You probably want to ask more questions now than before you read the letter. Let me start by giving you a bit of history. If you remember, the letter started as a ‘Thank You’ letter, which means I had to do something first.

I have worked retail for a big box store for the last five years. I started part-time while I was still in high school and sixteen years old. I earned just one dollar more than minimum wage, which was okay for a teen still in school and living at home, but not so much for an adult who wants to live on her own. It augmented my meager allowance rather than replace it. Even full-time after I graduated, it was too little to live on my own, much less go to college.

Dad was upper-level management in a large marketing firm and made loads of money. Mom was an assistant manager at the store I worked at, but it was nothing compared to what Dad brought in. Luckily, Dad was smart enough to plan for his loss. Whether it was death or unemployment, he prepared for it. Dad once said that he loved us so much he would never be happy in the afterlife, knowing he left us penniless or struggling.

So, with a massive 401(k) and a substantial life insurance policy, we would be set, right? Wrong!!! No matter how much insurance you pay for, there are always bills left over at the end. You see, Dad had cancer. He tried everything he could, even experimental treatments, which we all know aren’t covered by insurance. So after paying the leftover medical bills, paying off the mortgages on the house (yes, there were two), paying off the car, and getting me a used one, there wasn’t much left—just over half a million.

Living in this upper-middle-class house was draining our resources faster than the interest could replenish it, so Mom and I talked about selling the house and buying something cheaper. That was when I came across the ad. You see, the place we lived in was 6000 sq ft on 5 acres of land and a large in-ground pool. The maintenance and the utilities are what’s draining the reserves. So I was looking through the paper to see if something around 2000 sq ft and roughly two acres was available. I found two worth looking at advertised by local agents. I marked them and just kept looking out of boredom.

HELP WANTED

Young woman 18-25 To

serve guests at Private

Party. To schedule an

interview, please call

I immediately grabbed my phone and called the number. “Miles residence,” came the pleasant male voice.

“Hi. My name is Emily Stanton. I’m calling about the ad you have for a server for a private party,” I replied, trying to keep the nervousness from my voice.

“Please take down my email address. Take several pictures of yourself and attach them to the email. Include your measurements as well as your neck. You will have a response within twenty-four hours of receiving the email. Please make sure the pictures are taken with as little clothing as you can. Nude is preferred, but underwear or bikini will be fine,” he instructed.

“NUDE!? I’ll have to think about that. How soon do you need the email?” I asked.

“The party is next weekend. We will need to confirm staff and servants by this Thursday,” he confirmed.

“Alright, today is Monday, so that gives me a day to get the email to you and still give you time to get back to me and anything else,” I said, primarily to myself.

“I look forward to hearing from you, Emily.”

Asking for nudes was unexpected, and I wasn’t sure I could do it. I grabbed the newspaper and my phone and headed to my room. If I were going to do this, I needed to get it done to get the email back to him. ’Could I do it? I am not comfortable being naked in front of Mom. Would a stranger be any different? Maybe I’ll just take a few in my underwear. No. That won’t do. I am certain this is a sex party for the rich. If I can’t be naked here, how can I bring myself to do what I imagine will happen at the party?’ I thought to myself.

It was a good thing I was home alone. Mom was salary, so she spent a lot of time at work. I was full-time, but hourly so I didn’t stick around. Mom and I rarely saw each other. So, it was like I lived alone in this huge house. I took off my blouse and skirt and looked at myself in my full-length mirror. The standard bra and panties just wouldn’t do. I removed them and looked at myself nude. I knew I was beautiful but was shy about my body. A bit self-conscious. I took the requested photos: front, back, both sides, nothing too erotic. ‘I can’t believe I’m actually doing this. I hope Mom doesn’t find out. She’d be so angry and disappointed in me.’ I thought, just a lot nervous.

Considering the nature of the request, I could imagine that this would end up being a sex party. I was so nervous about sending the nudes that I put off transferring the pics to my laptop. But I continued to walk around the house nude. If I do this party, I needed to be comfortable with my body. It’s appearing nude in front of others that scared me.

I walked from room to room, then went for a swim, which took the most courage. Then I fixed myself dinner and watched a couple of movies in the living room. I heard the garage door open and knew Mom was home. I shot out of the room and slammed my bedroom door. I took a shower and put on my pajamas, and headed back downstairs. Mom had kicked off her shoes at the door like she always does. One of our rules is ‘no shoes in the house.’ The floors are heated, so it is nice walking barefoot in the house. Besides, it protects the floors from being damaged by debris brought in from outside.

By the time I got back to the living room, Mom was in her favorite place with her feet up. I sat on my end of the couch and finished watching my show. After the movie was over, I kissed my mom good night and headed to my room. I stripped off my pajamas, sat nude at my computer desk, and transferred the pics to the laptop. Attached them to a new email to Mr. Miles, added my measurements 4’ 11”, 95 lbs., 28B-24-28. With a neck measurement of 11”. I sat there and hovered the mouse pointer over the send button. I brushed my hair and braided it before I mustered the courage to click the send button. There was no turning back now.

I was so nervous about the email and the nude pics that I didn’t even think about this being the first time I slept nude -- ever. I checked my email as soon as I got out of bed. I sat there staring at the email from Miles, afraid to open it. It seemed like forever, even though it was just a couple of minutes before I finally opened the email.

From: B. Miles

To: Emily Stanton

Subject: Job Interview

Dear Miss Stanton;

During our initial phone conversation, you made it clear you were against providing nude photos. I am pleased that you managed to overcome your reluctance. It shows you are willing to set aside your fears to experience new things. I find your appearance to be more than acceptable, along with your courage, have qualified you for the next stage of the interview process.

Please be at my home Friday at 7 pm. Be prepared to stay the weekend. You will be free to leave at any time, but if you stay until the end at 7 pm Sunday, you will have passed and will be asked to return the following weekend.

Bring nothing with you except the clothes you have on. Wear a light summer dress and strappy heels. Nothing else. No make-up, no underwear, and no jewelry. Leave your purse in your car. That will be the first test.

B. Miles

Well, that settles it then. I had my weekend planned. I closed the email and shut down the computer. I went to take my shower before getting dressed for work, sans underwear. After work, I dragged my tired body home. Taking my shoes and my clothes off at the door, I carried it all upstairs. I got lucky. I heard Mom move around in her room, so I ducked quickly into my room. I don’t need to explain my nudity in my room, but in the rest of the house might be a problem. I must be more tired than I thought. I didn’t even notice her car in the garage.

I stayed in my room, hoping Mom would go back to work. Unfortunately, she didn’t, so I took a shower and put on a pair of shorts and a t-shirt, sans underwear. I haven’t worn underwear all week, and it is beginning to feel normal. I spent the rest of the evening with Mom.

Well, it’s finally Friday. I had to work today. Luckily, I got off at 3 pm, so I had plenty of time to prepare for my weekend. It was half-past three when I finally got home. I was home alone, so I stripped. I took a shower and shaved everything below the neck. I applied a moisturizing lotion after shaving, and I was as soft and smooth as I have ever been. I set my alarm and lay down to take a short nap. My job is more mentally stressful than physical, and I always feel exhausted by the end of my shift.

My rest was anything but restful. It was 6 pm and time for me to leave. I put on the summer dress, and the heels I had were 4-inch stilettos. A quick run through my hair with a brush, and I was ready. I can’t drive in heels, so I just carried them to the car and drove barefoot to Mr. Miles’ address.

The gate opened as I approached. Guess I was being watched. I pulled up to the front door and slipped my heels on before getting out of the car. A young-ish woman wearing a maid outfit opened the door. “Welcome to Mr. Miles Miles’ home, Miss Stanton. If you would give me your car keys, I’ll have your car parked out of the way. You are to remove your shoes and dress and give them to me as well. I will take you to Mr. Miles Miles’ study, where you will wait for him. You are to kneel on the floor so you do not leave marks on the furniture. Mr. Miles Miles will be with you shortly,” she informed me.

As she was instructing me, I was removing my shoes and dress. Now I was really nervous, being in a stranger’s house naked. It was most definitely a first for me. The maid noticed me shaking.

“There is no need to be scared or nervous, Miss Stanton. You will not be harmed here. I assure you, you are safe here,” the maid said.

She placed her left hand on the small of my back and led me to Mr. Miles’s study. She moved me to a spot in from of a nice leather chair. She put her hand on my shoulder then, with light pressure, directed me to kneel in front of the chair. I knelt as was required. She showed me where to place my hands on my thighs and left the room with my clothes. ’Everything is so elegant. The wood is all mahogany, even the bookshelves. Shit! I wish he’d hurry up. My knees are starting to hurt on this hard floor’ I was getting bored waiting (there is just so much you can see from the floor) when he finally entered the room. He stood in the entrance for several minutes before sitting in the leather chair in front of me.

The Interview

“Emily Stanton. It is a pleasure to meet you at last. Maria tells me you followed her directions without any complaint or resistance,” he stated matter-of-factly. “Those are the actions of a submissive. Are you submissive, Emily?”

“I don’t believe I am, Mr. Miles. I live an independent life. I am not looking for someone to control my life. I do that well enough on my own. I am a successful and efficient department manager where I work. I am sure you did a preliminary background check on me before inviting me here for this most unusual interview. If I didn’t mind doing as I was instructed, I could have left. I’m sure you are aware of the things some people will do to give themselves the best chance of getting the position they are interviewing for.

“I have been nude as much as I can at home, getting used to my body being on display. I am only doing this for the adventure and the money, which we still need to discuss. In only a week, I have come to enjoy being nude. The thought of attending your party nude in front of others is scary, intriguing, and exciting. I want to experience it at least once. I let my mom know where I will be this weekend if you agree to let me stay,” I told him.

“So, you’re not submissive by nature but know when to be compliant and obedient as well as when to say enough and leave?” Mr. Miles stated.

“Yes, that is a pretty accurate assessment of me. Everyone with a job is obedient and compliant or unemployed. That doesn’t make them submissive, Mr. Miles.” I told him, looking him in the eyes.

“I am twenty-one and know very little about what happens at private parties for the rich. I imagine the rich have these parties to indulge their sexual kinks without jeopardizing their public image. I thought coming to a private party I would get some experience.” OMG! I can’t believe I confessed that to a stranger.

“What have you done? Have you sucked a cock or licked a cunt? Have you had anal?” he asked.

“No, I have not done either of those. I have only had sex once with a boy in high school. I haven’t really made any effort to date. While I hate my job, I love spending time with Mom,” I told him.

“If you are willing to go through with this, then I have some paperwork for you to sign. One document is the contract for this weekend; it states that you will be nude for the entire weekend and work as a servant of my household. Maria, the maid you met, will be your trainer and boss for the weekend. You will call her Miss or Miss Maria and will obey her. If you make a mistake, you will submit to punishment. If you refuse to accept something, you will be dismissed and asked to leave the property.

“The second document is a non-disclosure agreement. Saying you will not talk about anything that goes on in this house, or if you go to the club I own, there as well.”

I signed the contract for this weekend and the NDA, but I could not sign the contract for next weekend. He gave it to me and told me to keep it in my room until Sunday evening. I was told to stand and follow him. He led me to a small room in the servant’s section of the mansion. I put the contract on the stand next to the bed, and I followed him from the room. I followed him upstairs, where we found Maria cleaning a bathroom.

The First Weekend

“She signed the documents you read. She is yours for the weekend. Make sure she understands what will be expected of her next weekend. According to the agreement, if she can’t handle it, she is free to leave.” He turned to me, “Your dress and shoes will stay in Maria’s room until you are ready to leave. You will have no access to any clothing until then.”

“Yes, sir,” I said. “Yes, Master,” Maria said.

“Miss, why do you call him ‘Master’? If you don’t mind me asking.”

“I was ten years old and living on the streets of Madrid, Spain. I saw him leave a really nice restaurant. He stopped and was getting into his limo when he looked at me from across the street. He crossed the street without saying a word, picked me up, not caring that I was filthy and smelled. He put me in his car, and we drove away.

“I thought he was going to use me for sex, but he never did. I have no papers, no certificate of birth, and no passport. I am in this country illegally. Mr. Miles packed me in a shipping crate to get me through customs. I was let out during the flight to America, then put back in after landing to get through U.S. customs. There were two small bottles of oxygen. He made sure the crate I was in was expedited by bribing the customs agent. I was loaded into the pickup that was waiting for us.

“I was stripped nude like you are, and the current maid cleaned me up. She taught me English and how to be a maid and cook. I apprenticed under her and the cook. I was left with instructions and allowed to work alone when I turned fourteen. By the time I was eighteen, the older maid had retired. She was in her seventies. I took over as the maid of the house. She called him ‘Master’ since before I arrived, so I just started doing it. No one objected, so I still do it. As I got older, I asked about it. We are servants but not slaves. He is the ‘Mr. Miles’ of the house, so it just seems right to call him that,” she explained.

“Should I call him Master? I am only here for the weekend and not a full-time member of the staff. I have been calling him ‘Sir,’ and he has not corrected me,” I inquired.

“He commanded you to call me Miss or Miss Maria, but if he did not specify what to call him, you may continue to call him ‘Sir’ until he changes it.”

Over the weekend, I was always tasked to be where I could hear the door. It was my job to answer it and announce all visitors. Their responses to my nudity varied. Smiles. Smirks. Comments. But none of them touched me. I lost count of how many times I was spanked by Maria in front of the rest of the staff, guests, and occasionally of Mr. Miles. Saturday evening, I was clearing the dinner table when I tripped over Mr. Miles’ foot as he was getting up. I broke several of the dishes I was carrying. I was terrified, not knowing what would happen. Since I was already on the floor, I got up on my knees and apologized to Mr. Miles. I began to clean up the mess with Maria’s help. When we were done, Mr. Miles said.

The Punishment

“Maria, take Emily to the basement.” Then he walked away.

“Follow me, Emily. I’m so sorry. The basement is not a place you want to be. It is for punishment only. You are to be whipped,” Maria stated.

I followed her to the basement and saw several pieces of furniture, for lack of a better word. Maria led me to an archway and told me to stand there. She went to a cabinet and brought restraints. She fastened them to my wrists and ankles, then attached them to rings in the arch. I was spread as wide as I could be. Being such a small person, Maria had to use short lengths of chain to attach my ankles. That left me almost two feet off the floor.

I hung there for a short time before Mr. Miles showed up. During the wait, Maria had removed her maid uniform to show she was nude under it. I wondered about that. She had selected a flogger and held it until Mr. Miles arrived, and she offered it to him. “Emily, this punishment and the next twenty-four hours of your life are the real ‘interview’ that will determine if you will get to return for the party next weekend. If you make it through it all, then you will sign the contract for the party. Working with Maria was just to keep you busy and out of the way while setting up the rest of your interview.

“No, Maria. You will be the one to administer her first punishment. Before you begin, she needs further preparations. I want a collar around her neck, a plug in her ass, and clamps on her nipples and clit,” he instructed. Only then did I realize the severity of my punishment. I was petrified now, and tears began to run down my cheeks.

“Yes, Master,” Maria said meekly.

She opened another drawer and pulled out a leather collar, brought it to me, and fastened it around my neck. Now I know why my neck measurement was requested. Once she was done with that, she went back to the same cabinet and pulled out a black latex butt plug from another drawer. I had never used one, but I have seen them many times in some of the porn videos I watch. Maria opened a tube of lube and put a generous amount on her fingers. Then put the tube in my ass and squeezed some in. Then slowly, one finger, in and out, then two fingers, then three. With each additional finger, my moans became louder, my breathing faster. I could feel my pussy getting wet and noticed a growing puddle on the floor. It was embarrassing, but there was little I could do. Endure it or use my safeword.

I knew if I quit, I would always wonder, not to mention what it would say about me having quit just because the road ahead was thought to be too difficult. If I endured it, I would have a life-altering experience for the rest of my life. So, I chose to endure and remained quiet except for my moans of pleasure. After I had reached my first orgasm of the weekend, Maria began to work the large plug into my well-lubed ass. The pain of it stretching my anal ring brought even more tears to my eyes and screams to my ears. Finally, it entered with a plop. I was close to my second orgasm when with a hard slap on my ass by Maria, I went over the edge into a massive orgasm.

Maria waited several minutes for me to recover before she started to apply the nipple clamps. At first, they felt good. Maria worked each nipple until they were a little longer than half an inch long (okay, so my nipples appear huge for such a small frame). Maria attached the clamps to my erect nipples. Little did I know she was just attaching them and had yet to tighten them. She seated them in the proper position and really began to screw them down. Again, I gave out a mighty scream only to have Mr. Miles shove a ball gag in my mouth. I know this kept me from using my safeword. I will take this up with Mr. Miles later. I still screamed, just not as loud. I thought the last two things were the worst pain I had ever felt. I was wrong. It was the clit clamp that hurt more than I could take, and I passed out. By the time I came to, Maria was done, and I was still in incredible agony. I was breathing hard and rapidly. Someone had put hooks in my nose and hooked it to the gag strap forcing my sinuses open. It made it easier to breathe, not that I was able to complain.

Just as I was growing used to the pain, I heard the ominous sound of the flogger swishing through the air. I tensed and shrieked as I expected pain from the inevitable strike, but nothing happened. The sound of the many strips of rubber was indescribable but one I would never forget. Then my world exploded into an entirely new and excruciating pain as the first of many strikes landed across my lower back as the strips wrapped around to spread their unwanted sting to my side and front. Over and over, Maria struck me with the flogger. Twenty-five lashes on my back, butt, thighs, and breasts, with the last two directly on my pussy and butt plug. I swear Maria was trying the see how much of my body she could whip with just twenty-five lashes. I had several orgasms during the whipping (not that I am into pain), but nothing compared to the final one when she struck my pussy and clit clamp. According to Maria, I was unconscious for ten minutes. Mr. Miles helped get me down, after which Maria tended to the marks on me.

Once I was aware enough to sit up, Maria attached a leash to the collar. I noticed the clamps were gone, but the plug and collar were still there. I asked about the collar and leash. Her only response was to pull on the leash. I had no choice but to follow. She led me to Mr. Miles’ study. I was directed to kneel next to his desk and office chair. Maria stood next to me, still holding the leash.

Mr. Miles finally acknowledged me. “You have passed the second test. Now for the next test. You will wear the collar and leash until you leave Sunday evening. The plug will also remain in unless you need to relieve yourself. Maria will remove it and put it in the sink; then you will take care of your needs. When you wash your hands, you will wash the plug and lube it. You will hand it back to Maria and she will re-insert it. From now until you leave, you will refer to Maria only as Mistress and me as Master. Understand?”

“No, Mr. Miles, I don’t,” I replied, my anger fueled by the indignity of his command. I reached up and removed the leash from the collar as I rose to my feet. Mr. Miles looked at me without changing the expression on his face. Maria did nothing to stop me. “I told you during our initial meeting that I was not submissive. While I will consent to many things required of me for a job, I will not be treated as a slave. I will give you the respect of calling you ‘Sir.’ Still, I will not call anyone ‘Master’ or ‘Mistress.’ I am interviewing for a hostess position, if it could be called that, for what I believe is a gathering of wealthy people to indulge in their sexual kinks they don’t want others to know about.” Done with my rant, I fell silent, waiting to hear what Mr. Miles would say.

“Maria, bring Miss. Stanton’s things here, please,” Mr. Miles commanded.

’Shit. I fucked it up. Now I know Mom will be disappointed in me.’ I stood in front of Mr. Miles, still naked, waiting for Maria to return with my clothes and keys. While I was waiting, I removed the collar and set it on Mr. Miles’ desk. Once I had my stuff, I put my dress and shoes on, took my keys from Maria, and stepped toward the study door.

“Miss Stanton? A moment more of your time before you decide to leave.”

I stopped and turned to look at him—a look of sadness on my face.

“You came here for an interview.” I nodded. “You think it was for a party.” Again I nodded.

“Your point, Mr. Miles?” I asked, getting irritated at him for dragging it out.

“If you stay until the end of your weekend contract, you will indeed attend the fundraiser I have planned for next weekend. That is the party the ad mentioned. It is not a sex party, although I have had a few of those, as well. I am interviewing you for an offer that has nothing to do with the party. You are welcome to leave as you have planned; however, I am hoping you will stay.”

“I know that if I leave, I will go back to work at a job I can’t stand but have no choice because I’m not qualified for anything else around here. Staying is the unknown. I could use the money for the party. I know it is just a drop in the bucket in the big picture, but every little bit helps. If you agree to stop all the crap with the collar and Master/Mistress nonsense and tell me what you have planned for me for the next 24 hours, I’ll let you know.”

“I don’t need you for the fundraiser. I thought it would be something you would enjoy doing. The fundraisers have been around since my grandfather made his first million. They are, as you guessed, for the wealthy to get together and relax without people taking pictures and selling them to tarnish reputations or public images. Maria has been a part of them for years. I hire caterers to serve the guests. What I want you to do is serve the guests naked. The rest you will find out next weekend. Not even Maria knows what I have planned.

“Starting tomorrow at noon, provided you chose to stay, you will be in the great room kneeling. You will suck my cock and swallow; then you will eat Maria’s pussy. Afterward, we will critique your performance, so you will know where you need to improve. At that time, Maria will remove your plug and return it to the basement after it is cleaned.” ‘Oops! I got so used to it being there I forgot it was still in my butt. I was about to leave with it still in my ass. I wonder if Mr. Miles or Maria remembered and just refused to say anything. Waiting to see what I would do.’ I thought quietly to myself, trying not to smirk. “Then you will service some guests one at a time for four hours. After each four-hour round, you will get a one-hour break so you can take care of your needs and shower. Maria will give you a douche and enema before returning. Round two will be pairs. Round three will be three men where you will experience being spit-roasted (one in your mouth and one in either of your ass or pussy), double-penetrated (one in your ass and one in your pussy), and airtight (one in all three holes at the same time). You wanted some experience, that is why you answered that ad is it not? Stay or leave, your choice, Emily. You will not be doing any of that at the fundraiser.” I removed my dress and shoes and handed them back to Maria.

“Thank you, Emily. You won’t regret your decision. Both of you have the rest of the evening off.” Looking at me, he said, “You will work with Maria in the morning until she brings you to the Great Room. Good night, you two.” With that, we turned and left the study.

The Following Day

Maria and I met Mr. Miles in the Great Room a few minutes before noon. “Kneel,” I was told by Mr. Miles as he pointed to the floor in front of him. I knelt as I was told and looked up at Mr. Miles. “Take my cock out and suck it. Just do what comes naturally.” I took his cock out and opened my mouth, and began sucking, moving my head up and down its length as I’ve seen in porn.

“That was the worst blowjob I have ever received, Emily. For the rest of the first round, Maria will use a riding crop on your tits every time one of the guests lets her know you touched their dick with your teeth.”