Diary of a Pain Slut Week 01

I was getting close. Time for the second clothespin. I could barely control my hand enough to get the clothespin to my breast. I tried to put it out on the tip just like the other one, but my hand was shaking too much and I put it on all the way so that the pin was actually pinching just behind the nipple itself. That wasn't as intense as the other nipple, but it was enough.

The whole world exploded. I trashed around violently on the bed. This was the most intense orgasm I had ever experienced. I was far from being a virgin. I had gone over the top with several men and a couple of women, but nothing I had previously experienced came anywhere close to this. I don't know if I squirted or peed myself or just ran that much juice, but my sheet was sopping wet beneath me and my ass was making wet smacking sounds as I bounced around on the bed.

I lay there panting as the world slowly stopped spinning. Then I could feel the pressure on my tits and reached up to release the clothespins. This time I was sure that the neighbors heard my scream as I pulled all three of them off my left breast with one quick motion. I clenched my jaw tightly shut and released each of the pins on my right breast individually. Doing it slowly didn't make it any less painful.

I lay on the bed massaging my breasts until the deep dimples caused by the clothespins slowly disappeared, and then... and then... and then I put the clothespins back in place, making sure that the one on my right breast was also way out on the tip so that it tightly pinched that most sensitive area. And I started rubbing myself.

I left the vibrator lying on the bed next to me, humming softly. I didn't really need it. But I did need the pain. I wanted the pain. I loved the pain. And with the pain from my nipples egging me on, I exploded once again into a mind shattering orgasm.

This time after the world stopped spinning, I reached up with both hands and pulled all six clothespins off my breasts all at once. I screamed from the unbelievable pain, but it was still a good pain because it was part of the sensations that had given me such unbelievable pleasure.

From that night on, almost every night that I had the house to myself, me and my plastic friend and my bag of clothespins would have a little pain party in my bedroom. I also started searching the internet for pain stuff. From the stories and the pictures, I found out that humiliation had the same effect as pain for some people. And for a few special people, the combination of pain and humiliation could bring about extreme sexual pleasure.

I decided to find out for myself. One Friday night when my parents were both out of town for the weekend, I took my clothespins with me in my purse and went out bar hopping. Shirley and Vicki and I go out bar hopping about once a month or so, but they weren't with me that night. None of my girlfriends were with me. And I guess I can't really call it bar hopping since I was going to only one bar, The Grease Pit.

The Grease Pit was located right next to the entrance to the race track. It had been around forever and looked like it. The sign with the name showed somebody in a grease pit, one of those old fashioned trenches beneath a car that they used to have in service stations. The sign was so weathered that you could barely see the image, and even if you could, most people my age wouldn't know what it was. I only did because my dad had one next to the shed so he could grease his truck.

The Pit wasn't quite a dive, but it was close... very close. It wasn't quite a biker bar either, but on any given night there were probably as many vehicles with two wheels parked out front as there were ones with four. A girl went to The Grease Pit alone for one of two reasons. She was from out of town and lost, or she was looking to get laid.

I was a local; I was alone; and I was dressed pretty slutty, so it was very obvious that I was looking to get laid. Several different men tried to pick me up, but I brushed them off. I knew exactly who I was looking for, and that somebody was Brad Summers.

Brad had a reputation for being kinky. I had once watched him order a girl who insulted him to get over his lap. She did, and he spanked her ass right there in The Grease Pit. As she kicked and screamed, her short dress rode up over her ass cheeks exposing them and the skimpy thong she was wearing to everyone in the bar. Brad whaled away until she her ass was starting to turn purple and she was crying and begging for him to stop. She went to the police the next morning, but he hadn't done anything sexual to her and she had willingly placed herself over his lap, so there was nothing they could do.

Brad had the hots for me, and was always hanging around us when we slummed at the Pit. I had slapped his face a while back when he tried to pick me up. I told him to get the hell away from me and yelled that I would never go out with a neanderthal like him. He told me that he was going to make me very sorry for that one day.

Yes, Brad was definitely the one I was looking for if I wanted pain and humiliation.

Brad was almost always at the Pit from about nine o'clock on every Friday night, but tonight he wasn't showing. I decided to wait for him, and sat there by myself in a booth for several hours sipping on bourbon and cokes and fending off various bar flies who wanted to take me home... or out into the parking lot... or just back into the bathrooms. I lost count of how many drinks I had, but I knew that I was in no shape to attempt to drive home.

It was almost two am and getting close to closing. I was starting to think that I would have to take up one of the barflies on their offer when Brad walked in. He looked upset. Someone called out, "Where's Jill?"

"That didn't work out," he answered curtly and then ordered a double Jack, neat at the bar.

I immediately slid out of the booth and staggered over to sit next to him. "What do you want?" he snarled.

I put the clothespins on the bar in front of him and said "I want you to spank my ass until I can't scream anymore and then take me somewhere and screw my brains out while these are clamped on my tits."

I don't know if that was what I had been planning on saying, but it was what I wanted. My voice was pretty slurred from the drinks. So was my mind, I guess, because I said what I said loud enough for everyone in the bar to hear me.

Brad got up off the barstool and pulled a chair out into the center of the room. "If any of it happens here, it all happens here," he said. Then he pointed his finger at me and said loud enough for everyone to hear, "If you meant what you said, get naked, put those clothespins on your tits and lay down over my lap. After I have warmed you up enough, I will fuck you senseless right there on the pool table."

Then he turned to the bartender and said, "Tommy, you'd better lock the front door a little early tonight."

Turning back to me he said, "If you're leaving, you'd better go before he locks the door. If not, get your ass over here."

In response I stepped out of my high heels and slid my dress to the floor. I hadn't worn any panties under it. I think I had been looking forward to having to show my naked ass to everyone in the bar as I squirmed under the spanking, but this was even better. I was so humiliated and ashamed, but at the same time I couldn't believe how turned on this was making me. I pulled off my top and stood naked in front of everyone. God, how could I actually be doing this?

"Over here," Brad said playfully as he tapped his upper leg. I walked over to where he was sitting and stood next to him.

"Do you really want this?" he asked. "I don't want you calling the cops tomorrow morning and saying I forced you."

In response, I began clipping the clothespins on my breasts. I had ten of them with me. I started with two just on either side of each nipple. Then I put two more outside of them right on the edge of the aerole. After I had eight of them in place, I turned around slowly so that everyone in the bar could see what I had done. Someone started clapping and soon the whole bar was filled with the sound of applause. What I was doing suddenly penetrated through my alcohol soaked brain and I felt slightly afraid, but more than that, I realized that these were all people who knew me. How could I ever face them again after doing this? The shame and humiliation was overwhelming, but it was doing exactly what I had hoped it would do.

I had been running juices down the inside of my thighs before I put the first clothespin in place, but now, I was absolutely gushing. I held up the next clothespin and then very carefully clipped it to the very tip of my left breast. That brought another round of applause and another flood of juice from my pussy. I repeated my actions with the clip for my right breast, and then draped myself over his legs. This combination of pain and humiliation was definitely working, and he hadn't even started spanking me yet.

Brad didn't waste any time working up to the spanking. He didn't stroke my back or my ass or say anything to me. He just put one hand firmly in the middle of my back to hold me in place and started whaling away on my ass. Most of the spanks hit right in the middle of the ass cheek, but once in a while he would hit lower, almost on the leg. That was a lot more painful and would cause me to kick my legs way up in the air and scream even louder.

I knew that each time I did that I was showing my twat to everyone who was looking. That added humiliation was driving me crazy with lust. I felt like I was on the verge of an explosive orgasm just from the pain and humiliation of it all, and then he stopped.

"Change of plans," he said sternly. Down on your hands and knees right here.

I did as he had instructed. At that point I think I would have done anything for anybody just to get that orgasm that was just over the hill in front of me.

"Tommy," he said, "I think you deserve a special tip from this little lady. You take her mouth while I take her cunt."

As he knelt on the floor in front of me, Brad added, "The only thing is that when she starts to cum, you have to yank all those clothespins off her tits. You got that?"

"Got it, Brad," he answered

His prick was already out of his pants and starting to get hard. I hadn't said anything about sucking anybody off, but I did want to be humiliated and there is nothing more humiliating than being forced to give a man a blow job in public. I gobbled his prick into my mouth and started slurping.

Meanwhile, Brad rammed himself into me from behind. I've never really been a fan of doggy style, but it also added to the humiliation. I started grunting and groaning and yelling out as much as I could around Tommy's prick. I was heading higher than I had ever been before. The pain of Brad slamming up against my bruised asscheeks combined with the humiliation of having Tommy's prick in my mouth and the fact that all of this was taking place in front of a crowd on the filthy floor of a dive bar was doing things to me that I had never felt before.

Suddenly I yelled out, "Take my ass. Now! Take my ass!"

I didn't know why I said that. I definitely do not, or did not, like anal. It is painful... and disgusting... and humiliating. Well, three for three. That's what I was looking for– pain, disgust and humiliation.

Brad pulled way back until he was clear of my cunt and then rammed forward in one thrust and buried himself in my ass. I screamed in pain, but as soon as his balls hit me between the legs, I started to climax. Brad and Tommy were both holding on to me as I screamed and thrashed and bucked like a bronco coming out of the shoot. Then Brad yelled, "Now!" and Tommy ripped all of the clothespins from my body.

My mind literally exploded. Everything was color and sound and flashes of light. In my next truly conscious moment, I realized that I was laying face down on the floor. Dave was pumping madly in my ass and Tommy was now spurting into my hair. Then I heard Dave say, "Who's next?"

He pulled out of my ass with a loud pop and almost immediately someone else took his place. This new person went for my pussy rather than my asshole, but I still squirmed and screamed and tried to get out from under him. Two more men from the bar came over and held my arms. One reached under me and squeezed my breasts and then pinched one of my nipples.

That was the magic button. "Fuck me. Fuck me. FUCK ME!" I screamed. The two men pulled me back up onto my knees and one of them put his prick in my mouth. I was too far gone to give him a true blow job, but it didn't matter because he was actually fucking my face. He didn't last very long and shot his load down my throat.

He was immediately replaced by another man, who also didn't last very long, but he pulled out of my mouth and shot his load all over my face. I think a different man took over behind me at that point because the prick was back in my ass rather than my cunt. My mind collapsed after that and I really don't know how many men had me or in which hole. I woke up really early the next morning lying naked on the barroom floor. My purse and $400 in twenties were laying on the floor next to me. There was a note that read, "Lock the door when you leave." My clothes, unfortunately, were nowhere to be found.

I was a filthy mess. I stunk so bad that I could even smell myself. It was a mixture of cunt and cum and urine and sweat and barroom floor. I looked for my clothes for a while and finally said out loud, "The hell with it. You wanted humiliation, you might as well top it off by driving home naked."

Luckily there wasn't much traffic that early on a Saturday morning and I was able to get out of town and home without being stopped by the police. One of the neighbor boys, however, was out mowing ditches and he did see me get out of the car and go into the house. I heard him gasp as he realized that I was naked and covered in cum. By the time I got in the kitchen door, I was once again burning with shame and embarrassment.

The night had been everything I had hoped it would be, but it was also a lot that I hadn't hoped for or really wanted. I now knew that both pain and humiliation took me to places that most girls can only dream of. But I also knew that if I kept this up, one morning I would find myself dead in an alley rather than just bruised, beaten, and hung over on a barroom floor. That was when I decided that I would be better off finding ways to get pain and humiliation a little more safely.

I went back to the internet and started looking at pictures and reading stories. There is a lot of bullshit out there, but every once in a while, there is a story or post or series of images that actually has something to do with reality. I found out enough to know that I am evidently a natural born pain slut and I also found that there might be third avenue to the explosive pleasure which I now craved. That third avenue was restraint.

Pain would take me over the top. Pain and humiliation would take me even higher. Would adding restraint to that put me in the stratosphere? And was there a way to do this safely?

There are actually quite a few good sites which give a lot of useful information about self bondage. I learned how to make a simple ice cube key release and tried that as my first attempt.

I didn't have a safety backup, but this was a pretty simple setup for test purposes. All I did was buy some cheap handcuffs and leg irons from an online store and put them on my wrists and ankles before one of my nightly masturbation sessions. If something went wrong and the key didn't drop down next to the bed like it was supposed to, worse come to worse, I could work my way downstairs to my dad's basement workshop and use some of his tools to cut myself free.

I lay back on the bed like I normally did and put the clothespins in place. I was now up to nine on each tit so that they formed an X with my nipple right in the middle. I was using my favorite vibrator, a jack rabbit. The jack rabbit not only has the rabbit ears to put a tingle on your clit, it thrusts in and out and spins as the same time.

At first, I didn't think that having my hands and legs cuffed together would make any difference. But then things started to heat up and I tried to open my legs. They would only pull open as far apart as the chain that held my ankles. I had to pull my feet almost up against my ass in order to open myself up like I wanted to. As I struggled against the confinement of the chain, I found myself responding to the inability to move freely. Something about not being totally in control was pushing me higher than just the pain and the jack rabbit.

It wasn't until I started getting close to where I wanted to be that I realized what it meant for my hands to be bound together. Normally as I approach that grand finish, I reach up and twist some of the clothespins on my tits. I sometimes even twist the one that is directly on my nipple. My right hand started to move toward my breasts, but it was attached to my left hand that was controlling the jack rabbit.

I heard myself groan out, "Noooooo." I wanted the additional pain of the twisted clothespin, but I also wanted to keep the sensations from the jack rabbit. In my previous sessions, I would sometimes let go of the vibrator to twist pins and play with my clit at the same time, but I never totally abandoned one area for the other. Now I had to choose.

I pulled my feet as tight into my ass as I could so that my heels were pushing against the jack rabbit. Then I raised both hands up to my breasts.

I couldn't even reach both breasts at the same time! I needed that little extra stimulation to take me over the top and I couldn't do it.

I bounced over to the edge of the bed so that I could lower my feet over the side and sit up. Now my weight was keeping the vibrator in place and holding it so that it could thrust inside me rather than just slip slightly in and out of my cunt. The only problem was that sitting on the jack rabbit was more like sitting on a jack hammer. It was pounding against the top of my cervix like an incessant woodpecker.

With the rabbit held firmly in place I went back to pulling and twisting the clothespins on my breasts. If I could just tweak both nipples at the same time, I knew I would go over the edge, but I couldn't. I was screaming and crying in frustration. I found myself begging the handcuffs to let me free. "Please, please, please, please," I cried out. "Let me make myself cum."

Then I realized that something else was happening. No, I couldn't cum... not yet, but I was still going higher and higher and higher. I was already in the mind bending range and I hadn't popped yet. I was chanting, "Please, please, please, please, please," but there was nobody there to listen except me.

I started bouncing up and down on the bed to drive the rabbit further and further into me. About the fifth or sixth time I bounced, a voice from the very back of my mind said, "That will work for your tits. Reverse it."

I pulled my legs back up onto the bed and got up on my knees. My hands were now between my legs pumping the jack rabbit in and out of my cunt. With its own motion and with what I was doing with my hands, I was almost there, but I still needed something more. I pumped up and down with my hands about ten times and then gave one final extra heavy push and fell forward onto my face on the bed.

All of the clothespins twisted at the same time. About half popped off. So did I. By the time I finished thrashing and screaming, I had knocked all of the clothespins off my breasts and deeply scraped my wrists and ankles with the cuffs. I realized there is a reason that you should buy the more expensive padded restraints. I also realized that a string that wound through the center of the spring on all of the clips would allow me to rip them all off in an instant.