The Unfair Bet!

Hello everyone, this is my first story so please feel free to had any comments or improvements I am always looking to improve. Everyone in the story is over 18. And a big thanks to Kenji for editing the story!!

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Everyone who grew up in a smallish town, knew of that one place in town where all the college kids, who were home for the summer, worked. That place in this town was a hotel called, 'The Desire'. The Desire was a very nice hotel by any standard, but for a town of only fifty thousand, it was spectacular. The rooms were large and modern, the food was better than any other restaurant in town, so it was always busy, but what drew in the most people--was the service. Like I said earlier, this was a place where all the college kids would want to work for the summer, and for the most part, the summer staff consisted of 18 to 24-year-olds.

Of course, this meant that the staff would always end up in trouble for one thing or another--drinking too much, partying too loud, or maybe even sleeping around--or in Chris' case, trying to sleep around.

Chris was a 22-year-old bartender, who was in a relationship with his high school sweetheart, Claire. They had met in high school, and had been dating ever since. Claire played for the college hockey team, so she couldn't work at The Desire for the summer. Chris was a charismatic young man and very friendly. He quickly made good friends with three or four other co-workers, some of whom were girls. He told Claire about this, but always 'forgot' to mention just how good of friends they were; he always left out the harmless flirting. He also made sure Claire never found out about his urge to fuck his female best friend, Olivia. 

Claire was a beautiful woman--long, red curly hair that went just past her shoulders; freckles that covered her face; a medium build, a nice-sized pair of 34C tits, with thick legs and a firm ass. Even though she was perfect for him in every way, Chris was a horny young man, and something about Olivia drove him crazy. She was the stereotypical girl next door. She was cute, friendly, small-but-not-petite; with long, straight brown hair that went to the center of her back; with big blue eyes, and a smile that would take your breath away. She had a pair of perky B-cup tits, and a small firm ass that you could bounce a nickel off, but most importantly, she was a server that Chris worked and flirted with every day. 

It was a Monday night nearing the end of the shift, when Olivia came up to the bar. 

"Hey, Chris, shift is almost over; got a hot date with Claire, tonight?" Olivia asked, with her amazing smile on her face. 

"Not a thing is going on tonight. Claire is out of town, so unless you want to invite me over, I am out of luck," he said, as he finished pouring her drink order.

"You'd be so lucky," Olivia said with a wink, as she walked her drinks back to the table.  

As she walked away, Chris couldn't help but stare and her outstanding ass. 'What did she mean by that? Does she walk like that on purpose? Is she attracted to me? What would she say if I asked her to hook up?' These were all the questions going through his head, as he watched her drop off the last round to the group of guys sitting at the table.

Chris knew he was a lucky guy with Claire; she was beautiful, great in bed, smart but most importantly, she was kinky. Chris knew that there was no way that one, Olivia would hook up with him; two, not tell Claire--a small town and they knew each other not well, but still; and three, she would probably not be as good or as kinky in bed. Chris decided to leave well enough alone, and stop his delusion of hooking up with Olivia, his best work friend. 

That was... until it happened.

Olivia came back to the bar after getting the money from the last table. "You know for guys who have all had their cocks in my mouth, they sure tip like shit." Olivia said, annoyed but serious.  

"What did you just say?" Chris asked, after spitting out his drink.  

"Well, that table was a bunch of guys that I know from school, and I have given them all blowjobs at different points. So I said that I was disappointed in their tips," she said again, this time laughing a little at her pun.

Chris went wide-eyed; sure they had talked about sex before, but Olivia was never this forward. Most of the time, small details would come out about her sex life, but normally only at parties and after one too many drinks. Chris took a minute,   thinking to himself, 'No way she sucked all their cocks; the table had like six guys. She is way too innocent to have done that.'  

"I call bullshit! There is no way you sucked all those cocks," Chris said, stunned.

What she said next blew his mind...

Olivia looked him in the eyes, "Bullshit? Really? I have sucked a lot of cock. I may only be nineteen and look innocent, but when I see a guy with a big cock I have to have it!" she told Chris, with a grin on her face. She left to go do some more work, as Chris stood behind the bar completely stunned. 

The girl he had dreams about bending over the bar, and fucking her 'til he cums in her pussy, was actually a bit of a slut. 'I have a big cock, maybe there is a chance after all,' Chris thought to himself, as he finished up the order he was making for another server. A few more hours went by, and it was just Chris and Olivia left in the restaurant, as they were the closers that night. 

Everyone was out of the restaurant at this point; everything was done, except for cashing out. They sat at the small table at the back of the restaurant, where they were both enjoying their drinks, as they finished the cash out. Chris had been trying to figure out how to bring up the conversation from earlier. 

Finally, he just said, "So, you are sorta a slut for big dick?" as he looked away immediately. 

Olivia took a minute to think about how to answer the question. She took a long sip of her drink, put the cup on the table and locked eyes with the nervous looking Chris. 

"Well, I wouldn't say slut, but I do enjoy big dicks. I can always tell when a guy has a dick I would enjoy, and when I decide I want the dick, I take it," she told him. She waited a minute, before continuing. "But I can tell your cock would be too small for me. That's why I can tell you all of this," she said, with a chuckle.

Chris' eyes went wide, as he was completely caught off guard. "Ummm, I have a big cock... your big-cock radar must be off," he said, with a tinge of anger in his voice.  

"Chris, it's okay. I am sure you have a normal-sized cock; it just would probably be the smallest I have ever had." 

Chris took this moment to finish his drink. "I bet you it's not even close to being the smallest," he said, louder than he wanted to. 

"Well, someone is confident, and I am betting a little horny," she said, laughing.  

"I mean it. Let's make a bet. If I show you my cock, and it's not the smallest you have ever had, I get to fuck you however I want." 

The confidence was spewing out of him, even though it probably should not have been. Chris was not small, by any means; he was a respectable size--five inches long and sort of thick--at least in his mind. 

Olivia took a few minutes to think about what Chris had just said. "Okay, but what do I get if you are the smallest cock I have ever had?" she asked, more curious than Chris would have thought.  

"I guess I will let you do anything you want to me, or have me do anything you want to you," he said, not thinking clearly, as he was currently thinking with his cock. 

Again, Olivia took a minute before answering. "Okay, I have a fun idea, but just remember you said 'anything'. If I look at your cock and it is the smallest I have ever had.... I get to peg you an--" 

Chris cut her off, "No fucking way I am not gay," he blurted out, overly defensive. 

"Chris, let me finish; you did say anything. So, as I was saying, if you are tiny, I get to peg you, but while I fuck your little ass I have a movie I made of big cocks fucking me you have to watch, as you take my dildo. I mean, you said you were big, so what's the harm in the bet?" she winked at him, and let off a little laugh.

Chris had to think for a minute. The thing was, he was no stranger to being pegged. Claire was kinky and loved to use toys on him, even if it took a while to convince him to do it at the start. "I think that... no, let's do it. You have a deal. My cock is big, I know it," Chris said, trying to pump himself up. 

"Okay, well I have a toy in my purse, I was planning on staying at The Desire tonight because I have to open tomorrow. The toy is comparable to the smallest cock I have ever had inside me. Let's go to my room and measure." 

Olivia stood up and led the way. They walked down the back hallways, so no one would see them. They get to her room 690. She opened the door and walked in.

"Why don't you head to the bathroom, and get hard; I will give you a few minutes to get as big as you can. I will get changed and get the toy out, so we can compare," she said, as she pointed to the door.

Olivia went to the bed and pulled out the toy and put it under her pillow. She got completely naked before going into her suitcase and pulling out a matching pair of red lace bra and panties.

Chris went into the bathroom. He splashed some water on his face, unzipped his pants and pulled out his cock. His cock was already very hard because of how excited he was. He still thought he could get a little bigger, so he slowly rubbed his cock getting himself close to cumming, so his cock would be as big as possible. Once he was ready, he opened the door; naked from the waist down, his hands covering his cock. As he turned the corner, he saw Olivia on her knees beside the bed, wearing her red lacy bra and panties. His cock almost exploded seeing her like that. 

"So, are we ready to measure?" she asked. 

"Yep, let's do it. I can't wait to fuck your little pussy," he said, overconfidently. 

The moment of truth came. 

Chris moved his hand to reveal his cock to Olivia. She took a moment to look at it, she laughed for a second, before catching herself. 

"Well, I can already tell I won, but I will still bring out the toy just to make sure," Olivia said, obviously happy about winning the bet. She pulled the toy out from under the pillow, placed it beside Chris' hard cock. She was right, the toy was easily two inches longer than Chris, and much, much thicker. 

Chris looked down with a mixture of shock and concern. 

After a few minutes, Chris finally said something. "So, you really do only fuck huge cocks. I guess you get to peg me," he said, not letting her know that he had, indeed, been pegged before. 

"And like I said, that was the smallest one; this might sound cruel, but I don't think I would even feel you," she laughed again. Chris didn't know it but he was slowly starting to like Olivia being mean about his small cock. "Go shower before we start. I like my whores clean," Olivia said to Chris. He had never heard her talk like this, but he knew what it meant--she was going to completely dominate him in every way.

When Chris stepped out of the shower and went back into the room, Olivia was waiting for him, standing beside the bed still wearing the red bra and panties. This time, she was also wearing a strap-on. Chris was hoping the toy she used would be smaller, but it was the one that she showed him earlier.  

She caught him looking at her cock. "Like what you see? Or are you jealous mine is bigger than yours? Now get on your knees," she told him.

Chris listened, and dropped to his knees. "It's weird but I think I do like what I--" 

He was interrupted by Olivia shoving the dildo into his mouth. She shoved her cock in his mouth and started to thrust slowly, until she noticed that he was not struggling to take her cock. Olivia stopped for a minute and took her strap-on out of his mouth. 

"You seem to be sucking my cock like you've done it before. Have anything to tell me? You and the boys having some fun at school?" she asked, with a lustful look in her eyes.

"What? No I have never sucked a cock before," he told her. 

She took her cock, and slapped him in the face with it. "Don't lie to me; you are sucking it like a little whore, not like the first-timer I thought you were," she said, angry that Chris lied to her. 

"Okay, fine. I have never sucked cock before, but Claire and I use toys sometimes, okay. She has a strap-on, too," he said, his voice full of shame. 

"You have nothing to be ashamed about, at least about the strap-on. Your tiny cock, on the other hand, that you might want to be ashamed of," she said meanly, as she started to fuck his face again.

As she pushed her cock further and further into his mouth, Chris started to drool and gag all over her cock. Olivia noticed his eyes started running. She thought the sound of his gags were extremely hot, her pussy started to get wet as she started to thrust harder and faster. Chris kept taking her cock like a champ, finally she stopped. 

"Stay on your knees, I need to go get the video of what real cocks look like." 

She walked to the other side of the bed and grabbed her laptop, opened it, and turned on a video. The title was 'Cocks that stretched me out'. The video started playing, showing Olivia sucking a monster of a cock. Chris's eyes became glued to the screen, as he watched her take the cock. 

"Enough sitting around; get on the bed, on your hands and knees. And make sure you are watching what real cocks do to me," she said, laughing again

Chris climbed up onto the bed, on his hands and knees just like he was told. As his eyes looked up at the screen, he noticed Olivia was in the same position, moaning as she was getting fucked in the video. Chris felt her hand move to his hips. 

"Better get a good look at this video, it's the only time such a small-cocked loser will ever get to see my pussy," she said, as she played with his ass with the tip of her cock. She lubed it up and slowly slid it in his tight ass. He started to moan, as she slowly started to thrust, making sure not to fully insert the dildo into his ass. His moan started to get louder, as Olivia started to fuck him harder. His tiny cock was dripping, between the video he was watching and Olivia's huge cock in his ass, he was trying his hardest not to cum. 

"You are taking this cock like a real whore! Claire must fuck you more than you fuck her! At least that's what would happen if I was dating a guy with a tiny cock like you," she laughed again, as she continued to fuck him. 

"Harder, please, Olivia. Harder," Chris moaned. He tried to catch himself, but the words were already out of his mouth. 

"What's that? You like this, don't you, Chris! You like a girl with a nice big cock teaching you how to fuck." 

Her words made his cock throb. The video screen went black, and another video started; this time, Olivia was riding a different guy with a big cock. Chris tried to reach down to rub his cock, so that he could cum. 

Olivia caught him and spanked him hard. "Don't you fucking dare. I am the one who gets to make that little cock cum. Do you understand?" she yelled. 

Chris nodded his head in agreement. 

She pulled out and lay on the bed. "It's time for you to ride my cock. By the way you take this, I bet you are a pro," she said. 

Chris readjusted himself, so that he was over her cock. He glided the cock into his ass and started to bounce on it. 

"That's right, ride my cock, you little whore. I love seeing your little cock bounce. Make sure to keep watching the video," she said, with a sinister look on her face. 

Olivia started to thrust harder and harder; this time, making sure that Chris took every inch of her fat cock in his ass. As this was happening, the video changed again. This time, there was another girl in the video. Chris got excited, as he was about to see Olivia lick a pussy. That was until the camera turned, and he saw Olivia's face laughing. Olivia started to fuck Chris harder and harder; Chris starting to moan extremely loudly. Chris had a pit in his stomach when he realized that the video on the screen was shot in the same room that they were in now. Olivia started to giggle when she looked at Chris' face, clearly in a panic. 

"Ummm, when did you shoot this video?" Chris asked, trying to contain his moans between Olivia's thrusts. 

"Last night. Why, look familiar?" she said, again laughing as she fucked him. She paused the video. "Get on your back now. I want to watch your tiny cock cum as I fuck you as hard as I can."  

Chris climbed off, both nervous and excited, he really loved getting fucked like this; he just never knew it. 

He lay on his back. Olivia moved the computer beside him and pressed play. 

"Make sure to pay attention to the video, and not me," she said, as she forced her huge cock back into his ass. The video continued. Olivia had a grin on her face, as the video started to move closer to the other girl, getting fucked by the biggest cock he had seen that night. 

"Ummm--" Chris started to say, as the camera panned to the other girl's face. 

It was Claire, his girlfriend--she was getting pounded by a huge cock. 

"Oh fuck, this is the best dick I have ever had. No way am I going to be able to feel my boyfriend ever again," Claire moaned in the video. 

Chris came instantly, between watching Claire's pussy being stretched and Olivia's cock in his ass. He exploded all over himself; it was the biggest load he ever had. Olivia pulled out and took off her strap-on. Now that your little cock is done, we have some things to talk about," Olivia said, leaving the video playing in the background. 

"So, as you can see, that is Claire and that is not your tiny little cock. I told her about you trying to fuck me all the time. We talked, She told me everything, from your tiny cock to how you don't make her cum, to the fact that you love getting fucked so much she almost convinced you to try a real cock one time!" she said. 

"Oh fuck, this pussy is yours. Cum in me now. If he wants to cheat, he will get a surprise," Claire said in the video, as the cock pulled out of her leaving a huge creampie; her pussy was red and swollen. 

The video ended with a time stamp, it was last night at 8:03pm. Chris noticed that, and realized that was right before she came to visit him after his shift.

Olivia was laughing, as she noticed Chris thinking. When he had gotten into work this morning, he told Olivia that last night, Claire only wanted her pussy licked, which was strange, and he asked Olivia for advice. 

Chris' world was turned upside down. "I knew, last night, her pussy tasted different. And she told me she came super hard, that's why," Chris said out loud. 

"Well, now you can say that you have had a mouthful of cum. She made sure to keep his creampie for you. Claire has another video for you, but it's time to take your tiny dick and to to sleep. We can talk tomorrow. But just to remind you, Claire is busy again tonight," she laughed, as she threw his pants at him. "Now get out. I have a real dick on the way."

To be continued.