Kinky Secretary on Vacation Ch. 03

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Kinky Crossdressed Secretary and Mistress go on Vacation.
1.6k words
4.49
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3

Part 3 of the 5 part series

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

"Fix us some breakfast and then we'll get you ready for the day."

I went to the kitchen and made coffee and a light breakfast of fruit and toast. Mistress insisted we eat on the deck. She had her nightgown but I was still in a very short nightie with wig and DD's bulging. I had no makeup and must have been a sight.

"A little embarrassed Darla? A common emotion for a woman caught not looking her best. Not really fair, but that's the way it is. Just another little lesson in Womanhood 101."

I cleaned the breakfast dishes and awaited her instructions which were not long in coming.

"You can take off your wig then shower and shave. And Darla, clean yourself inside too. Think of it as a douche. Yet another feminine thing men don't have to deal with. Besides, the plug goes back in and we wouldn't want an accident. Would we?"

I enthusiastically agreed with that and did as Mistress instructed.

"Now then, I do have some work to do on my latest writing project so I need a secretary today. A subservient, obedient secretary. Not one who just dresses for sexual excitement. Just enjoying crossdressing barely scratches the surface of womanhood. Put on the clothes and hair I've laid out for you, then do your makeup and move it, Darla. I've got work to do."

I dressed in a white blouse and black pencil skirt over a waist cincher pulled as tightly as I could. A wide black leather belt tightly buckled emphasized my constricted waist. I had black seamed stockings held up with a garter belt. I put on long red hair, just like the real Darla Crane. Our favorite bondage model. I had conservative earrings and a string of faux pearls. I did my makeup fairly conservatively per Mistress' instructions. I realized there were no panties and hoped this meant my clit might be freed.

"I'll bet you're wondering about your panties. Well I saved them for last since we need to plug that pussy. Now pull up your skirt and bend over."

She lubricated the invader and slid it home, using the locking harness to hold it in place. I was then handed a pair of black lace panties and pulled them up over the

CB6000 and the 'pussy' plug. I was ready for the day. She did allow me a Winston although I had to go on the deck, again exposing myself to anyone looking. I was glad the cabin was fairly secluded.

"Now then, your job is answer the phone in a professional manner, answer emails at my instruction and generally do whatever I tell you to do to make my day easier. Use your best feminine voice. 'This is Darla, Mistress' secretary, how may I help you.' Can you do that without screwing it up."

Sounded pretty easy really but I wasn't about to tell Mistress that. She settled behind her computer and started to work. I sat across the large work table and started fielding calls and emails. Typing the response was a bit interesting given my long red nails but I was able to make do. We took a smoke break later in the morning and Mistress went to use the lady's room. She came out wearing a generous strap on.

"Believe it or not Darla, some bosses aren't as nice as me. They expect their secretaries to do a bit more that answer the phone. Sometimes their job depends on it. Let's pretend yours does. Now get on your knees and use your mouth like you mean it."

I did as she commanded, holding the base of her strapon I flicked my tongue over the tip before sliding my fuck me red lips down the shaft, taking more and more in my mouth each time. I glanced up and Mistress was smiling and had her phone snapping pictures of my predicament.

"That's it Darla, deep throat it like the slut you are. You'll just love these pictures by the way."

I increased the pace, matching Mistress' thrusts until suddenly my mouth filled with a salty liquid.

"That's right Darla. I saved it from the last time you got lucky. Didn't you wonder why I had you wear a condom? Swallow every drop and think how poor secretaries feel when they are put in this position."

I swallowed without gagging and slid my lips off of the strap on, leaving it glistening with fuck me red lipstick.

"Let's have a light lunch and get back to work. And Darla, go fix your lipstick. You are a mess."

We ate on the deck. Mistress had a glass of wine. Water for me. She allowed me a Winston before we went back to work. More phone calls and emails. Mistress was a busy woman. We had been back to work about an hour when Mistress looked at me and yawned.

"I think I need a power nap, Darla. I'm going into the bedroom now. I'll call you when I'm ready for you."

She called me in, looking stunning in her slinky nightgown.

"What to do with you? Don't want you misbehaving while I'm asleep. I don't think the CB6000 is coming off but you can be a clever slut at times. I know. Put that chair at the foot of the bed and sit down."

I did as she asked. She then tied my hands behind me before securing my ankles and thighs. She fashioned a chest harness, fixing me to the chair. I opened my mouth and took the ballgag she held before me.

"I won't sleep that long but before I do, the sight of you sucking that cock got me all hot and bothered. I think I'll use the wand vibrator and you can watch! Won't that be fun!"

I groaned in frustration as she put the vibrator over her magnificent pussy. I so wanted to bury my clit in it but she gave no indication my torture was near an end. I leaned back in the chair as she orgasmed, smiled slyly at me then promptly fell asleep.

She slept for about an hour, stretched langourously and finally untied me.

"Just a couple more calls and we'll be done for the day."

We went back to the work table and I resumed my secretarial duties. Toward the end of the day, the phone rang and I answered as usual. The conversation started out innocuously enough. Then the woman suddenly asked if I took dictation. I answered that of course I did.

"No, no honeybunch. Let me spell it out for you. Do you take Dicktation? A little birdie told me you were quite the cocksucking slutty secretary."

I was aghast. Who was the women? I looked up and Mistress was smiling broadly.

"Don't you recognize the voice, Darla. It's our old friend Jane. She just loved the pictures I sent her."

Jane and her sidekicks were my erstwhile kidnappers. They had grabbed me, tied me up repeatedly and generally had their way with me. We later found out they ran a fantasy kidnapping service and had been led to believe we were fully aware that the kidnapping wasn't real. When it was all sorted out, we became friends and Jane had a chapter about fantasy kidnapping in Mistress' anthology of kinks. Mistress had me record my experiences in the Kidnapped Kinky Secretary stories. She then had me subimit them to Literotica where they were published.

"I think what Mistress is doing is wonderful. You had gotten entirely too comfortable and needed a reminder of who's in charge. If women like Mistress and I were in charge, the world would be a better place."

I couldn't argue with that. I just wished I wasn't encased and plugged as part of my lesson. We chatted for a while longer and Jane said she hoped she would see me soon. We didn't have anything planned and I took as just polite conversation. We finished for the day and had supper.

"You know Darla, when a boss buys their secretary dinner they expect something in return. To be a bit crude, time for you to 'put out'."

She pulled my panties off and unlocked the plug, sliding it out.

"Now lay back on your back and show me how much you appreciated dinner."

I assumed the missionary position and Mistress slid the still lipstick covered cock into my pussy, filling it up. The CB made sure my clit behaved. Mistress started thrusting deeper and deeper urging me to meet each thrust with one of my own. I felt the cock start to vibrate and knew it had to extend into Mistress' pussy. She pounded harder and harder until she screamed with pleasure and slumped on top of me before pulling the cock out.

"That was really nice. If there were ever a time for a cigarette, this has to be it. And Darla, it's so great to have a secretary who knows her place."

She lit her Winston with a satisfied afterglow look on her face while I smoked mine more in frustration. After we finished, Mistress had me undress and put on my short nighty. My long red hair stayed on as did the DD's and nails. She had me put on the leather wrist and ankle cuffs.

"Hands behind Darla. Since you did so well last night, we'll skip the connecting chain and just lock the cuffs together. You don't mind, do you? I thought not. You can tell me about the dreams tomorrow. Be sure to get plenty of sleep. We've got another big day tomorrow."

She slipped the blindfold in place and I tried to get comfortable as I wondered what tomorrow would bring......

cdDarla
cdDarla
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AnonymousAnonymousover 2 years ago

Hot, HOT, HOT!!!

Nicely written, good grammar and spelling just like a proper secretary should.

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