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 the 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 a 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 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, it's 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, or something like that!
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 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, probably more like 5”! 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 to look so good.
"Though in the meantime..." 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 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-boppers 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.
"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 a 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 to 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.
"You know you can't fall asleep, we still have to get cleaned up," she warned.
"I know," I muttered. "Maybe I'll just go home like this."
"Are you kidding?"
"Not really, I've always wanted to go out in other situations, maybe not in a costume..."
"You do realize your make-up looks like you were used and abused, right?"
"Well, it should, I certainly was!" I smiled.
"And I loved it. I hoped you enjoyed it, too." Anna raised her eyebrows at me expectantly.
"Oh hell, yes," I replied enthusiastically.
"Good," she smiled. "So you'd do it again sometime?"
"You mean, 'Absolutely, Mistress', right?" she teased. We both laughed. Then she got serious, "We really should get cleaned up, I still have to lock-up."
"Yeah, I should get changed, too. As much as I'd love to wear this home, I'm not sure a costume is a good outfit for an outing. Not yet anyway."
"Well, if you come back again, I'll try to have some more street worthy clothes for you," Anna offered.
"Really? You'd do that?"
"Sure, I'd love to see how you look, not all glammed up," she looked at me thoughtfully.
"Well, I can assure you, I'll be back again as soon as they want me," I said getting out of my costume. As I folded the costume up, a thought hit me. "Anna, any idea what the next costume will be?"
She smiled, "I think it's the Sexy Little-Bo Peep."
"Really?" I said taken aback.
"No, it's not, but we do actually have some of those," she grinned.
"Everybody's got their something," she shrugged.
"So, what's the costume?" I prodded.
"Oh no, that would be telling," she laughed. "But I'm pretty sure you're going to like it!"