Bobby’s Punishment

“Bobby, where is your report?” I asked.

“I...I left it in my dorm, Miss Janine,” stammered the tow-headed youth. His fingers twitched nervously at the top button of his blue shirt. “But it’s not completely done. Could I please have another night? I know I’ll finish it and turn it in tomorrow, miss.”

A hiss of inhalation showed how Bobby’s classmates reacted to this bit of mildly defiant nonsense. “I know you’ll turn it in tomorrow, Bobby, because you won’t want to repeat the punishment you’ll receive as soon as class is over.” I smiled, seeing him squirm in his seat. Other boys stole glances at him, not wanting to attract my attention.

Bobby just hung his head and mumbled, “Yes, miss.”

This was a World History class and we’d reached the 14th century. I discoursed on the Inquisition, relishing the irony. So did Sam, the class bully and Bobby’s tormentor. Sam, however, kept out of trouble, only pausing by the hapless boy’s seat to mutter, “Looks like the Inquisition’s got you today!” after the bell rang.

The boys, some of them snickering, filed out, leaving Bobby standing before my desk with his hands behind his back as he’d been taught. My red-nailed fingers tapped a few keys on the computer. I told Bobby to check that the classroom door was locked. Punishment was a private affair at the Searing School—usually.

When he returned, I had his record on screen. “Why Bobby, this is the third time I’ve had to punish you for not turning in your homework. I see you’ve also failed to do so once with Miss Melinda, but that you have a perfect record in other respects. Is the work too hard?” I knew his IQ was 125.

“No, miss, I just forgot. I’m ready to take my punishment and I promise to have the completed report here tomorrow morning.”

“It seems it’s difficult for you to learn to turn work in on time. As you know, Bobby, if a student persists in doing something wrong, his punishment is increased. The first time, I took you over my knees and spanked you until you were gasping and squirming. The second time I increased the pain and added a little embarrassment by having you pull down your pants and spanking you on your underpants. I noticed a bit of a tear in your eye after that session. Did it hurt more than the first one?”

“Oh, yes, Miss Janine, it sure did!” Eyes downcast, he shifted his weight from one leg to the other.

“But not enough to get you to hand in your work on time.” I glanced at the screen. “You turned 17 a couple of weeks ago. A bit old to be late with your work. This time, Bobby, to increase your punishment you’ll be naked and I’m going to go on with the spanking until I’m convinced you’re crying for real—no faking. If you act like a little boy, I’ll treat you like one. When you act your age, I’ll treat you like a big boy. Are you ready to take your punishment now?”

“Yes, Miss Janine. I’m sorry for not turning in my homework and I’ll bring it tomorrow.”

“Good, Bobby.” I tossed my chestnut hair and gave him a dazzling smile. “Now take off your shoes and pants, little boy.” Pulling a chair from behind a student desk, he sat, quickly removed his shoes and stood to undo his belt. A moment later his jeans lay on the floor. Shirttails partially hid his patterned blue underpants. “Your shirt will be in the way, Bobby. Remove it,” I commanded. His hairless chest and flat stomach had tiny nipples dimpled with goose bumps. The youth shivered though the room was warm. A bulge in his blue bikini style underpants showed his reaction. I smiled and breathed deeply. This was going to be fun!

“I’m glad boys are wearing nicer panties than they did when I was a girl. Those look cute, but they’ve got to come off.”

A rueful smile twisted his lips. “This is embarrassing!” Bobby put his thumbs in his waistband and paused, drawing in a deep breath. Then down came his bikini and the naked boy stood before me, awaiting my pleasure. His erect cock had a bit of fuzz around the base, the circumcised head pointing right to his belly button. Unlike many of the boys, he didn’t try to cover himself. Perhaps he left his homework in the dorm deliberately.

I walked from my desk to the straight backed wooden chair I kept in the corner. As I sat, I lifted the hem of my dress up my legs, exposing my stockings and garters, but stopping short of my panty crotch. Behind me, I heard Bobby’s breathing deepen. I opened my legs just enough so Bobby could tell my panties matched my black garter belt. I loved giving the boys just that glimpse before punishment. Wetness developed between my legs.

“Come here for your spanking, Bobby.”

Staring at my pantied crotch, the apprehensive boy took the a few strides to stand by my exposed legs. I looked frankly at his cockhead. The slightly bluish tip was tight with the tension of his erection.

Miserably, the boy sobbed, “Why are you looking at my thing, Miss Janine?”

It looked delightful, twitching as he clenched and unclenched his buttocks in anticipation of pain. The head overshadowed shaft. “I need to be certain you haven’t emitted a little semen, dear. Some of the boys do at this stage, and I can’t have you dirty my stockings or soil my thighs. But you’re still dry, so bend over.” I patted my legs where the garters snugged up my dark brown stockings.

“OK,” he sighed, and bent forward. He squirmed a moment and his cockhead rubbed my left thigh, his balls gently resting on my right stocking.

I massaged his exposed cheeks, lecturing him in my sweetest tones. “Bobby, you simply must learn to turn in your assignments on time. It’s inconvenient for me, and allows you to continue bad habits if you don’t. That’s why I’m punishing you—to help you learn good habits. Are you ready?”

“Yes, Miss Janine. Please spank me so I’ll learn to turn in my work on time.”

I curved my hand to his buttock and began to slap, not hard, but steadily. I got a lot of sound without hurting the boy much. Bobby was a very pretty boy, with pale skin and freckles. I expected him to redden quite nicely. I varied my aim, covering all of both cheeks and the tops of his thighs. The tip of his stiff cock jabbed against my leg each time he pressed down. I paused.

“This doesn’t hurt too much yet, does it Bobby?” I asked.

“No, Miss Janine, but I’m sure you’ll make it hurt more!”

“Yes, I will, Bobby. I hope it’s enough so you’ll remember to turn in your homework. Oh, and Bobby, if you feel you’re about to have an accident, let me know. I’ll pause in the spanking for that, but if you make a mess on me, I’ll spank you more than you could possibly imagine. Do you understand what I’m talking about, Bobby?”

“Yes, Miss Janine.”

“You’re a big enough boy for that to happen, aren’t you, Bobby?”

“Yes, I am, Miss Janine.” I barely made out his whisper.

“Then be sure it doesn’t occur!” With that I resumed the spanking. I put a little wrist action in, flicking the tips of my fingers across the pale cheeks. Bobby squirmed, his cockhead bobbing against me. “Does this hurt a bit more, little boy?”

“Yes, Miss Janine, it stings!”

“But not nearly enough to make you cry yet. Right, Bobby?” I alternately rubbed his behind and dug in my fingernails, causing him to gasp.

“Oh yes, miss, I’m afraid I’ll have to be spanked quite a bit before I cry.”

“Too bad for you! Wouldn’t it have been easier to have turned in your homework on time?”

“Yes, Miss Janine. I promise to do better after this.”

Spanking harder, I said, “I’m sure you will, Bobby” But I had my doubts. These spankings were probably the most erotic experiences in the young lad’s life, as I intended them to be.

I was certain I’d have him draped over my thighs for punishment again. Pow, pow, pow! I used more force and kept my hand straight, not curved.

“Oh!” Bobby cried with each blow. His bumcheeks were no longer white, but suffused with pink. I lowered my aim to the sensitive tops of his thighs. The cries rose in pitch. I began spanking in earnest, slapping quite hard all over his bum and upper legs. He began to beg as the pain grew. “Oh, Miss Janine! It hurts! It really hurts! OWW! Oh, I’ll be good. Please, Miss Janine, don’t spank me until I cry! It hurts enough already, believe me! I’ll do my homework forever, just please stop! OW!”

The punished boy bounced quite vigorously on me, his cock still erect. It jabbed me, and I felt his balls slap against my thighs. I decided to prolong the spanking with more humiliation. I gave him 10 or so more, very hard, enough so he yelled inarticulately in his pain.

Suddenly I stopped. I spoke in tones as controlled as my heightened breathing allowed. My panties were soaked. “Stand up and do not touch your bum, little boy.” Obediently, he stood. “Bobby, I’m going to help you avoid an accident. We’re not done; you haven’t begun to cry yet, so you haven’t been punished enough. But your little cock is still erect. I’m going to teach you a way to make sure you don’t have an accident.

“Grasp your cock down at the base. Yes, that’s right, near your balls. Now squeeze just a bit and slowly pull your palm up the shaft. Right at the top, squeeze again. Yes, there - see that drop of semen? You’d be in big trouble if that had gotten on me!” I handed him a tissue from the box on my desk. “Dab up that drop and throw the tissue away. There, good boy,” I said as he obeyed.

“Oh, Miss Janine! This is so embarrassing!” The sweet boy’s eyes glimmered with tears which he reflexively blinked back.

“Yes, it is,” I acknowledged, patting my legs invitingly. “Come back over my lap, Bobby. This is when you’ll learn to do your work on time. You’re almost ready to cry. I’ll go on a bit after you do, just to make sure you aren’t forcing or faking it.”

His reddened cheeks were warm to my touch already, and I really lit into him. I knew the brief respite would only make the globes more sensitive. I put more strength into my arm, slapping alternate cheeks in a steady rhythm. The boy began to kicking; he was past begging.

“Ow, ow, ow, ouch!” the punished lad cried with each blow. For a moment, I considered using my ruler or a paddle, but I liked the challenge of reducing this boy to tears with my hand - and my mind.

I stopped for a moment and rubbed my palm over one smooth warm cheek. “Take a deep breath, Bobby,” I warned. “This is going to hurt!” With that, I began to strike slowly, then faster and faster, harder and harder on the two tenderest spots of each mound - where the flesh was thickest. Slap, slap, slap, pow, pow, wham, Wham, WHAM!

“Going t...AAAHHH!” Bobby’s retort was cut off by rapidly growing pain in his posterior. The lad caught his breath, then sobbed “Oohh,” as the tears came. He couldn’t hold back any longer. Losing what little dignity remained to him, he resigned himself to tears, blubbering incoherently. I continued to slap his hot buttocks as hard as I could. The genuine tears (There was no question of his faking!) and uncontrolled cries excited me to new heights and I spanked him harder and faster than ever. His bouncing provided me just enough time between blows to clench my thighs, pressuring my sensitized clit.

“Ah, you’ll do your homework after this!” I managed to gasp as an orgasm coursed through my body. I closed my eyes and threw back my head, mechanically slapping as my hot cunt spasmed. My rhythm slowed as my arousal passed the peak. I kept the sobbing boy on my lap for a few moments, rubbing his inflamed buttocks.

“Well, Bobby, there you are. Do you think you’ll remember your homework in the future?”

“Oh, yes, Miss Janine,” he snuffled. “Thank you for the spanking. I’ll be on time, I promise. That hurt!”

“Go look at your behind in the mirror, little boy.” He stood, a bit unsteadily and took a tissue from the box on my desk. Pausing to wipe his eyes and blow his nose, he walked to a door in the wall on which there was a full length mirror.

“Oh it’s really red! And it sure stings!”

“I see that you’re still erect, Bobby.” I handed him the box of tissues. “That won’t do. Take these tissues into the bathroom behind the door with the mirror. While you’re in there, reduce your erection. Then clean up every drop and let me know you’re done. I’ll come in and inspect you and the room. Don’t flush your tissues with your semen, put them in the wastebasket.” I delighted in the miserable look on his face.

Docilely, the boy went into the bathroom. I sat at my desk, pulling my skirt up so I could palm my still inflamed pussy. I hadn’t spanked a young student in several weeks, and this had been a nice hard one. I was nearing a second orgasm when the door behind me opened.

I swiveled my chair and stood, giving the adolescent one more look at my stockinged legs as my skirt fell back into place. Striding to him, I said, “Well, Bobby, I see your erection’s successfully been reduced. Hold it so I can see that you cleaned it well. Good. It looks fine - no sticky semen on it. Now I’ve got to see the bathroom.” I went in, the frightened boy watching from the doorway.

“Well, there’s no cum on the floor or the toilet seat. And here’re the used tissues. I guess you did a good job. Do you feel a bit better now that you’ve reduced your erection?”

“Yes, Miss Janine. Thank you again for the spanking and for allowing me time to recover. Could I please dress now? I’m very embarrassed and cold.”

“Yes, little boy. Try to act more responsibly in the future.” He rushed to put his clothes on. With one more ritual of thanks and a promise to turn in his homework, he left.

Ironic, I thought. Now I’m frustrated, not the boy. Finish here in school? No, I’ll wait for my date tonight. Stimulate myself when I get home, be on edge when Frank calls for me.

Smiling to myself, I organized some papers, corrected them, and entered the grades. I locked the room and started down the hall, high heels tapping.

A tall young man approached. He wore tan slacks and a green polo shirt. Straight black hair hung to his collar in back. “Miss Janine!” He smiled and strode faster. “I’m Jeremy Alves. I was here about 6 years ago. I don’t suppose you remember me, but I never forgot you.”

“I do remember you, Jeremy. How have you been? You’re very handsome now that you’ve grown up. I’m a little late but you may walk me to my car.”

“Thank you. Miss Janine, you are as beautiful as ever - just as I remembered.” He tried but failed to maintain eye contact as he delivered this compliment. That was a good sign. “And I’m doing OK, in fact really well. I haven’t been in trouble since I left Searing. I always wanted to come back and tell the teachers here, you in particular, that I’m OK. I graduated from high school and I’m just starting college at Biltmore, so I’ll be in Riverway for most of the next few years.

“Miss Janine, you really helped me back then, and I want to thank you. I know

you’re busy but....” He hesitated and looked at the tarmac.

“You’d like to sit down together and talk for a while, right?”

“Yes, Miss Janine, that would be great!”

“That would be very nice, Jeremy. Well, I have a date with a man, so I must go shower and dress. How about if you come to my room at lunch tomorrow? Bring a sandwich or something. We’ll have our own private time for half an hour. OK?”

“Well, I gotta cut a class, but I do want to talk with you, Miss Janine. I’ll be there,” he promised. We’d reached my car. Gallantly, he held my door. I knew why. I gave him a dazzling smile as I got in and sure enough, his gaze dropped to my legs. I let him see just a bit - lower thigh, not even stocking tops. I’d practiced. We said our good-byes and I drove off.