The House on the Hill
Michael was exhausted as he re-entered the room where he had started the day. Although he had heard that they were going to be helped by a maid he was surprised when saw her dusting the desk in the corner of the room.
“Good afternoon, Miss Evelyn,” the maid said with a smile. “I am sorry if I surprised you but I thought it best to try to get your room in order before you returned. I cleaned up everything and made your bed and I also drew a hot bath for you so you could relax. Let me put this brush down and I’ll come over there and help you out of your uniform so you can get into the bath.”
“Now wait a second,” Michael began before remembering that he was supposed to do everything that she told him. “I…I know I am supposed to do everything that you tell me to but I feel uncomfortable about this. I think I can undress myself.”
“Can you take off your heels without this key?” the maid laughed while holding up a key.
“Well, I could if you gave me the key,” Michael replied sheepishly. “I am perfectly capable of taking care of myself. I’m sorry but I don’t even know your name.”
“My name is Colette, Miss Evelyn. Please understand that I have no choice here. I have been told to take care of your every need and that you are to do nothing except let me take care of you.”
“I understand, Colette,” Michael replied, “But I don’t think you understand everything. I don’t feel comfortable having you undress me.”
“Please forgive me, Miss Evelyn, but we are both required to address ourselves as Miss before our names as we are both maids,” Colette responded, “And as far as understanding everything, you are mistaken. Maids are required to serve their guests by anticipating their every need. Don’t feel uncomfortable letting me undress you. It will only be us girls in the room.”
“That’s what I’m trying to say, Colette.”
“It’s Miss Colette, Miss Evelyn.”
“I’m sorry, Miss Colette,” Michael replied before whispering, “But do you know that I’m not really a girl?”
“Don’t be silly, Miss Evelyn,” Colette giggled in response. “Of course I know that you’re not a girl. Your facial features are still fairly masculine and your body frame is still larger than a woman’s but you have the makings of a beautiful woman if you so desire.”
“I can’t believe you know all this, Colette,” Michael cried as tears began to fall down his cheeks. “Who are these people and how can they do this to me? I can’t believe you know I’m a man. Do you know how embarrassing it is to be dressed like a woman?
“I’m sorry to correct you again, Miss Evelyn, but you are required to call me Miss Colette. I will be punished if you do not learn this lesson before Friday. And please don’t be embarrassed that I know that you are a man. There is nothing wrong with being dressed as a woman. Women do it every day and they always try to look beautiful. You can look beautiful as well and that is what you must do until you get through Friday night’s dinner and go home.”
“I’m sorry, Miss Colette,” Michael sniffled through his tears, “I’ll try to do my best and I didn’t mean to insult you or women, in general, by saying I was embarrassed about being dressed as a woman. It’s just that as a man I’m not supposed to dress as a woman.”
“You have no need to apologize, Miss Evelyn. Don’t be embarrassed about being dressed as a woman. I have helped many men who have been guests here when they were dressed as women. I have seen it before and I am here to sympathize, encourage and guide you. My goal is to help you return home so please let me help you these next 2 days.”
“Ok, Miss Colette,” Michael smiled gently. “I can certainly use a friend here and if you don’t mind seeing my boy parts then I’d love to take a hot bath.”
“Thank you very much, Miss Evelyn,” Colette replied patting the back of the desk chair. “Your feet must be killing you wearing those hills for the first time. Why don’t you sit down right here and I’ll unlock your shoes? “
Allowing himself to relax, Michael watched as Colette unlocked and slipped off his heels and undid his garter straps and slipped off his stockings. Lost in thought Michael was surprised when Colette asked him to stand while she pulled down his petticoats and loosened his uniform before helping him lift it over his head. Realizing that his penis was completely exposed and he was standing in front of a woman Michael dropped his hands to cover his penis when he realized that he wasn’t even a little bit excited. Sensing his embarrassment, Colette told him not to be worry and then said, “Miss Evelyn, I need you to raise your arms to the ceiling. I need to get you out of this corset and it is laced awfully tight.”
Standing with his arms in the air and Colette working behind him, Michael asked, “Miss Colette, I just wanted to let you know that I not embarrassed because I’m nearly naked in front of you. It’s different than just that. I think I’m really embarrassed because I’m naked in front of you, a beautiful woman, and I’m not even a little bit excited down there. Do you find that unusual? “
“I don’t find that unusual, Miss Evelyn,” Colette began, “You have had a very long and traumatic day and I suspect you have exercised your boy parts already today. You are probably tired and that’s why you are getting some time to rest. There, I’m finished with your corset. Didn’t they do a wonderful job with your breasts? You can’t even see a seam on your chest they look so natural.”
Looking at his breasts Michael was stunned. Reaching down he cupped them in his hands and was amazed at how realistic they felt; not that he had sensitivity but rather that they had the weight and feel of a woman’s breasts. Looking at Colette, he asked, “Miss Colette, Can I really take a bath with these on?”
“It’s perfectly safe to bathe and do anything that you want, Miss Evelyn. The glue should hold them on for about a month or until someone applies a breast form adhesive removal product.”
“Well, hopefully, someone will give me some of that before I go home on Friday night, Miss Colette.” Michael said looking directly at Colette. “They will, won’t they, Miss Colette?”
“There are certain questions that I can’t answer, Miss Evelyn,” Colette responded with a sigh. “I’m sorry but I can’t answer any questions about what happened before you woke up today or what will happen tomorrow night. Here let me take your arm and help you into the bathroom.”
“I can do that myself, Miss Colette. Do you have other rooms to service while I am in the bath?”
“No, I’m sorry Miss Evelyn,” Colette replied. “I need to stay with you the entire time. Before you get into the bath I need to give you an enema. Have you ever received an enema before, Miss Evelyn?”
“You can’t be serious. No one is giving me an..” Michael replied without thinking. But before continuing he reflected on some of the things that he had participated in that day. “I’m sorry, Miss Colette. I know you’re here to help me. An enema is probably a good thing to do after all I’ve been through.”
“Why don’t you get down on your knees on the rug in front of the bath tub, Miss Evelyn? It is very soft so I think you will be comfortable there. Have you ever had an enema before?”
“No, Miss Colette,” Michael sighed knowing it was better to follow instructions and get this over with. “What should I do?”
“After getting on your knees then gently rest your head on the floor with your chest held close to your knees, Miss Evelyn,” Colette said while opening a package with two bottles inside. “Once you feel comfortable then raise your buttocks a little and then I will squeeze both of these bottles inside of you. The tops of these bottles are already lubricated and you won’t even feel them as insert them inside of you. There, it’s already inside and now I just need to empty it inside of you. Now this is going to make you feel uncomfortable, like you have to go to the bathroom. But I need you to keep it inside for about 5 minutes. Now here I go with the second bottle. Now bear down, honey, because you still have 4 ½ minutes.”
“Oh my God, I don’t think I can make it,” Michael cried after 2 minutes.
“No, Miss Evelyn,” Colette replied while placing a firm hand on Michael’s shoulder. “You have a little less than 3 minutes to go and I’ll let you up. Bear down and hold it in, dear.”
After what seemed like an eternity, Colette reached down and pulled Michael up and said, “Now hurry over to the toilet and relieve yourself, Miss Evelyn. That wasn’t so bad was it?”
Not wanting to have an accident Michael barely made it to the toilet before expelling his bowels. “That was awful, Colette,” Michael groaned. “But I’m glad we did it. I’m sure I’ll feel so much better after a bath.”
“You will, Miss Evelyn,” Colette smiled. “Here come and get in the tub and don’t forget the ‘Miss’ when you address me, dear”
After slipping into the perfumed bath water Michael look at Colette and asked, “Are you even going to stay here in the bathroom?”
“You forgot to say Miss Colette again, Miss Evelyn,” Colette sighed. “But, yes, I am going to stay. I even need to shave your legs to make sure they are silky smooth. This natural sea sponge will help exfoliate your skin. And while you and I are here in the bathroom a small cot will be delivered to the room where I will sleep. My job is to see that you completely relax and rejuvenate so just lay back and enjoy and I will start bathing you in about 15 minutes.”
“Do we have a schedule until I have to go to the beauty parlor tomorrow, Miss Colette?” Michael asked while luxuriating in the steaming water.
“Not really, Miss Evelyn. I am going to order a few salads for dinner and then you can read and relax. There are a number of magazines and books on the bookshelf in the room. I am sure you will find something that you like. Tomorrow I need to teach you how to curtsey correctly so you are prepared when you meet the guests. I also need to give you another manicure and pedicure as well as a massage. We need to have you feeling your best before I take you to the beauty parlor where they will make sure you look your best. Now relax and enjoy yourself.”
Michael couldn’t believe how quickly the time passed and yet here he was dressed again in his maid’s uniform sitting in the desk chair while Colette was locking his heels again with her key. “Why do we have to go to the beauty parlor, Miss Colette?” Michael smiled while adjusting his skirt. “You have me looking just like I look yesterday.”
“Tonight is a formal event, Miss Evelyn. You have to look your absolute best for your guests tonight. You will get a chance to decide if you’d like a more formal hairstyle; something elegant but practical because you’ll still be working as a maid. And you will get to decide whether you prefer an everyday look with your make-up or a more sophisticated formal look. If I were in your heels I’d think I’d go with a sophisticated updo with a more formal look with your make-up with smoky eyes.”
Michael couldn’t help himself as he smiled and thought back to all the formal parties he used to attend with his wife. She loved going to parties; the more formal the better. But she really loved going to the beauty parlor before the event. She always said it was more fun pampering herself and getting ready for a party so she always scheduled an appointment to get her hair and make-up done. I remember asking her one time why she always wore her hear up when she went to formal parties. We were already home and I was nearly undressed. Her reply seemed like it was etched in my brain. Because there is nothing more sensual than a woman’s neck, silly. A formal dress can accentuate a woman’s figure but an exposed neck highlight’s a woman’s soul. And I always wear it loosely pinned, dear. She smiled as she pushed me down on the bed, undid the zipper on her dress and let it fall gently to the floor. Pulling off her panties and bra, she quickly climbed between my legs before continuing. Do you know why I wear it loosely pinned? You should, honey, because I do it for you. I don’t want to have to struggle with it when I come home and want to ravage you. I just reach up and pull one or two pins and voila! A few quick shakes and I’m gliding my hair over your little friend here. Your little friend must love my hair massages because it only takes a few passes before he begins to wake up; a few more minutes of licking and he’s rock hard and ready to be ridden to exhaustion. Maybe he’d ask for an updo like Colette suggested; might as well have a little fun if he had to do it anyway.
“A penny for your thoughts, Miss Evelyn,” Colette said interrupting his train of thought. “Unfortunately I have to do 2 more things before we go. I need you to bend over while I insert this butt plug.”
“Do you have to do that, Miss Colette?” Michael moaned
“Yes, but it is really lubricated so it should be pretty easy.” Colette answered while quickly pushing the plug into his backside. “There, that wasn’t too bad. Now turn around, Miss Evelyn, and lift your skirt and petticoats. I know you’re not going to like this but the Mistress has ordered us to tie this pink ribbon and bell around your penis.”
“You have to be kidding me,” Michael exhaled.
“Please, Miss Evelyn, you have to say ‘Miss’ or I’ll get punished,” Colette replied.
“I’m sorry, Miss Colette, but I can’t believe you have to do this. Why do you think she is doing this?”
“I believe the Mistress wants the bell to announce your presence when you are coming and going while you are serving the guests. There I think that is perfect. We need it tight enough that it won’t slip off but not too tight that it will bother you. Now let’s get going because it’s 2:00 pm already.
Walking into the beauty parlor Michael realized that he was the last one to arrive. Looking over and seeing Isabel and Sophie smiling and paging through a hairstyle magazine, he was surprised that he was actually happy to see them. Chantal, Melanie and Christine were seated in the reception area unsmiling with their hands on their laps holding their purses.
“And you must be Evelyn,” a young woman smiled before he could say hello to everyone.
“Yes, Miss,” Michael replied. “I’m Evelyn.”
“Wonderful, it’s so nice to meet you. Isabel and Sophie are trying to decide on a hairstyle for the evening. Would you like to see a hairstyle magazine before we begin?”
“Do you have a magazine that has any updos?” Michael asked sheepishly.
“We certainly do, Evelyn. Here it is. I think you’ll look divine with an updo.”
“I never thought about an updo,” Isabel whispered to Sophie while turning to Michael. “Evelyn, what a wonderful idea. Did you come up with that on your own?”
“Well, my maid suggested it,” Michel answered. “But I also remembered that my wife always wore updos when we went to formal events. I figured that since I’m forced to look like a woman until this is over that I might as well have a little fun.”
“Would you mind if I get an updo, too?” Isabel asked.
“Me, too?” Sophie added.
“Certainly not, ladies,” Michael laughed. “The more the merrier. Let’s all have a little fun while we can.”
“Well, it’s settled then, Evelyn,” the receptionist smiled. “I’ll schedule you, Isabel and Sophie for updos. Chantal, Melanie and Christine seem less enthused about being here and just want simple blow-outs with just a little everyday make-up. Have you thought about your make-up for this evening?”
“Well, since it’s a formal event,” Michael began, “Can I get a more sophisticated evening look with smoky eyes? My wife looked so sultry when she went with that type of look.”
“I’m sure you’ll look beautiful, Evelyn,” the receptionist responded before turning to Isabel and Sophie. “And judging from both of your reactions I don’t think I need to ask either of you. I’m scheduling all three of you for a more formal evening make-up look.”
Three hours later the beauty salon receptionist instructed them to walk down the hall past their rooms to the stairs at the end of the hall. After going down the stairs they were instructed to turn left and enter the main parlor of the house. Michael couldn’t believe how he felt. Before leaving the salon he was able to look in the mirror and he was amazed at the results. He looked beautiful he thought. He couldn’t see any of the old Michael in the image in the mirror. He was almost embarrassed that he was wondering what he would look like in a formal evening gown instead of his maid’s uniform.
Hearing their heels click as they walked down the hall and stairs brought their reality quickly home. Each of them had been wearing 4” heels for nearly 2 days and they were becoming quite accomplished in them. Looking amongst themselves they saw nothing out of place. They looked like a groups of maids waiting for their evening assignment.