Chapter 9 - Round 5

Just as I asked Diane what her experience had been during the oral challenge of round four, Penelope started talking again.

All the men and women gathered around her in the living room. She gave us the times of when the last challenge would start. For the females, they would have to gather at 7.30 PM in the hallway. For the men, it started at 8:00 PM. Before they gathered, The men had to determine the order in which they would come in from first (one) to last (eight). The men would enter the room in twenty-minute intervals and she gave a printed schedule in case we were bad at math. Based on that the last man would go in at 10:20 PM. This looked like a long night.

I was still unsure what was going to happen, but it was going to be almost three hours long. Ashley asked what they were supposed to wear and Penelope said whatever they wanted.

“A three-hour-long gangbang”, Diane said as we walked to our bedroom to prepare. For Diane it would start in fifteen minutes, for me, it might not be until much later.

“Only one guy at a time”, I said as it didn’t seem likely that we would all fuck at the same time and switch somehow like we had done with the oral part.

“That would mean the mental torture will be insane.”, Diane said. “If it is indeed that we are going to be fucked every 20 minutes or so, we will just be laying there waiting, mindfucking ourselves.”

I could see her point and was thinking that it might not just be fucking that some guys might do. We discussed some strategies on how to recognize her and we agreed on a similar approach. I would try to penetrate her somehow, her ass preferably, and she would squeeze three times. The recognizing part wasn’t a concern. After seeing the images and I had felt every lady I was pretty sure I could distinguish each girl as I knew which ones I had identified incorrectly before.

“What is your strategy going to be?”, I asked.

“Depends on how the points are earned. Either be a dead fish or be very into it.”, Diane said. “I rely on you to see what the best strategy is”

She explained how weird it was. It was their competition, but the men held the most power and determined how the points were scored. I wondered if that had been the point all along of the competition, but could only guess at this point.

She kissed me passionately goodbye before heading out of the door. She hadn’t bothered changing clothes as they would probably have to come off soon.

Standing in the doorway, I watched her walking away. She looked over her shoulder.

“This is what it looks like when somebody is about to walk towards their own gang rape,” she said and blew me a kiss. She was smiling but I could see the concern in her face.

“Have fun okay, at least one of us should enjoy it.”, she continued as she disappeared around the corner.

This was the most vulnerable and caring that I had seen Diane. She wants to be ruthless all the time, but this weekend I saw another sight of her that was new to me. It would be hard to say goodbye after this weekend as it would feel like a breakup again.

A few minutes later I walked to the living room and saw the other guys already there. I was handed number eight, as I had been the last one there. I didn’t feel fair, but several of the guys didn’t budge and I took the number.

Hanging around with the other men didn’t interest me so I went back to our bedroom and started to strategize how I was going to spend my fifteen minutes. I wondered if voting would be the same and orgasm based.

In my mind, I had made up a whole strategy of how to quickly recognize each woman, find Diane, fuck her, and then move on. It made sense in my mind. The whole process did turn me on, and so I thought that I should at least try to stick my dick in all of them. Just to say that I had.

The waiting game started. I watched some TV but my mind kept going back to the other room and what was happening in there.

Finally, it was 10.15 PM and I walked over. At the backdoor, there was nothing, not even a form. Also, there were no instructions on what the challenge was or what the points would be.

I tried the door, but it was locked and when I tried to eavesdrop, I could hear some noises of what sounded like somebody walking and another noise that sounded like metal hitting metal, but nothing that I recognized.

At 10:20 PM exactly the door opened and Penelope was there. It was hard to see as the room was very dark and I could barely see. There were some glow-in-the-dark numbers, but that was it. The room almost looked empty. It was just dark.

“Please get undressed completely”, Penelope said, “You get 15 minutes in paradise with the ladies. There are seven ladies left for you. All the ladies have been restrained and are hidden behind the curtains and are unable to communicate. All girls have signed off that vaginal and anal penetration is allowed during this challenge.”

Penelope pointed to seven glow-in-the-dark markers with the numbers. There was an obvious gap at number seven and I was wondering who had given up and why. I hoped it wasn’t Diane.

“A clock will light up and count down the fifteen minutes.” Penelope continued, “After fifteen minutes, please gather your clothes and go outside. There you will find a form to fill in. Please drop it off in the dropbox once completed. The questions and points are identical to round four, both you and the females get points for recognition.

Fifteen minutes was less than I hoped for, but there were only seven girls. What I hadn’t anticipated was that I had to remember the order of the names.

Penelope went over some more rules. Condoms were required and they would be provided at each girl station together with lube and cleaning supplies. Only a filled condom would count as a favorite point for that female. The condom had to be left at the girl’s station after usage and could not be taken away.

This looked promising. I hoped Diane hadn’t dropped out, but it seemed we had guessed the challenge perfectly and our plan would work.

“Finally, no touching behind the curtains.”, Penelope stated, “Every female body part exposed is free to use how you see fit or to your liking without consequences. There is a large circular handle you can use to hold on to for stability”

I thought about the ramifications of what she just said. My assumption had always been that this challenge was about fucking, but it was just the same. You feel up some girls and find out who they are, not unlike the second round. Only the access had been extended. This was to test the girls on their endurance, as I believe most guys would score full points on this.

My eyes were getting used to the dark and I could now make out that there were chairs in the room in a half circle. Penelope told me to pick a number where I wanted to start and she would start my time as soon as I said ready.

For me, it would be easier to remember, if I started at number one, so I walked over. My dick was ready to go after the long wait and thoughts of fucking all eight women.

Even though my eyes had gotten used to the dark, it was still hard to see and I could barely see at stage one. The greenish glow-in-dark-style lighting was enough to see the outlines of objects, but I couldn’t see much more. I saw the lube, condoms, and towels and saw a lot of black sheets. I also saw the outline of a girl, but only her hips had been exposed, similar to the images of round three.

The number one had been taped right above the girl’s hips and glowing just enough that I could make out a vagina and the buttocks. The chair looked like some gynecological chair and I assumed her legs were spread around me, as there were sheets to the left and the right of me. I touched the sheets but was immediately stopped by some hard surface. It seemed only the area around her hips was not blocked.