Working for Halloween Ch. 02

"Well, I'll be glad to get these heels off," I said heading through the store.

Jamie smiled at me as I went by, "That was pretty crazy. I've never seen the costumes move like that from a sidewalk greeter."

"Yup, I told Tiff if she keeps going like this, corporate is going to have her working every day," Anna stated.

"That would be a good idea, I usually work the downtown location. I know we'd be happy to have you come down there," Jamie smiled at me.

I was kind of giddy. Here I was having girl talk with other girls. This was an odd thrill. "Yeah, that would be great. I'd love to."

"I'll talk with them and see about having it arranged," Jamie smiled at me and went back to the racks of clothes.

Anna led me into the back and as much fun as I was having, my feet were really starting to hurt. I was looking quite forward to getting them off. We went back into the office and I dropped on the couch and took the shoes off, and started rubbing my feet.

"There's a reason I hardly ever wear heels at work," Anna told me. "Partly because I'd be worried I was going to break my neck, but mostly because I know I couldn't wear them for an entire shift."

"Can you just wear them for a little at a time and get used to them?" I asked.

"Probably, but it's never been that important to me," she shrugged. "So, listen I have to go and close up. I'll come back in a little bit if you need help getting undressed or cleaned up or anything."

"Thanks, Anna, for everything," I smiled at her. She gave me a smile and a wink back. She headed out and I sat for a few minutes, stretching my legs and rubbing my feet. The phone rang at some point. I debated if I should answer it, but I guessed they could get it out front.

A few moments later, Anna stuck her in the door. "Oh good, you're still dressed," she said. I looked at her confused. "Would you mind putting the shoes back on for a moment? Brad wants me to send him over some pictures." She held up her cell phone for emphasis.

"Sure, no..." I started in masculine voice, then coughed and tried my femme voice instead. "Sure, not a problem, you know I like to show off."

I slipped the shoes back on, then struck a few poses as Anna snapped a few pics. This was fun, too. Maybe I should look into modeling?

"Great, these look good," Anna stated, more to herself than me.

"Can I see?" I asked shyly.

"Sure," she held the phone for me to see, but didn't hand it to me. So, I had to stand next to her to see them. I was very aware of the warmth of her arm as I brushed against her. I looked over the pictures as she scrolled through them. A few of them did look pretty good. I looked sexy and a few of the shots, I even looked pretty.

"Which ones are you sending?" I asked.

"This one and this one," she said, scrolling through two of the pretty pictures.

"Good," I stated, "would you mind sending them to me, too?"

Anna gave me a sly look and said, "You bet your ass I will. Give me your number."

I gave her my cell number and she sent them over to me, too. "Did Brad say why he wanted them?" I asked.

"Well, he wanted to see how you and the costume looked, since he's probably not going to make it back anytime soon," she told me.

"Oh, that's too bad," I said.

"You sound a little disappointed," Anna grinned. "How come?"

"Oh, no reason, I just wanted to see what Brad thought, I guess," I smiled trying to sound nonchalant. I was very aware of how close she was to me. I also realized that she must have been wearing heels now, because she was taller than me, which she hadn't been earlier.

"You sure? Nothing special?" she asked again. I was pretty sure she was teasing me, but I was a little unsure how to answer. So, Anna answered for me. She leaned in close and whispered in my ear, "I know what's going on, sweetie. I saw you and Brad here last time."

I gasped slightly. Great, not only was I a cock-sucking slut, but apparently it was well known, too. I wasn't sure what was happening now, I felt a little off balance.

"I saw the whole thing," she said, her lips brushing against my ear. "And it was fucking hot."

I looked up at her and I saw it in her eyes, she wasn't kidding, she was fired up. I felt even more off balance now. "I stood right outside that door, hiked up my skirt and diddled myself off. I was worried you two might hear, but you both seemed otherwise... occupied," she whispered.

"So, what..." I started, but she put a finger to my lips.

"Don't talk, I want you to listen," she said sternly. Again, something about her tone, made me want to listen. "The biggest thing, is I was trying to figure out what about it turned me on so much. I mean, I've watched porn before and I enjoyed it, but something about knowing you were a guy dressed as a girl made it that much hotter," she stalked around me. I could hear the click as she stepped, she was definitely wearing heels now. "Then I realized what it was," she paused as she came around front, looking down at me, towering over me. I felt so helpless, so in her control, and I realized my clitty was throbbing in my panties. So, I was enjoying it, too.

"What?" I whispered.

"I wanted it to be me instead of Brad," she smiled a predator's smile. "I wanted it to be my cock you were sucking, I wanted to have a crossdressed girl in my control. Are you a fan of female domination, Tiff?"

I didn't trust my voice, so I just nodded.

"I've become a big fan the past few days, and when Brad said he wasn't going to be able to make it back tonight," she paused again, "I knew what he'd promised to do to you, so I wanted to keep that promise."

I was a little confused, her cock? She was going to deflower me? Was Anna a guy, too? I looked down, trying to sort all this out and I saw the boots she was wearing. They were thigh high leather boots.

"Oh yes, I took your advice and decided to start working my way up through some heels? Do you like these?" she smiled again.

I nodded, and licked my lips.

"I asked you a question," she said sternly.

"Yes, Ma'am," I responded quickly.

"Good girl," she purred. "Since you like them, why don't you get on your knees and take a closer look."

Without thinking, I dropped to my knees and look at the boots. They were very nice black leather boots. They even had the laces up the back. They were extremely sexy. I know she hadn't been wearing these earlier, so she must have just changed.

"Sexy aren't they?" she asked as if reading my mind.

"Yes, Ma'am," I looked up at her, "very sexy."

"Would you like to worship my boots?"

"Yes, Ma'am," I answered breathlessly. My clitty was throbbing in my panties.

"Good girl," she purred again. "Come over here," she stepped over and sat on the couch. I crawled after, kneeling right in front of her. She held one of the boots up and rested her ankle on my shoulder. "Kiss it," she ordered simply.

So, I gently started kissing the soft leather of the boot. She was making some soft noises, so I continued, getting a bit bolder. I flicked out my tongue and began licking them.

"Good girl," she purred again. I stole a look and realized her hand was up her skirt, but her eyes were quite focused on me. So, I went back to my work and began licking up and down the boot, worshipping them as I would a goddess. I was so mesmerized, it took me moment to realize she was making more noise. I felt her tense and heard her gasp as she bucked and rocked on the couch as she came.

As she came back down, her eyes opened and she smiled at me, "That was very good, come here." I crawled up onto the couch and she kissed me. It was a passionate kiss, not the tender make out session like I had with Brad. This was a kiss of someone who wanted me and wanted me to know they wanted me. It turned me on even more, so I kissed her back, letting her know how fired up I was with my kiss. I felt her hands roaming over me, one hand running up my thigh, tracing along my crotch to my panties.

"My goodness, girl. You are soaked," she said surprised. I blushed a little, "You really are a wanton little slut, aren't you?" I nodded sheepishly, but she kept going, "You got off on all those guys looking at you, didn't you?" I nodded again.

"You wanted them, didn't you? You wanted all of them, didn't you?" I shook my head, but it was half-hearted. She knew I did, I could deny it all I wanted.

"Don't lie to me, you little slut, you're a cock-sucking slut and you love it," she then took my hand and pulled it under her skirt. As I reached up, I felt a thick, hardness. But it wasn't a cock, it was a dildo. She must have been wearing a strap-on. "Oh, yeah. You know you want it, don't you?"

I licked my lips and nodded. "Then get on your knees and show me what a little slut you are."

I slipped down to the floor, kneeling up as she slid forward on the couch and presented her "cock" to me. I started slowly, deliberately licking the tip with my tongue looking her in the eyes as I traced my tongue down the length and back up. I sucked the head into my mouth and started getting it nice and wet. It was quite dry, and the plastic had an odd taste, not bad, just different. It was quite different than sucking Brad, but I was so worked up at this point I didn't really care.

"Oh yeah, suck my cock, bitch!" Anna growled a little as she put her hand on the back of my head, practically shoving her cock in my mouth. I kept using lots of spit trying to get the whole thing wet before I started wrapping my lips around the shaft. I saw the red marks where my lipstick was marking my progress down the shaft. "Yeah, take me all in, you know you want it. Show me what a little deep throat slut you are," Anna was clearly in charge and clearly quite turned on.

So, I started on working the whole shaft down my throat, it took me a few tries but I got it all down. I started really going all the way up and down letting the whole shaft slide down into my throat. Anna put both hands on the back of my head and took control, she really started fucking my throat at that point. Then she held me all the way down and I felt her grinding. She must have gotten enough stimulation because she moaned through what seemed like a very long orgasm. It mostly seemed long because I couldn't really breathe. "Sorry," she whispered as she let go and I took several deep breaths, panting with both lust and lack of air, "Didn't mean to suffocate you."

"That's okay, it was hot watching you," I grinned up at her.

She smiled back, "You never asked me what my costume is."

I shrugged, realizing I hadn't, but I didn't think I had before. Then again, I don't really think that's what the game was here. "No I didn't," I replied. "What is it?"

"Uh-uh, it's not that easy. You have to guess," she smiled wickedly, that gleam back in her eyes. "And there will be a penalty if you're wrong."

I wasn't sure what she meant, but I played along, "A witch?"

She just shook her head. I took a longer look. All black, dark make-up, "You're a goth?"

She laughed slightly, "On the right track, but no."

Right track with goth? Hmmm... I looked down to the boots and back up, "A hooker?" Though that didn't seem right.

"No, do I look like a hooker?"

I shrugged, "Not really."

"Let me give you a hint," she stood and grabbed something from alongside the couch. She came back with a small leather paddle in her hand. "What do you think?"

All black, boots, a paddle... oh... "A dominatrix?"

She smiled triumphantly and nodded, "But you guessed wrong three times, so guess what your 'penalty' is." She hefted the paddle to give me an idea.

I gulped nervously, not sure about that.

"Don't worry, I'll be gentle... at first," there was that predatory grin again. "So get your ass up in the air, and put your face on the couch," she ordered.

I obediently stood and put my face down on the cushions of the couch. They were still warm from where she'd been sitting. Anna stepped around behind me and I tensed. She placed her hand softly on my ass, "Relax sweetie, I'm not going to hurt you... much". She then gave me a soft swat with her bare hand.

Well, that wasn't bad... then she gave me a harder swat with her hand. Not anything terrible, but it surprised me. I flinched, and I felt a rush of... something. Endorphins maybe? I don't know, but it was electrifying. She smacked again, the other cheek this time, harder still. This one hurt, not bad, just enough to sting for a moment.

"Now, we start. Here's your three swats, and you better count, or I start over," she warned.

Count? What did she mean start... "Ahhh!"

The paddle cut through the air and smacked in the center of my left cheek. It burned and stung at the same time. I jumped and my body shook for a second. It took me a moment to register, but that hurt! Again, not terrible, lingering pain. But an electric current, someone pinching your nipples just a bit too hard, biting your tongue during a French kiss pain. I kind of liked it, but I also kind of wanted it to stop. I heard the swish this time, and I was ready, but it still shocked me. I jumped, but didn't yelp this time.

"No counting? Really? Maybe you like this more than I realized," she practically purred. Another swish and crack against my skin, the right cheek this time.

"One, Ma'am!" I remember after a moment's hesitation.

"Good girl, but you should be calling me Mistress now. Understand?"

"Yes, Mistress, I... Two, Mistress!" The swat caught me off guard again.

Then she really wound up and gave a full arm swing. The paddle sounded like a shot as it hit my ass. I hissed and jumped, and through my teeth hissed out, "Three, Mistress."

Anna stepped up behind me, I thought she was going to fuck me right then, but she just ground herself against my ass, softly rubbing my red cheeks. She stepped away again for a moment, but stepped right back and pushed against my ass again.

"Now, since you guessed right, you get a present," she purred again. Her voice was really having an effect on me. Then her hands really had an effect on me, as I felt something cold on my ass and her fingers were teasing my hole. I started to groan and push back. After a few moments of fingering me, she then put something up against my hole. She slid a butt plug deep in me until the base was seated against my ass. "Mmmm, do you like your present?"

"Yes, Mistress," I moaned, very turned on.

"Good, now before I fuck your little sissy ass, lay down on the couch," she ordered.

I climbed up on the couch and laid down on my back. She quickly straddled my head and I was covered in darkness as her skirt draped over my head. I felt her very wet pussy touch my mouth. The message was obvious, so I began to tongue her slit. Teasing at first, working slowly around, but she was quite turned on, and didn't need much. It only took a few minutes of my tongue licking around before she was grinding down on my face, bucking and yelling. I wished I could see, but the darkness of her skirt was all I could see. It certainly sounded like quite a scene! I felt her tense, wrap her fingers in my hair and then she came for quite some time, grinding so hard on my face, I was worried she was going to break my nose! After she came down, I licked her gently and softly for a few until she stood and I could see again. She was smiling from ear to ear as she looked down at me. "Ready to be my bitch?"

I bit my lip and nodded. She stood and pulled me towards her. She turned me so I was facing the arm of the couch. I felt her reach back and start teasing the plug. I moaned as she played with it. After a few minutes of teasing me, she pulled the plug out and quickly replaced it with the tip of her strap-on.

She pushed gently, feeding the first few inches into me. Then she pulled back to just the tip and slid forward again. She kept going deeper and deeper like that, until she was pressed against my ass.

"You okay?" she asked me quietly. I nodded, though I felt I was being impaled on something. I guess technically, I was.

"Oh yeah," she purred. Then she quickly pulled all the way out and slid the whole length back in me. I was in shock as the mix of pleasure and pain was quite intense. It felt good, but I was still stretching out, too. After a few strokes, Anna found a nice rhythm and I opened up all the way, enjoying the feel of her sliding in and out of me. I was moaning and panting like a bitch in heat. I was really fired up and started to reach into my panties to play with my clitty.

Anna smacked my hand, "Did I give you permission to touch yourself?"

"No," I replied sheepishly. She smacked my ass hard. "No? No what?"

"No, Mistress. Sorry Mistress," I replied.

"Good girl," she started and picked up her pace. The stimulation was getting to be too much. I was moaning like mad. She then started slamming into my ass, pounding into me like crazy. She was moaning and bucking again, this time every thrust was punctuated by a grunt or groan until she finally slammed in one last time and pulled me back and ground out her climax with a muffled scream.

She was panting as she leaned against the back of the couch. "Oh wow, that was amazing. I hope you enjoyed that half as much as I did."

"I did, Mistress. May I touch myself?"

"No, not yet," she replied playfully. Oh my, I was so close.

"I want a show when you do cum," she replied sounding playful again. A show? Like what?

She pulled out the strap-on with a wet pop. That felt odd. I felt strangely empty. Anna smacked my ass. "Get on the floor, slut."

I climbed down and kneeled looking up at her. She undid the strap on and sat down, resting her boot on my shoulder. Her other boot came up between my legs, rubbing against my bulging panties. I shuddered and moaned as she rubbed her boot against my throbbing clitty. "I liked watching you lick my boots earlier. Worship them again and get them nice and wet."

I started kissing and licking the boots like they were my favorite thing in the world. I was also grinding myself against the boot between my legs. She rubbed her booted foot against me, and started teasing me. "Oh, are we nice and worked up? Are you humping on my leg?"

I nodded, blushing slightly.

"Good," she put her other boot down on the floor and leaned close to me. "So, that's what you're going to do. You're going to hump my boots and you get to cum, but when you cum, you have to lick my boots clean. Understand?"

I looked unsure for a moment, but she rubbed her foot against my clitty and any argument died as I ground on her foot and replied, "Yes, Mistress!"

"Good, get humping," she grinned down, clearly enjoying this.

I got myself in the bit of boot cleavage between the two boots and started fucking the boots, the soft wet leather felt so warm and tight as she pushed her legs together. I was grunting and pumping like I was possessed. I was so worked up, it only took a few moments for me to cum. I pumped out quite a load, leaving strings of white cum all up and down her boots.

I panted to catch my breath and Anna leaned down close to my ear, "Good girl, now get to cleaning." I nodded since that was all the response I could manage and leaned down, stretching my tongue out and licking up my jizz from her boots. At first I was a little hesitant, but once I got going and got into it, I started enjoying it.

I heard Anna panting and looked up to realize she was diddling herself, she was really getting into this! "Did I tell you stop, bitch?"

"No, Mistress," and I went back to licking all the cum off her boots and I heard her climax again. After I finished I looked up at her, she smiled down at me. She motioned for me to climb back up on the couch. I climbed up and she pulled me next to her. I snuggled in, resting my cheek against her shoulder.