Another chapter posted tonight! I'll work hard writing and posting this weekend. Please leave feedback and ideas for some of the future activities that the boys get up to! 
Chapter IV: Escalation
Ryan
I tried my best to hide it, but seeing Andrew helpless outside was turning me on. His usual blond hair was now soaked and hung in brown curls. His boxers, now see-through from being soaking wet, hung low on his waist and you could see his bulge, which was made smaller from the cold.
"Should we let him in?" Tyler asked from the couch.
"I have an idea," I said, walking to the door. Andrew had stopped knocking and instead was just standing pathetically, dripping water. I opened the door a small crack.
"Ryan, this isn't funny man," Andrew whined, "Come on, let me in!"
"What do you mean, you look like you're having fun!" I teased, moving to shut the door.
Andrew made a move for the door but I pried his fingers off and slide it shut.
"Dude, let him in now," Nick said, getting up, "look, it's freezing outside."
"Fine," I said, opening the door. I was slightly annoyed that the show was over, "you can come inside."
Andrew rushed inside and grabbed a blanket off the couch.
"It's freezing out there man! Like it's 5 degrees at the most!" He said, shivering.
"Alright, alright. Sorry. I took it too far," I said putting my hands up defensively, "besides, it's your turn now!"
"Fine," he huffed, "alright Ryan, truth or dare?"
"Truth," I said, worried, but somehow a little excited, about what revenge he had in mind if I picked dare.
"Okay. Answer honestly..." He said, calming down a little bit. I was still having trouble keeping my eyes off his dick, which I could still slightly see through his wet boxers. "Are you gay?"
"Well I--" I started, caught off guard.
"Even now, you can't keep your eyes off my dick!" He accused.
"Yeah, I'm gay I guess then. But don't single me out! Nick had a tent when he was showing off for the pizza guy!" I said, trying to change the subject.
"Woah, don't drag me into this--" Nick said, standing up quickly.
"Guys!" Tyler said loudly, cutting everyone else off, "we're all at least a little gay, Nick was horny near the pizza guy, Andrew looked like he secretly loved being locked outside, and Ryan was barely containing himself when he teased Andrew like that. Let's just get back to the game!"
The room was silent for a long 10 seconds before I decided to break the silence.
"Tyler, truth or dare?" I asked.
Tyler looked up and grinned before replying, "dare!"
"Take off everything you have except your underwear, you can't get dressed for the rest of the game," I said.
We all watched Tyler pull off his hoodie and t-shirt. He was the skinniest of all of us, he was 5'11" but only weighed about 115lbs. He dropped his basketball shorts to the ground, revealing his tight Fruit of the Loom briefs.
"Do you always wear tighty wighties?" Nick asked, "that's kind of hot."
Tyler put all of his clothes into his backpack and joined the rest of us by the TV.
"Nick, truth or dare?" He asked.
"Dare all the way man!" Nick said with a big smile.
"Okay, you like my tighty wighties so much, switch underwear with me."
"Oh... okay then," Nick said, getting up.
"Also," Tyler added, "put on the knee high socks that are in my bag too."
The two boys went to the other side of the room and quickly changed, facing each other. They returned about a minute later and Nick sat down on a chair to pull on his socks. Tyler's small briefs were very tight on Nick, who was at least a size larger. You could clearly see his 6" erection at the front, and the back barely covered his ass. Tyler, on the other hand, was way to small for Nick's Calvin Klein boxer briefs. The stretched material hung loose, and he had to keep pulling up the waistband so they didn't fall off.
Nick checked the time on his phone before turning back to Andrew.
"Dare!" Andrew said, before Nick could even as the question.
"Okay," Nick said, "Give me a lap dance for 5 minutes."
After setting a timer on his phone, Andrew got up and walked over to Nick. He bent over in front of him, putting his ass right in his face. Andrew slowly moved back and moved down, until his ass was just barely on top of Nick's dick. Instinctively my hand went down my pants and I slowly started rubbing my balls.
Andrew moved up and down on top of Nick, until Nick started to moan. Andrew suddenly stood up and turned to face Nick, with their eyes never parting Andrew straddled the chair and began to grind back and forth on him. I looked over at Tyler, whose eyes were glued to the show in front of us.
The room was filled with soft moans as Tyler and I pleasured ourselves to the sigh in front of us, and Andrew and Nick got to experience it. After a few more minutes, the timer on Andrew's phone went off. Andrew got off of Nick, giggling at a small wet spot near the head of his dick.
We sat silently for a few more minutes, thinking back on what just happened. Checking my phone, I saw that the time was now 9:20.
"Tyler--"
"Dare, I uh, I think we're past the truths at this point," Tyler said anxiously.
"Okay, I dare you to spend the next 15 minutes giving me a foot massage," I said. Tyler came over and sat on the floor in front of me. I lifted my feet and he pulled off my socks, tossing them in the corner of the room. As he started rubbing and pressing on my bare feet, he called over to Andrew.
"Andrew, I want you to go change out of your wet boxers, and put on Hailey's thong instead."
Andrew nodded and smiled in agreement and picked the thong up off the table next to him. Standing up in front of us all he dropped his boxers. His pubes were non-existent, but looked as though they'd been shaved. His dick stood straight out at about 5 inches, but was not held down when he put on the black thong.
Just as he was turning around to give us a view of his ass, we all jumped as the front door slammed shut and heavy footsteps were heard above us.