tagTranssexuals & CrossdressersHis Sissy Bitch Ch. 02

His Sissy Bitch Ch. 02

bykeptsissy©

The next day at work I felt my face flush every time I saw him, felt embarrassed and felt like stammering every time I spoke with anyone in the office. His office is across from mine, he's my boss and I have to see him daily. It felt like everyone in the office knew! I was so nervous I didn't speak to anyone, avoided everyone as best I could. He didn't say anything to me that Monday, caught him glance at me once and then look away. There I was, shaved baby smooth under my clothing, feeling like a complete fool for this man. It was the first time I'd ever done that, shaved legs, crotch, rear all baby soft with aloe moisturizer. I felt like all in the office could see through my clothing.

He ignored me all day, met with his clients in his office alone. When I went home that evening I felt rejected, felt like I'd made a huge mistake. Late that night he called, was terrified when I saw his number on the caller-id. I answered the phone.

"Did you shave like I told you to? He didn't even say 'hello'.

"Yes." I could hear him silently smile...at least I thought I could.

"Good. You were shaved baby smooth, top to bottom at work today?" I could hear his car radio, he was driving. "If I run my hand over you will I feel any hair or stubble?" He was very stern.

"No, I'm probably smoother than your wife." I felt my voice break, felt like crying. "Yes, I'm smooth for you."

"That would be better if you said 'Yes Sir'. "Yes Sir." He laughed as I said it.

"I want to see tomorrow night. I want you in something other than the woman's street clothing you wore the other night. You looked like a secretary, someone at work, with that blouse and skirt on."

I interrupted him. "It's all I had. I didn't count on any of what happened...I wasn't ready", he shushed me.

"I know. That's why tomorrow you're leaving work at noon. You're going to get an outfit, one I like. Get several. Think of this as pleasing your man, like real girls do. That's what you're going to do. My wife rarely wears sexy things. But you I want in sexy things when ever I see you. And I like slutty. I like lace stockings, heels, lace corset type things, small and lacey, turns me on. I like to fuck my wife and think about her dressed like that. She never does. Think of yourself as my second wife." he laughed loud, "Think of what my dick will do when I see my dirty little second wife dress up for me like that. You need to start thinking about things from that perspective. You need to start thinking about dressing to turn me on. Do you know why?" He was lecturing me, he'd never done that before.

There was an awkward silence and before I could respond..."Because you're mine now." I felt my throat close, choked up.

"I've been thinking about it, can't stop. I have masturbated thinking of you becoming my sissy, my complete and convenient sissy girl. Do you want to do that for me? I think you'd be very good at it, think that's what you were meant to be." He laughed again. "I knew there was a reason I hired you to work for me."

"Yes Sir." I felt something I never felt before, felt totally submissive to this man, most submissive I'd ever felt. I felt helpless. I felt a tear in my eye, felt choked up. "I would love to do that for you."

"Good. Tomorrow night, your place, dress to please. Because you're going to, my dick is hard right now. Does that make you want to see me? I know you couldn't take you eyes off of it the other night."

I felt myself start to get hard, put my hand on myself. "Yes Sir, masturbated a hundred times thinking about being yours, on my knees dressed for you. I'm sorry you didn't like my outfit. So sorry...", I started to gush. He shushed me again.

"I liked your outfit. You would look very nice in that in a bar maybe on the street. And start thinking about that too. You're going to do a lot of things you've never done before. Don't forget what started this all, remember the cross dresser in the bar last week?"

I mumbled 'yes'...He shouted "Yes Sir!". I answered him, "Yes Sir."

He was silent for an awkward moment. "But I want some very sexy well planned sissy things on you too, especially around the house. The two of us are going to make you a very real little girl. Want you to feel like I own your little ass, I don't want to see one hint of masculinity on you. When I see you all I want to think about is using your mouth or your rear. It's the fantasy I told you about in the bar. The more lacey and girl like you are, the better. Think about that. I have to go. You be ready tomorrow night. You dress real cute and I might let you do what you did Friday, might even let you put it in your mouth."

I could hear him breathing deeper as he laughed. "You looked very good with my cum down the front of you and on your face."

"Yes Sir." He laughed loud.

"One more thing and this will be hard for you. I want you thin. Start working on that, want you fem and thin. You're in pretty good shape, you're going to be in much better female-type shape. Do not work out to build muscle, work out to lose weight. Are you clear on that?"

"Yes Sir."

I started to say I would do that for him, do anything for him but he hung up.

My mind raced! I went up stairs, did an inventory on my fem clothing, made a list of things I needed. I was more excited than I'd ever been, could think of nothing other than being his sissy, his 'second wife'!

Ordered things on line that night as soon as I got off the phone, all I could think about was pleasing this man, making him want me. I masturbated five times, didn't get to sleep until way past 3am.

Tuesday afternoon I went 'girl' shopping. Left the office early and as soon as I walked past his office door he looked at me, smiled. I knew he knew where I was going.

I bought some very cute things and a lot of makeup. I left the office at 11 am and hit the shops downtown immediately for one truly drop-dead cute sissy outfit. I knew exactly what I needed to truly show off my desire to be his sissy bitch. I had something very special planned for this man, could hardly wait!

When he showed up at my place that evening I left the door slightly open. He knocked and I told him to come in. When he saw me he just stared, he was speechless. I liked that, knew I did what I planned to do.

I was wearing white 3" heels with lace top ruffled ankle sox. The super ruffled tops made my shaved legs look very inviting. I had a white lace waist cincher bustier that came up just below my nipples, which I applied slight red rouge to. I had a white lace collar choker around my neck. I wore way too much eye shadow, mascara and eye liner and I wore shiny pink lip gloss with a deep pink lip liner. I had on a blonde very sexy wig, bangs down over one eye, and large gold hoop earrings. I wore no panties. I had a pink ribbon tied in a big bow up tight around my balls, bow just on top of my soft little thing, made it stand out and showed off how small and little boy-like I was compared to him. I was his perfect present.

"This is much better than I thought it would be!" He just stood and stared. "I had no idea." He walked to me. Ran his hand over my rear and down over the back of my legs. "I like, I like a lot!" He ate me with his eyes..."Fuck, I had no idea."

"Thank you Daddy." I smiled at him. "I did it just for you."

"I wouldn't recognize you, it would be hard for anyone at work to even know this is you." He looked at my face, put his finger under my chin, he turned my head up and side to side. "I like."

Felt him pat my rear and then he turned me toward him and stepped back to look. "And I like the ribbon. I was worried about having to see that. I am not turned on by your dick, don't ever think I am."

"Yes Sir. You will never have to deal with it, I don't expect that." I looked at him, saw him slightly uneasy. "I want to please you, Daddy." I leaned forward and ran my hand over the front of his pants. He was hard. I knew he liked what he saw. He took my arm and turned me around, felt his eyes from behind. "I want to please you so much."

"Oooo, I like...no, I love it." He ran his hand over my rear, finger went up between my cheeks. He spun me around and with both hands spread my cheeks, felt him inspect me with his eyes. "I may get to like fucking you more than I do my wife."

He released my cheeks, slapped my rear so hard it made me pull forward and up on my toes, made me whimper.

"Get me a drink." He walked to my couch, sat.

I did as he asked, got him a vodka on the rocks and when I went back into the living room he'd taken his coat off and was sitting on the couch. I handed him the drink.

"Let me see you walk. I want to watch." I did as he instructed, walked as sexy as I could for him, made sure my rear moved back and forth like a model on the cat walk. I practiced that for an hour before he arrived. He ran his eyes all over me and sipped his drink slowly. My back was too him, I was posing, leaning on the chair across from him, pushing my rear out, smiled back over my shoulder at him.

"You are a very sexy little girl...come here." He stood in front of the couch, "Let's start where we left off the other night."

He put his hands on his hips. I didn't wait to be told what he wanted. I knelt in front of him. I undid his belt and unzipped his pants, pulling them to the floor. His cock stuck out of the top of his underwear, he was hard and wet on the end, stood straight up. I pulled his underwear down slowly, looked up at him as I did. His rock hard erection was right in front me. I was about to be the perfect little wife.

He was staring down at me, smiling. My hands were on the sides of his hips, cock standing straight up and bobbing in front me. I just did it, I leaned forward and I took him in my mouth. As my lips closed around him, heard him moan softly and jerk slightly back. I quickly flicked the end up right up the hole with my tongue. Pulled my mouth back off of it and looked up at him. His eyes were closed, I slipped him back into my mouth. I held his huge erection in place with my lips just behind the head and ran my pointy little tongue up the hole...teased and drove him crazy like that.

"Uhhhhhhh, fuck...ooooooooo, don't stop, keep doing that, whatever it is keep doing it!" Felt his hand go to the back of my head as I licked in little circles all over the head of his cock and up the hole, he was throbbing in my mouth. I did that for what seemed like forever and then started to pump him as far in as I could. He was lost to my mouth, felt him hold my head firmly as I sucked him.

And I was lost to him, wanted it not to end, felt his erection pulse in my mouth, at the back of my throat. It was time. I started to pump to make him cum, started to jack him off with my mouth.

When he came I held him by the sides of his hips, tightly. He pumped and whimpered, fucked my mouth with long strokes as he spurted into my throat. It was the first time I'd done this, I wasn't used to him, I choked, pulled back off of him. He reached down and with both hands held my head tight and in place. He pushed it back into my mouth roughly. I was his to use. Ignored my choking, he kept fucking me.

When he finished he released my head, pulled his cock out of my mouth. I looked up at him. Felt my lip gloss all over my face, saw it all over his cock.

"Fuck! You do that better than my wife." He looked down at me. He pulled me up off of my knees, I faced him. I felt his hand all over my rear again, up over the lace on my bustier. "Your make up is a mess." I reached down and took his limp penis in my hand, he was semi erect and still huge. He laughed. "Do you know how hard it's going to be to not walk into your office and fuck that mouth?"

"No, tell me, Daddy." I smiled, winked at him and looked down at his cock. I could feel and taste his cum all over the inside of my mouth. I stroked his cock, ran it through my hand.

"Well I won't be able to do it if you are dressed as a man. That's a turn off." He laughed.

"I don't want to dress like a man when you're around. Do you know how hard it's going to be to not be dressed for you? I want to be your sissy." He pulled away, laughed and sat on the couch, sipped what was left of his drink.

"I want to be your sissy girl, want to dress for you the way you like. I want you to think about fucking me, want to keep your cock hard, Daddy. You bring out a very submissive side of me, make my dirty mind race." He smiled. I knelt in front of him, took his cock in my hand. I started to lick the head.

"Fuck! You are a dirty little bitch. Go get me another drink and hurry up, want you back here just like this." He pushed his empty glass out at me.

I took it, set it on the kitchen counter and hurried upstairs to redo my lip gloss. I came back to him with his drink, he sat with his pants still down around his ankles...I handed him his drink.

"You're going to be doing this regularly." He looked up at me. I knelt in front of him. I leaned forward and took him in my mouth again. He sat, legs spread wide as I sucked him on the couch. All he said was, "Good girl."

I took my time, gave him a long slow blow job. Ran my hand up the shaft, held him straight up, ran my tongue up his balls and up the full length of his rock hard penis. I licked him slowly, got him all hot and bothered and wanting my mouth on it, he wanted to cum again. I ran my tongue down under his balls and played with the crack of his rear with it...ran my tongue slow and deliberate back up over his balls and to top of his cock. I pushed just the tip of my tongue into the hole and stared up at him. I watched him squirm and moan. I got his attention with that move. I pulled back off of him.

"I'm going to be jealous of her doing this for you, your first wife. I'll always do it better than she does." I looked up at him, "Daddy, I want you to cum in my mouth." I could hear him moan deeply.

I pushed him into my mouth, slow, as far as I could, started to jack him off again for the second time with my mouth. I could feel his eyes on the mirror on the wall just across from the couch. I thought about how much he must love seeing my sissy rear, lace ankle stockings just up under my round little cheeks, legs slightly spread and kneeling, little soft small boy like balls and soft penis dangling between my legs. I pushed my rear back and out for him to see, felt my cheeks spread wide for him, showed him my tight little hole in the mirror behind me as I sucked his cock. That's when I got serious. Then I started sucking to make him cum, fast and hard.

I felt his hands close on me, took my head in his hands again, this time so tight it hurt. "Do it...do it, bitch. Make me cum, swallow it all for me, baby. Oooo, fuck!"

He exploded in my mouth a second time. I swallowed completely for him. Didn't choke, didn't spill a drop of his cum, I swallowed it all the second time. Felt him run his hand down my back as he leaned forward, patted my butt softly then ran his and up my back. He took me by the back of my neck in one hand, he held me in place. He took his semi erection and ran the end back and forth across my lips. Wiped him self clean on the side of my face.

"Good boy. Or should I say good girl." He stood.

I watched as he dressed, pulled his pants back up and composed himself. I felt him look me over as I did my best pose for him, slutty bitch on the floor.

I knew he was through with me, he was done. He walked to my door, looked back at me and said, "Good girl."

"Yes Sir." I winked at him again, smiled at him.

I felt my make up all over my face, his cum still in my mouth. He closed the door behind him as he left.

After he left that night I stood in front of the mirror he'd been watching me in, watching me kneel staring at me from behind. I stared at myself for a long time, tasted him still in my mouth.

I was his to do with as he pleased. Started thinking about my next cute outfit, my next chance at pleasing my man.

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by devilspy05/21/14

Sissy is good at swallowing loads.

Besides chastity, sissy boy needs to get a six inch vibrator. Start lubing his pussy and using the toy on himself to get use to his Daddy's huge real man cock. It will not be long before Daddy is goingmore...

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous07/26/13

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