College Sissy Program Pt. 06

Lily laughed hysterically while firmly holding Hunter's planner. She got great thrill from seeing others in pain and suffering. Hunter stood there worried about what was so funny about his schedule.

"Well, what does it say, Lily? What is so funny?"

Lily manages to stop laughing for a few minutes and wipe a tear from her eye. " Well Sissy Jayne, if you must know, you are scheduled for plugging, then humiliation 101 then SAP. This has to be the best schedule I could have read. It's like they are trying to turbo you to graduation. I didn't get SAP for at least 2 weeks after plugging."

Hunter was confused at what Lily was saying. But from her demeanor, it had to be bad. "What does that even mean? What is plugging and SAP? And why are you so happy to see that on my planner?"

"You know the deal, sissy. I will give you answers once you do a task. Each task is 1 answer. And don't you tell her anything, Shawnee, or I might consider that undressing as a sissy and female relationship and have to tell staff."

Shawnee glares at Lily but knows not to cross her. She would sell you out for a compliment to boost her ego more. She shrugs her shoulders at Hunter and lowers her head while shaking it. "Fine, Lily, whatever. You cunt."

"Awe Thank you, Shawnee. I take that as a compliment. Now Sissy Jayne, I will tell you about plugging. But first you need to get me ready for the night as well, remember? Oh, and I do remember your reaction from lunch. So I'll make a similar offer to them." She takes out a tube of lipstick. "You remember this? It's the special lipstick that makes you super horny. If you can get me ready for the night with this on and not cum, I will answer all your questions with no sass for the rest of tonight. As many as you desire. I'll still answer per task as normal if you do cum, but you'll have to smear and cum, you drip, on the floor directly on your pretty face. Do you accept the deal, sissy? You don't have to use the lipstick, but this will fast-track things since I can tell you have lots of questions."

Hunter took a few minutes to think. This has got to be some sort of trap. He remembered the agony he felt while kissing all the clique's shoes at lunch. It was painful in more ways than one. Not only was the pressure in his cage almost unbearable, but his pride took a big blow while down there and being used for entertainment. Suddenly a random thought came through his head. "I hope I can please Lily. I wish I had her shoes." He shook his head a little and regained composure and kept pondering, saying to himself that he would worry about that weird thought later.

"Well, sissy, I don't have all night. Well, actually, we do. We can't leave the dorm after 5pm without permission. But you understand what I'm saying. Hurry the fuck up." Lily was getting impatient but was enjoying seeing Hunter struggle deciding on which is less bad. She knew which version he would choose in the end. And right on cue, Hunter answers.

"I'll take that challenge, Lily. But may I add a stipulation to the wager?"

Lily perked up in excitement and intrigue. "What do you have in mind Sissy Jayne?"

Hunter had seen Lily's personality type before. Most of the frats he joined and got in trouble for just to take them down had a few with her flavor. He had to turn the tables, even just a little, so he would have an advantage but make it seem like they still had a big advantage; that way they still feel superior. 'Well, Lily, I think you would much better enjoy showing me how much better you are than me at things rather than just proving how bad I am. I suggest a best 2 out of 3 contest of tasks. Winner takes all. We both wear the lipstick while doing the tasks. And if someone cracks before the best of 3 is over, then they lose by default." Hunter waited for her response. He didn't have to wait long.

"Oh, does the little sissy think she is a big girl now? Pretty ambitious for your 1st day. I accept, but since the rules have been changed, the wager itself should be changed a bit. If you manage to beat me, I'll still answer your questions, but I'll also add on one more request at your digression. But only if you win. Now, if I win, you will have to call me Goddess and Shawnee Mistress whenever you speak to us. Failure to do so will result in a kick in your cage down there. Also, for the next week, I get to write something on your back that you won't get to see; it will be like a daily tramp stamp for all to see but you. So sissy, are you prepared to take this challenge now?"

Hunter was expecting a counteroffer. These types always have to add more because of their high confidence level. They really love being able to rub it in when they win. This was now a bigger risk, but he felt compelled to take this to gain some ground and hopefully show he's not as pathetic as they want him to be.

"Ok, Lily, I see your game here. I accept. But to make it impartial, I suggest Shawnee gives us the challenges and is the judge of winners."

"Yeah, that's fine with me. I can't wait to see this little bit of defiance crushed under my heel, Sissy Jayne. Shawnee, first challenge, let's make this quick."

Shawnee looks at Hunter with a 'what the hell are you thinking' look and then thinks of the 1st challenge. "Ok, ladies, I'm honored to be the judge of this contest. Your 1st challenge will be bra brackets. The first to put on all the bras in their drawers all at once will win. All bras must be snapped close for it to count. Also, there will be the anti-horny spray in my hand in case you want to forfeit at any point. Lastly, of course, no shirts on for this. But that should be obvious. Remove them before I say, Go."

Hunter looks at Lily and sees her smug face. It makes Hunter more happy to wipe that off her face if he wins this. They take off their shirts. Hunter now got a better view of Lily's breasts than what he saw at lunch. They were basically popping out of her bra. Lily noticed Hunter staring and smiled in her typical evil way, knowing her big boobs would be a distraction for a sissy. She playfully shakes them a bit to see if that gets a rise. Hunter looks away, knowing he needs to concentrate. Shawnee walks over and applies the lipstick to both contestants. A nice thick layer at that. She gets into position.

"Contestants ready... Set... GO GO GO!!"

Lily pushes Hunter and quickly gets to her drawer and takes out her bras. Hunter looks at Shawnee.

"All pushing and distractions are allowed, Jayne. Now get going."

Hunter gets to his drawer and pulls all his bras out of the drawer. Then it hit him. He has never had to put a bra on himself before. He has only ever unhooked women's bras. He looks at all the bras and notices different styles. Some are very basic, some are frilly, and some are very thin. He counts about 10 bras; that shouldn't be too bad. has seen women put these on before. He glances at Lily for a quick check on how it's done, then separates the bras by style, making a plan on which ones to do in what order. His idea is the thin ones, then lace, then basic. As he puts his arms through the straps and reaches towards the back, his nails get in the way of getting a good grip. He's still not used to having to be nimble with long nails. He struggles to hook each hook on the back of the bra. Fingers slipping with each attempt. just barely missing. Then finally he gets it. and works on the next one.

"Contest over. Lily is the winner."

Hunter turns around and sees Lily had put on all her bras. He can't believe she was that fast and he barely got one finished. But then again, women should be experts. He just had to hope the next one wasn't as unbalanced.

"Awe, the little sissy bitch couldn't get more than one on. One day you'll be able to get them on faster. But that will take you time, sissy. Next challenge, Shawnee, I'm getting a little hot over here."

Hunter could see Lily trying to resist the lipstick's effects. She was sweating a little bit. But Hunter barely felt anything... until he thought about it. Then he felt the pressure in his cage, just like at lunch. But he had to move on. Lily takes off her bras and throws them on the floor next to Hunter, exposing her breasts.

"When we are done, you're going to have to put them back anyway, win or lose. Might as well have them closer to the dresser for you, sissy. Aren't I so nice?"

Hunter sighs in defeat and tries not to look at her breasts again but can't help taking a few peeks while getting up. He sighs and waits for the next challenge; he's more determined to get this one. He needs to win it.

"OK, ladies, that was a fun 1st round, but now for round 2. Jayne needs to win this one to tie it up, or else she is as big of a loser as we think she is. Your next challenge is wedgie sumo. Each contestant will put on 3 pairs of underwear. Then you each get a turn that will be longer each round. 10 seconds will be added each round. On your turn you will pull all 3 pairs of underwear on your opponent as high as you can and hold it until the time limit has ended. The winner will be determined by a person saying uncle or if you rip all 3 pairs off your opponent. Since Jayne lost the 1st round, she gets to go 1st in the pull. Ladies, go put on 3 of the lacy thongs in your drawer."

Hunter was a little weirded out by this challenge. He and Lily go to their drawers and take out their lacy thongs. Lily removes her skirt, showing off the rest of her perfect legs; no cellulite to be seen here. She gracefully removes her thong and flings it at the hunter's face. bullseye. Hunter quickly brushes it off his face as Lily chuckles and puts her thongs on. He secretly thinks to himself, "Man, I didn't know we were at the fish market." Then he removes his skirt and removes his thong and puts it in the hamper next to the dresser along with Lily's. The feeling of the lacy thongs being pulled up his legs gave him a good sensation. It made his cock tremble more in the cage. It was starting to get to him. He was breathing heavier, but so was Lily.

"Ok, ladies, it's time. Lily, turn around, and Jayne will begin." Lily turns around and slightly bends over. Hunter walks up into position and grabs the straps. "You can go whenever you are ready, Jayne." Hunter takes a deep, calming breath and forcefully pulls the thongs up, reaching Lily's mid-back. He never felt so vindicated as at this moment. Lily lets out a quick "eek," then a loud moan. The moan threw Hunter off a bit. Was she... enjoying this? He then notices something: the strings are pressed against it.

"Time's up! Lily, it's your turn. Jayne, turn around."

Hunter turns around and waits for Lily to begin her turn. Lily stands behind him and whispers in his ear. "I bet you noticed something about my ass. What you saw has to do with your plugging tomorrow. Don't worry; it makes this challenge more... let's say enjoyable." Then he swiftly pulls up on Hunter's thong. The pain of the fabric rubbing against his bare ass was strange at best, but it also put pressure on his cage, causing more discomfort. Luckily it didn't last long, but the lipstick was obviously having an effect. You could smell it in the air. the familiar fragrance of horny people.

The rounds get more intense each time: 20 seconds, 30, then 40. Each time, making them hornier and sweatier as they try to resist. Then round 5 happens. Hunter was in so much distress, and Lily could see it on his face and couldn't help herself but to poke at it.

"Looks like the sissy is about to explode. Just come already so we can get on with our night. There's no shame in being so turned on by getting the privilege of seeing me basically naked. Cum, you little bitch, cum."

Hunter shook his head in defiance and grabbed her thongs. And with one final pull, he rips all 3 thongs at once. It happens so fast he falls over on his ass. Lily lets out a huge, loud moan. You can see her vagina is getting decently wet under her chastity.

"Jayne is the winner. Challenge over!"

Hunter couldn't help but throw his hand up in the air in victory. He had gotten some redemption from Lily and showed he was capable of more than whatever they think a sissy could be. Lily didn't take too kindly to this sudden joy Hunter was experiencing. She stomps over and kicks Hunter in his cage again a few times.

"You little bitch. You are fucking nothing... that win means nothing. You are just a pervert. getting so horny over seeing me naked, probably. Getting to touch a woman like myself must be your fucking fantasy." She spat on him. Shawnee trots over to get Lily off him.

"Lily, calm down. It's just a game. You can still win the next round. There's no need to go that extreme. Get a fucking hold of yourself." She slaps Lily a few times. She knows how she gets when he is really horny and angry at the same time. Lily manages to calm down after a moment. Getting some joy seeing hunter on the ground in fetal position after being kicked so many times in the balls.

"Well, just take that as a warning, sissy. I'm still above you. Now let's get this last challenge off."

Shawnee offers her hand to Hunter. He grabs it and gets helped to his feet. Luckily, those kicks seemed to have lowered the horniness.

"Okay, ladies, last challenge..."

Suddenly an alarm goes off in the dorm. a big, loud, bellowing siren. An announcement comes over a speaker.

*crackle*

"Attempted escape discovered. All women, dress your sissy for head count. Outfit 23 for today. Bring all sissies to the cafeteria."

*crackle *

The announcement repeats over and over.

"Looks like we will have to finish this another time, Sissy Jayne. Let's get you ready for headcount."