tagTranssexuals & CrossdressersNew Job, New Life as as Sissy Slut

New Job, New Life as as Sissy Slut

bysdbottomslut©

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.

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by Anonymous

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by Anonymous05/28/14

love to have a big load in my mouth

I would love to be a sissy and be fucked every day in my pussy and in my mouth

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by sissymida04/01/14

lovely life

mmmmm lovely story it made me so horny I would absolutely adore having it happen to me

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by Anonymous03/01/14

I'm a sissy too

I too am a sissy faggot cocksucking slut bitch who loves sucking big cocks, swallowing lots of cum, and getting fucked by a hot studly well-hung man. This story turned me on so much. I can't wait to readmore...

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by CuckyJimmy12/27/13

Fantasy

I have these fantasies too sans hitting. I just like the idea of being someone's bitch.

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by Anonymous11/16/13

hopefully my new life

oh how I would love to serve mastermike like this

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