says as he stared at me way too long for my comfort as they left my face was burning red “Chris! What if he recognized me!?” I say almost mad at him “no he didn’t, he would have said it right away, and look at you, you look like a literal girl! No way he recognized you especially with the make up” just then Chris’s phone buzzed it was Sam he laughed and showed me the text. “Hot chick! You better tell me tomorrow all the stuff you did to her!”

I instantly blush what the heck is that supposed to mean? I never said I was gonna have sex with Chris, this is more of him helping me be more confident, it’s not like he’s my real boyfriend! “We’ll he may be up for a disappointing story when you see him tomorrow “ I say dismissively insinuating that Chris isn’t getting lucky without answering Chris reached over to on the table where my hand was resting and put his hand on top of mine “really? You don’t think I’ll have anything to tell him?” He asks slyly, his touch was electric, i don’t know what it was, it was like a power that was coming from him, I can’t explain it I think to myself. But I don’t fight his touch, rather I think about what he said, what does he mean, does he expect me to do something sexually, would I? Idk, I can’t think straight and before I respond he simply says “I’m just trying to help you, wouldn’t you rather explore in a safe place with someone you know than some stranger?” He says as he begins to intertwine our fingers and we are now holding hands at i feel….. idk I feel safe with him. I blush and look at our hands “Chris…..” but nothing comes out “Caly” he responds with a soft smile and as he does my cock tingles. I’ve grown fond this nickname.

We get our tab and head on out as I walk behind him I instinctively reach for his hand and without hesitation he holds my hand too, and I feel like a little school girl as he does this, I have a pep in my step in front of strangers dressed like a girl and have make up. It honestly feels like the best first date!! He opens the car door for me and as I get in he slaps my ass and I find it endearing. I actually smile as I get in and wait for him to turn the corner to get into the drivers side. When he gets in and starts the engine he placed his hand on my lap, it’s skin to skin contact as I was wearing my booty shorts and he asks “ready to go home baby?” He says which sends chills throughout my body again “y-yes, Chris” I say a bit awkwardly just cause I do t have a nickname for him. He keeps his hand on my lap and strokes it a bit which makes it difficult to hold a conversation he noticed and rather put my hand on his lap, but way further up his lap than what he had his hand. He looks at me and smiles “you didn’t notice did you?” He asks smiling as we’re at a red light “notice what?” I ask he then looks down at my hand and I look at it which is just sitting on his lap, he then get my hand and grips it on his thigh harder….. only it wasn’t his lap, I was touching his cock!!! It felt like part of his leg, I was going to pull away but he kept my hand there “Caly, it’s ok, just touch it, explore it a bit between now and when we get home” he says and he lifts his hand from me and I look down, it looks like it is very sizable, huge cock. He smiled and looked at me while I couldn’t keep my eyes off of it. I don’t stroke rather try to feel it a bit more the girth, the stiffness etc. once we pull up to our parking spot he looks at me and says “we’re here, how about we go inside and you can touch it without my pants on!” He says as he parks. I look at him and I take a big gulp as I was nervous what to do!