A Girl for Halloween: A Slow and Sweet Gender Realization Story

By: Mysterious Stranger AKA Jennifer Sweet

“Alright Dad, I’ll go to the interview!” I said, finally giving in after a long debate.

“You’re making the right decision, Jason.”

My father had recently lost his job working a desk job for a local brewery. Because of that occurrence, my parents were no longer able to contribute any more money to my college fund. So the circumstances were either I go to community college for a year, or I can go to a University right away, as long as I got a job.

Finished with the conversation, I made my way up to my room and called my buddy Kyle about the news.

“Good to hear man!” he said enthusiastically, “having a high school job will probably be good for you anyway. It’ll teach you some responsibility.”

We chatted some more about school and then said bye for the time being.

Even though it was a Friday night, my dad had scheduled an interview for me at this Halloween store chain that just opened up in our downtown area. Being a teenage boy, this was not ideal, as I wanted to go out with friends, but I told my dad I’d go. I threw some shoes on, and took the car to the Halloween store.

I pulled up and parked. The store was called 'Merlin’s', and had a picture of a cartoon wizard next to the fluorescent letters on the room above the store. It had rented space in our strip mall, so you could still see the remnants of the letters from the sign for the pizza place that used to be there.

I walked inside and the place looked surprisingly impressive. In the front were halloween decorations like fake skeletons, ravens, etc. In the back, were the costumes and a few changing rooms. There seemed to be a LOT of costumes; there were some for men, women, children, and even pets. But overall, the place was well decorated and looked like the move-in process was coming along for just being September 28th.

“Can I help you?” the woman at the counter asked.

“Yes, I’d like to speak to the manager. My name is Jason and I’m here for a 7 o'clock interview.”

“I can help you with that. I’m Sandy Hogan, store manager.”

Sandy was a portly woman with light-brown hair and kind eyes. I shook her hand and she walked me to her office in the back of the store. We walked past the decorations and the costumes on the way back. There were even more costumes than I previously thought from first glance. Only the men’s costumes, however, were hung up on the racks. The women’s ones were all piled up to the side of the store in their packaging.

We got into her office and told me to pull up a chair near her desk. “So tell me about yourself, Jason.”

We talked about school for a little while, and I explained that I’m a volleyball player at my high school, a pretty good student, and hoping to make a little money to help with college.

“Well, Jason, you seem like a nice kid, and we need workers, so it looks like you’ve got the job!”

“Thanks so much! When do you want me to start?” I inquired.

“Come in at 9am tomorrow to start with the organizing of the costumes. You’ll meet all the other workers then too.”

We shook hands again and I left the store and went home happy. For the rest of the night I hung out with my friend Kyle. I told him about my job and he seemed excited for me to start tomorrow.

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Saturday morning came along and I woke up at 8am, got ready (showering, combing my shoulder-length brunette hair, getting dressed, eating, the works) and then drove off to my first day.

I walked inside and was greeted by Sandy. “Welcome Jason! Are you ready to work?”

“You bet!” I responded cheerily. “What should I start on?”

“Well, all of the men’s costumes are already hung up and in their place. Val and Autumn are towards the back of the store checking out the female costumes and making sure they are the size they say the packaging indicates. You can go join them.”

I walked to the back of the store.

“Hi, are you Jason?” one of the girls asked.

“Yep!"

“Cool. I’m Autumn and this is Val,” the girl said.

Autumn was a moderately tall girl, at probably about 5’7”, with blonde hair and bright blue eyes. Val was close to the opposite. She had long black hair, and brown eyes, yet about the same height as Autumn. Both of them seem very friendly and peppy.

“Right now, we are just taking these costumes out of their packaging and checking them to make sure they are the right size.”

I grabbed the first costume I saw in the pile. It was a female vampire costume. The costume was a long red and black dress, with cut fabric at the end. It came with two-or-so inch heeled black shoes and a set of fake teeth.

Picking up the dress, I scanned the dress for a size indicator. I couldn’t find one. Then I looked at the packaging. Again, no size.

“Hey Autumn, where are the sizes on these?”

“Oh Sandy didn’t mention it to you? The costumes don’t have sizes listed on them at all.”

That seemed ridiculous! “Why not?”

“Well the people at Merlin’s get them really cheap from this manufacturer who doesn’t even bother to put sizes on them. I mean the packaging is just plain plastic with the name of the costume on it. There are extra-smalls through extra-larges for all costumes, so we just hang them up to what they appear to be.” Autumn explained.

“What do you mean ‘appear’ to be?”

“Just put it up against your body.” Val exemplified, swinging the material against herself, “If it looks like it will fit perfectly on me or Autumn, then it’s a medium. We then estimate from there.”

“Okay…” I answered. I picked up the vampire dress again and placed it against my 5’9” frame.
“What do you think?” I asked the girls.

“I think it looks like you’re wearing a dress...” Autumn joked. The girls laughed.

“Very funny guys. But actually?”

“That looks like it would fit you if you wore it…and you’re about 5’9”, so call that a large.” Val estimated.

I then grabbed a Hanger with an “L” on it (signifying a large) and put the dress on it, with the heels and fake teeth underneath the dress now hanging from the rack.

The girls and I did this for the next few hours, but we only completed about a third of the costumes. We decided since it was close to noon, we’d take a lunch break.

We left the store and walked a few stores down the strip mall to a Smoothie place. Autumn and Val both ordered mango smoothies, and I had a strawberry one.

We took a seat in the smoothie shop and started talking. I found out that the girls both went to a rival high school nearby called Norridge South. I went to Norridge North. Classes came up in the conversation and then Val kinda asked an out of the blue question.

“So Jason, why do you keep your hair so long?”

“Ummm, I don’t really know. I guess I just like it that way.”

“Well you at least take decent care of it,” Autumn pointed out, probably referring to the fact that it wasn’t as mangled as other guys with long hair, despite it being kind of limp and messy.

It was a kinda curly/wavy throughout, and wasn’t as neat as it probably should be.

Val then reached towards my head and pushed the hair from falling into my face to behind my ear.

“Here!” she said, “this should help keep your hair out of your eyes." She reached into her purse and found a plain black barrette. She pulled back my long bangs and held back to the left side of my head using the barrette.

“Oh, I guess that was kinda bugging me.” I said, saying my thanks.

“No problem. I have a million of those anyway. Ready to go back to work?”

We all got up and walked back to Merlin’s.

The first costume I picked up since getting back from lunch was a ‘Fitness Girl’ outfit. I took it out of the packaging and held it up against my body. The costume consisted of sneakers, a tank top, and leggings, and was a bit difficult to tell of the size.

Autumn looked over at me, noticing my confusion, “What’s up Jason?”

“It’s just that these leggings in the costume are a little difficult to tell what size they are. They are spandex and don’t really hang well. They look really small, but maybe it’s just because they haven’t stretched out.”

Autumn grabbed the leggings from me and hung them against her body, “Hmm that’s true. My bet is that they’d be large, but you should try them on to be sure.”

I laughed. “You’re kidding, right? I’m not gonna try on leggings.”

“Val and I always test out the costumes that are difficult to size up. It’s the only way we know that they’ll be accurately marked.”

“So you’re saying I should wear leggings?” I said, not trusting her judgment in the slightest.

“Well, yes. My guess is that they are a large size and if you fit into them well, that means they're large.”

Autumn didn’t seem to be messing around. I think she genuinely thought I should try out the leggings. That’s ridiculous. I mean, have you ever seen a boy wearing leggings that wasn’t named Richard Simmons?

“The changing rooms are in the back, Jason.” Autumn added. “And don’t worry, no one will laugh. You just try them on and then show us what they look like. Val and I will determine the size.”

I sighed. “Fine. But no snarky comments about wearing them.”

We all laughed (myself, uncomfortably). I took the leggings to the back changing rooms and stepped behind the curtain. I took off my jeans and went down to my briefs. I stepped into the leggings (which are actually kind of hard to get on) and adjusted them.

I took a deep breath and walked out to the store’s costume area. Val and Autumn started to giggle.

“Hey! You guys said you wouldn’t laugh!” I snapped.

They both stopped and apologized. “Okay let me take a look” Autumn said. She had me stand still and looked at me from the front and behind. “Those fit you like a glove, Jason!”

“Yeah…they are surprisingly comfortable too.” I added.

"Well you can keep them on if you want,” Sandy said, walking up.

I turned around quickly, embarrassed.

“I…I just tried them on ‘cause…they….the girls told—“ I stammered.

“Don’t worry Jason it’s fine!” Sandy assured, “You guys can try on whatever costumes you want as long as you’re still working hard. And Jason, those really accentuate your slender legs nicely.” Sandy winked.

The girls couldn’t help but giggle at my embarrassment.

“Alright though….Jason, you can keep those on, but just get back to work and finish up the rest of the first half of the costumes.

We did as Sandy told and finished up the costumes. Once we finished, we said goodbye to Sandy.

“See ya!” She replied, “I’ll see you tomorrow from 10-3 to finish up the costumes!”

I changed out of the leggings back into my jeans and drove home.

==========

I got home around 4pm, surprisingly exhausted from work. I plopped myself on the couch.

“Hey Jason. How was your first day?” my older sister Julia asked. She’s a freshman in college, but lives at home because she attends the local community college.

“A little tiring, but fun nonetheless. I work with some really nice girls.”

Julia looked me up and down, smirking. “I see. And was it one of those nice girls who prettied up your hair just a tad?”

I gasped for a second and realized I forgot to take the barrette out! I blushed and attempted to explain, but Julia said not to worry.

She sat down next to me on the couch. “I think it looks cute.”

“Well I don’t want to look cute! I just want to keep the hair out of my eyes. That’s why Autumn and Val put it in.” I explained, flustered.

“Okay okay don’t get your shorts in a knot.”

Julia left the living room and I relaxed in front of the TV for a while.

========

The next day rolled around and I woke up again at 8, but got ready by 8:30, even though I only needed to be at work at 10. I sat down and turned on the TV.

“Hey little bro. Whatcha watching?” Julia asked. I guess she gets up early too.

“Reruns of The Simpsons,” I said, disinterested in having a conversation.

“That’s cool.” She said. “Hey I notice you don’t have your barrette in any more.”

“It must’ve fallen off while I was sleeping.” I said apathetically.

Julia left the room for a minute and then returned. While just sitting on the couch, I felt something touch my hair from behind. I whip my head around and its just Julia.

“What’re you doing??” I ask angrily.

“Just helping you out! Jeez!” She says as she continues to put the barrette in my hair.

“Fine. Go ahead.” I said. I guess she was helping me.

I just kept on watching tv while Julia went back up to her room. She returned to the couch with some sort of two pronged metal thing. She plugged it into the wall near the couch and started clamping my hair.

“Hey!” I yelled. “What do you think you’re doing?"

“I’m just straightening your hair. Trust me, this will keep the messy curls from leaning into your face,” Julia explained.

I guess that made sense. And I HAVE been tired of hair getting in my face for a while.

However, her little “hair straightening” ended up being a bigger deal than I thought. She had to use multiple clips to keep parts of it up while she straightened the rest. It took about 20 minutes, but she finally finished.

“Alright I’m done.” Julia told me.

Now that my hair was straightened, It didn’t lean into my face like it used to. However, Julia still added her own pink barrette into my hair, just to be safe.

“Does it have to be pink?” I pleaded.

“It was the only one I could find. Chill out.”

Whatever. The barrette is doing its job and I’m happy. I looked at the clock and saw it was closing in on 10, so I left for work.

========

Walking into Merlin’s, Sandy welcomed me and pointed me back to the costumes as she had the last time.

“Wow your hair!” Autumn shouted in excitement.

“What, does it look bad?” I said, sort of concerned.

“No no no…It looks wonderful!” Autumn and Val stopped what they were doing and started feeling my new hairstyle.

“It’s just straightened, guys. It’s supposed to help keep it from falling into my face.” I said, trying to cool down their interest.

“Oh I’ve been trying my whole life to get my hair to look this pretty when straightened,” Val shared. “You REALLY pull this off, Jason.”

I blushed. “Well thanks guys. I guess my hair does look well-maintained at least.”

Autumn, Val, and I returned to work for a while, putting costumes up against our body and figuring out the size. I went through mummy, Frankenstein's bride, construction worker, and many other costumes. Then, Val interrupted me.

“Hey Jason, would you lend me a hand for a sec?”

I dropped the current costume I was working on and walked over to Val. She was holding a Ice skating dress.”

“I think this is a large, but would you try it on just in case.”

The dress looked like it would be tight to the skin, so I understand why Val would want me to try it on. But it also was a super girly outfit. Should I, a boy, wear such a girly dress?

“You mind? Just try it on.” Val asked.

“I…suppose.” I said reluctantly.

She handed me the dress and I walked back towards the changing rooms, wondering what wearing this dress will feel like. What if I ended up finding it okay? What…what if I end up…liking it?

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The remaining 12 Chapters of this story are available on Amazon/Kindle. Link is below!

Hope you enjoy, lovelies! :)

https://www.amazon.com/gp/product/B08FH75CC8?pf_rd_r=TPCHH27...