tagTranssexuals & CrossdressersWorking for Halloween

Working for Halloween

byshawnavinyltv©

I stepped off the bus and walked the short distance to the 'Costumes and More!' shop. I couldn't believe I had agreed to do this, but if I was ever going to buy a car, I needed to get the money. You've probably seen them, this particular costume shop always has someone in costume out in front holding a sign and waving to the cars driving by. They seemed to like to vary the costumes, I guess to show off their selection.

So, when Brad, who was the manager, called me about doing it, I wasn't too sure. Sure I needed the money, but who wants to dress up like Spider-Man and stand waving at traffic for two hours? After I was hesitant, Brad upped the ante and was willing to pay me a little extra. He said it was since he knew me.

I walked up and pushed the door open. A small bell rang with a chime like a church bell. I guess it was supposed to be spooky, but it was really just cheesy. Of course, the whole place was. I guess that was part of the fun really. The girl behind the counter looked up as I came in. She came over towards me.

"Hi, can I help you?" her name tag, read 'Anna'. She was dressed in a witches costume. Not one of the really sexy ones, which was a shame. She was kinda cute, a bit of a big girl, but still quite cute. I wondered if she'd look good as a vamped up witch. I've always had a thing for big girls. I also wondered how I'd look as a vamped up witch, or even in her plain witch costume. As a long-time cross dresser, I always wondered about those sorts of things. Halloween was a favorite time for trannies, but I hadn't had the courage to go out dressed yet.

"I'm Tom, I'm here to see Brad." I replied.

"Oh," she said, "I'll let him know."

She headed toward the back, and I turned to look through the costumes. Brad and I had gone to school together, though he graduated a year ahead of me. I barely knew the guy, but someone at school had mentioned they'd worked for him a couple of times, and the money wasn't bad. They'd usually let you keep the costume, too. Since they didn't do resales, they only sold brand new costumes. I'd mentioned something back about needing some money, and it sounded pretty good. I guess they'd mentioned me, because Brad called a few days later.

"Tom! Glad you could make it down." Brad came out of the back.

"Hey Brad, long time, no see." I casually replied.

"Listen, thanks for doing this, I know you were a bit hesitant, but I really needed someone for today." he said. "Come on in the back."

"How come?" I asked following him.

"We've got one of our regional managers coming by today."

As we went through the swinging doors, Anna headed back out front. I smiled quickly, but she didn't even look at me. Not too surprising really, I've never really turned heads. At 5' 6" and 140 pounds. I was definitely not "tall, dark and handsome". "Short, plain and cute", maybe. Sadly, very rarely did girls notice me. Sure, I'd had my share of girlfriends, but they never really stuck around.

"So, you've got an inspection or something?" I asked looking around at all the boxes of costumes, and wigs and make-up.

"Yeah, since I only just took over as manager a few months, they're still keeping tabs on me. They like to make sure I'm following all the protocols." he headed toward a door marked 'Manager'.

"They make you jump through a lot of hoops?"

"Yeah, they're pretty strict, but our sales have been good so far. So they're not too bad. That's why today is so important. I'm really hoping to get them off my back."

"What do you mean?"

He lead me into the office. "They have this 'schedule' that each store is supposed to follow for our 'street greeters'. That's you, by the way."

"I gathered."

"So, today you'll be our..."

He looked confused, then closed his eyes.

"Oh, shit." He sat down at his desk.

"What?"

"I screwed up."

"Why? What happened?"

"Today is supposed to be our sexy pirate girl."

I looked blankly at him for a moment until it settled in. "Ohhh."

"Yeah, what am I supposed to do now?"

"Well, I'll wear tomorrow's and you'll have to explain it. They'll understand, right?"

He looked up at me, and just shook his head. The guy I replaced messed up on scheduling before. That's part of why he was let go."

"Oh, well can you get someone else? Maybe Anna?"

He perked up for a moment, then thought, "No, she probably wouldn't fit the costume. Besides, then they'd want to know where my clerk was!"

He looked down and shook his head.

"Well, unless..."

"Unless... what?"

He looked me over for a moment. "Maybe you could still do it?"

My stomach turned a little flip for a moment. As a long-time cross dresser, this was like a dream come true, but I didn't want to seem too eager.

"I don't know, I mean, me?" I said, trying to sound doubtful.

"Well, you'd probably fit, it might be a little small, but I think it would fit. Anna could do the make-up for you. We've got plenty of wigs, so that won't be a problem."

"I mean, come on Brad, I'd never be able to pull it off."

"Pull what off? You stand there holding the sign and wave. Anybody comes too close, you stand partly behind the sign."

"Yeah, but what if someone, you know, figures it out."

"All right, what if I double your fee?"

That made me pause. Get more money, and get to cross dress?

"All right, but I want it in cash."

"Done!" He sighed with relief.

"One other thing, the costume is a bit... revealing."

"Okay." I looked at him confused.

"Well, will you need to shave?"

"Oh, well. I am still on the swim team, so I guess that won't really be a problem, huh?"

"Well, there's a bathroom in the back, go ahead and shave your face." He reached into his desk and pulled out his electric razor. "Just please wash it real well before and after. Hopefully, neither of us will have any reactions."

As I headed to shave up, Brad said, he set the costume in his office, to go ahead and change in there. He'd go and explain to Anna. He also kept checking his watch. I figured we were probably running a bit late, so I hurried and shaved quickly. Making sure to wash the razor very well. I hurried back to the office and felt myself getting excited seeing the sexy pirate costume complete with stockings, corset and boots.

I quickly slid the ruffled panties up and tucked my clitty away, to keep me from making an un-ladylike bulge! Then I wrapped the corset around and tightened it as best I could. It would do for now, I rolled up the stockings and pulled them up, delighting as always in the sensual feeling. I hooked the tops of the stockings to the garters off the corset. I then held up the PVC skirt, it was short, but flared, so it would probably show off my stocking tops. I guess that was partly the point though! The top was designed to show lots of cleavage with little of the shoulder sleeves. I stepped into the skirt and had just pulled the top on when I heard a knock. I was a little nervous, but said, "Yes?"

"You decent?" Anna asked.

It hadn't occurred to me she was going to see me dressed. What the hell am I worries about. I'm about to go stand on a major street and wave at passing cars!

"Yeah, come on in."

She entered and gave me an appraising look. "You actually look pretty good."

"Really? I don't look stupid? I feel pretty silly."

"No, you're a bit stockier than what most girls would be. Its a shame you don't have more cleavage. That would really make it convincing. Maybe we can get a corset or something."

"It had this corset, but I couldn't get it very tight myself."

"Oh, okay. Well, get the boots on and we'll get your make-up. Then I'll lace you in."

I slid the boots up and did up the zippers on the inside. I tried to stand, and had to catch myself on the desk.

"Easy there, sugar. I guess you need to practice with those. Good thing you'll just be standing in one place, eh?"

"Yeah, I just hope I can make it out front in one piece." I'd worn heels before, but these were way higher than mine. I was glad I'd just be standing in one place. Of course, I knew my feet were going to be killing me, but oh well.

"You'll be fine, just have a seat, and I'll take care of your make-up."

I was glad she was going to do it, since I'd done my make-up before, but it usually looked clownish, or at least amateurish. Hopefully, this would up my chances of passing, or at least not being noticed. I tried to pay attention to what she was doing, but with no mirror, and my eyes closed half the time, it was tough. After a few minutes, she pronounced me done. "Now, let's get this corset." She pulled the back of my top up and began tugging at the laces. I felt it getting tighter and making it harder to breathe.

"Whoa, okay."

"Just a bit more," she replied. I felt the corset squish down. "There you go, and now you've got some boobies."

I looked down and realized she was right. It looked like I had tits. My clitty stirred in my panties, but wasn't able to do much in its confines.

"Alright, let's get you out front. I think Brad has a wig for you, too. Oh, don't forget your sword," The costume came with a little belt, and a plastic pirate sword. I buckled the belt, and put the sword on.

I took a few unsteady steps, but with a little coaching from Anna, I was making a go of walking out to the front. I was starting to get really scared though, I couldn't believe I was going to do this. Oh well, too late to back out now!

I made my way through the back area, and was getting some confidence. Brad was there leaning inside the doors, "Oh great, Tom. I was just starting to... whoa!"

"What?" I stopped, and nearly fell. Brad caught me, and there was an awkward moment where he was holding me to steady me. I felt a weird flush, and felt my clitty twitching again.

"You okay?" he asked concerned, but with an odd smirk on his face.

"Yeah, is something wrong?"

"No, you look pretty good. You'll probably look great with that wig on." He pointed to a long-haired dirty blond colored wig. "It should fit, and will hopefully, look okay."

I grabbed the wig, and puzzled over how to get it on. Anna came over and helped me, showing how to adjust it right. She also used some hair pins to connect it to my hair.

"Well, I think we're going to do just fine. You look really good. Nice work, Anna."

"Thanks, he, err, I guess, she does look pretty good." Anna smiled proudly.

"Ready for your debut?" Brad asked.

"No, but I doubt I ever will, so let's go now, before I come to my senses!"

We all headed to the front, and I caught sight of myself in one of the display mirrors. I couldn't believe it! I really did look pretty good. Not beautiful, but certainly cute, and the costume practically screamed sex. I must have been staring open-mouthed, because Brad's voice came as a surprise.

"You okay?" he asked, close by my ear.

"Huh?" I stammered. "Oh, yeah. Fine, just surprised. I don't usually look this good."

He gave me another odd look, that in my surprised state didn't quite register. It also, didn't really occur to me what I'd just said.

I walked over to the door in a kind of haze. I could feel my clitty stirring again, and I felt a damp spot growing in my panties. My first outing as a girl, and I'm already dripping wet!

By the door, Brad grabbed the sign and held the door open for me. "I'll walk out with you, and help you get set-up."

"Good luck," called Anna.

We headed out the front door, the breeze zoomed right up my skirt. I could feel my precum as a cold reminder what I was doing. Not that I needed any really. My heart felt like it was going to explode out of my chest. Thankfully it hadn't gotten too cold yet, so even though the costume was revealing, I wasn't chilly. In fact, I was so nervous, I was sweating a little bit. Not very feminine really, but there it was. I tried to calm down, tell myself that no one would know it was me, to just relax and have a little fun. I also tried taking some deep breaths. Focusing on walking did help quite a bit. It took my mind of everything else anyway.

I stumbled at one point, and Brad wrapped a protective arm around me to steady me. I felt that flush in my stomach and clitty again.

"Thanks," I breathed out.

"You're welcome," he replied. When I said nothing further, he kept his arm about my waist.

Was I really getting turned on by this, and this guy? I mean, I'd fantasized about what it might be like when I was dressed, but I'd never really thought I'd find a guy attractive. I guess the fact that he was really treating me like a woman helped.

We got to the sidewalk, and Brad reluctantly let go. Seeing all the traffic zooming by really brought my situation back. I almost bailed out there, but then out of the corner of my eye, I realized Brad was looking me up and down. I smiled at him.

"Ready?" he asked.

"Still no, but I'm here," I replied.

He handed me the sign and went into a few quick things about playing it up a bit. I was in costume, so don't be afraid to put on a bit of a show. That kind of thing. I missed most of it, since all I could hear was my heart pounding. Finally, Brad handed me the sign and turned to head back in.

I faced to the traffic and waved shyly to a few cars. Several cars honked back. Okay, this wasn't too bad. I started to relax and get into it a bit. I even got a few wolf whistles. That really got me into it! I started tossing my hair, teasing a bit of leg, I even blew a few kisses. Hell, I wasn't nervous any more, I was having a blast!

Cars kept pulling in and people were heading into the store. I'd give them little waves and such, too. One guy couldn't take his off of me, and got into a bit of trouble with his girlfriend. I felt a little bad about that, but just a little.

After about ten minutes or so, something odd happened, a car pulled into the parking lot, but instead of heading over to the store, it pulled up next to the sidewalk, just a few feet from me. I started getting nervous again. Then I realized, the guy was holding up his cell phone and taking a picture. Wow! Someone wanted a pic of me as a sexy pirate! At first I was flattered, then I started to wonder where that pic might go. Oh well, its not like anyone would recognize me... right? That guy pulled away and I got more honks and wolf whistles. Even the guys stopping to take my pic became a bit of a regular occurrence! The third one that stopped even got out and came over to me.

"Hey," he said nervously.

"Hey!" I smiled and tried my best girly voice.

"Uh listen, you look awesome. Can I... get your number or something. Maybe we can go get coffee?"

I got dizzy and my head swam. I leaned on the sign for support.

"I..." Whoops, wrong voice. I coughed, and tried again in my girly voice, "I don't know, I'm working right now. Sorry."

"Oh, right, sorry. Okay, well here's my numbers if you change your mind." He handed me a slip of paper with a number and the name Keith on it.

"Thanks, I uh... have to get back," I pointed to the road.

"Right, okay, well I hope to hear from you."

He hit head on the roof of his car, since he was busy watching me. He drove off, and I was in shock. I can't believe some guy just asked me out! Its a shame, he was cute, too. Wait! What am I thinking? I'm getting waaaay too into this. Maybe I should call this off now? Nah, I could use the money, and I'm still having a ton of fun.

I did have the problem of what to do with his number, since I didn't have a purse, and women's outfits are often short on pockets. I eventually tucked it into my cleavage.

Another wolf whistle got me back into flirt mode. I was really vamping it up when I saw a very expensive luxury car drive into the place. I saw a tall, really good looking man in a sharp stylish business suit get out. He gave me a look and a smile. Then headed in. I wondered if that was the boss, since there weren't a lot of suits coming by.

The rest of the time flew by and I even got a few more numbers, several date offers, and other more lewd offers.

The shame was, all of the offers had the same effect giving me that tingling in my stomach and clitty. So, by the end when Brad came out to let me know the shift was up, my panties were soaked and I was hornier than I had ever been.

"So, how did it go?" he smiled.

"Not bad actually. My feet are a little sore, but it was actually a bit fun."

He took the sign and we started to walk in.

"That's great! You'll be happy to know, not only did we do a great business tonight, but we even sold out of the sexy pirate girl costumes!"

"Really? You mean this really works?"

"Well, not always. But tonight was great. We did way better than we usually do on a weeknight. We had lots of guys asking about you, too."

"Yeah, I imagine. I got several phone numbers, too."

Brad laughed as we came in the front door. He placed the sign I'd been holding next to the door, and the he turned the closed sign over.

"The best part is, my manager loved you," Brad was clearly happy, and relieved.

"He loved me?"

"Yeah, said you were the best sign girl we'd had yet. Maybe the best at any of the stores," he actually sounded proud!

"I find that hard to believe," I crossed my arms.

"Its true. Ask Anna. He couldn't stop going on about you. Right, Anna?" he asked the clerk, who was busily cleaning up.

"Yeah, he kept going on about it. I didn't think it would work, but it did."

I smiled at Anna, "The make-up really helped. I wouldn't be able to look convincing without it."

"No you probably could, you'd just have to shave really close," she laughed. "Brad, anything else you need?"

"No, Anna. I think we're good. Tom, do you need Anna's help?" he asked me.

"I don't think so, I'm guessing you've got something that will take off this make-up?" I returned.

"Of course, we sell it!" Brad replied.

"Then I should be good."

"Goodnight guys, err, gal or well, good night," Anna headed into the back room.

Brad and I walked to the back of the store, heading for the swinging doors. "So, I didn't tell you the best part yet."

"There's more?" I responded.

"Yeah, Mr. Davis, my manager, loved you so much, he wants to hire you to appear at all the stores. He even mentioned something about being in our catalog."

"Oh, come on, Brad."

We headed through the swinging doors. I saw Anna go out the back door.

"Seriously."

"And you told him I wasn't available, right?"

"Well, no. I mean I didn't commit for you, but you seemed like you really need the money. I can always tell him no later, but at least think about it."

"I don't know. I can't imagine being the 'Sexy Pirate Girl of Costumes and More'."

"Oh, I'm sure he'd want you to model some of the other costumes, too."

We headed into his office.

"I mean, you do look really good," he sounded genuine, and a bit, interested?

"Yeah, well thanks. It was fun, but I just can't imagine it."

"Oh, huh. I thought you'd be into it."

"What? Why?"

"Well," he hesitated. "You really put on a good show. You were one of the better greeters, we've had. But," he stammered.

"What?"

"Well, you seem very... natural."

"What do you mean?"

"Well, you didn't need any help getting dressed. Anna thought you'd at least need help with the stockings and garters. In fact, if it weren't for the fact that you seem to be having some trouble with the heels, I'd say you'd probably dressed up before."

"Well, that's, I mean..." my turn to stammer.

"Its not a big deal, if you did. Like I said, you look good, and are somewhat natural."

"Well, I..." I started towards the couch to get my clothes, but I tripped on the damn heels again. Wouldn't you know it, the bastard caught me again.

"Like I said, other than the heels..."

His lips were inches from mine, his arms wrapped around me. I felt that pulsing in my stomach and clit again. I was so horny now, I wasn't sure if I wanted him to kiss me or not. I had become really nervous again. We stayed like that for what seemed and eternity.

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