As I mentioned in a previous blog post, I’ve done a lot of masturbating and fantasizing this summer. My fantasies span a wide range, but the ones that always get me off the fastest involve a heavy bondage and domination element. I don’t judge, I just enjoy, and it makes me cum like a rocket, so I’m good with it. With the fantasy that I’m about to write, I never get past the first section of it before I cum, so I’m going to have to see if I can keep my hands off myself long enough to imagine how the rest of it goes and finish it.
The story begins like so many of my kinky adventures, with me trolling Craigslist. I had placed an ad looking for a “professional, older, executive type” guy with a kinky side. I like my partners classy not trashy, and I have figured out that I have a thing for older, “distinguished” gentlemen who know what they want and know how to take charge. Steve and I exchanged messages and agreed to meet. I let him know that I was very open to all sorts of possibilities and wanted to have him surprise me a bit. I told him that I wanted to submit to him and pleasure him, and as long as it was safe and sane, I didn’t really care what form that all took.
When I rang to doorbell I was pleased to see a handsome and trim man in his fifties with greying hair and a devilish smile. He invited me in, shutting the door behind me, and I could feel his eyes devouring me. He had told me that he would be taking charge and that there wouldn’t be a lot of chit chat before we started, so I wasn’t surprised when he ordered to undress right there in the living room.
I did as instructed and watched him watch me, hoping that he liked what he saw, and curious about what would come next. Once I was naked he came to my side and I realized that he was carrying a leather collar and chain leash. He placed the collar around my neck and told me that I was now his pet to use for the entire time that we were together. With the collar on I was only to speak when spoken to, and was to follow all instructions without hesitation. I nodded my consent and he swatted me heavily on the ass.
He directed me to turn around, and I realized that he had brought a dining room chair into the living room. He ordered me to bend over it, and then he tied my wrists to the chair, leaving my bare ass up and exposed to the world. Next he spread my legs and tied those to the chair legs as well, with my legs spread, leaving my ass open. I was pleasantly surprised at this, but what happened next really surprised me because I’d never had it done to me before. He reached between my legs and cupped my balls in his hand. He pulled my balls back toward my ass and stretched them as far as they would go, which was a good kind of uncomfortable. The next thing I knew I felt him place some hard wooden thing across the stretched skin of my testicles, and I could feel him lock it in place. The clamp rested against the back of my thighs and stretched my nutsack out, using my legs to keep it in place. It felt good, but intense.
He starts telling me that this experience is going to be the biggest mindfuck I’ve ever gone through…being tied to a chair, THAT got my attention, and I couldn’t help but wonder what I had gotten myself into. The next thing that got my attention was his lubed finger making its way into my ass. It was sudden, but he was an expert and I felt myself relaxing and letting him in almost instantly. His finger was replaced in quick succession by something hard plastic, but with a rounded shape. A little push and it was passed my lubed sphincter and it felt pretty good. I started to moan my approval but then I realized that he was still pushing and that this thing was getting bigger the further he pushed. He grabbed my hip and told me to breath, and with a sudden thrust, whatever it was found its way into my ass. It hurt with the thrust, but once it was in, it felt pretty good and I relaxed into it.
Just as I was getting used to it, Steve gave my ass a tremendous swat, which made me jump with surprise and the sting of it. And then I felt the vibration. The plug that Steve had put into my ass was an odd shape, but it had a powerful vibration, and that vibration was aimed directly at my prostrate. I’d played around with prostate milking before, but never had an experience like this. Within seconds of that thing vibrating my guts I felt this explosion come from inside of me and with no stimulation to my penis at all, my dick erupted with more cum than I thought possible! The cum shot across the chair and my guts felt like they were going to come out with it. My knees buckled and I was thankful to have the chair to brace onto. Steve just laughed. When I was done cumming Steve reached under me to the seat of the chair and swiped his hand through my jizz, and then he brought it to my mouth and simply commanded me to lick it clean. I like cum and I enjoy swallowing other men, but I always find tasting my own a little strange and gross, and somehow I think he knew that and was testing my bounds.
Once I’d licked his hand clean, Steve undid both my hands and feet and ordered me to follow him to the bathroom. There he lead me to a large shower stall, and he ordered me in to the shower. He instructed me to wash up and then he told me that I had to shave ALL of my body hair except the hair on my head. I was kinda surprised and confused, but as I told him, I was there to be his toy, so I was going to do what he said. He personally took command of shaving my crotch, and that made me hard as a rock. Once he was done he ordered me to stand with my hands on the wall, and before I knew it my ass was vibrating and I was cumming again almost instantly. That bastard had a remote control vibrating prostate massager that is also a butt plug…talk about control over someone!
I almost fell in the shower with my second orgasm, and Steve just laughed. When I was done he gave me a towel and told me to dry myself. When that was done he ran his hands up and down my body making sure that I was hairless. As I was hanging up the towel, I turned to see him standing with something stainless steel and shiny in his hands. Before I could process what it was, his hands were placing it on my cock. I stared for a moment with confusion, and he said “Your little prick now belongs to me. For the rest of the time you are here, your dick will be locked in this cage and I highly doubt that you will get to use it unless one of my guests requests it.”…Guests? Cage? Whoa… He’d placed my flacid, and now hairless cock into a male chastity cage complete with a lock. He locked the lock and placed the key in the medicine cabinet. My dick was now encased in stainless steel, and I wouldn’t be able to even have an erection, no matter how how the coming experience would be. He was in total control below the belt with a cage on my dick and a plug in my ass…and I was loving it. My head was starting to swim.
To keep the surprises going Steve grabbed the leash that was attached to the collar around my neck, and he lead me to a bedroom with a large dressing table. On the bed were clothes, and on the table all sorts of cosmetics. At this point as my mind was processing Steve informed me that I would be turned into the sissy bitch that I’d always wanted to be, and that I would be serving as THE entertainment at a party he was hosting tonight for some of his “business” friends. It was a lot to take in all at once.
Steve directed me to put on the clothes first which consisted of a woman’s outfit. Not quite “French maid” but close to it, all black satin, but it also had a very firm corset. I slipped into the stalkings and marveled at how they felt on my now smooth legs. I enjoyed feeling all the soft material sliding against my skin, and my cock strained in the cage, trying to get hard. Once I was dressed Steve ordered me to sit down at the table and he informed me that he’d worked in the wedding business for many years and had learned a great deal about prepping and make up. He expertly transformed me from a guy into a sexy woman, complete with bright red lipstick. Even I was impressed with how hot I looked when he was done.
Steve ordered me to stand, and he then took several pictures of me that he said would be added to his collection, and used for blackmail if need be. He grabbed the strings of the corset and tightened them impossibly tight, to the point that it was hard to draw a full breath. It was then that he gave me the first and only kiss that I would get from him…a deep, passionate kiss that had me reeling on my heels and straining against the cage. Then he pulled back and produced a ball gag from his back pocket. He placed the gag in my mouth and fastened it behind my head and told me that it was going in to prevent me trying to tempt him to engage in more kissing. I’d been with this man for a little over an hour and a half, and had two orgasms and a kiss, but otherwise no other contact, and I hadn’t even seen him with his clothes off!
Next he led me to the kitchen and he then told me that I was to prepare things for his guests while he watched and gave instructions. It was hard to mince around the kitchen in the super high heels he’d put in, with the plug moving in my ass at ever step. And then every once in a while he would randomly fire the plug in my ass and I’d be on the verge of cumming again…and then he’d turn it off, leaving me completely off balance.
I wanted to know how many guests were coming, and how this would all work, but I couldn’t ask him, I just had to do my work as he admired me from his chair. I did all that I could to be flirtatious with my body language, and I could tell he appreciated it by the buldge in his pants. I notice him look at his watch, and then he started up from the couch. He moved toward me, grabbing the leash and he roughly dragged me to the living room. He through a pillow down on the floor in a bit of a rush and he ordered me to kneel on it. He told to place my hands behind my back and then he bound my hands and arms with some elaborate and very restrictive rope binding.
There I was, kneeling on a complete stranger’s floor, dressed up like a hot woman, wearing heels and a corset, and a collar around my neck and a ball gag in my mouth. To add to my outfit Steve placed a blindfold on my eyes, and then he backed away. I could here him walking, and it sounds like he was taking pictures, but he didn’t say anything. I don’t know how long I knelt there like that, or where he went. My sense of time went right out the window and I was trying to figure out what would happen next.
And then I heard the doorbell. I heard footsteps and I heard Steve say hello in greeting, and I could hear muffled conversation, but it was impossible to tell how many people where there, or who they were. The crowd came my way and I heard Steve tell his guests that I was to be their party favor and toy, and that they should feel free to do whatever they wanted with me. I was delighted and terrified at the same time.
Steve had just finished speaking and I became aware of someone standing in front of me. Before I could even fully comprehend there was a hand pushing my forehead back and then there was a cock rest on my face! His balls were on my chin and the flacid but growing shaft was laid out beside my nose, and up to my forehead. As I adjusted to the sensation hands removed the gag from my mouth and just as I was trying to swallow the pool of saliva caused by the gag, that dick was peeled off of my face and jammed into my open mouth without warning. I felt hands on the back of my head and this man did all that he could to impale me on his cock.
I had no idea who this guy was, what he looked like or anything about him, other than he had his rapidly hardening, moderate sized cock in my mouth. When he got to full firmness he started to rapidly and ruthlessly fuck my face deep and hard. He told me to hold my mouth open and he kept jamming the back of my throat making me gag again and again. With my hands tied behind my back, and his hands firmly on the back of my head all I could do was relax and cooperate. I was just starting to settle into the rhythm when he pulled out of my mouth and shot his cum across my face with a deep groan. A hand (I don’t know who’s) wiped the cum off my face and then was jammed into my mouth with the instruction to clean it off like a whore, which of course I did.
As I finished licking the cum from the hand I heard another pair of pants being undone right in front of my face. I wondered who it was and what he looked like, and was answered with a thin but hard cock placed gently on my lips. This guy took his time, rubbing the head of his dick all across my lips and around my mouth. The ordered me to stick out my tongue he rubbed his dick softly all over my tongue. As he was playing with his cock on my face I felt a pair of hands start to grope my body, particularly my ass. There may have been two pairs of hands, I don’t know. They were everywhere and were firm and rough and insistent. One hand reached down to my cock cage and started slapping it roughly, and the room seem to roar with laughter and all sorts of crude and humiliating jokes. At the same time another hand found the plug in my ass and roughly tugged on it and wiggled it in my ass. All the sensations combined had me almost out of my mind. To top it off the plug in my ass began to vibrate and I came again, without an erection, almost instantly. The room roared again, and again I was presented with a cum coated hand in my mouth, this time it was my own jizz.
Meanwhile the cock at my mouth was now taking its turn fucking my mouth. This guy being smaller than the first, I could take him all the way in, and this guy made sure that I did. He would wrap his hand around my head and jam his cock all the way in so that my face was buried in his pubic hair and he’d hold me there as he ground into my face. It wasn’t long before he too shot his seed deep into my throat and released me head, letting me finally breath.
I lost track of the cocks…how many were there? How many times did each man cum? How long did this go on for? I don’t really know. There were at least three men, maybe as many as five. They attacked my mouth with various degrees of firmness and fucked the shit out of my throat. They came on my face, and in my mouth. They made me a slobbery mess and I was exhausted and my throat was sore. My knees ached, and in fact my whole body was sore. Interestingly, none of these guys fucked me, and none did anything more with the rest of my body besides grope me roughly and pull on the plug in my ass a few times and slap my bound up cock in its cage. The plug in my ass fired more times, too many for me to count, and eventually I would orgasm without ejaculating, which was a special kind of agony.
Someone put the gag back into my mouth, and after what felt like days the room went silent, and I could finally tell that the men had left. After an unknown period of time, I heard something behind me and realized that it was Steve unlocking the cuffs that held my hands behind my back. As he released my hands he roughly pushed me forward onto the floor and told me to stay there. He told me to stay until I heard the door close, and then I would be free to go. I wanted to ask him questions, but before I could form the words I heard him step toward the door, and then he was gone. I lay there for a few long moments and then I took the mask off my eyes, and the gag out of my mouth. Everything in my body was sore, but my mind was swimming with the thoughts of all that happened to me. I was desperately thirsty and went to the sink for a long drink. As I stood there taking in the scene I realized that there was an iPad on the counter showing a video. As my eyes focused I realized that the video was me, on my knees and blindfolded sucking strangers cocks! On the counter next to the iPad was a note. It told me what a good job I had done, and how pleased the guests were. The note also said that the video had already been uploaded to a porn site, and already had several hundred views. As I reeled in the shock of it all, I read the post script, which said “By the way, I’m on my way to the airport and will be gone till next Saturday. I have the only key to the cage on your cock with me…see you next week!”…