Lucy’s Debut
by : Patricia Marie Allen

 

Luke is an active high school freshman. His mother headed out one day without notice. A week after his sixth birthday, Luke came home from kindergarten and Mom wasn’t anywhere around. His sister Peg, who was 11 at the time told him that she wouldn’t be coming back. That left Luke’s father to raise him and his sister alone.

By the time Luke was eight, Peggy was very involved with lots of activities. She was in Blue Birds and later Camp Fire Girls. She took swimming lessons at the Y, volunteered in the children’s book section at the library and read to the elderly at a near by nursing home. Most days Luke got home an hour or two before she did. It was about that time when Luke became curious about his sister's clothes.

It first happened on a Saturday. Dad had to work over time. Peg was supposed to do the wash and fix dinner before Dad got home. While the whites were in the dryer, Peggy discovered that she didn’t have everything she needed for dinner. She would have to take the bus the store to pick up a couple of things. She checked the bus schedule and discovered that the round trip would take over and hour. She waited until the dryer stopped. She put the whites in a basket, transferred the next load to the dryer and started the last load. Then she asked Luke to fold the white clothes and put them away while she was gone.

Luke sat on the couch and watched television while he folded. He had seen Peggy do it that way. There were five pairs of Peggy’s panties, three bras and two slips in the wash. He wasn’t quite sure how to fold the bras so he just folded them in half. The slips caught his attention. They were still warm and felt so soft. The nylon tricot was a new experience for him. The panties were made of the same material. He folded them the same way he found his underwear folded. Fold the crotch to the top and the sides in by thirds. He put Dad’s away first. His were next. Peggy had the most. He made a separate trip for hers.

Luke had never handled her clothes before. He put the lingerie on top of her dresser and began looking in the drawers the discover where it went. When he found the correct drawer, he had to rearrange it so there would be room for everything. Some of the panties slipped out of the stack when he was putting them away. As he refolded them he was struck by the satiny smoothness of them. They were certainly different then his.

In an instant, he wondered what they would feel like on. Laying a pair on the bed, he quickly stripped off his pants and shorts. He studied a little to be sure that he was putting them on the right way. He put them on and thought how delicious they felt. The bras and slips were still on the top of the dresser. He was going to try them all on. First came the bra, then the slip. The bra needed help. He went to the bathroom and reeled off about ten feet of TP and stuffed it into the cups. Marching back into Peggy’s room, he studied his reflection in her long mirror. He decided to try on a dress.

Luke opened the closet and picked out a soft yellow one he always thought looked good on Peggy. It buttoned up the front and was a lightweight material that was barely opaque. In the mirror he could see the shadow of the slip he had on. He spun around and swayed back and forth, watching the dress in the mirror. Right from the time he first pulled on the panties, he knew he liked wearing girl's clothes.

He could hear the television in the living room. It went to station break. That meant Peggy would be back in less then fifteen minutes. He wasn’t sure just what was wrong with wearing her clothes, but he knew he’d better not let her, or Dad, catch him at it. Luke carefully put the dress back exactly as he had found it and put the lingerie away. By the time Peggy got back he was sitting on the couch watching television.

For the next five years, Luke explored his sister’s clothing almost daily. He did, for sure every day after school. He became proficient at fastening a bra behind his back. Putting on nylons became second nature to him. He even learned to walk in high heals. That all ended last fall. Peggy went away to college. She left almost nothing in the way of clothing.

It was about that time that Luke put his name on a list of young people willing to baby-sit. A young mother of a nine-year-old needed a regular sitter for the weekends and some days after school. That’s how Luke came to know Evelyn and Suzy. Luke began borrowing Eleven’s clothes the third time he sat. He put Suzy to bed about nine and for the next two hours he wore her dress.

Evelyn wanted to go to a Halloween party and asked Luke to baby-sit for her. When Luke arrived, Evelyn and Suzy were both in costume. Evelyn was a gypsy princess and Suzy was a ballerina.

"Where’s your costume?" Questioned Suzy.

"Oh I don’t have one."

"Why not? It’s Halloween. Everyone is supposed to wear a costume."

"I didn’t have anything to make a costume out of."

"My mother is a good costume maker. She can make you a costume. Mommy, can you make Luke a costume? He doesn’t have anything to make a costume from, at his house."

"Well sweetheart, all I have around her are girl's clothes. If I made him a costume, it would end up a girl’s costume."

"Well, couldn’t he be a girl for Halloween? You have a wig and everything."

"I guess he could if he wants to."

"You want to, don’t you Luke?"

Luke’s heart skipped a beat. "I don’t know, I never really thought about it before."

"Come on, it’ll be fun."

Luke looked at Evelyn. She shrugged her shoulders. "It’s up to you." She told him. "I have plenty of skirts and dresses. I’m sure we could find something you could wear."

"Come on Luke. We’ll have fun."

"OK. I guess it won’t hurt me to pretend to be a girl for one night. How often does Halloween come on a Friday night anyway."

Evelyn led the way into her bedroom. She opened her closet and picked out a full dress with an elastic waistline. She held it up to Luke. "What do you think, Suzy?"

"Yeah that one."

"Oh, I'm not sure. This one is pretty thin. I always have to wear a slip with it so it can’t be seen through in back light."

"He can wear a slip. I want him to wear that dress. You can wear a slip, can’t you Luke?"

"I guess."

Evelyn shrugged again and got out a slip. She opened her lingerie drawer and got a bra. "Take off your shirt." She told Luke.

He followed instructions and she fastened the bra for him. She studied the situation a little and then picked up three pairs of panties and stuffed them in to one of the cups. Three more went into the other cup.

"Do you want to wear nylons too?"

"Yes Luke, wear nylons." Suzy chimed in.

"OK." Luke said trying to subdue his excitement and seem a little board with the whole idea.

Evelyn got out some nylons and a garter belt. It was wide, with a waist nipper built in. She fastened it around his waist.

"You can pull it up and take your pants off. Do you think you can manage nylons by yourself?"

"Yeah I think so. I saw ‘Elmer Gantry’ when I was little. There was a scene in there where a woman put on nylons. You just gather them up and point your toe in to them and let them loose slowly as you pull them up your leg."

"That’s right. Here when you get them up, you fasten them like this." She said, demonstrating the garter strap catch. "You’re on your own from here. Oh. I always wear my panties over top the garter straps. You might want to do the same. It makes going to the bathroom much easier." Evelyn herded Suzy out of the bedroom and shut the door.

Luke took off his pants and shorts he put on the nylons and, after some deliberation, took a pair of panties from the still open drawer and put them on. He put on the slip and dress he went to her closet and found the pair slippers that he thought might really be shoes and put them on. They were a beige color with an open toe and heal. They had a slightly raised heal. He knew from experience that these were the only ones she had that would fit. Her wig was on her dresser. He put it on, and gathering his courage, he stepped into the hall. It was the first time he let anyone see him in a dress.

"Oh Luke. All you need is some make-up."

Evelyn took him to the bathroom and did make-up for him.

"Well, what do you think. Are you going to be able to handle being a girl tonight."

"I think so." He said rustling his dress with his hands. "Really, this feels kind of neat. I’ve always wondered about dresses. I thought they would be like wearing a bathrobe. It’s not though. It’s entirely different. I kind of like the way it feels when I walk. I’ve never felt anything quite like this."

"Well, have a good time. I have to get going. I’m late. Be good Suzy." Evelyn went to the door and opened it. Turning back to Luke she said. "You can take that stuff off anytime you want. You don’t have to stay dressed that way all night. The cold cream in the medicine chest will get the make-up off just rub it in and wipe it off with tissue." Then she was gone.

Luke was in no hurry to take off the dress. After Suzy went to bed, he intended to just sit around for a while and change before Evelyn got back. However, he got involved in a Halloween movie and was still dressed when she came in.

"Well, I thought you would have bailed out of that dress at your earliest opportunity. Did Suzy badger you to stay in costume?"

"No, I really had a good time. I did intend to change before now, but I got involved in a movie. I just kind of forgot how I was dressed. I think this dress is very comfortable. A lot more then the pants I wore over here. Too bad men can’t wear dresses."

"You should have been born in Scotland. Men there wear kilts. They’re like skirts." Evelyn laughed. "I feel like some ice cream, you want some before you go?"

"Sure."

"Oh by the way. My sister wants to go out tomorrow night and her baby-sitter canceled. Would like to sit?"

"I guess that would be all right. I’m not doing anything."

"She wants me to go with her. If she brings her daughter over here, would sit for both of us? It would be twice the pay."

"OK, sure."

As they sat at the kitchen table Evelyn remarked. "You do make a pretty good girl. With a little work I bet we could make you pass for a girl. You’ve got the right natural walk."

Luke blushed and looked down at his ice cream.

"Oh, I'm sorry, I've embarrassed you. I didn’t mean to tease you I was just making an observation."

Luke showed up at 5:00 on Saturday. Evelyn’s sister was already there.

"Luke this is my sister Mary. Mary, this is Luke."

"So this is the guy Suzy’s been talking about. The one that looks so good as a girl." Luke blushed. "You really dressed up like a girl, make-up and every thing?"

"Ah, yeah, I did."

"I’d liked to have seen that."

Just then, Suzy and Janet came in. "You can do it again, Luke. My cousin Janet wants to see it too."

"Yeah I want to see it." Janet confirmed.

Evelyn laughed. "Are you up for a command performance Luke?"

"Please Luke please." The girls chimed together.

Luke looked at Evelyn. "I don’t mind if you don’t mind." She told him.

"Come on Luke we’ll have fun just like last night."

"Oh, OK." Luke said.

"You know where everything is." Evelyn told Luke. "You’ll have to hurry if you want me to do your make-up."

Luke went in and put it all on again. Evelyn did make up for him. The girls were ecstatic. Mary commented on what a nice looking girl he made. "You even have good looking legs." She told him.

"Doesn’t Luke look good as a girl?" Suzy asked Janet.

"He sure does. Let’s call him Lucy. If he look's like a girl, he should have a girl's name."

"Hi Lucy." Suzy giggled.

Mary laughed. "Lucy. I like it. Well Evelyn, we’d better go if we don’t want to be late."

"OK. Luke, you know you can change back when you’ve had enough."

"Just put the girls to bed by 10:00. Janet’s spending the night. I’ll pick her up in the morning." Mary told him as they were leaving.

When Evelyn came in at 1:00, Luke was still in his dress watching TV.

"I see you elected to stay in my dress all evening again." She smiled.

"There never seemed to be a time that was right to change until the girls went to bed. By then, I was used to it. Besides, like I said last night, this dress is more comfortable then my pants."

Evelyn smiled, started to say something and then stopped. She just shook her head and laughed softly.

Two weeks later Luke answered the phone.

"Hi. This is Evelyn Dorfman. I’m going out with my sister again this Friday. When I asked Suzy whom I should get to sit for her, she said ‘Lucy’. I said ‘who’s Lucy?’ She said ‘You know Luke in a dress.’ Well, I told her I wasn’t sure that ‘Lucy’ would be available. She might have to settle for Luke. She insists that you can come over and be Lucy. She’s quite adamant about it. You wouldn’t want to do it again, would you?"

"Ah, are you asking me to come over and put on your dress to baby-sit?"

"Well yeah, I guess I am. It really seems a strange thing to ask, doesn’t it?"

"Yeah. Are you sure that you want me to do that?"

"Well, Suzy really wants you to. If you will, it will make her happy. I hope this won’t embarrass you, but you did seem to enjoy it. You even said it felt good and that the dress was more comfortable then your pants."

"I know, but I didn’t think it would be a regular thing."

"Well that’s OK. I can tell Suzy that you don’t want to do it. She can stand the disappointment."

"Well it’s not so much that I don’t want to, it’s just a strange request."

"Does that mean you’ll do it?"

"Well, ... OK, if you think it’s all right."

"Fine Lucy should be here at 5:30 so I can do her make-up."

Luke hung up the phone. He just sat for a while looking at the wall. She had invited him to come wear her clothes and she was going to pay him while he did it.

Luke was there at 5:15 on the appointed day.

"Hi, Luke." Evelyn said letting him in. I’m just now putting on my make-up for the night out. You should have time to change while I finish up. Then I’ll do your make-up before I leave. You can pick any dress you like."

They walked down the hall together. Evelyn turned right into the bathroom and Luke left into the bedroom. He closed the door and began getting undressed. He put on her wig and got out the bra and panties to stuff it with. After that was on, he put on the waist nipper garter belt and stockings. When he had donned a pair of her panties, he turned toward the closet and was struck with his reflection. Just then, he heard the water running in the bathroom. The strangeness of it all began to hit him as he pulled on the slip. Here he was putting on a woman’s clothes, she was still in the house and fully aware of it and what’s more, she had invited him to do it and, ... was going to pay him while he wore them. Still ruminating on it, he picked a shorter dress with a full skirt. He had gone from sneaking into her clothes to being invited to wear them. "How long will this last." He wondered.

When he got to the bathroom, Evelyn was just blotting her lipstick.

"You’re just in time." She told him picking up her mascara. In a few minutes, Luke looked like Lucy.

"I’ll be back about 2:00 a.m." She told him on the way out the door. "I’d tell you that you can change anytime you want, but I’m convinced that you won’t want to. At least, you conveniently found reasons not to, twice before." With that, Evelyn left.

Luke spent the evening as Lucy and Suzy told him how great it was to have him be Lucy. She also told him that her cousin, Janet, thought it was neat too. Lucy and Suzy played together all evening. Luke was really enjoying this. He was sure that Evelyn would tire of it soon and he’d have to go back to sneaking into her dresses. While this lasted though he’d make the most of it.

Evelyn was back shortly after 2:00 a.m. as promised. As she suspected, Luke was still in her dress.

"Hi Lucy." She said as she came in. "I’m back. Was Suzy good, tonight?"

"Oh yeah, we had a great time."

"You know, you coming over to be Lucy was a great novelty for her. When I told her that you had agreed, that was all she could talk about. She even called her cousin, you remember Janet, and told her you were going to be Lucy. I heard her say that she hoped you’d be Lucy every time you baby-sat."

"She did?"

"Yes. I think she’s serious. She really likes it when you put on my dress."

"I didn’t think she would like it. As a matter of fact, I thought you would veto the whole idea before it got started. I was really surprised when you thought it would be OK to do it again on the Saturday after Halloween. Then when you called me up and asked me to do it tonight, you could have knocked me over with a feather."

"Well, to tell you the truth, there’s something about it I like. I’m not sure why, but I do. Maybe, I've always been just a little uncomfortable about a boy baby-sitting. I think in my subconscious I don’t see men as being caring and nurturing. When you put on a dress, that expresses to me a feminine side of you that I like. Does that sound crazy?"

"I guess not. I just thought that everyone would think I was crazy to do this. You and Suzy seem to think it’s great. But some how I don’t think that everyone should know about it. I mean, Halloween was one thing, but tonight is something else all together. I’m not sure why I agreed to do it."

"Maybe there’s something in you that likes it more than you think. I thought about it a lot tonight. It almost occupied my whole thought process when I wasn’t doing something that required me to think. What I finally decided was that Suzy thinks it’s OK and I somehow like it, so ... if you want to, you can be Lucy here as often as you like."

"You mean I can or should wear your clothes every time I sit?"

"Yeah if you want to. I know as of now Suzy wants you too. How do you feel about that. Did I read you wrong? It seems to me that you like it too. Am I right?"

Luke felt a little trapped. He hoped this wasn’t some kind of sting. He swallowed hard and answered. "Well ... yeah, I do like it. I don’t know why exactly, but it’s really neat. I mean, somehow I feel really free when I’m wearing your dress. Is that crazy?"

"No crazier than me saying what I've told you tonight."

"I’ve never admitted any of these kinds of feelings to anyone before. I’m glad someone knows I like this. It takes a real weight off me."

"Well, I guess I have a new baby-sitter. Luke is gone, Lucy is here."

On Monday, the phone was ringing as Luke came in from school. It was Evelyn’s sister, Mary.

"Hi I’m Janet’s mother. You remember, Evelyn’s sister?"

"Oh yeah, sure. Hi."

"I’m going out Friday night. Janet asked me if I'd see if ‘Lucy’ would come over and baby-sit. She said that ‘Lucy’ had sat for her cousin Suzy last Saturday. Was that right?"

"Well, ah, yeah, I did."

"Janet is real competitive with Suzy, if Suzy had ‘Lucy’, she wants ‘Lucy’. I’m sure I have things that would fit you. My feet are bigger than Evelyn’s so my shoes would fit better, I think. The only thing is you’d have to be a blond over here."

"That would be OK."

"Well fine. I live just a mile from Evelyn. The address is 12038 Parker Avenue. Just turn left two blocks before you get to Eleven’s and go about fifteen blocks. It’s on the left. If you get here before 5:00, I’ll throw in dinner. Does that sound good to you?"

"Yeah, sure."

"Fine, we’ll see you then."

Luke began to laugh when he hung up the phone. This was getting crazier. Now there were two women who wanted him to wear their dresses when he baby-sat.

On Friday Luke came home and dropped off his books. He had to do some chores around the house before he left. About 4:00 he finished up and rode his bike to Mary’s house. He arrived a little after 4:30. He parked his bike and knocked on the door. Mary answered.

"Hi Luke. Come on in. You can change in my bedroom. It’s down here." She said leading the way down a hall. "I’ve laid out some things for you. Evelyn tells me that you use three pairs of panties in each side of the bra to stuff it out. Is that right?"

"Ah, yeah three in each side."

"Well, I’ve laid some things out on my bed. I think everything will fit OK. If you have any problems just slip on the robe on my closet door and come tell me. The wig is on the closet shelf." She closed the door when Luke went in.

Luke put on the wig first and undressed. He put on the bra and counted out three pairs of panties and stuffed them in the left cup one at a time. Turning his attention to the right cup, he repeated the procedure. When he picked up the next to the last one, there were still two pairs on the bed. One was black like the rest of the lingerie. He checked, there were three in each cup. She had laid out seven pairs, not six. She must intend for him to wear the black pair. The rest had been various pastels. She had a girdle that started just under the bra and went to the top of his hips. It flared slightly at the hip and garter straps hung from the bottom. He put on the stockings and the panties. He stole look at himself in the full-length mirror. "How sexy." He thought. He put on the dress and tried on the shoes she had out for him. They were a pair of sling back heals. They completed the outfit. He came out into the kitchen where Mary was fixing dinner.

"Ahh. There’s Lucy at last. Come on into the bathroom and I’ll do your make-up."

When they sat down to dinner, Janet talked on and on about how neat he looked. Her mother had done a much better job on his make-up than Suzy's mom. It was true. Luke thought he did look more feminine after Mary got through.

"Oh, by the way Lucy, Evelyn and I have to go up to Seattle for a for a wedding on December 6th. We’ll want to drive up Friday evening and would be back sometime in the wee hours of Sunday morning. It’s a distant cousin of ours. She was a dear when Evelyn and I were growing up. We haven’t seen her in years. Neither of the girls knows her at all and wouldn’t know anyone else up there. The drive and almost nonstop activity would really be wearing on them. Would you be interested in baby-sitting for a couple of overnights? You could sleep on the hide-a-bed in our family room. I have a sexy black nightgown you might like to wear."

"Stay overnight two nights?"

"Yeah, you could be Lucy the whole time. We’ll have to teach you how to do your own make-up for Saturday. I’m sure you’ll catch on easy enough. What do you say? Will you do it?"

"OK. I'll have to ask my Dad. He may want to call and make sure that it’s for real. Oh! He doesn’t know I become Lucy when I baby-sit. I’d just as soon he not find out."

"Oh I wouldn’t dream of telling him."

December 6th came quickly. Luke showed up right after school and changed in to Mary’s clothes.

Mary seated him on a stool, in front of the bathroom vanity. Standing behind him she began to instructed him in the application of make up. She told him how to do the base makeup. Then she did the mascara on his right eye and had him do the left eye. They followed this pattern through eyeliner, shadow, and blush. Then she had him do his own lipstick. After they were through, she had him take the whole thing off and apply it all again by himself. She was satisfied that he could do a credible job and left it at that.

Evelyn showed up with Suzy and the five girls had dinner. Mary went in and packed after dinner. When she came out, she informed Luke that she had put some things in the family room closet and in the drawer in the coffee table for him to wear over the weekend. Evelyn and Mary left in Evelyn’s car. Lucy had a ball that weekend. The girls treated him as if he were really a girl baby-sitter. That night he checked the family room closet. It was small, but there were three dresses and another slip hanging in there. The floor held three pairs of shoes. On a hook behind the door was a really sexy nightgown. In the drawer in the coffee table, he found two pairs of panties and a bra. In the morning he put on another dress and did his makeup. He found it wasn’t as easy when there wasn’t someone there to correct him as he went. In the end, he did manage to get a pretty good job. However he was sure that Mary could have done much better and even Evelyn would have turned out a better job. No matter, he had fun and the girls had a good time.

Luke put on the nightgown about midnight and went to bed. He woke up about 7 and could hear the television. He knew the girls were up. He got up and put another dress. In the bathroom, he put on his makeup. It went a little smoother this time. Although, he did wish there was someone to give him hints on how it should be done.

He fixed the girls' breakfast and washed the dishes. At eleven o’clock, Luke was surprised to see Evelyn go into the kitchen and get a cup of coffee.

"I didn’t know you were staying the night last night." Luke said as she sat on the couch to sip her coffee.

"Well we didn’t really plan it that way. When we got here at 4 this morning, I was too tired to drive the mile home, so I just came in and shared a bed with my sister." Evelyn took a long drink of coffee with her eyes closed. When she opened them, she looked at Luke. "Well Lucy, it appears that you have become proficient at putting on makeup. I guess when you come to sit at my house, I can just turn you loose."

Mary was up by noon. Lucy made lunch for the group. As he was doing the dishes, Mary came in for another cup of coffee.

"Evelyn and I were talking on the way back. We will each need a daytime sitter during Christmas break. Are you interested? You can pick up $ 20 a day between the two of us. Plus you get your choice of whose wardrobe you want to dress from."

Luke jumped at the chance. Before Christmas, he sat at Mary's and after at Evelyn’s. On Christmas Eve he was given gifts. Mary gave him a set of "days of the week" embroidered panties. Evelyn gave him a set of falsies. A rather nice set.

Between the two sisters, he was Lucy at least three evenings a month for the next three months as well as two Saturdays. He was Lucy every day during spring break. That summer, Lucy was hired to do day care of the two girls. And so his life went all through high school. He had a complete wardrobe at each house, including shoes, as well as makeup that was really suitable for his skin tone. By the third year, he was comfortable enough with his appearance as a girl that he would answer the door. By the fourth year, he would occasionally take the girls to the movies during the day.

After high school, he had developed such a relationship with Mary, Janet, Evelyn and Suzy, that he would come by on the weekend and get dressed and just hang out. He often stayed for dinner. He was of course invited to all the birthday parties. (That is Lucy was invited.) Lucy even went on vacation with them a couple of those years.

 

– finis –

 

*********************************************
© 2000 by Patricia Marie Allen. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.