Cindy's Bikini - Homeless Lover

Teddy and his friends started pestering me about when I wanted them to claim they were the actual fathers of my former best friend's child currently growing inside of her. I had completed all of the sexual favors they had requested. Thus, it was their time to pay me back. However, the situation has changed significantly. Due to me not being on birth control, as I had previously thought, I have discovered I am pregnant again. In my dumb request for revenge, I got myself back into the exact same situation I worked so hard to fix before. Shawn and his asshole friends got me into this situation, but I kept getting myself back into them.

With my last pregnancy scare, I had gone to Shawn for help. Which, in the end, he did. But before that, he had me participate in a group orgy and make porn. The situation now is more complicated. The clinic we went to before is now closing, I have learned. My next best option will require a plane ride and an overnight stay. All of which means I need more money than last time. I am also committed to being done with Shawn and his schemes to humiliate me. I was going to get this money myself.

I needed to get a lot of money and fast or risk my pregnancy starting to show. I kidded myself for a bit, trying to think of some clever ways to do this, but eventually accepted that I was going to do what I knew from the start I would. I was going to prostitute myself more. This time, though, I would be in complete control. No more using Shawn or anyone as a pimp. I would choose my clients and take 100% of the money. What I didn't know was how to secure clients without advertising that college student Cindy is fucking people for money.

My biggest asset was my notoriety as a sex worker or at least a major slut. Not Cindy, but as the woman in the bunny mask. The news has reported on the giant sex orgy the police broke up in which the bunny girl was the star. My other sex adventures while wearing the mask were almost equally famous, including my sex tapes and prostitution. I was sure some people would pay good money to get with a local celebrity like the 'bunny slut' as she is known online. The risk was that the police were actively looking for her. I would need to be careful.

I scouted around town, trying to find a safe area to 'solicit' customers at night. I ended up finding a small but clean-looking alley that was off a moderately busy road. That evening, I watched the alley in my parked car and saw nobody walk through it. Foot traffic was decent and included a lot of men walking by themselves, which was perfect. I went and examined the alley on foot. It was very dark, and anybody walking by it would not notice someone standing in it. This would be my plan, then. I would wear my mask in the alley, covered by the darkness. I would wait for a harmless-looking man by himself to walk by and welcome him to talk in the alley. We would agree on a price, and he would pick me up and take me to a hotel. In the best case, I would only need to do this five or six times and make them regular clients, further reducing my risk. My confidence in the plan was rising. I could make this work.

The next night, I pumped myself up to take a shot at this. I packed a small bag with my mask in it and drove to my alley. I parked my car on the next street over. I wanted to be able to get to it quickly if need be, but have some distance between it and the alley to be able to lose anyone who may be following me. I wore a simple black dress that probably hundreds of women in the town owned. I walked as casually as possible to the alley and then waited for ten minutes. Anyone who may have seen me duck into this alley would have either moved on or already come and checked to see what I was doing. I figured it must be safe to put on my mask.

With my mask on and me in position, I watched people walk by the alley. As I had hoped, no one could see me from where I stood. At first, I was far too timid. Men would walk by that I realized would have been perfect to proposition, but I let them go by. Finally, I steeled my resolve and knew I needed to approach the next man who fit the profile I was looking for. This turned out to be a shorter, balding, middle-aged man walking by casually. Taking a deep breath, I walked just a bit into the light and addressed him.

"Looking to have some fun tonight? I'm available for a reasonable cost," I said, startling him.

"What? Oh my gosh, you're the bunny girl on the news! Are you whoring yourself out here? No, I'm not going to take that risk. Have a good night, miss," he said, walking on with a wave. What just happened? Did I just come upon the one guy in the whole town that wouldn't fuck me for money? I would admire him if it didn't piss me off so much. Now, I had to repeat the whole process again with another man. However, the next three men I approached also denied me. My plan was falling apart.

I was about to call it a day and remove my mask when someone approached me from the other side of the alley. "Are you selling sex? I'd be interested in that." The man startled me, especially as I was about to remove my mask. A few more moments and this could have been very bad. The man was a bit tall but didn't act as a threat. He looked like he could have money, so I decided to risk it and agree.

"I am. Two hundred dollars and I'm all yours for an hour," I said, trying to act like I wasn't scared out of my wits.

"Nah. Let's do a blow job for 50 dollars," he countered. I hadn't considered what I would charge for just a blow job, but that seemed low.

"100 dollars. I'm that good," I said, not having a clue what I was talking about. I wasn't even sure what counted as a good or bad blow job.

"If I'm paying that much, you better get naked for me as well," he said, looking at my body. Doesn't this idiot know you can see videos of me naked all over the internet?

"Fine. Get your car and pick me up. There's a hotel down the road." He gave me a confused look.

"I'm not paying for a hotel for this. Just do it right here in the alley. I don't care."

"I'm not getting naked and blowing you in a public alley. You can take me to your place if you must," I said, not liking this deal more and more.

"I'm not taking a whore to my house either. This isn't a date. This is you getting mouth fucked for some pocket change. We do it right here and now, or I walk. I know you haven't been getting any bites tonight. I might be your last chance to earn money today," he said with a devious smile. He wasn't wrong. The alley was very dark, too. I couldn't believe I was considering this, but I needed to come away with some money today.

"Fine," I said, dropping my dress to the ground. I wasn't wearing a bra, and the man's eyes immediately went to my now naked tits. Seeing his gaze, I realized I was being stupid. Not for whoring myself out in public like this. That was a whole other level of dumb. He hadn't given me a cent yet. "You want the rest? Hand over the money," I said, using my stern voice.

Without breaking eye contact with my nipples, he handed me some cash. I counted it up and was satisfied he had paid the agreed-upon price. I stuffed the money into my dress laying on the ground of the alley. Pulling my panties off, I told the man to get his cock out, which he did. I got on my knees and took his penis in my left hand. For a brief moment, I stared at it and considered the situation. I was outside and naked in a public alley. Anyone could walk through here and see the entirety of my nudity. For a measly 100 dollars, I was going to take this stranger's dick into my mouth and swallow his load. All because I was pregnant for the second time with an unknown guy's child. Worst, this may not be the lowest point of my life when I think of some of the other things I've done in the past few months.

I sighed and put my lips around his shaft. Moving my mouth up and down his cock, he started vocalizing his delight. "Oh god, you have the lips of an angel. You are easily worth the money. Fuck..." The taste of his cock soon filled my mouth. My tongue teased his head as I tried to make him cum as fast as possible. A slight breeze ran across my ass and reminded me I was very naked still. He rested his hands on my hand and started to push me closer to him. As a result, I took more and more of his cock into my mouth.

I was about to tell him to back off, but before I could, he drained his balls into my mouth. Yet another man whose cum I now knew the taste of. As I withdrew his dick from my mouth carefully to avoid spilling cum on my body, I heard a new voice coming from one entrance of the alley. "Okay, miss. Stay where you are. You are under arrest for prostitution."

Looking to the person speaking while I swallowed my mouth full of cum my worst fear was realized. It was a cop. She was cautiously approaching me with handcuffs already out. "Jesus Frank. You weren't supposed to actually have her blow you. Just get her to take the money," a voice said from the other entrance to the alley. Swinging my head in that direction, I was met by the sight of another cop. They had me surrounded.

"Hey, what can I say? I wanted to make sure," the man whose cum I just swallowed said. I looked up at him, still on my knees, inches from his deflating cock. "But seriously, you are under arrest. Thanks for the blow job, though," he said, looking down at me. Did I just blow a cop?

I stood up and backed up to the wall of the alley. The cop I blew started getting his pants on while the other two slowly approached me, holding their hands out to try and keep me calm. There was no way I could allow myself to get arrested here. I thought about offering sex to them in exchange for letting me go. I seriously doubted they would go for it, especially with one of them being a woman. All that would do is probably get my voice recorded by their body cameras. I seriously hope the undercover cop that I blew didn't have any way of recording me.

My only option then was to try and run past one of the two officers blocking the way out of the alley. But they could easily grab me as I tried to. Without much thought, I approached the male officer who was blocking one side of the alley. "Ma'am, I need you to turn around and put your hands behind your back," he instructed me. Rather than do that, I shook my tits at him, which threw him off guard. I took the opportunity to then run past him before he could snap back to reality.

I was now naked on a public street for the third time in my life. However, this time, the streets weren't empty. The sight of a masked naked woman quickly caught the attention of the several dozen pedestrians and numerous cars driving by. Soon, the phones were out to add more to the online library of my sexual humiliation. This was not my immediate concern. I quickly realized I was going in the opposite direction from where my car was parked. I could also hear the police yelling at me as they pursued me. Thankfully, I was still wearing my shoes. I bolted as fast as I could across the street.

I had no clue where I was headed as my naked tits swung all over the place. I went down a small side street and onto another busy street, giving a new crowd of people a live view of my naked body. I was putting some distance between me and my pursuers, but I knew soon they would call for backup and a police car would show up. I would be in real trouble then. I needed to hide. Crossing two more streets, I was no longer in view of the police. I ran down another alley, knowing I had to find a place to hide there.

In the middle of the alley, it opened up to a small parking lot with no cars. What it did have was a tent set up and a man sitting nearby it. This was a homeless man's encampment, but as the saying goes, naked women running from the police can't be choosers. I ran up to the man, likely startling him half to death while giving his other half a boner. "If you let me hide in your tent, you can fuck me all night long," I blurted out to him. He was speechless and still taking in the situation. His eyes darted between my face, tits, and his tent. I didn't have time for him to consider it. "Seriously, I'll be your sexual plaything all night. Anything goes. But you must agree to it right this second," I pleaded.

Finally, the man's eyes showed he understood, and without saying a word, he directed me to the tent, and I practically dove into it. He joined me, and I zipped it up without even asking. "All that I ask is we stay quiet for a bit. The police are looking for me. I promise I haven't done anything bad like murder. You can probably guess what kind of crime they want me for by what I'm wearing." The homeless man nodded, and we sat in the tent silently. As I caught my breath and prayed this would work, I examined my soon-to-be home-free lover. He had a heavy beard and very worn clothes. But he smelled reasonably clean, which I was thankful for.

My thoughts were interrupted by my two police officer friends running by, not giving the tent any care. With that, I finally let myself relax a bit. "Okay, thank you so much. But I'll need to stay a bit. I'm assuming you want to...," I said, followed by an enthusiastic nod by the man. He has yet to say a word but started undoing his pants. I, conveniently, was already naked, of course. He indicated with his hands he wanted to do me from behind, so I got on all fours and stuck my ass out. It only took about two seconds after I got into position until I felt his cock slip into me. I have blown a cop and fucked a homeless guy, all in the comfort of an alley. It took only twenty seconds of pumping me until he filled me with his cum. Who knows how long it has been since we was with a woman.

I sat down, and he held up a finger, telling me to wait. He exited the tent and walked off out of sight. I worried he might be going to turn me in to the police, but what could I do? I still had no clothes to speak of. Five minutes later, a new man entered the tent. I quickly covered myself with my hands. "What the fuck! Get out of here," I cried out.

The man didn't stop entering the tent. "I paid Silent Joe five dollars to have sex with you. He indicated you were willing to do anything sex-wise. Is he wrong," the man asked, looking at my naked body. The homeless guy is whoring me out to other homeless men for his own financial benefit. Forget about blowing a guy in an alley. This was now my lowest moment. But what could I do? If I denied sex with this man, Silent Joe, as he is apparently called, would likely kick me out of his tent.

I lay down on the floor of the tent and spread my legs. "Yeah, you can fuck me," I said, defeated. He practically dove into me, licking my nipples extensively.

"I've read stories about young women getting so horny they fuck guys like me. I figured they were just stories of fiction. But now I see they are based on fact. I haven't fucked a girl since the Reagan administration," he said, slobbering all over my tits.

"Hurry up, Cotter, some of us are waiting for our turn," a voice from outside the tent yelled. Oh god, there's a line of them, I realized. I have a line of homeless men waiting to creampie me. I hope this crowd doesn't draw the attention of the police. That would be the icing on this fucked up situation. For my true identity, Cindy, to not only be revealed as a prostitute but to be caught while having an orgy with these street vagrants.

But the police never did show up. But I did end up taking the cum of six different down-and-out men. Some fucked me without saying a word. Some told me I remind them of old flames of theirs. One had me masturbate for a while before plowing me. All of them paid only five dollars to fuck me. Finally, Silent Joe rejoined me in the tent. "Hey, thanks, asshole, for whoring me out. That's not what I meant when I said we could do whatever you wanted," I told him, mad as the sperm of these six men tried in vain to impregnate my already pregnant womb. As silent as ever, he motioned to the door of the tent, indicating that I was welcome to leave whenever I wanted. It was apparent now that Silent Joe was mute. How he communicated to the other men that he had naked women in his tent who he would let them fuck in exchange for five dollars remained a mystery to me my whole life.

"No, I understand. You helped me out by letting me hide here. I just wasn't expecting you to become my short-term pimp. I need clothes. Do you have anything you can give me? I'll bring them back, I promise," I said. It had been almost two hours. I was confident the police had probably given up the search, but the appearance of naked women, mask or not, would get their attention again. Joe made a series of motions with his hands, and after some back and forth, I finally figured out he wanted me to spend the night with him. In the morning, he would have clothes for me.

I was at the mercy of this homeless man, so I did just that. I slept naked next to him overnight in a tent in the middle of the town. In the morning, for breakfast, I served him a blowjob. Apparently, that was the price to borrow his extra set of clothes. I made short work of his dick, and with his cum sitting in my stomach, I got dressed. For the first time in almost half a day, I wasn't naked on the street. The pants he gave me were way too big for me, and I had to hold them up to keep from flashing my pussy. The t-shirt was also oversized, and lifting my arms too much would reveal my tits. I thanked him, not that I think it was needed after sexually satisfying him twice. Facing away from him, I took off my mask and exited the tent. No one was around. I grabbed some loose newspaper and wrapped my mask in it.

Despite my oversized outfit, I made the five-block trip back to my car without issue. Inside, I quickly grabbed my phone and started looking through local news sites and social media. There were, of course, stories and videos of me streaking through the streets. I didn't need to see my naked tits bouncing like that ever, but the videos were now available. However, I was relieved to see no news from the police. No audio of my voice was being posted publicly. I somehow managed to make it through this whole ordeal without my identity getting revealed. But barely.

After getting into the house and up to my room without my parents noticing why I came home dressed like I was, I considered my options as I changed. I could no longer try to pick up customers on the street like that. It was probably filled with undercover police looking for me. It became tempting to go to Shawn who had been able to find people willing to pay for sex so easily it seemed. But I quickly tossed that thought from my head. Shawn doesn't fix my problems, he only adds to them. I needed to change my strategy. I would have to prostitute myself as college student Cindy. If I kept my sexual activities to a small group of people, I could make this work.

Before anything, though, I felt obligated to return the clothes to Silent Joe. He had whored me out, but only after I had told him that was precisely what the police were chasing me for. Thus, I couldn't be mad at him for that. I returned to his alley but without my mask. It was risky. However, he still wouldn't have any clue who I was nor any proof of my identity. I found him outside his tent as I had the first time. I handed him the clothes, and he suddenly realized I was the girl in the mask. I also gave him twenty dollars. After all my efforts yesterday, I have ended up with less money now than before I started prostituting myself. He smiled big when I handed him the money. "I trust you will keep my secret," I said, smiling back.

Joe then gave me a devious look I didn't like. Rather than immediately nod in agreement like I assumed he would, he motioned to the tent. You mother fucker, I thought. "Are you kidding me? I fucked your brains out yesterday and gave you twenty dollars just now, almost doubling the money you made from selling me to your homeless friends. Now you are saying I need to fuck you again for your silence," I yelled a bit too loud. Scanning the area, no one else was around to hear my vagrant orgy confession. Could Joe even turn me over to the police at this point? He didn't know who I was, just what I looked like. How would a mute even manage that? But if there was even a chance...