After years of reading countless stories, watching videos, staring at pictures, and dreaming, I decided it was my time. Although I had no doubt the people depicted were experiencing real pain, I wanted to know for myself what they were actually going through. It seemed that the more pain the people were feeling in what I was seeing, the more turned on I became. Now, it was my turn.

I was familiar with Ms. Boss and The Compound from the internet. I wrote to Ms. Boss with somewhat of a skeleton scene that I had imagined. It took all the nerve that I had to press the send button. Once my initial email was sent, I knew there was no turning back. Ms. Boss replied, we confirmed a date, and exchanged a couple emails. The day of the session, we spoke on the phone. To not make it seem like the entire scene was scripted, Ms. Boss told me that she would design the scene around things that she thought I would like based on conversations, but I would not necessarily know when or how to expect what and when exactly what was going to happen. I will tell you, she did not disappoint.

The scene was to be a judicial punishment session with a sensual twist. Ms. Boss greeted me at the door dressed like a strict disciplinarian. She had her hair tied back behind her head. She wore a black blazer, that was buttoned enough to look professional but low-cut enough to show how sexy she was underneath. Her skirt was short and form fitting allowing her very firm legs in black stockings to be noticeable. She wore a set of high-heeled shoes to further accent her legs. Ms. Boss appeared to be very authoritative yet incredibly sexy at the same time.

Ms. Boss asked if I knew why I was there which I nervously acknowledged. Ms. Boss showed me her collection of restraining devices on the mantle just inside the foyer. She then proceeded to place me in handcuffs and shackles. From there I knew that this was for real! She led me three flights upstairs to a room on the top floor. As we walked up the stairs, I could see various rooms used for other types of punishment, torture, and most of all, pleasure. I was taken to a room where I was to be prepped for what was about to come. Ms. Boss removed the handcuffs and shackles. Upon removal of the hardware, Ms. Boss swiftly removed my clothes. She left my underpants in place, although they would not stay in place long.

Ms. Boss then took me to the punishment room where I was able to see the fate that awaited me. She gave me the opportunity to take a quick look around the room. On the far side of the room, I could see there was a very large collection of paddles, canes, and straps hanging on the wall. A punishment box was on the floor directly in front of the largest collection of punishment devices I could have imagined. A large sturdy chair sat just beyond the opening of the doorway. The left side of the room had a large collection of books, hence the library. By far the most dominant feature in the room was the Berkley Horse. The large wooden structure was in the shape of an A-frame standing nearly 6 feet tall. The victim end was at an angle of about 35°. For now, the more unusual features of the room were going to wait. Ms. Boss had plans for me using items that are more “conventional”.

Before I knew it, I was looking straight down bent over Ms. Boss’s lap as she sat in the firm wooden chair. Her firm grip and swift motions gave me no chance of hesitation. Ms. Boss gave me a chance to realize what a vulnerable position I was in as she explained what was about to happen to me. While fearing what was about to happen, I could not help notice that Ms. Boss’s legs were just as firm as they looked. I thought to myself that if her arms were in as good of shape, I could be in some trouble! She explained to me that I was to receive 500 spankings with her bare hand! The 500 spankings were to serve as a warm-up and I would receive a break in between each set of 100. I was thinking that 500 sounded like a huge amount! How would I ever survive an hour?!?!

It was now time to begin the first phase of the punishment. Ms. Boss grabbed the waistline of my underpants and pulled them down to my thighs to expose my bare ass. A sudden rush came over me as she was taking them down. She gently rubbed my ass with her hands in preparation for what was about to come. Through the entire ordeal, Ms. Boss fully explained what was going to happen while being the firm disciplinarian that I was quickly finding out she was. And then it began.

She applied her hand rhythmically and alternated on each side of my ass. The first 100 seemed to go on for quite a while and then suddenly ended followed by a gentle caress. The pain was intense but very much bearable. Soon the next set of 100 began just as firmly however seemed to cause much more intense pain. I could feel the fire beginning to ignite on my ass. It was tolerable…..at least for now. Soon, 200 spankings were completed. I was feeling confident since I had made it through 200, yet realizing that I was not even halfway through just this first stage of the punishment, and this was only the warm-up! Once again, after a brief caress of my ass, the next set of 100 spankings began. By this time, it seemed as though the pain was 3 times as worse as when it first began. In my mind, I was thinking that I am almost halfway through, but at the same time thinking, I AM ONLY HALFWAY through! The third set seemed to go on forever then all of a sudden, there was relief. The intensity of the searing pain was even more intense but I thought that I was over halfway there. I could make it the rest of the way. The fourth set of 100 began before I knew it. As feared, I had the urge to get up to escape, however on this set of spankings Ms. Boss had my arms pinned behind my back. There was no escaping her firm grasp even if I had tried. I felt myself screaming in my mind while I tried to take the focus away from what was happening to my ass. Suddenly, the 400 spankings were completed. By this time, the pain seemed to have drained most of my energy. I took comfort in knowing that there was only 100 left, however, there was still 100 left. Once again, after a brief caress, the final set of 100 began. It almost seemed as if I was in a different place and time yet it was impossible to ignore what was happening to my ass, which had never taken a punishment such as this. Somehow, by some miracle, 500 spankings were completed, and I actually survived. The bad part is that this was only the warm-up as Ms. Boss reminded me about at the end of this phase.

A look in the mirror revealed my ass beginning to bruise. Ms. Boss had me take a break by sitting bare on a wooden chair for a few minutes while the next phase of my fate was prepared. I was given a small bottle of water to drink.

For the next phase of the punishment, Ms. Boss took me to the punishment box across the room with my underwear pulled up. The punishment box was about waist high on the back end, and sloped upward toward the front. Ms. Boss had me approach the bench at which point she affixed heavy leather cuffs to my wrists. Ms. Boss had me bend forward over the box. Ms. Boss firmly attached the cuffs on my wrists to the punishment box in such a manner to allow little, if any, up-down or side-to-side motion. Ms. Boss laid a couple leather paddles on the floor in front of me to observe while she finished the restraining. She then affixed similar cuffs to my ankles and secured them to the bench in the same very restrictive manner. After Ms. Boss had me affixed in place, it was apparent that I had even less of a chance in getting out of this predicament than I did while over her lap.

I was informed that there were to be 6 strokes of the leather slapper on each side. After each stoke, I was to say “thank you, may I have another?” when prepared for the next stroke. Once again, Ms. Boss came behind me and took my underpants down to my thighs. She pressed her body up against mine to give me another sensational rush of pleasure before the punishment was to begin once again.

The next phase of the punishment began with a loud crack that seemed to send waves through my body. Each slap of the paddle seemed to be worse than the last. Somehow, I managed to find the strength to utter the phrase that would award me another blow. The first six strokes finally ended, however, that was only half of the strokes Ms. Boss was to administer using this implement. The next six strokes continued on the opposite side, which also seemed to get increasingly more intense. With each painful blow I wanted to scream out, however, I managed to keep some dignity. Instead, I was able to utter the phrase and receive another blow. By the sixth stroke, I was barely able to get the words out of my mouth. The disturbing part is that this was the less brutal of the implements that Ms. Boss was using in this phase of the punishment.

For the next phase at the punishment box, Ms. Boss was to continue the punishment using the prison strap. This implement was leather like the leather slapper; however, it was thicker and appeared to be much heavier. Similar to the first stage on the punishment box, prison strap was to be administered with six strokes on each side.

After a very brief break, Ms. Boss delivered the first stroke of the prison strap. It was immediately apparent that my initial observations were correct. The prison strap indeed was much heavier than the leather slapper. The difference between the leather slapper and the prison strap was very easy to distinguish. Each blow seemed to have 10 times as much force behind it due to the added weight of the strap. Prior to the start of this phase, it seemed that the punishment could not get any worse. The prison strap proved that theory wrong. Each blow sent a tidal wave of pain through me that made me try to break free from the bonds, but it was of no use. I came to the reality that I was not going anywhere until Ms. Boss had completed what she was there to do. I had no choice but to take the punishment that I had asked for. Reluctantly, I forced out the phrase required. Blow after endless blow Ms. Boss carried the punishment out. The sheer weight of the prison strap felt like it was penetrating through the full thickness of my ass. In this very bent over position there was not much density to my ass to absorb the thrashing being dished. Much to my disbelief, this phase of the punishment actually ended. Shortly after, Ms. Boss released me from the punishment box. However, the complete punishment was not over.

The final phase of my fate was to take place on the Berkley Horse. Once I was standing on the Berkley Horse, Ms. Boss placed my cock and balls through a sort of stockade, which consisted of a hole between 2 planks of wood that fit together and she locked in place. Ms. Boss then secured my wrists above my head on either side of the horse. My feet were a few inches apart at the base of the horse. She then connected my ankles to the horse using straps so that I was unable to move once again. Ms. Boss then informed me of the good news which was that my ass was going to get a rest. She then informed of the bad news in that my cock and balls were next in line for punishment.

Ms. Boss set a box of clothes pins were set on the floor in front of me. It was obvious that something was about to happen of which I had only seen in pictures. Ms. Boss started with a little gentle hand slapping to my cock. I could feel my cock growing more erect by the minute. After a little stimulation by hand, one by one, Ms. Boss applied clothespins to my cock up one side and down the other. I have no idea how many were applied but it seemed like quite a lot. Ms. Boss then attached several clothespins to by balls. Quite to my surprise, the pain was actually a turn on. This was about to stop.

With my ass having enough of a break, it was time to rekindle the fire once again. Ms. Boss applied another series of blows with the leather slapper. Yet still very intense, the upright standing position seemed to be less severe due to have less stretched muscle, therefore more density to absorb the blow. Due to the increased tolerance of pain, Ms. Boss decided it was time to introduce my ass to the tawse. Ms. Boss warned that the tawse was going to prove to be much more intense than anything I had endured thus far. The concept of anything worse seemed nearly impossible. The tawse is merely a leather strap that seemed to be no more than an inch wide with half of the strap split down the middle in two straps. The tawse did not seem like a formidable device at all. Once again, Ms. Boss proved me wrong. The first blow by the tawse did not feel nearly as heavy as the prison strap; however, it had the stinging sensation like nothing else had to this point.

After the first blow with the tawse, Ms. Boss decided it was time to try the ball gag. Ms. Boss thought that having my wrists, ankles, cock and balls was not enough. She then decided that although it was impossible to break free physically, it was necessary to render me further helpless by not being able to beg for the punishment to stop. The gag fit securely and rendered any speech inaudible. It was now up to Ms. Boss to decide when to administer the next stroke. Each stroke made me feel weaker until I was to the point of being dizzy. Three strokes of the tawse were almost mind numbing. The pain that Ms. Boss delivered by using the tawse was searing. The punishment stopped to let me regain full awareness to continue.

Ms. Boss took my hands from above my head and strapped them straight down to my sides on either side of the horse. Ms. Boss removed the ball gag and the punishment to my ass continued. Ms. Boss applied a series of blows to each side of my ass while she held my hand down to keep it from being struck. The sensation of human contact seemed to take my mind away from the punishment that was happening. After a few more strokes of the strap, Ms. Boss decided to focus attention elsewhere. The clothespins Ms. Boss connected to my cock and balls were still connected, but there was not nearly the firmness in my cock as there was at the beginning of the phase on the horse. Considering the fire burning on my ass, it is no wonder that the cock was no longer erect.

Ms. Boss then brought out two devices that looked like wands with a round flat pad on one side. She showed me how they worked by applying it to the underside of my cock. The sensation that I felt was unlike none that I have ever experienced. Ms. Boss stopped the stimulation. After letting me settle back down and switching devices she began again with the next. This time while Ms. Boss applied the stimulation, she would place her face next to my face. The close contact was driving me wild. It was incredibly erotic to feel the sensation while touching her cheek next to mine. All the while, I could smell her scent and feel her body pressed up next to me.

The series of stimulation and teasing occurred for a while each time getting closer. Finally, Ms. Boss gave me permission; however, it came with a price. Directly after, Ms. Boss was going to administer three severe swats with the very large wooden sorority paddle. The way I looked at it, any price would be worth it. I knew that I would not have this opportunity every day so I decided to go for it. (However, I do not believe that I had much of a choice in the matter.) The sensation was maddening to the point where I could hold back no longer. After my breathing calmed down Ms. Boss reminded me that I was now to get three blows with the sorority paddle. The strokes of the large wooden sorority paddle were going to be extremely intense and would not feel good at all now that I achieved orgasm.

The first blow, as promised, was delivered and it hit me like a truck. I felt like I was going to break away from the horse, but I knew that was impossible. The pain in my ass was searing. After a few moments, I was able to catch my breath. With some forced effort, I was able to lay back forward on the horse and relax. Soon after, the second blow with the paddle landed. This time it was equally as intense, if not more. It was almost as if a truck hit me the first time, followed by a second larger truck. Again, it took me a while to recover from that one but somehow I managed to slow my breathing, relax, lay forward, and brace for the last blow.

Ms. Boss informed me that this was to be the most intense and hardest stroke of the night. At this point, I could not have thought that there was any way that it could be possible. In my mind, I knew that after what seemed like hundreds of blows to my ass, surely I could take one more. Out of the corner of my eye in the mirror, I saw Ms. Boss draw back the paddle as if she was getting ready to hit a home run. The last one landed on my ass like a clap of thunder. That last one seemed like it was a culmination of all of the other blows of the evening combined into the intensity of one. Should I not been braced by a firm surface at the front, I am certain that it could have broken me in half. The intensity was almost unimaginable. I was nearly dizzy after the intensity of the pain.

With that last and final blow, my first ordeal concluded. My ass was on fire, beet red, bruised, and welted, as never before seen. I could not believe what I had gone through. Somehow, I had endured all that Ms. Boss had planned and carried out.
The motto on Ms. Boss’s website says that this will be the best mistake you will ever make. As it turned out there was never a more true statement. My only regret is that I wish I had made this mistake sooner. Luckily, I am a slow learner. It looks as though I am going to make the same mistake again.