Cindy's Bikini - College Age Hooker

Note to reader: All characters are 18 years or older, even if not specifically stated in the text

My best friend was pregnant. She became pregnant from having a large amount of unprotected sex after she became entangled in a blackmail scheme that already had me fucking a handful of teenage boys. The father of her unborn child could be nearly one of a dozen men. Some of the possible fathers are 18 years old, others are in their fifties. Some are high school dropouts, some are married and already fathers. One of them is by brother. When news of her pregnancy comes out, she will be pressed to identify who she had unprotected sex with. Guessing the wrong guy will then lead to more names getting released until it becomes obvious to everyone just how many people she let cream pie her pussy over a couple weeks time.

Worse, it will become clear to everyone that I also participated in these orgies. I'm not pregnant, but my parents, friends, and the whole community finding all about the large amount of sex I let myself get roped into will ruin me.

Ashley has come up with a solution to this problem and I have agreed to help. Shawn, one of the boys who fucked and inseminated us countless times, will agree to proclaim himself the father of her child. With the fatherhood being uncontested, no paternity test will be needed and it will seem Ashley only partook in unprotected sex with one partner. A partner still in high school, but at least just one.

We met with Shawn and he presented his demands he wants fulfilled before declaring himself the father. I argued with his demands and got what concessions I could, however he was holding all of the cards. Ashley was silent for the meeting. The details mattered little when you were a few months away from confessing to the world that you were pregnant with a high-schoolers kid. We shook on the agreement and left. A little over a week ago I thought I was done fucking anyone especially these high school losers, but now I knew I had a lot more sex with teenagers in my near future.

The following weekend we fulfilled the first of Shawn's requirements. Don gave it the name 'Summer Fuck Fest', which I refused ever say out loud, but the name wasn't an inaccurate description of what was going to occur. With Bobby's and my parents out again for the weekend, we hosted a pool party. Every participant in the original incident that started all of this was present. Shawn, Don, Richie and my brother Bobby. As well as Grant and Teddy. With the exception of my brother of course, all of these guys have seen me naked, have had sex with me multiple, if not dozens of times, and came inside my pussy. Ashley can say the same, thus why she likely got pregnant.

The purpose of this pool party isn't clever. It's purely for Ashley and I to get fucked again by these boys, over and over with all of them watching. We were to follow any instructions we were given. Shawn also announced this would be the last time anybody besides him could use Ashley. After the pregnancy is announced, they will start a relationship. She was essentially agreeing to let Shawn fuck her the rest of her life. However he soon back tracked and stated that on occasion he might let other men fuck her. Stand up guy.

After the guys had all arrived, Ashley and I stepped outside in our bikinis. Ridiculous, tiny bikinis that barely covered any of our skin. Richie had taken the liberty of buying us these slutty swim suits for this event. I felt it was a waste of money anyway because they were going to have us get naked and stay naked for the entire day I was sure. The one stipulation I made about this whole event was no pictures or filming would be allowed. The boys had put their phones well out of reach.

With us now in our tiny bikini's and in front of six horny teenagers, things started getting out of hand. We had multiple requests being thrown at us, some of which were entirely at odds or physically impossible to do simultaneously. While I was happy to let them argue for the entire day while we stared at them, Ashley for some reason took charge and created a system for each person to take turns giving us our embarrassing orders. The day started off with Ashley and I being told to make out 'with tongues.' We had done this before. In fact they couldn't think of a single sexual act we haven't done before. But that gave me little comfort. Again I felt my best friends tongue in my mouth. I still wasn't a lesbian but I rather do this with her for hours in place of any of these morons.

Her hands explored my hips and back while we made out. Just as we had before, I felt that we should be putting in the minimum effort during these lesbian activities but Ashley seemed to never get that message. The boys finally told us we could quit and you could already see their obvious boners in their swim trunks. While I may have wondered how big their dicks were on that first day when I was alone with them out here naked and masturbating, I no longer had to wonder. I had spent hours seeing and feeling their erect penises. Feeling with my hands, mouth, tits, pussy and in one case my ass.

They next had us strip each other of our bikinis. Bikinis which, as I suspected, we never put back on for the rest of the day. Now fully nude in front of these boys for what could have been the twentieth time, we awaited our next order. Still holding off on fucking us themselves, they requested Ashley and I fuck each other in a 69 position. In previous individual encounters with some of these guys, we had lesbian sex with each other in numerous fashions. However, not all of the boys had requested and seen us do this. God forbid they not all see me lick the pussy of my best friend.

For 69ing, I was on the bottom again. When Ashley's bare pussy positioned itself a few inches above my face I felt her warm tongue start rhythmically licking my pussy lips. After the initial shock of the feeling of my best friend going down on me again, I started up licking her in a similar fashion. I began tasting the salty sweet taste of Ashley's pussy that I was ashamed to admit was familiar to me now.

"These girls are total lesbians," Teddy yelled out despite having sex with us himself as a man multiple times.

"Are they going to make each other cum?"

Shawn knew the answer to this. "When they did this for me, they made each other cum multiple times."

I knew Shawn was right. Despite me and Ashley not being lesbians, we were able to get each other cum with more and more ease. Today would be no different. Despite the boys being very anxious to get their dicks wet in our pussies, they weren't going to be satisfied until we both came. I leaned into Ashley's pussy and started licking more rapidly. In response, Ashley did the same. It was difficult to judge from my perspective how well I was doing, but Ashley was making very good progress getting myself to an orgasm. Frequently I would find myself stop licking for a few moments while I let out a particularly loud moan. I'd open my eyes and see my best friends wet pussy in front of me and be reminded what I was suppose to be doing.

I felt I was maybe less than a minute from cumming due to her tongue going to town on my clit while being watched by six dudes. All of a sudden it was Ashley that stopped licking me and let out a large moan of "Oh Cindy... don't stop." Having her call out my name like that seemed unnecessary, but I took that to mean keep licking whatever spot I was on and a few seconds later she came. Once she was done riding her wave of pleasure she picked up where she left off. I continued lightly caressing her labia with the tip of my tongue but quickly stopped as I went through my own orgasm. Half a dozen teenagers had now witnessed my best friend making me cum.

"Okay, we both came. Are we fucking you guys now?"

The words I spoke surprised me and I debated them in the my head. Was it better to continue having lesbian sex with my best friend or proceed with the teenage orgy. Knowing these guys were going to fill us to the brim with everything ounce of cum they have regardless of how many times Ashley and I fucked each other in front of them, I think I made the right call.

Ashley rolled off of me and before we even could get up we both had an 18 year old on top of us with their dicks finding their way into our pussies. Teddy, to my dismay, was my first partner of the day while Shawn was taking his first turn on 'his girl.' Teddy was very anxious with me. Pumping me like he was a horny 18 year old loser who just witnessed two hot girls have lesbian sex with each other. He lasted about 30 seconds before giving me my first creampie of the day. Next to me, my former lesbian lover's new partner lasted longer. He didn't end up cumming until my second partner, Grant, came inside me at the same time. The only plus side was at this orgy, Ashley wasn't at risk of getting pregnant again.

What was odd is that Shawn insisted Teddy already get another go at my pussy, even though the other boys complained that they hadn't had any girl yet. Teddy insisted it was because he was the best at making the girls cum which got laughs. Shawn instructed Ashley to start blowing guys as well as taking loads in her pussy. Teddy didn't wait for the other guys to stop complaining and started fucking me again. With one orgasm already under his belt and inside my womb, he was much calmer in his humping. It was still irritating as hell having to have sex with this loser at all, but at least he calmed the fuck down. He started trying to kiss me which I turned my head to avoid. A few more attempts to kiss me and he got aggravated and told on me.

"Shawn, Cindy isn't letting me make out with her."

He couldn't have sounded more pathetic. But as whiny as he sounded, he was plowing my pussy at the same time.

"Ashley... are we having second thoughts about our deal? Are we going to leave poor Ashley's future child without a daddy?"

The words were rather hollow coming from the man who was letting the mother of his child get gang banged outside by the pool. I relented with one final complaint.

"No. But Teddy fucking smells."

I turned and faced Teddy and let him stick his tongue in my mouth. I thought that this was likely his first kiss. I just gave a boy his first kiss after having fucked him multiple times over the past several weeks before that. The kissing must have been very exciting for him and he gave me my 2nd load of his cum for the day.

From there Ashley and I spent the next several hours with at least one dick in us constantly. They revisited a few of their favorite poses from before, including positioning me and Ashley face to face to make out while two other boys fucked us from behind. They then got the great idea to use this same position but have us take on a 3rd dick together via a dual blow job. Somehow that ended up with me getting the majority of the cum from that 3rd dick sprayed on my face. I soon got the familiar feeling of cum squirting out of my pussy every time I shift my body. Seeing this sight again, it was no wonder Ashley got pregnant. Thank god for my own birth control.

What pissed me off the most, despite this being my third orgy with high-schoolers, was that Shawn had me focus on fucking Teddy a lot. More than one third of my 'partners' seemed to be him and he always was told to fuck and cum in my pussy. Shawn must have known how much I hated the fucker. Or he knew Ashley hated him as well as was playing favorites, causing me to take the guy's loads. Knowing how Teddy would probably always be a loser, I could end up being the women he has had sex with the most in his whole life, by far.

Finally, the sun was approaching the horizon and the guys were losing steam. We would go five to ten minutes without a erect dick ready to penetrate us. Soon each boy started declaring themselves spent and finally after one last thrust and burst, I had fucked my last guy of the day. The boys left for their homes and Ashley and I laid outside naked and panting, once again completely soaked in the cum of these guys.

With the 'Summer Fuck Fest' concluded, I only had one more part I needed to do in order for Shawn to be declare himself the father to Ashley's child. This would only involve me which really irked me. While I know this would help hide what I've done with these high-schoolers from the community, it was really Ashley's mistake we were fixing. She is the one who was off birth control, even after that first day of unprotected sex. Yet I was the one that was working towards the solution. A solution which of course would involve me fucking more strangers.

To sum it up very bluntly, I was going to prostitute myself out in order to raise money for Shawn. I would fuck six clients. Shawn himself would find the clients and handle the money. All I had to do is fuck them. No condoms of course as Shawn wanted to maximize what he could charge. Now obviously I, as an outstanding college student, would never be caught seeking out people to fuck for money. Instead, I would be a nameless girl whose face and hair would be concealed by a mask. I would procure the mask myself and wear it while working as a hooker.

When Shawn presented this idea to me, I was surprised how I didn't hate it. I greatly disliked the physical act of engaging in sex with all of these guys to date. However, I think what bugged me most was they knew it was me, Cindy. Everything they knew about me made having sex with me more exciting for them. And now every time they would see me, they would immediately think of me laying naked with my pussy filled with their cum. Having sex anonymously was really going to take the bite out of the humiliation I had been feeling. Sure I was still going to be selling my access to my pussy and continuing to increase my body count. All for the benefit of this scum bag loser Shawn. But it wouldn't be known that Cindy was doing this.

I found a mask online that fit my purpose well. The mask covered my entire head except my mouth and holes for my eyes. I could conceal my entire hair in it if I tied it up. It was dark purple and had two bunny ears attached to the top. This might sound like an odd choice but I felt it made me look a lot less like some bdsm sex object compared to the mask without ears. When I put the mask on in the bathroom at home, I looked like I could be anyone. The mask also had multiple straps securing it. A simple tug by some curious sex partner wasn't going to pull this off. This was going to work.

Shawn secured a room at a sleazy hotel at the edge of town. I arrived first in the room and got myself ready to be fucked by yet another stranger. Shawn promised the people he brought in would be verified 18 years or older and not relatives of me. Shawn would stay in the room for the act. He would do all of the talking allowing me to stay silent.

I wore only a black bra and thong. No point in wearing anything else I owned as it would only increase the chance I could be recognized later on. I waited patiently for Shawn to bring in the client, the first guy I would be fucking for money. How Shawn, a high schooler, was finding men to pay for sex with me was a mystery.

The first client he brought looked to be in his forties. This was not surprising, I figured almost all of the men I would be fucking for money would be middle age.

"Nice! You weren't lying. She is very hot. I haven't been with anyone but my wife for the past 20 years of my life. I just want to blow some steam off without the chick thinking I'm going to leave them for my wife. You know I'm just here to fuck you and leave right?"

I nodded my head. Fantastic, I get to help this creep cheat on his wife. The man started getting undressed.

"And no condoms right? My wife makes me wear condoms cause she doesn't want to have any more kids. Are you on birth control?"

Shawn answered for me as was the plan.

"Nope. She is as fertile as they come. You might very well impregnate her and make your kids a half-sibling. But don't worry, she has had so much unprotected sex with so many different guys lately, she'll have no idea who the father is."

This was a lie as I was firmly on birth control. Having sex with a bunch of dudes was another story though.

With everything settled the now fully naked middle age father aggressively started fondling my ass and breast. Not even five seconds later he took off my bra and thong in order to fondle me naked.

"Man I missed tits like these. Your ass is something else too."

He was becoming fully erect and I wish he would move on to the sex already. I was now at a point in my life where I was waiting on a middle age man to state he is ready to fuck me, dear god.

"You say she has fucked a lot of guys lately? Is her pussy tight?"

Shawn smiled. "I can tell you from personal experience, her pussy is the tightest."

Hearing one guy recommend sex with me to another was not something I needed to hear at my age or ever.

He finally had me lay on the bed. He didn't request any blow jobs, tits jobs, or anything else. After groping my body he was ready to fuck. I spread my legs, he gave my open pussy another good look, then plunged his dick in me.

"Oh fuck, you are right. She is tight."

This was now at least the second man I've helped cheat on their wife. I can't even say for sure it's only the second as I have no idea if the stereo installer or pizza guy was married. Hell, I didn't even know their names but still let them fuck me.

The married man took his time, despite how quickly we got to fucking. He slowly moved his dick in and out of me. Had he given more foreplay and was actually someone I wanted to have sex with he might be able to get me to orgasm. But with me playing hooker tonight, it was all about his pleasure. He didn't kiss me which I appreciated. I started lightly running my hands on his body. I figured it was an easy gesture that might get him to cum sooner. A few minutes later, he looked at me and asked.

"Are you sure you want me cumming inside you?"

As pathetic as it sounds, I was a bit touched that he asked. Every other guy who had fucked me over the last month creampied me without even a word asking what I wanted. I smiled and shook my head yes. It wasn't that I really wanted to feel this man twice my age ejaculate into me, but it was what I had agreed to with Shawn.

My consent to receive his seed, and as far as he knows maybe be impregnated, put him over the edge and he came inside me. He then exited, got dressed, and left without a word. I had officially become a prostitute. But I was doing it for my friend and for my own benefit. I left the hotel not too long after and headed back home. Laying in bed that night, it was weird how much more icky it felt knowing I had let this man have his way with me for money. Even if I wasn't seeing a cent of that money. All of the other sex I have had felt like blackmail and I didn't have a choice. This felt like I was actively allowing strange men to fuck me.

Two nights later I was back at the same hotel room, wearing the same thing, expecting for another middle age man to enter the room and cum inside me. The man who entered with Shawn was familiar to me, but I couldn't remember how exactly.

"What the fuck is with the bunny mask? What kind of hooker wears that?"

"The kind who is trying to hide the fact that she is an outstanding member of society that isn't fucking dudes for a bit of money. You might know this girl. She could be serving you coffee tomorrow, passing you by on the street, or the daughter of a co-worker," Shawn said.

Mother fucker. Hearing that made me realize who this was. This was my dad's boss. Dad was constantly complaining about him. How he is overworking him, is disrespectful, and a womanizer. He is constantly hitting on women in the office and trying to have affairs. At a previous holiday party he even tried to proposition mom. And here he was, about to have sex with his coworker's daughter.