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New Job, New Life as as Sissy Slut

By: sdbottomslut



I was nearing my thirtieth birthday and times were getting tough financially. I had gotten laid off from my job and was collecting unemployment and doing some part-time work helping out friends with odd jobs. One of them suggested that I look into cleaning houses. I've always been very neat and people often thought I was gay. I had dated many women, but never met anyone who might be Ms. Right. I must say that I sometimes fantasized about being taken by a man, but I never acted on it. I bought some dildos and practiced sucking on them and occasionally worked them into my ass. I thought that was as far as my fantasies would go. I had never really fantasized about cross dressing, though I did love seeing women in stockings and garters and other lingerie and I loved when they wore high heels. I never envisioned me wearing those things, but little did I know what lay in store for me.

I put an ad on Craigslist to offer my services. I would charge $75 or so, depending on the size of the house. There were a few calls, but we couldn't work out a price, then one day I got a call from a man asking me to stop by and give him a price. It turned out to be a very nice house. The man answered the door. He looked to be in his late thirties and in good shape. He was wearing a dress shirt, slacks and dress shoes. He asked me inside and I had a look around and he handed me a list of things he would want done; the list was what I expected: dusting, dishes, laundry, and general cleaning duties. I offered to do it for $80 once a week and we shook hands in agreement. 

"So I'll see you on Tuesday at noon?" he said.

"Yes, sir," I replied. He smirked at my response.

I would go over each Tuesday. I figured it would take two to three hours to do and those few hundred bucks per month would really help me out. I bought cleaning supplies and started my new job.

The first few weeks went by without a problem. Once I learned to multi-task it only took me a little more than two hours. Rick, the homeowner, worked out of the house. Even though he was working at home, he always wore a dress shirt, slacks, and dress shoes. He apparently did some video conference calls from his study and wanted to look somewhat professional. We saw each other when I showed up and I usually didn't see him again until I was about to leave so he could pay me.

One day I was polishing the feet of the dining room table—they were silver and the table top was glass—and suddenly there I saw bare feet. I looked up and there was Rick wearing only a bathrobe. He was looking down at me and smiling.

"Doing a good job there?" he said.

"Trying to."

"You like polishing things?" 

"Well, I don't know about like, but I think I'm good at it," I responded.

"Good, huh?" he said and then opened his robe to reveal a huge hard cock staring straight at me. "Well, why don't you polish this." I was stunned and didn't know what to do. I'd had those fantasies, but I never thought I'd be on my knees before a hard cock. It must have been at least nine inches, cut, and it was thick and veiny. It was a magnificent specimen, but I was frozen and didn't know how to react. Ken then took a step closer and began slapping my face with his cock and it got harder when he did and was pointing at the ceiling. He ran his cock softly across my face and then pressed the head to my lips and without even thinking I opened my mouth and his cock slid in. I looked up at him and had a grin on his face. "I knew you were a submissive little cock slut the moment I saw you," he said. I was struggling with how big it was. "Relax your throat," he said. I did and it was a little easier, though I still only had about half of it in my mouth. He put a hand on each side of my head and began to slowly fuck my face. My own cock was now rock hard and I found myself fondling his balls while he face fucked me. He was moaning now and I was gradually able to take more and more; my nose was nearly buried in his pubic hairs. The musky, masculine smell and taste of him had me mesmerized. He started pumping faster and then he began cumming down my throat. I wasn't expecting the taste, nor was I expecting such a huge load. I swallowed as much as I could, but some spilled out. When he was done he pulled out and scraped the cum on my face onto his cock and then ordered me to clean it. I did. "That's one more item on the list that you will be performing each week. Understood?"

"Yes, sir." He smiled and then closed his robe and left me to my cleaning. My head was buzzing. I had just sucked a man's cock and swallowed his cum. Not only that, but many more new things were about to come my way.

The next few weeks were somewhat of a repeat. As I was cleaning he would walk up to me and snap his fingers and point at the floor. I would immediately drop to my knees, unbuckle his belt and pants, then fish out his cock and get to work on it. It was such a great cock. I found myself thinking about it when I was lying in bed at night and I would jerk off and imagine it in my ass. I would finger my ass and pretend it was his cock. I would also wonder if it would go any further or if he just liked getting a blowjob. That question was soon answered.

One day, after I had swallowed his load, he pointed out that I had forgotten to empty the dishwasher. I had remembered filling it and turning it on, but I realized that I had been so preoccupied with the impending blowjob that I had forgotten to empty it and put the dishes away.

"You will need to be punished for that. Do you agree?" he asked. I couldn't get any words out in response, but felt myself nodding. He had a slight smile on his face but he also looked stern. He pulled out a kitchen chair and sat down. "Drop your pants," he said. I obeyed. "Now the undies." I was wearing boxer briefs. I hesitated. "Now!" he barked and I fumbled and managed to slide them down around my ankles. My cock was not hard anymore; I was kind of afraid of him. "Get over here," he commanded. I walked over and he spun me around and threw me over his knees, my face only inches from the floor. He spanked me. Very hard. I yelped. Spank. Yelp. He gave me a dozen or so and my ass was on fire and I had tears in my eyes. "The penalty for that transgression is ten whacks," he said. "Count off." I had already gotten more than that, but they were apparently only a warm up. Spank. Yelp. "One." He got up to nine and then informed me that I didn't thank him after each one. Spank. Yelp. "One. Thank you." He got up to nine again and then informed me that I didn't address him after each one. Spank. Yelp. "One. Thank you, Sir!" Finally he reached ten, then he shoved me off his knees and onto the floor, where I lay in a quivering heap.

"Thank you, Sir, for the punishment. It won't happen again," was all I could manage.

"Get your ass off my floor and pull up your pants. Your money is on the table in the hall. Also, I've been thinking. . ." His voice trailed off. Uh oh. "Since you are basically my maid, I think you should start wearing a uniform. When you get here, let yourself in. Your uniform for the day will be on the couch in the living room. You will put it on and present yourself to me for my approval. Is that understood?"

"Yes, Sir. I understand."

"Good. Now get out of here." My head was swimming. A uniform? Was I basically going to be his butler? I had to wait a week to find out.

When I arrived the next week I let myself in and walked into the living room. On the couch was a pair of red lace panties. That was it. What the hell? Was I supposed to wear only those, or was I supposed to put them on under the clothes I was wearing? I didn't hear him enter the room.

"Well, why aren't you in uniform?" he growled. He did not seem in a very good mood.

"Um. . ." was all I could manage.

"You have thirty seconds to get out of your clothes and into your uniform." Well that answered that question. However, I stood frozen, not computing what he was telling me. "Now you have twenty seconds," he said, looking at his watch. I fumbled with my clothes; when I went to untie my shoe, it knotted. Of course. It took at least a minute for me to stand before him wearing the panties.

"Sorry, Sir," I mumbled, averting my eyes by looking at the floor. He walked around behind me and fondled my ass, which made my cock twitch and get a little hard.

"They look good on you."

"Thank you, Sir," I stammered. "And thank you for the uniform."

"You're welcome, slut. We will be adding a piece or two each week. Next time you might want to get here earlier so that you can be presentable at precisely noon."

"Yes, Sir."

"You were late in being in uniform at noon today, so you know what that means." I actually didn't know what it meant, but I knew it wasn't good for me. He walked over to the couch and sat down on the edge of it on the middle cushion. I silently walked over and lay myself across his knees. He proceed to give me another hard spanking session, this time giving me probably fifty whacks in all; at one point he turned me around so he could use his left hand as well. I made sure to count off once he had warmed up. My ass was on fire again and I had tears in my eyes. I was lying across his thighs at one point and could feel his rock-hard cock bulging against my hip. When he was done he ordered me onto my knees and shoved his cock in my mouth. He had always cum in my mouth, but this time he pulled out and sprayed his load all over my face and in my hair. He stood smiling as he looked down at me, admiring his handiwork. It was an impressive load of cum. "Keep that on there until I tell you to clean it off," he said, then left the room. I did my cleaning that day with his cum all over my face; it felt like my entire face was covered. Before I left that day I gave him another blowjob and he blew another load on my face. He was kind enough to let me wash my face before I left. That would not always be the case, as I would find out. I was curious what the next week's "uniform" would look like.

I spent the week wondering what my next uniform would be. I was also jerking off more than ever. I couldn't stop thinking about his cock and fantasized what it would be like to have it inside me. I fucked myself every day with the little dildo I had, which was much smaller than his cock.

As I quietly entered his house, I slipped into the living room. On the couch were pink stockings, garter, thong, bra, and a studded pink dog collar. Sitting on the coffee table were a tube of lipstick, a butt plug and a bottle of lube. Wanting to avoid another vicious spanking, I quickly slipped out of my clothes. I was trembling with excitement as I pulled on the panties and garter, then slipped the soft stockings on each leg and clipped the garters to the stockings. They felt so sexy. I then put on the collar and applied lipstick as best I could without a mirror. The butt plug was about five inches long but pretty wide. I lubed it up then pulled aside the thong and straddled the butt plug on the coffee table; it took a few minutes but it finally popped in and filled my ass; I have to admit that it hurt a bit. Even so, my cock was hard and was barely contained in the frilly pink thong.

I felt ready and went into his office for presentation. He was working at his computer and turned to look as I walked through the door. He smiled, obviously pleased at my appearance. He then looked at his watch and the smile disappeared.

"It's 11:58," he said.

"Yes, Sir. I wanted to be early today."

"What time did I tell you to present yourself?" Darn. He had me there.

"Noon, Sir."

"Is it noon?"

"No, Sir."

"Get over here." I proceeded to lay myself over his knees and took another spanking, this times thirty whacks after his regular warm up. He then, again, shoved me unceremoniously to the floor, then he stood up and started unbuttoning his shirt. This was something new. "Take off my shoes and pants," he said. I climbed back up to my knees and bent over to untie his black dress shoes; as I finished each one he lifted up his foot so that I could slide the shoe off. I then unbuckled his belt and pants and took them off. I then, at his command, removed his socks and his briefs, which did nothing to hide his huge hard cock. He was now naked before me. I hadn't really noticed before how muscular he was. He had a large chest and arms and his pecs and abs were ripped. He was an impressive specimen. And here I was, small and weak and on my knees before him, wearing women's lingerie and a dog collar. He shoved his cock in my mouth. I felt like such a slut. I was expecting the normal blowing of his load on my face or down my throat, but he suddenly yanked me by the hair and pulled out of my mouth. He walked around behind me and roughly placed his hand between my shoulders and forced my face to the carpeted floor. 

I saw him go over to where his clothes were on the floor. He slipped the belt from his pants. I cowered before him. For the next few minutes, he whipped my ass with his belt. Between whips with the black leather belt, he was calling me "slut" and "whore" and "sissy" and "cum dump" and other names. Just when I thought I couldn't take any more, he stopped. He then reached down and pulled out the butt plug; it made a popping sound and I felt empty. That didn't last long as I felt him pull my ankles apart and then I felt him kneeling behind me. I was about to get fucked. I was about to have my cherry popped.

"Do you want to get fucked by my big cock, sissy slut?" he said. He was mocking and humiliating me and loving every minute of it. What shocked me was how, deep down, I was loving every minute of it too. A man I barely knew and was afraid of was about to make me his bitch. I managed a moan. He grabbed my hair at the back of my head and yanked hard, so that my face was facing the wall. "I said, do you want to get fucked by a big cock, you fucking little sissy slut."

"Yes, Sir!" I cried.

"Say it!"

"Please fuck me with your big cock, Sir!"

"And?" He pulled harder on my hair.

"And make me your sissy slut, Sir!" 

"That's better," he said and let go of my hair. I laid my head on the carpet again and waited. He lined up the head of his cock at my hole and gently started working it in. The butt plug had helped to open me up some, but his cock was a lot longer than the butt plug or than my dildo at home. Within a few minutes he had worked his cock all the way in; I could feel his balls touch my ass. He slowly pulled almost all the way out, then slowly filled me up again. He gradually started to pick up the pace. I was getting fucked and fucked good. Finally, he just started pounding my ass and calling me every name he could think of. He had me scream "I'm your bitch" over and over. Next, he turned me on my side and lifted my leg over his shoulder. It was a whole new angle and a different sensation. It was getting less painful and more pleasurable with each stroke and I was moaning like the slut that I was.

The position that totally made me feel like the slutty whore I was was when he flipped me onto my back, put my legs over his shoulders, and began fucking me harder. My toes were actually touching the floor behind me and my knees were practically touching my ears. My ass was straight up in the air and he was putting all his weight behind each stroke. His balls were audibly slapping my ass and I was moaning and moaning as I was getting fucked so hard. Finally, after about fifteen minutes in this positions and who knows how long overall, I could tell he was about to cum. He slid his cock out and slid his body down so that he pinned my legs over me. He pointed his glistening cock at my face and said "Open wide." I opened my mouth wide and he proceeded to dump the largest load of cum I've ever seen all over my face, hair and neck. He got off me and stood up. My legs were still folded over me and my gaping ass was in the air.

"I'm going to take a shower. Leave that cum on your face until I tell you to clean it off. There are going to be some changes around here. We'll talk before you leave. Your life is in for some changes." He smiled, his muscular body glistening with sweat as he walked out of the room. As I lay there, wearing lingerie and covered with cum (and I still had all the cleaning to do), I wondered what changes were in store for me. 

New Job, New Life as as Sissy Slut Ch, 02



I was left lying on the floor, my face completely covered in cum. I was wearing lingerie and a dog collar and I had just been fucked long and hard by my "boss." My virginity had been forcefully taken. The thing is that I loved it. I loved being manhandled by this muscular man and I really had become his bitch.

I got up and began cleaning, very much aware of the feeling of wearing lingerie. I loved the way the stockings felt on my legs. My ass was raw and felt as though a baseball bat had been shoved up it. I could hear him in various rooms about the house. I tried to make sure I didn't make any mistakes because my ass still stung a lot from the spanking and the beating with his belt. He had taken serious pleasure in beating me. I didn't mind the spanking as much because it felt more intimate with me over his knees, but the belt had hurt and he had seemed cold and callous as I yelped with each blow. 

It took about three hours to do the cleaning; I was moving more slowly than usual and also I wanted everything perfect for him. Finally, I was done. I went into his study, where he was reading some papers. "I'm done, Sir," I meekly said to him. He turned and looked at me and smiled. I think he had forgotten about the cum all over me. It had dried and felt sticky.

"Get over here." I walked over and stood before him. He looked at me and I could tell he liked me wearing lingerie. I guessed that the studded pink dog collar was a symbol of his control and power over me. "From now on, I want you here twice a week. You will come on Tuesday and Friday. The hours will be longer. You will come here in the morning and put on your uniform. Then you will give me a wakeup call at exactly eight thirty. By wakeup call I mean you will awaken me by sucking my cock. I like to blow a load when I wake up and now you will do that for me. You will clean and be used by me all day, then you can leave at five o' clock. Is that understood?"

"Yes, Sir." I started to say something, then stopped. I didn't want to risk another beating. He seemed to know what I was thinking.

"Don't worry, I will compensate you for the extra hours. You will also be able to earn a bonus for other activities, which we will get into later. You won't need to worry about looking for a job for a while."

"Thank you, Sir. I appreciate it."

"Well, you can show me your appreciation right now." He stood up, snapped his fingers and pointed to the floor. I immediately dropped to my knees and he walked over and stood before me. I unbuckled his pants and took his already-hard cock into my mouth. I wanted to give him the best blowjob he had ever had. I liked being used by him. I was now kissing and sucking his balls, running my tongue all over his cock, and then sucking for all I was worth. He was moaning and fucking my face now. He was close. After another minute or two, he pulled out and blew his second massive load of the day all over my face. "Very good, slut. You're getting better."

"Thank you, Sir."

"Get out of here. The money is on the table in the hall," he said as he zipped up and buckled his pants. He started to turn back toward his desk, then stopped. "Oh ... one more thing. Drive home with my cum all over your face. When you look in the mirror you will be reminded of your place from now on. Goodbye, sissy." I got up and left the room and got my money. I would drive back streets to limit how many cars and people I would see. I hesitantly opened the door and let myself out, wondering what other things he had in store for me.

That Friday couldn't arrive fast enough. I jerked off many times thinking about how hard he had fucked me while I wore lingerie. I wondered what other things he would make me wear and how often he would fuck me. It was impressive how he could have such huge loads of cum after he came only a couple hours earlier. I had driven home that day covered in his cum and, yes, I did look in the rearview mirror a lot. The drive went without incident and I don't think anyone saw me.

I arrived Friday morning at about eight and immediately went into the living room to see my uniform for the day. This time there was a full maid's uniform. It was purple. There was the dress with the apron, stockings, garter, thong, bra, and this time there was a pair of purple high heels. I guessed that the heels were about four inches long. Also, this time there was a wig of shoulder-length brown hair, and there was also makeup and lipstick. Again, there was a dog collar, which was also purple. I quickly undressed and pulled on the thong, garter and stockings. He hadn't bought cheap lingerie, either. This was quality stuff. Next came the bra and then the dress. It fit pretty well. I am a fairly small guy and I imagine he'd guessed the sizes. 

I put on the collar and then came the high heels. Surprisingly, they fit. They were a little tight, but not too much. I got up and wobbled around in them for a few minutes, constantly looking at the clock to be sure I had his cock in my mouth at exactly eight thirty. He had been kind enough to leave a little mirror this time and I applied the makeup as best I could. The lipstick and eyeliner were a lighter purple than the uniform. I applied those and some blush and thought I looked okay. The wig came last. It was a little snug and I knew it would get uncomfortable after a while, but I would have to learn to live with it. 

It was almost time and I walked up and stood outside his bedroom. He slept with the door open and I watched the clock on his nightstand. When it hit eight thirty, I crept in, softly climbed onto his bed and pulled back the covers. He was naked. I bent over and licked his balls. He stirred. I then licked his cock and then took it into my mouth. It hardened immediately and he moaned. I was good now at taking all nine inches of it into my mouth. My head bobbed up and down and then I felt his hand on the back of my head. He pushed down on my head and began bucking his hips, his cock hitting the back of my throat. I gagged a little and he moaned more. A minute later came the torrent of cum down my throat. I managed to swallow all of it.

"Now that's what I call a wakeup call," he said, his voice still filled with sleep. "Now get downstairs and make me breakfast. Two eggs, scrambled, toast and orange juice. I expect it on the table when I'm done with my shower. Now get going." I got up quickly and left the room, wobbling on my high heels. Now I had to cook for him? He hadn't said anything about that. I was a pretty good cook, so I wasn't worried about that, but I wondered how often I would have to cook for him.

I got downstairs and went into the kitchen and began preparing his breakfast. I couldn't help but notice a piece of paper on the kitchen table. It was a list of chores. There were the original chores that I had been doing, but there were also a lot more, some of which would be time consuming: Waxing the floor, cleaning the refrigerator and freezer, cleaning all the equipment in his gym in the basement, ironing, even cleaning the furniture on the patio in the back yard. That meant I would have to be outside in my maid's uniform. Obviously, these weren't things that would need to be done twice a week, but I would still be doing them.

I got his breakfast on the table about a minute before he walked into the kitchen. I had also gotten the newspaper from the front porch and placed it on the table by his plate. He was wearing his normal dress shirt, slacks and dress shoes. He looked at me, checking out my uniform. He seemed happy with my appearance. "From now on, you will curtsey when you see me and after I give you an order." He eyed me expectantly and I managed a curtsey. "That needs some work," he said, sitting down to his breakfast.

"Yes, Sir," I replied. I started cleaning up what mess I had made from making him breakfast. After a couple of minutes, he cleared his throat.

"What the fuck is this?" he growled. Oh no. Now what?

"Sir?" I croaked.

"Have you been reading this list?" he said, pointing to the list of chores.

"Um . . . I just noticed it, Sir." He stood up. He looked pissed off.

"How dare you read anything of mine without my permission!" He walked over, grabbed me by the arm, and pulled me over to the table. He put his hand on the back of my head and pushed my face to the table's surface, so that the list was sticking to my face. "You need to learn a little respect. This is a good chance to try out one of my new toys," he said. I heard him walk over and open one of the drawers. Next, he was waving a black leather paddle in front of my face. Then he roughly yanked my dress up over my hips, leaving my thong-clad ass exposed. 

I hadn't even been there a half hour and I was already about to get my first beating of the day. Whack! I screamed in pain. It hurt even more than the belt. The paddle was about ten inches long and four inches wide and I could feel every inch. Whack! I was crying by the third blow. After seven or eight, he ordered me to count them off. I did so, taking twenty more whacks on my raw ass. When he was done he ordered me to my knees and he whipped out his cock, which was rock hard. He apparently really got aroused by beating me. He shoved it into my mouth, where it had been only a half hour earlier. He grabbed the hair of the wig and furiously fucked my face, then he pulled out. "Bend over," he barked. 

I stood up and bent over the table and he shoved his cock in my ass and began pounding. The table was rocking and sliding as he roughly fucked me. He would fuck hard and fast, then he would slow down when he was about to cum. He would pull his cock so that only the head was in, then he would shove it all the way in so that I felt like it was going to come out my mouth. After what seemed like a half hour I felt a gush of cum in my ass. It would be the first of many loads that he would dump in my ass.

When he was done and zipped up, he complained that his breakfast was cold. He told me that I would be punished for that later and that I needed to make breakfast all over again. I still had tears in my eyes as I made his breakfast again. It wasn't fair that I was to be punished because the food was cold. After all, it got cold because he wanted to beat and fuck me instead of eating. He seemed so aggressive and he was bent on taking out those aggressions on me. I hadn't been there an hour and my ass, inside and out, was screaming for mercy. His cock was so big and thick and it just ravaged my ass. I could feel his cum leaking out of me as I stumbled around in those heels. I was getting better at walking in them, but it would take practice, which I was apparently going to get plenty of.

He beat and fucked me three more times that day. He enjoyed using that paddle and it hurt like hell. I don't know where he got his stamina, but it was impressive. Near the end of the day I found myself lying on my back on the kitchen table, my high heels pointed toward the ceiling. My ankles were over his shoulders as his cock jack hammered my poor ass. He had me screaming "I'm your bitch!" and "I'm your sissy slut" over and over. When he was about to cum he forced me to my knees and came all over my face and in my mouth. He zipped up and laughed at the scene: me in a purple maid's outfit, high heels, wig, dog collar, with his cum all over my face. 

"That was a good first day as my full maid," he said. Easy for him to say. He came four times that day and I hadn't cum once. "Wait until next week. I've got some more ideas for you. We are going to take full advantage of every hour you are here. I've been busy shopping online for things, so be prepared for lots to do for me." I heard those words with both dread and excitement. "I'm going to take a shower and am headed out with friends. I can't wait to tell them about my new maid. Now get cleaned up and get out of my house. Your money is in its usual place."

"Thank you, Sir," I said meekly. He walked out of the kitchen and I went to the bathroom and cleaned the cum and the makeup from my face. It felt good to get out of the wig and the heels, but I knew I had to get used to wearing them. On the table was $250, which was a nice surprise. As I was leaving, I realized how exhausted I was, not just from the beatings and the fuckings, but also from being afraid all day. I was constantly afraid of messing up and getting another beating. It also scared me how much it turned him on to beat me. Whenever he paddled or spanked me, his cock was so hard and I knew sucking and fucking were sure to follow. I did not know what lay in store for me and was a little afraid at finding out.