All the way home in the jet I thought of ways I could be punished. To my surprise the fantasies I developed were not dreaded. I found instead that they excited me. I finally decided that the most humiliating and therefore the most painful would be a spanking but not with his hands but one of the whips. I eliminated the pussy whip immediately since it did not hurt. I did not have the nerve to suggest the braided whip and decided to leave the choice to him.
"I have decided I acted like an irresponsible child. I should be punished like a child with a spanking but not with your hand. Something that hurts more."
"We both know the braided whip hurts a lot. Is that what you deserve?"
I shuddered at the thought but said, "I guess so if you think I should be hurt that much."
"No. It is your decision."
I realized his wife must have volunteered to suffer for him and I wanted to prove I could do it too and even more.
"Yes! Use the braided whip. I deserve it!"
"I agree but how many spanks? Fifteen?"
"No twice as many. Give me thirty!"
I could hardly believe I had suggested that. I realized I would not be able to sit for a long time. He made it worth it by saying, "I am proud of your bravery. You are an amazing girl. This will keep you aware of the coming event."
He had me pull up my sweater then took out the braided whip and tied it tightly around my waist. All the way back to his penthouse I had mixed feelings of fear and excitement feeling the whip dig into my waist with my breathing and every move.
When we got to his place he kissed me then pulled my sweater off while I held my arms up for him then took off my skirt and panties. He patted my butt then said it was perfect for spanking, being round and firm. He told me to give him the whip and my fear and excitement rose rapidly as I fumbled with the knot.
I instinctively dropped to my knees to kneel as I handed him the whip saying, "I have been bad. Please whip me."
He took my hand and led me over to a leather easy chair. The back was low so I spread my legs to let my stomach settle on the top and gripped the arms of it with my hands.
Just as I got settled I felt this searing pain across my butt cheeks and gripped the arms as I screamed. It went on each as bad as the first as I gripped the arms with my hands and the sides of the chair with my knees to resist running away.
At the tenth lash he stopped! He came around to hold up my tear stained face to say, "You are in a lot of pain aren't you?"
"Oh yes! It is terrible!"
"Do you want me to stop?"
Oh God did I! I hoped he might be merciful so I sobbed, "Do what you want to do."
He kissed me and said, "That's my brave girl." and began whipping me again. I found that he had done me no favor by stopping after ten. My nerves had begun to get numb. By stopping they were alive again. Thankfully they began getting numb again and when he quit on the thirtieth I could have taken even more.
When he quit he stepped behind me and drove his monster into my pussy from the rear. To my amazement I was wet and it went in easily. The slap of his thighs against my butt added just the right amount of additional excitement to make me go into one glorious orgasm after another.
After he came he carried me over to the bed and laid me down on my stomach where I caressed the welts on my butt while he opened a bottle of champagne. He gave me a glass then took some lotion out of the end table and began soothing my smarting butt as he said, "I think we will get along very well. I am no longer going with the girl I had when I met you. Would you like to be my girl?"
"Oh yes! I'll do anything to make you happy."
"That is what my last girl said but she didn't do it willingly. She told one of my friends she was just going along with me until I married her. After that she would do as she wished. Thankfully I believe in long engagements that let me find out what a girl really thinks."
He got up and went to the closet and brought back a beautiful, black, beaded cocktail dress. He told me to put it on then went to a drawer to get a beautiful, what I thought was a diamond necklace to put around my neck to take me out to dinner.
He had a sports car in the basement parking garage. When I sat down I felt the beads digging into my welts. My butt was aching by the time we got to the restaurant. I was dismayed to see they had wicker chairs. I knew he realized I was suffering as I squirmed in the chair to find a better position but he just dawdled over his drinks and meal till all I could think of was my aching butt.
I am sure he took the road home that had the most potholes but he said he was proud of me for being such a lady even though he knew I was uncomfortable.
That night he went down on me for a long time to insure I would have orgasms when we fucked.
That formed a regular pattern. Anytime I was hurt I was rewarded later by presents and love. The more I was hurt the better the present and the more foreplay to guarantee orgasms.
The next morning I woke up early out of habit and did not know what to do. He had not asked me to stay with him and if I was going to go to work I needed to hurry home for work clothes.
I decided to wake him to tell him I had to leave for work. When he was awake he said, "Do you want to work? You can quit and stay with me if you like. I think I want you to be my new girlfriend."
"Really? But how will I pay my apartment rent?"
"You don't need an apartment if you are staying with me, dummy. Just call your boss and tell him to take his job and shove it. We will get your things from the apartment later."
I was so excited I kissed and hugged him till he told me to leave him alone because I had worn him out and he needed more sleep.
I was too excited to go back to sleep so I made coffee then went swimming. The warm water on my nude body felt wonderful and when I looked in the mirror I saw that my welts were now just dark red or purple lines that did not hurt and went away completely in a few days.
I called the office as soon as it was open to quit my job. My boss was really mad I gave him no notice but I didn't care.
Jon got up about ten and told me to dress to go to my apartment.
He didn't like any of my things and told me just to keep things I was attached to and the other stuff could go to charity. I felt a little hurt since it had taken a year to pay off my furniture but had to admit it would look cheap in his place. I ended up with just a box of photos and other momentos. He called my landlord and told him he could keep the furniture or give it away and where to mail my damage deposit. By the time he deducted cleaning it only amounted to fifty dollars.
For the next few days I was not hurt but I was treated just like a pampered pet. He dressed me in clothes he picked out if I wore clothes at all. He ordered all the meals at restaurants except for snacks I made from groceries he ordered over the phone and had delivered. I especially felt like a pet dog when he wanted to watch TV because he would have me kneel next to his chair and idly stroke my hair or body while he watched.
I realized just how dependent I was on him when I got the deposit and realized I had a total of seventy five dollars in cash, no job, no recommendation from my employer to help me get another, no clothes suitable to work in, and no place to live if he tired of me.
Just as that reality set in to frighten me he said,
"It just occurred to me that we have not tried the thong whip. It may give you orgasms like the pussy whip. Would you like to try it?"
"I thought I would just be whipped or spanked if you were unhappy with me?"
"I will be unhappy if you do not get on your knees and beg me to whip you."
This was the first time I knew that no matter how much I pleased him I could not avoid pain. I was confused by my feelings about that. I was beginning to enjoy being his total slave and also was excited by the prospect of being whipped. Even my terrible spanking evoked memories of my fantastic orgasms after it was over rather than the pain.