Way Too Competitive
by Purple Knight
Copyright© 2025 by Purple Knight
Erotica Sex Story: A woman desperate to win back her lost money from a poker game, agrees to be a prostitute for an hour and a half to a man and his roommate...
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Mult Reluctant Humiliation Sadistic Orgy Anal Sex Exhibitionism Masturbation Oral Sex Size .
Dad always said I was too competitive for my own good.
Tonight, I was proving him right. I looked at the cards in my hand, actually a respectable hand-a full house of three jacks and two 9s, and then I glanced at the pot. Just about all the money my parents had sent me for the month was on the table, which was not helping my confidence level at all.
One of my opponents, Ricky, had already folded, leaving only his roommate Billy and myself in the game. Billy had that smug expression on his face that he had been wearing for most of the evening, that expression that conveyed the message that he knew he had this game won. That look was doing even less for my confidence.
As I looked back down at my cards, I couldn’t help but marvel at how fast this evening had gotten this far.
Billy and I had been dating for about two weeks. By dating, I meant we had met for coffee at the school café each morning and had had dinner out a couple of times. We had slept together twice, but nothing out of the ordinary. When he called and asked if I would like to play cards with him and his roommate it seemed harmless enough. As I lived in an apartment off campus and they lived in the dorm we decided to meet at my place, which seemed logical; though we had never dated, I had known Ricky for over a year and felt he was safe enough.
I also didn’t see the harm in playing poker for actual money. My father was in the Navy and had taught me how to play at a very early age. I actually considered myself pretty good. I also felt that I was a bit adept at exposing just enough skin to maintain an innocent demeanor, but still be a distraction to male opponents. As the evening started, it was actually going real well for me. In the first hour, I had made a little over a hundred dollars. However, from there it had all gone down hill.
For the last two hours, I had been consistently loosing to Billy every hand. A perfectly sane person would have quit before now, but competition always got the best of me. I was starting to think Billy had realized this and was playing on this weakness.
However it worked out, this was the last hand though. I had already lost about half of my monthly allowance provided by my parents for rent, food, utilities, you name it. I had to bet the other half in an attempt to win back what I had lost. What made it even worse was that I was already a month behind on rent thanks to some rather expensive nights of partying last month. The eviction policy was crystal clear when it came to 2 late payments. That was a call I would never be able to make to my parents.
I looked over at Billy, trying to gauge his expression to see if he was bluffing. All I read was that same smug arrogance that he had been displaying all night. I glanced over at Ricky, who had already folded, but he was staring steadily at my cleavage that I had displayed boldly in an attempt to distract Billy. He caught me looking at him and looked away smirking.
“Well, what’s it going to be, Carrie? Do you fold?” asked Billy.
“No. Do you?” I replied, with just a bit of desperation in my voice despite my best effort.
“No” he replied, “I was actually thinking about upping the pot some.”
Despite myself, I let some of my panic show as he said this. Every dime I had was on the table, if he upped his bet and I could not match, it would be the same as folding. Billy saw my panic and laughed.
“Okay,” he said, “then I call.”
I laid my hand on the table. Ricky gave an appreciative whistle at my full house.
Billy only smiled wider as he laid down four Kings.
“Well, it’s been fun,” said Billy has he started to pick up the money, “maybe we can do this next week.”
“Wait,” I pleaded. “That is all the money I have for the month, let me just pay you in payments, I should be able to pay in two to three months, tops”.
“That’s not the way you play poker and you know it,” was his reply.
“Please,” I continued anyway, “you have to at least leave enough for the rent; I told you I was already behind. If I don’t make this payment they will evict me.”
“Just call your dad and tell him to send you more,” volunteered Ricky.
“He won’t do it,” was my honest answer. “My allowance is part of his “trust” of me. He told me he would send it once a month and it was up to me to manage it, and that he would not send me a penny more, I know because I have already tried.”
“Well, it sounds like you have a problem,” was Billy’s reply. “I really wish I could help you.”
“Please,” I begged, “can’t we just work out some payment plan or something? I’ll do anything.”
As soon as I said these words a strange look passed over Billy’s face. It almost appeared as if I had finally said something he had been waiting on. What he said next further confirmed my suspicions.
“Maybe I have an idea that can help you out. Ricky and I had already decided that if we won enough money tonight, we were going to get us a slut tonight. It seems to me that we have more than enough money now. What if I were to say that I would be willing to give you back all the money I won from you tonight, Ricky too, and all you have to do is be the slut for us.”
I was so shocked by that statement that I just stood there, dumbfounded. I felt more than a little betrayed by Billy, and I also felt desperation welling up as the money went closer and closer to the door. “Please, Billy,” was all I managed to get out.
Billy stood staring at me for a bit, but then sighed and grabbed his jacket. “C’mon Ricky, lets go find us a slut.”
“Wait,” I said, actually surprising myself. “1 hour. I understand that prostitutes get paid by the hour. I will agree to it for one hour.” I was surprising myself with every word, but I was also thinking of what would happen if the money left the door. Besides, I wasn’t a virgin or anything, though I had never done two guys at once. Hell, I had already slept with Billy a couple of times, and Ricky seemed nice enough.
Unfortunately, Billy wanted to drag the negotiations out a bit.
“I figure we could get us a cheap whore for about 2 hours with this money. One that would do anything we tell her to do.”
“How about an hour and a half?” I replied.
“I don’t know Billy,” chimed in Ricky, “you said that she was not really that great in bed. I was actually hoping for a wild night with a slut that would do whatever we wanted. I’m not sure I want to blow that much money on a boring fuck!”
That statement actually made me mad. I would grant that I didn’t have that much experience, but to be referred to as not really great in bed was unacceptable to my ego. Just the second time my need to compete was going to get the better of me tonight.
“I can make it worth it for you Ricky,” I said as coldly as possible.
“I don’t know, Carrie, Ricky has a point,” said Billy, but when he saw the anger growing on my face he quickly added, “But I have an idea that could resolve it.”
“And what would that be,” I said, all the while not sure I wanted to know.
“Maybe you could put on a little show for us in order to convince us that we should do you instead of some slut. If you can convince us that you would be just as much a slut as any cheap whore we could hire, we will agree to fuck you. If not, we will take our money and leave.”
I thought for a moment, I had already agreed to be a prostitute for an hour and a half, what did it really matter if I put on a little show first. Besides, it was obvious Billy wanted me to beg him to fuck me and this was going to be the only way to get my money back.
“Okay,” I said. “I will make you want to fuck me, but the moment one of you asks me to do anything to you, the clock is starting and you both agree to give me my money after it’s done.”
Casually discussing such a transaction was starting to feel a bit odd, but Billy was not done.
“We will agree to that, with the added condition that if we ask you to do something in that hour and a half and you refuse, then the deal is off and we keep all the money, regardless of how much time has passed.”
(Did I happen to mention that Billy and I were both pre-law, and at the top of our class?)
I did not like those terms at all, but saw little choice. I believed Billy was not bluffing when he said he would leave now with the money, you could see it in his face.
I would just have to hope they would not tell me to do anything too outrageous, although I realized that I would probably be doing stuff tonight that I had never thought I would do before. I was also realizing that this was probably Billy’s plan all along and knew he was going to try to keep the money after doing me by trying to suggest something that he thought I would not do.
“Okay,” I said softly, “whatever it takes.”
“Well, lets see what it takes,” said Billy. “Make us want to fuck you, slut.”
Calling me that shocked me a bit, but then I realized that I wanted them to fuck me and then pay me-if it walks like a duck and talks like a duck...
I was wearing a tight fitting button up blouse and a pair of jeans. I motioned for the guys to sit on the couch and started to unbutton my shirt. As I started taking my clothes off, I noticed Ricky was getting far more excited than Billy, who was sitting back with that damnable grin on his face. I realized I could probably get Ricky to “the point” first and decided to concentrate a bit more effort his way.
I had removed my panties and was standing completely naked in front of the guys. Ricky had a noticeable bulge in his pants, but Billy just kept on grinning.
At somewhat at a loss for what to do, but not wanting to give Billy an excuse to leave now that I had stripped for them, I tried to get some prompting in the most wanton matter I could:
“So, what do you want your prostitute to do,” I asked in a voice I hoped would pass for sultry.
Ricky was about to respond when Billy interrupted.
“First,” he said, “we don’t want a prostitute; we want a cheap dirty whore. If you are not going be a cheap dirty whore, we can just leave now.” He said this with emphasis, but I noted he was not making an effort to get off the couch. “Are you a cheap dirty whore?”
“Yes,” I replied.
“Say it,” he demanded.
“I am a cheap dirty whore,” I said, quickly adding “and I will do what ever you want.”
To my surprise, Ricky jumped in with, “You don’t look like a cheap whore to me; tell me why we should think you’re a cheap whore.”
I was a bit confused at how to respond to this, I mean here I was naked in front of two guys for crying out loud, how much more of a slut could I be?
Billy picked up the cue though, “Yes, tell us what you will do for us that makes you a cheap whore, slut.”
I thought as fast as I could. What do guys want?
“First, I will give you both blow jobs,” I offered, but to which Billy replied, “A cheap whore would say she would suck our cocks.”
“Yes, I will suck both of your cocks,” I quickly corrected. “I will suck both of your cocks until you come all over me.”
“Will you swallow the cum?” asked Billy.
Having no choice, and realizing just how far this was going to go, I replied, “Yes, I will swallow every last drop.” I was also starting to get into the role a little, so I added, “That’s what makes me a cheap whore-I love swallowing cum.”
“What else do you like to do that makes you a cheap whore,” asked Billy.
“I like to be fucked, hard, over and over again.”
One look at Ricky told me he was about to explode, but Billy was just casually sitting there. Part of me was hoping we could get this going and subsequently over with, but another part was starting to get turned on, as much by what I was doing as the challenge of getting a response from Billy.
“I want you to fuck me, here, in my pussy,” I started.
“You mean your cunt, don’t you slut?”
“Yes, right here in my cunt,” I quickly added. For effect, I turned around, spread my legs slightly and bent completely over at the hip. Running my right hand up my thigh onto my crotch and dipping the middle finger into my pussy I said, “I want you to fuck me hard.” I continued to insert my middle finger into my pussy, beginning to go in and out in fast, hard motions.
“Use two fingers, bitch,” came Billy’s reply, but this time I sensed some excitement.
I quickly complied, barely noticing he had called me a bitch. I guess the language was just part of it. I continued, inserting my right ring finger as well. I had my head down by my knee and could get a good look at both guys. Ricky was literally trembling. Billy was also sitting a bit tenser and less relaxed, though he still had that grin on his face.
“Man, I really want to fuck her Billy!”
“I don’t know. I still think we could get a cheap whore that would do more for us. What do you think, Carrie? Could we find a dirtier whore than you to fuck?”
“No,” I quickly replied, picking up all to easily on the verbal cues “I’m the dirtiest whore you could fuck. I will do anything you tell me to.” The whole time I was talking, I was continuing to fuck myself with my fingers.
“Use three fingers bitch. Fuck yourself like a slut would.”
“Yes,” was my only throaty reply. I was actually getting pretty excited and my knees were growing weak.
“Suck on the fingers of your other hand, show us how you suck a big dick”
I quickly formed three fingers into an appropriate shape, sucking them in as deep as I could. I moaned as loud as I could (I couldn’t do much else with three fingers in my mouth after all.)
Ricky had already dropped his pants and was masturbating on my sofa. Billy had unzipped his pants, but had not reached in yet.
They let me continue at this for a while. Ricky kept looking at Billy, obviously waiting for the signal to begin fucking me. I had to fall to my knees, as my legs were getting weak. I took my hand out of my mouth to support my weight. Hoping they would not hold it against me, I immediately started begging.
“Please fuck me guys. I am your cheap whore and all I want to do is suck your cocks and let you fuck me hard. Please, Please, fuck my cunt, cover me with cum.”
Billy’s reply was short and unexpected.
“Can we fuck your ass?”
I actually stopped for a moment. With my hesitation, Billy seemed to smile triumphantly.
“See, Ricky, she isn’t a cheap whore, she won’t even let us fuck her ass. Let’s go”
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