tagTranssexuals & CrossdressersHis Sissy Bitch Ch. 05

His Sissy Bitch Ch. 05


I'm scared to death. Feel apprehension, I've never been 'outted' before, never been out in public dressed fem. He will not be dissuaded, told me I had to do it. As I sit and try to concentrate on work I can see him across the hall in his office. See the people he meets with, know he could out me to them if he liked, and I know tonight I may be seen by any one of them. He's taking me to a club, so he says; don't even know where that is.

He looks up from his desk, looks through his class window wall of his office, looks right at me, smiles. I feel my face turn red. I feel the penis restraint he keeps me locked in, feel it under the silk panties I wear for him under my pants. In the office I dress straight, would never even hint at being what I actually am for him. But he knows. And so do I, feel his control over me every time I move. I'm reminded of what I am to him every time I have to go to the men's room and sit to urinate. Feel it every time I pray that nobody else in the office notices.

My office phone rings, it's him.

"Are you looking forward to tonight?" I look up see his door closed; his blinds have been pulled on his glass walled office. I can 'hear' him smile through the phone.

"Yes, sir, I am."

"Good. I want you to leave early today, want you to take extra care to be all prettied up. Surprise me, something to make any man want to fuck you as soon as he sees you. And I want it tight. I want you in the tightest skirt or dress you have, want you to wear something extra tight and show off that ass of yours. And wear a panty girdle too, keeps those buns of yours all tucked up tight and super smooth. You know what men like. Do it." He stops and listens to me breathe, can feel him through the phone, he knows that too. "Like to spank you like that, don't I, Princess, spank that tightly wrapped ass."

Hear him laugh to himself as I answer, I am blushing bright red, hoping he's not talking in front of someone. "Yes, you do. You do, Sir." I look all around the office through my open door; try to see if anyone passing by can hear our conversation. His secretary is just outside of his office, can't help but feel she knows. I live in fear of the rumors, teasing, tension it would cause. But that doesn't stop me from being his bitch. I couldn't stop now even if I wanted to. I'm his total slut.

"I'll see you tonight. Remember, tight. Be cute, pretty, and be extremely fem. You know what the boys want. Make me proud of you when I take out, baby." He hangs up. My heart skips a beat.

As I hang up the phone I feel the real effect that man has on me, feel my little penis strain to get hard in its locked harness. CB6000 cock harness he locked me in, never get used to it, would never in a million years complain, I wear it for him. He's my man and that's what he wants.

I feel the head of my tiny penis try to push forward as I think about dressing for him, gets me very hot. It always does.

I go back to finishing my work and look at the clock. 2pm, time to leave and start planning how to dress for Daddy. Daddy, right across the hall, my boss, my employer...my owner, I am truly his 'little bitch' as he refers to me now. Can't think about my office work, can only think about what I want wear to please him tonight.

On my way to shop before going home to dress for him I think about what he said to me. He told me he was going to take me to a club. Until now I've dressed any way he likes, done hair and makeup, done it all for him. I've done all the dirty little sex things he wants me to do but it's all been at my home. Now he insists that this is the next step for me. He wants to take me out in public and show me off to others. He says he knows just the place to start at, has a very special place in mind. That makes me very apprehensive, nervous, but gets me hot too, want to masturbate thinking about that. If my little dick were not locked up tight in its' chastity cage I would.

I have been working hard for him, working to be as passable as possible, working toward this night. I've lost weight to the point of being beyond thin, very fem for my height and sissy like, I AM the part. I exercise to keep my rear tight and firm but never to build muscle. I have become his perfect baby soft sissy girl. I talk very fem around him now, never sound masculine. And I try in every way to be 'a good wife', his second wife.

And that makes me all of a sudden jealous. When I think about her doing things for him, trying to suck him as good as I do it makes me mad, get jealous thinking about him fucking her instead of me! I think his wife can't possibly know how to please him like I do! I do the things she won't do.

Tonight I'm going to be everything he imagines and more. Tonight he's going to get everything he hoped for.


I'm wearing a leopard skin print dress; it's off the shoulder and accentuates my thin and now very fem shoulders. Extreme form fitting, very soft and clingy in all the right places, looks like it's painted on across my rear end, this dress was worth every penny. Form fitting sleeves, to the wrist and slightly flared, they show off my shiny silver bracelets, wore a ton of them, sexy when I move. I look very cute and I know it. The dress is so tight, feel that when I move even slightly, tight like a hobble skirt, holds my legs together just above the knee. I wore black hose, lace top silk stockings, his favorite. I have on leopard print heels, 3" spikes with ankle straps, very pointy toe, you can't help but notice these fuck-me shoes! I wore a very sexy silver chain on my right ankle to match my clinking bracelets. My auburn wig is shoulder length and almost covers one eye, very hot look '40s film star look he'll love! My make up is dark, noir, way too much eye liner and shadow, and to set it all off I have bright red lips and off-red lip liner. I have a tiny leopard skin hand bag, sets off my red nail polish. When he opens the front door of my house he sees me, I stand at the end of the hall, feel my heart leap. My tiny penis is pushed tight back between my legs, harness held tight and in place by my black panty girdle. I feel it stir as he looks at me.

"Oooooooo, fuck, you just keep getting better. I can't believe what you have done with your sissy ass. Baby, you are hot!" I walk slowly to him, feel his gaze, his eyes are all over me.

"Daddy, you like?" I smile at him, long hair covering one eye as I look at him from the side.

Penis pulled back between my legs makes me walk very cat like too, model on the runway strut. He likes that too, can see the bulge in his pants as I start to walk to him.

He runs his hand up over my rear end, feel his strong leg push up against me; feel him press his cock on my outer thigh. He's rock hard. Feel him rub his huge erection against my leg. He knows he drives me crazy when he does that, want him to take me there, right up against the wall. I reach for him. He pulls away.

"Not yet, Princess, it's very nice that you're dirty little mind is focused. But not yet." He reaches into his coat pocket, pulls out a box. "I have something for you, before we go out, a present. I love surprising you with presents, baby." He smiles. I feel my heart jump; last present was my penis being put into locked chastity harness. I look to the floor, back up at him.

"Come here." He takes my arm, tight, leads me to my living room.

"Now just relax, I don't want you to mess yourself up, you're perfect right now, couldn't be prettier." He holds my arm as he guides me over the back of my couch, pushes me face first over the back it, face toward the cushions, leans me forward, rear up over the couch back. I hurry to reach down and support myself on the cushions of the couch. Feel his hand run up and over my rear, then I feel him slip my dress up carefully. He rolls the top of my panty girdle down almost to the bottom of my cheeks, exposes my tiny hole.

"Baby, you are incredible, butt like a teenage girl. Stay still, don't you move. Put your legs apart slightly, be a good girl."

He reaches into the gift box. I look back over my shoulder and see him take out a rounded butt plug, tapered with a stop on it at the end, curved rubber to hold it in. Keeps it from slipping all the way in and holds it in place once it's all the way in. I've seen these before, never had one used on me, have been afraid of the huge ball like shape.

"Daddy, please, don't...please..."

"Be quiet, don't mess up that perfect makeup. You'll get used to this just like you did your cock harness." He reached down with his free hand, ignoring my plea, opened my cheeks with his fingers and put the tip of the huge bulbous plug to my rear. He pushed it in slowly.

I cried out, struggled to remain still. It was very thick and it didn't go in easily, felt like my tiny hole was being ripped wide open. When it did finally go all the way in I felt my tiny little hole close tight, almost snap closed around the thin round end of it that held it in place. Felt the sides of the extended rubber push up tight between my cheeks. I whimpered, struggled not to cry out, it hurt.

Felt him run his hand up the crack of my rear, up and down feeling the rubber butt plug, making sure it was securely in place. Felt him spread my cheek to the side, bend forward to inspect it, looking to inspect the fit at my hole, ran his index finger around it. Then he stood.

He rolled my panty girdle back up slowly over my rear end, felt it squeeze the huge plug up inside of me as he did that, pushing my cheeks together tight, felt him gently pull my dress back down and into place. He petted me, ran his hand all over my butt, petted me softly.

It felt like he'd pushed a football up into me. It was very uncomfortable, I hated it.

He slapped my cheek hard. "Walk for me, baby. Up and down the hall. Let's see how my little super model walks with a plug in her rear end. Better not let that slip out." He stood and watched as I got up off of the back of the couch very carefully.

I walked for him, did my best to act as if I didn't have that thing in me. Could hear his approval as I walked the length of my hallway, heard his satisfaction seeing me do that for him.

"Mmmmm, I like it. I jacked off twice last night thinking about putting that into your ass. And it's the next level of your training, baby. Trust me. It'll be explained later."

I walk back toward him. He takes my arm, pulls me up close to him. "What do you say, Princess." He's breathing like he does when he fucks me, very hot.

"Thank you, Daddy." I look to the floor. Feel slightly more comfortable but know I will never like this thing he's making me wear. Feel like my rear is stretched completely open.

"Don't worry, baby, I'll be taking that out when it's time. For now you just deal with it." He feels me start to push up against him. Laughs, "I know you love how I treat you." He watches as my face flushes. I feel his hand slip down my back. He runs his hand down my dress, over my rear end to the bottom of my curved cheeks, holds them both in his large hand. He pushes up gently on me from behind, makes me come up on my toes toward him. "I like that too. You're such a willing little bitch." He kisses my cheek.

"We'd better get going, stay here much longer and I won't be able to control myself, rip that dress off you and fuck you right here on the floor." He moves away from me toward the door.

"Let's go, Princess. It's time for my special little girl to go out, see what's next for her in the big bad world."

As we walk to his car I feel as if everyone in the world is watching me. So scary, never been out from behind closed doors as a sissy. I look to all the houses on my street, check to see if anyone is watching.

He opens my car door for me, just like a perfect

gentleman. As I wiggle into to seat he looks down at me. "I hope everything is still in place underneath that cute little butt, baby, it better be." He smiles. Closes the door before I can answer a meek 'yes, sir', he walks to his side of the car.

As we drive I can't help but think every other car is looking at me. Feel dread, feels like everyone 'knows'. I feel like a man in a dress. Somewhat seized with fear I stare straight ahead as we drive, afraid to look out the window and see someone staring back at me. He says nothing to me, I feel him put his hand on my leg as we ride, rests it on my lower inner thigh, slightly raises my dress up. Can't help but think that's how he drives with his wife.

We drive for what seems like forever, just under an hour. When we finally pull in the parking lot in what looks like a restaurant I feel my heart leap, feel dread set in. Feel panic set in. Feel close to terror set in. He pulls into a parking place. My mind is racing and I feel like running, jumping out and running. I feel so afraid. He shuts the car off. He looks are me.

"I know what you are feeling; I can see it in your eyes. And believe it or not you are hotter than ever right now, beyond cute. So submissive. So sexy, you are beautiful right now." He leans over close to me. Feel his hand slide over the back of the seat and take the back of neck gently, his other hand runs up over my thigh, up the top of my right leg, over my stocking top. He spreads my legs slightly. I feel his finger play with my penis, rubs the cock harness I wear through my girdle.

"I want you to walk into that bar, sit at the bar and be a good girl. All by yourself, sit at the bar, not a table, you sit at the bar. Cross your legs like a lady, do not disappoint me. You're a woman tonight, act like one. And if any man wants to buy you a drink you let him. Be polite, sexy and as feminine as you can, Princess."

He smiles, kisses my cheek again. Feel his hand slide back out from under my skirt. "You can do this, Princes." He leans back in the seat, moves his hand away from my neck.

I grab his hand, desperately, cling to it, hear my panicked voice stammer, "You are not coming with me?? Please, Daddy, don't send me in alone, please..." He puts his finger up.

"Shhhhhhhh, quiet, be a good girl. You cry and spoil that makeup and I'll spank right here." He looks sternly at me

I look at him, almost feel a tear in my eye. "Are you going to leave me here?" I hold back crying, force it back.

"Go, you'll be okay. You know you can trust me. Do this for me. Be a good girl. I'll be close by, be in with you soon. Now go." He looks out through the windshield. I slowly open the door, know that he's done talking.

"Baby, I would not do anything to hurt you, you're my good girl. You can do this." I hear him say as I close the door to his car, look back at him.

As I walk to the bar door I look back at him, he's watching me, smiling. I see him on his cell phone. He motions me with his hand, hurries me on toward the door.

I swallow, get the courage up to enter, I reach for the door. I open the door and am immediately met with the sound of a crowded and loud room, many people chatting. I am thankful for that, it's not well lit. I don't stand out. I enter start toward the bar at the end of the hallway I think to myself, I can get through this.

I feel the huge dildo butt plug held in place by my tight panty girdle push up into me as I place my rear on a stool at the corner of the bar. I struggle to make sure anyone watching would not suspect I wear it. I notice nobody is even paying attention to me. See a few men look my way, check me out, but nobody laughs, nobody points, nobody ridicules. I can do this. I can do this. I keep saying that to myself, I can do this.

The bartender is busy and as he looks at me, nods, smiles at me and winks. I smile and look away. I feel actually sexy all of a sudden. I feel a burst of what an attractive woman must feel, making an entrance into any room. I like it. I can do this.

"What would you like to drink, honey?" I'm shocked as the bartender appears in front of me, was lost in my silly thoughts, lost...he called me 'honey'...he knows, they all know. Feel my face flush, and I feel my throat choke up. "The gentlemen would like to buy you a drink, what would you like?" I look down at the two men he nods toward, they sit at the opposite end of the bar, one smiling at me, the other just stares. He knows, knows I'm not a woman, he knows I'm a sissy bitch. I can barely get it out, hear my voice crack, "I'll have a margarita, rocks please." The bartender looks at me, huge smile. He knows too, they all know. I feel very much alone, struggle to compose myself.

The drink takes some of the edge off. When it comes I hurry to drink it, drink it almost too fast, I ask for another. Very slight margarita haze fills my head, sitting on the barstool, legs crossed hikes my dress up a little. I feel the 'attractive woman' burst again, feel like I don't care anymore, feel kind of sexy being out here, feel kind of dangerous. I can get through this. That's when I felt the hand brush across my rear end.


He was a very big man. I mean big, probably 6'4" 270 at least, dressed very nice, coat and tie, could see his in-shape muscled body through it, looked down at me and smiled. He brushed my ass, did it so innocently but he DID brush his hand across my rear as he moved to sit next to me. There was no mistake about that. He just sat right down, right next to me.


I looked at him. He kind of laughed but not obviously, he knew I was nervous. He motioned for the bartender, pointed to my drink. The men that bought my first two drinks were staring at the two of us. I could feel the tequila. Could feel the huge dildo my boyfriend had put up my rear end, felt it shift around, it made me feel so vulnerable, submissive. I liked that.

He was very charming, chatted with him while I sipped my drink and struggled to get comfortable on the leather seat of the barstool. I told him I was waiting for someone, told him I thought he was very nice but that I was spoken for. He ignored that. Complimented me so much I felt myself start to get turned on by him. He never once said anything about what I thought was obvious, that I was a sissy CD 'girl'. I felt him put his hand on my knee, I moved to brush it off. That didn't stop him. He put his hand on my knee tight, kept it there. I let him.

Sat there sipping the drink he bought me, flirting with him, when I realized I had to go to the little girl's room. Told him I had to go potty, smiled a very dirty little smile at him when I said that, ran my hand over his knee and up his thigh. He just laughed.

"The ladies room is over there." He pointed to the restroom hallway. "I'll be here when you get back."

I went to the hallway and saw the two restrooms, 'MEN' and 'WOMEN' signs on the door. I panicked, didn't know where to go, men's room or ladies room. I was completely confused, my first time out fem. I stood there so nervous, decided to go to the ladies room, would look over the top conspicuous dressed as I was to walk into the men's room.

Went to a stall and sat to pee. I reached back and held the butt plug in so hard, terrified of it falling out. I heard another woman, then two more come in, stayed frozen in the stall until they left. Got up to leave and as soon as I did two more women entered. I went to the mirror, touched up my lipstick. Saw them both look at me, smile. THEY KNEW.

"You look real, cute honey. You actually do. I love your dress, and those shoes, oooo they work for you, honey." She laughed. "I'm serious, girlfriend, a lot of them can't pull it off. You're doing a good job."

They both laughed. Felt my face turn red for the thousandth time, hurried to leave and go back to the bar. "You be a real good girl, now." I heard one of them say that, then heard both laugh out loud as I left the ladies room.

He was still at the bar, no sign of my boyfriend. I sat back down, delicately, next to the huge, big strong man. I could feel the margaritas. I liked that, kept me calm.

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