KInky Secretary, Jane's Punishment

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Kinky Crossdressed Secretary and Mistress punish Jane.
2.1k words
4.32
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Part 55 of the 56 part series

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

"Darla, I've thought long and hard about what to do with Jane."

Jane was the head fantasy kidnapper who had kidnapped me along with her sidekicks Joyce and Lynne. I had been tied up and used by them several times. We had subsequently become friends but Jane had taken advantage of that friendship a couple of times without Mistress' permission or approval. At Jane's urging I had received a bondage blowjob from Penny King whom I had helped Jane fantasy kidnap. Mistress was very possessive of 'her clit' as she referred to it. Jane then had me pose as a bondage model for pictures for her site. After taking the pictures she used her strap on at my expense and had me eat her pussy despite promising Mistress to behave. She had left a locking butt plug in my 'pussy' as a final touch. Mistress had been plotting her response and had come to a decision.

"I'm going to have Jane come over and you're going to carry out her punishment. You've already paid for your part and I'm going to enjoy watching Jane get hers."

I wondered how Mistress would get Jane to agree since I knew Mistress would never cause harm or do anything non-consensually. As usual, Mistress was far ahead of me.

"Watch and learn Darla. Jane is a very bad girl, but basically a good person and as we would agree, lots of fun. We both have enjoyed getting to know her and her friends but she needs to learn her limits. Meaning what I say goes and nothing more."

I quickly agreed. Mistress was used to being obeyed. Certainly by me. She called Jane and put it on speaker.

"Jane dear. How are you? I wonder if you would mind coming over so we can discuss your latest little liberties with Darla without my permission and contrary to my instructions that you behave. It's time for you to take your punishment."

There was a pause on the other end. "Mistress, I just don't know what comes over me. Let me say I'm truly sorry for tying Darla up, using my strap-on, having her eat my pussy and leaving a locked plug in her all without your permission."

She didn't sound very remorseful as she listed her mischiefs.

"Jane, Jane, Jane. You don't sound very sorry to me but you will be later. In case you were wondering what kind of leverage I have, let me explain. First of all you took pictures of Darla in various states of bondage to post on your website to help you garner customers. Darla withdraws her permission for you to post them as of now. Furthermore your business has taken off largely as a result of the fantasy kidnapping chapter in my kink anthology which was largely written by Darla with help from me. I would hate for Darla and I to have to post a negative review on your website or on yelp. That would definitely be very bad for your business. I happen to know you'd like to quit your tech job and go fulltime in the fantasy kidnapping business. I think that's enough said. I will expect you here in a couple of hours."

Mistress hung up before Jane could respond and assured me she would be here.

"It seems only fitting that you're in your secretary clothes. We'll take some nice photos for even more leverage. Now go get dressed. Black pencil skirt, white blouse, waist cincher and your Darla Crane red hair. Oh and your 4 inch stilletos and fishnet hose. Go heavy on the makeup. I want it to really pop for the pictures. One last thing, put on your 'bitch' collar today because you're going to be one!"

I hurried to do as Mistress instructed though I still didn't know exactly what she had in mind for Jane. The next hour was a blur of makeup, feminine attire, long nails and luxurious long red hair. I took a last look in the mirror and buckled the collar on, freshened my deep red lip gloss and took a sip of wine to settle my nerves. I lit a Winston and waited for Jane.

Soon enough, the door bell rang and a contrite appearing Jane walked in. No doubt hoping Mistress had changed her mind and and her halfhearted apology would be deemed sufficient. No such luck for Jane.

"First of all, strip. Everything off and no arguments."

Jane sighed in resignation and did as Mistress ordered. She crossed her arms over her chest in an attempt at modesty. Mistress handed her the butt plug harness she had locked in me and told Jane to put the plug in and buckle it in place. Mistress had put a vibrating plug in the harness which featured a remote control. Mistress had me tighten the straps, exposing her pussy fully as the tight straps opened her up.

"Now then, sit in this chair with your arms over the back. Darla, start with her wrists. Let's get Jane a little less comfortable."

I wrapped and cinched her wrists then attached them to the chair. Mistress then had me pull her elbows together. Jane was slender and very flexible. Mistress paid no attention to her protests. I wrapped rope above and below her C breasts and cinched the harness between her arms and chest on either side, running the rope through the chair. She was stuck, but good. Mistress had me tie each leg to the respective chair legs, leaving her pussy wide open. Mistress handed me the ring gag. Perfect for having Jane drool all over her exposed breasts. I snapped some pictures with my phone then handed it to Mistress who took pictures of Jane with me standing by her smiling at her predicament.

"Just a couple more things Jane. If you thought a simple tie up and plug was all you were in for, sorry but no."

Mistress handed me a wand vibrator that I knew had fresh batteries in it. I pushed the head against her pussy and secured it tightly in place with more rope. Mistress gave me the nod and I turned both vibrators on, causing Jane to twitch against the tight ropes.

"Not much punishment. Right Jane? I mean tied up and brought to orgasm. What's the problem. Darla would volunteer for that treatment in a minute. Right baby?"

I quickly agreed as Jane started to get rather obviously excited.

"The thing is, forced orgasms start out as great fun but as they come again and again, it's my understanding they become progressively less enjoyable. We're going to find out. Enjoy, while you can."

Jane bucked against the ropes as she had her first. I lit Mistress' Virginia Slim and a Winston for me as we sat on the couch with a glass of wine to enjoy the show. Jane slumped against the ropes after her orgasm, drool already collecting on her tits but the vibrators were relentless. She quickly came again violently and had a pleading look in her eyes. Mistress just smiled as sweat started to mix with the drool. She bucked again as she was sent over the edge. I took video of each orgasm with lots of still pictures also.

"Enjoying yourself dear? I hope so. We certainly are and in case you were wondering, we're not nearly through."

Jane's eyes rolled back as as she exploded again. It was obvious the pleasure was rapidly lessening.

"Darla, let's give Jane just a brief break. I'll bet she could use a smoke. She always says how sexy it is to watch you smoke while you're all tied up. It's only fair she does it. Darla is going to take the gag out dear. Don't bother asking for us to stop. If you do, I'll just add more orgasms. Understand?"

Jane gave a resigned nod and I took out the ring gag. I lit a Winston and placed it between her lips and watched her take a deep drag and a long slow exhale.

"You know, I've got an idea you'll just love Jane. Darla, put the clover clamps on and whatever you do Jane, don't drop that cigarette. That would piss me off and you don't want to do that."

Jane clamped her lips around the Winston as I pinched her nipples and put the clover clamps on. Having worn them myself, I didn't envy her.

"Now turn the vibrators back on Darla. Jane, let me remind you not to let that Winston fall out of your mouth."

Jane shook her head no but to no avail as her body jolted with the renewed vibrations. She quickly had number 5 but managed to keep the cigarette in her mouth. I thoughfully caught the ash so it didn't mingle with her drool and sweat. I took it out after she had smoked it down successfully.

"Open wide Jane. Darla, put the harness gag on her. The one with the 2 inch ball."

I strapped it tightly in place while managing to 'accidentally' brush her clover clamped nipples, much to her chagrin. I rejoined Mistress on the couch, lit a Winston myself and sipped an excellent Merlot Mistress had opened for the occasion. I looked over and grinned at Jane, in the throes of number 6.

By this time Jane looked like she had been 'rode hard and put away wet' as they say. I glanced at Mistress to see if she had seen enough. She just laughed and we kept going. By the time number 7 shook Jane her response was considerably more subdued. She was getting worn out.

"Just one more Darla. I think that's enough and nicely symmetric. 4 before her cigarette break so 4 after. Turn the vibrators up a notch. Let's make sure she doesn't get bored."

Jane looked anything but as I cranked both up to the max. She pleaded with her eyes as they did their work and Jane climaxed again. MIstress had me turn the vibrators off and take the gag out. She stayed tightly bound.

"I think I've made my point. Do you agree Jane? Do I have your promise to behave in the future. And just to be clear, Darla needs discipline and punishment from time to time. If you're good, I might let you help me with that since I do just love bad girls. You have a deliciously twisted mind and a mind is a terrible thing to waste. Now that's a slogan someone should use."

Jane quickly agreed and Mistress allowed me to untie her and take out the plug. Jane hurried into the bathroom and came out wearing a robe after freshening up a bit. She collapsed onto the couch, completely exhausted. I lit a Winston and handed it to her along with a glass of the Merlot.

"Mistress, I underestimated you. I can't say I enjoyed this but I guess I had it coming. I really do promise to behave from now on when it comes to Darla. She's so, so lucky to have you."

I knew that all along. Jane slowly dressed and left, properly chastised. I started into the bedroom to get undressed.

"Just a minute Darla. I wanted to compliment you on your makeup. You look really hot today and watching you with Jane has me a bit hot too. Here we are with the perfect bondage chair, miles of rope, gags, the whole nine yards. Seems a waste to stop now. Have a seat sweetie."

Needless to say, I was soon helpless. clit at full attention. Under Mistress' command, where I longed to be. What a perfect end to the day. I thought again I had to be the luckiest girl in the world.

We settled back into every day life. Jane published her pictures of me in various bondages on her fantasy kidnapping site. She tells me that business has taken another jump. We offered the pictures and videos of our punishment session. Jane declined to post them on her site. I'll admit to watching the videos a few times for my private enjoyment. She eventually sent Mistress a text.

"Mistress, the pictures of Darla have been great. Lots of activity. Joyce and Lynne were wondering if they could borrow Darla for a few bondage model shots of her at their hands. I've warned them of the price of overstepping your set limits. They understand, believe me."

Mistress turned to me with a smile on her face. "Let's hope they do, Darla. It would be such a shame to have to punish both of them. Somehow, I think it may be necessary to do just that. Think you could manage to get them to misbehave? You might just have to tie the both of them up. I have to admit, Domme Darla is a real turn on for me."

"Oh yes Mistress. I've started to enjoy being Bitch Domme Darla every now and then. You can count on them misbehaving. I'll see to it."

Mistress texted Jane back with a devious grin on her face. I can hardly wait.

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