Mistress Haile stood blocking my exit from the room, dressed in her black leather panties, her leather boots, glossy red lips and nails, her beautiful long blonde hair gently framing her beautiful face. She scowled at me and told me to kneel on all fours facing the window. My cock was beginning to swell and throb now following Mistress Haile’s handiwork! The cock ring gripping the base of my cock and balls like a vice. The spiked sheath was now beginning to become agonizingly painful as my erection grew! My balls were stretched and separated with the ball spreader and Mistress Haile was surely smiling now watching my discomfort grow!
The next think I knew, Mistress Haile faced me as she commanded me to open my mouth and accept the gag! I was being gagged with a pair of Mistress Haile’s fragrant panties that she had been wearing all day. I was told to stay still, do not move an inch and wait until she returned. My heart raced as I wondered what was in store for me now! My cock was pulsing, my erection growing but then subsiding as the sharp spikes bit into my flesh and the pain cut off the moment! I so desperately wanted to release my member from it’s tight confines and let it expand to it’s full length! But Mistress had other plans and the wicked CBT contraption prevented any erection even though my mind was commanding it to grow and grow! It had been five long days since my Mistress Haile had allowed me to cum, my balls felt as if they would explode.
I was naked except for the wrist & ankle cuffs and my slave collar. My panties were removed earlier, along with my regular clothing too. I felt so vulnerable not knowing what my Mistress would do to me next, but knowing that whatever she did to me, I would oblige regardless of how I felt. It sometimes scares me knowing that I no longer own my body and having surrendered it to Mistress Haile who delighted in inflicting painful torments, disciplines and punishments made my stomach churn! The combination of her beauty and her evil kinky desires have me imprisoned in her servitude, to do anything she likes to me! I am addicted to her and her manipulations of me and always will be.
I heard her come back into the room, but she wasn’t alone. Who was with her? What was going on? No sooner had I wondered who this new woman was that, Mistress spoke to her companion.
“This is my little slave boy I have been telling you all about, what do you think of him?”
Her companion started to laugh, I could tell from the soft laughter that she too shared some of my Mistress Haile’s desires for tormenting men like me!
“Haile, Does the poor boy know what you have in store for him this weekend?”, she replied.
Mistress Haile just started laughing, telling her friend that I had no clue what was going to happen, but that they had all weekend to show me and she finished by saying that the both of us would be enjoying it immensely!
Finally, Mistress Haile spoke to me. She told me that her companion’s name was Jennifer and that I should address her as Mistress Jennifer whenever I spoke to her! I would also be surrendering myself to Mistress Jennifer as if it were Me she said! I could see she was also petite and had long blonde curly hair, blue eyes and a beautiful trim figure similar to Mistress Haile’s. She explained that Jennifer was an old friend from school whom shared her penchant for Dominating boys, and that she had invited Jennifer to spend the weekend with us and explore some new toys and techniques!
I was embarrassed to be naked and exposed like this, my cock and balls all trussed up and kneeling before these two women like this!
Then Mistress Haile grabbed her favorite wooden Ping-Pong paddle and showed it to Jennifer.
“So, I see our little slave boy is in need of some bottom warming for not greeting you properly Jennifer!”
Mistress Haile handed the paddle to Mistress Jennifer, and told her to do the honors for my rudeness and lack of manners in not saying hello and greeting her properly! Mistress Haile asked her how many swats would be appropriate for my misdeed?
“Well Haile, I am a firm believer in harsh and severe punishments, so I will give the slave twenty of my best to his exposed bottom!”
“That sounds good Haile, and when you are finished, I will match those twenty too, plus an additional ten for embarrassing me like this in front of you!”
Mistress Haile handed the paddle to Jennifer and she took up her position behind me now. Her swats were fast and furious and I gasps as the first swats caught me off guard. I tried to remain still and accept my punishments as I knew Mistress Haile would surely inflict much more severe punishments if I dared move or jerk around! It was obvious from the tone of her voice as she counted out each stroke that Mistress Jennifer enjoyed this as much as Becca too! I could feel the redness spreading has my ass cheeks were getting warmer! My cock was still throbbing trying to grow to it’s full length, but unable to expand past the confines of the small spiked sheath! Finally Mistress Jennifer reported “20” and brought the paddle down to my ass with an even harder swat! Mistress Haile now joined her friend behind me and soon I would be feeling Haile’s punishment being delivered to my reddening backside!
Then before I could capture my breath, another set of swats rained down on my bottom! Mistress Haile’s swats were as hard and fast as Jennifer’s had been. One after another until I heard her say “30”!
“Now slave, have you learned your lesson or do we need to repeat it again for you?”
I quickly thanked both of my Mistresses for punishing me properly and then I greeted Mistress Jennifer and asked her forgiveness for my earlier oversight in not greeting her! Mistress Haile chastised me for my error and said that I should be more aware this weekend and on my best behavior in front of her guest! Mistress Haile also reminded me that if I did fail her of Jennifer in any way this weekend, that I would be receiving double punishments as both Mistresses would be delivering them!
“Did you enjoy that short little punishment slave boy, I know I did, and so did Miss Jennifer too!” “But this is only the beginning, we have much more in store for you slave boy”!
Mistress Jennifer told Haile that she had enjoyed it very much and wanted to play with me some more. She commented that I had a very “spankable ass” and that she hoped my pain threshold was high as she would love to decorate it with stripes and more color too! Then I could hear Mistress Haile whisper something to Jennifer but I could not make out the whole conversation, only bits and pieces like asshole and strapon.
Mistress Haile then removed my panty gag, and showed it to Jennifer.
“He really is a devoted little oral slave, and you will find out that soon enough, but I think he has a hunger for something else right now!”
Mistress Haile ordered me to go and get the strapon dildos, the black one and the blue ribbed one!
I suddenly realized that these were our two big dildos, the twelve inch ones, and one was ribbed with thick rings along it’s shaft. That one was always more painful as it popped my stretched sphincter with each ring along it’s shaft! My sphincter clenched immediately, knowing that these two strapon’s could only mean one thing! My ass was going to be punished by these two Mistresses while they stuffed all twelve inches of their strapon’s into me! I handed Mistress Haile the two dildos, but she stopped me and said that I should give one of them to Mistress Jennifer too! She asked me to choose one of the dildos and then to beg Mistress Jennifer to really punish my asshole very hard with it for not remembering to be hospitable to her!
I looked down at the toys and remembered just how brutal Mistress Haile was with the blue ribbed one. This was indeed a tough choice, if I handed Mistress Haile the blue on surely she would give me a hard painful fucking, but I know was to beg for a hard painful fucking from Mistress Jennifer! I decided to hand the black one to Mistress Jennifer and asked her to please forgive me and please have her way with my asshole giving me a hard fucking with this strapon!
Mistress Haile then told me that I was to also beg her for the same, as she stated earlier, my punishments would be given by both of my Mistresses this weekend! The stirring deep inside of me told me that I would receive exactly what I was now begging Mistress Haile for, a good hard anal fucking with this thick ribbed blue dildo!
I was ordered into the playroom, face down on the punishment horse as Mistress Haile and Jennifer both began to strap the dildos in place! And then Mistress Haile proceeded to tell Jennifer that I loved sucking cock and eating my cum almost as much as loved being fucked with them! “My slave boy is a cock sucking whore, who loves being fucked up the ass but also loves sucking cock too!” “Isn’t that right slave boy?” “Tell Jennifer how much you enjoy eating your cum and sucking on my cocks!”
I proceeded to tell Mistress Jennifer that Mistress Haile always requires me to eat all of my own cum and that I must first suck on her cocks before she fucks me with them! I asked Mistress Jennifer to please allow me to suck on her cock and kiss and lick it before she fucks me with it!
Mistress Haile secured my wrists and ankles to the four legs of the horse, and placed two pillows under my hips to elevate my ass for what was to come! A platform which I built was placed behind me so my Mistress would be at the proper height and leverage to fuck my hole while standing behind me!
I sucked on Mistress Jennifer’s big black dildo, kissing and licking it properly. Then Mistress Haile’s blue monster was at my lips as she grabbed my head for support!
“Here is how it will go slave boy”. “Since you begged for a hard anal fucking that is exactly what we are going to give you!” “First Jennifer is going to plow you deep and hard and without mercy!” “Then we will switch places, you will suck Mistress Jennifer’s cock with just finished punishing your hole, while I will proceed to give you what you begged for, a hard anal fucking with the blue ribbed toy!”
Mistress Haile holding onto my face thrust her cock between my lips and told me to suck it good, just like I did for Jennifer!
I started kissing and licking the head of the blue toy and then licked around it licking toward the shaft. Then I felt the cold wet tip of Mistress Jennifer’s dildo at my asshole, and felt her hands on my hips. In a steady pushing motion the head squeezed it’s way inside of my rectum as I moaned onto Mistress Haile’s cock! Then, the huge black dildo was thrusted deeper as Mistress Jennifer continued pushing until the entire length of the toy was embedded deep into my rectum! Then she withdrew it slowly until it popped right out. Again, the head was inserted, then a short pause and another deep full thrust until Jennifer’s hips contacted my hot cheeks! This continued, long deep full thrusts starting with just the head at my asshole entrance! With each hard deep thrust I would let out a low deep moan onto Mistress Haile’s cock! Then Mistress Jennifer moved her hands from my hips to my separated spread balls, and she would pull on them as she thrusted hard into me, each time her dildo slammed into me, she would squeeze my balls and a new shrill moan escaped my lips as she plunged hard into me!
Mistress Haile watched and commented on Jennifer’s new technique and told me that she hoped I would be moaning equally appreciative when she drilled me with her blue dildo!
Mistress Jennifer was really getting a rhythm going now, deep hard and faster thrusts as she continued to squeeze my balls with every thrust, only the faster she fucked me the harder she squeezed me before pulling all of the way out again! Mistress Jennifer fucked me for what seemed like an eternity, before finally one final hard deep thrust! Jennifer just stopped, the huge dildo stuffed all the way into my butt as deep as it would go, and her hands just squeezing my poor punished balls! She was breathing hard, and catching her breath. I was moaning and quaking beneath her, unable to stop the dull aching going through my balls! Mistress Haile held my head and tried feeding more of her blue dildo deeper into my mouth! Then, Mistress Jennifer released her grip on my balls and as I gasped and sighed from the release. Mistress Haile’s blue cock gently eased farther into my mouth before it too was pulled free!
I lay panting as Jennifer pulled free from my punished asshole!
All to eager to continue, Mistress Haile switched places with Jennifer and before I could relax The monster blue dildo was poised at my dilated asshole! Mistress Haile instructed me to accept her punishment to my already sore asshole, and to proceed in sucking Mistress Jennifer’s cock now!
With that said, Mistress Haile plowed into me with a savage thrust drilling me to the core with her blue toy!
Mistress Jennifer lifted my head and held her huge cock in her other hand as she pressed the now warmed up toy into my lips!
“Suck me good slave boy!” “I would hate to have to have another reason to punish your pretty little ass now!”
Mistress Haile chimed in and said, “Jennifer, you never need a reason to punish this slave boy’s ass, whenever you feel like it go right ahead, you don’t need a reason!” “Then when we ask slave boy to tell us why he is being punished, he will usually inform us of a misdeed he has committed that we may have overlooked!” “Then his punishment gets doubled for that too!” “Or it gets doubled if he doesn’t have an answer for us too!”
Mistress Jennifer loved the idea, and said that right after Haile’s anal fucking, she would be ready to punish my bottom again!
I sucked and licked on Jennifer’s musky dildo as my butt was being fucked raw by Mistress Haile! Mistress Haile would reach under me and grab my cock and squeeze! This made me scream into Mistress Jennifer’s soiled dildo as the tiny spiked pierced my cock flesh!
After another hour long anal fucking, Mistress Haile pulled the blue toy from my punished rectum, making sure to watch my sphincter grip each ring of her favorite punisher dildo!
I rested briefly, and felt the cool air entering my very dilated asshole!
Mistress Jennifer commented that my gaping hole was very arousing and that she just might have to fuck it some more! Haile showed Jennifer her assortment of dildos, plugs and vibrators, and after a short while they returned with a large cone shaped butt plug!
“Look what Mistress Jennifer found slave boy!” “She wants to see if your asshole is still hungry for more cock!” “So I want you to be very quiet, do not utter a sound, and do not move an inch while Mistress Jennifer fucks your hole with this very wide butt plug!” “All she wants to hear is your wet anus as it kisses and sucks at the huge cone shaped toy!” “This will tell us if you are still hungry for more cock today!”
With that, I tried to remain absolutely still, and felt the cold tip enter my dilated hole! Mistress Jennifer pushed it in slowly while Mistress Haile pulled my cheeks wide apart! Then the butt plug was removed and I heard some giggling, then the toy was back at my hole. Only this time I could feel it had been lubed, and now Mistress Jennifer pushed it into my hole. When she reached the widest part she stopped, and it was stretching me painfully wide back there! Then she just started to pop it back and forth between my stretched anus ring, this caused a nice wet popping sound with the lube she applied!
“Ahh, I hear your hole is begging us for more slave boy!” “We will have to see what we can do then for it!”
With that the huge butt plug was pushed deep inside of me and my Mistresses let go of my butt.
I then saw Mistress Haile return with a riding crop in hand, presenting it to Jennifer to do the honors!
Mistress Haile asked me what had I done to deserve this punishment now?
I begged for forgiveness and said I was sorry, please do not punish me again I pleaded!
“Punish you for what slave boy?” “What did you do?” “What are you sorry for?”
I didn’t know what I had done, maybe nothing, but I wasn’t sure, so I begged for mercy and asked for her forgiveness. Mistress Haile asked Jennifer if there was a misdeed or poor performance that I failed her in.
“Yes, slave boy was very hesitant to suck my cock after I punished his asshole so good with it!” “I had to force feed it to him!” “He should have been grateful to me for punishing his hole so well!”
“Hmmm, I see Jennifer.” “I’m sorry that you had to witness that, I can assure you slave boy is going to pay dearly for this mistake!”
“You will accept twenty-five swats from Mistress Jennifer for failing to suck her cock after she had just finished punishing your hole with it!” “Then, for lying about it when we asked you what you did to deserve this, another twenty-five swats with the crop!” “And, because Mistress Jennifer wanted to punish your ass just for fun another twenty-five for that too!” “Then I will take the crop and repeat the punishments to your flaming backside as well!”
Mistress Jennifer proceeded to really swat away at my plugged bound helpless ass, and I knew that before long my cries would be louder as the cumulative swats of the crop cut into my backside leaving countless red welts! I tried to remain quiet, but every so often a sharp stinging swat would cause me to vocalize my torment as a loud moan! Over and over the cropping continued! I couldn’t even begin to count the number that was being applied to my butt! I was crying steadily now and my moans were following each swat of the crop! I couldn’t see who was yielding the cropping, it could have been either one, they were both making small talk as they continued to punish my ass without mercy!
Then the cropping had stopped as I whimpered and adjusted my breathing back to some normalcy!
“You accepted your cropping very well slave boy!” “I should reward you for that, in fact Jennifer had mentioned something to me just a minute ago that I think would be a nice reward!” “Mistress Jennifer is going to give you five more nice swats with the crop as her reward!” “Only, Jennifer is going to swat you right on your ass crack, and we will remove the plug so that your hole can accept the kiss of the crop!” “I will also be giving you five good swats along your crack when Jennifer is done too!” “Now, I want you to remain perfectly still and quiet for this reward!” “If I hear even one sound from you, your punishment for this will make everything up to now fail in comparison, is that clear slave boy?” “If you cannot accept the terms of this reward, then I want you to beg to be gagged with this butt plug and we will double the amount of swats with the crop!” “What is it going to be slave boy?”
I was really nervous now, I truly wanted to please Mistress Haile and take these ten swats without making a sound, but the truth be known, there was no way I could do that, and I am sure Mistress Haile knew this as well! I thought about it some more when one of them started to squeeze my balls again in an attempt to hear my response!
“I am sorry Mistress I will accept the gag and the additional swats Mistress Haile!”, (I stammered out my response)!
“Hmmmm, What do you think Jennifer, that isn’t quite the terms I set forth were they?”
“No, they aren’t Haile, I believe slave boy was to beg for the gag and the additional swats, which should now be redoubled again, I think!”
“Excellent Jennifer, OK slave boy, last chance, before you get more punishments!” “We are up to forty swats on your open hole and ass crack, do you want more?”
I sobbed out another apology and begged my Mistresses for the butt plug gag and the additional swats of the crop!
Jennifer once again lifted my head and presented the warm butt plug to my mouth. This time I opened wide and she shoved it in an inch at a time. It was too large to go all the way in, so she just kept pulling it out then turning it and putting it back in! Mistress Jennifer was making me lick and suck the whole plug this time!
I soon felt the first violent swat of the crop right on my open hole and it caused me to literally jump in my bindings! Mistress Jennifer even commented when my muffled scream escaped my lips!
“There There slave boy, only 39-more to go!”
Mistress Haile showed no mercy in delivering her twenty to my punished hole! Then they switched again, and Mistress Jennifer proceeded to rain down the short quick swats to my asshole and crack! My mouth was just open as my moans became one endless string! I was unable to suck or lick as I was constantly moaning now with each brutal swat!
Mistress complimented me on accepting her reward, then said that it was actually Jennifer’s reward really, as she was the one who thought it up!
Mistress Haile then handed Jennifer the huge blue dildo and said that we should really use this one instead of both, and she said it was slightly bigger and contained the thick ribs to give slave boy more pleasure!
(More pleasure I thought, that was far from true, the ribs caused me far more torments, and once again I caught that evil little glint in Mistress Haile’s eyes that proved to me that she also was aware of this too)!
Then Mistress Haile pulled a stool to my head, and said that as my ass hole was being punished, my mouth would be put to work on Mistress’s pussy and asshole, as she wanted orgasms from both! And said that when it was time to switch, I should tongue and lick Mistress Jennifer there too, giving her as many orgasms as she wanted! It turned out that Jennifer wanted three orgasms, and Becca got her two! My asshole got the punishment Mistress Haile intended for it as it was mercilessly fucked hard and deep for the next two hours straight!
When I was untied from the horse, Mistress Jennifer said that she doesn’t like to be so one-sided in her punishments, and after I was given a rest period, she wanted to spend some equal time tormenting my cock and balls like that of my asshole!
Mistress Haile agreed, and after my rest, I was positioned back on the punishment horse, but this time face up. My legs and arms strapped and cuffed to the legs of the horse.
Mistress Haile removed my cock sheath and my member sprang to life! Mistress Jennifer massaged it to it’s full size and it felt great to have it out of it’s small cramped and painful confines!
True to their words, my Mistresses took turns punishing my cock and balls, using various torments, they beat, punched, cropped, waxed, and froze my cock and balls, dripping black wax then using ice cubes! Over and over they repeated their abuse in various forms on my helpless genitals!
Mistress Haile then shifted gears saying that it was time to feed me some protein! For the rest of the night, my Mistresses would take turns straddling my face and either had me lick and suck their pussies or their assholes, while they both milked my cock and balls dry! I must have cum four times straight, and after each orgasm, my cum was force fed into my waiting mouth! I was ordered to swallow this and show my Mistress’s my appreciation for their efforts!
Mistress Jennifer then whispered something to Haile again, and Mistress Haile announced that tomorrow, Mistress Jennifer’s slave boy would be joining us tomorrow and that she wanted me to taste my first man! I would be dressed in my sissy panties, and Jennifer’s slave would then use my mouth to deposit all of his pent up cum! Mistress Jennifer wanted her slave to shoot a nice big load of cum into my asshole, so she could fuck me with the huge blue dildo again and have me suck all of the fresh cum from it that she could get out! Mistress Haile was delighted at this idea, and said that maybe that would be how we would introduce me to the taste of another man! Either way, I knew that I would be eating more cum tomorrow and my wicked little Mistresses would keep coming up with more torments for this slave!