Max is Checked In

This topic contains 46 replies, has 2 voices, and was last updated by  Androgynous 3 hours, 30 minutes ago.

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    I shake my head as you suddenly become a little body conscious and forget my training already.

    “Stand straight and arms behind your back” I’m quick to remind you in a not so pleasant tone.

    There’s a pause as I lean back and put my feet on the desk but instead of speaking of punishments I instead say “alright then, lets see you get hard and ready to fuck me”


    The silence after your words is deafening. As soon as I realize you’re serious, I nod and reach for my cock.

    I can do this, I think.

    I start to stroke myself slowly, trusting that my pent up, under-stimulated cock would leap to attention with little effort. Sure enough, I start to harden.

    Trying to be subtle, I allow myself to look at you. Taking advantage of my view of you with your legs up on the desk, I try to imagine myself being close to you, touching you, fucking you. Based on how you’ve treated me, it seems so far away and impossible. But the idea gets me going nonetheless. It its mere moments before I’m hard as a rock.


    I smile as you get hard very fast, you have such a nice cock it’ll be such a shame when I belt it.

    “Good boy” at least I can have fun with it though as I beckon you to come closer “now rub it against my leg”


    Very conscious of how naked I am and how ridiculous I must look, I round the desk and stand at your side. Tentatively, I hover beside your leg and begin to gently run its length along your thigh, using my hips to form long, slow strokes.


    It almost seems that I’m laughing at you, a point that is reinforced when I actually do laugh “is that the best you can do? I want a real man to fuck me, not some pansy sissy boy who only likes to take it up the ass” I give your bare ass a hard slap for added emphasis.

    The phone rings and I answer it while your trying to hump my leg!

    I talk like normal, something about a shipment being late or delayed?  Either way I’m not to pleased by it either.


    At last my frustration boils to the surface. I’ve been doing my best to be compliant since I entered this building, and I still don’t properly know what’s going on. At this point, I feel like I’m going to receive the worst of your punishments no matter what I do. With a burst of completely unearned confidence, I turn your chair so that the leg propped up on your desk leaves you open.

    I reach for your underwear in an attempt to pull it down.


    I manage to cling on to the phone as you attempt to get into my panties!

    Reacting quickly I’m already swatting away your hand as I tell however it is to hold on a minute.

    My attention now completely on you I look like I could hit you but I don’t “and just what do you think you are doing?” I look from my leg to your face “does that look like my leg to you?”

    I adjust my skirt “is that your idea of trying to show me what a manly man you are?” it’s like I’m laughing even more at you after your ridiculous stunt “is that what your Master would want you to do to his wife?”


    Fuck. Now I’m royally screwed. 

    I stutter and look all around, not sure where I could be allowed to focus my gaze.

    How I could let myself do something like that? 

    I take a step away from you and do my best to salvage what is left of my composure, which isn’t much.

    “No, ma’am. It isn’t. I…I need to learn. I just don’t know what to do or what I’m doing here.” My heart sinks as I come to realize that my outburst has doomed me to far worse treatment than whatever I was going to receive before. But I can barely imagine what even that was going to be like.

    “Please, ma’am, can you tell me more about what I’m doing here? Or at least tell me what the next step is? I am so lost.”


    I shake my head, your so pathetic “if I were you the only thing I’d be concerned about is doing what your told and doing a good job of it” I shouldn’t have to but I spell it out for you but then again if you weren’t a pampered spoiled slave then your new Mistress wouldn’t have sent you here.

    “Now let’s have less of that yapping and more of you doing as I instructed you to” I wave my hand dismissively at you as I resume my phone conversation as if nothing had happened.

    Knowing how thick you are I snap my fingers at you and point to my leg so you know that I expect you to go back to your task.


    I take a breath and focus on my instructions.

    Just do what she says, and it’ll be okay. 

    Reminding myself of this makes me feel better. My cock has softened noticeably, but it is still sufficient for what I need of it. With a posture as neutral as possible, I gingerly place my cock against your leg as you return to your phone call. Very slowly, I begin to rub, up and down, fearing your wrath with each stroke.

    My mind races and I’m tempted to say something. More than once, I take a breath as if you ask you a question, but I think better of it.

    Just focus on what you’re doing. Nothing more is expected of you.

    This final thought calms me.


    I watch you like a hawk even while talking on the phone, seems you’ve wised up a bit but your cock is disappointingly soft.

    This time I don’t even bother to ask the person on the phone to hold on as break off to I lay into you “don’t insult me with that limp thing” I point at it “play with your fagot ass or do whatever else a sissy like you needs to do to get hard”



    “Yes, Ma’am,” I say.

    Sissy? I think. What’s that all about?

    Not wishing to disappoint, I reach for my ass and begin to play in and around it. My fingers tease in and out with ease, and I moan almost silently.

    I pull every trick in the book to get hard again. I try to fantasize a woman sucking my cock. The harder I force the image into my head, the less effective it becomes. Gradually, I shift my attention away from imagining the way my cock feels with a mouth on it, and I instead find myself fantasizing about the way my mouth feels with a cock in it.

    It is only moments before I’m hard again.


    You take an age to get hard even when playing with your ass which between you and me you were a little to eager to do.

    “It’s about time” I giggle as I admire your nice looking cock rubbing against my stocking clad leg, it’s just a shame it’s attached to such a sissy.

    “Oh, you’d better not get my stocking dirty” I point out a little too eagerly as I see the tip of your cock getting a little juicy!


    I gulp and try to squeeze off any more precum from flowing. I silently beg that little drop at the tip to stay put, even as I continue to rub against you.

    Despite my best efforts, the little clear drop begins to run down the bottom of my shaft, and before I can do anything about it, soaks into your stocking.

    I cringe.


    I almost laugh, there’s no way any man could do what I asked of you but that doesn’t stop you from trying, you look even cuter all desperate and fearful.

    And of course I see the tiniest spot and point it out as if it’s under a magnifying glass “looks like someone doesn’t have any self control” I wag my finger at you but don’t react in any big way letting you continue to degrade yourself.

    You probably wish I had stopped you though as the alternative is much worse “your lucky I’m so nice and am willing to give you a second chance!”


    I don’t know what I did to deserve a second chance. Relief washes over me.

    “Thank you, ma’am!” I stutter. It takes everything not to collapse from shame.

    Judging by your voice, and from the fact that you’ve forgiven me for losing control, I fear the worst. I fear what you’re planning. But looking at myself, I can’t find any way out of it. If I try to change anything, it can only get worse.

    I keep my mouth shut, and continue to rub my sad, dripping cock on you, desperate for approval.


    Your attempt at a do over is the expected train wreck as your soon dribbling uncontrollably, and on top of that your going soft again!

    I shake my head looking at you with perhaps a hint of disapproval or is it annoyance? Either way you don’t say anything so we continue with silence between us until I hold out my hand to signal for you to stop.

    Tension builds as I stretch another pause out for 10-15 seconds before finally speaking “do you have nothing to say for yourself?” I poke your pathetic manhood with my well manicured fingernail “the least you could do is clean up your mess”

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