Working for Halloween Ch. 03

Story Info
Costume fun, then to a bar and bookstore.
12.7k words
4.83
20.1k
40

Part 3 of the 3 part series

Updated 06/07/2023
Created 07/15/2009
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My phone rang and I saw it was Brad from the Costumes 'n' More shop where I'd been working recently, and playing, if we're being honest. I answered excitedly hoping he was ready for me to come down again, so to speak.

"Hey, uh... Tom, its Brad," he said somewhat hesitantly. I wondered why he was hesitant, I debated answering in my femme voice since I'd been practicing it like Anna had taught me, but I didn't want to confuse him, not at first anyway.

"Yeah, I know," I answered brightly, "What's up?"

"Oh good, yeah, so listen, there's a couple things. First, are you still good for your next costume showing tonight," he stated rather than truly asking, sounding a little more sure of himself now.

"That sounds wonderful, hun! Do I get to know what it is?" I asked in my best femme voice, I hoped it sounded good.

"I... whoa, that sounds wild. Have you been practicing?" he asked, sounding a bit thrown off again.

"Yes, I have!" I replied keeping the voice, figuring this was the best way to practice. "Is it okay?"

"I... yeah, it sounds good," he replied. "Uhm, kinda sexy actually."

"Oh really?" I practically purred back. "Hopefully I can show you more tonight."

"I'd really like that," Brad said back, I could practically hear him grinning.

"So, was there something else?" I asked softly, not really wanting to disturb the moment.

"Oh, uh yeah, the boss, my Manager wants to meet you. I think he wants to talk about working at more locations, and maybe that calendar thing I mentioned," he said quickly.

"So, you told him I'm not available... or something, right?" I said moving back to my regular voice.

"Well, I just told him I'd let you know. I didn't want to speak for you. What you do with that is up to you," he explained. He gave me the number to the office so I could schedule an appointment.

"And did you tell him who I really am?" I asked uncertainly.

"We didn't really get into that," he answered quickly.

"So, what should I wear?" I asked.

"I... I don't know, I hadn't really thought about that," he said.

"Welcome to my world," I replied. "Okay, was that everything?"

"No, Anna wants to talk with you when you come in, too."

"Okay, any chance you're going to tell me the costume, or do I have to wait?"

"I like it to be a surprise," he laughed back.

"Fine... hopefully there'll be lots of surprises," I added mysteriously.

"Yeah," he added distractedly. "So, I'll see you later?"

"Ab-so-lutely!"

I hung up and looked forward to heading in. I had some time to kill, but wanted to make sure I got a shower and did all my preparations. I decided, against my better judgment, to call the big boss. Thankfully he wasn't in, but they were able to schedule me an appointment to come in the following week, so that would give me some time to think of how I was going to approach that.

I stepped into a nice warm shower and let my concerns wash away with the water. I've always loved a good shower, it was one of my favorite ways to relax. I also enjoyed shaving and some of the other prep work I did in the shower. So, I had a lot of reasons to enjoy it.

Naturally I shaved everything below my eyebrows. I did a once over on my face, but I'd shave that even closer when I got out. I made sure to use a nice moisturizing soap, I also took my time making sure to really soap up my ass, figuring that was probably going to get a bit of a workout, at least if Brad had his way. Well, okay, I was pretty excited about it, too. I almost kind of wished I had some outfits other than costumes to wear. I kind of felt like dressing up in something girly and fun and going in to the store that way.

Other than my two costumes, I mostly just had panties and stockings. Really the few items I had were pretty slutty and while I doubted Brad, or Anna for that matter, would really care. I'd feel a bit weird riding the bus in a mini skirt and tube top. I wasn't sure I was ready for that, yet, but it fueled me fingering my ass.

I stopped short again of actually playing with myself since I wanted to be fired up again for tonight. I did pull on a pair of black panties before putting my drab boy clothes on. I grabbed a backpack and tossed some of my girl clothes into it at the last moment. I thought maybe I could see about wearing some of it home. Maybe?

I arrived pretty early, but I figured that would give me time to get dressed and talk with Brad and Anna about whatever it was they wanted. The familiar bell over the door greeted me, though I was surprised no one was out front when I came in.

I heard a voice from the back call out, "Be out in a second!" A few moments later Anna stuck her head out and was about to do a greeting when she spotted me. "Oh, its just you," she said with a snooty accent.

I mocked a wound to my heart, "Really? You stab me with your words."

"I'd rather stab you with something else," she smirked and pantomimed stroking an imaginary cock.

I smiled, and blushed bright red. She smiled triumphantly and strolled over to the counter. I realized she was wearing a ringmaster costume as I regained my composure and walked over to her, "Brad mentioned you wanted to talk with me?"

She smiled mischievously for a moment, then said, "Yes, I was wondering which of us you were going to be taken by tonight?"

My eyes opened wide in surprise, my mouth opened but I couldn't actually form any words. Anna jumped in first, "Don't worry, I'm fine with you getting with Brad, I think it's his turn anyway." She laughed a little at my embarrassment. "Actually, I have a present for you," she added in a much gentler tone.

"A present?" I said, still a little thrown off. "Do I dare ask?"

"Oh, I was just messing with you, don't be such a sissy... so to speak," she shook her head and laughed. "Sorry, not what I meant, I just... I realized some things about myself the other night thanks partly to you. Also, it occurred to me, you're getting a nice collection of costumes, but you could use some other femme clothes, especially if you're going on a job interview."

I raised my eyebrows, but then it occurred to me, she and Brad probably talk all the time. She handed me a fairly large shopping bag. I opened it and looked inside, seeing a bunch of clothes. I looked up in surprise, "Wow! Anna, thank you."

"You're welcome, hun," she grinned, then added excitedly, "I tried to get a mix of stuff, there's some practical stuff, a nice suit, a sexy dress, some other fun stuff."

"Wow! Where did you get all this?" I asked.

"I work in a costume shop, do you have any idea the amount of clothes I have access to?" she grinned.

I laughed, "I getcha, well thank you, this is awesome."

I heard a girl's voice from the back, "Anna, I got all the new costumes entered." Jamie entered from the back, she was wearing a Flapper outfit that looked like it would be fun to wear. "Oh sorry, I didn't know you were with a customer."

Anna shook her head, "Actually this is our greeter for tonight."

"Really?" Jamie looked surprised, "I though the greeter tonight was Tiffany from the other night..." she then looked at me and her eyes narrowed. "Wait a second... that was you?" she asked.

I blushed a bit and nodded. Damn, was everyone out to embarrass the hell out of me?

"Cool, you make a really cute girl then! I hope you like tonight's costume," she added.

I perked up at that. "Oh, what is the costume?" I asked casually.

"You don't know?" she asked. "Well, I don't want to ruin the surprise."

Dammit!

"That's good," added Brad entering the room. "She'll get to see it soon enough! Good to see you," he laughed a bit.

"Always good to be back," I smiled, feeling a little awkward. I was already getting turned on, and I hadn't even started dressing yet.

"Anna, did you get everything you needed?" Brad asked her.

"Yes, but I've got more, I'll talk while I'm doing make-up, though," she smiled at me.

"Great, come on back, we'll get you started," Brad waved me back.

"I can't wait to see how you look!" Jamie said excitedly.

I blushed a little and followed Brad back into his office. He went over to the desk and picked up a box. He was smiling as he handed it to me. I looked and saw it was a... French Maid costume! Oh la la!

I looked up at Brad, my mouth open in surprise and he laughed, "I thought you'd be excited about this one."

I nodded excitedly. "Absolutely, I can't wait to try it on!"

"I can't wait either," Brad said and winked. "I'll leave you to it. Hopefully you know where everything goes," He winked again as he headed out.

He headed out of the office, and I grabbed the box to see what I was getting myself into this time.

I opened the box to get a better look. This wasn't some little one wear outfit, nope this was a heavy duty vinyl maid outfit. I rubbed the shiny material feeling myself getting aroused already. It was the traditional black and white French maid outfit with the white frilly parts done in a lighter, white vinyl, while the main dress was a heavier, thicker gauge of black vinyl. The skirt flared out widely, and looked like it was going to be quite short. The better to show off the black and white ruffled panties, I guess? Or maybe the black seamed stockings? The top showed off a fair amount of cleavage, but wasn't completely exposing. It did have short cap sleeves and came with some wrist length gloves, a white apron and little white cap, all in PVC. This looked like it was going to be amazing. Plus there was a heavy duty PVC corset, though that didn't look like it was standard part of the costume. Nice to see I was getting the special treatment again.

I started stripping down while setting out the various pieces of the outfit. I was quickly in my little black panties, but those seemed tame in comparison to the ruffled ones.

I pulled mine down and quickly pulled on the ruffled panties, trying to tuck my rapidly hardening clit before it got fully erect. It hurt for a moment, but the pain helped me get control and I was able to tuck myself into the tight black underwear. The cool vinyl felt amazing and I was very much in heaven and getting really excited.

I picked up the dress and realized it was pretty heavy, so I decided to finish the undergarments first. I grabbed the stockings and rolled them up. Sliding the silky material up my legs, my head swam slightly as they gripped my shaved legs. My breath came short as my excitement spiked. I really debated jerking off quickly, but I wanted to be fresh for any fun later. I was really tempted though.

The stockings were designed as stay-ups, but I wanted more of an old school look. I dug around in my new bag that Anna gave me. Sure enough, I found a black garter belt and fastened it on. Feeling very sexy as I connected the garter tabs to the stocking tops. Connecting them around the stay up nubs was a bit of a pain, but I managed.

I then pulled out the corset, this really was heavy duty. I could feel the stays were very strong, probably even metal, and the PVC material meant this sucker wasn't going to have much give at all. I undid the laces and slid my portable prison on. It was very tight, I only had it slightly done and I was already out of breath. I got it positioned and tightened it enough that it wasn't going to fall down, then I started working on the laces. I knew I could only get them so tight, but I had a feeling my bosses were going to want this sucker tight.

I tied off the ends of the laces to the door handle and leaned in, feeling the bones squish me in and literally take my breath away. I untied the laces from the door, doing my best to tie them off behind me without having the lacing slip too much. It was pretty tight, but I knew it could go tighter. Though really getting it tighter both scared and thrilled me.

I dug around in my bag and found the nice silicone inserts from last time and slipped those into my corset cups. Between the falsies and the corset, I had some pretty nice tits. The cleavage shown by the dress would actually be some of mine!

I debating doing the dress, but I figured I should probably do make-up first. I pulled out the kit and set-up in front of the full length mirror in the office. Thankfully, the light was pretty good, so I was able to see myself clearly and had a good idea of how I wanted to go.

First, I put on foundation. This kit was pretty comprehensive, so it contained several colors and types of foundation. I found a nice match for my skin tone and applied a smooth base coat. I knew I wouldn't need too much since it was mostly dark out there. Just enough to keep a sheen off and hide any blemishes or anything.

By that same thought, it was going to be dark, so I knew I had to go kind of big with the make-up. The trick I'd found while practicing was being able to balance a big look without it looking like clown make-up. So, I started with the eyes; since the outfit was black and white, I wanted to put my splash of color in my make-up. I decided to go with red for the eye shadow. I know technically the make-up doesn't need to match the lipstick or anything, but it made things simpler for me if it all worked together. That's why I also just went with straight red. I'd been practicing blending colors, trying for a smoky effect and the other cool things, but I wasn't ready to try them while being out yet.

I started from the inner part of the eye and carefully brushed on the bright red color. It was disorienting looking with one eye while holding the other closed. I guess that's why its easier to have someone else do the make-up? Anyway, it took some time, but I was able to get the color to the shade I liked. I used my finger to smudge the edges and blend the color a bit, trying to get a nice faded look.

Once I was happy with the shadow, I moved to the mascara. This part always seemed so simple, but was deceptively complicated. It was just running the brush over your eyelashes, right? However, it was easy to get the mascara on your eyelid and mess up your eye shadow. And then trying to get that off screwed up your whole look. Believe me, I'd been practicing enough that I'd done all of them. The tough part was getting it all over without clumping, and I managed that pretty well. Like I said, it was going to be dark, so mascara was a bit extra for this. I pulled out the liquid eye liner and ran a quick line across the bottom of my lower eyelid. It was a real pain in the ass to do, but I managed it. It helped highlight the look, so I decided it was worth the irritation.

Next, doing some blush was fairly easy. Using the large brush, I put a bit of red on my cheeks. The trick was to blend it all out so it didn't look like you had red splotches, just a nice color highlight. Then onto the lips. This was also deceptively easy. I found it was really easy to go too big and look freakish. I wet my lips and filled in the outline of the lip, covering the whole natural area getting a nice reddish look. I debated putting on some lip gloss or lip liner, but again figured that was a bit much.

I took a look in the mirror and smiled at myself. I looked pretty good, and I managed it myself. I blew myself a kiss and began digging in my bag for a wig. I was trying to decide between the two I had when there was a knock on the door. I absentmindedly answered and kept digging in my bag.

"Ready for your make-up... oh?" Anna said, then trailed off as I looked up. "You already did your make-up?"

I smiled, "Yeah, how does it look?" I screwed up my face, waiting to hear it was terrible.

"Pretty good actually. I probably would have gone a little heavier, but I guess if you're just out on the street, it doesn't really matter."

"That's kind of what I was thinking," I said holding the blonde and black wigs in my hands. "Which do you think goes better with this outfit?"

"I think we should keep going with the red theme," she said holding out a red wig. I realized this one was very long, probably at least shoulder length, maybe even longer. My mouth came open in surprise. I'm not sure why, this was a costume shop, they had a ton of stuff, but it was just another dream come true for me. Now I got to be a red-head!

I took the wig and settled it in on, Anna helped me, getting uncomfortably close. I could feel the heat from her breath on my neck and her breasts gently rubbing against my shoulder. As we got the wig settled to a nice location, Anna whispered in my ear, "I like the garters, nice touch." She reached down and plucked one of the straps, snapping it against my skin.

My breath caught as I gasped in excitement and my clit surged in my panties. "Hey, I'm already worked up, teasing like that is not nice," I grinned.

Anna just chuckled evilly and said, "I know. How about I take your breath away?"

"I... wha..." I started to ask, then she pulled on the laces for the corset, and my breath was squished out of me. She tugged on the strings for a few minutes before getting everything nice and settled and retying the back laces.

She then turned and started heading out, calling over her shoulder, "I was going to tell you a surprise while doing your make-up, but I guess you'll just have to wait. Oh, and Brad left shoes on the desk for you."

I looked back at the desk, I hadn't noticed them but she was right. There was a pair of white and black pumps, I believe they were called saddle shoes. These had a super high heel, probably at least five, maybe six inches. Good thing I'd been practicing walking in heels, too.

I figured I should get the rest of the dress on, not that it seemed anyone would be upset if I pranced around in my underwear. So, I pulled out the dress itself, I undid the zip in the back and realized that was probably going to be a pain in the ass to do by myself. I slid the cool, slick PVC over my head and let it drop down, tugging the tighter part down to my waist, I could feel how wide the skirt flared out. As it settled I realized there was some kind of built-in petticoat or something causing it to flair. I slipped my arms through the shoulders and settled the collar around my tits. I struggled a little getting the zipper done, especially with how limited my mobility was from the corset, but I eventually got the zip all the way up.

I reached back into the box, and pulled out the little apron and tied it around my waist. It was cute and the splash of white helped offset the mostly black uniform. I pulled out the little cap and looked it over. I wasn't completely clear on how it fastened to my hair, but I figured I should do that before heading out. I gave it my best, but it didn't quite sit right, so I'd have to ask about that.

I took the shoes and sat down to slip these on. Good thing I waited, these were really high heels. Holy hell, I couldn't believe it! I stood and felt like I was on stilts. Even with all my practice this was going to be a challenge.

I tottered back over to the desk, focusing on keeping my hips centered over the shoes. I picked up the gloves and slid them on. These were also PVC, but much shorter than the elbow length gloves from last time. Instead these just came slightly past the wrist and then the white flared out. They again gave a nice pop of color.

I looked myself over in the mirror, and man did I look like sex on heels! I couldn't believe the sexpot in the mirror was me. It made me feel really confident about going out this time. So, I turned and headed out of the office. I came into the stockroom area and saw Jamie was working on some boxes and items. She looked over and whistled, "Wow, you look fantastic!"

"This old thing?" I asked waving her off. "Really, though, thank you that makes me feel better about going out."

"Girl, you're gonna knock 'em dead. You'll probably have job offers to come and be someone's maid. Maybe even some marriage offers!" She laughed and winked, settling back into her work, but stealing a quick glance as she did.