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Slave Stephen’s sissy humiliation

Dear Mistress, This was a brilliant session in which you humiliated me completely. Having obtained suitable items as requested I set out to do as you commanded. First I stripped off for you to stand in front of the camera butt-naked, all too aware of my short-comings exposed for your inspection and derision. This made me feel very small indeed as I could imagine you taunting me and tittering while I stood helpless and blushing.

If that was bad enough then worse was to come as you forced me to wear a bra and panties, and once again stand shame-faced for a photo. I could imagine all sorts of uncomplimentary comments coming from you as I was made to stand before you in ladies’s underwear, while all I could do is cringe with embarassment. I imagined it was you actually taking the photos no doubt in order to bring them out to humiliate me at some later date. 

Next you make me put on some tights and I’m beginning to wonder just how far you will make me go? Seeing my legs all covered in black lacy patterns is just so mortifying, and I feel my masculinity being slowly stripped away as more female clothes are being heaped upon me. I can imagine you adding a few choice words of derisory encouragement, which does nothing to help the humiliation I feel. 

Another embarassing snap follows, then you order me to put on a skirt. I managed to find a skimpy floral skirt with some red on it as ordered, and slipping in to this was so embarassing. When secured I felt quite degraded as coupled with the tights it made me feel forcibly humbled. No doubt you would have been chuckling at my discomfort and making more comments to provoke more reddening of my cheeks, as well as snapping away in order to preserve the occasion. There was very little of me left that felt male, and from the waist down I looked a complete girl. Furthermore I felt quite vulnerable in a skirt especially one so flimsy, as it could be lifted far too easily to expose my private parts. Thank goodness for the tights, I found myself thinking.

By now you had me looking utterly ridiculous (or re-dick-u-less), and I’m sure you would have found more ammunition with which to ridicule me. However, my predicament was not yet over as now I had to slip into a bright red blouse to complete the outfit. Once this was on I felt utterly degraded, and a complete pansy. I imagined you would be cackling with delight and making all manner of rude comments to rub it in. There I was dressed from head to foot in women’s clothes feeling quite exposed in my skimpy skirt and blouse wondering how on earth I could convince you to take me seriously as a man?

This not being enough humiliation, next you demand that I put on makeup. Wearing ladies clothes is one thing, but putting on makeup as well is even more degrading. I thought Mistress really is determined to make me look as big a sissy as possible. I applied some pink eye-shadow and blusher, laying it on thick as you requested. Then some red lipstick to match my blouse. I even remembered to write Online Mistress with a highlight pencil across my forehead, which I think marks me nicely as your property, and a thoroughly humiliated slave to whom you have just taught who is the boss. Looking at myself in makeup I thought I looked awful, and I’m quite sure you would have marched me to a full length mirror to show me your handiwork and watch me cringe with embarassment. Mortified at being the butt end of your sissy jokes I would have been completely under your will and unable to resist your commands.

In the next stage I find myself lying on the floor imagining you standing over me commanding me to masturbate into my panties. Slipping my hand under my skirt and down my tights I begin pumping. It’s a little restricted down there but I manage to find enough movement, even though my cock is squashed against the fabric like a fish in a net. I feel quite degraded having been made to dress in girls clothes, and then get down and masturbate at your feet still wearing them, and have the strange sensation of feeling like a girl playing with herself.

The thought of you standing there watching me makes my cock hard, and I can’t help the odd moan of pleasure. I suddenly become resolved to put on my best performance for you, and squirm on the floor pump faster and faster. The moment arrives, and I try to squirt out every last drop in tribute to you, as a white glob of my seed suddenly appears through the pink of my panties. It ends in quite a mess and as I wipe my hands on a tissue I’m suddenly rudely aware of how I have abased myself for you. Sitting there in women’s clothes and makeup with a sticky, sweet-smelling mess in my crotch.

I remove my girlie clothes and feel a little more male again, but this is short-lived as I have to remain in the panties. What’s more there is an awful mess in them. I wash the make up off my face all the while aware of a now cold wet patch in my undies. With my lust now spent this feels particularly uncomfortable, especially the musty odour emanating from it. My instinct is to jump in the shower to clean myself off, but you have commanded that I remain in them for another 12 hours which will take me to 10:30 pm. The thought of this is not very appealing and I wish I could take them off and I’m very tempted to do just that. With considerable effort I pull my trousers back on and try not to think about it. However this becomes impossible as whenever I move there is a cold wet sensation from my penis, and I can’t escape that musty odour of my own sperm. I am forced to recall just how much you are in charge, and if Mistress commands that I sit in a pair of my own spunk-stained panties for 12 hours then I must comply no matter how uncomfortable I feel.

After a while the scent becomes quite alluring, and serves to remind me of Mistress and my lesson in humility. I become quite stiff thinking about it. Whenever I go to the loo, I have to try and squeeze my cock out of my panties sideways with a pang of humiliation, as there is no slit as in my boxer shorts. I also catch a musty, pungent scent from it, as my sperm has dried all over my cock. After a few hours of this I’m wanting to perform the lesson all over again. What’s more for the rest of the day I feel very conscious of wearing a pair of ladies pink panties under my normal clothes, and this feels most humiliating. Another sign of how much she controls me, I thought. I am becoming her mere plaything, and when she clicks her fingers I perform.

Later that evening I have a shower and good scrub as I feel I smell like a walking sperm bank, but feel most grateful that I was allowed to make such a tribute to the Online Mistress. More often than not, these days, my masturbation fantasies revolve around her.

This has been an excellent lesson Mistress. Many thanks for it, and I look forward to the next!

Yours most gratefully,

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