I just want to say that I really love and appreciate this thread.
I think I will try this challenge myself in the next time. Its really an amazing idea!

So I couldn't sleep and decided to jump back into the game.

Firstly I went to the nearby cave and met Team Aqua again for an easy battle, while there I caught a Zubat called "Flapper"

Making it up the volcano I caught a Numel on the path to the Fourth Gym, I called her "Hot rock" because I am terrible at naming things.

I then took my Pelipper and Azumarill and challenged the gym which is the easiest gym I've come to so far. Deep Throat destroyed everything from the entrance to the Gym leader, but almost for beat by her Torkoal, I switched into Bubble for the final hit and won the gym.

And now for the dares.

Because I used Deep Throat I went and got a banana from the kitchen and gave it a blowjob for 5 minutes, while I was in the kitchen I got a glass of water and poured it down my pajama bottoms because I used Bubble.

Gonna keep playing a bit more and hopefully will feel the need to go to sleep soon.

<3 Kah

Moving on from the fourth gym I went into the desert and caught a Sandshrew I named "Dig Dig Dig" and then I focused on training Mr Punchy until he evolved so I could challenge the 5th gym, I beat his first Slaking and Vigoroth with a little struggle, but his second Slaking almost destroyed Mr Punchy so I switched to Bubble and used her Power Up Punch and high defense to overpower it and defeat it.

After winning the battle I poured a glass on water down my underwear, I'm wearing a skirt today and didn't think things through and soaked the carpet in my bedroom. While I sat in soaking panties I took off my top and twisted my nippled back and forth for 2 minutes leaving them very hard and clearly showing through my top when I put it back on.

<3 Kah

After the 5th gym I went to route 118 and while surfing I caught a Tentacool I called "Squidy" and on route 119 I caught a Gloom called "Emo." The game also gave me a Latias I called "Jet." The route just after the 6th gym had me encounter a Kecleon I called "Voyeur"

I set out to do some training before the 6th gym, wanting to evolve my Numel into a Camerupt before challenging it. Disaster struck however when my Hot Rock was OTK'd by a critical hit Areal Ace, killing him and forcing me to switch him out with "Dig Dig Dig" who I am going to train up until it evolves into a Sandslash.

My punishment for losing Hot Rock is a 10 minute cold shower. I will be breaking this up into 5 separate 2 minute session, which I will complete before my next play session.

<3 Kah

Here lies Hot Rock, a cunning team member who wanted to train to be the best, but through unfortunate luck lost his life to a critical hit.

After training Dig Dig Dig until she evolved I went straight for the 6th gym hoping to use Zeus to sweep her team. I started off great, using its mega evolution to get even more power from his electricity I destroyed her first pokemon, she then brought out Alteria and feeling uneasy about fighting it I used Zeus's 'Volt Switch' move to deal damage and run out of battle before any damage could be dealt to Zeus. This was the smartest choice I could have made because Alteria used Earthquake and had a good shot of killing my little Zeus. I switched into Wingspan who kept chipping away some damage, but a constant stream of Roost made it hard to deal the final blow. Eventually Wingspan took too much damage and I had to switch, I switched into Deep Throat hoping to use 'Supersonic' to have Alteria stop using roost, but that failed and I nearly lost my inappropriately named Pelican. I had a tough choice to make on who to switch into next, My options were Latias, a powerful Pokemon, but its dragon type was weak against the Alteria's Dragon Breath, or I could bring out Mr Punchy and hope he could stand up against Alteria's attacks. I chose Mr Punchy because he had less risk of getting beaten and I was lucky that Alteria hurt itself in confusion. I used Mr Punchy's move 'Dual Chop' to deal super effective damage, but it wasn't enough to defeat it. I had to risk one last attack because whoever I switched into would have been beaten by her next attack, I used Dual Chop again to defeat it.

The other 2 pokemon she had I used Zeus to defeat them with no struggle at all.

And now for my dares for the pokemon I used.
Zeus means I have to do 20 puchups, easy.
Wingspan makes me wear pegs on my nipples.
Deep Throat has me give an object a blowjob, I'll use a banana.
Mr Punchy makes me twist my nipples.

I will be doing all of these dares naked.

Current team status:
Matectric/Zeus - LVL38
Pelipper/Deep Throat - LVL 32
Swellow/Wingspan - LVL 40
Machoke/Mr Punchy - LVL 34
Latias/Jet - LVL 33
Sandslash/Dig Dig Dig - LVL 22

<3 Kah

Moving on from the 6th gym I advanced in the story, just trying to power through the boring stuff so I can actually play the game and not encounter cutscenes every 5 seconds. To that avail I caught some new team members, Magikarp called 'Period,' and a Shuppet called 'Dolly.' Disaster struck early as Dolly fainted immediately as I started trying to train her. Killing my ghost before I had a chance to bond with her. And Banette is one of my faves too >:(

I hadn't had time to assign a dare to Dolly, so I'll take my punishment for losing her as 5 days in denial.

Next up is the Team Aqua hideout, can't wait to get past the boring Aqua stuff and go back to playing the fun parts of the game.

<3 Kah

Here lies Dolly, a member of the team I was so excited to have, but in my haste to have her meet the level of the rest of the team I let her die in the first battle while training. We will miss you my little Dolly.

Another day, another gym beaten.

Before that though I sped through the Team Aqua hideout, just wanting the boring part of every pokemon game to be over ASAP, and then I jumped on the back of Deep Throat and swam my way over to the island with the 7th gym. Before challenging it I sent to the nearby cave and caught a Spheal, I named her "Blue Ball," and quickly evolved her into Sealeo. I also discovered shortly after that my new friend has Pokerus, which is going to make this challenge a Hell of a lot easier.

(If you don't know, Pokerus is a rare virus that pokemon can sometimes get that makes them get stronger faster, and this virus can be passed onto other pokemon you own making your whole team get stronger faster.)

I then went into the gym and when meeting the twin gym leaders I realized quickly what my mistake was. I remember the two of them having 4 pokemon between them, but in the version of the game they only had 2, meaning sending out Zeus first was a huge mistake as he was completely ineffective against them. I quickly switched into Bubble, so her and Deep Thoat could combat the two floating rocks with their water moves.

Bubble had to quickly make a retreat after she was hit with a Solar Beam and reduced to 1 HP, I had a mini heart attack after that happened and screamed for joy seeing that she survived. I quickly switched into Jet just as Deep Throat defeated the Solrock with Surf. I then used a combination of my Mega Evolved Latias and Pelipper to gang up against Lunitone and beat it easily.

DARES
Firstly, for using Zeus, I performed 20 push ups.
I then got a banana and gave it a very generous blowjob.
After I took my glass of water and poured it into my underwear, I was wearing a dress today (Naked right now thanks to TallGuy2241) so the water made quick work of soaking underwear and then the floor.
To finish up I had to dance naked for 10 minutes for using Jet. I made the choice to search for "Stripper dancing" on YouTube and tried to copy it as best I could, praying the whole my brother or his wife wouldn't come into my room.

Current Team Status:
Manectric/Zeus - LVL 47
Azumarill/Bubble - LVL 43
Latias/Jet - LVL 42
Sealeo/Blue Ball - LVL 36
Pelipper/Deep Throat - LVL 46
Swellow/Wingspan - LVL 47

<3 Kah

And another gym is defeated.

But first I had to wrap up the Team Aqua stuff. I ran through the cave with a repel active and avoided all Aqua Grunts, I faced their leader and beat him with Zeus alone. I fought Kyogre and didn't want to catch it because I really hate how the games force you to track the Legendary Pokemon, I must proffer the original games where hunting the Legendary Pokemon was optional and by doing so makes you able to roleplay more into the game as someone who is actively trying to fill the dex and not accidentally stumble into it.

ANYWAY...

I beat the 8th and final gym with minimal effort. Using Mr Punchy to combat the Wishcash and Zeus to fight the rest, as well as using Deep Throat for a clean switch when I needed it without risking heavy damage. Next stop, the Elite Four.

DARES:
Mr Punchy made me twist my nipples hard for 2 minutes, leaving them so hard they poked through my dress as I walked downstairs to grab a banana to give a 10 minute blowjob to. And finally ending with 20 naked pushups.

Current Team Status:
Manectric/Zeus: LVL 52
Machoke/Mr Punchy: LVL 46
Latias/Jet: LVL 45
Sealeo/Blue Ball: LVL 42
Pelipper/Deep Throat: LVL 50
Swellow/Wingspan: LVL 51

<3 Kah

DISASTER HAS STRUCK

My first battle in Victory Road has lost me 2 members of my beloved team. At first I was doing great, Zeus OTK'd the trainer's Sigaliph easily, but then his second Pokemon was a Rhyperior and it nearly destroyed my entire team. I switched to Mr Punchy to try to use the type advantage against it, his strongest attack barely scratched the big rhino, and his attack almost killed Mr Punchy. I desperately switched to Deep Throat to try to avoid getting hit by its ground type move, but then it used Stone Edge and killed Deep Throat. Hoping to get another type advantage against it I switched into Blue Ball and did decent damage with an Ice Move, but then Stone Edge killed Blue Ball too. I switched into Zeus to try to use it's Bite attack to finish off the last bit of health it had, but it wasn't enough and Zeus almost died too. Finally I switched into Wingspan and luckily dodged a ground type move. I used Brave Bird to finish Rhyperior off, but now I mourn the loss of 2 of my beloved team member, and am about to suffer the punishment for letting them die.

PUNISHMENTS
For losing Deep Throat I must now give a 20 minute blowjob to a banana (fun -_-)
Next for losing Blue Ball I will have to put 2 handfulls of ice in my underwear until it melts.
And finally I will spank myself equal to their levels combined, which adds up to 92 spanks.

Tonight is not going to be a fun one.

<3 Kah

Today me mourn the loss of 2 of our dear friends.
We mourn Blue Ball, who despite being a new member to the team, was exceptionally useful in many battles and always came through when it counted.
We also mourn Deep Throat, someone who has been a crucial member of the team ever since the start of my journey, and is responsible for me winning several gyms and making it all the way to Victory Road.

Today I challenge the Pokemon League.
My first opponent has been defeated, Sidney the Dark type user. I started with Mr Punchy and easily dispatched his Mightyena. He switched into Shiftry and I sent Zeus, using his Flame Thrower to easily defeat it, and then he sent Sharpedo and a quick Discharge cooked that fish. I switched back to Mr Punchy to use his Cross Chop to defeat his Absol, and finally back to Zeus to set his Cacturne aflame and win the match.

DARES:
Easy could of dares, first I twisted my nipples for a few minutes to get them nice and hard and sensitive. I then performed 20 pushups and am now ready to combat the next Elite Four member.

<3 Kah

The next Elite Four member has been defeated.

Phoebe is the Ghost type user and to combat this I but Jet in the front line, with his Psychic and Shadow Ball he was a perfect pokemon to use here. Unfortunately this battle was more of a challenge than I had anticipated. It took the combined effort of 4 of my pokemon to defeat her Dusknoir, which has resulted in a humiliating set of dares.

DARES:
Jet required me to dance naked for 10 minutes. Once again I looked up a Stripper Dancing tutorial online and copied it as best as I was able to.
Then for using Zeus I performed 20 pushups.
Mr Punchy twisted my nipples again.
And finally, Wingspan has required me to keep my nipples pegged for 10 minutes. After twisting them for so long they are very sensitive and made the pegs hurt so much more than usual.

<3 Kah

Easy fight, I beat the 3rd Elite Four member with Zeus alone. 20 pushups and I'm ready to challenge number 4.

<3 Kah