Kinky Secretary on Vacation

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Kinky Crossdressed Secretary and Mistress go on Vacation.
1.4k words
4.34
12.6k
9

Part 1 of the 5 part series

Updated 06/11/2023
Created 10/11/2021
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cdDarla
cdDarla
116 Followers

I find myself in my Maid's outfit made even more kinky with a pair of thigh high shiny boots and a posture collar locked on my neck. My makeup is over the top slutty. My head covered with a long blond wig pulled into a pony tail with a black velvet bow. Dressed as I am, I would love to have a Winston but I am gagged tightly. My hands are cuffed in front and I would be tempted to unbuckle the gag if it weren't locked in place. My ankles are enclosed by police style leg cuffs limiting me to mincing small steps which was Mistress' plan all along. With my hands in front I could reach under my short skirt and play with my own clit except for the fact it is locked in a CB6000 chastity device. My pussy is filled with a plug held in place by a diabolical harness that is also locked in place. My task is to clean our vacation cabin. Punishment is guaranteed if I don't please Mistress with my efforts.

She sits smiling, smoking one of my Winstons deliberately frustrating me even more. Perhaps I should explain how I came to be in my current predicament.

It started a couple of weeks back. We had both been working very hard with little time to play and I will admit looking back that I had not been as attentive to her needs as I should have been.

"Darla, I've decided we should take some time off. I have normally delegated the arrangements to you but this time I plan to do it all myself. You'll find out what I have in mind when we get there. I will pack for you and don't bother asking what we're going to do. It will piss me off if you start badgering me. Keep that in mind."

The weeks crawled and I managed to hold my tongue, curious as I was. I had visions of lots of kink and lots and lots of sex. The day finally came. I had worked in the morning and when I came home, Mistress had me change clothes for traveling. The suitcases were already packed. I loaded the car and off we went. The distant mountains got closer and closer. The temperature dropped and the leaves were splendid in fall colors. We finally pulled into a secluded cabin and I unloaded the car. The interior was well appointed and there was a deck with a spectacular view. The kitchen was already stocked. We wouldn't have to go out at all. I was getting excited at the prospects for the next few days.

"I need to run to the store down the road for just a few things. You jump in the shower while I'm gone and be sure to shave also. I'll put your clothes in the washer. Get moving!"

I didn't need to be told twice and stepped out of my clothes and into the shower. When I had finished, I shaved as Mistress had asked. I looked around for clothes but there were none. My suitcase was locked and there was nothing in the washer. What the heck was going on. Just then Mistress walked back in empty handed.

"I'll bet you're wondering what's happening. Well I'll tell you. You've gotten a little too comfortable lately. You're topping from the bottom. You want to play on your schedule and as soon as you've cum you head straight for the shower. Then you sit in front of the TV watching sports. Your makeup is sloppy to boot. The next few days are going to be a reminder of just who's boss and also a reminder of what we women go through to be attractive. Now if you can't accept that, we will turn around and go home and you can plant yourself in front of the TV while I write. Do you understand?"

I knew she had a point but if I had known all that was coming I might have chosen sports on TV.

"Good. I thought you'd see things my way. And by the way, I told you to shave. I want you hairless from the neck down. I'll make it easy. Get back in the shower and use this."

She tossed me a bottle of hair remover. I guessed I wouldn't be going to the gym any time soon as I watched my hair spin down the drain.

"Good, that's the first step. Now put this on."

She handed me the CB6000 and I reluctantly put it on and clicked the small padlock on.

"You'll earn any sex you get and it won't be easy. Now get busy with supper."

I did as she asked. She did allow me a glass of wine and a Winston before announcing we would be going to bed early as tomorrow would be a big day.

"Just because you won't get any doesn't mean I won't. I always sleep better after an orgasm so use your tongue and send me to dreamland happy."

I did as Mistress commanded, my clit straining against it's prison. She drifted off to sleep much more easily than I did. I hoped tomorrow would bring some relief but she seemed determined that I would suffer. Little did I know how much.

Mistress shook me awake, had me shave my face closely then fix coffee and breakfast. We sat on the deck with a last cup of coffee and a Winston.

"Well then, let's get started shall we. That's not a question, it's a statement. Go put your makeup on and do it right. Your usual lipstick and I want blue eyeshadow with long false lashes. Put your long nails on with glue, not the adhesive pads. I'll decide when they come off. Use the long blond wig over a cap with bobby pins holding it in place. I do not want it coming loose! And by the way, there's some nail polish for your toes. When you've done that, we'll take the next steps reminding you how hard I work to be beautiful for you."

I did as she asked, taking extra care to line my lips carefully before a coat of lipstick topped with shiny 'fuck me' red gloss. Mistress nodded her approval so far.

"Just a couple more things. I want you clean inside as well as out. Here, you know what to do."

She tossed me an enema and sent me to the bathroom to do my duty. I finished and went back into the main room where Mistress was holding a harness and plug. She had gloves on and spread lubricant on the plug before supervising it's insertion into my 'pussy'. She buckled the harness tightly and locked it in place. It wasn't coming out until she decided it was. She then reached into a box and brought out 2 DD sized breast forms with lifelike looking nipples. I didn't see a bra and Mistress smilingly told me I wouldn't need one. She then proceeded to glue them in place.

"That's waterproof glue so you can shower. It should wear off by the time we leave. If not, too bad. Now go get dressed in what I have laid out for you. By the way, I took your clothes with me and dropped them in the mail. They are scheduled to be delivered the day we check out. In the meantime, you'll dress and live as a woman. It will be instructive for you to go through everything I do each day."

I did as she asked and then meekly submitted to the posture collar which she also locked on. I opened my mouth for the locking ballgag and held my wrists out to be cuffed.

"Now get started cleaning. Here's everything you need. And do it right!"

I started with the vacuum cleaner and hadn't been working 5 minutes when she spoke up.

"No, no, no Darla. Short dainty steps. You walk like a football player. Maybe this will help you."

She put the leg cuffs on which certainly took care of that. She lit one of my Winstons and sat back to watch. I started cleaning again preoccupied by the fact that my clit and pussy were both out of service. I had to wonder what came next when Mistress popped my rear with a riding crop.

"Having fun yet, Darla?"

I nodded yes even though it wasn't what I had in mind. Mistress can be very creative and diabolical when she wants to be. She seemed particularly determined to teach me a lesson. I put my mind to cleaning well, knowing it probably wouldn't be enough......

cdDarla
cdDarla
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2 Comments
AnonymousAnonymousover 1 year ago

So much smoking. Ugh. Nothing sexy about it at all. Ruins the story. And it's not necessary to the story. Ruins the whole series for me.

MissLouisecdMissLouisecdover 2 years ago

lost interest when you kept mentioning having a winston, smoking is disgusting

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