Bottomed Out

I used to peruse the personal ads on a particular website every few weeks. It's not so much that I was desperately looking for love as I was simply lonely, in a new town and a few months out of a failed relationship. One day, two weeks ago, as I was browsing the females-seeking-males ads, and finding no one of any interest, I noticed that the site had a section entitled "casual encounters." Slightly guilty, and slightly embarrassed, but very much needing human contact, I clicked over to the casual encounters page. Scrolling down the list I saw every imaginable desire being advertised. Desperate young women looking for wealthy men for sugar daddy relationships; horny men in town for one night looking for a woman near the airport to ass fuck; and many, many, men looking to suck another man's cock, or to have their cock sucked by another man.

I had never been with another man, but looking at the pictures posted, and thinking about how easy it would be to just get myself off in any mouth, I was intrigued. What surprised me even more was that I started to think about what it would be like to be on the receiving end, with another man's warm and hard dick pushing into my mouth. I wondered what cum would feel like filling up my mouth; what it would feel like dribbling down my chin. I found myself tugging lazily at my penis as I scrolled down, seeing pic after pic of men who wanted to put their cock in my mouth.

Just at the point where my raging hard-on and my need to be pressed against another body had made me decide that I would take a weird step and answer one of the ads, I saw a posting whose headline read "pussy boy needed." Even with women I had been a little submissive, having one of my girlfriends tie me up and grind her cunt against my blindfolded face for hours on end, but I wasn't sure I was ready to be a "pussy boy" for another man. One look at the picture on the ad changed my mind. "master," as he signed his ad, was tall and solidly built with chestnut hair and, amazingly, a penis that seemed as thick as his wrist and which stretched up almost to his chest. It looked as if it was easily eleven inches, putting the six inch cock in my hand to shame. I closed my eyes and sucked on my fingers, thinking about what it would be like to have such a huge cock stretching my lips. I knew right then that, whatever master wanted me to do, I would do it just to be able to feel that cock.

I took my eyes from the picture and read the body of the message: "I will arrive at your home. You will be completely shaved and wearing panties, heels and lipstick. You will do what I want, when I want, for as long as I want. If you do not do it well enough, there will be consequences. You will be used until I am tired of you. In exchange, you will get nothing but the pleasure of serving me. Reply with a picture and your address. If I choose to use you, I will show up at nine. – master"

I was nervous about everything in the ad, but I was surprisingly sure that the pleasure of serving that penis would make whatever he would do to me worth it. I quickly got out my digital camera and took a picture of myself lying in my bed with my little cock in my hand. I sent off my reply with my address and immediately began to worry that he actually might choose me. Nevertheless, I couldn't stop myself from preparing for him. I dug through my drawers for the odds and ends my ex-girlfriend had left behind when we broke up. I found several pairs of her panties, a shade of red lipstick, and a pair of tall, pointy black heels which I was sure were too small for me. I chose the black satin string bikini panties which had always driven me crazy and lay my outfit down on my bed in front of me. I couldn't believe that in less than two hours I would be wearing only those three things, waiting for a strange man to show up.

I got into the shower and spread shaving cream over my legs, chest, ass and balls and picked up a fresh razor. Shaving took longer than I had thought it would, as I had never shaved anything but my face. I saved my ass for last, thinking it would be the hardest. As I added a little bit more shaving cream my finger grazed my tight little hole and I flinched. Soon that tight little hole might be stretched wide by the biggest cock I had ever seen, I thought. I let my fingers remain there for a little while, slowly making circles around the ring of muscles, going so far as to push my index finger in to the first knuckle. My whole body tensed as I did this, but my cock rose straight in the air and I could feel lightning bolts of pleasure racing from my asshole straight to the tip of my penis. I slid my finger in further and was soon forcing another finger in as I wildly finger-fucked my asshole, jamming my hand between my cheeks harder and harder, not believing the feeling that I had never before experienced. I hadn't even touched my cock when my body tensed again, this time in orgasm, and I sprayed cum in long spurts along the shower wall.

I collected myself and finished shaving, resisting the urge to continue playing with my tender hole. Even without intentionally playing with it, having my hand and the razor so close to it was enough to keep me hard while I shaved away the last of the hair on my body. I cleaned myself up and stepped out of the shower, at this point so excited about unknown prospects that slipping into the panties and applying the lipstick didn't faze me in the least. I even managed to dig up a bottle of my ex's perfume which I had kept to remember her by. The heels, however, were a little difficult. They were, as I had feared, a size too small, and they were so tall that, even after I had squeezed myself into them, I could barely stand upright.

With twenty minutes of practice I had convinced myself that I could at least move slowly in them without falling over. I looked at my watch and saw that it was five minutes to nine. I stood in my foyer and waited nervously, praying madly that I would hear his knock on the door. At five minutes past nine I was just starting to feel let down when he knocked, loud and hard on the door. My cock jumped upright and I had to wedge it back painfully between my legs to keep it from stretching the flimsy satin of the panties.

I shuffled to the door and looked through the peephole. It was him, standing two feet away from me. I opened the door and stepped back. Master looked me up and down and grimaced a little bit. "You look like a filthy whore," he said. I looked down, disappointed that I had already failed to please him. Master reached out roughly and grabbed my chin. "You look at me when I am addressing you, you hear that cunt?"

"Yes," I said softly.

He slapped me hard across the face. "Yes, master" he shouted back at me. "You had better start doing better or the next few days will not be easy on you."

At the word 'days' my eyes widened. He was going to use me for days? I was scared, but I replied, "Yes, Master. I will do better Master."

With that he pushed me down on to my knees. I thought he was going to put his cock in my mouth right then, but instead, he walked past me, leaving me kneeling in front of the still open doorway in my panties and lipstick. I looked straight forward and tried to keep from sobbing as I heard him unzip the bag he had brought with him and begin taking items out, arranging them on my living room floor. I heard him walk once around the house and chuckle to himself softly before he returned to me and put a hand to my neck. He buckled a cold leather and steel collar around me. In the front of the collar was a small box with two electrodes sticking out of it which stuck directly into my throat. I recognized it as a shock collar used to train dogs. He fastened a leash to the back of it and immediately tugged down hard, pulling me off my knees and onto my back with my feet still drawn up beneath me. In this position my hard cock, still wedged between my thighs, was being pulled down in an excruciatingly painful way.

Master must have figured out why my face looked pained, because he looked down at my panties and said "That looks like a nice little pussy you've got there slut. Maybe you will be able to serve me after all."

I couldn't believe it, but I actually found myself blushing at this, and said, "Thank you, Master. I really want to pleasure you well."

"Good, cunt, then get on your feet and get me a beer," master said as he walked into the living room and sat down on the couch, flipping on the television. I got to my feet and carefully started walking my way to the kitchen on the tall heels. He looked at me and sighed, then got up and grabbed the leash trailing behind me. With one tug I fell to the floor. "Are you such a little whore that you aren't even used to walking? Well, if you are only used to being on all fours, then I guess that's how you'll have to get me my beer." As I crawled towards the kitchen he spanked my ass hard and I cried out a little in surprise. "The next time you cry like that, you'll find out what that little box on your collar is for, cunt," he said. I became quiet and crawled to the kitchen to get his beer.

On all fours, I couldn't hold the beer in my hand, so I held the long neck of the bottle in my mouth, imagining the bottle to be master's cock, and crawled back into the living room, where Master had turned on pay-per-view porn. A woman was lying on her back on screen while one guy fucked her pussy, another her mouth, and several others rubbed their cocks in anticipation of their turns. I thought that I might enjoy being in her place.

Master drained the beer in one gulp and demanded another one. I crawled to the kitchen to get another one, which master again drained in seconds. When I came back with the third, master had stripped off his shirt and pants and lay on the couch in nothing but his bikini briefs. I could see the outline of his semi-erect member through the briefs and thought it was just as big as in the picture. I brought him the beer and he told me to lick his feet and toes. I did as I was told and began to lick the sole of his feet, taking his toes into my mouth and sucking on them occasionally. After fifteen minutes of this, master pulled his foot from my mouth and, with a small flick of his ankle, slapped me across the face with his toes, smearing my own saliva across my cheek. He got up and grabbed the leash, pulling me so quickly across the room that I didn't have time to crawl along with him, I was just being dragged by my neck.

He pulled me into the bathroom. "Listen Cunt, I'm not sure you are fit to take my cum into your mouth or your pussy yet. But I could see the way you were eyeing my cock and I could tell that you wanted me to spray something in you, so this will have to do. He pulled my head back over the toilet with one hand and brought his now near-erect penis out of his briefs with the other. I knew what he was going to do and was disgusted, but didn't care. All I wanted was his cock in my mouth, and I didn't care if that meant that he was going to be pissing while it was in there. I opened my mouth as wide as I could, but instead of putting his cock inside, he simply held it a few inches away and let go a stream of piss straight into the back of my throat. I choked on it at first and it spilled down my chest and onto the floor. "The more that gets on to the floor, cunt, the more you are going to have to lick up. So I suggest you start figuring out how to swallow this," Master said as he kept pissing into my open mouth. It was bitter and salty, and despite myself, I felt my cock throbbing as he continued to spray my mouth. But, try as I might, I couldn't seem to swallow more than a little bit, and most of it ended up on the floor.

"You are going to have to clean that up bitch. Get on the floor and start licking." While I began to tentatively lick up the piss on my bathroom floor, Master went back into the living room. When he came back he had shed his briefs and was holding a small leather covered paddle. "Next time I give you something to swallow, you will swallow it." And he smacked me hard with the paddle across my upturned, panty covered ass. I yelped again and then immediately realized that I shouldn't have. A shock ran through my body as the collar came to life. When it finished, I was lying on the floor in a pool of Master's piss, almost unable to move my arms and legs. Master swatted me one more time on my ass, hard; this time I was too spent to make a sound. "Now clean all of this up, rinse yourself off, and come meet me in my bedroom, little piss whore. We'll see if there's anything you're good at."

At the prospect of seeing if there was something in the bedroom at which I was good, I immediately perked up. Despite the humiliating treatment (or maybe, I would realize later, because of it) I was unable to think of anything but pleasuring this man who had so far controlled me almost completely. I quickly lapped up all of the now fetid urine, swallowing it in gulps in order to get into the bedroom faster for my master.

I crawled into the room to find that master had set up some of the things from his bag: the headboard and footboard now had ropes coming from the four corners with loops at the ends of them. Master slapped me across the face and took off my collar. I was relieved, at first, to be free from the dog training box. However, Master simply removed the box from the collar and put it on another, much smaller collar. "lower your panties to your knees and bend over," Master commanded. I did as I was told, and became very aware all of a sudden that my little penis was still wedged between my thighs, after all that had happened. It was now sticking out behind me beneath my exposed and freshly shorn ass hole. Master fitted this collar around my cock and balls and cinched it painfully tight. With a flick of a remote control, Master set the box pulsing and agonizing pain shot from my cock through my body. "Now you know what it will feel like from here on out if I am not happy. That box will not get taken off until I leave, so get used to trying very hard you filthy cunt. Now raise your panties and lie on your back on the bed."

I did as I was told, and Master attached one leg and one arm to the headboard, the other two to the footboard, so I was spread open with my head hanging off one edge of my twin bed, and my ass hanging off the other. The ropes cut into the flesh of my ankles and wrists uncomfortably, but I thought to myself that the pain would be bearable once master's cock was in my mouth. I salivated at the though of it and my widespread asshole twitched excitedly. My small penis was throbbing underneath my panties despite the collar wrapped tightly around it. Master stood above my head looking down at me. He took his soft but still huge cock in his hand and slapped my back and forth across my face, smearing my lipstick and raising red lines across my cheeks. Just as I thought he was going to finally fulfill my wish and let me suck his penis, he got onto the bed, straddling my chest with his ass staring into my face. He pushed back shoving his ass onto my mouth hard.

"Lick my asshole, cunt. Lick it well or I will not be pleased. Taste what it is like to be a little pussy boy and be glad that your master is letting you touch him at all." I hesitantly slipped my tongue past my lips to touch Master's tight little ring of muscles. It tasted warm, musky, and sweet, the taste immediately filling my mouth and nose as I uncontrollably, almost unconsciously began devouring Master's asshole. I licked around the edge of his hole, taking the flesh into my mouth and rolling it between my lips. I licked his crack from the soft skin beneath his balls to the edge of his crack beneath the small of his back. I stuck my tongue out as far as I could to lick his asshole with the broad part of my tongue, ravenously devouring all of my Master's flesh that I could get my tongue and lips onto. As my tongue circled Master's hole he quickly pushed his body down onto my face even harder, forcing my outstretched tongue up into his tight asshole. The feeling of my tongue surrounded by the tight walls of my Master's ass was glorious and I strained to push myself deeper into him, my chin and nose grinding against his ass crack. "That's a good little slut. You can't get enough of my asshole, can you bitch?"

"No sir," I mumbled into his asshole, "I need to eat more and more of your hole Master."

At that, Master pulled his ass away from my face as I strained to follow it with my tongue. He stood up above my head again and slapped my face again with his now hard cock. This was my first look at his cock in all its erect majesty. It was huge, the knob a deep purple with long, hard veins crisscrossing the length of the shaft. I needed that beautiful cock in my mouth and couldn't stop myself from begging Master for it.

"Please, Master, please put your big cock into your little cunt's mouth. She needs it, master," I pleaded.

Master shook his head at this and reached for the remote to the shock collar. My eyes filled with fear and then tears at the pain that was shooting through my cock and balls. My whole body shook with pain and I struggled not to cry out, not wanting to make Master angrier. When Master finally turned off the shock collar he slapped me, backhanded, across the face. "Good little sluts don't beg their Master, you hear me. Good little sluts do as they are told and that is it. Now you will have to wait to have Master's cock in your mouth. Instead, Master's going to have to fuck your little pussy."

With that, Master moved around the bed to stand between my outstretched legs. His rough hand grabbed the crotch of my panties, and, in one quick movement, tore them off of me. He took the pre-cum dripping from his slit and rubbed it around his cock, making it glisten as I watched nervously. In one long stab his penis was inside me as far as I thought I could take it. It stretched my tight little "pussy" and felt like it had impaled me halfway up my body. I looked down and saw that only half of Master's tremendous cock was inside me. With a grunt he pushed the rest of himself into my pussy. I screamed in pain as his balls slapped against my ass cheeks and his cock filled my entire body. He slapped me in the balls and I knew that I had to be quiet, no matter how much it hurt.

He ground his cock in and out of my pussy short, fast, and hard strokes while his hands grabbed my nipples, pulling and twisting them roughly, only stopping occasionally to slap my face or my balls. The pain was enormous and everywhere at once, but with each slap and each thrust of his cock into my pussy my cock twitched and electric feelings of pleasure shot through my body to mix with the pain. Master continued to fuck my pussy raw and dry for what seemed like hours as I writhed in a mixture of pleasure and intense pain. Finally, just as I thought I couldn't take it anymore Master's thrusts got shorter and harder, and I could feel his legs and back tense. With one last thrust and a grunt he buried his cock fully into my pussy and I felt him release. I could feel load after load of hot cum splashing against my insides, coating me. The feeling of his hot jizz and still hard cock inside of me shook away any doubts about who or what I was; I was my Master's cunt, his bitch, his pussy; I was his little girl. This feeling of release pushed me over the edge and I couldn't stop my balls from exploding. I knew as I shot long ropes of cum out of my little penis that my cumming would anger Master, but I couldn't stop. I wasn't just his pussy, I was his pussy boy, and my little pussy boy's balls were emptying over my little pussy boy's stomach and chest.

Master waited until I was finished, then he scooped up my jizz in his palm and slapped me again, smearing my cum over my cheeks and mouth. He shoved his hand into my mouth and I tasted my own juice, warm, creamy and bitter. I cleaned his hand with my tongue, swallowing all of my jizz and then licking my lips and trying to taste as much of it off of my cheeks as possible. Master pulled his soft dick out of my pussy and straddled my chest. His member hung in front of my face for a second, covered with his cum, before he plunged it into my waiting mouth. Master's cum tasted even better than mine, mixed with the sweet taste of my pussy. I couldn't get enough of the taste of Master's cum or of the feeling of even his soft cock against my lips as I sucked him clean.