Femboy chronicles

When Chris opened the box I saw things that I wasn’t even sure what they were and the box was filled to the brim “now don’t freak out, I’ll explain some of this as it looks like you’re not sure what they are” he said pulling a few items out, first was some of the common things, a whip, a ball gag, a dildo (significantly bigger than the one I had), a butt plugg, also bigger, handcuffs and restraints. As he pulled some of this stuff out he was looking right at me. And I was getting a bit curious and felt a twitch in my crotch that he couldn’t see because of my oversized shirt.

He laid out the toys in the space between the us on the couch. I didn’t touch anything but was in awe of the collection he had “you see I do like to be the one in control, but I do so with the consent of my partner, I’m not a jerk after all” he says sarcastically “see anything you like Caly?” I roll my eyes at the name but I don’t object “ I mean I don’t know, I had never considered using any of these” I say still looking at them “well sure, but how do you feel seeing all of it?” He says probing as he’s curious to my response. What do I tell him, do I lie, do I defer, I am sitting in femboy clothing, he knows I’m curious about boys, should I protect whatever dignity I have left? In my confusion all I say is “I don’t know”

“Lift your shirt up a bit” he says as he knows my shirt is not showing my crotch. “What, why?” I ask but reaching to my shirt “I just want to see, you may be saying you don’t know how you feel, but your body may tell me the truth. I don’t know why I don’t fight it, I don’t know why I just obey him l, maybe it’s because I have to listen to him and work? Nonetheless I simply lift my shirt up to reveal my booty shorts and a small hard on I had pitching the smallest tent you’ve ever seen. I look down at it knowing he can see it also and turn red from embarrassment

“You see, your body says it likes it, do you like the toys in general. Like do you want to see them be used or would you want them to be used on you?” He asks “idk man” I say moving my shirt back down and covering my tent “look man it’s ok, you’re petit and feminine, so I can say confidently that you’re on the submissive side, I bet you’d like these used on you. And you’d let a dominant man have his way with you given the chance” I’m in shock at the assumptions, I open my mouth to object but nothing comes out. Was he right? Am I a submissive kind? I always knew I’m the smaller type of guy, I’m not strong, I shave my privates by choice and I dress up as a girl, it seems to make sense? I think to myself

“Look, I’m not gonna do anything I promise, but I just want to see if I’m right” he says in a low voice “do you trust me”

Again don’t know why I don’t fight him or question it, but I just knod yes I do trust him. “Ok well I’m gonna put the handcuffs whined your back, I’m not gonna do anything, I just want to see how it makes you feel” he says as he stands up, when he stands up so do i without saying anything “now turn around and put your hands behind your back Caly” this stupid name, he’s only called me this afternoon, but ….. I like it? Idk what the heck is happening!!?!? I think to myself as I put my hands behind my back and he puts the handcuffs on me, not too tight and holds my arm to turn me back around facing him, my cock grows to its max of 4 inches and I’m pitching my best tent in front of my boss “how does it feel?” He asks rhetorically as he looks down “I- I uhm I” I say turning red and slouching to try and hide my hard on “spill it out caly “ he says softly “I, I …… I think I like it?” I say pitching at the end making it sound like a question. “Can I lift your shirt a bit?” He asks “y-yeah s-sure” I say crackling voice to show my hard on poking my shorts. “Before I uncuff you” he says as he looks at my hard on and looks at me “you stood up when I stood up, you turned around and put your hands behind your back at my direction, you let me pull up your shirt, you did all of this willingly, you love being told what to do, and you enjoy giving up control. You have. Hard on!” He says chucking “I’m not saying this to embarrass you, I say this so you start to feel comfortable with who you are” he says as he lets my shirt fall back down covering up my shorts “here’s a quick test if you do t believe me…. Would you like for me to uncuff you?” He looks at the in the eyes and I think about this as my initial response was going to be “if you want to” but wait, if I said that I’m proving his point? Why is it if he wants to, what do I want!? Do I know what I want!? Why does what he want the first thing that comes to mind? Like to me it doesn’t matter what I want, I instinctively want to do whatever he wants to Do; before I answer he says “you see, you’re having an internal battle with what to do or what to say, I’ll make the decision for you, I’ll uncuff you for now, but I guarantee that this won’t be the last time you wear them” he says as he reaches over as we’re still facing each other and removed the cuffs, his plain chest rubbed. A bit on my chin/ nose area and for a smell of the body shower he used and it smelled so good I think to myself. “Thanks man- I , I’ve never felt like that before” was all I could say to him. “It’s ok Caly, now it’s time for bed, but before I go to bed, I’m gonna test you a bit, and this is an effort for you to find yourself, between now and the next time I see you, I want you to used your dildo “ he says “I work a morning. Shift tomorrow, I’ll be gone before you even wake up” he says as he begins to gather his toys and put them back into the box “oh uhm, yeah I don’t know” I reply “that’s ok Caly, you’ll have the night and morning to think about it” he says as he walks out the headed towards his bedroom “good night!” He says “night” I say back a bit more faintly to him.

As I feel my eyes get heavy I head over to bed and think about what Chris said, he wants me to use my toy by the time he gets home, should I? Could I lie to him and tell him I used it when I didn’t? But initially I feel like I want to because I want to make him proud of me….. wtf proud of me!? Why would I need him to feel proud of me? Why is that my driving incentive? Is it because he told me to do it, I feel like I need to obey it? Wtf obey?? He’s not my parent or family? All these thoughts in my head and I couldn’t get them out so it left me for a mostly restless night. Sure enough when I woke up Chris was gone, it was 8am when I woke up and it was weird waking up not in my house, but glad to wake up in fem clothes like I always wanted to. I casually stroll into the kitchen and make myself some coffee, and a light breakfast. When I go to the living room the lounge around as I didn’t really know what to do with my free time, I decide to go into my bedroom and get dressed for the day even though the most I might to is sit outside as I was still scared to be seen in public in femboy clothing. As I got a tight tank top and booty Jean shorts I came across my dildo, I had such a relaxing start of the day that I had forgotten about this. Chris wanted me to use this, it’s still early in the morning he won’t be home until around 3pm today, I set it on the counter as a ‘maybe’ option For me. I go and watch tv but bring the dildo with me so I wouldn’t forget I think to myself. As I doze off into a random movie I look over at my dildo “would he be mad at me if I didn’t do it, do I want to make him mad at me? Why do I care if I make him mad? Maybe I’ll just to it to get it out of the way and I won’t dwell on it all day? All these thoughts go in my head and the movie is done before I know it. I decide I need to keep my mind busy so I put on some music and for some reasons start cleaning, I think it was a defensive mechanism for me. If I don’t do it he’ll at least be happy that I cleaned? He’ll be proud of me? Wtf Proud of me!?!  Never mind that, time to get this palce nice and clean! I take the next hour sweeping, moping, washing dishes, cleaning countertops, even decide to start Chris’s laundry, I decided not to snoop rather just start it. Once I was done it was only 10:30am, and I look over and the dildo is still staring right at me. I decide I’m gonna drive myself crazy and won’t be able to concentrate if I just don’t do it  on and get it out of the way!

I go over and decide that I’m gonna do it in the living room, I’m home alone anyways. I decide to take my bottoms off along with my panties go to my room really quick and grab some lube. I sit back on the couch squeeze some lube on my hand and massage my tight Hole all over it, I was really tight since I last used this three weeks ago and even then it was only for about five minutes. I then put my index finger slowly through my hole, just slowly going in and out to at least relax it a bit. With my free hand I squeeze some lube on my dildo and then rub it all over with my hand, i don’t put a second finger in, rather line up the dildo. Before I start to push it in I notice that I’m rock hard, don’t get me wrong I have gotten hard before when I’ve used this but it wasn’t until after I got started, why was I turned on before? Is it because I know I’m doing g this because of Chris’s direction? I try to get that thought out of my head and slowly apply some pressure into my hole with the dildo. Slowly and a bit painfully it breaches me and I take a deep sight “ohhhh” I say to myself, it feels different because there is no sense of urgency I can take my time. I slowly push every centimeter in, I wanted to feel it all. I eventually push ball 6 inches in where I am barely holding the suction cup at the end. I hold it there and sigh deeply again loving the feeling even if it hurts a bit. I then start to slowly take it back out, leaving only one inch in before again going slowly all the way back in, it would take about 30 seconds to go all the way in and all the way out, I was enjoying the slow movements and I was enjoying the sense of freedom of not being rushed. I started moaning a bit loudly as no one was around to hear me, I loved it, I loved the dildo in my ass. I kept thinking Chris told me to do this, I wouldn’t be fucking myself if Chris didn’t tell me to. But he was right, I feel like this is what I should be doing, this is who I am. I moaned “thank you Chris” I said as I was picking up the pace a bit.  I decide to get on all fours and put the suction cup against one of the coffee table legs and was going to fuck myself that way as I wanted to go faster and I always imagined that doggy style would be my favorite. I apply more lube on my dildo. I then stick it in and it feels like it is going. Deeper, it is barely touching my prostate, but as an inexperienced person it was enough. I was going faster and faster losing myself in the moment, even losing track of time. I kept moaning “fuck yes, fuck me, deeper, faster, thank you Chris etc “ I was so lost in the moment that I never heard the front door open as Chris walked in and saw me on all fours facing away from him with the dildo lodged in my ass and me Moaning his name.