Jacob had been the headmaster at Holy Cross School for Girls for five years. A young man for the position, he often drew attention from the girls and mothers alike. He prided himself on the job he was doing in keeping the girls pure and unspoiled by the temptations of the outside world. The girls at Holy Cross did not have the typical distractions of modern television and pre-pubescent boys.

Jacob sat at his desk looking over the courtyard at young girls milling around. He admired a small group of senior high girls gathered around one of the more popular girls, Cassie Parks. He noticed Cassie had a growth spurt lately and her long legs now made her red plaid uniform skirt too short barely covering her round, tight bottom. As Cassie bent over to pick up her bag, Jacob wished another girl hadn’t been obstructing his view. He was sure that her movement would have exposed a beautiful ass being covered by what he imagined were pure white cotton panties. His thoughts were interrupted by the realization of the tightness growing in his trousers. He sat up, adjusted himself and tried to get back to work.

His work was disrupted when he began recalling a conversation with Cassie his first year at Holy Cross. Then just 16 years old, Cassie was brought into his office. It was very awkward for Jacob to explain to Cassie that her breasts were now so large she needed to wear a bra all the time during school. He laughed to himself as he pointed out her nipples, round and pert, were visible through her white uniform blouse and the top was now too tight to hold back her ample breasts.

He taught her about modesty and told her to write her mother and have her send bras and a larger shirt for her. Her mother had been offended by his comments and had come to see him the next week. When she got there, she was able to see what he meant and apologized for her reaction. Cassie’s mother, Cassandra was also a beautiful woman. Divorced and wealthy, she was quick to offer up a token of apology by suggesting they go out for dinner. Jacob, not wanting to offend an important donor to the school, accepted.

At dinner, Cassandra had made her real intentions clear by cornering him throwing herself at him in the alley behind the restaurant when she insisted he walk her to her car. He ripped off her panties and took her against the alley wall. She was fit and acrobatic and balanced herself while riding him like a professional. He was amazed at her tenacity and sexuality and ever since then, he waited to see if Cassie would develop like her mother. She was so blissfully unaware of her effect on the opposite sex but the male teachers made regular comments about what they would do with her when she got older. Jacob thought she would never be as free sexually as her mother.

Now eighteen, Cassie was still naïve but her full womanhood was painfully obvious, she had to be a least a D cup and they bounced under her shirt in such a rhythm when she walked that Jacob so badly wanted to titty fuck her he could barely contain himself. He found the most prudent way was to avoid being alone with her, unsure he would be able to resist her. He looked up from his daydream again, the courtyard was clear- classes were back in session. Fairly sure he would be uninterrupted; Jacob took the time to free his cock from the restrictions of his pants. 

He looked down at his erection pleased that at age 40, he was still very willing and able to fuck all night. Although his last all night love making session had been a few weeks before and he was understandably horny. “What the Hell,” thought Jacob to himself as he began to stroke his shaft under his desk. Looking around to be sure he was alone, Jacob rubbed his cock, till he felt he was fully engorged imagining Cassie walking in and taking his cock fully in her small mouth, sucking the cum out of him and lapping it up.

He was just about to explode when a knock at the door caused him to jump.

“Just a moment” Jacob yelled as the door swung open.

Sliding himself under the desk, he hoped he was fully covered from view, his dick going limp in his hand. Exasperated, Jacob chastised the secretary, trying to hide his frustration about being interrupted.

The secretary apologized, “Sorry Jacob, but Sister Mary sent Cassie Parks down, she won’t be still in class, do you want to see her?”
 
“Yes, send her in”, Jacob said putting his cock back in his pants and discreetly pulling his zipper up.

Cassie and her tits bounced into his office. With her big blue eyes and long brown hair, she was quiet striking. While she was wearing the required Holy Cross uniform, it looks like a stripper outfit on her. Her skirt barely long enough and her top unbuttoned to show her ample cleavage. 

"Ms. Parks, Come and sit down," he motioned to her to sit on a leather couch in his office. He sat a safe distance away in the chair. She plopped down briefly revealing her panties- white, cotton- just as he had thought. “Cassie,” started Jacob, “what’s going on?”

Cassie looked shyly down at her feet. She started in by saying she was sorry, she just had to move around because it was so distracting.
 
“What is distracting, Cassie?”
 
Cassie pointed between her legs. “I keep having sensations between my legs, like a tingling pressure and my panties keep getting wet,” she continued, “I don’t know why but if I move back and forth in my chair it helps me feel better.”
 
Jacob let out a groan; damn he thought to himself, this was going to be hard. Holy Cross had prohibited sex education at the school and most girls only knew what their parents told them about sex on school breaks. Cassie’s parents clearly hadn’t instructed her on any of her body’s sexual functions. He thought for a moment how he could give Cassie some clue without telling her too much to cross the line; he was still trying to stay on the safe side.

“Cassie,” he started “do you know what masturbation is?” He laughed nervously while she shook her head. "Well, if you rub yourself between your legs with your fingers, you will get some release." 

Cassie smiled and put her hands under her skirt and started rubbing furiously.
 
“Stop!" Jacob grabbed her hand away, "You can do that but you need to do this quietly in your own room and not in class.” 

“Do you understand what I am saying?”

Cassie shook her head yes and asked if she was going to be punished? Jacob thought to himself. The normal punishment for disrupting class was a paddle. Jacob didn’t think he could not paddle her for fear of being unfair but he knew spanking her would be a major turn on. He instructed her to bend over his desk. He took his paddle and spanked her ass hard in one swipe. She raised her hips up to meet the paddle. 

“My God”, he cried out.

Cassie turned around. “Is everything okay Mr. Smith?”

“Yes Cassie, but you can leave now.”

Jacob sighed when she left his office. Can there be any more temptations? He flashed back to her hips rising to meet the paddle, thinking he probably made her horniness worse; she seemed to like being spanked. Jacob sat back down at his desk and pulled his cock out and quickly rubbed one off .
As he spewed his creamy white cum in estatic release, he thought to himself, " I can't wait any longer to fuck her."