tagTranssexuals & CrossdressersA Working Sissy Girl

A Working Sissy Girl


I look up at my boots. Cute! Received delivery just day before yesterday, my boy friend hasn't even seen them yet. He'll like them, know he will. 3" spike heel ankle boots, very shiny patent leather, I look up at the one on my right foot. I run my hand down the thigh-high lace top seamed nylon coming up out of that boot and let my finger feel the boot heel, sharp! You could hurt someone with these boots if you weren't careful. That's exactly the image I was looking for when I ordered them.

I look over at the balding head moving up and down between my legs, the top of his head is all I can see, my thighs closed softly around the sides of his face. He's trying to please. I know that and actually he is, feels real good having my ass licked like this. But I'd never let him know that. His face is buried between my cheeks. I have my legs pulled back to my chest, spread slightly and just enough to hold him in place, make him have to work for it. I look back up at my boots, raised up above me as I lay on my back on the bed. I made the right choice, they are very hot, so very cute!

I bring the riding crop I'm holding in my right hand down across his back. Not hard enough to leave a mark but hard enough to make a 'snap' noise, get his attention, feel him shudder as the crop meets his flesh, "I told you, long slow strokes! Can't you do anything right!" I bring the crop down across his outer left arm. He's naked and on his knees, hands cuffed behind his back. He's kneeling at the edge of the bed I'm lying on. I'm on my back, my rear end right at the edge of the mattress and up in his face. He starts to apologize...

"Mistress, I'm..." I cut him off before I hear the next word. I know it was going to be 'sorry'.

"Shut up you fucking bitch, shut up! I'll tell you when to talk. You just lick until I tell you to stop, show me you love me. You can do that for me, can't you? Should I have you stop? If you love me you'd better find a way of showing it!"

I see his face raise up toward me, put the crop to his lips before he can speak. I stare sternly back at him. "Lick!" I pull my legs up tighter, expose the crack of my rear completely. I feel his broad flat tongue start to run up full length between my cheeks, feel it as it brushes across my tiny hole repeatedly. He really is trying to please me.

That makes me think about my boyfriend and how it must feel when I do this for him. Like to do that for him on my knees, kneeling behind him, feel his super muscled tight cheeks in my hands. Sometimes pull his cock back between his legs from behind and suck him like that as I lick him too. I think about him using my tight little rear end the way he does. Want him to use it good later tonight, want him to fuck me silly. I need that. It's all I can think about, feel my little thing start to stir as I picture him walking through my front door.

I look down at the man between my legs. He's older than the other two men I see, has to be in his late sixties. He's out of shape, overweight with just the hint of man-boobs. And he has a little dick too. Not as small a tiny little boy thing like mine is but he's a man I would never choose to have sex with in a million years. And although he's not unpleasant to look at he's not my type at all, not what I consider a real-man.

He's been worshipping my rear for almost forty-five minutes now. Started with me having him kiss my cheeks very soft and gentle, I had to have him please me like that before I allowed him to do the real good stuff. Feel his tongue just touch the base of my tiny soft balls and then start over at the small of my back. "That's right baby, now you're doing it the way I like." I pat his head, look over at the two of us in the mirror. "You remember that technique, I like it."

I look at my dress pulled up around my waist. Soft leather, so tight, had to wiggle it on up over my hips for him. I look at the black lace panties dangling from the ankle of my left boot. Those boots again, love them! I look down and see my little thing, not even a hint of erection from this man at my rear. Soft little sissy girl penis, think of my boyfriend again, feel it stir.

I look at my watch, ten minutes left to go. I reach down and push his head away. I snap my fingers and point to the floor. He shuffles back on his knees from the edge of the bed, almost falls over. He is quick to correct himself and fall forward, puts his face to the carpet. I straddle him, unlock his cuffs. He stays completely submissive and motionless on the floor before me. I take it all in, like it, completely naked and helpless. I toss the cuffs to the side of him, hear them make a loud 'clank' as they hit the floor. He looks pathetic like this, so vulnerable. I wonder if anyone ever sees him in their mind's eye in court like this. He after all is a judge, a very powerful judge I'm told.

"Dry me. You got me all wet and messy, you naughty little boy. Move!" He takes a towel he took from the bathroom earlier and carefully folded as he knelt before me, had me inspect it before he asked permission to lay it on the bed, corners perfect. He gently runs the towel up between my cheeks, wiping my rear end dry and clean. He is very good at this, so gentle. I turn my back to him, reach back and spread my cheeks.

"You may help me dress." I don't wait for him to ask, he knows what I want. He helps me step both feet back into my panties, pulls them up and as I reach down and tuck my little penis back between my legs he raises them up over my rear. Feel him staring at my rear from behind, I push my butt outward very close to his face. "Kiss, baby." Feel him kiss each cheek once, gently. He pulls my dress back down over my rear, adjusts it just above my knees. I tap my hand with the crop I'm holding.

"You want to show me that you love me, don't you, baby? Want to show me how much you really care?" I look back over my shoulder at him, glare down at him.

"Yes, oh yes, please. I do love you, I...", I walk to a chair and sit, cross my legs so that he gets it all in, sees my legs spread slightly and then close. I let one cute little boot move slightly up and down, "...please, I..." I can see his small erection poke up from between his folded legs, sitting back on them hands at his sides. I know all he can think about now is touching it. I stare at him.

"Shut up. Do it." I watch as he starts to masturbate. Think about my man and his very big cock, nothing like this less than average man. I think about wearing only these boots with white lace ankle socks showing just above the top, think about being made up, clean baby smooth and slippery when he comes through the door. I think about being pushed up against the wall and felt up, think about kneeling in front of him a real man...I start to get hard.

"I love you. Mistress, I love you." His eyes are closed and he's rocking slightly back and forth on his knees. He's pumping his dick with one hand, holding his other hand out in front of it, he breaks my thought, feel anger for a split second. I turn my attention to him

"Not one drop on the carpet, you spill any of that disgusting stuff on the floor and I will whip you! I'll send you home with stripes on your ass!" I uncross my legs, lean forward. "Not one fucking drop, baby!" I pick up the crop and slap the floor hard with it.

He pumps hard, struggles at it. I smile to myself. And then it happens. He cums into his hand, tiny spurts, more like it softly drips out. He catches every last drop. Makes me think, he really is a good boy. He finishes. His whole body goes limp, like his little dick. Then I see his head hang, looks down at his hand, his shriveled penis, I know what he's thinking. The whole think took less than three minutes.

"Good boy, very good boy. You please your Mistress very much." He says nothing. I know where he's at now and I'm going to exploit it. I know where he is in his head. He's ashamed of what he is, but powerless to stop it. After we cum, that's when we feel it.

I stand, walk to the front of him, "Show me!" He raises the hand full of his cum, keeping his head and eyes lowered. I walk around him, let my crop brush across his shoulders and down his back to the crack of his rear. "You feel shameful, isn't that right, baby?" He mumbles 'yes'. I pat him hard with the crop across his butt, pat the back of his balding head, "Say it, say it now!"

"I feel shameful, feel ashamed of myself, Mistress, for what I do, what I am." I drop the riding crop at his side. I reach down and run two of my fingers in the cum in his hand, bend forward and pull his chin up toward me. I smile down at him. I run my fingers around his slightly quivering lips, let them just tease inside his mouth...he wants to cry, I can tell. "You want to cry for mama, right, baby? It's okay. Come on, you're such a good little boy. Cry for mama." He starts to whimper and then cry softly. "Let it out, this makes your Mistress happy." I pat his head, watch him sob softly, real tears come down his fat cheeks.

"You know what your Mistress wants now, baby. You know." I watch as he licks the cum from his hand, tears in his eyes. He can't look at me. He truly is ashamed of himself. I say nothing, just watch as he cleans his hand with his eyes closed. When he finishes he keeps his head bowed.

I walk to the mini bar, pour a drink, bourbon. I check my make up in the mirror. Not a smudge, still the perfectly cute sissy girl I was when I walked in the hotel room a little over an hour ago. I look at him in the mirror. "You may dress, baby. I'm through with you for now." I look back at myself in the mirror. Black leather mini dress comes up around my neck at the top, shiny silver large hoop earrings, tight black spiky hair, curls up just around my ears, very nice. I look like a real girl. Just a hint of the sissy boy I actually am. I like that, really like that. I reach back and smooth the rear of my dress, check myself out in the mirror.

"You want a drink, honey?" I smile at him. I don't wait, I fix him a vodka, one ice cube, know what he likes. I walk to him as he is buttoning his shirt. Hand it to him. "You were wonderful today, really were. Did you have a good time?"

He takes the drink, "You know I do, just go through the adjustment period after all this over." He raised the glass to his lips, tosses the whole drink back and swallows.

"Believe me, I know. But you can't stop, neither can I, the itch will start again soon." I reach down and put my hand on his dick through his underwear. "You'll be thinking about this, jacking off all week to this dirty little thing we do, you know you will, baby, probably as soon as you get back to your office today."

He laughs. "Yep. You really are the best." He puts his hand on top of mine. I pull it out from under it, slowly. Give his dick a gentle pinch as I pull my hand away.

I walk back to the bed and sit on the edge of it, sip my drink as I watch him dress. "So does your wife do anything like this for you, treat you all mean and nasty like the dirty bad little boy that you are?" I smile at him, give him sexy wink.

"Fuck no, she'd never even think to do any of this. I get a blow job maybe once a month, at best. And she's not even good at that. She has no idea what I'm about. For her, it's about the country club, cars, summer homes and dinners." He ties his tie, stands in front of the mirror.

"But I know you, don't I? Your dirty little therapist that knows the real you, honey, that's me." I stand, walk up beside him and fix myself another drink. "You want to make this a regular day thing or just keep it on-call?" I sit on the edge of the dresser, stare up at him. "We can do every Tuesday, or if that doesn't work some other day. And we can do more than one hour too, if you like. We can do evenings too. Up to you, baby." This is the fifth time I've seen this man, I know him inside and out. He'll be seeing me much more.

"I'll call you. I like the regular thing, maybe a scheduled day and time." He turns to me. "I think about you all the time, think about doing what I do for you. Masturbate sometimes twice a day, have done it at my office, like you just said!"

"I know you do, baby. Believe me, I know you do. And that pleases me like you'll never know, love it that you think of your Mistress. And she knows just what you need." I lean forward, pat his shoulder, kiss him on the cheek. "Ooo, you have hot red lipstick on your cheek, better not let her see that." I laugh and walk back to the chair, sit and watch him wipe it off, finish dressing.

I also know the drill. Can't leave the hotel room until he's one half hour gone, I sit back and pick up the tv remote, turn on the set. He turns and reaches into his pocket, pulls out a money clip. He takes three one-hundred dollar bills off of the clip and as he approaches me I hold out my hand. I sip my drink as I look up at him. I take the bills he places in my hand, fold them and tuck them into my bag next to the chair. I wink up at him as he smiles. I set my drink on the table in front of the chair, stand and walk to the door with him.

I push myself up against him, push the soft leather of my dress against his very expensive suit, feel his hand go to the small of my back. "Ooooooooo, baby. Purrrrrrrrrr, never had you touch me like that before. You want to kiss me, baby? Ever think about that?" He starts to move toward my lips, I move my head to the side, dodge him quickly. Whisper in his ear as he runs his hand down over my rear end, "You gotta work harder to be a real good boy for that treat, I'll let you know when, French kiss my little bitch when he least expects it. Maybe even touch your dick with my hand, I know you think about that." I sigh into his ear, up real close, "Mama says 'when', not you, honey." I can feel him start to push up against me, feel his erection start to grow in his pants. I run my hand up over it, "You think about me, you think about me and only me. I am your only Mistress." I pull away from him, slap his rear hard with my hand. I reach up and flip the latch lock at the top of the door 'open', step back away from him brushing his hand off of me.

"Say it."

He looks down slightly, sheepishly. "Thank you, Mistress. Thank you."

"Who do you love? I stare at him as he looks up so submissively.

"You, Mistress, I love you, adore you."

"Good boy." I walk back to the bar, one more drink, I have a half an hour to kill. "Go!"

I don't look at him but see him in the mirror as he opens the door and closes it behind him as he leaves. I walk to the edge of the bed, sip my drink slowly and put the glass on the table. I wiggle my skirt up underneath me, put my hand down into my panties. I pull my soft penis up from between my legs and slip my panties down around my ankles. I think about my man. The man that introduced me to the judge, the man I hope to please later tonight. I think about sucking him, think about how he tastes in my mouth. I feel my penis get as hard as it can.

When I cum, I stand and do it onto the floor. Watch in the mirror as my tiny thing spurts out and onto the floor of the hotel room. When I finish I take the towel from the edge of the bed and wipe myself clean. Standing there with my dress up and my panties hanging off the tops of my boots I lean down and pick up the glass from the table. I toss back the last of the drink in it. I put the glass back on the table, pull my panties back up and lower my dress. I walk to the mirror and take my lipstick out of my bag, fix my lips bright, bright slutty red. I adjust my dress and blow a kiss into the mirror.

I hurry to pick up all of my toys. Put the cuffs and riding crop back into my huge bag, put it over my shoulder and walk to the door. I look back into the room to make sure I didn't forget anything. I see my cum all over the floor. That makes me smile. I close the door behind me and head to the street to catch a cab home. Have to get ready for my baby, I smile as I walk to the elevator and head to the lobby. I hear my pointy little dangerous boots as they move across the tiled floor, 'clicking' so cutely. I made the right choice with these boots. It's been a good day.

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