When I was 18, I met and began to date Karen. Karen was 27 years old with beautiful, long wavy red hair, gorgeous green eyes and big tits. Hey, at 18, that’s all that matters. After our very first date, she rented a motel room and we fucked all night long. I fucked her pussy, I fucked her mouth, I fucked her tits and I fucked her ass. She was the horniest woman I ever met.

The next day, after we both recovered, she invited me over to her apartment. When I got there, she was wearing a low cut, tight mini-dress with stocking and 5″ pumps. It was obvious what she had in mind for the day. She invited me in and told me to make myself at home while she finished putting on her makeup. As I looked around her place, I was surprised at what I saw. On her walls hung two strange and erotic drawings of women being punished and tortured. As I looked more closely, I realized more precisely that the women were having their tits tortured. One woman was wearing rat traps on both nipples while another had wood clamps crushing her areolas. To be honest, I was absolutely fascinated. And I got the idea that Karen must like this sort of thing. While I was studying the drawings, she had come up behind me.

“Do you like them?” she asked.

“Yes, I find them strangely erotic,” I replied. “Where did you get them?”

“I drew them,” she said.

I turned to look at her with many questions in my eyes. Instead of answering them, she just kissed me with a deep, passionate kiss. As we parted, I noticed that her nipples were hard and pushing out of her dress. On an impulse, I took both nipples between my thumb and forefingers and squeezed hard. She let out a scream, more of shock than anything. But she did nothing to stop me. So I continued to pinch harder and twist her rock hard nipples. She began to moan and suddenly she placed her hands behind her head, thrusting her tits out even further, increasing their vulnerability. She was obviously enjoying this.

“Put you hands down at you sides,” I commanded. To my surprise, she complied immediately. I grabbed the straps of her dress and yanked them off her shoulders and down her arms exposing her lovely, lily white breasts. I slapped her left breast and commanded, “Replace you hands behind your head.”

As she did, I slapped the other breast. She said nothing, just stood there with her hands behind her head and her eyes closed.

I decided to test exactly how much she could endure! I again grabbed both of her nipples, squeezed them tight and pulled them up and away from her body. She arched her back slightly to relieve the pressure. I pulled harder and then twisted. There was a sharp intake of air and a loud moan, but again she said nothing. I continued pulling, pinching and twisting for several more minutes. She moaned and began breathing hard as the pain in her tits increased.

I was hard as a rock and my cock was straining against my pants. I would need some relief soon. I wondered if this activity was having a similar effect on her. I released her nipples and stood back.

“Spread your legs,” I commanded. She opened her eyes and looked at me. She dropped her arms to her sides and spread her feet until they were 3 feet apart.

“Did I tell you to move your hand?” I asked as I slapped her breasts sharply. Quickly, she returned her hands to their former position behind her head.

I lifted her dress and saw her cunt juices dripping down her legs. This woman was a pain-slut. More specifically, she was a pain-slut who got turned on by having her tits tortured.

“I see you are enjoying our little game. I think it is time we got a little more serious. Do you have any of the toys in your drawings?”

Her face drained of it’s color slightly as she stared at me. “I-I..um-have never actually done those things,” she replied. “They are fantasy representations.”

“Well then, I think it is time for you to experience your fantasies!” I exclaimed.

“I don’t know… it will hurt too much,” she answered.

“Who are you kidding. You love the pain. I’ll bet I can even make you cum without ever touching you.just by causing you pain! I am going to run to the store to pick-up some supplies. I want you to get on your knees and wait there for me until I return.”

“I told you I’m not sure I want to do this,” she said somewhat demurely.

“OK, then I’ll just leave and you can go on being a frustrated, unsatisfied slut,” I replied calmly. With that, I went to retrieve my coat. When I returned, I found her on her knees in the middle of the room.

“Ah, so you’ve changed you mind, have you. Well, I think it is too late. I’ll be seeing you around,” I said cruelly.

“Oh, Jack, please don’t go,” she said, her voice trembling.

“What do you want, Karen?” I asked.

“I want you to stay,” she replied.

“And do what?”

She paused and looked down at the floor, then said, “I want you to punish my tits.”

“Beg me, slut!”

“Please Jack, please punish me,” she begged.

“You will address me as Master Jack from now on, cunt!” I commanded.

“Yes Master Jack,” she said, eyes still downcast.

On an impulse I asked, “Do you have any more drawings other than the two hanging on that wall?”

Surprised, she answered, “Yes.”

“Go get them.”

She got to her feet and began to walk towards her bedroom.

“Who told you to stand up,” I asked in a loud voice. “Get back here.”

She came back quickly and got on her knees immediately.

“That’s better. Now go get the drawings and when you return, I am going to whip your ass as punishment for being presumptuous,” I said.

She crawled into her bedroom and returned about 3 minutes later with some two dozen drawing in her mouth.

“Come here, lay them in lap,” I commanded. She crawled over to me and dropped the drawings in my lap.

“Now, reach back and pull up your dress in preparation for your punishment.”

As she complied, I began to look at the drawings. The first one was of a woman tied spread eagle standing up. Another woman was standing next to her whipping her large, exposed tits. The next one depicted a woman on her back on a kitchen table, her hands and feet tied to the legs of the table. Jumper cables were attached to her tits while a woman whipped her vulnerable cunt. The next was of a young girl in a nightie with her arms held from behind by an older woman while a man was cruelly twisting her tender nipples.

Man, this woman had some imagination. Her best drawings (actually, it was a series of 3 drawings) portrayed a young woman with large tits tied spread eagle standing up. A rope around her waist attached to a wall behind her held her in place. Attached to each nipple was a large binder clip. Bungee cords were attached to each binder clip, stretched tight and attached to the opposite wall.

This poor girl’s nipples were being pulled in a most painful manner. To increase her pain, a older woman (who looked like her mother) was whipping her ass with a belt. I can only fantasize about how her nipples got pulled out even further each time the belt connected with this young woman’s tight, red ass.

Needless to say, these drawing fired up my imagination, among other things.

“Very nice,” I said. “You certainly have an active imagination! I take it from the drawings that you are not only a pain-slut, you are a bi-sexual pain-slut.”

She looked up at me and answered, “Yes Master. I fantasize about both men and women punishing me.”

“That’s excellent. I have a friend who is going to love punishing you. She and I are going to have lots of fun with your sexy body, slut.”

I stood up and stood in front of her. “Up on your knees and remove my belt. It is time to begin your punishment,” I stated.

She immediately raised up and undid my belt and began pulling it through the loops. I grabbed her hair and yanked her head back.

“With your teeth, bitch,” I said as I slapped her face lightly.

She grabbed the buckle of the belt with her teeth and began to tug. After several tugs, the belt came free and was dangling from her mouth. I took the belt and said, “Alright, cunt, stand up, go over to the side of the couch, spread your legs wide and bend over the arm.”

She meekly complied.

“Pull up your skirt you silly bitch,” I barked.

She immediately reached back and pulled up her skirt giving me a perfect view of her tight ass and wet, hairy cunt.

I moved over next to her, doubled the belt over, raised it high over my head and brought it down hard on her ass. WHACK. To her credit, while she flinched, she didn’t move out of position. I raised the belt again and whipped her ass again. TWACK. She groaned and dug her fingers into the couch. Again and again I belted her ass. During this whipping, Karen proved to me what a pain-slut she really was. As her ass got redder, she began to lift her ass into the air to meet the belt.

When I finally stopped, she lay over the arm of the couch panting and moaning. I caressed her hot ass and then let my finger wander down to her pussy. It was hotter than her ass and absolutely drenched.

I decided her poor cunt needed some attention. I had tortured her tits (although I was far from through with them) and whipped her ass. I just wouldn’t feel right if I neglected here hot little pussy.

“Turn over,” I commanded.

She looked at me over her shoulder. I could see the animal lust in her eyes along with confusion.

“Turn over with your ass on the arm of the chair, your feet spread wide on the floor and your hands on the couch. I am going to whip you pussy now,” I said in a matter of fact voice.

“Oh, nopleeeease, Jack,” she squealed.

That got her several very hard spanks on her already sore ass.

“I told you to address me as Master! And the next time you say no to me, I will take you out into the street and whip you in front of all your neighbors! Do you understand?” I queried.

“Yes, Master,” she whispered.

“Good. Now do as I ordered.”

She slowly turned over, placed her feet on the ground and very gently placed her butt on the arm of the couch. Then she arched her back and placed her hands on the seat of the couch.

I placed my foot against her left foot and slid her legs another foot apart. This had the effect of sticking her pussy out even further. I knelt in front of her (and slightly to the left), grabbed the belt (buckle end) with my right hand and the doubled up end with my left, aimed carefully and in one fluid motion, let go with my left hand and flicked my right wrist. This brought the belt down on her wide open pussy with a crack. She jumped and howled (both from the pain in her pussy and the pain in her ass as she landed hard back on the arm of the couch). I repeated the process several times and her pussy got very red. However, just like with the ass whipping, she began to lift her hips off the arm of the couch just as the belt struck.

All of a sudden, after about 6 or 7 strokes, she exploded in an immense series of spasms as she climaxed. I continued to whip her poor pussy and she continued to cum for a good five minutes. Finally, I stopped and she collapsed on the floor.

I picked her up off the floor and laid her on the couch. It was another 15 minutes before her breathing returned to normal.

I came over to her and sat down beside her on the couch and began caressing her breasts. Her nipples immediately got hard and she began to moan softly. Yes, I thought to myself, she is an insatiable pain-slut.

“I want you to go take a nice hot bath and then take a nap,” I said. “I am going out to pick up supplies. I’ll be back later with my friend Nancy and we will attend to those beautiful tits of yours just like you always fantasized about.”

She gave a long, deep moan and replied, “Yes, Master.”


This story is taken from the missing site:


Special thanks to: BondMaster

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