Working for Halloween Ch. 02

Anna Kendrick

As I hung up the phone, I shook my head and wondered what I was thinking. It was just a few days after my “outing” (quite literally!) at the costume store, and here I was agreeing to go again.

Sure, I’d enjoyed the hell out of it. Both the dressing, and the, uh… extracurricular activities with Brad afterwards, but I couldn’t keep pretending to be a girl. Especially if they were talking about trying to have me do a catalog or something! Hopefully, that was just something Brad was talking about, and they weren’t serious about it.

Also, I was feeling that usual guilt I got after dressing. After all, no real man would want to wear women’s clothing right? So, what the hell was wrong with me that I would? I didn’t think I was gay, since I still found women attractive, but since I’d enjoyed being with Brad, I guess I was bi? I don’t know, it gets confusing quickly.

I often get like this after dressing. It was also part of the reason I’d always tossed out all my clothes after dressing. “Purging” is the technical term. The idea is, if I toss out all my girl clothes. I won’t be able to dress in them, so I won’t be tempted to dress at all. The problem? I just go and get more clothes. I was definitely not throwing away the sexy pirate girl costume I’d gotten last time! That costume now had a special place, both in my mind and my collection.

Brad had explained to me the costume for tonight was the Sexy Ladybug. Apparently, they didn’t go for creative titles with these costumes. He explained it to me, and it sounded cute, but I wasn’t sure what it was going to look like when it was on.

I hopped into the shower. I knew I had time to shave before I needed to be at the store. I briefly wondered if Brad would want to have another tryst afterwards. As I soaped up in the shower, I remembered what he’d promised to do to me. I began sliding my soapy finger around my ass, then slipped it into myself.

I toyed with myself for a few minutes, until I started getting really excited. Then I realized I’d want to be ready for tonight, so I stopped fingering myself, and finished up in the shower. I’d been a swimmer all through high school and college, so keeping my body clean shaven was nothing new to me. However, I took more care in it now than I usually did. I was also annoyed to nick the back of my knee. How long had I been doing this? I guess I wasn’t usually this nervous.

So, I took the bus over to costume shop, the whole way both very excited and very nervous about going. I opened the door and the little bell rang.

Anna was working out front again and gave me big smile, “So, you decided to come back, huh?” I saw she was in another dark costume, though I wasn’t sure exactly what this one was. It was similar to the witch costume from last time, but looked a little more… severe.

I blushed a little, “Yeah, I figure it worked so well the first time.”

“Got a real kick out of it, I’m guessing then?” Anna needled me.

“Something like that,” I was really blushing now.

“Don’t worry, I think it’s awesome. It’s very refreshing to see a guy who isn’t afraid to express himself,” Anna continued.

“I, yeah, well thank you,” I stammered, not sure how to react.

“Besides, you look really damn good, and it certainly moves the costumes! Brad is in the back, I think he has everything ready again.” Anna nodded towards the back.

I headed through the swinging doors and into the crowded back storeroom. There were even more boxes piled up than there were last time. I headed over to Brad’s ajar office door and knocked. He was on the phone. He smiled up and held up one finger. It sounded like he was wrapping up the call.

“Yeah, that’s fine. No, it’ll be about 15 minutes or so… uh-huh… see you then,” Brad hung up the phone and smiled up at me. “Hello, glad you decided to come back.”

“Me too, though I have to confess, I’m kinda nervous,” I responded.

“Don’t worry, you’ll look great. Hopefully better than last time,” he gestured toward the costume box sitting on his office couch. I blushed looking at the couch thinking about what happened there last time.

“Sadly, I won’t get to see it, I just called into a last minute meeting and I’m going to be leaving very soon,” he sounded really disappointed. “Oh, well. Hopefully I’ll be back before you’re done.”

“Oh, that’d be good. So, it’ll just be me and Anna?” I asked, looking through the costume pieces.

“No, we have another associate coming from another store to help, though she doesn’t know who you really are, so we’ll keep that under wraps.” I nodded appreciating his discretion. “I’m going to head out in a bit, once you get the costume on let Anna know, and she’ll give you a hand with your make-up again,” he stated as he started gathering paperwork up.

I nodded thoughtfully, “I guess I should get her to show me how to do the make-up. That way I can start doing it myself.”

“That’s a good idea. I’ll get you one of the basic make-up kits so you can şişli travesti practice at home, too,” he said heading out of the office.

I opened up the costume box taking a look at it, pulling out all the pieces, trying to get an idea of what it would like when on. It looked more cutesy than sexy, but I’d have to see it on.

Brad came back in and saw me looking at the pieces, he came over to hand me a small bag, “This has a good selection of various make-ups. Anna can show you what everything is.”

I took it and opened it up, taking stock of the contents. I didn’t even know what most of these were!

“I have to get going,” Brad stated, then lowered his voice, “Try to have Anna get some pics for me. I’ll try to be back before you’re done.” He smiled, the implication obvious.

“You better get going,” I whispered.

He took a quick breath, “See you later, I hope.”

“Me too,” I smiled and turned to start getting undressed.

As I looked over the costume I realized there were no underwear. I don’t know why I’d be surprised by this, that’s not the sort of thing that always came with the costume. I had worn a pair of plain white cotton panties, but they just didn’t seem right. Certainly not for an outfit being described as ‘sexy’!

I leaned out the door and yelled for Brad, but I guess he’d already headed out since Anna came back, “What’s up?” she asked me.

I grinned a little sheepishly, “I just realized I don’t have any underwear for the costume.”

“Yeah, they don’t include any with most of them,” she said.

“Is there something I could wear that might go with the outfit?” I asked.

She paused, then smiled a bit, “Sure, we have some stuff that’ll work. Worried someone’s going to see up there?” she teased me.

“Well, if they do, I want to keep the image of ‘sexy’ going,” I teased back.

She thought for a moment, then she said, “Yeah, we’ve got some stuff that’ll work, hang on I’ll be back in a few.”

I went back into the office and got the outfit ready. It looked kinda cute actually, in a weird sort of way. I heard a quick knock at the door and Anna came in. I realized as she came in that I was just in my panties and t-shirt. “Oh, sorry,” she stopped. “Do you want me to come back?”

“No, its fine,” I shrugged, realizing she’d seen me dressed last time, so there was really no reason to suddenly get shy, besides she seemed quite interested in staying. Or was I just reading too much? Maybe it was because I was already pretty turned on by the thought of parading around in costume?

She handed me a bright red pair of panties. I was worried they looked a little small, “Are you sure these are the right size?”

“Yeah,” she said, “They’re vinyl so they stretch a bit and they’ll help… hold everything in.” She grinned at me as she said that.

I smiled and laughed a little back. I pulled off my plain cotton panties and pulled up the red ones. They felt wonderful sliding over me. I very quickly tucked everything away before I started getting too turned on.

“See?” Anna said, “They’re perfect, and they keep that sexy look going.” She winked at me as she headed out of the office.

My head swam a little as I tried to figure out if she was flirting with me. It occurred to me, she might not even know!

I focused back on the task at hand as I knew I would need all my time to get ready, and to get made up, too. I started by slipping the first stocking up my legs. I realized these were vinyl, too. The cool material felt very smooth sliding up my legs. I would have to check out more vinyl, I was really enjoying this material! I smoothed out the stockings, trying to ignore the sensations that were causing me to make a bulge in my panties. I focused instead on getting the rest of the costume on. There was a top with lots of polka dots, I guess it was supposed to look like a ladybug. There was also a frilly ruffled skirt, a set of wings that went on the back and a headband with little deely-boppers that were supposed to be the antenna.

I put on a red bra and slipped in my breast forms to give a nice illusion of breasts. Then I pulled the top down and tried to arrange so my tits were on display without showing the forms. I then put the loops for the wings over shoulders. I then pulled up the ruffled skirt and arranged it so it fell all around my thighs. It did little to cover anything, good thing I was wearing those panties! If I bent over everything would be on display. Then again, that was probably the idea!

I arranged the wig on my head, this time the wig was jet black. I used the hair clips to secure it onto my head. I put the headband on and felt the antenna balls bouncing around. Those were a little weird, but I guess it was a part of the look. I looked in the mirror and realized that I looked pretty sexy. I would still need to style my hair and get my make-up on, but I didn’t look bad, just plain. This would be a lot of fun bakırköy travesti again!

I must have been fixated looking at myself since I never heard Anna come back in, “You look good,” she purred. “Hopefully we’ll move those like you did last time.” She smiled at me and handed me a pair of red and black shoes in a Mary Jane style with some pretty high heels. Thankfully they were chunky heels, so I’d probably be able to manage them.

“You don’t think these are a bit… high?” I asked, a bit worried.

“They are, but I’m sure you’ll manage,” she said. “I want to see how you look in them.” She grinned that grin again, and I felt myself somewhat compelled to follow. I’m not sure what it was, maybe the look in her eyes. There was a sort of a… gleam. I shook my head as I slipped the shoes on. They were very cute and sexy, but man were they high. It was at least a 4″ heel. I wasn’t sure I’d be able to stand on them the whole time, but I guess you have to sacrifice for beauty sometimes!

“Ready to get your make-up?” she asked.

I nodded, “Yes, but I’d like you to tell me how to do it this time, so I can hopefully start doing it myself.”

“Practice makes perfect,” Anna giggled and grabbed a make-up kit. She sat me down and sat down next to me. She opened up the kit and began pulling out brushes and colors. She explained the various types of brushes and what worked best for different looks. It was a lot to take in.

“To start with though keep it simple and work on building as you get the simple stuff down,” she explained. She started with the foundation. “This will help cover your facial hair and make your face look rounder and more feminine. It can also conceal blemishes or anything like that.” She showed me how to spread it and blend it in. She then showed me the eye make-up, which was probably the trickiest to do, especially with trying to do mascara, eye shadow and eye liner! Finally she put a little blush on each cheek, not a lot just enough to give me some color. Finally we came to the lips. She put on a layer of bright red lipstick, showing me how to fill in and make my lips look fuller.

“You really should paint your nails next time,” she said looking at my hands. “It will make your hands look more feminine.”

“I guess I’ll have to practice that, too.” I shook my head, realizing how much it took look so good.

“Though in the mean time…” she trailed off looking around thoughtfully.

I raised my eyebrows questioningly, but she wasn’t looking at me. She stood and went out of the office. I wondered if I should follow her, but she came back a few minutes later carrying something black.

She handed me some gloves, “These will help cover in the meantime.” She smiled at her own ingenuity.

I pulled the gloves on and realized they were vinyl just like the outfit. They felt very cool and slick on my hands and wrists. I admired the way they made my hands look. They felt quite nice, too. I realized Anna was watching me and I blushed a little embarrassed.

“Don’t be embarrassed, sweetie. You look good, you look better than most girls would in that outfit,” she just shook her head. “I’ve got to head back out, I’ll be back to get you in a few minutes and we’ll head out.”

She stood and headed out, so I practiced walking in the heels. I guess I was going to have to practice that, too! Well, at least it gave me a good excuse to dress at home. I briefly wondered if I’d have the courage to try going out other than here at the costume shop. I’d always wanted to go to a club or something, but I was so scared someone would see I was a guy. Of course, I was getting ready to spend a few hours being ogled in a sexy Halloween costume, but that seemed a bit different. For one, I didn’t have to talk much, and the focus was less on me and more on the costume. I thought going to a bar or club or something would probably be a whole different experience.

“All set?” Anna leaned in the doorway, she gave me a big smile.

I took a deep breath and nodded, not really trusting my voice. Anna gave me a sideways look. “You know, you should try to practice your voice, too.”

“I feel like I’m in a play, I have all this stuff to practice,” I joked.

“You’re not far off, really. You’re playing a part, you’re just playing the part of a woman, and most women are going to know you’re a guy pretty quickly. Now, guys will just see the sexy outfit and be mesmerized. Guys are kinda stupid that way.”

I nodded, “Yeah, we are, I mean, they are, I mean… I don’t know.”

Anna laughed then gave me some pointers. “Did you ever really open up and speak super loud?”

“Like projecting your voice,” I nodded.

“Exactly, well you want to do the opposite. Sort of close your airway off, so you’re using less air. It will make your voice sound a bit… breathy, like a Kathleen Turner kind of thing, but it beats the hell of some lame falsetto,” she explained.

I tried istanbul travestileri it, “Something like this?” I tried to keep my throat constricted as I talked. My voice did sound lighter, more feminine. Not really a woman’s voice, but less obvious than my usual voice.

“Not bad, keep practicing that, maybe you’ll get it,” she smiled.

“I don’t know if I can keep up with all this,” I said in my femme voice.

“I know, it seems like you’ve got a lot to practice for tonight,” she smiled slyly at me again.

“What do you mean tonight?” I asked breathily.

“Nothing,” she said but pointedly looking at the couch, then back to me. I raised my eyebrows taken aback for a moment. Did she know something? I started to ask, but she’d already headed into the storeroom. Then again, maybe she was just teasing me. Even more confused and finding myself getting turned on again, I followed her out into the store.

I saw a few shoppers browsing. I also saw a short blonde with really short hair and a pixie costume working the register. Anna swung by the counter and introduced us. “Jamie this is… ” Anna paused realizing she was getting ready to say Tom, and thought better of it.

“I’m Tiffany,” I said in my best femme voice.

Jamie looked me up and down, “Wow! You look so amazing. How did you guys find someone to pull off this costume?” Jamie looked to Anna.

Anna gave me a sly smile, and I wondered if her faux pas was deliberate. I was getting all sorts of weird vibes from her tonight. “Brad actually knew Tiffany here from school, so we were pretty lucky to get her.”

“Well, good luck, you’re awfully brave. I don’t think I could do that,” she said.

“I’m sure you could, I love your costume, it’s very cute,” I said back. Jamie smiled real big.

“Thanks, I did a lot of it myself,” she said, obviously proud. She was cute, too. Not really sexy, but the pixie look definitely worked on her.

“Have fun out there, Tiff,” Jamie wished me.

“Oh she will, don’t worry about that,” Anna assured her.

As we headed out the door, I felt those butterflies starting to come back and I started getting nervous again. Then I remembered how much fun I’d had last time and focused on taking some deep cleansing breaths. I also really needed to focus on the heels. Thankfully Anna carried the sign for me.

We got out on the sidewalk by the road and Anna set-up the sign.

“Are you good? Do you need anything?” she asked.

“I just need to relax and get into it, and have fun again,” I told her.

“Well, good luck, you really look awesome,” she looked me up and down one more time, shook her head and then headed back in.

Reality settled in again and I had that moment of panic. Someone honked as they drove by and I remember how it went last time. So I started vamping it up again. I started teasing some leg, shaking my head so my hair flowed around and the little deely-boopers shook around. Once I started getting more honks and wolf whistles, I remembered how much fun this was. The exhibitionist in me started getting off, and my clitty started leaking again.

I remembered why I enjoyed this so much the first time! I was getting lots of honks and whistles. Again, I had several guys stop by to take cell phone pics. This time instead of worrying about it, I just posed and vamped it up even more. Several guys gave me their phone numbers, which was a little weird, but also quite thrilling.

I also got to practice my feminine voice, since several guys stopped and tried to talk with me. One guy came up and looked a little nervous.

“Are you okay?” I asked.

He smiled and looked sheepish, “I just wanted to tell you that I think you’re super hot.”

“That’s very sweet,” I smiled back. “Thank you, but I really can’t talk, I’m kind of working.”

“Oh, right. I understand, that’s cool. Well listen, if you want to get a drink or coffee or something sometime…” he trailed off and turned away.

I was surprised at how nervous he was. Then I thought about it, if I was trying to walk up to a strange girl who was really sexy and pretty, I’d probably be super nervous, too.

I was having so much fun, I didn’t even notice how tired my legs and feet were getting until Anna came out to get me to head back in. I was glad because it was starting to get cold, even though the costume covered most of me, the flowing skirt definitely let a strong breeze up there. Since my panties were just as wet as last time, that meant it also got cold very quickly!

As Anna led me back in, she updated me. “Just like last time, we sold out of those costumes again. You keep this up and they’re going to have you back every day!”

I smiled, “Well, that wouldn’t bother me, too much.” I put on my best femme voice, “I could use the money, and I have a really good time doing it, too!”

“Yeah, I could tell. You definitely put on a show. The guys were talking about you the whole time they were coming in. Some of the girls, too.”

I laughed at that, “Nice to know I was popular.”

“I think some of them might have been a bit jealous,” Anna said in a low voice. “I think they got the costume so they could ‘show you up’.”

I was a bit taken aback by the idea that any girls would be jealous of me. Anna didn’t seem to be too upset by it.

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