My Mistress decided to put me through a grueling scene with a Professional Domme that would guide her through some anal training techniques. This was her anniversary gift to me, celebrating 1-year of my submissive service to Her.
On Friday of our "special weekend", I awakened my Mistress with the usual oral services She expects of me. After her orgasm, Mistress turned over on Her stomach, and ordered me to service Her rear opening. She told me to take my time and give Her a very pleasurable and long tonguing and licking of Her rosebud. I did my best, licking around Her tight passage. Sticking my tongue into Her tight passage, and easing it into Her anus. I licked Her for what seemed like an hour. (actually, it was!).
When Mistress grew tired of my oral attention, she told me to go over to the bench and secure myself to it. Mistress went on to the bathroom to relieve Herself, while I secure my legs and arms to the cuffs attached to the four legs of Mistress's sitting bench. Usually, when I am secured to the bench, it means I have earned a punishment from Mistress. My fears were true when I saw Mistress come out of the bathroom. She picked up a paddle and a box from under the bed. Mistress informed me that I would be getting a hard paddling for my "good" oral attentions of her rear hole. Mistress removed a large butt plug from the box, and showing it to me, She said that this was only part of my anniversary present. I would be wearing the plug for most of the day, and She informed me that I was NOT to remove it all day!
I knew that my punishments would be far greater for me if I did remove it, then to leave it in, so I obeyed my Mistress.
Mistress started to push it against my anus. She would push it in, and then wait, watching my anus twitch and tighten, not wanting to be invaded. The Mistress started to swat my ass cheeks hard with the paddle. "This is for not opening your butt for the plug!" "You will open up for me now!" Mistress spanked me hard for about twenty swats. Then She ordered me to accept the plug. I forced my sphincter to open when She pushed the plug into my ass. Mistress pushed the tip into me very slowly, only going in about an inch or so. Then She would withdraw it and start over. Finally, She pushed it in hard and the widest part was in! But she just continued to play with it, turning it with Her fingers and then pulling it back out. Then She would start all over again, just teasing my anus with the tip, then forcing the widest part of the plug in and pulling it out. Mistress would pull it out very slowly, so the widest part of the plug was at my anus, stretching it soooo wide!
I was groaning each time Mistress would pull the plug out or push it in. Mistress told me that I would be punished additionally for making so much noise! Finally, Mistress pushed the butt plug into my asshole, and came around to face me. She was holding up a pair of her soiled painties, and she rubbed her juices into the crotch right in front of me. She told me that these would have been my gag, but since I had displeased Her with my moaning, She would have to find something else. That something else turned out to be my own shorts, which she used to jack me off with, and I emptied a huge load into them, and She them stuffed them into my mouth. Mistress then took her soiled panties and positioned the crotch over my nose. "There my pet, you can now smell me with every breath you take, and you can eat every drop of your cum since I allowed you to orgasm!"
"I am going to give you a nice hard paddling for licking my asshole so well, and for making so much noise when I was putting your butt plug in!" "I want you to just take your punishments, no matter how much your ass hurts!"
With that Mistress started to really paddle my ass hard. Sometimes, She even hit the butt plug which forced it deeper into my asshole! Over and over Mistress kept up Her assault on my rear. After a good hour of paddling, Mistress stopped and released me. My Mistress usually punishes me depending on Her mood, and on how I pleased or displeased Her. I have found that Mistress will punish me for at least an hour, but sometimes it can last all day, or weekend, or whatever She deems appropriate. Other times She will punish me just to pleasure Herself. She likes to use me as Her toy!
I was untied, but warned again not to remove the plug in my asshole. I readied myself for work, and before leaving read the note Mistress left for me. Upon returning from work today, I was to bath and have dinner ready for three people. I was confused, and wondered who would be the third person. Also, the note indicated that I should be dressed in my slave attire. Usually, that meant I was to be naked, or with just my underwear on. But I wasn't sure how Mistress wanted me, with or without?
Work was frustrating, with the large butt plug stretching me all day, and making a Friday even more uncomfortable! The drive home was fast, as I could not stop thinking about what Mistress had planned for me today!
Upon entering the house, I showered and prepared the meal as directed. I then decided to get "dressed", or should I say undressed, for my Mistress. I decided to just wear a pair of plaid boxers, as my slave attire.
Mistress arrived soon after, with a beautiful blonde woman. Mistress introduced Her as Mistress Tanya. I was to serve Her as my own Mistress, and to accept any punishments from Her if I displeased Her in ANY way! Mistresses then went upstairs to get themselves ready. Mistress then looked back, and said: "Remove the boxers, that is not how a slave should be dressed, and We will be punishing you for that when We come back down!" "I want you to place yourself, face down over the back of the sofa, and wait for your punishment."
I did as ordered, wondering just what Mistress and her beautiful assistant had up their sleeves! I soon found out, as I watched Mistress enter the room. I just waited as Mistress informed Tanya how good I am at orally servicing Her and at how fond I am of anally servicing Her. Mistress Tanya said she couldn't wait to find out! Both Mistresses then went to the playroom for a moment and came back with a couple of items. Mistress Tanya showed me a long white dinner candle, and asked me if I knew what this was for? My Mistress was busy attaching cuffs to my wrists and ankles, and then a spreader bar was attached to my ankles. Mistress Tanya proceeded to tell me how She was going to insert "All" of the candle, deep into my asshole. She would be twisting and rotating it, and then leave it there for about five minutes. Mistress told me that if there were any signs of my dirtiness on the candle, my punishment would be extreme and last all night!
With that warning, I was really getting nervous. I had relieved myself earlier, but was this a test by Mistress to find out if I had removed the plug? Or was she expecting me to be dirty so she could punish me with her friend? Mistress Tanya then handed my Mistress the candle and turned around and dropped Her panties. My Mistress then commanded me to "entertain" Mistress Tanya with my oral talents on Her asshole. I was also ordered to be very quiet while receiving the "white candle" test!
Mistress Tanya pulled the armchair over, so that she could lay down on the couch and chair, making Her bottom easily reached by my mouth! I stuck my tongue out as Mistress Tanya pushed Her butt into my face. I smelled Her musky fragrance as I tasted Her back hole.
My Mistress slowly removed the butt plug that was embedded in my asshole all day. She twisted and rotated it before pulling it out, this caused me to jump and moan as the plug rotated in my sensitive asshole. Mistress Tanya then said that I should receive a good paddling and reaming for making noise, and my Mistress agreed! I concentrated on being quiet as the widest part of the plug was stretching my anus wide!
Once the plug was removed, Mistress started to insert the cold white candle into my gaping hole. I could feel my anus was still open, from the plug being in there all day. Mistress was working the candle into me deeper and deeper, twisting it as she went. I struggled to not moan, but the feelings were getting more and more intense. Mistress would push it in a couple of inches, then pull it about half way out, then push it in deeper. I failed to contain my moans as I felt the candle go in really deep! I could feel Mistress's fingers at my asshole, so I knew that she was holding the candle by the wick now. Mistress then reached around and clamped two sharp clips to my nipples, and said: "This is for making noise again after Mistress Tanya told you not too!" Mistress Tanya looked back and saw the alligator clips being applied to my nipples. Mistress Tanya then said: "I think our little anal slave needs to experience a good hard dildoing and reaming too! What do you think Diane?" Mistress answered immediately: "Oh I couldn't agree more! and I think we will have to use the monster dildo on him too!" Mistress Tanya just moaned out a: "Ummm Hummm!"
The five minutes had past, so Mistress Diane proceeded to pull out the candle, and ever so slowly, made me feel every inch of that long thing! Finally, it was out! Mistress brought it over to Tanya, and told Her it was clean. Mistress Tanya then got up and put Her panties back on after telling Diane my oral skills were good! Mistress Diane then told me to put my nose on the candle and not to move. Mistress grabbed a couple of books from the coffee table and placed them on the back of my head. Mistress informed that She and Tanya were going to eat now, and that I was not to move an inch, or else! Mistress Tanya just laughed as she watched, knowing I was kissing and smelling the candle that had just invaded my rear hole!
Mistress Tanya then picked up the paddle and told Diane that she thought I needed to receive a few good swats for moaning earlier. "Thats right Tanya, and after you give him twenty I will give him twenty!" "And don't you dare move or cause those books to fall slave!" I couldn't answer as that would require me to move my head so I just had to stay still as Mistress Tanya really paddled me hard. Then Mistress Diane took the paddle and really gave me twenty more good ones! My ass felt as though it was on fire! This paddling just reminded me how tender my ass cheeks were from my earlier morning spanking!
Mistress finished and then handed the butt plug to Tanya. Mistress Tanya then slowly worked the plug into my butt and gave it a little twist. Mistresses then went to have their dinner, informing me that my punishment would start when they finished eating.
After dinner, my Mistress untied me and told me follow them into the playroom/dungeon. My hands were cuffed behind my back, and I was placed in the center of the bed. Mistress Tanya then climbed onto the bed, and straddled my chest. Mistress Tanya began to toy with the clamps that were biting into my nipples. Twisting and pulling on them as She spoke to me. "Mistress Diane tells me that you are equally as good with your tongue in pussies as in assholes, is that true slave?" "Yes, Mistress" was all I could hiss out as She tormented my sore nipples! "Well, lets just see if you are." With that, She moved up and slowly sank down, pushing Her pussy onto my mouth! Mistress Diane told me to do a great job, and: "Don't disappoint me slave, or else!"
As I began to apply my best oral skills to Mistress Tanya's pussy, I could feel hands on my hard erect cock. My Mistress was lacing up my cock with a thin leather strap. She was tying my cock in the leather sheath very tightly! I was forcing myself to continue sucking and licking Mistress Tanya's pussy, despite the pain I was feeling in my cock! Next Mistress got out Her small penis whip. Mistress then began to whip my genitals, which made me jump with each swish of Her whip. "I think our little slave forgot that he was to be punished!" Mistress Tanya added: "I think we should place a time limit on his oral servitude, don't you?" "Yes, you have five minutes to give Tanya a great orgasm, so you better get working slave!"
I sucked and licked for all I was worth, in spite of the lashing my cock and balls were getting! Finally I could feel Mistress Tanya starting Her orgasm, She continued to ride my face through Her nice long cum! Mistress Diane continued to whip my cock and balls, even though I gave Mistress Tanya a good cum! Mistress Tanya got up from my face and thanked me for a giving Her such a good orgasm. Then my two Mistresses pulled my arms and legs to the corners of the bed, and secured them to the cuffs. Mistresses then left the room shortly, but returned with a bowl.
Mistress Diane then climbed onto the bed and told me to give Her a very good orgasm. Mistress Diane positioned Herself facing my cock, and then lowered herself onto my face. My nose was suddenly trapped against Her anus, and She must have sensed this, because she pivoted slightly to allow me to breathe. Mistress then told me to enjoy her anus when I breathed in, and she rocked backward occasionally forcing me to sniff Her rosebud.
As I was licking and sucking Mistress Diane, I suddenly felt the sharp pain in my nipples as Mistress Tanya removed the clamps! Then I felt another stinging sharp pain at my nipples, when I realized the bowl they brought back was filled with ice cubes! Mistress Tanya continued to torment my aching nipples with the ice cubes, rubbing them all around! I was moaning into my Mistress's pussy as they continued to torment me. Mistress Diane reminded me to concentrate on my oral duties, as She was counting the time!
As the burning and stinging in my nipples continued, I finally brought off my Mistress as She bucked in orgasm! Mistress climbed off me and told me to rest up for the rest of my punishment. She said that She would be back in five minutes! As I laid there trying to catch my breath, the thoughts of "the rest of my punishments" ran through my mind!
I was suddenly brought back to reality when my two Mistresses came back to untie me. I was then led over to the horse, and laid face down on it. My wrists and ankles were again bound to the cuffs, and the spreader bar attached to my ankles. Mistress Tanya had selected a dildo and asked Mistress Diane, "Is this the one?" Holding up our largest dildo, a thirteen inch monster. Mistress Diane then responded: "Well, he is being punished so, yes, lets use that one on him!"
I wanted to whimper when I heard that, but seeing the position I was in, and being punished for making noise earlier, I decided to be quiet!
I watched as Mistress Tanya attached the huge dildo to the harness, and adjusted it so it was jutting out from Her! Mistress Diane pulled over a high bar stool and placed it in front of my face. "While Mistress Tanya is having Her way with your little asshole, you will be orally servicing my asshole! There is no time limit this time slave, when Tanya is tired of raping your boy pussy She will switch places with Me!" "Then I will take over raping your asshole!" "I also expect you to give Us each a few orgasms, so this may take a few hours!" "Maybe next time you will try and obey your Mistresses, OK slave?"
"Yes Mistress, please punish me so I will learn and be a better slave."
Mistress just laughed, and said: "I don't think you will be so eager and begging for a punishment when We get through with you slave boy!"
With that I was presented with Mistresses asshole, as she held her butt cheeks apart for me. I licked and sucked on Her rear hole, anticipating the huge strap-on that would soon be reaming my butt. Only too soon, did it happen! Mistress Tanya held the head of the dildo at my rear hole, then told me to: "Open up and accept my punishment slave!" With that She pushed hard, in a few inches and then out. This continued until She had buried the massive dildo into my asshole. The final thrust brought out a deep moan from me as She thrust the whole thirteen inches into me! "I think he really likes this, Diane!" "I guess I will have to be a little rougher with him!"
Mistress Diane said: "I think he needs it A LOT rougher!"
Mistress Tanya proceeded to pound my ass hard with that huge strap-on. She was really huffing and puffing, slamming it into me. She wasn't holding back at all! I was being stretched wide, the pain felt as though I was being ripped open! Over and over She would slam that dildo in deep, pulling it all the way out and slamming it all the way in! Mistress Tanya finally called "switch", and pulled out the dildo. I was given a short reprieve, as Mistresses switched the harness, and Mistress Tanya laid herself on the stool. I started to lick and suck Tanya's sweaty crack, and tried to perform well for Her also.
That was until I felt Mistress Diane yielding the strap-on! Mistress placed the huge dildo at my asshole and just pushed it in deep in one thrust! I nearly passed out from the pleasure/pain! I groaned loudly into Mistress Tanya's asshole!
My own asshole was not spared any mercy by Mistress. She worked it over slowly at first, making sure to pull all the way out, and waiting a second or two before shoving all the way back in! Then after She tired of this, She just started fucking my asshole with shorter thrusts of the dildo! Over and over this continued. She would go back to slow deep thrusts, pulling all the way out, and back to short ones.
Both Mistresses needed a break, so they pulled the dildo out and let me have a rest too. I thought that they were finally through with my punishments, but I should have known when I was still tied to the horse!
After about a half an hour they returned. In Mistress Tanya's hand was another ice cube, and she said: "I bet you wonder what I am going to do with this slave, don't you?"
"Please Mistress, I am sorry, please don't punish me anymore, please?" I was begging for relief, begging to be untied and to be set free! Mistress Diane said: "Too bad slave, you not only will get to feel this nice cool ice cube as Tanya tries to cool down your asshole, but you still are not finished receiving your punishments! You will learn to obey my every word, even when I tell you to be still, or be quiet!" "Is that clear slave?"
"Yes Mistress, I am sorry to have disobeyed you, and sorry to have made you punish me!"
"Well slave, you should be! And for begging me to stop, Tanya will be applying those nice nipple clamps to your sore nipples too!" "And, I think your butt needs to be warmed up some. What do you think Tanya?"
"Oh yes, and lets cool off his asshole a little first with this ice cube!" "Then we can each paddle his butt red again, before giving him the rest of his ass fucking!"
I felt the ice cube as it burned my tender asshole. Mistress Tanya rubbed it around and pushed it into my sore asshole. Then the nipple clamps were reattached to my aching burning sensitive nipples. I could not contain the moan and scream when they bit into my tender flesh! Mistress warned me to be quiet again!, and said that soon I would have her pussy to gag me, and muffle my cries!
Then they started to swat my ass very hard, each working one of my ass cheeks! I held back my cries and tears ran down my face as they beat my ass for fifteen minutes!
"Are you ready to behave now slave?" Mistress asked me. "No more begging me to stop your punishments. Can we continue with your previously earned punishments now?"
"Yes Mistress, please continue, I am so sorry for my begging". I sobbed out my answer, as Mistress Tanya laughed and snickered behind me!
"Mistress Tanya will be fucking your asshole while you orally pleasure me slave, then we will switch again!" "We will continue this until I say it is over, is that clear slave?"
"Yes Mistress, I am yours to do as you please, and yours to train. I will accept whatever you wish. Thank You Mistress for punishing me"
"I expect you to thank Tanya as well!"
"Thank You Mistress Tanya for punishing and disciplining me."
"Well, you are welcome slave, but don't think I am going to give into you by making it any easier on you. In fact this fucking will be nothing compared to your first one!"
After that, Mistress sat down on the stool, and pulled my head into her sex. I started to lick and suck on Her. I was actually happy to be owned and loved by Her that She would take so much time to discipline me!
Mistress Tanya started her assault on my sore asshole, and I jumped when that huge dildo speared my ass! Mistress Tanya was true to Her word. She was like a woman possessed, as She brutally fucked my asshole. Mistress Diane switched with Tanya, and She was equally as brutal on my asshole. They switched one more time and continued to ream me hard. Finally, Mistress Diane asked me if I would obey Her every word? "Yes! I will Mistress!" I sobbed and Mistress then took a candle and lit it.
"We will see if he truly will obey me now!"
Mistress Diane and Mistress Tanya, then went around behind me. Mistress Tanya slowly pulled the huge strap-on out of my asshole, and then held my burning ass cheeks open wide. This exposed my gapping open asshole to Mistress Diane.
Mistress Diane then said: "Do you want to obey me now slave?" "I am going to test your obedience now. I am going to drip this hot wax on your fucked boy hole, and I don't want to hear a sound out of you, is that clear?"
"Yes Mistress, I will obey you!"
With that my Mistress proceeded to drip the hot wax into my asshole and all around it, until my hole was completely covered and closed with Hot Wax! I remained quiet, although Mistress Tanya had to really hold on tight, as I jerked and fought back my screams! Mistress said that tomorrow She was going to work on me, saying that: "I was moving around too much for Her!" But that is another story.
I was finally released and went to shower and clean myself before going to bed.