Old Man's Maid

"You clean the floor now," he ordered and obeying, I fell to my hand and knees.

This was the first day he really watched me clean the floor. If I turned towards him, he ordered me around so that my face was away from him and he had a better view of my ass and tail. The plug was uncomfortable at first, I guessed it was an inch wide and a few inches long. I couldn't and didn't dare try to expel it on my own. The hair swished like a real tail would as I worked, a very odd and strangely arousing sensation.

Towards the end of my four hours, he called me back over to him. "Bend over," he said. I did as he said and he grasped the base of the tail, his bony hand brushing my ass. With a quick tug, he pulled out the plug and I gasped at the sudden pain and emptiness. I turned around, needing to see it. "Every day," he said waving the plastic plug at me. I nodded my agreement.

****

So every day afterwards before I started my work, I would bend over in front of him and pull my ass cheeks apart so he could insert the tail. Sometimes he'd lick and finger fuck me to an orgasm before inserting the plug. Other days he seemed to enjoy my writhing when he pushed it into my protesting ass hole without any foreplay.

The best sex I've ever had was a few days later when he asked me to sit on cock. His hands and mouth immediately went to my breasts, pulling and teasing the sensitive nipples. He let me happily bounce up and down on his cock and I ground my clit on him on the down stroke. Just as I was about to cum, he pulled the tail from my ass and I screamed so loudly in extreme pleasure that I'm sure the neighbors miles away heard me. He seemed very pleased with me that day and held me in his lap for a long time, sucking my nipples and caressing my pussy in teasing strokes without inserting the butt plug again that day.

****

His additions to my costume didn't stop at the tail. A few days passed again and after inserting the plug in my asshole, he ordered me to turn around. He tugged the material down from my breasts and twinked my nipples into stiff buds. He then attached a tiny clamp with bells on each. I squeaked in protest as my nipples were pinched and keep hard by the clamps. I then went about my cleaning, the jingling of the bells announcing my every move.

Before leaving that day, he asked me to face him on his lap and one at a time, he removed the clamps. The rush of blood hurt a bit and his mouth went over the nipple as the clamp came off, helping the flow return. I gasped and wiggled and after the second clamp came off, my pussy was dripping. He then tugged at the butt plug but didn't remove it, just fucking my ass hole ever so slightly with it. My nipples felt more alive and sensitive than ever in his mouth and when he finally pulled the plug out of my ass, I moaned loudly with pleasure at finally having a release from the small tortures he was doing to my body.

****

He wasn't done yet with the painful acts of sex. I never imagined how close pain and pleasure could be until working for him. The afternoon began as usual, he licked my pussy ever so briefly before inserting my tail. I'm ashamed to admit how much I enjoyed having it in my ass, I was very tempted to buy my own to wear at home. My nipples tighten at the sight of the clamps, making his job easier to clip them on. Instead of allowing me to go clean, he ordered to me to lay across his lap.

I did as he said, stretching my arms and legs to reach the floor on either side of the chair with my stomach over his legs. He adjusted me forward so my hands were planted firmly on the ground and I was on my tip toes. He flipped my skirt up and smoothed it over my back, my tailed ass facing up in the middle of his lap. He moved the tail forward too so the hair fell on my back, pulling the plug into a slightly different position in my ass hole.

And then he spanked me! His bony hand came down hard on one of my ass cheeks without any preliminaries. And then on the other and then first cheek again and so on. I yelped in protest and his other arm came down on my back, pressing my chest into the arm rest of the chair. My breasts were hanging free with the little bells ringing with the impact of the spanking.

No one had ever spanked me before, not even my parents. And it hurt! Tears ran down my face but I didn't dare ask him to stop. I knew I was such a whore at that very moment when I was willing to let my ass be beat in exchange for money. The butt plug and nipple clamps were a bit painful but nothing compared to this. I cried like a little baby over the sound of his hand smacking my butt and the nipple clamp bells jingling.

After several dozens hard slaps, I was slumped over his lap, no longer trying to hold myself up over him. My butt burned and I'm sure it was cherry red with his handprints. He stopped spanking me and rubbed his hand over my cheeks instead. I flinched as the sensitive skin was touched gently. The warmth and the massaging began to feel good. I was shocked to feel my pussy becoming damp. The butt plug wiggled as he rubbed away the redness, reminding me of the fullness in my ass hole. His hand dipped between my legs and I blushed as his fingers touched my wetness. What I had already done with him was kinky but to be turned on by being spanked? I felt I had sunk to a new low of debauchery.

The spanking seemed to prime my body though and he began to finger fuck me, one then two then three of his bony fingers working their way in and out of my pussy. I gasped and moaned and cried as he brought me closer to orgasm. His hand that had been holding me down moved to my ass and with a couple of quick smacks on my rosy cheeks, I screamed my release and my cum soaked his fingers in my pussy.

I went limp on him. He didn't ask me to move and I wasn't sure I could have. My body felt used and wore out like never before. He rearranged the hair of the butt plug over my red ass and gently stroked the hair of my head until the doorbell rang announcing the nurse. He carefully pulled the plug from my butt with me moaning a bit at the soreness of my rear end. I almost fainted as I stood as the blood rushed from my head. He unclipped my nipples and for the first time ever, placed his thin lips on mine in a gentle kiss. I'm sure I was a mess, tears streaking my makeup and my red ass with cum juices running down my leg. I hurried out of the house, barely covering myself with my trench coat as I rushed head down past the nurse.

****

That night, I had to tell someone about this. I called my oldest and dearest friend Jim and invited him over as soon as possible. I trusted him with my life above all others. He arrived and kissed my forehead gently, noticing my trench coat and tear stained face.

"Tish, what's happened?"

I sat down on the sofa with him next to me and told him the whole story from the beginning, the secretary and the confidentiality agreement. The cleaning, the old man, and the uniform. The oral sex and butt plug and nipple clamps. And finally the spanking.

I hadn't changed out of my work clothes so I stood and removed the trench coat. His eyes went wide at the little French Maid uniform. I turned and flip up the skirt to show him my red hand printed ass. As I turned around, I sniffed back tears.

"Oh Tisha," he said holding his arms out to me. I curled up in his arms and cried. He patted my back and made soft comforting noises until the tears stopped.

"You wanna know what I think?" he asked. I nodded, hiccupping a little. "You are being paid to have sex with a perverted old man. But you know that already." I nodded my head again, blushing until my face was as red as my bottom. "The oral sex, the butt plug, the way he's gradually working you up to kinkier sex, it's all a dom/sub game."

"A what?" I asked incredulously. This was a game?

"Dominant, submissive, it's a sex role thing," he said. "You are obviously the submissive. He starts with something little like the oral sex. It bothers you but you think it away as nothing. And then he goes a bit further. And again it bugs you but you already let him do the first thing so you think what's the harm in doing this as well? And you are getting both pleasure and money from it so it's easier to accept. Right?"

I nodded, ashamed at myself that I hadn't figured this out on my own. "Where does it end? I mean what could he do next?"

Jim shifted me in his lap and I squeaked as my sore butt rubbed the rough denim of his jeans. "Oh sorry," he apologized. "Well," he began. "Since he spanked you today and he's been adjusting your asshole to the plug, he probably has a butt fetish and will try anal sex with you soon."

"Yes, I could see that. He has inserted his finger in there before."

Was it my imagination or was Jim looking a little pink in the face now? He cleared his throat. "That's probably a definite then in the future."

I thought about it. I could do anal sex with Edward. What was I thinking? I was just spanked like a little girl and I was considering going back to that job? "What else?"

"Some other dom/sub games include restraints-"

"Tying me up?" I interrupted.

"Yes. There's also denying orgasms until commanded to release but he doesn't seem to mind you cumming."

My pussy tingled a little at the thought of all the orgasms that horny old man had given me. "Anything else?"

"You really are sheltered," he said to me. "Get up." He took me over to my computer. He sat down at my desk while I stood over him and watched him google "dom/sub games." Thousands of sites popped up with everything from ball gags and cock rings to wax pouring and bestiality.

"He might make me have sex with an animal?" I felt sick to my stomach.

Jim gave a short laugh. "I doubt it, that's a pretty rare fetish. Although since he likes to see you clean almost naked, he might eventually bring someone else in to fuck you so he can watch."

I took a deep breath. This was going too far, I decided. It was one thing to be licked and fucked by one old man but to have another do it while he watched? Or what if he brought in a woman? Could I do that? And right now I was free to move about the room, I could get away if I had to. What if he started tying me to his wheelchair or other items in the room? Then I'd be trapped to endure whatever his perverted mind thought of.

"Has he ever had you suck his dick?"

I started, forgetting Jim was even there. "No. Should he?"

Jim shrugged and I noticed a ridge forming in the front of his jeans. "No, I guess not." He stared at my body, my breasts threatened to pop over the tight bodice and I had forgotten how little this outfit covered. "Would you suck mine?"

I was shocked my friend had the nerve to ask me such a question after everything I had just told him! But then again, I had to admit it had even made me a little bit horny talking about it. Besides I hadn't sucked a hard cock in a long time, I felt a little deprived that Edward had never asked. I dropped to my knees between Jim's legs and began undoing his jean zipper. He let out a breath I hadn't noticed him holding and the ridge in his pants grew.

And oh my, how it grew! I pull his hard cock out of his boxers, it was longer than my hand and I could barely wrap my palm and fingers around it. I licked a drop of pre-cum off the tip, enjoying the taste and his groan of delight. I went down on him hard and fast, leaving him gasping for air. I wanted to take his dick in my mouth so badly, I didn't want to waste any time. I sucked and licked and hummed and deep throated his cock while one of my hands massaged his chest and the other fondled his balls. I was possessed, I had to have his cum in my mouth!

"Oh Tish, oh god, oh Tish, I'm cumming!" he cried, his hand going to the back of my head and holding me down on him. Not that I had any intention of pulling off. I slurped and swallowed all his cum, loving every bit. He let go of my head and sunk back in the chair. "And that," he said trying to catch his breath, "is why he should have asked you to suck his dick."

I grinned and climbed up in his lap to give him a hug for being such a great friend.

****

After my conversation with Jim, I had made up my mind to quit the next day. Things were becoming too extreme for me and I felt duped and used. I put on my costume out of habit and there was a nagging thought in the back of my head. If they begged and promised me it would only be vanilla sex from now on (I had spent the rest of the night reading up on "kink" and so forth on the internet) and offered me more money, I would probably stay. I couldn't help it, the thought of that man's mouth sucking my breasts and his fingers up my pussy still makes me wet.

But when I arrived, my choice had already been made for me. There were several cars in the driveway, including an ambulance. The secretary and nurse met me at the door.

"Come in," the secretary ordered and they rushed me into the office. I saw an EMT coming down the stairs as they shut the office door behind me.

"I might as well just say it," the secretary sighed. The nurse looked sad and accidentally let her own trench coat open just a bit. She was wearing a very similar outfit to my own only a little white trampy "nurse" dress with white thigh highs and garters. I wondered what exactly her "duties" had been after I left every day!

"Edward died in his sleep last night."

"Uh, what?" I asked, my mind still thinking over what the nurse and the old man had been doing in the evenings.

"They think he had a heart attack. He was eighty six years old you know."

I didn't but I nodded my head anyways. Just like that, my job as a paid whore was over.

"He left you both these checks in case of his death. He greatly appreciated your services to him." The secretary handed us both slips of paper. I tried not to let my jaw drop when I saw "one million dollars" written under my name. I couldn't believe I had just become a millionaire!

"May I keep the outfit?" the nurse asked quietly.

"Me too," I chimed in, surprising myself.

The secretary looked a little confused but agreed. "Actually there were two boxes left in his room, one with each of your names on them. I guess he meant for you to have them as well." She stood up and took two small plain shoeboxes from a shelf. "I have no idea what's in them, I haven't begun to go through his personal effects yet."

My box jingled a bit as she handed it to me. Just to make sure my guess was correct, I nudged the lid off a bit and peeked inside. There laid my horse tail butt plug and two little nipple clamps. I quickly shut the lid embarrassed to see the items and remember how Edward had pleasured my body with them over and over again. I noticed the nurse was also blushing at whatever was inside her box.

"Thank you again and I ask you in memory of Edward and whatever you had with him, that you not speak about this with anyone else." The nurse and I nodded and we turned to go.

As I drove home from the mansion for the very last time, I thought about exactly what I had had with Edward. It was certainly not love but I had grown quite fond of him. Especially the way he touched me and brought me to orgasms like no one else. I drove one handed all the way home, my other hand playing with my bare pussy as I remembered just exactly how Edward could get me off in the kinkiest ways.

Walking into my apartment, I set the check and box down on my desk and immediately called Jim. I thought he might like to come over and see my "entire" outfit and watch me clean my apartment.