What Could Go Wrong?

"Looks like someone is getting nervous," Bill said to me.

"You wouldn't make them actually run around naked, would you?" I asked.

Bill laughed. "Rules are the rules!"

Brent and Hilde both hit their shots, again, and Tammy and Tom were down to their final cup. Hilde missed her next shot on the send backs, and Brent picked his ball up from the water cup when I had an idea.

"Hey Tammy!" I said. "Why don't you play a little defense?"

"What do you mean?" she asked, confused. But Hilde got what I was saying, and laughed.

"She means, maybe give him something else to look at," Hilde called back.

"Oh," said Tammy, blushing.

"Better than him having everything to look at!" Sam laughed.

Tammy must have decided it was worth it, as she reached both her hands down the neckline of her dress and pulled it down a good bit. She had smaller breasts but they were very shapely, and her bra was black, like mine, and lacy too. She kept them out and staring at Brent as he lined up his shot - and missed!

"Oh well," he laughed.

On his next shot, Tom finally hit one, and Tammy let out a relieved woohoo and hugged her partner. They lost the game but Tammy almost looked like she had won, just haven escaped showing her birthday suit to the group.

"How about we play something else?" Hilde suggested.

"Fine with me," I said, but Bill suddenly looked sad. Maybe he really wanted to play beer pong with me, I thought. I should go along with it. "Maybe one more game, Bill and me versus you guys, then we can switch to something else?"

That seemed agreeable, so we refilled the cups and reset them on the table. I had never played before, so I figured I would be pretty bad, but once Hilde and Brent missed their first shots, I took the first for our team and it dropped right into the front cup!

"You're a natural," said Bill, as he took a shot and hit one too!

"Rats," said Brent as he drank his cup, "no shutout this game, either."

As he said it, though, I took my send back shot and hit it again. "Maybe there will be!" Bill countered, and he made his too.

I missed my next shot but whatever magic Brent and Hilde had from the first game had abandoned them this time around. We were up 10 to 4, and I hit another shot. Hilde, who hadn't gotten nervous up until then, suddenly started to look like Tammy had in the first game. I realized that if she wound up having to streak in front of these boys, Jeff might hear about, and I wondered what he would say about that, and whether Hilde would tell him in the first place.

Meanwhile, Hilde made no move to reach for the cup that still had my ball in it, and neither did Brent. They argued over whose turn it was to drink, and meanwhile Bill lined up his shot and sunk it - right into the cut that still had the ball in it.

"Death cup!" Bill yelled.

"What's that?" Tammy asked from the sideline.

"It means if you hit a shot into a cup the other team should be drinking, it's sudden death!" Hilde and Brent started to argue, but Tom, the most senior of the boys, chimed in and concurred.

"Do we get rebuttals, at least?" asked Hilde, her face now white as a sheet.

"I guess so," said Bill. "It's only fair."

It was no use, however, as both Hilde and Brent's cold streak kept up and both rimmed their shots off the back right corner cup. Bill was beaming like the sun, and Sam and Tom were clapping. "Take it off!" Sam shouted. "Take it off!"

Brent started by removing his sports coat and then his dress shirt, leaving him just a wife beater and his slacks. He sat down on a chair and started to untie his shoes.

"Wait," said Hilde, "wait wait wait."

"C'mon, Hilde," said Brent, untying his other shoe, "it's the rules. You knew that!"

"Besides," said Tom, "It's not that cold out."

"We have to do it outside!?" Hilde yelled. "No way!"

"Sorry, dear, but even you knew the rules when it started." said Sam.

Hilde was crying now, and I felt terrible for her. Here was my friend who had stood up for me before, and I wasn't going to let this happen to her.

"Wait!" I said. "Hold up."

"What's that?" asked Bill, confused.

"How about we play double or nothing?" I asked. Hilde looked at me, and I could see through her tears she was touched I was standing up for her.

"What do you mean?" asked Tom.

"Let's play another game, and if Hilde and I win, she doesn't have to run the naked lap."

"And if you lose?" asked Tom.

I swallowed. "She and I both do it."

"What about me?" Brent asked. He was sitting there with no shirt and one shoe on.

"How about you play something, Monica and Hilde against you and Bill, and losers have to run the naked lap while the winners don't?" suggested Tammy.

"Easy for you to suggested," Bill said. "I won, why should I have to get naked?"

"How about this," Tom suggested. "Let's all play a game, here's how it'll work. We'll deal poker hands or something, and each hand, whoever has the lower hand has a choice: they can either take a shot of whiskey or vodka, or they can remove an article of closing. And, let's say, the first group to be out of clothing, guys or girls, has to do the naked lap, as a group."

"But those two already lost!" Sam said, indicated Brent and Hilde.

"And why should I have to, I didn't get shut out?" Tammy said.

"Don't you want to support your sisters-to-be?" asked Sam.

"They'll start with fewer articles on," Tom said. "Let's do it like this, to make everything fair. I'd say each girl has, say, five articles of clothes." We all counted in our heads: dress, two shoes, panties and bra. That was right. "For the guys, we'll do it as five articles too: first for both shoes and socks, second for sports coat, third for shirt (including any undershirt), fourth for pants and fifth for boxers. Each of Brent and Hilde can start down, say, three articles." He turned to his frat brother. "Brent, buddy, I think you can take your other shoe off but otherwise I think you're good." Then he turned to Hilde. "I think you know what you have to do. Still, better than with nothing on outside, right?"

Hilde nodded, without saying anything, she kicked off her shoes and then started to unzip the back of her dress. It dropped to the ground, revealing her perfect body. Then, stepped out of it, and stood before the group in her underwear. Unlike Tammy and me, she hadn't worn anything sexy, just white cotton panties and a white under wire bra. But one her, even those on here were sexier than Victoria's Secret on anyone else. The guys didn't even bother containing their smiles, and Hilde blushed and tried to cover up as best she could, one hand over her cleavage and the rest over her panties.

We all sat down at one of the dining tables, and Bill produced a deck of cards, a bottle of vodka and bottle of whiskey from upstairs, and a shot glass. Tom shuffled and dealt the first hand. Sam wound up with the lowest, just a nine high. He shrugged and took a shot of Jameson. Tammy lost next, and started freaking out before she realized she could take a shot of vodka instead of stripping. She did so, and her face started looking flush.

For the next few rounds, no one did anything other than take a shot, but soon I realized that couldn't last. I had been drinking for hours now, and I was definitely feeling it. When I turned my cards over on the next hand and saw I had nothing, I started to sweat. I handed in three and got nothing better in return, so when we laid down our hands, I was low card.

I eyed the vodka bottle longingly, but knew this night would end poorly if I drank any more. Instead I removed a shoe, making a show of flinging it behind me. The boys hooted and slapped five. I saw Bill smile at me, and I smiled at him back.

Bill lost the next round and removed his shoes, and Tom lost the next one and removed his jacket. It seemed like everyone had about reached their limit. The next two hands were Tammy's turn to lose, and she removed her shoes, one after the other.

The next hand was also Tammy's, and she got that frightened look in her eye as she decided what to do. She went so far as to full the shotglass with vodka, but the smell of it made her almost upchuck right there. She dropped her head and started to undo her dress from behind, but couldn't reach all the way down. I got up and helped her, and she had to stand up for me to get the zipper all the way down. She discarded the dress and stood in front of everyone in that black lace bra she had shown the boys during the beer pong game, and, a black lace thong that barely covered anything other than the triangle around her crotch. Tom insisted that she spin around to satisfy the condition for losing, and she did, giving us all a great look at her toned ass. She sat down quickly and, like Hilde, tried to cover up.

Bill lost the next hand and removed his shirt, and sat back down with nothing above his belt on, his shaved chest bare. He must have worked out because he had he budding evidence of a sixpack and his pecs looked pretty developed. He must have seen me staring because he smiled at me, and winked. I got embarrassed and turned back to the game.

But luck was starting to turn against me. I lost the next hand and removed my remaining shoe. Tom lost the next one and removed his dress shirt, revealing a sweat-stained undershirt beneath that he also discarded. I hid a smile, which he might have noticed, but as we dealt the next hand I realized I had nothing, and after asking for more cards I was still left with rags. I decided to take one last shot of vodka, rather than removing my dress. It was one thing for the likes of Hilde and Tammy to show their gorgeous bodies, but I was a short, chunky girl without their beauty. I almost gagged as I chocked the shot down, and knew that next time I lost, I would have to take off the dress. I felt it, tight and clingy, wrapped around my thicker thighs and the flab on my tummy.

Brent lost next, and at this point had to take his pants off. He removed them to reveal a set of grey boxer briefs, and he saw quickly to hide his boner that was clearly visible through the thin cotton.

"Oh no, you gotta spin around!" said Tammy, and Brent grudgingly obliged, going fast to get it down with, which had the effect of making his dick whip around, to the delight of myself and the other girls. Tom lost a couple and was soon down to his boxers as well.

Hilde lost the next hand, and she too made a reach for the vodka, but decided better of it. The boys started hollering again, and she reached behind her to unsnap the hooks on her bra, letting it dangle off her great bosom. She slid one arm across them, under the cups, then removed the bra with her other hand, leaver her topless with only her forearm to cover her boobs.

"Oh no," said Sam, "no covering." Hilde sighed and moved her arm out of the way, revealing her breasts to the group. They were perky and perfect, with smaller nipples than I would have guessed, the size of a large grapefruit each, and the boys were loving it. Hilde slouched down and tried to use her cards to cover them for the next hand, but she could only hide so much.

Bill lost the next hand, removing his pants this time. He was a lot less bashful than Brent had been, sliding them down slowly, savoring the moment. He wore bright green boxers that also didn't do a great job of hiding his erection, and he turned around slowly to give the group a look before sitting down. He smiled at me again, and this time I smiled back.

I wasn't smiling for long though, as I lost the next hand and, to my shame, started to cry. I couldn't let the boys see me in my underwear, especially compared to Tammy and Hilde! But Hilde walked over and gave me a hug, uncaring that the boys got a great look at her rack, and told me it would be ok. I stood up and Hilde helped me out of the dress, which took some wiggling on my part since my fear had caused me to sweat, and the dress to stick. When it was finally off, I turned around quick, but not too quick for Tom and Sam to catcall at me, telling me they loved my curves. Bill, quite the gentleman, didn't so much as open his mouth, and when I sat down, trying to cover, he smiled warmly.

Sam lost the next one and was down to just his pants and boxers too. I was hoping for some good luck that maybe the boys would wind up being the ones to streak around the house, but it was Tammy who lost next. To her credit, she was quick to snap her bra off and even give them a little shake to show the boys what she had. Maybe compared to my flabby body, she didn't mind showing off her goods. And her goods were worth showing off. Her breasts were the size of oranges, with pointy nipples, and poked upward at an impressive angle - she barely needed a bra! And now, without one, she was set to play again.

At this point I saw Tom inch closing to Tammy, and Tammy closer to him. I wondered if there was something there.

I didn't have much time to wonder, though, as I lost the next hand. The guys high fived again, as each girl would now be topless and the one to lose would be destined to show themselves off totally naked. I reached back to unhook my bra but I was too drunk and too scared, and again Hilde helped me out. I dropped the bra to the floor and hoped they would stop staring soon. My boobs were big but a little saggy, with pepperonis for nipples. I was embarrassed like I had never been before. The furthest I had ever gotten with a boy was second base and even then that had just been getting felt up under the shirt, never revealing myself to anyone, let alone four boys and two girls! I prayed they'd deal the cards soon.

They did, with Sam losing his pants. At this point, everyone was down to just one article left, and the losers would soon be bared before the world.

It occurred to me our bet wasn't good for us, numbers wise. To get all the boys out, four of them would have to lose, while for them to win it would only take three of us. I started to protest, but Tom said rules were the rules.

"But wait," Bill said, thinking things through. "What happens when you're out but the rest of your team isn't yet? Do you still play, and if you lose, what do you do?"

"Hmm," Tom thought on that. As the eldest, we all instinctively deferred to him. "How about, once you're out of clothes, but before the game is over, you stay in and if you get low hand, the high hand gets to give you a dare?"

"No way!" said Tammy.

"No offense, but that sounds kind of sketchy," Hilde said.

"I agree," I said.

"Ok, fine, how about this," Tom countered. "If you're out and you lose a hand, someone from your team has to remove their clothes, and the highest hand on the other side gets to pick who?"

"That's fair, I guess," Hilde agreed, and we all nodded.

Next hand was the big one, first person to be totally naked. They dealt the cards and it was Sam. The girls all signed in relief as he stood on the chair and dropped his boxers. He revealed his rock hard dick, about six inches long and with a truss of black wire pubic hair. He spun around, revealing a hairy butt, too. It was our turn to catcall and high five, thought the boys didn't mind as our boobs jiggled with each slap we gave each other.

Next loss went to Hilde, and she took it with grace. She followed Sam's lead and stood on a chair before she dropped her white panties, revealing a neatly trimmed bush and a perfect little vagina. The guys clapped as she spun to reveal a perfect ass and then back around to her gorgeous front. She sat down quickly and demanded the next hand be dealt.

This time it was Bill who had to bare his goods, and I found myself getting excited at the prospect. Bill, who had been without shame the whole game, suddenly got a little nervous, shaking a bit as he stood on his chair and dropped his green boxers. His little man was at full attention, too, And little was a fair description. It was smaller than Sam's, by about an two inches, and he had shaved off his pubic hair, maybe to give it a little bigger look, but ultimately making it look more like a little kids. He turned around real fast, revealing a nicely muscled posterior, before taking his seat. None of the guys said a word, but they were smirking a bit, and Tammy was smiling. I looked at Bill and tried to give him a brave smile, which I hoped he appreciated.

The odds were now even, two on two, me and Tammy versus Brent and Tom. I was starting to feel we might win this when the cards came out and Hilde was last again, and Brent the top man. By rule, he could pick either me or Tammy to strip. He looked back and forth between the two of us, clearly enjoying toying with us. Finally, smiling like the Cheshire Cat, he made the obvious choice. "Tammy," he said, "that lovely thong doesn't leave much to the imagination, but I think it's time to see what's underneath."

"Wait, that's not fair!" Tammy said. "First, Hilde gets shutout at beer pong, but instead of her taking the naked lap, I have to play this game, and now she loses and I have to strip?"

"You guys agreed to that rule," Tom said. "We offered up dares instead, but you preferred this way."

"How about I do a dare?" Hilde offered. "I wouldn't want Tammy to lose because of me."

"What say you guys?" Tom put it to Brent, Sam and Bill. Bill shrugged, Sam shook his head ambiguously and Brent looked like he was thinking about it.

"My hand, my pick of the dare, right?" Brent asked.

"Sure," said Hilde.

"Ok, dare it is then." Tammy breathed a sigh of relief, her thong to remain on her tight little bottom for at least another hand. "Hilde, here's your dare: for the rest of the game, you have to sit on my lap."

Hilde opened her mouth to argue, but she didn't say anything. It was an interesting dare, not particularly naughty on its face, but given the state of dress everyone was in, it was certainly a bit of a line to cross.

Seeing Hilde look conflicted, Brent continued, "or I guess Tammy could lose the thong, and you girls would be one loss away from streaking naked around the house?"

"Ok, I'll do it," Hilde said. She got up and sat down on Brent's boxer-clad lap. She shifted her weight around a bit, no doubt feeling Brent's python pushing against her naked rear through his boxer briefs. She ultimately settled on leaning forward, her weight more on his knees and thighs, but I could bet he was enjoying every sensation of this pseudo lap dance.

They dealt the cards and this time Brent wound up on the bottom. Hilde jumped up, seemingly uncaring that she was butt naked in front of four frat boys in the basement, and Brent gave her a little smile before dropped his boxer briefs unceremoniously to the floor, not bothering to stand on the chair. It didn't matter, though. We all stared in awe at Brent's manhood, a great deal longer than Sam's and certainly Bill's, he had done some manscaping around the great, hard protrusion that stared at us like a giant soda can, only almost twice as long. He forewent the traditional spin, too, and sat back down. I looked over a Bill, who was even more uncomfortable now at the comparison. Hilde moved to go back to her own chair, but the guys all protested.

"The dare was to sit on his lap the rest of the game," Tom pointed out. "Game is still going."

Hilde slouched her shoulders but had to agree that was the dare. She climbed on top of Brent, sitting on his thighs with his mammoth cock at attention, pressed against her the small of her back like the back of a chair. She shifted to get her weight balanced again, and Brent smiled in obvious ecstasy.

It was two on one now, and when the cards were dealt, Bill was the loser, Tammy with the high hand among the girls.

"Well well well," Tammy said. "So what will it be, does Bill take a dare or does Tom lose his boxers and you all do the naked lap?"

All contents © Copyright 1996-2024. Literotica is a registered trademark.

Desktop versionT.O.S.PrivacyReport a ProblemSupport

Version ⁨1.0.2+1f1b862.6126173⁩

We are testing a new version of this page. It was made in 15 milliseconds