This is the story of a year in my life. Well, maybe a little more than a year. It takes in from the middle of my junior year in high school, until the end of my senior year. It’s the story of my meeting the love of my life, Katie. And, what kind of trouble my brother got me into at the spring dance. Katie’s the love of my life, and we’ve learned a lot of things together. But, she had some ideas about Halloween that I wasn’t sure about. Then, Gwen go to the mall? Ah, I don’t know.
A Year In My Life
Part I-3
Saturday, September 30
It felt good being a senior. Knowing that there was a light at the end of the tunnel, at least until we went to college. What was really nice, I no longer had to walk Kate to school. I just picked her up at her house. And, being seniors, and only needing a few classes to graduate, neither of us had classes the last two periods of the day, so we could leave school early.
Jimmy Yamashita, or should I say Jackie Yamashita, looked just like any senior girl, and from what I saw everyone was treating her like a girl. And, she even sounds like a girl.
Kate had finally shown me the book that her mother had. And, it was an illustrated copy of the Kama Sutra. Now, Kate is in very good shape, and very limber, and I get a feeling that she wants to eventually try everything in the book.
We had just spend an hour in Kate’s bedroom, and as we lay their looking at each other, she said, “Halloween’s next month, we need to start figuring out what Gwen’s going to wear.”
“You really want to do this don’t you?”, I asked.
“You know it lover.”
“Why?”
“Like I said, it was fun the first time. And, I think we can make it more fun this time. Besides Gwen is cute.”
“More fun?”
“Sure. There’s two Halloween parties that we should go to.”
“Two?”
“Like I figured, there’s one at the country club the Saturday before Halloween. And, Ken Green is having one the Saturday after. So, you’ll only need two costumes.”
“Two?”
“You can’t wear the same costume to both parties.”
“Why?”
“The people that were at the first party, who are at the second, would know who you were.”
“So? Who’s going to the country club party, that’s going to be at Kens’?”
“Lover. Part of the fun is people not knowing who you are. And, who knows who’s going to be at both. Maybe no one.”
Kate and I went to a movie that evening, and afterwards we cuddled together in the pool house, enjoying a fire in the fireplace. After I left, and was on the way home, my cell phone rang, it was Kate, I answered it with a, “Hi.”
“Hi. Did I forget to put my mother’s book back?”
“No. After we read that one part, and tried it. You took the book back to her room, and I straightened up your bed. Why?”
“It’s sitting on my night stand.”
“You’re kidding?”
“No. I’ll try, and put it back in the morning. If they find out . . . ”
“It’ll be fine.”
“I hope. I’ll see you tomorrow.”
“Love you.”
“Love you too.”
Just as I was crawling into bed, my cell phone rang, and it was Kate again, and again I answered it with, “Hi.”
“She knows.”
“Who knows what?”
“My mother. About us.”
“What about us?”
“Having sex.”
“Are you sure? How do you know?”
“Yea, all most sure. I looked at the book, and it’s new. And, there was a slip of paper sticking out of it.”
“A slip of paper?”
“Yea. A note from my mother.”
“And, it says what?”
“Just, ‘Kate. We need to talk. Mom’”
“Maybe she thinks you were curious, and was just reading her book.”
“Yea. But, she knows that I was snooping in her room. And, that I found her other things.”
“Other things?”
“That’s not important. What do I do?”
“I guess, have a talk with her.”
“That could be interesting.”
Sunday, October 1
I was jarred out of a sound sleep, by my cell phone ringing. It was Kate’s special ring, and I answered it with a “Good morning. I hope.”
“Good morning yourself.”
“What time is it?”
“A little after ten.”
“What are you doing up so early?”
“I wanted to talk with my mom this morning.”
“A talk?”
“Yea. Remember the book?”
“Oh. Yea. The book.”
“Come on. Wake up.”
“Sorry. So what happened?”
“I’ll tell you when I see you. But, it was interesting.”
“Is she mad?”
“More over me snooping in her room, then anything else. Want to go to the park this afternoon?”
“Sure. Is it safe to come over?”
“Sure.”
When I picked up Kate at two, I saw her mother, and there was nothing other then the usual pleasant talk between us. We headed to the park. And, after we’d hiked to the waterfall, we sat, and she cuddled up next to me. We sat there quietly for a while. Finally I said, “Are you going to tell me?”
“About what?”, she asked.
“The talk.”
“Oh. The talk.”
“Yes.”
“I was a little afraid of this talk. But, it went better then I thought it would. I waited for my dad to leave for his golf game, before I came downstairs. And, my mom was sitting in the kitchen, and I just flat out asked her if she wanted have a talk.
“The first thing she asked me was if I’d been in her room looking through her things, and I just told her that I had. She got on me about people’s privacy. I told her that I was sorry, and I wouldn’t do it again.
“Then I asked about the book. And, mom said, that she had noticed that hers had been moved several times, and thought that getting me my own copy might open up a way for her and me to talk about sex. Then she came right out, and asked me if you and I were having sex. And, I just told her yes.”
“I’m dead.”
“No, you’re not. Let me finish.”
“Sorry.”
“She said that she was a little disappointed that I broke my promise, but was happy that I had waited as long as I had. I told her that I had waited as long as I could, and that was until your eighteenth birthday. And, that it wasn’t you that started it, but me. She asked if I was on any kind of birth control, and I told her of course I was.
“Then she told me that she a little unhappy, but wasn’t surprised, that we had started to be intimate, but was happy that we were taking precautions. Then she went on to tell me that there was just something about the women in this family. She mentioned Wendy becoming sexually active at fourteen. And, Wendy’s younger sister, Amanda, when she was fifteen. And, she told me that she knew my older brother, Zack, was active at sixteen. Then she admitted that she had been sexually active, like Zack, at sixteen, and so had her sister, Vicki. All this, except Wendy, was news to me.
“So, I got all the family dirt. She also told me that they had asked me to abstain because they didn’t want me to become pregnant. But, she said, that they were very happy that I had found you, and had accepted that we were going steady. And, that they liked you very much. I told her that I was glad, because I was in love with you. And, she just looked at me for a few seconds. Then said, that they had wondered about that.”
I just sat there for a minute. Then I asked Kate, “She didn’t say anything about us stopping, did she?”
“No she never even hinted at it. But, she did mention that we were eighteen. I did ask her why the book, and she told me it was to help her and me open up to talk about sex, and the relationship between men, and women. And, she told me that you and I should both read the book. Then she told me, that when dad had gotten her the book, that she though it was funny, but she actually read it, and so did he. And, it’s made a big difference in their love life.
“She suggested that we read it together”
“I always thought that your parents were a little straight laced.”
“I did too. But, I guess what happens in the bedroom . . . “
“Is she saying that it’s all right for us to have sex?”
“I’m not sure. But, it sure looks that way. Maybe she’s telling us that she feels we’re old enough, and mature enough, to make up our own minds on such things.”
We sat there a little longer, then started walking back to the car. As we were walking, Kate said, “I also told her that Gwen was coming back. And, she asked me who Gwen was? I reminded her that it was your girl’s name when you went to the dance. And, she asked, why you were going to be using it again. I told her that you wanted to go out to a couple of Halloween parties as her.”
I said, “You told her I wanted to?”
“You do, don’t you?”
“Yea. Kind of. But, whose idea was it?”
“Ours.”
“Whose?”
“All right. Mine.”
“And, why did you tell your mom?”
“We’re going to need to get you ready, and we’re not going behind her back again.”
Tuesday, October 3
As Kate and I were leaving school today, she asked, “Do you have anything important to do right now?”
“No.”, I replied, “Why?”
“There’s some place I want to go.”
“Where?”
“You’ll see. Head toward the airport.”
I followed her instructions, and before long we were at a costume shop. And, I said, “Why here?”
“So we can get some good Halloween costumes before they get picked over.”
“I should have guessed.”
We walked into the shop, and started looking around. This was a big shop, that had almost everything you could think of. We walked up and down the isles looking at women’s costumes. Kate would stop every once in a while, and take a close look at something. We looked at all kinds of things, witches, cowgirls, Cinderella, school girls, scary things, kimonos, etc.
Kate finally headed back to where we’d seen the witch’s costumes, she took one off the rack, and held it up. It was, as you’d expect, black, but it was also very low cut, and very short. Kate shook her head no, and put the dress back on the rack. She picked up another one, looked at it, looked at me, looked back at the dress, and put it back on the rack. She picked up a third dress, looked at it, and said, “Hmm. I like this.”
I just looked at her, and said, “At least it’s long.”
The dress was, of course, black, but it had a sparkle to it, long see through sleeves, the skirt looked like it might hit me just below the knees, then there was a longer see through outer skirt that looked like it might reach the floor. And, it wasn’t cut too low.
“We’ll look good in these.”, Kate said.
“We?”, I asked.
“I thought that we’d go to the country club party as twins.”
“Twins. Now, that would be different.”
Just then one of the clerks walked up, and said, “Hi. Can I help you with something?”
Kate said, “Yes. Would you happen to have this in his size?”
The clerk looked at me, didn’t even ask what size I wore, and said, “I think we might.”
And, she started looking through the rack, and pulled out a couple of the witch’s costumes. And, said, “One of these should fit, and he can try them on. If he wants.”
“He will.”, Kate said, “Now, how about the same one to fit me.”
She looked at Kate for a second, then pulled two more costumes off the rack, and said, “One of these two should work. Let me show you to the dressing rooms.”
The clerk took us back to the dressing rooms to try them on, and she was going to put each of us in a separate one. But, Kate asked, “Is there room for both of us in one room?”
“Sure.”, the clerk said.
She showed us into one of the rooms, and said, “Let me know if you need any help.”
After we closed the door, Kate said, “You first lover.”
I just looked at her, and she said, “Go on. It won’t hurt.”
I took off my shirt and pants, and Kate helped me into the first costume. She zipped it up, looked it over, and said, “Lets try the other one.”
She unzipped this one, helped me out of it, and into the other one. She again looked it over, and said, “This one will work.”
Kate then took off her blouse and pants, and was standing there in her bra and panties. I couldn’t help but smile at her, and she said, “What are you grinning at?”
“You look so cute in just panties and a bra.”
As she slipped on her costume, she said, “Behave, and zip me up.”
She looked at herself in the mirror, and just nodded yes. We helped each other out of the costumes, and got dressed. As we walked out of the dressing room, the clerk walked up, and asked, “How did they look.”
Kate said, “Great. We’d like to reserve these for the weekend before Halloween.”
“That shouldn’t be a problem.”, and with a grin, she added, “You guys going to be twin witches for Halloween.”
“Yea. We thought it might be fun.”
“That should be cute.”
“And, we’re going to need two more costumes for the week after Halloween, for another party.”
“Twins again?”
“No. Something different, and sexier.”
“Lets get these reserved for you, then we can look for something.”
As she was writing up the reservation, the clerk said, “There’s a witch’s hat that goes with these. Did you see anything that you liked?”
Kate thought for a second, and said, “Yes. There was one where the tip of the hat was curled up, and it had some black feathers on it.”
“I know the one. So, two of those?”
“Yes.”
Then we started looking through the woman’s costumes again. And, Kate was looking at some very sexy school girl costumes. She picked one out for herself, that the clerk said was based on a Harry Potter character. It was a very low cut gray dress, with a very short skirt, that was pleated at the bottom. It also had black cape with attach white collar, and yellow and red neck tie. I could see a smile come over Kate’s face as she looked at it, and I said, “I hope that’s not for me.”
“No way lover. You look sexy in a dress, but this one is a little too low cut for you.”
“And, maybe you too.”
“Jealous?”
“Yea. I also don’t want anyone else seeing that much of you.”
“Love. Look at some of the bathing suits I wear.”
“I have.”
She just smiled. The clerk pulled a couple of these costumes out of the rack, and set them aside. Then Kate started looking at other school girl type costumes. After she had looked at a few, she turned, looked at me, grinned, and said, “If you had breasts, and cleavage, this would be so much easier.”
I just looked at her, then said, “Well, I don’t.”
The clerk overheard us, and said, “We can help with that.”
I just looked at her. But, Kate said, “How?”
“We have some really nice prosthetics.”
“Maybe later.”
Kate finally found something for me that she really liked. It was a short pleated, plaid, skirt, with plaid suspenders. The blouse that came with it was a little too see through. But, the clerk said, “You can use a regular white blouse with that. And, it would still look great. And, it comes with a pair of white thigh high patterned nylons.”
Kate just smiled. And, we took these back to the dressing room to try them. Kate looked really sexy in hers. But, mine, in my opinion, was way too short. But Kate said, “With a pair of satin panties, it’ll be perfect.”
“Who’s going to see the panties?”
“With a skirt that short. A lot of people.”
I just looked at her.
As we were reserving these costumes for the weekend after Halloween, the clerk looked at me, and said, “So, you’re going to be a girl for Halloween week?”
“Ah . . . no. Just for the two parties.”, I answered.
Kate looked at me, and said, “Hmm. All week. That could be fun.”
Again, I just looked at her.
As we were about to leave the costume shop Kate, she said, “You know, I was thinking of using some spray hair coloring to give both of us black hair for the witch’s costumes.”
“That would work.”
“No. Not really.”
“Why?”
“I want us to be twins. And, your hair is much longer than mine.”
Kate was right. She kept her hair short because of all the swimming she did. And, mine hadn’t been cut since the dance in May, and would lay on my shoulders when not in a pony tail. So, I said, “They’ve got some nice wigs here.”
We looked at the wigs, and Kate saw a couple that she thought would work. So, we tried on a couple different ones, and settled for one that was long, straight, black, and went well below either of our shoulders.
As we were driving back to Kate’s house, she said, “Now, all I’ve got to find us are some shoes.”
“They had some at the costume shop.”, I said.
“I saw those, but didn’t like any of them.”
“It’s a shame that Mary’s away at college.”
“But, her mother isn’t.”
“You wouldn’t?”
Sunday, October 22
The past three weeks had been the usual things, school, dates, and the like. But, today I was going to meet Kate at her house, and as she had told me last night, ‘It was time to start finding Gwen.’
I got to Kate’s at about one, and she met me at the door. As we walked through the house, we found her mother in the kitchen, and with a grin, she said, “Have fun you two.”
Kate smiled at her.
Then, as we went out to the pool house, I asked, “I take it, you told your mom?”
“You knew that I’d told her that you were going to be Gwen for Halloween.”
“But, that grin?”
“I told her that we were going to start to get you ready, and she thinks it cute.”
“What’s with everyone thinking that this is so cute?”
“Because it is.”
I just gave her one of my, yea right, looks, then gave her a very long, deep kiss, and said, “All right, what do we have to do, and why are we starting so early?”
“We’re starting this early, for two reasons love. First, you need to get use to walking in heels. And, I want to work on your look.”
“So, I didn’t have any problems with the heels that I wore at the dance.”
“The shoes that I have for us to go with the witch’s costumes, are a little higher than the ones that you wore for the dance. And, so is the pair for the school girl’s costume.”
“Higher?”
“They both have about a four-inch heel.”
“Four inches! That’ll make me six feet tall.”
“I know. I had to find a pair for me, as close to yours as I could, that were even taller. Mine have platforms, and will just get me to five-eleven.”
“So, get me a pair with a shorter heel, and we’ll be the same height.”
“Wouldn’t look right.”
“So, what are we doing?”
“First, I got a hold of the shoes that you wore to the dance. So, you can start wearing those to get use to heels again.”
“How did you get those?”
“Mary’s mom.”
“Mary’s mom?”
“I called Mary at school, and told her what we were doing. She called, and talked to her mom. And, her mom is cool with it. She thought it was cute.”
“Not another member of the cute club?”
“It’s also where your other two pairs of shoes came from. She had a black pair that looks almost like a pair of platforms that I found. I just hope that they’ll fit.”
Kate gave me the shoes that I had worn at the dance, I put them on, and fastened the ankle strap. Then Kate brought out a small case, set it on the table, and took out a bunch of makeup. I walked around for a little while, and Kate watched me. Finally she said, “Not too bad in those heels’ lover. Just remember, small steps, and heel in front of toe”
“I didn’t have any problem with them last time.”
“Just wear them for a while. Then you can try the higher ones.”
“But, why all the makeup? We’re going to be wearing masks.”
“But, people will still be able to see your eyes, and most of your face, including your lips. So, they have to look good. Besides, they’ll probably have us take off our masks at some point.”
Kate began by working on my eyebrows, and she really worked on them. To the point that I was worried that she was doing too much. As she was working, she said, “We shouldn’t let them get this bad.”
“Why?”, I asked.
“Because they really do look better if you keep them neat.”
Once she was done with my eyebrows, she went to work on the rest. Moisturizer. Foundation. Eyes. Blusher. Lipstick. And, she spent a long time on my eyes. When she was done, she took a long look. Then said, “Not bad. I love the blood red lipstick on you. But, we need to go a little heavier on the eye shadow. And, with a black wig I think it’ll work. I just wish your eyes weren’t blue. But, I guess I’ll be the green eyed witch, and you’ll be the blue eyed witch.”
She took my hair out of the pony tail, brushed it out a little, handed me a large hand mirror, and said, “Take a look.”
I looked in the mirror. There was Gwen again, but with a sexier look, and this time I didn’t look that much like Anne. I wasn’t sure who I looked like. Maybe this was Gwen. What Kate and Mary had done for the dance, was the makeup a seventeen year old girl would wear for a school dance. This new look was very mature, and very sexy. I looked at Kate. She smiled, and said, “Welcome back girlfriend.”
“Again, the girlfriend thing?”, I asked.
“Sure. Girlfriend. And, you do look very nice.”
“I do?”
“Yes. And, you don’t look that much like Anne this time.”
“I know.”
“It’ll be interesting to see how you look in the black wig.”
“What about the other shoes?”
“The pair for the witch’s costume are ankle boots, with a four inch heel. And, that heel is a spike, and you’ll have to be careful.”
“Four inch spike heels. Are you sure about this?”
“Mine are spikes, with platforms. Want to try those?”
“No thanks.”
“I want you to walk around in the heels that you’re wearing a little longer, before you try the others.”
I did as she asked, and spent a good amount of time just walking around.
Finally Katie said, “Want do you think. Want to try the higher heels, and see if they fit?”
“Why not.”
Kate went, and got the boots. And, after seeing them, I wasn’t sure if I could ever walk in them. They were shinny black, and laced up the front to well above the ankle. And, Kate was right, they had a spike heel. I looked at her, and said, “Are you sure?”
“Just try them, and if they won’t work, we’ll find something else.”
I took off the heels that I was wearing, took the boots from Kate, and unlaced them. I slipped the right one on. It was a little tight, but not bad. I started lacing it back up. There were twelve metal loops on either side. And, as I tied the bow, I looked up at Kate, and asked, “Where does Mary’s mom find shoes like these? And, why?”
“I don’t know, and I didn’t ask. But, you should see her closet.”
I then put the left one on, laced it up, and tied the bow. I again looked up at Kate.
Kate asked, “Want to try and stand up?”
I reached my hands out to her, and said, “Help me.”
She reached out to me, and helped me stand. It was a weird feeling standing up in four inch heels. But, I did it.
Kate continued to hold my hands to steady me. Then she said, “Just move around a little bit. Try carefully to turn side to side.”
After I’d done that for a little while, she said, “Now try to take a few steps.”
I did, with her still holding my hands. I was a little unsteady. But, Kate said, “You’re doing fine. But, remember to keep your legs straight and as close together as possible. Point your feet as straight in front of you as you can. It just takes practice.”
“Yea. Years of practice.”, I said with a smile.
“No. You’ll be surprised on how quickly you get use to them.”
She continued to help me walk around. Giving me encouragement. Finally she said, “All right. Now try it without hanging onto me.”
I let go of her hands, and carefully took a couple of steps. I felt a little off balance at first, but the more I walked, the better I did. She keep repeating, “Small steps. One in front of the other. Keep your legs together.”
I was amazed. In a very short time, I almost felt comfortable in the heels. Maybe too comfortable, as I got stupid, tripped myself up, and fell. Luckily, I didn’t hurt myself. Kate helped me back up, and said, “Tried to do too much love?”
“Yea. But, actually these shoes don’t feel too bad.”, I said.
“Just wait until you’re in them for a few hours.”
“Why?”
“Your feet will be killing you.”
“Then why do girls wear them?”
“To look sexy for the men.” It wasn’t Kate that had answered, both Kate and I looked at the door to the pool house, and it was her mother. And, she continued with, “I’m sorry kids. But, I was curious, and had to see.”
“That’s all right, Mrs. Branson.”, I said, forgetting how I looked, “Come on in.”
Kate’s mother walked over to us, and took a close look at me, then said, “So, this is what Gwen looks like. The pictures in the paper didn’t do you justice, and this is better then what I saw last time.”
“This is her new look. The one for the party at the country club.”, Kate said.
“So, you’re really going to go?”
“We’re planning on it.”
“You know we’ll be there, and so will Gary’s parents.”
“Yes.”
“As long as you know. But, in looking at Gary, I don’t think I’d recognize him especially in a costume.”
“We’ll see. But, no cheating. You know what our costumes are. So, no telling.”
“I won’t. Just be careful in those shoes. We don’t want you in a cast for the party.”
“Me either, Mrs. Branson.”, I answered.
“That’s why he’s going to be in them every day after school until the parties are over.”
“I am?”
“Yes. You need to be able to dance with me.”
“Am I going to lead or follow?”
“I don’t know.”
With a big grin, her mom said, “I’ll leave you two girls alone.”
“Thanks mom.”, both Kate and I said. Then all three of us laughed.
After her mother had left, Kate said, “Mom?”
“It just came out.”, I said with a big grin.
“All right, back to work. Keep walking.”
“Yes master.”, I quipped.
It wasn’t too much later we heard her parent’s car pull out of the driveway, and Kate said, “They’re off to the country club again.”
“They live there. Don’t they?”
“It seems like it. You hungry?”
“Kind of.”
“Where do you want to go?”
“Looking like this? No where.”
“Why? You’d pass.”
“Maybe from the neck up and knees down.”
“Neck up? Yes. Knees down? No.”
“No?”
“Yea. Your legs are hairy again.”
“Are we going through that again?”
“You got it love.”
“Come on. Lets get Gary back, and I’ll take you out for something to eat.”
“Okay.”
I sat down, to take off my shoes. And, as soon as I had them off, Kate leaned over, and kissed me. A very soft, gentle, kiss. As usual I returned it. But, she stopped me, and said, “Girls don’t kiss that way. Try again.”
I kissed her again, this time trying to be softer. She let me kiss her a little longer, then pushed me away, and said, “Better. But, be softer. Hold me like I’ll break if you squeeze too hard.”
I tried again. This time she didn’t push me away. But, we sat there, and kissed very softly for a long time. And, our touching was also very soft. And, that led to . . .
It was a good hour later that we finally had all my makeup off, and were on the way to Greg’s Drive In. As we pulled in the parking lot, we sat there for a minute, I turned, looked at Kate, and I said, “Katie. I’m confused.”
“About what love?”
“Why you want me to kiss like a girl?”
“It’s to help get your mind to think like a girl. To think soft. To think gentle. To think pretty.”
“But, we had sex with me looking like a girl.”
“So?”
“A little weird maybe?”
“No. I knew who was there. Who I was making love to, and who was making love to me.”
“But, my face was a girls.”
“But, you’re still my Gary underneath. Aren’t you?”
“Of course.”
“Do you remember what I told Mary about you before the dance?”
“I think?”
“That, I love Gary when he’s Gary. And, I love Gary when he’s Gwen.”
“Yea. I remember that.”
“What I was saying was that I love you for what’s in your heart. And, I don’t care what you look like.”
“But, the softer, gentler, thing?”
“What’s wrong with being that way? You don’t have to be macho for me. I have my big, strong, Gary when I need him. But, there are times, that I need your softer, gentler, side. Your Gwen side.”
I looked at her for a few seconds, took her face in my hands, and gave her a very soft, gentle kiss. When we broke the kiss, we just looked at each other, finally she smiled, and said, “I love you.”
Friday, October 27
After school today, I figured that I’d be back in the boots. And, I was right, but it didn’t happen right away. As we walked into the pool house, Kate said, “We need to get rid of some of your body hair.”
“Do we really have to do that?”, I asked.
“Your legs are hairy, and you know how bad that looks in nylons.”
“Yea. I guess.”
“In fact . . . “
“In fact. What?”
“I think we need to do your arms too.”
“No. Why?”
“Look at your arms, then look at mine.”
I looked, and said, “Yea. So.”
“How hairy are mine?”
“I don’t see anything.”
“And, yours?”
“They have some hair.”
“How do you think they’d look in the costume?”
“I guess, not so good.”
“So.”
“Go ahead.”
“All right into the changing room, and put on your Speedo this time. Not mine.”, Kate said with a grin.
About half an hour later, I was back in the heels, and we were practicing dancing. And, I was minus the hair on my arms, legs, and chest. Kate even wanted to do the rest of my body, and I was able to talk her out of doing everything but my chest, as the costume did show some bare skin there. But, she said, “We just might have to do more for the other costume.”
Saturday, October 28
The past week, I had been wearing the heels whenever I was at Katie’s, and had gotten fairly comfortable in them. Kate had also worn her heels a couple of times, so we could practice slow dancing. When I led, it was fine. But, when she led for the first few times, we both had problems. We worked on it, and it didn’t take us long to get to the point where either of us could lead, or follow. She’d reworked my makeup, and went heavier on the eye makeup. And, she was very happy with the look.
This morning, Kate had gone over to the costume shop to pick up the costumes. And, when I arrived right after an early dinner, she had everything setup in the pool house. Including a fire in the fireplace. She walked up to me, and gave me long, deep, kiss. Then she said, “Are you ready to become a very sexy witch?”
“Why?”
“Because you can.”
“And?”
“Because, I love you.”
I smiled, and then she said, “All right lover. We don’t have all night. Out of the boys clothes, and into the girls. So I can do your makeup.”
She handed me a black bra and panties set. I looked at it, and said, “Black. Didn’t I wear white for the dance?”
“Yes. But, you can’t wear white under black. So, now you have two sets of underwear.”
I just shook my head, and said, “Two sets of girl’s underwear.”
It was her turn to smile.
I undressed, and slipped on the panties. I never realized that girls underwear was so soft, and comfortable. Then Kate helped me with the bra, while saying, “You need to learn to do this yourself.”
I didn’t say anything, but just shook my head.
“All right love, have a seat, and we’ll get started.”
I sat at the table, and she went to work on my nails. Like for the dance, she added fake nails over the top of my own. But, these were blood red, to match my lipstick. Then she took my pony tail out, and put something over my head, and I asked, “What’s that for?”
“It’s a wig cap.”, Kate answered, “It keeps your own hair under control, so the wig will work.”
“Oh.”
Kate then worked on my makeup, and it seems to take her less time each time she does it. When she was done, I looked in the mirror, and there was that girl again. Gwen. But, Kate had added something to the makeup, and I asked, “What’s the black mark for?”
“Every witch needs a mole.”, Kate said with a smile.
Then she handed me a necklace, and earring set. The necklace was a spider, and the earrings were smaller spiders. As she fastened the necklace around my neck, she said, “I got us matching sets.” Then she put the earring on my ears.
I looked down at my bra, and said, “Don’t I need something in these?”
“Oh yea. I borrowed something else from Mary. And, her mom didn’t even know she had them.”
Kate got the three boxes of enhancers, and handed them to me.
I looked at them, and then at her. And, I guess the look was a puzzled one, because she said, “You’re helpless. Give ‘em here.”
I handed her the boxes, as I said, “Gee. Sorry if I don’t know what to do with these. I’ve only had them on a couple times.”
“I’m sorry.”
“It’s all right.”
She put the three sets of enhancers in my bra, smiled, and said, “That’s better.”
“Don’t they make these so you don’t have to use three sets of them?”
“Yea. But, I think they’re very expensive.”
“But, wouldn’t it be easier?”
“Yea. And, it would probably feel better.”
Kate then undressed, and put on a bra and panty set that matched mine. Then sat at the table, put on a wig cap, and went to work on her own makeup. I sat there, and watched her. It amazed me on how quickly, and expertly, she did it. When she finished, she turned, looked at me, and smiled. Her makeup was flawless, and was a duplicate of mine, right down to the mole. She said, “Want to learn?”
“Learn what?”, I asked.
“To do your own makeup.”
“Ah. No. I don’t think so.”
“I’ll teach you.”
“No.”
“It’s not that hard.”
“Sometime. Maybe.”
She added the same necklace and earrings that she had put on me, except her earrings were for her pierced ears, and it looked really sharp.
Then she said, “Wait until you see what else I got at the costume store. You’ll just love them.”
“What did you find now?”, I asked.
She walked over to where she had the costumes, and came back with two packages. She handed one to me, and it was pantyhose. But, these had a pattern. A pattern of spider webs. And, she said, “I thought these would look so cool.”
I looked at them, and said, “You’re right. I think these will look cool.”
“So get them on. And, be careful with them.”
I sat down, and carefully started putting on the pantyhose. Again, the interesting feeling of the nylons on my hairless legs. I stood up, finished pulling the pantyhose up, and smoothed them out. I could see a smile on Kate’s face, as she said, “That looks so good.”
Then she said, “Better put your boots on before we get you into the shaper.”
“I have to wear the shaper?”, I asked.
“Sure. Got to get a feminine shape to your body.”
“You didn’t get me a new one of those too? Did you?”
“Can’t wear white under black.”
I just shook my head.
Then Kate said, “You’d better hit the restroom. And, there’s a pad in there for you to use.”
I sat down, put the high heeled boots on, got up, and walked toward the changing room.
Kate said, “Girlfriend. You walk in those heels like you were born in them.”
I turned, looked at her, grinned, and said, “Well sweetheart, I was.” Then I continued walking toward the changing room.
Kate added, “And, you’ve got a cute little wiggle.”
I just kept walking. When I came back out, Kate had put on her pantyhose, and boots. And, she was right, the pantyhose were cute. She was also waiting with my shaper, a new black one, and helped me into it. Again, it was very tight. Then she disappeared into the changing room, and when she came back, she put on her shaper.
Then I watched as she put on her own wig, and brushed it out. When she turned around, she really looked different. The makeup, and black wig had really changed her look. She was sexy to start with, but this look . . .
“All right lover. Let’s get your wig on.”
I sat at the table, she put the wig on me, and brushed it out. She spent a little longer on me, then she had on herself. Then she said, “Take a look.”
I turned, and looked in the mirror. And, just like with Kate, the wig made a big difference in how I looked. I didn’t see me any longer, but I saw a girl, a pretty girl, with black hair. I turned, looked at Kate, and I guess the look on my face made Kate ask, “What?”
“I just look so much like a girl.”
“So?”
“I’m a guy.”
“Yes you are. And, you can make yourself look like a girl. It’s something that I think is cool.”
“But, won’t people start wondering about me?”
“Wondering what?”
“That I might be . . . I don’t know. Maybe strange.”
“Lover. How do you feel about it?”
“Honestly?”
“Honestly.”
“What scares me, is that I am beginning to like it. It’s fun doing it with you. The clothes feel very nice. I just worry about what others think about it.”
“What’s important is how you feel about it. How you feel inside. And, I do love doing this with you. It’s fun.”
I sat there for a few seconds looking at Kate, then said, “You’re right. It has been fun. The humiliation that I felt at the dance, went away when people reacted the way they did. And, no one has treated me any differently. And, I can look like a pretty girl, so I guess, why not do it.”
“See. You do like doing this. So, just do it. Now, I’ve got something else for you.”
“What?”
“You’ll see. But, lets get your dress on first.”
Kate helped me into my dress, zipped it up, stood back, and just grinned. She then said, “That looks so good. Gwen, you are one sexy witch. Now help me with my dress.”
I helped her into her dress, took one look, and then said, “We’re not going.”
“What! Why?”
With a big grin, I said, “I don’t want anyone seeing my girlfriend looking so sexy.”
“Gwen!”
“Sorry.”
She walked over to the table, and back, then said, “We need purses. And, these fit the costumes.”
She handed me a purse shaped like a coffin. And, she had a matching one. I just smiled at her, and said, “I don’t know about you.”
“One more thing, then we can head for the country club.”, she said.
“What now?”
“Our hats. We need to see how we look with them on.”
She got the hats from the table, and we tried them on. The witch’s hats with the curled up top, looked really good with the rest of the costume. Then she handed me a mask. It was black with a silver spider web design on it. I carefully slipped mine on, and looked in the mirror. Kate asked, “Know who you’re looking at?”
“No. Who?”
“A very sexy witch. And, this sexy witch wants that sexy witch. And, if we don’t get out of here soon, I won’t be responsible for what happens.”
As we got out of the car in the parking lot of the country club, we had to get our hats out of the back seat. There was no way we could sit in the car, and wear them. So, before we walked to the building, we helped each other arrange our hats, check our makeup, and put on our masks. Then, as we walked up to the door, the door man opened it for us, and said, “Good evening ladies.”
Kate said, “Thank you.”
And, I just smiled.
Katie whispered to me, “Feels good being called a lady. Doesn’t it?”
We walked into the ballroom, and there were a number of people there. Most of them were our parent’s age, some were older, but there were also a few couples our age, or a little older. The band was good, Kate and I enjoyed a number of dances, and we were both asked to dance by others.
And, unlike at the spring dance, we knew there was a photographer. We allowed her to take a number of pictures of us. And, we knew she also took candid pictures of the crowd from time to time. So, we figured that we’d probably have pictures of these costumes.
Everyone gave us the once over, but it didn’t appear that anyone recognized us, except Kate’s mother. After we had finished one of our dances, she walked over to us, and said, “Hi kids.”
“Hi mom. You didn’t tell, did you?”, Kate said.
“Not really. You both look really great. And, if I didn’t know this was Gary, I’d swear she was a girl.”
“It’s fun helping him dress like this.”
“Your father never figured out who either of you were. But, he asked me if I knew who the two witches were. I looked at you two, and told him that one was his daughter. It was funny when he looked back over at you, and said that he thought that Gary was coming with you. His voice just trailed off as he figured that one of the two of you was Gary.”
“Did he say anything else?”
“Yes. He’d been dancing with everyone, and said he was just about ready to come over, and ask Gary, sorry Gwen, to dance. I asked him why he just didn’t do it. That I thought that she’d be happy to dance with him.”
I looked over at Kate’s dad, and smiled. He just looked at us for a few seconds, then walked over. Kate and I were standing side by side, and he had actually asked Kate to dance, but I beat her to it, and said, “I’d love to.”
His eyes got really big, but I took his arm, and walked him toward the dance floor. He was a little stand offish to start with, but he actually relaxed as we danced. I saw Kate and her mom watching us, and Kate was trying very hard to keep from giggling. Kate’s dad finally said, “Gary. I don’t know about you son. You just look too good as a girl.”
“Thank you, Mr. Branson.”, I said, “Katie worked hard at doing this. And, it’s been fun.”
We talked some more, and the more we danced, the more he relaxed with me. We finished the dance, and as we were walking back to where Kate and her mom were. I saw my parents talking to them. As we walked up, Kate’s dad said hello to my parents. And, my mom, who’d figured out who Kate was, asked her where I was. Kate got a big grin, looked at me, and said, “Don’t you recognize Gary.”
My mother looked at me, and said, “Gary!?”
“Hi mom. Dad.”
“Gary!”
“Well, tonight it’s Gwen.”
“You . . . You look really nice.”
“Thanks mom. Katie really gets all the credit.”
“I didn’t think you were going to do this again?”, my dad said with a very straight face.
“I did to. Until Katie and I talked about Halloween. Then we figured it would be fun.”
“Well, I guess it can’t hurt, and it is Halloween. And, it does look like you’re having fun.”
“We are. The four of you are the only ones, so far, that know I’m a guy. I don’t think anyone else has figured it out.”
“So, twin witches.”
“Kate’s idea. We though it would be fun to come here, and see how many people can figure it out.”
“And, you can walk in those shoes?”, my mother asked.
“Yea. It took a lot of practice.”
Now, there were some good costumes here. My parents were a cowboy and cowgirl. It was actually a little lame. Kate’s parents went a little further, and made a half way good looking Anthony and Cleopatra. There was another guy there dressed as a girl, and his date was dressed as a guy. He was a big guy, and it wasn’t hard to tell. But, his date made a half way good looking guy. Plus all the other costumes that you’d expect to see around a Halloween party.
One reason I didn’t like coming to things at the country club, is that someone always gets drunk, and made a fool of themselves. And, it happened this time. One guy, who was dressed as a clown, was getting drunker and drunker. And, he picked on Kate and me. He wanted to dance with both of us at the same time. We kept saying, sorry, thanks but no thanks. But, he kept insisting, and got louder and louder.
Finally this guy’s wife came to our rescue, and dragged him away. She came back later, and apologized for him. I told her, “That’s all right. I don’t think he would really like to dance with a guy.”
“You . . . You’re a guy?”, she said.
“Yes.”
“God. You make a pretty girl.”
“Thank you.”
“Wait till he sobers up, and I tell him. He’ll have a stroke.”
We watched as she walked back through the room telling everyone she knew that I was really a guy. She’d stop, say something, and point. And, who ever she told would look in our direction.
I whispered to Kate, “Now you know why I don’t like to come here.”
Kate said, “I see what you mean. Everyone in the place is going to know you’re a guy.”
“And, it’ll only take five minutes.”
“If that long. Want to go?”
“Yea. Lets say goodbye to our parents, and get out of here.”
We found our parents sitting together at a table, and my dad asked us what all the commotion was about. We told them about the drunk and his wife. And, Kate’s dad said, “Mr. O’Riley?”
I said, “I think. It was the guy in the clown suit.”
“It was him, and it figures. They need to ban him from here.”
Then my mom asked, “What are you kids doing tomorrow night?”
I looked at Kate, then said, “Nothing that I know of. Are we Katie?”
“No. We don’t have anything planned. Why?”, Kate asked.
“You two want to hand out candy tomorrow night?”
“Tomorrow night?”, I asked.
“It’s Trick or Treat.”
“Oh. Well. Yea. What do you think Katie?”
“That would be fun.”, Kate said, “Aren’t you going to be home, Mr. and Mrs. Cutwright?”
“Yes. But, I thought it would be more fun to have two witches hand out the candy.”
“Mom! You want us to hand out candy dressed like this?”, I asked.
“Sure. I figure the children would have fun with it. And, the two of you did go to a lot of work to look this good. And, you need to show it off more.”
Katie squeezed my hand, and said, “The costumes don’t have to be back until Monday. So, I guess we could.”
“Well. Okay. We’ll do it.”, I said.
After we had said our goodnights, and were walking to the car, I said, “Are you nuts.”
Katie took my arm, and said, “Yes.”
“But, dressing up again, and handing out candy.”
“Why not?”
“Because my feet are killing me.”
“I told you they would. So, you don’t want to be my sexy witch again?”
“Your sexy witch? Yes.”
“It’ll be fun.”
“I guess.”
“Did you see your dad’s face when your mom asked us?”
“No.”
“It was priceless.”
When we were back at Kate’s, and in the pool house. The first thing both of us did, was sit down, and take off our shoes. Then Kate found the remote, and started a fire. I looked at Kate, and said, “How do you wear these things for more than a few hours?”
“I don’t.”, Kate said, “You know I don’t wear heels very often.”
“I know, and I can see why. And, we’re going to do it again tomorrow?”
“It’ll be fine. We can sit down ever once in a while.”
“Yea. But, remember we’re dealing with little kids, and we’ll have to bend down, or something.”
“Oh. Yea. That’s right. We’ll survive.”
We started to help each other out of our costumes. I unzipped Kate, and she unzipped me. Knowing that we were going to wear them again, we carefully hung them up. Kate then took off her shaper, and helped me take mine off. Then I carefully took off the pantyhose, and watched as Kate took hers off. For some reason, it was very sexy.
After she had taken our pantyhose, and put them with the other things, she said, “Lover. Come on over here, and I’ll get your makeup off.”
I walked over to her, and instead of sitting down, I took her in my arms, and kissed her. It was a very soft, very gentle, and very long kiss. When we broke the kiss, she looked me in the eyes, smiled, and just said, “Gwen.”
I picked her up, carried her to our favorite couch, carefully laid her down, and . . .
A while later, we were laying there, naked, cuddled together, and Kate said, “That was wonderful.”
“I thought ever time was wonderful?”, I asked.
“It is. But, that was wonderful in a different way.”
“How?”
“We’ve never made love in such a slow, soft, gentle, way. It was just fantastic. Wasn’t it Gwen?”
“You told me that you like things soft and gentle when I was dressed as Gwen.”
“Lover. That was so wonderful that I thought I’d died, and gone to heaven.”
I gave her a very soft kiss, and she held me very close. She finally whispered, “Lover. We’d better get this makeup off, and you home.”
Sunday, October 29
I arrived home about one in the morning, and there were still lights on. When I walked into the house, my mother was sitting, and having a cup of tea. She looked at me, and said, “A little late?”
“Kate and I were talking.”, I said.
“Your father was very surprised with you. He wasn’t expecting you to dress up as a girl again.”
“I figured that from his reaction when he found out at the party. But, you really surprised me when you asked Kate and me to give out candy in costume.”
“It was just on a whim. The two of you looked so good together that I figured it would be fun to have you give out candy.”
“Katie said, that dad got a really funny expression when you asked.”
“He told me that he wasn’t happy to see you dressed as a girl again. But, it appeared that you were having fun at the party. And, he hasn’t said much about me asking you to give out candy in costume.”
“Would it be all right for us to change here tonight?”
“I don’t see why not. Why don’t you invite Kate for dinner?”
“She’d like that. How will dad feel about us changing here?”
“He’ll live with it. And, you know, you do make a convincing girl.”
“It kind of bothers me.”
“Why honey?”
“I’m a guy. I shouldn’t be able to look that good as a girl.”
“I know. But, you do. And, it looks like you and Kate have fun with it.”
“We do. A lot of fun. I just don’t want to upset dad.”
“You won’t. He’s more liberal then you know. And, I know you and Kate are very close. Where do you see your relationship going?”
“Huh?”
“Where do you see your relationship with Kate going?”
“Well . . . I’d really like to marry her some day.”
“Does she feel the same way?”
“Yes.”
That evening after dinner, Kate and I took the costumes, makeup, and everything else up to my room. Kate looked around, and said, “We need somewhere to sit, and do makeup. And, a mirror would be helpful.”
“Be right back.”, I said.
I ran downstairs, and asked my mother if we could use her room and her dressing table. Without hesitation, she said we could, but I noticed a strange look from my dad. And, as I was going back up stairs, I heard my dad ask my mom, “Why did you ask them to do this in costume?”
I didn’t stay around to listen to the discussion, but I told Kate when I got back to my room, “I think my dad is having a little problem with this.”
“Why?”, she asked.
“He just asked my mom, why she had asked us to do this in costume.”
“Do you think we should?”
“I don’t know. Lets give them a minute, and I’ll have mom come up.”
I waited a few minutes, then called down the steps, and asked my mother to come up to her room. When she had, I asked, “Is everything all right?”
“Yes. Why?”, my mom asked.
“Dad seems a little unhappy with Kate and me doing this.”
“He was. But, we talked. And, I think he understands.”
“Understands?”
“Yes. That the two of you see this as a fun thing to do. That you can do it, and look good doing it. And, that I think it’s a lot better then some of the other things that you could be doing. He was just worried that you were gay or something.”
I saw Kate get a little smile, and then say, “He’s not gay.”
My mother’s reaction wasn’t anything like I’d expected. She looked at Kate, and said, “I have heard that.”
“Huh?”, I said.
“Honey. Kate’s mother and I do talk. She told me about knowing, for a while, that you two were sexually active. And, it doesn’t surprise me.”
“Ah . . . Does dad know?”
“He’s never said. But, I wouldn’t be surprised that he does in his own way.”
“So, he’s not going to have a problem with us doing this.”
“No. I don’t think that he’ll admit this to you. But, he just told me that you two looked really nice last night.”
My mother left, and Kate and I got our costumes on. We spent about an hour and a half handing out candy to the kids, some small, and some big. Some in very cute costumes, and some, usually the bigger kids, in no costume at all. But it was fun. And, stooping down in four inch heels is an interesting experience.
After we were done, my mother asked, “Would you two like something to drink?”
“Sure Mrs. Cutwright.”, Kate answered.
We took our hats off, and followed my mother out to the kitchen. We sat, while she got us something cold. As we were sipping our drinks, my dad walked into the kitchen, and said, “I guess you two girls gave out all the candy, and there’s none left for me.”
I nearly choked, and said, “What did you say dad?”
“I said, that I figured that you gave out all the candy, and there wasn’t any left for me.”
“No. The two girls’ thing.”
“Oh that. Well, my son’s not here right now. I only see two witches.”
“Okay.”
“Son. If this is fun for you, and Kate. It’s fine by me. It’s just taken a while to sink in, that I have a son that can look like a daughter.”
I looked at Kate, and she was smiling. I looked at my mom, and she said, “See I told you that he wouldn’t have a problem with it.”
I looked at my dad, opened my purse, handed him a half a dozen mini Three Musketeers bars, and said, “I hid these for you. I know they’re your favorites.”
He smiled, and said, “Thanks.” Then, he sat down, and joined us.
We talked for a while, like a family. Discussing a number of things, including my dressing as a girl. First I reminded my dad that it had only been twice, the dance, and now for Halloween. And, that it was only clothes and makeup, and that I was the same person underneath. But, since Kate and I had fun with it, to not be surprised if it happens again.
It was a good hour after the last trick or treater had left that Kate and I finally went back upstairs to change. We helped each other out of our costumes, and shapers. And, like last night, we were standing here in panties and bras. Kate looked at me, and said, “You know, this is just like two girlfriends.”
“But, I want to be your boyfriend.”
She walked over to me, wrapped her arms around me, looked me in the eyes, and said, “Lover you are my boyfriend. And, you are my girlfriend. And, it’s fun.” Then she kissed me.
I knew we were both feeling the same way, but I figured that my parent’s bedroom wasn’t a good place to have sex, especially with them downstairs. We finally got dressed in our regular clothes, and everything packed into Kate’s car. She said goodnight to my parents, and she and I said a long goodnight.
Friday, November 3
Tomorrow was the party at Ken Greens’. So, the past week it was in heels again, and working on a look. The shoes were different then the witch’s boots. Kate called them a Mary Jane. They were a black patient leather closed toe shoe, with a strap across the instep, and the heels were only three and a half inches compared to four. And, the heel of the shoes was a clunkey heel, so no balance problems.
Kate had found a white blouse that would work with the short plaid skirt. The blouse had long sleeves with ruffled cuffs, and red trim on the cuffs and down the front. When I first tried it on, with a bra and the enhancers, Kate had unbuttoned the top two buttons. She stood back, shook her head, and said, “It sure would look better if you had breasts.”
“Lend me yours.”, I said, with a big grin.
She frowned at me. Then said, “That costume has a necktie with it that matched the skirt. Maybe that will camouflage your lack of cleavage. Because it would look better with three buttons undone.”
She had also started working on my school girl look. I didn’t need a wig, or to change my hair color, as my hair is already a dishwater blond, so she worked with my hair to see what she could do. And, she came up with something that she thought looked really good. She used a curling iron on it, to give it some curl. Then she mussed it up a little, and put two red bows in it. It fell across my face, and just made it to my shoulders. She loved this look.
Kate then worked on my makeup. She came up with a sexy look for my eyes. And, we settled for a really red lipstick, and made it as pouty looking as she could. And, the eyebrows took another hit, and I thought she’d gone overboard. My nails were again to be red, but redder than what I’d worn to the dance.
We weren’t going to wear masks to this party, but somehow she’d also come up with a pair of sexy wire rim glasses without prescription lenses in them. And, when we put all this together, it was a sexy look for Gwen.
This evening, we went out to eat, and to a movie, with a group of our friends. Then after the movie, Kate and I went back to her house. I had to get ready for tomorrow nights party, and that included hair removal, as my legs were getting stubbly. And, Kate wanted to be sure that I didn’t have any chest hair.
After I had gotten out of the shower, and before I had a chance to put my clothes, Kate handed me a package, and said, “Try these on.”
I looked inside, looked at her, and said, “Not another bra and panty set?”
With a smile, Kate said, “Love. A girl needs to be fashionable.”
I shook my head, and took the bra and panties out of the package. They were red. A bright red. And, they felt . . . Well, they felt very soft.
Kate then said, “They’re satin.”
“I guess.”, I said, “But, didn’t you tell me, no black under white, and no white under black?”
“Yea.”
“But, red under white. Won’t that show?”
“Sure.”
“But?”
“It’s part of the look. You want a sexy bra like this to be seen through your blouse.”
I slipped the panties on. Kate then helped me with the bra. I then said, “Who’s going to see these panties?”
“Under that short skirt, almost everyone.”
“I don’t have to wear the shaper. Do I?”
“Sure you do.”
“But, I wear the panties under the shaper.”
“Not this time love. We need to hide the shaper, and let everyone see your pretty panties.”
Kate looked me over, walked up to me, and gave me a deep kiss. And, in the middle of the kiss, she grabbed my butt, and pulled me closer. When we broke the kiss, she whispered, “Lover. You look so sexy in red panties.”
“And,”, I whispered back, “you look so sexy in nothing at all.”
“If my parents weren’t home tonight, I’d . . . “
“I know.”
Saturday, November 4
Kate had again picked up our costumes this morning, and we was having dinner with parents. So, right after dinner we started getting ready for Ken’s party.
I made the stop in the restroom, then put on the shaper. It felt funny putting the shaper on without panties. Then, as she was about to help me with the bra, I surprised her when I said, “Let me try it by myself.”
“All right.”, she said with a little smile.
“I’ve watched you put one on, and I think I can do it.”
She handed me the bra, I slipped my arms through the straps, reached behind me trying to find the ends of the band, and finally did. I took the ends of the band in each hand, and tried to pull them behind my back. With a smile, she watched me struggle for a little while, and then asked, “Do you want me to help you.”
“Not yet.”, I said, “How do you do this?”
“Practice.”
I struggled for a little longer, then said, “All right. I give up.”
“It does take a little work. You’ll get it. But, try this. Take the bra off, wrap it around you so the fastener is in front. Fasten it, spin it around, and slip your arms through the straps.”
I did as Kate said, and it was easy. So, I asked, “Why don’t you do it this way? It’s easy.”
“I’m just use to doing it the other way.”
I then slipped on the panties, and Kate put the enhancers in the bra. Then she went to work on my hair, makeup, and hands. When she had finished working her magic, Gwen was back. But, a blond, blue eyed, Gwen.
Then Kate worked on her look. And, as usual, it amazed me on how quickly she could change her look. She had gotten a long, curly, dark brown, wig to cover her own short hair. And, when she put that on, she didn’t look like Kate.
Kate then took a black satin bra and panty set out of another package. She slipped off her panties, and put the new ones on. Then she changed bras. This new bra, pushed her breasts up, and gave her some nice cleavage. I couldn’t help but smile at her new look. And, she asked, “You like what you see?”
“Very much.”, I replied.
Next came the costumes. I helped her into hers, by zipping up the back. She fastened the collar with attached cape, and neck tie, around her neck. And, she looked really sharp.
I put on the blouse, and had a little problem with the buttons on the wrong side. I then stepped into the skirt, or what there was of it. Pulled it up, she zipped the zipper, and I pulled the suspenders over my shoulders. She then fastened the matching neck tie around my neck.
I had buttoned all the buttons on the blouse, and Kate unbuttoned the top two. She stepped back, looked me over, and said, “I’d really like to undo one more button, but without real breasts it won’t look right. But, you look really cute. All right, nylons and shoes next.”
She handed me a package of thigh high white nylons with a pattern, and said, ”These should stay up on you. But, you may need to pull them up every once in a while.”
I took them out of the package, sat down, and started to put them on. Kate watched me, and said, “Girlfriend. Be careful how you sit. You’d better keep your knees together, or your legs crossed, or everyone is going to see what you have.”
“That short?”, I asked.
“You had better believe it. And, don’t bend over.”
As I was putting my heels on, Kate was putting on her nylons, and there is just something very sexy about her doing it. So, I stopped what I was doing, and watched her. She looked over, and said, “Something wrong?”
“Not a thing. But, there is just something about you putting on, or taking off, nylons that is just down right sexy.”
“And, you think you’re not sexy doing the same thing?”
“Yea. Right. A guy putting on nylons is sexy?”
“Girlfriend. You’re Gwen right now.”
After we’d finished putting on our shoes, we looked each other over, and Kate said, “One sexy little school girl.”
“Harry Potter,”, I said, “and all the rest of the boys, and maybe even some of the girls, would be chasing you all over Hogwarts.”
She got a wicked little smile.
We had decided to not wear masks to this party, just use our costumes, and makeup to maybe disguise us a little. And, the wire rim glasses, that we were both wearing, helped.
We arrived at Ken’s at about eight, and, had to park well down the block from the house. When we got into the house, it was full of kids, not only from our school, but others. The house was a very big one, bigger then Kates’. And, Ken was a football player, and very popular. We walked into the house, and started wandering around. It appeared that no one recognized us, or if they did, they didn’t care. There was dancing in the great room. Some sort of games going on in the diningroom. There were groups of kids in the livingroom just talking. And, piles of food in the kitchen. I even saw some kids out on the patio dancing. And, it wasn’t long until Kate and I were separated. Something that we didn’t want to happen.
The first thing that happened to me, was that someone grabbed my ass. I tried to turn around quickly to see who did it, but it was too crowded. I wandered around looking for Kate, and she was probably looking for me.
I wandered out onto the patio, where it wasn’t so crowded. And, I was asked to dance, and it was by a guy I knew from school. It was obvious that he didn’t know who I was, because I had to keep moving his hand off my ass. So, I guess I didn’t look like me. He tried talking a little bit, but I just smiled, and mumbled yes, or no, in response to his questions.
After we finished the dance, I wandered around some more looking for Kate. I ended up in the great room, dancing again. Afterwards, I had someone hand me a glass, and say, “Hi sweetheart. It looks like you’re by yourself. Have a drink.” I took the glass, and it looked like Coke. But, when I took a sip, it was Coke, but it tasted like there was something else added to it.
Just then Kate found me, and said, “Gwen, love. Here you are. I was getting worried about you.” And, she took my arm, and led me into the kitchen. And, when we got there, she said, “Love. You’ve got to be careful who you accept stuff from. Someone is spiking the soft drinks with booze.”
“That’s what I tasted?”
“Yea. Love. I got a taste of it earlier, and it’s strong. And, who knows what else they’re putting in it.”
“I don’t know if I like what’s going on at this party.”
“I know. I wandered into the game room in the basement, and the smell of marijuana was really strong. And, there was a couple doing it in a dark corner.”
“You’re kidding me?”
“No. They were really into each other, and didn’t care who was watching. And, I know both of them.”
“Do you want to get out of here?”
“Might be a good idea, before anything happens. I haven’t seen any chaperones, and I know some of these kids are underage.”
“All right.”
We started walking back through the house toward the front door, and got separated a little. Kate was in front of me, and we were separated by about ten feet. Some guy, dressed as Robin, from Batman and Robin, pushed me up against the wall, and said, “Where you going baby.”
I tried to push him away, but he had me off balance, and I could smell liquor on his breath. He really had me pinned against the wall, and then he tried to kiss me. He was able to make lip contact. And, I felt his hand on my chest. At that point I was able to push him away, and slap him. I should have punched him, but I didn’t. He got a little angry, but Kate stepped between us, and in a voice that meant business, told him, “Jeremy Walsh. If you touch her again, it’ll be months before you’re able to have sex again.”
Kate grabbed my hand, and pulled me through the house, and out the front door. We stopped just outside the door, and Kate asked, “Honey. Are you all right?”
“Yea. I think.”
“Jeremy didn’t hurt you, did he?”
“No. But, I really didn’t like it when he tried to kiss me, and stick his tongue in my mouth. And, he had his hand on my chest.”
“He didn’t.”
“He did.”
“Come on. Lets get out of here.”
We walked back to the car, and got in. Kate looked at me, and said, “Love. You need to fix your makeup.”
“Why?”
“Honey. What’s wrong?”
“This party was supposed to be a good one, and it’s crap. And, I wanted us to have fun. But, all I got my ass grabbed a couple of times. Guys that I danced with wouldn’t keep their hands off my butt. And, then there was that asshole Jeremy. Not to mention the booze and drugs.”
And, for some reason, I started to cry. Kate held me, and tried to calm me down. And, it took a little while. As we were diving away, a couple police cars were coming down the street. I said to Kate, “I wonder where they’re going.”
“I bet I know.”
“Ken’s party?”
“Could be.”
We drove around the block, and back up the street. By then, there were four police cars in front of the house, and the officers were just walking up to the door. Kate said, “I think we got out of there just in time.”
“I think you’re right.”
“Lover. You were treated just like a lot of the other girls that were there were treated. I even got my ass grabbed a couple of times. At least no one tried to kiss me.”
“Is it always like this for girls?”
“Some times. Want to go some place.”
“Where?”
“Greg’s”
“Dressed like this?”
“Sure. It’s still Halloween. And, at this time there won’t be many people there.”
“I . . . I guess.”
I drove over to Greg’s Drive In, and Kate was right. There were only a half a dozen cars in the parking lot. As we walked in, and I still wasn’t sure about going in, Kate pulled me into ladies’ room. And, said, “We’ve got to make you presentable again.”
“Presentable?”
“Crying never does anything good to a girl’s makeup.”
I looked in the mirror, and she was right, my makeup was a real mess. Kate worked on me, and when she was done, she said, “Take a look.”
I looked in the mirror, and you couldn’t even tell that I’d been crying.
Kate then asked, “Now. Are you really all right?”
“I think.”
“And, you’ll be all right sitting in a booth?”
“Yea.”
We walked out of the ladies room, and to a booth. We did get some looks from the few customers that were there. We sat across from each other, so we could talk. One of the waitresses came up, and took our order. And, then I just sat there looking at Kate. And, she asked me. “What are you thinking?”
“How much I love you. And, how sorry I am that tonight was a bust.”
She smiled, and said, “Tonight wasn’t your fault. You had no idea what was going to happen. And, I doubt Ken did either. It just got out of hand. And, I love you very much too. But, tell me, why did you slap Jeremy instead of punching his lights out.”
“I don’t know. Maybe it was being in character.”
“I know some girls that would have punched him.”
It wasn’t much later that the waitress brought our food, and we started eating. We also talked about what the cops might have been doing at Ken’s.
Just as we were about finished, we noticed a number of cars pull into the parking lot. And, it wasn’t too much later that people, in costumes, started coming into the restaurant. Kate looked at me, and whispered, “Most of these guys were at the party.”
“I know. I wonder what’s going on?”
“I don’t know. But, we may find out.”
At the back of the crowd of people was Jackie Yamashita. She stood there with some guy, and was looking around for a place to sit. I whispered to Kate, “Jackie Yamashita is here. I thought I saw her at the party. Should we invite them to sit with us.”
“Sure.”, she said, “We might find out what’s going on.”
I caught Jackie’s eye, and waved for her to join us. She saw me, looked a little questioningly, said something to the guy she was with, and then they walked over.
Jackie said, “Do I know you?”
“Doesn’t the voice give me away?”, I asked.
Jackie got a surprised look on her face, and said, “Yes. Kind of. But, I still . . . The dance. You were the other girl. You’re Gary. Right?”
“Yea. But, tonight it’s Gwen. Would you like to join us?”
“Sure.”
I got out of the booth, and sat next to Kate. Jackie and the guy scooted into where I’d been sitting, and Jackie said, “I didn’t recognize you right away. Girl. You look so good this way.”
“Thanks. Katie loves it when I play girl.”, I replied.
“This is Ben, my boyfriend.”
We introduced ourselves. And, Ben asked if I was like Jackie. Kate told him that I wasn’t, but I liked to dress like a girl once in a while. And, he said that I made a very convincing girl. I thanked him.
Jackie and Ben ordered their food, and we started talking.
Jackie asked, “Didn’t I see you at Ken’s party?”
“Yea.”, I replied, “We were there for a little while.“ And, then I went on to tell them what had happened to me.
“That sucks.”, Jackie said, “You must have left just before the cops got there?”
“They were pulling up just as we were leaving. We saw four cars.”
“There was a lot more than that. From what we heard, some of the neighbors complained about the big party, and the noise. So, when the cops got there, they asked to talk to the home owners. But, Ken’s parents weren’t there. So, they started talking to Ken, and they spotted some drunk kids. They checked them, and found out that they were under age. So, they called for more help, and started checking everyone.
“I guess they found the drugs downstairs, along with a few people that were stoned. And, then all hell broke loose. They called the parents of all the kids that were underage, or were drunk, to come and get them. A couple of the older guys got arrested, and I think that was because they got mouthy with the cops. Those that got caught with the drugs were also arrested.
“One young girl was even claiming rape.”
“Brandy Robinson?”, Kate asked.
“Yea. I think that’s who it was.”
“That’s who I saw going at it with Jeremy Walsh in the basement. She’s only fifteen, and he’s nineteen. And, it didn’t look to me like she was complaining.”
“He’s one of the one’s that got arrested.”
“Good. He’s the one that went after Gwen.”
“Ken is going to be in major trouble over this. I guess his parents are out of town.”
We continued to talk for a while longer, and as we were saying goodnight to Jackie and Ben, Jackie said, “Gwen. You are so pretty and passable that you should have been born a girl.”
I smiled at her, and said, “Thanks.”
After Kate and I were back in the car, I said, “I should have been born a girl?”
“No way love.”, Kate said, “You were born as you should have been, a boy. You are perfect the way you are, and I don’t want you any other way. You don’t think you should have been born a girl, do you?”
“No. No way.”
We drove back to Kate’s house. And, as we walked into the pool house, I took Kate by the shoulders, and said, “Katie. I don’t know what I’d ever do without you.”
She took my face in her hands, and gave me a very soft, sensuous, kiss. Then said, “Lover. You’ll never ever have to find out. I’m yours. And, only yours.”
Sunday, November 5
It was almost one by the time I left Kate’s house. And, we had decided that it was best to tell our parents what had happened at Ken’s party. My mother was still up, as she usually was, I sat down with her, and had a long talk about what had happened.
I was shaken out of a sound sleep by my cell phone ringing. It was Kate. And, I answered it with a, “Hi.”
“Hi.”, Kate said, “The cops were just here.”
“What!” And, I was wide awake.
“They heard that I saw Jeremy Walsh and Brandy Robinson together last night, and they wanted my statement.”
“Did you tell them everything?”
“Everything about Jeremy and Brandy, the booze, and stuff. And, I might have to testify.”
“Testify?”
“Testify at Jeremy’s trial, if it goes that far.”
“Wow.”
“Yea. Can we go to the water fall today?”
“Sure. When?”
“As soon as you can get here.”
“I’ll be on the way as soon as I get dressed.”
Kate was very quiet on the drive to the park, and our hike to the falls was usually hand in hand. But, today she held onto my arm the whole way. We sat quietly for a long time, until I asked, “Katie. Are you all right?”
She looked at me. And said, “I’m . . . I’m worried about us.”
“Us? Why?”
“This whole thing with you dressing like a girl. I started this whole stupid thing with you doing it, and it was fun. I suggested that we go to the Halloween parties, and they weren’t fun. I’m just afraid that all of this will come between us.”
“Katie. It would take a hell of a lot more than that to come between us. Ever since we got to know each other, you have been very special to me. Someone that I love very much. And, you didn’t start it, my brother did.
“The country club party was almost fun. The drunk guy wasn’t fun. But, watching his wife run around telling everyone that I was a guy was funny. And, handing candy out to the kids was really fun, especially when that one little girl said, ‘Mommy. Look at the two pretty witches.’ Not to mention my mom and dad afterwards. Things like last night just happen, and you have no control over it. We were there to have fun. But, the party got out of hand. It wasn’t your fault.
“I’ve had fun being Gwen. And, the main reason was you. You had fun with it, which made it fun for me. You enjoyed making me look like a girl. And, I enjoyed you doing it.
“Katie. There’s nothing that will ever come between us.”
“Promise me?”
“I promise you.”
She wrapped her arms around me very tightly, and we just held each other for a long time. As I was holding her, I whispered, “In fact, my mom and I were having a talk, and she asked me where our relationship was going. Do you know what I told her?”
“No.”
“I told her that one day I wanted to marry you.”
She sat back, looked at me, and said, “You didn’t?”
“I did.”
“You mean that?”
“Do I ever say anything I don’t mean?”
“No.”
“Well.”
We just looked at each other, and I saw a smile come back into her eyes. Then, with a sly smile, Kate said, “You do know, that I really love your brother.”
“You what!?”
“I love your brother.”
I looked at her, trying to figure out what she was getting at.
Then she said, “I love your brother because he was part of that stupid prank.”
“You’re kidding me?”
“No lover. If he hadn’t done that, then I would never have gotten to know you. And, he might even make an all right brother-in-law.”
Monday, December 25
I could tell you that Kate and I exchanged some nice Christmas gifts, and we did. I could also tell you that we spent part of Christmas day with each others families, and we did. I could also tell you that I gave her an engagement ring for Christmas, but I didn’t. We just had a very nice Christmas together.
Since Halloween, things had been very good for us. School was going very well. We’d both been accepted to most of the universities that we had applied to. And, we had settled on going to the same one. You had doubts. It was a university that wasn’t too far from home, but too far to drive every day, so it was going to be dorm life for us. And, we’d be able to go home on weekends.
Thursday, December 28
Kate and I drove over to the university to visit, and check out all facilities again. They had a very nice indoor swimming facility, which made Kate happy. Kate would be there, and that made me happy. The only thing that made us both a little unhappy, was that our dorms would be on the opposite side of campus from each other, and that was actually farther apart then our homes were. This was a very large campus.
As we were sitting in the student union having something to drink, I saw a smile come over Kate’s face, and I asked her, “Katie. What are you thinking about?”
“Just something stupid and silly.”
“What?”
“Nothing.”
“Katie.”
“It’s just a silly idea.”
“Tell me?”
“Well, I know how we could solve our dorm problem.”
“How?”
“You live as a girl, and we share a dorm room.”
I looked at her for a couple of seconds, then said, “Silly. Yes. But, I love your thinking.”
“You’d do it!?”
“If there was any way to possibly be with you. Maybe.”
“You’re kidding?”
I smiled, and said, “I just might. But, in your dorm, there are two girls to a room, and four rooms share one bathroom and a common room. That’s eight girls to the bathroom. Now, if one of those was me, just how long do you think it would take the other six girls to figure out that I was a guy?”
“Yea. It would be a little hard to keep that secret for very long.”
“Also, all my records say, Gary Kenneth Cutwright, male. Trying to change those would be next to impossible.”
“Yea. I told you it was a silly idea.”
“Yea. But, I like your silly ideas. It’s that this one would be almost impossible to do. But, if there was a way, I just might do it.”
Sunday, December 31
Kate and I had been invited to a couple of New Years parties, but had decided to spend the evening together. We’d moved a television set into the pool house, had some good snacks, and a fire going. Her parents were, where else, at the country club for a party, and we knew they wouldn’t be back until really late. We sat there cuddled together just watching the fire, and didn’t even turn the television on until eleven-thirty.
Monday, January 1
At midnight, we shared a very long kiss. And, this led to other things.
Later as we laid there, just looking at each other, Kate asked, “Want to go to the mall tomorrow?”
“Sure.”
“As Gwen?”
“As Gwen!?”
“Yea. She’s a great girlfriend.”
“You really want me to go to the mall, in the daylight, as Gwen?”
“Lover. You know you make a passable girl.”
“Yea. In a costume, or all dressed up, and in the dark.”
“And, I’ll bet you’ll look just as good in casual clothes.”
“If we do it. What am I going to wear?”
“Hmm. My clothes won’t fit you.”
“If you say Mary’s mother . . . “
“No. No way. Any way, she’s a lot shorter than you are. We may have to go shopping first.”
“Go shopping?”
“Sure.”
“Where?”
“Well. I’ve heard some of the girls talk about the thrift stores. And, that they’ve found some really good deals, and the selections can be good. Even some designer things.”
“What would we need?”
“Probably just a top or two, a pair of slacks or jeans, and a pair of shoes.”
“So, if we go shopping tomorrow, then we couldn’t go to the mall.”
“Why not. We go shopping in the morning, and to the mall in the afternoon.”
“I was going to sleep in.”
“Well, mister lazy. You can just get up, come over here, I’ll even make you breakfast, and then we can go shopping.”
“Oh all right. What time?”
“Breakfast will be at nine.”
“Nine!?”
“Yea. And, be on time.”
“Yes ma’am.”
That got me shoved off the couch, and onto the floor. Kate quickly joined me on the floor, and we did something we’d never done before . . .
Comments
Another Great Story Teddie :)
Thank you so much for bringing your magic back to treat us to a wonderful read Teddie. You have a permanent fan in me to read your loving stories as the magic they bring me in living as the target character brightens my life. You have your home here with us at BigCloset and always with me. *HUGS* Please always keep writing!!!!!!!!!
Love
Sephrena Lynn Miller
Looking
I'm looking forward to more of this interesting well written story. The characters are complex and well described. The situations are plausible and thought out. Although clues have been given, the ending is far from easily discerned.