Help Wanted


Brian found a table at the coffee shop, and sat down. This shop was his haven during the day. He had been applying for jobs since being laid off three months ago, and would use the shop's free internet. His savings were running out, and Brian was starting to feel desperate.

"Order ready for Brian" the barista called out. Brian quickly grabbed his coffee. As he sipped the warm dark roast, he opened his laptop and began browsing new postings.

"Any luck finding a job?" the voice standing over him said.

"Not so far, it's been a rough few months." Brian replied. He looked up and saw the barista standing over him.

"I'm Jessica by the way" the barista replied. "I've seen you in here quite a bit, I assume you're looking for work?"

"What gave that away?"

"Young guys like you don't spend all day at the coffee shop" said Jessica, trying to contain her laughter.

"I suppose you're right." said Brian. He sighed a bit, realizing that his situation must be obvious to everyone.

"I hope you don't mind if I sit here." said Jessica, after seating herself.

"No, not at all!" Brian replied.

"Good, I've been standing all day." Jessica said, looking Brian over. He was of average height with soft facial features, and his hair was starting to get long, clearly due to lack of funds for a haircut. "You know, I might know someone who is looking for help. It would be labor, and not a particularly glamorous job, but I'm sure you could use the money."

"Really? I'm not sure about that, my last job was in IT and I'd like something in the field." said Brian. He was thankful for her offer, but knew that this sort of job would only delay his career, and perhaps get him stuck going work he had no interest in.

"Think it over, it's my Aunt and she treats her employees well. She owns a small bed and breakfast outside town and pays a good wage." Jessica handed him the card as she spoke, Brian placed it in his bag.

"Thanks for the offer, I appreciate it" said Brian. Jessica stood up and stretched.

"Well I need to get back to work, I see a customer coming in. Good luck!" Jessica walked away before Brian could reply. He stared at the card. It was from a place called Red Oak Bed & Breakfast, which Brian had never heard of. He decided he would at least call and get more information. After he finished his coffee, of course. Brian checked for job postings one more time. A few times he peeked up from his computer, and Jessica gave him a knowing smirk. He found her attractive, but was sure that she would have no interest in homeless man sitting in a cafe all day. He slowly grabbed his things, and went back to his car.

Brian had been living in his car for about a month, so it was quite a mess. Before that, he had been living with his parents, but was forced to leave. After a long argument in which his mother called him all sorts of nasty things, Brian found himself kicked out, with nothing but his clothes and a few personal items. He got in the driver's seat and called the number on the card.

"Red Oak B&B, this is Anne, how can I help you?" said the voice on the other end.

"Uh, hi. My name is Brian Taylor and I was given your card by your niece at the coffee shop, she said you might have a job" Brian nervously said.

"Oh wonderful, yes we do have an opening, would you be able to come by at 10 to discuss the job?" said Anne, in a very warm and cheerful tone.

"Yes, thank you, I'll be on my way." Brian replied.

"Wonderful, see you then!" Brian checked in the mirror to look himself over. He combed his hair and grabbed a button down shirt to put on over his t-shirt. He looked up the address on his phone, the B&B was on the edge of town, but he was sure he could make it in time. As he drove, Brian wondered what kind of job a Bed & Breakfast owner might be offering. He assumed it would be some kind of maintenance, maybe yard work and such. Probably not a well paying job, but it would at least be some kind of income, and Brian could always continue searching for something better.

Brian approached the sign for Red Oak B&B. The building was not visible from the road. In fact, if not for the sign, one would mistake it for a lonely grove of trees surrounded by farmland. It was about 5 miles outside the city, and you could just make out subdivisions beyond the trees. As Brian turned into the driveway, he was treated with a picturesque tree covered drive to the main building. At least he would be working somewhere nice, he mused to himself. The main building came into view, and it was a breathtaking sight. It was a large Tudor style mansion, with the driveway leading to a large circle in front of the main entrance, with a fountain in the center and a large porte-cochère at the entrance. Brian parked near the front, checked his appearance in the mirror, and made his way to the door.

Brian hesitated, and knocked at the door. He tried to calm his nerves by drowning out his thoughts in the sounds of the forest around him, but to no avail. The door opened and he was greeted by a classy, yet sexy maid. She was wearing a classic black french maid dress with a white apron, the skirt ended before the knee. She black stockings and heels, and as Brian noted, great legs. She even had the little white hat on top of her long dark red wavy hair. Oddly enough, she seemed to be wearing a rather elaborate leather collar. It was about the thickness of a dog collar, and had a metal plate in front that seemed to have something engraved on it, but Brian couldn't read it. He was sure she was a model of some sort, she was taller than most women and was quite well endowed. Brian must have been standing there awkwardly speechless, she blushed and greeted Brian.

"Good Morning, you must be Mister Taylor." said the maid, "I'm Allison, please follow me. Miss Marks is waiting for you in the parlor."

"Uh, yeah thanks" Brian sheepishly replied. He quietly made his way inside unsure of what to say and entered the foyer, a large grand room covered in rich dark wood paneling. Beyond the door were several large entrances to other rooms, and a grand staircase in the back. Brian dutifully followed Allison, unable to keep his eyes off her legs and butt, her dress swishing to each side as she walked. They walked into what must have been the parlor.

"Miss Marks, Mister Taylor is here to see you." Allison gracefully declared. Seated in a large armchair near the fireplace was a woman as beautiful as Allison, if a bit older. She had dark brown hair with a fire grey whips here and there, and was wearing a smart and tasteful grey suit with a pencil skirt.

"Oh wonderful Allison, thank you. Mister Taylor, Brian is it? Hi I'm Anne Marks. Why don't you have a seat here and we can chat." Anne motioned to the identical armchair on the other side of the fireplace as she spoke. Between the chairs was a small table, and the walls were covered in artwork and more dark wood paneling. Brian sat down in the chair, and Anne motioned to Allison.

"Allison dear, will you please prepare some tea for us?" Anne said. Allison dutifully nodded and left to prepare the tea.

"Now, Brian, I understand you are interested in the position I have available. Please, tell me more about yourself." Anne said. Brian noted that she had a very sweet and caring tone when she talked, he felt oddly comfortable around her.

"Yes ma'am, I've been searching for a job for quite some time. I've been going to a coffee shop in town to fill out applications and the barista there gave me your card, she said she was your niece." with a noticeable quiver in his voice.

"Oh yes, Jessica. She's such a wonderful girl, and she has such fine taste, bringing me a well mannered man like you!" Anne sweetly replied. "Part of the atmosphere we try present here is that of a fine formal country estate, a place for our guests to unwind and be pampered by luxurious surroundings."

"This is quite a beautiful place, I can imagine it's popular" said Brian

"Oh yes, this was once the home of the founder of the local department store, I bought it from one of his grandchildren and decided to run it as a B&B. How long have you been out of work?" Anne asked.

"About three months, my previous job was as a desktop support technician at First National Bank downtown, I was laid off due to a the merger." Brian replied.

"Oh yes, I've heard about the layoffs, it's such a shame to see good people such as yourself lose their jobs." said Anne. They chatted for a bit, mostly about Brian's interests and work history. Anne looked up as she spoke, Brian turned around and saw that Allison had returned with a tray of tea, served on what looked like fine china and silver serving dishes.

"Oh wonderful, Allison, please serve us each a cup. Sugar, Brian?" Anne asked.

"No thank you." Brian replied. Allison placed the tea trey on the table between the chairs, and bent over to prepare the cups. She had positioned herself right in front of Brian, who couldn't help but stare at her garters and the bottom of her panties. He was unaware that Anne was watching, giving a slight smile at Brian's gaze.

"Allison is just wonderful isn't she? She's been with me the longest, almost ten years now, and she still looks amazing. Don't you agree?" Anne said, Brian sheepishly nodded his head and squeaked out "yes, she is"

"Thank you Allison, you may return to your chores." Anne said, in a loving yet commanding tone. Allison curtseyed and left the room.

"You would never believe that when I first met her, she was a man down on his luck much like yourself." Anne stated. Brian was taken aback. There was no way that beautiful woman was ever a man, he decided it just wasn't possible. Anne couldn't hold her excitement as she watched the gears in his head turning to put together the pieces. She had had this same meeting with several other men who eventually came to work for her.

After a minute of silence, Brian finally replied "is this the job you want me to take?"

"On honey, what I want doesn't matter. If you want to become one of my maids, then I would certainly be willing to make that happen." Anne said, returning to her previous loving tone. "Tell me, where do you live?"

"Err..." Brian didn't know what to say. He didn't want to tell this nice lady that he was homeless, she might not want to hire a homeless man to work in such a fine place.

"Brian, honey, you can be completely honest with me. I saw your car when you drove up, that's where you live isn't it?" Anne asked, with a caring look that Brian couldn't hide from.

"...yes." Brian sheepishly said.

"Were you evicted?" Anne asked.

" I was living with my parents. You see..." Brian drifted off, not sure whether to tell her about this secret. After all, Brian's parents had only been the first people to ever discover his secret.

"Whatever it is, it's okay, you can tell me." as she spoke, Anne grabbed Brian's hand and stared into his eyes.

Brian sighed "You see, I like to wear women's clothing. While I was doing laundry, I left a load containing some panties in the washing machine, and my mother found it."

Brian was almost tearing up as he spoke. "She called me terrible things, faggot, tranny, etc. and kicked me out."

"Oh, you poor thing!" Anne exclaimed. She hugged Brian, attempting to console him.

"I'm so sorry for what's happened to you." Anne said, releasing Brian from her grip.

"Let me get down to business. Allison and Stephanie have more work than they can handle, and we really could use another maid. Of course, I only hire female maids." Anne said, with a smug grin.

"I..." Brian stammered, unsure of what to say. A part of him really wanted to be a sexy maid like Allison, but he wasn't sure he could ever look as good as her. Brian had assumed that she wanted him to be her handyman, that was at least a normal job, and something he could easily leave. The maid job... not so much.

"You don't have to decide now, come, I'll give you a tour of the house. When we're done, you can give me your answer." Anne said, gesturing to the door. Brian stood up to follow her out of the room.

"So you've been in the foyer, the dining room is that doorway opposite the parlor. I only use it for formal events, the informal breakfast area in the back is used for most meals." Anne said, motioning to the arched entrance to the dining room. Inside, was a large, heavy wood table surrounded by matching chairs. A large china cabinet filled with very fine looking china and silver serving dishes sat on the opposite wall. The rest of the wall space was covered in artwork.

"Before we continue on the tour Brian, there's something I must explain to you." said Anne in a serious tone. "Red Oak is a Bed & Breakfast catering to a very specific clientele."

"How so?" asked Brian.

"We specialize in providing weekend getaways for people involved in various kinks. This place is sort of a secret playground for those with, shall we say, exotic sexual appetites to fulfill them." Brian was unsure exactly what she meant. Maybe like bondage stuff he had seen online? He wanted to ask but wasn't able to get the words out.

"It will all become clear later. Please, follow me upstairs." Anne motioned to the large staircase, Brian followed behind. As the ascended the staircase, Brian took a look at the artwork on the walls. He hadn't really noticed bit before, but many of the subjects in the paintings were naked, and taking part in unusual acts. He saw a naked woman pretending to be a cat, what was clearly a man in a floor length gown, and more like that. He was starting to be unsure of what he had gotten himself into. Anne was silent, she knew better than to say anything. She had found that with new prospects, it was best to let them take it in slowly.

They reached the top of the stairs, which ended in a long hallway extending for what looked like an eternity in each direction.

"This is main guest floor, each of these doors are full guest suites. Quite novel for it's time, every room in this house includes an en-suite bathroom, including the servants quarters." Anne said. Brian was in awe, he had never been in a house so large.

"Please, follow me down the hall. We have one more flight of stairs. I'm afraid I can't show you any of the rooms, they have just been readied for guests." said Anne. They turned right and at the end of the hall, turned right again to see another staircase, this one much smaller and more plain.

"This is the service stairs, it's what the staff uses, which will include you should you take the job. Staff aren't allowed in the main hall and main stairs unless performing tasks which require it, such as greeting and escorting guests." Anne stated, motioning to the stairs going up, Around the back was another staircase going down. "Down those stairs is the kitchen and laundry" Anne stated.

They ascended the staircase, finding a plain hallway to match the plain stairs.

"This floor is the servants quarters, where the maids sleep and spend their off day. Each maid at Red Oak gets one off day per week, which she can spend as she wishes." Anne said. "I also require maids working here to live on the premises. It just makes things easier. I doubt that will be a problem for you!" Anne said, again with a smirk. Brian could tell she was trying to sell him on this job, but he was unsure. He just wanted a normal life, and this was further from that than he ever thought he would get. At the top of the stairs, was a large open area with a hallway crossing through. On one side was a small sofa and a medium size television, and on the other, two modest armchairs sat opposite a bookcase. Anne lead Brian through this room and into the hallway exiting out the other side.

"I'll let you look in the empty room, it's at the end of the hall on the left" Anne said. She opened the plain oak door, and motioned Brian to enter the room. Inside, was a plain but well appointed bedroom. The room was lavender with white trim, and appeared to be just under the roof. The large window was in a dormer and had a window seat. On the right side was the bed, a large full bed with a lavender bedspread that matched the walls and a white wood headboard. On either side, were small matching nightstands. On the opposite wall, a dresser and two doors. There was also a desk opposite the window.

"This is beautiful" Brian gleefully exclaimed. After living in a car for a month, the idea of living in a room like this was overwhelming.

"Would this be my room?" Brian excitedly asked. "...If I take the job." he was quick to add.

"Yes, across the hall is Stephanie's room and the door at the end is Allison's." Anne said. "Usually the maids spend their off days up here in either the lounge we walked through or their bedrooms. Maids are not to be seen aimlessly roaming the house of their off days." Anne stated.

"It's actually Stephanie's off day, why don't I introduce you?" Anne excitedly asked. Before Brian could answer, Anne knocked on the door.

The door opened, and beyond it stood Stephanie. She had long blonde hair, and was wearing an almost identical outfit as Allison was. This time, he could read the text on her collar, it said 'Maid Stephanie' in elaborate script. She wasn't as tall as Allison, but still beautiful. Brian suspected she was also a man, both due to what he knew about Allison as well as Stephanie's more severe bone structure.

"Yes Mistress, how may I help you?" Stephanie obediently replied. She stood at the door very reserved, her hands clasped behind her back.

"Stephanie, please meet Brian. He's considering joining the staff." Anne said. Stephanie lit up, as if she wanted to say something, but held it back.

"Stephanie, please tell Brian what your average day is like" Anne commanded.

"Yes Mistress. I wake up at 5 am, and have exactly 1 hour to get ready. I then meet Allison in the kitchen and we prepare breakfast for the guests. Guests eat breakfast starting at 7 am, and lateness is not tolerated." Stephanie recounted. She seemed very careful to choose her words. "After guests have been served, we are then allowed to prepare and eat a quick breakfast. By 9, we begin chores for the day, cleaning the house, doing laundry, that sort of thing. At 11, we start making breakfast, which is served at 12. Like with breakfast, we eat after guests have been served." Stephanie continued to explain. Brian was starting to feel very overwhelmed, this was starting to seem like a lot of hard work.

"We spend the afternoon doing whatever chores have been assigned for the day, and begin making dinner at 5 pm. Dinner is server for guests at 6, and we eat after dinner. We then get the rest of the day to ourselves, unless something else is required." Seeing the look on Brian's face, she reassured him. "It's not as hard as it sounds, life is pretty good here and can be a lot of fun!"

"Thank you Stephanie, you may close the door." said Anne.

"Yes Mistress" Stephanie dutifully replied. She curtseyed and closed the door.

"Do the maids stay in uniform even on off days?" Brian asked.

"Oh yes." Anne replied. "Wearing the uniform is an important part of daily routine, and it makes things easier should she have to leave her room. Maids are not allowed to be out of uniform outside their rooms unless given special permission."

"I see. And why did she call you Mistress? And they both had collars on, are they like slaves?" asked Brian.

"In a sense, the collars represent their obedience to me, as does calling me Mistress. I require all of my maids to call me Mistress." Anne stated

"Let's finish the tour with the gardens, and then we can have a little chat." said Anne. She showed Brian the rest of the house and the surrounding gardens.

Brian had to admit, that even though he would be required to work, it would be nice living in such a beautiful home. He was starting to warm up to the idea of taking the job. After all, he already dressed up in women's clothes for fun, this would just be taking it to the next level. After finishing the tour, Anne and Brian met in Anne's study to discuss the job.

Report Story

bymaidgirl© 24 comments/ 61874 views/ 66 favorites

Share the love

Report a Bug

2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: