I had been dating Rachel for 3 month when she told me of her dilemma. She had received an offer from her ex-husband. He was extremely wealthy. He made his money during the PC revolution. Anyway, during the divorce, she got screwed. He hired expensive lawyers and left her penniless.
Her ex had heard she finally had boyfriend. And he was ready to make a deal. Money for pain. Rachel had hurt him badly and now he wanted retribution. He was willing to give her the money she wanted if she would be willing to be punished. BY ME!
He had called her and told her he would be willing to renegotiate their divorce agreement. He would be willing to give her 1 million dollars if she would accept 1 hour of punishment per day for the next year.
Now I was in the middle!
She wanted to do it. I didn't. She said it was an opportunity to get what she deserved. I said it could destroy our relationship!
Her ex sent a first class airline ticket to London for me if she was interested.
I went to London!
He told what he wanted and that all sessions would be video-taped so he would know what he was buying. I told him he could dictate to her but not to me. He could determine what she wore and the punishment plan, but I was responsible for the actual punishment.
We agreed.
He gave me 3 bags; one contained clothes for Rachel to wear during her punishment, one contained sophisticated video equipment and one contained implements of punishment; whips, paddles, clamps and various other devices I wasn't sure about. I prayed I wouldn't get stopped at customs.
I returned to Rachel and again voiced my disapproval. I described his plan to her. Each day, we would video me punishing her for 1 hour. She would do whatever I commanded her. At the end of each month, she would receive a check for $100,000.
She agreed.
Rachel has a classic hour-glass figure…big tits, thin waist, wide hips and a big ass that was going to be a lot of fun to spank. She was very self-conscious of her wide caboose and always wore loose fitting skirts or pants. She also knew that her large tits attracted men like moths to light. She always wore tight tops which were usually low cut. She had a overactive libido, always wanting me to do her.
Her ex-husband knew she used her tits to attract men and his plan for her punishment paid special attention to them. At least half of each session was devoted to punishing her big breasts.
The deal was finalized. The money was put in escrow. She would be my slave for 1 hour each day. I would receive an email each day describing the plan for that day's punishment session.
Rachel unpacked the bag of clothes while I set up the video equipment. When I finished, I went to review the clothes. Her ex definitely wanted her to be dressed like a slut for her punishment! The clothes were all tight with the tops low cut and revealing and the skirts very short and revealing. To complete the outfits, there were garter belts, stockings and several pairs of 4 to 5" pumps. Rachel had a distressed look on her face. We went through the toy bag together. I figured she should know what she was getting into. It contained several leather whips including one small one, two wooden paddles, a riding crop, a large wooden hair brush, a wooden spoon and a long, heavy metal spatula, several pairs of alligator clips, several boxes of binder clips of varying sizes, a pair of pliers, two adjustable vice wrenches and a bag of wooden clothespins. It also contained wrist and ankle cuffs and several coils of rope. Rachel was white as a sheet. I tried one final time to dissuade her although I secretly wanted her to do it now.
"No," she said, "I need this money. Besides, I might even enjoy it."
We begin.
The email from her ex stated she was to wear a tight, very short and very low cut black dress with spaghetti straps and black stockings with 5" black heels. I told her and she went to change. While she went to dress, I reviewed the rest of the email. I was to begin by whipping her tits. Then the alligator clips were to be clamped on her nipples while I gave her a hand spanking. Next, her tits were to be punished with the riding crop. Finally, her pussy was to be whipped. I didn't share this part of the email with Rachel. I wanted her punishment sessions to be a surprise.
I made a final check of the video equipment. Finally, after nearly an hour, she entered the room. She took my breath away. The outfit made her look more naked then if she actually was. Her large tits were barely covered as the dress was open in front to her navel. I noticed with amusement that her nipples were already hard, pushing on the thin fabric of the dress. She had done her makeup to perfectly compliment her outfit. All in all, she looked like a very sexy slut.
Before we started, I told her if at any point she could not go on, she should simply say 'monkey' and it would all be over.
I turned on the video camera.
"OK Rachel, your first punishment session will begin now," I said. "Place your hands behind your head."
She looked at me with a puzzled expression on her face but complied.
"Rachel, for the next hour, you will be my slave. You will do everything I tell you to do immediately and without question. You will not speak unless ordered to do so. When you do speak, you will address me as Master or Sir," I finished.
"You are going a bit over the top, don't you think?" she said.
"These are the rules for your punishment sessions. If you question me again, your punishment tonight will be extended to 2 hours," I replied sternly.
Her face showed concern and a little fear. I knew she was wondering what she had gotten herself into.
However, all she said was, "Yes Sir."
I walked over to her, grabbed her hair and pulled her head back.
"That's a good slave."
Then I released her hair and took her nipples between my thumb and forefingers and pinched them hard.
"Aggghhh," she moaned.
I pinched and pulled and twisted her engorged nipples for several minutes. By the time I finished, she was moaning loudly and gyrating her hips. Her eyes had glazed over. Was she enjoying this? It was hard to tell. I knew one sure way to find out but decided to wait awhile before venturing there.
I released her nipples and took a step back to admire her. Her nipples were rock hard and fully an inch long.
"Hands at you sides," I commanded.
She complied immediately. I took the straps of the dress and slid them down off her shoulders exposing her large, white breasts. The contrast to the rest of her well tanned body was dramatic. Soon I knew those white tits would sport red stripes.
"Put your hands back behind your head," I ordered.
Slowly, hesitantly she did as she was told. It was then she realized that her tits were about to receive more punishment. I went over to the table with the implements on it and selected the small whip. It was all leather with a braided handle attached to 4 thin thongs. I returned to her and took the whip in my right hand grabbing the thongs with my left hand. I brought in up to shoulder height and flicked my right wrist down as I released the thongs. CRACK. The whip came down on her left breast leaving a red mark. I repeated the process another nine times hitting different spots on the top of her left tit. By the tenth stroke, there was a nice red glow. I repeated the process to her right breast. This done, I grabbed one of her breasts and squeezed hard. Again, the process was repeated to the other breast.
Next, I used a sidearm motion to whip the side of her large tits. Ten stokes to the right and using a backhand motion, ten to the left. By the time I had completed these punishment, Rachel was crying and screamed with each new stroke.
I now took her left nipple between the thumb and forefinger of my left hand and used it to lift her breast. With an upward flick of my wrist, I whipped the underside of her breast. She yelped. Ten on each breast.
Finally, I again grabbed the thongs of the whip in my left hand and with the whip slightly lower, let if fly. THWACK. The thongs of the whip landed direct on her already sore and swollen nipple. She moaned. Twenty times I whipped her left nipple and twenty times I whipped the right nipple.
Again, I took a couple of steps back to admire her. Her tits were well used and abused with several many red stripes. And her poor nipples were purple. And they were about to be abused further.
