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The Fundraiser/Or How I Was Volunteered For The Womanless Beauty Pageant

Author: 

  • Nina Adams

Audience Rating: 

  • General Audience (pg)

Publication: 

  • 7,500 < Novelette < 17,500 words

Genre: 

  • Illustrated

Character Age: 

  • Teenage or High School

TG Themes: 

  • Contests, Deals, Bets or Dares
  • School or College Life
  • Sweet / Sentimental

TG Elements: 

  • Hair Salon / Long Hair / Wigs / Rollers
  • Shopping

Permission: 

  • Posted by author(s)
Pre-pageant2_0.jpg
The Fundraiser Part 1 of 3
Or How I Was Volunteered To Be In a Womanless Beauty Pageant
By Nina Adams

My life as I knew it gets turned upside down for a fundraiser at my High School. What started as just an embarrassing request leads to so much more.


 
 
I couldn't believe that Kayla had nominated me for the spring fundraiser. She was my best friend what she had not told me was that she wanted me to volunteer for the big Glenfield Academy Spring extravaganza. Each spring the private school situated in the heart of the wealthy north shore of Chicago, put on a benefit. Half the proceeds from the event went to the school foundation, which it used for various programs and the other half of the net proceeds was always used to stage the spring prom.

The extravaganza is a very big deal for the school and widely supported by all of the students and their families. Each year the theme would change and it seemed to get bigger and bigger. There would always be some sort of show followed by a silent auction of some pricey donated items. The Senior Student Council with the oversight of a small faculty advisory committee would select the theme for the show. In recent years the show had included, short plays, American Idol style competitions, spelling bees, fashion shows, and last year a talent competition.

It was usually a big honor to be part of the entertainment, but it was also strictly on a volunteer basis. This year in an effort to do something completely different the student Council had somehow come up with the idea to do a womanless beauty pageant. They had heard of other schools having put on similar shows and this was one of the few ideas that the school had never done before.

When the idea was first presented to the faculty advisors, they were not keen on the idea. The school staff researched other pageants and found that many of these pageants were tasteless, often sexually offensive and made fun of women. These were not concepts that they wanted to support or teach the student body.

The Student Council was persistent and got the advisors to agree if they followed some strict guidelines. The most important aspect of the rules was that the pageant had to be staged respectfully and in an entirely classy format with a program along the lines of a traditional beauty pageant. There would be no bawdy outfits, or no contestants sexually mocking women with outlandish get ups. The contestants would have to dress and look tastefully at all times and would be evaluated not just for their stage beauty, but would be interviewed during the week prior to the show. The faculty committee would expect to see that they learn something about gender roles and had gained some empathy for what actual pageant participants might feel.

Each official entrant would be part of a team. The team would include a female student and a parent sponsor. It was believed that by including an adult and a female classmate that there would be the highest probability that the show would be dignified. All student entrants had to be nominated by another student and they had to turn in their acceptance by the 2nd week of January. Upon the nominees acceptance, the team application had to be submitted and approved by the Student Council. All of this took place long before the mid-April event so proper preparation by the teams and staging plans could be arranged for.

Any student entrant that did not follow the rules would be immediately suspended from the competition. Additionally, any student whether participants or not that insulted the volunteers or created any embarrassment for the school would be banned from the fundraiser and potentially suspended from school.

The Student Council agreed to the terms, but expressed that some of the campiness was what made the show so much fun. The faculty advisors said it would still be entertaining if it was done professionally and with the appropriate fanfare and staging.

I was so stunned when Kayla told my mother and me in the car coming home from school that she had nominated me for the fundraiser. She was my best and oldest friend and she wanted to set me up for total humiliation and embarrassment.

I looked over at her and barked “NO FUCKING WAY!”

My mother nearly jumped out of her seat. Not over the nomination, but because of my foul language. “Lucas we do not talk like that in our family. If I hear one more piece of ugly language like that from you, then you will be grounded for the weekend.”

“But mom, did you hear what she did. That's crazy!”

“I heard clearly what she said and that does not excuse your language. Kayla, I hope he does not talk like that to you when I'm not around.”

“No Mrs. Everdeen, Lucas is normally so sweet.”

“Good then, so tell me more about this nomination.”

“There will be 12 to 15 students in the pageant depending on nominations and team sponsorships, with prizes and honors for the winner and their student teammates. It's probably going to be very competitive and very extravagant. I've already heard that some teams have been formed and are taking it very seriously. Mrs. Gunther has already agreed to back her son Steve for the show. You know how she is when she puts her mind to something.”

I knew Mrs. Gunther as one of the town's biggest socialites. She came from old money and always loved to put her name and stamp on all community shindigs. Her son Steve was the youngest of 3 boys and sort of an under-achiever. He was a quiet kid with long straight hair and a lean frame. I never thought of him being effeminate or anything, but under the circumstances I could see him probably passing as a girl.

My mom never really liked Mrs. Gunther or some of the other rich town women that always managed to find a way to flaunt their money. Sure some of them got involved in charities, but in the case of Mrs. Gunther and a few others, it was strictly because they had the money to take center stage. Everything Mrs. Gunther did was showy and attention getting. Even her mansion was ridiculously big and on one of the most beautiful pieces of property on the lakefront.

The funny thing was that my mother was probably as wealthy or even more so than the Gunthers. My grandfather was an inventor and among his patented products was the pop top on the aluminum cans used by Coke and others. We were very wealthy, but few people suspected it. My mom was very charitable, but usually on an anonymous basis and our home was nice, but very modest by Glenfield standards. My mother even owned a florist shop in the center of town that she managed. She certainly did not need to work, but with my dad having passed away nearly 10 years ago it gave her focus. I worked at the shop on occasion and some of my classmates, even Kayla, would sometimes call me the flower boy.

“Well Lucas we should at least give it some thought. It would be kind of nice if the Mrs. Gunther's of the world didn't always get all of the limelight. Don't just dismiss the idea without thinking about it.”

“I thought about it and I don't want to do it. You may not like some of the other mothers, but I don't want to be a big joke. I'll be the one making a fool of myself.”

“I understand your initial reluctance, but just keep an open mind. I'm not sure about it either, but let's at least table it for now and think about it later. Nobody is going to force you to do this. Okay?”

“I'm not going to change my mind, but whatever you say mom.”

“Okay then, we will talk about it over the weekend. Kayla please give me a call later. I want to know everything about the fundraiser.”

“Sure Mrs. Everdeen.”

CHAPTER 2

Over the next 3 days I could not get the pageant out of my mind. I couldn't figure out why Kayla wanted me to do it, because we were very close friends and I am sure she was not out to ruin my life. We were as close as a boy and girl could be without actually being a couple. I often wished we were more than just friends, but for now I had to settle for just best buds. What also made our platonic relationship so tough was that Kayla was such a pretty girl with her long dark hair and perfectly conditioned athletic body. She also always looked so stylish but never dressed over the top. We grew up together from a very young age so despite her being a bit out of my league as girlfriend material, we always remained best pals.

Kayla was nearly as tall as my 5'7" frame and I probably did not outweigh her by that much. I had inherited my mother somewhat delicate features and her blonde hair. My hair color was a washed out blond shade that could almost be considered a light brown, but I was definitely a blond. Maybe it was from being around Kayla all the time, but I had allowed it to grow so that it was now shoulder length. I even had to brush it back and wear a headband when I participate in sports. It always seemed to fall into my face. It was obvious to even me that I needed to get it cut soon.

pre-pageant 3.jpg

I was only a sophomore at the school, but I liked school and was a pretty good student. Kayla was also a sophomore, but she looked a little older. She had a brother that was a senior at the school. As a result, she always knew the ins and outs of everything happening and was privy to a lot of the interesting gossip.

I was a couple of months shy of turning 16 and looking forward to getting my drivers license. I thought it would be kind of cool to get a motorcycle or maybe a car when I got my license and had already begun pestering my mother about the idea. I was pushing for the motorcycle since so many North Shore teens had cars, but not many had motorbikes. Kayla thought my idea was cool too and was pushing her parents to get her a Vespa. I liked Vespas, but I thought a motorcycle would be more manly.

On Friday my mother mention the fundraiser at breakfast and I immediately slumped my shoulders.

“Can we talk about it later? I am not in the mood at the moment to talk about it.”

“Well Lucas Edward, I have been thinking about this and we should have a civil discussion about it. Don't be so negative. I only want to talk it through.”

“Not now mom. How about later or over the weekend?”

“That's okay, but it's not getting pushed back beyond this weekend.”

“Fine! I'm with you on that. Let's put it to bed over the weekend.”

With that I went up to my room and got ready for school.

In second period Kayla sat down next to me and the first words out of her mouth were, “Are you in?”

“What?”

“You know what I'm asking.”

“Not you too? My mom started in on me this morning.”

“And?”

“And what?”

“What did you decide?”

“I just told her later.”

I could clearly see that my last remark was very disappointing to Kayla. She made a scrunchy face before responding. “It'll be fun and we can spend more time together. Your mom said she would do everything to make it easy and worth your while.”

“What do you mean worth my while?”

“I'm not sure, but she wants you to have fun and feel good about it.”

“I can't imagine how, but I agreed that over the weekend we would discuss it. I just think it's crazy.”

“If you are still undecided after talking with her, call me or come over and maybe I can convince you. Maybe some of my girlish charm can persuade you.”

That comment got me distracted and thinking in a different direction. “I'd like to see you try.”

“How about Saturday? You could come over for dinner and we could finish up our schoolwork together and then I can work some on my girl magic on you.”

“I'm in! I can't wait to experience some of your feminine skills and …..” My comment got cut off as the bell rang and we had to turn our attention to the class.

I was excited to see what she had in store and more so to know if she had any special ideas about us. I guess I would have to play along.

Mom came home from the flower shop around 6 with some pasta and salad from one of my favorite restaurants called Hole In The Wall. On Friday nights we didn't always eat together because of social activities and plans, but with Hole In The Wall on the table we sat down to enjoy some good food together.

After a couple of rhetorical questions about school she wasted no time turning to the fundraiser. Without trying to show too much initial enthusiasm, she talked about how important these things were for the school and how this was an opportunity for some new faces to wipe away some of the smugness from the old blood that looked down on everyone else. She mentioned how the past contest winners got to be honored at school and featured in the yearbook. I really did not want her to know that scared me even more.

When she was done talking about all of the virtues of the event and its importance to the school she turned the conversation on me.

“Lucas you have so much acting talent and natural good looks. You've told me time and again you that just needed an opportunity to show the drama department your skills.”

“Not like that mom.”

“Honey, so many of the great actors and actresses have achieved acclaim by taking roles like this and captivating the audience. If you do it well and put yourself into it, you will impress the right people.”

“Maybe, but I will also be the butt of tons of jokes.”

“I'm not saying it will all be easy, but to truly impress you will have to be focused and not worry about some jokes from kids you don't care about.”

“I can tell you really want me to do this and I'm not sure why.”

“I'd be lying if I said I didn't care either way.”

“So why?”

“For two basic reasons. First, as I said before, I'm sick and tired of a small circle of families at the school looking down on the rest of the families as if they were extras in their game. I think it would be fun to knock them down a peg or two when they don't expect it.”

“I get that, what's the other reason?”

“Well Lucas, the others is a little more personal. I'm not sure how to put it without upsetting you, but for me, I think the competition might be a once in a lifetime opportunity.”

“The opportunity to humiliate me?”

“No! No! You are my only child and you know how much I love you, but I have also wondered what it would be like if I had had been blessed to also have a daughter to spend some time with. If your father and I had been fortunate to have more time together, we were hoping to have a boy and a girl.”

“Do you not like having a son?”

“I love you and always will, but a few weeks of teaching and showing you something about how the other half lives, sounds like a rare opportunity to me.”

“I just don't know mom. I would do anything for you, but the price just looks so scary to me.”

“I don't want to force you to do anything you are not comfortable with. If you are going to do it, then it cannot be just for me. You have to be resolved to putting in your best effort.”

“It just seems like such a big commitment with a potentially deadly carrot at the far end of the stick. It's not something to look down the road and feel good about.”

“I don't want this to be the only reason, but how about I give you something else to look forward to.”

“What's that?”

“Well if you give it your best effort, I will get you a motorbike for the summer and some sort of car in the fall. The bike is just for fun, but you'll be needing a car pretty soon, as its getting more difficult for me to get you to all of your activities.”

“Really? You will get me both if I do this?”

“Honey, I was going to get you a car at some point anyway, so the motorbike is really the only extra carrot.”

“Wow!”

“If the only reason you might do this is for the bike, then I don't want you to do it. I want you to think about all of the other things we talked about and consider those. Think about all of the good reasons for doing this and not just some bribe.”

“What kind of bike can I get?”

“I don't know. I guess we'll play that by ear, but not too big and something safe and appropriate. You are going to have to work at least part-time over the summer to pay for the upkeep and gas.”

“That's fair.”

“I want you to think this through. Come Sunday I want an answer, but not right now, while you are fantasizing about a new bike. Think it completely through. If you agree to move forward I want you to be committed, because both Kayla and I will be planning this through and we will expect total cooperation.”

“It can't be that much planning?”

“You have no idea! If you are in, we plan to win and you will need to be a perfect thespian.”

“Okay then, I will decide over the weekend. Tomorrow Kayla said she was going to put in her two cents on the subject too. I think she wants this as much as you mom.”

“Kayla and I chatted and she also likes the challenge. She has already gotten the scoop on 3 other serious teams. She thinks we have a good shot.”

“So you two are conspiring? ”

“No we just talked, but if we enter, then yes, we will be on the same page.”

“That's enough for now. My head is spinning… What's for dessert?”

CHAPTER 3

Friday night my dreams alternated between riding a Harley Davidson and being paraded around in a dress. It was a very restless night of sleep, but I was wide awake early Saturday morning. After a pretty boring day, mom dropped me at the Miller's just before 6 o'clock and said she would be back to pick me up at 11 following dinner and socializing with some of her friends.

In a typical week I probably met up with Kayla 2 or 3 times to study, but tonight I was extra excited to see her. In our last conversation she made it clear she would go all out to convince me to enter the show. I dressed a little nicer than usual and brushed my hair over and over until it looked its absolute best.

When I walked through the door, I quickly discovered that Kayla’s excitement level matched my own. Kayla gave me a big hug as soon as she saw me. She almost never did that, so I know the evening was off to a good start. She whispered in my ear, “After dinner and homework, I can’t wait to get my hands on you.”

I almost wet my pants when she said that. I was even more aroused when her hair brushed across my neck and face. I could've easily skipped dinner and headed up to her room, but I was ushered to the table to join Kayla and her brother Jack and her mother.

The meal was very good and Mrs. Miller was as always so nice to me. She complimented me on how nice my hair was looking and how great it should look by spring.

As we were finishing up the last of the roasted chicken, she asked me if I knew any of the students that had committed to the fundraiser so far. I politely told her, “I had not given it much of my attention and that I didn't think there was any official list as yet.”

Jack jumped in, “That may be, but Kayla has been talking nonstop about the potential competition.”

“You know Mrs. Miller, your mischievous daughter nominated me without asking.”

“Yes she told me, and I think it will be a great experience for both of you.”

“That may be, but I have not decided for sure if I'm going to do it. Did Kayla tell you otherwise?”

“She only said your mom and her were going to be your sponsor and teammate. I just assumed you planned to enter.”

Jack added, “She thinks you can win.”

“Kayla! It's not a done deal. I still need to think about it. Mrs. Miller, Kayla promised to do her best to convince me tonight. So maybe you should ask her again about it later.”

“Sorry Lucas. I didn't mean to push you or anything.”

“Oh it's okay. I know I have to decide soon.”

“Mom can we be excused to go upstairs?”

“Yes dear, just put your dishes in the sink.”

With that we scampered upstairs to Kayla's room. As soon as we were out of the kitchen she grabbed my hand and practically pulled me up the stairs.

“Lucas we are going to have so much fun, so let's work hard to get our homework out of the way.”

“Sounds good to me. I don't have that much.”

“We can get started with the fun stuff, as soon as we are finished.”

I was thrilled about getting to see Kayla use her feminine guile to convince me to enter, but she was talking about it in a vague way. I didn't understand why she had to wait to turn on her feminine charm… Why not while we did homework? I decided not to push things too hard.

We spent a quiet hour doing our work. There was a minimum of conversation during that time. I would look at her every so often and smile and she usually smiled back. I was first to finish up and proudly announced “ALL DONE.”

“I still have some math, but I can finish it up later or tomorrow. Are you ready Lucas?”

“I am all yours, convince me.”

“Before I start on you I want you to take a shower. I want you clean as a whistle.”

“I can't shower here.”

“And why not? I’m not doing anything until you have showered.”

“I'm already clean.”

“I want you to smell fresh and I want your hair damp.”

“I don't get it, but okay.”

“There is a robe on the door. After you shower just put that on.”

With that I was getting both nervous and excited. I had very little experience with girls and she wanted me nearly naked. I was also concerned her mother downstairs might walk in on me with my clothes off. Kayla sensed my fear and locked her bedroom door. I made my way to her private bathroom.

It was such a girly bathroom with all sorts of cosmetics and makeup and it smelled like lavender. I stripped down and quickly got in the shower. I could hear Kayla yelling for me to condition my hair.

I took a long shower out of nervous fear and anxious anticipation. I was starting to get scared that I might not perform well enough. I didn't want to blow anything between us.

Kayla’s body wash smelled good but so flowery. When I was done I was very clean, but hardly smelled manly. When I emerge from the bathroom wrapped in her light blue cotton robe, Kayla practically mugged me. She grabbed my head and planted a big wet kiss on my lips.

“You are such a good sport. We are going to be a perfect matching pair. I am going to want to kiss you all of the time.”

I can live with that.”

“While your hair is still wet let's get started.”

“Started with what?”

“Your hair.”

“What about it?”

“I am going to give it a little bounce and brush it out. I want you to get an idea how nice it can look and show you your potential.”

“So that's why you wanted me to shower. I feel like an idiot.”

“This will be a blast.”

“I thought you wanted something else from me, if you know what I mean.”

After a moment of hesitation, Kayla moved back to my side on the edge of the bed planted another slower and more passionate kiss on my lips.

“Lucas I have always felt something special about you. The fact that you are here and hopefully entering the pageant only adds to my fascination with you. It's just something unique and special we can share.”

“It's just strange that you want me to do this.”

“Lucas, you know I am into boys but I think I am also into girls. I've never kissed a girl, but maybe with you I can get the best of both worlds. It may be selfish, but with you I can kind of get a boyfriend and girlfriend all-in-one. It's all for fun and I think it will make us closer if that's possible. I want you as a boyfriend, but the pageant is a bonus.”

“What's wrong with me being just the boyfriend and you the girlfriend?”

“We already have that, but I get extra excited thinking about sharing this little role-play game.”

“Both you and my mom seems set on this. I am having a hard time sharing your enthusiasm.”

“Give it a shot. If I am right I think it will grow on you. I mean after you get over your resistance were going to have the best time together.

“I know I am going to look like a fool and get laughed at by everybody.”

“Now I know you are wrong. If you play along no one will be laughing and the experience will be amazing.”

“I guess I can play along a little. What do you have in mind?”

“Tonight as I indicated earlier I want to work some of my feminine skills on you ensure you that you have a chance.”

“Okay, but I want this just between us for now. I don't want your brother spreading stories around school.”

“Don't worry he was leaving after dinner and he won't be back until very late.”

“So what now?”

“Just follow my lead.”

With that Kayla got out her brush and curling iron. She parted my hair down the middle and started giving it some body. When she was done she had given me soft curling tendrils, mixed in with waves that ever so slightly curled under. Not a hair was cut, but it was certainly a much more feminine looking style. She even spritzed me with hairspray, before saying that I can wash everything out with a little hot water later.

“Well I guess that wasn't too bad.”

“We are just getting started. Come sit in my bathroom while I brighten up your face.”

“I was afraid of that. Please don't put that much stuff on my face.”

“That stuff is cosmetics and makeup. You need to learn as we go along.”

Kayla spent nearly 30 minutes. working on my face. She even plucked a small amount of what she called stray eyebrow hairs. This time I didn't get to see myself until she was finished. When I finally got to see my face in the mirror I could feel my blood heat up a degree or two. My hair now adorned a face as pretty as any at school. There was very little sign of Lucas staring back at me. I could see myself being attracted to that girl and after my initial shock had passed. Kayla reached over and gave me another kiss. Some of my red lipstick stuck to her lips after our brief kiss.

Pre-pageant 4.jpg

“We are nearly there.”

“Where?”

“Shush.”

She handed me a set and girl’s briefs and told me to slip it on. It seemed silly at this point to fight it. After I had it snugly in place she told me to take off the robe.

No sooner than the robe hit the floor she was slipping one of her matching bras around my chest. For a brief second or two, I was grateful I had no breasts to fill in the cups. Almost as quickly as she had snapped the clasps in the back, she inserted foam falsies into the brassiere. I now had a pair of prominent breasts to go with my facial makeover.

I started to have a strange urge in my now panty clad groin. It was hard to hide the tent that had quickly emerged.

“Now we are both excited” chimed Kayla.

“I don't know what came over me, this is all just really confusing.”

“Nothing wrong with that. It just means you are enjoying it. Down the road we will need to take care of that. For now we just have to cover it up.”

“Kayla then handed me a cream colored silk dress that I remembered that she occasionally wore to church.

“Step into it this and I will zip it up the back.”

Like a trained animal I followed her command. I could feel the soft material delicately cascading down my increasingly stimulated body. She pulled the zipper into place and I felt encased in soft feathers. I had a hard time not showing how good it felt.

She finished off my ensemble with a conservative black two inch patent leather pair of pumps. Despite the modest heel I had a hard time initially keeping my balance. I am not sure whether it was the heels or just the cumulative effect of what I was wearing.

Kayla walked me over to the full-length mirror on her closet door. I was totally spellbound. “Kayla what did you do to me?”

“Really not that much. I just helped bring out a little of your potential.”

“I look like a girl.”

No a pretty girl!”

“This is too surreal. I don't know what to think.”

“Enjoy it, it's fun being pretty.”

“For a girl.”

“Well at this moment you look like one, so try and enjoy it.”

I stood there staring at myself for a long minute before Kayla came up from behind and put her arms around my midsection and her head on my right shoulder. Together we stared at my reflection.

“I love how you look. I should probably add some jewelry. You know my sweet Lucas, now I really do feel like I have a girlfriend and a boyfriend wrapped in one. Sometimes it will be more boyfriend, right now I am enjoying the girlfriend side.”

With that last statement she slowly spun my docile body around and gave me another passionate kiss. This one lasted by far the longest and was beyond any sexual feelings I had ever experienced. I was on total emotional overload and unsure of what to do next. After I caught my breath and sat down, I then folded my hands almost instinctively over my lap.

“Lucas you look so cute. Tomorrow I should take you with me to church in the morning.”

Kayla’s suggestion broke my transient mood. “No way! I am not leaving the house looking like this. This was just a little fun between us, so don't get carried away.”

“That's a shame, but I won't push you yet.”

“Don't push me period.”

“You have been enjoying the evening… haven't you?”

“Well I've enjoyed being here with you, but remember I'm still a boy.”

“I know, but you are a special boy.”

I gave her little smile and then tried to change the conversation.

“Maybe I should change back now. I guess you proved your point.”

“Lucas it is only about 9:30 and your mom isn't getting you until about 11. It'll only take 5 minutes to take off the makeup and a couple of minutes more to change your clothes. I'll make sure you get started by 10:30, okay?”

“What now then?”

“Nothing much, I want to spend some time with you. I'll put on the soundtrack from the Hunger Games.”

After the initial shock of my makeover faded I was able to relax with Kayla and just hang out. We flipped through some gossip and entertainment magazines with the music in the background. We laid on top of her green bed laughing and even giggling at some of the stupid photos in the magazines. Kayla always made a point for both of us to comment on the fashion sections in each magazine. It was getting close to 10:30 and the last 45 minutes seemed to fly right by. There had been no additional passionate kisses, but a few friendly pecks on each other’s cheeks.

The whole evening had been such a radical new set of feelings, but strangely I almost didn't want it to end. My peaceful mood was shattered when there was a knocking at the door. Mrs. Miller was telling us to come downstairs to join her and my mother who had been chatting in the family room enjoying some tea.

Kayla answered first, “Give us ten minutes mom and we will come down.”

“Come down now Kayla, Mrs. Everdeen wants to talk with both of you.”

“In a few minutes mom. We're in the middle of something.”

I think at that point Kayla's mom could hear us scurrying about and the increasing tension in Kayla's voice.

“I want you to open the door at once.”

“Please give us a moment.”

“NOW!”

I was going to lock myself in the bathroom, but I knew that would only delay the inevitable.

Kayla looked at me as I straightened my dress and she walked over and unlock the door. I could see Kayla's mother's eyes light up when she saw me.

“I see we have been playing dress-up.”

“Please Mrs. Miller, Kayla just wanted to prove to me that I would not look like a clown if I decided to participate in the fundraiser.”

“Calm down Lucas, you certainly do not look like a clown. If I didn't already know it was you, I would have just thought you were one of Kayla's girlfriends.”

“Nobody was supposed to see this. Please don't tell anyone. Please give me a minute so I can go change.”

“Never mind that. Your mom wanted to talk about the fundraiser with you and Kayla, so there's no point to change now.”

“Please Mrs. Miller!”

“You did your little dry run for the fundraiser, so it's only fair that your mother gets a look at you.”

“I can't face her like this.”

“You look absolutely darling. I'm sure she will feel the same. Please walk down with me and I will prep your mom before you step into the family room.”

Descending the stairs in Kayla's heels was a very difficult task. Even if I was not scared to death, I would have had to hold tightly onto the railing. Just before the entrance to their family room, Mrs. Miller told me to wait just outside the door and take a few breaths. Kayla and her mom walked ahead towards where my mother was seated.

I could hear the conversation pretty clearly. After some polite greetings between my mother and Kayla, Mrs. Miller interjected.

“Kayla and Lucas have had a busy evening and clearly have been discussing the merits of entering the beauty pageant. One of Lucas fears is that he would come off as some sort of clown. With much persuasion and some deft skills, Kayla has made her case to Lucas that he will do just fine.”

“I don't understand Claire, what did she say and where's my Lucas?”

“With no further delay I give you Ms. Lucas…. Come in now Lucas.”

I shuffled my way along the wood floors until I was standing about 8 feet in front of my mother. I expected to see her in shock, but instead I could only read a mild surprise. She scanned me up and down and her smile grew slowly wider. She was clearly fine with my little charade.

“Lucas, I guess you have decided to enter the fundraiser after all. You look very nice for a first effort.”

“Kayla just wanted to show me that I would not look like a joke. It still feels crazy doing this, but I guess I could look worse.”

“She did a nice job on your makeup and the dress is certainly very lovely. With some work and practice I think you will make a fine contestant.”

“What do you mean work and practice?”

“This is not a Halloween party. This is a competition and if you are going to enter you will need to be completely ready.”

“Mom, it's still just a fundraiser.”

“This is a big event with lots of students and families depending on its success. I don't want to waste my time if you do not plan to do everything possible and give 100% effort.”

“How much is there to do?”

“You need to learn your part like a method actor and we need to tweak your appearance so that you look more like a beauty pageant contestant. You also need to get proper outfits and get over your obvious nervous apprehension.”

Kayla could not hold in her enthusiasm any longer. “Lucas, I will be there at every step so that you enjoy the experience like we did tonight.”

“Kayla I know you'll be very important if this is going to be a success. You have a unique perspective being the same age as Lucas and you can certainly be a great role model.”

“You both have this figured out so I guess I can give it a try.”

“A try is not good enough. I am going to put in a lot of effort to guide you through this and once we are all committed there will be significant financial investments in getting you prepared.”

“It's so far off, can't we just go slow?”

“There's barely enough time if we want to do it right. If you agree, I do not want you to later change your mind. Some of the costs of competing are quite substantial.

“This whole thing just seems so mind boggling to me.”

“That's why you have so much work ahead. Hopefully by the benefit you will not feel that way.”

“Kayla will you have my back during this whole thing? I'm going to need help with my reputation at school.”

“Lucas you know I will. I'll do my absolute best so it goes smoothly.”

“Okay then mom. I'll do it.”

“Wonderful. So from now forward you need to follow my orders and not question Kayla and my instructions. Is that understood?”

“I hope I do not regret this, but yes, you can count on me.”

Lucas dear you may not realize it now, but this is going to be a great adventure and I'm sure you'll make me proud.”

“Thanks mom. I think now that we have this figured out I am going to go up and change.”

Mrs. Miller stopped me. “Lucas you don't need to change now. Kayla has not worn that dress since the fall, so think of your outfit as our little gift.”

“That's alright Mrs. Miller, but I can't go home like this anyway.”

“Lucas, please thank the Millers. That is such a nice gesture. Don't worry about going home. It's late and dark outside, besides you look just fine. No one would think you were anything other than the pretty girl sitting in front of me.”

“Come on Mom, I may not look like it right now, but I am still Lucas.”

“You make one good point. You don't really look like a Lucas. We're going to need a new name for you for the competition.”

“Really? Everyone will still know I'm Lucas.”

That may be, but you should have a more appropriate name for the show and while we are getting you ready. Do you have a girl name that you really like?”

“Yeah, Kayla.”

That got a few smiles from everyone and an air kiss from Kayla.

I think if you choose something from your initials that would be nice. Something with an L or E or both.”

Kayla blurted out, “Ellie.”

“That starts with an E, Kayla.”

“Sounds like L..E.. What do you think?”

“I don't really want a girl's name, but it's an okay name.”

“Kayla that is a nice idea. Lucas has a great aunt who passed away a couple of years ago named Eleanor. Ellie would be a nice way to honor her.”

“Mom, it's just for the show.”

“I know dear, but names are important. When I call you Ellie I wanted it to be an appropriate name.”

“Fine then, you can use Ellie for my competition name.”

“It's settled then. You're going to be the future pageant queen Ms. Ellie Everdeen.”

“Oh God!”

“Honey, watch your language and go put your old clothes in a bag so we can head home.”

Kayla walked me up to her room and as soon as we got into her room and out of sight she gave me another long wet and hard kiss. She was clearly the aggressor and I was her prized little toy.

“Ellie I am so happy. You are going to be the belle of the ball and I am going to help you become perfect.”

“Not too perfect I hope and its Lucas not Ellie.”

“Trust me. We are both going to love your time as Ellie.”

“Kayla my head is spinning. I think I need to go home and figure out what I got myself into.”

The ride home was uneventful, but still I hunched down in the car seat to avoid being seen. At home my mother sat me down and showed me how to properly remove my makeup. She was very instructive and wanted me to learn the right way so, if necessary, I could do it on my own. When we were done she had me moisturize my face. The whole evening experience took a lot out of me and I was asleep in a flash.

It was another uneven night of sleep. I had so many strange dreams and they all revolved around me dressing or acting like a girl. I remember only bits and pieces, of the dreams, but I remembered attending school as Ellie and even being a member of the cheerleading squad. The most vivid memory I had was from just before I woke up. In that dream my mother insisted that I attend Sunday's mass in the dress Kayla had given me. She wanted me to get good use out of the new clothes and didn't think there was anything odd about me attending church in a dress.

On Sunday morning we did go to mass, but fortunately my dreams quickly were forgotten as I resumed my life as Lucas. I still had some weird thoughts at church as I looked around and saw some girls my age dressed much like I had been the previous evening. I couldn't help but ponder myself as one of them. I was having thoughts that were undoubtedly out of place for a place of God.

The Fundraiser/or How I Was Volunteered For a Womanless Beauty Pageant 2

Author: 

  • Nina Adams

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • 7,500 < Novelette < 17,500 words

Genre: 

  • Illustrated

Character Age: 

  • Teenage or High School

TG Themes: 

  • Contests, Deals, Bets or Dares
  • School or College Life
  • Sweet / Sentimental

TG Elements: 

  • Fancy Dress / Prom / Evening Gown
  • Hair Salon / Long Hair / Wigs / Rollers

Permission: 

  • Posted by author(s)

Part 2

Pre-pageant2_0.jpg
The Fundraiser Part 2 of 3
Or How I Was Volunteered To be in a Womanless Beauty Pageant
By Nina Adams

My life as I knew it gets turned upside down for a fundraiser at my High School. What started as just an embarrassing request leads to so much more.

Part 2

Chapter 4 ----

Thankfully my life seemed to return to normal. My mother after successfully convincing me to enter the pageant had backed off and stopped pestering me about it. Over the next 10 days hardly anything at home seemed out of the ordinary. We never even chatted again about the unusual events of Saturday night at the Miller's. The only noticeable oddity at home was a shift in our diets. At dinner on Monday, my mother declared we both needed to eat healthier and get in better shape. Neither my mother or I was overweight, but she insisted that we could both benefit from a better diet.

Mom's definition of healthier was mostly just less. My daily lunch sandwich had been replaced with either, yogurt, chicken broth, or a small salad. Dinner was equally skimpy and also low-cal. After about three days, I was grateful for my small bowl of cereal in the morning. Even an occasional clementine orange seem like a splurge. I protested the meager rations, but mom somehow persuaded me to stick with it for a while. The first week alone I dropped 3 pounds.

Kayla also started in on a lighter diet, so it was hard to get any sympathy from her. Our relationship had taken a step up, but it was not a lovefest like I had been dreaming about. In public, it was mostly handholding, hugs, or an occasional cheek kiss. When we were studying or in private we might actually kiss or lay together, but it was not as passionate as on that strange night. Much like my mother, Kayla had backed off bombarding me with talk about the fundraiser. On occasion she would mention the rumored nominees or teams that had formed, but she avoided teasing me about further dressing up. I certainly thought about that night and wondered what might be in store for me in the future.

On Friday, almost two weeks after I had made my commitment, the official nominations and approved teams were announced over the school's intercom system. I was grateful it was during last period. The fundraising benefit had managed to achieve a full set of contestants. 15 students had been coaxed into the contest and it was obvious that the program was off to a successful start.

I knew most of the students to some extent and they were freshmen, sophomores, or juniors. All of the seniors had managed to avoid being part of the gauntlet. The group had a few students that Kayla had already mentioned, including Mrs. Gunther's son. The remaining kids that were in the field only surprised me a little. Three of the students I knew from theater and two more from the school swing choir. I really did not know the four freshmen entrants that well, but of the junior contestants, the one I knew the best was a boy named Bill or as his friends call him Billy.

Billy was one of the few openly gay people I knew. He was a nice kid, but anyone who met him would know instantly about his lifestyle. Some of the other nominees were similar to me with long hair and most of those were average or below average in physical stature. Two of the juniors were really big kids and I was sure they would probably play for laughs off their obvious masculine looks. My first impression was that five or six of the boys could probably make passable girls without too much difficulty. At least from a visual perspective, I thought the winner would probably come from that pack.

I tried exiting the school as quickly as possible, but I received a lot of attention before I could clear. Most of it was good-natured or attempts to be funny, but I still wished I had been a million miles away. One of my old friends, the one that gave me the nickname flower boy, smiled at me and said, “Now I will have to call you flower girl.”

I felt my heart sink a little as a couple of the kids standing within earshot then added, “Good luck flower girl.” I never really hated the flower boy name, but now I was afraid the new nickname would also catch on.

I took my iPhone out of my locker and saw that Kayla had left me a text. “Now that it is official we are going to have to start getting you ready. I will touch bases with your mom and give you a call later.”

I made my way home with a new sense of dread. I was now officially a beauty pageant contestant and all of my classmates knew it. The calm that had followed my dressing experience at Kayla's house would soon be turned into a storm. I was certain that Kayla had all sorts of crazy thoughts now spinning around in her head. I knew it would not be long before I started hearing them. I was grateful I had no commitments for the weekend so I could just stay at home and hideout.

At home I retreated to my room and listen to some music. As was my daily routine almost every day after school, I went to check Facebook to find out what was up with my friends. The chatter was mostly focused on the fundraiser. One of the girls on the student council had posted the question, “Which contestant do you think will make the cutest girl?”

The comments section for this question already had a massive string of responses. As I suspected, there was a small group of contestants that got most of the attention. I was clearly one of the Facebook favorites. It wasn't enough that some of us were mentioned, but many of the comments were tough to ignore. They weren't intentionally cruel, but included statements like: future babe, will be a hottie, chic want-to-be, and prom queen material. I wanted to defend myself with a post, but I couldn't think of anything clever to fight back with. I just read the statements and didn't involve myself in the chats.

My mother got home just a little later then usual with some soup and salad from the Corner Bakery. She could see my shaken mood and I eventually filled her in on the afternoon events.

“Honey the news is out. You no longer have to worry about it. Now you can focus on getting yourself ready. No more secrets… Just be the best Ellie you can be.”

“I will mom, but it doesn't just make all of the embarrassment go away.”

“As you get closer and more comfortable in the role it will become much easier, maybe even second nature.”

“I doubt that I will ever get comfortable. One night in a dress convinced me to do this, but I still felt like a boy in a dress.”

“We will work on that. You just need some practice and grooming.”

“Kayla is probably dying to work her skills on me again.”

“You are probably right, but tomorrow it's Lulus turn.”

“Lulu! Isn't she the woman who cuts your hair?”

“Yes, she agreed to help us work on your styling.”

“What!”

“She's my friend. Lulu is going to work on getting get your hair in shape. At first it will be mostly hair treatments with very little cutting. However, before the big show she will give you a winning style. She styles a lot of the girls at your school so don't worry.”

“Yeah, but I'm a boy.”

“Hair is hair and now you can make good use of your long locks.”

“Do we have to start so soon?”

“You have a 10 a.m. appointment. It will be a great way to get you into the right frame of mind. I am getting a color and cut too.”

“Gee that sounds so wonderful.”

“Don't be sarcastic.”

“Fine. Just don't let her do too much.”

“Okay dear. Just trust Lulu.”

The next morning I wore jeans and a blue V-neck sweater to the salon. I wanted to be invisible the moment we went through the front doors. I could feel the eyes of some of the patrons staring at me. The five minute wait before I was called seemed like an hour.

Lulu introduced herself to me as she scoped out my hair and face.

“You have a lot of your mother's features. She probably looked a lot like you 20 years ago. I look forward to bringing out your inner beauty. You are going to have truly beautiful hair.”

“Thank you, but it's just for the show.”

“Your mom wants you to look perfect. I'll help you achieve something that if you are open-minded will look great. Just relax; I don't plan to dramatically transform you overnight. It will be gradual.”

“That's good since this thing is over 3 months away.”

“That's probably just enough time.”

“I think that's ludicrous, but what do you have in store for me today?”

“Enough with the questions. Ginger is going to wash your hair now.”

I had never had my hair washed by anyone other than my mother and that had been a few years ago. It felt very relaxing and the scalp massage was a real bonus. I was whisked over to Lulu's chair and a long silky red cape was wrapped around me. Lulu brushed my hair out and then went to work with just a comb and scissors. She hardly cut much off. When I asked what she was doing she said she was just evening off the length and trimming some damaged ends.

When she finished with the trim she spread some sticky substance above my eyes and before I knew what she was doing she had ripped out some of my eyebrow. I was shocked by the pain, but even more so that she had thinned out my brows. I started to complain, but she just said I was lucky they were not waxing my whole body today.

I thought they were done with me when I was ushered back to the hair washing area. This time they worked some smelly stuff into the roots along my scalp and then spread it throughout the rest of my hair. They then had me wait there for nearly a half an hour. Finally Ginger washed the treatment out and dried it off with a towel. I was shifted back to Lulu's chair where she blow-dried my hair. I tried to get a look at myself, but I was intentionally hidden from her big mirror.

It took less than 10 minutes of blow-drying before Lulu declared that she was done. “That's it for today. I will see you at the same time in 3 weeks.”

Pre-pageant 5.jpg

I finally got a chance to see myself and I was dumbfounded. I had thought she was just treating my hair, but instead it had been dyed to a more traditional blonde shade. My mousy color was now a shiny light golden blonde. It almost perfectly matched the color of Reese Witherspoon's picture on the cover of people magazine. I only remember that, because Kayla had asked me what I thought of her hairstyle. I liked it on her, but now I had it too.

Lulu had kept my hair straight with just a touch of under-curl at my neckline and shoulders. My eyes looked bigger because of the thin eyebrows that now framed them. The image was still me, but I clearly look less masculine and much more Ellie like. I did not know any boys with that shade of hair and the thin eyebrows certainly added to the ambiguous image. It was not an overtly girl style, but at best, I now had an androgynous appearance.

I knew it would be impossible to hide my new hair color at school. My mother did not share in my concern. She was quick to compliment me and told me it was a big improvement. I just wanted to get out of there before they did anything else to me.

After paying our tab mom looked at me with a very delighted expression, “Let's go to the claim company at Northbrook Court Mall and split a salad?”

“How about we pick up a pizza and go home?”

“It's not on our diet and besides I want to make a couple of quick stops at the mall.”

“I don't want anyone to see me looking like this.”

“Don't be silly. You look 100% better and besides you need to just get used to it.”

“Fine, but let's not hang out there forever.”

“Just as long as we need to.”

I enjoyed the chopped salad and was grateful for the bread roll that came with it. I felt fortunate that I did not see any friends while we were eating. After we paid the check, mom quickly led us out towards the atrium.

“Where are we going?”

“To pick up a few things and to get some professional advice.”

“Okay but where to?”

“Well the first place is only two doors down. If you remember, we talked about going there 3 or 4 months ago. I decided not to make you wait until you are 16 to get your ears pierced.”

“Huh, you want me to get my ears pierced?”

“Yes. It will help us down the road when you’re accessorizing.”

“Mom I only asked to get my left ear pierced, not both.”

“Doing both is just as simple and later if you choose to only wear one earring, no one will notice the other hole.”

“But for a while I will have to wear posts in both.”

“It was Kayla that suggested getting it done now so the holes will have plenty of time to heal.”

“I knew she was going to be trouble. How about after my next cut?”

“Stop whining. We are here now and I have already scoped out some nice gold studs for you.”

“Great. Anything else you have planned for me today?”

“One additional stop, but let's take care of this first.”

It only hurt for a few seconds and clearly added to my already androgynous appearance. I think a couple of the young girls in the store thought I was a girl getting my ears pierced. Rather than give them dirty looks I flashed a friendly smile at them. It was easier to play along than to be defiant.

“That wasn't so bad was it?”

“It's not the pain, but rather all of the changes coming at once.”

“You just look like a cuter version of Lucas. I'm sure it will pay benefits with Kayla.”

She was probably right about that, so I felt a tiny bit better.

“Let's get the other stop over with and go home.”

“Follow me, but if you see something in any of the windows that catches your eye let me know.”

“Where now?”

“We are off to see my old friend Rachel. She will be expecting us.”

“Expecting us for what? Where are we meeting her?”

“She's up on two and works at Soma’s.”

“Isn't Soma a place in California?”

“No, that is Sonoma, and this place is here at the mall.”

When we reached the front entrance I could see that Somas was a lot like Victoria Secrets down on the first floor. I always enjoyed looking into the window at Victoria Secrets, but had never been inside. Sensing my surprise my mother casually grabbed my hand and led me straight up to the counter. A beautiful woman that was probably 5-10 years younger than my mother reached out and greeted us.

“So you must be Sarah’s precious little Lucas. I think it's wonderful that you are throwing yourself into the Glenfield fundraiser. I can't wait to see you in the show.”

“Thank you. I didn't think many people knew about it already.”

“Your mother asked me to help out with my specialty.”

“I'm afraid to ask, but with what exactly?”

“Your mother asked me to help you get fitted for various types of lingerie. She said your current pieces were hand-me-downs and that you need to get some new items of your own.”

“This is ridiculous, I can't…”

“Quiet Lucas. Rachel is doing us a big favor. No one will see you and you can stay in the changing room.”

“I don't need this stuff. Kayla's mom gave me that set the other evening.”

“I have returned those. You are going to need all sorts of items. Some for special outfits and some for more everyday types of clothes.”

“Why so many?”

“Well for one thing you are not so naturally endowed. We will need things to give you better proportions.”

“I asked this before, but why so soon?”

“You cannot wear anything else without proper undergarments and more importantly you need to get used to them. Starting to wear a bra takes some getting used to for all girls.”

“Rachel may be good at this, but remember I am not built like her regular customers.”

“That's why you need her professional help. She works with people who have had cancer and have to live with other physical issues; besides she tells me that she has had a fair number of men and boys as customers before.”

“I can't believe I am here for this.”

Rachel showed me to the changing room where she told me to strip down to my panties. She seemed surprised when I told her I had jockeys on. I felt so naked as she measured by body from almost every spot. She even grabbed my chest to see how much lose fat I had around my breasts. They were a little flabbier than I would have liked, especially since I had lost some weight.

In an attempt to make light of my dilemma I joked, “I guess I really don't have that much to fill a bra in with.”

“I sell a lot of bras to girls with less and besides we have silicone inserts for you for those time when you want or need more shape.”

Rachel’s comment didn’t make me feel any better.

“When you pick out your gowns for the fundraiser you will probably have to come back for matching lingerie; until then, we will select a few traditional styles.”

“A few?”

“You need some for when you dress up more completely and others for when you are in boy mode.”

“I am not wearing them when I am in boy mode.”

“Honey, Rachel was going to fit you with some underwear that only you will know you are wearing. I want you to get used to them so it won't be a big deal every time you need to put them on. You won't have to wear them all the time, but you need to get over all of your anxieties.”

“Your mother is right. You will like how the seamless bras feel. Even the newer push-up styles are comfortable if you have the right fit.”

I spent the next fifteen minutes getting in and out of more than a dozen different brassiere style. The silicone inserts were only meant for a ‘B’ cup size, but they felt like mountains hanging from my chest. Even the bras that were not to be worn with the breast forms felt like they gave me a protruding set of breasts. I noticed that some of those had built-in padding. Rachel said the padding was to keep them smoother and more invisible, but they also added some cleavage.

After I had put on the last bra, a pink padded style, Rachel nodded and said, “We are done with the bra fitting for now.”

I was then handed a black thong like item that looked like a girl's skimpy bathing suit bottom.

“We don't sell these here, but I ordered you a couple when your mother explained the situation. I will leave the room and you can tuck your boy thing all the way back between your legs and pull this over the top. It should give you a flat front so you can try on some briefs.”

At this point nothing could have added to my over-the-top humiliation, so I just tried to comply. It was awkward at first, but I found that my body had a natural cavity for my balls and this allowed my thing to lay flat. The gaffe then created a flat illusion. It was pretty disconcerting not to see any lump showing.

“Okay I have it on.”

“Try these on over the gaff.”

I slipped the lacy pair of pink panties up my legs and they snugly covered the gaff and my hips. I couldn't help but stare at my figure in the full-length mirror. I now had what looked like a young girl's body and with my golden blonde hair the image no longer looked androgynous. I looked like a girl. I saw little sign of a boy staring back at me.

I started to get lost in my thoughts and began to feel my penis begin to stiffen under the gaffe. It was a little uncomfortable, but the feeling was hard to ignore. I was not paying attention when my mother came in with a handful of other panty styles. She probably could not see my erection under the pink panties, and she must have caught my transfixed look on my face.

“Ellie looks pleased with herself.”

Her comment pulled me quickly out of my trance.

“Oh I was just thinking about how strange this makes me look.”

“I don't think strange is the proper adjective. You look different, but in a good way.”

“Mom, I’m just feeling very overwhelmed.”

“We are almost done. I picked you out a few alternative boy style briefs. This pair looks just like your old jockey style, but without the fly. You will quickly learn to like the feel of these more than your old ones.”

“It's just bizarre looking at my flat front. I have a hard time absorbing that.”

“The flat front will give you more confidence to try different clothing options, especially if you find yourself really enjoying the new sensations.” At that point I could see my mothers devious smile.

I was too embarrassed to directly respond to her obvious point. “I don't care which pairs you pick. They all looked the same to me.”

“Okay then, I will select for you some matching sets and a few plain white ones to replace your old jockeys.”

“I'm not going to need many.” My comment didn't even receive an acknowledgment.

“You don't need to try anything else on. I am going to pick up a few other items, but I know they will fit.”

“I can't imagine what else I need, but as long as I am done for now I don't really care.”

“Alright, just slip your pants and sweater on and we can go.”

“Where are my underpants?”

“That old pair was completely worn out. I want you to wear what you have on so you can begin getting used to the feeling.”

“Mom! Come on! Haven't I done enough today?”

“Let's not have a fit in the store. Rachel did you a favor today.”

“Can I at least take off the bra?”

“It's just a “AA’ cup! I will remove the tags. I am not asking you to wear one with inserts. No one will know.”

“I'll know and it may not be as big as one of the bras that have room for the breast forms, but it is padded.”

“That’s the whole idea. I want you to know that you are wearing it. I wanted it to eventually feel second nature and not like a costume.”

“Mother, with my new golden blonde hair shade, the new earrings, my thin arched eyebrows, and the new underclothes; I feel like I am practically turned into a flat-chested girl.”

“Would you rather have one of the bras with the silicone breast forms? Would that help?”

“Funny mom. Please tell me we're done for the day.”

“No more shopping this afternoon unless you want to, but I did invite Kayla over for dinner.”

“She's the only one besides you that will think this is great.”

“She wanted to come with today, but I thought it would be easier for you if we went without her.”

“That's the first sensible thing you have said today.”

I felt so different after I pulled up my pants and covered over my new bra with the sweater. My pants look very different to me because I was too flat for a boy in the front. I am sure I noticed it more than others would, but I couldn't get it out of my mind. I was also worried that my bra might be visible under my sweater, especially with my slightly increase breasts.

The day's multiple activities were more than I had anticipated, but now I was somehow grateful that my mom did not have even more planned for me this afternoon. I felt so conspicuous as I walk through the mall on our way back to the car. I kept my head down even though I was looking around to make sure I didn't see any of my friends. My mother told me to correct my posture and keep my shoulders back.

“You're walking like a great ape, you need to be more graceful. Point your toes a little more in-word, keep your elbows in, and try and keep your head and shoulders back a little. If you walk more gracefully you will look less out of place.”

“That's easy for you to say, please let's just get home.”

When I got home I went right up to my room. I closed the door and immediately went and looked in the mirror. The experience had finally sunk in and I wanted to see for myself how I looked. I could easily see how I might be mistaken for a girl, but I tried to mentally convince myself that with regular outer clothes on I still looked more like a boy. I am not sure what possessed me, but I found myself posing like a girl to see if that made any difference. I even turned my head a couple of times to get my hair into a more sexy appearance. I think I would have died had anyone seen me at that moment. I pulled myself together and grabbed my schoolbooks so I could get my mind off the strange events of the afternoon.

Chapter 5 ---

The afternoon went by quickly and it was almost time for Kayla to come over. My mother insisted that I continue to wear the new undergarments and I pretended to complain. I knew it was crazy for a boy to be dressed like I was, but part of me knew that Kayla would enjoy seeing me this way. The last time we had been together had been a special evening between us. If this is what it took to get her attention, I didn't mind pushing the envelope a little bit.

Kayla arrived almost exactly on time at six for dinner. I knew that dinner was only an excuse for Kayla to come over and see the changes that my mother had coaxed me into. As soon this Kayla laid sight on me I could see her excitement level skyrocket. It had been the first time I had seen that bubbly personality of her's, since that night she had managed to get me into one of her dresses.

“You look so wonderful. I love the new hair color and it looks so much prettier. Now that your ears are pierced, I will be able to share with you all of my earrings. Maybe after a while, I will be able to borrow some of yours.”

“This was a lot more than I expected today so give me a break.”

“I'm not trying to be mean. I really love the new you. Try not to fret, because this is going to get more and more fun. I promise.”

As if to make her point, she planted a kiss right across my lips. I didn't realize it until later, but her lipstick rubbed off on my lips. It wasn't until after dinner that I noticed the transfer.

Later after dinner my mother suggested that I show Kayla all of my new purchases. She told me that she had put them in the dresser drawer where I kept all of my underwear.

When I opened the drawer, Kayla look like a child on Christmas morning. Her eyes lit up and she practically took everything out at once.

“Wow you really stocked up and now you have almost as much as me.”

“Yeah, mom went a bit overboard.”

“Not at all! You just have a lot of options now.”

“I can't imagine needing so many different styles and colors.”

“Look at these. They look so real. Why aren't you wearing these now?”

“Come on Kayla isn't it enough that I am wearing what I have on now?”

“I love that you wore some of your new lingerie for me, but I really want to see you with these on. Please. Pretty please.”

“Why are you so keen to see me looking so totally girlish? Between you and my mom, it's getting hard to be myself around here.”

“Well for a while, why not just go with the flow. We are the two people who care about you the most and want only the best for you. I would never do anything to you that I didn't think you would ultimately enjoy or ever try to hurt you. Sometimes a little adventure has its rewards.”

Almost on cue, she put her arms around my waist and pulled me in. “Ellie, it turns me on to think of us as two babes with our bodies wrapped around each other. For me I get my best friend with a lot of extra benefits.”

“I guess that is a sort of sexy thought, but underneath it all I'm still a boy.”

“I know that, but nobody is perfect.”

We both got a chuckle out of your last comment. I knew that Kayla would not settle for a half Lucas—half Ellie get up. She was going to want me to fully address again. I wanted to please her and though I wouldn't admit it, the thought of us making love to each other as girls was starting to grow on me. In one breath it felt so mind-boggling, but I also had never experienced somebody desiring me like Kayla did when I was dressed so effeminately.

“If it makes you happy I will change bras and wear the inserts.”

“You know it will, but I want you to be happy too.”

“I'm happy when we are together.”

“You aren't just a cutie, you are also a sweetie.”

I pulled my sweater off and needed a little help from Kayla un-clasping my bra in the back. I put on a black satin brassiere that had much more structure than the one I had taken off. Kayla slipped the silicone breast forms into place and marveled at how perfect my pert chest now looked.

“I wish we were at my house so I could dress you in some of my more stylish clothes. I guess I will have to settle for girl trying to look like a boy.”

I was about to put my sweater back on when she stopped me.

“Your mother got you some other cool stuff to help with your boyish figure.”

“Like what?”

“I see a cinch and a padded brief.”

“What are those?”

“Take your pants off.”

“Excuse me!”

“I'm not going to attack you, at least for now.”

I even removed my pink panty. I was still covered by the gaffe, which brought another smile from Kayla.

“With that covering your little triangle, you could pass for a girl in any clothing.”

“I then slid up the padded brief which had thick pads on my fanny and hips. She then wrapped the elastic cinch around my waist and attached all of the hook's to their clasps. It was very restrictive and made breathing hard at first.

I now possessed a body shape that was full of curves. This was not the shape of a teenage boy.

Kayla took the dress she had given me out of my closet.

“As good as this looked before, you are going to look 100% better now.”

After slipping it over my re-shaped body I could not get over how amazing my figure looked. When I slipped on the heels my posture and figured looked phenomenal. Even I knew I looked good in the dress.

“Kayla this is freaky. My shape looks too much like yours.”

Ellie, it might even look better. You are going to be a heartbreaker.”

Pre-pageant 6.jpg

“Stop that.”

“I really mean it. I wish I had my makeup kit so I could finish you off all the way. I have some tinted lip gloss and my eyeliner, but that's it. Maybe your mom will lend you something.”

“I don't want to ask. God only knows what she would say or do if she saw me now.”

“Okay then, but hold still while I outline your eyes and cover your lips. Thankfully you have naturally thick eyelashes.”

The final image was even more shocking to me than the first time I had put on the dress. With my enhanced figure and the changes in appearance from my excursion to the mall, I now appeared completely female. I had not asked for any of this, but the truth was, I now had a growing satisfaction that I looked attractive.

“Ellie, you have to show your mom. She knew we would be playing around so she won't be surprised.”

“I don't know. This has gone so far so fast.”

“That may be, but that doesn't change how great you look. Wait here while I go and find her.”

“But,….”

Moments later my mother was in my room asking me to spin around. “Well Ellie you have really grown up.”

“Mom, is this what you expected?”

“Honey I knew you would look gorgeous. I'm so happy that you like dressing this way.”

“Who said I like this?”

“Let's not play games. It didn't take that much for you to blossom into the beautiful lady in front of me. If you really hated this, none of this would have been possible. We may have pushed you, but you took to it like a fish to water.”

“I just wanted to please everyone.”

“And you have. There still is over two months before the big show for you to enjoy the new you and refined your persona. After that you can put an end to this fun if you really want to.”

“Just because I'm willing to dress like this doesn't mean I want to stay like this. Heck, I've only done this a couple of times now.”

“That's true if you don't count the two Halloween's when you dressed as Cinderella and then the following year as Dorothy from the Wizard of Oz. I could see then how much you enjoyed getting into costume.”

“That was so long ago. That doesn't count.”

“Whatever you say, but you have always enjoyed hanging around girls. Even at the flower shop everyone always says you have a good feel for what girls would like.”

“I'm just saying that you can't assume I really want to be a girl. I'll always be Lucas.”

“I love my Lucas. You are everything any mother could hope for. I will love you whether you are my little prince or princess. Don't worry about tomorrow. Let's just take this day by day and hopefully Ellie will have fun now and then later in the pageant.”

“I'll try, but some of the changes are going to be very hard to cover up.”

“Honey, other than the obvious padding, everything else is just a style statement. I bet most of the double-takes will be positive in nature. For every strange look or comment you will probably get 10 people thinking you look fabulous. I don't expect you to wear your pads or breast forms to school, unless you want too.”

“Yeah right. If I showed up wearing those I would be laughed out of school.”

“Actually, if you weren’t trying to look like a boy with big breasts, I suspect hardly anyone would laugh. For now let's ease our way into the pageant like we have planned.”

“All of this training is okay for me here at home, but I know I am not ready to handle things at school.”

“We will focus for now on exploring things outside of school. I am sure Kayla will give you a crash course in girlhood. You have a lot to learn and unlearn.”

“I will Mrs. Everdeen. I’ll have him thinking and feeling like a girl before you know it.” The rest of the evening Kayla and I hung out in my room. We talked about everything from school to music. The discussion was decidedly girl talk. We talked about ‘other’ girls at school and even boys. She kept pushing me to say which guys at school I thought were cute. I resisted as much as I could, but under pressure mentioned a few boys I thought were handsome. She even teased me a little about what it would be like to go steady with one of them.

I joked back that I couldn't because we were going steady. She countered that we were special girlfriends, but boys can be fun too. I wasn't certain I completely liked what she was implying, but we were having such a good time hanging out and snuggling.

“I can't wait until you and your mom begin to fill out your wardrobe. She also mentioned to me that she would get you your own set of cosmetics. She wants me to teach you how to make yourself look perfect.”

“My mom is certainly not holding back on buying me stuff for this benefit. I'm sure just like she did with the underthings, she will probably go overboard.”

“She just wants you to be happy and enjoy the new you…. And so do I.”

“I'm enjoying things with you right now.”

With that, we kissed for one last time for the evening. It was nearly 11 o'clock so my mom suggested we drive Kayla home even though she lived very close. It was dark and I agreed to go along for the drive in the dress. Unlike my first excursion out, I was much more comfortable this time.

When we got home my mother gave me a box that said Soma on the outside. Inside the box were two sets of pajamas. The first one was a dark purple silky combo, which included a camisole style top and matching bottoms. The other item was a soft sleeping gown made from a light yellow cotton material.

“You made so much progress already that I thought you might like to wear one of these after you wash off your makeup.”

All I could say was, “Thanks mom, they are very pretty.”

I slept in the combo set because I just loved the way the material felt. I knew that I should not be thinking like that, but I was losing my resistance to dressing.

On Sunday, I came to breakfast in a robe with the tap set underneath. Part of me did that to please my mother and part of me because I liked wearing it. After breakfast my mother told me she had a lot of errands to run and would be out for a big chunk of the day. Her only instructions for me, was to select from my new lingerie something to wear under my clothes. I nodded okay.

I spent much of the day doing homework and trying to get a little ahead for the week. I didn't change out of the pajamas until nearly noon. As instructed I put on a matching white pair of panties and a bra. I was tempted to put a bra that needed the breast forms to fill out, but managed to put the idea to rest. I didn't want to come across as too enthusiastic. With the T-shirt I had on, I could faintly make out the straps from the brassiere.

My mother did not return until almost 4:30. She said she was tired, but had gotten a lot done. She needed to make multiple trips to her car to bring in the bags from her excursion. I asked her if she got everything she needed and she said enough for today.

After she spent nearly 45 minutes in her room we went out for a bite to eat. I was thankful to be wearing a coat that covered my slightly visible bra lines. At dinner my mother pulled a hairpin out of her purse and used it to pull one side of my hair out of my face.

“I love how nice your hair looks but you have to keep it out of your face when you are eating. Sometime this week we should go to a nice department store like Nordstrom's and let you pick out some nice accessories, like hair barrettes. Nordstrom also has a great shoe department and you could pick out a few new pairs. I would have bought you some today, but I really think you should try them on in the store first.

“I am not sure I'm ready to try on girl shoes at a department store.”

“It will be fun and besides Nordstroms is not that close to home and nobody there will bat an eye.”

“I guess.”

That was pretty much the end of the conversation that related to Ellie. The next morning I asked her where she put my regular underwear will and she told me it was in the attic stored away.

“What am I supposed to wear then?”

“Do I really need to answer that?”

“What if someone notices?”

“You are done with gym for the year. How often do you take off your clothes at school?”

“But Mom!”

“No butts…. Do you want me to pick or do you want to do it yourself?”

“Okay, okay.”

I put on the most basic white pair of panties. They were the pair my mother said looked like my jockeys without the fly. When I came down to breakfast my mother came up to me as if to do an inspection, and then shook her head.

“What's wrong mom? I am wearing the new panties.”

“You should be wearing a matching bra.”

“To school?”

“Yes. I want you to get used to wearing them; besides, no one will notice with a shirt or sweater on top.”

“I don't know. My new hair and other changes are already going to be hard for me to explain at school.”

“Okay then, today you can go without a bra at school, but then I want you to wear one with breast forms when you get home. If you are not going to wear one of your nearly invisible brassieres to school, I want you to make up for that, by wearing one of the more substantial ones when you get home. That will be the rule between now and the conclusion of the fundraiser. Are we in agreement?

“Deal!”

I was surprised that my styling changes at school hardly registered with my classmates. I received some odd stares, but no real insults. A few of my guy friends gave me funny looks and some light barbs. Overall, I was grateful that I did not get any really hurtful ridicule.

I actually got a few compliments from some girls in swing choir. They generally liked my new hair color and said it looked more stylish. It felt reassuring to know that my appearance blended in without too much of a hitch.

I saw Kayla a few times during the day and she was full of smiles, but she did not show me the same level of sexual affection that she shared over the weekend. She was very friendly, but seemed to keep enough space between us to avoid potential kissing opportunities. I hoped that I was just overreacting to the situation.

After a couple of days of adjusting at school and wearing the full-sized breast forms at home I was settling into a more comfortable routine. I didn’t leave the house while wearing the larger breast forms, but after only two evenings with them on at home they didn’t feel so foreign.

End of Part 2

The Fundraiser/Or How I Was Volunteered for a Womanless Beauty Pageant 3

Author: 

  • Nina Adams

Audience Rating: 

  • General Audience (pg)

Publication: 

  • 7,500 < Novelette < 17,500 words

Genre: 

  • Illustrated

Character Age: 

  • Teenage or High School

TG Themes: 

  • Contests, Deals, Bets or Dares
  • School or College Life
  • Sweet / Sentimental

TG Elements: 

  • Estrogen / Hormones
  • Fancy Dress / Prom / Evening Gown
  • Hair Salon / Long Hair / Wigs / Rollers

Permission: 

  • Posted by author(s)
PART 3 (conclusion)

Pre-pageant2_0.jpg


THE FUNDRAISER PART 3
or
How I Was Volunteered To Be In a Womanless Beauty Pageant

by Nina Adams

Chapter 6

On Thursday, I received a big surprise when I got home from school. My mother had taken the day off and she obviously used much of the day to prepare some new changes for me.

When I walked into my bedroom I immediately discovered some of the most obvious changes. My bed was no longer a adorned by the rustic green bedspread. It was now graced by a fluffy white comforter with pink pillows that had lacy fringes. There was now a vanity table where an old unused chest used to reside. A floor-to-ceiling mirror had replaced the small mirror on the back of my bedroom door. Even the curtains now matched the obviously feminine bedspread. My mother had taken it upon herself to transform my living space into a girl's room. It seems so extreme and unnecessary, but not that surprising based upon my mother's enthusiasm for my training.

Just as I had each of the previous days, I changed into my larger “B” cup sized brassiere and slipped in the silicone inserts. After checking to make sure everything was positioned perfectly, I open my closet door to pick out a T-shirt. I was greeted by an even bigger surprise when the door slid open. Most of my clothes had been replaced with new garments. The clothing was decidedly more colorful and even without close inspection, I could tell they were obviously girl's clothes. There were tops, slacks, skirts, and even a few dresses filling most of my hangar space. On the floor was a new shoe rack that had only two pairs of my old shoes, along with a new pair of clogs and a lot of empty space. On the side of the closet there were some new hooks which had an assortment of girls belts draped over them. Despite having a small amount of my old clothes still hanging there, this was not a boy's closet. I was much more stunned by this turn of events than the superficial changes to my room. Where as my room was a private place, the clothes were meant for me to wear both inside the house and possibly out.

I would have stormed down to my mother, but I knew she was not home at the moment. I spent a few minutes flipping through some of the new items with a strange fascination. I found a black T-shirt that look plain enough and pulled it over my head. Unlike my old tops, this shirt hugged my curves and accentuated my new found cleavage. The collar also was styled with a square neckline. None of my old shirts looked anything like this on me. I left it on as I perused the rest of the new wardrobe. After getting over the initial shock I found myself holding some of the items up to my body to see what they looked like.

As I was holding up a sleeveless green chiffon dress to my body, I did not notice my mother walk in.

“You know Ellie, you’re going to have to go with me to get shoes that go with that.”

“Mom you startled me!”

“I’m sorry honey, you were just so focused on the dress.”

“I, I was looking at all of this stuff. There is so much here.”

“I hope you like everything.”

“I can’t believe how much you bought. I will never be able to wear most of this.”

“Don’t be so sure. I selected some outfits that are very casual and some for more dressy occasions. Quite a few of them will be perfect for school.”

“School! I can’t wear these clothes to school or even out of the house for that matter.”

“Ellie, I bought you very casual items for school that are not that different from your old clothes. The items are just cut a little different or in nicer colors. I don’t expect you to show up tomorrow in a skirt.”

“But mom, I don’t want to be a laughingstock. This is just more than I bargained for.”

“I saw how you were looking at that beautiful dress. I just thought you would be happier to have some nice new things.”

“I appreciate you picking out all of this, but I can’t just show up at school as a girl. The fundraiser is still two months off.”

“A lot of what you see is just T-shirts, blouses, sweaters and slacks. You said that your other new style changes went over well and I bet the new tweaks will too. A lot of your classmates including Kayla love the androgynous look.”

“I just don’t know mom.”

“You can work into it and build up your comfort level.”

“How’s that?”

“Tomorrow wear the purple T-shirt and a pair of new jeans. You needed some new clothes anyway. At home you can get comfortable with the more feminine pieces. Try and keep an open mind. It will just be more fun that way.”

“Where is the rest of my clothing?”

“Most of it was old or nearly out of season. I boxed up those things for Goodwill. If you need something you don’t have we will just go shopping. We still need to get you some new shoes. I think we will go after school Friday.”

“I can’t believe I committed to all this to get a motorcycle.”

“Sure you did.”

“What do you mean?”

“Nothing Honey. By summer I hope you don’t feel that way. Now go upstairs and pick out something that looks nice with that black top you selected.”

There were so many new items packed into the closet that I didn’t know what to choose. I just grabbed the first pair of jeans I saw even though they were at a light yellow color. I noticed they had cuffs at the bottom, but with my already feminine appearance I really didn’t care. When I pulled them on I discovered they were only covering my legs to mid calf. Looking in the mirror I had to admit the capris look cute with the top I had selected earlier. They had a snugger fit than my old jeans and I decided to leave them on. With my shapely chest and the new clothes, there was little that could be mistaken for androgynous.”¨

I finished scoping out the new clothes and even shifted a few items closer to what was left of my limited supply of boy things. I moved over the least feminine items. There were some pants, shorts, T-shirts and a sweater that didn’t appear overly girlish from a quick scan. I picked out some long bluejeans that I thought would go with the purple top for school on Friday. Other than a squiggly design on the back pockets, they just looked like new jeans. I placed them next to the purple top on my chair so I would not pick the wrong pair in the morning.

I had a busy night of homework and had very little extra time to do anything else. My mother stopped in my room before bed and saw the jeans hanging over the chair.

“Ellie, those are very expensive jeans and have a slightly different cut than you are used to. When you get dressed in the morning I suggest you wear your padded brief, otherwise they will probably be slipping down your waist and drawing more attention to them. They just need a little more hip to rest upon.”

”But, I don’t want to look bigger around my hips.”

“Honey you have lost some weight and you won’t look fat down there.”

The next morning I pulled the black padded brief over a pair of white panties. The padding was very smooth except for a small lump between my legs. I tucked my manhood under my legs as I had many times before and the lump disappeared. I was probably going crazy, but the smooth bottom seem to look more appropriate in the black garment.

I pulled the jeans up and they fit nearly perfectly. They hugged my midsection and accentuated my flat front. I was a little concerned that they seemed to lift up my rounded bottom. The only other problem I quickly discovered was that these jeans were longer than my normal pants. I was concerned that I would be tripping all over them. I pulled the polished black clogs from my closet on a whim. They easily slipped on and the larger heel did the trick on eliminating the extra pant length. The pants mostly cover my shiny shoes, so I figured that would be my best option to avoid tripping.

The purple top was just a T-shirt but it seemed to hang differently. It had some extra weight to it and it was made of Rayon. I couldn’t help thinking how it might look if I was wearing a padded bra or my breast forms. As unconventionally as I knew I looked, I was no longer upset by my appearance. I was starting to enjoy looking more stylish.

It took me only a short time at school to adjust to my newest changes. With the padded brief firmly holding down my manhood and the necessary adjustments to the higher heels, I found myself taking smaller strides. The heels also seem to alter my posture a bit with my hips pushed forward a small amount.

Fortunately, I didn’t encounter any new school problems. The classmates who looked at me strangely after my salon visit continued to give me strange looks. I did sense that some of my guy friends were not as chummy, but I was clearly drawing more attention from the girls. One of the girls in first-period even commented how much she wished she had a pair of “True Religion Brand” jeans like I was wearing. It was kind of funny because I didn’t even know what brand I was wearing. I just smiled back and thanked her.

When I saw Kayla later that morning she gave me a great big grin and asked me to do a 360.

“You look Bitchin!”

She made all sorts of comments about how great my outfit was and that I was finally developing a fashion sense. Everything she said was meant as a compliment, but it was all girl talk. There was nothing about us, just encouragement for my changes. I was happy be she was happy, but I really wanted to relive the feeling from the last time we got together.

Moments before the bell was to ring she asked me if I would like to go to the mall Saturday and maybe have dinner. Without thinking it through I jumped at the chance to spend time with Kayla.

“You’re on!”

The final school bell sounded and the beginning of the weekend felt so relieving. The weekend had arrived and I didn’t even have that much homework. I made my way home through the cool spring air.

Chapter 7 ---

As I had each day this past week as part of my compromise with my mother, I slipped on the full-sized bra and inserted the breast forms. I put back on the same T-shirt that I had worn all day.

With my well rounded chest my appearance screamed girl. I even started running my hands through my hair while getting absorbed in my strange fascination with my image.

It was not that long before my mother got home from the flower shop. She quickly tracked me down and asked me if I was ready to go.

“Where are we going?”

““We discussed this earlier in the week. You need some shoes.”

“Can’t you just buy them like you did all of the clothing?”

“Trust me, you just can’t buy someone else shoes. Besides, the sizing is so much different than with boy shoes.”

“I don’t want to try on girl shoes at the store...people will laugh at me.”

“Only if you act like a boy and complain.”

“What if I see my friends?”

“We will go down to Nordstrom’s at Old Orchard. That’s 20 minutes away and your friends rarely hang out there.”

”Alright, give me a few minutes so I can go and change.”

I suggest you wear a skirt. It’s so much easier when you are trying on different styles.”

“What! I was just going up to take off my bra.”

“No you don’t, we had a deal. Besides, the top looks so nice with the curves.”

“Mom. I can’t go like this. No boy has breasts.”

“Honey you’re shopping for girl shoes. It’s better that you look like they belong on you.”

“Please don’t make me do this.”

“You will be fine. I really think the faux blue A-line skirt would look great with that top, but I won’t force you to wear it.”

“I’m sticking with the jeans.”

“Suit yourself, but you will wish you had something shorter on.”

As we were heading out the door my mom gave me a pair of oversized Prada sunglasses. They had a very feminine design, but I was thrilled by how they changed my appearance. I looked even more girlish, but less recognizable as the boy under the feminine façade.

We parked just outside the east entrance to Nordstrom.

“Before we go inside I want you to relax and try and enjoy this. Shopping for nice things should be fun. I want your opinion of what you like or don’t like, let your mind go a little. Try and think like Ellie would. You are just a cute girl out on a shopping excursion. I want you to think like that. If you can’t open your mind this will be so much harder. Just follow my lead and don’t fight it.”

“I will do my best, but I know people will see through me.”

“I am sure you will get some attention, but only the kind a cute teenager deserves.”

I could see the massive shoe department as we entered the store. Before we had gone more than a few steps in that direction, I was steered off to the right. I found myself squarely standing between the Chanel counter and a Mac counter in the middle of the cosmetic section.

“Ellie, you need to get some of your own cosmetics. You can’t keep borrowing Kayla’s and my things. This is a good time to get professional help matching your skin with all the best quality products.”

“But...”

“No buts, hop into this chair.”

It was nearly 45 minutes later before I left that chair. In addition to purchasing a shopping bag full of products, I had received a glamorous makeover. My Prada sunglasses were now back in my mother’s purse and my new look was on full display. My eyes had been highlighted, outlined,and shaded and what could be described as seductive artistry. My eyelashes had been thickened and my whole face look brighter and naturally feminine. I was now even tagged with plump rosy red lips. My painted face clearly added to my attractive appearance and I thought I looked a couple of years older.

With each increase in my transformation my mild resistance disappeared. I knew I looked all girl and I was beginning to feel that way. I no longer question how I would be perceived, as a result I was no longer feeling like a frightened boy.

“Mom this is incredible. I never thought I could look like this.”

“You certainly look fabulous.”

“I’m not sure if I’m attracted to my reflection or just like looking this way. Is there something wrong with me?”

“There’s nothing wrong with feeling pretty. I suspected you would enjoy this total makeover when you let your guard down.”

“I know I shouldn’t like this, but this is the first time I ever really felt attractive.”

“You’re going to have to get used to that.”

“I guess I will enjoy it while I can.”

“Since you are getting in tune with your feminine side, can we get you something else to wear before we try on shoes?”

“I’m all yours mom. I’m not sure what I wear matters anymore.”

Up the escalator we went into the women’s fashion department. We were quickly greeted by a consultant that inquired as to what we wanted. We exchanged introductions then my mother answered.

“My daughter is looking for some age appropriate clothes for when she is a little more flirty.”

I went a little red under my make up when I heard my mother’s response. I liked looking pretty, but flirty would not have been my answer.

“Follow me, I have some great new styles that just arrived. Most of them will be great for the spring and summer, especially if your Ellie has a boyfriend.”

I had the beginning of a dry mouth. My mindset started to shift into a daze..

I felt like a mannequin as I tried on more than a dozen dresses and a few mix-and-match tops with skirts. My focus was not on the price tags, but I was shocked by the prices on some of these items. My mother seemed indifferent to the cost. She was only focused on my appearance.

Instead of buying just just one skirt or outfit, I ended up with three dresses, two more blouses, and two short skirts. I ended up wearing a formfitting deep burgundy dress that had a lace tiered skirt that flared at my hips. The dress had a matching wide ribbon styled belt that accentuated my narrow waste. My wardrobe was expanding at a geometric pace.

Our consultant quickly pointed out that my shoes look very clunky with the new dress.

“As soon as we pay for these things I plan to take Ellie down to the shoe department and get her some new heels.”

As we headed down to the shoe section I began to have new confusing thoughts. When we left our house I still felt like a boy wearing sissy clothes. Now I knew I looked completely like a girl and I could sense people looking at me for different reasons. As I went down the escalator I saw a boy nearly twist his head off giving me a hungry look as he road up the opposite escalator. I was now attracting unexpected attention.

I was grateful my mother had no financial issues, because the tab for the shoes we bought was ridiculous. The price we paid for a pair of Jimmy Choo shoes was more than all of my old pairs combined. I felt like a klutz walking around on some of the higher sets of heels. In addition to some dressy pairs, I ended up with wedges, sandals, a pair of tall black leather boots, two basic plain flats, a pair of Mary Jane’s, and a shiny leather pair of low ankle boots which I wore out of the store. If we could have carried more, I am convinced we would have still been shopping.

With every thing safely stored away in the back of the SUV, my mother announced it was time to eat. I was exhausted from the experience and from overcoming my earlier anxieties. I was ready to go straight home.

“Let’s have a celebratory dinner.”

“What are we celebrating?”

“The birth of Ellie. I am very proud of you tonight. This was a real coming out for you. Despite your modest resistance you have blossomed into a beautiful young lady.”

“Mom! I’m just trying to be cooperative.”

“Tell me you didn’t enjoy this.”

“It’s not that simple. It was fun, but underneath it all I am still Lucas.”

“You are still the same wonderful child, but I don’t think the name Lucas it’s very appropriate anymore.”

“Mom!”

“Okay honey, now what’s your favorite restaurant?”

“I can’t go to my favorite places looking like this. I could run into someone I know.”

“Well Ellie, you can’t stay inside for the rest of your life, besides you look so beautiful tonight.”

“The rest of my what?”

“How about Sushi Kushi in Lake Forest? You love that place and it’s not that close to home.”

“Okay, but straight home from there.”

It was after nine before we pulled into the garage. The evening had been a whirlwind and almost out of body experience. I had always been tight with my mother, but now there seems to be a new bind between us. I actually looked forward to continuing my role-play and wearing some of my new purchases. After carefully putting away my expensive hall, I was ready to crash on my bed. I reluctantly removed my beautiful makeup and hung up my bouncy layered dress. I didn’t even bother to remove my breast forms, bra or panties as I slid under the covers. I was asleep in a matter of minutes.

I slept until nearly 10 AM. It had been a restful night of sleep, although the breast forms were a little warm under the blankets. I brushed my teeth and combed my mess of hair. I was a little sad that my reflection did not look as nice as the previous evening. I worked on my hair for quite a long time until I though it looked acceptably feminine. I actually thought of putting on some of my new makeup, but I took pause. It had been a crazy and yet enjoyable evening, but my sense of reality was reminding me this makeover was meant to be temporary.

It no longer felt like a game. I knew deep down that I liked my new image. When I looked at my reflection I no longer saw a stranger. There was a subtle emerging smile that glowed throughout my face. It was a happiness I never knew as Lucas.

My mother yelled from downstairs for me to come down to breakfast.

I pulled over my head and lingerie a long lavender nightgown that I had not yet worn. With my shapely breasts, the gown took on the look of a silky evening dress. The gown wrapped my body without overly hugging it. I was sure my mother would be pleased with my choice of breakfast apparel.

As I entered the kitchen I was shocked to find Kayla and her mother already sitting at the table.

“Ellie dear, aren’t you going to say hello to our guests?”

“Hi Mrs. Miller, hi Kayla.”

“That’s a beautiful nightshirt Ellie.”

“Thank you Mrs. Miller.”

“Hey girl.”

“Hey Kayla, why didn’t you tell me you were coming over?”

“Sorry, but I didn’t know until we we were almost out the door. You sure look cute.”

This was the one group of people that knew what I was going through, so after the initial shock I was able to relax. The breakfast conversation quickly covered all aspects of our shopping excursion and most of my new purchases. I tried to imply that I just went along with it, but I was pretty sure they knew how much I had really enjoyed it.

“Honey after breakfast Kayla is going to help you organize your new cosmetics and give you another makeup lesson. Also please change into something more appropriate for the day.”

Up in my room Kayla's mood shifted from happy to almost giddy. She rifled through all of my new clothing, shoes, and cosmetics.

“Wow you have as much stuff as most teenage girls, and most of it is top quality. Anytime you want to swap clothes, just let me know. You picked out some great new outfits.”

“I know, but now I have way too much.”

“Well a girl cannot have too many pretty clothes.”

Kayla selected a black super short skirt and some maroon tights. She settled on a multicolored peasant style blouse and handed it all to me.

I few moments later I was standing in front of her and striking a decidedly feminine pose.

"Kayla, can you help me with my makeup?"

"Sure girlfriend."

Kayla made sure she showed me how to touch up my face for daywear. When she was done I put a pair of hoop earrings through my new holes and some matching silver bangles around my wrists.

"How do I look?"

"Well girl, we are going to have to take you out of the pageant."

"What?, Why?"

"Don't get your pretty little self worked up."

"I don't understand. What did I do wrong?"

"Wrong! Nothing... This is a womanless beauty pageant. It wouldn't be fair. You are a girl. I knew you would make a cute looking girl, but I am not looking at a boy in a costume. I really like what I see, but all I see is Ellie."

"Please don't tease me."

"I'm not. I meant it all as a compliment. You have emerged as a confident pretty girl. Be honest with me, aren't you happier this way?"

"Its been fun, but..."

"Be honest."

"I do like it, but I am not really an Ellie."

"Yes you are..."

"This is all just temporary."

"It doesn't have to be."

"Are you serious?"

"Ellie, if you are happier now, you have to stay this way."

"Like my mom would allow that!"

"Come on, your mom is way ahead of you on this. Are you blind? I haven't seen her so full of life as she has been during your emergence from your shell."

"She is just really into winning the contest."

"Come on. If that was all, she wouldn't have to buy you all this stuff and practically reprogram your life. She enjoys having a daughter and is trying to help you become the girl you are..."

"This has all happened so fast. I didn't ask for this... I can't just wake up one day and go from boy to girl. It's not natural."

"You took to it because down under the desire was really there. We just brought it out. It will still take time for you to emerge fully, but I think we both know that is going to happen."

"It's so surreal."

"You need to stop your token resistance and tell your mom that this is no longer a contest for you. I am sure she knows, but it has to come from you. My guess is that she has already thought that possibility through."

"I can't just flip a switch and start living as Ellie. It's a lot more complicated than that."

"I know. It will take time I am sure. Just let your mind focus on the possibilities."

"I do like being pretty. I never thought I would ever say that."

"Get used to it. You are pretty and I bet you will get even prettier. I am going to get jealous of all the attention you will draw."

"That I don't know if I can handle, but I do like your attention."

"I like your attention too, but at some point the boys are going to be all over you."

"I like girls."

"Me too, but boys can also be nice."

"Umm"

"Don't worry, everything in it's time."

"Help me Lord, what have I gotten myself into?"

"For now, I am going to just continue helping you to become the girl you were meant to be. I'll take good care of you."

"I will try and talk with my mother later... It won't be easy."

As it turned out, Kayla was only partially right. My mother was actually surprised when I brought up my feelings later that afternoon. She knew that I would enjoy my time as Ellie, but was not expecting me to come forward so quickly declaring my womanhood. She actually thought that at some point I would want to return to my old boyish ways. She expressed some honest concern when I told her I was happier as a girl than I ever was as a boy.

Two days later she made an appointment for me with a psychiatrist who had experience in this area. She was careful to explain to the doctor that my feelings had emerged from a simple experiment dressing, so that we could see if I should compete in the school womanless beauty pageant. She was concerned that she might come off poorly for her enthusiasm for my cross dressing escapades. She even suggested to me that I tone down the discussion about how much she had spent on the experience. She implied that some would think her efforts and spending were excessive.

The Doctor was very nice and we spent quite a lot of time talking about things that seemed to have little to do with my gender issues. Over the weeks that followed we talked more and more about my acceptance of my feminine feelings and whether I really felt I was a girl inside. After about 8 sessions over 6 weeks she determined that my desires were not just a phase and that I would need to explore the possibility of living fully as a girl.

Up to this point I had continued to dress and behave at school much the same as I had prior to coming clean with Kayla and my mother. I would dress up as much as possible at home and both of them spent as much time as possible teaching me the things girls usually knew by my age. So as not to draw to much attention to myself, I had even attempted to tone down my now androgynous appearance at school. I was not real successful at that and I often forgot where I was and acted overly feminine. Many of my classmates just assumed I was gay, which was actually fine with me.

I elected to stay in the pageant at school and I began to look forward to. It would be the first time I could show off my total look to my school mates. Kayla even helped me go shopping for a gown after school a few weeks later. The sales woman never even suspected that I was buying it for a womanless pageant. It was quite a rush to be in that environment without them knowing. She must have assumed it was for a party or something.

The Doctor recommended that I finish out my Junior school year as Lucas, and then try living full time over the summer as Ellie. She even prescribed some drugs for me to slow my testosterone flow and begin a small dose of estrogen to see how I would adjust. She indicated that if all went well that both dosages would be increased at the appropriate time.

Kayla and I continued our close friendship and did fool around a little from time-to-time, but we never did have actual sex. We both thought about it and even talked about it a couple of times, but we didn't want to ruin what we had. She seemed keen on me having my first experience with a boy. I was not so sure about that, but as I became more and more comfortable, the thought began to creep into my mind.

When the womanless Beauty Pageant finally rolled around I was so excited to get on stage. A part of the program each entrant was interviewed about what they had learned about beauty pageants and woman. I certainly had a lot to say and I am sure I raised the judges eyebrows more than a little. Each of the entrants had the option to come to school and the pre-pageant assembly dressed as a woman. Of the 14 of us still in the contest, 10 of us came fully dressed. I even took off half the previous school day so that I could get my hair and nails done to look my best. There was nothing even remotely boy about me that Friday when I strolled through the school's front door.

Pre-pageant 1.jpg

Ready for school the day before the Fundraiser

The competition was enjoyable, but I felt just a bit awkward when it hit me that most of my cheers were because I was a boy dressed as a girl, rather than because I was a knockout beautiful girl. As I suspected, many of the other contestants had gone the whole nine yards. It was a very difficult task to narrow the field and select the five finalist. I was certain that most of the finalists would not be wearing dresses for their last time.

My mother was so proud when I was named the queen. She was so happy for me and for Kayla. I saw her look over at Mrs.Gunther, and I knew that she was happy for some other reasons as well. Mrs. Gunther's son Steve looked beautiful and was among the finalists. All of the finalists received prizes that included spa treatments for their teams and them. As victorious Queen, I even received a gift card at a very chichi boutique in town. The store only sold woman's clothes. I nearly squealed when I saw it. I am sure they thought the card would be passed to another family member, but I couldn't wait to get in there and try on some new styles.

The fund raiser was a huge success and proceeds helped pay for one of the fanciest Proms the school ever put on. The prom was three weeks later and that was a whole other story.... let's just say, I got to enjoy some of the funds I helped raise.

When school let out the first week of June, my days as Lucas were history. I worked at Mom's flower shop over the summer as Ellie "the flower girl". I happily settled on a red Vespa instead of a Harley, it was exactly the same as the one Kayla bought. It took some time for my friends to adjust to the new me, but I now have more friends than I ever had before... some of them are pretty handsome.

The End


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