Cindy's Bikini - Fucker of Brothers

My plan to prostitute myself was going terribly. I needed money to take care of my unexpected pregnancy before it progressed far enough along for people to notice. Trying to sell my body on the street resulted in me almost getting arrested and becoming a sex toy for my parent's friends. Taking a much more low-key approach and convincing a guy at my college to pay for sex didn't go any better. He didn't understand that I was going out with him for the purpose of money and ended up blackmailing me into having sex with him. All I had accomplished thus far was getting laid multiple times for free.

I couldn't give up. That would push me into the life my slut of an ex-best friend Ashley had gotten herself into. I wasn't going to be baby trapped into fucking some losers for the rest of my life. Trying a different approach, I began scanning local forums and postings online. There was no shortage of guys looking for hookups, but no one brazen enough to say they would pay money for it. Finally, though, I found a post that caught my interest. A male-female couple was looking for a female to join them for a threesome. They claimed to be students at the college and were even brazen enough to post a picture of themselves. I didn't recognize them but posting an image made me think this was legit.

Of most interest to me was they claimed to be willing to 'provide a valuable gift, ahead of the act being performed to anyone interested.' That, to me, meant they would pay for sex and not even wait till after the deed. I stewed over it for a few hours before finally sending them a private message, informing them I was also a student and interested. But I sought clarity on whether they were offering money to participate in this threesome. Ten minutes later, they responded, stating they were offering money. Two hundred dollars to join in the threesome, provided anything goes. After some back and forth, I ended up providing them a picture of me as proof I wasn't a scammer, and they agreed to pay half now and half at the hookup.

Not wasting any time, we both agreed to initiate the threesome tonight. The deed would occur at their apartment, not far from the college. At the agreed-upon time, I knocked on the door, and instantly, it opened as the couple seemed to be anxiously awaiting my arrival. The girl wore a red corset, matching red panties, and a choker around her neck. The guy was wearing a G-string and nothing else. We hadn't discussed a dress code, so I simply came wearing a skirt and shirt. I wore no mask. I was coming as myself. Risky, but I couldn't get myself associated with the bunny mask anymore. Even wearing a different mask connected me to it.

"Wow, you guys are ready to go, aren't you?" I asked, nervous I wasn't going to meet their expectations.

"We enjoy wearing what feels good when we are home. Please come in. Cindy, right?" The girl said, inviting me in. "I'm Gillian, and this is my boyfriend, Lewis. Here, I believe we owe you this," she said, handing me the last hundred dollars I was owed. Regardless of how tonight goes, I have money to show for it. I had graduated from slut to whore.

"We are going to do this in the bedroom. You can go ahead and strip. Might as well start you off nude," Lewis explained. Following them, I did as they recommended and took off my skirt and shirt prior to entering the bedroom. Inside, they had a large, king-size bed. Next to that, though, and facing right at me was a video camera blinking red.

"You didn't say you were going to film this," I exclaimed, stepping back out of the room. However, I knew it had already got footage of me in my underwear.

"Cindy, we agreed anything goes. We film ourselves fucking all of the time. This threesome will be no exception. We plan to fuck each other while watching it in the future. Is that going to be a problem," Gillian asked. I already had their money, and they had seen and filmed my face. Backing out and leaving them disappointed would only add risk.

"No, sorry. I just wasn't expecting to see the camera," I said, walking back into the bedroom. "You'll keep this video to yourself, though?" I asked as I became more aware of how lustfully the two were starting to look at my underwear-clad body.

"If that's what you want," Gillian said as Lewis descended on me. Lewis embraced me and then directed his hands onto my ass. I took this to mean we were starting. I had participated in group sex in the past but never with another couple. I wasn't sure what the best protocols were. But for now, Lewis was handling me. Continuing to grope my butt, he stared at my chest. "Take off your bra, Cindy," Gillian said from across the room. I didn't like how much they used my name, especially while being filmed. I reached behind my back and got the hook undone. Before I went further, I looked at the camera. I was about to let my tits be filmed. Not that I hadn't had that happen before. But I was either in control of those videos or wearing a mask. This was no longer the case. Except then I remembered Allan was now holding onto a video of me. Taking a deep breath, I pulled off the bra, revealing my naked tits.

"God damn, she has nice tits, Gillian. She is worth every penny," Lewis said, moving his hands onto them. I almost spoke up, asking them not to mention that I was being paid for this on camera, but that would only draw further attention. As Lewis started licking my nipples extensively, I wondered how his girlfriend was reacting to seeing him with another woman like this. But she was on the bed with her fingers under her panties, masturbating to the sight. I don't think jealousy was going to be an issue.

"Bring her to the bed and have her suck your gorgeous cock," Gillian commanded. He led me to the bed and had me get on my knees while he got his dick out. Once he was in position with a hard-on ready for me, I bent over and took it into my mouth.

"Oh fuck, babe, she is going to town on my dick. You can tell she's done this before." You have no idea, dude. I couldn't even estimate the amount of men that had unloaded in my mouth at this point. He probably wasn't even my hundredth.

"God, I could get off just staring at this glorious ass of hers." Gillian was positioned directly behind me with a clear view of my panties. I couldn't see her, but it was a safe bet that she was still masturbating. As I continued to run my lips along Lewis's cock, my pussy felt a breeze as Gillian removed my panties. "That's the view I wanted," she said, giving my ass a slap. I went into this threesome wondering about the sexuality of the girl and was now quite sure of it. I continued taking in the taste of Lewis's dick in my mouth as his girlfriend flicked the bean to the sight of my bare pussy.

Gillian began shifting on the bed, and I wondered if she was getting close to cumming or changing her view. After a bit, though, I felt a large object start to press into my pussy. I attempted to lift my head to yelp and check out what was going on, but Lewis's hands kept my head locked onto his dick. "Fuck that pussy hard, babe," he yelled out. Gillian had equipped a strap-on dildo and was now fucking me with it. The dildo was wide, long, textured, but thankfully well lubricated. In the position I was in, all I could do was take the pounding while I continued to get face fucked by Lewis's cock.

My grunts and moans were muffled by the penis in my mouth. My pussy was being satisfyingly stretched by the dildo while the texturing on it served to manipulate sensitive areas inside me. Gillian did not ease up and pounded me hard. It got to the point where I couldn't focus on blow Lewis at all and just sat there moaning while his dick rested static in my mouth. Finally, he withdrew from my mouth. "Holy shit Gillian, take it fucking easy on me," I pleaded.

But she paid me no heed. Instead, she only seemed to thrust her artificial dick into me deeper. Lewis, despite me no longer blowing him, kept his dick in front of my face. I looked up at his to see if he intended for me to start sucking him again, but I was met with his cum spraying all over my face. "Fuck! Why did you take it out of my mouth if you were about to cum," I complained.

"Cause you look fantastic with cum on your face. Don't wipe it off. Keep it there," Lewis commanded. Another deep thrust of the dildo made me squeal out loud.

"Maybe... maybe we give the dildo a break," I said pathetically with a face covered in cum.

"She's close, Gillian. Keep it up," Lewis responded with a smile. He was right about that. Gillian grabbed my hips and used that leverage to drive even harder into me. I closed my eyes and let my moans echo in the room. Each thrust from then on started building up a fire in me that grew larger and larger. Finally, when it got to the point where I couldn't even breathe from the intensity of it, the fire exploded, and I came on the fake cock. A few more shoves of the dildo in me for good measure, but then thankfully, Gillian withdrew out of my pussy, and I collapsed on the bed.

I stared blankly at the camera while my customers convened. These two strangers now had me on camera cumming from a dildo fucking, all while my face was covered in cum. Best of all, it was stated on camera that I was paid for this. If they felt like it, they could expose me as a prostitute and sexual deviant. Obviously, they would be shown involved in this as well, but considering they were publicly advertising they were looking for a woman to fuck for money, I doubt they would care.

"Did you enjoy yourself, Cindy? I know we did," Gillian said, coming up behind me and putting her hands on my tits.

"I did, but what is most important is that you did," I said, remembering I was here because they paid me. I needed to keep them happy.

"We want to do what we just did again, but in reverse, if you understand," she explained. I understood. Gillian took the same position as Lewis had before. Her strap-on was gone, and I was now left with the sight of her open pussy in front of me. The woman who had just been pounding me now wanted sexual pleasure of her own. I crawled over to her and went down on yet another woman. As a straight woman, I was abnormally experienced in giving oral pleasure to women.

Her pussy was already moist, as was her whole body. The dildo-fucking she gave me was a workout for her, and she was sweaty from it. But it was apparent her vagina was wet for other reasons. Fucking me with the strap-on really must have excited her. Or maybe she liked seeing her boyfriend get pleasured by me. Whatever the case, this woman was ready for a tongue fucking.

My tongue started off teasing her clit, which she instantly reacted to by squirming and grabbing her tits. I ran my tongue up and down the lips of her pussy, spending a little more time by her clit. I was continuing this pattern until I felt Lewis's hand on my ass. Knowing what he was preparing for, I stuck out my ass, giving him easy access to my pussy. He took advantage and slid his cock inside me. Compared to the inhuman size of the dildo I was just fucked with, his cock was a welcome relief. My pussy was left sore but sensitive. Lewis knew what he was doing and found just the right angle of his cock to rub its tip along a pleasurable area inside me that so many of my lovers seem to fine. I didn't want to seem like I was already working towards another orgasm, but that seemed to be the case.

I focused on getting Gillian off. Seeing his girlfriend cum from another woman going down on her may put Lewis over the edge and have him cum early. I wasn't keen on cumming on camera again. Although of all the things I am being filmed doing, that was admittedly a tiny boundary to set. I focused my tongue exclusively on Gillian's clit while introducing three of my fingers inside her pussy. Gillian was writhing on the bed at this point and using her hands to pinch her nipples. However, Lewis's stupid dick was feeling really good sliding inside me. I could no longer hold back the moans being caused by the pleasure I was getting from getting fucked.

I increased the pace of my fingers penetrating Gillian. 'Fucking cum already, you bitch.' I thought as I became more desperate to finish her off before her boyfriend finished me off. Finally, Gillian's hands slapped down on the sides of the bed, and she yelled out as she orgasmed due to the tongue fucking I was giving her. But despite witnessing his girlfriend cum from having lesbian sex, Lewis prevailed.

"Fucking fill me up with your cum already!" I yelled back at him in frustration. I immediately regretted that as I was now filmed practically begging a stranger to cream-pie me. Even worst, it didn't work, and the sounds of his hips slapping against my ass continued to fill the room. The fire was building up in my pussy like before and was practically blazing. I gave up the last bit of hope I had I could avoid cumming on camera a second time and accepted it. Finally letting go of my tension, the orgasm hit me and pulsed pleasure across my body, even into my fingertips.

As the orgasm finally faded, I realized Lewis was no longer in me and had finished at some point, inside me. With my ass still sticking up in the air, I could hear the couple admiring the cum filled pussy before them. "Man, you make a lot of cum. Especially for your second load in such a short time. You got this slut pregnant for sure," Gillian said, having recovered from her own orgasm I gave her. They could speculate all they want about what that sperm in me can and can't do right now. I was smart enough not to admit on camera that I was already pregnant.

Sitting up, I worried we weren't done yet. "Cindy, you are free to go. We want some one-on-one time together. We're both real anxious to see the video," Lewis explained. That was a relief. The sex had been intense but short, which I could live with. Most importantly I finally had money in hand to go towards my internal issue.

"But this was fun, Cindy. You should come back at the same time next week," Gillian suggested. That was actually good news. I could use these guys as repeat customers to raise more money. That would be one less customer I would need to seek out on my own.

"Sure thing. You can give me the two hundred dollars then," I explained. I think we had built enough trust that I didn't need money ahead of time.

The couple looked at each other and then back to me. "Cindy... I thought we made a connection tonight. Lovers don't charge each other for sex," Lewis said in a tone I didn't like.

Stammering a bit, I responded. "Look, you guys are cool, and it was fun. But I'm not your lover. I'm happy to return, but for money." I stood up and started to find my clothes, feeling like I should leave. However, both Lewis and Gillian walked over to me. They got very close to me before I could put anything on.

"You're a smart girl, Cindy. You agreed to us filming you. I'll point out we have not stopped recording you either. You are admitting to being a whore on camera. We can keep the film to ourselves, but only if you are our lover. And what do lovers do," Gillian asked as her hand ran all over my naked body. The fuckers had me. I continued to be taken advantage of.

"They don't charge each other for sex. I'll see you next week," I said, defeated. Gillian kissed me on the lips while Lewis gave my ass a spank. I got dressed and left. My schedule was quickly filling up with people who expected me to fuck them in exchange for keeping the blackmail they had on me to themselves.

The next day of classes I was feeling down again about my situation. I had a small amount of money and was hesitant to seek out additional sex work, even though I knew I had to. Towards the end of the day, I was approached by a freshman student at the college named Frankie. Frankie was part of the debate club, and he thought I could help out with something. "Frankie, I have no interest in joining debate, sorry," I explained, walking away.

"You misunderstand. We fully recognize you are not debate team material, no offense. But there's another way you can help and make some quick money in the meantime," he said, catching my interest.

"Who said I'm looking to make money," I asked nervously. Had word gotten out about my prostitution?

"Lewis recommended you. He also told me to tell you that your secret is safe. He only told me, and I won't tell anyone else. Trust me, I don't want to get on Lewis's bad side," he said, showing a bit of fear in his eyes.

"And what did that asshole tell you about me?"

"You will perform sexual acts for money," Frankie said, laying it all on the table. That fucking asshole Lewis. But maybe this is just what I needed. There was no harm in finding out about the job. The kid already knew my secret.

"So what, you want me to fuck you?"

"No! I mean, yes, but no, that's not what this is about. Sorry. Anyway, the debate team is having an upcoming match against City College. It pains me to admit, but they are going to whip our butts. We've had a rough year, and I'm worried a loss like this could end our team."

"I don't care, Frankie. Just tell me who I'm fucking already," I said, realizing I should maybe keep an eye on who was walking by during this conversation.

"The City College team. They'll be staying in a hotel nearby. I want you to show up to their room and fuck them so they miss the debate that morning, making us the winner by default."

"How many people are we talking about here? I have only so many holes, you know..."

"The team is composed of seven people. All 18-years-old. City College has five guys and two girls on the team. They need three people to show up to avoid the forfeit. So you will need to keep all five guys busy," he explained. Keeping the girls busy as well isn't out of the question, I thought to myself.

"I'll pay you two hundred dollars upfront. If you force the forfeit, I'll pay you another three hundred. The debate is at 9 am, so if they are still fucking you by that time, we win. Deal?" Five hundred would go pretty far. I also liked that I would be fucking strangers from out of town. Frankie would have no proof of what occurred to blackmail me afterward.

"Deal," I said, committing myself to yet another orgy.

Saturday morning, I arrived at the hotel where the City College team was staying. Frankie informed me the team of seven was in suite #7. At 8:30, I knocked on the door. I had thirty minutes to distract at least five of them for a half hour. I wore a small black dress with a black bra and panties underneath. Although I didn't plan on keeping them on long. A young man answered the door. "Are you guys the City College debate team," I asked him. He nodded yes, and I lightly pushed myself into the room. It was a lovely suite with a central living area connected to multiple bedrooms. It looked like all seven were hanging out and ready to leave for the debate.

"Can we help you with something miss," one of the boys sitting asked.

I pulled the straps of my dress off my shoulders and let it drop to the floor. "You can help me get royally fucked by you guys," I announced. The sight of me standing only in my underwear seemed to really have an impact on a number of the boys. I was probably the first woman they had seen in person wearing so little clothes.

One of the female debaters was less impacted and spoke up. "We have an important debate in 30 minutes. We don't have time for you, nor are any of us interested in a tramp like you," she said, eyeing me judgmentally.

"Speak for yourself. Who wants to take off my bra," I asked the group staring at my body. Nobody stood up to volunteer, but it looked like many of them wanted to.

"No need to be shy, guys, but I can help you out and do it myself." I unhooked the bra and pulled it off as six pairs of eyes watched my naked tits get revealed. I walked a lap around the room, letting them see me from a variety of angles while also enjoying the sight of my boobs slightly jiggling.