Cindy's Bikini - Money for Cum

All characters presented are 18-years-old or older. Even if not specifically stated in the text.

I had taken on four jobs thus far as a prostitute. A prostitute who wasn't even financially benefiting from selling her body. What was weird was how normal the situation had become in my head. One day after class, I was talking with a few classmates.

"Hey, what if this evening we meet up and knock out this assignment together," Jerry asked the group.

Jerry was a longtime friend who was in the same class as me.

"I can't," I replied, "I have a job tonight." I froze and regretted using that as my excuse. It was the truth, but now I had to explain what I meant by 'a job.' I certainly couldn't say that job involved me fucking one or more strangers in a sleazy hotel room.

"I didn't know you had a job. Where are you working?" Jerry asked.

I panicked. I confined in Jerry a lot, minus the obscene amount of sex I was having. He would likely tear apart any non-convincing answer I gave based on how well he knows me.

"I've started tutoring. Primarily high-school seniors."

I impressed myself with that lie. Worst case, I had several high schoolers I could convince to cover for me. I know them because they have been blackmailing me to cum extensively into my orifices, but that still counts as knowing them.

"You a tutor? That seems far-fetched. You hate teaching." Greg, another old friend, commented. "I'll be you have a new fling you don't want to publicize after you broke up with Mike."

"Not likely," Jerry said. "Cindy doesn't flirt with a guy without telling me, let alone hook up with one."

"Yeah, that's very true Jerry," I laughed. That was very, very not true ever since my first unwilling orgy with all those high-school-age guys.

I only have two more jobs until my life returns to normal. After that, I won't risk accidentally revealing I let guys cum inside me for money. Money that I don't get to keep a dime of as I allow a teenager to take it all for himself. That's what I told myself as I headed to the hotel again that evening. Arriving at the hotel, Shawn had only one thing to say as I was getting ready.

"Heads up, it's another group today."

"And I'm fucking all of them?" He nodded and then headed out the door to meet with my group of future lovers.

I was wearing my mask and black underwear when Shawn entered the hotel room, followed by 5 high school seniors.

"Holy shit Shawn. I thought for sure you were bullshitting us. How in the world did you become a pimp for this hottie?"

Shawn smiled. "I'll let you use your imagination for that. But yes, this is real. This hottie will gladly take all five of your virginities. She'll do it barebacked as well, like I promised. No condoms allowed."

"Seriously? She's on birth control, right?"

"What fun would losing your virginity be if you weren't risking knocking up the woman at the same time," Shawn replied.

When Shawn first told me of this terrible plan for me to be a prostitute for him, I figured he would be having me exclusively fuck other seniors at his school. He could easily approach them in between classes. I think he also knew how much it would piss me off, which I became more and more certain was his actual fetish. The number of guys in the senior class at high school I will have taken the virginity of was beyond embarrassing. Attending my brother's high school graduation next May will be a parade of former sexual partners of mine. Each time a name is called, I'll be reminded that I know what their dick feels like when they cum inside me.

"Do you think she's a classmate of ours? She could be Heidi or maybe Val. I could see those girls selling their bodies."

"No, she looks older than high school age. She's probably just some homeless chick desperate for money. Everyday women don't just decide to fuck teenagers for money."

"You're probably right. Hey! Let's see some tits. Take off your bra."

Silent as always, I showed off my tits to the five guys who had just agreed I must be a homeless chick. As men always do when I take off my bra, they stared in amazement. Without even asking, one of them approached me and started fondling them. A second went behind me to feel up my ass while a third got on his knees and started rubbing my pussy over my panties. The last two joined in by sharing my tit with the first guy, while the last kissed my neck. Ten teenage hands had their way with my body. My panties were quickly removed, and I had no more secrets to hide from them other than the identity of the girl they were mercilessly groping.

The hands gave way to their mouths, and soon they were licking my pussy, tits, and neck. All while I stood there. It was intense having that much male attention on my body. But finally, I was shown mercy, and one of the boys declared, "I'm too horny to wait any longer. I'm going to fuck her on the bed."

The five of them were going to have sex with me one at a time. I laid on the bed and without any more foreplay, the teenager drove his dick into me. He made the usual comments that virgins always say when they fuck me, which, unfortunately, I had a lot of experience with. 'You're so tight,' 'You feel so good,' and so on.

The guy thrusted his dick over and over into my pussy. He didn't even bother looking at me, making me feel like a sex toy. He finished inside me and left without even a thank you, not that I wanted one. The guy gets to celebrate having sex while I add another guy to list of people whose names I don't even know and have came inside me.

The second of them took a very different approach. He didn't immediately want to fuck me. Instead, he started making out with me. He was a very gentle kisser who, if it wasn't for the fact that he was a teenager who paid to fuck me, I might enjoy being with. We kissed for a while until he gently started having sex with me. Slowly moving his hips while still kissing me. At one moment, I lightly pushed him away from my face as I needed to catch my breath. We made eye contact and he smiled very sweetly at me. I pulled his face back in and continued to make out. The intimacy was starting to get to me, and I was lightly moaning. He finally finished in me without much fanfare and never stopped kissing me. He pulled his head back and lightly caressed my cheek. He gave me a final kiss and left the bed.

The next guy told me to stick my ass in the air and took me from behind. The teenager slapped my ass continuously as he fucked me, making untold comments about how he was a cowboy and I was a wild steed to be tamed. He thankfully didn't last long, and my ass stung from all the slapping.

Number four in my high-schooler bang train told me to sit on his dick. I did most of the work humping while he continued to fondle my breast, abruptly cumming and telling me to get off him. The last guy wanted to try every position in the book. Me on top, missionary, fucking me from behind, sideways, and a bunch that we didn't really know how to do. His friends finally hounded him to stick with a position and seed me, which he eventually did.

"Have fun with our babies, don't write!" The guys said as they walked out, having all lost their virginities.

I got dressed with the sperm of five more teenagers in my womb. A win-loss situation if I ever knew of one.

The next several days went by without issue. A couple of months ago, letting five high-schoolers have bareback sex with me would have been all I could think about for weeks, but now I barely gave it a second thought. I had one more 'client' to please.

Ashley was getting anxious. Every day, her pregnancy was progressing further along. She wanted to get her ducks in a row before she started showing and the story got out. She continuously asked me when I would be having sex for money again. It was far from a typical situation in which your best friend is asking when you are next prostituting yourself so she can claim a baby daddy from all of her orgies. But that's the life we live in.

Night came, and I arrived at the hotel for the last time. The final time I would ever agree to have sex with someone without me actually wanting it. No more blackmail, no more favors. This is the second time I've told myself that, but I knew it had to be true now. Shawn brought three men into the room and my heart sank. I knew all three of them.

Jerry, Greg, and Alan. My three closest guy friends who I have known for years. They had supported me through numerous breakups, including my last one with Mike. In some ways, I think they knew me better than even Ashley, minus all of the sexual stuff she and I had done.

Now, I was staring at the possibility of having sex with them. I saw these guys as my brothers, maybe even more so than Tommy, my actual brother. The idea of getting sexual with them was not something that had ever popped into my mind. I seriously considered popping off my mask and revealing that it was me. True, if I did so, I would have so much embarrassing explaining to do, but it would prevent me from having sex with my friends. I'm sure they also would like to avoid having sex with their close friend as well. While I was complementing that option, my friends started talking.

"Wow, you are right; her body does look a lot like Cindy's. Nice job dude," Jerry stated. Shawn gave him a fist bump.

"Hey, I'm here to please. Like I said, she will keep the mask on and not talk. You can project whoever you want onto her in your mind."

Greg spoke up. "Eh, it's close, I guess. She looks skinnier than Cindy. Cindy has that jiggly ass, you know? I doubt her thighs would be that small. But sure, I can look past that and imagine she's Cindy."

Alan agreed. "The important thing for me is the girl's tits look almost identical to Cindy's. When my face is deep into her boobs, I want to convince myself they are hers. I've stared at Cindy's tits for so long."

What the hell was going on? Why were these guys talking so sexually about me? Did they hire a hooker to pretend they are fucking me?

"I thought for sure when she broke up with that asshole Mike, she would finally date me. But it's been weeks, and all she does is talk non-stop at me. I've listened to so many boring stories from her. But when it comes to putting out, she always looks elsewhere." Jerry was showing me his true colors.

"Don't forget, though, when you eventually convince her to date you, you'll get us recordings of her fucking right? Any nudes she sends you, you send to us," Greg said, still staring at my legs.

Jerry nodded his head. "I got you those panties, right? That was risky to take when I was at her house last."

"She has posted like no bikini pictures this year. I jerked it to last year's pictures for like the thirtieth time last night," Alan said.

I couldn't believe what I was hearing. These assholes had been pretending to be friends with me for years just so they could possibly 'earn' sex with me. I've heard this nice guy shit before, but I didn't think these guys would ever dish it out themselves. I wanted to leave this room and destroy everything these guys have ever given me and every picture I have of them. But I couldn't. If I left, Shawn would use this as an excuse to make me fuck twice as many guys in even worst situations. I'll fuck these guys before telling them to fuck off forever.

"Okay, okay, okay. Cindy's a tease who will one day feel our cocks unloading in her pussy," Jerry said, getting the three guys to focus on him. "But today, we are here to fuck this girl as a proxy for Cindy. Let's consider it practice for when we get the real thing."

My three 'friends' then focused their attention back on me. "Yep, my dick is ready. Cindy! Take off your bra and shows us your tits. We've been waiting years to see them," a very anxious Alan said.

Hearing them call me Cindy was startling. I knew they were using me as a stand-in for....myself. But hearing them ask for Cindy to show them her tits really made me paranoid that Shawn had actually arranged this whole thing by telling them who I was and giving them instructions to pretend they didn't know. But I couldn't prove that without revealing myself to them. Instead, I just had to expose my body to three guys who have known me and apparently been lusting after me for years.

My bra hit the floor, and the guys kept their role-play up.

"Holy shit Cindy your tits are awesome. You are so horny for us that you would let all three of us see them and feel them right here and now?" Alan didn't wait for an answer and helped himself to two handfuls of my boobs.

The guy apparently masturbated to the sight of my boobs in a bikini for years, and now I was letting him feel them up fully naked. Jerry pulled him back and spoke.

"But that's not all you want to show your dear friends, right? You think we deserve more?"

Rolling my eyes behind my mask, I dropped my panties.

"Turn around and bend over Cindy. I want to see your pussy from behind."

"Now rub your tits with your hands."

"Lay on the bed and spread your legs as far apart as possible."

"Cindy, rub your pussy, then stick your fingers in my mouth."

My three closest male friends were relentless in having me pose or do whatever perverted thing they could think of. And I did them all without hesitation or complaint. All while they called me by my real name.

"Okay, Cindy. You've shown off every inch of your body to us. Let's give you what you really want now. What you've wanted from us for years but have been too shy to ask for. Our dicks inside you," Jerry proclaimed.

The three men proceeded to fully strip naked in front of me. I was now looking at the erect dicks of three guys I, before tonight, thought of as brothers. I would rather take on ten more high school teenage dicks before these three, but I knew this was coming.

As directed, I got on the bed on all fours with my ass sticking out. Unlike the high-schoolers I fucked last time, these guys wanted me to pleasure them at the same time. Alan got behind me with his dick inches from the entrance to my pussy.

"You really think it's a good idea for me to fuck you without a condom Cindy? Geez, you are horny, but okay."

My friend was then inside me and started fucking me hard. He really seemed to enjoy the sound of his skin slapping my ass cheeks when he humped me.

"As you insisted, Cindy here's my dick for you to suck on. It's crazy that you couldn't decide which of us to fuck first, so you just decided for us to fuck you at the same time," Jerry said as I accepted his member into my mouth.

"And here's my dick for you to work on with your hand Cindy. But don't worry. As you begged, we will all be cumming inside your pussy." Greg laid nearby, and my hand started working his shaft.

This morning, I talked to these guys about the shoes I bought. Now all three of their dicks were getting pleasured by my body. When I see these guys next, I'll probably still have some of the cum in my womb.

"Are you sure you want me to cum inside you, Cindy? Aren't you off birth control? You don't care if I impregnate you as long as I'll keep fucking you? Okay..." Alan then splooged inside me.

He was no different than every guy I had interacted with in the past few weeks. I was a cum dumpster to him. Even if he didn't know who I was, that's all I was to him.

Jerry and Alan traded places. Alan told me to 'clean him off,' and I no longer had to wonder what his cum tasted like, not that I ever needed to know.

"Wouldn't it be better, Cindy, if we did this later by ourselves? You want to feel all of our cum inside you at once? Okay..." Jerry then penetrated my pussy.

He held onto my ass hard and got in deep in me with his dick. Jerry, my 'good' friend, was six inches deep in my vagina with nothing between him and my womb when he inevitably cums. Will I have any friends who haven't felt what the inside of my pussy feels like with their dicks and/or tongues? Because the current trend is telling me I will not.

"Get fucking pregnant bitch!" Jerry yelled as he came, gripping my ass cheeks even harder. For my last 'friend' Greg, he had me flip over and pulled me to the side of the bed. Jerry put his dick in my mouth because, god forbid, I don't get everyone's cum in my pussy and mouth. Alan meanwhile played happily with my tits.

"Cindy. I've imagined this moment for so long. I'm glad you finally let me do this. I promise when you inevitably get knocked up from this, I'll continue to agree to treat you as a cum slut, even as your giant titties are overflowing with milk."

After that beautiful speech from my latest lover, Greg thrust his member into me. "Oh fuck that's fucking good." Greg didn't last 30 seconds before, as he said, 'gave me what I deserved. A pussy full of his cum.'

The guys didn't have in them to fuck 'Cindy' a second time tonight. Apparently, they masturbated to my bikini pictures and used panties too much over the past few nights. They got dressed and told me they'd see me tomorrow before class, which was weirdly accurate.

Once the door closed, Shawn, who watched this scene, asked me, "Did those guys know you?" He laughed.

"You didn't give them any clue as to who I am, did you," I asked, eating a Tic-Tac to get their dick taste out of my mouth.

"I admit I sought out your friends to see if they were interested in fucking a random hooker. The idea of you fucking more of your friends was too funny to me. But no, they don't know they fucked the actual Cindy."

"You are such a fucking asshole."

"Nice tits, by the way. Anyway, apparently they have done this before. When I asked what they wanted, they described wanting a girl that fits your description. I didn't know they wanted to picture you while doing it."

I got dressed and was about to leave, happy to never need to be back here again. But Shawn stopped me. Oh god, what fucking loophole was he going to pull to convince me I didn't meet his requirements, and now I need to take the virginity of another bus full of losers.

"Nice work, that completes what you agreed to. I'll be claiming Ashley's orgy child as my own." I was very relieved to hear that. But that couldn't be why he had me stay behind. "I have an additional proposal. One that is completely optional with no negative consequences should you say no. In looking for the six clients, I ended up finding seven. The seventh one is still very interested in a session with you, so I figured I would throw out the offer to you."

"I am done fucking guys for you. I am not your whore anymore." I felt like I should leave then, but I didn't.

"You're not. But the difference with this one is you would be getting most of the money. If you agree to sleep with this man, he will pay you 2,000 dollars. You don't need to answer me right now. Take until the end of the day tomorrow."

I didn't immediately shoot this down. Was I actually considering this? I had fucked so many guys already, and 2000 dollars is a lot of spending cash.

"There's one last condition he has, though. No mask and you will be required to talk."

"What? No way. I'm not revealing my identity, that would ruin me!"

Again, I was ready to walk, but I felt there was no harm in listening. "I know, I know. But the guy is from out of town. You have never seen or met him before. You don't need to tell him any information about yourself. If you agree, you can wear the mask initially, see him for yourself, and ask whatever questions you want. You can then agree to remove your mask, get paid, or walk."

"I'll think about it." I walked out of the room and left, very embarrassed at what I had just said. I had just admitted to Shawn I was considering being a whore, as myself. Nobody is blackmailing me, no deals for friends, nothing. This was me considering letting a guy fuck me in exchange for money.

The next day, I was very distant. I wish the idea would be utterly repulsive to me, thus making this an easy thing to say no to. But it wasn't. I've let so many men and a couple of women have their way with my body. I've swallowed so much cum, taken so many virginities, and probably had a literal gallon of cum sprayed into my womb. Adding one more to that pile was nothing, and I would finally have something to show for it.