Millie's Release,

Being tonight is Halloween, I've decide to post my one attempt a using Halloween as the catalysis for discovering one's feminine side

It was written years ago and I offer it up now unchanged or edited.

Twelve-year-old Milton was about to end his Halloween trick or treat career. This was to be his last year. He had run the gambit of costumes. He had done all the usual costumes. He wanted something special. Something that would be remembered that he could say was his crowning achievement. He had never won the costume party prize at school for the best costume. This year he wanted to. Next year he would be in middle school. The kids there were too old to participate in such foolishness. At least the boys were. Some of the girls still went to costume parties, but even they didn’t go trick or treating.

Then there was his family party. This would be his last year to dress up there too. The older boys didn’t dress up. They usually just pulled practical jokes on the rest of the kids. The girls some how saw the whole thing differently. They dressed up just like the little kids and the adults. Milt was of the opinion that the adults got more of a kick out of costumes then the kids did. Some of their costumes were really elaborate.

That gave him an idea. Tuesday evening, after dad left for his bowling league, he was watching TV with his sister Anne. His mother had just finished the dishes and joined them.

“Mom, this is going to be my last year to go trick or treating isn’t it?”

“I imagine so. I don’t believe that I’ve ever seen an eighth grader at my door on Halloween, unless he was taking a younger brother or sister around for his parents. I think that most of them do that just to get candy. Most people like to reward the older kids for helping out their parents that way by giving them candy too.”

“The older boys don’t dress up for Halloween at grandpa’s party either do they.”

“I expect that they think it’s a little too childish for them.”

“So I guess that since I’ll be in the eighth grade next year, I won’t be dressing up then either will I?

“If you do, the other boys will tease you. You remember what happened when Charles wore his cowboy hat and boots to the party when he was fourteen. They accused him of coming as a cowboy and teased him all night until he went home early,” Anne reminded him.

“Oh yeah, they did didn’t they?” Milt said with obvious dejection in his voice.

“Are you going somewhere with all this, Milton?”

“Well, I just can’t come up with a really good costume. Since this is going to be my last year, I want it to be something that I haven’t done before and it has to be really great too.”

“Well, let’s see. We only have three weeks so it would have to be something that we have around here. All we have a lot of is your sisters old clothes. We bought enough new ones for her at the start of school this year. You wouldn’t’ think being in high school would mean such a drastic change of wardrobe.”

“Mom, really, I couldn’t go to high school wearing the same clothes I wore in middle school.”

“How’s this going to help me decide on a costume for Halloween?” Milt said, hauling the conversation back to the problem at hand.

“Well, you could go as a girl. Like I said, we have plenty of your sisters old clothes around.”

“Yeah, I’d be glad to help you look really good. I’d even be willing to lend you some of my jewelry and fix your hair for you,” Anne put in.

“A girl? I’m not to sure about that,” Milt said, balking at the idea.

“Well, Milton,” his mother said. “I’d say that’s the best offer you’re going to get. I’m sure that Anne has something that would make you look special.”

“I’m not sure. I think I’ll try too come up with something else,” Milton said heading for his room.

“Let me know if you change your mind,” his mother called after him.

Friday after school, Milton hadn’t come up with anything. He came in and plopped on the couch, obviously upset about something.

“What’s the matter Milton,” his mother asked.

“I still haven’t got a good costume for Halloween and it’s just two weeks away,” he retorted.

“Well there’s still a girl.”

“Do you really think that I could look really terrific dressed up as a girl?”

“Well, your sister said she’d help.”

“I really want to look good. I don’t want to look silly; I want to be the best girl a boy can be. It has to be good enough that people, even people who know me, will have to look twice to see that it’s me.”

“If we get the right dress, I’m sure that you could look that good. Your sister offered to do your hair and I’m sure that she’ll help you coordinate your outfit so it would be just right.”

“Well all of that won’t do any good if her clothes don’t fit right. That would be a sure give away.”

“Well, your sister is at Karen’s house tonight. They’re going to a football game after dinner and then she is spending the night. But we could look at the clothes and see if they fit. That is, if you’d like to.”

“I have to do something. If this doesn’t work out, we won’t tell anyone, OK? I’m not sure I can go through with it even if they do fit.”

“OK sweetie. Your father won’t be home until 5:30 so we have some time. We won’t even tell him if you try it and don’t want to go through with it.”

In Anne’s room, they opened her closet and his mother pushed her new clothes aside. Taking several dresses that Anne had worn to school last year, she laid them on the bed. In turn she held each one up to Milton. He stood there feeling strangely uncomfortable and excited at the same time. There was something taboo about all this, yet attractive. He found himself simultaneously attracted and repelled. It was like the forbidden fruit.

His mother finally chose a blue dress that had a boat neck, cap sleeves and a full skirt. Milton stood there mutely as she unbuttoned his shirt and slipped it over his head. She zipped it up and looked at the front. “Oh dear we’ll need to do something about a bust line,” she said. She quickly unzipped the dress and had it off over his head before he knew what it really felt like. She turned to Anne’s dresser and rummaged through a drawer. “Oh good, it’s still in here.” She turned around holding a bra. The cups were ridged. They looked as if there were already boobs inside. “Here,” she said, “turn around.” He did and she reached around him and slipped the straps over his arms and fastened it behind him. Turning him around she studied his chest. She took out a some stockings and put one each in the cups of the bra. She smiled and said, “Let’s try this again.” Picking up the dress, she put it on him again. Zipping it up, she began pulling it down on his hips. “You’ll have to take those pants off or this dress will never hang right,” she told him. He hiked up the skirt and unfastened his jeans and unzipped them letting them and the dress fall at the same time. He put a toe against the heel of his sneakers and pulled his foot out, stepping out of his jeans and losing his sock in the same motion. He repeated the process with the other foot.

He was standing in a dress. It felt really strange. Not at all what he thought it would feel like. Somehow, he thought it would be like wearing a bathrobe. But it wasn’t. It was different in some way he couldn’t define. Maybe it was the bra. He never wore a bra with his robe. His mother stepped behind him so he could see himself in the mirror. She began pulling his longish hair back and lifting it all sorts of ways. He was a long way from looking like a girl.

“I wish Anne were here. The dress fits just right, but I’m just not that good with hair. I go to the beauty parlor every week. When I was in high school, I was the one with the straight flat hair. Fortunately it was the seventies just barely and I could get away with just letting it grow long and be somewhat in style. Anne could really do something with this hair.”

He sure hoped so. The dress fit OK, but the rest of him looked just like what he was, a boy in a dress. “I’ll need shoes,” he said. Not wanting to reject the idea out of hand. But still he wasn’t to keen on it just yet. His mother took out some flats and he tried them on. To his amazement, they fit better than the dress. Well, there went that objection.

“We’ll have to let Anne have a crack at your hair. And she’s a genius with make up. I’m sure that a little of her magic there will help a lot to. You really have to let her try.”

“OK. I’ll have her try tomorrow and I hope she’s as good as you say she is.”

“I have to get dinner started,” she said. “You can change your clothes and hang up the dresses.”

With that, she turned and left him standing there still wearing the dress and shoes. He turned to face the mirror again. He squinted and swayed around a little. He looked a little like a girl. The skirt of the dress brushed his legs. Some how, that felt good. He became aware of the nothingness between his boxers and the rest of the world. It made him smile to think of walking around school like this. He struggled with the zipper a while. He almost called his mother back because he couldn’t get it low enough to reach from the bottom. But then he took one hand and pulled the dress up a little so he could use the other one to zip it down farther. After that he could reach the zipper from the bottom.

Taking the dress off he hung it in the closet. He still had on the shoes and the bra on when he picked up the next one. As he started toward the closet he caught sight of himself in the mirror. The dress was right in front of him. He stopped and held it up to himself. It was a shirt waist dress. The sleeves were three-quarter length and the skirt was full. It buttoned up the front and was made of a really light weight material. He decided to try it on. He unbuttoned the front and stepped into it. After fastening all the buttons, he looked in the mirror. With the light from the window behind him he could see the silhouette of his body right through the dress. If he was going to wear this one, he’d have to wear a slip under it. He could see why his mother discarded this one.

The thought of wearing a slip sent little shiver down his back. That would be entirely too girl like. As he unbuttoned the dress to take it off, he thought again. And wondered, “Just what would that be like?” He had to try it. He remembered a slip in the closet. Letting the dress fall to the floor, he got the slip and put it on. Stepping back into the circle of the dress, he pulled it up and re-buttoned it. Looking in the mirror again, he saw that the slip took care of the silhouette problem. Looking closely he could just tell there was lace on the bottom of the slip. And the lace on top just showed through as well. He turned and looked at his profile. Pulling his shoulders back he laughed out loud at the sight of a bust line on his chest.

He went to the window and walked back toward the mirror, watching himself walk. He looked pretty good. Except for his hair. His face was still young enough to not have too much of masculine shape just yet. He really kind of liked the way the dress swirled around the slip. Reluctantly he took it off and hung it up next to the other one. He crossed back to the bed and put on the next one. It zipped up the back and had a tight skirt that struck him just above the knees. He zipped it as far up the back as he could. Then he pulled up on the dress with one hand and got a hold of the zipper with the other and let go with the first hand he pulled the dress down with it and the zipper up.

This one was confining and didn’t fit as well, he was supposed to have hips. His were pretty much the same as his waist. The part below the waist was just kind of baggy. He struggled out of that one and after hanging it up, tried the next one.

The next one was straight shift. Sleeveless with a boat neck. He dropped it over his head and studied it in the mirror. It would look better if he had hips. He flounced back and forth in front of the mirror. He didn’t like it as well as the ones with a full skirt. That one in the closet he picked up another.

It was one of those short full skirted things with a layers of fabric and cap sleeves that buttoned up the back. He unbuttoned it and stepped into it. He wondered how he was going to manage all those buttons. He decided to start at the top. Buttoning the top button first, he worked his way down until he couldn’t pull the dress up any farther. Then he pulled it down and found he could easily reach the rest. He straightened the dress in front of the mirror. He smiled at the look of it. It was really feminine. He rocked his hips back and forth. The dress swayed. As it did, the slip just showed under it. Somehow seeing the lace peek out amused him. He remembered how much he liked to see that on the girls at school. Here he was seeing it over and over. All he had to do is move a little.

One by one, he tried each of them in turn. Seven in all. Then he quickly put the slip back where it came from and just tossed the bra back in the drawer where his mother got it from. He pulled on his pants and shirt. He picked up his shoes and socks and went back to his room. He felt really guilty. His mother had picked out the dress she thought he should wear and tried it on him. She told him to hang it up along with the others. She didn’t tell him to try on the others, just to hang them up.

He must have been in there for at least an hour. He needed an excuse for what he was doing all that time. He looked desperately around his room. Thankfully, his reading book was on his dresser. He was behind in it. He picked it up and laying on the bed, he began to read, then he realized he would need an excuse why he hadn’t read very much. So he laid the book on his chest and closed his eyes and pretended to be asleep. He almost really fell asleep when he heard a knock on the door.

“Milton,” his mother called as she peeked in the room.

“Oh mom, I was trying to catch up on my reading and fell asleep,” he told her.

“Well dinners about ready, you’d better wash up.”

Saturday afternoon Anne came home. Milton was at the table doing home work. His mother was straightening up the kitchen after lunch.

“Hi Anne, Milton decided to try our suggestion for Halloween.”

“Neat. We’ll have to pick out something nice for him to wear.”

“Well, I think I’ve found the dress. I had him try it on yesterday after school. It fits really well. Your shoes fit him as well. He’s concerned about his hair and face. I assured him that you could work miracles in that area.”

Milton stopped and listened. “I’m not too sure about it now. I looked like a boy in a dress. That’s not exactly what I had in mind.”

“So what are you going to do for a costume then?” Anne asked with a challenging look.

“Well I don’t know. I guess I’ll have to let you try to make me look like a girl. But if you don’t do a really good job, I’ll have to come up with something else.”

“Well, let’s see what I can do. Come on upstairs.”

Milton followed her upstairs. She instructed him to take off his shirt. She took him into the bathroom and washed his hair in the sink. Taking her blow dryer, she began to style his hair. It wasn’t overly long but it did cover his ears. She used brushes and combs. Late in the process, she sprayed it lightly with hair spray and teased it, brushing it back down gently. She took his chin in her hand and turned his face back and forth.

“You could use a little help,” she told him, picking up her mascara. She began stroking his lashes with the brush. Then she put a little blush on his cheeks and smoothed it with a big brush. She turned him toward the mirror. He looked really strange. Just the opposite as he had yesterday. This time it was his face that looked out of place on his boys body.

Anne led the way to her bedroom. She rummaged through the same drawer his mother had and brought out the same bra. She helped him on with it and put some stockings in the cups. “What dress did mom pick out,” she asked opening the closet.

“That one,” he said pointing at the blue dress.

Anne took it out and held it up to him. “It’s a nice dress, but I’m not sure you’ll get anything spectacular out of it. Put it on and we’ll see.” He stepped into it and turned around to let her zip it. “I should really make you do this for yourself. Girls do it all the time, you know.” She had him turn around and walk for her. “Well, your jeans make the waist ride up, but I don’t think that’s the best we can do anyway. You’re going to have to have try on some others,” she told him. “If all you wanted to do was pass as a girl,” she continued, unzipping the dress, “this would do.”

He stepped out of the dress and handed it to her. She hung it up and started looking through the rest. She turned to him and said. “You’ll need to lose the jeans. Here,” she told him, handing him the slip he had on yesterday. “Put this on and take off your jeans.” She turned back to the closet. He did as he was told.

For a second time he was standing there in a slip and bra. Only this time, someone knew. He wouldn’t be in trouble if anyone found out. She took out a dress and looked at it. Holding it up to him. It was the short one that let the slip peek out. She shook her head no and put it back. She took out another one. It was fancy. It had a low cut neck line and was sleeveless. Dropping it over his head, she zipped up the back. The skirt was very full and fell in loose folds. He liked it very much. The way it brushed against the slip when he walked was even more delightful then the one yesterday.

“Nope. To look really good you’d need a lot more bust line than we can stuff into a bra,” she said unzipping the dress.

The next one had three quarter length sleeves and a side sipper. It also had a full skirt. He liked it too, but she vetoed it saying he didn’t have enough hips. Off it came and was soon replaced by the shirt waist dress from yesterday. After a few turns around the room, Anne began to dig through her closet again. Milt knew this one was a no go too.

“I know!” Anne said turning around quickly. She turned back and pushed the new dresses all the way against the old and took out a garment bag. Laying it on the bed, she unzipped it. Inside was a burgundy dress. It was really fancy. “I wore this to the eighth grade graduation dance last year. It’s the only thing from last year that I would wear to a high school function,” she said holding the dress. “Jake Hawthorne kissed me in this dress.” She looked dreamy eyed for a few minutes.

It had a high neckline and a low back. Its knee length skirt had built in petticoats to make it stand out. There was some kind of rose colored sheer fabric draped across the front at the neckline and it continued over the shoulder and down the back.

Milt remembered this dress. When he saw her in it, it was the first time he thought his sister looked pretty. She unzipped it and had him step into it. As she zipped it up, he couldn’t help but feel special, almost regal. He was facing the mirror. The other dresses he had liked had made him look like a girl, but this one paled their effort. This was it. He knew it.

Anne knew it too. “We’ll have to redo your make-up. This dress calls for more than a little mascara and blush,” she told him, tying the sash in back. Back in the bathroom, she got out all of her make-up. Draping a towel across his chest, she put some kind of cream all over his face. She rubbed in real good with a little sponge. Then came a really light powder that she applied with a puff. Then came something that looked like a large artist’s brush. He thought she would brush off all the powder. She then redid his mascara, framing it with some liquid eye liner. That she topped it off with some eye shadow and darkened his eyebrows. More blush followed by lipstick. Shaking her head, she redid his hair.

She went to her dresser and took out a large wooden box. She brought back a bracelet and matching necklace. Another trip to the box and she produced a tiara. Settling it on his head, she led him to the full length mirror.

“Perfect!” he almost shouted. “I look like a princess.”

“You do. Don’t you just feel like a princess too?”

He did, kind of. But he didn’t want to say so. “I guess. I don’t know what a princess should feel like.”

She reached into a pocket on the garment bag and produced a pair of squash heeled pumps. He put them on and discovered that with even that low a heel, it wasn’t easy to walk. She had him practice a little. Soon he was able to look steady in them.

“You have to promise to be extra careful in this dress,” she told him.

“Oh I will. I won’t run or rough house at all.” Then he smiled. “I’ll be a perfect lady.”

Anne laughed. “You’d better be. Let’s show mom.”

Anne led the way down stairs. Milt discovered that negotiating the stairs required some concentration. Anne had him wait in the hall. She went just in the door of the family room. He could hear her say. “It gives me great pleasure to present Her Majesty the Princess of Sellwood.” With that, she put her hand through the door and motioned him in. He walked in and curtsied.

“Oh Milton, you look great!” his mother said. Just then, his father walked in from his garage workshop to see what all the fuss was about.

“Ki ki mo mo! It looks like I have two daughters,” his father said. “When you told me he was going to be a girl for Halloween, I didn’t think he was going to be this much girl,” he continued looking at his wife.

“Well, he wanted something special for his last Halloween costume,” she told him. “And Milton, you’ve got it. Walk around and let me see how nice you look.” Milton walked to the window and back. “You look every inch a girl and you make a very convincing princess. However, you still move like a twelve year old boy.”

“If he’ll spend the rest of the day in the outfit, I think we can teach him to move more like a girl,” Anne suggested.

“That’s a good idea. But perhaps we should use another dress for him to practice in. I’d hate to see him get that dress dirty. It has to be dry cleaned you know,” Mom agreed. Dad just shook his head and went back to the garage.

Anne took him back up to her room and put the one with the buttons down the back. Back in the family room, Anne demonstrated how to walk. Milton tried his best to imitate her as his mother watched. Anne and mom critiqued his walk. He had to walk from room to room with them following. Then mom got an idea. She went to her bedroom and brought back the video camera. She sat it on a tripod and began taping him as he walked. Then she taped Anne walking the same course. Every now and then, she would rewind the tape let him watch himself walk. He could see the difference between him and Anne. He tried again and again. Each time he watched the tape, he could see improvement. After an hour, they started working on sitting and standing up. They brought in a kitchen chair and set the camera in front of it. He sat down and at their request crossed his legs. Mom just laughed and stopped the camera.

“Anne, maybe you’d better put on a dress and demonstrate for him,” she said. Anne was back in a few minutes. She sat for the camera and crossed her legs. They played the part with Anne for him first and then rewound the tape some more and let him see himself followed by Anne. Watching himself, he could see his boxers when he was just sitting and they were really on display when he crossed his legs. In the section with Anne, try as he would to see, there was no hint of what kind underwear she was wearing. He tried it again. He had to concentrate on keeping his legs together. When it came to crossing his legs, he found that it was necessary to cross his knees rather than put an ankle over a knee. Another hour went by before he became comfortable with that.

“Oh look at the time,” his mom said. “I’ll need you girls to help if I’m going to have dinner on time.” She led the way to the kitchen and began delegating duties. Milton sat the table while Anne pealed potatoes. Mom began preparing the Swiss steak. She had Milton prepare chocolate pudding. They made quite a team. Dinner was on the table in 45 minutes.

At dinner, dad kept looking a Milton and shaking his head. Mom had Milton serve desert since he made it. Conversation was centered around what a great hit Milton was going to be on Halloween and what the rest of the family was going to wear to grandpa’s party. After dinner Milton helped Anne and his mother clear the table and do the dishes. It just seemed natural. Before that, he had complained loudly if he was even asked to take anything but his own plate to the kitchen. After they were through, mom gave Milton an uncharacteristic hug.

“If this is an example of how helpful you are in a dress, maybe I should put you in a dress every night,” she teased.

“Yeah,” Anne said. “You never did that before. Maybe I should move my old clothes into your closet. Lord knows I could use the room.”

His mother gave him another hug and kissed him on the head. She smiled. “You know I’m just teasing, don’t you?” she said walking him into the family room. He looked up and shook his head. However, something stirred inside when she said that. As they sat watching television, Anne nudged mom and pointed at Milton’s legs. They were spread open like a boy.

“Put your legs together young lady!” Mom said sharply. “Everyone can see your underwear.” Milton snapped his legs together and blushed. “Perhaps, we’ll need to practice again tomorrow.”

At bedtime, Milton found he regretted having to take off the dress. That surprised him. He never thought it would fun to wear a dress. But it had been. There was something exciting about it. As Anne was removing his make-up, mom had instructed him to put the clothes on again in the morning. So he did. Anne caught him going by the bathroom.

“If you’re going to dress like a girl, you’d better look like a girl in case someone sees you through the window,” Anne told him. She did a light make-up job on him and combed his hair and sprayed with hair spray. Out of spite, she doused him with perfume. He blinked in surprise, but didn’t object. As he headed toward the kitchen for breakfast, he wondered why he didn’t object. The last time she did that he screamed and tried his best to wash it off. This time, he kind of liked the scent that followed him.

After breakfast, he cleared the table and helped Anne wash the dishes. His mother commented on how much help her “part time daughter” had been. Milton blushed at that. Their dad remained silent about the whole thing and left for his golf date just after breakfast.

The rest of the day was spent video taping Milton as he performed simple actions, followed by watching the tape and critiquing him. After he would try each thing again. Dad came home about 4:00 PM. All he could do was shake his head. In the evening, they lightened up on him. Mom put the video camera in the corner pointed to the area that Milton habitually occupied and turned in on. By bedtime, Milton had almost gotten the moves down to a second nature, but he still had to concentrate on some things like keeping his legs together. In the morning he went to school as usual. Through the week his dad made only one comment. “It’s nice to have my son back again. I was beginning to feel out numbered over the weekend.”

Friday when he came home, his mother came in from the kitchen. “Milton, your sister and I were talking.” She paused. “How confident do you feel about your princess costume?”

“OK I guess. Why?”

“Well, I was watching the tape of Sunday night and there are still some rough spots. Most particularly keeping your legs together and sitting down. Anne and I thought maybe you like to practice some more. What do you think?”

“Well, I don’t know. I thought I was doing pretty good.”

“Why don’t you look at the tape, and then decide,” Anne suggested. They went in to the family room. Mom already had the tape cued up and started the VCR. Milton watched. As he saw himself walking around the room, he felt a little of the excitement of last weekend. At different points, mom or Anne would point out little errors he committed. In the end, he allowed that he wasn’t as good as he thought. Dad had come in near the end of the discussion.

“Does that mean, I’m going to be out numbered again this weekend?”

“Well dear, you want Milton to be really good don’t you? He wants to win the prize for best costume. He needs to be really good for that.”

“Forget I asked.”

Dad was quite at dinner. After dinner Anne took Milton upstairs and gave him a pile of clothes. He took them to his room and put them on top of his dresser. It excited him a little. He noticed the dress was the shirtwaist dress that required the slip. That made sense. The skirt was the same length as the one he was going to wear for Halloween.

In the morning, he got up to get dressed for the day. He found himself a little excited. As he sorted out the clothes he found that Anne had included a pair of panties. He carried them across the hall and knocked on her door.

“Yeah?” she called from inside. He opened the door a crack and stuck the panties inside.

“What’s with these?” he asked pointedly.

Anne appeared at the door tying her robe. “I thought you might want to wear them. After all, you’re going to wear everything else,” she teased.

“Really!” he said with a frown.

She smiled coyly. “I dare you.”

“Get real.”

“What’s amatter? Chicken?”

“No!”

“Double dare you.”

“Dad would kill me.”

“So, we don’t tell him.”

“What about mom?”

“She doesn’t need to know. I figure it will be an incentive to for you to keep your legs together. Not to mention the fact that your boxer shorts hang down a lot farther. These will be easier to keep out of sight.” Her logic was impeccable. “Are you going to do it, or are you chicken?” she continued.

“I’m no chicken.”

“Enjoy,” she said closing the door.

Milton went back to his room. He found himself shaking as he put the panties on. His breath was labored for a time, but as he was buttoning up the dress he got it under control. Just then, his sister knocked on the door. “Ready for make-up?” she called.

“Yeah,” he said slipping his feet into the shoes.

In the bathroom, Anne did her magic on his face. She got him to put on his own lipstick. As he was leaning in toward the mirror, Anne lifted his dress and slip.

“Hey!” he said jumping back. “What do you think you’re doing?”

“I just wanted to see if you were wearing the panties.”

“Well I am!” he said indignantly.

“So I saw, your butt looks cute in them.”

“Gee thanks,” he said. “How would you like it if I did that to you?”

“I’ll do it for you,” she said, turning around. She lifted her skirt and stuck her pantied butt out for a second before letting her skirt fall. Turning back she said. “There. Now we’re even.”

Milton spent the rest of the day practicing his feminine mannerisms. Anne had been right. Wearing panties was an incentive to keep his legs together. At lunch mom complemented him on the improvement. He blushed, thinking, “If only she knew why.” He was still working on his walk and hand movements. He was having trouble with the hand movements especially. He was very distracted. Every time he shifted his weight or while he was walking, he was very aware of the panties. It made it hard to pay attention to anything else.

Dad spent the day in his workshop. He was only in evidence only when he came in for coffee or to use the bathroom. He even took lunch out there. Milton could tell he wasn’t thrilled about having his son wondering around in a dress. Mom must have tricked him into agreeing to it and wouldn’t let him out of the agreement.

While he was washing off the make-up in the bathroom, Anne stuck her head in said. “I put some things on your bed for tomorrow.”

He went in to find the blue dress that mom had pick first and another pair of panties. He smiled and put the panties on his dresser and hung the dress in his closet. Getting undressed he hung up today’s dress. He put the slip on a hook next to his bathrobe. He stripped out of the panties and put them in his hamper and put the bra on his dresser next to tomorrow’s panties.

In the morning he woke early. Excitedly, he got out of bed. Smiling, he put on the panties and bra. The slip felt delicious. He put the dress on and worked his trick on the zipper. Slipping on the shoes, he went to the bathroom and put on lipstick. He was brushing out his hair when Anne came in.

“Well, I see you’re into it early. Lipstick and all.” She reached for his dress.

He quickly clapped his hand over his butt and said, “Yes, I’m wearing them.”

“Prove it,” she said.

He carefully lifted the side of the skirt far enough to show the side of his panties. She laughed and took over on his hair. When she was through she talked him into putting on his own mascara. “You’ll have to know how in case you need to touch it up an Friday,” was the line she used to convince him. She left him to go get dressed. Milton spotted her perfume on the counter. He picked it up and sprayed it behind each ear and on his wrists the way he had seen Anne do.

Another day of practice and an invisible dad. But by 4:00, Milton was a convincing girl. They sat watching the “candid” (not really candid, just running from the corner to catch all of Milton’s actions as naturally as possible) tape of the afternoon. Mom and Anne both failed to find anything to fault him on.

Thursday night, Milton was instructed to take a bath and wash his hair with Anne’s shampoo and use her conditioner. He did as instructed. In the morning, Anne awakened him early. She told him to dress as far as the slip and meet her in the bathroom. By now, fastening a bra was as easy as doing the waist button on his jeans. The panties she had provided for today were red, with large lace panels at each leg. They had lace outlines of roses in black. He dropped the slip over his head and relished the feel as it slid down his body. He nearly ran to the bathroom.

Once there, Anne did the heavy make-up she had done two weeks before. She put the necklace and bracelet on him. Turning her head slightly with a wicked smile, she picked up the perfume. She nodded slightly as a question. His heart raced a little. Then he shook his head. He leaned his head back as she sprayed his neck on either side. Then he held out his wrist she sprayed it and he rubbed it against the other one. Then she reached down and sprayed the back of each knee taking his arm she sprayed the pulse point above the elbow on inside of each one.

They went to her room and got out “the” dress. Milton looked outside. There was a heavy frost. “It’s cold outside. I hope my legs don’t freeze.”

“If I were you, I’d wear pantyhose.”

He sucked in his breath and asked. “Pantyhose?”

“Sure, why not? If you wear nude most people won’t even notice.”

After a heart racing pause, he agreed. She got out a pair that were sheer to the waist and helped get them started but made him pull them up once they were at his knees. She maintained that he would have to know how if he had to go to the bathroom. Finally, he got them on and was in the dress. Anne produced a white wool cape and red purse that matched his shoes.

They had a quick breakfast and mom offered to take him to school. He couldn’t very well ride his bike like he usually did. On the way out the door Anne caught her mothers attention. Mom motioned him to get in the car, and stayed behind to see what Anne wanted.

Looking into the garage to see that Milton wasn’t listening she whispered hoarsely. “I dared Milton to wear panties and he did it.”

“You did what?”

“Well, I figured that he needed an incentive to keep his legs together, so I dared him to wear panties. He took the dare.”

“Oh my God. I hope he does keep his legs together. You’d better hope none of the guys catch him in the bathroom and pull up his dress to see what he wearing underneath.”

“He was worried about his legs getting cold so I gave him a pair of pantyhose to wear too.”

“Anne, do you have any idea what kind of teasing he’ll go through if anyone figures it out?”

“He’s young. He’ll get over it. Besides, all the trouble he’s given me the last couple of years he’s got a little teasing coming.”

“By rights, I should bring him back in here and get that stuff off. But he would be mortified if he even thought I knew. If anything comes of this you are in serious trouble young lady,” she said as she went into the garage.

At school two friends were waiting. He had confided in them. They each bet him five dollars that he would chicken out. His mother let him out of the car at the main entrance. Bill and Mike didn’t recognize him when he got out of the car. He almost did chicken out when he saw them standing at the door. He turned to tell his mom to take him home but she had already started to drive off. He couldn’t get her attention without yelling. He turned around and bucked up his courage. He set his chin and put on his best girl walk and headed for the door. He didn’t look at them directly.

As he got abreast of them he heard Mike say to Bill, “Who do you think she is?”

Bill answered. “I don’t know, but I’m sure gonna find out.”

Milt began to snicker. By the time he got to the door, he was shaking with laughter and had to hold onto the door frame to keep from falling down. Regaining a little composure, he turned to his friends and said “If either of you two makes a pass at me, I’ll deck you.”

Bill and Mike blinked and looked at each other. “Milt?” Mike asked in disbelief.

“It’s me.”

“Oh my God” Bill said. “I’m going to be sick. I thought you were the best looking girl in the school. I was gonna ask you to be my girlfriend.”

“Milt. I still can’t believe it’s you. You really look like a girl. But now that I look, it is you.”

Milt put out his hand and said, “Pay up. I’m here and in the costume I said I’d wear.”

Mike and Bill each reached into their wallets and forked over the five bucks. Just then, the bell rang. The three of them headed for class. Bill was in a very predictable hobo outfit. A pair of his dads jeans with a rope for a belt, and old pair of shoes and crumpled hat with a ragged shirt. Mike had pirate outfit. It consisted of a large brimmed black hat. A white shirt and black pants and boots. He had a wooden sword through his wide belt. Compared to his costume, Mike and Bill’s costumes were lame. He was sure to win if this was the kind of competition he had.

In class the teacher called role. Appraising each students costume as he called their name. He came to Milton. “Milton Johnson.”

“Here.”

Mr. Larson looked up. “Milton Johnson?”

“Here.”

Mr. Larson shook his head and went on with the role. The class was a buzz with whispers about Milton’s costume. The schedule called for morning classes and a big afternoon party in the gymnasium. Mr. Larson’s seventh grade English and social studies class was all but a waste. He did manage to assign some homework for Monday, but that was about all. When the lunch bell rang everyone crowded around Milton.

All the kids wanted to know if it was really him. Whose clothes he was wearing. Who did his make-up? It took nearly half of the lunch period for Milton to make it to the cafeteria. While he was eating, he was treated as if he were the most popular kid in school. Even the eighth graders paid attention to him. The girls anyway. The guys avoided him like the plague. None of them were wearing costumes.

After lunch the they reported to their first class for role call and then gathered in the gymnasium. At first there was the usual knotting of groups you might expect. Next the principal used the PA system to announce the afternoon’s activities. There would be apple bobbing, a tug of war, an on going dance in one corner and at 2:30 they would begin the costume judging. All those wearing costumes were to line up and walk in front of the faculty. Each of the teachers would rate the costumes on a scale of 1 — 10. The five students with the most points would then each present themselves for the final judging.

Milton didn’t want to bob for apples because it might mess up his make-up. He couldn’t participate in the tug of war in high heels and he sure didn’t want to dance. So he just sat on the side lines of the dance and watched everyone else. Every seventh and eighth grade girl came by and complemented him on his costume. The sixth grade girls were gathered in little knots. Looking at him.

Milton made the mistake of drinking a lot of spiced apple cider. He headed into the hall and started for the bathroom. As he started to go into the boy’s room, the janitor challenged him.

“Aren’t you going to the wrong room? You want the one over there,” he said pointing across the hall to the girls room. Milt just looked embarrassed and nervously went to the girls room. Inside, he quickly entered a stall and locked it. He hurriedly hiked up his dress and pulled down the pantyhose and panties. He reminded himself he should to sit in case someone else came in. While he was pulling his panties up, another girl did come in. He was terrified. His hands shook as he pulled up his pantyhose. He had to try three times to get it right. Luckily she was in a stall when he got through. Milton quickly stepped out of the stall and beat feet for the hall. He nearly ran to the gym.

Shortly the costume judging began. It took nearly half an hour for everyone to give their name, get a number and walk in front of the panel of judges. The results were tabulated and finally the finalists were announced. Milton was elated to be among them. He was competing against a harem girl, a magician, an Indian chief and fire fighter. In the final judging, each contestant had to give their name, grade in school and a short description of the creation of their costume.

The harem girl was an eighth grader named Patricia Lucus. Her costume was part of the wardrobe for a community play, where her mother was costume mistress.

The Indian chief was a sixth grader named Johnny Wolf. He was one quarter Sioux. His war bonnet had belonged to his great-great-grandfather and his mother made his imitation buck skin shirt and pants.

The fire fighter was a seventh grade boy who’s father was a fireman and got him a real turn out coat, rubber boots and helmet.

The magician was a sixth grade boy who had always liked magic and could really do a few tricks. His mother had rented the tux and top hat for him and made him a cape.

When Milton gave his name. Every staff member looked up and scrutinized him closely as he explained that his dress belonged to his sister as did the jewelry. And that she did his make-up and hair. There was a short conference amongst the staff and Milton was asked to join them. Here he was questioned about his identity. Mr. Larson explained that Milton was in his class. While he couldn’t say that he looked much like Milton, there was a resemblance and it was indeed Milton’s voice. They thanked Milton and dismissed him. Shortly the winners were announced.

The Harem girl was fourth runner up, the fire fighter was third runner up, the Indian chief was second runner up and the magician was first runner up. Milton was grand prize winner.

The principle, Mrs. Melvek told him that his princess costume was good enough to get him into the finals when most of the staff thought he was a girl. When they became convinced he was a boy the question then was “where did the rest of the group rank?” Milton was the hands-down winner.

Milton’s mother picked him up from school at 3:45.

“Well, how did it go,” she asked.

“Terrific. A lot of people thought I was really a girl. Mike and Bill didn’t recognize me until I talked to them. They thought if I really went through with it, I would look really dorky.”

“Did you win the costume contest?”

“I sure did,” he said showing her his certificate and the small scarecrow trophy.

“Well, there is just the family party and trick or treating tomorrow to get through and then you can get back to being a full time boy.” They rode the rest of the way in silence. When they were in the garage, his mother turned to him and said. “To tell the truth, I think I’ll miss my part time daughter. It was fun teaching you to be a girl. What did you think of it?”

“Over all it was fun. It was a lot of work but I enjoyed it.”

“What about Anne. Did she do anything or ask you to do anything that you didn’t like?” she fished.

Milton shrugged his shoulders and said, “No, I felt a little strange at first, but I got used to it.” Milton had to admit to himself that the last three weeks, he and Anne had gotten along better then ever. She used to get on his nerves on the weekends, when she didn’t have anything else to do.

Inside Milton ran over to Anne, giving her a big hug. “Thanks for doing such a good job, I won the best costume award. See?” he said showing her his certificate and trophy. He stayed in costume until after dinner. Truth was by 8:00 he was bushed and ready for bed. It had been an exciting day.

He woke up about 10:00 in the morning to find Anne in his bedroom. “I just brought you some clean underwear for today,” she told him.

He got up and sure enough there was a fresh pair of panties on his dresser along with another pair of pantyhose. He went to the bathroom and after combing his hair out, he slipped down to the kitchen to get a bowl of cereal. His mother came in as he was rinsing out his bowl.

“Hi hon. have a good night?”

“Ah, yeah, I guess. I slept through it,” he smiled. “Mom, when do you think I should put on my costume today?”

“Well, we won’t be leaving for grandpa’s until 1:00, but I’d say you could put it on when ever you want,” she said.

He went up and looked at the pantyhose and panties. These were really lacy. They were almost the same color as the dress. He put them on. The pantyhose followed closely behind. He was amazed at how easily he was able to get into them with so little experience at it. He put on the bra and slip and went into the bathroom where he tried to make his hair do what Anne had done with it the day before. He wasn’t entirely successful. He did, however, get a reasonably girlish style. He put on his robe and slippers and lounged around the family room.

His mother brought him a sandwich at noon and told him that she was going to get into her costume. He ate the sandwich and went up to his room and put on the dress and shoes. He found Anne and she did his make-up and hair. After she went to get into her costume, he borrowed her perfume.

At grandpa’s party, he was hardly noticed because they were one of the last to arrive. After about an hour, Anne brought Cousin Shirley over to see his costume.

“Milton? Oh my God. You look like a real girl,” Shirley told him. “I thought that was a pretty good princess costume, but I thought it was Anne. Then I saw Anne and asked her who you were. I thought she was kidding when she told me it was you.”

“Well it’s me and your not the only one who thinks my costume is pretty good. I won ‘best costume’ at school yesterday,” Milton told her proudly.

“You wore that to school?”

“Un-huh.”

“Oh no. Really? Oh wow. Wait until everybody finds out it’s you Milton. Milton just doesn’t fit you. You need a girls name. I know. Milton, … Millie. It’s a natural. Come on Millie I’ve got to show you to mom. With that Shirley marched Milton/Millie around the party introducing him as Millie to everyone, especially the adults. She took him to her mother first. She was talking with his Aunt Linda.

“Mom, Aunt Linda, have you two met Princess Millie?”

“Princess Millie? Whose girl are you,” her mother asked.

Shirley began laughing. “Mother, you really don’t know who Millie is?”

“No, she looks familiar as if I should, but no. I don’t know Millie.”

“Millie is Cousin Milton.”

“Milton? Charlotte’s boy?”

Milton smiled. “None other.”

“Oh my goodness! Linda did you recognize him?”

“No, I would have thought it was his sister Anne, but I saw her earlier.”

“Well young man, you have the most convincing costume at the party. Making it look like a princess costume was a stroke of genius. I’ve seen other men dress like women at costume parties, but they always just dressed like women. The ones that were able to really look like women stood out because they didn’t look like they were wearing a costume. Wearing a girls costume was a great idea.”

“Anne picked out the costume. My mother suggested that I go as a girl. Anne actually picked out the dress and added the jewelry and cape that make the whole thing look like a princess outfit. She did my make up and hair too.”

“Well, she certainly did a good job. Don’t you think so, Linda.”

“Indeed she did.”

“Aunt Linda, where are Angela and Kim? I want them to see Millie.”

“Oh, they’re spending the night with a school friend from school. She had a party and the girls really wanted to go.”

That scene was repeated all over the party. Everyone was amazed at his costume. It seemed to Milton that every one of the girl cousins came and talked to him that day. They invited him to go trick or treating with the girls group that evening. Traditionally, the girls and young boys went in one group and the rest of the boys in another. This was because the boys group usually deteriorated in to tricks late in the evening. Milton decided to go with the girls because he figured he couldn’t run in the heels and if he took them off, he’d ruin the nylons. He really didn’t want anyone to know he was wearing nylons. They might question what other things he might be wearing.

Sunday morning, he returned all the things to Anne. Returning to his room, he discovered that he was a little let down. It somehow seamed strange not to be putting them on.

* * *

Things pretty much got back to normal. Although, he did find himself a little wistful on weekends. He didn’t have any more excuse to dress up in Anne’s clothes. After three weekends in a dress, he had gotten used to the idea. It was three weeks later, the Friday after Thanksgiving, that he went to return Mike’s football. On the way home, he was riding his bike lazily down the street. He really didn’t have to be home. He had all day because of the long Thanksgiving holiday. Anne was home and she was back to getting on his nerves like before. Suddenly he was pulled abruptly from his thoughts.

“Hey Milton! Hi!” It was Jennifer. She was in his class at school.

He pulled up at the curb. “Oh hi Jennifer. I didn’t know you lived here.”

“Yeah, I saw you ride by earlier. You were going really going fast then.”

“Oh, I was on my way to take Mike’s football back. I borrowed it over Thanksgiving so my cousins and I could play football.”

“Where ya going now?”

“Aw, home, I guess.”

“You guess? You don’t know?”

“Well, yeah, I know. I just don’t really want to get there to fast.”

“You could always stay here for a while. I’m supposed to rake the leaves in the back yard. Maybe you could help me,” she said, practicing the use of feminine wiles.

“OK, it’s better than going home and having my sister bug me to do something for her. At least, you want me to help you. She’d want me to do it for her. I rather help you than slave for her.”

Milton parked his bike next to the porch and followed her around the back. He began raking leaves while she bagged them. There were three trees and a lot of leaves. Milton was able to get them in piles faster then Jennifer could bag them. After about an hour, Milton had all the leaves raked into piles and Jennifer was eight piles behind. Milton began helping her bag the leaves.

Just then, it began to rain. If they stopped and waited for the rain to stop, the leaves would get all soggy and be hard to handle. So they stayed at the job until all the leaves were in bags. Then they ran for the back porch. Jennifer didn’t take the most direct route. Milton found out why. There was a low spot in the lawn that collected water. Milton ran right through it. His tennis shoes did nothing to keep the water out.

“Come in and we’ll put your shoes and socks by the register to dry out. I’m sure my mother won’t mind.” Milton stopped at the door and removed his soaked foot wear.

“Thanks. It wouldn’t be much fun to ride home in the rain with soaking feet,” he told her as he put his shoes and socks on the news paper she placed near the heat register.

Jennifer told him how impressed she had been with his Halloween costume. “You know that was a really neat costume you wore for Halloween. Some of the sixth grade girls thought you were really a girl dressed as princess.”

“Yeah, most of the teachers thought I was a girl too. When they found out different, Mrs. Melvek told me that I was shoe in from that point on.”

“Well, you should have won. You went to a lot of trouble to make the costume realistic. Pantyhose and panties and all. I think you were terribly brave to go that far. Most boys would have worn a pair of swim trunks or shorts. But you went all the way. It must have helped you stay in character. I know I was impressed by your thoroughness.”

Milton was mortified. “I … I real … really didn’t think anyone could tell. My sister told me that the pantyhose would keep my legs warm. She said the nude pantyhose wouldn’t be noticed. And … and … well they wouldn’t fit right over my boxer shorts. I had to borrow my sisters underwear.”

“The only ones she had were red lace?”

Milton turned redder then the panties had been. “She picked them out, I just put on what she gave me.” He neglected to say how pleased he had been with her choice or that he had worn panties during his practice sessions. “How did you know about them? I was really careful to keep my legs together when I sat down.”

“Yes you did, but when you dropped the purse you were carrying, you didn’t keep your legs together when you picked it up. I just happened to be the one to be in the right place to notice,” she told him.

“I suppose it’s all over school that I was wearing panties and pantyhose,” Milton said hanging his head.

“No, I didn’t tell anybody. I wouldn’t embarrass you that way,” she smiled. “If you want to wear panties, it’s nobody’s business but your own.” Milton was visibly relieved. “Do you think you’ll ever do anything like that again?”

Milton’s heart began to race. He had thought of that a lot. He had secretly hoped that Anne would be gone today, but had considered himself lucky she wasn’t. He’d have been severely tempted to do just that. “No!” he said, just a little to emphatically.

“To bad, you really look good as a girl.”

Milton turned to look out the window. He needed to get out of there, before she read his face. He had lied to her and he knew he wasn’t a good liar. Jennifer was quiet. Milton had just begun to wonder why, when she put a wig on him. He whirled around. “What are you doing?” he said breathlessly.

“I just wanted to see how you’d look with blonde hair. It looks good on you. Let me do a little make-up. I’ll bet you’ll make a really good looking blonde. You have the complexion for it.”

“Make-up? Ah … no, not a good idea. It was one thing for Halloween, but not now. I couldn’t explain this to anyone.” His heart was pounding like a steam engine. He had to stop this. But how? His shoes were still wet. He couldn’t just leave.

“Oh come on. I won’t tell anyone. I didn’t tell about your panties on Halloween.”

“Well OK. But just a little.” He couldn’t believe what he just heard his mouth say. She sat him at the table and got out a make-up kit and began. He sat in disbelief as she did foundation, blush, mascara eyeliner, eye shadow and lipstick.

“There!” she said. “Come look in the mirror,” she told him, pulling his arm. Standing in front of the mirror in the entry hall Milton saw that Jennifer wasn’t quite as skilled as Anne.

“I don’t know,” he said. “I think I look like a boy with make-up.”

“No. You look like a girl. You’d be able to see it if it weren’t for your flat chest. Wait here,” she ordered. She came back with a blouse and a heavily padded bra. “Here. Put these on,” she ordered.

In a daze, he unbuttoned his shirt and let it slide off his shoulders. In a trance he put on the bra, failing to disguise his adeptness. Taking the blouse he had it on and buttoned before he realized how easy it was for her to get him to do this.

“Now look in the mirror.”

He turned. The combined effect was showing. Milton felt warm. His breath was short. “I … I still look like a boy in make-up,” he lied. The feel of the polyester blouse was intoxicating.

“No you don’t. Come here. She pulled him down the hall stopping him in front of a full length mirror. “Wait here.” Again she was so forceful in her command, that he waited just as he was told. She reappeared after several minutes with a half slip and a mid-calf skirt. “Put these on,” she told him. She was like a runaway locomotive going down hill. He knew he had to stop her but didn’t have the strength. Every time he took another piece of clothing, he could feel his resistance ebbing. Knowing he shouldn’t he stepped into the slip and then the skirt. The skirt was a blue print that was also polyester like the blouse. He looked into the mirror. “You’ll have to take off your pants to get the effect.” Numbly, he lifted the skirt and slip and let his pants and the skirt fall at the same time. He stepped out of the pants.

“There,” she said. “Now, put these on and walk down the hall and come back. You’ll see what I see. You look like a girl.” She handed him a pair of silk knee socks and a pair of flats. He did as he was told.

Again, he denied it. “I still look like a boy.” She disappeared for just a moment and returned with a pair of red panties.

“I think you need to put these on to get into character.” Now he did get nervous. He licked his lips and shook his head slowly and deliberately no. “Oh come on. No need to get scared now. With what you already have on, what difference can these make,” she asked, pushing them into his hand.

He trembled slightly as he reached behind pulling up his skirt and slip to drop his boxers. He felt faint as he stepped into the panties. He was careful to be sure the skirt hid what shouldn’t be seen as he pulled them up.

“Now. Try it again.”

He walked to the end of the hall and turned. He was so fascinated with his reflection, he didn’t even notice that she had removed his pants and boxers. “Well, what do you think,” she asked as he reached the mirror.

“OK so I look like a girl.” There was a long silence as she smiled and he couldn’t take his eyes off his reflection. “I should get home soon,” he said, beginning to get nervous about being there dressed as a girl. “I wouldn’t want your mother to catch me doing this.”

“Oh don’t worry. It’s barely noon. She won’t be home until 5:30.”

Taking him by the hand she led him to the kitchen. “Let’s have lunch and then we can bake the pie my mother wanted me to bake today.”

Before he could object, she had soup on the stove and was making tuna salad for sandwiches. He was intoxicated by the happenings of the last hour. After they ate their soup and sandwiches, Jennifer put a frilly apron on him and a plainer one on herself. She assembled the ingredients and assigned duties. Milton fell into his helpful role that had characterized his practice sessions.

Jennifer slipped away long enough to get her 110 camera. She snapped two pictures before Milton even knew she had the camera. When he found out, he was at first put out and then thought it would be neat to see what he looked like in the pictures.

When the pie went into the oven the “girls” retired to the living room. Where they noticed that the sun has come out and again. Jennifer stepped out onto the back porch.

“Milton. Come on out. We can sit on the swing. It’s really warm.”

Timidly he stepped out. “Milton doesn’t seem right I should be calling you something else, considering how you’re dressed.”

“My cousin, Shirley, called me Millie on Halloween,” he offered.

“Millie! I love it.”

She got several pictures of “Millie” standing on the porch, sitting in the swing and standing in the doorway. Inside there were pictures of “Millie” in the kitchen, at the table, on the couch and in an overstuffed chair. He stayed dressed that way until about 4:00. Then he changed back to his own clothes.

Jennifer went out on the front porch with him as he left. “You ride your bike to school everyday, don’t you?”

“Yeah. It gives me more time with the guys in the morning and I get home quicker too.”

“What way do you ride to school?”

“I go down Kelly right over there,” he said, indicating the next street over.

“I’d like to ride my bike to school, but my mother doesn’t want me to ride alone and I don’t have a lock for it.”

“I have a long chain, you could lock your bike with mine,” he offered.

“Well, I’d still have to ride alone.”

“I could come down your street as easy as Kelly. You could ride with me.”

“OK,” she said smiling. “I’ll ask my mother and call you. Give me you phone number.”

On Monday Milton altered his course to school and picked up Jennifer on the way. It became a habit and Jennifer became a close friend. Milton was sure that she never said anything to anyone about his activity that Friday.

Two weeks later as they were riding home Jennifer informed him. “I got those pictures back from the drug store. Would you like to come over tomorrow and see them?”

“Yeah, I guess so.”

“Why don’t you come over at 9:00. We can make a day of it.”

He was there at 9:00 on the dot. He was anxious to see the pictures. All he had was the video tape of his practice sessions. He was sure that mom would tape over those the first chance she got. So he wouldn’t have that for long. Parking his bike, he mounted the steps and rang the bell.

“Hi Milton, you’re right on time. Come on in.”

“Hi,” he said nervously. “Ah, I hope we can look at the pictures without your mother wanting to see them,” he continued in a hoarse whisper.

“Oh don’t worry about that, she’s at a doctors appointment. She won’t be back until after 1:00,” she assured him. “Go into the bathroom and tell me what you see.”

Milton thought she might have put the pictures out on the bathroom counter. He thought that would be a strange place to look at the pictures. He figured they might set on the couch, at the table or maybe on the porch swing. In the bathroom he didn’t see the pictures. Instead, there was a pair of panties and the wig. There was a full slip and dress hanging from the shower door. On the floor were a pair of white flats. Milton paused a long moment and returned to the door.

“What are these in here for?” he asked shakily. He was sure that he already knew the answer.

“I thought it would be fun for you to wear a costume, while you saw pictures yourself wearing a costume. You don’t have to wear them, if you don’t want to see pictures.”

It was a kind of blackmail. He stepped back into the bathroom. He surveyed the clothes. The dress was a full skirted polyester shirtwaist dress. He knew it would feel delicious. He closed the door and began to strip.

“You know of course, this is blackmail.”

“I know, but we won’t tell anyone,” she said from the other side of the door.

He pulled on the panties and put on the bra. The slip virtually floated over his body. He stepped into the dress and buttoned it. He found his breath was a short and there was a pleasant warmth in his stomach. He put his feet in the shoes and opened the door. Jennifer was standing there smiling. She came in and opened a drawer. Taking out some makeup, she worked deftly on his face, without asking permission. He couldn’t bring himself to protest.

“It’s kind of nice out. Let’s look at the pictures on the porch,” she said, leading the way. Milt was amazed he looked so much like a girl in the pictures. He didn’t think a seventh grade girl like Jennifer could have enough experience with make-up to do such a good job without over doing it. There were ten pictures in all, almost a full roll.

“These pictures really came out good. I thought they would show some defect that would give me away as a boy, but they don’t.”

“I’ve got some more film for my camera. Why don’t I take some more? You look even better in that dress.”

“Oh well, I’m really scared that someone will see these. The fewer pictures of me in a dress the better, I think.”

“I’ll be sure that no one sees them that shouldn’t. I’ve got a special hiding place. Since we have these, what’s a few more? I’ll keep them all in the same place. I think it’s neat to have these pictures. This is so much fun. We’ll want to remember it when we get older. Please. I’ll be careful to see that no one finds them by accident.”

“Well OK, but I’m trusting you to see that they stay hidden.”

It was dry day. She got him to go out in the yard and pose for pictures. They had a high fence and it made a good back drop for the pictures. He posed like a model. In front of the fence, leaning against a tree, sitting on the steps and in the swing on the porch. They moved inside here she had him looking in her closet, as if to choose a dress. He had him pose in front of the bathroom mirror with lipstick in his hand as if he were putting on his lipstick. Back in her room she had him sit on the bed. At noon, he hurriedly removed his make-up and changed his clothes. He took the picture of him standing by the window in her living room when he left. He hid it when he got home. There was a place in his closet that gave access to the attic space. He put it in a box and buried it in the insulation.

School was out on the 11th for Christmas break. Milton was looking forward to the time off. He found himself laying in bed wide awake at 8:00 in the morning. After about fifteen minutes, he got up and went to the kitchen for breakfast. While he was eating, the phone rang.

“Milton, it’s for you,” his mother called from the family room.

He went to the phone. “Hello?”

“Hi Milton,” Jennifer’s voice said.

“Oh hi Jennifer.”

“Whatcha doing?”

“Eatin’ breakfast,” he told her.

“I mean later.”

“Oh, I don’t know. Nothing really.”

“I got my film back. Why don’t you come over and look at them?”

“I don’t know. Your mother probably wouldn’t like me over there when she’s not there.”

“It’s up to you. I just thought you’d want to see the pictures. They turned out really good.

“Oh you know what? My cousin is getting married next month. I’m going to be a flower girl. I’m supposed to walk down the aisle and scatter rose pedals just before bride does. Mom brought my dress home last night. It’s gorgeous. You should see it.

“It’s lavender and strapless. It has an empire waist and the material is several layers of real silky cloth. The skirt goes down past the knees in the front and all the way to the floor in the back. In the front each layer is a little higher then the one behind it. There is a sheer thing that goes over my shoulders. I’ve got a new bra for it. It’s kind of a strapless thing mom calls a ‘buster.’ It’s like a strapless bra only the back goes way down. Almost down to my waist.

“Underneath, I have a lavender half slip and panties to match. Guess what, I’ve got pantyhose. They’re kind of lavender too. They are real silky. The shoes are three inch high heels. It’s so cool.”

Milton found himself morbidly interested in her description. Especially the lingerie. “It sounds really cool,” he told her.

“I think you’d really look good in it. Only, you couldn’t wear it all day. We can’t take a chance of getting anything on it. My mother wouldn’t like it if it needed cleaning before the wedding. But you could wear another dress after you try it on. You know, while you look at the pictures.”

“Oh, yeah, I understand,” he said. His mother had come into the kitchen and he couldn’t talk freely.

“Can you come over right away? That way we won’t have to rush with flower girl dress. Or anything.”

“Well, I don’t know.” Milton was beginning to shake. Just thinking about wearing such a beautiful dress made him feel all mushy and warm inside. “I haven’t even gotten dressed yet.” He turned so that his back was to his mother. “I’m not sure what mom has going today. She might need me around here,” he continued softly.

“Well, get here as soon as you can. I know that you’ll want to see the pictures.”

“We’ll see. I have to get dressed.”

“OK. I’ll be waiting for you. Bye.”

“Bye.”

“Who was that dear?” his mother asked.

“Oh, Jennifer a girl from school.”

“Oh yes, she called on the first of the month, didn’t she?”

“Ah yeah. She wanted to know if she rode her bike to school, would I lock it with mine.”

“Did you do that for her?”

“Yeah, her mother wanted someone to ride to school with her. I go within a block of there, so I just swing by and ride with her.”

“That’s nice of you dear.”

“Well, it makes things easier since I lock her bike with mine.”

“She must be someone special. I know how young love is.”

“Mom! She’s just a friend.”

“OK dear. What ever you say.”

Milton went up and got dressed. As he put on his boxers, he was reminded how different panties felt. Pulling on his shirt, he missed the slip that would have gone next to his skin. Putting on his pants, he felt their coarseness and longed the pantyhose Jennifer talked about.

“This is crazy!” he thought. “I’m a boy. Boys don’t think about wearing stuff like that.” He went down and got on his bike. He needed to do something. Anything. Riding around with nowhere to go he burned off energy.

He didn’t know where he would go. He just rode fast. As fast as he could go, where didn’t matter. The more demanding the better. He needed to keep his mind occupied. Turning corners just to be turning, he raced at breakneck speeds. After a time it began to sprinkle. At first he ignored it, but when he bike lost traction and almost slid out from under him on a turn, he decided that the roads were slick enough to make riding at that kind of speeds dangerous. If he couldn’t ride fast, he might as well go home. He turned in that general direction. About a block down the street, he realized he was about ride by Jennifer’s.

He was by the intersection and the rain was getting serious. Backtracking would get him wetter. As he approached the house, he looked at it. Jennifer was in the window. As soon as he came in sight, she ran to the door and stood on the porch.

“Hurry Milton,” she shouted, “you’re getting all wet.”

He turned in to her driveway. Parking his bike under the eves of the porch, he ran up on the steps.

“I knew you’d come,” she said opening the door for him. Once inside, she literally dragged him to her bedroom. There, laying on the bed, is the dress and all the under things. She grabbed the buster, panties, pantyhose and half slip. All the while she was rattling on about how much fun this was and how she would take lots of pictures of him. She was like that locomotive again, only this time the hill was steeper and the throttle was full open.

Before he could say anything, he was standing in the bathroom with the lingerie and shoes. His instructions were, “Put these on and then I’ll do your make-up.” Still unsure of why, he stripped and put on the panties. Followed by the pantyhose and buster. With the slip in place, he opened the door.

Jennifer rushed in and began his make-up. She went all out. When she got through, she fitted him with the wig. Back in the bedroom he found himself holding the dress up while she zipped it. She draped the sheer top piece over his shoulders and fastened the hidden catch around his neck.

Out in the hall, he was looking at his incredible reflection. He was every inch a girl. The feel of the dress as he walked out here nearly drove him out of his mind. He went to the end of the hall and watched himself walk back the effect of seeing himself and the feel of the dress was intoxicating. He was positively giddy when she led him into the living room and had him pose by the window.

She snapped pictures. Not one, not two, not three but five. She took five shots. Each one just a little different. Then, she showed him the pictures from the last episode. They were really neat. The pictures outside were the best. He looked most natural. After looking at the pictures, she suggested that he should change to another dress.

She led the way back to her bed room and helped him out of the dress. Removing the buster, she replaced it with his usual highly stuffed bra. She dropped a full slip over his head and he took off the half slip.

“Pick out a dress you’d like to wear while I put this back in it’s protective bag,” she told him. Milton looked in her closet and chose a yellow, almost summery dress and put it on. At Jennifer’s suggestion, he put on some yellow pumps. They spent the rest of the day watching afternoon soaps.

At 4:30 while Milton was changing back, he noticed a run in the pantyhose. “Oh Jennifer, I’m sorry, I didn’t realize it until just now, but I put a run in your pantyhose,” he said coming out of the bathroom.

“Oh no! My mom will kill me. I’m not supposed to be fooling around with this stuff.”

“What kind are they and where did you buy them? I’ll replace them.”

“We got them at Victoria’s Secret. In Washington Square.”

“How much did they cost?”

“I think they were $ 6.00.”

“OK, I’ll go tomorrow and buy some more. You’ll have the replacements tomorrow.”

* * *

Saturday morning, Milton was at the mall when it opened at 9:00. He was upset that it Victoria’s Secret didn’t open until 9:30. He was right there when the lady finally opened the doors. Reaching in his pocket, he handed the package to the lady and said, “My sister put a run in her pantyhose and needs a replacement right away. She sent me down here to get them while she does her make-up.” He thought it was a good lie. But he felt uncomfortable when the lady looked puzzled at the package for a moment and then gave him a smile and winked at him.

“OK They’re right over here,” she said, leading the way to the hosiery rack. She took just a second and compared packages. “That’ll be $ 5.95.” Milton reached in his pocket and took out two five dollar bills and handed it to her. She walked to the register and made change for him. “I hope you-your … ‘sister’ will be more careful in the future,” she told him as he put the change in his pocket.

His bus dropped him off near Jennifer’s house at 10:15. He rang the bell at 10:20. He didn’t even think. It was Jennifer’s mother that answered the door. He nearly panicked.

“Ah… is Jennifer here?” he asked nervously.

“Yes she is. Won’t you come in?” she invited, then turning she called. “Jennifer, there is a young man here to see you.”

“Oh, Milton,” said Jennifer arriving from the living room. “Mom, this is my friend Milton from school. Milton, this is my mother.”

“Oh yes, you’re the young man who rides with Jennifer on the way to school.”

“Ah, yes ma’am.”

“It’s nippy out there. Would you like hot chocolate?”

“Oh yes ma’am, thank you.”

“Jennifer, why don’t you take your guest’s coat, while I make some hot chocolate.” Her mother smiled walking to the kitchen. Milton waited until she was out of sight. Unzipping his jacket, he handed her the new nylons. She looked over her shoulder and took the package. She slid it on the shelf just under a small box. Then she hung his coat on a hanger.

As they sat on the couch in the living room, they heard the microwave timer sound. Her mother brought them hot chocolate and some sugar cookies. After serving them, she sat in a chair.

“You live near here, don’t you, Milton?”

“Yes ma’am, I live about six blocks that way,” he said indicting the direction to his house.

“Milton won the prize for best costume at the school Halloween party,” Jennifer informed her mother.

“Oh really? What kind of costume did you wear?”

“I, ah … I went as … ah … a princess,” he said nervously.

“A princess? Really?”

“Oh yes mom, he really looked good too. Everybody thought he was a girl in a princess costume.”

“Well, I couldn’t have done it without my sister. She lent me her fancy dress and did my face in make-up and styled my hair for me. She had the tie… tee… ah… the crown thing and some other jewelry.”

“He was very convincing.”

“I wish I could have seen that.”

“Maybe we could get Milton to reenact his performance while he’s here.”

“How could he do that?” her mother asked. Milton nearly choked on his chocolate when Jennifer made her suggestion.

Jennifer eyed Milton with glint in her eye. “I think that my clothes would fit Milton. I have that party dress that I got last spring. And then there’s that blonde wig.” Her mother looked at Milton.

“I believe you’re right Milton could wear your clothes.”

“How about it Milton, would you show my mom what you can look like as a girl?”

“Well, I, ah…” he started, blood racing in his veins.

“Oh please do Milton. If you were good enough to win the best costume, I would really like to see it,” her mother said smiling. She seemed to be genuinely interested. There was no hint of sarcasm in either her voice or expression.

Jennifer stood and took his hand. “Come on Milton,” she said pulling on his hand. “I’ll help you.”

Milton stood knowing he should protest or make and excuse to leave, but he just allowed himself to be led to Jennifer’s bedroom. As Jennifer began to get out underwear for him, he found his voice.

“Ah, if I’m going to do this, I don’t think it’s such a good idea if I wear panties. I mean, suppose your mother notices?”

“Don’t be silly. Why would my mother want to look up your skirt?”

“Well,” he said, his ears burning, “you did.”

“Well, yes, but I was trying. I wanted to see what you were wearing. My mother wouldn’t do that. Anyway, these are plain white. If she notices, she’ll think that you wore them over here. She can’t tell mine from someone else’s, unless you wear something fancy. Now take off your shirt.”

Soon Milton was standing there in panties, bra and slip. Jennifer fished a really nice dress out of the back of her closet. It was mint green with cap sleeves and a full skirt. She got out a petticoat that would make the skirt stand out a little like the dress he wore on Halloween. She helped him into first the petticoats and then the dress. She zipped the dress and took him into the bathroom. She did make up for him and fitted him with the wig. Lastly, she put a pair of two inch heels on his feet and led him back to the living room. He was a little nauseated and wanted to go back, but Jennifer had a firm hold on his hand and was insistently propelling him along.

Her mother turned as they came into the room. “Oh Milton, I can see why you won the best costume. You make a very convincing girl.”

“His cousin called him ‘Millie’ at their family party.”

“Millie, how perfect. You look like a Millie. Turn around and let me see you.” Milton did slow turn, falling into his feminine walk as if it were natural. “Oh that dress looks really nice on you. Walk a little, so I can see how the judges would have seen you.” Milton walked to the kitchen door and turned back. Every move from the placement of his feet, to the swing of his arms screamed girl. “Oh how perfect, I can see how you won.”

“Mom, would it be OK if we got some pictures of Millie? I guess his family didn’t take any and the ones that were taken at school, will stay there.”

“Why sure dear, do you have film for your camera?”

“Yes, I do.”

“Well then why don’t you get it. Oh, I know, put on a nice dress and I’ll take some picture of the two of you.”

Jennifer left Milton standing there feeling sheepish. It was one thing to wear a dress to practice for Halloween and quite another to be in some else’s house during Christmas vacation dressed like this.

“I can’t get over how good you look. Even your mannerisms wouldn’t give you away. How did you get so good at acting like a girl?”

“Well, when my mother and sister came up with the idea, they realized that I would give the whole thing away if I didn’t make my actions more girl like. They made me practice for two weekends before the school party.”

“Two weekends. Did you wear your costume while you practiced?”

“Well, not exactly. It was a really special dress my sister has. It’s even more fancy then this one, so they had me wear different ones.”

“What did you do about hair?”

“Oh, my sister is a genius with hair and make-up. By the time Halloween came around she had done it enough times, that she could get me ready in about fifteen minutes.”

“So let’s see, the school party was on Friday, and Halloween was on Saturday, so that means with your two weekends before, you’ve been dressed up like a girl for six days in all then.”

“Ah, yes ma’am,” he allowed. He didn’t realize that he had given that much information.

“Well, all that time certainly paid off, you could fool anyone. Why I bet, that if we took you to a shopping mall, no one would take any notice of you unless it was a young man wishing he knew you.” Milton blushed, remembering Bob’s reaction at school.

Just then, Jennifer came back, she was wearing a yellow sheath and heels. She had touched up her make-up. “Here’s the camera Mom.”

“OK you girls stand there by the window and let me get a picture.”

She took two. One with them standing hands clasp in front and one with them with their arms around each other’s shoulders.

“Get one of us out on the porch.”

“No, I think candid shots would be better. Jennifer, why don’t you two put on something more causal and just hang out doing what ever you would do with any other girl friend. That way Millie will have pictures that are more natural.”

“OK, come on Millie,” said Jennifer taking him by the hand and striding forcefully toward the bedroom. She helped him out of the dress and petticoats. She then picked out another one for him and helped him into it. As he was smoothing the skirts, she turned and asked him to unzip her. He did and she immediately let the dress fall off her shoulders and stepped out of it. Milton was amazed at how casual Jennifer was around him. Never before had he seen a girl, not even his sister, take off her dress in front of him. She hung the dresses up and chose a school dress for herself.

Back in the living room her mother suggested that since it was nearly noon, that they fix lunch. Milton fell into that helpful mode again. As they made up egg salad sandwiches and soup for lunch, Jennifer’s mother snapped pictures of them. Again, the camera snapped as they ate. More pictures were taken as they did dishes.

After lunch, they watched some television. And then, Jennifer put some music on the stereo and they danced. The weather cleared and it actually got warm out. (60‚°F) The girls went out on the back porch and sat on the swing while they discussed school. All the while, the camera snapped.

At 4:00 Jennifer’s mom came in and said. “Girls, I’m about to start dinner. Millie, would you like to stay for dinner?”

“Ah, OK, sure.”

“Well, why don’t you call your mother and see if it’s OK.”

Milton went to the phone. “Hello, mom?

“I’m at ah, Jennifer’s, her mother wants to know if it’s OK for me to stay to dinner.

“OK, I will. Thanks I’ll be home at nine.”

Millie stayed for dinner. Of course, Jennifer’s mom got some more pictures of Millie and Jennifer. As Milton operating in his helpful mode led the way in the kitchen. After, dinner, they watched television until about 8:00. As he got up to change clothes, Jennifer turned to her mother.

“Mom, can Millie come over again tomorrow?”

“I think that would be fine. That will give you some company while I go shopping. In fact Millie if you’re here by 8:00, you can have breakfast with us,” she told him.

* * *

“Hi mom,” Milton said as he stuck his head in the family room. “I’m home, right on time.”

“Have a nice time dear?”

“Oh yeah, as a matter of fact, they want me to spend the day tomorrow.”

“Over at the same girls house two days in a row? I think Milton has a girlfriend,” Anne teased.

“Anne, if you want to know the truth, I want to go over there because you make it hard to stay around here.”

“Now you two, simmer down. You’re not around one another thirty seconds and already getting on each other’s nerves. Why can’t you cooperate and get along like you did before Halloween. I swear, Milton, I sometimes think I should put back in a dress. At least then, you two didn’t bug each other.”

“Is it OK if I go over there for the day tomorrow or not.”

“Well, if you and your sister can’t get along, you might as well. I think, however, I should talk to Jennifer’s mother. Do you have her telephone number?”

“Ah, yeah, she gave it to me, in case I needed to stay home from school some time.” Milton got the number from his room.

“What’s her last name?

“Michaels.”

“Hello, Mrs. Michaels? This is Mrs. Johnson, Milton’s mother.

“Well I was just checking to be sure that Milton is invited to come over tomorrow.

“Well good, I always like to check on these things, especially when it’s a young lady’s house he’s going too.

“Yes, I think we should. Maybe at the next school function.

“OK, well, thanks so much. Bye.

“She sure seems impressed with you. She said that you were very well mannered and very helpful. She said that you were welcome anytime.”

* * *

Jennifer met Milton at the door at 7:45. He was dressed and in the kitchen in time to help set the table. By 8:15 Jennifer’s mother, Jennifer and Millie were enjoying French toast.

“You know Millie, I think that blue is your color. I don’t think that dress ever looked so good on Jennifer.”

“Thank you, it’s a very nice dress. Jennifer is lucky. She has so many nice clothes.”

After breakfast, helpful Milton washed while Jennifer dried. About 9:30 Mrs. Michaels left for the mall. Millie and Jennifer were left on their own for lunch. Milton suffered through another session of pictures. In the past three days, Milton had been the subject of enough pictures to fill four rolls of film.

Mrs. Michaels returned about 3:30. “Did you two girls have fun while I was gone?”

“Un-huh. I took more picture of Millie,” Jennifer told her.

“Well, many more, and we’ll have to get an album and dedicate to Millie,” her mother laughed.

Milton stayed for dinner that evening too. As he was about to leave, Mrs. Michaels stopped him. “You know dear, you’re one of the nicest girls among all of Jennifer’s friends. You should feel free to come over any day during the Christmas break. Jennifer gets mighty bored while I’m at work.”

“Mom, do you mean Millie or Milton?”

“Why, I hardly know Milton. Just those few minutes on Saturday. I can’t say what kind of person Milton is, but Millie is a very delightful young lady.”

* * *

Milton went home excited about the possibility of coming over to Jennifer’s during Christmas break. Sunday night, he had misgivings about it. Why is Mrs. Michaels so quick to accept him as Millie? Why am I so ready to dress-up and be Millie? Is there something wrong with me? Are there any other boys doing this kind of thing? He didn’t sleep that well.

On Monday, he called Jennifer and made an excuse for not coming over. He had too many unanswered questions. He spent most of his day in his room. He got out the pictures that Millie had let him have and looked at them. He was at a loss to explain how he felt about them. Looking at them, he couldn’t help but smile. Wearing a dress made him happy. Why?

Then there was the dichotomy of how he felt and behaved. As Milton, he was a macho jock. He liked football, basketball, baseball and rough housing in general. Ask him to so much as carry some else’s glass to the kitchen and he was offended. After all housework was woman’s work and he was no sissy. However, as Millie, he would pitch right in on doing the dishes, why during his practice session, he had done laundry, vacuumed and dusted. He had been into woman’s work right up to his elbows. What’s more, it felt natural.

He remembered the tug-of-war in his mind when the idea was suggested. Then he remembered the thrill of trying on the dresses, after his mother left him alone. That combined with the excitement of wearing panties, the feel of a dress rustling around a slip as it slides across his legs. He needed to talk to someone. But who? His mother thinks he dressed up for three short weekends and she didn’t even know about the panties and pantyhose. Anne was out. The only time he ever had a decent relationship with her was while she was training him to be a girl. Dad would come unglued if he admitted to him that he liked his Halloween costume let alone that he had continued to dress-up after.

He was stuck. The only people who he could be sure of sympathy from would be Jennifer and her mother. Could he admit, even to them, that he really did like wearing girls clothes? OH MY GOD! I really do like wearing girls clothes. Oh man! I like it. No, really? Oh God yes, I do.

It was a devastating realization. He really wanted to go over to Jennifer’s. Truth was, even if Jennifer hadn’t conned her mother into permission, he would have been there anyway, hadn’t he already been party to sneaking the experience? He had another sleepless night.

Tuesday morning found Milton wide awake at sunrise after dozing fitfully. He lay in bed watching the minute hand crawl around the face of his clock. He heard his dad leave for work at 7:30. A few minutes later, he got out of bed and dressed. After a quick stop for breakfast, he rode his bike straight to Jennifer’s.

“Hi Milton, I’m glad you came. I missed you yesterday,” she said. “I thought you’d be coming today, so I have some things laid out for you on my bed. You can pick any dress or skirt and blouse you want. Milt went down the hall to her bedroom. He found a very pretty selection of lingerie on the bed and that blonde wig on her dresser.

The panties were a cream colored satin like material. They had some fancy flowers sewn on the front panel. The bra was just as fancy with lots of lace and the slip likewise. They felt delicious as he let the material slide over his body. He put on the wig and went across the hall, to try his make-up. He did a pretty fair job. He kind of felt naughty walking around in a slip. The dress he picked out was tight at the waist with a flaring skirt that gave the illusion of hips.

He spent the day doing girl things. Watching soaps on TV, listening to popular music on the radio and just generally hanging out. Mrs. Michaels came home at 5:00.

“Oh hi Millie, I’m glad you could make it today,” she told him. “Jennifer was really disappointed when you couldn’t make it yesterday.”

He was invited to dinner. He of course helped prepare it and clean up after. That evening, he got up his courage and spoke to Jennifer about what had kept him up the last two night.

“Jennifer, can I ask you a personal question?”

“Well sure, you’re just about my best friend.”

“It, … it’s kind of unusual for a boy to pretend to be a girl, isn’t it?”

“Yeah, I guess so… is that your ‘personal’ question?”

“No, I was wondering, why it is you and your mother are so willing, not only to let me, but you both actually encourage me.”

“Oh, the question isn’t to personal, but the answer could be.”

“What answer?” Mrs. Michaels asked coming in from the kitchen.

“Ah, Millie was wondering, why we like it when he’s ‘Millie’.”

“It’s a fair question. I suppose it deserves a fair answer. Wait here.” She left the room and returned shortly carrying a photo album. “In here, is a member of our family you haven’t met. It’s a shame too. You, … well look first, I’ll tell you after.” She opened the album. “This is Harriet.”

The first page was a little girl, about 7 or 8 wearing a white taffeta dress with a large, floppy brimmed hat. The hat had a long yellow ribbon around it and streaming out behind it. The next page had a not much older Jennifer and that same girl playing on a backyard swing set. As the pages went by both Jennifer and Harriet got older. The last page had a photo that must have been really recent. Jennifer was wearing the swim suit she got last summer. Milton had seen her at the park swimming pool and heard the other girls asking her about it.

“She’s a good looking girl, who is she?”

“Millie the reason I said it was a shame the two of you haven’t met, is because you and Harriet have a lot in common.”

“We do?”

“Yes Harriet is Jennifer’s little brother.”

“… … … Little Brother?”

“Yes, you see when Harry was 7, he got into Jennifer clothes. When I found him, he had the most God awful combination of clothes on. A blue green blouse and purple skirt. I told that if he wanted to wear her clothes, that he’d have to learn to color coordinate them. I suggested that he stick to dresses until he learned what colors went together.

“Then, I helped pick out a dress and introduced Harriet to Jennifer. They hit it off. Unfortunately, his father didn’t enjoy his son becoming his daughter.”

“Yeah, my dad isn’t too keen on it himself. He hid out while I was learning to be a girl.”

“Well, my husband finally gave me an ultimatum. Either I see to it that Harriet never visited again or he was divorcing me. When I first discovered Harriet, I did some research and found out, that once a boy begins to like wearing girls clothes, he never stops for good. The worst thing that can happen is for his family to berate him about it. That ends up causing deep seated guilt feelings that haunt him the rest of his life. I wanted Harry, … Harriet to grow up well adjusted. Try as I would, couldn’t convince my husband of that it was necessary to allow it for his emotional health.

“He carried out his threat. At the divorce, he showed the judge some pictures I had taken of Harriet and asked for custody of Harry. He argued that I was twisting him and asked the judge to protect Harry from me.” Here, she began to cry. Jennifer took her hand. “I’m sorry, it was only three years ago. It still hurts. Fortunately, my lawyer was skillful. While my husband did win full custody, I get Harry, that is Harriet for one week a year. At his fathers house, he sneaks his step-mothers clothes. He lives in fear that they will catch him. But while he is with us, he has free reign to be Harriet.

“So you see Millie, from when I first heard that you had been a convincing girl for Halloween, my heart went out to you. When you told me that you spent two weekends, prior to Halloween weekend, dressed as a girl, complete with make-up. I knew you needed acceptance and love as Millie. I want you to come over when ever you like and to be Millie, as much as you like. I know I’m running the risk of going against your parents. But I’m willing to risk it. All I ask from you is that you do everything you can to not let them know I’m involved in this. If you’re caught, Jennifer has agreed to take the fall for it and I in turn will see to it that her punishment never happens.”

With that, Millie began to be a regular at the Michaels household. As a matter of fact, he was there everyday during Christmas break except Christmas day. After Christmas, Millie got a dream invitation.

“Mom, what are we doing for New Year Eve?” Jennifer asked.

“Nothing really. Why do you ask?”

“I was wondering if I could have Millie over to celebrate.”

“Well, that’s fine with me. But after midnight is a little late to expect her to go home. I’ll have to call the Johnsons and ask if it would be all right for Millie to stay the night.”

“Be sure to call him Milton when you talk to his mother.”

“I will, you know I always call your brother ‘Harry’ when I talk to your father.”

The arrangements were made and Millie came over early New Years Eve. They watched rented movies and ate junk food. At 10:00 Jennifer and Millie put on nightgowns in preparation for retiring after the New Year arrived. The nightgown provided for Millie was a powder blue layered affair. It had and opaque layer of nylon tricot next to him and three layers of sheer taffeta over that. It was so feminine. At midnight, Jennifer and Millie took pans out on the back porch and banged them together. By 12:30, Millie was in the spare bedroom (Harriet’s room) snugly in bed, reveling in the feel of the nightgown.

After that, Millie showed up at least one day of every weekend and most weekends it was everyday. He found out that the spare bedroom closet was full of Harriet’s dresses. His usual routine was to let himself in, calling out to Jennifer and her mother to tell them he was there, go straight to Harriet’s room and change into Millie. Then he’d join them in the kitchen for breakfast.

Jennifer liked having Millie around so much, Mrs. Michaels occasionally trumped up excuses for him to spend the weekend. Things like the need to leave early to go to the mountains for a snow day or a drive down the valley to some sort of festival. What surprised Millie, was they actually did what ever idea, Mrs. Michaels came up with. The first time, he thought it was just a story that she told his mother. But when he spent the night, she woke him at 6:30.

“Millie, rise and shine. We’ve got a big day today,” Mrs. Michaels said, shaking him gently. “I’ve laid out some warm clothes for you on the foot of the bed.

“Oh my Gosh. We’re really going to the mountains,” he thought, looking around. On the foot of the bed were his warm clothes. She had put a pair of gray plaid wool stirrup pants and a very fuzzy gray turtle neck sweater in one pile and a peach colored satin camisole and matching pettipants (like a half slip only legs like pants) in another. On the floor were a pair of fur lined boots with a one inch narrow heel. The fur turned over at the top to form a little feminine cuff. Milton thought he would never feel feminine in pants. But this outfit put the lie to that thought.

He was scared to death as they piled in the car and started down the road. After all, he had only been as far as Jennifer’s back yard as Millie and then, he had been wearing a wig. Today, they just brushed out his hair and put barrettes in it. They told him that the wig might fall off. Halloween didn’t count. On Halloween, everyone is expected to wear strange clothes. Even if people figured out he was a boy, they wouldn’t care. But now, someone was sure to object.

“Oh Millie, don’t worry. Remember, people, and even people who knew you, didn’t know you weren’t a girl on Halloween. No one will know now,” Jennifer told him when he expressed misgivings about going out in public. “Remember how the janitor at school thought you were a girl and told you to use the girl’s room?”

“How did you know that?”

I was behind you in the hall when it happened. I was on my way to the bathroom myself. I was going to wait until you came out, but I couldn’t. So I just waited until I was sure that you were in a stall and went in anyway.”

“That was you? I thought it was someone else. I thought that the girl in there just thought I was another girl.”

“They would have. The janitor did. The only mistake you made is that a girl would have spent some time in front of the mirror before going back. If you have to go today, be sure to take me with you. Then you can just follow my lead.”

They had a great time playing in the snow and sure enough, he did have to go. When he told Jennifer, she calmly walked him right into the ladies room. She took one stall and he the other. He took off his faux fur lined coat and hung it on the hook behind the door. As he began to pull down his pants, he remembered Jennifer’s whispered caution as they came in, “Remember to sit.”

He sat down and relieved himself. He heard the toilet paper being pulled out in the stall next to him. He wasn’t sure why, but thought he should do it too. Pulling up panties, pettipants and stirrup pants, he flushed the toilet and put his coat on. Jennifer was at the counter washing her hands. He joined her. After she finished, she leaned in slightly and looked appraisingly at her face and then produced a brush and stroked her hair a little.

“Wanna borrow my brush,” she asked handing it to him. They had decided on his own hair today, since he would be wearing a hooded coat most of the day. He brushed it a little, although, he didn’t know why. Jennifer hadn’t really made any appreciable difference in her hair. And neither did he.

The whole episode in the restroom had stretched his acting abilities to the limit. He was so uptight, he almost couldn’t relax enough to do what he had come in there for. For all of that, not one woman or girl in the restroom acted as if there was anything unusual at all. After that, Milton learned to brush his own hair into a girls style. It felt more natural then the wig.

During Spring Break, Milton’s family went to the mountain cabin his uncle owned, so that Milton and his dad could get in a little high lake fishing. Milton normally enjoyed fishing with his dad. The fishing was fun, but he found himself day dreaming about what he would be doing if they had stayed home. Every time he thought about it, he imagined Millie and Jennifer doing something really fun together. One day, after lunch, he and Anne went for a walk and found a patch of late snow. They had fun throwing snow balls at each other. It made Milton remember the snow day he had had with Jennifer and without thinking about it he fell into his Millie character.

The last time he had done this with Anne, he had been almost blood thirsty about it. This time he was light hearted, the way he had been with Jennifer. Instead of packing the snow into tight, hard balls, he made them light so they wouldn’t hurt when they hit. When they were through, Milton threw his arms around Anne and gave her a big hug. Anne was taken aback by his show of affection. The rest of the day, Anne looked at him strangely when ever she thought he wouldn’t notice. She wasn’t sure why he had hugged her affectionately. He hadn’t done that since he was six. Except for last Halloween, when he brought home the best costume award from school.

Mrs. Michaels announced to Jennifer on a Saturday in June. “I’ve made the reservations for our cabin at the beach for vacation.”

“Mom, can I invite Millie?”

“I thought you would, that’s why I made sure that it still had a hide-a-bed when I called. I’ll sleep in the hide-a-bed any you and Millie can each take a bedroom.”

“Thanks Mom.”

They assured him that the cabin is on a secluded beach and it would be safe for him to swim as a girl. Milton stayed the night with Jennifer Friday after school and they left Saturday morning. When the girls took the suitcases to the car, the big one Milton had brought from home stayed right were he put it when he came in with it. They only packed his ditty bag containing soap, shampoo tooth paste and tooth brush. They arrived at the cabin at 10:00.

They were getting out of the car when Jennifer looked up and said. “Mom, I don’t remember that over there before.” Indicating a new looking building about 100 yards away.

“It wasn’t there last year.” Just then a car pulled up.

“Mrs. Michaels, I’m glad you’re here right when you said you’d be,” the driver said, getting out of the car.

“Oh Mr. Swenson. It’s you. You’ve got a new car.”

“Yeah the old one gave up the ghost during the winter. Here are the keys. I wonder if I could impose on you for a little favor. My daughter just left for the hospital. I was supposed to be here to give the key to the new cabin to the Nelson’s at 11:00. Could you give it to them for me? I’d like to be there when my grandchild is born.”

“Oh sure Mr. Swenson. You go ahead. Your daughter will be glad to you have there.”

“Thank you. The new cabin is real nice. We had so much demand for this one we built that one last fall. Maybe next time you can stay in it, you’d like it. Take a look at it,” he said getting back into his car.

“I guess I won’t be able to swim this week after all,” Milton said

“I wouldn’t be too sure. Wait until you see the swimsuit I packed for you,” Mrs. Michaels said.

It was yellow one piece. The top part had a halter style strap that fastened behind his neck and there were sewn in pads, that were placed just right to look like a twelve year old bust line. The bottom part had a white pleated skirt that covered all but the very back of his fanny. In front of the mirror, he had to admit that there was nothing to suggest anything but “girl.”

The Nelson’s were late. The girls sat impatiently on the porch railing swinging their feet.

“Mom, they’re here. I think,” Jennifer called as the car ambled down from the highway. Mrs. Michaels stepped out and went to meet the car.

“Hi,” she said as the car pulled to a stop. “You must be the Nelson’s. Mr. Swenson asked me to give you the key. He had to go to the hospital. His daughter is having her first baby.”

“Yes, thank you. I’m Mark Nelson; this is my wife Janice. The two wiggle worms in the back seat are Karin and Martha, our daughters.”

“My name is Joan Michaels the girl sitting on the rail is my daughter, Jennifer and the other girl is her friend Millie.” Mr. Nelson nodded while Mrs. Nelson leaned down to see better and nodded. Karin and Michelle looked out the back window, smiling. The Nelson’s took the key and drove on to the other cabin.

Mrs. Michaels accompanied the girls to the beach. They were soon joined by Karin and Martha. They found out that Karin was 11 (almost 12) and Martha was 8.

The Nelson’s were really nice. It turned out that they had tried to get their usual place but the demand had been so high that it was already booked up solid by the time they asked for reservations.

“We were really fortunate to get this place. We just happened to see an add for it when we were at the beach during Spring Break.” Mrs. Nelson told Mrs. Michaels. Milton was a little nervous the first weekend, but, when none of the Nelson’s gave any indication that he was anything but a twelve year old girl named Millie, he relaxed.

On Friday, Mrs. Michaels asked the Nelson’s if they would keep an eye on Jennifer and Millie while she drove into town. “It’s a surprise for the girls. Jennifer’s sister Harriet is coming on the bus. The girls were split during the divorce. This year, Jennifer went to be with her father for the week Spring Break and I get Harriet this coming week. My ex agreed to let her come on the bus at the last minute.”

She packed a small bag and left at 10:00. In town, at the bus station, she met Harry. In the back seat of the car, Harry changed his shirt for a blouse and pulled a skirt up over his trousers and took them off. He changed into a pair of panties and when no other cars were on the road, he crawled into the front seat. Smoothing out his skirt, he fastened his seat belt and slipped into the flats. He pulled down the vanity mirror and brushed out his hair. He skillfully ratted and teased it into a nice girls style. They stopped at a rest stop long enough to put polish on his nails. He also took the time to put on some brown mascara.

Back at the cabin, Mrs. Michaels was glad to see that everyone was at the beach. Inside, Harriet changed into a swimsuit. As they walked across the sand, Jennifer looked up. “Harriet!” she screamed and ran toward him leaving the other girls standing in the surf. “Mom, I thought you said that Harriet wouldn’t be able to make it this year,” she said hugging him tightly.

“Your father said he couldn’t get away to bring him and I couldn’t go get the extra time off to go get him. He also said an absolute ‘NO’ when I suggested that Harriet come alone on the bus. But last Friday he called me at work and said he would be putting Harry on the bus this morning. We had already made plans for Millie, so I couldn’t disappoint her. I decided to make it a surprise.”

“Come on Harriet. I want you to meet Millie. I wrote you about him.”

Introductions went around. Millie and Harriet shared the bedroom with a double bed. They hit it off famously. The week was spent comparing notes. Everything from what clothes they liked best, to where they had been as a girl. Milton found out that Harry was an old hand at passing for a girl. His mother had begun taking him out when he was nine. Milton listened in rapt awe as Harriet described his adventures out buying dresses; how he had been to restaurants and movies.

He showed Milton tricks that made it easier to get his hair into a feminine style. The five girls all had a good time on the beach. The Nelson’s took the whole bunch into the local theater and out to drive-in restaurant for lunch one day. All too soon, the week was over. They had to get Harriet back in time to catch a bus so they turned down the invitation from the Nelson’s to join them at the aquarium in the next town.

Back at Jennifer’s house, Millie and Harriet crossed back over the gender line and Milton went home. He was tired but happy. He has met another person who had come to grips with what he thought was his own personal peculiarity. When Milton came in he took his suitcase to his bedroom and dumped it into his hamper. Downstairs, he found his mother in the family room watching television.

“What are you watching?” he asked.

“I came across the tape we made while you were practicing for your Halloween costume,” she told him. Walking into the room he turned to the television. It was on the part where he was learning to walk and what to do with his hands. He smiled as he saw how awkward he had been. He knew now, he could pass in any situation. He was surprised to find out his mother had taped him in the kitchen helping Anne do the dishes and that the camera had been on while he vacuumed and dusted. His mother stopped the tape when they got to the part where they just taped the evening of that last Sunday.

“You know,” His mother said, “there’s a part of me that wishes Millie could come back to visit now and again. I kind of miss her.” Milton is touched by her sentiment.

“Mom, can I share a secret?”

“Sure dear. What would you like to tell me?”

“Well, it’s not about me. It’s about the Michaels. Can you keep it between you and me? I don’t even want the Michaels to know I told you. It’s nothing bad. It’s just I think they might be embarrassed if you knew. I kind of found out by accident.”

“Well, if it’s nothing bad, I’m not sure why you want to tell me. But as long as no one is hurt, I can keep it a secret.”

“It turns out that Jennifer has a brother. His name is Harry. He was there the second week at the beach. Well, Jennifer told him about my Halloween costume. He assumed that I liked that sort of thing.”

“Well, if I were to go by what I saw on the video tape, I’d say he was right,” his mother interrupted.

Milton went on without acknowledging the remark. “He told me that he liked it too and that his mother let him do it when ever he wanted. Jennifer confirmed it and showed me some pictures of him all dressed up. Some of them were from a long time ago.

“I guess that’s the reason the Michaels got divorced. Mr. and Mrs. Michaels couldn’t agree on it. She thinks it’s OK for him to dress up like a girl and his dad doesn’t. I guess she still lets him dress up when he comes to visit. Do you think Mr. Michaels is wrong? If he likes it and it doesn’t hurt anyone, should Harry be allowed to dress up in girls clothes?”

“Well, if no one is being hurt, I don’t suppose that it’s ‘wrong’ in the sense of what is right for Harry. But it is sure to cause friction between his parents considering how Mr. Michaels feels.”

“It’s terrible that Mr. and Mrs. Michaels had to get a divorce over it.”

“You’re right on that one. It just goes to show what level of commitment he had to his marriage. I’m glad to say I know that your father would never be that shallow,” she bragged a little.

“Really? How do you know?”

“When we were engaged, we knew a couple with teenage boys. One of the boys went to college when he was just 18. They found out that he was gay while he was there. His father wanted to disown him over it. His mother wanted to show her support of his lifestyle decision.

“Your father, while not particularly approving of homosexuality sided with the mother. He stated outright, that you must accept your children as they are. And when a child faces a disturbing time in his life like that, the boy needed unified support to adjust not to feel the guilt of causing his parents divorce. He then promised me that he would stand by me and our children if we ever had to face anything like it. Your father is a man of his word.”

“But dad has said that homosexuality is unnatural.”

“That’s true. He thinks it is and so do I. But that doesn’t alter how we feel about our children and the sanctity of the family. That’s why I agreed to marry your father. He told me that his commitment would be to the family come what may. He promised me that our children would know his love, no matter what life style choices they made even if he thought they were wrong. I believed him then and I still do.”

“I don’t think Harry is gay, he told me about his girlfriends. I don’t think anyone with that kind of relationship with at girl is gay.”

“I don’t think he is either. After all, I think you really enjoyed Halloween and you’re not gay.”

“Oh, I didn’t enjoy it that much.”

“Are you sure? You certainly looked like you enjoyed it. I asked you straight out if anything you had to do or were asked to do by me or Anne made you uncomfortable. You told me no. Not even what Anne asked you to do.”

“What Anne asked me to do?”

“Yes. You know the underwear and all.”

Milton blushed. “I didn’t know you knew about that. She promised no one would know. I… I hope you don’t think I’m gay. I’m not. I like girls you know.”

“I just told you I didn’t think you were gay.”

“You do know that Anne was the one who thought I should wear the panties. The first time she suggested it I was going to refuse, but she dared me. I couldn’t let her think I was chicken so I did it. I… I really think it helped me to stay in character. You can see the difference in the tape. The first weekend, I am really boyish, but the next weekend when she dared me to wear the panties, I became more feminine without even really trying.”

“Well, you certainly did better the second weekend. By Halloween, you could have fooled anyone. You even fooled most of your relatives, that is until Shirley went around and introduced you to everyone. Even your father had to admit that you looked good as a girl when we watched to tape of the party.”

“You taped the party?”

“Yes. Wanna see it?”

“OK.”

She went to the VCR and replaced the tape. As it played he was amazed how much footage was of him. Almost all of Shirley’s introductions were on the tape. He couldn’t imagine his father would have taped that much of him in costume. Then he saw his father on tape and realized that it was his mother doing the taping. He smiled as he relived that night. Eight hours of party was compressed into two hours of tape, but it showed every significant happening that he had been involved in.

When the tape was over Milton asked, “Can I share another secret?”

“I think I can keep another one.”

“I sometimes wish that ‘Millie’ could come visit too. Looking at the video, I just now decided that I can’t deny it anymore. I fit in with the girls when I was dressed like that. What’s more, I did enjoy it. It felt right. Can you understand that?” he asked fearfully.

“When your father watched the tape, he noticed that too. You know what he said?”

“No.”

“He said, ‘Maybe we should move Anne’s old clothes into your closet like Anne said.’ When I asked if he was serious, he said, ‘Seeing how much you enjoyed yourself on Halloween, he wouldn’t be surprised if you were to make a habit of it.’ I don’t think he was kidding. He sounded serious.”

“He didn’t really say that did he?”

“I sure did, his father said from the doorway.” He walked across the room and picked up the remote for the VCR. He ran the tape back to where it showed Milton sitting around with his girl cousins. He was laughing and joking with them in a most natural manner. The look on his face was one of inner peace and happiness. “Look at that and tell me that you weren’t having the best time of you life. Can you really, honestly tell me that you wouldn’t like to do it again? I wouldn’t be surprised if you already have. Son, while I won’t try to tell you I understand why you enjoyed it so much, but I can tell you that I love you. No matter what kind of underwear or outer wear you choose to wear. What I want for you is that you should grow up to be happy with the person you become. I think success should be measured by how you feel about yourself, not what you do.”

“Thanks dad, I needed to hear that.”

“Now don’t get me wrong. I’m not asking you to be my ‘part-time’ daughter, but if that’s what you are, it won’t change how I feel about you. I only ask that it be ‘part-time” I like having a son to go fishing with. OK?”

“Don’t worry dad, I’ll always be your son. I like to go fishing too you know.” Milton wasn’t ready to come out and admit that he was or would be wearing girls clothes. But it was nice to know that he could.

Milton decided to go see Mike. After two weeks of 100% girl, he needed to reaffirm his masculine side. Like most boys, he wore the same jeans for several days only changing his underwear and tee shirt. It was Wednesday before he needed to get into his closet again. He was surprised to find that his usually roomy closet was half taken up with Anne’s old dresses and that on the floor were several pair of girls shoes. He turned around and saw Anne standing in his door grinning like a Cheshire cat.

“I can tell by the look on your face that you haven’t opened your closet since Monday. I’ll bet you haven’t looked in your top drawer either, have you?”

“No.”

Anne walked in an opened his dresser drawer. In there, he saw there were panties and the push-up bra that he had worn for Halloween. “You haven’t changed your pajamas since then either.” She opened the drawer with his pajamas. There, next to his PJ’s were three nightgowns.

“Mom told me about your conversation that you guys had when you watched the video from Halloween. So I thought you might as well have these things. I’m not surprised. I saw the look on your face when I got you to wear panties that first time.” With that, she smiled and walked out of the room.

Thursday morning, he met Anne as he was coming out of the bathroom. “Where is Millie,” she asked.

“Still in the closet,” he answered, oblivious of the pun.

He spent Thursday at home. Mostly he was in his room staring into his open closet door. He only came out for meals or to use the bathroom. Friday evening. His mother was watching television alone. Milton came in and sat down.

“Mom, did you know that Anne moved her old dresses into my closet.”

“No, did she?” she asked not even looking away from the TV.

“She also put some panties and a bra in my top drawer. Not only that, she put four nightgowns in with my pajamas.”

“That was nice of her to share like that. I hadn’t thought of what you might like to wear to bed,” she said smiling pleasantly.

Saturday morning, Milton got up and put his pajamas in his hamper instead of under his pillow. He stripped his bed to so that when mom came up to get his laundry, his sheets would be in there. Then he went to pick out a new pair of pajamas for the next week. His eyes fell on the nightgowns. He picked up one it was really nice. It was a blue waltz length gown. The top was like a loose bra and the bottom was a full skirt. He put it back and closed the drawer. Walking to the closet he began looking at the dresses.

One of them really caught his eye. It was a light rose in color. It was light cotton. It would require a slip. There was one, on the back of the door under his bathrobe. He hadn’t even noticed it. He picked out a pair of panties. He took them, the bra and slip to the bathroom. His heart raced as he stepped into the shower. He used Anne’s shampoo and conditioner. He toweled himself off and used some of his mothers dusting powder. He might just as well go all the way. The panties were followed by the bra and then the slip. He used a brush and a hair dryer to style his hair.

Then he used the tricks that Harriet taught him to tease it and give it body. He carefully sprayed it with just the right amount of hair spray. He put on a light coat of lipstick and mascara. Back in his bedroom, he put on the rose colored dress and a pair of white flats.

He went to the linen closet and got out some clean sheets. Returning to his room, he made up the bed. While he was at it, he heard his dad leave for his golf game. He knew it was business and he would be gone until late afternoon. Milton put a nightgown under his pillow then took his hamper to the laundry room. The other laundry was already there. He sorted it according to color like his mother had showed him before Halloween. He put in the first load of whites and went to the kitchen. After breakfast, he gathered all the dishes left behind by his father and sister. He washed the dishes and went to the family room, where his mother found him watching television.

“Morning Millie,” she said as she came in. “Did you start the wash?”

“Yes, I brought mine down and thought as long as I was there, it was the least I could do.”

“You cleaned up the kitchen for me too, I see.”

“Yeah.”

“Thank you sweetheart. I really like having a part-time daughter like you.”

About 10:00 Milton was coming out of the laundry room after changing a load from the washer to the dryer. Anne was in the kitchen. “Millie, it’s good to see you again,” she said giving him a hug. She sounded sincere to Milton. Anne even pitched in when it came time to fold the fresh clothes from the dryer.

After that, he wore nightgowns to bed. He really liked waking up wearing them. Somehow it just made the day start better. It wasn’t long after that he decided to wear panties, even when he went to play baseball with the guys.

The next weekend, he spent at Jennifer’s. Both days. Jennifer asked if he was going to spend some days through week over there. He said he would.

At home as Millie on Wednesday he decided he needed to talk to his mother again. The family room became his counseling room. The afternoon soaps were on.

“Mom, I told Jennifer about my decision to wear Anne’s old clothes.”

“Did she take it well?”

“Yes, she thought it was great. So did her mother. Jennifer wanted me to dress-up over there.”

“Oh. And did you?”

“Huh?”

“Did you dress-up over there?”

“Well, I … ah, I, I guess I did. I’m sorry she just made it seem OK.”

“What did her mother think about it.”

“Well, she liked it. She let me borrow some mascara. She complimented me on my helpfulness in the kitchen,” Milton told her excitedly.

“Are you sure they won’t tell anyone about you?”

“Oh yeah, I know about Harriet.”

“Who is Harriet?”

“That’s what they call Jennifer’s brother, Harry, when he’s dress as a girl.”

The next weekend, Milton got up and dressed. He went to the laundry room and started the laundry, as had been his habit these last few weeks. After he had eaten, he called Jennifer.

“Hi, it’s Millie.”

“Millie? Does that mean that your friend Mike wouldn’t recognize you?”

“Not the way I’m dressed.”

“What are you doing now?”

“Oh the same as every Saturday, I’ve got the laundry going and I’m waiting for it to get done.”

“How long will it take?”

“Quite a while, I’ve got seven loads to do.”

“I was hoping you could come over today. You were over here only once this week.”

“I know, but you know I can’t spend all my time as Millie. My dad said that a part-time daughter would be all right, but he didn’t want a full time daughter. Too bad you couldn’t come over here.”

“Too bad who couldn’t come over here?” asked his mother as she came in from the kitchen.

“Oh, I’m talking to Jennifer.”

“Won’t her mother let her come?”

“I don’t know.”

“Well, you could ask her if you want.”

“Hey, Jennifer, would your mother let you come over here?”

“I think so, is that an invitation?”

“Sure.”

“Just a moment. Mom, can I go over to Millie’s? … … Thanks. Millie, my mom said yes. How do I find your house?”

Jennifer was there in fifteen minutes. She was as helpful at Millie’s house as Milton was at Jennifer’s. Mrs. Johnson invited her to dinner. When Mr. Johnson got home, he looked into the kitchen. Millie and Jennifer were fixing dinner.

“Who’s that in the kitchen with Milt, … Millie?” he whispered hoarsely.

“Oh, that’s Jennifer. You remember, Milton went to the beach with her and her mother.”

“But Milton is Millie,” he whispered.

“Of course. You know that on Saturday he helps me out by doing the wash and stays Millie all day.”

“But, … Jennifer?”

“She knows all about Millie now. I talked with her mother last week; I had long conversation on the phone with her. She told me some very interesting things about Milton and her son Harry and others like them.”

“Like them? Her son Harry is like Milton?”

“Yes it seems that the library has a number of books on transvestites or cross-dressers as many prefer to be called.”

“Transvestites? Cross-dressers? Books? Why on earth did you talk to her about such things?

Because we both have sons who like girls clothes, and she has been dealing with hers longer then I have mine. Since she knew about Milton’s Halloween costume, she assumed that Milton was like her son. As a matter of fact, she was aware of it even before we would admit it to ourselves. She introduced him to Harry.”

“So that’s why he decided to make this a regular activity.” He was beginning to get a little tight jawed.

“Oh calm down. She didn’t introduce him until after she had every reason to believe Milton was already immersed in the routine.”

“How could she know that?”

“Jennifer is very perceptive, what with having a brother who wears girls clothes. She wheedled it out of Milton, that he liked it right after Thanksgiving. Then she got Milton to admit it in front of her mother.”

“Milton told them. Oh my God. I just assumed he would be to embarrassed to tell anyone about it. Now I find out that he has a girl friend and her mother that knew it before I did. Who else knows? Oh of course Harry and who ever else he decided to tell. Is it normal for cross-dressers to yell it from the roof tops?”

“Calm down. We have a guest in the kitchen. It’s not normal for them to tell very many people, but it is normal for them to grab every opportunity to dress up when they can. I’m told that sooner or later, he’s going to want to go somewhere dressed. Well, Jennifer and her mother know about it. When he feels the need to go somewhere, he can go there.

“But most of all, he needs acceptance. He needs our acceptance and the acceptance of friends. Jennifer and her mother qualify as friends who accept him. If he is going to have any chance at self-esteem, we have to give him room to express himself and facilitate his interaction with people in his roll as Millie.

“It’s as though he were two people. Milton and Millie. He needs to be able to reconcile that dichotomy. To fuse Milton and Millie into a single personality.

“Mrs. Michaels has done a lot of research on the subject. She’s given me a list of books I should read.”

Later that evening, Mrs. Johnson loaded Jennifer’s bicycle in her trunk and took Jennifer home. Millie rode along. Mrs. Michaels invited them to come in.

“It’s so nice to meet you after all this time,” Mrs. Michaels said.

“Yes, it seems that we have more in common then I would have guessed when we first talked on the phone.”

“Millie is so lucky. I understand your husband accepts Millie.”

“Well, yes. He’s not happy about it, nor is he comfortable with it. But thank God he realizes that his children need his unconditional love.”

The conversation lasted about an hour and they left with the offer from Mrs. Michaels for Mrs. Johnson to call or come by anytime.

Millie gained a lot of freedom over the next year. Soon his mother and Mrs. Michaels were taking their daughters to lunch and a movie.