What Could Go Wrong?

Tom must have walked around behind where Hilde and I saw watching, Hilde still crying on my shoulder. "Sorry, Monica," Tom said, leaning forward near my ear. "I'll get Bill back to you real soon."

After a couple more minutes of watching Tammy suck on Brent while jacking off Bill and Sam, Tom made his way around to her rear and finally dropped his boxers. He was somewhere in between Sam and Brent in terms of size, big but not a monster, and he had let his public hair grown in a wild shamble around its base. He leaned in near Tammy's behind and stuck two fingers in her vagina, causing her to let out a surprised sound from her mouth, an inarticulate "hhmph!" around Brent's cock in her mouth. Tom teased the fingers in and out, then stuck his thumb into her puckered butt hole. Again, she let out a muffled noise as her last hole got filled.

Tom then removed his fingers and shoved his raging hardon into her vagina, fucking her in a syncopated rhythm to Brent's thrusting in her mouth, pushed one way and then, before she could recover, pushed from the other end, all the while move her hands up and down Bill and Sam. She was building speed on that front, Bill and Sam starting to groan as well as she handled them deftly with her tight fists. Tom stuck a finger back into her ass, then another, and then a third, probably stretching her sphincter wider than anything she'd ever experienced. I held Hilde tight against me. She was crying less now, and like me, just watching in awe at Tammy servicing - or getting serviced by - four boys at once.

I figured Tom would last the shortest since he was the only one who hadn't cum already this evening, but he was still going strong, balls deep in Tammy's cooch, when Sam began to spurt into the air above her fists. She kept stroking him but very slowly, wringing every bit of seed from him. Bill started bursting, too, his little pecker spouting sticky streams into her hand as well, and she kept on pumping him as well.

Brent and Tom still had more stamina, working Tammy between them like two lumberjacks running a long saw across the trunk of a tree, back and forth, in sync now, knocking her back and forth through their cocks in her mouth and vag. Bill and Sam just stood their, their soft cock and empty balls still getting massaged by Tammy. Tom still had three fingers up Tammy's ass, for good measure.

Eventually, Brent stopped thrusting, instead sticking his cock as far back in Tammy's throat as physically possible, using both hands now to pull her face towards him, but even so there was an inch or two of length that couldn't get past her lips. Her mouth starting leaking his cum, there not being much more room in there to hold any, and she was really gagging now, unable to breath except through her nose, and it seemed like enough cum was coming out that it must have been seeping out her nostrils too. Brent at last withdrew his sausage and the last ropes of white hit Tammy right in the eyes, blinding her and mixing with the rest, which already had been mixing with her sweat and her saliva and her tears.

"Oh, no," said Tom, not even a hint of disappointment in his voice, "we were all supposed to come at once. I guess you'll have to take a forfeit." Tammy was crying too hard to say anything.

Tom stopped thrusting and removed his cock from Tammy, still hard and dripping with Tammy's juices. He withdrew his fingers from her ass and, unceremoniously, rammed his cock back into that now-empty hole.

"AHHHH" Tammy screamed in raw pain. She wailed and thrashed as Tom plunged her rectum, going deeper with each trust, Tammy feeling every milometer as Brent held her head in place so she couldn't escape the chair. Her back arched and squirmed, but she soon realized that the more she angled her ass, the more it hurt. She had let go of Bill and Sam and they retreated back to the table, Bill sitting down next to me and Sam next to Hilde.

After what seemed like an eternity, Tammy's screaming got horse and ragged and eventually muted to a sustained, low whimper, her crying audible again.

Finally, Tom slowed his motion, and must have cum and gone soft since Tammy's stopped whimpering. Tom stepped back, softening cock pulling out of Tammy's ass with a loud 'pop' and moved to Tammy's head. He helped her untwist from the chair and she stood, legs shaking, barely able to stand, and she almost fell, but Tom caught her and helped her back to the chairs, handling her almost tenderly. He sat her next to Bill and Brent took a chair too.

We all sat in silence for a moment, the only sound ringing in the quiet basement of the frat being Tammy crying. She shifted on her chair, her hand pressed against her still tender rectum, trying to clamp it back to its previously tight space.

"So," said Hilde, "that's it, right? Can we all go now?"

"Sure," said Tom, pulling his boxers back up, "but one thing I think you guys should know first." He walked behind us and came back with a cell phone, and he pressed the scream a few times before it started playing a video - Hilde bouncing up and down on Brent's cock, his hands grabbing roughly at her breasts, her screaming in pleasure.

"Oh my god!" said Hilde, her eyes almost flying out of her sockets. "I -"

"Wait wait," said Tom. He closed that video and pulled up another. It was me, laying on the floor, covered in Bill's come, masturbating furiously.

"And one more," Tom said, this time showing Tammy getting her face fucked by Brent as she jacked off Bill and Sam. Despite the placement, you could clearly make out it was Tammy, furiously stuffing as much of Brent's penis in her mouth as she jerked off the other two.

"What . . ." Hilde started, but Tom kept talking.

"Jeff, right? That's your boyfriend? I found him on Facebook. I'm sure he'd just love to see this video of you having an absolute ball without him." He turned to Tammy, who was fighting back her tears to watch the video of herself. "And Tammy, your dad is a local politician in Philly, right? I'm sure he'd love to have this little clip come out next time his city council seat is up for election." Tammy said nothing, just continued crying. "And I'm sure your pledge master at the sorority would love to know what kind of pledges they have this year, and maybe the whole campus would love to see how you gals spend a Friday night. Hell, maybe the school would put these on their website, it would be great recruiting material."

"What do you want?" I asked, myself now starting to tear up. The idea that anyone - my friends from home, my parents - seeing me pleasuring myself on a frat basement was just too much. I'd be ruined. I'd have to change my name and move to another country. Somewhere without the internet.

"I just want you gals to have a good time with us," he said. "Whenever, and however, we want. Understand?"

We all nodded, not knowing what else to do.

"First, I'd like a little more for the library." He had us pose for pictures, standing up, front and back, sitting down and pulling our lower lips apart to give the camera on his phone a great view of our feminine secrets. We pulled our ass cheeks open and showed our brown buttons, Tammy's still stretched out from Tom's penetration earlier. He had me kneel down and Bill and Sam stick their dicks in my mouth, Tom acting like a real photographer and angling the shot to get my face and as much of their cocks as he could fit in the frame. He repeated the same with Hilde, then he and Brett did the honors for Tammy, who was still crying as she fit as much of their large members in her mouth.

"Very nice," said Tom, finally satisfied. "Now I'll just need your phone numbers, so we can give you instructions whenever we get the urge." He entered them into his phone's contacts, and found the phones themselves in our purses to make sure they were right, texting us each a picture of ourselves with two cocks in our mouths. He rummaged through and found contacts for our parents or anyone with the same last name and copied those over, too. "Great. Now, the night is getting late and it'll be morning soon. If you ladies want to make it back to the dorms without getting seen, I suggest you leave now."

"What do you mean, without being seen?" Hilde asked. "We did the dares, we get our clothes back, right?"

"Well, you did do the dares, but I'm guessing you'd rather make the run back naked and not have to worry about Jeff seeing this video, rather than make the walk back in your dress but then wake up the next morning to a text from Jeff wondering what he just saw.

"But that's not fair!" I screamed, knowing that I sounded like Tammy. "We did everything you asked, and you promised we wouldn't have to do a naked lap and now it's so much more."

"Monica, you surprise me," Tom said sadly, "I thought you were the best sport during our game."

"But you're not playing the game as we agreed!"

"Ok, have it your way, Monica," Tom said, taking out his phone again. He made a big show of pulling up my video and starting a text chain with my father. "Do you think he'd prefer text, or email?"

"No!" I yelled.

"Good," said Tom. "No more resistance from you?"

"No," I answered.

"Everything I say, goes, right?"

"Yes," I said.

"And no talk of not obeying?"

"No."

"Good." He smiled, then whispered something to Sam, who pulled on his own boxers and ran up the stairs. "Come over here," he told me. I had no choice but to walk over to where he pulled a chair over. "Lean over and grab the chair," he said, and I leaned over, my ass to the group, my hands grabbing the edges of the seatback. I stood there in silence until I heard Sam return down the stairs, not seeing him given my angle. Tom thanked him, and suddenly I felt a giant stinging on my ass.

"Ouch!" I screamed, my butt fat still jiggling and the feeling of the sting percolating through me.

"The preferred response is, 'thank you sir, may I have another?'" Tom said, calmly. "We won't count that one, in any case."

He walloped me again, with what I assumed was a wooden paddle, and it stung worse than the first, my skin already raw and red from the first strike.

"Thank you sir, may I have another?" I whimpered, hoping that would do it, but Tom just took the recitation at face value and gave me another, this one again harder and more painful than the last. I gave the correct response and he wailed on me again, and again, and again. I think it was about ten in total but it was hard to focus between the pain and taking all my concentration to ask him for another. At last, after I made my forced request, another wasn't coming.

"I think that should make my lesson pretty clear," Tom said, an edge in his voice now apparent that I had never heard before. "No more problems from you, right, Monica?"

"No," I whimpered, still arched over the chair.

"No what?" He asked.

It took a second before I could figure out what he wanted, then finally I answered "no, sir."

"There we go. Now, just one more thing to let you friends know I mean what I say. Sam, hand me the other thing."

I started getting scared, not know what the 'other thing' would be. Tom walked in front of my, and I could see he was holding a pool cue.

"Open on up," he said, and I opened my mouth. He stuck the cue in there, but not hard, just inserting it and letting me place my lips around it. "Get it all nice and wet." I did, licking it and tasting it's hard, lacquered wood, a hint of chalk on the tip. After a minute, he removed it and moved behind me.

"Now Monica," he continued, "in the spirit of our last chat, any objection to me doing what you think I'm going to do?"

I had no choice. No choice but to cry, and say, "please, sir."

"Excellent," he intoned.

I felt the cue jammed up my ass, hard and sharp and without much help from my saliva. It hurt, hurt worse than the paddle and anything else I'd ever felt in my life, sharp pain rippling through my spine like I was getting gutted from the inside. Thankfully, he didn't make multiple thrusts after its initial entry, just slowly pushing it further and further up. I knew I was screaming but couldn't even hear myself over the pain. He kept pushing and I kept screaming, like I was dying, like the pain in my ass was a sharp blade that would slice me in two. I couldn't imagine it could go any further, but it did, and then another inch, and I screamed that much harder.

When he finally stopped, the pool cue still in my ass, I thought it was over. It almost was. He let is sit there for a few second, then twisted it, sharply, clockwise, and I screamed again, then he jerked it counterclockwise and I screamed louder. My insides were churning and grinding and he twisted back and forth, back and forth, back and force, and I thought I would pass out from the pain.

He pulled it out all at once, and it hurt but finally the pain felt good, and my ass puckered back but not fully, still stretched out from the pain of the cue. Tom walked back around to my front and presented the tip of the cue. It smelled like shit as he pressed it to my face, and commanded me to clean it. I licked it and took it in my mouth again, ran my lips up and down it as far as I thought it might have gone. It tasted different, now, not just the lacquered wood and chalk but my own anal juices and, to my shame, tiny flecks of shit that he must have dislodged.

Tom patted me on my butt and told me it was ok, he was done with me now. I stood up and almost fell, I was so weak, and I felt a poop coming that I wasn't sure I could keep in. I tried to flex my sphincter but it was so pummeled that I couldn't get it closed all the way. I shooed away Tom's help, and he started growing cross but when he saw the brown stuff leaking out of my ass, he started laughing, and taking out his phone to get me involuntarily pooping on the floor, still naked, still with Bill's dry cum on my face.

"Ok, ladies, I think we know the stakes here." He looked at a clock on the wall. "It'll be morning soon. I suggest you gals make your run back now, before first light. It's a mile away and I think if you start now, you'll get back before then. We'll be in touch."