Chapter 3 - Round 1

On the other side of the room was a thick dark black cloth sheet covering a large section of the room. The sheet went all the way from the ceiling to the ground, like a straight theatre curtain. The sheet had some strategically placed holes and poking through the holes were eight sets of boobs, evenly spaced out.

It was quite a sight, seeing eight pairs of boobs and I was imagining what the scene looked like from behind the sheet. I pictured eight topless girls, standing on some steps to make their height equal, and sticking out their boobs through the holes in the sheet. It must be a silly sight, and probably rather humiliating. From my viewpoint, it was a much more eerie sight seeing eight pairs of floating naked boobs, not attached to any person.

The assignment was clear now. We had to recognize the girls by their boobs. This was something I could do and went into game mode. A few of them seemed easy. Gemma had the biggest pair and only one pair looked bigger than the others, so I wrote that number behind Gemma’s picture. Next, I looked for the smaller pairs. I saw two pairs that looked smallish and assumed those were Brianna’s and Carolyn’s. Looking around, I noticed what I thought looked like Diane’s based on the nipples and so that left me four pairs to identify.

Since Emily was a redhead, I picked the one with the lightest skin and nipple color as being hers. Even from the distance we were standing, I noticed some moles and figured that might be Fran. The other pairs seemed fairly similar and just had to make some wild guesses based on nipple size and nipple and skin color and the shapes that I seemed to remember till I had a unique number for each female.

The last action thing I had to do was to write down my favorite. I was not sure what the strategy would be of the other men, but mine was to always fill in what I thought would benefit Diane. Therefore I marked what I thought were Diane’s boobs as my favorite. Truth be told, the ones next to her, the ones I had identified as Emily’s, looked spectacular from every angle.

There were still eight minutes left, but I stayed to enjoy the view and to verify my answers. They had taken our phones when we arrived and that was a good thing. If I still had it, I might have been tempted to take a picture of this absurd scene.

Some other men seemed to be enjoying the view as well or maybe they were trying to sheet but I noticed that they started signaling each other and pointing to boobs. Penelope noticed it too and wasn’t having it and immediately took their forms and they were instructed to leave the room. I was not sure what the impact of that event would be, but I assumed they would either get zero points or the form was counted up to the point that they had completed. Either way, it was good for me and Diane, I thought.

After the time ran out, all the remaining forms were collected and all men were asked to leave the room through an outside door. As soon as I stepped outside, I heard men discussing the boobs that we had seen. A small group was discussing whose was whose, and others talked about how yummy they looked and wanting to grab and lick them. Based on some of what I was hearing it sounded like I had guessed well.

As a group, we slowly walked back inside. Once inside I immediately went for the alcohol as I needed it after the event. I barely had taken a few zips before Penelope walked back in.

“Please all come back to the barn.”, Penelope instructed us, “We have a situation to resolve.”

Like a group of sheep, we followed Penelope back to the back room. Everybody was whispering what they thought was the situation she had referred to, but I didn’t hear any good guesses.

Once inside the room, I noticed the dark sheet had been opened. The girls were still there, but six of the eight girls stood together and were dressed again, or at least back in their pajamas. The two remaining girls were standing by themselves, topless. I recognized Gemma and Ashley as the topless girls. I felt a slight sense of guilt staring at them. In a different setting, this would be fun to look at, as both girls are easy on the eyes. Ashley looked stunning in her lace panties and Gemma wore a regular set of undies that had been covered by the T-shirt before but her undies and big tits were now out in the open.

Ashley looked a bit embarrassed and was looking down, but Gemma just stood there as it was another day in the office. Neither girl was covering their nudeness. I assumed they had been instructed to not cover themselves and so they stood exposed like undressed mannequins in a clothes store.

I looked at Diane and stared at the two topless girls again. My slight sense of guilt quickly evaporated. The girls had chosen to participate and I was going to enjoy this weekend to the fullest.

Diane walked up to me and explained what was happening.

“There is a tie, both Ashley and Gemma were identified correctly by all eight of you. I guess Ashley has slept with more men than I thought.”, she said with a laugh.

I was going to reply that I hadn’t and had just guessed, but Penelope started talking. She explained about the tie and how it was going to work. The men were going to draw a number and we would take turns putting clamps on the girl’s breasts. The first girl to give up would be the loser.

“This is going to be fun”, I whispered to Diane and she smiled back in agreement.

I picked number three and was given a handful of clamps by Penelope. I discussed the strategy with Diane and she said she wanted Gemma to lose as she felt she might be the biggest competition because of her bigger features. I wondered if it had to do with the argument they had during Twister where Gemma had called Diane out for rubbing her boobs against her boyfriend.

There was no time to further discuss as the tie-breaker had started. The first person had put one on Ashley’s left nipple. She flinched but otherwise seemed okay. The next person placed their clamp on Gemma’s left nipple.

Now, it was my turn. There had not been many rules mentioned so I took some liberties and see if anybody would stop me. I walked over to Gemma and without hesitation grabbed her left breast and lifted it. With my other hand, I placed the clamp directly on her breast tissue and let it drop.

“Motherfucker”, said Gemma as the clamp now pinched the soft flesh of her underboob and pressed against her skin. I showed an evil smile to her in response as I walked back to Diane.

“Well done”, Diane said. Her ruthlessness was coming out. I knew how much this competition meant to her and I would go to great lengths to help her win.

Next up was Ashley’s boyfriend. He was not going to put it on his girlfriend and so he walked over to Gemma too. He fondled her right breast but placed the clamp on her left nipple.

“Nice tits”, he said as he walked back. Gemma didn’t reply and bit her teeth. It had become harder to hide that the clamps were hurting her.

The rest of the guys put on their clamps. Penelope indicated that the first guy had to place another clamp and so we went full circle again. By the time it was my turn again, Ashley had three clamps on her tits, but Gemma had eight, five on her left breast and three on her right breast.

For my turn, I went back to her left breast and lifted it again. With my other hand, I opened the clamp wide and placed it on top of the clamp that was already on her nipple, doubling the pressure. Gemma’s facial expression changed instantly and the pain seemed to reach her pain threshold.

I looked Gemma straight in the eyes and whispered “Shouldn’t have argued with Diane”, and lifted her tit further before letting go and letting gravity do its thing. The heavy boob slammed on the clamps attached to the underboob of her tit.

Gemma yelped out. The clamp at the bottom was piercing in her tit and the rest of the clamps had swung as I had dropped her tit. She grabbed her tit and started taking the clamps off. “Fine, I give up. You win.” She didn’t look at Ashley as she said it. She looked at Diane.

“Congratulations, we have a loser.”, Penelope Gold said. “Ashley, you can get dressed. Gemma, you stay.”

Everybody was watching in silence as Ashley put her lace top back on. I felt like a voyeur and it was turning me on. Gemma just stood there, defeated, and was rubbing her painful breasts. I think she had forgotten that a group of men were watching her do it.

“Gemma”, Penelope said, “for having the most recognized breasts as well as receiving the most votes using the clamps, you get the Attention Whore prize this round.”

It was hard to contain my smile hearing Penelope say this sentence. It was not something that I expected from a lady her age and with her stature.

Penelope walked to a back wall and opened a chest. Everybody followed her with their eyes to see what she was going to do. She took out a riding crop and walked back to Gemma.

“Nobody likes an attention whore.”, Penelope continued, “The prize you receive for this reward is a stroke with this crop to your breasts, handed out by one peers’ partners.”

This was crazy. First, the girls had to stand topless as their breasts were being judged. I assumed that it had been rather humiliating by itself. And now Gemma was punished for having the biggest breasts I felt, not something that she could easily change. And oh yeah, because there was a so-called tie-breaker, her tits had already been tortured and now she was going to be tortured more. I am glad this wasn’t Diane that it happened to as I am not sure how I would have reacted. Gemma’s boyfriend didn’t seem to mind and seemed to be waiting in anticipation of what was going to happen next. As if he was watching a porn movie.