Detention

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Lucky has detention. Truant supervisor fulfils a fantasy.
9.3k words
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Part 3 of the 3 part series

Updated 02/01/2024
Created 01/19/2024
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"Lucky" got her nickname ironically. She had struggled in her regular high school because she was always studying the wrong material, misunderstanding the instructions of an assignment, or just forgetting about an upcoming test. Now at the age of 18 she was enrolled in the Lovemore Academy. Hopefully the curriculum, designed to leave no-one behind, would be easy enough to boost her grade point average.

One typical day she had arrived late because she had been sure it was a holiday. When she arrived she managed to hit her head on the door she was opening. Now nursing a bruise on her head, she had tried to hurry to her class.

Lovemore had plenty of students that did not take schedules seriously. The halls were often full of students that were leisurely making their way to class. Lucky found that she was alone in this hallway, her new shoes squeaking as she walked.

"Excuse me, young lady!" A prissy voice echoed through the hall. Lucky stopped dead, with dread creeping over her. She turned, knowing who she would see.

"Good morning, Mrs. Humpworthy," said Lucky, looking at the truant supervisor.

Mrs. Humpworthy was a sixty four inches tall, a bit shorter than Lucky. She had coal black hair pulled back into a tight bun. Her pale white skin had only a trace of makeup, to even out her skin tone. She wore horn-rimmed spectacles which were obviously fashion-frames. Her face was currently twisted into a sour expression.

"Elenor, I believe we have had this conversation before," said Mrs. Humpworthy. She placed her hands on her hips and shook her head in consternation. "We cannot learn if we are not in class!"

"I know, I understand. I just read my calendar wrong."

"If your calendar informs you that Monday is part of the weekend, you should get a new one." Mrs. Humpworthy produced a black notebook and began writing on one of the pages.

"This is your third offence, so you'll be receiving detention," She said in a satisfied voice. Lucky only heard this absently. She was looking over the truant supervisor's shoulder.

"Good morning, Mrs. Humpworthy," came a low, rumbling voice. Mrs. Humpworthy jumped in surprise, and turned around. Standing directly behind her was James, the only male in the school.

Her expression changed from stern to sweet in a moment. "Oh, good morning, James!" She cooed. "How are you today?"

"Late, Mrs. Humpworthy." James glanced over at Lucky, and made eye contact. Lucky felt butterflies in her tummy and her hair begin to stand up. "You'll have to write me up as well."

Mrs. Humpworthy scoffed and waved her hand dismissively. "Oh, well, I don't know if that's necessary. You haven't been making trouble as a habit. A little mistake now and then is nothing to be concerned about!"

"I seem to recall being let off with a warning a few times, Mrs. H. I think if I'm not corrected now, it will only get worse." James had still been looking at Lucky, but now turned his gaze on Mrs. Humpworthy. She swallowed hard, glancing all around. She began fanning her face with her hand. Lucky was feeling a bit warm herself.

An idea struck Mrs. Humpworthy. Her sunny expression returned. "Yes, of course. A little detention would be just the thing to set you on the right path. I'll be there to supervise personally!"

Mrs. Humpworthy quickly resumed writing a new script in her book. When she finished, she ripped it out and handed it to James. When he took it, she stroked his hand. She looked lovingly into his eyes as he looked at it, and then looked at Lucky. "I suppose I'll see you there," he remarked warmly.

The truant supervisor seemed only now to remember Lucky was there. "Oh, yes. Detention for you." She ripped off a note and handed it to Lucky. Lucky tried to take it, but it slipped out of her fingers and fell to the ground. Lucky quickly bent down to pick it up, and nearly bumped heads with James. Her breath caught as he took the slip in his fingers. He took her hand, placed the slip in it, and then helped her stand up again.

Mrs. Humpworthy's sour expression had returned. She put her nose in the air and stalked off, her heels clacking on the granite floor. She put a bit of sway into her hips, causing her tight pencil skirt to wrap around her large, round bottom.

Lucky turned back to James, who was still standing very close to her. She breathed out. "Hi. Thanks. At least I won't be alone in detention."

He leaned in to murmur in her ear. "We'll have to think of a fun way to pass the time together."

Lucky's mouth fell open and she covered it with her hand. "Y-yeah."

James took her arm and the two began walking together. "I'll walk you to class."

To have something to say, Lucky replied, "What class are you late for?"

"I don't have a class right now. Free study period."

Lucky was puzzled. "But if you don't have a class, how can you be late?"

"I'm not. I just didn't want you to have to deal with that tiresome business by yourself. It's not really your fault, is it?"

Lucky sighed, savouring his arm around hers. "That's me. I'm just can't stop being Lucky."

James murmured something, his deep voice causing her knees to get weak. "I was really hoping to get lucky too."

***

The day dragged by. Lucky related the adventure that morning to her friends, who demanded she tell it again. They attempted to dissect every detail.

"When he picked up the paper, did he touch your hand?"

"He took my hand in his, then placed the paper in my palm."

"Wow."

She, Jenny, Forsythia, and Pam were seated right next to each other in art class. They had pulled their chairs and easels closer so they could talk. Some of the other students were straining to hear as well.

The art teacher, Miss Moorhead, called out to them from across the class. "Excuse me, ladies, but if you wouldn't mind focusing on the art? The model isn't up there for her health."

Reluctantly, the girls turned their attention back to the platform. Today's life-drawing model was a nude woman. It was Heather's mother Ms. Jocelyn Pancake, who was apparently well known for modeling in the community. Most of the girls in the class were jealous of Ms. Pancake. She was as beautiful as her daughter: Tall and graceful, with every limb perfectly formed. She exercised her muscles for maximum tone. Her long, straight blonde hair hung down to her mid back. She had smooth white skin, with only a dusting of freckles across her chest. Presumably it was the area that got the most sun, since Ms. Pancake liked to wear tops that showed off her cleavage. Her large breasts were firm and round, but hung in a way that suggested they were natural. If any further evidence was needed, one class over Heather was currently putting a white blouse through strenuous testing. Small pink nipples poked out eagerly. She had a flat tummy, with abs that were 'defined' without being 'muscular.' The students around her side could see that her bottom was pert and round as well. Clearly the lady did plenty of squats. Her green eyes were visible through smoky lashes as she scanned the classroom.

"I heard that you got a boy in your school," she said to Miss Moorhead. "Where is he?"

"He is in the other art class with your daughter," Miss Moorhead replied.

Ms. Pancake considered that. "Oh." That seemed to content her for now. Like her daughter, she was not a verbose woman.

Lucky attempted to draw Ms. Pancake using a pencil. She tried again and again to get the curves right. They always seemed to come out flat and pointing the wrong way. She sighed and tried to erase a line, only to tear through the paper entirely. Embarrassed, she tore it off and began again from scratch.

"Just try to picture what it would look like from all the different angles," suggested Jenny. Her drawing was much more lifelike. The face seemed to be looking in the viewers' direction, and the breasts were popping out of the page. She had even managed to capture the way Ms. Pancake was standing, a sort of challenging half-step forward that showed off her hips.

"You're so good, Jenny," cooed Forsythia. "I wish I was as good as you."

Jenny blushed. "It's just practice. I do a lot of drawing. But I still need more work with life drawing."

Pam gave a wicked grin. "I wish we could get James in here to do some modeling." The other girls giggled, and Lucky tried to cover her face. She could feel a blush forming. Now through the whole detention I'm going to be thinking about him naked.

***

That afternoon, after the last bell rang, most of the students milled around for awhile. This was their chance to make plans and gossip without teachers writing them up. Lucky was a bundle of nerves as she walked through the halls, clutching her bag. She stopped in the ladies' room to freshen up. With only a few minutes to spare before detention started, she tried to fix her makeup. Her hands could not stop shaking, and she dropped her eyelash brush in the sink.

"Oh, honey, let me help you with that." Another girl came over. It was Alyssa, who rumour had it had gone all the way with a certain hot newcomer. Lucky began to feel very nervous. Alyssa began using her own makeup kit to doll up Lucky.

"Off somewhere special this afternoon?" Alyssa asked. Lucky had never had much to do with Alyssa, but also had never heard much reason to dislike her. She was charismatic and friendly, which is no doubt how she had attracted James.

"I'm going on a-" Lucky paused. It wasn't a date; it was detention. "I've got detention. Late, again. Um, James was there. That is, he'll be there too." She struggled to avoid squeezing her eyes tight shut. She was half-expecting Alyssa to explode at her.

Alyssa's face remained calm as a spring day as she continued her work, their faces mere inches apart. "We're not exclusive or anything. He can do whatever he wants."

Lucky began to breathe again, though she was waiting for the other shoe to drop.

"You want my advice?" Asked Alyssa, as she re-capped the brush.

"Um, sure."

"Do whatever he wants." Alyssa was matter-of-fact, with a totally serious tone.

Lucky swallowed. "Like, whatever?"

"Whatever-whatever. You won't regret it."

Lucky tried to parse all this. "And you... You won't be jealous?"

Alyssa gave a wry smile. "Girl, he fucked the jealous out of me. Just tell him I said 'hi.'"

***

Ten minutes later, Lucky hurried into the classroom designated for detention. She was just barely on time, and expected to be chewed out for lateness anyway. She kept her head down, trying against all logic to go unnoticed.

"Still having trouble with promptness, I see," said Miss Humpworthy. The truant supervisor was standing at the window, arms folded behind her back.

"It's four o'clock exactly," replied Lucky, trying to avoid being petulant.

"Do you know, dear, that in the military they have a saying: if you're not early, you're late."

Lucky sat down at a desk, using all her willpower to avoid responding. She glanced around at the classroom, empty except for the two of them.

"Where is everyone else?"

"Just the two of you today," replied Mrs. Humpworthy, still gazing out the window.

Lucky noticed a few things were different about Mrs. Humpworthy. She had taken off the severe blue jacket, leaving her in a mint-green blouse. She seemed to have raised her skirts' hemline, leaving more of her calves and a bit of thigh visible. It was wrapped rather tightly around her large round bottom. She was wearing sheer black tights. Her high black heels added about three inches of height and made her legs look good.

Lucky, in her white blouse and pleated plaid skirt, felt underdressed. She had glanced in the mirror after Alyssa had finished and her eyes certainly looked good. Lucky quickly took out a tube of lip gloss and began to apply it.

About five minutes passed, and Mrs. Humpworthy did not change position. Occasionally she would sneak a glance back at the door, or give an irritated look to Lucky. Lucky retrieved a book from her bag and began reading it. She had homework to do anyway.

James walked in. Lucky looked up to see him and was not disappointed. His shirt was mostly unbuttoned. A wide patch of short, course chest hair decorated his pectorals. He was fairly glistening with sweat. His hair was wild.

"Apologies. Gym class. Had to get changed," he explained as he sat down in the seat next to Lucky.

Mrs. Humpworthy turned around as he entered. She had been planning a scenario to intrigue and arouse the young man. She was unprepared for the sight of his bare chest, though. She bit her lip and tried to avoid staring.

Lucky couldn't concentrate on reading. She could smell the sweat on him and it was making her dizzy. Her heart pounded as he leaned over to murmur to her.

"Do you think you could go to the washroom for a few minutes?"

Lucky took a moment to parse this, then nodded. She help up her hand.

"Mrs. Humpworthy, may I go to the washroom?"

Mrs. Humpworthy glanced at Lucky, then waved her hand dismissively. Lucky sprang to her feet and left the room. The last thing she saw on the way out was James getting out of his seat and approaching Mrs. Humpworthy.

Lucky went to the washroom, not because she needed to use it but just to kill time. She got a drink of water and went to her locker. She waited about ten minutes before heading back to the detention class.

Mrs. Humpworthy was nowhere to be seen. James was half-sitting on the teachers' desk, his shirt completely off, facing the door. He smiled at her as she entered.

"Where is she?"

"I told her she could take a picture of me with my shirt off if she left us alone for the rest of the time." He beckoned her. "Come to me."

Lucky felt like she was in a dream. She fell into his arms and they kissed. He wrapped his arms around her, holding her tight. She pressed her hands against his chest, feeling his strength and his fuzziness. He moved from kissing her lips to dotting her cheek and neck with kisses. "You have such soft lips," he murmured to her. She smiled, enjoying the kisses.

"You do too. Do you want to use your tongue?"

"Oh, sure."

Lucky had been expecting him to french kiss her, but instead he spun her around and lifted her up. Before she knew it she was seated on the desk. James hooked a chair with his foot and dragged it over to him, then positioned it in front of her. He sat in the chair, now looking up at her. Lucky's heart was pounding.

"Can you lift your hips up a bit?" James asked, as he ran his hands up her thighs towards her skirt. She felt clumsy as she used her arms to lift herself up. It was just enough for him to reach under her skirt, grab the band of her panties, and pull them down. She sat back down, breathless with anticipation. James ducked his head under her underwear, still stretched between her thighs, so he was right between her legs. She looked down at his head, feeling lightheaded.

"Okay. Can you lean back a bit?"

Lucky complied, falling back onto her elbows. She watched him as he flipped up her skirt and began to kiss her vulva. He slid his arms under her thighs so she was resting them on his shoulders. He wrapped his left arm around her right thigh. He used this to position her leg to allow him to get his right hand between her legs as well. He managed to get his left hand around and over as well.

James used his left hand to part her vulva. He began to lick her clitoris with short, gentle strokes. Lucky's arousal grew immediately. She could feel herself getting hotter and craving more stimulation. She got it when he slid a finger into her vagina. Her eyes popped as she felt him stroking her g-spot. The different sensation blended with the strokes on her clit to overwhelm her. He started doing longer, firmer licks while he stroked her g-spot with his finger, over and over. He sucked on the clit for a moment, then gave it a few licks, then sucked on it again. Lucky could already feel an orgasm building. He slipped another finger inside her. He applied more pressure to her g-spot, increasing the sensation. She let out a long gasp as she reached orgasm. He felt her tense and heard her breathing change, so he adjusted the pace. He gave medium-length firm licks and firm, rapid strokes inside her. Lucky's orgasm lasted longer than any she'd ever had.

Panting, she lay back on the desk. Her legs and arms felt like jelly. All she could do was stare at the ceiling. James took his fingers out and his tongue off her, letting her vulva settle back into place. He stroked his hand up and down across the whole thing. He kissed and nuzzled her thighs. She managed to raise her head enough to see him down there, and smiled at him. He looked at her with a faux-serious expression, then bent back down again.

Lucky's eyes widened as James got back to work. He once again opened her vulva to expose her clitoris and vagina. This time he used his fingers on her clit and his tongue on her pussy. He put two fingers across the clit and rubbed it. He rubbed it up and down a few times, then back and forth. He placed his tongue inside her, then swirled it around. This wasn't quite as intense as his previous effort, but it felt very nice. She closed her eyes and basked in the sensation as he gently rubbed her clit in little circles. His tongue inside her felt wicked, and she laughed. When he heard herself laugh, she slapped both her hands over her mouth, embarrassed. She bent her neck forward, trying to see how he had reacted. Not at all, apparently. James switched back to licking her clit and plunging his fingers. Lucky reached down to run her fingers through his hair. All her senses were overcharged, and merely touching the soft hair felt like an out-of-body experience.

It didn't take long for her to come again. She was more ready for it this time, but the blended sensation was still wonderful. She felt like a puddle of bliss as she lay on the desk. James placed his large, strong hand over the entire area and rubbed it gently in a circle.

Once Lucky had almost caught her breath, James stood up. He took her panties off the one leg they were still hanging on and put them on the chair. Then he unbuttoned his pants and pulled them down. He wasn't wearing underwear. His penis, already hard, popped out. He got closer and began to line up his hips with hers.

"W-wait," she said. He stopped and looked at her.

"You don't want it?"

"No, I do. I do. But... Can I return the favour first?"

James grinned at her. He helped her sit up, then stand up. She relished the feel of his hands holding hers. She sat down in the chair in front of him, and he stood as close as he could.

Lucky was eye to eye with James' penis, poking straight out at her. She gently reached out to take it in her hand and stroke it. She knew what men wanted to hear at this moment. She opened her eyes wide as if in shock.

"Wow, it's so big," she said, her voice full of wonder. She looked up at him and pouted. "I don't know if I'll be able to get all this in my little mouth."

James gave a soft little chuckle and scratched the back of his head. "Thanks," he said.

Lucky got to work. She rolled the foreskin back, revealing the bulbous red head. She opened her mouth and took it inside. She bobbed her head back and forth, then gradually started going further on it. She went about halfway down the shaft, which was about the limit before she would start choking for real. All acting aside, his penis was wider and longer than she'd seen in real life. Lucky did not have enough practice to deep-throat a cock like this. She slowly slid back off it, rubbing her tongue left-and-right along the bottom as she did. When she had the head only in her mouth, she swirled her tongue around it. She could feel that every inch of it was engorged now.

James groaned in pleasure as she worked, and she redoubled her efforts. She sank as far as she could on it - maybe she could go a little deeper than she first thought -- and slowly withdrew. She sucked as hard as she could on the way back, and dragged her tongue along the bottom. She heard him breathing hard and felt him quiver. Any moment now, she thought with satisfaction.