Chance Encounter Ch. 04: The Auction

Chance Encounter 4 -- The Auction

After Rhonda and the gurls cleaned me up and touched up my makeup, they returned me to Mark. "Well Toya are you ready for your special treat?" "Yes Master," I replied because I knew that was the only acceptable answer. I must have looked less than enthusiastic as Mark grabbed my face and roughly turned it to him. "Toya -- you are being trained by us as a sissy slut whore. We have invested time and money in you, you old bitch, even though there has been some skepticism about your ability to attract business. We are gambling on the novelty of a granny tranny whore who can pass for a respectable woman on the arm of an older gentleman. Do you understand sissy?"

"Yes, Master."

Mark led me to the stage at the front of the room. As he approached the microphone, the room settled down.

"Mistresses and Masters it is time to auction of the virginity of this cum slut. Who will open the bidding?" Someone in the group shouted out

"Ten dollars for the old hag!" A murmur went through the room. I was terrified that this is what the men thought of me and that I would fail Mark.

"Two hundred," said another man.

"One thousand dollars" said Mr. Levenson with a smirk.

"Two thousand dollars," cried out the silver-haired man.

Not to be out done by the silver-haired man, Mr. Levinson bid $5000.00.

As the bidding progressed, I noticed that Lacy and Sherry approached the man who had disrespectfully made the $10.00 bid. He was smirking at the process. His wife stood next to him.

"Excuse me Master, Mistress. Frank and Bethany? Peter would like to see you in the Red Room for a private party so that you might be spared this event. "

"We would love to," said Frank. "I guess Peter understands how pathetic this old hag is."

"Yes, I agree with my husband,Mark must have been out of his mind when he put together this travesty, " Bethany said effectively sealing her fate"

Lacy and Sherry led the couple to the Red Room. Lacy and Sherry seated the couple at a nicely appointed table with a bouquet of dildos as a centerpiece. They were offered drinks as they waited for Peter. "What's happening?" said Bethany as she swooned and passed out. Lacy eyed Frank who was also having difficulty staying awake. "Well asshole, you and your cunt wife are going to learn the price of disrespect. Here is a taste of what you can expect." Lacy kicked Frank in his jewels, he groaned and then passed out as well.

After securing the couple, Lacy and Sherry returned to the main room where the auction continued.

These two bidders kept raising the bid until it reached $10000.00.

The room was silent, I was stunned, and Mark had a great big grin on his face.

"Are there any more bids? If not, I am closing the auction and the winner is Paul Whitely." Master Paul approached the stage with his wife Casandra. What a stunning couple.

"Congratulations Paul and Casandra."

"What do you have to say, Toya?"

"Thank you so much for generosity Master and Mistress, I gushed"

"I have a question" said Casandra "After Paul takes her virginity, may I have a turn with her as well?"             

"Of course, smiled Mark, "You may do whatever you like in the honeymoon suite."

"Toya return to your room. Mandy and Rhonda will help you get ready. Rhonda took my leash and with a little tug we were off. Once we got to my room, the gurls and I got busy. First, they helped me undress and showered. Of course, I applied the depilatory cream all over. I just love the feel of my hairless body.

Next Rhonda handed me an enema bulb filled with milk. "This is to help you be ready for your big event." After cleaning me inside and out it was time for me to get dressed.

Rhonda handed me a pair of white stockings which I lovingly rolled up my legs. This was followed by a beautiful white garter belt that the gurls help me hook up to my stockings. Next came a beautiful white lace bralette that lovingly caressed my little breasts.

Rhonda helped me with a beautiful white under bust corset that she cinched up tight. When she was done, I asked if she could go a bit tighter as I wanted to be the best I could be for my Master. "Good gurl Toya." Rhonda walked over to me and kissed me passionately. I was not expecting this, but I quickly responded and returned her embrace.

"I have something special for a special sissy gurl." It as a jeweled butt plug that she carefully lubed and inserted. Rather than feeling intrusive, it felt like it was right where it belonged. Next Mandy touched up my makeup and hair. As I stood in my stocking feet and looked in the mirror, I was stunned by the beautiful mature lady that I saw. I swooned a little contemplating all that happened since the coffee shop. I had to admit that I loved this new me. Next, Rhonda put on my new, white sissy collar and handed me a pair of white pumps with four-inch stiletto heels. "Try these on sweetie and see if you can manage them. If they are too much, we can get you a pair of kitten heels." As I practiced and gained confidence with my new heels, I realized that I was eager to please my new Master and lose my virginity. To finish off, I put on my veil and a princess tiara. Next, they helped me into a long, lacy see-through white gown.

"OK, it's time to go to your Master, Toya and get you properly deflowered," she chuckled."

We three were off to the honeymoon suite. Rhonda in the lead, holding my leash, I followed next loving my outfit and the vibrations coming from my butt plug. Mandy trailed behind holding the train of my dressing gown.

As we entered the honeymoon suite, the first thing I noticed was Paul smiling at me.

"Welcome Toya, I am so glad to see you."

"Thank you, Master, I am pleased to be here."

"Rhonda, you may hand me the leash and then leave."

"Yes, Master," said Rhonda.

She handed the leash to Paul and then Mandy and Rhonda left. I'll admit to being a bit nervous since I was alone with strangers. Casandra and Paul both wore masks to conceal their identity from the ever-present cameras. Paul had a simple mask, but Casandra had a latex hood that complemented her full latex cat suit. Paul dropped my leash and approached me.

"Toya, I am going to make this as special an experience as I can for you."

Paul took off my robe and veil. As I stood in front of him, I was surprised when he started to slowly get undressed. As he did, he continued to gently smile at me. Once he was naked, I knew what to do and got down on my knees and took his cock in my hand and lowered my lips to its tip gently kissing it. I proceeded to plant little kisses on hos cock as I moved down its eight inches until I reached his balls. I took each one in my mouth and gently sucked while I swirled my tongue. His gentle moan told me that I was doing well. I made my way slowly back up to the tip and took him in my mouth. I retraced my earlier route by taking more and more of him until my lips touched his balls.

I continued ministering to Master Paul until he told me to stop and stand up. I was surprised when he gently held me and then kissed me deeply in a way that made me swoon. He led me to the bed and had me get down on all fours at the edge of the bed while he stood behind me.

"Are you ready, Toya?"

"Yes, Master, please take me"

Master lubed his stiff cock and pressed against my boi pussy. As he entered me, it hurt as he stretched me, and I yelped. As he continued to move ever deeper into me, I felt a release and my pain was transformed by his penis into pleasure. I found myself pushing back to meet him as he thrust forward.

"Oh, Master, please don't stop! Please fuck me -- fuck me harder"

I wanted this to never end.

As he withdrew from me, I whimpered, not from pain, but from the loss of his cock inside me.

"Toya, lie on your back and spread your legs to welcome me back ."

"Yes, Master," I said as I quickly scooted up the bed, lay on my back, spread my legs, and looked lovingly up at this man who had so deftly taken my anal virginity and gave me the best sexual experience I had ever had. And we weren't done. He quickly moved between my legs and put his stiff cock back into my hungry boi pussy.

"Oh, Master, please fuck me.

"Toya, your tight cunny feels exquisite, and I am not sure how long I will last" he said as he continued to fuck me. "I want you to look at me while I fill you with my seed."

He eyed my clitty and noted that since it was so stiff, I must be having a good time as well. He took one of his hands and caressed my penis. The feeling was electric causing me to shudder. Soon after I felt myself getting close to orgasm and at the same time Master's thrusts became more urgent. I focused on meeting him and serving his needs.

When he came, filling me with his cum, that sent me over the edge and my clitty erupted as well. When he withdrew this time, I moved to clean him up. As I sucked his cock clean, I felt a hand on my ass and a plug put in my boi pussy.

"We don't want to waste any of that do we sissy," Casandra said.

"No, Mistress."

I was in heaven and forgot that Casandra was there. I was soon to find out that I would be very aware of her presence.

Paul helped me undress and naked we showered together. We soaped each other up and he hugged me close. I could feel my clitty and his cock dancing together between us. He looked in my eyes and kissed me long and hard. After drying off, I noticed that there was a robe for Paul, but my clothes were gone.

"You won't be needing those clothes, sissy. I have other plans for you."