The Penetration of Caitlin

Eloise looked sympathetically at the girl, "I don't have to watch but I'll see you eventually."

"Um," Caitlin hesitated, "That would be nice, yeah."

"Ok, it is easier that way," Eloise answered. She tilted her head to her right, toward the rug between the two beds, "I'll stand there, and you will have the desk between us."

Caitlin nodded, agreeing that that sounded good, "Ok."

The older woman took a couple steps to the side and Caitlin could see that she turned her back and faced the closed window at the back of the room. The student liked that the woman seemed committed to making it as easy as it could be. It's not like Caitlin could have stopped her from staring as she disrobed so to have her volunteer to turn her back felt good. It's not like she was going to run away. She wanted to be here at Ridgefield, and she'd have to drop out if she didn't take the punishment but, obviously, it was still good for it to be as easy as possible.

With a deep breath, she started, telling herself it was just like being at the gym. She knelt down and fiddled with the buckle on her right sandal and slipped it off before repeating herself with the left. Caitlin kicked the shoes to the side and tried to get on with it.

Her hands crossed in front of her chest and took the bottom of her t shirt and pulled up. Her stomach was pale and flat with a long slit of a navel. When she sucked in, her ribcage was visible and as she got the garment higher, she revealed a nude colored 28A bra that completely enveloped her small breasts. She pulled her shirt off over her head and then pulled her arms out one by one and dropped it on the floor, nudging it out of the way next to her sandals.

Caitlin fixed her hair and shook it to get it back straight after her shirt messed it up and then her hands went to her shorts. They were high waisted, almost reaching her navel, and she opened the metallic button and pulled down the zipper. She pushed them down, wiggling her hips to get them off. Caitlin was quite small, and her hips were narrow, so they came off quickly, falling to her ankles. She wore a nude-colored thong that matched her bra. Small, slightly lighter lace went around her waist. The girl was happy that Eloise was looking away. She hadn't thought about it this morning but if she had then she wouldn't have worn such sexy underwear. If a picture in her underwear was required, then it would be much better to have fully covering briefs, after all, and even if there wasn't a picture it still felt strange to wear a thong before a punishment for some reason, she couldn't quite pinpoint. All she wanted was to not have panty lines but now that choice made her stomach turn.

The teenager told herself it didn't matter as she pulled down the straps of her bra. She pulled her right arm out of the strap and then the other and then, doing it quickly before she got scared, pulled the band down to her waist. Her small breasts were spaced far apart and came to pointy, small nipples with tiny areola only barely wider than her nub. With a deep exhale, she turned around the bra and opened the clasp and dropped the garment on top of her shirt and nudged her jeans into the pile as well.

There was only one thing to do, and it was both the easiest and the hardest. There were no claps, no buttons or zippers, and no arms to get out of the sleeves. It wasn't going to mess up her hair either but dropping her panties and standing naked in her dorm room was still the most difficult step. She chewed her lip and hooked her thumbs in the elasticized lace. Her nose flared as she took a deep breath and let them drop. The fell down her legs and pooled at her feet and her sex was open to the still air of her dorm room. Curly dark hair covered her mound and extended down to her thin, slightly dark lips. The hair on her labia was thinner and couldn't hide that pink labia minora poked through along the length of her slit from her clit on top all the way down and under her body to around her opening. She slid her thong into the pile of her clothes and covered herself, crossing her legs to hide all but the top of her bush and holding one breast in each palm.

Caitlin prepared herself to be seen naked for the first time, first time as an adult, at least. Andy had seen her tits at and said he liked them as he kissed her neck, but nobody had seen her vulva in years. It was probably middle school since her mom had seen her naked and she didn't have any sisters to share a bathroom with. "Ok, I'm ready," she said weakly.

"Good, are you feeling ok?" Eloise said as she came back from the closed window, having gamely stared at nothing for a while.

"I've been better," Caitlin answered, "Nervous."

"That's a fair feeling to have," Eloise replied, affirming her, "Are you dizzy?"

Caitlin checked herself, "No, um, kind of hot."

Eloise looked at her, "You are flushed but I think that's explainable."

The teen laughed awkwardly, "Yeah, well..."

"Let's just keep going," the technician suggested, "It's just two pictures."

Caitlin nodded, again taking a deep breath, knowing that she was going to have to uncover. Awkwardly, she took a step back to stand against the wall.

"Good," the woman said, as Caitlin went back to the spot, "You do have to..."

"I know," Caitlin answered before Eloise could finish.

"Ok," Eloise said. She picked up the tablet and tapped the screen and held it up, "I'm ready when you are."

Caitlin nodded, her cheeks burning, as she stared at the lens. She took a deep breath and dropped her hands and uncrossed her ankles. Her tits and bush and lips were out for Eloise and the camera to see. "Do it quick, please," the girl squeaked.

Eloise's finger went to the button on the side of the screen and clicked. "All done," she announced.

As quickly as she could, the girl covered herself again. That was a scary two seconds, and her heart was beating fast. "At least it was quick," she told herself.

"Ok, that was great. Thank you. Now I need you to turn around. There's one more picture," the woman told her.

"Yeah," Caitlin said. She'd already figured that, and it was nice to be able to turn her front from the camera. She put her nose against the wall for the second time and put her arms and feet in position. Her butt was small, but she thought it was nice and round. Unlike her boobs, she kind of liked it, but, in the circumstances, it seemed ominous, and she could feel her asshole tighten in preparation. Stripping had almost made her forget the punishment that lay ahead of her. She told herself that she had made the right choice, but she was getting more and more nervous.

While Caitlin was lost in thought, the technician finished this part of her job. Eloise lowered the tablet, "Ok, that was the last picture."

Caitlin nodded but she was still embarrassed. The fact that they were just test pictures and none of her classmates could ever access them really didn't make it feel any better to know the files existed somewhere out there on a college... mainframe, database, server... she didn't know the exactly how all that stuff worked but she didn't like that they were out there somewhere. She looked over her shoulder to see the technician looking down at the tablet. She took a deep breath and spoke quietly, "Now what?"

"Just a moment," Eloise said, "I have to get these uploaded and then we can continue." The woman looked down, looking a bit confused but caught herself and checked in, "Tell me how you're feeling?"

Caitlin hesitated to think. The technician kept checking in and it never got any better. "About the same," the freshmen answered as she covered herself and turned around. If anything, she was even more flushed, her neck and shoulders growing red just like her cheeks.

Eloise nodded sympathetically but didn't offer to spare her in anyway. "Ok, we are almost ready to start," she said, looking at her screen, "As soon as... yep, pictures are done. We can now move on to the actual punishment. We are almost done. I'll be gone in ten or fifteen minutes, and you'll be able to get on with the school year."

"Ok," Caitlin said, unsure of exactly what to say to that. She hoped so but she didn't really think she was going to just get over it.

Eloise stepped out of the way to allow Caitlin a path back to her bed. "Come sit on your bed and we will talk about how it's going to work."

Caitlin kept herself covered as best she could as she walked two steps past her desk and turned toward the covered windows and turned left to sit on her bed. She could still, even though she'd never once thought about it before today, feel her butt tightening. The teenager told herself she was just imagining it, but she was really debating begging to take another penalty. Getting her tits groped didn't sound so bad when her ass seemed like it was actively making her punishment worse as it approached. "Paperwork's already signed," she reminded herself, telling herself she was just nervous as the moment approached.

Eloise held her tablet in front of her like she was double checking everything as Caitlin climbed onto the tall bed. With no clothes on, she wasn't going to sit cross legged, so she sat with her legs hanging off the bed with her ankles linked. She kept her left hand over her bush and her right hand cupped one breast and she hid the other in the crook of her elbow. "Ok," Eloise said, hesitating for a moment, "With your permission, I'd like to use your pillow, there, and a towel. It will make it easier and more comfortable."

"Yeah, that's fine," Caitlin agreed, seeing no reason to complain.

"Thank you," the technician said, "Where do you keep your clean towels?"

Caitlin tilted her head to the wardrobe next to Alice's desk, "In the closet. Mine is the pink one."

Eloise went to the closet and opened it. It was full of dresses and a blazer that Caitlin bought 'for interviews' that she hadn't needed yet. On the back of the now open door were two towels, Caitlin's pink one and Alice's light green. "Is it clean?" Eloise asked.

"I've only used it once," Caitlin said.

"Ok," the woman replied before taking it, closing the closet, and returning to stand between the two beds. She placed the towel down on Caitlin's bed to the teen's left and continued, "In a minute, I'm going to ask you to put your pillow in the middle of the bed and cover it with the towel. Then you'll lay on your stomach with your hips on the pillow. Do you understand?"

"Um, yeah," Caitlin answered. If anything, she felt a little better. She'd imagined being on her hands and knees pointing her vagina and ass to the woman. This seemed much nicer. She'd be in profile to the woman and her front was pressed down on her comforter.

"When you're ready, I'll start the process by touching your anus with my fingers. I suggest you try to just relax because I will attempt to enter you with a single finger."

Caitlin exhaled. She could feel her butt clenching and she blushed at the thought.

"It will be painful," Eloise admitted, "But it is a punishment. I do have the option, if I believe it will make the procedure more effective, to use a second finger."

Caitlin's eyes went wide, and she fought back a gasp. The technician must have noticed as her voice softened and she tried to assure the naked student in front of her. "If I use a second finger then I will introduce lubrication."

"What?" Caitlin interjected.

"Oh, I can show you," Eloise said, turning to the bag of her equipment that still sat on the floor.

"N-no, I know what it is, but you don't start with lube?" Caitlin asked, worried and stunned.

Eloise stopped before she bent down to her bag and answered, "Yes, I will start the punishment without lubrication and I will use as little as is necessary if it turns out that you need it for the first finger."

"Oh no," Caitlin said, more to herself than to the other woman.

Eloise responded with a thin-lipped smile. In her hand was a white bottle with a pump top that looked like what would hold conditioner or bodywash. "I know it sounds harsh," the technician started, "But I'm certain that you will make it through. It's not as hard as it sounds, I think."

Caitlin's eyes stung as she felt tears come to her eyes. "I...I," she stuttered.

The technician looked concerned. "Caitlin," she said soothingly, "Don't cry. It's going to be over in just a few minutes if we can focus and get started. Would you like me to keep explaining or..."

Caitlin spoke haltingly, interrupting the other woman, "I don't think I can." It had come out of nowhere. She'd chosen a punishment and got naked and stood for pictures without cracking but as soon as she heard the way it was going to happen her calm was broken. The teenager tried to hold in her tears, but she had to wipe her red eyes before her cheeks were streaked with moisture.

Eloise hesitated as Caitlin wiped her eyes and struggled. "Of course you can. It's scary and uncomfortable but..."

"I can't," the student repeated, cutting the technician off again.

Eloise hesitated. She pressed her lips together in a look that Caitlin could interpret as either concern or debating what to do next. Caitlin stayed silent and then Eloise surprised her. She stepped forward and put her arm on the girl's shoulder supportively. Caitlin inhaled and looked down at the technicians hand, with slender fingers and short, well-manicured, red painted nails.

"I know you can do it. You've been brave since I got here. I think it's best if we just begin," the technician said, deciding it was better to not upset Caitlin further with more talk. She spoke calmly, with kind authoritativeness, like an older sister trying to get her sibling to just trust her.

Caitlin could feel her heart beating quickly as fear and uncertainty raced through her. "Eloise wants to begin? I'm not ready. It's going to hurt. What do I do? Can I say no? Should I just drop out of school?" With all the questions racing through her head all she managed to do was look up at the woman and nod in agreement.

"Good, I'm glad you agree," Eloise answered, "You're going to be fine. I know you're worried but it's not as bad as it sounds. Put your pillow in the middle of the bed."

Eloise wasn't giving the teen a chance to question anything. Maybe that was good as Caitlin complied with her directions. She scooted to her left and grabbed the pink pillow that sat at the head of the bed in the direction of the window. She moved it into position and muttered, "Just lay down?"

"It's very easy, isn't it?" Eloise answered, "Put your head down on your hands and try not to move them."

"Ok," Caitlin agreed.

"When I start, just keep your hands under your head. I really don't want to have to restrain you, but I can if you don't hold still. I want to make this easy," the technician warned her.

Caitlin didn't want to be tied up either and nodded, "Easy is good."

"Definitely. Now lay down. Head that way," Eloise said, pointing to the desk at the foot of the bed.

The girl went to follow directions. She stayed careful to keep her breasts and sex covered until they were pressed against the bed. It felt disorienting to lay in the bed like this. Even though the bed was flat, it somehow made her feel upside down to have her head down by the desk. She pulled her hands out from underneath her and put them under her head as she pressed her hairy mound into her pillow and A cups into the comforter. Caitlin turned her head toward Eloise and looked up at the technician waiting.

"Thank you," Eloise said after Caitlin got in position. She looked up and down the naked girl prone in front of her. "I'm going to move the pillow back. Lift your hips just a little bit, please."

Caitlin complied and felt the pillow move just a couple inches closer to her feet. The new position lifted her butt a bit higher. For now, her ankles were still linked as she was trying to keep some modesty, but she sensed that it wouldn't take much for Eloise to have a perfect view of her asshole and vulva. Against her wishes, she could feel her muscles tighten in her butt. A shiver went through her. This was going to suck and being so tense was just going to make it worse.

"Just get comfortable, ok?" Eloise said, "I have to put gloves on." Caitlin watched Eloise set down the bottle of lubrication that she wished would be used more liberally and go to the floor to sort through her bag.

"Comfortable? No way," the girl thought. Her heart was beating fast, she could feel her skin crawling at the thought and every muscle was tense. Maybe somewhere out in the student body there was a girl who could relax and get comfortable before a technician rooted around in their ass, but not Caitlin. She was scared and anxious and adrenaline was rushing through her getting her ready to run from Eloise but there was no chance of that. Instead, she just froze in place taking short breaths as the technician prepared.

Eloise returned to stand next to the bed now with cream colored vinyl gloves stretched over her hands. She reached out and picked up the lube and moved it to the corner of the bed, far from Caitlin's feet and spoke, "I'm going to touch you now. Hold still."

The teenager nodded and held her breath as Eloise's left hand touched the small of her back. She rubbed up and down from Caitlin's midback down to the top of her raised butt, causing her to jump. Caitlin's ass had been grabbed before, but this was different, more sustained. Eloise didn't even seem like she was preparing to begin yet. It was like she wanted Caitlin to get used to feeling her hands on her. As the technician's right hand touched the back of her thighs down near her knees, the teenager knew that was going to be impossible. The unnatural feeling of the vinyl made her skin crawl as the technician's hands moved slowly down her back to the top of her butt cheeks and up toward her crotch. She could feel her heartbeat everywhere: her temples, her fingertips, and where she'd never felt it before, her clenched anus.

Caitlin was still holding in breath as the technician's right hand inched upward toward her crotch. Time seemed to slow down, and she closed her eyes as she just knew it was about to start. Eloise applied pressure to her inner thigh. It was clear what she wanted, and the teenager complied. She unlinked her ankles and slid her legs apart. She felt the bed shift slightly and opened her eyes. Eloise was bending over and looking straight between her legs, surely eyeing her target. Caitlin's stomach was roiling with nerves as she felt eyes on her privates.

"Just relax," Eloise whispered as her right hand went to the bottom of the student's cheeks. Thumb on one side on her bottom hole, and fingers on the other, Eloise fully exposed Caitlin's ass. The girl exhaled and quickly sucked in another breath. It was so close now and she couldn't believe that it was even possible. Her asshole felt so tight as Eloise touched it for the first time. The tight material pressed on her butt, but it didn't give way.

"Oh," Caitlin gasped as lightning bolts of... not pain... just weird, strange vibrations rocketed from her bottom in all directions. She wiggled but not enough to distract the technician who continued to rub over her spoked hole. "Ugh," the girl continued to groan as the technician added pressure. The woman's finger was moving up and down and around outside her hole as she pressed in.

"Just relax," Eloise repeated, pressing and rubbing.

Caitlin couldn't. She had no control over her clenched muscles which were terrified of being invaded. Eloise, though, knew what she was doing. The circular motion was making headway and her butt couldn't resist. "Ughh... uhhh," she whined as the gloved finger made headway.

"Here we goooo," the woman cooed as if it was an achievement for both of them.