Chris and Missy Part 1 of 5

Chris was enjoying himself window shopping on Main Street. He had just arrived in town, had gotten settled into his apartment, and was ready to start his first year of college. He was learning his way around the city that would be home for the next four years. There were two downtown department stores within easy walking distance of his apartment. He had wandered through one and he was working his way down the street when he happened upon one of the few surviving old fashioned lingerie shops. He was surprised to see it because this is not a large city, but it is a state capital, so perhaps there's just a bit of residual formality here. He stood in the foyer out of view of the street to simply admire the display window.

"Which would you rather wear?" a voice from behind him interrupted.
He turned around finding a pretty girl there. "Pardon me?"

"I asked you which of those girdles you would rather be wearing. Would you prefer the open bottom girdle or the panty girdle? Or would you like to be wearing the all in one up above them? I don't see a wedding ring on your finger so I figure you are looking for yourself, even if you are just fanaticizing about how wonderful it would be to feel the firm embrace of such a garment. I saw you looking at the dresses in Macy's and at ladies shoes up the block so I took an interest in you. Clearly you are a transvestite so, which of those girdles that you are ogling do you wish you were wearing right now?

"I wasn't ogling! Which would you wear?"

"Yes you were ogling and don't try to change the subject. This isn't about me. I'm not the one standing here fantasizing about wearing women's girdles, you are. So which one is it?"

"I don't know who you are, or why you followed me, but please mind your own business! You are being very rude."

"Oh, you are polite too. I like that. Most people don't say "please" before telling someone to mind your own business. In fact many people would include a bad word or two as well. It is my business. I'm looking for somebody for a specific project and you might fill the bill."

"I'm not looking for a job, so leave me alone."

That's OK. I wasn't offering you a job. I'm offering you a chance to earn an opportunity to be considered for the job. But it is also an opportunity for you to learn and explore, in a safe environment, your interest in women's clothing that you try to hide from the rest of the world."

"Ok, stop talking in riddles. Come straight to the point. What do you want?"

"Right now I want to join you window shopping for women's clothing and get your opinions. I'd like to get to know more about you because we have a common interest and I'll even take you to lunch in exchange for your time. It's time to summon up your courage, be honest about yourself and take a chance on a stranger. If you say no, I'll leave and it will simply be a road not taken for you. You will never know what opportunities you have missed, but if you to take the risk, you won't regret it."

A college freshman new in town gets picked up by a mysterious girl on the street - what could possibly go wrong? He said, "Ok, I'm game. I'll go with you." He went along with the realization that this would probably not end well, but what the hell, it might be an adventure. "I don't have enough money to be worth robbing and my family isn't rich so I'm not worth kidnapping, and there's always the remote chance that you are on the level, so let's go."

She is very pretty after all and, who knows, he might get lucky. And, as people say; "Nothing ventured, nothing gained." So, they went to the other department store and he followed her as she led him through the various departments. She was a tease and a flirt, which he found rather endearing, but not enough to let down his guard.

They went into the lingerie department and she would pick up a teddy or a short nightie and hold it against herself asking if he thought it would look good on her. Of course the answer was always yes. Then occasionally she would hold one up against him which would embarrass him and tell him how adorable he would look in it. This went on until he threatened to leave.

When they were in the dress department she told him to pick out which dress he would like to see her in and she tried it on for him. Of course, he picked the sexiest one he could find. When he complimented her on how cute she looked, she said "you should see me in my work uniform! It's really cute." Then she asked for him to pick out his favorite dress, the one he would wear "if you were a girl that is". When he finally settled on a well tailored business suit with a straight skirt, she said. "Now I know what you like. And I even know which of the girdles in the window you would want. Do you want to know how I can tell?"

"Sure, have at it!" he said.

"Well, from the fact that you have gone this far, you are obviously straight, because straight guys will do almost anything for a pretty girl in the hope that they might get laid - You won't get laid by the way! I'm not that easy. Then there are those feminine features each guy has a personal preference for. Some guys are leg men, some are boob men, and some only see the face or butt. I guess a guy with a shoe fetish would key in on the shoes a woman picked and wore, but you are a flat tummy guy. You like a flat tummy and a small waist. Am I right?"

"I like all of the features you listed, but you do seem exceedingly perceptive. Yes, if I were a woman, I would want to have a flat stomach and a small waist and that suit would show it off to greatest advantage. It's impressive how you figured that out from a few questions. By the way, which girdle would I pick based on your method?"

"See, you are already learning things about yourself. In my opinion you would have picked the panty girdle because it has the most tummy and waist control, but that would have been a mistake. I would put you in a corset, if you were a girl that is, or if I were dressing you up like a girl, which I intend to do. A corset would give you the figure of your dreams. And, I know just the corset I would pick for you too. Would you like to see it?"

At this point things were getting a bit too real for Chris and his fight or flight instinct was telling him to cut and run. But, she could tell by his facial expression when she suggested a corset that she had him hooked. Her instincts were right; he was a good candidate for what she had in mind. She then told him that the suit doesn't count because she said "pick a dress". "Pick one that you would want your date to wear on an evening out."

After a brief detour through the shoe department, where she insisted on measuring his feet, and getting his opinion on shoes, they headed for the promised lunch. She offered him a choice: a restaurant or home cooked meal where she lived just a few blocks away. With red flags waving in his brain he imagined headlines "Missing Student's Body Found - Organs Harvested" or "University Freshman Lured into Alley on Life Support". But he ignored all the warning signs that clearly indicated this was a very bad idea. Against his better judgment he opted for the home cooked meal. Of course he did! And, against all odds, it was a good choice.

"Wow! Nice house. Your family must be filthy rich!"

No, it's not my house. It's my bosses' house, but I live here. Shall we just raid the kitchen or would you prefer to eat in the dining room? We can have sandwiches, soup and salads, or leftovers, all of which I assure you are better than any food we'd get at any restaurant on Main Street. He has a professional chef five days a week. Let's just raid the refrigerator. What would you like to drink with your lunch? We have everything.

After lunch she told Chris that she had to change into her work clothes to start her shift, but if he could wait a few minutes for her to change, she would like to talk with him a bit more. He waited in the library and was kept occupied admiring all the books and other material stored there including a map collection and art work. About fifteen minutes later she reappeared in her work clothes.

He couldn't believe his eyes. She was stunning in her little satin maid uniform with its frilly petticoat, stockings and patient leather pumps. A little white cap, gloves and an apron tied in a great big bow at the small of her back completed the outfit. It is a French maid outfit with the skirt hem about eight inches above the knee. Not something vulgar or tacky but really cute.

His jaw dropped. "Holy cow! What an outfit. You're the prettiest maid I've ever seen."

She said, "Oh really? How many maids have you seen before?"

"In person? None, but on TV and movies..." He was embarrassed by his obvious excitement at the sight of her and moved behind a chair.

"Don't bother hiding behind the chair. It's too late I've already seen it. I can see that you like the outfit a lot! Maybe I'll let you try it on some day. The first thing I wanted to ask you is; Are you glad you took a chance and went shopping with me? Wasn't it more interesting than fantasizing at that display window?"

"So far, yes, it's been fun. How can you work in those high heels and white gloves? Is that uniform really for work or just to look cute in?"

No! I work hard and sometimes I can't keep it clean. I've got regular long cotton uniforms too, but I like wearing this one. I told my boss, if I'm going to be a maid, I'd rather be a cute French maid. I feel pretty in it and he gave me permission to wear it when things are not busy. He won't say it, but I'm sure he enjoys seeing me in it. He doesn't leer or make comments so we maintain a professional relationship. If you keep the house clean all the time, there aren't that many dirty jobs. I don't wear the gloves that often and sometimes I kick my shoes off or wear flats if I'm the only one here. You get used to the heels though. But, when Bob or his guests are here I'm in a proper uniform and must look my best. I love my job and he's a great boss.

"Come back after classes start and it will be even more fun. I told you I intend to dress you up like a girl and I will do it right. When I spotted you it was clear that you had an interest, and you are not too tall or too heavy, your shoulders are not too broad, you have a nice neck and face and your head is not too big, so you looked like a good candidate for a makeover. The next time the two of us go shopping nobody will be able to tell that you are a boy. We'll have lots of fun."

Just then a man walked into the library. "Who's this Missy?"

"Oh, Mr. Greenwood, this is Chris who is just starting at the University this semester. I met him ogling the window display at Brenda's shop and we have been window shopping. Chris, this is my boss Bob Greenwood."

Pleased to meet you Chris. Welcome to our fair city. Are you a transvestite? That's one fine display window that Brenda has. Isn't it?"

Well, that's one fine way to strike up a conversation with someone you just met, isn't it? Chris was an honest kid and not prone to lying, by the same token this is not an admission he had ever made to anybody before in his entire life. It was his big secret and why should he blurt it out in front of two strangers? Then again Missy is cute and this might be going somewhere. On the other hand she already said no to sex. But, all girls say that at first and he hadn't even asked yet, so it might not count. And this is her boss. Is this a job interview for a job he already said he didn't want. What should he do?

From the way things were going with Missy a moment of truth was looking inevitable anyhow, so after a split second decision, he blurted out the answer, "Yes sir. I am a cross dresser and yes it is a fine display window." He was obviously embarrassed by the admission.

Bob smiled and said, "Good for you Chris. The one thing I can't abide is a liar. I place a high value honesty. So Missy might work her magic on you? You're one lucky boy. I've got to go. I just wanted get the newspaper to take with me."

"When will you be home, Mr. Greenwood?" Missy said.

"Supper at 6:30 please. Don't care what it is. Got to go. It was nice to meet you Chris. Hope to see you in the future. Bye."

"Well Chris, that's the boss. He can be a bit direct at times.

"Gee, you think?'

You took a big step just now. I'd bet that was the first time you ever said that out loud or to any other person. Wasn't it? When did you first discover that you liked pretty clothes?

"Yes it was the first time. I've just put a lot of trust in you Missy. You really are very perceptive, and I hope I don't end up regretting it. I guess I've known since I was about five years old when I discovered how soft my sister's underwear was compared to mine."

"You won't regret it Chris. I'm certain of that. This is a big house and I've got a lot of work to do before supper. Today, and tomorrow I'm also the cook. The chef is here only on weekdays. Here's my phone number. Please write down yours in this pad and we'll get together as soon as you know your class schedule. I promise I'm trust worthy and I promise we'll have fun, but we won't do anything that will interfere with your classes. That is, after all the main reason you're here in town so academics come first." They spoke as she escorted him to the door.

"Missy, it has been delightful spending the morning with you. Thank you for pestering me. I still have time, if you want, I can help you with your housework."

"That's sweet Chris, but it would not be appropriate. Next time with Mr. Greenwood's permission, I'll show you around the house. You won't believe his courtyard. Also, there's a certain satin corset I have to show you - actually, I'll do more than show it to you. Bye for now. It was wonderful meeting you to."

The door closed and he walked the few blocks to his apartment. College was going to be more of an adventure than he had expected.

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