A Girl for Halloween Part 4: A Date with a Boy

A Girl for Halloween Part 4: A Date with a Boy

By: MysteriousStranger

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I’d hesitated enough. I don’t care if I get caught outside in girls’ clothes.

“Sure Michael! I’d love to!”

“Really?” he said, shocked and excited, “How bout after work tomorrow we can walk the few blocks over to Oberweis!”

We said goodbye and with that, he left. Once the door closed behind him and he was out of sight, I was mobbed by Val and Autumn with hugs.

“Oh my god Jacie! You have a date!!” Val said exuberantly.

“And a cute one too!” Autumn added.

They’re right. I DID land a date. With a cute boy too! Me—Jason. I mean Jacie! A girl—a real girl.


The next day, Thursday, I couldn’t handle my excitement. School was off, so I just hung out at home until 3:00. I also couldn’t care less about what Kyle thought of me. I was simply exuberant! The best part of it was that Michael went to another school, so nobody needed to hear anything of me being a girl. It was perfect!

Once 3:00 came, I drove over to work. I was about to go inside, but saw that Michael had already beat me there! I can’t go inside like this, wearing boys clothes!

I pulled out my cell phone and texted Autumn to meet me outside, and to bring me clothes. Within two minutes she came out, wearing a pleated red skirt and a white top.

“You’re not in costume?” I said surprised.

“No, when we got here, Sandy said we could take a break from costumes.”

“Well that’s a huge issue then!" I said, worried, “The only girls clothes that I can wear are costumes! I can’t go in there looking like a boy.”

We stood there for a few seconds, but soon after Autumn had a eureka moment, “I know! There’s a PINK store in this strip mall! We could buy you some clothes real quick!”

I didn’t really want to spend any money, but if it meant not blowing my cover, than I guess it had to be done. Plus, having girly outfit of my own would be quite the experience!

I agreed with Autumn’s plan and we walked down to the PINK store. Walking in, the place smelled of perfume and looked like a teenage girl’s dream. I actually recognized a lot of the clothes that were in here from seeing girls wear them at school. Anywhere from dresses to yoga pants to jewelry. It was a weirdly familiar place.

“Alright, so let’s pick something out quickly and get you back to Merlin’s in time so you’re not TOO late to work.” Autumn said, hurried, “So what catches your eye?”

I was looking at everything and soaking it all in. I just LOVED the feminine aura I was feeling from the store!

“How about these?” I said, referring to the pair of black yoga pants. The waist of the yoga pants folded over my butt and read “Love PINK” in pink letters.

“Oooh good choice Jacie! What about for a top?”

I picked up a cute white top that hung off of one shoulder. It was a very thin material.

“I like that,” Autumn said, “but I think because it’s so thin, you’ll need to get a bra with it. Go back to the changing room and I’ll pick out a bra for you.

I went to the changing room and stripped down to my briefs. By the time I was unchanged, Autumn came back with not just a pink lace bra, but a pair of pink lace panties as well.

“I know you don’t NEED panties, with this, but if you wanna feel extra feminine, this will help.

My own pair of panties! This was turning out to be quite the momentous day!

I put on the panties and bra. Even though my face and hair didn’t look too girly, my body was perfect! I had much more natural curves than an average boy my age, so the bra and panties only made me look more dainty and feminine. Having no body hair even added to that.

I picked up the yoga pants and stepped into them. Boy did they feel heavenly! They hugged by legs tightly and made my butt look plump and girlish! I threw on the top and admired my new look in the mirror. Autumn tossed some pink flats into the dressing room and I put them on. Now I had pretty feet too! I stepped out to show Autumn my new look.

“I love it Jacie! Your butt looks so cute in the yoga pants too! All the boys will be chasing after you!”

We both laughed.

“There’s only one issue though,” I added, “I feel pretty on my body, but not my head. Is there anything you can do Autumn.”

“Well, I mean you look girlish enough as it is, but I’m sure I can help that cause.”

She reached into her purse and pulled out a few items.

“First, how about we brush your hair a little bit,” she said. Autumn brushed my hair for about a minute and gave it a softer, more voluminous and pretty look.

Next, she pulled out a tube of mascara. She applied to the my eyelashes—top and bottom lashes of each eye. Then came the chapstick. She said that it would help my lips be more “kissable”, not that I was necessarily planning on that. On top of the chapstick, Autumn applied some pink, shiny lip gloss. She put plenty on and it made my lips look REALLY pretty.

“I know it’s not too much, but it should do for the night right?” Autumn asked.

“Oh my gosh thank you! I feel so…so…natural,” I admitted.

“Oh! And I almost forgot!” Autumn said, pulling out a bottle of perfume. She put a few sprays on me. I now smelled nice and flowery.

“NOW you’re ready,” she said smiling.

We walked back over to work. Going inside I got a subtle thumbs up from Val, indicating that she liked my new look. Sandy didn’t notice us come in late I guess, so we just got straight to work. About 20 minutes into me being there, Michael came up to me.

“Hey Jacie, you looking forward to our date tonight?”

Oh my God! HE called it a Date! So I guess this really IS a serious thing.

“Of course I am! I’ve been to Oberweis many times and love it every time I go there.”

“Me too!” he said, “Looking forward to it!”

With that, he walked away and continued working. It was a pretty busy Thursday night so we didn’t get a chance to speak for the rest of the night.

To be honest, I was REALLY nervous that whole time. I mean, it was an excited nervous instead of a scared one, but it still FELT scary. This is a date with a real boy, who also doesn’t know that I’m a boy. Should I tell him…? This probably isn’t the best time. I mean, I wouldn’t want that information to ruin the night.


We closed around 7:30. All the customers slowly left the store and we swept and closed up. Sandy said goodbye to us, and Autumn, Val, Michael, and I all walked outside together.

“Have fun you two!” Val said walking away. Both girls were giggling with excitement for me. They got into their respective cars and drove off.

“They’re weird, aren’t they?” I said to Michael, to break the ice.

He laughed, “Yeah but they seem like good friends. How long have you girls been friends for? You seem really close.”

“Actually we just met at this job. We just became fast friends. I guess it was because of all time we had to spend together organizing costumes.”

We started walking down to the Oberweis. It was only a few blocks, but it still felt really cold. I guess Michael noticed this and offered me his jacket. I didn’t really need it, but somehow by accepting his offer, I feel like would appreciate it and feel more like a gentleman.

So he took off his jacket and laid it over my shoulders. The jacket was already warm from his body heat and it made me feel a lot more comfortable. We got to the Oberweis and approached the counter.

“It’s on me,” Michael said with a smile. Wow! It really IS a date if he’s paying. Now obviously I didn’t want to impose, so I just ordered a small soft-serve vanilla. He got the same, but with sprinkles.

I guess it was just now that I really noticed how handsome Michael is. He has great chiseled facial features, a well maintained short haircut, and astounding blue eyes. As far as his body went, he was about 6’2”, fairly taller than I, and I wouldn’t say “buff”, but definitely in shape, as he IS a basketball player.

I guess I was staring into his blue eyes a bit too long that he asked, chuckling, “Everything alright Jacie?”

I snapped out of it, “Oh! Sorry, I was just zoning out!”

“No problem,” he said still laughing, “wanna grab a table?”

I agreed and we sat down. We chatted for a bit while eating our ice cream. However just as we were finishing up. Three girls walked in.

“Heyy Michael!” one of them said. She was pretty, blonde, thin, and I did NOT care for her.

“Hey guys…” he managed to squeak out, “what’re you guys doing here?”

“We’re just getting ice cream, like everyone else in here,” said the short brunette girl. She was also very pretty.

Then the pretty black haired girl spoke up, “Who’s that you’re with Michael? Introduce us!”

“Umm okay…This is Jacie, she’s a friend of mine from work. Jacie, these are a few friends from my school.”

“Leslie’s his ex-girlfriend!” The brunette girl blurted out, referring to the Leslie, the pretty, thin, blonde girl.

“Yeah…she is…but that’s been over for a few months now,” Michael said, whispering to me.

“Well, it was good meeting your girlfriend Michael, see you later,” Leslie said walking away.

“She’s not—“ Michael tried to yell, but they had left already.

“Wow, what was that about?” I asked, breaking the awkward silence.

Michael sighed, “Oh that was just my Ex and her friends. It was kind of a bad breakup and I was a little salty about it. I’d rather not discuss this now though.”

Oh geez, so he had his heart broken? But he mentioned that this was a few months ago. Does that mean he’s still in the grieving period. He can’t be—it’s been a few months already, he should be over it by now, right? So does that mean that I’m just a rebound?

“Hey Jacie, you fine to leave now?” Michael said, a little more upset than he was before he saw Leslie.

“Yeah I’m good to go.”

We left Oberweis and started walking back towards Merlin’s where our cars were parked. Merlin’s was all empty with the lights turned off.

Michael looked very down. He wasn’t as happy as he was before the date. Was it Leslie? Was it…?

“Michael, be honest, is anything wrong?” I asked, concerningly.

He sighed and sat on a nearby bench. I sat next down next to him.

“Seriously, Michael, was it anything I did?”

He picked his head up after hearing that. He then looked me in the eyes, grabbed my hands, and kissed me on the cheek. “That should tell you,” he said somberly.

He then got up and walked to his car. He got inside and drove away without even looking at me.

Two thoughts were swirling through my head. First, what was wrong with Michael? Will I ever get to the bottom of what happened with that break-up?

And second…I was just kissed by a cute boy!


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Hugs and Kisses! -MS

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