Roy And The Road To Renee - Chapter 4.
By Pentatonic

Saturday, November 1, 2014:

The Queen of the Night was a mess. The sun was shining brightly when I awoke the morning after the Halloween party. I squinted at the clock; it was nearly 10:00 a.m. I looked about. My dress from last night was loosely draped over a chair, not hung up as it should have been. I came to realize that I still had my bra on but minus one insert, along with panties, garter belt and nylons. I had no idea where my slip was. My shoes had been abandoned in the middle of the room. Thankfully, I had put on a nightgown, or at least I was wearing one.

I got out of bed, somehow found a robe and made my way to the bathroom. My face was a mess; I hadn’t removed my makeup, but I, or someone, had removed my wig. I absently wondered where it could be.

Surveying the wreck in the mirror, I decided to remove the makeup as a first step to normalcy. Normalcy? How could I consider myself as anywhere near normal. After I cleaned off my makeup I stripped off the remainder of my clothes and stepped into the shower. First thing to do was to clear the cobwebs from my brain. A good shower was just the thing to do that.

After my shower, I put my robe on and picked up my discarded clothing from the floor of the bathroom. I stepped into the hall, and surprize of surprizes, came face to face with my mother. “Well, it looks like someone had a good time last night,” she said as a greeting. I just grunted as a reply.

“What time did I get home?” I wanted to know.

“Late,” she answered, “but you then flopped onto the couch and feel fast asleep. Your sister and I finally got you to your room and into a nightgown. I hope that you appreciate that we didn’t undress you any further than we did, although your sister wanted to, but I talked her out of it.”

“Thanks.” I mumbled.

“Get dressed and come down for some breakfast. It’ll make you feel better.”

It appeared that my Renee side didn’t object, so I had no problem getting dressed as Roy, with the exception of a pair of lace trimmed panties to please my Renee side. Although there may have been something incongruous about being dressed as I was I went down to the kitchen and started removing my black nail polish. My mother told me that Becky had called while I was still asleep, and that I should return the call.

“Guten Morgen, Konigin, wie gehst,” Becky said. Both Becky and I had studied german, and she liked calling me “Königin der Nacht,” which is german for Queen of the Night. My response was a brief grunt. “That good?” she replied. I told her that I had promised to help Joe with some repairs to his car, and she was welcome to come over to keep Joe and me company. Otherwise we could meet later.

After completing the call, I noticed a bowl of Halloween candy left over from last night. As I reached over for some, my Mother announced, “No you don’t! You’ve got to watch your figure.”

“Why?” I said.

“You may think that you are finished with your Renee side, but my female intuition tells me otherwise,” she said. With that I went back to my room to hand wash that which had to be so washed, hang up other clothes and put the balance in the laundry hamper. I finally located the wig, put it on its form and brushed it out some. Satisfied, I went back downstairs to be greeted by Joe who was polishing off some bacon. Bacon, that my Mother had prohibited me from eating, because of ‘my figure.’ Between my mother’s dietary restrictions and some hard exercise on my part, I was able to lose some weight, mainly around my waist, but none on my butt. I hungrily watched the last piece of bacon disappear into Joe’s mouth.

“Ready to start?” Joe said, with his mouth full of bacon. Last summer the heater core in his car had sprung a leak. Rather than replacing the core in 95 degree heat, I had bypassed it between the thermostat and water pump so cooland could still circulate in the engine. With November weather in the air, it was high time to get the heater working.

“Did you get the parts?” I asked.

“Naw,” he said, “I was waiting for you. When I buy the parts by myself, you always complain that I got the wrong ones, so if wrong parts are bought, it’ll be your fault.”

“Okay,” I said, “pull your car over to the side of the driveway, and open the hood. We’ll let it cool off while we take my car to the parts store.” I looked over Joe’s car, and made a shopping list and we headed off to get the parts.

When we were in the car, Joe turned to me and said, “That was some party last night, wasn’t it?” I just grunted. “You were the foxiest girl there. If I didn’t know, I would have hit on you,” he added. “Of course, Becky was keeping an eye on you.”

Not enough, I thought. I remembered his patting and squeezing my behind, along with his hand reaching in the slit of my skirt and pulling on my garter straps. He had hit on me, but now was not the time to mention it.

By the time we returned from the parts store, the weather had warmed up, so I took off my sweat shirt so I wouldn’t get any grease on it. Because working on a car can be dirty work, I had put on an old and rather tight t-shirt which had already had grease and grime stains on it from previous forays into auto repair. Likewise for my jeans.

I started by draining the antifreeze into a clean drain pan. To do this I had to get on the ground and open the drain cock on the radiator, after which I started removing the old heater core and hoses. Some of this involves climbing under the dash board. Thankfully Joe’s car did not have air conditioning. All this activity caused my jeans to slide down a bit, but I ignored it and didn’t pull them back up, reluctant to add more grease to my jeans or dirt on the panties I was wearing, because by this time my hands were grimy.

I then turned to removing the by-pass I had put on last summer. This involved bending over the fender and stretching my arms out. It isn’t hard to figure out what happened next. The waistband of my panties were very visible. I felt Joe pull on the waistband and let it snap back. “Nice panties,” he said with a chuckle.

“If you don’t like the way I’m dressed, you can fix your own car,” I said in a huff.

“No, No, I do like the way you’re dressed,” he said. Just then Becky walked up the drive and heard Joe’s last comment.

“You like what?” she said, joining in the exchange.

“How Roy’s, or maybe I should say Renee’s, panties look,” he said to Becky.

“Let me see!” she said with a gleeful smile, and she walked up to me and pulled up my t-shirt. “Very nice,” she said. “So a little bit of your Renee side decided to get up on a Saturday morning.”

Renee never slept, I thought to myself.

It took the best part of an hour to do the whole job and at last I was squatting down to close the drain on the radiator before replacing the antifreeze. Squatting down is a sure way to display underwear, and this was no exception.

“Hey Joe, I talked to Sue, and she should be here any minute,” Becky said, “Maybe we can do something today.” As she said this Sue walked up the drive. My back was to her and I didn’t notice her arrival until I heard her say, “Nice panties.” Oh great, I thought sarcastically, why don’t we invite the whole block to come over and see my panties?

“He, or maybe I should say ‘she’ likes to wear panties,” Joe said with a laugh.

“No, I wear them because Joe likes cheap thrills,” I said.

“How come Joe’s all clean and you’re all dirty?” Sue asked.

“Because I’m doing all the work. Joe’s only here to pay for the parts and to admire my panties. I think he’d like to wear a pair,” I said. “How about it Joe? I can find a nice pair for you, and you can pick the color.” Joe began to blush. Maybe there’s something there, I thought.

“Joe, start your car and let it get hot so we can check for leaks,” I told him. Like I said, I’m a fairly good mechanic and there were no leaks. When the engine was hot enough to open the thermostat, the welcome flow of hot air came out of the vents on the dashboard. Another good job, I thought.

Just about this time my mother stepped out of the kitchen. “Hey, it’s way past lunch time,” she announced, “If you want, I can fix you lunch, at least for three of you. The grimy one will have to wait until he’s cleaned up.” Becky, Sue and Joe went into the kitchen, while I went to the wash tubs in the basement, where I had a goodly supply of industrial strength hand cleaner. The best way for me to do this is to first strip down to my underwear, or in this case, my panties, otherwise you can clean you hands, only to get them dirty again when you remove grimy and greasy clothes. I threw my jeans and t-shirt in the washer, poured in a good quantity of soap, and started it. I finally got all of the grime and grease off of my body, and was ready to go up stairs for a well needed shower, to get the rid of the hand cleaner residue. Oops, I thought, I have to go through the kitchen to go upstairs, and all I have on are my pink lace trimmed panties. I looked for anything to use to cover up, but finding nothing I decided to brave it. There were a lot of giggles and laughter when I stepped into the kitchen.

“You smell like industrial cleaner,” my mother said, “and your face, hands and arms are all red with that cleaner. After you take your shower, use some of my skin lotion.”

“Okay,” I said. When I passed Joe, I wiggled my panty clad behind at Joe. I don’t know why I did, it must have come from my Renee side. After a good hot shower, I dried myself by patting, not rubbing, and used the lotion. It’s awfully girly smelling, I thought, but I used it anyway. I wrapped my damp hair in a towel, turban style and got dressed.

When I got back to the kitchen, my mother handed me a salad. I needed something more than a salad, and I frowned at her. “Your figure, dear,” she said. Everyone, except for me, giggled and laughed at my discomfort.

Becky moved closer and sniffed. “Wow,” she commented, “You smell great, all flowery.”

What could I do? I just smiled and said, “Thanks.”

Becky, Sue, Joe and I spent the rest of the afternoon riding around in Joe’s car, giving it a long test drive, with stops here and there. We hit some fast food joints and I was finally able to get some substantial food. We started the test drive with Joe driving and my riding in the front passenger seat. We ended up with Joe and Sue in front, with Becky and me cuddling in the back.

About 5:30 Becky reminded us that she had a babysitting job that evening, and we all went to our respective homes.

Sunday, November 2, 2014:

Becky called and annouced that some of the stores in the mall were taking applications for extra holiday help. “I’m going over there,” she said, “We’re both 16 so we are legal for a job. Want to come along with?”

“I heard that it’s a bad idea for two teenagers to be with each other on a job search. Maybe you should go alone,” I suggested.

“But I want Renee with me,” she said, “that way you can browse the merchandise without calling attention to you while I talk with the hiring people.”

“Okay,” I said, “give me 45 minutes to an hour, and I’ll come over and pick you up,” I said.

“Great,” she said, “and dress nicely. Pantyhose, bra, nice blouse, and maybe the plaid skirt. Bring your makeup, and maybe I can do something with your hair.”

About an hour and a half, two well dressed young ladies headed off to the mall, one seeking a holiday job, the other just along for support.

It seemed that a lot of other people had the same idea, and about two hours and two stops at the washrooms, we found ourselves at a quieter part of the mall, but with no job. We noticed two unique stores. One was a corset shop and the other a women’s store for tall women.

“I didn’t know that anyone still wore corsets,” commented Becky. The other store actually had a ‘holiday help wanted’ sign in the window. We went in the store for tall women.

A tall woman approached us. “May I help you, girls?” she asked.

“I want to apply for the job,” Becky said, pointing to the sign in the window.

“We only stock clothes for women over five-eight. How tall are you?”

“Five-seven,” Becky replied, “but I can wear heels.”

“That may be true, but the clothes are cut for taller women, and you’d be on your feet all day. Not a good idea.”

The woman then looked long and hard at me. “How tall are you, Honey?”

“Going on five-nine,” I answered.

She took my hand and studied my nails. The repairs on Joe’s car had talken their toll.

“What in heavens happened to your hands?” she exclaimed.

“I was repairing a friend’s car yesterday,” I replied. “I just didn’t want to put on a set of acrylics, since I’m not the one looking for a job.”

“But if I hire you, your auto repair days are over,” the tall woman said. “Are you interested in a job? It seems that the current crop of females are all short.”

During this exchange Becky was smiling excitedly.

“Come into my office,” the tall woman said. Once in the office she introduced herself as Marge Shay, the owner of the store. Becky and I introduced ourselves. She invited us to sit.

“Before we go any further, I have to tell you that in addition to our women customers, we have our ‘special’ customers.”

I got the drift of what she said. “You mean cross-dressers?” I said.

“Yes, and if that bothers you in the least, I’m sorry, I can’t use you.” Both Becky and I laughed at this statement.

“What’s so funny about that?” she demanded.

“Well, I have a secret, and once you know it you might not want to hire me,” I said.

“Show her your IDs,” Becky suggested, and I did.

Ms. Shay took them and when she had noticed that my name was Roy, and that I was genetically a male, a broad smile crossed her face. “Excellent! All the more reason to hire you she declared, When can you start?”

“You mean I have the job?” I asked, not quite believing what I had heard, “But I was not looking for a job.”

“Maybe not, but a job just found you. You are exactly what I am looking for. When the men hear about you, and how good you look, they’ll be crowding through the doors. How do you manage to look so feminine?”

Becky and I explained the research and essays we had written. “Once I started getting in touch with my feminine side, that side no longer just touched; it grabbed on wholeheartedly.”

“I can’t pay a lot hourly, but I can give you a 60% discount on anything in the store, and you get commissions on your sales. Still interested?”

“Yes,” I answered, “but I am concerned about Becky getting a job.”

“Becky helped you in your transformation, right?”

“Yes, I couldn’t have done it without her.”

“I’ll tell you what,” Ms. Shay said, “let’s all three of us walk over to the corset shop.
A lot of my customers also shop there, if you get my meaning.” We did.

Ms. Shay introduced us to Mrs. Sands, who owned the corset shop, and explained our situation. Mrs. Sands smiled approvingly. “What do you know about foundation garments?” she asked Becky.

“Unfortunately, very little,” Becky admitted.

“Then lets corset up your friend, and you’ll learn a lot. How does that sound? What I like is that you’ve already dressed a boy, so our male customers won’t offend you.”

“Okay, I guess,” Becky said uncertainly.

“Go into the fitting room, and strip down to your panties.” Mrs. Sands commanded me to do, “You are wearing panties, I presume?”

“Of course, pink with lace trim,” Becky answered for me.

“Very fetching, I’m sure,” Mrs. Sands said.

For the next hour, I was fitted into a series of foundation garments, each one more painful than the previous one.

“Pick out one that you like,” Ms. Shay said. “I’d like you to wear it when you are at work. I’ll advance the cost and put it on your clothing account at my store.”

“60% off, Mrs. Sands, as usual” Ms. Shay asked.

“Naturally,” Mrs. Sands replied with a smile.

“Both stores get busy at Thanksgiving, and stay busy through the new year. Can you work evenings and weekends through the first of the year?” We both assured that we could, as long as it didn’t interfere with our school work.

I was still wearing my foundation garment when Becky and I rode home. “It really makes you look good,” Becky said.

After dropping Becky off I drove home. The first person I saw was my mother, who stared at me with surprise. “You look different,” she commented, “what’s going on?”

“Becky and I have jobs for the holiday season,” I answered, and explained out jobs.

After I finished, with a lot of questions from my mother, she finally said, “What will your father think?”

Thursday, November 6, 2014:

After Mrs. Benson said that she was sending Becky’s and my essays to a college professor, I more or less put the matter out of my mind. Imagine my surprise when she called Becky and Me into her office. With her was a distinguished man who was the professor to whom the essays had been sent. He started out praising our work, calling it original. Then he got to the point.

“I don’t know about your college plans, but I want you to at least consider choosing a college or university that has either a women’s studies major or a gender studies major. You both seem to have an aptitude for this area.”

When we talked some more, I disclosed that I was dressing as a female and working at a store that specialized in catering to the transgender community.

“Excellent!” he said, “might I suggest that you maintain your journal and note your observations. It may become a valuable tool for you and others to use. Naturally you won’t use names and you’ll keep it anonymous. When you are looking at colleges, could you have Mrs. Benson apprized of your progress? I’d really like to keep in contact with both of you.”

Saturday, November 8, 2014:

It was a gloomy and rainy Saturday afternoon, and I was in my room practicing different makeup looks. I heard a knock on the door and my mother ask to come in. There I was, fully dressed. She looked at me with a critical eye. “Too much dark eyeshadow,” she observed. We looked at each other for a few moments. “Time to talk with your Father,” she added, “less makeup is better in this case.”

“Okay,” I said, and removed my eye makeup and reapplied it under my Mother’s gaze.

“Better,” she commented. “Let me look at you first.” I stood up and turned aroung for her. “Okay,” she said, “Let’s go downstairs,” and with that she gave my hand a squeeze.

Dad was sitting on the couch, reading a magazine. When he heard us, he looked up. “Why are you dressed like that?” he asked, “I thought you were done with it.”

I paused a moment, and ignored his question. “Remember that I told you last Sunday that I had a seasonal job at the mall?”

“Yeah, I’m really happy for you getting a job.” he responded, “So?”

“I didn’t tell you where I’ll be working or what I’ll be doing.”

“Yeah, you kind of omitted any details.”

“Well when Becky and I went to the mall, only Becky was looking for a job. I was just there for support. Well, there’s this store that specializes in clothes for tall women; taller than 5' 8. Well, Becky is too short, but when the lady who owns the store saw me, she said I was tall enough.”

“So, what does this mean? When you were there, you weren’t, uh, dressed up like a girl, were you?” Dad said.

“Well, to be blunt, I was,” I said. “You see, it just worked out better, Becky wanted me to, so when she was talking to the employment people I could pretend to browse, and not call attention to myself,” I added.

“I’ll bet that’s not how things worked out,” he said with a slight smile.

“There’s something else,” I said, “the store has what the owner calls ‘special customers.”

“Special customers?” he asked.

There was no way to hint around until he knew what I was trying to say, so I went directly to the point. “Men who dress in women’s clothes. As you can suspect a lot of them are taller than most women, so, since the store caters to people who are taller, they like to shop there. As you can see, I’m a prime example.”

“Does the store owner know that your birth name is Roy?”

“That came out, and once she knew it, she told me that I was hired. I’m a sales clerk.”

“So, you’ll help other men look like women?”

“I’ll wait on anyone who comes into the store, but the owner thinks that because I am male, it will help sales.”

“I can see that,” Dad said, “if you wait on the men, they’ll be less embarassed.”

“Precisely,” I rejoined.

“Then what you wear will be more or less like a work uniform,” he observed.

“I’m glad you see it that way,” I said.

He frowned. “I may see it, but I don’t like my son prancing around in women’s clothes.”

“Is it okay if I promise not to prance?”

Dad laughed at this. I was making progress. “I have always encouraged you to make your own decisions, and I’ve always told you that your mother and I will support you. If this is what you’ve decided to do, I don’t have to like it, but I won’t prevent it. Remember, I’ll always love you, no matter what.”

“Thank you,” I said, “that means a lot to me.”

Nothing was said for a few moments. Then my father asked, “What about Becky? Does she know? How does she feel about this?”

I decided to answer all three question at once. “Becky was with me when I got the job. She seems very happy about it. By the way there’s a corset shop nearby and she got a job there.”

“A corset shop?” my dad questioned, “I didn’t think there were any of those left.”

“Just remember ‘special customers’ and you’ll understand.”

“I do,” he said and smiled.

A concerned look then crossed his face. “What you’re doing may be dangerous. A lot of people might want to physically harm you. Have you figured out how to protect yourself?”

“Becky and I are aware of the problems and are working on them. If it gets too difficult, I can quit,” I explained. Dad, Mother and I then spent the next hour discussing potential problems and how to avoid them. I felt that I was ready. My Renee side was very happy.

Finally, my father asked me, “Do you feel that you are really a girl? You don’t have to answer that right away, but think about, and we’ll talk about it later.”

Monday, November 10, 2014:

I had Monday off, and Joe came over to study for a test we both had on Tuesday. “I heard about your and Becky’s jobs. Weird!”

“Maybe, but I’m earning money, that’s more than you can say.” I replied.

“You know, you look different. Becky says that’s because you’re always wearing a corset,” he said.

“Yeah, all the time, except when I’m in school. If I don’t it’s uncomfortable when I have to put one on again,” I responded.

Joe was staring at me. “Are you wearing one now?”

“Yes.”

“Can I see?”

“Why do you always ask that? What is your fascination with women’s underwear? Sometimes I think that you want to wear some. Do you?”

“Well, umm,” Joe answered.

“Okay, just this once I’ll show you, but if I do, you have to wear panties, not just now, but all day tomorrow.” I figured this would be a deal breaker.

Imagine my surprize when Joe said, “Okay.”

“Go into the bathroom and put these on,” I commanded, and I handed him a frilly sky blue panty. When you come back, suitably attired, I’ll play show and tell.”

I had felt a bit tarty that morning and under my skirt and blouse I was wearing a full length corset with a built in bra, and I had nylons attached to the suspender straps of the corset. Naturally, I was wearing lace trimmed panties. Since my skirt was not lined, I was wearing a half slip. I had taken off my skirt and blouse when Joe walked back in. I couldn’t know if he was wearing the panties because he had put his jeans and shirt back on.

“Okay,” He said, “let me see.”

“Not until I see the panties,” I answered. “Strip!”

He took off his jeans and shirt, and there he was, wearing the panties. Well, I had made a deal, so I took off my slip.

“Wow,” he said. “I want to touch.”

I could see that he was getting excited. “Okay,” my Renee side answered.

When Joe touched me it was a feeling I had never experienced before. My Renee side was loving it.

And then he kissed me.

That surprised me and I quickly stepped back. “Why did you do that?” I demanded to know.

“I’ve wanted to kiss you for a long time. Now just seemed like a good time for it,” he said.

We just stared at each other for a few moments, my body tense with surprise. “I didn’t mean to shock you,” he said as he gently touched my cheek with his fingers. I visibly relaxed.

My thoughts were running wild. My Renee side was doing cartwheels.

“You liked it, didn’t you?” he said.

I didn’t want to admit it, but I did, or at least my Renee side did. “My mother’s home,” I said, “maybe we better stop this.”

“Okay, maybe later.”

I changed the subject and said, “You like wearing panties, don’t you?”

“I do,” he answered.

“Would you like to go with the whole look? Completely dressed as a girl?”

“I think so.”

“Okay, we’ll look for a time when no one will disturb us,” I said.

It was just about the time when Joe was getting ready to leave for home. “You know, I really appreciate all the help you’ve given me with school work and my car. I’d like to make it up to you by paying for a movie and pizza on Saturday night,” he said.

“Does that include Becky?” I asked.

“I heard that Becky has a babysitting job on Saturday,” he answered.

“If not Becky, then who else?” I asked.

“No one.”

“You mean just you and me?”

“Yeah.”

“You know, two guys going to a movie with each other, and pizza afterwards might give the wrong impression to some people,” I said.

“It wouldn’t if you went as Renee,” he said.

“Now let me get this straight,” I said, “You want to go out on a date with me, as Renee? Is that about it? I’ll be your girlfriend?”

“Yeah, that’s about it,” he answered.

“Why?” I asked.

“I’ve been attracted to you, at least your Renee side, Remember, we already have kissed each other.” he said.

“That was a mistake,” I said.

“I don’t think so,” he replied.

“Well, no matter what, the answer is ‘No’,” I said.

“Don’t be so quick to say No. Think about it.” he replied.

“Okay, I’ll think about it, but don’t get your hopes up,” I said. With that he picked up his backpack with one hand and gently brushed my cheek with the other. Renee desperately wanted to kiss him, but resisted the temptation.

“Enough,” I said, “now go!”

Tuesday, November 11, 2014:

After a restless night, thinking of what had happened between Joe and me, I caught up with Becky at lunch. First order of business was to confirm what Joe had said. “Are you busy on Saturday night?” I asked her.

“Yeah, I agreed to babysit. Why do you ask?” she said.

“Something came up, is all, but since you are busy, it doesn’t matter,” I said. “However, I do need to talk with you about something else. Could I give you a ride home and talk in the car?”

“Sure,” she answered, “It’s not something terrible, is it?”

“Naw, it’s something that’s bothering me, and I need to talk with you,” I answered.

“Okay, I’ll meet you at your car at the end of classes,” she said.

She was waiting at my car when I walked out of school. I opened her door and she got in.

Once I was in the car, she said, “Okay, what is it?”

“Joe,” I answered.

“He’s not in trouble, is he?”

“No, nothing like that,” I answered.

“Okay, then what?”

“I think that he’s attracted to me, as in boy to girl,” I responded.

“Is that all?” she laughed. “For those who know you and Joe, that is no secret. What, did he kiss you?”

“Well, yes,” I said, “but that’s not it. He asked me for a date on Saturday. Me, in this case, meaning Renee.”

Becky began to softly laugh. “It’s not funny,” I said.

“Yes, as a matter of fact it is,” she said. “All of the girls noticed that he couldn’t keep his hands off of you at the Halloween party. They wanted to know if it was also true when you aren’t wearing a skirt. So, has he?”

“Yes, but only when he sees that I’m wearing panties under my clothes,” I confessed, “He also told me that he now wears panties every day, except for days when he has PE.”

Becky snickered and said, “It sounds like he has gender issues, as Mrs. Benson would say.”

“But if I go out with him, people could say the same thing about me,” I complained.

“If that’s all there is to it, just tell him no,” She paused. “But that’s not all there is to it, isn’t it. You’d like to know what it’s like for a girl to go on a date, isn’t it?”

“Well, maybe, I’m just not sure. You’re my best friend, and I like to think of you as my girlfriend,” I said.

“And you think that our friendship would end if you went on a date as a girl? Is that it?” she said.

“Well, that certainly is an important part of it,” I said. Becky paused to collect her thoughts.

“Well, first of all, I am pleased and flattered that you consider our relationship to be so important to you,” she said, and with that she gave me a long kiss, which I returned with delight. “However, we need to remember that you getting in touch with your feminine side started with that essay, and I have to remember that I encouraged you to do so and actually did a lot to help it along. You can’t stop examining that side. I’m sure that you have wondered what it would be like if you were a girl on a date with a guy. So there is only one way to satisfy your curiosity, and that is to go on a date with Joe.”

“So, it’s okay?” I said.

“Yes, as long as you and Joe keep your hands, and other body parts, where they belong.” she said. “By the way, after the date I want details,” she added with a smile. “The date is on Saturday night, right?” she asked. “Come by my house on Saturday afternoon and I’ll help you get ready.”

Wednesday, November 12, 2014

The next day Joe caught up with me as we walked to our cars after school. “Well, what’s your answer, sweetheart?” he asked.

I quickly looked around to see if anyone could have heard what Joe said. “Don’t call me that,” I said.

“Okay, I won’t. But what is your answer?” Joe said.

“Okay, I’ll go on a date with you,” I said, “but only this once, and you have to behave yourself as a gentleman. No untoward touching, and no kissing.”

“The same goes for you. But remember, if you start anything, beware of the consequences,” he said. “I’m so happy, I want to kiss you,” he added.

“Not the best of ideas in the school parking lot,” I said, and with that we both got into our cars.

Saturday, November 15, 2014:

When I awoke on Saturday morning, I began to plan my day. The big problems were what I would tell my parents, and how I could avoid my parents when I got home, since I would most likely be wearing a skirt. My first step towards a solution would be to buy a little suitcase for all of my girl clothes and makeup. This was easily accomplished. While I was out shopping I also bought some makeup cleaning wipes, a hairbrush, some cold cream, and a roll of paper towels. While at the checkout line I noticed that there was a display of condoms nearby, and I impulsively bought some. I had no reason to do so, since I had no plan where they would be used.

A further stop yielded some feminine pads and a nice purse with a shoulder strap. I did indulge myself and bought a scarf.

Back at my house, I set aside some panties, stockings and my garter belt, which I could wear under my boy’s clothes. I carefully packed what other feminine clothes I had in the suitcase, along with my other purchases. My plan was to drive to Becky’s, get dressed with Becky’s help, put all of the clothes which I was not wearing in the suitcase and leave it in my car. Joe would pick me up at Becky’s house. I planned to have Joe drop me off at my car, and I would change into my boy clothes in the car, and remove all of my makeup before I drove home.

That afternoon I drove to Becky’s house to start my date. I had prepared a cover story for her parents which turned out to be totally unnecessary, since Becky had told her parents the complete story of what was going to happen.

“So, another walk on the wild side,” Becky’s father said to me. “I guess that your initial research didn’t include being a girl on a date with a boy. I can see why that would be important. By the way, are you still keeping a journal?” I confirmed that I was doing so.

“You may not know it, but most fathers give their daughters sound advice before her first date. You wouldn’t know it because you are a boy. But in this case, you are a girl, so I’m going to assume the role of a father. First, if there are any problems, you call for help. Second, don’t let things get out of hand. Boys will lie like a rug to get what the want from you. You just have to be firm and make sure they behave themselves. Now, go get ready, have a good time, and I expect a report from you.”

Becky’s mom asked me about how I was going to change out of my girl clothes and into my boy clothes, and I explained my plan.

“Since there is no secret here, bring your clothes in here and change back to Roy here,” she said, “now let’s get you ready for your date.”

I didn’t have that much to bring in, but I laid it out on the bed. “I’m wearing my corset, panties, garter belt and hose that I wore as Queen of the Night,” I said, as I removed my jeans and sweatshirt.

“Then you’ll need a dark skirt and top to cover the black underthings,” Becky said. “I have a dark green box pleated skirt and green blouse which you may borrow.”

“Thanks,” I said. “Oh,” I added, “I have your wig, and would like to wear that.”

“Sure,” Becky’s mom said.

We must have done a good job, because Joe was dutifully impressed. “You look wonderful,” he said when he first saw me. As he came closer to me he could smell my perfume. “You even smell wonderful,” he added.

Joe took my hand as we walked to his car. I could feel the breeze under my skirt. It was such a girly feeling, and Renee approved of it.

When we entered the theater, Joe kept my hand in his and steered us to the back of the theater. Joe sat in an aisle seat with me to his right. He kept my hand in his for a while. He then put his right arm around my shoulder and gently pulled me closer to him. I was enjoying this and rested my head on his shoulder.

Then I felt his left hand on my knee. “Stop that,” I hissed. He moved his hand away, but only for a while. His hand returned to my knee and began to slide up under the hem of my skirt. I had to admit to myself that it felt good, and after a few moments I took my left had and moved his had to the armrest of his seat. “Enough,” I whispered. He, however, kept hold of my hand, and shortly thereafter he had put my hand in his lap.

I jerked my hand away, and in a reproving voice whispered, “Any more of your antics, and I’m marching out of the theater and taking a taxi home.”

Joe was dutifully chastised and refrained from any more untoward touching, but only if I kissed him. I admitted to myself that I actually liked it when he touched me, but I realized that if I hadn’t stopped him things could very quickly get out of control.

As Joe drove to Becky’s house after first stopping off for pizza, he said to me, “I liked our date. How about you?” I just mumbled a response.

Joe pulled the car to the side of the street about a block from Becky’s house. “How about a kiss? Otherwise I’ll plant a big one on your luscious lips when I walk you to Becky’s door.” His threat worked, and we kissed. Frankly, I loved it.

Becky was home from her babysitting job when I walked through the door. We went to her room so I could change back to being Roy, during which time I gave Becky a full report.