They live in a relatively small town as many towns around them have tens of thousands of people, some more than fifty thousand people, while their town barely had six thousand, including outside of the village proper. Some people complained that they all knew one another it was only partly true. If one grew up in the town like Bruce did, one knew or recognized nearly all of them. Deanne Tremble had moved here with her family just a few years ago and she’s still considered and outsider. While she’s more beautiful than most of the girls; she didn’t get recognized as such. It was embarrassing the way guys made a fuss, over her to the point that it became an embarrassment. Some of the guys may have a girlfriend they were dating; many more were afraid to even talk to Deanne because they thought she was so beautiful and were staring at her, or worse, calling her name but acting like they didn't, calling her home and hanging up. Being annoying and not accepting her as one of us.

It was the spring of my freshman year in high school and Deanne, a junior, was walking fifteen feet in front of Bruce as he was walking home through the downtown. Numerous guys riding around; what we call making the loop. Some were riding by to get a good look at Deanne. The funny thing most were too afraid to talk to her let alone ask her for a date like they wanted.

Finally, someone riding slowly by, yelled to Bruce, “Hey Bruce! Are you going to ask her for a date?” Bruce waved them off as Deanne turned around and looked at me. He was walking by, when Deanne asked, “Were you going to talk to me and then changed your mind?”

He paused, looked up, and was sure he blushed. She then asked, “Are you afraid of me?”

He smiled and said, “No, but I’m embarrassed and feel sorry for you?”

She started to giggle and caught herself. “Sorry, for me, why would you be sorry for me?”

He stopped, “Not sorry because you’re in need. But my oldest brother says beautiful girls are some of the loneliest people. He says some very attractive girls stay home on weekends because everyone’s afraid to ask you out. They assume you are already going out. He did pretty good in dating before he went away to the navy.”

She giggled at what he said.

Deanne stopped in a small store to get something for school tomorrow and asked him to stop with her if he was willing. She asked him as they went in if he knew Roxanne; Roxanne was her sister.

He said, “Of course, we’re in the same grade and we are one of the smaller classes. She’s nice like you are, but please don’t tell her I said that.”

They were back walking together about a block from where she lived. The two were at a corner when some guys came again racing around the corner. Bruce stepped in front of Deanne as he knew there was a dirty rain puddle the car was going to drive through.

The front of his clothes got wet and dirty, soaked and ready to fall to be more exact.

Deanne said, “You didn’t need to do that. I’m not as fragile as you think.”

He shrugged his shoulders, “I didn’t think that. It is just a habit. You have only lived here three years and we consider that new.”

They giggled and she remarked, “You have a beautiful giggle, that’s so precious.” Then she changed the subject, “I think I’m going to call the police and complain about what Robert just did.”

They crossed the street and she asked how much further he had to go. It is six or eight blocks, nothing he couldn’t handle. It was cool and windy and he was carrying some of her packages to her house. “Well, thank you for walking with me and carrying my packages. I’m sorry if I disappoint you, I won’t say yes to a date.”

He laughed, “That’s funny, you thought I was going to ask you for a date. I probably couldn’t get a date with Roxanne let alone you. But I think she looks at the guys a year or two older than me.”

She said, “Then why were you being so nice to walk with me.”

“Awe, I got my reasons. Let’s say I like walking with pretty girls. It’s nice for me.” Deanne sensed there was more and would leave it at that. “If you’re willing to carry my package into my house; I’ll do something special to make up for you getting wet and all dirty.”

He said, “I planned to carry your extra package anyway. You don’t need to do anything.”

She asked, “So what are your reasons for walking with me?”

He said, “They’re private, I’ve enjoyed walking with you. Did you know you’re as interesting as you are pretty?”

She giggled again, “I guess that was a compliment, because if a girl is pretty she can’t have much more going for her?”

He admitted, “I said that wrong, I’m sorry. You see what an attractive girl does to a silly guy like me.”

She pointed to her house and they walked up onto her porch. It is one of those old-fashioned porches meant for sitting outside. She took her package and asked him to sit and wait right there. He did, though he wasn’t sure what he was waiting for.

Finally, she came back and asked him to step into the house. He said, “I can’t, I’ll mess up your rug and house.”

Deanne said, “I took care of that just follow the old sheets to the bathroom.” He did as she asked, and then she said, “Now take off your clothes and I will quickly get them dry.”

He argued as he wanted to get home, but Bruce was losing time arguing and she wasn’t letting up. Even her sister Roxanne was now outside the bathroom door telling him he wouldn’t win the argument.

He threw out his pants, shirt, and even his spring jacket. But Deanne complained that he didn’t throw out any underwear. And he insisted he wasn’t going to. Finally, Deanne said, “You can’t stay in there as other people will need to use the toilet. Plus I have bad news and good news…” When he asked, she said, “The bad news is our Dad is the only guy in our house and Dad weighs over two hundred and thirty pounds. You won’t fit in his clothes, not even his robe.”

He asked, “And what is the good news?”

Deanne said, “You are close enough to our sizes that you can wear some of my clothes; they’re clean and dry.”

He stepped back from the door and Deanne pushed in a pile of folded clothes to choose from. One piece was training pants that would hug his body showing everything. The top was a pink Teri-cloth pullover with a unicorn head. And then he heard Roxanne say, “Make sure you wear the panty or she’ will never wear the bottom again.”

He asked, “What’s with the skirt? Am I supposed to wear that over the pants?”

There was giggling again and in unison, they said, “No, we thought you might like the choice?” Roxanne whispered, “I thought you might like to say you got into Deanne’s skirt?”

He thought and said, “If you don’t mind, I might wear the skirt in preparation for crossover day next week.” No sooner was he out of the bathroom, walking to the front room, that Deanne hurriedly went in to snatch up his underwear, saying, “You’ll have to wait a little longer as I need to start washing everything.”

We were visiting when the backdoor opened up and another girl called in. “It’s just me, Roxanne. Did you forget you were to come over?” Tally stepped in before Bruce could move to hide. And Tally was soon kneeling on the floor laughing. “Who’s this, never mind, why’s Bruce dressed in Deanne’s stuff? I didn’t know Deanne’s a cougar!”

Tally was soon sitting next to Roxanne and everyone was staring at Bruce. Deanne tells the story, and he's cupping a hot cup of tea to warm up. He wouldn’t have included the part about crossover day but Deanne did and it was out in the open.

Tally was rattling off clothes that Roxanne and Deanne had that he could wear. And then added, “We could get a pair of falsies from the drama department, but you couldn’t look like a tramp wearing the stuff to school. You would need to try to look presentable as a girl.”

He grumbled when his clothes weren’t ready in fifteen minutes. Deanne said, “If I just dried them; the dirty water would have set as stains. I had to wash them first, just be patient. Being with us won’t hurt you.”

It was 5:10 and his clothes were now in the drier when Mrs. Tremble arrived home and walked into the house to discover that a strange boy was there. “Chivalry is not dead, and the favor has been turned around. What happened?”

“Mom, you should have been a fly on my shoulder as I walked home with this young gentleman. He’s so sweet and truly has the kindness you rarely find anymore. He even knows why a girl like me might be alone on weekends.”

She makes him repeat what he learned from his brother. Deanne tells her mother, “I met his brother Randy when we first moved here and he dated lots of attractive girls.”

Deanne got his clothes out of their dryer and then she bemoaned. “Mom, the seat of his pants ripped; I bet it caught on that old wicker chair on the front porch.”

Mrs. Annette Tremble apologizes to Bruce, “I’m sorry, but if you can wear what you have home I’ll give you a ride and replace the pants later.”

He changed and used his coat around my waist to cover the tear. “My mom will say no to replacing my pants.”

“Well then since you don’t have any sisters and you are going to dress for crossover day. Let us help you get dressed and made up for the occasion.” He didn’t think much of the suggestion and hoped no one would remember tomorrow or the next week.

Mrs. Tremble had him home at 5:50. She and her daughters escorted him to the door and his Mom greeted them with a big smile. “And what do we owe to the escort you have young man?”

All he wanted was to say thanks and get up to his room. That wouldn’t do for the women. He knew Roxanne brushed out his hair; he thought it was his usual informal style. Instead, it was brushed to be a little girl-like.

Deanne told of their walk to her house, and the need to wear her skirt and top while he waited for his clothes to be washed and dried. Mom said, “So is that where his softer hairstyle came from?”

Both girls explained that he said, he was dressing as a girl for crossover day. Mom nodded with approval, but Bruce wasn’t sure what that meant. She did ask if someone had taken a picture of him in the skirt and pink unicorn top.

Mrs. Tremble said, “I did ask before I took this picture; I hope it is okay to show it.” There was no way Bruce was saying no at that point. Mom fussed over the pictures and then his brother Dan came down to see what was happening.

That he was surprised to see Deanne or Roxanne there was an understatement. Bruce told him to shut his mouth before he caught any flies. Their Mom told Dan, that your brother had impressed the Tremble women by being nice enough to talk with them.

Dan knew of his plans to cross-dress for Crossover Day and joked. “Well did you tell them of your idea of dressing up as a girl and ask them for help?”

Deanne said, “Smarty, he didn’t ask for help but we have offered it to him. I don’t remember in three years you being nice enough to say hello.”

Dan said, “I have had enough girlfriends I don’t need to ask.”

Roxanne said, “She wasn’t talking about dates, just being nice enough to be friendly. It sounds like your male ego is fragile enough, it couldn’t handle a skirt.”

Mrs. Tremble spoke, “Roxanne apologize that was rude and not called for.”

Roxanne was going to say something, but my Mom cut her off. “No apology needed, the young man acted as a poor host and deserved it. He’s the one who owes the apology.” Dan ran upstairs instead.

His Mom said, “Thanks for the offer of the clothes. I’m not sure about the help to get ready next Wednesday. But we’ll consider it.”

Mrs. Tremble said, “If you could get him up and over to our house by 6:30 Wednesday morning. I’m sure I and the girls can get him all prettied up. Mrs. Sanders, if you can be there you would be welcome.”

“Um, um… what about me,” Bruce asked.

Deanne said, “Since you brought crossover day up; we assumed you already agreed.” She hugged me and whispered, “If you want out, just speak up.” She then joked, “You will probably be so beautiful, that no one will ask you for a date.”

Everyone laughed, though Dan did it mockingly from the top of the stairs. “I’m afraid that he’ll embarrass me.”

Bruce said, “I’m not going to embarrass anyone. Over a third of the students are expected to take part.”

Mom said, “Randy did it as well. I think he did it the first or second year it was done here.”

Dan said, “But they thought Randy was cool. Bruce just happened to be shadowing Deanne and she’s being nice to him. Maybe he should go to the dance next Friday and see if anyone will dance with him. Then he can experience what it’s like being with a real guy.”

That hurt, and Mrs. Tremble hugged Bruce, “Don’t listen to your brother. I think he’s jealous of the attention you’ve gotten.”

“It’s okay, I’m used to him. I want to thank Deanne and Roxie for being nice. It was a change from coming home and being stuck with Dan being here.”

Dan mocked him, “Did you like dressing in her clothes? Did you feel pretty?”

Bruce stuttered before his thoughts caught up with his words, “Wearing a skirt was just the outer dress to looking into their world. If that is what it takes, I’ll do it gladly.” Deanne stood up and had him do the same as she hugged Bruce.

“Mrs. Sanders, we should let your family get on with your evening, but we’re proud to have met your younger son. If we can help him next week that would be great.”

Mom walked out with them, thanking the Trembles and talking for another fifteen minutes.

Mom waited until after dinner to come up and talk with him. “Bruce, you made some great friends today. The Trembles were impressed with you as the mature and good thinker you are… They were surprised that you have trouble with your school work and learning… They said you were very good with them; like when they visited here.”

“Deanne wondered if you might benefit from studying with them after school on Tuesdays and Thursdays. Would you consider doing that?”

He said, “Mom, I’d consider it, but I think, it would be a waste of their time.”

Mom said, “If that is your biggest objection why don’t we try it starting Thursday after school? You don’t need to walk with either of them.

Mom said the next day, “I talked with Mrs. Baker from the school and she says, you’re right. Boys seem intimidated that Deanne is not only quite attractive but quite smart.” Mom was amused and understood why Deanne had sent home the panties I had worn there.

School on Thursday was nothing special except his reading demands were building up on him. Roxanne did remind me to bring some of his reading to their house after school. He was worried that his poor reading skills would embarrass him in front of them.

Deanne spent her time for his first fifteen minutes listening to him read. She asked him at the end of that time about what he read. She then commented, “Did you realize that you were reading better the longer you read?”

He said, “It was easier because you were listening to me. You didn’t get angry with me, not even when I had trouble.”

Deanne said, “I think you need to practice more.” Deanne allowed him to read on my own as she was reading nearby. It was getting close to 5:00 when Deanne stopped him next. She asked, “What page are you reading now?” It was 547 and she reminded him that he had started at page 512.

He was surprised as he had never read more than twenty pages at a time before. She even asked him to reiterate to her what he read.

Roxanne was now there and she too had read these pages. Roxanne said, “You remember that and you’ll do well on the quiz tomorrow.”

He could tell that Deanne was thinking of something as they visited across a table. Finally, she got up and went to her room but was soon back. She asked, “Would it be okay to use a facial cleanser on you? It would help your complexion.”

She had him move over to another chair big enough that he could lean back against her. She then started to apply a wet gooey substance. Halfway through, he heard it was a cleansing mask that needed to stay on for a minimum of ten minutes. He was silent as he guessed it was too late to say no.

Roxanne used some hair clips to be sure he didn’t get his hair stuck into the mask. She was the one who said, “This will help you for next week when you dress for Crossover Day. Your makeup will hold better and not show the usual boy blemishes.”

Roxanne began to ask him questions about what he read and what was likely to be on my quiz the next day.

Finally, Deanne asked questions, “Do you prefer skirts or jeans? Do you like your hair styled or straight?”

Once, he caught on to the questioning, he said, “He prefers to look at girls. Yes, I sometimes wonder what it would be like to be like you. But one day would be more than enough.”

Deanne said, “I hope you won’t mind this nosey friend. I was just wondering…

To be Continued…