The Blue Dress - Part 3

by MonicaS

Copyright © 2021 Monica S.

After Chris got bullied for being girly and finally was forced to wear a dress at school, he decided to live as a girl. With support from friends, he got transformed into a passable girl, bought essentials, and learned the first lessons for girlhood. He had a long talk with his mother and went to school as a girl again the next day. For the weekend, Chris planed more shopping and a sleepover with his friends.

* * *

On Saturday morning, I dressed in my self-made shorts, combined with a black top, pantyhose with an overknee look, and the ballerina flats. I expected a lot of walking while shopping, so no heels this time. I wanted to look good as a girl, and I always liked how girls in heels look, but I guess sometimes comfort trumps beauty. At least the flats were quite cute with a red stripe on top. Altogether I liked my outfit.

I packed a duffle bag with all my makeup, some spare clothes, and toiletries for the sleepover. I had to buy new sleepwear, though, as my boy pajamas just weren't suitable. I was so excited that I couldn't wait until Anne arrived to pick me up. I put on my leather jacket and took my bag and purse to wait outside for her.

Susan and Paula were already in the car when Anne arrived. Because I didn't have that much money and needed tons of clothes, Anne decided to look through thrift shops first. The girls knew where to go, and it didn't take long to arrive at our first destination.

Most of the clothes in the stores were unfashionable or stuffy and didn't appeal to me. Or they were outright crazy. We had some fun with the crazy stuff, though. The girls took some of the outlandish clothes from the racks, held them to their bodies, and acted like excentric divas. You just had to laugh at their antics.

When we were more serious, I found some gems, for example, a cute yellow jacket, a shiny black dress, and beautiful black ankle boots. And there was the standard but okay stuff like jeans, sleepwear, some tops, sneakers, and heels. They had a lot of underwear too, but who buys used underwear?

In one jewelry section, I found some necklaces and bracelets. I picked up a beautiful pair of earrings but didn't have pierced ears. I hadn't paid attention to it before, but all girls wore earrings. Anne and Paula even had a nose piercing.

"Does it hurt to get your ears and nose pierced?" I asked.

"It stings for a second or two, but then the pain is mostly gone, just like a needle shot," Paula answered. "Are you gonna get pierced? I think you'd look cute with them."

"Where do I get pierced?"

"Some stores have piercing guns, but it's better to go to a professional piercer, especially if you get your nose pierced. I can give you the contact info for where I went. You'll need permission from your Mom, though."

"Oh, I wonder if she'll allow it."

"She allows you to be a girl, so what is a piercing compared to that? And most girls have piercings, so why not?"

"Yeah, you're right. I like these. I'll buy them. And these. And these..."

"Remember, you only have two ears and no holes yet," Paula interrupted before I went overboard.

In the end, I paid well over a hundred dollars, but I got many items. I'd probably be broke if I'd got everything new. The girls found some stuff too but spent much less.

We were a bit worn and decided on a lunch break at a cafe. After resting a bit, we continued shopping with new vigor.

I didn't have any lingerie yet, just some basic underwear. The girls decided I had to remedy that. Susan knew just the right store with affordable lingerie, so we went there.

I felt like a kid in a candy store. I had never been in such a feminine domain. There were mannequins with beautiful lingerie sets all over the place. It was good I wore tight underwear as I got a bit aroused. I had looked at women in lingerie on the internet. What boy didn't? But I never saw it this close in real life. I always avoided the lingerie section when I went shopping with my Mom. I didn't want to be considered a pervert. Now I could look as much as I wanted.

It hit me that I would be the one wearing these alluring items soon, to look sexy for others. But who would see me in them? No boyfriend for sure, as I still liked girls. And girls would only see me in underwear in the locker room, and I'd rather not wear lingerie there. And perhaps in the changing booth while shopping, but that didn't count.

"Who do you wear this for?" I asked the girls. "I mean, do you all have boyfriends?"

"I don't wear lingerie for my boyfriend," Anne replied. "I wear it for me, to feel sexy. Even if nobody sees it."

"Ah, okay." I liked that idea. I could be sexy for myself. "But what should I get?"

"I like a full set of bra, panties, garter belt, and stockings," Anne replied.

"Garter belts are too fiddly," Paula countered. "So just bras and panties for me."

"I like bodysuits," Susan added.

"That is about everything they have," I said. "It doesn't make selecting easier."

"Just look around to see what you like," Anne said.

"Look through everything?"

The girls laughed.

"Okay, I'll try a set with a garter belt."

"Hmm, you are limited, after all. As you use the breast enhancers, you need something that hides them. So no see-through or low cut bra."

"Oh, yes. I guess I'll start looking for that. Most bras here are more or less see-through."

So I went on a hunt for bras. With the help of my friends, I found some suitable ones that I liked. I proceeded to try them on in a changing booth but couldn't make it work.

"Damn, it just doesn't look right," I ranted.

"I'll help you," Anne announced and entered the booth. "Here, let me push this up and the enhancer a bit more down. Yes, that works. Now the other side."

I was quite flustered as Anne manipulated my breasts unashamedly. I felt my personal space invaded with her doing that without asking, but I didn't do anything about it.

"There. The bra looks beautiful on you. Do you want me to help with the others too?"

"Umm, no. I think I can manage." The cubicle was small, and standing that close to Anne made me uncomfortable.

When she left, I looked at myself in the mirror. Even if her methods were questionable, the result was astonishing. I had massive cleavage. I liked how sexy I looked. I examined what Anne had done to be able to replicate it.

In the end, I selected four bras that worked well, colored black, blue, white, and red. I found matching panties and garter belts for each of them and added stockings in different colors. Then I summed the prices up.

"Oh no, they cost too much. I should buy at most two sets."

"That would be a shame," Anne said. "All sets look so good and work for you. And you'll need different color options. You know, I'll buy one set for you as a gift."

"I'll pay for one set too," Susan declared.

"Me too," Paula added.

"Oh no, I can't accept that," I replied. "You've done so much for me already. You can't pay for my clothes now."

"Oh yes, shopping with you is fun," Anne responded. "It's like watching a fledgling spread its wing for the first time. Think of it as a belated birthday present."

"My birthday was in May."

"So what? Do you have a robe yet?" Anne asked, changing the topic.

"Umm, no."

I added a robe to my items, and then we paid. I thanked each girl again with a big hug.

The next goal was getting some more makeup for me. I thought I had plenty already, but Paula said I lacked evening makeup. I ended up with an enormous eyeshadow palette, false eyelashes, and a lot of sparkling stuff.

Finished with shopping for the day, it was finally sleepover time.

* * *

When we arrived at Anne's home, I discovered that she lived in a mansion. Her family had to be rich.

We went upstairs into Anne's room, which was a lot bigger than mine, certainly big enough for six to find a space to sit. Anne had prepared as there were glasses and snacks already, and she brought cold drinks now.

"Do you have sleepovers often?" I asked.

"I didn't have one for some time," Anne responded. "I used to do it a lot as kids. As you couldn't go to a sleepover before, I decided to let you experienced it now."

"You only do this sleepover for me?"

"Nah, it was time for one anyway. We'll all have fun."

Shortly after, Jamie and Becky joined us, and we were complete. I secretly had a crush on Jamie. She had these killer legs, deep blue eyes, and was always nice to me.

"Let's get glammed up," Anne proposed. "Did everybody bring a dress?"

Everybody confirmed. I had the blue dress from my first day as a girl and the black dress I bought that day.

"So let's get changed. Chris, you could wear your new sexy lingerie with your little black dress."

"Hmm, okay, where can I change?"

"We usually just change here in the room. We're all girls, after all."

I hesitated. I had changed with the girls in the locker room, but there everybody had casual underwear. I wasn't so sure now because of my lingerie. I'd have to adjust some not-so-female parts.

"Are you getting shy now? Well, you can change in the bathroom behind that door if you want."

I took Anne's offer and went into the bathroom. It was bigger than our main bathroom with a large bathtub and everything.

I decided on the red set with black stockings. It took some time to change into it. As I didn't trust the dainty red panties to hold my pecker securely, I kept my tight white panties on underneath. I was extra careful with the stockings and then had some trouble fastening them to the garter belt. I adjusted the breast enhancer to make it invisible and give me cleavage again. Then I slipped into the shiny black dress. I was happy to be flexible enough to close the zipper in the back. Finally, I put on the new high heeled ankle boots and added some jewelry. I made sure the stocking tops didn't show when I sat down. I wanted to be sexy, not slutty. When I returned to Anne's room, all the girls had changed into classy dresses.

"Took you long enough. We were about to send a search party," Anne said and laughed.

"I guess I'm not an expert in changing clothes yet," I said with a frown.

"Leave her alone, Anne," Paula defended me. "She's a girl for what, two days now? Chris, I'm proud of you. I still remember how I first dressed in lingerie. I managed to punch a hole into the brand new stockings with a garter tab. Still don't like them." That was the first time somebody spoke up against Anne.

"Thank you. I think I managed not to damage my stockings."

"And I nearly dislocated my shoulders trying to get a bra on until I discovered the trick with closing them in the front and then rotating them."

"Oh, there is a trick? I just close them in the back. It's not that hard."

"So much for not being a changing expert."

Then we laughed all together.

We proceeded to put on heavy makeup, suitable for an evening out. Paula gave me tips and helped me with the fake eyelashes. I used an eyebrow pencil and blusher for the first time. I kept with brown eyeshadow, though, while some girls used very bright colors. As the last step, we all painted each others' nails.

We then took photos, in groups, and one at a time. I tried to strike sexy poses. I wonder if I succeeded.

So there we were, all dressed up and nowhere to go. Well, we could party on our own. Anne played some music, and we started to dance and sing along. I danced with Jamie too. She had even longer legs in heels and a short minidress. Usually, she dressed a bit more conservative, but now she showed an enormous amount of cleavage. I had to think pure thoughts to avoid getting uncomfortable. We had a lot of fun, but eventually, we wound down again and had some pizza.

"Let's play truth or dare," Anne suggested after the meal. Well, one of the typical Anne-suggestions that everybody follows. She got a bottle and paper snippets with dares and questions. She put the snippets into two cups, so we could draw one when it was our turn.

Anne spun the bottle, and it stopped pointing to Jamie.

"Truth or dare?" asked Anne.

"Truth," Jamie replied.

Anne pulled a question out of the cup and read, "Who did you kiss first, family excluded?"

That would have been easy for me because I never kissed anybody except Mom.

"Oh, that was Mark Peterson," Jamie answered. "What a mistake. He then wanted to have sex with me. And when I said no, he called me a tease and dumped me."

"You're better off that way. Just think of Olivia," Anne replied.

"What is with Olivia?" I asked.

"She was his girlfriend. And when she wanted to break up, he hit her so bad that she had to go to the hospital."

"Oh, I didn't know."

"Uhh, it's a secret. Officially it didn't happen. Olivia got some money for keeping quiet. Unfortunately, that meant that Melanie went through something similar, as she didn't know. Well, at least everybody knows from Melanie now."

"That didn't help me though."

"Yeah, sorry. But it brought us together. Sometimes something good comes from something bad."

"Yes. Life is much more fun now. Thanks to you all."

Then Jamie spun the bottle, and Becky chose dare. Jamie's draw was, "Eat a bite of a banana peel."

That was easy, in my opinion. So when the bottle picked me, I chose dare too.

"Remove your outer clothes until the end of the game."

I blushed. I shouldn't have listened to Anne and put on my lingerie. I agreed to the game, though. So I had to follow through. I wondered what a tough girl like Anne would do. Perhaps a striptease? I got up and struck a pose, then opened the zip and slowly removed my dress while trying to move seductively. I ended with posing in my lingerie.

The girls seemed to like it as they cheered the whole time and gave applause at the end.

"Wow, you look great," Jamie said. "Are you sure you were a boy two days ago? I can only see a girl."

"Thanks." I blushed again. She seemed to like how I look. Could there be something more between us?

I sat down, and we continued. I had some more questions to answer and dares to perform, but nothing too embarrassing. Then the bottle pointed to me again. I chose truth this time.

"Who is your secret crush?"

No, that can't happen. Is fate playing a cruel joke on me?

I looked at Jamie but couldn't keep eye contact. So I looked down again and barely audibly said, "Jamie."

"Oh, I had no idea," Jamie said. "I'm sorry, Chris. I really like you, but not that way. You are a girl to me, and I'm attracted to guys. I'm sure you'll find somebody, though. You're a lovely person."

I was devasted and replied, "I may seem to be a girl to you, but I'm still a boy in here. And being close to you girls isn't always easy. Anne, when you helped me shop for bras, do you know how you made me feel? When you touched me in the cubicle, I felt quite uncomfortable."

"Oh, I'm sorry," Anne said. "I didn't mean anything by it. I just thought of you as a girl."

"That's the problem," I continued. "I'm still attracted to girls, and you're all so beautiful. I'm sitting here in my sexy underwear and have a hard time not to get aroused. I somehow had hoped a girl could like me like this enough to become my girlfriend. But Jamie, you made it clear that won't happen. You love boys, and I'm not boy enough anymore. I'll probably stay alone forever."

"Hey, cheer up," Jamie responded. "I know somebody who'd probably like to date you. Lizzie the lesbian."

"Lizzie the lesbian? Isn't that cruel to call her that?" I asked.

"She introduces herself that way, probably to clear the fronts. Anyway, she broke up with her girlfriend recently because her girlfriend identifies as male now. And she isn't attracted to him anymore."

"But I'm male too."

"Did you look into a mirror recently? You're certainly more girl than Lizzie's girlfriend ever was. What's the harm in trying? Do you want me to ask her?"

I knew Lizzie was a lesbian but hardly ever talked to her. She was cute with short hair but not in a butch way, and she wore makeup too. I never saw her in a skirt, though.

"If you really think she could like me, okay."

"I'll ask her. Meanwhile, why don't you put a robe on or something? I don't want you too uncomfortable. And I think that's in line with your dare."

So I got my new robe. When I put it on, it was more seethrough than expected. It covered me somewhat, at least.

"I don't know if it helps," Jamie continued, "but I guess Lizzie would feel the same as you in this situation. So you're in the same boat, and she can perhaps give you some tips. Are you okay now, or do you want to stop playing?"

"I'm okay," I said and spun the bottle.

Some turns later, the bottle pointed at Becky, and she got "Kiss the person to the left of you." That happened to be me.

"Chris, you don't have to kiss," Anne said. "I'll fill in for you."

"No, I'll do it," I said. "I mean, if it's okay for you, Becky."

"Sure, I've kissed a girl before," Becky replied and winked at me.

She proceeded to lean towards me. I expected a little smack on the lips, but Becky gave me a real kiss. It started tenderly but progressed more and more, and our tongues got involved. Finally, it ended, and I was stupefied. It was my first real kiss, and I liked it.

"Yes, you kiss like a girl," Becky announced.

"What does that mean?" I asked.

"The boys I kissed were much more aggressive. You were just like the girls I experimented with."

Am I too much of a girl? Perhaps I should just stop thinking of myself as a boy and fully embrace being a girl.

The game continued a bit further but eventually ended, and we prepared for the night. We put some mattresses on the floor and got blankets for everybody. Then we changed into sleepwear. I chose to use the bathroom again. I selected a light pink silk pajama from my haul earlier the day.

When I was about ready, Anne knocked on the door and asked, "Are you decent? We all need the sink to remove our makeup and brush our teeth."

"Umm, now yes."

The girls came in with very different sleepwear choices, from onesies over pajamas to flimsy nightgowns. It got quite busy at the sink, and with Anne's nightgown not hiding much, I decided to wait my turn.

Once everybody was ready, we proceeded to lay down on our makeshift beds. The day wasn't over, though, as we still had a lot to talk about. That included boys and sex. I never thought girls would talk dirty like this. I was quite jealous of some of their experiences, but not everything went well for them either. I hoped for Lizzie to agree on a date and perhaps more in the future. I fell asleep smiling.

* * *

The next morning we had breakfast in the kitchen, still in our sleepwear. I met Anne's mother there.

"So you're Chris, who Anne talks about a lot recently," she said. "I think you're very brave. It must be hard to be born in the wrong body and then to transition."

"Umm, the girls here help me a lot." So Anne told her the transgender version of my story.

"Well, if I didn't know, I'd never guess that you were born a boy. You are very pretty."

"Thanks." Does she really think that? I don't even have makeup on.

"Well, have fun today," Anne's Mom said and left.

After breakfast, we got ready for a street market. Paula had to leave, so we remaining five girls squeezed into Anne's car. We had some fun at the market but didn't buy much. I had bought all I needed, for now, the day before.

After the market, Anne dropped me off at home.

"Thank you all," I said. "This weekend was awesome. Even if Jamie broke my heart." I laughed and hugged everybody.

"It was fun for me, too," Susan agreed. "Having a sleepover again was a good idea."

The other girls concurred.

* * *

Mom asked about my weekend. I told her about some stuff we did at the sleepover but kept the intimate details to myself. I told her about the shopping too, and that led to the earrings for pierced ears.

"Mom, can I get my ears pierced? All the girls have pierced ears."

She sighed but eventually said, "Okay."

"Paula gave me the contact info for her piercer. Can we make an appointment? I need you with me as I'm not 18 yet."

"Okay, I'll look into it tomorrow."

"Can I have my nose pierced too? Anne and Paula have theirs pierced too." I looked at Mom with doe eyes.

"Christoper! I mean, Christine, you're trying cutesy tactics on me now?

"Comes with being a girl."

Mom shook her head. "You've changed a lot in a few days. It's hard to recognize my little boy in you. We'll see about the nose piercing. I want to talk with the piercer first."

"Okay, Mom." I smiled. That wasn't a no.

* * *

To be continued