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Old 08-14-2010, 02:06 AM   #1
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Default Painful Punishment, Anal Discipline

Slave's punishment

This punishment report is being written during my punishment. Only when I finish writing it am I allowed to ask for my buttplug to be removed and my punishment to end.

On the 7th of Aug, Mistress Michelle was leaving for her business trip but before she left, she ordered me to wear my medium buttplug and wear it for until her plane take off, about 3 hours later. Only then can I remove it.
Thinking she was in a rush, I didn't think she would actually check if my buttplug was in and so I did not wear it. But just as she was about to leave the house, she gave me a hug and reached for by butt, I know I was in deep trouble. All she said was I'm going to regret that.

Just before her flight took off, she sent me an message and wanted me to make a poll, http://www.misterpoll.com/polls/495827 to decide the severity of my punishment as it was already the third time she caught me not wearing my buttplug after I was ordered to. Since Mistress Michelle was going to be away for two weeks, I am to admister my own punishment or get our best friend, Mistress Elizabeth to punish me.

Days leading up to the punishment

As the day draws nearer, I was informed that Mistress Elizabeth will admister the punishment and her Slavegirl Simple (Named Simple as it was simple to control and punish her, spanking her pussy will make her submit immediately) will be helping her. Two days before the punishment day, Mistress Elizabeth says looking at the poll, it is most likely I will be punished by urine enemas, as such from that time forth, I have to pee into bottles for storage.

On the day of the punishment, Mistress Elizabeth and Simple will arrive at 10.30am. I should be fully shaven, gagged with a large ball gag, have the medium buttplug in me and knee beside the door of the house with my hands handcuffed behind my back waiting for them to arrive, prepared for my punishment.

Day of the punishment

For some reason, my alarm clock failed to ring and I woke up at 10am. When I ssaw the time, I panicked. I knew I would have barely enough time to prepare myself. I got out of bed, went into the shower and got myself ready. By the time I'm done shaving myself and taking my shower, it was already 10:20am. I got my ball gag, fasten it around my head and heard the car rolling into the garage. I grabbed the heandcuffs and secured them around my wrist behind my back just as I kneeled down beside the door.

Just as the door opened, I realised that I forgot to wear my buttplug again. But it was already too late, there was no way for me to get it in unless I was released from my restrains. Mistress Elizabeth walked in holding a leash connected to Simple's collar and Simple crawled in behind her.

Mistress Elizabeth disconnected the leash and ordered Simple to check me to ensure that I am prepared the way I should be and get the punishment gear from the car while she went to the toilet to relief herself. Simple quickly went to get some equipment from the car and placed it on a table behind me so I couldn't see what they were.

She then proceeded to check me. After spotting my mistake, she whispered into my ear "You're in so much trouble, Mistress Elizabeth hates it when I fail to prepare myself for the punishment the way she orders me to. Just get ready for a severe punishment."

As Mistress Elizabeth exits from the toilet, Simple reported to her. The next thing I know, I was being pushed over and my ass was exposed. Mistress Elizabeth was mad beyond description. She commanded Simple to get the bottles of pee. By now there were 4.5 liters worth in 3 1.5 liters bottle. I was placed on a leash and dragged to the room she wanted my punishment to be admistered. Mistress Elizabeth made me watch as she made some changes to the pee collected. The first bottle was placed in the fridge while the other two had alot of liquid soap pumped into it and placed in tub of hot water. Only then did I realise what I was about to get. A cold pee enema and warm and soapy pee enemas.

Mistress Elizabeth said to me "You are truely a naughty slave who needs severe punishment. After I'm done today, you'll wear your buttplug without anyone asking for fear of another punishment. Today you'll be the lowest lifeform, lower than Simple. She can do anything she wants to do to you." She then ordered Simple to get all the equipment ready while she went to watch some television. As she left the room, I looked up at Simple who had a grin on her face. She ordered me to roll on my back and I did. After all the equipment was brought to the room, she picked up my medium buttplug and placed a small amount of lube on it. She then lifted up my legs as if I was a baby who was getting his diaper changed and started to pushed the buttplug into me. The insertion hurt more than usual, and all I could do was let out a moan. Once that was done she left the room and I was left there for what seemed like forever.

Finally, Mistress Elizabeth and Simple came back to the room, it was already lunch time. Mistress Elizabeth brought some left over which was fed to me by Simple. The removal of the large ball gag hurt, my jaw felt numb and every chew felt weird. At the end of lunch, the ball gag was inserted again.

The handcuffs were removed and I was ordered to go on all fours facing a corner of the room and a blindfold was placed over my eyes. Soon, I could hear the sound of flowing liquid which I can only imagine was the cool bottle of pee poured into the enema bag. Without warning, the buttplug in me was pulled out agressively and left with a 'plop' as it pass my sphicter, and a nozzle was pushed into me. I couldn't see how big it was, but it's larger than usual and it hurt going in.

The click of the enema hose clamp signelled the start of my punishment. Instead of the cold pee enema which I expected, the liquid that flowed into me was warm, it must've been the warm soapy pee. Before I knew it, heavy cramps hit me and I tried to beg for relief but everything that came out of my mouth was a blur of words. Suddenly, the nozzle in my anus started to move. I could hear Mistress Elizabeth's voice "Cramping? Too bad, I don't care. I'm just going to fuck you with the nozzle and make this experience worst for you. Simple, clamp the slave's nipples." The sudden pressure on my nipples took my concentration away from the cramps in my stomach for a moment. The clamps hurt, but there was nothing I could do about it. Finally, the enema bag was emptied, I heard the click of the clamp again and felt some relief.

"Simple, remove the slave's nozzle and insert the anal beads into his ass. Then bring him to his feet and make him spread his legs while you hook the 500g weight on the end of the beads"

"Yes Mistress Elizabeth"

"Slave, there are five beads in that string and you're going to hold that in for 30 minutes. I don't care if four of them fall out, but if the fifth one gets out, I'll give you an additional 10 swats on your anus spanking later. But to make it more interesting, I will give Simple 20 swats on her pussy with the riding crop. What she does to you after that is your problem." As she said that, bead after bead was pushed into my anus. I knew the feeling, it was my own anal beads, not like the new enema nozzle which Mistress Elizabeth brought with her. I was then helped to my feet. The pressure now increased as I have to fight against gravity. The cramps became much worst. And beofore I can adjust to it, a felt a strong pull on the anal beads. I struggled to clench my anus to keep it in.

"Good girl, come" and the door slammed close.

I was left alone in the room, not knowning how long has passed. Before I knew it, the first bead fell out of my ass. Due to the weight it was connected to, the sudden jerk caused the second and third bead to fall out. I clenched my anus with all the strength I had left to prevent the last two beads from falling out.

Just as I heard the door open again, the forth bead fell out. I was hanging by a thread. "Look at that Simple, four of the beads are out. You know what
happens when the fifth one comes out. He has another 5 minutes to go. I recommend you pursuade him to keep it in."

"Look slave, you better keep it in. If it drops out and my pussy gets spanked, I will coat the next thing that goes into your butt with vicks and itching powder. Just imagine how that would fel in you for the next 30 minutes." Her threats worked, I clenched my anus as hard as I could over the next long 5 minutes. The cramps were incredible, my legs were shaking and I didn't know how much longer I could keep it in.

"Simple, remove the weights and the last bead, lead him by the leash to the toilet and let him release his enema. Stay and watch. I want him to lose whatever dignity he has left. Give him 10 minutes, I want him back in position for the next enema within 15. Every minute late will result in you getting 10 swats on your pussy"

The removal of the weight and last bead gave some relief. Next, my blindfold was removed and I was ordered to go on all 4 and began my crawl to the toilet. Once I got there I was allow to expel, but with Simple standing and watching, I was too shy to release it. "Look, honestly, I don't care if you release your enema. You have about 7 minutes left. At the end of that 7 minutes, regardless of whether you still have any pee inside you, I'll clean you up and drag you back into the punishment room. Mistress Elizabeth won't care, she'll just add another 2 quarts into your bowels. I'm not risking my pussy for you."

I release my bowels without any further hesitation. The stench of poo, pee and soap filled the entire toilet, it burned slightly coming out. Once I was done, I was dragged off the toilet by the collar and my ass was sprayed with freezing cold water, making me squeel. Without being dried, I was dragged by the leash into the punishment room.

The 2nd enema was already waiting for me. Again, the nozzle was shoved up my ass, but before the valve was released, I was given earplugs and a noise cancelling headset and a blind fold was placed over my eyes. I couldn't see, I couldn't hear. The sudden rush of soapy warm pee into my bowel startled me, but all I could do was stay in position and take my punishment.
Once the entire bag drained into my bowel. The nozzle was removed and I felt something very cold push against my anus and something tickled my thighs. I realised that it was my large ponytail buttplug. Mistress Elizabeth must've placed it in the fridge in preparation for this punishment. Usually when Mistress Michelle use this plug on me, she would make sure I was comfortable and slowly ease it into me. Moving it in and out slowly until my anus was ready to take it and then push it into place. But Simple or Mistress Elizabeth who was behind me wasn't going to be as nice. The was a constant growing pressure as it pushed up against my anus. I began to lean forward but soon I was grabbed around my waist and pulled back. The large buttplug slipped into place and stayed there. It was cold and very uncomfortable.
I was then left there alone, but I guess what must've been 30 minutes later, I had my blindfold, headset and earplugs removed. Simple reached down and removed my nipple clamps as well. The blood rushing back to them caused me to scream through my ball gag. I was then dragged to the toilet like pony and made to release my enema.

This time however, Simple failed to get me back into position in time. We were both going to be punished. Mistress Elizabeth got Simple to spread my ass check, revealing my anus and begin raining down blows on it with the wooden spoon. After about 5 spanks, she stopped and picked up the riding crop. "That wooden spoon is not going to teach you anything, we need something meaner." The smacks of the riding crop hurt alot more, and I was screaming through the ballgag by the end of the last smack. I can only imagine how Simple will feel when she recieve 20 swats on her pussy.
Simple was amazingly disciplined. Once my spanking was done, she laid on her back and spread her legs. She would count each swat and thank her mistress. Towards the end, it was obvious that she was struggling, her pussy lips was pink and her legs were trembling.

"I'm sorry Mistress Elizabeth, I will complete the task on time next time. I promise" Simple said at the end of her spanking. I now understand where her name came from.

"Get up, go give him the next enema. You can do what ever you want to him and hands her the riding crop. Remember, this is a cold pee enema, I don't want the slave to get hypothermia. He doesn't need to hold it for 30 minutes. Let him expel after 5 minutes." I could hear the door slam shut and I was left in the room with only Simple.

Her eyes were full of hatred. Through the gag, I said I was sorry, but I don't think it made a difference. "Do you know how much that hurt?! I hate getting my pussy spanked. You're so going to get it." She shoved the nozzle into my sore anus which made me scream through the gag. She then unclamped the hose and let the cold pee flow into me. It was freezing and the cramp came immediately, it was worst than anything I experienced. Without any warning, she started to whip my ass with the riding crop. All I could do was beg and apologise through the gag. But she didn't care.

Once the bag was emptied, she removed the nozzle and spanked my anus with the riding crop. I struggled and the blows became harder. In pain, I couldn't hold the enema any longer and it sprayed out onto the floor and onto simple. The cold pee made Simple scream.

The door swung open and Mistress Elizabeth entered the room. "Go wash up, you're really useless, you can't even make him hold an enema. You're going to get another 20 swat on your pussy, and he will be administering it." Upon hearing that, Simple left the room sobbing.

"You! You're going to clean up this mess before you can release the rest of your enema." Mistress Elizabeth removed my ball gag and shoved a spounge into my mouth. It was almost impossible to clean up the mess with my stomach in knots. It hurt too bad. Simple came back into the room, grabbed a cloth and help me in the clean up. She then lead me to the toilet where I expelled my enema. She stood watch as I emptied myself.

When we got back into the punishment room, Mistress Elizabeth made Simple spread my asschecks and gave me 20 rapid swats on my anus which left me crying. "You're lucky Mistress Michelle doesn't want me to hurt your balls and penis. Get up, I want you to whip Simple's pussy. You better make sure you do it hard. If I find it satisfactory, I'll give her another 30 swats myself."
Without any further instructions, Simple assumed her position. Part of me wanted revenge for spanking my anus but another part of me felt sorry for her as she was only getting punished because of me. I begin the whipping and she started counting. At the 17th swat, she lose control, closed her legs, placed her hands around her pussy and begin rolling on the floor. I could tell she was in alot of pain. Mistress Elizabeth forced her legs and hands apart as I gave her the last 3 whips. Her pussy looked swollen and red. I wondered how she was going to pee later and felt really sorry for her.
Mistress Elizabeth grabbed me by the hair and dragged me to the corner and admistered the next enema. To my relief, it was a warm water enema. But as I recieve the enema, I can hear the sobbs of Simple in the background, she was moaning like an injured puppy. Again, I was plugged roughly by the pony tail buttplug and Mistress Elizabeth left the room.

I crawled towards Simple to ask her how she was and to apologise. I guess somehow she understood me through the gag. "Please just give me a hug, I'm in alot of pain. I know you're worried about Mistress Elizabeth and Mistress Michelle." I thought about it for awhile, but I couldn't do it, we were both naked. It would be like betraying my Mistress. I held her hand instead.
"Go back to position", is about time for you to release your enema. She got up and lead me into position. Not long later Mistress Elizabeth came in. "How's your pussy? Go bring him to the toilet so he can expel his enema."

"It hurts Mistress, but I know its my fault. I'm sorry.

"I want you to give him another 3 enemas in the toilet to wash him out before the next punishment."

With that, I was lead to the toilet and cleaned out completely. After that was done, I was lead back into the punishment room where Mistress Elizabeth was waiting.

Mistress Elizabeth removed my ball gag and said "I want to hear you scream as I spank your anus, we'll see if you ever dare to misbehave again." she then moved to get more restraints and tie my legs apart, exposing my anus. "I want you to count out every swat, if you fail, we'll restart the punishment. You should know what the poll results are. More than 50 spanks until you cry. I'm going to make a small change to it. More than 50 spanks, until you cry and then another 15 swats after that. Simple will admister the last 15 swats.

She then moved behind me and begin whipping my hole. Each strike burnt, and I struggled to count out loud. By the 35th Whipped, I was already crying and begging for her to stop. I don't have nearly as much disciple as Simple. Mistress Elizabeth ignored my cries and continued my whipping. After the 50th strike, she passed the riding crop to Simple who continued my whipping. At the end of 65 swats, Mistress Elizabeth spread my ass cheeks and examined my anus. "Look at that red anus. No bleeding, no visible damage. You'll heal over the next few days. Look on the bright side, your bowels are completely empty, you won't need to use the toilet for awhile." She then left the room and made a phone call to Mistress Michelle while Simple release my bounds.

"Your Mistress wants to talk to you", Mistress Elizabeth held the phone against my ear.

Mistress Michelle: "Slave, have you learnt your punishment?"
Me: "Yes Mistress"
Mistress Michelle: "Well, your punishment isn't over. You're now going to be plugged by the large ponytail buttplug and forced to orgasm 3 times."
Me: "Mistress Michelle, please no more, it really hurts, I don't think I can take the buttplug"
Mistress Michelle: "Too bad, that's what the poll said, perhaps next time you'll remember this pain when I tell you to wear your buttplug"
Me: "Yes Mistress"
Mistress Michelle: "I want you to please Mistress Elizabeth and Simple orally until they cum and then write a report on this punishment, only then can your buttplug be removed."
Me: "Yes Mistress"

Mistress Elizabeth then picked up the ponytail buttplug and smiled. She then gave it to Simple. "Remember how he caused your pussy to be whipped? You can have your revenge now, I want to you insert this into his sore sore rectum. But first, I want to play with it."

The last line scared me. Mistress Elizabeth went behind me where I couldn't see what she was doing. She touched my anus with her fingers. Even the slightest touch hurt. The next thing I felt was a very cold object on my anus. And then I realised, she is holding an ice cube against my anus. At first the cold seemed to ease the pain, but it soon made it worst.

By the time she was satisfied, Simple had the plug fully lubed up. She slowly pushed the buttplug against me but my swollen anus refuse to accept the entire toy. I was too tired to scream by that time and could only moan. After 15 minutes of trying, the buttplug finally slipped in. Mistress Elizabeth then went to touch the buttplug, every touh sent shockwaves through me. When fully satisfied, she had Simple roll me over.

"Remember how I force you to have multiple orgasm Simple? Remember how that hurt? I want you to force him to orgasm now. He should orgasm 3 times over the next 10 minutes. If you fail, you'll be spanked on your pussy 10 times for each minute that you go over." Mistress Elizabeth then clamped my nose, blindfolded me and place earphones and headsets on me, making sure I won't be distracted by any other senses except the sense of touch.

Simple quickly grabbed my cock and sucked on it hard. With the buttplug in my ass pushing against my prostate and all the stimulation I already had, I came in less than 1 min into my stimulation. As I cum, my sphicter contracted, drawing the buttplug deeper into my anus which hurt badly and made me scream. I've never felt such pleasure and pain at the same time. My semen shot into her mouth, but she kept her pace. I guess she swallowed the semen. As she continued, my sensitive cock became more and more sore. Soon after, I cummed agan. Every stroke started to hurt more. She then continued without using her mouth and stroked my cock with both hands. After a long time, I cum the 3rd time. If felt really sore by the end of everything.

Everything except the buttplug was removed and I regained my senses. "My dear Simple, it seems like all that oral training didn't do you much good. You took 12 mins and 54 seconds to make him cum 3 times. That'll be 30 swats on you pussy. I want to round it up. But I'll give it to you after this slave makes me cum" and sat over my face.

My tongue begin laping and sucking on her pussy. She gave a couple of moan and cum all over me. Her varginal fluid squired out of her pussy and sprayed all over my face and hair.

She then ordered Simple to get into position and begin her whipping. As always, Simple counted out loud. But this time, it was more of screaming out the count rather than saying it out. By then end of all 30 swats, her entire pussy was swollen, red and a little bruised. I now understood what Mistress Elizabeth was trying to do, she wanted to make Simple's pussy as sore as possible before allowing her to cum. "Come slave, make her cum." I was lead by the leash to Simple's pussy where I begin to pleasure her orally. But she moaned in pain. I could feel her pussy radiating heat as I started to suck on it. After a long time, she finally came.

I was then lead to a chair where a laptop has been placed and made to write this report while kneeling. Every 5 minutes, Mistress Elizabeth would come and tug on my ponytail so I can feel the pain in my ass to remind me of the pain as I write this report. Simple was allowed to go to bed and rest as her pussy healed from the punishment it was given.

This report was completed after 2 hours of typing and 24 hard and painful tugs later.

By Mistress Elizabeth

This slave has successfully completed his punishment. But unfortunately, his anus is so swollen that it hurts so much to remove his buttplug that he would rather keep it in for another 2 hours when its better and then remove it. I sent him to the room where Simple is resting and allowed them to hug each other to bed after Mistress Michelle agreed that they had enough and should be allowed that.

We also made a deal that if this slave is willing to wear his buttplug overnight and Simple is willing to wear the same ponytail buttplug of her own overnight, they can have intercourse tonight. But we'll only tell them that later tonight after dinner.
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The following 3 users say Thank You to enemapunishment for this post:
Old 08-23-2010, 02:24 AM   #2
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Thanks for sharing this story, I really enjoyed reading it!
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Old 08-23-2010, 09:13 AM   #3
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This is more of a story format than a punishment idea, moved.

Boop Boop de Boop.
female, engurrland.
Ask me anything, click.
My tumblr. 18+

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Old 08-26-2010, 01:56 PM   #4
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Is this non-fiction?
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Old 02-23-2011, 03:20 PM   #5
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wow i feel bad for simple not so much for you though but i would love a mistress like MISTRESS ELIZABETH

Last edited by crazy_go_go; 02-23-2011 at 04:14 PM.
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Old 05-17-2011, 04:39 PM   #6
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Sounds like a fun day
Go have fun
lifes short
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