Andrew's Property Ch. 04

This is the fourth installment in this series. It obviously helps to read the previous parts. This installment revolves around submission and pain and how it can be so pleasurable. I hope the story provides pleasure to you the reader.

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I woke up in the dark. But I heard distant voices. It took me a minute to remember where I was. My hands were tied over my head, and my legs secured to corner posts of the bed. It wasn't really a bed, more of a table covered with a thin layer of padding. I was guessing the surface was black pleather. The practical side of me figured that would be more sensible than real leather.

I was at Kassie's apartment in her dungeon and I was her submissive pet for the evening. Her brother Andrew owned me, well he and his Theta Chi brothers. He owned my wife too. Amazingly we started the day as a boring set of married professors.

But our day was anything but boring. I smiled when I thought about the fact that I sucked three cocks today, fucked a smoking hot co-ed, and had just about the best orgasm of my life getting ass fucked by Kassie while watching my wife getting split roasted by two Theta men. And that's the short version of my day.

I had no idea where my wife was, but my guess is she was serving Theta Chi men somewhere. My wife and I had flirted with submission before but never acted on it, certainly not in the way we had today. But here we were, and I was actually happy. I had a deep-seated need to submit and Andrew had brought that out fully and as far as I was concerned I had no plans to put that back under wraps.

I was thirsty, and hungry. And as if on cue, a very tall, very beautiful woman entered with a big bottle of water and what looked like granola bars.

Without saying a word, this goddess of a woman came over to me and used a control module to raise the head end of my bed. I was still bound but now I was sitting up.

She came over and stood next to me. Her ample breasts were pushed up and together by the black tank top she was wearing. Her midriff was bare and there was not a millimeter of fat on this woman except exactly where it was supposed to be. Her legs went on forever as they came out of a tightly wrapped white skirt and her feet were adorned with some serious fuck-me boots that came almost up to her knees. The lines of her body were perfect for her outfit, and her outfit accentuated her perfect body.

She opened the water and poured some in my mouth. I drank vigorously.

"Thank you" I said sincerely.

"Mistress Kassie demands silence from her slaves. Speak only when spoken to. And you can call me Mistress Hanna."

I just nodded at her. She proceeded to unwrap two granola bars, but instead of giving them to me she put them on the table between my legs.

Without saying a thing, she brought her long fingers to my dick and slowly and methodically untied the ropes that had bound my dick for the last few hours. She then started to give me a hand job. I remained quiet, but my dick sprang to life. Her touch was amazing. She was expertly pushing me towards ejaculation. Her expression was one of disinterest, but her actions and her look created a situation where I just didn't care.

"Inform me when you are ready to cum."

"Yes, Mistress Hanna," I replied. Although that moment was SOON!

"I understand you got to watch your wife get taken by two Theta men and you loved it."

"Yes, Mistress Hanna."

"You like when real men take your wife, don't you?"

"Yes, Mistress Hanna."

"Think of that and cum for me." She said as she increased both the pace and the pressure of her stroking.

"Yes Mistress, I am about to cum!"

She used her free hand to grab the granola bars and she held them as I ejaculated onto them and her hand. She milked any last cum from my softening dick and made sure the granola bars were covered. She then smiled, said "now you can eat" and put the first bar into my mouth.

"Mistress Kassie wants you to fully enjoy both bars"

I ate the bars and my cum while continuing to enjoy this amazing creature that was feeding me. I finished the second bar and then she fed me the remaining cum on her hands. Finally, she gave me the rest of the bottle of water, then got up to leave.

"Mistress Kassie will be in soon," was all she said as her near perfect ass walked away from me.

I remained silent, but hoped that Mistress Hanna and I would interact again soon. I wouldn't hesitate to eat my or anyone else's cum in order to be in her presence.

It was about 10 minutes later when the door opened and Mistress Kassie entered. She was quickly followed by four men. Each man was naked and had a thick leather collar on their neck and a leather harness on their cocks. The cock harness had one loop around the base of the cock, one that constricted the ball sack, and one around the cock in front of the ball sack loop. It made each cock somewhat aroused. Each was a different shape and size although one looked like it was the size winner of the group. I laughed at myself that my first observations about the men were their cocks. I never found men attractive, but for some reason I found cocks irresistible.

Kassie looked amazing. She was wearing black panties that might have been latex or spandex and were more like very tiny shorts than typical panties. Her stomach was bare and all she had on up top was a severely cut off grey t-shirt that was so short that the bottoms of her amazing breasts were clearly visible. Her torso was strong and sculpted and she had no shoes on. She had a belly button piercing that made the whole look come together. The look was beyond sexy.

None of the four men said a word as they stood off to the side of my bed/table.

"I hope you enjoyed your snack." She teased me. "My slave Hanna is quite the expert at getting men to frost their own snacks."

I didn't speak as her approach did not feel like a question.

"James, come over here and suck this man's dick."

The third man in the line didn't hesitate, and came over immediately and bent over and started his task.

Kassie just looked at me without saying a thing while James went porn star on my dick. After a good five minutes of this Kassie suddenly snapped.

"Back in line slave!"

James immediately complied and disentangled himself from my dick and returned to his previous position.

"Ice Water" Kassie commanded and seemingly out of nowhere, the biggest guy on the end passed her a pitcher of ice water.

"Ask me to pour this over your dick!" She commanded me.

"Please pour the water over my dick Mistress."

And she did, with the obvious effects. It hurt as it was very cold and it shrunk my aroused dick.

And this was Kassie's game. For the next 30 minutes she had each man suck my cock and get me aroused, and then had me ask her to pour the ice water. By round four of this my balls ached. She enjoyed this up and down (literally!) and kept teasing me that she totally controlled my dick and any potential pleasure I might receive from it.

After round four, my small, flaccid cock was done. I am not sure it could get hard if Kassie herself took a turn. But that was her plan. She went over to a table and returned with a chastity device.

"You will beg me to put this on you and then beg me to keep the one and only key. I will lock you up and thus from this point forward, for as long as I want, your time here, or time with any Theta men will be only about the pleasure of others. Certainly, your wife won't miss your little dick as she will be receiving pleasure from Theta cock pretty much every day. So, start begging and if you convince me I will lock you up."

"Mistress Kassie please lock my worthless dick away. My pleasure is in serving. My hands, my mouth and my ass are all hungry to create pleasure for you and any and all Theta men. Please keep the key and help me focus entirely on the pleasure of others. I promise I will never ask you to unlock me. I am your submissive slave and will enthusiastically accept your complete control over my dick, and every other part of me. So please Mistress lock my dick in the chastity device and keep the one and only key to use solely based on your whims and desires."

I said all of this sincerely. As a long-time submissive this was actually a dream come true. I am easily controlled when you have my dick hard and aroused but I have always wanted to test myself beyond that. Now I will truly get to see if the obedient slut I always claim to be while my dick is hard and throbbing is equally submissive when my sissy dick is locked away and unable to do my thinking for me.

Kassie smiled and said, "Request accepted." Then she immediately started to lock me away. The device was clear plastic and held both my balls and my dick. She put the device on quickly, this was obviously not her first time. She spoke to me as she did.

"I am using the smallest cage because damn you have a tiny dick when it isn't aroused. No wonder your wife orgasmed like she did today. I doubt anyone will miss your little dick. It will be at least a month before I even think about unlocking you. You'll need to sit when peeing and clean it regularly. Jacob over there will show you how. He just finished a full six months locked away. After two weeks I will milk you, that will actually be very pleasurable for you. Or at least as pleasurable as it is going to get for a while. There we are all done. What do you say?"

"Thank you, Mistress Kassie. My dick truly belongs to you now. I look forward to focusing entirely on obedience and the pleasure of others."

"And that is where we are going next. My four slaves here have all served me for at least 6 months and Kevin over there has actually been serving me for almost 2 years. You are going to earn your way into this group, but in the mean time they are your teachers. Tonight, you be trained to suck cock and get fucked in ways that provide the most possible pleasure for the man involved. Are you ready to start your training?"

"Yes Mistress, I promise to be a serious student."

"While I appreciate your sentiment, I want to let you know that failure to make progress will be dealt with harshly. And just to be sure you fully understand harsh, I am going to punish you. Not because you have yet done something wrong, but so you truly understand the consequences of disobedience or lack of real mastery on your part."

I did not respond as I was unsure of what to say. In a flash Kassie snatched her riding crop and hit me on the chest.

"Beg me to hurt you, my pathetic sissy!"

I guess I should have responded to her first information for me. But after the encouragement created by her riding crop, I jumped in right away. "Please help me experience pain and accept it as part of my obedience to you. I understand that at times I might earn the pain because of my poor behavior, and other times simply because you wish to inflict it. Either way I am yours to use and I beg of you to enjoy yourself and know while the pain may be severe, I am grateful to be able to serve you."

"That was very poetic, now just beg me to hit you!"

"Please Mistress hit me. Hit me hard!"

I guess I didn't have to truly beg because a barrage of crop hits came next. Each was painful, but the series of them took my breadth away. My whole body screamed in pain.

"Again!" Kassie roared with a definite sadism in her tone.

"Please Mistress hit me again! I am your loyal slave and servant!"

This time she instructed her cadre of slaves to reposition me back to hanging from the arm pullies but didn't secure my legs. As soon as they had me secure, the assault began. Kassie paid special attention to my ass and the back of my legs. After 6-7 hits she swung for the back of my thigh and I moved, mostly involuntarily, in a way that made the hit indirect.

"Don't you dare try to avoid my hits!" So, she left my legs unsecured to test me. It was a hard test. Your body has its own set of natural reactions to pain and the first one is avoidance. That means I had to will myself to take the hits and not try to shield my legs by moving out of the crop's direct path. I chanted in my brain, "obey, don't think, just obey" and it helped me.

Kassie repeated the blow. I took it directly. She then started slowly, but methodically working up both sets of legs. She took her time between hits. "Stay focused on serving, accept each hit with pleasure my slave!"

I did my best. At this point is was hard to stay focused. I was crying. I mustered all my focus and stayed still as she made my legs and eventually my ass explode with pain.

"Bring me the clamps." She directed toward her slaves.

A large tray of various clamps was brought to her. The younger guy with the largest cock held the tray.

She took a pair of clamps off the tray and help them out in front of me. "For your nipples," she said as she put one back on the tray. She used her free hand and rolled my nipple between her thumb and forefinger to make it hard. Then she secured the clamp. It hurt bad! She repeated this with the other nipple. The only good part is the nipple pain made me less aware of the pain still throbbing from my legs and ass. That relief was short lived. She went back to using the crop and must have hit me 12-15 times. Now I forgot about the nipple pain.

"Round two!" she said with a devious grin. And now she applied four or five clamps to my face. My nose, my eyebrow area and even my tongue. My whole face area was on fire. And then, once again, she picked up the crop. I was barely holding it together. She could tell.

"You are a dedicated slave Jimmy Boy aren't you?" I couldn't really talk with a fancy clothes pin on my tongue and another on my lower lip, so I nodded a yes. "And you want to keep pleasing Mistress, right?" I nodded. I really did. This is a submissive's dream come true, but the fantasies and the current reality had one big difference: real pain. "Take the pain for me. Stay obedient. Understood?" I gave her one more nod. Her talking to me and the quick break help me build my resolve.

"I am going to hit you again. It will please me. Tell me you want to please me."

I tried to say, "Enjoy yourself Mistress, hit me all you want." Although I doubt that is what it sounded like as I struggled to speak. She laughed and said, "I'll take that as a green light."

Slap! The riding crop hit me. Then again. Then again. She spun around me with a playful approach, but there was nothing playful about her hits. "This is such fun!" she proclaimed as she hit the back of my thigh, my stomach and then my ass as she twirled around me.

She stepped lightly over to the clamp tray. "Hmmmm, six more clamps. I think I should secure three, enjoy my riding crop, secure the other three, and finish with a big flurry of hits. Like a grand finale! Yes, that's what I will do!"

The first three clamps went on my arms hanging over my head. She grabbed just enough flesh to secure the clamps. She did this quickly and while there was some pain, it was mild in comparison to what I was already enduring.

"Let's try something new!" She came over to me and with an evil grin said, "I think you are going to like this!" I wasn't so sure, but I continued to remind myself serving my mistress was my desire.

"Gentlemen," she called to her slaves, "grab a toy; a whip, a cane, or one of the other crops, and let's give our new arrival a faggot slave welcome."

There was a "yes Mistress" in unison by her four slaves. Quickly I was surrounded by all four men. They each held an instrument of pain. Two of them had gotten hard in this short period. I focused my attention on one of the cocks and thought about sucking it. It was my way of distracting myself from the existing and soon to come pain. It was a nice cock. He was cleanly shaven and it was a smooth, averaged sized cock with a slight curve up. I was picturing myself on my knees sucking his cock when my distracting little fantasy was interrupted by my Mistress.

She was looking and speaking to me, but obviously the instructions were for her slaves too.

"I am going to ask you a question, you will nod, then I will instruct my boy toys here to smack you. Four hits for the price of one. How delicious. Gentlemen, as a practice go ahead and hit our new faggot here on the count of three, two, one..."

FUCK! The four blows, especially the one to my ass made my body light up with pain. It was overwhelming. My breathing got ragged and I had to use all my will power to not beg Mistress to stop. The look on my face must have revealed my pain and my struggle.

"OOHHH, that was the trick. Boys, I think we have our new slave's full attention. Just to be sure, hit him again now!"

And once again a blast of pain hit me. This time I let out an uncontrolled yelp. I was definitely crying.

"Yup, we have his attention for sure!" Kassie laughed.

"Now, I have three questions for you. I want you to nod your yes and then I will have the boys hit you. You can nod no, and I will release you and send you home and you will never see me or serve me again. So, are you ready?"

I nodded a yes. I still couldn't really speak with the clamps on my tongue and lip.

"Question one, you enjoyed sucking my brother's cock, and those of his Theta brothers, today, correct?"

That one was easy and I nodded yes. I almost got a full pleasant thought completed about how I enjoyed those three cocks before that thought was thrust from my brain and replaced by the pain of four hits.

"Excellent boys!" She praised her slaves and then spoke to me. "Only two more to go, each will hurt just a bit more, but you will accept and cherish that pain as you know it pleases me. So, question two: You want your wife to become a full-time, always available, Theta slut and fuck toy, correct?"

I nodded my yes. Because it was true. It was very arousing to think about my wife as the fuck toy of other men, especially younger men who are supposed to be behind us in the power structure but instead will be our masters. I also knew that they would fuck her and provide her pleasure in ways I could never.

Again, my thoughts were cut short. The four men had rotated once around me and now the pain distribution was different. It was the cane that hurt the most and this time that blow came across the back of my calves. If I weren't tied up and hung, I would have collapsed.

"Splendid. Our newest slave wanna-be is learning that being a slave is not just fun and games but requires real commitment and real sacrifice. Oh, and at times it hurts like a banshee! Ain't that right boys?"

The pain inflicting four all let out a "Yes, Mistress" without hesitation. Fuck I was torn. This has been my dream, to have a master and a mistress, especially having both. But dammit, this hurt. I am not sure what was cycling faster, my nerve endings or my brain. I tried to take longer, deeper breadths and calm my entire self down. It had limited effect. I was engulfed in pain, in confusion, in happiness, and in arousal. Kassie cared not for my struggles and pushed forward.

"Question Three: You want to be a cocksucker and fuck-toy for men, always putting their pleasure ahead of yours, correct?"

The answer was YES! But my nod was more subdued. Pain will do that to you.

And the pain came. Kassie just nodded at her slaves and again they hit me in unison. One of the whips hit my arms, and hit them hard. The blow also activated the pain from the clamps and because I was somewhat hanging from my wrists, there was no way to lessen the pain. I gritted my teeth, but obediently remained silent. The other blows hurt too, but slowly I was absorbing and accepting the pain. And in fact, after this round my biggest response was arousal. I was getting whipped for my Mistress, and she was a goddess! My dick was now pushing hard against its cage. I was realizing that my Mistress could have me in an aroused state even if my dick was caged.