“Come on Jerry. It'll be fun. I really want to see how your look in it.” Virginia told her friend.

Virginia Carpio and Jerry Powell had been friends ever since they were kids. Now that they were in their lower twenties, they were still friends. They enjoyed each other's company. There weren't any secrets between them. There wasn't any reason to have secrets, they weren't lovers, they were just good friends.

Jerry worked as a truck driver. He was a member of the teamsters and was paid good money. He liked his job, as it gave him lots of time to himself. He liked to sit in his truck and listen to music as the miles went by. He could also listen to books or listen to television shows. He didn't have to see the action to know what was going on. All in all, he was happy with his life.

Virginia was equally happy. She was a live-in maid of a nice family. There were two maids and they worked alternate weeks. One week she worked Monday to Sunday and then she would have a complete week off to do as she pleased. The work wasn't all that hard as she constantly kept the place clean, so it wasn't overwhelming.

Virginia hadn't any plans to leave her job, the family she was employed by was moving to Europe. She could go with them if she wanted, but she preferred to stay here. Thus, she created resumes for herself and sent them out to her many prospects. She didn't want to work for a service, she wanted to work for a family.

Virginia had just purchased some new uniforms and planned to wear them when she went out on her interviews. It was a pretty black cotton uniform with white polyester accents. It was designed to be worn with a white apron tied in a bow in the back. The uniform was very conservative with a collared neck and long sleeves that covered her entire chest. Most of the buttons were concealed except for the topmost white button between the collars. The skirt was elasticated at the waist with a pleated skirt that flared out somewhat. Virginia's bodice had been professionally tailored for her ample breasts.

She wore it with thick taupe-colored tights and white rubber-soled shoes. There was also a slip worn underneath to give the skirt more body as well as a smooth line from shoulder to knee. As a final touch, Virginia always wore her uniform with a permed wig. Her employers like the professional-looking appearance of her permed hair. This style made Virginia look a decade older. She wouldn't want to be seen with her hair like that when she wasn't working. So, she bought some wigs to wear during her working hours.

Virginia wanted Jerry to try on her outfit. She thought it would be a hoot to see him in it. She had always thought that her best friend Jerry had somewhat fine features and with the proper apparel could pass for a woman.

“I don't want to,” Jerry whined.

“Why not, I think you'll look cute.”

“I don't want to look cute.”

“You know what I mean. It's just for fun.”

“It probably won't even fit.”

“It will. It might be a little tight at the waist, but don't worry about that, it flares out after that.”

“What about the chest?”

“So, it'll be loose there, big deal.”

“I'm taller than you.”

“Doesn't matter.”

“Look I just don't want to!”

“Do it anyway.”

“What's gotten into you all of a sudden.”

“Nothing, I just want to see you in it.”

“OK, but you're not going to take pictures.”

“Of course, I am.”

“Then I'm not going to do it.”

“Yes, you are!” Virginia insisted.

“No, I'm not.”

Jerry and Virginia went around like this for a few minutes more, but Jerry would come around eventually. They had been friends and Jerry wasn't worried that she would show the pictures to anyone. Besides he was curious himself. It was only his male pride that prevented him from immediately accepting Virginia's request. I believed if he gave in too quickly that she would think he was a girlie man. He had to hold out just for the sake of appearances.

Jerry stripped down to his briefs. Virginia had seen him this way many times, it wasn't any big deal. She didn't say anything about him wearing her panties. Neither cared about that. But they started with the thick, opaque nude tights. Jerry sort of knew how to put them on. He had seen women put on tights and pantyhose before. It wasn't much of a mystery. You ball it up in your finger and then you pull it up your legs. Jerry didn't have to be very careful as these were thick tights, not the sheer hose, so he didn't have to worry about getting runs in them. He didn't give it a second thought. The little hairs he had on his legs were completely hidden by the tights. He could see the outline of his dick under the tights, but that didn't matter.

Next came a slip with tank sleeves that came down to his lower thigh. Virginia didn't suggest he wear a bra underneath. The slip was full which hid any hint of his penis from view.

Jerry then put on the dress uniform and buttoned it to the top button. It was followed by a white half apron that Virginia tied in the back with a bow. Between the slip, dress, and apron there wasn't any hint of Jerry's dick or that his waist wasn't narrow nor that his hips weren't relatively wide. There was even a slight bump in the back to make his butt look slightly rounded.

Finally, Jerry slipped on the shoes. He had to sit down to tie the laces.

“What do you think?”

“Your bodice sags,” she said regretfully.

It was true, the bodice had been tailors specifically for a larger chest, without big breasts underneath it didn't look right.

“So?”

“I think you should put on one of my bras and stuff it with socks or tissue or something to get the proper look.”

“Why?”

“Why not?”

In the end, it was decided to stuff Virginia's '18-hour bra' with socks to give it some weight. Just tissues wouldn't look right.

They finished with the wig.

“What about makeup?”

“Sure.”

Jerry expected the makeup to take a while, but that wasn't the case. Virginia's employers didn't want their maids to be heavily made up. All that was needed was foundation to high any blemishes and smooth the skin and some lipstick. It really only took a few minutes to apply. The maids were supposed to look professional, not overly pretty.

“Now what?”

“Looks good. Just one last thing. I don't usually wear this, but I think you have to.”

“You need a little eyebrow pencil to make your brows look feminine. It's either that or we pluck them.”

“NO PLUCKING.”