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.
