Chris was as embarrassed by his French maid uniform as Rachael was by her nakedness. Both had put themselves in the situation voluntarily and both were surprised by the encounter.
But, Chris didn't expect to be embarrassed. He had heard Rachael laughing as he walked away and felt ashamed. When he got back with her ice tea she was gone, and he would not see her again during her visit. He wasn't embarrassed in front of Bob or Missy, so why the difference?
Meeting Rachael wasn't like going out shopping with Missy. Other people in the stores didn't know he was a guy, but having a pretty girl know it was a guy in a dress and laughing at him was humiliating. Also, he had anonymity in the department store, but she would know who he is and she would remember that moment for the rest of her life. The circle of people who know his secret was expanding beyond his control including Missy, Bob, Rachael, Brenda and the ladies at her shop, the owner at the restaurant, the new household chef and the gardener.
This could come back to haunt him in the future. He has no way of knowing what the future holds in store for him. He remembered the comment "The kid bagging your groceries could be your doctor in ten years. And your maid could be the governor of the state one day." That might apply to Missy, but it sure won't apply to him if people knew he had been a sissy maid.
What if he runs for public office thirty years from now? Or, what if he is appointed to some high office? He is doing nothing wrong, just something unusual but that might be enough to dissuade some people who are less tolerant than Bob or who just don't want to be bothered to go to bat for anyone about anything. It's not as though people will tell him, "We aren't appointing you to this judgeship or giving you this security clearance because we read this in your FBI file". Things don't work that way. The short term fun might have long term consequences.
And now it was no longer even fun. The corset, makeup and wig were needless work. Right now he regretted his choice to be a maid, but he was stuck with it. A French maid outfit was designed to show off a pretty girl's shapely figure and lovely long legs, features for which a young woman is biologically and culturally valued. Boys are not generally valued for those features. Missy could flaunt her beauty secure in the knowledge that Bob, chef and others knew she was much more than just a pretty package. They could enjoy her beauty and value her many talents as well. What an ego boost that must be for her, but Chris can never experience that. He could aspire to feminine beauty, but ultimate he will always be a counterfeit, like a fake Rolex watch. It may look like the real thing, but it is of no value to most, compared to the real thing.
The problem is, most people just don't respect a guy who dresses like a French maid and most people, including Chris, want respect. He not only wanted respect, he deserved it. Missy and Bob aren't just being polite, they really do respect him. Missy knew he was polite within one minute of meeting him, and Bob's direct question the first time they met demonstrated that he is honest. Those are traits they respect. They know he is hard working and smart, more traits to respect. Rachael only knew he was the guy in a dress. Some people just can't get past that.
Bob was exceedingly tolerant to allow him to choose the maid outfit, but the next day when guests were in the house for Thanksgiving, both he and Missy were required to wear traditional maid uniforms. And Missy, with two uniformed temp maids did all the serving while Chris had kitchen duty helping chef. Bob might tolerate Chris's attire when few are present, but he wasn't going to inflict it on his guests. Chris understood Bob's obligation to his guests as a good host.
The Thanksgiving feast left a major cleanup project for Missy and Chris on Friday and Saturday and they were glad it was over. But that meant Christmas was coming and decorations had to be placed. By now Chris was working over twenty hours a week and he was confident if things went as planned, that he could get through college debt free and with enough money saved up to buy a nice car for cash and have emergency money left over. Bob had really driven home the evils of consumer debt when it comes to long term prudent financial management.
Putting up the decorations, Chris did most of the grunt work while Missy directed him and the house was beautiful by the time they had finished. The gardener has set up a tree in the courtyard and one in the front parlor that could be seen from the street. Some of the Christmas decorations were ancient. Chris guessed that was the result of one family occupying the same house for so many generations, so he treated them with extreme care. Bob took note of the care Chris showed and quietly appreciated it. He admired Chris's work ethic and his inquiring mind.
Rachael arrived home for Christmas break secure in the knowledge that she would not be blindsided by the presence of a sissy maid again. She had done her research and perused the Internet to learn all about the subject. Unfortunately, Chris had not. He had never even heard the term "sissy maid" and did not even know that such a subculture existed. He had no time to peruse the Internet for recreation. With his class load and work, he barely had time to eat and sleep. While he always thought they were cute, the idea of trying on a maid's uniform had first been introduced to his consciousness by Missy's offhand comment the first day they met.
Rachael was not like her brother. She tended to be more aggressive than polite and had become a bit coarser than the little sister that Bob has sent off to an expensive college for women two years before that was supposed to instill refinement. She seemed to blame Chris for her embarrassment at Thanksgiving and had not forgiven him. It never occurred to her that he too was embarrassed. She regarded him as a peeping Tom. She had a point in that regard! She planned a bit of payback for her humiliation and a bit of fun at the same time.
When she arrived home in the evening she was glad to see Chris was still there in his cute little uniform. She made sure that he carried her bags up to her room and while she was up there she said to him, "I'm surprised that Bob still has a sissy maid working here. I guess Missy keeps you in a little chastity cage. I've seen on websites that all sissy maids are kept locked up tight. Does it hurt? Can I see?" and she lifted his short skirt and petticoat. He jumped back pushing them down and she continued, "You don't need that little pecker to satisfy a woman, you know. I understand that sissy maids use their tongues. I'm going to sit on your face tonight!" – He was uncomfortable with her comments but equally intrigued. "You were peeping at me, so now I'm going to give you a good close look at what you wish you had between your legs." He quickly retreated, humiliated, insulted, but still intrigued by the possibilities.
Down in the kitchen he asked "Missy, have you ever heard of a sissy maid? Or, heard of something called a "chastity cage"?" She smiled and looked at him like he was an idiot. "I forget how young you are Chris. Just out of high school in a small rural town. No offence, but you really are a hick. You have access to Google. Use it! But, do it on your own time."
"I don't have my own time Missy. I'm not happy with my life at this moment and I think Rachael just called me a homosexual. I guess I can't blame her. Look at me." he replied. Just then, Rachael called down and asked if Chris could bring up some hot chocolate for her before she goes to bed.
Missy smiled and looked at him. "Yes Miss Rachael, as soon as I can make it, I'll send him up." And she began heating some milk. "Well, based on your questions, this could be shaping up as an interesting night for you! As your boss, I want to remind you that you signed a code of conduct in your contract. Be on your best behavior – no excuses! Remember, you don't work for her, you work for me. Deliver the hot chocolate and get back down here."
The fact is, Missy should have gone up with the hot chocolate instead of Chris. I guess she had a bit too much confidence in his judgment or in his will power, because she sent him up.
With some trepidation, Chris was at her door with the tray in hand and knocked. "Come in." He put the tray down and poured the hot chocolate into a cup for her. Standing by the bed in a cotton tee shirt with "I have the pussy, I make the rules" silkscreened on it. Rachael said, "I'm going to have my way with you, sissy." And, with that, Missy's instructions, given to him just two minutes before, vanished from his brain - poof! "Are you scared yet? You should be, because your balls are going to turn blue inside that little cage of yours." He was not going to give her the satisfaction of admitting that he had no idea what she was talking about so he just stood there and said nothing. He wondered if cage might be another term for a corset.
She had rightly determined that he was very shy and hadn't had a lot of experience with girls. But she wasn't exactly worldly either. While lacking firsthand knowledge, she had plenty of advice from the other girls at school on how to debauch and humiliate a sissy maid. None of them had ever actually seen a sissy maid, but that's what the Internet is for, right? "Take your shoes off sissy. Come on over and sit down. I'd like to get to know you better. Are you an obedient maid?"
He did as he was told and removed his shoes, "Yes Miss."
"Would you rub my sore feet if I asked you to?
"I guess so"
"Well, my feet and legs are sore and could use a good massage. Would you do that for me?" she said with a poutty face.
"Ah, I guess so." He looked like a trapped animal. She had him exactly where she wanted him. She could see the uncertainty in his eyes and she got a rush from the power she held over this pathetic creature. Handing him a bottle of massage oil she brazenly slid her panties off in front of him looking him right in the eye the whole time. He didn't dare look away from her eyes. "You know you want to look at my body just like you did at Thanksgiving." She flipped the panties up with her foot and caught them without ever breaking eye contact, placing them in Chris's free hand. "Would you be a dear, and put my panties over on that chair with my bra and other clothes." She then climbed onto the bed and presented her feet to him as he returned to the foot of her bed.
"OK Chris, get to work! I'm watching your eyes. You're not a pervert, are you? Oh wait; you're a boy dressed in a little French maid outfit. I guess you are a pervert. Remember, I'm watching your eyes." Thoroughly humiliated, he began massaging her feet and ankles and as he worked his way up she audaciously spread her legs, teasing that sissy, secure in the knowledge that he was harmless. "I'm still watching your eyes, sissy. Do you want to lick that? I want you to lick me right here until I say stop."
Just then Chris truly regretted the French maid outfit. Its one redeeming quality was that she couldn't see how excited he was. Time to run! He told Rachael he was very sorry for staring at her by the swimming pool at Thanksgiving and that he was as surprised and embarrassed by what happened as she was. He told her he truly regretted it and he would really like to leave now.
At that point, she could have ended it, with total victory but she didn't. She was having too much fun tormenting him. She simply said "apology accepted Chris. Here's your chance to make up for it. Start licking!" He climbed onto the bed, placing his head between her legs and did as instructed. Chris had always delighted in pleasing other people, perhaps that's why he liked his maid persona, and he was gratified with the results of his efforts. From the quivering and sounds Rachael was making, she was certainly pleased and he began to work his way up, massaging and licking her flat tummy, and eventually her breasts.
Rachael was about to learn that a slogan on a tee shirt might get hearty endorsements from her friends at school, but in reality Mother Nature makes the rules. A naked girl on her back with her legs spread apart and a boy on top of her is no position to be making rules. Also, while it's easy to devise a plan, managing it to fruition is hard and her plan was about to go awry.
She was quite proud of her plan to punish the sissy maid. Everything was going as intended when suddenly with one thrust, she was deeply impaled. She let out a loud yelp as her body and breasts began moving in contrary directions. It was immediately apparent that he was not as harmless as advertised by the consensus of her friends at school. He was neither caged, nor small. Her intellect immediately objected, but her body at that point was completely willing and her mind surrendered to her body without a word of protest.
Apparently, not all sissy maids are locked in a chastity cage. Who knew? She should have been more persistent when she lifted his petticoat and more through in her examination. She was no longer "making the rules" and he was going to do his all to please, as was his nature. It was now too late for regrets by either. In the ensuing hours, the maid outfit ended up on the floor with her tee shirt and she ended up in the corset. For the next five hours they were blissfully intimate.
Unfortunately, her room was right above Missy's bedroom and Rachael screamed whenever the spirit mover her – which was quite often. When the fun was over Chris started thinking about what had just transpired and decided being caught in her bed was not good for his job prospects. He kissed her and asked if she had any regrets and she said no. She asked him if he had any regrets and he too said no. Both of them would have regrets soon enough! Chris was right about being caught in her bed, but being seen leaving her room naked with his clothes in hand was even worse. He couldn't put his French maid dress back on because she was still wearing the corset. He made his way down stairs, changed into his street clothes and went back to his apartment before Missy woke up from her much interrupted night's sleep.
He wasn't scheduled to work on Thursday, but went over to see if there was any fallout from Wednesday night. Missy was fuming. "How's that homosexual lifestyle working out for you Chris? You know her room is right above mine don't you? The walls of these old houses are thick but the floors are not. I thought the ceiling was coming down. What the hell were you thinking? I know what she was thinking; because she was screaming it to the whole world.
I recruited and trained you and set you up with a good situation that would pay your way through college as long as you wanted to stay and you pissed it away for a piece of ass. Now Bob is going to be left in the lurch and have to call a temp agency and do all the training himself. He really likes you. You have no clue what opportunities you have just pissed away. You really are a dumb ass! Bottom line is you're fired. Give me the door key – NOW! And, here's your damn corset! I recovered it when I went up to retrieve the tray and tea service"
By now Missy was in tears. She had failed Bob. She was just one of a long line of students he had put through college and mentored in this way. Her carefully planned exit strategy was in ruins. "At any time you could have said no to Rachael and walked out. She has no authority over you. Your contract is with Bob, not her, and you worked for me. Your obligation was to us! Bob saw you this morning leaving her room. You know he gets up early. He can't fire his sister and she didn't sign a code of conduct that you violated the hell out of last night. I've been training you for three months and I'll be leaving for California in two weeks. That gives me less than two weeks to train someone I know nothing about. I thought I carefully evaluated your character. I'm not as perceptive as I thought. Rachael wasn't the only one you screwed last night."
Chris felt terrible. "Everything you said is true. I let down a friend. Actually, I let two friends down because I have come to regard Bob as a friend too and I betrayed him as well. I also let myself down. All I can say is I'm so sorry."
Just then Bob came in. He rarely goes into the butler's pantry but had heard their voices and wanted to see Chris before he left. He could see Missy was crying – Chris was also in tears. Knowing it would make no difference in his job status; Chris apologized to Bob for everything that transpired and most of all for betraying his trust.
Bob actually placed far more blame on his sister than on Chris, but there was no reason state his personal opinion openly. He knew that most boys Chris's age would have done the exact same thing if presented with such a willing girl, but he would never say so in front of Missy whose contempt for the male of the species at that moment needed no reinforcement.
"Just so you both know, Rachael came to me this morning and pleaded Chris's case assuming full responsibility for what transpired. She asked me not to fire you and said that she was truly ashamed of her behavior. I too am ashamed of her behavior. I told her it was not her call to make and that you would most certainly be fired for violating your contract. Perhaps we can all learn from our mistakes, because in this matter there is plenty of blame to go around."
Bob and Missy escorted Chris to the same door he had entered three months earlier on the day he met them both. It had been an adventure for him and as the door closed, so closed Chris's short career as a sissy maid.
When Rachael got back to school, after Christmas break, her friends clamored to hear how she humiliated the sissy maid. She confessed that she had humiliated him up to a point, but by doing so she humiliated herself far more. It reminded her of an adage she had heard in a movie; "When seeking vengeance, first dig two graves".
She explained that all the stories they told her about sissies wearing chastity cages were greatly exaggerated and this particular sissy maid didn't have a chastity cage and worse yet didn't tell her. So, she ended up getting much more than she bargained for.
With that, several of them laughed at her saying they couldn't believe she was so gullible and naive that she believed their made up accounts that all sissy maids were locked up. The joke was on her. Then she realized they had been setting her up for humiliation too. At that moment, she saw some of her "friends" in a new light and she mitigated their joy by adding that Chris had turned out to be a real credit to the male sex.
She told them, while they all viewed it as entertainment and of little or no consequence; it had potential life changing ramifications for Chris. She said that when she got to know him, he was just a kid. Up until then, the "sissy maid" had been a caricature for all the girls to joke about. But now for her he was a real person whom she had harmed.
They all took financial security for granted. It was easy for them to forget people like Chris who would struggle to better themselves or just to make ends meet. She told them that Chris was just as embarrassed by the courtyard encounter as she, and that he had apologized for staring at her and after that she should have stopped. But she went ahead with their plan to humiliate him knowing it was wrong.
She confessed that she enjoyed the power she had over him at that moment, and admitted that she continued so she report back to them so they could all laugh at him. At that moment, she promised herself that she would ever again fall prey to group thinking or allow herself to abuse power. From now on she would think for herself and act on her beliefs. She also told them that Bob was now questioning if she would be better prepared for life by attending a large state university where she would meet and get to know a wider variety of people. With the revelation that she too had been set up for humiliation, she was now concluding that he was right. In Bob's view, her system of ethics needed a bit of refinement.
She told them that Chris's family couldn't afford to pay for his college education and he couldn't pay for it without the job he had now lost because of her. He might now be faced with a choice to go deep in debt or have to drop out of school and have a lower standard of living for the rest of his life because of her cruel joke. With that, reality began to sink in to the other girls.
They now saw him as a real person and most of them had empathy for his situation and felt bad that they hadn't recognized another person's humanity earlier. Some of them reflected on how lucky they were to have wealthy parents and vowed to consider how their actions will affect others. With wealth comes power and with power comes responsibility. If there was one positive result of Rachael's misadventure that night it might be that she and some of her friends had become less selfish.