tagTransgender & CrossdressersCaitlin and Mistress Vicky Ch. 03

Caitlin and Mistress Vicky Ch. 03


I was sitting nervously in front of the mirror in the newly decorated guest room. Chad was set to arrive in half an hour. My wife was getting ready in what was for now our bedroom. She had told me to dress up for the occasion, though I was still to wear my maid's outfit. I opened my jewelry box and tried to decide how to accessorize.

I selected a lace choker with a teardrop-shaped diamond. Fastening it around my neck, I checked my appearance again. My blonde hair was nicely done in a ponytail with two long bangs on either side of my face. Some tastefully applied light blue eyeshadow set off my eyes and a cherry-tasting lipgloss had made my lips quite shiny. Without careful examination, I looked like a fairly attractive woman and I knew Vicky would be pleased. As a finishing touch, I picked up the bottle of Princess perfume by Vera Wang (given to me with a bit of a smirk by my wife) and dabbed at my wrists and below my ears. Perfect!

I glanced around at the guest room. A stranger might have guessed that it belonged to a teenage girl. Liberal amounts of pink and white were all around me, from the curtains to the posters. Vicky said that I would be allowed to decorate it, but that turned out to be only a choice between several things she picked out for me. Between a poster of cartoon ponies and a poster of some kid named Justin Bieber, (apparently he was popular) I picked the second one.

The one thing I appreciated was the large white canopied bed. After confessing to my wife that I had always been jealous of my sister's bed when I was younger, she bought one that was very similar. I was actually quite keen to sleep in it; the soft mattress and transparent lace curtains looked inviting. There would be plenty of time to try it out later though, until then I had some unwelcome tasks ahead of me.

Standing up, I gave my image one last glance and headed to our bedroom, intentionally not looking at what was laying on top of the dresser. For once I appreciated my high heels clacking on the hardwood floor, as it would help ensure that I didn't end up peeping at Vicky.

I had been tempted to go earlier and catch a peek of my wife changing but didn't dare. Seeing her naked figure, as lovely as it was, wasn't worth the spanking I would definitely get. Dealing with Chad showing up would be difficult enough without being unable to sit down. Still though, my chastity device-encased clitty tried to stir at the thought of seeing her naked. I smoothed my skirt and knocked, not wanting to risk it.

"Come in." came the voice of my wife through the door.

I opened the door and saw she was at the mirror just as I had been. Vicky was wearing a green silk gown and black heels. I knew her favorite color was green, mostly because it matched her eyes. Her straight black hair fell evenly around her and went halfway down her back. Several emeralds spaced out on a silver chain around her neck completed the look.

I walked over to her and watched her putting on her earrings. She picked up the hairbrush and wordlessly handed it to me, her eyes still on her reflection. I felt a pinprick of jealousy as I started brushing her long hair. She mostly wore simple and plain outfits for me, and she was obviously dressing up for him. In fact, I don't think I'd ever seen that dress before. Seeing her eyes in the mirror move to me brought my attention back to the moment.

"You're looking very pretty tonight Caitlin. You're not trying to seduce Chad yourself, are you?" she asked with a teasing smile. Unable to stop myself from going red, I shook my head quickly.

"N-no Mistress Vicky." I lisped, stammering slightly.

"And did you practice today sweetie?" she said, her smile widening.

The "practice" she was referring to had to deal with the dildo that was on top of the dresser in the guest room. My wife had told me to practice sucking on it everyday, in preparation for the inevitable blowjob I would have to give Chad. The first few times I practiced were under her supervision and I was incredibly embarrassed as I responded to her directions on how to deep throat, how hard to suck, and how to move my tongue around.

I would always be on my knees in front of the bed with her sitting on top of it next to me, with my skirt flipped up and panties down. Any hesitation in following her commands were met with a very hard smack with her hand on my sensitive ass. Once she was satisfied with my technique though, she left me to do it alone, with the condition that I had to pleasure the realistic dildo for ten more minutes each day. Today I'd sucked on it for a tiring forty straight minutes.

"Yes Mistress Vicky." I lisped softly, my face as red as could be.

"Good. You know what you need to do tonight, right?" she asked, looking at me in the mirror. I nodded and looked away.

"Good girl! Alright, let's head downstairs. I want you to mix some drinks for Chad and I. He likes a martini." she said, standing up.

I followed her downstairs, checking the clock as we went by. Fifteen minutes to go. Butterflies starting fluttering around in my stomach as I imagined opening the door when he arrived. Chad wouldn't be the first man to see me dressed as a maid, but he would be the first I had known previously.

Would he keep it secret from all the people where I used to work? I knew it didn't really matter anymore as my wife had made it quite clear that I would be a homemaker from now on, but it still bothered me slightly. Everyone there thought I was gay (despite my insistence otherwise) and the news that I was a sissy maid would be greeted as a satisfying explanation of our marriage.

News of our engagement surprised everyone there. Most people were politely incredulous when I told them. In fact, some of them didn't believe me and asked Vicky if it was true. After the first few times that happened, I learned to let Vicky break the news.

Unsurprisingly, she made every decision regarding the wedding, including my tux, who would be invited, and even what my wedding vows would be. I was pretty embarrassed that the "honor and obey" part that some women vowed would actually be said by me instead, but I didn't want to risk ruining things by complaining. Thankfully, only a few titters were heard as I said that during the ceremony. I knew my sister was one of them though, having plenty of memories of her giggling at me.

Suddenly I was brought back to the present and seized with the impulse to ask her something. Hesitating for half a second, I spoke up.

"Mistress Vicky?" I lisped. She stopped and turned around.

"Yes sweetie?" she said, her eyebrows raised.

"Do you still...I mean..." I lisped, looking at her meaningfully but unable to finish. She looked at me for a second or two, then smiled warmly.

"Of course I do honey. I'll always love you no matter what. This thing with Chad is just a physical attraction. He's an excellent lover and a very good choice for fathering a child. Once we're sure I'm pregnant from him, he won't be around here at all. At least until I'm ready for another one." she said, cupping my face in her hands. I nodded slowly, somewhat reassured.

She moved closer and kissed me on the cheek. I was a little bit disappointed, wanting to feel her lips on mine, but that was only for special occasions. From my days as her secretary I knew she was a shrewd manager of people. She probably wanted to reassure without rewarding me for that behavior. Still though, I couldn't complain about feeling her lips and I smiled back. Vicky turned around and we kept going.

We split up at the end of the hallway, my wife headed to the living room while I went to the kitchen. I pulled out the drink cart and got to work mixing their drinks. Pouring the gin made my mouth water slightly. I had enjoyed liquor in the past, but it made me somewhat intolerant of Vicky's orders and that was unacceptable to her. As a result, she hadn't let me have a drink in several years. I suspected she enjoyed teasing me about it too, judging from the satisfied sound she started to make after every sip of hers.

I was longing to take a drink, mostly to calm my nerves. I sincerely didn't want to suck Chad off, despite people believing I was gay. That rumor had been going around since the middle of high school for reasons I won't go into just yet. More broadly speaking though, I was aware of several effeminate mannerisms that I had a very difficult time getting rid of. The girls at the office had certainly picked up on them.

Back when I was Vicky's assistant, they'd seen me blush whenever they talked about guys. The other secretaries started trying to fix me up with their gay friends and even setting up a profile for me on a gay dating site. I complained to Vicky about it, but she told me she had much more important matters to take care of. Though she sounded indifferent, I could of sworn she smiled as she turned away in her office chair.

*Ring Ring*

The sound of the doorbell nearly made me drop the bottle I was holding. He was early! I put down the vermouth and headed to the door, trying to will my stomach to stop fluttering. I stalled for a few seconds by checking the peephole. It was Chad alright. Taking a deep breath, I opened the door.

"Greetings Sir, welcome." I lisped, curtsying and remembering the honorific Vicky told me to use.

Chad's first reaction was one I've experienced before. A slight widening of the eyes and his lips curling upward as he realized I wasn't really a woman. At least he was polite enough not to burst out laughing, though just barely.

Chad was several inches taller than me, even though I was in high heels. He had a handsome face and short but tousled brown hair. He was wearing a suede jacket that didn't hide the fact that he was well-built.

I remembered most of the secretaries had their eyes on him, but wouldn't make a move because of his rumored relationship with Vicky. It was the other way around for me. I was far too intimidated to talk to Vicky as anything other than her assistant with guys like him around.

Naturally I no muscles to speak of. Though Vicky had assigned me workouts to keep myself toned, they were all cardio and usually only something a woman would do, such as butt-lifting and (I still haven't lived this down) pole dancing.

"Thanks Caitlin. I didn't recognize you right away. You certainly look...different." he said, coughing slightly as he suppressed a laugh. As usual, I couldn't help turning red.

Clearly they'd talked about me, otherwise he wouldn't have known the nickname that had stuck to me like glue. Wondering what other embarrassing things he might know, I backed up a few steps and moved to the side of the hallway, my head still bowed submissively as he walked inside. I starred at his shoes and gave the slightest cough, trying to respectfully request him to remove them. Chad got the hint and took them off, watching me as I bent down to put them in the closet.

"This way Sir." I lisped in my practiced tone, walking past him and bidding him to follow.

As we went to the living room, I was pretty sure he was looking at me from behind. Vicky had taught me to walk suggestively during the early parts of my training and by now it was the only way I walked. Was he staring at my ass? Suddenly I wished my skirt was a little longer.

We walked into the living room and my wife stood up. I hurriedly got out of the way and watched them embrace. It wasn't long before they kissed. The pinprick of jealousy I had been experiencing became a full blown stab as I saw them start to use their tongues. Though it had only been a week since I'd last cum, my clitty starting dripping at the sight.

Finally they ended the kiss. My wife glanced at me, her pale skin somewhat flushed. I quickly took the hint and went to the kitchen to finish their drinks as they settled down on the couch. Placing the olive inside Chad's martini, I went to work on my wife's Cosmo. I really, really wanted to take a sip of one of these drinks, especially considering the task I had ahead of me. But if Vicky found out about it I would be sleeping face down for the next couple of days. Sighing regretfully, I picked them up and headed to the living room.

They were talking as I entered. My wife looked up at me from the couch and broke off whatever she'd been saying. I was a little curious about it but knew better than to ask. I set down their drinks on the table and stood there uncomfortably, not sure what I should do. Vicky motioned me down on my knees and I obeyed immediately, which unfortunately put me closer to Chad than her.

"Caitlin, introduce yourself." she said to me, taking a sip from her Cosmo.

"Hello Sir. My name's Caitlin, I'm Mistress Vicky's...sissy maid." I lisped, so embarrassed that I barely finished the sentence.

"Hi Caitlin. I'm Chad. Your wife's man." he said simply, a ghost of a smile on his lips.

"I'm happy you're here Sir. Would you please make my wife happy, since I can't anymore?" I lisped, knowing what Vicky wanted me to say.

"Oh? And why can't you?" he said, looking mildly curious.

I looked at my wife for a moment and then stood up. This would be far worse than the several embarrassments I had gone through so far. Closing my eyes, I lifted my skirt in front of them. This time Chad did burst out laughing. He likely knew I was in chastity, but seeing it was another matter.

The entire area was smooth of course. My small clitty was encased in a pink chastity device and further covered by a see-through black thong. I opened my eyes to see Chad was looking at it with interest while he sipped his martini.

"How long do you keep her locked up like that?" he asked conversationally.

"A few weeks, depending on her behavior." my wife said, now running her hand over his leg lightly.

"And if she behaves badly?" he asked, putting his drink down.

"Then she goes longer, not to mention going over my knee. But don't worry, I have her pretty well trained by now." Vicky said, her hand resting over his crotch.

My wife looked directly at me now, motioning me to my knees again. I sank down slowly as I watched them kiss. Vicky unzipped his pants, bringing out his half-hard cock. My eyes widened when I saw it; Chad's cock was twice as big as mine even though it wasn't nearly at full length. I felt a surge of jealousy as I mentally compared my clitty to his cock. At the corner of my vision, I could see my wife undressing.

Vicky put her hand on the back of my head and firmly pushed my head closer to his cock. Ignoring the sinking feeling in my stomach, I leaned forward and licked the tip. It immediately responded and grew larger. My clitty had been trying to do the same, but was mercilessly prevented by the chastity device. I took the head of his cock in my mouth and sucked gently, going a little deeper as I felt him get to full size.

I was getting into a rhythm now with my tongue moving all along the underside. Suddenly I felt Vicky's hand pulling me off his cock. I took a few deep breaths and leaned backward, grateful for a few seconds of rest. My wife broke off their kiss and swung over onto his lap, facing him with her arms around his neck. I had a bird's eye view of her pussy slowly sinking onto Chad's cock.

Vicky gasped as his cock went all the way in, likely touching places I never had. Chad started to fuck her now, putting both hands on her hips and moving her up and down. I leaned forward again and lapped submissively at his balls. Soon enough my wife started talking between gasps.

"Ohhh...that's amazing...you...you're so...big..." she said, bouncing up and down on his cock.

I could do little more than continue to lap at Chad's balls. My clitty was dripping badly by now and desperately wanted to get hard. After about ten minutes of slow fucking, they were both moving faster now, kissing each other and moaning. I knew it wasn't long until they both came.

Vicky threw her head back and shrieked softly while Chad pushed her all the way down on his cock. I could feel his balls tightening with my tongue. He was cumming inside her! I could hear Vicky gasp each time he pumped another spurt inside her pussy.

She collapsed against him, both of them breathing heavily. Not knowing what to do now, I kept licking Chad's balls. From my viewpoint, her pussy was filled stretched slightly by his thick cock, and that kept his cum from dripping out. My wife recovered soon enough and addressed me.

"Okay sweetie, I'm going to get off now. As soon as I do, keep your tongue over my pussy. We have to give Chad's sperm time to knock me up." she said. Even though I couldn't see her face, I knew she was smirking at me.

Vicky swung back over to her side of the couch and I quickly plugged her pussy with my tongue. His cum had a bitter taste as it slowly seeped onto my tongue. My clitty had soaked through my panties by now, but no one seemed to be concerned about that.

I heard Chad get up to go to the bathroom. My wife was putting her bra back on, but from where I was I couldn't get a good view of her breasts.

She drank down the last of her Cosmo and sighed contentedly. By now most of Chad's cum was just sitting against my tongue. Imagining that his cum might be impregnating her at that very moment made me squirm uncomfortably, trying to adjust my chastity device. Finally I felt a couple taps on my head. I looked up and saw Vicky smiling at me.

"Alright sweetie, lick it up." she said, her eyes gleaming.

A big load of cum moved into my mouth the second I lowered my tongue. Grimacing slightly at it's bitterness, I swallowed it. It had a stronger taste than my own and the amount of it was several times more than I was capable of producing. Vicky encouraged me to continue with her hand, alternately stroking my hair and pushing me deeper into her pussy.

After Vicky was sure that I'd licked her pussy clean, she stood and pulled her panties back up. My wife smiled down at me, seeing my smudged makeup and wide eyes. I hadn't stopped blushing since Chad arrived, and my cheeks were no doubt still bright red.

"Chad and I will going to the bedroom now. Remember to make breakfast for him too in the morning, and when you warm up the shower for him, he likes it a little hotter than I do." she said, stroking my hair.

"Yes Mistress Vicky." I lisped, standing up and curtsying.

I waited for her to head to the bedroom, and I slowly crept to the hallway, trying to minimize the sound of my heels on the hardwood. Chad had gone to the bathroom earlier and I wasn't eager to bump into him. I peered around the corner and saw the bathroom door was open and the light was off. Whew.

I quickly entered the bathroom and shut the door. As I washed my face in front of the mirror, it gave me time to think. On the whole, it wasn't quite as bad as it could have been. Chad was nicer than I'd expected. Having my mouth on his cock and balls was unpleasant, but I'd gotten through it. I didn't get to cum, but that was hardly surprising, as it was only a week since my last reward.

I sat down to pee before going to bed. To my shock, I sank down right into the toilet! Pulling myself out of it, I looked and saw that the seat was up. Apparently Vicky had unfastened it and Chad had left it up! I experienced a surge of annoyance that would be familiar to most women. However irritated I was though, I knew didn't have the guts to complain. I could only clean myself up and forget about it.

Afterwards, I took off my heels and walked to the guest room. I paused for a few seconds at the bedroom door and listened in. All I could hear was a muffled conversation, followed by Vicky laughing. As curious as I was about what they were talking about, getting caught eavesdropping wasn't worth it. Sighing softly, I went past the door and into the next room.

-A Few Hours Later-

I never really grasped how thin the walls in our house were before. Despite the softness of the bed that Vicky had picked out for me, (our bed was a little firmer, which matched her preference.) I couldn't sleep. Not with the sounds I kept hearing from our bedroom. Apparently their quick lovemaking on the couch earlier was nothing more than a warm up.

Report Story

byJemina004© 17 comments/ 83446 views/ 19 favorites

Share the love

Report a Bug

2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: