cross- dress

You come home to find the place empty, a single handwritten note your only clue as to what lies ahead for you this evening. My scrawl is unmistakable and the instructions simple,



“Everything is laid out on the bed, I will return at 7. Be an amusing toy for your Mistress and you will enjoy yourself a great deal more. Make sure you take care in getting ready, I expect a pretty nancy boy awaiting my arrival.”



Mystified and with growing excitement, you enter the room to find everything as promised. Your cock jerks in response to the myriad of small containers, brushes, and glosses that meet your eyes. You unstopper a few of the bottles and find a scent you like, applying it gently to your pulse points.



The small brush feels strange in your large hand as you dip it into a pot of powder, noticing that the colors chosen all suit you well. A million tiny kisses sweep across your skin as the soft covering falls into place. The creme’s and pearl pressed eyeshadow go on next, feathering softly.



The cold gloss feels foreign on your lips, now full wet and pouty… perfectly slutty. Your eyes skate over your reflection, astounded at the marked change in your appearance. A rush of blood fills your cock and it swells in appreciation at the visual reminder of your submission.



You rise from your seat at the vanity, and approach the outfit laid out for you carefully on the bed. You allow your eyes to drink in the sight before you: a long waisted pale pink corset edged in black, falling from the bottom of the corset is a 4in sheer black ruffled skirt with pink lace accents; a small white lace apron; accompanied by a black lace garter belt and long seamed thigh highs, with pretty pink bows at the tops. A matching set of heels sits in adorable girlish innocence off to one side, from the wicked height you can tell your feet will hurt by the end of the evening.



Your stomach clenches and tingles run down your spine as you contemplate the humiliation of donning such an item and then being paraded about like a common piece of slut ass. Your cock grows steadily harder. Throbbing with your heart.



You slide the silk stocking up your leg luxuriating in the grip of the fabric against your skin a constant soft reminder of your servility. Carefully you fasten the belt around your hips, hooking each strap gently to the thigh highs, careful not to snag. You happen to catch your reflection in one of the many mirrors I have positioned to face you. Your cock stands from your body, hard and erect rising from a nest of lace, the thigh highs line and accentuate your legs.



Your face burns in shame as you remind yourself you do this for my pleasure, to show me what a good boy you are.. good enough to be treated to a proper hard fucking.



You wrap the corset around your body, I must have some how measured the garment to you, because it fits like a glove as you begin to fasten it into place. Your chest and stomach constrict as the casement about you tightens inexorably. Elongating and trimming your figure for my amusement and pleasure, a frilled hourglass shape for me to taunt and punish. You tie the delicate lace strings about your now much smaller waist, their gentle pressure yet another reminder.



Your breathing increases with your excitement and your chest strains to expand completely, too many shallow breaths and you begin to feel light-headed. You can’t help the moment of panic that swamps you and you tell yourself to breathe with your both your diaphragm and lungs equally, allowing for the most air with the least movement. Your changed breathing another token of your dedication of service to me.



You sit, perched on the edge of the bed; posture perfect- such a good slave boy. As you reach for the shoes a shiny black leather collar catches your eyes, unnoticed before it sits beside those innocently wicked stripper heels. Your stomach tightens and your hands tremble slightly as you fasten it tightly around your neck; it’s high form pushing your chin up, stretching your neck so prettily.



The shoes slip easily onto your feet, though you find it hard to bend to tighten them. You straighten and stand; this time deliberately surveying yourself. Face made up in a whores mask; curvaceous body hugged in soft pink satin; Legs displayed; muscles showing from your added height; chin held up proud from the leather collar. Such a pretty, fuckable boy toy. A proper little slave puppet for his Lady Mistress.



Your cock throbs and spasms, you have to catch yourself before cumming into your pretty outfit, as the grandfather clock in the hall chimes 7. You groan as you realize the night hasn’t even begun……



*****



The sound of the front door snaps you from your revery, and your heart beats impossibly faster, thudding against the wall of your corseted chest. The click of the latch is followed by a flood of girlish voices, you are able to pick up mine effortlessly and you think you might recognize a few more. All in all, you figure there must be around 4 or 5 women in the entryway, seemingly intent on using you devilishly. The conversation becomes more clear as we enter the main room and the front door latch snicks into place.



“Stephanie love, I thought you said there would be a fun surprise waiting for us after our shopping?”



“And there certainly should be, perhaps he’s feeling a little put on the spot.” I raise my voice slightly to carry across the house. “Come now pet, don’t be shy; all these pretty ladies are dying to see you. They have been so looking forward to our little evening, and we wouldn’t want to disappoint them.”



You turn and start toward the door, aiming to please before you even realize your intentions. You can see me when you step into the hall, our eyes meet once and you can see the pleasure and appreciation in my gaze before yours drops to my feet. Standing just outside the entry I watch you make your way towards the front room, steps measured. Everything about you screams glorious adorable submission, your tightly corseted frame, frilly sheer skirt only emphasizing your ragingly hard cock. Simply delightful.



Your scent washes over me, so much like the picture you present;sharp sexual male barely contained, lightly fettered with the trappings of woman. Right before your pass through the door and onto the view of all, my voice finds you again.



“Don’t speak unless I tell you, don’t move if they touch you, forget everything but pleasing all before you. Now go on and be a good boy for me, my Simon” I give you an encouraging slap to the ass and watch mesmerized, at your reaction to the reception you receive.



You falter for a second at the coos of delight and laughter that welcome you. A blush builds across your skin when their hands descend and your realize the full extent of your humiliation. The countless fingers prodding and caressing you. Discussing between themselves the girth of your cock, the curve of your ass; whether or not you can cum enough times to satisfy them all. Tingles of shame and humiliation as you recognize the faces of some of my closer friends amongst the women.



Nikki is there, tiny body and hot round little ass; Sheila as naughty as ever, looking for all world like she would like nothing better than to gobble you up. Two unfamiliar faces as well, Lola standing almost 6′ has long inky black hair and wonderfully perky tits; and little Morgan, ridiculously huge anime eyes taking up the majority of her face, so very innocent looking.



You feel like an object standing there surrounded by grasping, jeering girls; roughly fondling your prettily dressed form. Becoming more aware of the depths of your subservience to me, you submit to their pulling hands. Perfectly postured, hands clasped properly behind your back; you are a lovely sight to me, as I approach. You feel more than hear the lead I attach to your collar, seconds before it pulls you downward to your hands and knees.



“He has such a lovely ass doesn’t he, ladies?” Your head is level with my boots and all you can see around you are the jeweled tones of many cruelly shod feet. “Go ahead have a look and a little tease with it, he enjoys it well enough. Such a good bitch really.”



You feel your ass spread roughly, followed by giggles and probing fingers. Your desire is stretched so tautly honed sharp by hours of anticipation, you can’t help the wanton moaning and ass shaking that accompanies the first penetrating digit.



“My, he really does like it doesn’t he?”



“Mm-mm. such a good boy” an emphasizing slap is added here for effect and the fingers begin working in and out of your tightly stretched hole. You buck backwards against the driving hand, causing Nikki to giggle in appreciation of your zealousness. “What a find you have here, I’m so glad you decided to share his finer vices with us.”



“It seemed like to perfect an opportunity to pass up, dear little Simon here, needed to be shown how much of a whore he really is… and we needed some entertainment.” Your ass continues to be teased and fondled, now and then, an occasional curious hand grasps the shaft of your cock, testing its hardness.



“Oh, more’s the pity, I was hoping this was a punishment.. I would have liked to get a few good licks on that pretty white ass of his.” A cool, unfamiliar voices chimes in. You can’t help but shiver at the promised cruelty in her tone. My chuckle thrills you, and your cock jerks in the unknown hand that grips it tightly.



“Don’t let that stop you Lola, I’m sure we can manage to find something to punish him for, if not simply your amusement. I have quite a few straps, the mere sight of which, makes him tremble so delightfully. In fact, cock-toy, why don’t you run in and fetch them for us.” This statement is followed by an imperious twitch on your leash. You whimper longingly, as the fingers leave you. “Hmm, I have just the thing for you, stay kneeling for a moment.”



You hear the rustle of packaging being removed; the ice cold lubrication startles you, but warms quickly under my ministrations. You feel the head of the plug push against your ass, a moment of pressure then it slides inside. You arch your back, grounding yourself against the palm of my hand, taut with need. I pat your backside lightly before instructing in a soft voice,



“Now be a good lad for your Lady Mistress and fetch our dear friend Lola some straps to abuse you with.” I reach down and unhook the lead from your collar, releasing you to follow my instructions. You struggle for a moment to rise, unused to the tight confines of the corset.



By the time you return, straps dutifully held in your hand, the scape of the room has changed. The coffee table has been cleared and moved to the center of the circle of seating. You can’t stop the immediate falter when you notice the straps fitted around the table legs. The fine ladybirds arrayed around the room, are no longer dressed for shopping. Smart outfits, chosen for style have been switched; traded in for long peekaboo satin gowns, and flirty little teddies all geared towards your soon to be sampled talents.



Our eyes meet and I smile at you; proud excitement, thrilled at the turn of events, the look you return to me is quiet coquettish and send tingles firing through my body. I nod towards the table and you can feel 5 sets of eyes mark your progress across the room, the forced sway of your hips in those torturous heels; Your whores face, eyes downcast properly. Rising to meet you in the center of everything, you can feel the energy running high under my skin. I hold out my hand for the straps,



“Kneel, whore.”



The wood of the table feels cold and unyielding beneath your hips as you settle down on to it. The straps bite into your skin before I set them comfortably but securely around your arms and thighs. The hard swat I lay cross your ass serves as a tiny warm-up as I take my seat at one of the many places around the room, to watch. I position myself where I can see your face as your whipped and humiliated for the pleasure of an acquaintance. Another smile curls around my features while I watch your eyes track Lola; she leaves your field of vision and you tense- foolishly trying to brace yourself for the coming blows.



She teases you mercilessly, stroking you like a skittish colt; prolonging your trepiditous anticipation of the coming pain. Working you like a master player she draws the strap across the skin of your ass, letting you luxuriate in the texture of the leather. A whimper escapes you as she enters your peripheral and you see her arm pull back to deliver a wallop- supple leather caresses, not what you needed; ached for. Your skin itches with the need for chastisement, wanting the harsh strap- you can’t help another wanton little waggle of your delectable ass.



The room fills with giggles at your reaction, frilly skirt shaking around your hips. You feel a firm hand on the small of your back and Lola’s voice penetrates.



“Such a good line here, little slut. Is that hot ass ready to be hurt?” Unsure whether the question was rhetorical you choose not to respond, instead whimpering and pressing back into her hand. A hard slap rocks you forward, stinging hotly. “We are waiting for a polite response, here I heard you had manners about you.”



“Yes, Ma’am please punish me for your amusement. Let me please and serve you.” Your voice is breathy and sounds adorably whorish.



“Since you asked so prettily..”



The first crack throws you forward against your bonds and draws a cry, the quickly following second and third spread the heat over your skin, fiery balm to your already desperate need. You jerk upwards not sure if you are running from the strap or seeking it, dancing beneath it’s kisses. A pause, you feel the room close about you and hands descend to tease and play at your newly sprouted welts.



Murmured discussion and the bodies shift, once more the strap falls. You can tell a new chastiser had taken Lola’s place, these feel less sure but sting more for it; making up in zealousness what they lack in technique. The next break leaves you striving to catch your breath, body heaving. Small hands playing occasionally with the plug still buried inside you.



Again, the strap changes hands. You feel my presence at your head, my hand wrapping familiarly in your hair. Pain explodes through your body over and again, twining hotly with your desire; your world fades to only this. Beautiful bodies swimming around you, lost in a haze; reduced to physical inputs and a burning pool of desire, liquifying deep inside you.



You’re not sure when we moved you, sliding the thick plug free; cock raging with need. The rough feel of the carpet against your welted ass draws your consciousness back, and you feel your arms being restrained above your head; your ankles, somehow, to your thighs. A small pillow is slid beneath the small of your back cocking your ass upward nicely.



Small hips slide into your vision, and a tightly shorn cunt lowers itself to your waiting mouth, you sigh into the delicious musky scent, the velvet texture; letting your tongue swirl and pleasure. You push your face upwards burying yourself in her pussy, cajoling and pleading for the sweet cum you so desperately want. Another hot wanting pussy lowers itself over your body, onto your jutting cock. Your cry is muffled into the snatch perched over your face, tantalizing hot cunt surrounds you.



You feel more small hands gripping your ankles, stretching your legs part painfully; before Lola settles between them, a large strap-on standing out from her pelvis. Your cock spasms inside Nikki’s cunt when the tip presses into your ass. She penetrates you pushing in slowly, making sure you mark every inch as it plunges deep. Suddenly her rhythm takes over and your lost within the machine, your cock only thrusting upwards when she pushes, your mouth working hard on pleasing the cunt above it.



Too much, unable to take it anymore you release; crying loud, your whole body riding the rocking in passion as it crashes over your senses again and again. Nikki moans, her mouth nipping at Morgans breasts, and rides your spurting cock her own orgasm gripping her deeply; Morgan presses her cunt down onto your face cum drenching your probing tongue.



A few small giggles as their bodies relax, though you aren’t allowed to achieve the same, Lola continues working in and out of your ass, quickly returning your cock to it’s former glory, still inside Nikki. She climbs off your giving your cock a tender kiss, before taking Morgan place perched above you. You feel me climb onto your used cock, and it slides into my tight cunt with little resistance.



“Clean her like a good boy, Simon” My pussy works your cock, as Lola fucks your ass hard. You place your lips to her dripping snatch licking your salty cum from it crevices. On the edges of your senses you recognize the sounds of a camera shutter; capturing you pinioned along the floor, legs spread, ass speared on a hard shaft, dressed like my lovely little whore.



Your world narrows further, all attention focused on them pleasing those around you. Thick cock driving into my snatch with the force of Lola’s thrusts behind it. The commingled essences coating your tongue and filling your mouth with spunk. Countless finger tweaking your body, pinching your delicate little nipples; Lola’s hands cupping your sac.



It takes longer for your cock to twitch this time, hips jerking up into my pelvis… emptying gobs of cum into me. My velvet cunt milks away, pulling your hot spunk deeper inside me, for your soon-to-be hunting tongue.



Before I allow my hot dripping little twat to descend over your mouth, my face swims into your pleasure-hazed vision.



“Mm-mm, kiss me Simon… I want to taste it all.”



Our mouths lock together, tongues entwining; the manna of sweet passion fills my mouth and I feel you groan into me- body rocking.



We take our turns, using you like a slut, each time teasing your cock back into painful hardness, working your ass hard. Wheedling every drop of cum from your exhausted body, and you clean it all every last salty drop; making me so proud.



We retire into the kitchen, making some drinks and plans for later, leaving you tied and spread, resting that delightful cock… still tasting your own cum, dreaming fitfully about what might come.

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