shawnavinylltv@gmail.com
Tom willingly submits further to Anna. She gives him the full female treatment!
(*The following story is a work of fiction and a fantasy. Any resemblance to real persons, living or dead, is completely coincidental. Safe sex practices should always be followed)
I sorted through the bag of outfits I had received from Anna, trying to find something appropriate for lunch. Anna had messaged me and said she wanted to get together for lunch... and she wanted me to come en femme.
I wasn't sure how to feel about that. On the one hand I was excited about the idea of going out and doing something fun and non-sexual dressed. On the other hand I was freaking out about trying to pass and worrying about being 'clocked'.
I knew I was getting better with make-up and my overall feminine style, but I also knew I had a lot to learn. Add in trying to use feminine mannerisms to do something as simple as have lunch at a restaurant, and I was more than a little nervous.
I decided on a simple outfit, just a nice blouse and skirt. The blouse was a teal color that seemed like it would go well with my eyes, while the black skirt was just above knee length. Since it was fall and still a bit cool, I figured I should go with some stockings or maybe tights or leggings. All the decisions to make as a girl. I guess this was part of the point Anna wanted to make?
I took a quick shower to make sure my shaving was all caught up. For some reason, the cleansing spray of the water always helped me relax my mind and get into a different head space. I made sure to shave my face after the shower, too. Once I put on some moisturizer and skin cream, I was ready for my make-over.
I started with some light foundation. Thankfully Anna had given me several options, most of which were pretty close to my skin tone. Since this was just lunch, I wanted to keep it simple, so I went with a light eye shadow, just a light tan that put a little color on. I did go with some mascara since I loved that look. Again, I just kept it light.
The same with some blush, just a light pink for some color, nothing too crazy. I wrapped it up with some light pink lip stick. I did indulge and also went with some lip gloss in a nice pink. I figured a little splash was nice to mix things up.
I checked my reflection and the result was nice. I looked like a young lady ready to go to work or to meet some friends. I looked through the selection of wigs I now had and decided on the dark red. It was a medium length and seemed to be the most natural looking color I had. It wasn't quite my usual dark brown, but I didn't have anything in brown. Maybe that would be the next wig selection?
Once I had the wig nicely secured with a few hairpins, I realized I needed some lingerie. Again, I wanted to keep it simple, so I grabbed a nice bra and panty set. They were both basic black, nothing too crazy. I was trying to decide which pair of stockings I wanted to go with when I saw a pack of pantyhose and figured I'd try those. There must be a reason women generally wore those for functional things like work, right?
I got the hose on enjoying the feel being wrapped so fully in the stocking material. Having the control top portion around my groin and ass felt a little odd, but it was nice. As I slid the top over my panties, I made sure I was tucked down well. Didn't want to make any unladylike bulges!
I also realized that if I needed to pee, I'd have to pull the whole thing down That seemed like a bit of a pain in the ass, but that also sounded like a problem for future me. So, I got the black bra on and slid in a pair of falsies. These weren't huge or anything, just enough to look like I had some tits, probably about a B cup, but I wasn't really sure.
I slid on the blouse and checked that the bra wasn't visible. I'm not sure why I cared, but maintaining the illusion somehow seemed important. I slid up the skirt, the material easily gliding over the pantyhose and settling into my natural waist. I felt like something was missing, so I dug in the bag and found a few belts. I didn't really need the belt for this outfit, but when I buckled on the wide black leather belt it was the perfect accent.
I decided to go with a nice pair of wedge heels. I figured sensible footwear for an occasion like this was best. Once I had the heels on, I looked myself over in the mirror. I actually looked pretty good. Not super sexy certainly, but cute and definitely girly. I was a little thrilled that I'd managed such an evertday look since everything else I'd done to this point was so far over the top.
I realized I needed a purse, but thoughtful Anna had tossed in a couple of different bags. There was a shoulder bag, a small clutch and what looked like a messenger bag. I figured the shoulder bag was my best bet this time. I put my wallet, my keys, my phone and some extra make-up in the bag. I think I was ready. Now the reality of going out had me really nervous.
I'm not sure why. I mean, I'd been out in some pretty ridiculous and outrageous outfits. This was very simple. Why was it freaking me out? I guess that was it. Before it was all about being seen and showing off. This was about blending in and just being one of the girls. I hadn't really practiced trying to blend in before.
I called Anna and told her about my little identity crisis. She said if it helped, she's meet me near my apartment and we could walk to lunch together. Amazingly, that idea really helped me settle down. I packed up, took a deep breath and opened the door to step out into the world as Tiffany.
As I hit the street, my heart raced again, but I found that having something to focus on helped me keep from getting to nervous. So, I instead focused on finding Anna. I spotted her just a half a block from my apartment and waved slightly to her. She gave me a knowing smile and a little hug when I got to her.
She stepped back and looked me over, “You look good, very feminine and subtle.”
I smiled and nodded suddenly a little nervous about my voice, “Thank you, I thought it looked pretty good.”
“And you sound good,” she nodded, taking my arm and walking down the block. She leaned close, “We do need to work on your walk, you still walk like a man.”
“How do I fix that?” I asked.
She told me to try and swing my hips more while keeping my balance and to try step directly in front of my other foot. She kept giving me pointers on my stride until we got seated at a cafe.
“That sounds like a lot,” I noted.
“It is, but most genetic girls have been training that way all their lives. You need more of a crash course,” Anna laughed.
I finally took a moment to look over Anna's outfit, and she had gone with a very dark look. I said, “I like your black dress. Going Goth?”
She made a face at me, “No, I'm going Domme.”
That made me heart race and I wasn't sure how to respond to that. Thankfully our server came up and we had to order, which was also another test of my voice.
“So, this is your Domme look?” I asked looking over the clingy black dress with the knee high boots and fishnets. She also had a few bags she had set under the table.
“Oh no, I'm usually in a corset and my make-up is much more 'Rowr'!” she laughed. “But I really did want to tell you that I am training with a Dominatrix.”
“Wait, what? You're really becoming a Domme?” I asked, momentarily thrown off.
Anna nodded, “Yup, after... topping you the other day, I had some realizations about myself. I mean, I've always liked things a little kinky, but having you under me like that was just like... oh yeah! So, I wanted to thank you for helping me have that realization.”
I was a little flummoxed, but also flattered, “That's great! I'm glad you opened up. Oh wait, is this why you're leaving the shop?”
Anna nodded, “It is, so that's very exciting but also a little nerve wracking. I also wanted to ask you something important about that.”
I looked at her a little unsure where this was going, “Like what?”
“I'll need a submissive to train on a few times a week with Mistress Lyral. Will you be my little sissy sub?” Anna smiled a predatory smile that told me she already knew the answer, but asking the question was clearly important to her.
“Of course, Ma'am! I'd be honored!” I smiled back.
Anna smiled, “Thank you, sweetie. I knew I could count on you.”
So, we chatted about what her training was like. Her mentor required her to spend some time training as a submissive before she moved over to being a Domme, but she would also have some lessons on dominating while training, so she'd have a beta submissive to her. That was where I came in, apparently.
“So, you have some exciting changes coming?” I asked her as our food arrived.
“Yes, but you're the one with the changes going on. Speaking of which, when do you meet the “Big Boss”?” Anna asked as we ate our lunch.
I sighed, “In a couple hours. I still think I should cancel.”
“Why?” Anna looked sternly. “Here you are out and about, looking and being femme. You can clearly be a girl. Why not be one?”
“Is that really how I want to start my interview?” I asked.
“Well, you're working as a street greeter for ladies costumes and I think they want you to do more, so if you show en femme, that'll show you're ready,” she noted.
“I don't know, it feels... dishonest,” I shrugged.
“If its who you are, its who you are,” Anna shrugged.
“Yeah, but what happens when they find out?”
“Why do they have to find out?”
“I... I don't know,” I replied. “I guess I just assumed they'd know. I mean, isn't it obvious?”
Anna shook her hear, “If you're looking sure, thankfully most people just see the outfit and hair, and move on. They might look a bit closer, but they're not going to look to clock you, and if you look this good, they're not going to care!”
I shrugged, I could see where she was coming from, but I still didn't feel confident enough to wholeheartedly agree.
“So, now the more important question... what are you going to wear?” Anna asked,
I looked up at her blank for a moment, “For the meeting?”
She nodded and looked at me expectantly, I guess my blank look was all the answer she needed. “Ah, you hadn't even thought about that yet. Yeah, you still have a lot to learn about being a girl.”
“To be fair, I've only been a girl for a few weeks now!” I laughed.
“Okay, well then I better come over and help you get ready,” Anna said.
“Oh you don't have to do that, I'm sure I'll be fine,” I replied.
“I wasn't asking,” she said in a stern tone that indicated there was no argument. For some reason that tone got me a little excited. I guess I really was a submissive at heart.
We wrapped up lunch and headed back to my place. I was a little excited and also a little scared. I wasn't sure where this was going, but I was sure it was going to be interesting. Once in my place, Anna took me by the hand and we sat on the couch.
“So, honey, I'm going to help you dress, but I want to play a little first. Are you okay with that?” Anna asked, gently but sternly.
I nodded, “Yes, Ma'am.”
“Good, is there anything you want to do?” she asked.
“I... I don't know,” I stammered. Blushing I said, “I really like going down on you.”
She practically purred, “Oh yes, well that's an easy one. How about me spanking you?”
I nodded and swallowed a little nervous, “Yes, Ma'am. I, well, I don't know if like is the right term, but I'll do that.”
“Good, girl,” she patted my head. “And you're good with me using the the strap-on again?”
I blushed a little, “Yes, Ma'am, I like that.”
“I seem to recall you REALLY like that,” she teased and I blushed deeper.
We talked through a few more things. Her making sure I was okay with her calling me names and she was allowed to take pictures among other things. I was down for all of it.
“Now, my little sissy girl, are you ready to be my little toy?” she asked.
I nodded, “Yes, Ma'am.”
Anna corrected me, “You will be addressing me as Mistress now.”
“Yes, Mistress,” I nodded.
“Now, get out of those clothes, I want to see what kind of lingerie you wore underneath.”
I began getting undressed, but she stopped me, “Slowly girl, make it a show for me.”
She smiled as she sat down and watched me expectantly. I took a breath to steady my nerves, then I looked at Mistress as I began to shake my ass to a slow song beat in my head. The smile on her face told me I was doing well, so I went to the same mode when I was at the costume shop and started shaking my ass and hips, making it a slow, sensual grind.
“Oh yeah, you sure look like a dirty little sissy slut,” she purred. “Make me think you want it.”
I smiled as I continued to shake. I slowly peeled my blouse off and used it to cover my bra and fake tits. I let the top slide and kicked off one shoe. I then turned and bent completely over, pushing my ass right in front of Anna as I slid my other shoe off.
As sudden smack on my ass made me jump and squeal, more in surprise than pain. Anna giggled, “Oh, I thought that was a target.”
I laughed as I hooked my fingers in the waist of my skirt and slowly twirled around a few times, moving the skirt down more each time. When it went to my knees, it quickly slid down and I kicked it aside.
“Hose, eh?” Anna noted. “Very practical, I hope you're planning on something a little more sexy for your meeting.”
I nodded, “Yes, Mistress. I'm hoping to be... sexy, but not slutty, well, not too slutty.”
“I hope you're going to be slutty now,” she smiled, chuckling evilly. I'm not sure why, but the laugh scared me and thrilled me. “Take off your hose and come here.”
After I took down the hose, I was in just my panties and bra with my falsies. Anna ordered me to climb up next to her and bend over the arm of the sofa.
She began petting and stroking my ass, making me shiver with excitement. When she ran her nails across my skin, I moaned softly.
She whispered in my ear, ”Does my little slut like that?” I nodded and she laughed, smacking my asscheek hard. “Answer me, bitch!”
“Y-y-yes, Mistress! I love it,” I stammered.
“I can tell by the wet spot your tuck is making,” she made that evil laugh and continued running her nails all over me until I was just a bundle of nerves.
The next ass smack caught me by surprise and I yelped in pain, “You think that's a lot. Wait until I really get going.”
I shivered in fear and anticipation, shaking my ass as a target for her. She delivered a few deft swats, making me moan in pain and arousal. She was soon delivering a series of wicked blows to my ass, and then rubbing her hands on my ass after mixing the pleasure and pain so that my head was swimming.
“Do you have a hairbrush?” she asked, close by my ear.
I nodded and she smacked my ass hard, “Is that how you answer your Mistress?”
I shook my head, “Sorry, Mistress. Yes, I have a hairbrush.”
“Go get it, now!” she barked and I jumped off the couch to obey. I ran into my bedroom and grabbed the large, flat hairbrush I would use to brush out my wigs. I grabbed it and scurried back in the main room.
I knelt before her and held the brush up with both hands, “Here, Mistress.”
She smiled and simply said, “Good girl.”
She took the offered tool and smiled down at me, “Now get your cute ass back over the arm of the couch. I'm going blister those lovely cheeks of yours.”
I draped myself over the arm of the sofa, my ass up as a tempting target. Anna rubbed her hands over my cheeks, snapping the waistband of my panties. She took a few swats to get the feel for the brush.
“Oh, this is nice. You'll now be counting each stroke and thanking me for each one. And if you don't seem sincere, we start over. Understand, sissy?”
“Yes, Mistress,” I said nervously, my clit dripping steadily into my panties.
She stood slightly to the side, her hand on the small of my back, holding me down as she brought her hand back the hairbrush cracked on my asscheek sounding like a gunshot in the quiet apartment.
My cheek flashed with the sting and I gasped with the pain. I then remembered and said, “One, thank you, Mistress.”
She chuckled, “Almost forgot, didn't you, sweetie?”
“Yes, Mis...” She smacked my other cheek hard with the brush, causing me to gasp mid-sentence and then stammer, “Two, thank you, Mistress.”
“Good girl, keep going and I may let you worship me,” she put her crotch right next to my face and ground herself against me. I could smell her arousal already, so I knew she had to be quite wet. As she let me sniff her, she proceeded to blister my cheeks over and over, making me count each one.
The stinging on my ass making my tucked away clit throb in my panties. The smell of her arousal and the feel of her hands on my back making me crazy with lust.
She made me count over and over until we got to thirty. My ass was red and I knew it was going to be sore, but the pain was also matched with a powerful thrill of taking my punishment and pleasing my Mistress.
Anna rubbed my sore ass, dragging her nails painfully over my welts and red spots. The pain sending a surge through me, making my tuck throb painfully as Anna teased me.
“Oh my, you were a very good girl for that. Are you ready to show appreciation to your, Mistress?” Anna asked.
“Yes, Mistress,” I said eagerly.
“Get on the floor, slut,” she replied sternly.
I knelt at her feet. She presented her booted foot to me and said simply, “Worship.”
I began kissing and licking all over her booted foot, she murmured words of encouragement, “Yes, good girl, worship your Mistress' boots. Lick and clean those sexy boots. Polish them nicely for me.”
I kept licking the shiny leather of the boots, my clit throbbing where it was trapped in my panties. She obviously noticed and lightly tapped my panty bulge with the toe of her boots, “Is my little slut enjoying worshiping her Mistress?”
I moaned as she lightly kicked my throbbing members several times before I could gasp out, “Yes, Mistress.”
“Then get back to licking and maybe I'll give you a reward,” she continued lightly tapping her boot on my clit and moving down to tap my balls.
As I licked to the tops of the boots, she placed a sharp nail under my chin, “I want to bust your balls, will you try that for me?”
I nodded, “Of course, Mistress. Please bust my sissy balls.'
She smiled, but not in a nice way, “Good girl. Spread your knees as wide as you can.”
In my kneeling position, that wasn't very far, but it was hopefully wide enough to be a good target. I looked up to see Anna smiling that predatory smile, “Your panties are wet, you little slut.”
I looked down and I was surprised to see a very large wet spot near the tip of my throbbing clit. I was a little embarrassed at how much I was getting off on her debasing me and I could feel my cheeks flush with my embarrassment.
Anna ran her nails over my neck and chin, “Blushing? That's adorable. You really are a cute little slut. Now I want you to beg for it, I like hearing you beg.”
I looked up, my cheeks flushing deeper crimson, “Please bust my sissy balls, Mistress. Please punish me for your amusement.”
“Good girl,” she smiled as she swung her foot forward, kicking me hard right in my panty bulge.
I gasped with the shock of the sudden pain. I started to fall forward, but Anna pulled me close, my face basically buried in her crotch. As I gasped for air, all I could smell was pussy and I knew she had to be soaked. I could feel the wetness of her panties on my face and through the fading pain all I wanted was to taste her.
“Smell me, pet? I am really enjoying you today, you're being such a good girl. I hope I can get you in the dungeon soon and really lay my claws into you. She ran her nails over me as she held me in her crotch. “But first, I want to bust your balls some more, that was fun. Can you take more?”
I nodded enthusiastically, “Oh yes, Mistress. Please bust my balls. I love knowing that I'm making you wet.”
“Oh, you like smelling my wet pussy? I bet you really want to taste me, don't you sissy girl?”
I nodded, biting my lip as my clit throbbed remembering how she tasted last time, “Yes, Mistress! Please may I taste you?”
“Oh, you've been so good. A little taste,” she reached down into her panties and ran her finger over her womanhood, moaning softly as she did. She then pulled her finger out and rubbed it across my upper lip so her aroma filled my nostrils.
“Lick my finger clean,” she ordered.
I obediently put out my tongue licking her juices off her finger relishing the taste. “Ready for more, sissy?”
I nodded and added, “Please, Mistress?”
She brought her boot back and swung it forward connecting hard. I doubled over, grunting with the pain and trying to breathe through the overwhelming pain. Again, I felt my face being pressed into her crotch, I could distantly hear her order, “Lay down on your back, now!”
I dutifully laid on the floor, looking up she knelt down over my face, her ass just inches away, “Kiss and worship my ass, and then I'm going to smother you.”
I kissed her ass cheeks, working my lips and tongue over her ass, teasing over her thong as I did. She reached back, pulling her thong to the side, “Get your tongue in me.”
I licked up to her crack, teasing my tongue up and down her ass a few times before she pushed back, covering my face with her ass. My world became her ass as I could only breathe her in and began to tongue her asshole. I could feel her moan as my tongue entered her.
She was grinding back on my face, lifting up just enough every few moments for me to take a quick breath. Then I could feel her finger and realized she was diddling herself while grinding her ass on my face. She leaned back putting her full weight on me as she thrashed through an orgasm.
She stayed like that for a moment, catching her breath. “Very good, sissy girl. How's your air back there?”
I mmmpphhed into her cheeks since I could just barely breath in this position. Of course, all I could smell was her like this, so I was enjoying her scent, but it was tough to get much air. She obviously knew that, leaning forward and back to give me a little more or less air as she covered my nose. Through this, I kept licking up and down her crack.
She lifted up and I took a deep breath, panting to catch up on my air.
“Enjoying worshiping your Mistress, sissy girl?” she smiled down.
I smiled back, “Oh, yes, Mistress! Loving it.”
“Good,” she said and planted her pussy on my face. I happily explored her womanhood with my tongue again, thrilling at being her living sex toy. After a few more minutes, I could hear her saying something about finishing up, but I couldn't hear much of it with her thighs squeezing my head.
She lifted back up and at first I tried to keep my lips and tongue tight on her, but being pinned down I could only look up.
I saw her smiling down at me and she reached down to gently caress my cheek, “Such a good little cunt-licker, but you know there's only way this session going to end, right?”
“I'm not sure, Mistress,” I said, a little confused.
“Let me show you,” she climbed off and went to her bag. I watched as she pulled out a familiar strap-on harness.
“Oh,” I said, biting my lips with excitement.
“I want to see marks on my cock, so refresh your lipstick while I get ready,” she ordered.
I went over and quickly put lipstick back on. Once I was done, I turned and Anna had the harness with a bigger cock installed than my first time. It probably about 9 maybe 10 inches long, but it was quite thick. She pointed directly in front of her and I obediently kneeled before her.
“Worship my cock, slut,” she growled.
I dove onto her faux dick, licking and kissing all over the shaft, down to the balls and up to the tip. I wrapped my tongue around the tip, flicking it with my tongue as I looked up at her. She panted with arousal and bit her lip, smiling down at me, but it wasn't a nice smile.
As I started sucking the tip, getting the shaft wetter with each downstroke, leaving a lipstick mark further and further. Pushing the dildo deeper into my throat, gagging slightly. I bobbed to that point several times until on one downstroke Anna grabbed the back of my head and shoved. Her cock buried in my throat and I flailed in surprise.
“Oh yeah, take it all, bitch,” she growled as she held me down. “Keep your hands behind your back, sissy.”
I diligently put my hands behind my back and she proceeded to absolutely skull fuck me. Pistoning the large strap-on into my throat over and over, my eyes watering, my mascara running down my cheeks and my drool running down my chin to drip onto my cleavage. I really wanted to reach down and play with my tucked clit, but I was pretty sure I'd get in trouble for that. Thankfully Anna was done using my mouth.
“Bend over the arm of the arm of the couch, I want to pound your sissy ass,” she ordered.
I hurried to obey, laying my chest over the arm of the couch, my ass lewdly up in the air. Anna stepped up behind me and I felt the cold of the lube as she fingered my ass, I moaned as she worked one finger, then two and finally three into my hole.
“Oh yeah, so nicely open. What do you want, slut?” she asked, smacking my already red ass.
“Please, Mistress? Please fuck me, please take your little sissy slut,” I begged.
She smacked my ass again, “Oh you can beg better than that, you hardly sound desperate.”
So, I babbled, pleading and begging for her to fuck me and use me, to ruin my asshole. All of that, must have worked as she lined up the head of her cock and pushed. I stretched a little at first, the delightful stretch as I opened for her impressive girth.
Suddenly, my ass opened and a large section of her dick slid deep into me. I groaned with the sudden fullness, pushing back to try and get it all. I felt a smack on my ass as she pulled back almost the whole way out and then pushed again, nearly the whole length sliding into me.
She pulled back and forth a few times until one push and she bottomed out in me and started grinding on the harness, “Oh yeah, balls deep in your sissy hole. You ready to be my little fuck puppet?”
“Yes, Mistress! Take me, please rail me,” I begged.
And she obliged! She started pounding my ass, the loud smacking of flesh on flesh only drowned out by my desperate moans and pleading. Anna found a nice rhythm and was steady sawing in and out of my ass. In my bent-over position, I was helpless to do much but hang there and take it. I started to try and reach back to play with myself, but hand was literally smacked.
“Not yet, sissy girl. When I tell you. Instead, focus on the sensations in your ass,” she barked.
I concentrated on the waves of pleasure rolling out of my ass and I realized something was building, it was small at first, but it grew like a flame consuming my whole body, until I was panting desperately, just needing a little bit to over the top.
“Please may I play with myself, Mistress?” I pleaded.
“No, focus on your ass. Feel that pleasure button back there,” she said.
She then started smacking my ass while pounding me and that was all I needed. Five or six really hard smacks and I was begging, “Please Mistress, may I cum?”
“Yes, slut, but no touching your clitty,” she replied.
“Yes, Mistress! Ohhhh!” I moaned as I hit my crest and began to thrash, clawing at the sofa cushions as the bizarre wave ran over me and my orgasm hit like an explosion. I bucked and thrashed and panted as Mistress hammered away with short, fast strokes that seemed to draw my climax out. My legs shaking uncontrollably as I panted for air.
When I finally came down, I collapsed as best I could in my awkward position. Anna panting breathlessly as she leaned down on me. I could feel her large tits on my back as my ass milked her dildo.
“Mmmmm, good girl,” she purred as she pushed herself back up. “I'm going to pull out.”
With a wet pop she came out and I slid to the side, collapsing into a sex puddle on the floor. Anna pulled me up onto the couch. She wrapped her arms around me and cuddled softly with me. Petting my hair and rubbing my shoulder. My breathing finally under control, I nuzzled her shoulder.
“Wow!” I said, “That was intense.”
She chuckled, “You should try coming to the dungeon sometime, then we can really cut loose and not worry about pissing off your neighbors.”
“Sounds great to me! When should I come by?” I asked, partially joking, but also serious.
“How about Saturday afternoon?” she asked back.
“Really?” I asked. “Are you serious?”
She nodded, “I told you, I need someone to practice on. I figured it would be ideal with someone that I already have a connection with. And more importantly, I was ordered by my Mistress.”
I laughed, “Well, then I should be sure to help you. I wouldn't want you to get your ass blistered.”
“Oh that will happen anyway,” she chuckled. Biting her lip thoughtfully.
I was about to ask what she meant when she hugged me close, “You ready to find your outfit for the interview?”
I shrugged, “I guess, I mean. I'm still not sure about this.”
“Well, let's see what we find, and then we'll see what you think,” she said as we both stretched.
So, Anna went to the bag of clothes, “You haven't hung this stuff up yet?” The look she gave me indicated I was going to be in trouble for that. “We'll address your... behavior modification later.”
I shivered in a mix of fear and excitement.
She pulled out a few gray items and asked, “Do you have a steamer or an iron?”
I got out my steamer. She hung the items and started steaming the wrinkles out of them, “Pull the rest of the stuff out of the bag and start hanging it up, now.”
I scurried to obey, pulling out everything and hanging things up, folding a few items and putting them away.
While concentrating on what she was doing, Anna said, “There will be a black lace merry widow and pantie. Grab those and put them on. There should also a pair of black, sheer stocking. Put those on as well.”
How did she know... oh yeah, she got the stuff together for me. It did make wonder, not all of this is costume stuff, where the hell did she get it?
I found the set she was talking about and damn! This was a sexy set. Almost like a teddy, but open at the bottom. I guess kind of like a corset, but with no boning. The merry widow still had the same look. It also had garters attached that would just happen to go well with the stocking.
I stripped off my lunch outfit, including my very sticky panties. I was really going to have to clean those later. I then hooked the lacy garment on and it felt even better than it looked. The soft lace felt absolutely delightful on my skin. It was a similar material to the stockings, which was one of my favorite sensations when dressing up. So, I followed the sexy lingerie with the stockings and I was in heaven rolling the sheer stockings up my legs. If I hadn't just cum, I would probably have started getting excited. As it was, I slid the delicate panties up and shivered with the sensation of tucking myself into them.
I looked up at Anna, my breathing already getting a little ragged from excitement.
She smiled at me, “Down girl! You do look good though.”
I walked to the mirror to admire myself and damn she was right. I looked like an absolute vixen in this.
“Wow!” was all I could say.
“Now, go wash off your make-up, and try doing a subtle, but sexy style,” she said right by my ear. I had be so engrossed watching myself, I didn't even hear her come up.
I nodded, “Yes, Ma'am.”
I went into the bathroom and looked in the mirror. I really looked like a well-used slut, with my lipstick smeared and my mascara streaked down my cheeks. I used my face scrub to clean up and get fresh faced. Then I looked over my make-up options and considered what would look subtle, but sexy. I figured I'd go with a dark and dramatic look.
I needed a solid base, so I guessed I was going to have to go with the liquid foundation. I got the color I'd found I liked that seemed to match my skin tone well. I took a few minutes getting the creamy paste on and then blending until I was nice and even.
Then I got the black eye-shadow. I did the inner portion of my eyelid in the black, then used a very light gray, just off-white, on the outer portion of my eyelid and blended the two to make a very dramatic contrast with the shading. It took a bit of blending to get the shading right, but it turned out nice.
I then pulled out the fake eyelashes. I'd only been practicing with them a bit, but I figured if there was a time to try them, now was it. I got them glued on with a minimal amount of fuss. I was amazed at how dramatic the effect was. Mascara could look good, but these were like having weights on my eyelids. It did take some getting used to feeling the extra tug every time I blinked.
Next, I did the eye liner. I was getting better with the liner and I could finally get a nice wing effect, too. That definitely added to the whole mystique. I did a little bit of rouge on the cheeks just for a spot of color. After blending that in, I had lightly rosy cheeks.
Next, the capstone, the lipstick. I considered doing black or something equally dramatic. However, there was really only one option here. I picked out the bright fire-engine red and took to filing in my lips, fully to the edges. I pursued my lips and blotted the excess off. Looking up with the make-up and the lingerie, I was absolutely a sexpot like this, and damn was I feeling sexy and powerful.
Anna came up behind me with a long, jet black wig in her hands. She settled it on my head and handed me some bobby pins to secure it while she brushed it out. When I looked up, the pin-up vamp looking back at me was still a shock.
I took a few moments to drink myself in, before Anna said, “You ready?”
I nodded, but not really sure what I was ready for. Anna pushed on my back, until I was bent over. She pulled my panties aside and began sliding a lubed up finger into my ass. I groaned as she quickly moved to sliding three fingers into me.
A moment later she pulled out and replaced her fingers with the butt plug. Did she really expect me to go to a job interview with a butt plug in? I was going to be so horny, I'd jump the first guy I saw. Maybe that was her plan?
“Let's do your nails,” she said and sat me on my bed and pulled out a fire-engine red to match my lipstick. I was amazed how quickly she had a quick layer on my fingernails, the smell was pretty bad, but the look was so worth it. We chatted for a few minutes while they dried. She talked me through some of the ways to do the nails, about different coats and top coats and such. I was amazed again that ladies went through all of this all the time.
Once my nails were dry, Anna led me over to where the power suit was hanging. First, she had me slip in my falsies. They weren't much but at least gave me the illusion of some tits. I then put on a low-cut black top. It was basically a stylish bustier really. The nice thing was the push gave me even more illusion of some cleavage.
Then she handed me the dark gray pencil skirt. Wow, paired with the stockings, this was a really sexy, sleek and powerful look. She handed me the matching jacket. I squared it up and looked back at the mirror.
The sexy, and slightly slutty, business woman looking back at me was a bit of a shock, but damn, it really was an amazing look.
“You're not done,” Anna said holding up a pair of patent leather pumps.
“Oh wow,” I muttered amazed at the sexy heels. However, I was a little worried, “Those are really high heels.”
“Yup, they are. And you will wear them and you're going to keep practicing. Otherwise you're not going to be able to manage the 6” heels on the boots that Brad left for you at the store.”
I'd almost forgotten he was going to get me a pair of thigh high boots.
“You wear these, and I'll bring the boots over tomorrow,” she said leaning into my ear. “If you're a really good girl, I'll lock them on and take you out in them.”
Okay, that made me squirt a little with excitement, “Yes, Mistress. As you wish.”
“Good girl,” she purred as I bent down to slip the heels on.
Thankfully, I had been practicing walking in heels, but these things still felt like stilts. Anna went over some of the pointers about even distributing your weight, squarely planting the heel, then shifting your weight to the toe, keeping steps shorter and trying to keep weight centered over the heels and such.
After walking back and forth a few times, I had my stride down. Was I really ready to do this? Anna snapped a few quick pictures and texted them to me. She also showed me her favorite. Yeah, I looked like a vamp all right. I guess I was ready for this.
I made my way to the headquarters office. I started to get nervous until I caught a glimpse of my reflection in the lobby and remembered how I looked. Then I noticed all the guys that were checking me out. Hell, some of the girls were checking me out.
Then I decided to amp it up. It was like I was working the street. I mean, outside the costume shop. I got into the character and began really shaking my ass as I walked. Making a show of it. Getting on to the elevator, I did a little spin and the guy who was staring at my ass as I walked, looked up and I gave him a smile.
He smiled back as the doors closed. Damn, that was fun.
I strode into the office of Costumes and More like I owned the place. I strode up to the woman at the desk, “Hello, I'm Tiffany, I have a meeting with Mr. Darien Davis.”
She smiled up politely, then her mouth sort of opened and closed a few times, “Uhm, yes... he's... he's expecting you. Please go in.” She gestured to the door behind her desk with a sign reading 'Darien Davis, C.E.O.'
Wait, C.E.O.? Did this guy own the company? Why did I just think he was like a manager or something? I guess I should have paid more attention when Brad was talking about this stuff. Oh well, I was here now, nothing to do but vamp it up and see where things went.
I knocked and the voice from the other night called, “Come in, please.”
I took a deep breath to steady my nerves. I could hear the administrative lady on the phone behind me quietly saying, “No, she's here now. She's like sex on heels. You should see her.”
I smiled and felt good about that. I opened the door and strode confidently in.
Darien was standing in front of his desk as I entered. He started walking over quickly at first, but then slowed down, drinking every inch of me. Damn that was a fun reaction. So, I slowed, making it more of a sensual walk, even tossing my hair over my shoulder.
I could see by the look on his face, that he was transfixed. I guess I would have probably had the same reaction. I wondered if he was as turned on as I was, my ass reflexively clenching on my plug. He was too damn good looking and I was way too horny. If I wasn't careful, I was going to be thrown over his desk and getting royally fucked! Well, hopefully any way.
I've noted before, he was ruggedly good looking. He had gorgeous green eyes. He was just slightly taller than me, at least in the monster heels Anna had me in. Flat footed he probably wound have been a half a head taller than me.
He smiled and recovered, then walked over to extend his hand. We shook and I looked into his eyes. I could see the hunger there. I mean, I was dressed like a sexy she-demon, I should have expected that reaction. He gestured to a pair of chairs and I sat down, smoothing out my skirt and crossing my legs.
He sat and started, “Well, thank you for coming. I will say, everyone's been really excited at the response you've been getting. At the store, I mean.”
I smiled, winking, “Well, thank you, its been a lot of fun.”
“Well, we're hoping to get you to work as a greeter at more stores. We only have a few other girls right now. Which is why we usually have two days of guys and only day for the ladies,” he explained.
I nodded, “Yeah, Brad had mentioned something about that.”
“Good, we also do some promotional shoots for costumes, including a calendar that I think you'd fabulous for. Honestly, I was going to ask you to come to a shoot and try out, but I think this look shows you can manage a range of styles,” he said.
“This old thing?” I smiled. “I do have to say, Anna helped me a lot with this look.”
“Yeah, Anna's pretty great. I think I mentioned the other day, we're going to miss her, but she's graciously offered to stay on until Brad can come back,” he said.
“Oh, is he going to be a while? I thought he just had to go home for a few days?” I asked.
“No,” he said. “Apparently, he's going to be a few more days at least, maybe another week or two.”
Well, I hoped everything was okay, but I honestly was a little disappointed we weren't going to have any more trysts after the shifts. Well, Anna was still going to be there. Of course, there were the other stores. Maybe those managers would... damn I was too horny and I really needed to stop doing that.
“Gotcha, that's too bad, hopefully everything is okay,” I said.
“So, would you be interested in working the other stores and the photo shoots?” he asked.
I paused, was I really ready for this. Well, I did wear this sexy, power suit today. I guess I was ready for anything, “Sure, what the hell.”
“Are you sure?” he asked gently. “You seem a little hesitant. You don't have to, I just think you'd be a great fit.”
I think it was time to come clean. “Can I be completely honest with you?”
“Sure, what's wrong?”
“Well, there's nothing wrong, its just that... well, I'm a crossdresser, so I don't want there to be any backlash if you include me in other things,' I explained.
“Oh, I see,” he said, as though I just explained something that was confusing him. “Well, you look amazing and extremely feminine, so I have no problems with it. I can't say all of the stores will go with it. Actually, maybe we could get more female greeters if we started using trans girls?” He wondered aloud.
“I think its a great idea! I really get into the character. Being vampy and sexy can be a lot of fun,” I stated.
“I see that,” he smiled. I blushed a little, but I also batted my eyelashes.
“Well, that does change things a little, but let me talk with the others and see what they say. As I said, I think it will be fine, but I appreciate you being honest about this,” he smiled.
We chatted for a few more minutes about some of my experiences and things he was hoping to do with the company. As we wrapped up we stood and he walked me over to the door.
As he made a corny joke, I laid my hand on his arm as I laughed. Was I really flirting with him? More importantly, was he flirting with me?
As we got to the office door, he turned and looked at me,” Listen, do you want to have dinner sometime?”
“I... what?” I wittily replied. Was he asking me out?
“Would you want to have dinner or coffee or something?” he asked.
“Even after I told you... about me?” I asked.
He nodded, “Yup, I'm bi, and I usually go more for guys, but there's just been something about you from the first time I saw you. So, I'd love the chance to get to know you better.”
Oh wow! Okay, I thought I might get bent over his desk, I hadn't really expected a date!
I nodded and smiled, “Yes, I'd love that.”
“Great! Are you free Friday night?”
I nodded, a big grin plastering on my face. “Absolutely! I can't wait!” I leaned in and gave him a quick kiss on the cheek.
He looked at me and smiled, then pulled me in close and kissed me tenderly. Oh my, this was something else. I'd been kissed, but with his arms wrapped around me, I about melted into his embrace. This was a deep, soul sucking kiss.
We came up for air and I looked into his eyes, I could see the hunger there again, only it was ramped up even more now.
I grinned, “Did you want to get an early start on getting to know each other?”
He raised his eyebrows, “Are you serious?”
I reached down and rubbed the throbbing hard, and what felt rather large, cock poking through his pants, and licked my lips, “This is because of me, right?”
He nodded, his breathing coming raggedly, “Well, kind of yeah. You do look amazing.”
“And kind of slutty?”
“I'd say sexy,” he smiled back.
“Yeah, but slutty is much more accurate,” I rubbed even harder. “If I just left you all hard and pent-up, I'd feel bad. I'd rather make you feel good. Besides, its my fault, I should take care of it.”
He seemed like he wanted to argue, but what guy was going to say no to sex? I slid to my knees and undid his pants, pulling out his already rock hard dick. Rubbing it and licking around the tip. I looked up as I flicked my tongue over the tip. The look on his face was a mix of disbelief and excitement, like he couldn't believe this was happening, but was thrilled it was.
I licked up and down his shaft as I massaged his balls, then I switched and stroked his shaft as I licked his balls. The moans he was making were all the encouragement I needed. I licked up and began sucking him into my mouth slowly. Getting him wetter with my tongue and mouth as I bobbed up and down, taking him deeper with each stroke. He was a good size, probably 9 inches long and pretty thick around. Just slightly smaller than the dildo Anna used earlier.
So, as I got him deeper and deeper, it was getting to be more of a challenge to take the whole thing. First, I got a nice steady pace going taking him as deep as I could, slurping and sucking away. Once I had a nice pace, I worked trying to get him into my throat to take him all the way.
I gagged the first time, and came up for air. He started to ask if I was okay, but I attacked his dick like I was hungry for it, which I was.
His question was cut off as I took him deep again, several times, eventually getting him into my throat and taking him most of the way. A few more deep strokes and I was able to get him all the way down. Holding him there and milking him with my throat.
“Oh wow, you keep this up, I'm going to cum,” he said breathlessly.
I came up for air, “Isn't that the goal?”
“If that's what you want,” he smiled.
“Unless you wanted to cum somewhere else?” I looked over to his desk.
He raised his eyebrow questioningly. I just nodded and he pulled me to my feet. We kissed as we made the way over to his desk, my jacket, skirt and top coming off in the process, so I was just in my gorgeous lingerie.
“Damn!” was all he could say, “You are sexy as hell.”
I bent over the desk, shaking my ass in the air, “Please take out my toy and fuck me.”
“Toy?” he asked. “My, no wonder you're all worked up.”
He reached down and toyed with the plug, making me moan and groan until it came out with a pop. He lined up his cock with my hole and began to push. With how lubed up and open I was, he pretty much slid all the way in. I gasped with the fullness and gripped on the side of his desk, trying to not scream with delight.
“You okay?” he asked softly.
I nodded, “Oh hell yes, just please fuck me, I'm so worked up. I just don't want to scream.”
He chuckled, “We need a ballgag for you. I guess I could gag you with the plug.”
I quickly turned my head and opened my mouth. He looked unsure, but I opened wider and circled my tongue. He pushed the large plug into my mouth. He then pulled back until just the tip in and then slowly pushed in, letting me feel every inch. I groaned around the plug, tasting the lube.
He pushed in and said in my ear, “If you're that kind of girl, then you better keep that plug in your mouth, or you're going to get punished.”
“Promise?” I asked around the plug.
“Try me,” he grinned down.
I pulled the plug out of my mouth very clearly, and just and just said, “Please?”
I put the plug back in my mouth. He reached back spanking me as he started fucking me, slowly at first, then picking up speed. He plowed me for several minutes before he leaned down and panted in my ear, “Oh yeah, I'm going to cum. Are you going to?”
I nodded and mumbled, “I'm close.”
He reached down, wrapping his hand around my clit and stroking it. He found a nice pace where he was stroking in time to fucking me and after a moment, it kind of felt like I was fucking myself. It was a bit of a head trip and really pushed me up so that I was panting and groaning.
“I'm gonna cum,” I moaned. “Are you going to cum?”
“Oh hell, yes,” he hissed.
“Oh yeah, fill me up with your cum, make me your bitch,” I begged as I bit my lip, trying to hold back my orgasm, hoping he'd cum soon.
I guess my dirty talk had the right effect, since he grunted and began driving hard into my ass. Between that and stroking me, I couldn't hold back and began groaning as I pumped his hand. As he drove into me and gripped my hips, cumming deep in my ass. I shot my load into another pair of panties.
I was going to need to start buying panties in bulk if I kept creaming them like this!
We both lay there panting, and Darien began gently kissing the back of my neck and shoulder. That was really nice. I shuddered as the echoes of my orgasm faded.
“I'm going to pull out,” he said.
“Put my plug back in, so I don't drip all over,” I said.
He gently slid the plug in, with how open I was and his cum as lube, it slid right in. He pulled me over to a small couch and we collapsed, me resting my head on his shoulder.
“Damn,” was all he could say.
“Mmm-hmm,” I replied. “I get pretty worked up from being dressed.”
“Clearly!” he teased.
“Imagine how I'm going to be for a date,” I smiled up. “I did say I was looking forward to being had.”
He nodded, “Well, I'm looking forward to having you a whole lot more.”
“Sounds good to me!” I looked up and he kissed me again, that deep soul sucking kiss once more. I could get used to that.
“Sadly, I do have to get back to work,” he said.
“I know, but a girl can dream. I'm really looking forward to Friday now,” we kissed and he walked me to the door.
I walked out, feeling like a million dollars. Excited about where things were going and all my chances to get dressed and enjoy some more extra-curricular activities. My soaked panties and dripping ass a testament to how much fun I was going to have.
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Reach the Author at:
shawnavinylltv@gmail.com
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