Cindy's Bikini - Money for Cum

I'm not materialistic. I don't own a closet full of shoes or buy new clothes every week. But I could get a lot of enjoyment out of two grand. Especially after everything I've been through, this money could give me the comfort I need to rebound from all of this.

With every thought in my head considering doing this, a cold sweat would come over me. Deep down, I knew I was going to do this. For a single night, I was going to take money for sex. What scared me most was, what if Shawn offered up a second client? Is doing this one more time that big of a deal? Is three? Is twenty? No. I do this once and never look back. I'm in college. Every girl has their slutty stories during this time in their life. I got out my phone and didn't let myself pause again to think. I texted Shawn, simply saying, 'Okay. Just tell me when.' Five minutes later, he told me it would happen tomorrow night.

At the agreed-upon time, I walked into the hotel room where I thought I would never be again and prepared for the client to arrive with Shawn. I elected to not wear just my underwear. I didn't want this man to see any of my body in case I decided to walk. I wore blue jeans and a white T-shirt. No unique clothing that could be used to identify me. My mask was securely on, only to be removed if and when I agreed to the transaction.

Shawn brought the man into the room. He wasn't bad-looking or very old. In fact, he was mildly good-looking, skinny, and in his early to mid-forties. Most importantly, I had no clue who he was. I didn't recognize him in the slightest.

"Hello. I see you are wearing your mask. I trust our friend told you I will only pay for the mask being off."

"Yes, and I trust that he told you I will only take the mast off when and if I agree. We'll start with questions."

He smiled, removed his coat, and sat in a chair by the bed.

"Of course. I will also have questions as well, but please. You can start."

What questions did he have for me? Why did he need to ask anything?

"Show me your driver's license, I want to see that you indeed do not live here."

I thought it was likely that he wouldn't be agreeable to this. Men don't hire hookers and then turn around and tell them where they live and their full names. But without any protest, he pulled out his wallet and handed me the card. Flint Ferguson lives in Boston, which is almost halfway across the country. I gave the card back to him and asked more questions.

"How did you hear about me, and why do you want to fuck me specifically?"

"Do you normally interrogate your clients?"

"Just the ones that want to see my face. Also, why are you so far away from home?"

"I've been in the area for a couple of weeks for business and will be leaving a new few days. Are you not aware of the internet presence you've been creating?"

"What? No. What is being said?" That wasn't good. I didn't need this kind of attention or any, really.

"There is just a lot of buzz about a hot masked woman selling her body for money with a teenage pimp. Also, she is fucking without requiring any protection and isn't on birth control. Your previous clients indicated they were very satisfied with you." I found it weird that people were talking about how much they enjoyed having sex with a particular hooker. Still, in truth, I found the idea of paying for sex weird in general.

"I do let people fuck me without condoms, but if those idiots really believe I'm not on birth control, well, that's on them. So you want to fuck me because some guys said they enjoyed fucking me online?"

"There are tons of women walking the streets selling their bodies. This is their life. You, however, are hiding your life from this. You may have a boyfriend or husband. A job or schooling. Friend and family. Tonight you are fucking a stranger for money. Tomorrow, you may be in class trying to understand advanced calculus. It's the mystery of you that fascinates me and makes me want you. I could be fucking anybody."

I thought the answers seemed genuine and logical. I came here with the intention of fucking another stranger for money. My fears have been calmed, let's get this over with I thought.

"Okay. I'm satisfied by your answers. I agree to have sex with you. Go ahead and pay Shawn."

He handed Shawn what looked like a large amount of money. Shawn counted it and gave me a nod. He then got up and left as this man didn't want an audience. I started to undo the straps holding my mask in.

"Wait! I will tell you when I want you to remove the mask. We're going to take things slow. I would like to ask you questions first. But go ahead and take your shirt off."

My hands left my mask and pulled my shirt up, revealing my lacy pink bra. "You can ask whatever you want, but I'm under no obligation to reveal anything I don't want to."

"Of course," the man said, sitting beside me on the bed. "Why did you start selling your body?"

As he was asking, his hands found my breasts and started lightly feeling them up. I could lie to him, and he wouldn't know. But I also had no reason to lie.

"I was forced into this to help a friend. That's all I say."

"Fantastic! That fits even more with my idolized vision of you. Normally you would have never sold your body, but here you are."

He got closer to me and started kissing my neck. "Next question. Do you have a husband or boyfriend?"

"No... I broke up with him before I started doing this."

He started undoing my pants, getting ready to take them off. "How many sexual partners did you have before you started doing this?"

I found that harder to answer. He had no need to know such things about me. "I'm not going to answer that," I said instead.

He had my pants off and was starting to rub the outside of my panties. "That answer tells me plenty. Why don't you make the men you sleep with wear condoms?" With a single hand, he was working on getting my bra off.

"To make more money." That I considered the truth, but I knew it was more complicated than that.

My bra was now off, and his hand started exploring my naked tits while the other stayed focused on my panties. "Please, I don't believe that. Men would pay you a lot of money to have sex with someone like you, even with condoms."

I didn't respond to that. His hand was now inside my panties, fingering my pussy. "Why did you agree to have sex with me without the mask?"

"Because I don't know you, and you don't live here." He had now taken my panties off, and I sat fully naked on the bed with him, wearing only my mask.

"But are you sure? Maybe one of your previous clients paid me to find out who you are?" He laid down on the bed and got fully naked. As I climbed on him and prepared to take his penis in me, I addressed his last question.

"I could still leave right now if that's what you want. Why are you making me doubt your purpose here?"

"That is not my intention. I am not here to reveal anything about you. I apologize." The ease I felt earlier after I convinced myself he was just a stranger looking to get laid was fading. I began to doubt my decision. But I didn't stop, and I had his dick now inside me while I humped on top of him.

"How many men have cummed inside you in your life?"

"A lot. That's the job. That's what you are going to do, isn't it?" What guy wants to hear how much sex his hooker has had before him?

"Had anyone ever come inside you before you started this line of work?" At this point, I was humping him vigorously, trying to get him to cum. These questions were unnerving. Again, I chose to hide anything about my sex life before I started having sex for money, i.e., Shawn.

"Do you consider yourself hot? Beautiful?"

"Sure. I have a lot of confidence in my looks," I replied.

"I'm going to cum in the next minute, I want to see your face when I do. Please go ahead and remove the mask." As my legs continued to lift me up and down on his dick, my hands started undoing my mask. I had taken off my bra and panties for many men in the past month. But taking off my mask today felt like it did when I first took off my bikini for those boys back at my pool. Like, somehow, this was a bad decision that was going to significantly affect my life. With the last strap undone, I lifted the mask off, and Mr. Ferguson saw the face of college student Cindy fucking him. "You are beautiful. I have one more offer while we are in the last moments of being carnal. I will pay you another thousand dollars if you tell me your name. Just your real first name."

"What? Why do you want to know that?" It was a weird situation. I had shown this man my naked body. Let him touch me and put his dick in me, and would soon seed me with his cum. But I didn't want to tell him my name.

"No reason. That's my offer. Tell me before I cum or the deal is off."

I slowed down my humping while I thought. But he just made up for the slower pace by thrusting his dick harder into me.

"I could just lie to you. You wouldn't know."

"Ah, but if you want the money, you will need to ask your friend outside to tell me your name as well. If they don't match, then no money."

That would verify if I was lying or not. Shit. I would increase my take by 50% by speaking a five-letter word. He was about to cum, I had to make a choice.

"Cindy, it's Cindy!" I yelled right when I felt his cum enter my pussy. I stared at him as he finished his orgasm. Did that count? Did I say it soon enough? Was that enough information that he could now figure out everything about me? I asked these questions to myself as I sat on the naked man that I had just told my name to. A man who could expose that Cindy, the college student, has been selling her body to the world.

I got off him and got dressed. He got another wad of cash from his wallet and handed it to me. Without confirming my name with Shawn, he left the hotel. As I was getting dressed, Shawn handed me the money. "Don't say anything. No more offers, no more deals. That was it. Bye forever," I said, leaving the room.

And that was it. I had no more reason to ever engage in this behavior again. I was clear to focus on being an ordinary college girl. I didn't even have an appetite to date anyone or do casual hookups. I think it was going to be a long time till I'm ready to face another dick. And I will never be ready again to face another vagina.

Shawn kept his end of the deal completely. Ashley revealed her pregnancy to her shocked parents the next day, with Shawn present. They made up a story about meeting by chance and falling in love, which led to the pregnancy. The idea of having to pretend to be in love with Shawn and possibly spend your whole life with him seemed magnitudes worse than the prostitution I had just done. Word of this spread quickly at both the high school and my college. Ashley constantly had to explain why she opened her legs to a teenager. Meanwhile, Shawn became a legend at his school. None of this was surprising, but it felt so unfair.

This news shocked and concerned my parents as I was her best friend. I went along with the story and said I suspected she had a boyfriend, but she was too shy to share the news with me. I said she finally confessed to me that she was pregnant with Shawn's baby and that I encouraged her to tell her parents. I think the last part comforted my mom and dad, knowing I encouraged her to be honest with her parents. But they were still worried and announced they were taking me off birth control. Their logic made zero sense, but they thought that being on it would only encourage me to be more sexually active. I didn't argue, as I had no plans to be sexually active for a long time. I would finish the week supply I had left and that would be it.

The excitement of Ashley getting knocked up was starting to fade, and most of my days were spent studying and relaxing by myself. I cut off my male friends Jerry, Alan, and Greg. At first, I just blew them off, claiming to be busy. Eventually, I stopped responding to them at all. Their messages to me became increasingly angry until I blocked them entirely. I rarely saw Ashley anymore. She dropped out of school and focused on her orgy baby, as I called it in my mind. Life was quiet and I liked it. Everything was good.

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Except my period was late a couple of days. That's fine. It's probably just the stress of the recent events. It can happen to any girl.

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But a week later, and still nothing. I was now in full panic mode. There was only reason for this to be happening and that was impossible. I had just taken my last birth control pill, and it had been 2 weeks since I had any 'male contact.'

I spent the whole day in denial, but I finally got myself to go to a corner market (20 miles out of town, just to be safe) and bought a pregnancy test. With shaking hands, I waited for the result, and it showed me what I already knew. I was pregnant.