Kinky Secretary on Vacation Ch. 05

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Kinky Crossdressed Secretary and Mistress go home.
1.9k words
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Part 5 of the 5 part series

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

I awakened after another night in bondage. My captive clit strained against its prison fueled by the incredibly erotic dreams my situation seemed to produce nightly. Knowing Mistress was so close by but so unavailable on anything but her terms was frustrating but oh so sexy. She reached over and took off my blindfold.

"Morning sweetie, I hope you slept as well as I did. Your talented tongue saw to that. But enough about my orgasms and your lack thereof. We do have to go home today but I arranged for a late checkout so we have time to continue your Womanhood 101 training. Isn't that great!"

I had hoped to be fully retrained by now and desperately wanted the CB6000 off. I put a smile on my face and agreed with Mistress that she was indeed thoughtful and considerate to spend her time teaching me. She sent me to the bathroom to shower and 'douche'. My clit was judged to hairless enough so I wasn't restrained and shaved again though I would have loved it! Mistress slid a generously sized plug into my pussy and locked it in place.

"Go fix our coffee and breakfast. then do your makeup using what I have out for you. You've gotten better the last few days and this is a final exam of sorts."

I did as she said. The makeup was more suitable for daytime although the deep red lips were a constant. I put a stylish dirty blond wig on over my wig cap and bobby pinned it firmly in place. It was just below shoulder length and more conservative than what I had been wearing the last few days. I pulled the waist cincher tight and slid a pair of black leggings on. I topped it with a baby blue mid thigh length dress that was tight enough for my DD's to strain against it, outlining the nipples clearly. Still a little bit the slut, I guess. I put on a string of pearls and smaller hoop earrings. My shoes were open toed sandals with my painted toes clearly visible. I brushed and fluffed my hair then put just a little more shiny red gloss on my lips before presenting myself to Mistress for inspection.

She looked me up and down then had me slowly twirl around before pronouncing my efforts satisfactory.

"I suppose you're wondering what today's lesson is about. I'll tell you but first you do need to be tied up for this."

She led me to the low backed chair, guiding my arms over the back and expertly wrapping and cinching them together then attaching them to the chair. She did the same to my ankles and attached them to the lower rung of the chair before binding my thighs together just above the knees. She finished it off with a completely superfluous chest tie over and under my breasts that held my arms tightly to my sides and made my boobs seem even bigger. She cinched it using the chair back. I was completely stuck.

"Open wide sweetheart. You need to be gagged too."

She used the larger 2 inch red ballgag, silencing me completely. She stepped back to look at her handiwork and nodded her approval. She lit one of my Winstons and slowly circled me as a predator would her prey. She described the morning's activities.

"I think you're appreciating more and more what women go through every day to be attractive. I'll continue to remind and instruct you in the future but I think we're off to a good start. The other lesson to be learned is that my needs come first. I know you love your sports, though I can't for the life of me understand why. I'll remind you again how quick you are to get out of your female clothes, into the shower and in front of the TV. Well today, it's all about me. I'm going to take off the CB and I'm going to fuck you. You'll probably cum in a couple of strokes given the past few days. Here's the twist. You're going to stay tied up until you're hard again and ready to give me the ride I deserve. And don't even think about whining or I'll leave you tied up even longer. Do you understand?"

I nodded yes. I could tell by the look on her face she was serious. With that she pulled up my dress, pulled down my leggings and unlocked my clit which immediately sprang to attention, much to her delight.

"Look who's glad to see me. So cute."

She pulled up her nightgown and slid her wet pussy over my clit. I tried to hold back. I really did, but it was over as quickly as she had predicted. I slumped against the tight ropes thinking that this was when I was usually untied. Not today.

Mistress sat back and lit a postcoital Winston as she regarded her captive.

"I think I'll write some thoughts for my next blog post. I know how badly you'd like to be untied right now and sit back with a Winston. Just keep thinking about how happy it makes me that you're here to satisfy my needs. It should make you really happy too."

I nodded yes even if I wasn't quite as happy about things as Mistress.

"I'm going to leave the gag in for now so you're not tempted to start whining. Maybe if you're good I'll take it out in a bit."

Mistress fired up her computer and started typing, looking up and smiling at me every few minutes. Finally, she walked my way and stood over me.

"Think you can refrain from whining and begging?"

I nodded yes. I wanted that big gag out at least for a while. She seemed satisfied and unbuckled the gag.

"Poor baby! Let me clean you up. You were just about to drool on your dress and your lipstick could use a freshening."

She patted the saliva off my lips and chin then repainted my lips with gloss. She put a Winston between my freshened lips and lit it for me.

"That will help you keep quiet. Isn't that sweet of me to help you out?"

I nodded yes as she giggled at the thought that keeping me tightly bound after an orgasm was sweet.

"Now then baby, I'm going to put the gag back in to help you concentrate on making me happy. We don't have all day and if we have to leave before I'm satisfied things will go badly for you. I will help you out a little even if you don't deserve it."

She reached in the rope bag and brought out a cock strap that she tightened at the base of my clit. Then she took thin cord and pulled my 'ovaries' down and away from my crotch. She took several turns around then twisted the cord and separated them. Tying it off tightly. Even recovering from an orgasm, having a beautiful woman treat me this way was supremely erotic and exciting.

"I can't get over how considerate I am to help you out so much. I just know you appreciate it and would thank me if you weren't gagged. Looks like it's working. Let's give it a bit of time. I want you fully erect. After all, it's about my pleasure, honey."

I looked down at my strapped and tied package as it slowly engorged. Mistress smiled seductively and slowly slid her slick pussy over my clit. She fully impaled herself then just sat there, her face inches from mine. It seemed forever when she leaned forward and kissed me over the gag before starting to slowly move up and down.

"Don't move a muscle, Darla. I'm going to completely control this and I want it to last."

Last it did. She moved up and down then stopped to finger her own clit before painting my lips with our mixed ecstasy.

"Ooooh, baby, this is just wonderful and I guess you've suffered enough. You can cum now cause I surely am!"

She thrust faster and faster, head back and panting before we exploded in thunderous orgasms.

"I'm not going to ask if it was good for you, Darla. First of all, you're gagged, but all kidding aside, that was fantastic. I'll take the gag out then while it's fresh in your mind, I want your thoughts for the blog. A debriefing, if you will."

She took out the gag and unwound my clit as I described as best I could how the experience was both frustrating and incredibly sexy. To have someone you care about take complete control in such an erotic way was hard to put in words but I tried. When she had written her notes, she finally untied me but not before putting me back in the CB6000. I immediately crushed her to me and kissed her deeply again and again.

"Down girl! Not that I don't love the attention but unfortunately we have to get on the road. You can sit on the deck with a Winston while I dress and pack. But first, fix your makeup. You look like you've been rode hard and put up wet as they say. I guess it's because you were. The CB is just one last reminder of who's in charge."

She smiled as she said it and turned toward the bedroom. I redid my lipstick and lit my long overdue cigarette on the deck. I did wonder why the CB and where my clothes for the trip back might be. Mistress walked out dressed elegantly but casually.

"I guess I must have sent your clothes to the home address by mistake. Well really acccidentally on purpose. Your last lesson is about to start and the CB should keep you agreeable, don't you agree?"

I groaned as it dawned on me I would be making the trip home en femme.

"That's right doll, not only are you going home just as you are, but we're stopping at that cute cafe on the way. I'm famished and in the mood for a leisurely lunch. If you get leered at, well it happens to women all the time so get used to it. And one last thing, you're driving. Your heels will make it interesting but you'll do fine. Just one more thing women have to put up with. Let's get the car loaded and on the road. Don't want to miss the lunch crowd at the cafe, do we?"

I certainly did want to miss the lunch crowd but I knew it was the only way the CB was coming off. My face was probably red enough to match my lips and Mistress thoroughly enjoyed my embarrassment at lunch. The snickers and smirks were thick and fast although our waitress whispered that she thought it was really cool. Mistress briefly told her about my 'training.' She told Mistress that her boyfriend had also been less than attentive lately. Mistress slipped her a card with the blog url and wished her luck with her own boyfriend. I did manage to drive home without getting pulled over and cuffed by the local constabulary. After threatening to leave the CB in place, Mistress finally removed it along with the plug. The DD's peeled off without taking too much skin and acetone took care of the nails. I took the nail polish off and was back to my outwardly conservative, straight laced male self. I looked in the mirror and couldn't help thinking how I would really love to see Darla staring back. The good news is, I'm sure the lessons will fade and Mistress will need to correct my behaviour in the very near future. I can't wait.....

cdDarla
cdDarla
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