Becoming a Mistress

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She gives you, a crossdressing submissive, what you want.
1.8k words
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Chatting on the internet allowed us to meet. The anonymity of the screen gave us the chance to explore what we couldn't have discussed face to face. Inhibitions lost in the technology we used. We became interested, curious. Tempted by the secrets shared between us. New ideas offered thrilled as our own thoughts hadn't. What we wanted to do to each other, in graphic detail. Late night cyber chats led to day time texts, then phone calls. Eventually, of course, we both felt we had to meet. In person. Real human contact. Suddenly the possibility that we might, actually might, do these things; fulfil these shared fantasies, was too wonderful an opportunity to ignore. Our meeting was arranged. The time and place agreed. A Hotel close by booked. A script decided upon. Excitement at the pleasures anticipated overcame our reservations.

On the day, I was late and you were already waiting at our rendezvous. Flushed and breathless from running, I walked over and introduced myself. You, being a perfect Gentleman, stood up and kissed my cheek. Then you smiled at me, looking pleased with what you saw. The spark of attraction was mutual. Yes! We had clicked. This would happen. My thrills of anticipation doubled. Flocks of butterflies took nervous wing inside my tummy. Calmly you took my bag from my suddenly nervous hand, and walked towards the Hotel. I followed as eagerly as puppy at your heels. As I stood gazing around, slightly awed by the magnificence of the lobby, you dealt with the formalities of the reception desk. Mr and Mrs. Double en-suite room. Signed forms and finally, keys given. Room number checked, you lead the way, carrying both of our overnight bags easily. Walking steadily straight ahead.Looking very much as if you belong here, that this is your natural environment. Marble floors and plush oriental rugs, gilded fittings and discrete decor have always meant home to you. Watching your immaculately tailored suit back makes me feel dowdy. Not quite suitably dressed. Ashamed of my plain neat dress and modest jacket. My shoe heels sound too loud on the hard floor but the carpets are so thick I fear to stumble. Too quickly we arrive at our door. A moments panic fills me. Taking a deep breath, I quell the instants urge to turn and run. Instead I step through the door behind you, closing it as I do.

As soon as we enter our Hotel room I unzip you. Reaching to unbutton your suit trousers, pulling them down.Taking your underclothes with them. I kneel at your feet, bending forward to lick the tip of your cock. You stand still and allow this. No words spoken, no other contact. Just me sucking the cock of my new sextoy. It's already hard and pleased to see me. Just a little lick, a taste. I stroke you, enjoying the feel of your skin, then grasp your rigid manhood. Gently and slowly I wank you. Just for a moment. Slide my hand between your legs, up between your buttocks, brush against your tight new fuck hole. You gasp with pleasure. Shock. Fear of knowing how soon it will be violated. Carefully I remove all of your clothes, leaving you naked and vulnerable before me. I casually drop my jacket and strip off my own dress, revealing myself to you. Standing in my red basque, matching panties, sheer black stockings. Black high heel shoes. My finger nails and lips coloured the same shades of red. I lick them shiny as they slightly open with lust when I gaze at you. The only sound our breathing. I carefully touch your skin. A painted finger tip trails along your arm, across your chest. Pausing to circle, but not touch, your peaked nipples.

"I shall redress you as my sex slut Bitchboy," you quiver slightly at my order.

Sheer stockings with lace tops are carefully unrolled up each of your legs. A suspender belt of white lace fitted around your waist, then attached to your stockings. Pretty white girlie panties; see through and soft, clinging to the outline of your hard-on within are eased on next. I play a little; amusing myself by stroking and kissing you. You ask nicely if you may be allowed to fondle my breasts. Wanting to touch my nipples. "Kiss them perhaps?" You beseech softly, hopefully. I nod to permit this. Shaking hands tenderly reach for my tingling breasts. Lifting one easily from it's lacy cradle. Allowing you to reach it's hard rosy peak and nuzzle it. Suckle from me. Take the swollen teat into your mouth and flick the tip with your cool tongue. As your breathing quickens and catches, I move away, pulling myself from your mouths grasp. A small disappointed moan escapes you.

"On with the rest of your outfit," you're told. I lick, kiss and suck your nipples before we cover them in their bra, leaving them wanting more contact. The pvc is cold. Clammy against your warm skin.The fake implants slipped inside to fill the cups. Giving you an almsot believable bust. Adding finally the blonde wig. It needs brushing. Leading you by the hand, I take you to sit in front of a mirror. I press my full breasts to your back as I lean against you, gently straightening your new shoulder length waves with a hair brush from the dressing table. Smiling into your startled eyes through the glass. A little make-up for you. Lipstick - sweet pearly pink, then black mascara; framing your sparkling blue eyes. "I want my Bitchboy to be pretty for me." I tell your reflection, smearing blue cream eye shadow across each of your lids in turn. White glossy high heel shoes are placed on the floor before you, for you to step into.

You walk unsteadily across the room. Around the huge high bed. Showing me how your hips sway and wiggle. Gasping as you feel the brush of your balls against the silky panties. "I want you to Strut for me slut." I say. Urging you to show off your body for my pleasure. "Know how sexy and desirable you look. Know you will soon be mine. Totally. All of you," huskily instructing you.

I lie on the bed to watch, panties pulled aside, fingering my own slit. Licking my pussy juice off my fingers. Gesturing for you to come closer. I kiss you, letting you taste me on my lips. I allow you to lick my fingers as they dip in and out of my tight wet quim.

"I'm so horny from watching you" I whisper as I cum, shuddering with pleasure and desire. "I want my Bitchboy to nuzzle my crotch, through my damp panties." I order. You can smell my musk, as you lick at my pussy; separated from your eager tongue by the sheer silk. So close to your ultimate goal, and yet, unable to fully enjoy my slippery clit against your mouth. "Oh please?" you beg "Pretty please Mistress. I crave the taste of you" I smile slowly. Loving the idea of giving you a small reward, an incentive to please me. "You are permitted to touch and taste my warm wetness. Just for a few moments. Then you must please me to earn more." Quickly your fingers hook aside my covering as you rush to bury your eager tongue into my wet cunt. Sipping the nectar of my pleasure from my swollen pussy lips. Lapping at my hot, hard clit. Making me clench as I cum again. When finally my shudders subside, I release your head from the grip of passion holding your mouth pressed into me. We kiss, sharing my juice with entwined tongues. Smearing each others lipstick as our mouths meet.

We look into each others eyes. Both knowing this is the moment we have been waiting for. Cherry popping time. "I want my pretty Bitchboy slut on all fours in front of me," you're told firmly. You move to kneel at the end of the bed. Bum towards me. Accessible to my hands, my fingers, my tongue. Waiting for me to take whatever pleasure I wish from your pretty body. Any part of you that pleases me. I stroke your hot cock contained within slippery panties. Ease them down to your knees, and tickle your warm full balls. Bending under your body to suck your knob head. Lick down your thick shaft. I reach to pinch your nipples hidden beneath your clothes. I kiss your sticky lips, taste the lipstick on them. Slipping my warm tongue into your mouth. Little darts of my tongue fucking your lips, sucking your tongue...and all the time my warm hands are gently caressing your bum. Sliding down and up the crease. Brushing against your puckered bud. My fingers spread my cum juice around your little hole, making you wet and slippery. Then I laugh at your gasp of surprise when cold lubricating gel meets the hot of your ass.

When I think you are almost ready, you ask me nicely. "Please Mistress?" you whisper. One fingertip, just one to start with, circles your tight pleasure place. It nudges against you. Pressing more urgently, testing the seal. Now I move behind you so I can lick where I touch. Begin to press with my tongue. Rhythmically touching your exit until it relaxes and allows me entrance. My finger slides inside. Gently, slowly, pushing deeper. Feeling you tighten and release as the waves of guilty pleasure overcome instinct. In and out, thrusting further each time. Your hips start to buck as I finger fuck your ass. Unconsciously pressing your butt to my hand. Forcing my touch deeper within. Your constrained cock bulging hugely within its silken cage. Whimpers and groans of delight at this new experience escape from your compressed lips. Internal muscles clench at my intrusion, speeding you towards a climax. I thrill to hear my sweet Bitchboy moaning with pleasure, begging his Mistress for more, harder, deeper. Telling me how it feels to be finger fucked for the first time. I can feel your body writhing with delight. Arching against me. Showing me how much my pretty slut enjoys being my sex toy.

The delicious new sensations make you cum. Your cock visibly throbs as your hot cream pours forth. Wetting your new girlie lingerie. Seeping though the fabric, making them transparent. Your balls pressed tight within their confines. Tormented by the thong against your still tender, newly fucked hole. When you finally regain control of your breathing, you look up at me smiling shyly. Make up smeared and sweated off your face. "Oh good Bitchboy." I praise. Glorying in the power and control I have. "My own personal sex slut." I say quietly. Smiling as I bend to gently and tenderly kiss your un-coated lips. I have claimed you as mine. Fully thrusting into your soul and truly becoming your Mistress.

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7 Comments
Greyfox69Greyfox69almost 13 years ago
Why?

Why did you stop writing? I thoroughly enjoyed your story. Please don't stop. Thank you.

AnonymousAnonymousabout 15 years ago
Great!

Loved this...take me just this way...my panties are wet!

AnonymousAnonymousover 17 years ago
mmmmm

Bizarre...but so very sexy....my mind said "not sure" but other parts said "yes"

AnonymousAnonymousover 17 years ago
Made for the Mistress role

You certainly enjoyed the role Carol. You seem to relish the thought of having a male plaything and you certainly like to play! I'm sure many a man would succumb to you if you dressed like you describe.

AnonymousAnonymousover 17 years ago
I would were it be me

It is very easy to picture myself in the place of your gentleman. The story conjured up images that excited me, and maybe I shall try to recreate it in some way. I dont usually wear ladies' nice things, but the circumstances are within my sphere of activities that I would like to try. Thank you

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