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.
