Madison’s Challenge

You keep trying to get to sleep, but before you can get too much the balls leash and the cock cage do their part to prevent you from getting any real rest. Before too long, the sun is shining and it’s already 9 AM. You sigh, still tired and worn out from how long of a day yesterday was, and the night wasn’t much better. You look down and still see the cage tightly compressing your dick to an inch. You adjust your position a little bit, trying to get a little bit more comfortable before you lean your head back and close your eyes again hoping that it can make time go by faster. The next thing you know, you see Madison open up your cell door.

“Wakey wakey Lucas! It’s 11 AM.” She says. You see Emily walk in a couple seconds later, still looking kinda upset and disappointed after yesterday. You have no idea what she did after she left, but you imagine it probably involved her complaining to the other girls about whatever you said or did that made her upset.

“Now Lucas I have a game for you to play, okay? I know, I know, you’re probably wondering why Emily isn’t telling you this instead of me, well, because it was my idea and I’m taking credit for it and I’m surprising her with this too.” Madison starts.

“Just get on with it, what are we doing?” Emily says crossing her arms looking at her.

“Today we have your first challenge, Lucas. So here’s what we’re going to do. Every day or every week, one of the five of us girls will be giving you a different challenge to make you a better boyfriend candidate next school year. You’ll be learning different skills that will make you a better boyfriend, or more attractive, or will be fun little games for you that may be testing you on skills you already have. If you do well, and prove you’ve learned the new skill, have at least made really good progress, or that you already have that ability, then as an additional reward to the learning experience or the skill, you’ll also get time free from the cock cage as long as you behave and don’t make yourself explode while you’re free. Got it?” Madison informs you. This sounds incredible, you think. You get to learn new skills and develop, you get to maybe try new things, and on top of that for proving you can listen to the girls you also are getting time out of the cage guaranteed if you succeed?

“That sounds awesome, I love it. What’s first?” You ask enthusiastically. Emily looks surprised and curious by your willingness.

“Perfect! Game number one, we are testing your patience. All of these objectives, tasks, challenges, tests, whatever that day or week will all of course be testing your ability to listen to girls, do what we say and follow directions. That’s a given. You have to be able to do that to get time out of the cage. But the focus for this task is on patience.” Madison says. You look curious.

“Now, you may notice that Emily looks a little bit different than normal right now. That’s because she’s not in one of her normal school outfits, and because it’s summer break, she didn’t feel the need to do her makeup yet.” You look at Emily and you can see a little bit of a difference in some spots. Mostly her cheeks and eyes, but she still looks cute. You look at her outfit and it’s definitely a bit more muted and plain than the one she was in yesterday and what you’d seen her wear in her pictures while scouting her out before the gender wars.

“Madison you told me not to for this, this wasn’t my choice.” She says defensively.

“You’re right. Because here is Lucas’s first task. Before you on this table, we have a cheap breakfast of plain toast and an english muffin. At any point in time, you may eat from that plate, but, you only get what’s on that plate before dinner time in about 10 hours from now. So you have to go the whole rest of the day without food. Plus, your balls will be immediately leashed back up to the wall and you won’t get any time out of the cock cage if you take even a single bite from that plate.” Madison explains. You grimace at the idea.

“However, if you display good patience, listen to Emily and follow her directions during the game, you will get a full breakfast, your leash will be unlocked from the wall until after dinner, and your cock cage will come off until after dinner as well, assuming you behave and don’t play with yourself.” Your eyes bulge in excitement and happiness at the possible rewards. You look genuinely happy as Madison smirks and Emily looks on confused.

“So, what do I need to do? What is this patience game I have to pass?” You ask. Madison chuckles and smirks.

“And what does it have to do with me wearing a boring outfit and no makeup?” Emily chimes in still kinda upset Madison gave her those instructions this morning.

“Well, one thing a good boyfriend has is patience for his girlfriend to get ready before they go out somewhere. Whether it’s a date, or dinner, or a party, or a trip to the grocery store, girls need time to get ready to leave their home. So… The challenge is… You’re not allowed to touch anything on that plate until Emily completely finishes her hair, makeup and picks out her outfit for the day, and then spends up to an hour doing whatever she wants to give you a makeover.” Madison smirks mischievously. Emily chuckles a little bit, surprised but slightly intrigued, as you still feel pretty good about this. A good breakfast, several hours out of the cage and your balls being unlocked from the wall? Worth it.

“Sounds kinda fun and interesting, not gonna lie. Think you can handle that, Lucas?” She looks at you, finally showing a little bit of positive vibes for the first time towards you in a while. “I’ll even toss in a boy treat if you behave too.” She adds.

“Oh, and also, because this is a patience test, anything encouraging Emily to hurry up, go faster, increase her pace, take less time, etc. etc. is banned and is also a fail condition immediately as well. No rushing your girl during her getting ready routine. Got it, Lucas?” Madison looks at you, as Emily smirks happily. “As for Emily, you can’t intentionally delay or screw anything up and you can’t restart at any point. It’s supposed to be authentic and genuine, not a delay and draw this out as long as possible. You still have stuff to do today as the girls leader and you can’t do it until you finish getting ready.” Emily nods, agreeing to that condition.

“So does this mean I get to see how Emily does her makeup and hair?” You ask curiously. Emily looks intrigued.

“You’re interested in how I do my hair and makeup?” Emily asks confused and curious.

“I mean, yeah. Is that not a normal thing to pay attention to or..?” You ask back. Emily smirks.

“Fine then, I have a bonus game for you. If you pay close enough attention to details, I will give you a short three question quiz at the end. If you pass, not only will you be able to keep the cage off until after dinner, I’ll even let you sleep with it off until tomorrow morning when we wake up if you get all three questions right. But don’t think it’s going to be easy, I’m not going to give away or tell you the answers.” Emily smirks.

“That’s the spirit! Now you two have fun, I’m going to go check on our girls lunch.” Madison says as she exits the cell, leaving you alone with Emily in a much better mood than she was in the last time you left her.

“Okay, I’m going to go get my makeup bag, hair supplies and, well, I guess you won’t be able to see me pick out my outfit since it’s in my room, but I think I already know what I want to wear today so it won’t take me too long to get changed. And no, I’m not getting changed with you watching yet if you were thinking that. Though I guess I could since you’re leashed and caged. But I’m not ready for that yet.” She says. “I’ll be back really soon. Oh and I should probably unless you to see if you go for the muffin and toast plate while I’m gone huh?” She says as she unlocks the balls leash from the wall, giving you freedom to go around the room while you wait for her return. She leaves the cell happily as she heads to pick out her outfit and get her hair and makeup supplies, leaving you hopeful and optimistic yourself that you can pass this challenge and use this as a chance to impress her and prove yourself, but also get those very nice rewards.