His Sissy Bitch Ch. 01bykeptsissy©
It started after a transvestite walked into the bar. Sounds like the start of a bad joke but it's not, we were in a party bar after work, me and my boss. My boss and I were having a drink after work; he was more than a little high. An obvious cross dressed man with several friends came in and sat at the bar. 'She' was very cutely dressed, stylish and sexy. My boss kept staring at 'her'. We both did, 'she' was obviously a man, about 90% passable. My boss looked at me, "Cute, no?"
He told me that a very kinky part of him liked that, liked things different and "dangerous". He told me that he had never done anything with a cross dresser but had been turned on by that, said his wife would never entertain his kinky fantasies, that it was a problem for him. He said that he was not gay but a part of him liked the idea of dominating just the right sissy cross dresser if he could find one.
I could not believe what I was hearing. He was slightly drunk but we'd been there, done that many evenings after work. He never talked about sex, his wife or things of that nature. I acted without thinking, just blurted out my fantasy, or lack of it in my real life. That's when I told him I was just the opposite. I told him I had cross dressed before, told him I had dressed for my ex wife. I was more than a little high too, told him my ex and I were into female dominance. Told him that I had been 'just the right sissy man' for my ex wife. He stared at me and smiled.
The next thing he said started it all...the next thing he said was as exciting as it was terrifying.
"If you lost some weight, put a dress on, you'd be more fuckable than my wife." He laughed out loud, made me look around the room. My face turned red. He did it in a very macho way, almost making fun of me. I could swear everyone seated around us heard him. I couldn't look him in the eye but felt him staring at me.
That's how it started. After that he asked a million questions about what I wore, kinds of female clothing I had, did I have makeup, made me describe outfits I liked and wanted. I gave in totally, I got into it. It turned me on more than a little, felt like a dirty little secret talking softly so that no body else could hear, felt the power of knowing I was getting him hot. I was getting him real hot.
The drinks kept coming, made it very easy. Then he said "I want to see." He stared at me. I asked if he was serious, told him I had very little fem stuff left, hadn't 'played' in a long time, not since my divorce years ago. He said it again. "I want to see, now."
He stood and put his coat on. "Let's go." He just put money down for the tab and started for the door. I hurried after him, felt him in control even then.
He drove to the bar so he had to drive me home in his car. All the way to my house I sat silent, was terrified. I'd never done anything like this before. The more I thought about it, more I sobered up. The more I sobered up the more it didn't turn me on, made me very uneasy. He was adamant, wanted to see me fem. He was nice about being forceful but he was most definitely forceful. He was a lot bigger than me. I told him I didn't think I could do this for a man let alone my boss, someone I worked with. He leaned over to me in the car and took my arm, squeezed it so hard he made me try to pull away. It hurt. That was a feeling I'll never forget. It was the first time I knew I could never say 'no' to this man.
"You're gonna do this, my dick is hard thinking about it. I have to see. Just do it." I didn't say anything. He stared at me, stern. I looked out the window as he started the car and drove to my house.
When we got to my house he just sat on the couch looking at me. "I'm waiting.", was all he said, smiled at me. Didn't say anything to me as I went upstairs, he just watched me walk up the stairs.
I sat on the bed. I was truly afraid. Slowly went to the closet and took out my 'secret box', my make up box. Had not done make up or dressed since before my divorce, had only played with my ex wife like that. I took a blouse and skirt from the closet, laid it on the bed. Thought about all the fem things that I hadn't worn in long time, I started to undress.
Was naked and in the bathroom doing make up, and I could hear him down stairs. It was then that it got kind of exciting. I started to think about the stockings and panties I was about to slip on, started getting into it on a very submissive level.
That night was quick, very quick first date so to speak, just did make up, wig, tight white blouse and lace bra and short skirt, panties, stockings and heels. It was one of maybe three outfits I could pull together. I came down stairs and he started to laugh as soon as he saw me. I felt so stupid! I thought he was laughing at me. He stood and motioned me with his finger, had me turn for him.
"Not bad. I like." Felt his hand pat my ass, I felt him squeeze my rear, never felt that before. I liked it.
"So, you don't think I look ridiculous, don't think I look stupid dressed like this?" I couldn't even look toward him, looked at the floor, at my feet in high heel shoes.
He took my hand and put it on his cock, through his pants, pushed my hand over it and held it there. "I told you the thought of a man dressed as woman makes me hard." And it did. He was hard, rock hard.
I didn't resist, kept my hand on him, traced the outline of his huge erection with my fingers, I pumped him slowly through his pants. I heard him start to breath deeper. I'd never done anything with a man before that night. It was more a feeling of being controlled that turned me on than it was sex. But I did want the sex, wanted him to make me do things, all kinds of dirty things right there!
He slid his other hand up under my skirt and felt the tops of my stockings. Pushing his hand down into the rear of my panties, he slid them down over my butt. He cupped my cheeks, felt his large hand grip tight in the crack of my rear, felt his finger brush across and tease my tight little hole. I didn't say anything but remember wanting so badly for him to stick his finger in me, make me feel like a girl, feel like his bitch. I pushed back against his hand, moaned soft for him.
"If you're going to do this right you're going to have to shave." He laughed out loud again. I felt shame that I was not sexy enough for him, felt my face turn bright red. I looked down at the floor. He pulled his hand out of my panties and slapped my rear so hard I whimpered, jumped up onto my toes, "Baby smooth next time." I heard him breathe deep as he looked at me.
I knew there was no turning back. No stopping him, he was turned on. I looked up at him, felt my face turn even redder as he ran his hand again over the back of my panties, felt me up like he was in total control. He took his other hand off of mine, I did not take my hand off of him, squeezed his cock hard through his pants. I wanted him! He put his hand on my shoulder, felt him push my shoulder hard, I felt him push me to my knees. I thought this is what women must feel like with a large man handling them, I wanted more of it.
I just did it. I knelt and undid his belt, took his pants down fast. I took his pants down to his ankles and then pulled his underwear down do his knees. His cock sprang out and stood straight up in front me, fell out of his underpants in front of my face. He was huge! I liked that. I could not stop looking at it, stared deeply at it as I took him in my hand. I ran my tongue up over his balls as I held him straight up, licked him as I started to pump it. When I heard him moan it drove me crazy. Felt my sissy little thing start to get hard inside my panties, that felt inappropriate to me...felt like I should remain sissy soft for this man.
After running my tongue up and over him, driving him crazy, I just wanted to look at his erect cock, wanted to just keep looking at it. I didn't put him in my mouth, just watched my hand run over him, felt the submissive pleasure of pleasing this man!
I jacked him off. I knelt in front of him and gave him a hand job, tried to give him the best hand job he'd ever had. He was so big! All I wanted to do was run it smoothly through my hand, make him moan like he was doing. I felt control like I never had before, submissive in control of serving MY man...I liked that too!
I masturbated him, made him moan, played with him for over half an hour, I put him in my mouth but only a little, just enough to make him wet, make him slippery and slowly drove him crazy. When I felt him start to pump hard against my hand I stroked him full length, held him up straight...pumped as fast as I could. I knew what he was about to do. He was going to cum for me.
He came all over the front me. Came hard and came a lot, I was covered in it. He came into my face. And he came all down the front of my cute fem blouse and onto my skirt. I remember the white drops on my black skirt.
After he came I just looked down at the floor. Felt his semi erect cock pulled from my hand as he stepped back, I didn't want to let go. He pulled away from me. I felt his warm cum all over my face and on my neck. I didn't want it to end. After he came he sobered up a little. Felt scared by what he--we'd done. I could tell he wanted to leave almost immediately. He was very uncomfortable. He would not look at me, just wanted to pull up his pants and run. At least I thought that's what he wanted, that's how I read the situation.
He hurried to pull his pants back up, got his coat and started for the door. I felt like a fool. I was still on my knees, his cum all over me.
He looked back at me when he opened the door, just stared at me. I was ready to get up and just go upstairs, felt like crying.
"I want more of this. I want a lot more of this. We'll talk." I was shocked. He liked it. "You and I have a lot in common, more than just work at the office." He laughed.
"Start thinking about doing this a lot more, and do start thinking about sexier outfits." He turned and left, closed the door behind him. I was half in shock, half turned on. I went upstairs and jacked off, his cum still all over me.
All weekend I masturbated thinking about what I'd done for him. Thought about seeing him at the office on Monday, I liked it, liked it a lot. That's how it started.
I'd never done any gay things, never been turned on by the thought of sex with a man. But when he started pushing me I did it. I not only did it, I loved it. Loved doing all the things he asked and demanded. And he demanded things right from the beginning.
After our 'first date' he called me that Sunday at home. Told me not to feel awkward at work, told me no one must know about what we did...he told me that no one must know what I was going to become for him. He told me I was going to be his 'little girl', his sissy bitch.
That made me feel as much afraid as it did feel excited, he made me even more concerned about all of this. I was very hot about what happened, fantasized about being dressed for him the first time, feeling his hand up under my skirt, for the first time. I thought about being spanked by him! Little did I know at that time that he'd do that to me and much more.
So when he called and told me he expected me to not only act completely normal a work and not be nervous, but that he expected me be shaved completely baby smooth just like a woman and see him again early the following week I felt fear. I felt scared to death that I now had a man telling me what to do...and could not say 'no' to him. But I did as asked, as told. I shaved my legs, under arms, rear, crotch, totally, became like a little girl for him.
That's when it started, that week. It was the start of me becoming his kept sissy 'boy'. I went about making myself the perfect smooth and soft sissy for him. After I got off the phone, after his call on Sunday the week of our first time, I made up my mind that I'd pursue this. I started looking at fem clothing sites on the computer, started planning to be the sexiest little CD slut he could find! My initial fear gave way to erotic fantasy, couldn't wait to be on my knees in front of this man again!
That's when it all started.