Working for Halloween Ch. 03

The door swung open and Brad came into the back, "Did you need something, Jamie?" He then spotted me and his jaw fell open. "Wow!" was all he could manage to say.

I struck a pose, smiling and blinking. "So, it looks good then?" I asked.

He just nodded dumbfounded. He came over and took my hand, leading me out to the front. He must have recovered a bit since he leaned through the door and said to Anna, "Hey Anna, may I present our greeter for the night!" And pulled me through the door.

I struck a pose again and Anna just shook her head, "Even with the preview I had, you really have surprised me again."

Brad nodded, probably not realizing he was still holding my hand, and I didn't really feel like breaking contact. Brad added, "You really outdid yourself, Anna. Her make-up looks amazing."

"Actually," Anna interjected, "She did her own make-up."

"She did, did she?" Brad asked, though more to me than Anna.

I smiled and nodded and said in my best femme voice, "She sure did, but I had a good teacher." I gave Anna a knowing wink.

"She is great, that's why its going to be tough running things without her," he added, letting go of my hand somewhat reluctantly.

"What do you mean without her?" I asked suddenly.

"Oh, she didn't tell you? Anna gave her notice, she'll be done in two weeks," Brad said matter-of-factually.

I looked at Anna and raised my eyebrow questioningly. I realized this must have been what she was going to tell me while doing my make-up. Anna shrugged, "Well, I guess you got some of the surprise. I'll fill you in on the rest later."

Brad interrupted, "Sorry, but we do need to get you started, Tiff." I had a little momentary thrill as Brad called me by my girl name that made me forget about my confusion.

"Okay, we can talk more after," I said to both Anna and Brad. "Oh, I wasn't sure about this cap and how to secure it. Could you show me?"

Brad showed me how the fastener worked, but he went ahead and fastened it on me. As he did so, he brushed up against me, I could feel his hard cock. I had to bite my lip to keep myself from rubbing him. Anna just smiled knowingly at me. My cheeks flushed, as if I wasn't aroused enough already.

We made our way outside, Brad wrapping his arm around me. I wasn't sure how much he was helping with the heels and how much just being close, either way it felt quite nice. We got to the sidewalk and Brad somewhat hesitantly let me go, handing the sign over to me. He smiled as he looked me up and down, "Damn, you really are amazing!"

"Awww, thanks sweetie!" I leaned in and kissed him on the cheek. I'm not sure why, I guess I wanted to do more, but knew we couldn't, at least not right now.

Brad smiled wider as I rubbed the lipstick off his cheek. "You need anything else?" he asked.

I smiled slyly and said, "I do, but we'll have to wait for that," I winked and turned to the passing cars. Already a few had honked. So, I waved back. Brad just shook his head and trekked back inside.

The shift passed very quickly again. It was amazing just how into playing it up, I could get. Between waving to cars, posing for pictures, getting several phone numbers and e-mail addresses, not to mention offers for dates and yes, even a marriage proposal, I was in sissy maid heaven. The big event happened after about an hour or so into the shift.

Several cars had pulled in, with guys getting out and coming over to talk to me, however the one an hour into the shift was a bit different. First, he was wearing a suit, no tie, but he was also tall, confident and pretty good looking. He approached me and stood watching for a moment. So, I posed thinking he was going to take a picture.

Instead he said, "Hello, I'm Darien Davis, we have an appointment to meet in a couple days, but I wanted to meet you beforehand."

My mind blanked for a moment... who? Appointment? What the hell was he talking about? Ohhhhh! This was the boss. Brad's boss specifically. I recovered somewhat, "Oh hello, its nice to meet you!"

It wasn't exactly witty repartee, but it covered the fact that I had no idea what to say. Also, I wasn't sure how he'd react to me being a cross dresser. I know attitudes were changing with that, but this was a company and a business. As I got a closer look, he was really good looking. Not like male model pretty, more rugged or dashing, but definitely turn and check him out again, good looking.

"Well, its great to meet you. You've only been at this a couple times, but everyone has raved. Especially Brad and Anna," Darien explained.

"Well, they've been super sweet and have been really showing me the ropes," I smiled brightly. I almost added 'so to speak', but didn't really want to explain all the sexual liaisons I'd had with the staff.

He smiled back, and he had an odd look, like he saw something, but wasn't sure. Had I been 'made'? One thing about trying to pass as female, is when someone realizes you're not. This is being made, and I thought maybe he'd figured it out, but then he smiled warmly again. "Yeah, they've been a good crew, we'll miss Anna, too. I was hoping she'd move up to manage her own store soon, but seems she's got other plans."

I nodded, "Yes, she told me a little, but we didn't have much time to talk about it."

"Well, you look like you're busy, so I'll let you get back to it," he gestured to the traffic.

"As you like, you're paying me, so I probably should get to work," I joked with him.

He smiled, shaking his head a bit, he then took my hand and kissed the back of it. Holy hell! I didn't think guys really did shit like that? But the gesture as outdated and ridiculous as it was, really hit me. I was so excited to be treated like a lady, that I actually squirted a little. Yeah, I know, not very lady-like, but I'd only been a lady for a couple hours.

I could only gasp slightly for air as he did that. So, he added, "You really look amazing. I look forward to having you in my office."

I smiled and nodded, "I'm looking forward to being had."

He held my hand just a bit longer, and seemed reluctant to let go, but he did eventually. Then headed inside. Well, the shift had been a breeze up until that point. And by breeze, I mean the highly flared skirt just let any and all cold breezes right up there, so even though I was creaming my panties most of the time, it also got pretty chilly where I was.

So, after Darien introduced himself, the rest of the shift passed in a daze and it wasn't long before Brad was back out to recover me. When he walked up, I looked surprised, "Wow! Already?"

"Already? You were done about 10 minutes ago, Anna and I had a bet on whether you'd realize on your own... I lost," he added.

"Oh, yeah, I'm just... enjoying playing it up out here. I guess I like showing off?" I shrugged not sure and not really caring to be honest.

Brad reached over to take the sign, "Well, we're closing in just a bit, so unless you're planing to go home dressed in costume..."

I looked thoughtfully, "I wonder how this would go on the bus?"

"The bus? Most folks probably wouldn't even notice!" he joked.

I shrugged and took his arm and we started walking back in.

"Would you really wear that home?" he asked.

I shrugged, "I guess so, I mean, I've always wanted to try going out as a girl, but I've never really had the guts, or anywhere to go."

"What about Sixth Street?" Brad asked.

"The gay bar? I dunno, I guess I figured it was always just guys, so..." I shrugged.

"Would you want to go?" Brad asked raising his eyebrows.

I looked surprised, "You mean, to say, tonight?"

Brad shrugged, "I don't know, maybe, I was just thinking, it might be fun."

I smiled mischievously and leaned in closer, "What about any... extra-curricular activities?"

"We could still do whatever, we'd either have to come back, go to one of our places... something," Brad smiled brightly.

"Oh, you want to show off your hot piece of ass? Is that it?" I teased.

"I'll admit, it would be pretty awesome to be seen with you on my arm," Brad teased back.

"And being on your arm would make me a lot less nervous going out," I emphasized the 'a lot'.

Our conversation was interrupted as we re-entered the store. Anna looked up as the bell dinged, she looked ready to tell the customer they were about to close when she saw us. She was just about to go back to her work, when she looked at me leaning on Brad's arm and gave me a little eyebrow raise. I just shrugged and smiled.

Everything went to their usual routine, Anna, Jamie and Brad went about closing while I headed back into the office to take off my shoes and sit down for a few minutes. I took advantage of this time to start going through some of the items that Anna gave me in the bag and see if there were any good outfits. I was getting a good inventory when I hit a couple of solid items that I first thought might be shoes. I pulled them out and realized they were a bag with a... holy shit! A dildo, butt plug and tub of lube. Wow! Anna really did think of everything.

I thought for a few minutes and decided. I quickly took the plug and the lube into the bathroom. I nervously pulled out the plug from the pack, looking at the tapered shape and flared base and wondered briefly it it was going to fit. Well, only one way to find out.

I took a generous amount of lube and greased up my ass. Sliding the first part of the plug in was a strange sensation, the cool smoothness slid in easily to a point, then it hit some resistance and my ass really started to open up. I hit a point where I had to ease off and start basically fucking myself with the plug, then I opened up and the rest of it slid home. My ass closed around the flared base and I couldn't believe how full I felt.

I stood up and was amazed at how difficult it was going to be to walk with this up my ass. Maybe this wasn't such a good idea? I decided to give it a few minutes and see how I felt. I could always take it back out.

As I started walking, the combination of the plug and the heels really had me swaying my hips and focusing on my walking. I began really focusing on my posture, not that I had much choice with the corset on. Anyway, I made it quickly back in the office and sat on the couch. The short walk helped me get comfortable with my new friend. So comfortable, that when I sat down I sat right on the plug in my ass. I almost yelped and jumped, instead I sat leaning to one side. Sitting definitely put a lot more pressure on the plug, making me very aware of it.

Brad came in a few minutes later. "Hey, I... oh wow," he started, then fumbled as he caught sight of me.

"What?" I looked confused.

He grinned, "Nothing, I just thought you might have started getting changed."

"Oh," I looked a little embarrassed, "I thought you might want to... check it out more."

Brad smiled, "I do! Can I get a pic?"

As he held up his phone, I told him, "Only if you send me copies!"

I posed and he took several pics. He then sat on the couch, and I sat next to him. I was very aware of my plug and how horny I was. Brad kissed me, softly and tenderly at first, but then quickly he kissed me hard and I kissed him back. It only took a moment before his hands were exploring my body. One was rubbing my stockinged thigh, the other tracing the bones in my corset. I leaned in, feeling the heat radiating off his body. In this position, I couldn't really move my hands much, so I put one arm around his back and just held on, enjoying the sensations of his mouth and his hands.

He moved his mouth down to kiss my neck and I wrapped my fingers in his hair, moaning loudly as he nibbled on my skin, sending little electric sparks along my skin. He kissed around on me for several minutes, moving up to nibble on my ear, then back down to my neck, just driving me completely wild. As much as I wanted this to keep going on, I was getting out of my mind with lust and needed him soon.

I slid my hand down from his hair, running it over his chest and down his stomach to his crotch. I could feel his cock was rock hard and I wanted it bad. As I rubbed it through his pants, he started making grunting sounds while kissing my neck.

So, I rubbed the whole length hard, feeling him groan through my neck. I unbuttoned his pants and slid my hand in, he scooted up and I slid his pants and underwear off. I took his hard cock in my hand, stroking it softly, seeing how excited he was. As I was doing this, he started kissing my neck again. This got me moaning and stroking him harder, which got him nibbling and sucking on my neck more, and we got into this hot cycle of teasing and exciting each other.

After a few minutes, I couldn't take any more and leaned forward to lick his cock head. He groaned and I slid my legs onto the couch, so I could really get down and suck him. He sat back and began playing with my legs with one hand. The other stroking my wig gently.

I took my time, making a nice, long slow production, getting him very worked up. Licking from the tip down to the balls, teasing them, feeling how heavy and full they were. Licking back up, working my tongue the whole way. It only took a few minutes before his hands slid up my legs, lifting the short skirt and he started playing with ass.

I looked up and smiled with a twinkle in my eye, "You might find a little... friend... back there." I smiled and went back to licking and slurping on his cock. He just raised his eyebrow and traced his hand along my panties, making me shudder with pleasure.

His exploring found the base of the butt plug a moment later, "What is this?" he asked. He leaned over a bit to get a good look as pulled the thong aside and said, "Oh my!" He started playing with plug and I started making all kinds of purring and groaning sounds. Needless to say, that just encouraged him more.

I lost my focus on sucking him as the pleasure in my ass took over. He'd pull the plug out slightly, letting it slip back into my ass, fucking me with the plug. I simply laid on his lap, moaning and squirming as he teased my toy.

"You are a really bad girl," he stated. I looked up and he was smiling like he just won a jackpot. I tried to answer but could only manage brief gasping and moaning. "I mean you'd have to be a real slut to wear something like this under a French maid dress."

I squirted a little when he called me a slut. I really was, and the amazing part was I didn't care. "Are you a dirty little slut, Tiffany?"

I nodded, "Oh my, yes!"

"What does my little slut want?" he asked, pulling the plug all the way out.

"Oh my!" I grasped his cock. "I want you in me," I moaned, stroking him.

He pulled me up, and sat me on his lap. I reached back and lined him up with my asshole. Thankfully, I was very lubed from the toy, so his head slipped right in. I gasped again and moaned as I sank slowly down on him, feeling every inch slide into me. I shuddered in pleasure as he moaned his pleasure.

I stopped for a moment, letting my ass adjust to being so full again. I looked at him, "Was it worth the wait?" in my best sexy whisper.

"Oh fuck, yes," he replied, running his hands down my corseted side down to my stockinged legs. I gave a little shudder of pleasure as I slowly slid up, feeling his cock sliding out was such a delicious feeling. As I got about half of him out, I slid back down moaning the whole way. I stopped again, but just to catch my breath.

I bounced back up, starting into a nice slow pace, riding his rock hardness. My own hardness was straining the front of my panties, I was so aroused, I though they might rip. I debated pulling myself out, but I was just lost in the haze of pleasure coming from my ass. I didn't really want to lose that focus right now.

Instead after a few minutes, I wanted to really get fucked. I leaned into Brad's ear, "Do you want to fuck me?"

"I thought I was fucking you?" he smiled back.

"I mean change position," I moaned somewhat desperately.

"How do you want to be?"

"I don't give a damn, I just want you to plow the hell out of me," I breathed raggedly.

Brad pushed me up, I climbed up. He reached up and unzipped the back of the dress, and I let it fall off my shoulders and bunch up on the floor. Brad pulled me in and kissed me hard, as he bit my neck, he moved me over to his desk. I was about to ask what we were doing, when he spun me around and bent me over the desk. As I leaned down, I felt him slide up behind me and line his cock up with my ass. He thrust in and went balls deep in one stroke. I gasped and moaned at the same time, and before I could fully recover he was sliding in and out with long, slow strokes. He pulled most the of the way out, teasing me, before sliding deep back in.

"What did you want, my little slut?" Brad asked, pulling most of the way out.

"Fuck me, please fuck me hard," I begged, pushing my ass, trying to get him back in me.

Brad took pity on me and began fucking me, and I mean fucking me really hard. The sensation was almost overwhelming. The sounds of flesh smacking combined with the feel of his dick sliding in and out of me had me clawing at the desk.

"Ohhh, I think she likes it," he growled without slowing down.

I nodded vigorously, "Oh hell, yes! You can fuck me like this any time!"

"Really? Any time?" Brad asked.

"Yes, just please don't slow down," I begged.

"I'm gonna cum soon, we keep going like this," Brad laughed.

"Oooh, you gonna cum in me?" I teased.

"You want me to cum in you?" he asked, picking up his pace.

"Oh fuck, yes! Fill me up with your hot cum! Breed my sissy ass," I half-moaned, half-begged.

I slid my hand down into my panties, didling myself. I was so worked up, I was pretty sure I was going to cum in an instant. Me playing with myself, seemed to fire Brad up even more. He really picked up the pace, absolutely slamming into my ass. My moans were pretty steady and I could feel the orgasm building up in me, it felt strange though, different. I could only guess it was the rubbing on my prostate that was making this build up differently. That or the excitement of him cumming in me. I'm not sure why that idea turned me on so much, but it really did.

Brad began groaning, so I picked up didling myself and in just a few moments, I was arching and starting to spasm on his cock. I began pushing back, trying to get more sensation before I shuddered and screamed, shooting my girl cream in my panties.

My orgasm made my ass tighten up and Brad moaned loudly grabbing tightly onto my hips and pulling me deep on his cock. I could feel him spasm and he thrust several times as his cock pulsed and shot his load into me. It was such a strange sensation, but I loved it. I started humping slowly, milking the last bits of cum and Brad's orgasm as I panted for breath.

"Holy shit," was all Brad could manage to say.

I smiled proudly, teasing, "I think he likes it!"

Brad chuckled, "That was fucking mind-blowing... wow."

"That was amazing," I agreed.

Brad leaned down to trail kisses down my spine, making me shudder. I could feel him starting to shrink and after a few moments he slipped out. "Oohhh," I moaned disappointed.

"Sorry, babe. Gotta come out eventually," Brad said.

"I know, I'd just... gotten used to being filled. I feel... kinda empty," I said.

Brad chuckled, "Well, hang on a second. I can fix that." I could hear him step away. I turned my head to the side, looking back as best as I could since I was still laying on the desk. I was trying to stand up, but my legs felt pretty wobbly and I didn't trust my wobbly legs on the heels. Brad stepped back over a moment later, and started playing with my ass.

"Oooooh, you ready to go again?" I smiled.

Brad held up the butt plug and started teasing my asshole, making me gasp suddenly. Then I moaned as he slid the plug back into me. I shuddered as the plug slid right in all the way to the base with no problems this time. I guess my slutty ass was all stretched out.