Rachel’s Dilemma


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 görükle escort 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 bursa escort bayan 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.

I went to the implement table, dropped the whip and picked up the two alligator clips. Squeezing the handles together for the first time, I realized that the spring was very tight. The wicked looking teeth on the jaws were going to dig deep into her swollen areola.

I returned to her and cruelly showed her what I had in my hands. Her eyes grew wide as she recognized my intention..

“Oh no, I can’t take that,” she cried.

I reached out and slapped her right breast hard.

“I told you not to speak unless you were told,” I scolded.

Then I slapped her left breast. She cried out more in horror of what was about to come. I again grabbed one of her nipples with the thumb and forefinger of my left hand and pinched it. With my right hand, I squeezed the handles of the alligator clip opening the cruel looking jaws, placed the jaws over the nipple and slowly released my grip on the handles. She began screaming when I was only half done and began shaking her breasts madly when I had completely released the little torture device trying to throw it off. Quickly though, she realized that this only increased her agony. I grabbed the other nipple and quickly snapped on the other clip. She howled again. After several minutes, she composed herself. I decided to test this new found composure. Quick as a snake, I shot my hand out and flick both clips. She jumped in pain and cried out again. Then she turned trying to shield her breasts from me. I grabbed one of the clips and pulled her straight.

“OWWWWWW,” she screamed.

“Don’t try to pull away from me or your punishment will be much worse,” I said.

I left her to ponder this while I went into the kitchen to get a glass of water. This was thirsty work.

I returned to find her with her eyes closed.

“You will be happy to know that we are finished with your tits for now,” I said. “I want you to go over and stand in front of the dining room table.”

Very slowly she walked over to the table so as not to shake her tortured tits least they hurt more. Once she was there, I followed and stood behind her.

“Spread your legs,” I commanded.

She moved here legs about two feet apart.

I gave her ass a hard swat and said, “Wider!”

Quickly she spread then further apart.

“Now bend over the table,” I said.

She slowly bent at the waist, moaning as she did because her tits were now hanging down. I put a hand in her back and pushed her down until here tits were pushed flat by the table. She screamed as the alligator clips dug in deeper when they made contact with the wooden table. She struggled to raise herself off the table but my hand easily kept her in position.

The combination of her legs spread wide and the obscenely short skirt caused her entire ass and pussy to be exposed when she bent over. Now was the opportune time to see if she was enjoying this. I took my index finger and ran it along her cunt. It was soaked. The slut was turned on like I had never seem her before. She was literally dripping. When she felt the contact with her pussy, she pushed her hips back trying to bury my finger deep. But I was too quick for her as I retracted my finger and gave her another hard swat on her now exposed and vulnerable ass.

“This is punishment, slut. If you are very good and take you punishment like a good slut, maybe I will permit you pleasure when we are bursa escort done,” I said looking into the camera with an evil grin. Let the bastard suffer a little at the thought of me banging his ex-wife when this was over.

“Now it is time for a good old fashion spanking, slave,” I said.

With that, I drew back my hand and brought it down hard on her large ass. It jiggled nicely and left a nice red hand print. I began to spank hard and fast. Soon she was crying again as another part of her anatomy was punished. Again and again my hand landed on her vulnerable ass. Soon she was gyrating her hips in a vain attempt to relieve the burning. I gave her about 300 swats although to be honest I lost count early on. Suffice it to say, I didn’t stop spanking her until I couldn’t lift my arm anymore and my hand was really sore. I made a note to talk with her ex about coupling hand spankings with paddling or whipping in the future.

When I could spank no further, I roughly rubbed her ass. It was very hot to the touch and extremely red. My fingers wandered down to her pussy and I found her clit rock hard. Again, she tried to buck her hips in order to plunge my finger inside. Again, I anticipated her move and she received several hard swat on her thighs for her trouble.

“Alright slut, stand up,” I said.

Slowly without removing her hands from behind her head, she stood up straight.

“Turn around,” I commanded as I walked over to the implement table and retrieved the riding crop. Again, I showed her the next instrument of her pain and saw a look of panic come over her when she realized the probable target. I was sure I was going to hear ‘monkey’ in the next moment. But I didn’t.

I reached out and removed the alligator clips from her nipples. As the blood began to return to her tortured nubs, she screamed in pain. When the waves of pain subsided, I swung the crop and landed it on the top of her breast. Ten to the top of each breast, ten to the side and ten to the bottom. The first one that landed on her poor nipple caused her to scream again. Again, I thought I might hear the safeword but no. Twenty stokes to each nipple and she nearly collapsed to the floor when it was over.

I gave her a minute to compose herself. The hour was nearly up and I needed to complete her punishment. I went to the implement table and retrieved the small whip.

“Sit on the table,” I commanded.

Somewhat confused and unsure of what was coming next, she hopped onto the table. The minute her sore, red ass touched the table, she jumped.

“Now lay back,” I said. She did as I commanded still confused and a little concerned.

“Now raise your legs and grab your ankles.”

Suddenly, she realized what was in store for her.

“Noooo,” she squealed.

I gave her ass a few good, hard swats.

“You will receive fifty lashes on your pussy. Forty as you are and for the last ten, you will spread your cunt lips wide so I can punish your clit.”

“Oh please, haven’t I had enough?”

“This is the last of it,” I said sympathetically.

I moved in front of her and without hesitation, raised the whip and brought it down on her exposed cunt. She cried out but held her position. I landed the whip there again and again. She wriggled and squirmed and cried. Finally I was done except for the last ten.

“Now, I want you to reach your hands down and spread you lips,” I commanded with a stern voice.

With a resigned look on her face, she placed one hand on the back of each thigh and spread her cunt wide with her index fingers.

Taking careful aim, I landed the whip square on her hard, throbbing clit. She screamed but held on. Again I landed the whip on her clit. Again she screamed. After three more licks on her clit, Rachel began to convulse wildly. She was cumming. Quickly, I landed five more directly on her exposed clit. She continued to convulse for the next several minutes as wave after wave rolled over her.

Her punishment complete, I quickly went to turn off the video camera. I needed release and I would be damned if that rich bastard was going to get any more than he paid for.

I quickly stripped off my clothes and shoved by pulsating cock into her sore pussy. She screamed and we both exploded together in an incredible orgasm.

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