08 Sister Annes First Time

This is a work of fiction. Names, characters, events, and incidents are the products of the author's imagination. Any resemblance to actual persons, living or dead, or actual events is purely coincidental. All characters are consenting adults over the age of 18.

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As much as he enjoyed spending his mornings watching Sister Roberta bounce and jiggle as she cleaned his office, it merely served to whet his appetite. He needed more, and Sister Anne was a perfect choice.

She would be obedient and discreet; all of the nuns were. But she was also the youngest and newest teacher; unlikely to resist his advances.

All he needed was some way to convince her - and now that Roberta had disclosed that Anne shaved her pubic hair, that might do the trick. He knew that she often swam laps in the school's pool on Saturday mornings. His plan was simple enough: wait for her to disrobe, and capture a photo to use as leverage.

As headmaster, he had access to every part of the school. The pool would not be busy this early on a Saturday morning. He simply dismissed the student receptionist and hung the "Closed" sign. Now he just had to watch and wait. Sister Anne was the only adult in the pool. There were a few girls, but since the faculty and students had separate changing rooms, they were not a concern.

He watched as the young nun reached the far end of the pool, pushed off, and began swimming back. She was doing the backstroke, and it provided a nice view of her breasts. He was looking forward to seeing them without the bathing suit.

He didn't have to wait long. After two more laps, she pulled herself out of the pool and headed to change. He listened until he heard the shower running, and then entered with his cellphone camera recording. Sister Roberta's description was accurate; Anne was almost completely shaved, with just a thin strip of golden pubic hair. He captured a short video, put away his phone, and then waited for her to notice him.

"Oh! I'm sorry Headmaster, I thought I was alone." The faculty changing area was technically co-ed, but there were so few male faculty that it was rarely an issue.

"I couldn't help but notice your shaved pubic hair Sister Anne."

"Oh, I see. Well... that's none of your business... sir."

"Everything that goes on at this school is my business, Sister Anne. It would be wise for you to realize that. Now give me that towel, and put one foot up on the bench. I need to get a good close-up picture for my files."

"What? I will do no such thing!"

The Headmaster smiled and stood. "I was hoping you might try and resist." At 6-foot-3, he loomed over the young and slender 5-foot-2 nun. She clutched the towel and tried to back away from him. Grabbing her forearm, he spun her around, and pulled both of her hands behind her back, holding them tightly in one hand.

"Please, Sir... I'm sorry! I didn't mean to anger you..."

"It's too late for that, Sister. I simply cannot tolerate such disobedience to my authority." His voice was quiet but firm. He slipped off his leather belt with his free hand and brought it down hard against her damp bare bottom. Smack! Smack! Smack! She cried out in shock and pain, but twist as she might, she was unable to break free.

He looped the belt around her arms, just above her elbows, and tightened it. Although her hands were free, she was unable to move much, and a sharp tug on the belt quickly discouraged her from struggling.

He turned her around and pushed her down hard onto the bench, onto her bound arms. Then he pulled his phone from his pocket and took several pictures - starting with her full body and gradually zooming in to get a closeup of her neatly trimmed bush. "Spread your legs," he ordered. She hesitantly complied, but not quickly enough for him. "Wider!" he demanded, using his knee to force her legs apart.

He held his phone within inches of her pussy. With one hand, he spread her lips apart and exposed her clit. He captured several more pictures before finally tucking his phone away. He unzipped his trousers and pulled out his hard cock. Anne's eyes opened wide. He rubbed the engorged head up and down between her lips, grunting as he spread his precum on her.

"Please Headmaster! I'll obey you... you don't need to do this," she begged. "I'm a virgin!"

He paused for a moment, and then took a step back.

"Thank you, Sir..." she said, relieved that he had changed his mind.

But he had not. He smiled tightly. "You can thank me afterward, Sister," he told her, picking her up and flipping her over onto her stomach. He pushed her legs onto either side of the bench, spreading her open.

Then he rummaged through her locker and found her panties. Holding her head up by her damp hair, he forced them into her mouth, gagging her. "This is going to hurt; I don't want your screams to attract any attention."

Then he took the bottle of shampoo she had just used in her shower and squirted it onto his cock. He stroked it a few times, coating it with the slick gel. Then he spread her cheeks with both hands and pushed his cock against her tight asshole. He ignored her struggling and her muffled screams.

Anne was tight, but he forced his thick cock into her. He had been hard most of the morning, watching Sister Roberta struggling as the weights he had hung from her nipples, labia, and clitoris dangled and swayed back and forth. Now he watched as his slick cock slowly pushed into Anne's young virgin asshole, stretching her open. The pink stripes left by his belt contrasted with her fair skin.

After a few minutes of this, painful at first for her but intensely pleasurable for him, he pulled out completely. Then he rolled her over onto her back, her arms still bound and now pinned beneath her, lifted her legs onto his shoulders, and thrust back into her ass.

He considered reaching down to rub her clit, but he knew she was far too distraught to appreciate it. Perhaps another time, he thought. Instead, he continued to fuck her, deep but slowly.

After a few minutes, he bent down, pulled the panties from her mouth, wiped them between her legs, and tucked them into his pocket. Along with Miss McCoy's white cotton panties, and Sister Roberta's thong, he had the start of a fine collection.

"Well?" He asked her.

Anne had no idea what he wanted. Dazed by the experience, she didn't respond.

"I'm waiting for a thank you," he explained. "Or shall I take your virginity too?"

"Please don't! Th- thank you, Sir, for using my... anus..." she managed to stammer, barely controlling her sobs.

As he neared his orgasm, he pulled out of her, turned her around on the bench, and thrust his cock into her mouth. She gagged for a moment; not on the taste of her ass, but on the frothy residue of shampoo still coating his slick cock.

But he ignored her and pushed deeper into her throat. She could feel his cock throbbing as it squirted over and over, filling her mouth with his warm cum. He held her head pressed against him, forcing her to swallow.

Finally, he finished. She gasped for air as he pulled out and zipped his cock back into his pants. Then he lifted her into a sitting position and retrieved his belt. "I look forward to our next encounter, Sister," he told her. She simply nodded. He left feeling more satisfied than he had in months.