College Sissy Program Pt. 09

Whatever could a sissy pageant even consist of? He had to know. Turning his head up to meet Shawnee's eyes, he smiles, remembering what just happened between them, and whispers. "What's a Sissy pageant?"

Shawnee looks over to see if Lily is poking her head out, convinced by seeing her shoes and clothes by the bathroom door that she can safely assume she is actually taking a shower.

"Well, it's both exactly like you think it would be and also not what you expect it to be at the same time. You will be asked questions and be made to pose and model in different outfits. But that's where all the similarities to things like Miss Universe end. You also will have to perform tasks given to you and will be judged by the princesses on each task. It's all in secret, so we don't know where anyone places until the top 5 are picked for the finals. Remember, the pink princesses can only have 1 or 2 sissies total, so they might pick the top 2."

"Why is Lily so pissed off about that? Does she secretly like me or something? She didn't want to lose me and seemed to not want someone to take me from you two. Who is that?"

"Well, something you don't know is that Lily was once in the Pink Princesses. But due to her being... you know how she is... they requested her out of the clique. She has actually been in all the different cliques, and all have kicked her out, so they stuck her here. We are technically the lowest-ranked clique in the totem pole. they dont kick people out of this place. They dont know what to do with her. She hates that she was tossed around and not accepted by the rest. So she doesn't want the leader of the princesses to get you. It's her rival, Angelica. They both fought to be leader of the princesses. It wasn't pretty. Lots of backstabbing, like in all those shows us girls love to watch. Eventually Angelica got the upper hand and got her booted. I don't know what for. But I assume it was pretty big."

Hunter now had a better understanding of why Lily was the way she was and her determination to make things like shit for him. He was about to ask another question when Shawnee heard the showerhead turn off and put her finger over his mouth and signaled him to get back down. Lilly walks out of the bathroom naked except for her hair in a towel and, of course, her chastity. She walks over to Hunter and Shawnee. Hunter gets an immediate chill feeling her behind him.

"Well, well, well, Sissy Jayne. Sounds like you've been a bad girl today. Today isn't your lucky day since I've had a shitty day. So I'm going to take out my frustrations on you. Shawnee, grab me a few pairs of my shoes, my whip, and Barney from the closet."

Shawnee sighs and grabs the items as Lily stands and rubs Hunter's ass in anticipation. She also plays with his plug, making him grunt. She laughs, "Oh, this is going to be fun."

Lily puts on some clear heels with purple lights flickering in the clear part. They were easy slip-on heels with no straps, about 5 inches, and a 3-inch platform. She picks up her whip and slaps it in her hand.

"You may turn around and face me, bitch. I want you to see and admire my body while I punish your pathetic ass." She cracks the whip across Hunter's ass. He winces and turns around on the bed, sitting in front of her. Lily was towering over him like a giant, and he was a tiny speck, her eyes full of fiery rage. There was no remorse for what she had planned. It scared Hunter a little bit.

"Hands on your ankles, bitch, and hold them there, then lean back and don't let go. I know you can't help but stare at my perfect body all naked, you pervert. You make me sick. Finding new ways to see women naked. You probably do bad things on purpose just so I can punish you. I like that, but it isn't what a little girl like you should do."

Hunter tried to interject. "No, I don't." but Lily whips his hands. "Don't talk unless I ask you a question Sissy Jayne. You need to learn your place. I thought you were learning these past few days, but it seems like I was wrong. Now hands on ankles and lean back."

Hunter stared at Lily in anger, but he knew if he attempted too much, then what was in store could be worse. He could be removed from Shawnee and their new friendship? Friends with benefits? Well, whatever it is would be in jeopardy, and he needed an ally. So he begrudgingly grabs his ankles and leans back, his ass and cage on full display for Lily to see and do as she saw fit. Lily quickly puts some fuzzy handcuffs on each hand and leg so they are connected and can't be freed from that position fully. Hunter tries to pull back on the cuffs but only gets, like, an inch. These were not like normal cuffs that had some slack. These had like 2 links, so there was virtually no movement. Lily sees him try to let go and lifts her leg and steps hard next to his head.

"I said don't fucking let go. I guess you really want this after all. Hands on ankles the whole time, or we start over."

Hunter looks over at Shawnee and sees the fear in her eyes and mouths sorry and shakes her head. He gulps and puts his hands back on his ankles and menially prepares for what is going to happen.

Lily paces back and forth, patting the whip in her hand, staring Hunter down. Every so often raising the whip to see his reaction. She is pleased to see him close his eyes every time. She then walks on the bed and bends down over his face. Her big ass right there in front of his face. She shakes it and looks to see if any reaction in his cage appears. nothing, so she shakes her ass a bit more. Still nothing. She then just sits on his face, smothering him. She looks again and sees the cage shaking a bit.

"You freak, you must love the 'smother me, mommy' memes." You must jerk off to them. You dirty girl. Well, I am tired. I think I'll stay here for a little bit while we play."

Lilly gets off his face and puts it back down a few times, making Hunter struggle to breathe each time. After a few minutes, she whips his cage, and Hunter muffles a scream under her.

"Awe, is little Jayne having trouble enjoying herself? Well, I can help with that. Shawnee, give me Barney."

Shawnee hands Lily the device. She turns it on, and a loud vibration can be heard. She lifts herself a little to flaunt it at Hunter. It was a vibrator. It had 3 different segments, all different sizes, but all had the shape of a dickhead. She sits back on his face and places the device by his cage, making it vibrate and making Hunter twitch in pain.

"You like that, Sissy? Remember, no cumming, or else I won't be the only one punishing you. But Barney is a good one; it works wonders on everyone. You know what? You should have it for a while. Luckily, it has a key ring."

Lilly sits up, letting Hunter breathe, and hooks the vibrator to his cage, causing many spasms by Hunter. She was satisfied with this and got off the bed and changed into black boots. They went up to her knee and had spikes all over the base of the shoe. They were 6 inches with a 1-inch platform. She put her foot by Hunter's face so he could see the shoes, then walked away and observed a few feet away as Hunter struggled. The vibrator felt so good, but the cage caused any hardness it gained to cause massive pain. He let out a few grunts and was breathing heavily. Eventually the breaths turned into moans.

"Well, now you are having too much fun. Can't be having that, can we?"

She walks over and whips his cage and places her hand on his plug, rubbing her finger around the base.

"Have you had sub ass play yet, sissy? You may speak."

Hunter didn't want to answer. He was cramping up being in the position he was in and breathing so heavily. He just shook his head.

"Well, it's the best class ever, Sissy. You get to learn so much about your anatomy and pleasure centers and how to stretch an asshole to accept so much. Like this plug, for example. I bet it feels weird now, but in time you will love it like a family heirloom."

An evil grin appears across her face, and she quickly grabs the plug and pulls it out of Hunter's tender asshole. He lets out a bellowing scream. The pain of the sudden removal of the plug left his ass sore. He felt the cool air of the room touch the irritated area. It felt good but weird. Shawnee and Lily were right. Since it was in there for a few days and he got used to it, not having it there felt off.

"Why am I feeling like that thing belongs in me? I don't want anything in my ass. I'm not gay and don't like anything near my ass." he thought to himself. Did he get more programmed during his trauma episode than he realized? Or was this a natural reaction?

Lilly laughed at Hunter's distress and piled it on by whipping his ass, making red marks with each whip. Enjoying every second of his struggle to not cum while getting brutally whipped, she breathes heavily, obviously turned on. She then walks over and unclips the vibrator from the cage, and Hunter sighs in relief. Lily inspects the cage--no cum, not even precum. This kind of frustrated her. She wanted him to fail. Shawnee could tell something was up. She saw Lilly thinking hard, then smiling again, and lifting the vibrator high.

"Well, it looks like I'm going to be your first class in SAP." Shawnee quickly runs towards Lily as she is holding Hunter's leg and moving the vibrator towards his asshole. Just before it reaches its mark, Lilly is pulled back by Shawnee, and they both go on the floor.

"What the fuck are you doing, Shawnee?. You shouldn't prevent me from punishing this fucking loser."

"You know you can't shove that up a sissy's ass unless it's one of your assignments, and I know it's definitely not. They have to have had 3 classes of SAP before any of us get that assignment, and usually the sissy tells us it's part of their homework. You'll get in so much trouble. You know you are on thin ice."

Lily screams in frustration and throws the stuff on the ground and stomps into the bathroom, picking up the clothes that were at the door. Shawnee uncuffs Hunter and gives him a wink. Then she picks up his plug.

"You should probably put this back in. Don't worry, I'll be gentle." She grabs a bottle of lube and places her hand on Hunter's stomach and slowly inserts 'the plug. A few grunts later, it's back in, and she pulls him up into a quick hug, then pushes him back and shakes her head while mouthing, We can't let anyone see that.

The Next day:

Hunter woke up to his alarm at 6 am. He looks at his calendar. It was laundry day; he had almost forgotten about that in his guidebook. He went to the closet as instructed and found the laundry attire. He sighed. He had expectations of what it might be, and he was right. It was a maid outfit. Of course it was that. He took off his clothes and put on a new thong and bra and tossed his in the hamper. It was pretty full. The dress was luckily stretchable and didn't give too much trouble being put on. It was black with purple puffy cuff sleeves that only covered the shoulders. It reached only just a bit lower than the school skirt. The frilly parks at the bottom were also purple and tickled his hairless legs. It was finished off with a hairpiece for his head and a choker that said his clique's name. As much as he hated this, he needed to see what this was like and where it would send him. He looked at his device and opened the notes section. It gave him specific directions on the way to the laundry room. Grabbing the hamper full of clothes, he walks out the door, following the instructions and paying attention to as much detail as possible.

A bunch of other sissies were also carrying their hampers but all seemed focused to a T. He tried to make small talk, but it was useless; they all just said they needed to get this done, or else they would be punished. Hunter left the dorm and took in his surroundings as he followed the crowd. Empty walls and cameras every 20 ft. No guards today, it seems. He passed by the cafeteria and the classrooms to another empty hall with a single door at the end. It was narrow compared to every other hall. He didn't see a spot that could be used for escape while on the walk. All the sissies stop in front of the door, hampers in hand, and wait.

crackle

You may enter the laundry room now. You have until 11 am to complete all the clothes. All power to machines will be turned off at the designated time. Anyone still with a hamper of clothes or things still in the machines will be getting their room a demerit, and you will have to stay down there until instructed otherwise.

Crackle

"Well, that can't be good. I bet there aren't enough washers and dryers for us all to get it done in the time frame," he said to himself. The door opens, and the sissies file in. When he reaches the door, there is a spiral staircase. He couldn't see the bottom of them from the top. "Of course it has to be the most inconvenient way to get to a place. Walking down stairs in heels while carrying heavy baskets that are hard to carry." He carefully stepped down the wood steps. Each one creaking as everyone stepped down. After a few minutes he got to the bottom and placed his hamper down and took a look at the room. Exactly like he thought, only 3 washers and 2 dryers. Once all the sissies came down, the room went quiet. A voice in the distance said, Begin.

With that, the sissies started going at each other. He wasn't expecting that. They were grabbing hair and kicking over each other's baskets. They kept saying how their roommates needed to be done first. Hunter was in shock seeing all the maid-dressed sissies act like wild animals. Two came charging to him. He quickly stepped to the side and whacked them with the basket on the way. The two fall on their faces and cry like little girls that don't get their way. Well, he knew what he had to do. He was hoping to get some frustration out. He walks towards one of the washers as multiple sissies try to stop him. He has gotten more used to his heels, so he was easily able to dodge and stomp on some people as he walked. He shoved a group that were all pulling each other's hair to the ground with a hamper by lifting it over his head and smashing it on them. He reached the washer and noticed some tape around where he was standing. It said safe zone. The others seemed to ignore him while he was there. He loaded the clothes into the top-loaded washer.

There was a sign on the washer.

To keep the door shut, sit on top of the washer.

"Oh, that makes sense. Definitely a sexual thing; it probably vibrates like a motherfucker. They do all the cliché stuff here, I guess."

After loading, he sits on the washer and turns it on. And, as expected, it vibrates a ton. It feels so good on his cage. "This must be what all the women mean when they mention this. Wait, why am I fucking enjoying this? This is war. I need to finish these clothes. This school must be fucking with my mind subconsciously.

After a few minutes, 2 sissies come from the crowd and put their clothes into a washer. They then take off their maid outfits and put them in the wash. Then turn it on and get on. "Oh shit, I didn't think they counted the laundry outfit as well. I guess since they make us fight for washing rights, it would get dirty and need cleaning."

He quickly hops off the washer and stops the machine. He takes off his outfit, puts it in the machine, then turns it back on and sits. He feels kind of bad for wasting more time for the others, but he figured they knew what they were in for. Looking at the bright side, his feet get to rest instead of standing. The vibration from the machine does trigger his dick a little, but he can manage it better. He took it as more of a full-body vibrating massage. Once finished, he took the clothes out of the washer and back into the hamper. He surveyed the room. The dryer is directly on the other side of the room from the washer. With the clothes wet, it would be harder to get to the other side. The crowd seemed to have thinned a bit; sissies littered the floor, either tired or probably knocked out. He looks for an opening and goes for it. Managing to do a quick walk without rolling his ankles while carrying the basket. From behind, his hair gets pulled and gets pulled back. It was the two sissies that were also as the washers. The determination in their eyes was fierce. Both luckily and unfortunately, the wigs are glued on to everyone's head very well, so they won't just pop off, but it does feel like you're really getting your hair pulled.

Hunter drops his basket and turns to see his foes. They go to kick him in the dick, but he turns, getting kicked in the thigh instead. He throws up his hands and takes a swing at one of them, clocking one of them right in the jaw, dropping her instantly. The other girl looks in shock and takes a step back, holding her hands in fists.

"Oh, so it's about to go down, is it?. Have it your way."

He eyes up and down his foe. Her heels were higher than his, and the fake boobs were also way bigger, at least a D cup. Her body was still masculine, but you could see a slight hourglass beginning to form. Her arms looked thin and toned. Her legs, though, look like no leg day ever got skipped. They weren't bulgingly muscular, but you could tell by the firmness that they had some kick to them. If he didn't know better, he would assume it was a female athlete. He realized that this was where he was headed the longer he stayed here.

The sissy makes the 1st move, giving a left hook. Hunter dodges but gets hit with an immediate kick to the side, causing him to lose his breath. She increases her advantage with a leg sweep, causing him to fall to the ground. Being satisfied with a victory She grabs her basket and tries to walk away. Hunter grabs her ankle as she gets away. "I didn't hear no bell."

He pulls hard, causing her to fall flat on her face. Hunter quickly gets on top of her and puts her in an arm bar while kicking her back. She screams in agony with each second of the armbar and each kick. Hunter tries to reach her logic center. "Look. We are the only two able to reach the dryers since your partner over there is knocked the fuck out. Let's just end this battle and dry our shit before others finish their wash cycle."

The sissy is crying from the pain and agrees to the terms. Hunter lets go and grabs his basket. He sees his former foe get up. There are some drops of liquid on the ground where she was on the ground. Did she get turned on by that? Then he noticed she was wearing black and remembered what Shawnee told him about the Cliques. Then black bitches love pain, so she must have been enjoying the pain but didn't want to cum. He took a second to let that set in and then walked to the dryer.

Once at the dryer, he puts the clothes in. It's a front-loading dryer. After it's full, he tries turning it on. It didn't work. There was another sign that said to activate the hold button inside of the tumbler for 10 seconds and then close the door. He looked inside, and indeed there was a button on the back of the dryer. He knew what this was referencing. He reached inside and pushed the button. As he was there, he laughed to himself and joked, "Oh, stepbro, I'm stuck." Once completed, he closed the dryer and started drying and watched the carnage in front of him as some more sissies got to the washer. Every moment another few drop and crawl in pain. It wasn't a pretty sight. A few more make it to the dryer. But they have to wait. It is another safe zone, so there was no animosity. The dryers buzzed, and Hunter started pulling out his clothes and asked, "Do we put our maid outfits back on, or do we just walk back to our dorms in our underwear?"

One of the 2 girls that got their answer. "You walk back in what you are wearing and put your stuff away." Hunter recognized the voice that answered. "Belle? Is that you?"

"Omg, Jayne! You look so pretty. What's your beauty routine?"

Hunter never thought he'd see her again. But something was different about her. She actually had some normal talking patterns, unlike the other sissies.

"I haven't seen you since Cosmo. What happened?"

"Well, I was a bad girl for cumming while you were getting all pretty. So I was punished and sent to counseling. I am thankful for all their help. They made me see the errors of my ways."

Counseling? Error of her ways? It sounds like brainwashing to him. He offered her the dryer he was using. Belle was thankful and hugged him, their cages touching as she embraced him. Hunter felt weird and pushed her off, navigated through the room, and got back unscathed.

Once back in the room, he saw Shawnee and greeted her; she was in the bathroom doing normal bathroom stuff. He started putting away the clothes and noticed Lily wasn't there. He looked at his planner: 8:30 am. Man, was he really down there that long? So many sissies must get punished each week; no wonder they are feral.

"So where is Lily?"

"She got called to counseling. They saw her try to use the vibrator on your ass and weren't happy."

"How long will she be gone?"

"A few days. That should be good news for us; we can talk more about things." She gives him a sexy wink. "She should be back before the pageant starts, though."

After putting the clothes away, Shawnee and Hunter talk about what he witnessed doing laundry and what he theorizes about what he witnessed. Shawnee isn't shocked but comforts Hunter and explains the dynamic they both have to adhere to for them to continue planning and not get caught. That night, Hunter got to sleep in Lily's bed at Shawnee's request, but he had to sleep while cuffed to keep Shawnee's cover. It was still better than the floor or at the foot of a bed where the girls kick in their sleep.

The next day Hunter woke up and saw the cleaning day notification and got to work. Outside was a bucket with supplies, a brush, cleaning chemicals, and a little vacuum. He began with the bathroom since Shawnee was still sleeping. Her planner was empty for the day. He cleaned the tub and was working on the sink when one of the patrolling guards walked in.

"So far so good, slut. Keep up the good work." She smacks his ass and waits for a reply.

"Thank you, miss. I'm glad I am doing well for you. Thank you for the ass slap." Hunter rolled his eyes as she walked away and continued cleaning.

Shawnee wakes up about 9 am and walks into the bathroom and pretends to scold Hunter and points him to the part of the bathroom the cameras can't see. She pretends to crack a whip at him but purposely misses and laughs while winking at him. She drops the whip and walks over and kisses him. She kisses not only his lips but his neck as well and grinds a little on him, making his cage twitch. She then tells Hunter to vacuum but pretend to be hurt from the whip so it looks believable.

He goes and limps as he vacuums. The guards check every 2 hours as expected and do the same ass-slap routine until the final inspection. She carefully inspects the room from top to bottom, then stands in front of Hunter.

"I will now give you your cleaning grade. turn around."

Hunter turns around, not knowing what to expect. The guard takes out a marker and writes something on his lower back above his thong. then slaps his ass 10 times.

"It's not often a slut like you gets a perfect 10 out of 10. Good job. Your teachers will be happy to see such good scores. Your roommate can now clean you out. Have a good day, you two."

With that, she exits the room. Hunter looks confused at Shawnee. "What does that mean, and what did she write on me?"

"I think you should see it. Come to the bathroom." They walk to the bathroom, and Hunter turns around to face his back to the mirror and turns his head. It was a butterfly that had the words wife/maid material written on its wings. It covered all along the bottom of his back. He was confused. Shawnee said she had never seen that phrase before. Usually it says things like "dirty slut" or "needs work."

"Well, now you need to be cleaned out for the next plug that you will most likely get tomorrow. Every Monday or Tuesday they change our plugs. I guess they care about being sanitary sometimes." Shawnee said while grabbing an enema bag and starting to fill it up.

Hunter didn't like any of this but knew he had to endure it, plus he trusted Shawnee. After the bag was full, she told Hunter to bend over and pull his thong down. Hunter did as instructed. Shawnee grabbed his plug and slowly removed it. Hunter moaned a little. Shawnee was being careful to not hurt him and make it at least a little pleasurable. Once out, Shawnee inserted the tube from the bag up Hunter's open asshole. It slid in fairly easily. As the water started filling him up, he shook his ass playfully for Shawnee to see. She laughed and gave a playful slap. Hunter could feel the water slosh around inside him until the bag was empty.

"OK, now I need you to hold it in there and do some squats so you are as clean as possible. If any leaks out, they make us make you clean it up, but not with any towels. You can probably figure out how. I'm grossed out thinking about it. So don't drip any, ok? Now you need to do 20 squats, and then I must spank you 20 times. Let's go, Jayne. I can't wait to see that body work it." A big smile and a few winks are flashed at Hunter.

He nods his head and starts squatting down. The pressure from all the water is intense. Shawnee tells him his ass needs to touch the ground for each squat to count. Hunter sighs. Of course it has to be that extreme. He can feel all the water in his stomach as he moves up and down. When he goes down there is massive pressure on his asshole. He takes a few seconds to compose himself, making sure it doesn't leak, before he goes back up. After 10 excruciating minutes, he finishes, and Shawnee spanks him for a good job and tells him to sit on the toilet to let it all out.

Hunter feels a huge sense of relief when the water quickly evacuates from his bowels. taking a few deep breaths after getting it all out. Shawnee let him linger for a while, then told him to get up and bend over for the reinsertion. Hunter gets up and bends over. Shawnee applies lube to the plug and puts it back in and slaps his ass when the deed is finished.

"So what do we do now?"

"Surprisingly, Sunday is a free day. We can walk all along the halls until 5 pm. It seems like a good time for us to search around for things. Of course I can go by myself, but you must be escorted by a woman. So you want to scout out the place?"

"For sure, let's go."

To Be Continued