Curt and the Charity Auction

In this chapter, our hero, Curt, gives his first, and much-anticipated blowjob. Tina is there to reassure him and to add to the sexiness of it. If that's not your thing...

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Tina sold me for $20,000. Four groups paid $5000 each to own me for 24 hours. I was standing on stage wearing my over-the-top sissy maid outfit and starting to feel self-conscious. Tina was negotiating the terms of my "service" and starting to schedule my encounters.

The group of eight women from a local insurance office agreed to get together in three weeks at one of their houses. I would be the main attraction, of course.

Mrs. Robinson, the widow, said she needed work done around her house in 2 weeks; whatever that meant.

Mrs. Jones said she could wait until next Saturday. It was obvious she would have preferred that I went home with her immediately. I thought she was just lonely, but then she mentioned that next week was better for her "husband".

That left Mr. Smith. I overheard him negotiating with Tina. He was on the staff of a wealthy family. I couldn't understand what was going on, but Tina was very animated. Finally, they shook hands and she came over to me.

"So Sissy, what a night! Can you believe $21,000 because of you? It's amazing. You've been so good tonight. I have one more big favor to ask, though. It's a big one, but I'll be here for you," she said cautiously.

I had no idea what was going on, but I knew it was big because of the way Tina was acting.

"You see baby. Mr. Smith was sent by his employer to find "talent" for a party he is hosting tomorrow. From what I can discern, it's a pretty kinky affair. And I just negotiated an additional $1,000 donation! But you have to do one more thing for me. Well, you have to do something for him right now...to him," she said with a little smile.

I stood speechless in my sissy outfit. Was she saying what I thought she was saying? Did she just sell my mouth to this man?

"Um baby, I don't get it. Why do I need to do that here? Tonight?" I asked.

"Well, they want to be sure you're going to deliver at the party tomorrow. Remember when we discussed everything you would do? Well, it's time for you to start my little PantyBoy. I'm going to be here with you, Curtsy. Come with me baby. We'll take him back to your changing room and get started."

I paused and took her into my arms. "Tina, this is a big deal. A big step for me. We've done everything possible with plastic toys, but we are about to add a real cock to our play. I want it, but I need you to tell me it's ok," I said.

"Jesus Curt, you're such an insecure little Bitch. Of course it's ok. I just told him you're my panty-wearing Sissy and you can't wait to orally pleasure him with me present. He agreed to do it like you described to me in your fantasy. Now, I want to see it. I want to watch you be a dirty slut and blow him. For fuck's sake, get into the moment and enjoy yourself. I know you're a strong manly-man, but you're also into men and you're about to take a cock into your mouth. Got it!?" she was practically shouting now.

"Yes Tina. I got it. I'm ready. I want to do this for us."

She held my hand and then her face lit up. "Oh my God. Of course. That's way better," she said to herself.

Then she turned to the various guests milling around (my future masters), "Ladies and gentlemen, my Sissy Curtsy is about to pleasure his first cock. She has asked me to be here for moral support, but I think it will be even sexier if she has an audience. Will you be so kind as to watch her give herself over to Mr. Smith and suck his cock? Pretty please".

My head dropped to my chest. I didn't know if I was ready for all of this at once. Could I humiliate myself in front of all of them? Is this what I wanted?

"Oh hell yes!" replied several of the office girls.

"I would like nothing more," said Mrs. Jones.

"Since you asked so nicely," smirked Mrs. Robinson.

Then Tina said, "Mr. Smith, our little Sissy is an inexperienced cocksucker, but she's eager to get started. How would you like her to present herself to you?"

"I've found that on her knees is an excellent starting position," he said.

I was starting to feel lightheaded. Tina led me to the center of the room and knelt down next to me. She held my hand and reached around my back to hold me.

"Oh my, such a pretty slut on her knees. This is so hot," someone gushed.

"So tell us Mr. Smith, have you been part of many cocksucking auditions like this? May we know what you're looking for? Curtsy here is a rookie, but she's very enthusiastic. Do you have any advice or qualities you're looking for?" she inquired.

"My employer expects him...er her to service his guests and he wants it to be a pleasurable experience for all. Please do to me what you have enjoyed in the past. That's all," he said in a matter of fact way.

"You heard him Curtsy. You have wanted to do this for a while. Let's make this the sexy experience you've been looking for. Mr. Smith is a very handsome man. Why don't you find out what's in his pants, baby" she guided me.

This was it. The moment I had told her I wanted. I told her how I wanted to do it and she made it happen. She was going to make me a cocksucker.

"I've always wanted to see this in real life," I overheard from the crowd of women gathered around.

I looked up into Mr. Smith's eyes and reached up to his belt. He removed his tuxedo jacket and handed it to Tina. Belt undone, I unbuttoned the waistband and pulled the zipper down. With his hands on his hips, he looked down at me.

An observer would have seen me: a 6' man in a short powder blue maid dress with white thigh highs visible. I was on my knees with cute high heals tucked under my buns. I was wearing a blonde wig with a white hairband and a big bow. I, The Sissy, was pulling another man's pants down, revealing his silk boxers.

I paused to untie and remove his shoes. Then I unbuttoned the bottom of his shirt up to his nipples. With his shirt open, I turned and kissed Tina who was kneeling next to me. Then, I leaned in and put my face into his groin.

"Fuck babe. You're doing great. Nuzzle his cock for me. Stick your nose in there. Search for his balls with your tongue. Good girl. I'm very proud of you," Tina praised.

I concentrated on how sexy I felt. My penis was still soft and tightly bound in my shiny white panties. I reached up and grasped the bottom of his boxers. I slowly pulled down as his pubic hair became visible.

"Take your time sweetie. Enjoy this. You only get to suck a cock for the first time, once. Feel him a little first," she instructed.

"I love how Tina speaks to him. She is strong, but compassionate. I'd love to own a man like that," someone said.

I reached up the leg of his underwear and touched his balls. I continued up and lightly wrapped my hand around his shaft. I smiled because I liked the size and shape of what I encountered.

"You're going to love this Sissy. I can't wait to watch you discover something you were born to do," she whispered.

I couldn't wait any longer. I wanted to pull his underpants down. I wanted to see his cock from the underside. Tina knew it and was trying to maximize my enjoyment. I pressed my face into his crotch and looked at her pleadingly. She smiled and nodded so I began to slowly pull down his underwear. The shaft of his penis became visible as the fabric descended over his thighs. Finally, I saw his tip as it slowly rose towards my face. He was getting hard as I watched. It was becoming alive.

"Oh Sissy, you got a good one for your first time. Good girl. I'm so happy for you," she gushed.

"Now, start with your hands. Gently stroke him and caress his balls. Save your lips and tongue. Build the anticipation, baby," she instructed.

I reached up began fondling his cock and lightly touching his balls. The organ continued to swell and it got harder. The veins became more pronounced and I could feel his heartbeat through it. I loved the velvet texture and licked my hands to make it slippery.

"That's so sexy Curt. Now lean in. It's time baby. Show me what a good little cocksucker you can be. Open your mouth girl. Stick out your tongue. Touch the tip. Lick the tip. Take him between your lips. Do what comes naturally. There, stop there and savor the experience."

I closed my eyes and focused on the cock in my mouth. I started moving my tongue rhythmically as I took more of him inside me. I breathed through my nose as I pulled back. I pulled all the way off and turned my head towards Tina.

"Thank you Tina. This is what I needed," I said as we leaned in and kissed.

"Aw, they're so sweet together. She's totally getting off watching her 'man' give head," a young voice said.

"Now suck that cock Curtsy. It's time for you to be a slut and swallow his load. Get going," she ordered.

I reached around and grabbed his buns as I impaled my mouth on him. I took him deeper than before and began bobbing rapidly. The thought of doing this with an audience of women made it even hotter.

"Oh shit Curt. I need to get a video of this for you. You're going to love it when you look back," she said as she aimed her phone at me. "Look at me, slut. Show us what a good cocksucker you are Curt. So enthusiastic! You're going to make him cum soon, baby" she said into the recording.

I looked up into his eyes and grasped his shaft in my hand. His cock was covered in saliva and I added more as I pumped my face into him. I was applying suction and rubbing the underside of the shaft where it feels good on me. He was looking into my eyes when he reached out and grabbed my head.

"Oh my God. That's soooo sexy. Now I know why men love doing that to me," one of the young women said. The others giggled.

"Oh gawd, Curtsy. This is so sexy. I'm so glad we waited until I could be here with you. Baby, he's going to fuck your pretty face! Your mouth is like a pussy for him. Just relax and let him fuck you baby," she said as she reached into her panties.

I dropped my hands to my sides and relaxed as he began to thrust into me. I was proud that I could stick my tongue out and feel his balls when he went deep. He was gripping my head and pumping his hard rod into my virgin mouth. I stared into his eyes to make it sexier for him. Sweat was forming on his brow and he began to grimace. "Mmmmm, yes!"

Then, he grunted and said "Now! I'm cumming Sissy..." as the tip swelled and my mouth was flooded with his warm cum. "Swallow it. Swallow it all," was his next command as he continued to hump and shoot into my mouth.

I sucked him until he was limp and clean, then he pulled out and pulled his pants up. "You did well. I'll inform my employer. Please forward the video to me. We will see you tomorrow. Thank you," and he exited the room.

"Holy shit, baby. That was so hot. Oh my god! You did it. You're a cocksucker Curt. You got down on your knees and blew that guy. And you swallowed his cum. I came too," Tina said excitedly then kissed me deeply and explored my mouth with her tongue.

"That's it ladies. Show's over. We hope you enjoyed Curtsy's first oral experience. There will be many opportunities to play with him in the weeks to come. Good night," Tina said as she led them out.

I was a little overwhelmed as I looked down. I was still on my knees. My jaw ached a little and I had his semen in my mouth. My wig was pulled to the side because he was holding my head so tightly. I burped, and tasted him again.

"Let's go honey. I need to get you home. You have a big day tomorrow and I won't be there with you. You're going to have to be a Big Girl all by yourself. Come on, Curtsy" she said as she helped me to my feet.

We went home, showered together and I fell asleep immediately.

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The next day was beautiful as Tina dropped me off outside the mansion where the party was being held. We decide that I should show up in casual clothes and bring my sissy maid outfit in a garment bag. Tina wasn't very clear on the details of the event, but after the "blowjob audition" I had been subjected to I assumed it would be very kinky.

"Ok honey, here we are. They told me to drop you off out front and someone will let you in. Don't forget your sissy outfit. I'm so proud of you! Now go on in and have fun. I can't wait to hear how many cocks you suck and other fun stuff. Bye baby," and she was gone.

I turned and the wrought iron gate opened. I walked up the driveway and saw about 10 cute women (20-30 years old) standing around outside the house. They were wearing assorted versions of the same outfit: yoga pants, tank tops, flip flops and all had little backpacks. I was wearing the male version of the same concept, but I was carrying a large bag with my dress inside.

"Hi ladies, what are we waiting for?" I asked as I approached.

"Um, we're all a little early to be let in. We are performing tonight. What are you doing here?" one of them asked.

"Actually, I have no idea. I'm not sure if I'm 'performing' or if I'm just here to help," I answered vaguely.

"Well, we were all told to be here at 3 pm sharp and then told they would let us in when all ten of us were here. Looks like you're #10," she offered.

"Oh, well I guess that could be the case," I replied.

Another girl asked, "I don't get it. Did you audition like the rest of us, or what?"

I felt very self-conscious then. I wasn't ready to admit to nine pretty women what I was doing at 11pm last night. "I'm not sure. What was your audition like?" I asked innocently.

"I don't know about you girls, but I had to suck an old guys cock while he videotaped me! Did all of you have to do that?!" she asked.

"Me too", "Same", "I did too", "I blew two guys!" they all began to answer at once. "How about you?"

I was on the spot now. I had to decide if I was going to play it cool or admit to everything. I decided that if I was going to be part of the slutty entertainment for the night, I might as well try to fit in with my co-workers.

"At least he had a nice cock. Am I right? And his cum was yummy," I offered.

"Oh my god! You blew him too? Why? That's sooo dirty," one of them asked.

"Long story, but my girlfriend, Tina, sold me at an auction and these guys own me for 24 hours. I have to do whatever they say. Last night was my first BJ ever, but I kinda liked it," I answered.

"A cute brunette with a smokin' body came over and put her arm around me. Honey, that sounds sexy, but you never have to do anything you don't want to with your body. You can say 'no'. We will help you if you don't want to do this. I'm Candy by the way," she said quietly.

"Thank you very much for your concern. But, I'm a Sissy and I get off on the humiliation and degradation. I'm a little afraid of what will happen tonight, but I've been through a lot of sexy situations with Tina. She has pegged me at parties, made me suck dildos, stripped me and made me crawl around under the dinner table and make all her friends cum. I hope tonight is fun too," I told her.

"That's some kinky shit. Ok girl, what's your name?"

"Call me Curtsy tonight, please" I said.

"Ok Curtsy, I've worked one of these parties before. I'm not sure what's in your bag, but you probably won't need it. Last time, they supplied sexy outfits and we all matched. There was a boy at that party too. He did everything we did and he got a lot of attention. I was shocked that with a bunch of hotties like us, some of them were still super-hot for the Sissy. You'll be fine, I'm sure. I just hope you're ready to be on your knees a lot tonight if you know what I mean."

It felt good to know that I would just be one of the girls tonight and that some of them might look out for me. I was intimidated about what we would wear and what I would have to do. I had pleasured one man in my life and now I might have to take care of a room full of men.

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"Come in ladies. Welcome. We are very pleased to have you join us tonight. Please come in and follow me. We have your costumes set out in the guest quarters. You will find your names on the packages. Tonight's theme is Playboy Club. You are all bunnies tonight, Enjoy!" said Mr. Smith, the man whose cock I sucked last night.

I had butterflies and felt weak in the knees as we followed him. I realized that I had a girlish crush on him and was hoping he would acknowledge me or at least my first oral performance. I was also embarrassed to be dressed as a boy after what I did. It was easier to do sissy-things when I was dressed as a dirty girl.

"Ms. Curtsy, your costume is here. The fabric is velvet, slightly different from the other bunnies, but it was the best I could do on late notice to find a black leotard for a 6' man. All of the accessories are enclosed. Enjoy your evening. I'm sure all of our guests will enjoy you," he added.

"That's high praise baby. You must have given him a great BJ last night. Did you lick his balls and finger his asshole too?" Candy asked jokingly.

"A cocksucker never tells," I answered in my girlish voice.

We all proceeded to strip and slip into our bunny costumes. They fit amazingly well considering the different shapes of women's bodies; not to mention mine. I stepped into the sexy black strapless leotard and pulled it up. I took the opportunity to tuck my cock straight down and tried to curve it toward my ass. I pulled my costume up very tight and asked for a zip.

"Put your pantyhose on first, Darling" one of the women said.

"Oh, of course. Sorry, thanks," I said.

So I stripped back down and stepped out. I pulled out the high quality, tight fishnet hose and proceeded to pull them up. Girls walked by and complemented me on my technique and my sexy legs. Once they were on, I found I could tightly secure my cock against body. I pulled up my leotard again and asked for a zip.

A cute redhead came over and looked me up and down. "You need boobs," she said and walked away.

She was right, the fabric was bunched my chest looked empty. I balled up my socks and stuffed them into the cups under my nipples. It helped, but a blonde came over and brought some tissues and more socks. She spent about five minutes expertly crafting my tits using whatever she could find. When she was done, several others offered a quiet round of applause and told me to jump and bend over. They held tight.

"Bunnies, don't forget your ears and puffy tails. We are meeting our guests in five minutes," Mr. Smith said from the hallway.

The girls were finishing their hair and makeup frantically. Someone called me over and put on lipstick and a little eye liner. I felt so pretty and included. I couldn't wait for our reveal.

We filed into the hallway single-file and paraded down a large staircase to the foyer. Men and women were milling about waiting for our arrival. "Ladies and gentlemen, please welcome the Bunnies!" the host announced. I recognized him from the newspaper, but still didn't know his name.

I was the last bunny in line and we all held hands as the guests ogled our bodies. I was intrigued that the women seemed as excited and turned on as the men to stare at the lovely ladies (and me) dressed in our sexy costumes. Granted, they complemented our boobs, pussies and asses very nicely, but these guests were really enjoying the flesh on display.

"Now bunnies, please relax and get to know our guests. Introduce yourselves and be sure to offer your best hospitality. We have bedrooms upstairs if you make friends," the host said.

One of the other bunnies came up to me: "Listen: they like lap dances, they will feel you up, there are no rules, the women play too. If you want a lot of tips, don't be shy. Shake your ass, rub their cocks and then pull them out. No reason to be shy. You're here to fuck and suck. Good luck girl," she said and then she was gone.

That was very blunt, but helpful. It cut out any premise of good behavior. This was a sex party and we were the hired hotties. I decide that I would have the most fun with couples. I had fantasized about MMF action so I decided to work on that.