The Penetration of Caitlin

Caitlin's mouth hung open, unable to do anything but sigh as first a fingernail entered her. It was so tight! The rim of her ass stung as the gloved finger rubbed it, spreading it from a new direction it wasn't meant to open. Her eyes shot open as it got to the first knuckle, and she stared at the drab wood of the back of her desk. The woman's push slowed for just a moment. The finger wiggled and a full discomfort radiated out as she changed the angle of the push. Caitlin could feel it worming into her, burrowing side to side, moving her walls aside as it pressed deeper in. "Grrr," she grunted. The feeling was hot and rough as friction built in her unready ass.

Eloise continued digging as the teenager groaned. Progress was being made. In less than a minute after she touched Caitlin's dark hole, her finger was buried up to the second knuckle. "You're doing it," the technician said calmly, giving the girl credit for her own work.

Caitlin wasn't listening in her own world of squirmy discomfort and stinging heat. It felt so unnatural to have anything entering her butt and her instinctive pushing and muscle spasms weren't helping. There was no forcing the woman out and each tightening of her sphincter only caused more pain to radiate outward from her hole. The finger just kept coming in. Rotating slightly, it sunk in deeper and she felt the knuckles of Eloise's other fingers touch her cheeks. One finger was all the way in!

The technician kept her long slender finger still, totally inserted, for a few long seconds. The lack of movement didn't make it any better for Caitlin who still squirmed and sighed as her walls contorted and flexed but ultimately failed to push out the woman's fingers. She could feel her hole trying to close back to its natural position and each attempt only made her butthole sting as it pressed against the digit.

Then Eloise finally decided to continue. Her finger started wiggling like she was telling someone to come toward her from across the room. "Agh, agh," Caitlin groaned with each curl of the woman's fingers that pushed against her tight insides. Shortly, the woman added a twisting motion; each time her finger straightened, she rotated it slightly, rubbing the vinyl against her sensitive tissues, and curled her fingers again.

Caitlin's hands gripped the comforter, and she gritted her teeth as she continued to stare, wide eyed, at the back of her desk like she still couldn't believe what was happening to her bottom hole. It was like her brain just couldn't comprehend, despite the fact she'd picked this punishment from the list, what Eloise was doing for her, and it kept getting worse. Behind her, Eloise was starting to move her finger in and out of the teenager's bottom. With no lube, it burned and scratched, and Caitlin's eyes filled with tears, making her blink as the woman's finger penetrated her ass over and over.

The teenager just laid there and took it. She wasn't tied down. Perhaps, the technician's left hand could have held her down, but it just rested lightly on Caitlin's lower back. Still, she just laid there despite the lack of restraints. Not once did it go through her head that she could resist. All she knew was that the only way out of her predicament and the only way to stay a student in good standing was just to let Eloise keep fingering her ass and there was still more to come.

Caitlin groaned as the finger was finally withdrawn. Her hole closed again, still aching but much relieved. "Oh, god," she moaned as she instinctively reached back now that her butt was free.

"Stop!" Eloise hissed, before softening her tone, "I'm adding lube."

The punished girl knew that meant a second finger was about to be pushed into her. "Oh, please," Caitlin begged even as she put her hands back under her head, "I-I can't..."

"You can," Eloise said, continuing the whisper softly, "The first finger is the worst, I promise."

"Please..." Caitlin moaned as she heard the soft pah of the plunger on the bottle of lube release air in it's tube.

"Just relax," Eloise responded.

"I didn't know," Caitlin continued. She really didn't once think that the hot plate broke the fire codes.

"You were told," Eloise reminded her.

Caitlin knew it was about to start again. "I'm sorry," she said.

"I know. We are almost done," Eloise said as she touched the teen again.

Caitlin gasped as wet fingers touched just above her anus. Lube dripped down over her hole, and she shivered as it continued down onto her labia and dampening her dark pubic hair on her lips. "You said," the teen started intending to argue she didn't need the second finger since she'd learned her lesson.

The technician interrupted her though. "Ssshhhhh," she shushed, as two gloved fingers rubbed small circles on Caitlin's asshole. Easily, her middle finger slipped in up to the second knuckle before pulling back out, leaving lube inside. "You're ok," she said as two fingers plunged into the girl's ass.

"Aaaggg aaaahhhh," Caitlin groaned, squirming, her hips wiggling. However, maybe it was the lube or perhaps the first finger loosening her ever so slightly, both fingers went in half their length quickly and without resistance. Then the work started. Caitlin gripped the blanket and whimpered as Eloise forced her fingers inside.

The technician continued stretching the student's anus as she worked her way inside. Her fingers moved a little out and a little in, a little to the right and a little to the left, and a little up and a little down as she changed the angle to force Caitlin's clenched muscles to yield and allowed her deeper inside the girl's ass.

Despite the lube, it burned. The stretched rim of Caitlin's ass was on fire as it opened to the diameter of two fingers. She whimpered and shook her head as if she was signaling 'no' to the whole punishment. But there was nothing she could do. Eloise was slowly going all the way in, and Caitlin was feeling parts of her body she didn't know she had as her wall's were opened. All the while she groaned, the moans filling her dorm room.

Ignoring her whines, Eloise finally got both fingers fully into the girl's butt. Again, she paused with both fingers still for ten seconds or so before beginning to wiggle her fingers inside. Caitlin gasped loudly at the new sensation that just kept getting worse and worse. "Almost done," Eloise cooed.

"Uuhhh uugghh," the freshman answered, unable to form words, overwhelmed by the stinging and fullness in her bottom. It just kept going as Eloise kept moving. It felt like she was trying to spread her fingers like a peace sign fighting against her muscles trying to keep them together. It was impossible to get them fully apart, but the effort was excruciating and made worse by the tensing and contracting of her ass trying to fight the technician's fingers.

After a minute of stretching Caitlin's ass, Eloise moved on to the last part of the punishment. The teenager felt the gloved fingers moving out from her ass and she sighed but they weren't totally withdrawn. The tips of the woman's fingers stayed in her hole while she heard the sound of the lube again. She held her breath knowing more was coming and two fingers were quickly shoved back as far in as they could. The new lube made it easy and the technician didn't stop.

"Uuuggghhhh grrrrr uuugggghhhh ggrrr," Caitlin groaned. The woman pumped her finger in and out getting faster as she went on as the poor girl grunted in terrible pain. Her hips rocked side to side and Eloise increased pressure with her free hand holding her lower back down. Caitlin could hear squush squish coming from her ass as gloved, lubed fingers fucked her ass over and over. Tears flowed as her punishment reached its crescendo and she screamed, "Aaaaaggghhh!"

Then it ended. Eloise's fingers slowed and stopped pumping and Caitlin could feel the walls of her ass close as the technician withdrew. The teenager was left with a rumbling pain emanating from her insides and a burning asshole. She buried her face in her hands as she realized it was over. She sobbed, her body shuddering in relief that her ordeal was over. How long had it taken? Ten minutes? Five minutes? It felt like forever to her.

Eloise touched her upper back and Caitlin jumped. "It's ok," Eloise said softly, "It's over. I'm going to check you quickly." The girl didn't answer but Eloise continued. She touched the girl's buttocks and leaned down to look at her ass. "You're fine. You're fine," she repeated soothingly, "I'm going to clean off the lube. Do you have a robe so you can get dressed?"

Caitlin still didn't answer, but she was wiping her red face. She looked at Eloise who was in her bag. She came back with a soft, gauzy cloth that came from a packet and touched her ass again to soak up the lube. "Do you have a robe?" she repeated.

"Mmm hmmm. Closet," Caitlin spluttered, her eyes directing Eloise to the open door where the towel had been.

Eloise peeled off her gloves and put them in a plastic bag she'd brought with her. She went to the closet and fetched the pink robe that hung from the hook on the back of the door and came back to Caitlin who was sitting up from the bed, covering her breasts. "Here, let me help," Eloise told the girl holding the robe open.

Caitlin let Eloise put the robe around her, deciding that it wasn't so bad for the woman to see her tits again after all that had happened. Still, she quickly got the robe closed and tied the belt. She exhaled, feeling weight fall off her as she was covered again. She looked up at the woman who still stood over her, "Now what?"

"The punishment is complete," Eloise said with a wan smile, "I'm going to sign the certificate that it's done and leave it with you and leave you a pamphlet with suggestions if you'd like to speak to anyone about what just happened."

"Ok," Caitlin said, not sure what else to say.

"You'll get an email with the same information," Eloise continued as she pulled papers out of her bag. She went to Caitlin's desk and signed the certificate and then began to close up her bag. "Do you have any questions?"

Caitlin shook her head before deciding to be brave, "Why?"

Eloise's lips pressed into a thin line like she knew this was an awkward question, "Why what?"

"Why this?" Caitlin asked, looking down at the floor.

"Better than a fine, supposedly," Eloise answered.

Caitlin shrugged, "I don't know."

Eloise shrugged as well, "It's a new world. I'd suggest not breaking fire codes again."

Caitlin nodded and Eloise picked up her bag and turned to leave. The woman went out the door and Caitlin was left to ponder. Introduction to Ethics was going to be a fun class this semester.