A Most Degrading Evening

After several long, stressful, busy weeks at work I was in a bind. I'd had barely any time to masturbate, let alone any time for dates or even to call the small number of people I trusted for a hookup. And the thing with me is that the hornier I get, the worse treatment I feel like I need.

So I posted what I thought was a pretty straightforward ad, looking for a stranger to answer it and give me what I wanted. "Willing slut looking for humiliation and degradation" is a to-the-point title, isn't it? In the ad I listed some of what I was into, I described myself physically, posted a non-face picture and gave my general location but indicated I needed whoever answered to host.

The typical dick pics and one-word answers came in, and as I was deleting them one of them stopped me cold. Right there, from my frigging ex-boyfriend, was an email that just read "Sasha?!"

My instinct was to ignore it - he couldn't prove it was me, even if the picture did feature a top he had given me. Lots of girls had that top. And had a body exactly like mine. And lived in my neighborhood. Shit.

So I should ignore it, or I could email him back and tell him to fuck off, but also...it was really hot to learn that someone who knew me had some clue as to what a slut I was when I was in this state. I was thinking hard about what the best way to play things was when all of a sudden I found my magic wand had somehow gotten into my hand, and one screaming orgasm later I knew I had to lean in to this.

"Hey Josh." I wrote back. He replied instantly, asking why I hadn't told him this was what I was into and how we could really have been something. I typed out a whole laundry list of reasons past this why we wouldn't work, then deleted them all and wrote back "Prove it." He replied instantly again, telling me his new address and telling me to get there Saturday at 4pm.

His new place turned out to be a four-floor walkup, and according to the panel at the door he lived on the fourth floor. I buzzed his apartment.

"Hello?" squealed out of the speaker.

"It's me," I told him.

"Me who? Do I know you?"

Ugh. Why was he doing it like this? My phone pinged. "Not letting you in until you announce what you are and why you're here."

"There are people out here," I texted back. There was no response. I took a deep breath. I should have just called it off, gone home, re-posted the ad and ignored anything else he sent. But I had on my sexiest underwear under a satin skirt/suit jacket set and I looked fierce and sexy and honestly I was horny and wanted to get fucked.

"Hello?" the box squealed again. "Who's there please?"

I punched the response button. "A slut."

"Speak up please, I can't hear you."

I grimaced but punched the button again. "A SLUT," I said louder. There was no response from upstairs. I closed my eyes and took a deep breath. "ITS A SLUT, I'M A HUGE FUCKING SLUT DOWNSTAIRS TO SEE YOU" I yelled into the box. When I opened my eyes I saw a girl my age and her boyfriend staring at me. I gave them an awkward smile just in time for the box's response.

"And why are you here?"

I practically drove the button through the wall trying to respond. I just wanted to get this over with. "I'M HERE TO GET FUCKED, I'M A HUGE SLUT AND I NEED YOU TO FUCK ME, OKAY?" I wasn't looking any more but I heard the boyfriend laugh at me. The door buzzed and I ran inside.

There was a box on the bottom step with my name on it. I opened it to find a leather dog collar. My phone pinged again, but I didn't need to read it to know what it was telling me to do. I fastened the collar around my neck and headed upstairs. There was a woman coming down but if she noticed that I was wearing a collar she didn't make a big thing about it.

I was grateful for that, but I also had a fleeting thought where she noticed and made me confess what I was and what I was there for and she decided to drag me back to her apartment and take advantage of me before my ex could. Random women you meet in apartment stairwells always own huge strapons, right?

I decided to check my phone after all as I headed upstairs and sure enough, the first text said "put it on." The second one, though, told me to kneel in front of his door and wait for him to open it.

I thought about how his apartment was either at the far end of the hall or right in front of the stairwell, and I prayed it was at the end. It was not. Mercifully, though, he was probably also incredibly horny because he did not make me wait long enough for someone else to find me.

The door swung open and he stood to the side. "Crawl" he said. I hurried in just in case someone was just around the corner. I didn't get much farther than the door when he told me to stop. Crouching behind me, he pulled my skirt up over my hips and grabbed my ass, which was nicely framed by my garter straps and sporting a black lace thong. He ran his fingers between my legs, on top of the lace. I squirmed under his touch. Slipping a finger under the lace, he murmured.

"So someone enjoyed debasing themselves on the street and walking upstairs in a collar?" I whimpered and he gave my ass a solid smack.

"Yes," I spat out.

"Good slut." he said. "I was just fixing a drink. I made one for you. Crawl over to my chair." I crawled over to face the chair as he walked to the kitchen. "Next to, not in front!" he called to me. I took up position next to the chair and he walked over and pushed me with his foot so that I was right up next to the chair.

He placed a drink on the floor in front of me and sat down. Thankfully it had a straw. I sipped it; I wasn't mad at a drink to take the edge off and he always made good Manhattans. Raising my head from the sip I felt his glass settle in on my back. "Careful now," he said. "There are consequences for dropping it."

We got about halfway through our drinks, me timing my sips to when he picked up his drink. Then he might have been bored, because he moved both drinks to his table and told me to stand in front of him. I did so and the way he looked at me floored me more than ten drinks could.

It was more than lust. There was that, but it was also a knowing look, like he knew that I would have been in this position for some random stranger and it was just a bad coincidence that I found him. He knew what a slut I was now and he was going to take full advantage.

"Take the suit off," he said. I did so and he stared at me in my underwear for a moment. "I want a lap dance," he said. I gave him a look and gestured at the air around us, notably lacking any music. "Your problem," he said, "not mine." I sighed inwardly and tried my best to queue up a song with a decent beat in my head.

Dancing without music can be phenomenally awkward, and I was doing so in my finest underwear and stilettos. I felt silly, and the knowledge that I was doing this because someone else had taken charge and had told me to do it. You can fantasize about degradation all you want but having someone else call the shots adds a whole entire layer on top.

I was grinding my ass against his crotch as he sipped his drink, and I could feel his hard cock through his pants. Without realizing what I was doing I whimpered.

"Is the little slut horny?" he asked. I whimpered again. "Good," he said, "on your knees." I rose up off his lap and turned to face him, trying to look irresistible as I sunk to my knees. He was dropping his pants and I could see the outline of his cock through his underwear. Of all the reasons we had broken up, his cock absolutely wasn't one of them. It was on the large side of average in both length and thickness and I stared at it, desperately wanting it in me.

He dropped his underwear and I went in without being told to do so. I took the end of it in my mouth and ran my tongue around it, trying to work the underside hard. I heard him moan and felt him sink further into the chair, so I went at it harder.

"Take it deeper," he told me. I did so, trying to breathe out as I sunk down on it and trying to let it rest farther inside my mouth. His hands sunk into my hair as he pushed my head forward, and I found myself without air.

He continued pushing down for a few seconds, then released me and I sprang back, gulping in breath. Much sooner than I would have liked, he grabbed my head again and forced his cock to the back of my throat, again cutting off my air. I did my best to swallow his entire dick, and this time he waited until I was squirming and slapping at his leg before he let me up.

"That won't do," He announced, and stood up, grabbing a fistful of my hair as he started walking away. I cried out and hustled in my heels to keep up.

We stopped at the side of his bed and he shoved me down, at the same time reaching down to rummage through his nightstand. I was face down on his bed, and I felt him grab my hands and pull them together behind my back. The unmistakable click of handcuffs sounded and he rolled me back over, dragging me to position my head hanging over the side of his bed. One again he buried himself in my throat, and this time I could do little but take it.

Reaching down while his cock was still at the bottom of my throat, he rubbed the crotch of my panties against my very, very wet vagina. Making a sound like he'd gotten an idea, he pulled out of my mouth and climbed on to the bed, climbing down to my feet and roughly pulling my panties down.

Crawling off the far side of the bed and walking around to where my head still hung, he drew the panties down over my face, the very wettest part lining up just under my nose. The smell was intense, to say the least.

I lay there trying to revel in the humiliation of having my panties across my face. He went back into the nightstand and pulled out a pair of nipple clamps joined by a short chain, which he quickly affixed to my nipples before placing the middle of the chain in my open mouth. The result was a steady tension on my nipples. A lot of sensation was building. I took deep breaths and squeezed my thighs together.

He stood back for a moment. "This is what you're good at, isn't it?" he asked. "Letting men do whatever they want to you?"

"Yes," I said around the chain and with about 1000% less attitude than the first time. "Please use me to amuse yourself and for your pleasure."

"Fucking slut," he said as he placed two pillows on the bed next to me and then rolled me over so my hips were across them, my ass in the air. I felt his cock pressing against my pussy, before he shifted slightly and the length of it ran across my lips. I whimpered. He did it again, pressing lightly and then sliding past.

"Please fuck me," I said.

"Hmmmm," he responded before pressing & sliding again.

"PLEASE" I said again, my desperation an honest expression of how badly I wanted his cock in me. I had cursed this guy up one side of the street and down the other the last time we saw each other, and all it took to get me begging for his cock was for him to gain one ounce of knowledge about how badly I needed it. I wasn't playing the desperate slut, I was one.

"Please what?" he said.

"Please bury your gorgeous cock in my disgusting little pussy," I said. "Please treat me like a little fuckhole. Please just fuck me, please, please, please please ple-"

He cut me off by sliding a lubed finger into my ass. We had engaged in a fair bit of ass play when we were together - fingers, toys, mine, his, basically everything except fucking, so while I was a bit surprised at the suddenness of it I wasn't shocked. He worked the finger briefly before it was joined by a second and he worked them back and forth in a steady rhythm, working my ass and helping me relax.

He did so silently for a minute or two, both of us just listening to my panting and my whimpering and my moaning. "I don't think you deserve my cock in your worthless little cunt," he finally said.

"I know I don't," I said. "Please just pity me, please I don't deserve anything I just need your cock in me, I just need it," I said. A third finger slid into my ass and he fell silent again. I could feel him gently spreading his fingers outward, stretching me. Finally his fingers withdrew for a moment before returning loaded with more lube, this repeating itself twice more.

There was a momentary pause and then I felt something a lot more sizeable at the edge of my asshole. He paused again for a moment, maybe giving me a chance to say something. There was a lot I could say.

My cunt was dripping, aching, incredibly hungry. I found getting fucked in my pussy very satisfying, generally speaking, on both a physical and emotional level. I did not feel the same way about my ass, and the fact that this was how the evening was developing made the feeling of being lesser than, the humiliation, and the arousal just built and built.

I groaned as he slid in. He gave me a moment to relax around his cock, to breathe, and then he started pumping. I must have been tight back there, because it wasn't long before his breath was getting quicker and he was digging his fingers into my hips.

I heard him grunt and felt him stiffen up, and then before I knew what was happening he was pulling out of me and grabbing me by the shoulder. He pulled me into himself, grabbing me in a bear hug and squatting down. I involuntarily squatted with him and I could feel his cum leaking out of me.

He stood up with me and then used my cuffed wrists to take me a few steps back, steer me to my knees, then bend at the waist. One eye was blocked by my panties but the other was free. I could tell exactly what he was doing, and I relaxed and let him do it. He dragged my head forward and swiped my face through the puddle of cum on the floor, smearing it across my skin, the panties over my face, and in my hair.

I had something of an out-of-body moment as he guided my head down. I saw myself, on my knees, hands locked behind my back. Wearing what would ordinarily be very glamorous, fine lingerie and heels, except the panties were soaking wet and drawn over my face, the bra was pulled below my boobs so that the nipple clamps could be applied, and my stockings had taken a beating from all the time on my knees.

Zooming out from my body I saw myself in a strange apartment, with a man that I lowkey couldn't stand but found myself needing, his cock glistening with lube from having had his way with me, my asshole doing a tiny little gape as it recovered from its first ever fucking.

I came. Without a vibrator, without getting fucked, without touching myself, just the image of such a desperate, disgusting slut, and the knowledge that that image was me, was enough to drive me into orgasm.

I didn't know I was even capable of such a thing, but there was something about the totality of the moment where I just felt it overwhelm me and my body clenched and then there it was, the rolling waves of pleasure that are an orgasm. I screamed, I shuddered, and I fell in a heap, my hands still locked behind my back, my face smeared with cum.

When I came to, I was on the bed, unlocked, and feeling exhausted. There was a fleece robe draped over me as a blanket. Josh sat across the room in his desk chair, sipping a drink, his feet on the bed, staring at me. I thought back to what had happened and marveled at the fact that I still felt so full, before i put together that he had put a plug in my ass. I reached back and touched it, confirming that it was there.

"That's how you're going home," Josh said. "No shower. Plugged. This isn't a one-time thing, so I need you to stay available back there." There was a part of me that wanted to cry. A larger part of me couldn't wait.