Another write up from Ru. 🙂
So here I am again, a night after another session with Sir Soxster. I’ve been hesitant to do this write up because writing up a report is a sort of conclusion to the whole experience, an end if you will to a journey that you’ll be remembering for the rest of your life. Last night was the same and there is no way that something like last night will ever happen again, unless you get to lose your ass virginity twice.
Throughout the week, I had been promised by sir that I would lose my ass virginity, something I promised to lose to him during our very first season. But masters can change their minds and slaves just have to deal with it. I also had to deal with the prospect of losing my ass virginity to a random top via way of raffle. While the stuff of dreams in theory, the practical idea of losing my virginity via raffle was daunting. I guess society has a way of positioning virginity something pure and special and the thought of someone seeing me as just another hole and another point on the scoreboard sounded humiliating. However, I came around and realised that I was my masters little bitch, a piece of property that could be used in any way he saw fit. Unfortunately that didn’t work out and only two other people showed up, two fisting buddies of sirs that were big and beautiful bears (at least I think they were because I could only feel them). Nonetheless, I feel that all four of us had a very good time…I think.
So the session started off well before the guests arrived. Prior to the session, I was told to stop jerking off two days before the session, failure to comply would result in hits to the balls. I was instructed to arrive 1 hour before everyone else so that I could be prepared and tied up for the guests. However before that, I was told by sir that I needed to provide a write up on what I thought was going to happen during the session, on a train full of people. To say the very least, it was humiliating. With barely enough space to put my hands in a comfortable typing position, I was forced to write about my sexual fantasies in a train carriage full of people. Paranoid at the thought of someone looking over and reading about my desperation to have a cock in my hole, I was relieved to stop writing and send the story to sir once I had arrived at the station closest to sirs apartment. Then it set in, the fear and realisation that I was going to leave sirs apartment a virgin no more. I was terrified, but like all the other times, my hands knocked on the door and I turned my back and faced outwards.
With blindfold on, I was once again escorted into sirs apartment. Led to bathroom, I was instructed to strip my clothes off into a container and relive myself in preparation for the events of the day. For the first time in sirs apartment, I didn’t have a blindfold on. It was lot larger than what I thought it would be. Having been showered blindfolded the week prior, I expected the space to be a lot smaller given the amount of things I had hit my head on. Being blindfolded, your senses are heightened but are often mixed up. It’s funny to see things differently from what you imagined them to be, there’s a surreal aspect to it and it’s kind of strange to evaluate the differences between what is in your head and what is actually in front of you.
Blindfold back on, I was taken out and quickly led back into the toilets for a pubic hair trim. Sir had mentioned that my pubic hair was too long and that shaving it would make my dick look bigger and be more pleasureable for masters to play with. A win win situation. Having my hair trimmed was a weird feeling. This may be a bit of an obscure reference but having my pubic hair trimmed was very similar to the scene in the Lion Witch and the Wardrobe, where the evil ice queen shaves off the lions mane before stabbing him with a knife. The feelings involved were very similar but instead of mane and murder, it was pubic hair and cock… Sir took extra care in doing it though, but I was very afraid. I feel the fear was justified considering that I was naked and blindfolded in someone’s apartment with a razor going around my penis… I’m sure sir knew what he was doing though.
After my dick was properly shaved, it was time for a pre session make out. This was the first time that I had been with sir while his shirt was still on. This part of the night was a bit of a blur, but I remember taking off sirs jock strap and sucking his penis for a little while. Usually when I arrive at sirs house, he is properly showered and cleaned so that I can work myself all over his hairy body. This was different, for the first time I was able to smell his scent and take it all in. I remember inhaling his dirty jock strap like a pathetic little slut boy while he laughed at me in disgust. From there, I was thrown onto the bed and we made out for a while and spooned. Finally it was time to tie me up for when the guests arrived. While tying me up, the doorbell rang and my heart skipped a few beats. I knew that sir had sent my pictures to a few other people and asked them to join the session. With my pathetic body and lack of any training, I was almost certain that nobody would even have the slightest interest in fucking me. I was very glad I was wrong and once sir had finished tying me up in his leather restraints, I was left to ponder what was about to come while the masters had a chat in the lounge room.
When you’re blindfolded and tied up in a bed that isn’t yours, your mind begins to wander. Horny as ever, I tried my best to listen for signs of life. With a hood covering my head, my hearing was also slightly impaired while I waited in agony for sir and his friends to come and play with me. Without knowing how long or when anything was going to happen, I lay there with a million thoughts running through my mind. This was it, tonight was the night I was going to get fucked. No turning back now.
Finally, after what seemed like a lifetime, it was time for the masters to see the new toy that sir had arranged for them to play with for the evening
After laying bound and helpless in sirs bed for what seemed like an eternity, I finally heard the sound of people approaching me. “So this is the boy” said one of sirs friends as he slowly glided his hands along my bare body. I was aroused and I was very sure that my dick was showing it very clearly, much to the delight of sir Andrew and sir Jeremy. From there I remember my head being dragged to the side of the bed, with mouth open it was time to suck my second dick. I had my second dick shoved forcefully in my throat and it was heaven. I could tell straight away that this penis was much younger than that of sir Andrews, similar to mine but a little bit more experienced. At the risk of sounding like a cock slut, I did notice the size difference between Master Jeremy and Master Andrews cock. After having been trained to suck and deep throat Master Andrews cock over the past 3 sessions, the introduction of a new and much smaller cock was really weird but also extremely satisfying. Master Jeremy tried very hard to throat fuck me and make me gag, but Andrew had trained me well and I was able to handle it like a good little sub boy.
This went on for a little while, my mouth being used as a filthy hole for the cocks of two masters. I felt so used and violated, I couldn’t pull away, I couldn’t scream, all that I could do was take the cocks and service them to the best of my ability. All the training that I had undergone was being tested and Master Andrew was always checking to make sure that I was putting into practice what I had been taught. Once both masters were bored with shoving their cocks in my face, a make out session occurred between the two of them. Blindfolded and tied up, I was only able to hear the sounds of kissing and moaning literally centimetres from where I was. It was extremely frustrating. I was so horny and wanted desperately to be a part of the action, but all I could do was lie there and wait in agony while both my tormentors were enjoying each others company. Another buzz at the doorbell and Master Kin arrives at the door.
This is where things start to get really really blurry. I apologise in advance to all masters for what I am about to write next, both in terms of clarity of events and my opinions on what occurred. I was in a constant sense of fear, agony, pain, horniness, delight and every other emotion in between. However I will try my best to put into words the mind blowing experience that all three of them gave to me that night.
As Master Kin arrives and gets undressed, I remember sir telling Master Jeremy that I enjoyed nipple play… it’s funny how the things you thought you liked could be turned against you in such a sadistic way. I’m unsure as to who was doing what but once all masters were in the room, I was played with like the slutty little toy that sir always said I would be. One master was sucking my cock and teasing me with his hands while another master one going at my nipples like no one else had ever done before. Master Andrew had always been fairly gentle with my nipples, but it felt like Master Jeremy really wanted me to go home with no nipples. Even today, 2 days later, my nipples still throb from the abuse that went on during that session. While this was all going on Master Andrew went about looking for toys to use on me while also surprising me with his fat cock in my mouth. Being used is such an amazing feeling, being a person that doesn’t have the greatest body, I have always felt that people would get sick with disgust once they saw my naked body. But here we were, three beautiful bears working on a helpless little boy, from their interactions it seemed as though they were enjoying using my body and that made me feel great. Did it hurt when the masters played with me, hell yes. But the satisfaction and joy that I felt when you come to the realisation that you’re pain is their enjoyment definitely outweighs the pain and the constant fear of wondering what will happen next. Then it was time for the toys.
The pin wheel was something that I had seen in many porn videos in the past, something that looked like a bit of fun that couldn’t hurt that much… but once again I was dead wrong. At first it was a little tickle, but once Master Jeremy began applying greater pressure, it felt like tiny little scalpels were piercing my skin. All around my newly exposed skin from the pubic hair trim and all over my sensitive worked on nipples, I was begging for him to stop, but apparently all that I was able to let out of my mouth was please… Apparently my painful moans and cries for mercy were satisfying for the masters and Master Andrew thought to make the pain more excruciating and terrifying, by introducing a new toy to my body. I had read masters blog about passing on electrical current through the pinwheel and onto a slaves body, it was one of the most scary things that I had ever read and I prayed that master wouldn’t do it to me today. As he fumbled around I was praying for anything else, a whip, a ball stretcher, chains, literally anything other than the violet wand. Then I heard the flip of an electric switch and I froze in fear, my nightmare was about to become a reality.
The violet wand was a device that is hard to describe. It is almost feels like that electrical buzz you get from touching an AC power brick from your laptop if you’ve left it idle for a long enough time, albeit at a much more higher intensity. Master Andrew was demonstrating the tool to Master Jeremy who was new to this whole thing, slowly zapping me and moving the device all around my body. Then he introduced the use of passing the electricity through his body and onto mine. It. Was. Hell. I didn’t know where the next zap was going to be or how it would effect me. Sometimes it was hard zap and at other times it was a dull buzz, sometimes it was with a finger, sometimes it was with the wand itself. There was no consistency and the anticipation for what was to come next was torture. Then Master Jeremy found the perfect torture device, passing the current through the metallic pinwheel device and right onto my sensitive nipples. He would roll them up and down my nipples and all over my body, the feeling of the electricity and sharp edges of the pinwheel were all too much and I begged once again for mercy, unable to stop what was going on. Instead of stopping, Master Jeremy went harder, to the point where I don’t remember what happened next… I was in so much pain and pleasure that my mind left me at that point. I mentally blacked out and I came back to reality once again when I was untied and instructed to service the 3 cocks on Master Andrews bed.
So it was finally happening. I was finally ready to transition from an inexperienced slave boy to a full fledged cock sucking slut. Waiting in front of me were 3 erect cocks, ready for sucking. It was overwhelming, but I knew what I had to do if I wanted to lose my virginity to one of those cocks that night. So off I went, putting to practice what I had learnt from sir in our previous session. Mix it up, use your hands and read the situation to see what gets the person hard. Sounds like an easy task, but when you’re blindfolded and tasked with servicing 3 different cocks the simple instructions become much more harder to follow. However, I tried my best and soon enough I had my head on one cock while my hands were jerking off the other two masters.
It is funny that you can tell the relative age of someone from their cocks. Master Jeremy had the youngest cock, being really firm and hard, unlike those of my other two masters. It was easy to arouse and make hard and it was a really great cock to suck and pleasure, a cock that I assumed was the most similar to mine. Master Kin had a cock that was well used. It was more difficult to please than Master Jeremy’s but once I found out that he also liked to have his nipples played with, his cock also became rock hard. And finally there was Master Andrews cock, I’ll just say that its huge and hard to please (there are a lot of literary pieces surrounding the size and notoriety of it, so I will leave it out to save some space).
Once again I was being used by three big bears, a toy that was only there to serve them. They were’t here to please me, I was there to please them. As they chatted about musicals and other interests I was working hard to make sure that their cocks were being well serviced. It was degrading to feel that I was nothing more than a piece of furniture for them, making me try even harder so I could maybe divert their attention towards me. But that didn’t work out, if I did a good job I was ignored and left to continue while they went about their conversations. If I wasn’t performing to the standard the masters desired, I would get a stern warning and a decent slap on the ass. If they felt like it, they would grab my head and shove their cocks deep into my throat, forcefully to ensure that I wasn’t there to just enjoy their cocks.
Being a cock slut is a lot harder than it sounds. You would think that it would be easy to switch between cocks and be used, but three times the cocks means three times the stamina needed to please the cocks… it was tough, but I knew I needed to finish my job if I wanted to leave. A sneaky little trick that I used during all of this was to sneak up and start making out with the master I was servicing. Like a swimmer bringing their heads to the surface for a gasp of air, I would slowly make my way up to the masters lips and start making out with them. This would give me a bit of rest and meant that I was still in the position of pleasing my masters. However, towards the end, I think they caught on and they shoved my head right back into their cocks whenever I tried to catch my breath.
Then it was time to become an actual toy. As Master Andrew went to freshen up for the deflowering, Master Kin and Master Jeremy decided to take turns and use me as their little drum set. As one master held me still, the other one would slap my ass as hard as the could, making some beats and enjoying themselves while I yelped in pain and begged them to stop. They didn’t, and felt that my pain meant that they should go harder on me. I feel that my ass was very red and hot after they were done with me.
Finally, it was time for the main event. The deflowering of my virgin asshole. Unfortunately there were not a lot of attendants, so the raffle was downgraded to a half arsed conversation between the three masters as to which one of them would fuck me. After about 10 seconds of conversation, it was decided that my ass would be taken by Master Kin, because he had never taken an ass virginity before. People spend more time deciding what kind of cereal to buy at the super market and here I was tied up in a sling while three men I had never even seen before, casually discuss who would be the first ever person to fuck me. It was absolutely humiliating and I hated them all for talking so casually about such a special part of the human journey. On the other end of the coin, the conversation made me extremely horny, here I was transitioning from an innocent little slave boy to full fledged slut. Who else can say that their first time was decided in such a way.
So it was time for Master Kin to finally fuck me. As I lay there in the sling, I thought to myself that this was really the point of no return. Was it something that I really wanted or was it something that I was doing just to please my master. Would I enjoy it, what were the repercussions of enjoying, what if I hated it, what if my ass started bleeding again. The amount of things that were going through my mind were insane and I drifted off into a world of blurriness. Before I knew it, Master Kins cock was up my ass. It didn’t hurt as much as I thought it would but it did hurt a lot. I expected my ass ring to be ripped apart and feel the pain that would be similar to having a butt plug being pushed in and out of you at a rapid pace, but it was smooth and free flowing, very easy to take and become accustomed to. It felt like I was a part of someone and that we were connected in the most intimate way possible. It was hot and I was in absolute heaven. Master Kin didn’t have any trouble getting into my hole and he managed to pound it for quite a while. All that I remember during that moment was the satisfaction that I was giving my masters, it felt so good to be able to please them and let them enjoy my body like a worthless little toy to fuck the brains out of.
While this was going on I heard the camera go off with Master Andrew taking pictures and videos from all different angles. Further adding to my feeling of slutty hornieness, I felt that I was nothing more than an object for all of these 3 men. Looking back at the videos is a strange thing. In my mind, I remember screaming at the top of my lungs, begging for mercy and for them to stop hurting me. But looking back and listening to the video footage, all that came from my mouth was breathless pleases and pathetic dog like whimpering. It’s amazing how your mind can play tricks on you and how heightened your senses become when you’re getting fucked in a sling….
While all of this was going on, Master Jeremy was looking on in delight. I thought that would be the case for the whole fucking session, but Master Andrew had other ideas. Armed with pegs and a cattle prong, Master Jeremy went to work on my body while I was getting fucked. When I least expected it, I would get a zap on the nipples, then on the stomach and then near my penis. It was absolutely terrifying and I was freaking out. However, because I was already in Euphoria from the fuck, all I could let out was a pathetic whimper, unable to communicate in English that I was in pain. It got to the point at one stage where I just stopped responding and Master Jeremy thought that I had passed out from all the things that were happening to my body. I was still very well aware, but my senses were so overwhelmed that my mouth just stopped working and I just lay slumped like a limp puppet in the sling, accepting my fate.
After what seemed like an eternity, or less than 5 minutes, Master Kin was done with fucking me and let me lay in the sling. It was a confusing moment in my life. Firstly, I was still trying to process what exactly went on, my ass was in so much pain and I was so mentally and emotionally drained that I was unable to express feelings or even move my body properly. Adding to this, I was wondering why the stop was so sudden, did I do something wrong, was someone tired? It was only a little while later that I understood that Master Kin had been going at my asshole for about 30 minutes and that I kept begging for more, I don’t recall doing this, but the proof on Master Andrew’s phone says otherwise (oh what I would give to have his phone for just 1 day). I also expected there to be a climatic cum shot where Master Kin would rip off his condom and cum all over my naked body, this also didn’t happen, but I have recently learnt that sex isn’t all about cumming. It was all over, I had finally lost my ass virginity after 23 years.
After the fuck, I was told my Master Andrew to get out of the sling so that others could have their turn. Emotionally and physically exhausted, I don’t remember much that went on when Master Kin and Master Jeremy were in the sling. I was so out of it at the time (processing what had just happened to my asshole and how I had changed) that I turned into a robot. Pass this, put this there, insert this in that. I honestly had no idea what was going on and remember spending most of my time just laying their in masters bed while everyone else played with each other. After master Kin and Master Jeremy had finished in the sling, it was time for Master Kin to leave. I got a passionate goodbye kiss from Master Kin and hoped that it wouldn’t be the last time I got to taste his lips. Then it was time for Master Andrew to get into the sling and he wanted to make sure that I was actively partaking in the events of the night again.
As Master Andrew got into the sling I was instructed to come over and work his balls while Master Jeremy tried to fist him. Playing with Master Andrews balls for a little while, I was then instructed to come close and make out with him. As I came up close to meet Master Andrews face (difficult when you’re blindfolded and have shit co ordination skills), Masters index finger made a beeline straight for my asshole, it would stay there until Master Jeremy was successful in getting his whole fist inside Master Andrews. I have already described in detail about an amyl prostate massage and amyl breath control in previous write ups so il try my best to not repeat myself, but this experience was entirely different. When Master Andrew hit a roadblock when his ass ring wouldn’t open up, he would take a hit of amyl and breath it in and out of my lungs. I was a part of the process and Master Andrew made sure that I was feeling everything that he was feeling too. When the amyl hit and I tried to pull away, I was pushed back into masters chest and prostate massaged intensely as punishment for pulling away. When Master felt pain, I would feel it too because he would attack and hit my prostate with much greater force than usual. I felt like I was taking the fist with him. It was the greatest feeling of connectedness I have even felt and I really did think that I was a part of Master Andrew. I keep saying that my latest experiences with Master Andrew top the previous sessions, this was no exception.
After Master Andrew decided he had had enough fisting, it was time for Master Jeremy to leave also. After a bit of chatting and banter between the two, I was left once again back in the same position that I was when I had first met Master Andrew. Naked and lying in his bed. I thought that the session was wrapping up, but Master Andrew had one more thing up his sleeve that was meant for just the two of us.
After what seemed like an eternity of Master Andrew making out with Master Jeremy, it was finally time to go back to where it all started. Master and slave lying naked in bed with each other. Lying in bed with Master Andrew was safe, finally after so many hours of torment and pain, I was finally able to relax and lay there to enjoy sirs company. For a long time, both of us just lay there and felt each other, with the occasional kiss and cock tug. After being tormented and used for so many hours, it was a great relief to finally be able to lay there and feel like I was being looked after by Master Andrew. During the time in bed, Master Andrew just reassured me that I was a good little slave boy, asked me if I enjoyed the session and what I thought about it. From someone that was just attacking my asshole and controlling my breath with amyl, Master Andrews words were reassuring and comforting, in direct contrast to the dominant nature that had been used throughout the past 5 hours. I felt safe, and I loved it. I was being gently caressed by a big adorkble bear and I loved every moment of it. Exhausted from all that had happened during the day, I just lay there and enjoyed the moment to it’s fullest.
Then master Andrew asked if I wanted to try one more thing for the night. I gladly accepted his proposition and even though I felt like I had just run a marathon, I wanted to know what he had in store. So sir led me out of the bedroom and onto the a massage table in his lounge room. I was to get a sensual massage and jerk off before I was send out and on my way.
I’m typically a person who is used to remedial massage, people attacking knots and pains in the muscle so that flexibility is increased and physical pain is minimised. A sensual massage is the complete opposite. After slowly rubbing his hands up and down my body with massage oil, I felt his hands and fingers in my asshole and on my cock. It was amazing and instead of the pleasure/pain that was felt during our bondage sessions, the smooth motions and sensuality made it an amazing experience. For the very first time, I was able to lay there without a worry that there would be a slap on the balls or a zap from the violet wand. I just lay there in pure bliss. But that didn’t last long though, soon enough I was back to being a slave and it was time for master Andrew to see if I could put these new skill into immediate practice.
Being blindfolded and giving a massage is quite an interesting thing. For one, you can’t find where the massage oil in and you don’t really know where things start and where things end. With my brain and physical senses completely annihilated from the 5 hour session that I just had, I defaulted straight to a remedial massage and got to work on loosening up sirs back muscles. This was obviously not what was expected, but with a little bit of coaching, I was able to head in the right direction, right into sirs asshole… after a while, sir decided that he wanted to cum and gave me an option of whether I wanted it on my chest or in my mouth. This was no question and I gladly sat up and awaited sirs hot load in my mouth.
It took a while and I was quite disappointed that my pathetic body and sheepish presence we’re not enough to get sir to ejaculte. During the whole process I remember begging for sir to cum, right into my mouth so I could taste his beautiful load. Eventually, after what seemed like an eternity, sir forcefully grabbed my head and ejected his load right into my mouth. I felt like the dirtiest slut on the planet and I absolutely savoured every single drop, licking my lips to make sure I didn’t miss anything. I asked sir if I could swallow his salty hot load and he said that I could. It was a very good reward for such a shocking massage job.
Finally it was my time to cum and after saving a 2 day load and serving 3 master over 5 hours I couldn’t wait. But the torture was not over. I wanted to touch my nipples and feel my body so I could finally cum, but sir instructed me to have my hands behind my back while he jerked me off. I was not allowed to cum until he said so, otherwise I’d get hit in the balls. Sir is an expert so he knew exactly when I was close to cumming and made sure to stop when it was just about to happen. Finally after what seemed like another eternity, my cock gave way and I couldn’t hold my cum in for sir any longer. I remember apologizing profusely and hoping that I wouldn’t get punished. I felt like such a useless and pathetic pig at that point, but I also felt relieved that the session was over and that my 2 day cum load had been expensed.
After I caught my breath, it was time to shower off the mess that I had created. Sir got into the shower with me and tried his best to get all the lube, cum and Crisco off his body. After this, sir instructed me to get on my knees, asking me what he thought I was going to do. I had no idea. Moments later, a stream of hot piss splashed all over my body, I was being pissed on. It was a signal that I was masters property and nothing more than a filthy toy for his use. Like a dog pissing on everything to mark their territory, it was sirs turn to show me that I was his property and he could do whatever the hell he pleased. It was humiliating, disgusting and degrading at the same time. I literally felt dirty from the golden shower, but I knew that it had to be done so that sir could show me that I was his. It was still a hot exprience and the degrading nature of it all reaffirmed to me my position as a sub and my desires to serve master Andrew for as long as he wanted me.
From there I was left in the bathroom to shower and dress myself. After I was done I knocked on the door and was escorted out the door. It took some time to adjust to the light, in the corridor and once I did the door behind me had already closed. Back to the door, I was taken back to where I was 5 and a half hours ago. Back to reality
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