I was sure to win this time. However, I had been sure before and been wrong, so I didn’t put my hopes up too much. Would any of the other girls really get naked. There was only two other girls that got topless. As my boss had said, it was highly unlikely that anyone would have a nude photo shoot done.

When the email came back from my boss, I opened it right away and read it.

Dear Cherry,

It was a pleasure to hear from you again and to see that you are still in the competition.

However, I have bad news for you – another girl made an indoor nude photo shoot too, so it wouldn’t really be fair to say that your photo shoot was more daring. Although, if I had to be subjective, I would say it was. But I can’t allow myself to be subjective, it wouldn’t be fair to the other girl, would it?

It was nice to see you get this far. And listen, let’s stop this contest now before it goes too far. I will tell this to the other girl too.

Ben

Nooooo! Why would she do that? Is she crazy, having nude pictures taken for a stupid calendar. Hell no, I was not gonna stop now. Good news is, he would tell the other girl to stop too, so because she would think we are stopping, I could surprise everyone by taking the next step – and winning the contest!

So, what would be the next step. I looked closely at the email again. “Indoor” he had written. Hmm, could this mean that he would regard an outdoor nude photo shoot as more daring. What was I thinking, of course it’s more daring! That’s it! I’m gonna do it!

I went to my friend’s house that has a pool. It’s a really nice big house – I quickly stripped naked and had him take pictures of me outside.

I poured oil on myself, just as he had taught me before and kept posing so I would have plenty of pictures to choose from for the calendar. I was really getting comfortable with this nude modeling. Perhaps I did have a future career in this. I mean, there would be already two nude photos of me publicized in the calendar, if there’s interest, I might as well have more taken.

“I was thinking …” my friend said “What if the other girl is also having an outdoor photo shoot?”. “That’s crazy!” I replied “Why would she do that, she even thinks the contest is over!”

“Yes, but that’s what you thought every time!” my friend said. “Perhaps you should take it to the next level”.

“The next level?” I asked … “and what might that be?”.

My friend looked thoughtful. “Let me ask you this, Cherry – are you a virgin?”. I shook my head. “Does people think you are a virgin?” I shook my head again.

“So what’s the problem? If people doesn’t have any illusions about whether you ever had sex before, why not show them how it’s done – and be sure to win the contest at the same time?”

He had a point – of course I had sex before and people knew that. They would also see me naked and admittedly indignified in several revealing positions. We might as well put the two things together – and make me a lot of money in the progress. “And who would … be the … male model?” I asked. Right then and there, my friend knew that I was open to the idea.

“Well” he replied “One of my friends is visiting, I’m sure he would do it. Let’s go inside”.

The friend was waiting on the couch when we came in. “Is this her?” he asked. My photographer friend nodded and took a picture. “I’m Andy, it’s a pleasure to meet me” he said humorously.

“What’s going on?” I asked the photographer, “Did you set this up?”

“Set it up – we’re doing you a favor here! You’re the one who wants to win the contest, remember?”

He had a point. “OK, let’s take the picture before I change my mind.” I said. Andy stood up and took his clothes off. Then went to me and gently pushed me towards the couch, then he sat down, took my hands and pulled me down with him.

“Good, you’re already oiled up” he observed. He then fiddled for just a moment with his now stiff cock, then he let it inside.

*SNAP* – a picture was taken, then another. Holy crap, I was having pictures taken of me having sex – and they would end up in a calendar for public display. Everyone in the night club would know what I had done to win. It would be right there in the calendar.

I don’t remember much of the following moments – just that he had cum on my breasts and that they had both had a great time reviewing the pictures. I was dizzy from the experience. I went home that night and contemplated whether I should send them to my boss. I could still back out – or could I? Well, I could send the picture and win the calendar money – or I could be the girl who fucked a stranger and never got anything for it.

I ultimately decided to send the picture.