A Boy With Girly Hair - Part 13

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Lunch Outfit

The three of us Trista, Jenna, and myself – pondered over the best way to acquire an outfit for me and cause the least possible suspicion. Needless to say, I was the most paranoid, considering I had never actively stepped outside dressed fully as a girl. The very thought of it was nerve-racking and made me sweat.

“I’m sure a t-shirt and pants will be fine, right?” Trista proposed. “You guys drove to my salon wearing just that and had no problems.”

“But this is different,” I said jumping in. “First, we were driving in the car, not walking outside. Second, I didn’t have makeup on OR a new haircut. I look like two different people. That’s going to be jarring.”

Trista’s salon was situated in a small strip mall area, and across the parking lot was a Dress Barn. Shorter than a two-minute walk. Jenna came to my defense. “Sam looks visibly uncomfortable right now. There’s no chance you’ll get better by going outside.” She then turned to me. “Sam, would you just said that you’d be okay walking around a bit as Sammi, right?” I nodded. I suppose I did say that, but that didn’t change the fact I was getting more and more concerned with the idea as the minutes passed. “Well,” she said, “how about we switch clothes? Trista doesn’t have anything extra to wear here, but you already fit into my stuff.”

We all agreed that was an optimal enough plan. After all, Jenna wasn’t going to arouse any suspicion because she had a girl’s figure and plenty of confidence.

“Girls wear boy-style clothes all the time. I don’t mind.”

“…alright then. Let’s swap.”

Trista gave us a little privacy while we both stripped down to our underwear. Jenna handed me her skinny jeans and a crew-neck sweater. It wasn’t a particularly feminine outfit, though tight girls’ jeans and a pink crew neck would suit me much, much better. After all, what was it for, a two-minute walk?

Within a moment we were done. Trista came back in, complimented both of our appearances, as well as our quick-change abilities.

The three of us walked along the covered section of the strip mall, passing by a pizza joint, dollar store, and a nail salon.

We made it inside the Dress Barn. I’d never been to one before, but it looked close enough to a Kohl’s or any other clothing retailer – minus the men’s section. It wasn’t super packed which made me feel a little more at ease. The fewer eyeballs to suspect anything, the better.

However, as we walked by the front counter, I got stares. I quickly turned on edge.

“Dang dang dang Jenna,” I whispered. “We gotta go. Now.”

“You know they’re not looking at you because they think you’re a boy. It’s because you’re so dolled up at this time of day.” She then turned to Trista. “Maybe we overdid her look for errands.”

Trista walked us to a back part of the store, near the changing rooms where I was instructed to wait. I had no say in picking anything out, and honestly, I was okay with that. Trista and Jenna scoured the store for an outfit for me to wear to lunch.

At this point, I started to realize something. Why couldn’t we just go to lunch with the swapped clothes? Why spend time finding an outfit we don’t need?

Trista and Jenna returned, shepherding me into one of the changing rooms. Jenna went into the one next to me.

“Hey, why are you changing too?” I asked. She didn’t answer verbally but instead responded by hurling her panties over the top and into my stall.

“What? Hey!” I wasn’t too thrilled about having my sister’s used underwear landing on my face.

“You’ll need this for some of the outfits. Give me your boxers.”

“No way! I’m not wearing your used underwear, Jenna. These boxers fit just fine – and why do you wanna wear mine?”

She groaned, somehow unable to understand my argument. “Just do it, Sam. Trust me, they’ll fit better. You’ve worn panties before.”

I figured it wasn’t worth fighting. I stripped back down and threw my boxers over the wall. I could hear Trista giggling at our exchange.

“And this!” Jenna said as I felt her bra fall onto my head.

“Really?” I asked with distress. “Jesus, what do you have for me to wear?”

Just put on your underwear so Trista can come in. I slipped on the panties over my naked body. They were snug, but soft comfortable material. Plain, which was good. I’d worn panties before, so it’s nothing new.

I also tried to attach the bra but had a little trouble. Enough that I asked Jenna to come inside to help me out. She helped out and my undergarments were complete. She stood behind me, staring at her brother with a fresh haircut with wavy, bouncy curls running down his back complemented by a full glam makeover. She started to tear up as she often does and gave me a big hug from behind. She smelled my hair, burying her face in it. Jenna was so happy.

All I good do was stand there. I knew what this meant to her, and I had to say feeling her love felt good to me too. I felt close to her, and that’s the reason I’m doing this.

She snapped out of her trance. “Let’s get you into something!”

Jenna decided to stay in the stall with me while I was to try on clothes. Both of us knew I’d need help.

The first one Trista handed me was a light blue t-shirt swing dress. It hung just above my knees and was quite flowy. Jenna asked me to do a little twirl and the skirt of the dress flew around as I did so. Jenna smiled. “Notice the pockets?” she said. I placed my hands along the side and to my surprise felt deep pockets. A nice addition for sure, as I hate carrying my phone or wallet.

“Alright, that'll work,” I said.

“No no no! We can’t just stop now. How do you know you won’t like others?”

I knew where this was going. This was more for her than me. She wanted me to try on a bunch. I really didn’t care for shopping but understood what she wanted. “Trista, you okay if Jenna wants us to stick around?”

“Only if you come out and model for me!”

I stepped out of the dressing room for the first time and caught a big grin on Trista’s face – almost a look of pride. “Let’s try more,” she said.

We carried on with a few more dresses that Trista and Jenna had picked out. I tried on several. The next was a floral bohemian-style button-up sundress. Light blue with white speckles. The skirt hung much lower but the spaghetti straps were a new touch. Trista told me I had “nice shoulders.” The floral was a bit out of season, however, so we moved on.

Jenna found me a sweater dress to try on next. The top was off the shoulder and a bit slouchy showing one of my bra straps. The beige fabric was comfortable and warm, though somewhat short. “What if I sit down?” I asked.

“Then you close your legs,” Jenna instructed me. I gave it a shot and felt good enough. “But I’m not sure that your straps are supposed to show with this one…” Again, we moved on.

“How about this?” Trista proposed, holding out an off-white piece. She called it a trench dress. I tried it on. Simply put, it looked like a trench coat, but a dress. And significantly more feminine. The fabric wasn’t soft, but it was comfortable. It hung a little above the knees and was sleeveless.

“This is pretty fancy, guys. I’m not sure,” I said, checking myself out in the mirror.

“Perhaps. Unless we get shoes.”

I told Jenna no immediately. We’re not getting shoes. We’re not even supposed to be buying clothes, but here we are.

I finally walked outside to the small remaining pile of clothes that the girls had picked. I grabbed what Trista told me was a polka-dot print tea dress. Short, flowy, comfortable. “Let’s do this.”

I threw on the dress and showed it to Trista and Jenna. Both were pleased, but I could tell they wanted to try on more. I eventually had to refuse as we were under a time constraint.

The dress worked, I thought. It went with Jenna’s converse, it was casual and autumn-styled enough, and best of all, it wasn’t too expensive. I changed back into the crew neck and we approached the counter.

“On me, girls,” Trista said. We both immediately thanked her, though I realized it was a little weird I was thanking her for a dress that she bought me. Was it mine now? What was I going to do with it?

After changing at the salon into my new dress and Jenna changing back into her original clothes, it was time for lunch. Trista gave us instructions to a location closer to the actual city of Milwaukee and Jenna and I followed in the car. Strange, I thought, how this day was going. At first, I was nervous about being caught by Trista for being a boy, and only a few hours later she’s dolling me up, buying me clothes, and taking us to lunch.

The restaurant she chose was casual. American-style food – burgers and such – and a full drink menu. The host sat us in a booth, and we ordered our salads.

Now that we knew Trista was on our side, we decided to go deeper into filling her in with our background. Jenna and I explained all about how she started doing my hair and then tried an Instagram account that had now well over 30,000 followers. I told her about some of my close calls, such as getting my nails painted and the girls in my class suspecting my identity.

Though there werea zero reasons for anyone to suspect I was a boy, I made sure we kept our voices low. That turned out to be a smart call because 20 minutes into the meal I noticed a table of boys sitting nearby. I don’t think they could hear us, but they were definitely looking our direction.

“Hey, quiet up a bit.” I reminded my table, gesturing towards the boys.

“They’re just checking you out, Sammi.” Trista laughed.

“Yeah, I’m not interested, though they don’t seem to know that.”

“Well a cute one is looking at me,” Jenna noticed. She smiled and did a little wave.

The table of 4 boys – late high school age by the looks – gave shoves to the guy Jenna noticed. Buddying around.

“Talk to him,” Trista suggested. “I won’t mind.”

Jenna thought about it for a moment, and as if this trip weren’t crazy enough, she got up and walked over the table.

The table was a little out of listening distance thanks to the background noise of the restaurant, but she appeared to be introducing herself and quickly hitting it off.

“God, why is she doing that?” I said, shoving my face into my hands.

“She’s a good-looking, friendly girl. Very brave to do that too. I just hope they’re nice.” Trista said trying not to look too much.

Then I saw her pick up the boy’s phone. She was typing something in. Oh God, was she giving out her number?

I couldn’t believe it. I’ve never seen Jenna act this bold before. She returned to the table to keep eating.

“Aaaand that’s how it’s done. Brad has my number.”

Trista gave a short little applause. I still was embarrassed. Anything that drew attention to me or our table was unwelcome in my mind.

“Oh, cheer up Sam. He’s not gonna call. That was just for fun.” I had a hard time believing that.

We finished lunch and drove back to the salon to reset my look.

Trista had given us our $500 for our time, which we had agreed in advance to split. Though she really went above and beyond what I thought.

“Let’s go take that makeup off.” Trista ushered us to the sink, but suddenly Jenna called out.

“Hold up. Hold up.” She was one her phone, typing something. “Okay, now listen. Brad just invited me to hang out tonight.”

What? This guy works fast.

“And quote, ‘you can bring your sister if you want.’”

Jenna looked up from her phone straight at me. She was about to ask me for the biggest favor yet.