Rachel's Dilemma Ch. 2

When I arrived home the following day, there was a package waiting for me. I opened the package to find two items; an old-fashioned clothes hanger designed for a woman's suit and weights. The hanger was wooden with a metal rod going across the bottom. The rod had two spring clamps on it from which to hang a skirt. The clamps could be moved along the rod to adjust their position. The spring clamps were very tight so even heavy wool skirts would be securely fastened.

The other item was a small bungee cord with the standard hook at one end and weights attached to the other. It must have weighed 2 pounds at least.

I had a good idea what these devices were to be used for and got hard just thinking about it in spite of myself. Rachel's poor tits were in for another long evening!

I then went over to my PC to retrieve my email. The first one was from Rachel's ex-husband. Here is what it said:

The slut is to wear the white cocktail dress with white stocking and the 5" white pumps. Her punishment will begin by having her tits spanked with a hairbrush. The hairbrush will then be used to spank her ass and inner thighs. Next, the suit hanger will be attached to her nipples and the weights hung from the hanger. Standing with her legs spread wide, her pussy will be whipped. Finally, with the hanger still attached, her tits will be whipped.

I could feel my excitement mount as I read this. When I had agreed to this little arrangement, I had not planned on getting turned-on by punishing my beautiful and sexy girlfriend. Was I weird? I had certainly heard about guys who got turned-on by causing women pain. But I had never been one of them! But here I was, excited and hard just thinking about my next punishment session with Rachel.

I called Rachel and told her I would be over in an hour to begin the session and relayed the dress code. A little over an hour later, I rang her doorbell. She opened the door and took my breath away. She was stunning. The tight, low cut dress displayed her large, luscious tits perfectly. The tight skirt came to just above her ankles but was slit up to her waist on both sides. Each step she took gave me a great view of her stocking covered legs. And since she was not wearing panties, her ass swayed and jiggled invitingly as she led me into the dining room. Her make-up was done perfectly to accentuate her natural beauty.

"Go stand by the dining table," I commanded.

I went to the implement table and deposited my new toys then went over to the video equipment and started recording. I then went over to my willing victim.

"Hands behind your head," I told her.

As she did this, I ask, "How are your nipples feeling today?"

"They are a little sore," she replied.

I reached out and slapped each of her breasts hard. She gasped.

"They are a little sore, SIR!" I said.

""They are a little sore, SIR!" she repeated demurely.

"Well, they are about to get a lot more sore," I said.

With that, I grabbed each of her nipples between my thumb and forefinger and pinched them hard.

"Aggghhhh," she groaned.

Again, as with the first session, I spent the next five minutes twisting, pinching and pulling her nipples eliciting moans of pleasure/pain.

Releasing her nipples, I commanded, "Remove your dress and then return your hands behind your head."

I went over to the implement table and retrieved the large, wooden hairbrush. It was an impressive instrument, wide and heavy.

I turned and saw Rachel clad only in white stockings and heels. Gorgeous. Her large tits stood out proudly topped by rock hard nipples.

"Spread your legs," I demanded.

As she meekly complied, I was treated to a nice, clear view of her pussy lips peeking out from beneath her triangle of hair. I grabbed one of her nipples and twisted it cruelly.

"Are you excited, slut?" I asked.

"No, it hurts!" she exclaimed.

With a smile on my face, I said, "Then your pussy won't be dripping like last night, right?"

She didn't answer. I'm sure she knew how wet she was. I confirmed it by running my index finger over her pussy. It came away drenched as expected.

"You enjoy having you tits punished, I see. Well, you will be beside yourself by the time this nights work is complete."

With that, I whacked the side of her left breast hard with the hairbrush. I followed this up with several more swats in the same spot. I then smacked the right breast several times.

By the time this little warm up was done, she was moaning loudly with her eyes closed. I moved to stand beside her and landed the hairbrush smack in the middle of her large tit. I continued whacking her breasts and engorged nipples with the hairbrush for several more minutes. Now she was crying out with each stroke.

"OK slut, turn around and bend over the table. Your ass needs a little attention," I said.

She did as she was told but I was not satisfied. I gave her a whack all my strength. She jumped off the table.

"Owwwww!" she screamed.

"Spread your legs, slut," I commanded.

Rachel spread her legs but again, not to my satisfaction. I whacked her inner thigh hard.

"Oh god that hurts," she cried.

"Spread your legs wider slut. I want to see your cute little asshole which I plan to fuck good tonight after I finish punishing your sexy body," I said.

Reluctantly, she spread her legs wide so her pussy was wide open and her anus peeked out.

"Good girl! Now I think you need a good, old-fashioned paddling."

And so, I started to spank her ass hard and fast with the cruel hairbrush. I landed the hairbrush ten or fifteen times in the same spot and then would move to the other cheek. Over and over I landed that brush on her ass. Rachel's reaction went from moaning to crying to screaming as her ass went from pink to red to scarlet. Once I was satisfied with the condition of her ass, I moved down to the sensitive area on the back of the thighs. The hairbrush made quick work of this area. Before long, they were also an angry red color on both sides.

"Alright Rachel, now I want you to get up and sit on the table."

She stood up and turned around and her tear stained face was a mixture of pain and pure lust. She very carefully got up on the table. Sitting on the solid oak surface on her battered butt must have been pure agony.

"Good slut. Now I want you to place the bottom of your feet together," I said with a cruel smile.

She looked at me with horror on her face. I think my beautiful slut thought I was going to spank her vulnerable cunt with the nasty hairbrush. But no, the pussy punishment would have to wait. My current target was her creamy white inner thighs. I raised the heavy brush and brought it down hard on her right inner thigh. She howled and immediately closed her legs. Annoyed that she moved form her position, I slammed the hairbrush on each breast.

"Get back into position and if you move again, I will tie your legs down and use the hairbrush bristle side up on your pussy after I've finished with your thighs," I commanded with another whack on her tit with the bristles of the hairbrush.

"Owwww," she screamed.

And quickly she returned her legs to their position. I noticed with satisfaction that her right thigh was pink where the hairbrush had landed. I knew she was going to have a very difficult time holding this position as I paddled her sensitive inner thighs. Well, she was the one who wanted this, not me (although I certainly was enjoying myself).

WHACK. I brought the hairbrush down on her other thigh. WHACK. WHACK. WHACK. I continued paddling her poor thighs. After about 5 minutes of this treatment, she was begging me to stop.

"Oh, pleaseeeeee stop. I can't take anymore," she begged.

Indeed, her thighs were an angry shade of red and very hot to the touch. Even though I thought she had enough, I was determined to continue a little longer so she didn't think her pleas were effective. I landed about ten more swats on each thigh. By the time I had finished, she was screaming in agony.

To give her a few minutes to calm down and get control of herself, I went into the kitchen to get a drink of water. Returning about five minutes later, she was still sitting with her legs wide apart. The screaming and crying had stopped and she had calmed down. I went to the implements table, dropped the hairbrush and picked up the coat hanger and weights.

Looking over my shoulder, I commanded, "Alright, Rachel. Stand up with your hands behind your head and your legs spread wide."

She slowly got off the table and obeyed.

I turned and approached her carrying the hanger and weights, watching her closely for her reaction. At first, she just stared at the stuff in my hand with a confused look on her face.

Then, as she realized what was about to happen, she cried, "Noooooo. Please, Peter, you can't be serious."

I reached out quickly and slapped her tits hard with my free hand several times.

"I don't want to have to tell you again, slut. You will address me as Master."

Then, without waiting for a reply, I grabbed her right nipple, pinched it tight to get it hard and quickly slipped one of the clamps from the hanger over it and released. She moaned loudly as the tight clamp crushed her sensitive areola. I slid the other clamp so that it lined up with her other nipple and quickly clamped it. Her moaning grew louder. I pulled the hanger away from her, stretching her nipples cruelly.

"Nooooooo," she screamed again.

"Oh, you want me to stop?" I asked.

I let go of the hanger. The heavy wooden hanger dropped yanking her nipples down. She yelped. I then held up the weights for her to get a good look at.

"Guess where these go," I teased.

"Oh Master, haven't I had enough?" she whined.

"I don't make the rules in this game, sweetness. I am just the hired help, remember?"

"You certainly seem to be enjoying yourself," she spat.

"There is no law that says a man can't enjoy his work," I said.

I hooked the weights on the hook of the hanger and let go slowly. When I was no longer supporting the weight, her poor nipples were being pulled downward in a most painful fashion.

"Oh, my poor breasts," she cried.

I lifted the weights a little.

"I must agree with your ex-husband. You use your beautiful tits to get your own way. Therefore, it is only fitting that they be punished severely."

With that, I dropped the weights.

"Aggggghhhhhh," she screamed.

"OK, I'll leave your tits alone for now. It's time to whip your pussy."

I returned to the implement table and selected a leather whip with 4 braided thongs. I returned to her, whip in hand.

"Now Rachel, I want you to spread your legs wider," I said quietly.

She slid them a few inches further apart. With my arm hanging down, I brought the whip up sharply with a flick of my wrist. The leather thongs whipped her exposed and spread cunt. She jumped and then howled as her tits bounced and suit hanger and weights bounced with them.

"Oh my tits!" she wailed.

"Interesting. I am whipping your pussy and you complain about your tits. Well, I'll let you in on a little secret. Once I am done whipping your cunt, I am going to finish by whipping your tits," I said cruelly.

She looked up at me in horror even as I flicked my wrist again. Again she jumped a little and again the movement was enough to cause the weighted hanger to bounce further torturing her nipples. As I continued to whip her pussy hard, she tried hard not to move. Towards the end, the pain to her pussy got the better of her and she jumped, trying unsuccessfully to ignore the pain it caused her tits.

After about 30 strokes, I stopped. I went over to her and roughly fingered her newly punished pussy. Again she jumped, both in pain and lust. Her cunt was dripping and her clit was rock hard. When my fingers ran over her clit, she bucked her hips trying to increase the pressure. I immediately removed my hand.

"Your pleasure needs to wait. It's time to finish. And, like last night, we finish off by whipping your tits. Unfortunately for you, your ex specified that this whipping was to be done with this device still attached," I said I indicating the coat hanger clamped to her nipples.

Teasingly, I flicked the whip at the weights causing them to bounce slightly. Each time they came back down, she moaned loudly. I noticed that her eyes were closed. Did she not want to see the whip striking her already red and sore tits or was she turned-on?

I raised the whip and brought it down on her right breast. A loud moan escaped her beautiful lips as she thrust her hips out. I brought the whip down on her left breast and again she thrust out her hips like she was trying to fuck something. I repeated this process a few more times but I was so hard and excited myself, I needed to get this done so I could get relief.

I moved to her side and brought the whip across her tits, the leather thongs striking both her nipples simultaneously. After a few more of these, Rachel suddenly began convulsing and gyrating wildly. I couldn't believe my eyes. She was having an orgasm. Again and again the convulsions ran through her body as I continued to whip her tits.

Finally, I could not take anymore. I dropped the whip and quickly went over to the video camera and shut it off.

"On your knees, slut," I commanded.

"But the session is over," she protested.

I lifted the weights hanging from the hanger and dropped them. Rachel screamed.

"It is over when I say it is over. Now get on you knees."

She quickly complied to my demand. I slowly undressed as she watched, mesmerized. When I was completely naked, my hard cock stood proudly erect. My lovely slave/slut was staring right at it, licking her lips. I took a step closer and before I knew what was happening, she had the entire length of my hardness in her mouth. Soon, I came like a volcano erupting. I discharged so much cum that Rachel could not swallow it fast enough and it dribbled down her chin and onto her breasts.

When I was done, I told my lovely girlfriend to stand and I removed the suit hanger from her nipples. As the blood returned to her deprived nipples, she experienced a new wave of pain. The fact that I was pinching them to get the blood circulating again only stimulated her more. Before I was done, she was moaning and thrusting her pussy out again.

It was going to be a long, erotic night!