The Penetration of Caitlin

Caitlin found herself grinding her teeth as she sat in the wooden desk chair that Ridgefield College provided in every dorm room. Her laptop was open, and she was looking at her Econ 101 slides, trying to distract herself, but her heart wasn't really in it. Her eyes kept glancing to the bottom right of her screen. It was 8:57 and the college punishment technician was supposed to knock on her door in three minutes.

It was a new program here at Ridgefield based on the Punishment Codes established a few years ago by the legislature that allowed low level crimes to be punished with corporal punishments. The Office of Student Behavior, a department inside the larger Office of Student Affairs, assured all new incoming students that the first trial of the so-called Ridgefield Codes was designed with input from all stakeholders of the college, administrators, faculty, staff, and students, and that their incorporation into the fabric of the institution was going to be slow and iterative, with changes, based on feedback, incorporated after each semester.

Only new students, freshmen and transfer students, were subject to the Ridgefield Codes. Sophomores, Juniors, and Seniors were still subject to the old disciplinary system of administrative write-ups, fines, and potentially a student trial. Each year, as seniors graduated and a new class joined the college, a higher percentage of the student body would enter the program and, in four years, the transition would be complete.

The cautious and contemplative approach to the codes did nothing to make Caitlin feel any better. She had seen in the student newspaper, the Ridgefield Current, that the first punishments had been carried out the previous week, but she still knew that she must be among the first dozen or so students to get the dreaded knock on the door.

KNOCK KNOCK KNOCK

Caitlin jumped and looked over her shoulder at the door. This was so unfair. She'd broken the rules, but she still didn't think she'd done anything wrong. It was just a hot plate! Her mom had bought it for her so she could boil water for spaghetti and ramen, and she hadn't even thought twice about putting it out on the edge of her desk. When the fire marshal came through, which apparently happened the first month of every semester, it was confiscated, and she'd gotten written up for possessing a fire hazard.

She took a deep breath as she closed her laptop and got up. She knew she wasn't even the only person in her dorm hall to have a so-called hazard. Her friend, Tatiana, a few doors down had a whole espresso machine, but she'd known to hide it until after the marshal came through, the benefits of having an older sister at the school.

Her desk was right next to the door so it took less than one step to reach out and turn the knob. When it opened, she was surprised. "That could be much worse," she thought as she beheld the woman that stood in front of her holding a large black bag. The woman was young, maybe only a decade older than Caitlin, and dressed in dark blue medical scrubs with dark blonde hair pulled back in a ponytail. She was skinny, slightly rosy cheeked, and a few inches taller than Caitlin, which wasn't hard as the teenager was only 5'3".

"Hello," the woman said, reaching out a hand, "I'm Eloise Wendell and I'm from the Office of Student Behavior."

"Yeah, um, I figured," Caitlin said, ignoring the woman's hand and stepping back and letting the woman into her dorm room.

"Thank you," the woman said, acknowledging the invitation into her room. She entered and looked around the cramped bedroom. The room was rectangular. Across from the door was Caitlin's wooden desk, with a tall back and shelves and covered in notebooks and pencils. Behind the desk was Caitlin's bed, covered in a pink bedspread and a pillow against the far wall. In a mirror image, her roommate's (a nice girl named Alice who was avoiding the room for the next hour) setup was the same. A dark blue blanket covered Alice's bed and her desk was covered in magazine cutouts of celebrity men she found attractive. Near Alice's desk was the one small closet they shared. A rough blue rug covered the tile floor in between the two beds and a wooden dresser, provided by the college and matching the pale wood color of the desks, stood underneath the window that usually looked out over a patch of woods on their rural campus, but Caitlin had drawn the shades, knowing what might happen in the next hour. The beds were tall, owing to the limited closet space, and each of the girls had brought plastic boxes to hold most of their stuff which was under their beds. Underneath Alice's bed there was the low hum of their shared minifridge that held water bottles and diet soda. "Could you show me your ID please?" the woman said, using a pleasant tone.

"Yeah," Caitlin said. She reached toward her desk and took her phone which had a holder for her cards. She took out her college ID and handed it to Eloise who examined it. Caitlin had brown hair that went just below her shoulder. It naturally had big loose curls that she often had to brush out from her eyes. On her ID, she had a nice smile, and a strong jawline and cheeks with a slight bump in her nose that she could never decide if she liked or not.

"Caitlin Riordan?" she asked.

"Yep," Caitlin answered before correcting herself, "Yes, ma'am."

"You don't need to be formal. I know this is hard but I'm not here to make it harder than it needs to be. Feel free to call me Eloise," Eloise said.

"Ok," Caitlin answered.

"Why don't you sit down. We have some things to talk about," Eloise said.

Caitlin nodded and sat down at her desk, turning the chair to face Eloise who stood at the opening of the corridor between the two beds.

"As I said, I'm Eloise Wendell and I'm from the Office of Student Behavior. I'm here to carry out a punishment given to you by the Office which you have decided to not contest. Is it true you don't contest the finding that you had a prohibited fire hazard in the dorm?"

"Yeah, that's right," Caitlin said, looking a little past Eloise, unable to look her in the eye.

"Ok, good. A little bit about myself then. Officially, I am an Assistant Punishment Consultant, though usually I would just call myself a punishment technician. Before being here at Ridgefield, I worked in a government judicial center, so I am an expert and I want you to know that you're safe in my hands," she continued. Caitlin raised her eyebrows and tilted her head. "I know that might not make you feel better, but I decided to come here because I want to work in a position where the punishments are less severe and focused on changing your behavior. I know that what I do isn't fun and I have a duty to teach you a lesson about breaking rules but I'm going to make it as easy as I can."

Caitlin shrugged and looked down at the floor. She was unenthused as she answered, "Ok, I guess that's good."

"I think so too, and the Ridgefield Codes give the both of us some latitude to make it easier, ok?" Eloise responded, with cheeriness that Caitlin thought did not fit the situation.

"What does that mean?" the teenager asked.

"It means the punishment happens here in your dorm instead of a center or a public place, for one, and it's me here, alone, instead of a man since we have a commitment to same gender technicians. It also means that if you listen to directions there won't be any cuffs or other restraints," Eloise answered.

Caitlin hadn't thought of those things and found herself nodding along, "Ok, but what do I have to do. I still don't know what the... punishment, I guess, is going to be."

"You're right," the technician said, "There are two parts to the punishment and one of those parts is actually up to you."

"What do you mean?" the teenager wondered.

"So the first part," Eloise continued, not answering her directly, "Is that we are going to take some pictures, both clothed and unclothed."

"What?" Caitlin jumped, her eyes going wide.

"Just relax. No one is going to see them except me. The Codes are still being tested, for now, and in the future it's possible that publication of pictures will be part of the punishment but for now we are still testing the technology."

"I don't get it," the student reiterated.

"Again, no one is going to ever see them. We are just testing the software where the pictures are taken and uploaded to a secure server. In the future only other members of the Ridgefield community will be able to see the pictures but you're just part of a test," Eloise explained.

"So we are taking the pictures for no reason?" Caitlin said, trying to stay calm.

"Well, it's still part of the punishment," Eloise answered, "But it's not as bad as it could be."

Caitlin's eyes were wide and she looked around the room, avoiding eye contact with the technician. "Totally naked?" she asked.

"Yeah," Eloise answered slowly, breaking bad news.

She knew, or rather suspected, that she was going to be at least partially undressed. It was no secret the Ridgefield Codes were based on the Punishment Codes where criminals were paraded naked through city parks and on to stages for corporal punishments, but she hadn't really thought about it so concretely. Caitlin bit her lower lip and fought back panic. Her mind was racing but she took a deep breath and gulped, "Ok, I understand."

"Good," Eloise said slowly, like she was expecting more from the student sitting in front of her but when nothing was forthcoming, she continued, "The next part is up to you."

"How so?" Caitlin answered.

"Well, this is an interesting way in which the Office has organized the codes," Eloise responded, "The punishments are organized into different categories and students are given a choice of punishment from within a certain category."

Caitlin processed the news slowly, "So I get to choose what happens to me?"

"What punishment you receive, yes," Eloise confirmed.

"Wow," Caitlin said slowly, the opportunity dawning on her.

Eloise bent down and opened her black bag which sat near her feet. She extracted a white tablet and tapped on the screen, "You have been given a category three punishment and get to choose from a list of four."

Caitlin realized this was a big deal. She wasn't sure what she was most scared of happening, but this was a way to make sure it never did. She just had to pick the punishment that was easier than the others or at least easier for her. "It might still suck but it will suck less," she told herself, as she waited for the technician to read the list.

The older woman looked down at her until she realized that Caitlin was waiting for her to continue and then she began to read, "One: You can choose for me to cane your buttocks and thighs. Two: You can choose for me to pinch and squeeze your breasts in a painful manner. Three: You can choose for me to spank your vulva with my hand. And four: You can choose for me insert my fingers into your anus, again, in a painful manner."

Silence, except for the low hum of the mini fridge, hung in the air. Caitlin could feel blood rushing to her cheeks as she blushed. "Oh, wow," she said to nobody.

"You can have a couple minutes to choose," Eloise said.

The teenager's mind raced. They all sounded so bad and now she had to choose one to happen to her! "Uh, uh," she stuttered.

"Just take your time," the technician said soothingly.

Caitlin had heard of caning and imagined herself leaning against her bed and a big stick, which would surely emerge from that black bag at Eloise's feet, slamming down on her ass. She could picture the big red lines and not being able to sit down during class and she dismissed that one as an option.

Then her mind went to having her boobs groped. Her breasts were very small and sometimes she was embarrassed of them. Only one person outside her family had seen them, a boy named Andy just a few months ago she'd met on vacation. She'd gone through all of high school without a boyfriend and she saw her chance with a stranger, a year older than her, that she caught staring at the hotel pool. She found a way to talk to him and they had made out on the dark beach that night where her bikini top ended up on the sand. He'd played with her tits, and it felt nice, but he was definitely excited and a bit rough. She could only imagine what would happen if someone was trying to hurt her boobs, so she didn't like that idea either.

Choosing to have her vulva spanked was quickly thrown out as well. Andy had touched her over her short shorts, but he was gentlemanly enough to not even try to go under. Caitlin realized she was about to be naked for pictures but assumed that getting spanked down there would mean exposing much more with her legs open for another person for the first time. No way she could do that, plus, she could imagine getting her but spanked or her nipples pinched but what would it even feel like to have her pussy spanked? Could she even take more than one? Her stomach turned at the idea and she just knew she would throw up like a boy being kicked in the balls.

Finally, her mind came to the final option. Was having fingers in her ass even that bad? It would definitely hurt. She'd heard whispered rumors about girls letting their boyfriends try it. It always hurt but this was just fingers. Somehow, it seems less sexual than the choices involving her vulva or tits. She looked up at the woman and her eyes flickered over the woman's fingers on the back of the tablet. They weren't huge.

She crossed her arms defensively over her chest and couldn't believe that's what she was really going to choose. Her mind just kept concluding it was the best one. There would be no scars and it seemed to her the least sexual of the punishments. Her asshole just didn't seem sexual in the way her boobs or vulva did. "Does that make any sense?" she asked herself. Caitlin knew people did butt stuff during sex but somehow it just seemed different for her.

Eloise bent over and began to rummage in her bag. She noticed that Caitlin was watching her, "Oh, just ignore me. Take your time to think."

Caitlin was struggling to change her mind but was annoyed how quickly one punishment jumped out to her like the fingering did. That was probably a good sign right. "Go with your gut, right?" she reminded herself, but the other woman was giving her time, shouldn't she take it?

Eloise pulled out a sheet of paper and held it against the tablet, waiting.

"I-I think I'm ready," Caitlin mumbled.

"Are you sure?" Eloise asked, "I'd rather you not have second thoughts."

Caitlin tightened her arms over her chest, but her mind was made up. She looked up at the technician and tried to look serious, "I know my choice."

"Ok, then," Eloise replied.

The girl gulped and could feel her heartbeat quicken as she answered, "I want the... as... anus fingering." As she said it, she could feel her muscles tighten in her butt and she bit her lip. It was the right choice but now it felt very real.

The technician looked down on her, noticing her nervousness, "Are you sure?"

"Yeah," Caitlin answered quietly.

Eloise wrote in pen on the piece of paper she'd extracted from the bag. When she was done, she handed it to the girl. On a mostly typed form, in block handwriting on a line, was written CATEGORY 3: ANUS FINGERING'. "Sign that where it says 'student' and date and put the time. It's, uh, 9:12."

The student complied, writing her signature in pretty curly cues she'd practiced since elementary school. "Here," she said, handing it back.

"Thank you," Eloise responded, taking it back and awkwardly signing her own name, "Do you mind if I use your desk?"

"Go ahead," Caitlin answered, pushing her chair away from the furniture and wondering why she didn't use Alice's.

Eloise stepped closer to her and bent over the desk. Caitlin watched as the woman took a picture of the now signed paper. Her heart was beating fast at what she'd just agreed to do, and she got the feeling that now that the paperwork was being signed there was no backing out. She gulped again and tried to figure out what was next. The only thing she could think of was stripping. Her skin crawled at the thought of it, but she tried to remind herself that nobody was going to see the pictures and she was lucky. Eloise was a woman and seemed perfectly nice. Embarrassing but it was just them. She was even in scrubs, just like she was at the doctor with a nurse.

"Ok," Eloise said picking up the now signed sheet, "I'm transmitting an image of what we both just signed to the Office for recordkeeping. When we are done, you'll get the physical copy and a digital copy. Are you ready to begin?"

Caitlin was getting more nervous and answered honestly, "I don't know."

"I understand, but the first part is easy," Eloise answered, "Just pictures. Clothes on."

Oh right, stripping wasn't next she remembered. The girl sighed, "Fine, I guess."

"You have to stand up. We'll use the bare wall there," the technician said, looking at the off-white wall that was between the door and the desk.

Caitlin looked at the wall as she got up from the chair and pushed it under the desk, "Just stand there?"

"Mmmhmmm," Eloise hummed with a nod, "Just standing. Hands at your side. Ankles can be together, but they can't cross."

"That's easy, I guess," Caitlin said, reminding herself more than stating it for the technician.

"You're going to be fine. This is hard, but you'll be ok," Eloise assured her, smiling at the girl.

It felt nice to hear the words even if Caitlin found them a bit hollow coming from the woman about to finger her anus. She nodded as she got into position. Absentmindedly, she pulled down on her shirt, getting out the wrinkles.

The directions she'd gotten in her email had told her to wear clothes she'd be happy to wear to class. Caitlin had wondered why and now she knew it was because in the future the college wanted students being punished to be recognizable around campus. "Well at least they don't want me in a mini skirt," she told herself. Instead, she'd just gotten dressed as normal. She had a class at 11, PHI 112 Introduction to Ethics, and she planned to wear what she was wearing now to the lecture hall.

The teenager had a t-shirt with wide grey and white stripes and jean shorts that went a third of the way down her thigh. On her feet, she had strappy, brown leather sandals. Her feet were small, and her nails well taken care and her fingernails were painted light pink. She chewed her lip as she straightened her shirt and pulled her shorts down as long as they could go and looked up.

The technician was holding up the tablet, the camera lens in the corner glinting in the fluorescent light from the ceiling. "Smile," the technician said.

Caitlin wasn't in the smiling mood, but she pressed her lips together and gave them the smallest of an upturn for the other woman who tapped the screen.

"Back toward me," Eloise requested.

Caitlin turned, feeling better to not have her face in the image. Even if no one ever saw the pictures, they were still going to exist. She stood with her nose to the wall showing her small round butt, for now still in jeans, and waited for Eloise to tell her to continue. Again, she felt a tightening in her bottom and her stomach dropped at the reminder of what was to come.

"Ok," the woman said, waiting until Caitlin looked over her shoulder, "Now I need you to take you clothes off."

The girl bit her lip. Her face burned but she nodded that she understood the order. She knew it might happen. It was the one part of the punishment that she knew about, or could assume with any certainty, before Eloise arrived. "I really should be more ready for it," Caitlin chided herself, but she really wasn't prepared.