Cindy's Bikini - Homeless Lover

"God damn it," I said, going into his tent. I angrily got undressed and laid on the floor with my pussy spread, ready to get rammed by Silent Joe again. This time, however, he didn't immediately dive into my pussy. Instead, he climbed on me and started kissing me very tenderly. I had prepared myself for a quick fuck, but instead, Joe was taking things very slowly. He moved his kissing to my neck, where his large beard felt oddly nice, tickling my chin. He moved down lower to my breasts, but this time, he didn't slobber all over them but rather lightly caressed them with his tongue. My toes started to curl together, and I realized my body was starting to react to him.

Not wanting to spend my morning being pleasured by a homeless man on the streets, I tried to convince him to get on with it. "How about you stick that dick of yours in me and we get this show on the road," I asked. But Joe seemed to ignore me completely.

Instead, he went lower. First, tickling my belly button but then finding my pussy. With his tongue now exploring every inch of my labia, I couldn't keep up my facade of apathy any longer. "Oh fuck...," I said out loud involuntarily as a wave of pleasure caused my muscles to spasm. He didn't let up and continued to go to town on me. I gripped the tent's floor, and my legs writhed back and forth. Just as I was beginning to accept my inevitable orgasm from this homeless man, he stopped. He brought himself face to face with me and penetrated me with his cock. I gasped and made a face that clearly showed him my ecstasy.

He humped me slowly, but my hips started pushing him deeper into me. He got the message and started fucking me hard. My moaning turned to wailing, and I was soon filling the alley with sounds of my pleasure. I wrapped my legs around him, and in a final thrust, my climax reached me, and for that moment, I was in love with this man. But soon, that feeling faded, and I was hit with the realization that a homeless had made me cum while fucking him in his alley tent. Sometimes, I think the terrible names Shawn and the boys called me were accurate.

Joe withdrew from me, and I found myself with his cum inside my pussy. I came here to thank the man, and I think my work was done. "She is very pretty. Why was she hiding her face before? Anyway, Silent Joe, I got another five dollars for your whore," a voice from the tent door said. I turned around and was faced with the same line of vagrants I had been whored out to yesterday. Only this time, there were eight of them, and they had how all seen my face.

I looked at my latest lover. "No, I'm not doing that again today," I pleaded. He gave me a look that was hard to interpret, but I took it to mean it was my choice. Denying these men came with a risk now that they had seen my face. Unlike Joe, these guys were rather vocal. "Fine. I'll fuck your friends, but I keep the money," I said, knowing they only paid five dollars a piece for the pleasure of being with me. Joe put two of his fingers together and then pulled them apart, holding up two individual fingers. "Fine, you can have half. Twenty for me, twenty for you," I said in the saddest compromise of my life.

I then finished out my morning by banging eight more homeless men. I was relieved to say none of them managed to get me to cum again, although, at times, it was closer than I would have liked. Some of them didn't even seem to make the connection that I was the same girl as the masked woman they fucked yesterday, making me doubt that I ever had to agree to this. But with the cum of nine men inside me, Joe handed me my cut. With the twenty dollars I had already given Joe as a thank you, I had nothing to show for this morning except more men added to my body count. I got dressed and left the alley, making a note never to go by this area again. The last thing I needed was to pass by a homeless guy with some friends who would then remember I was the girl he railed in an alley that one time.

I got home and had lunch with my Mom and Dad. They were curious where I had been all morning, and rather than telling them I whored myself out to nine homeless guys for a grand total of zero dollars, I lied and said I went for a walk in the park. They didn't question that, and I was reminded I needed to change my cum soaked panties before long.

At school the next day, I decided to take a chance and try a new strategy. Allan was a quiet guy with whom I had been in two classes with. From working with him on a couple of projects, I knew he was single and had little luck with the ladies. I got him to a secluded area and made an offer. "Allan, I was wondering if you want to go to dinner with me tonight. There, we could talk about a proposition I think you will find interesting," I said, trying just slightly to hint at something sexual.

"Are you asking me out on a date," he said, surprised.

"Of course," I replied, thinking he had gotten the hint.

We arranged to meet at a restaurant that evening, and we greeted each other with a hug before sitting down at the table. "Cindy, I can't believe you've developed feelings for me. I always had a crush on you, but I figured I never had a chance with you. Thank you for asking me out like this," he said, smiling.

Hearing that worried me. Maybe he didn't pick up on what I was hinting at before. "I do think you are awesome, Allan. But this isn't a regular date. Sorry if I wasn't clear on that before. After dinner, I am open to... additional activities if you are willing to pay for them, of course."

Allan's face looked confused. "I don't understand. Are you saying we can go to a movie after this as long as I pay? There's not anything out I want to see, though."

I shook my head and tried again. "That's not what I am saying. We can have some fun tonight, but only if you make it worth my while," I said, winking.

He still wasn't getting it. "I'll try and make the date as fun as possible, but I think the girl should be expected to put some effort into that as well."

God damn it, fine. I leaned in and whispered. "If you pay me two hundred dollars, we can go back to your place and have sex."

Finally, Allan's eyes lit up. "You're a prostitute," he said loudly.

I looked around and saw numerous tables staring at us. "How dare you! I am no such thing," I said aloud. Then I leaned back in and whispered to him. "Yes, I am but shut the fuck up about it. It's not something I'm advertising and is just for the very short term. You are the first and only guy I've offered thus far." That was a total lie, but somehow I doubted Allan and those homeless guys I fucked were in the same social circles.

"Is that the only reason you asked me out tonight, to get money out of me? You realized how much of a confidence booster it was when I thought you asked me out. I see now you have no real interest in me," he said, sulking in his chair.

I reached out and took his hand. "No, that's not true, Allan. It's like I said. You were the first guy I reached out to. I've offered my body to no one else. Yes, I am looking for money, but I'm not looking to do it with anybody. I want to do it with people I like."

He sat up and smiled at me, and I thought I had turned this interaction around. "How about we get out of here and go back to my place, and I fuck your brains out. But for free, of course," he said.

"No, Allan. I'm not going to do that without getting paid. I'm sorry." I was about to leave and give up on this when I heard my previous words being played back to me.

I turned around and saw him holding up his phone. "You fucking asshole. Turn that off and delete it," I asked, knowing he would not.

"Cindy, I'm not the kind of guy who would blackmail a woman into having sex with me," he said, pausing afterward. "I am, however, willing to blackmail a girl who tried to trick me into paying for sex instead of actually liking me."

"I was not tricking... you know what? Fine. Let's go to your place and fuck. Then that recording gets deleted," I said.

"We'll see," Allan said.

A short ride in his car later, and we were back at his small apartment. "I don't have any condoms. I wasn't planning on the date resulting in sex or anything other than talking. Is that okay," he said as we walked in.

"Yep, no issue here," I said, thinking about the bastard growing in me. I was about to bang this guy without a single dollar to show for it. I was really turning out to be the world's worst hooker.

"I have to admit one more thing. This will be my first time," he added. Of course, it is. It was my destiny to de-virginize every loser in the county, right?

He guided me to the bedroom, where we then stood awkwardly. After a few seconds, I finally broke the silence. "So what do you want to do, Allan? You're the one blackmailing me, after all."

"I guess, strip for me? I'll sit on the bed, and you can be my personal stripper. I'll even put on some music for you." He did just that, and soon I was shaking my bare ass as he sat on the bed. As I took off my bra and shook them inches from his face, I wondered how many girls in their early twenties had been blackmailed into sex because I feel like I've had it happen about a dozen times to me.

"Get on the bed. I can't wait any longer to become a man," Allan said, standing up and taking off his pants. I lay on the bed, and he got right on top of me. He attempted to direct his penis into me but fumbled, trying to find the right spot, almost putting it in my ass once. Finally, I reached down and directed it myself and off to the races he went, plowing his cock into me.

"Is there any way I can convince you to pay me for this?" I asked in a final attempt to get the money. He answered me while using his dick as a ramming rod inside my pussy. "It's a bit late to ask that, don't you think Cindy? Especially... now," he said as I could feel him pour cum into me. He raised a good point. Smart hookers don't get the client to agree to pay after they have been inseminated. I, as the evidence showed, was a moron of a hooker.

He pulled out and paid me no more attention. Instead, he walked around his room and cleaned things up. "So you won't tell anyone I'm a prostitute, right? I took your virginity, and now we are even," I tried to confirm.

"I'll see you here next week. Same time, we'll say," he said without looking at me. Fuck.

"Can you at least give me a ride back to the restaurant where my car is parked," I asked.

"Just call an Uber," he replied. With his balls drained, he couldn't care less about me. I called for the car, and once I was back in my car, I was down thirty-two dollars. I was officially the worst whore ever.