Kinky Secretary Auctioned Again

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Kinky Crossdressed Secretary is Auctioned once more - Sort of.
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Part 14 of the 56 part series

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

"Darla, it's your auction purchaser, Joan. She wants to talk to both of us. I'll put it on speaker."

"Darla dear. I hope your bottom has recovered. You were such fun to play with. I have a proposal for the two of you. I understand the auction was successful in raising a good bit of money for the women's shelter. Unfortunately there is still a need for more. Apparently the general public is not as generous as our kink community, sad to say. As you no doubt realize, I am not without means."

I quickly agreed. Joan lived in a gated community that was clearly exclusive. The guard at the gate didn't bat an eye as I was driven past in her car tightly bound and gagged.

"I am willing to make another generous donation to the shelter that would more than make up for their shortfall. This is where you come in. I would like to propose a 'play date' so to speak. Well really, the Dommes would play, you would would be played with. As you might expect, there will be some discomfort involved on your part."

I had no doubt of that. Joan was a paddling and flogging enthusiast. I hadn't been able to sit comfortably for several days after my visit to her home.

"To make it interesting my sub Beth will go back to her usual pain slut role. I am a bit disappointed that she didn't take more advantage of her opportunity as a temporary Domme. I plan to show her just how disappointed I am."

I had no doubt of that.

"I have also contacted Jane and Penny. Penny is willing to serve as the third sub in our little get together. Linda has graciously offered to donate her studio and will serve as Penny's Domme for our little soiree. Jane just wants to watch and will make a donation for the priviledge. She's less a Domme than just seriously twisted. She's bad, that one, in a really fun way."

"I should mention the format. I envision a sort of kink olympics and as with any contest, there will be winners and losers. The winners will be rewarded, the losers won't. What do you say girls?"

Mistress spoke up. "It sounds fun. Darla is such an exhibitionist, she'll love the chance to show off. And of course, it's for a good cause."

"It's settled then, this Saturday at Linda's. Darla, I want you in your catsuit, tight corset and no skirt. 4 inch heels please. Locked on. I'll leave the choice of makeup and hair up to you. The other contestants will be dressed the same. Mistress, please bring your flogger. Darla mentioned that you had one. See you soon! And by the way Darla, I expect you to arrive tightly restrained and gagged."

Wow, it sounded exciting but Mistress had never whipped me. How would she feel about it. I had to ask.

"I've thought about it a lot Darla. I don't want to hurt you, but I want you to hurt for me if that makes sense. I know if I asked you, you would say yes but I need to make it happen. It won't be a regular thing, unless you want it to be. It just seems like one more thing strengthening our relationship. Is it ok with you baby. If it's not, say so and we'll call Joan back and bow out."

"I would be honored to hurt for you Mistress. Just promise me one thing."

"And that would be?"

"Don't hold back. I'll know if you do. Let me have it with all you've got!"

Mistress held each cheek with a hand and smothered me with kisses.

The days crawled by and I alternated between excitement and apprehension. Our favorite makeup artist arrived Saturday morning and the next hour was a blur of airbrushing, foundation, blush, brow pencil, eyeliner, shadow, long false eyelashes and 'fuck me' red long wearing lipstick. My long deep red nails were glued in place. Mistress zipped my catsuit over glued on DD's with extravagant nipples straining against the fabric. I chose a black leather corset which Mistress helped me lace very tightly. I had hipster pads glued in place to give me an hourglass figure. I pulled on a wig cap and topped it with a long blond wig gathered into a pony tail with a black leather scrunchy. I used bobby pins to hold the wig firmly in place in anticipation of some vigorous activities. Large silver hoop earrings went into my pierced ears. I stepped into my 4 inch stilettos and Mistress used small padlocks to secure them in place. As a final touch my SLUT collar was locked on.

I lit a Winston and checked my look in the full length mirror. 6 feet seven inches of crossdressed slut in my heels. Mistress had dressed in tapered black leather pants with a white silk blouse. Her seamed stockings peeked out between the pants and her own stilettos. So Sexy! As usual, her bracelets and rings were perfect. A black and white houndstooth scarf competed the ensemble. In her hand was the flogger we had purchased at the fetish fair. She had both of our purses over her shoulder. I suspected my makeup would need freshening at some point.

I followed her to the garage where she clipped my leather cuffed wrists together behind me. She used a leather strap just under my breasts to pin my arms to my sides. I sat on the car seat with my feet out while she used straps around my ankles and above my knees. I leaned forward and accepted the bright red ballgag. I swung my legs into the front seat and Mistress belted me in. We were off.

I got a few looks and smiles at traffic lights but a friendly wave from Mistress and a smile over my gag reassured the onlookers that it was completely voluntary. We pulled into Linda's secluded home and studio. Mistress kindly unstrapped my legs, clipped a leather leash to my collar and led me inside. Penny and Beth were already there, sitting side by side in low backed chairs. Both strapped and gagged. Mistress led me to the third chair and rebound my legs. She went over and greeted Linda and Joan, accepting a glass of white wine.

Jane came over and immediately raided my purse for a Winston. Would she ever buy her own? She lit it with an evil grin and whispered in my ear. "I can't wait to see Mistress whip that bottom. I just wish it were me doing it. Maybe someday."

Not if Mistress had anything to do with it. Jane had taken liberties with me in the past and Mistress had punished her for it. She would pay severely if it ever happened again.

Joan walked over to us. "Ok you bound beauties, let's get started. Our first event is a race. When I give the signal you will each stand and hop to the yellow line you see on the other side of the room. When you reach it, turn around and hop back to your chairs. The winner gets a reward. The losers, well you can guess. You damsels will be in distress."

I loved this. My long legs gave me a clear edge over Beth and Penny who were of average height.

"On your marks, set, GO!"

We stood and started hopping to the line which was at least 20 feet away. Linda's studio was quite spacious. As I had surmised, my height gave me a clear advantage. The only challenge was keeping my balance as I made the line and had to turn around. I easily made it back and sat back down. Now for my reward.

"Very good Darla. Congratulations. As the winner, you get to watch while the other two losers are punished for their puny efforts. By the way, when we're done with them, you get yours too. You just get to think about what's coming. You didn't think you got off without it, did you?"

Beth was led to the spanking bench first. She was bent over and her collar clipped to a D ring. Joan firmly gripped her paddle and really laid into her with 10 hard strokes. I saw Beth smiling over her gag. A pain slut indeed. As a final touch, a large plug was inserted after Joan had finished with the paddling.

"You know what happens if that comes out. Another paddling and not that gentle one you just had."

Penny was next and Linda certainly didn't hold back. Penny grunted into her gag, clearly not enjoying it as much as Beth. Jane on the other hand, clapped and cheered as her significant other took her punishment. Penny's plug was inserted, much to her discomfort.

Penny was unclipped from the table and sat down gingerly.

I hopped to the bench and bent over to be clipped in. Mistress kissed my cheek and let me have it. She had wanted me to hurt for her and I did. I held back the tears and tried to think how happy it had made Mistress. Joan handed Mistress my plug. There was a definite pear shape. I felt my 'pussy' stretch as it went in. It popped into place and my sphincter clenched tightly around it. I was determined to keep it in place. I hopped back and gently lowered myself back into my seat.

"Ok girls. We'll take your gags out briefly for a water break. It's so important to stay hydrated."

Mistress took my gag out and held a bottle of cold water to my lips. I drank greedily. It had a slight aftertaste that I couldn't quite identify. Mistress put a Winston between my lips and lit it for me. Jane did the same for Penny after taking another for herself. Joan regagged Beth after telling us she was trying to quit. A most effective stop smoking program without a doubt.

"Now then ladies, sluts that you are, you'll love what comes next. Since you have one hole invaded it seems only right to abuse another one. We're going to replace your ballgags with ring gags. They are wonderful for stimulating drool while keeping you silent. They also take a cock quite well. We'll step into the other room and gear up, as it were. Don't go away!"

The ring gags were buckled tightly in place and the Dommes left the room. I fought to control it but soon I was dripping saliva onto my catsuit as were Penny and Beth. The Dommes walked back in, each sporting a large strap on over their pants. Now I knew why none of them were in skirts.

"Ok girls, here's the way this works. Each of our cocks is the same length. Since you each have such sexy red lipstick it will be easy to see who can take a cock the deepest. I'm betting on Beth, but I'm sure you'll all give it your best effort."

A padded cushion was placed in front of each of us and we were helped to our knees. How considerate!"

Each of the Dommes held their cocks and slid them into our respective mouths. The ring gags had guaranteed lubrication would be plentiful. Mistress slid her cock in gradually before pumping it more vigorously. I slid my lipstick over the ring to leave a mark and tried not to gag. She went as deep as she could before stepping back. I looked to each side and saw Penny struggling with Linda's cock despite Jane cheering her on. Beth on the other hand, had taken every bit of Joan's huge cock. It was no contest.

Joan patted Beth on her head and was congratulated my Mistress and Linda.

"Beth, great job. You go last. You get to watch this time and think about what's coming your way. What a great reward, right?"

Linda unstrapped Penny's legs and took off her chest strap. She led her over to her hoist and attached a spreader bar to her ankles. She clipped her cuffs to the hoist and raised her arms into a strappado. Linda took a flogger off of a rack festooned with all manner of equipment and wasted no time whipping her already sore behind. Penny squirmed but could do little. Jane hooted and cheered again with each blow. Penny was lowered and led back to her chair where her legs were rebound.

My legs and chest were released and I was led to the hoist. The spreader bar was attached and I felt my arms inexorably pulled upward as I bent forward. Mistress again kissed my cheek before gripping the flogger she had brought and making my sore ass even more tender. I mentally counted the twenty strokes as I watched the drool drip onto the floor out of my still ring gagged mouth. She didn't hold back and I had a sub's pride in hurting for her. I concentrated on not letting the plug slide out. I had no doubt what would happen if it did.

Linda lowered my arms and Mistress whispered in my ear. "I love you more than ever baby. It means so much that you did this for me."

I was led back to my chair where my legs and chest were rebound. Beth was led to the hoist and Joan pulled her arms so far up I thought her shoulders would pop out. Beth just smiled over her gag as Joan gave her twenty strong strokes, paused and gave her five more. Pain slut didn't begin to describe her. She kept smiling as she was led back to her chair and restrapped.

The Dommes enjoyed another glass of wine and a cigarette as we squirmed in our seats on very sore bottoms.

"Ladies, and I use that term loosely, we're going to untie you for a little while. You can go use the rest room and freshen your makeup. Move along now."

I gratefully stretched my arms as did the other two. We went into the spacious rest room which was more like a locker room with showers and several sinks. We chatted as girls will do. Each convinced they had taken the most forceful blows. I asked Beth what came next but she claimed ignorance. I gave my hair a quick brush and redid my lipstick. Just perfect!

We walked back into the studio and saw piles of rope on a table.

"For our last event girls, you'll each need to be hogtied and of course gagged."

Mistress replaced my ballgag and I obediently sat down. Mistress tied my hands palm to palm then used a long rope to pin my arms to my chest. She tied my ankles and above my knees. Thankfully my elbows weren't tied. She helped me roll onto my stomach and put me into a medium strict hogtie, attaching my ankles to the chest rope so there was no extra pressure on my wrists. Penny and Beth were tied and gagged similarly on either side of me with about 6 feet between us.

"I suppose you're wondering how you can do much, hogtied as you are. The answer is you can't but therein lies the challenge. You all remember the yellow line, right?"

We nodded that we did.

The first one to get there and back wins the hogtie race. As usual, there will be a reward for the winner and for the losers, not so much. As an added incentive, we each have our crops to urge our 'ponies' on. And don't forget, if your plug comes out, you lose automatically and your punishment escalates. Without further ado, GO!"

Mistress popped my butt as I wriggled forward. It was painfully slow but the others weren't doing any better. It took forever for us to reach the line and turning around was even harder. The Dommes laughed at our pitiful efforts and laid into our rears with the crops. I started back toward the chairs and had a slight lead. I looked my left and Penny was gaining. My DD's were definitely not an asset in this contest. I glanced to the right and Beth was smiling. She turned sideways and was able to roll over again and again. She had clearly done this before. It was no contest. There was no way I could do that. I struggled on but couldn't hold Penny off. I was last to finish.

After the Dommes finished laughing at the spectacle, the hogtie ropes were released. We sat side by side on the floor and waited to see what Joan had in mind.

"It wasn't really fair. Beth may have had some practice but then again, no one ever said it had to be fair. The good news is you all get to have an orgasm. The bad news is they may not be as pleasant as the losers would like. Beth goes first."

Joan took a wand vibrator and pressed it to Beth's pussy. Beth moaned with pleasure as Joan brought her to orgasm. She left Beth tied up and panting. She handed Linda the vibrator but Linda motioned Jane over and let her do the honors. Jane pressed it into Penny's crotch and rapidly brought her to orgasm.

"No, no Jane. Don't stop. I said the orgasms might not be all that pleasant for the losers. I think Penny needs at least a couple more. As you know, the pleasure goes down with each succeeding one."

Jane smiled and pressed the wand back into Penny's pussy. Mistress had punished Jane with forced orgasms after her indiscretions with me. Jane was well aware that the pleasure dramatically decreased. Penny panted helplessly as we watched. Joan finally decided she had enough and Penny was also left bound and exhausted.

"As for you, Darla, we have something special in mind. Mistress please unzip Darla's catsuit."

My clit popped out, fully erect. Mistress rolled a condom onto my waiting member. She tightly velcroed a cock ring around the base then attached a vibrator to the shaft.

"Here's the deal Darla. Mistress will turn the vibrator on and you'll no doubt cum quickly and gloriously. We all know how deliciously sensitive a 'clit' is just after an orgasm and if we were kind, we would turn the vibrator off. Sadly for you, we're not. The vibrator stays on for a little post orgasm torture. But here's the best part, the vibrator stays on till you get hard and cum again. Poor Beth and Penny stay all tied up till you do. The plugs stay in till then also. If your plug slides out, all three of you sluts will pay severely. We did give you a little help though. We crushed some Viagra into your water bottle."

No wonder it had a little funny taste. I jumped as Mistress turned the vibrator on and the Dommes retired to a table and chairs. They chatted and sipped their wine as I quickly orgasmed. The intense pleasure quickly turned to torture as my oh so sensitive clit suffered. The discomfort gradually abated despite the continued relentless vibration. I looked over at my helpless companions, their eyes pleading with me. I concentrated on retaining the plug, clenching my pussy tightly. I don't know exactly how long it was but I felt my clit begin to stir again. I gradually stiffened and the vibrations again turned to pleasure. I groaned against my gag as I shot load after load into the condom, filling it with my cum.

"Just one more thing Darla. Mistress, would you please help Darla. She looks like she needs a snack after all that."

Mistress carefully took the condom off while Joan took my gag out. I swallowed every bit of it, much to the delight of my captors.

We were finally untied, the plugs were removed. What a relief. We were sent to freshen our makeup. It certainly needed it. We walked back into the studio where I lit a Winston and gave one to Penny and Beth. She could stop smoking another time. Mistress gave me a hug and a glass of wine. Penny and Beth were similarly rewarded.

We chatted for a while about the day. What an experience. Linda then escorted us to her dining room where a delicious catered meal awaited us all. What a delightful way to end an eventful day. As we started to gather our things to leave, Joan spoke.

"What a wonderful day girls. You are all to be congratulated and the shelter will be handsomely rewarded. Since you arrived bound and gagged, you'll leave the same way."

Mistress clipped my wrists together behind me, re-applied the gag and clipped the leash in place.

She said our goodbyes since I was now silent. Mistress led me to the car and strapped my legs before belting me in place then driving us home. She unstrapped my legs and led me in. Mistress immediately drew me into a deep kiss. Amazingly I felt an erection growing. Thank you Viagra!

Mistress led me to the bedroom, unzipped me and had me lay on my back. She mounted me and rode me to a thunderous climax. What a way to end the day. I was finally untied and allowed to undress. We lay naked together with a last glass of wine and a post coital cigarette. I drifted off to a contented sleep. The luckiest girl in the world!

cdDarla
cdDarla
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