tagTranssexuals & CrossdressersCaitlin and Mistress Vicky Ch. 02

Caitlin and Mistress Vicky Ch. 02

byJemina004©

I hummed softly as I put the finishing touches on the salmon. Teriyaki salmon was my wife's favorite dish and it filled me with pride to know that I was making her happy. My mouth watered slightly as I arranged the tray. (I would only be having a salad myself, as I had to maintain my figure.)

Taking out a pocket mirror from my apron, I checked myself to make sure I was presentable to her. My make-up was well-applied, my long blonde hair was pulled back in a sensible ponytail beneath my maid's cap, and my maid's outfit was spotless. All good so far. The lace bra I was wearing underneath was pushing my fake C-cup breasts up nicely, and my thong panties were hiding my chastity device that was covering my clitty.

All set, I picked up the tray and headed for my wife's study, my high heels click-clacking on the hardwood floor all the way. I knocked on the door quietly and waited for her to respond.

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

With a little bit of trepidation, I went inside. Alone among the rooms of the house, I was not allowed in her study if she wasn't there. I knew she kept her personal computer and business records here, as well as her bank account information and the household budget. None of which I was allowed to look at, of course. The paltry savings I had managed to accumulate before we got married had been transferred to her account. She said that it would be much better off in her hands and it was hard to argue. She had a MBA and was successfully running her family's investment firm.

I looked and saw her reclining in her expensive leather chair. I swallowed as I got a good look at my wife. Her long black hair, smooth skin and green eyes enchanted me just like she did when she was my boss. She was dressed in a beautiful though simple nightgown. I knew she had sexier lingerie, but she didn't seem to ever wear them around the house now. It was concerning, but all things considered it might be for the best. My clitty tried to stir enough even without seeing her like that.

Bringing the tray to her desk, I noticed she was talking on her cellphone. Now that wasn't unusual, but it didn't seem to be work related. My wife was laughing with whomever she was talking to. I couldn't remember my wife ever laughing when I was her secretary at her office. I stalled for as long as I dared, but no hints were forthcoming. Hoping it was a family member, I turned around to leave.

"Oh you liked it? I'll be sure to wear that next time." she said, giggling.

I stumbled and barely kept myself from falling. She was flirting with someone! As I looked at my wife twirling her hair with her finger, I felt jealously battling with arousal. Fidgeting with my clitty as it tried to swell inside the device, I kept my mouth shut. Complaining to her usually ended with a quick trip over her lap. I turned around quickly and left before I said something my bottom would end up paying for.

I returned to the kitchen and sat down. Glumly, I picked at my salad and thought about the situation. I had a pretty good idea who she was talking to. Chad Herring was one of the men who worked with her and I remembered him from my days there. He was very athletic and charming. Unlike most of the other guys from the office, my wife seemed to like him. Thinking back, he was popular with pretty much everyone there.

During lunchtime I usually chatted with the other secretaries, though I felt a little self-concious considering everyone but me was a woman. Guys around the office were a frequent topic. Some of the women were quite shameless about it, telling each other very personal things.

It was at that point that some of them asked me what kind of guy I liked. Choking a little on my lunch, I told them that I wasn't interested in men. The other secretaries were surprised. Apparently they were all convinced I was gay! I denied it repeatedly, but they didn't seem to believe me.

Regardless, Chad's name came up a few times. According to a few people, he had been with several of the women in the office, even Vicky! I wasn't sure if I believed it but they both acted familiar with each other, I had to admit.

I suppose it could be worse. Most of the guys there either acted like I was invisible or some kind of walking doormat, frequently sending me out on lunch runs for them. But Chad never did that. He even chatted with me occasionally. But still, the thought of him having sex with Vicky made me squirm in my seat.

Well, that wasn't the only reason I was squirming . My clitty didn't seem to want to give up trying to swell. My chastity device kept it from doing so of course, but it meant a steady drip of precum into my panties. It had been two weeks since she'd last let me cum and it was starting to take it's toll. I was so horny that I couldn't get the image of them together out of my mind.

Hearing the sound of my wife coming to the kitchen pulled me out of my imaginings. I quickly stood as she entered and curtsied for her.

"Yes Mistress Vicky?" I lisped.

"Come with me Caitlin." she said, her face slightly flushed.

I knew that look anywhere. She wanted my tongue to satisfy her and she wanted it now. I meekly followed her to the bedroom, fidgeting with my captive clitty behind her back. Looking down, I noticed immediately that she had taken her phone with her. Was she still talking to him?

Reaching the bedroom, she turned and motioned me down. I sank to my knees in front of my wife just as she lifted her skirt. Pulling her panties down gently, I could see that she was already wet. She laid down on the bed with her legs off the edge of it. I quickly scooted forward on my knees and began to lap at her pussy. She wrapped her legs around my head gently, though I knew that wouldn't last.

"Ohhh, my god. You'd do that to me?" she said breathily.

Looking up in surprise, I saw that she was talking on the phone. She was having phone sex with him while I was licking her pussy! The pain of my clitty desperately trying to swell would have made me wince, but my lips were occupied. Precum had soaked my panties by now and I had to squeeze my legs together in order to keep from dripping on the floor.

"Ohhh...ohhh...mmmm...fuck me...I want you to fuck me with that cock." my wife said into the phone.

I was licking her pussy like crazy now, desperately wishing I could touch myself. Though my clitty was fully encased in pink plastic, it was still pleasant to move it around gently. Of course my wife had forbidden me from doing that.

"Ohhhh! Chad!...I want you...I want you to cum inside me!...I want...I want your baby! ...Yeah! Knock me up!" my wife said panting, getting very close to orgasming.

Hearing my wife say that made me dizzy. Pregnant? She'd been mentioning that every so often lately, but as she didn't seem to be giving any hint that she was relaxing her policy of never letting me penetrate her again, I assumed she would be doing some kind of medical procedure with my sperm. The fact that my wife seemed to want to get pregnant by another man should have made me sick, but my clitty was dripping worse than ever now.

My thoughts were interrupted by her legs closing tightly around my head and drawing my mouth right into her pussy. She began to shriek as she came, arching her back and squirming her hips. Though I was getting a little light-headed by now, I kept my tongue moving in her pussy, trying to extend her orgasm.

Just as I was getting close to blacking out, she released me. Taking a few gulps of air, I shakily stood up and curtsied.

"Mistress Vicky, may I fix my make-up?" I lisped meekly.

She nodded and starting talking to Chad again. As I was leaving I heard her laugh.

"Wow that was great. Did you cum too? ...It's a shame to waste that, but there's always next time" she said into the phone, seemingly unconcerned with whether I was satisfied.

After reaching the bathroom, I sighed and washed my face thoroughly. As I reapplied my eyeliner, mascara, blush and lipcolor, I tried to calm myself. She probably just got carried away. I doubt she would actually have his baby. Or would she? She loved me but there was certainly a sadistic side to her.

After finishing my make-up, I opened the cupboard underneath the sink and pulled out one of the spare pairs of panties I kept there. My wife usually required oral sex twice a day while keeping me from cumming more than once every two to three weeks. This caused me to soak through my panties every so often, making me to have to change to a different pair. In order to keep from soaking through these too, I put a panty liner inside it.

Even though I had become very used to acting girly by now, changing panties and using feminine pads made me blush. I looked at the mirror to check my appearance one more time, then left the bathroom. I headed to the kitchen automatically, as my wife usually enjoyed a drink after sex.

Mixing an Appletini for her, I heard the sound of the TV turning on. My wife had evidently gone into the living room. I picked up the drink daintily and took it to her. Not looking at the TV, (I wasn't allowed to watch it.) I put it on the table next to her and curled up on a chair on the other side of the living room.

I could immediately tell she noticed. Normally I curled up at her feet, but her comment about wanting Chad's baby had perturbed me. I knew I was treading a fine line here. Letting her know I was genuinely unhappy without seeming disrespectful was important.

It wasn't long before she turned the TV off and motioned me over to her. I got up quickly and curtsied.

"Yes Mistress Vicky?" I lisped, a touch nervously.

"Okay princess, what's wrong? It's only been two weeks, you know pouting won't work." she said, giving me an even look.

She only called me "princess" when I was being sulky. It was a sign that she was concerned but that I should be careful not to push it. Fidgeting a little, I was shook my head.

"It's not that Mistress Vicky...I..." I lisped, then fell silent.

She patted the seat next to her and I sat down, smoothing my skirt. I was trying to figure out how to broach the subject respectfully when my wife suddenly pulled me over to her. I made a surprised sound, thinking she was going to spank me, but instead she pulled my head into her lap.

"It's okay sweetie, talk. I'm listening." she said, stroking my hair gently. Her fingers moving through my hair instantly soothed me.

"Mistress Vicky, it's about...the guy you were talking to." I lisped quietly.

"Ah. Yeah I probably should have explained that to you earlier." she said, a touch apologetically.

"First of all, it's purely a physical thing. I don't love him. I love *you*. You understand that right?" she said, looking right at me and tracing my lips softly with her finger.

I nodded, but I wasn't convinced yet.

"But you said you wanted his baby..." I lisped. She just looked at me until I remembered to say it. "Mistress Vicky."

She nodded, thinking for a moment.

"I did say that. I've been wanting a child for some time now. Look sweetie, I love you so much, but you have to recognize that a woman prefers a more...masculine and confident man to be the father of her children. It's mostly biological, if that makes you feel any better." she said, slipping her finger into my mouth.

What she was saying was a little hurtful, but to tell the truth I could see where she was coming from. Not very many women dream of having a child with a sissy maid. Sucking on her finger however, meant that I could only nod. She smiled at me and put a second finger in my mouth. Stroking my hair with her other hand, she continued.

"A woman just needs sex with a real man every so often. But afterwards they're a bother. I can't tolerate a lazy man. I would much, much rather come home to my pretty and obedient sissy." she said, her eyes sparkling.

I nodded again and continued to shyly suck on her fingers. I could tell she was pleased at my acceptance. Taking her fingers out of my mouth, she moved her hand down to my skirt. Flipping it up quickly, she fondled my chastity device through my panties, smiling as I gasped.

"So yes, I plan to have Chad impregnate me. But just because you won't be related to our baby doesn't mean he or she won't love you any less. Wouldn't you love our baby just as much?" she asked, pulling down my panties and exposing my chastity device.

Every time she reminded me that I wouldn't be the father made my clitty drip more. A fact that would certainly not escape her.

"Y-Yes Mistress Vicky." I said, squirming in her grasp as she moved her hand over my pink plastic encased clitty.

"I'm sure you'll be a great nanny for Chad's children. Just leave the work of making them to a real man like him." she said laughing, enjoying my embarrassment.

"Mistress Vicky! May I please please cum?" I lisped desperately, my horniness starting to overwhelm me.

"Oh I don't know...It's only been two weeks. By the way, Chad had me yesterday. And he's going to have me tomorrow too!" she said, her sadistic side coming out.

"Please Mistress Vicky! I'll do anything!" I begged helplessly. I absolutely had to be unlocked, I'd go crazy otherwise.

My wife unbuttoned her blouse and pulled out the key. Dangling it over my head, she laughed as my eyes followed it back and forth.

"You'll have to agree to a few conditions if you want to be unlocked." she said teasingly.

Nodding quickly, I was ready to agree to practically anything.

"But I won't tell you what they are, only that there are three conditions, and they all have to do with Chad." my wife said, a wicked smile on her face.

It looked like that was exactly what I was going to do. Still I hesitated, thinking of all the unpleasant possibilities. Seeing that, my wife made as if to return the key back under her blouse. Maybe she was bluffing but I couldn't take the chance.

"Yes Mistress Vicky! I'll do it!" I said, resigning myself to whatever she came up with.

"Good girl! Now you'll get a reward." she said with a touch of triumph in her voice.

My wife quickly unlocked the device and I gave a relieved sigh as my clitty was finally freed. Her fingers danced over it lightly as it grew to it's full length of three inches. She never missed an opportunity to make fun of it nowadays. It was her idea for me think of it as a "clitty", explaining that men had cocks, sissy girls had clitties.

"Aww, it looks cuter everytime. Needless to say, Chad is so much bigger. Almost three times as much in fact. But then, he has a cock." she said, tracing one finger along the underside.

My clitty was dripping just as much as it was earlier, and my wife took advantage of that. She collected every drop that appeared and brought it to my mouth. I meekly accepted her fingers, licking them clean.

"You know I might not get pregnant immediately. Chad and I might have to try for weeks or months. Just think of his huge cock cumming inside me again and again and *again*." she said with her eyes closed, likely enjoying the thought herself.

Her fingers were moving faster over my clitty, and I couldn't hold back for long. When I imagined Chad enjoying her pussy, which I haven't been able to do in years, I knew I was at the point of no return.

"M-Mistress Vicky! May I please cum?" I stuttered, squirming under her fingers.

"You may." she said, closing her hand over my clitty and pumping it quickly.

Seeing my clitty completely covered was the final straw. Closing my eyes and letting go, I immediately came, spurting into her hand and moaning just like a girl. When I opened my eyes, I was greeted with the sight of my wife's hand in front of my mouth.

"Come on sweetie, lick it up like a good girl." she said, enjoying this part far more than I did.

Giving a small sigh, I licked it up, swallowing everything on her hand until it was clean. My wife wasted no time in locking me back up. Jiggling my chastity device, she considered for a moment.

"I think it's getting a little too big for you now sweetie. You know how you keep shrinking. I'll custom order a smaller one soon, since even the tiniest one they normally make is way too big for you." she said, evidently not done teasing me about it.

Blushing, I stood and pulled my panties up. Curtsying, I remembered what to do.

"Yes Mistress Vicky, may I fix my make-up?" I lisped, well trained by now to fix my appearance after every sex act.

She nodded and turned on the TV. It wasn't until I had gotten to the bathroom that I remembered I hadn't asked her what the conditions I agreed to were. Applying my make-up, my mind ran through some of the possibilities. They all seemed to involve meeting Chad in some way. I knew Vicky would want me to be respectful to him too, I just hoped that was all she wanted.

Before returning to the living room, I needed to pee. My chastity device made it so that I had to sit down like a girl at all times, something my wife found both very proper and very humorous. She had even gone so far as to permanently fix the toilet seat down. When I was done I dabbed with some toilet paper and checked myself in the mirror again.

I looked presentable. My wife would want me to look happy too however, and she could always spot a fake smile. I made sure to look at the upside of the situation. Even though I wouldn't be a father in the traditional sense, (to put it lightly) I couldn't help but be excited at the thought of a raising a child.

Though I was happy with my life overall, just doing chores all day was a little dull. Having a baby to take care of would tire me out, but it would also enrich my day. It might bring me closer to Vicky too! I smiled back at my reflection and knew that it was real. Humming softly, I returned to the living room.

This time I sat down on the floor near her like I always did. She smiled at me and put her feet up. Rubbing them gently, I took the opportunity to ask.

"Mistress Vicky, could you tell me what the conditions are?" I lisped politely.

Though most people wouldn't have been able to tell, I could see that her smile was turning into more of a smirk. Seeing that made start to sweat.

"Okay sweetie. First of all, Chad will be coming over to the house from now on. Some nights he may stay over, if he does, you'll be sleeping in the guest room." my wife said lightly.

My unhappiness must have shown, because she bent forward and patted my head consolingly.

"It's not that bad princess. It'll only be for a few nights a week at most. We can even decorate the guest room for you. I'll let you put up your own posters and hangings. It'll be fun!" she said brightly, trying to cheer me up.

I nodded reluctantly. That had been about what I expected. Going back to rubbing her feet, I waiting for my wife to continue.

"Secondly, when Chad is here you will respect and obey him just like you would me. He doesn't have much experience with sissy girls, so you can come to me if you don't think he's being fair. Make sure it's worth my time though, or your bottom will be sorry." she said, smirking at me.

This time I controlled my reaction. Again, this is what I expected. I wouldn't like obeying Chad, but I could do it if my wife said so. Maybe the third condition will be okay.

"And thirdly..." she paused. "Just like you satisfy me, you'll satisfy Chad too, if he wants it."

My face paled considerably and I froze. This is exactly what I was afraid of. She knew I didn't like it, sometimes having me practice pleasuring one of her dildos as a punishment. My wife must have sensed that she was pushing my limits, because she was suddenly stroking my hair gently. I tried to turn away, but she firmly turned my chin to face her.

"It's okay sweetie. Look, I'll make you a deal. If you're on your absolute best behavior when he comes over, you won't have to. If not...well that sounds like the perfect way to make sure you abandon any vain hopes of competing with him." she said, not unkindly.

Report Story

byJemina004© 8 comments/ 50534 views/ 9 favorites

Share the love

Report a Bug

Next
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:

   Cancel