We meet in a bar, me, my best sissyboy painslut & you. We are all dressed in everyday office attire; you boys look so professional in your suits. I have on a tight white blouse which strains a little at the buttons, the sheer lace of my bra clearly showing through; a straight black skirt, net stockings & heeled patent black pumps. There are other such groups in the bar & we don't look out of place as we choose a quiet corner table; however I'm willing to bet that none of the other suited men have silk panties on under their pants, nor that any of the power dressed women are wearing open crotch rubber shorts under their sober skirts. We take our seats & you boys sit as instructed next to each other on the bench seat while I take a chair opposite.
I lean forward & make the introductions & ask whether you're both wearing your frillies. Painslut reaches into his waistband & twangs his thong elastic & you just look uncomfortable but nod yes. I smile, pleased that my boys are so obedient. I explain that I have booked a hotel room in the next street & tell you how much I'm looking forward to you boys getting to know each other better. You look very handsome & it's hard for me to reconcile that this is the boy whose cross dressing cum-shot I have as my home pc screensaver. The one where you're squatting in your red high heels, thighs open as far as they can go, your thick, red turgid cock sticking straight out at me from the crotch of your sheer black pantyhose, a thick rope of cum hanging from the swollen head.
I know that by this point painslut is hard & ready in his white lacy thong, just the fact that we are all here together is enough to make him hard & as I casually tell you both about my plans for the evening I'm hoping that you are getting hard too; your beautiful fat shaft throbbing in your red silk panties as I outline what I need you to do. I notice that you're flushed & ask you if your erection is making you uncomfortable in this public place, you look surprised that I know, then you smile & nod. Staring at you I tell you that you're not alone & reaching under the table I take your hand & put it on the bulge at painsluts crotch, squeezing his huge boner with your hand; he squirms a little with pleasure & slides his hand onto your lap, slowly stroking your hard silk clad cock, using 2 fingers to trace the outline of your cockhead as he smiles at you. You swallow & look at me noticing that my nipples have hardened & are showing through my blouse.
You tell me later that you felt terrified at this point, painslut & I have been sceneing for years but you didn't really know us at that point & could have been heading for a really nasty night, although you admitted you also felt so excited about finally making real the fantasies & desires we had chatted about online.
I suggest that we drink up & head for the hotel, we all know that it's not really a suggestion but an order. We leave the bar, me walking between you both a hand on each of your asses stroking as we walk the short distance to the hotel. I tell you both to hold the elevator as I get the key from the desk. We're the only ones in the elevator & I stand between you facing you both & gently rub your cocks through your suit pants as we climb to the 29th floor. Painslut moans & gazes lustily at you, then leans over reaches for the back of your head, pulling you towards him & kisses you full on the lips right in front of my face; your cock twitches under my hand at the kiss & I squeeze it lightly as you kiss him, your tongues entwined as I stroke you both.
The elevator stops & we walk to the room, this time I'm leading you both by the front of your pants. I open the door & hang the Do Not Disturb sign on the outside, locking the door as you both walk into the room. I tell you that I'm glad you're getting along but that there'll be no more kissing 'til I say so, I have you stand facing each other in front of the huge window. I draw back the net curtain & turn on a floor lamp so you are illuminated in a pool of light in front of the window; several lights are on in the office building across the street, I'm hoping there's someone working late. You gaze at each other as I sit on the end of the bed & order you to begin stripping each other.
I watch as you undress each other revealing your hard torsos, stiff nipples & sexy panties. Painslut's cock is clear of his thong by a full 2 inches & I see a smear of precum on his slit; your prick is clearly outlined by the red silk of your tight lace edged panties, pointing to the side, the dark stain of your precum spreading, betraying your arousal. You glance down at painslut's cock throbbing against his belly & swallow; I notice your cock twitch inside your panties as he reaches for your hips & pulls you close so that your silk clad shafts are pressed together. You are obviously longing to kiss again but I'm not about to let you.
With one swift movement I remove my skirt to reveal my shaved pussy framed by the shiny black latex, garter snaps holding up my net stockings, parting my thighs to show my slick rouged labia I reach into my bag & pull out a thick double ended jelly dildo & lay it on the bed beside me.
Walking toward you as you stand together hips pressed together & gyrating slightly, silk against silk, cock against cock, eyes glazed, breathing shallow, leaking precum as your darkened cockhead grazes painsluts, his tongue slipping out over his lips longing to kiss you.
I grasp both of your swollen tips in one hand & squeeze, then unbuttoning my blouse I free my huge tits revealing my saucer sized rouged nipples & offer them up to your mouths. You both bend to lick & suck my long stiff nipples; I bring them together, your tongues so close to each other now. Painslut groans & I ask what the matter is - please Mistress boy wants to suck - I smile & reach down to free your throbbing prick by guiding it out of the leg of your panties, watching as it bobs in the air stark against the red silk.
-Is that what you want slut? - I ask painslut, his eyes so big - oh yes Miss! - He replies. And what about you I ask you as I guide painsluts veiny 9 incher out the side of his thong - y,yes please Miss - you splutter. -Well I'm not sure that you know how to suck a cock do you? - you both nod as you gaze at each others dripping rods. - well we'll see about that-
I reach for a chair & position it in front of the huge window & sit while ordering painslut to fetch the double ended dildo from the bed. I order you both to kneel in front of me; your eyes are now level with my smooth wet pussy. You both look so beautiful with your massive swollen members sticking out from soft silk panties.
Parting my thighs wider I stroke the dildo along my pussy lips, the coldness so arousing to my fevered lips, you both watch silently as the head of the rubber cock becomes slick & I tilt my hips forward to take it inside my hungry cunt, squeezing the dildo with my pussy muscles making sure the hard cold head is right against my g-spot. I sit up a little to make sure that the flexible rubber dong is rubbing my clit. What a sight; Mistresses big rubber cock sticking out from between her stockinged thighs.
You both swallow as you gaze at me - so lets see whether you do know how to suck cock boys- I beckon you both to crawl nearer & position you one on either side of my jutting dildo, pushing your heads together, ordering you to lick it, take turns sucking the head & deep throating it. The sight of that dildo disappearing into your oh so male mouths making me so hot, so wet. As you grip the dildo to suck the head & stroke it like a real cock the other end moves inside me. The air is filled with squelching & sucking sounds, my head is reeling as the dildo rubs my g-spot & clit as you both suck & stroke its fat shaft, your mouths & tongues entwining. My cunt muscles clench in spasm & I shout out in climax as a movement in the building opposite catches my eye.
Still panting from my subsiding climax I look down to see that you are both still licking & sucking the dildo that juts obscenely from between my strong stockinged thighs but you are mainly doing so as a means to have your tongues touching, not quite the forbidden kiss but close. Looking lower I notice that there is a serious precum situation happening. I order you to both stop your attention to the dildo & kneel one at each of my feet, again you are both so obedient, so eager to please your Mistress.
Lifting my left leg I place my shinily shod foot on painsluts shoulder, his head immediately turns & he begins to lick the glossy black leather as he has done so many times before. Smiling at you I pull the dildo out from between my swollen lips with a sucking pop sound, I beckon you closer & hold it out to you, all slick & sticky with my juices. I notice painsluts eyes watching you as he worships my left foot, we both watch as your tongue snakes out to lick the dildo's sticky tip, your bottom lip staying full as you lean forward & take the head in your mouth, relishing the taste of my cum. –Good boy- I say as I push the dildo further into your mouth making you gag a little, - just relax now-
Painslut groans & I look to see he has abandoned his shoe worship & is staring wide mouthed at you as I fuck your throat with my cum coated dong, the tears springing from your eyes as you try not to gag. His cock is the hardest I've seen it without pain being involved & his eyes are so wide. Does he envy the dildo being in your luscious mouth? Does he envy you the taste of my pussy, though he's had that so many times before? Or does he envy the pain you're feeling right now? Either way he has disobeyed me by stopping licking my shoe & must be punished.
Removing my foot from his shoulder I kick him hard in the chest, your eyes swivel to watch but wisely you keep on sucking the dildo I'm feeding you. Painsluts eyes glow at the pain of the kick & he looks up with a contrite face – so sorry Miss, but I couldn't help watching- he whimpers; - exactly cunt! You just can't help yourself can you? Which is why you need so much training; turn around – he turns on his knees so that he is facing the big picture window, watching me in the reflection of the darkened glass. - Head down cunt, don't think I can't see you're still watching – he lowers his face to the floor & raises his butt in the air in the classic pose of submission.
You're still watching & sucking, drool cascading from your open mouth as you are face fucked by the thick rubber toy. I order painslut to open his thighs a little & as he does so I drag the 4 inch steel stiletto heel of my left pump up the inside of his hard well muscled thigh, leaving a long dark scratch as the metal tears his skin. A muffled moan escapes his lips & his cock jumps at the sweet pain, smiling I ask if he liked that – oh yes Miss! – he replies, face mashed into the carpet. I repeat the action on the other inner thigh, this time pressing harder, grinning as tiny drops of blood prick to the surface of the scratch almost immediately. I move my heel higher this time using it to press his right testicle upwards against his pelvis; he winces & moans as the sharp metal heel bruises his tight purple scrotum.
Leaning forward a little I aim a fat gob of saliva onto his twitching puckered asshole, he jumps as my spit hits the target, next I drag my heel up from his congested scrotum up the taught flesh between his balls & ass; he sucks his breath in sharply then moans again. Planting the toe of my shoe firmly on his coccyx I rock it back & forth a little taking aim with the sharp square heel of my shoe. Painsluts body is tense with anticipation; gooseflesh springs up on his back as I slowly plunge the metal heel of my shoe into his asshole inch by inch; he cries out with the pain & shudders as a thick stream of involuntary cum hits the plush hotel carpet, such a rare & special boy. You wince, your eyes on stalks as you watch a thin stream of blood trickles from painsluts asshole. I grin & reassure you that I won't treat you this way............yet.
Pushing the toe of my shoe on his back again I slowly withdraw my heel & order painslut to clean up his disgusting mess but to keep the cum in his mouth, we both watch as he laps his pain induced jism from the thick carpet, his cock still rock hard; I slowly pull the dildo from your mouth & ask you if you are enjoying yourself – yes Miss, of course Miss – you reply – good answer boy, now because you've been so good I'll let you kiss him- smiling painslut crawls over to you with a mouthful of his own cum, gazes lustily at you & moves in to kiss you. Your face shows distaste as you've never tasted another man's cum before but you lean in for the kiss anyway; after all isn't this just what you'd said you fantasised about?
Your mouths meet, painsluts tongue darting out to touch yours, transferring some of the thick cum right onto your taste buds; you reach out for him, pulling his face into yours & kiss him passionately – obviously you like the taste! I watch you kiss like teenagers, hungry for each others mouths, hands starting to roam over each others bodies, cocks straining against the leg elastic of your silky panties; getting wet again watching my beautiful sissy sucker boys getting it on. I think that it's almost time to test those sucking skills for real.
I walk slowly around the two of you as you kneel, passionately kissing, your hands exploring each others torsos, working slowly down to your straining erections still framed by your sexy silk panties. Watching you is so erotic to me, two well built handsome straight men making out with each other in frilly underwear because I have ordered & you're loving it!
When we planned this online, I told you of my fantasy to see two pantied sluts 69ing, becoming so wrapped up in the sensations & forbidden nature of what they were doing that they became oblivious to rest of the world; which would allow me to watch very closely & toy with them both if the whim took me. I feel that time is now here.
In front of the large window is a long, low coffee table, about 5 feet long & 12 inches high, still watching you kiss & fondle each other I move this table until it is next to you, right in the centre of the pool of light from the floor lamp. I stand behind you both, facing the window, watching your flushed faces & rapturous expressions, sensing my closeness you break the kiss. You both look up at me & painslut reaches for your balls, his touch making you shiver as he slowly cups your dark congested scrotum. I nod & he stands up still holding your balls so that you must follow, I then run my hands over the sensitive skin of your chest & belly & around your waist & buttocks; your cock twitching at our combined touch. I grasp your turgid pole firmly & guide you onto your back on the low table, your feet planted on the floor, your still rock hard prick standing proud & visibly throbbing in the air; what a view this must be for anyone in the building opposite.
Next I lead painslut around to the end of the table where your head is, his fat 9 incher pulsing in my hand, the velvety skin so familiar to me, tiny dark scars & imperfections reminding us both of past fun; he swells even more at my touch & smiles. Smiling back I come around the back of him & kick him hard in the right calf causing his legs to buckle, he falls to his knees, your face is tilted back to watch us & now you find his glorious, thickly veined leaking tool is almost touching your face; you inhale his musk & stick out your tongue to finally taste him as I firmly push his head down towards your cock.
His tongue snakes out as I push him down, licking your belly edging forward on his knees to straddle your face, you tilt your head back more & begin to lick his slimy precum coated cockhead; he shudders at your touch & I press his head harder into your groin & you feel his hot wet eager mouth envelope your painfully hard cock up to the hilt. Gripping the edges of the low table painslut begins to suck you up & down, his tongue swirling around your fat cut cockhead, flicking into your slit, his saliva dribbling over your balls & onto your asshole as he works you with his mouth. You moan at the fabulous intensity of feeling his hot mouth is giving you, after almost an hour of being hard with little physical stimulation being sucked is almost too much & you fight hard not to cum. Your tongue & lips are chasing his huge prick, longing to take him in your mouth, desperately wanting to give him the same mind-blowing sensations you're feeling; wishing that he would fuck your face, gag you with his girthy, well veined rod, feel his uncut foreskin unfurl in your throat.
But painslut is playing with you, using the advantage of being on top to tease you with his cock, bobbing up & down, just missing your eager mouth on purpose; you growl, a low animal sound of longing. I look up from where I have knelt by your hips watching closely as he sucks you, memorising the look on his face, his joy at finally sucking another man for me & see what he is doing; standing I quickly reach for my crop & bringing my arm back as far as I can I strike, the hard seam of the leather cutting into his buttocks, his body jerks with the pain, his cock pulses nearer to you mouth now – stop teasing him cunt, now fuck his virgin mouth – I growl pushing his ass downwards & kneel by your head to witness the moment you finally get your first taste of real cock.
Your eyes are wide as you feel his magnificent cockhead enter your eager mouth at last, his smoothly shaved balls brushing your nose as he pushes his cock home with a moan, his ass bobbing as he makes short slow thrusts, testing your gag reflex. Your eye is drawn to the thong string in his ass crack standing out starkly against his hard flesh, the string & his asshole still showing dried blood from his earlier shoe punishment; you recall his spontaneous ejaculation in response to that pain & begin to swirl your tongue around his thick shaft as he slowly fucks your mouth, you long to taste his cum again.
I watch as your eyes glaze over & your hands find his hips, gripping him as you mirror his movements & rhythm on your own cock so that it feels almost like you're sucking yourself; both losing yourselves in the intensity of the feelings the other is causing. Smiling I rise & resume my seat on the arm chair, selecting a slim curved vibe from my bag I watch the show that I have waited so long to see played out on a low table in front of the huge picture window. I speak breaking the reverie – now boys you must please Me before you please yourselves – I say switching on the vibe & slowly beginning to stroke my slick pussy lips with it, long slow strokes from ass to clit, teasing myself, dipping the head briefly into my cunt as I watch you deep throat each other.
–Now boys I want to see your faces properly, get up a little & worship each other's cockheads – your weight shifts as painslut adjusts his position, simultaneously you glide out of each others mouth & take hold of the others slimy throbbing cock, both gazing at the others beauty. You stroke painslut a little, watching his foreskin unfurl across his glans, exposing the dark helmet, licking it with your tongue outstretched making him shudder as he grips you & begins to lap at you too, tasting your precum. Watching you both licking as instructed knowing that you both want to plunge back in to a full 69 & fuck & suck 'til you're spent I stroke faster with my toy, rubbing my swollen clit with the base of my vibe as the head slides in & out of me but it's not enough, I need to be involved. – Next from the bag comes my strap-on harness with a thick black 10 inch dong attached, holding the vibe in place I step into the harness & secure the straps trapping the curved vibe against my clit & g-spot. Kneeling by your hips I shove the head of my strap on into painsluts mouth, leaving your cock exposed as he hungrily sucks knowing that the wetter he makes the dildo the easier it will be for him; my hand moving between your thighs, lightly squeezing your balls, sliding my middle finger into your slimy man cunt, massaging your prostate, your cock swells anew & you groan I know that if I continue you will cum so removing my finger I move around to the other end of the table, painslut resumes his licking of your beautiful cut cock, your hips buck slightly trying to push into his mouth as you so desperately need to cum.