Curt and the Charity Auction Ch. 01

This is my fourth story with Curt and Tina, but the first in this new series. Let me know what you think.

"All Eyes On Me", "Tina's Play Thing", and "Joe's Awakening" also include these characters.

This is a work of fiction.

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Tina is a very persuasive woman. That's how I ended up stripped and pegged wearing only lingerie on multiple occasions. That's also why she is in charge of the annual Charity Auction. She is very persuasive.

"Curt, I have a big event coming up and I'm going to need your help," she said.

"Ok darling, I'll do whatever I can" I answered as I handed her a cocktail.

We were staying in on a Friday and I was hoping she would indulge me by letting me dress up. I wanted to show her my new outfit and give her a chance to humiliate me. If I was lucky, she would spank my ass and make me tell her why I bought an ultra-sissy french maid ensemble.

We are a good match. She's a knockout brunette with a tight body and a desire to dominate her partner. I'm a strong, masculine, Type A guy who needs to be dominated and feminized as an escape from my stressful work. It's how I cope.

It turns out she was in a playful mood that night and let me debut my new purchases. She took a seat in the living room and opened her book, while I scrambled to transform myself into a pretty maid. I wasn't going to be "pretty", but that wasn't the goal. I was craving the humiliation of presenting myself to my lover and hearing her mock me.

Here's what I was rushing to put on: a very short maid dress in powder blue with white lace around the edges, bright white satin panties with a white garter belt and white thigh highs, white heels with matching blue accents and big ridiculous bows, and finally a blonde wig with a big white bow headband. This was over-the-top even for me, but I couldn't wait for Tina to see me.

"Come on princess. Present your slutty ass for inspection!" she called out after an hour of primping.

I was as ready as I was going to be as I tottered in heels down the hall and into the living room to hear my fate. "What the fuck, Curt? You are the biggest sissy I've ever seen. Turn around and grab your ankles. Ruffled panties? Jesus. This is absolutely unacceptable!" she shouted as she stood up and walked toward me.

I was loving the attention and trying not to smile. I knew it would only make her angry if I let on how fun this was for me. "Come with me young lady" she said as she grabbed my wrist and dragged me into the kitchen.

She bent me over the counter and flipped up my little dress in the back. WHACK, WHACK, WHACK, WHACK... She had pulled out the extra large wood and metal BBQ spatula I kept in a drawer and was wailing away on my buns and thighs.

My ass was on fire and she wasn't even pausing to check in with me. WHACK, WHACK, WHACK. "God damnit Curt! What have I told you about dressing up like a little sissy? Do you know what happens to bad girls that show off their panties?"

"I'm sorry Tina. I guess I forgot. So, do you think I look cute?" I asked knowing it would set her off again.

"Cute? Shut the fuck up Curt. I just want you to know that you have gone too far this time. I'm going to find a way to punish you like never before. Are you ready for the most humiliating experience of your life? Are you?"

I had no idea what that meant, but I was definitely ready for her creative ideas. I stood up straight, towering over her in my heels and began straightening up and dusting. She just watched with her arms crossed and shook her head. Slowly, a smile crossed her face and she interrupted my "chores" with a big hug.

"You just can't help yourself, can you? You love to look at yourself wearing pretty, girly things. Did you already dress up and masturbate wearing this outfit, baby? Did you lick it up? Did you eat all your warm, gooey cum?" she whispered as she drove me crazy.

I nodded and smiled as I looked down at my sexy shoes.

"You are ridiculous. Where did you find your pretty new things, baby" she asked lovingly.

"Well, I've been looking for the perfect maid dress for a long time and finally saw it in the window of that crossdresser store you hate. The rest of the things came together pretty quick. The shoes aren't a perfect match, but I love them."

"But I love them...Jesus you're teenage girl" she mocked ruthlessly.

"So why the maid outfit, baby? Is this a fantasy of yours? Do you want to feel subservient to your boss? Is it a cleaning fetish?"

"Well, I like it because it's ultra-feminine. It's so short you can see my thigh highs all time and my panties whenever I bend slightly. I like to imagine someone watching me work and sneaking peaks at my privates. Maybe my employer will lose control and order me onto my knees to service them. You know, dirty stuff."

"So tell me Curt, see...Curt/see...Curtsy! That's it! Holy shit! That's your girl name. You're fucking Curtsy!" she was jumping and giggling.

"I don't know Tina. Do I really need a girl name? I mean, Curtsy? Really?" I pleaded.

"It's decided Curtsy. Whenever you're dressed up, you will answer to your new name and do whatever I ask. Right?"

"Of course Tina. I'll be Curtsy and I'll do everything you say" I answered with a little apprehension and a lot of excitement."

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The next Friday, we were home again and I was cooking dinner. Tina was sitting at the kitchen island drinking a glass of wine. "So, remember the event I mentioned last week? It's the annual Charity Auction. I'm in charge this year and I'm making a few changes. We're going to start making some real money for the children's programs."

"That's great babe. What can I do to help?" I offered.

"Great question, Curt. I've decided that we are going to auction off men. The highest bidders will get to use their prizes for 24 hours. I'm going to play up the sexy side. You know: hint that the winners can do whatever they want with the men. I'll have to put some effort into finding guys with the right attitudes if you know what I mean. I already have a cop, fireman, construction worker, accountant and I'm looking for more."

"It sounds like you just need an Indian Chief and you'll have the Village People. I'll be happy to be your fireman, babe. Whatever I can do to help" I joked.

"Oh baby, I already have a fireman. What I need is a maid. I'm inviting Curtsy to the auction. You're going to put on your pretty dress and all of your sissy accessories and join me on stage to be auctioned off to the highest bidder. We are going to make a fortune. I think you'll appeal to a special audience of high end clients" she gloated.

"WHAT? No way, no way, not gonna happen!" I protested.

"Say 'no' one more time Curt and it will be your last - ever. Now this is not negotiable. You're going to put on your Big Girl panties and I'm going to sell you. Do you understand?" she threatened.

I was not going to defy her again, but I needed a little wiggle-room. I mean, this was a very public event. People I know were going to attend. It would have been bad enough to let her objectify my as a firefighter and auction me off like a piece of meat. But she wanted me to stand there in full "sissy mode" while all kinds of powerful and respectable people looked me over. My private desires, my dirty secrets would become common knowledge. I would never be the same.

"Darling, I will never say 'no' to you again. I am going to do whatever you need me to do. However, do you know what you are asking me to do? Do you understand that my life will change forever?" I said slowly and clearly hoping she would show some new compassion.

"Curt, not only do I understand what I'm ordering you to do, but I can't wait for everyone to see the real you. I'm going to lift up your skirt, I'm going to hint that they can use your mouth and ass all night. I hope that men and women get in a bidding war over you. You're going to be the final prize and the star of my auction!" she said with an intensity I didn't expect.

"Alright Tina. I will be ready for anything the night of the auction" I said and walked away.

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Tina had two weeks to prepare and I had two weeks to stress about the Auction.

How the hell was I going to pull this off? Could I act like the whole crossdressing thing was Tina's idea? What if she promised oral sex to the winner? What if a man won me? My stomach was in knots, but I was also excited about being "outed" in such a public way. Maybe this was exactly what I needed to finally embrace this new life I was enjoying with Tina.

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"Hi Sissy, I have a few details for Curtsy. Are you ready to listen?" she buzzed into the house as I was finishing cooking.

"Um, yeah babe. Welcome home" I said as I grabbed a pen and paper.

"Good girl. Now you need to shave your face, back, arms, legs and ass. Go ahead and leave some hair in your pits, chest, stomach and privates. Some women prefer that. Use an enema the afternoon of the Auction and insert the jeweled buttplug 'just in case'. Pay very close attention to all of your personal hygiene: nails, teeth, smells etc. I expect an immaculate presentation.

You will stand tall and gorgeous all night and make me proud. Do you understand?" she said with an authoritative tone.

I was resigned to being sold at the Auction. I agreed that my best strategy was to own my sissy presentation and be proud. I would just do my best with the public humiliation that was inevitable. I was less worried about anything sexual that might happen during my 24 hours of slavery. I'd already had plenty of sexual play and I enjoyed most of it.

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The Saturday of the Auction finally arrived. I was standing in a gray suit next to the other men up for auction. The event was being held in a large ballroom at the Conference Center. Approximately twenty round tables were set for dinner service. Everyone was mingling over cocktails while many people inspected the "merchandise."

Tina walked up to me and kissed my cheek. "Fuck, I should have you out here in your sissy dress" she complained. "I really screwed that up. Everyone would be buzzing about you, baby."

I agreed that I would have been the talk of the town, but I was glad she hadn't discovered that until now.

Several groups paid particular attention to me. Eight women from a local office were seated together in the back of the room. They all came to visit me together. "So, Tina said you do housework?" one of them asked. "How does that work?"

"Well ladies, I will be happy to do any work you need around your house. And yes, I do windows" I answered playfully.

"And will you wear the proper attire for a maid?" another one asked.

I flashed red and broke a sweat as they all giggled and whispered to each other. Tina must have tipped them off.

"As a matter of fact, I'll be wearing my uniform during the Auction. You'll be able to see what you're paying for" I offered.

A shy girl in the back asked "so, I'm on a budget. I want to make sure this would be money well-spent. Um, just to be clear - you will eat my pussy, right?"

"Jeeze Susan. Just come right out with it!" the other girls laughed and blushed.

"It's fine. That's actually a good question. Yes Susan, you can strip me and sit on my face. I will be yours for 24 hours to use however you ladies want."

"Oh goody, we can't wait" and they left.

An older woman approached me "Do I understand correctly that you will dress as a maid and come to my house to do chores for me?"

"Um, yes ma'am. I'll do anything your heart desires for 24 hours" I said.

"Oh my, I'll make sure I have my checkbook ready young man" she said as she winked and left.

That's when Tina walked by and said "we're starting soon. Get your little booty to the dressing area and start getting ready PantyBoy. You have a little over an hour to transform into a sissy-maid."

I started walking toward the adjacent meeting room where my costume was staged. I looked back and saw that all of the guys were following me to wait for their moment on stage. "Oh crap, I'm going to have to change into my maid dress with an audience of dudes!" I realized.

They all pulled chairs into a big circle and sat down with beers and snacks. I approached the rolling rack where my pretty dress and accessories were hanging off to the side. Tina stuck her head through the door and yelled for the accountant to come with her.

"Mark, you're first- let's go!"

"And Curt, don't fuck around. Get your ass into gear and be ready in one hour!" she shouted.

I gave her a thumbs up and began stripping. An hour can be a long time, but not when you had to do as much as I did. "Fuck it" I thought, these guys are all going to see me dressed up on stage so I might as well not be bashful. I stripped down completely naked.

"Dude, what's up with this? What does she have planned for you tonight? Are you just going on stage 'cock-out' and ready to rock?" Jake, the fireman from an adjacent city asked.

"Hey Jake, you have no idea. It's way worse than that. I'm wearing a full on french maid costume" I admitted as I pulled out the tiny package containing my undergarments."

"Seriously bro? Like a dress and panty hose and a wig too?" he asked with a big smile on his face.

"Yeah, the whole thing, man. It's gonna be pretty brutal. She's trying to get max bids tonight. Good luck out there, Jake. I'd be ready for anything tonight if I were you" I cautioned.

"Fuck man, I'll be fine. But you're actually walking out there dressed up?" he asked excitedly.

"That's the plan. Tina and I have been having a lot of fun and we are both getting off on this humiliation stuff. I don't love how this thing came together, but I owe her so- here we go!"

"Shit, good for you. Everyone is going to lose it when they see you. Good luck, I don't think I'd have the balls to get all 'sissied up' in front of hundreds of people. Let me know if you need anything, bro!" he offered.

While we were talking, I had pulled on my pretty, white satin panties with a ruffled butt. I sat and pulled on my white thigh highs - not my favorite color, but they made the outfit. As Jake started to leave, I asked if he would attach the garter belt straps on the backs of my legs close to my ass. I always have trouble getting those myself.

"Uh, sure Curt. I'm better at taking these things off, but I think I can hook you up" he said as he pulled the elastic band tight and pulled up on my nylons. I'll admit it was a little erotic to feel his hands on my thighs as he helped me.

"There you go man. I think you're all set. Um, I can zip you up later if you need help with that dress" he said.

"Thanks Jake. I'll probably take you up on that when the time comes" I replied with genuine appreciation.

I went ahead and stepped into my cute high heels to get used to wearing them. I sat in front of my tiny mirror and put on the wig. It took a lot of adjusting and pulling to get it looking and feeling just right. I finished with some eye liner and red lipstick.

Now it was time for the dress. As an experienced crossdresser, I knew to step into the garment and then pull it up. As I stood and pulled the dress up my body, I noticed that all eyes in the room were focused on me. I paused briefly and played with the straps for a moment to savor the attention. My hands were close to my cock as I gently adjusted myself and played with the fabrics.

Just then, Tina stuck her head through the door and called for the Construction Worker. "Ian, you're up!" she yelled as she looked at me.

"For fuck's sake Curt. Just put it on and stop giving the boys a show. And you guys stop encouraging this PantyBoy!"

The guys all looked away as I yanked the dress up to my shoulders. We knew we were busted. I took a few minutes to stuff my chest with socks and tissues. I had considered buying real breast forms, but thought that might be "too much."

"Um Jake, could you please zip me up?" I asked nicely.

He approached from behind and slowly pulled the zipper up. When it reached the top, he pulled the fabric at my shoulders and smoothed out some wrinkles. I turned to face him and he just stared at my chest.

"Yes, you can touch them Jake," I offered.

"Oh, um I was just. Ok," he said as he reached out and squeezed my tits. "They feel nice."

"But how do they look?" I asked.

"Fucking great. You look really great Curt," he gushed.

"Wow, I guess I'm ready then," I said with confidence.

Tina opened the door again and called for the cop. "Jake you're next after Adam! Stop flirting with my boyfriend and make sure you're ready for this. And Curt, did you put in your plug?" she asked.

"Shit, not yet!" I panicked.

"Jake, help him finish up," and she was gone.

"What was that about?" he asked.

"Damn, I have one more thing I forgot to do. Can you help?" I asked.

"Sure Curt. Whatever you need" he said as I handed him the jeweled butt plug. "What do I do with this, man?" he asked innocently.

I bent over with my legs spread and pulled my panties aside. "You can suck on it or just spit all over it and stick it in my ass. Don't worry Jake, it's clean" I replied.

"Oh shit, wow. This is some crazy stuff" and then he put it in his mouth. He swished it around and pulled it out with saliva coating it.

"Ok Curt, I'm gonna slide it in you, dude."

"Go ahead, Jake. It's not my first time by a long shot" I encouraged him.

He met a little resistance so I bent over more and pulled my cheeks more. "Just push in and twist it a little. I'll push out at the same time. And Jake, can you drip some more spit in my asshole?" I asked.

He leaned over my bottom and dribbled more saliva onto the plug as he pushed it in.

Tina opened the door at exactly the right moment to see Jake cramming the plug into my boy pussy and drooling on it.

"Jesus Christ, I can't leave you guys alone for a minute! Jake, come with me. Curt, brush your teeth and put on your perfume. I want you looking and smelling perfect" and I was finally alone.

I walked around the room trying to perfect my movements in high heels. Then I looked in the mirror to see how easy it was to show my panties. I lifted the front of the skirt and looked at my cute shaved legs and the V my panties made. My cock started getting hard so I sat down and calmed my nerves before my life changed.

The door finally opened and Tina came in. She sat next to me and put her arm around me. "Hi baby. How are you doing? You look amazing" she offered.

"I'm good babe. How is it going out there?" I inquired.

"We're doing so good. The previous fundraising record was $20,000 for the silent auction. We've already reached $24,000 and we haven't even sold our biggest ticket item yet - you!" she boasted.

"Wow that's great Tina! I'm sure I can get you a few hundred more dollars for sure" I hoped.

"Oh Curtsy, you're going to bring in thousands more. I know that for sure!"

"Ok Tina, whatever you say. I'm ready to do my best. Any last minute advice?" I asked.

"Honey, it's going to get a little wild out there. Just go with it. You are a special fantasy for some of these rich people. Don't try to understand it. I'm going to make all sorts of suggestions for things you will do with them. It doesn't mean they will actually happen behind closed doors, but you need to agree to everything. Do you understand me Curtsy? You will say 'yes' to everything. Got it?" she said with that familiar intensity.

"Yes Tina. I understand" I agreed.

"Good. Let's go you little cutie! Fuck you look and smell great. Thank you Curt. I'll owe you for this when it's all over" she said in a rare moment of appreciation.

The door opened and the buzz of the crowd was jarring. Then they saw us emerge from the side of the room and everyone erupted. Imagine a 6' man in a frilly maid dress, high heels and a blond wig walking out with Tina to the center of the stage. The eight women seated in the back of the room shrieked in appreciation. Others stood and clapped and some just covered their faces in embarrassment.