On a Dare Ch. 01

[This is a degradation story, and it isn't pretty. If that's not your thing, this won't be your story. Tags: trans, mf, rape, violence, degradation, public ]

- - - - - - -

I had been to see the guy I called Mister a handful of times, and it had been pretty extreme. I was into being degraded, and he was so good at it. I'd been Insulted, rejected, beaten, hurt, and cum on. Used for some fucked up shit. And it got me so fucking hot.

But I still had clear boundaries. I still had self-worth. See, the thing is, I kept my dirty, disgusting, fucked-up side compartmentalized. I seemed like a nice, normal person to people I passed on the street. I mean, seriously, I don't even read as transgender -- yes, I'm a trans woman -- never mind as a complete deviant. I waited until I was in private spaces with Mister to do the fucked up shit.

Well, up until one day.

The thing that killed me was, he didn't order me to do anything. That would have been way too easy. He just mentioned it in an email he sent. "I bet a worthless whore like you loves giving public blowjobs. I bet you're the kind of slut who would offer a blowjob to a random guy on the street, then duck into the nearest alley to give it. I bet you're the kind of cuntless fuckpuppet who would spend a day doing this, and even take selfies with all the dicks she swallowed and send them to me as proof of her depravity."

Nowhere was there anything in that message that told me to do it. All it did was express an idea that any person with even the tiniest amount of self-esteem or common sense would reject out of hand.

Spoiler alert: that didn't stop me.

The next day, I was out wandering down Pine in Capitol Hill. I couldn't believe I was really going to do it. I had a lot of eyeliner and some bright pink lipstick on, with a cute purse and an outfit that was suggestive but not overtly slutty.

I scanned the men out walking, wondering who in the hell I was going to proposition for this. And all I could think about was all the reasons it was stupid to do this. I'm a good person. I have value. I'm putting my life back together. I make a positive difference in people's lives. God has a plan for me.

And the thing is, I believed all those things. All of them. But my need to degrade myself, my need to impress a guy whose name I didn't even know, my need to show that I'm the kind of slut who doesn't back down from a dare -- these somehow outweighed all of the good, sensible reasons I had for not doing it.

So there I was.

I finally settled on this one guy. He was in his 30s with a bunch of tattoos, kind of looked like he was in a band. So I asked him if he wanted a free blowjob.

He stopped and looked me up and down. "From you? Eww, no." He started walking again and headed off down the street.

Oh shit, this was going to be humiliating. I'm fat, trans, and middle aged. It would be an understatement to say that not everyone is into me.

The second guy I asked, a businessman in his 50s in a suit and tie, barely broke stride as he said that he didn't bring his wallet. Figures, he thought I was a whore. Which I guess was basically true, just not for money. Really, money would have been a much better excuse.

But I caught a break with a sharply dressed twentysomething south Asian man. "For real?" he asked.

"Yes, for real. We'll just go over into that alley over there and I'll give you a blowjob."

"Wow." Finally somebody who was apparently horny enough to see this as good fortune. Then his expression changed to something skeptical. "Ok, what's the catch?"

"I need to take a selfie of me with your dick -- not your face or anything," I assured him. "So I can send it to my boyfriend. He gets off on this shit." I hesitated before admitting, "Ok, I do too." Not that Mister was remotely my boyfriend, but it seemed easier to explain that way.

He smiled, accepting the explanation. "Ok, cool."

We ducked into the alley and went a little ways in so we wouldn't be too obvious to people on the street. I pushed him up against the wall and opened his fly. His dick was already hard, and sprang free from his pants. It was decent-sized, maybe six inches, and I noticed that it wasn't the cleanest ever, but it's not like that was going to dampen my enthusiasm.

I licked it, then bobbed on it a few times until I had it balls deep. Then I snapped a selfie from the side.

I resumed my work. He clearly was super horny, and he didn't last very long. He shot his load into my mouth, but I held off swallowing right away.

Pretty much as soon as he was done he seemed to collect his thoughts, get embarrassed by his behavior, and take off. In his wake, two $5 bills floated to the ground. I hadn't had any desire to get paid, but apparently he had other ideas. Not only was I a literal whore now, I was a ten-dollar whore. Ouch.

I stuck my tongue out, looked at the phone camera, and snapped another selfie. Once I was done, I swallowed the cum. What can I say, a slut like me just likes it.

I glanced up to see an elderly woman staring at me with a disgusted look on her face. I looked down in shame, unable to meet her eyes, then fled down the alley to the other end. When I finally looked back, I was relieved to see that she was gone.

Looking at the picture, my lipstick was a mess, and I realized I had forgotten to bring any Kleenex or wet wipes or anything. Yikes. I reapplied my lipstick to my lips and tried to clean up the places where it was smeared using my fingers, but it mostly didn't help.

I quickly typed something up about what happened, then emailed that and the pics off to Mister.

- - - - - - -

I was walking down the street a few minutes later when I got a message back.

"You fucking disgusting whore,

"Is that the best you can do? Figures. I'm yawning here."

Ouch. Mister wasn't exactly effusive with praise, but I could usually get a response that was better than *that*. Time to try harder.

The way my makeup was messed up, most people were averting their eyes. But, scanning the area, I saw this tech asshole who was looking at me mockingly. Ok, he might be nasty enough. I went up to him and propositioned him.

He laughed condescendingly. "Wow, you're pretty fucked up, aren't you?"

I gave him a crooked smile. "Only one way to find out."

"Well then, come on, bitch, let's do this."

He led the way around the corner and into the alley. He found a recessed doorway behind one of the buildings where he could be pretty much hidden, but I was pretty much out in the open, maybe 10 feet from the street.

I knelt on the rough cracked concrete in front of him and unzipped his pants. He had a big cock, 8 inches and pretty thick around. I snapped a picture as I started going down on it, trying to get it all in. With a little work I was able to get the whole thing down my throat.

"You can do better than that, you disgusting bitch."

I tried to go faster, but he just grabbed my head and started facefucking me. I wasn't ready for it, and I started gagging as he rammed it in in and out of my mouth faster than I could handle.

I couldn't get his rhythm right, so I couldn't really breathe. I reflexively tried to pull my head back, but his hands were much stronger, so I was helpless to free myself. Panicking, I grabbed onto his legs tightly and sank my nails in through his pants, just desperate to have something to hang onto. I couldn't help crying uncontrollably. Meanwhile, he kept saying things like "Yeah, take it all, slut!"

After a couple of minutes, I felt lightheaded from lack of oxygen. By the time he pulled out, I was barely aware of anything. I gasped for air as he came all over my face, then I felt dizzy and fell over sideways. I looked up, and noticed that at the edge of the alley, a small crowd of onlookers was gathered. Most of them looked horrified, but a few of the men looked interested in me.

The man who had fucked me zipped up his fly and laughed. "Thanks, slut." He left down the alley in the opposite direction from the bystanders. It vaguely occurred to me to respond with some smartass response about him having been with a trans woman, but I was really in no condition to speak, so I just lay there and let that jackass have the last word.

It took me a few minutes to be able to move, and during that time, my audience mostly moved on. When I finally felt well enough to move, I picked my phone up off the ground from where I had dropped it and took another selfie. Looking at it, I looked absolutely wrecked. My eyeliner had run all down my face, my lipstick was spread around like crazy, and half my face was covered with cum. The right side of my face and a lot of my hair was dirty from falling onto the pavement. I looked like hell.

I was interrupted in my thoughts by a guy who had been one of the people watching. He came up to me and demanded a blow job. He seemed like a pretty timid person overall, but apparently, seeing the first guy abuse me like that, he had found his courage.

I shrugged and reached out a hand for him to lift me back up to my knees. I blew him and the two guys waiting behind him, but they all stood still for normal blowjobs. I took pictures as I went along to send off. The last of them found the guts to pull out and try to come on my face, but it ended up dribbling down instead, making a mess of my top and skirt.

Finally, after he was done, there was no one else waiting. I sat down against a wall in the alley and just tried to recover my senses. I wrote up an account of things and shipped that and the pictures off to Mister.

- - - - - - -

As I tried to build my energy back up to move again, I got a message back.

"Whore,

"This is the kind of thing you're good for! Glad to see you're not useless after all. I guess we'll see where you take it from here.

"Mister"

I laughed despite everything I'd been through. This was high praise, and it always makes me happy when I can do something fucked up enough to impress him. I was just disappointed that I hadn't captured the whole thing for posterity — I know he would have gotten endless enjoyment out of seeing me get abused like that.

Which gave me an idea. I found a place to hide my camera where I could capture video without it being spotted. When I was ready to get back up, I set it up and started recording. I blew Mister a kiss — which looked awesomely sick, as messed up as my face was now — and set off to continue my search.

When I got back out on the street, I was *invisible*. There are homeless people who just look a little worse for wear, but there's a certain way of looking like a street person, and I now looked fucked up enough to qualify. I was covered in a combination of destroyed makeup, dirt, and encrusted cum, and I completely set off everyone's "don't look" sense. They weren't merely averting their eyes like before, they were looking right through me like I didn't even exist.

This was going to make it tricky to find someone.

I wandered for a little bit, then I found someone who would see me no matter how bad I looked. He was a late stage alcoholic, and he looked as bad as I did. Worse, really, because he had all the lines on his face from living like this for what looked like years.

I told him I'd go down on him, and he followed me back to my spot in the alley, bringing his big backpack with him.

Not surprisingly, his personal hygiene was disgusting, and I had to steel my stomach to take him in my mouth. His crotch was incredibly dirty, and among the clash of different odors was a pretty strong scent of urine.

It took some work to give him a boner, and he wasn't really an active participant. But with enough time, suction, and deep throat action, I was at least able to get him hard.

I spent a long time trying get this disgusting penis to cum and pulled out every trick I knew. Playing with his balls, tongue swirls, jacking the shaft while I used my mouth to play with the head, grabbing his hips and ramming them into me, and everything else I had. I mean, performing all this work was really fun when I was doing it for someone who would appreciate it, but this guy was barely even present. Honestly, it was humiliating.

Finally, I unbuttoned his pants and pulled them down, along with his underwear. That allowed me to slip a finger up to his asshole and work it in. And that was even worse — his anal hygiene was just as bad as the rest, and the smell took my breath away. I tried my best to ignore it and keep working, and it did seem to get a positive reaction. Finally I was rewarded with him spurting into my mouth. It was a huge relief.

But the taste? It was truly vile. I mean, I'm genuinely happy swallowing all kinds of cum, but this was nasty in a way I'd never experienced before. I quickly stuck out my tongue on display for the camera, then grimaced and swallowed it before I had to think about it any longer. My stomach rolled over as I swallowed.

As I was doing that, he pulled his pants back up and got them rezipped. At that point, he suddenly showed more animation than he had this entire time. With a completely unexpected ferocity, he shoved me down hard onto the ground, then grabbed my purse and took off out the alley and down the street. By the time I had really realized what happened, he was long gone.

I just lay there in shock for a few minutes, then started to process all the crap I was going to have to deal with tomorrow thanks to having lost my purse, my ID, my debit card. What a mess. On the plus side, I had tucked the ten dollars that the first guy had paid me into my bra, so at least I had a little emergency cash.

Finally I got up and pulled my phone out from its hiding place. I noticed as I moved that my top was ripped on the side and that my skirt had a couple of tears in it as well. Great.

I didn't know what else to do at the moment, so I just sat down and watched the video. It was all almost as humiliating to watch as it had been to experience.

The whole thing was on the video, so instead of writing up what had happened, I just wrote a brief introduction and sent it off to Mister. This was well beyond anything I'd ever done before in terms of how gross and degrading it was, so I hoped that he was at least into it.

- - - - - - -

I sat there for a long while. I wasn't ready to get back up and go after that mess. While I was still there, I got a message back from Mister. He seemed pretty appalled by the whole thing. Maybe I should have had the basic sense to walk away from the drunk, but I just couldn't stop trying to see the dare through.

And the stupid thing is, I refused to stop even now.

I finally got up, set my phone up again, and went back out to the street. Once again, I seemed to be invisible to people in my disastrous-looking state. I wandered around a little bit, but I didn't have any luck. There were a couple of street people, but I wasn't up for trying that again. I tried propositioning a few guys. They avoided me like I was a panhandler, though one of them gave me a couple of dollars as he passed.

Finally I found a well-dressed guy who would look me in the eye. I offered him oral, and he just said "sure," without much emotion. Which seemed a little off, but I wasn't paying much attention to that by then.

I led him back into the alley. But before I could get started, he stopped me and spoke earnestly. "Look, you don't have to do this. I can give you some money, I can help you get some help, maybe get you into recovery. There are other ways to live where you this doesn't have to do any of this."

Fuck. This shit was the last thing I needed. "Thank you, but I don't need any help. Seriously, I just want to go down on you. That wouldn't be so bad, would it?"

He looked back at me, all sadness and condescension. "I'm sorry to hear that. I hope you find peace in your life." He walked out of the alley and off down the street.

As my eyes followed him out, though, I saw a cop standing there. Oh, shit.

"So, what are you up to?"

I was scared shitless. "I didn't... um... do anything? Actually? And I... well, I mean, I wasn't anyway asking for... for money."

"Sure." He rolled his eyes. "So, new at this?" It was barely a question.

"Um... I definitely haven't done this before. At all. Uh... officer." He could definitely see the panic in my eyes.

He eyed me appraisingly. "Well, maybe I could let you off with a warning. With the proper inducement, I mean."

I wasn't exactly thinking straight, but even despite that, I could follow that one. "Uh... of course. I'll do whatever you want me to, officer."

He pushed me back against the wall and mauled my modest tits. I winced a bit, but I certainly wasn't going to raise any objections, as scared as I was. I just hoped he wouldn't --

That was when he reached down to grab my pussy and found something altogether different down there. Oh shit.

I winced before the first punch to my face even got there. Despite already having my eyes closed, I just knew it was coming. A bunch more followed, I don't really remember the details. I think before too long I was on the ground curled up in a ball, getting kicked instead. I heard him calling me things -- I couldn't tell you what most of it was, though I do remember the phrases "fat pig" and "sick tranny faggot whore" at some point.

I was barely conscious when he stood me back up facing the wall. He tore down my skirt and panties and spread my ass cheeks wide. He spit on his hand and slipped a finger in my ass to lubricate things slightly. It didn't do much.

After a moment, I felt him entering me. I wasn't very present, but enough that it felt sick and humiliating to be raped. There was also a tiny part of me somewhere that was turned on, and it made me loathe myself. I think he was still saying things to me, but I had long since lost the ability to pay attention to words.

He went on for a few minutes, not lasting very long, but when he was getting close, he pulled out. He spun me around and positioned me on my knees naked in front of him.

His cock was right in my face. It was covered in my shit, but I was in no condition to resist him. So when he rammed his cock into my mouth, I just let it in. The smell was disgusting and the taste was even worse, but I just took it as he throat fucked me.

In less than a minute, he shot straight down my throat and he was done. He let me fall to the ground at that point. In one final indignity, he pissed on me. His words were still passing right by me, though I think maybe he was threatening me with something or other.

I lay there on the street for, as best I can figure, a few hours. Then someone was trying to drive a van through the alley, and I was in his way. So he tried to rouse me, and when he rolled me over he realized that not only was my skirt around my ankles, I had bruises everywhere and a face that was barely recognizable.

With that, his demeanor changed to be much more sympathetic. "Are you okay? What happened?"

I thought about it for a moment, then distilled it down to the central thing I felt. "I was raped."

"Oh, I'm so sorry. I'll call the police."

"Please, no police," I said, a look of fear and panic on my face.

After that, he looked at me more skeptically.

"Can you just take me to the hospital?" I asked.

"Um...." He thought about it for a second, sizing up whether it was worth the trouble for someone like me who was on the wrong side of the law. "Yeah, ok, sure," he finally decided.

"Can you stand on your own?"

I smiled a little for the first time, reached out an arm, and asked for a little help. He gave it to me, and I stood.

I steadied myself against the wall as I pulled my skirt and underwear up, then retrieved my phone and tucked it into my bra.

He drove me to the hospital. Thankfully, it wasn't that busy, so they admitted me pretty quickly. I got treated for my injuries -- I had a couple of cracked ribs and a concussion, but was incredibly fortunate to not have anything worse -- and was given a bed. I passed out again promptly.