tagTranssexuals & CrossdressersCaitlin and Mistress Vicky

Caitlin and Mistress Vicky

byJemina004©

*Clack* *Clack* *Clack*

The sound of my heels on the kitchen tile was distracting me right when I needed to focus. My wife, or Mistress Vicky as I'm to call her from now on, had left me quite a bit of chores to do today. I had just finished dusting and was getting ready to polish the kitchen floor when the doorbell rang.

*ring ring*

Swallowing nervously, I went to the door and looked out the peephole. Just as I thought; it was another package delivery. You might think this isn't anything to be concerned about, but you're missing two very important facts. The first is that I'm currently dressed as a maid, with black stockings, high heels and a maid's cap, not to mention the matching bra and panties underneath. Both pieces of lingerie covered something; Realistic C-cup breastforms and my own captive clitty. The second fact is that the delivery person is a man. Now I have no interest in men sexually, but it's still extremely embarrassing to be seen by one when I'm dressed like this!

After breathing deeply a few times, I opened the door. Remembering how my wife had trained me to answer, I curtsied deeply.

"Hello Sir, how may I help you?" I lisped in a practised tone.

I could see the surprise on his face slowly change into an intrigued look. From looking at myself in the mirror, I knew it was far from obvious that I wasn't a girl. My long blonde hair was (courtesy of the 100 brush strokes a night and expensive french conditioner my wife had ordered for me) quite silky and shiny. My make-up was well applied and my full bust seemed to cry out "female". Still, I was a little taller than you'd expect a woman to be.

"Got a package for you, need you to sign here." he said, clearly not sure what gender I was.

I took the electronic pad and signed my name as Clayton Adams. Seeing that on the screen reminded me how my wife had imperiously declared that I would be taking her name, not the other way around. Just like similar edicts from her, a combination of gratitude that such a beautiful woman had even noticed me and a little bit of spinelessness had caused me to nod agreeably.

At this point you may have the inaccurate idea that my wife is some kind of harpy, and that's certainly how most of her employees see her. But there are many different ways to show love. Keeping me feminized and in chastity is just her way of showing it!

Let me back up a little. We met at the office five years ago. Her father was the owner of a investment firm and she was poised to take over from him. I had interviewed for the position of her assistant or as she kept referring to it, as her secretary. I was tongue-tied and nervous and the whole thing had been a disaster. Or so I thought. To my surprise she called me the next day and told me what my hours would be.

I spent the next three months fetching her coffee and taking her messages. The entire time I was nursing an enormous crush on her, to which I thought she was oblivious. After all some of those messages had been from her many boyfriends. Next to those well-dressed and obviously successful men, I was sure I was invisible to her. What had happened however, was that her forceful personality had rubbed those guys the wrong way.

*cough*

Hearing the delivery guy cough impatiently snapped me back from my reminiscence. I gave him back the pad, took the package and curstied again. He looked at my name, but I hurriedly shut the door before he could look at me again.

Sighing, I put the package on the table and went back to the kitchen. I had grown used to walking in high heels by now, but the click-clacking was still distracting. I knew I had to hurry. There was a little more than an hour to finish polishing the tile and to get started on the laundry. The consequences of failing to finish my chores on time were never pleasant, but the stakes were especially high today. It had been three weeks since I'd last cum and I was determined to please my wife enough for her to give me a reward.

After getting the mop out of the closet, I started spreading the polish all over the floor. Keeping a house spotless and gleaming had given me new respect for wives in the 50's. How they could do this while raising children was beyond me!

The idea of having a child made me think. My wife had been hinting at wanting to get pregnant lately. How that squared with her stated intention of never letting me penetrate her again was a mystery. She had male friends at the office I knew about, a few of which I had known before we were together. One in particular; his name was Chad and they had always been friendly.

I knew very little about what she got up to there now. After we had married she terminated my position in favor of wanting me to be a homemaker. Every time I had asked her about any work related matter, she would reply that I shouldn't "worry my pretty head about that complicated stuff".

Could she be seeing Chad? Sometimes she came home late, but I assumed she had to put in more hours. She was a little disheveled on occasion too. Sometimes her pussy tasted a little differently on the many, many occasions that she wished for oral sex.

I felt the familiar mix of jealousy and arousal when I imagined her and Chad. My captive little clitty tried to swell up, but of course it couldn't. The cursed device down there never failed to keep me frustrated and horny. My wife had put it on a year ago when she caught me masterbating instead of doing my chores. I still remember that night, in particular my fiery ass cheeks, my aching insides from a soapy enema, and the thick buttplug keeping it in. She'd made me beg for forgiveness before she had finally released me, but not before attaching the chastity device with a satisfied air.

After that, I was lucky if I got to orgasm every three weeks. With that kind of leverage she had swiftly turned me from part-time sissy to full-time maid. My old clothes were thrown out and replaced with several french maid outfits as well as a few different dresses for special occasions. By then I learned not to complain or I would be facing both a longer chastity term and a swift trip over her lap. For a slender woman, she spanked very hard. I wish I could tell you that I had faced those spanking sessions bravely, but in reality I was always reduced to tears and helpless squirming.

I reached the end of the floor and looked at the clock. Half an hour left! I was making better time than I thought. Before heading to the bedroom to gather the clothes, I stopped at the bathroom to fix my hair and make-up. My wife said my appearance reflected on her and wouldn't be pleased if I didn't look my best.

Picking up her clothes hamper, I took them to the laundry room. Most of her clothing could be put in the washer but she was clear on wanting her panties hand washed. Seeing the expensive silk and lace reminded me of how this all started.

In the first year of our marriage, it was a wreck. I had been getting less and less tolerant of her commands and we were spending most of the time ignoring each other. It had been so long since we'd had sex that I was drawn to her panties. Every day I wanted to touch them, and everytime I did it brought back uncomfortable memories of stealing my sister's underwear. Just like when I was a kid; it wasn't long before I succumbed to the desire to wear them. I modeled her panties in the mirror and experienced the familiar thrill.

Seeing her face in the mirror behind me however, wasn't nearly as pleasant. I turned around and instantly got red as a tomato. Naturally I assumed that this would be the final blow for our marriage, but once again she surprised me.

Putting her panties in the dryer with plenty of fabric softener, I checked the clock. Done with five minutes to spare! I was proud of myself but there wasn't time to dally. I hurried to the kitchen and mixed up her favorite drink. No matter what, I was getting a reward today. I left it on the end table next to her favorite chair (with a coaster of course) and got into position.

Settling on my knees just past the door, I smoothed my skirt and used a pocket mirror to check my make-up one more time. Perfect! Now I just had to wait.

I felt a little hurt when I thought about her and Chad. I didn't exactly begrudge her having a man; clearly I couldn't fulfill the normal role of a husband now. She was always a very sexual woman. I had just mistakenly hoped that my tongue would be enough. But still, she could have at least told me.

Hearing the sound of a key in the lock pulled me back to the present. I clasped my hands behind my back and smiled. The door opened and my beautiful wife entered as if it she was walking into her castle. Just like the first time I saw her, my heart beat faster as I looked at her long, straight black hair, smooth pale skin and green eyes. Those eyes that used to look at me so sharply were now kindly taking in my feminized and subservient form.

"Did you finish your chores Caitlin?" she said with a smile.

Inwardly wincing at the teasing nickname I was saddled with all through school, I nodded.

"Yes Mistress Vicky." I said in my lisp.

She gave a satisfied nod and took off her heels, then walked into the living room. I paused to put her shoes in the closet next to the door and I followed her. She didn't bother to check whether I had actually finished my chores; I had been well trained out of lying to her by now. Reaching her favorite chair, I saw her notice the Red Velvet Martini on the table.

"Good girl!" she said approvingly.

Behind her and hidden from view, I couldn't help but give a slight bounce. She was pleased!

Taking a sip from the drink, she sank into the chair and put her stockinged feet up on the ottoman. I quickly dropped to my knees and rubbed her feet. She picked up the remote and turned on CNN. Not being allowed to watch TV or go on her computer myself, I haven't had any idea what was going on in the world for the last few years. I couldn't even get word of mouth usually, since whenever I left the house it was in my maid's outfit. Not so shockingly, people aren't in any rush to talk about current events with a sissy maid.

While she was watching TV and sipping her drink, I got the chance to take in her full appearance. She was dressed smartly in an expensive women's suit. Her breasts were nicely shaped and pushed up by a lacy bra underneath her silk blouse. Of course I was only allowed to touch them on very special occasions. My eyes traveled downward to her slender waist and long shapely legs, and from my position I could just see the tiniest peek of her panties. My clitty tried to stir at the sight but was kept small by the device.

Glancing up, I saw that she knew where I was looking. I gulped nervously, would she be mad?

My fears were dispelled as she smiled at me.

"You want to taste me there sweetie? Very well then." she said, her smile turning into more of a smirk.

She stood up and rolled her skirt up. Having done this many times, I knew it was my job to lower her panties. Waiting until I pulled them down gently, even reverently, she sat back down. Spreading her legs, I waited for her to point right at her shaved pussy before I scooted forward.

By now I was very familiar with how she wanted it. I lapped lightly at her pussy lips to begin with, waiting for her to get wet. From the top part of my vision I could see that her attention had gone back to the TV. (The guy on the screen was talking about "Twitter" or something like that, I had no idea what it was.)

Continuing to lick her pussy lightly, I could see that some wetness was beginning to appear. That was the signal to start paying attention to her clit. As I did so, I felt her hand settle on my head possessively. Her clit was poking out now and I was moving my tongue all over it. I could feel my wife starting to breathe a little more heavily. I knew she was getting close to orgasm when her hand that was resting on my head gripped my hair and I was pushed deeper into her pussy. This gesture was obvious; it was a combination of wanting me to lick harder and a statement saying "I'm in charge here." (As though I could forget).

She was murmuring "Good girl" several times over with her eyes closed and I knew she was about to cum. Knowing what my wife was going to do, I took a deep breath and then sucked and lapped at her clit. Just like I thought, she took both hands and grinded my face into her pussy, moaning loudly.

My face was soaked as she experienced an explosive orgasm. From between her legs I could barely hear her shriek of pleasure. A little light-headed by now, I waited for her to finish and release me so I could breathe. Finally she did. Peering out with one eye open, she rubbed my head.

"...Good girl, that was just what I needed." my wife said tiredly.

I stood up and curtsied for her.

"Mistress Vicky, may I fix my make-up?" I said subserviently.

"You may." she said, sighing contendedly.

I scurried to the bathroom. I had to make myself presentable but I wanted to return quickly before her good mood had a chance to disappear. My clitty had been trying to swell the entire time. Though it couldn't, I could feel a steady drip of precum collecting in my panties.

Incredibly horny, I tried to soothe myself with words while reapplying my mascara.

"It's okay, you'll get out soon, I know it!" I said, delicately applying volumizer to my eyelashes.

After reapplying my blush, lipstick and eyeliner, I was made-up properly again and returned to the living room. My wife had pulled her panties back up and sitting in her chair normally now. I sank down near her feet and began my attempt.

"Mistress Vicky, may I ask for a favor?" I began.

"Oh, what could this be about?" she said, smiling knowingly.

"May I please please cum Mistress Vicky? It's been three weeks and I've been a good sissy girl so far, really!" I begged, clasping my hands in front of me and making my eyes as big as I could.

"Hmmmmm." she said, putting a finger on her chin, well aware of how torturous her delayed decision was for me.

Though my desperation for an orgasm was clouding my judgment, I was confident that she would say yes. Like any good woman in a position of authority she knew to reward good behavior and punish bad. I had been studiously pleasing her all week and didn't give her any cause to punish me.

"Well..." she said, dragging it out. "...I suppose so."

I gave an involuntary squeal that she laughed at. Though I really wanted to begin, I knew that it would only procede at her pace.

She stood up and beckoned me to follow her. I did, fairly bouncing with anticipation. My wife went into the bedroom with me close by her heels. She went to the box of latex gloves on the dresser.

"Turn around sweetie. Put your hands on the wall and keep them there." she said, snapping on the latex.

I did as I was told, though I was nervous. I had been given a spanking in this position before. Because I could no longer see her, I strained my ears listening to clues. She was getting closer. There was a rustling sound, like she was unbuttoning something. I relaxed a little then, because I knew she kept the key to my chastity device on a silver chain around her neck that was underneath her blouse, resting between her breasts. I was a little disappointed that I wouldn't be able to see her stunning breasts, but I couldn't have everything.

"You've been a very good girl this week, it's true." she said, stroking my hair.

I felt my wife spoon me from behind, her arms going around me. I could feel her breasts pressed against me and that alone made my clitty try and swell up. With one hand she pinched the nipples on my fake boobs with a laugh, and with the other she dangled the key in front of me.

"Is this what my sissy girl wants?" she said, her breath on my neck.

"Yes Mistress Vicky!" I said quickly, nodding.

She laughed and lowered her hands. I looked down and saw her she was tucking my skirt up, showing my thong panties that were covering my captive clitty. She pulled down my panties slowly, exposing the tiny pink chastity device. I had kept that area completely hairless of course, as per her instructions. By now my clitty was dripping worse than ever and was straining at the device.

"Wow, would you look at that. Someone's really eager." she said, no doubt enjoying the embarrassed flush on my face.

She pretended to have difficulty opening the lock as I squirmed impatiently. She admonished me why slapping my ass a few times.

"Stay still!" she said, more playful than irritated.

I winced at the slaps since the back of my skirt's material was thin and my wife never seemed to recognize how strong she could be. Immediately I kept myself still and watched as she unlocked the device. My poor clitty instantly swelled to its size of three inches. Never very large to begin with, it had gotten progressively smaller each time it was let out. A fact that my wife never failed to remark upon.

"Aww look at that. It seems a little smaller this time too, don't you think?" she said, giggling.

"Y-yes Mistress Vicky." I said, deeply humiliated. "Well I wouldn't worry about it. I doubt it ever brought much pleasure to a woman anyway. Besides, it's not like the size of it effects your orgasm right? Or does it?" she asked, curious.

"I-I'm not sure Mistress Vicky." I stuttered, desperately wanting her fingers to move over my clitty.

"Maybe I'm being mean. Sorry sweetie, I should be helping you enjoy this." she said with an almost undetectable note of contrition in her voice.

Suddenly I felt her move to my left side and one of her hands turned my head to face her. Before I knew it, she was kissing me. She was actually kissing me! I hadn't felt her lips in months. For a few seconds I was so happy that I forgot all about my clitty. Until her fingertips started tracing the underside of it, that is. She must have felt my attention shift away from the kiss, because she slipped her tongue in my mouth right then. I was lost in pleasure as I felt her fingers rubbing my clitty a little more forcefully.

Finally she broke the kiss and asked me.

"Did you like that sweetie?" she said, never looking sexier than she did now.

"Y-yes Mistress Vicky! I loved it." I barely stammered out.

She laughed and moved her fingers all over my clitty. I would have preferred her bare fingers, but after three weeks in chastity, even latex felt amazing. With my attention on her fingers, I didn't notice until it happened; she had started sucking on my neck forcefully. Blushing as I thought of the obvious hickey that would be on my neck tomorrow, I felt my orgasm coming.

"M-Mistress Vicky! May I please cum?" I said desperately, knowing I had to get her permission first and not entirely sure that I could hold it.

"You may." she said simply, returning to sucking on my neck.

Finally I stopped trying to hold myself back and let the pleasure pass through me. Her fingers moved rapidly over my clitty as it started to spasm. I saw her other gloved hand move into position to catch my cum.

Letting out a rather girlish moan, I came. The only thought I came up with was that it was all worth it, everything, just for this.

When I came down from the pleasure, I realized that my knees had given out and she was supporting me. Laughing, she let me sink down. In her left hand however, was all cum that she caught. She brought it to my mouth.

"Come on sweetie, you know what to do." she said, her eyes sparkling.

Though I never enjoyed this part, I did indeed know what to do. Meekly, I lapped up all the cum in her palm until it was clean.

"Good girl. Now stay still." she said.

She bent down to reattach the chastity device. While I stood up and pulled my panties, she put the key back between her breasts. I tried to sneak a peek at them, but she had already buttoned up.

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byJemina004© 13 comments/ 118179 views/ 24 favorites

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