More daring – Chapter 5

Having send the picture, I knew my life had changed forever. I guess I could still work in the night club, but people would never see me the same way again. I would be the one who went ALL the way to win. That’s the positive spin on it, that’s the one I kept reminding myself of.

The negative spin was that I had sold my dignity for a few bucks (well, a lot of money, actually). I decided to block the negative spin out of my mind and focus on the positive. I was all positive when I got the mail back from my boss.

Cherry! I can’t believe you did that!

You fucked some guy just to be in the calendar and win a bit of money! Well congratulations!!

My heart skipped a beat. He wished me congratulations! I had won!

Congratulations on being so liberated and a free spirit that you do just what you want.

One of the other girls also made a photo shoot where she is fucking, so I can’t really give the money to you. I honestly hadn’t anticipated this! I expected maybe one of you girls to go topless, I never thought you would go and fuck guys just to be in the calendar.

But I’m happy you did! I’m sure this calendar will be a success!


What the fuck! I couldn’t believe it. In fact, I didn’t! None of the other girls would go through with something like that! That’s crazy. Going from a simple nude shot to a sex scene i ludicrous. I had done it, but I simply wouldn’t believe that any of the other girls would do it.

Instead of thinking about what to do next, I wrote back to my boss and challenged him. I said I didn’t believe him and that he was a jerk for lying. He replied back minutes later.

Hi Cherry,

I understand your concern and I was as surprised as you were. Especially at the fact that it was Cindy that chose to go all the way to win this thing.


She wasn’t as adventurous as you. She simply had a nude picture taken by her bed. What a nude picture. I was so thrilled to see that Cindy was happy to participate.

I told her that I thought we should end the contest, but she wouldn’t hear of it. I received this picture a little later.


And listen, Cherry – you know, this picture is actually more revealing than yours! Your picture didn’t actually show the penetration whereas Cindy sent the entire album with all the pictures – and all the details. On it’s own, enough for a calendar.

Let’s call it a draw, though.

Shit. That was certainly proof. But why would she do that. I had my suspicions. My photographer friend – I recognized the style of the photography. He had sold me out, maybe played her as he had played me, getting us both to go further and further.

But I was gonna get the last word …

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