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Problem Student Ch. 01

By: spamwich



Because of his excellent grades and great aptitude for computer science, James had earned a scholarship to a prestigious private prep school. Since the school was a long way from home, James boarded in a dormitory along with a dozen or so other boys. It was a co-ed school, but boys and girls lived in separate dorms.

Initially James was terribly nervous about the change. He soon got acclimated though, once he met his roommate and neighbors. They all had similar interest in computers and gaming and got along fantastically. 

Things were proceeding pretty normally for him until his first physical education class. The school had a dress code, which extended to the tee shirt, shorts, and sneakers worn for phys-ed. As soon as he looked at the uniform shorts, he realized the problem. 

Without changing, he left the locker room and sought out the teacher who was still in her office, joined by a hallway with the locker room. 

"Mrs. Myers?" James interrupted her, timidly knocking on the open door. 

She looked up at him with large dark brown eyes "What is it..." looking down at a paper on her desk "James, right? You're new here this year?"

James nodded.

"Why aren't you changed? We're starting class!" She asked, slightly annoyed.

"Umm..." James stammered "That's just it ma'am. There's a problem with the shorts."

"What problem, let me see..." she reached forward and James handed her the shorts. "34 waist...looks about right." James nodded. Looking them over she continued "they look fine to me, put them on and lets get started with class."

"Here?" James asked, shocked.

"Why not? I've seen it all before....I'll turn around if it makes you feel better, but get on with it." She turned and closed the office door, and began tapping her foot impatiently.

James took a deep breath then quickly undressed and pulled on his shorts and t-shirt.

"All set?" Mrs. Myers asked, and turned around without waiting for reply. 

James held his hands in front of his crotch, blushing furiously. 

"What's wrong?" The attractive young teacher asked "move your hands, let me see." She pulled his hands to the sides and saw at least two inches of James' flaccid, circumcised penis hanging out the right leg of the red running shorts. She gasped in spite of herself, and cursed silently as she felt her face flush.

She let go of his hands, which fell to his sides. His head hung down and he looked like he might cry. "Oh, I see the problem." she said, in the most calm voice she could manage. "Why don't you wear briefs?"

"I've tried." James said in a shaky voice they're really uncomfortable. I usually wear boxers, and just let...it...hang down." He still couldn't bring himself to make eye contact with the pretty teacher.

It was just as well since she was still staring at Jame's amazing organ. It had to be bigger than any she had ever seen, and it was soft! She quickly pushed the thought from her mind. 

Taking hold of James' shoulders, and looking him in the eye, she said "Listen James, you have nothing to be ashamed of, believe me." she smiled in a way she hoped was friendly, and not lustful "but we can't have you attending my class like this! Besides, you might get hurt."

Mrs. Myers wanted to appear confident, but she had never dealt with something like this before. "Okay, let's see if you can tuck it in behind the waistband." James jumped a little when she pulled down the elastic waist of his shorts. She then reached down with her other hand and closed it around James' member. Pulling it out, she was surprised at its weight and how little of it was covered by her hand.

James felt a wild thrill as the lovely teacher gently held his limp penis, several inches of it hanging down from her fist. He could feel the blood start to surge his organ, as Mrs. Myers stood motionless looking at it. She could feel it too, getting thicker in her hand until her fingers and thumb no longer connected on the other side. Before she knew it, James was fully erect, his manhood throbbing forcefully. It was now longer than her forearm, and the head had swollen to the size of an apple. She couldn't believe she was still holding this boy's huge erection. 

"Well," she said, swallowing hard. That's not going to work!" and forced a small laugh as she slowly released James' engorged member.

"Oh my god, I'm so sorry!" James exclaimed, now looking like he might try to run.

"Shhh..." Mrs. Myers said, putting her hand on his shoulder "it's perfectly normal for a boy your age. I'll excuse you from class today." glancing down at his massive erection "Take as long as you need to. Maybe even take a cold shower before you go. I'll think of something for next class. Come see me tomorrow, before it starts."

She would be thinking about hardly anything else! Flogging herself mentally, she headed out to teach the class. Feeling much warmer than usual.

Problem Student Ch. 02



The following day, James came to Mrs. Myers' office a few minutes early, like she had instructed. He looked a little nervous, but there was no sign of the near-panic from the day before. The teacher gave him a warm smile, which he returned. She really was quite beautiful. "Hello James." she said "I think I've got you covered." wincing at the unintended pun. 

Mrs. Myers produced a pair of the athletic shorts that all the boys wore, but these were several sizes larger than the ones James had the day before. She had taken in the waist so they would fit him, and hoped the extra length would conceal James' "problem". "Try these on!" she said brightly and tossed him the shorts.

James looked at the garment doubtfully, and Mrs. Myers turned around to give him some privacy, but when she heard him remove his pants, she risked a glance over her shoulder. She had to see it again, and she was stunned anew at how long and thickly it hung. She quickly turned away again and waited.

"Okay." James said, and Mrs. Myers turned around. The shorts did appear to cover him without too awkward a fit.

"There you go. I think we're all set!" The lovely teacher said cheerfully. Smiling, James began putting on his sneakers, but when he put his foot up on a bench to tie the laces Mrs. Meyers gasped as James' heavy organ flopped out from the leg of his shorts into plain view.

"Oh...my." the teacher said, consciously adding a tone of disappointment to her voice, trying to mask the thrill she felt again at seeing the boy's unique gift. "I guess this won't work after all."

James looked down, then put his foot back on the floor and smoothed the shorts back down looking embarrassed. "what if I just don't lift up my leg?"

"Well, let's see" Mrs. Meyers responded "jog in place."

James did as he was told, and almost immediately his penis began flailing around, popping out the leg of his shorts with every step. The teacher already saw that it wouldn't work, but was enjoying the show.

"Okay, stop. Now do some jumping jacks." she had to fight back a grin. James' manhood swinging freely with each jump. Suddenly she had an idea. 

"Nope, it's not going to work James, but I have an idea!" Mrs. Myers opened a drawer in her desk and pulled out an ace bandage. "Pull down your shorts and stand still" she ordered.

After a brief hesitation James complied, but covered his crotch with his hands, which looked comical since half his length was visible below his fingertips.

Mrs. Meyers knelt in front of him, unrolling the bandage. "Please move your hands James." she said softly "There's no need to feel embarrassed." Again, he complied, and the teacher was now staring at his over sized genitals, barely 18 inches away. "You really should have some support anyway, so I'm going to wrap this bandage around you to keep things in place." Looking up, she smiled and said "Just think of it like a custom jockstrap!" James smiled back, a bit uncertain.

The teacher started by placing the end of the bandage under his balls, going around just below his hip, around one buttock, back between his legs, and repeating on the other side. Much of the time his big flaccid member draped over one of her forearms as she held the bandage in place under his balls.

When she had to reach behind her face came very close to the boys dick. She wondered whether he could feel her breath on it. She made sure to exhale when near it, hoping that he could.

Almost immediately James' cock began to stiffen and its fat head eventually touched Mrs. Meyers under the chin. She felt a jolt of excitement at this, and had to resist a primal urge to wrap her lips around it.

James noticed the contact, and moved back, muttering an embarrassed apology. "It's okay James." Mrs. Meyers consoled "I know you can't help it. Let's just finish getting you wrapped up." She leaned in and continued wrapping the bandage. Pushing his growing erection to the side with one hand, she stretched the bandage over to secure it against his body. When she reached to pass the bandage around James' back, his now foot-long boner sprang out of the wrap and slapped heavily against Mrs. Meyers cheek.

"Yikes!" the teacher exclaimed "This thing's going to put my eye out if I'm not careful." she added, laughing. This seemed to put James more at ease, and he joined in laughing at her joke. She grabbed his massive erection firmly, near the base and tried pushing it down again, but it was too hard now. It was like trying to bend a small tree. She could push it back up against his stomach, but it looked ridiculous, extending almost to his chest. 

"What are we going to do with this?" Mrs. Meyers asked rhetorically, lightly slapping the head of James' huge penis against her cheek with each syllable. "We can't wait for it to go away, we're already latefor starting class." She frowned, thinking for a moment, absentmindedly tracing her fingertips up and down James' tremendous hard-on, sending waves of pleasure through his body. Suddenly she gripped the thick shaft firmly and said "you need to ejaculate."

James looked at her with a mixture of surprise and horror "Uh, you mean...?" he began to ask.

"Yes," the teacher replied "You need to masturbate, right now." 

"But..."

"Look, James, I'm not going to have you running around my class with this huge cock sticking out of your shorts!" She shook the meaty shaft at him for emphasis, like some kind of weapon, then released it and stood up. "You can use my restroom if you want some privacy. There's some hand-lotion in there, but I'm afraid I don't have any 'reading material' for you." Mrs. Myers added with a wink.

Still a bit dumbfounded, James took the remaining roll of bandage, turned and walked into the small bathroom, which contained only a toilet and a sink, and closed the door.

After a moment, the teacher could hear the faint slopping sound of James' efforts. She couldn't help but imagine what the boy looked like, stroking that massive tool, and it was making her very hot. She had never been very concerned with size, and her husband's equipment had always satisfied her. However, something about James' rare gift had her head swimming with lustful thoughts.

James seemed to be taking longer than she expected, so Mrs. Meyers opened the bathroom door without knocking and saw James with his eyes closed, leaning against the sink, stroking the full length of his incredible penis. "Is everything okay?" She asked.

James' eyes popped open and he looked his attractive teacher up and down in a way that would have earned most men a slap. He continued to stroke, but said "It's, um, just not working..."

Staring down at his raging erection, now shiny with lotion she replied "It certainly looks like it's working! Maybe you just need a little extra stimulation..." she paused for a moment thinking about what she was going to do then went on "James, have you ever seen a woman's breasts?" not waiting for an answer, she reached up and began to pull down the zipper of her jogging-suit top.

Mrs. Meyers was proud of her firm, full breasts, and rarely wore a bra, so when she pulled open the top, James was greeted with the view of her beautiful bare skin and reddish-brown nipples, erect with excitement. Almost immediately, James grunted, and began to discharge a load of thick semen, proportionate to his huge cock. It plashed against Mrs. Meyers' bare chest as James convulsed in orgasm. She let all the warm load hit her, but put a hand to her stomach to keep all the cum from running down onto her pants.

"My goodness James!" Mrs. Myers exclaimed as James stopped ejaculating. "That was quite something! Look at this mess...would you pass me some paper towels?"

As though snapping out of a trance, James said breathlessly "Oh my god, I'm so sorry!" still staring at her cum-covered chest. He pulled some towels out of the dispenser and thrust them at her.

"Well, that's what I hoped would happen, but I wasn't quite ready!" Mrs. Meyers replied, while mopping up semen from her torso. "Lets get you wrapped up and start class. We're already late!"

After wiping the rest of James' abundant seed off her body, she zipped up her top. Deftly, she finished wrapping him up with the bandage, securing his rapidly softening member against his pelvis.

"That should do it!" Mrs. Meyers said and patted the big lump under the bandage. "Let's get to class."



Problem Student Ch. 03



Thanks for the great comments and suggestions, I've tried to apply them to the third installment of the Problem Student story. Please enjoy!

=================

The teacher had asked James to take the bandage with him, and try doing the wrap himself before the next Phys-ed class, but to come see her before class so she could check it. James headed to the boys locker room a little early, and did his best to emulate the snug, and slightly complex pattern Mrs. Meyers had created with the bandage. After pulling on his gym clothes, he headed to the teacher's office, which adjoined the girls locker room, on the opposite side of the gymnasium. 

James knocked on the heavy steel door and heard Mrs. Myers' voice call "come in" from the other side. He opened the door and went in, closing it behind him.

"Hi James" the teacher said brightly, looking up from some papers on her desk. She looked different to James. Her dark, shoulder-length hair was wrapped in a loose bun, showing the fair skin of her slender neck. The upper of her thick, smiling lips protruded beyond the lower in a little overbite James had not noticed until now. Her lips looked darker, and more striking than usual, because of the lipstick she wore. She normally wore a much lighter shade, if any.

"James?" Mrs. Myers probed, waving her hand at James. He blinked and shook his head slightly. He had never looked long at this beautiful teacher who had been so nice to him, and he was nearly swooning as he took in the details of her face. Her nose was rounded, but not broad, with faint freckles across the bridge, continuing over the tops of her rounded cheeks, lifted by her smile. The light creases at the corners of her eyes gave her face a motherly quality, without detracting from her beauty.

"Uh, hi Mrs. Meyers." he croaked, then swallowed "You just look so beautiful!". The honest words tumbled out of his mouth before he realized what he was saying.

"Oh, why thank you." The teacher turned her head slightly, looked back at him, and her cheeks colored. "That's nice to hear from a handsome young man."

James' face became several shades closer to red and he couldn't think of anything to say.

Mrs. Meyers stood up from her desk, walked over to James, saying "Let's see how you did with your homework." and flashed a warm smile. She immediately pulled down his shorts and began to examine his work with the bandage. He noticed her sweatshirt was partially unzipped, allowing glimpses of the inner curves of her breasts. She tugged gently at various parts of the wrapping, especially near the obvious bulge it was meant to contain. James could feel the pressure as he began to become aroused.

"Oops!" Mrs. Meyers exclaimed "Look what we have here." James' rapidly swelling penis had slipped out between two layers of bandage, and the teacher had gripped it between thumb and forefinger and was flopping it up and down. "You did a good job James, but the wraps didn't overlap quite enough. Let's get it fixed up." She said and began undoing the bandage, starting at his waist. By the time she got it undone, his semi-hard dick was standing out, arcing down slightly, swaying by her left ear.

"Oh darn." the teacher said in an even tone when she turned to regard the huge erection forming inches from her face. "I guess I should have told you to masturbate before class." She pushed down on the massive phallus with one finger, causing it to bob up and down. "Not that it would matter I suppose, young men's hormones being what they are." Mrs. Meyers gently patted James' fist-sized scrotum. 

"Well, let's try to take care of this quickly." Standing up, she continued "Do you think it will help if I show you my breasts again?" Without waiting for an answer, the teacher stepped back, unzipped her jogging suit top and shrugged it to the floor. She then stood before James, hands on hips, her torso now completely bare, and drank in his reaction.

James had briefly seen the teacher's lovely breasts before a couple of days earlier under similar circumstances, but was no less stunned when she stripped off her top. His eyes widened and wandered over her half-naked body.

Her torso was slender but not bony. Her breasts hung down slightly, protruding out from her chest at angles. They were about the size of softballs and came to gradual points where her dark nipples pointed gently upward. Mrs. Meyers' slim waist was exaggerated by the way her plump breasts extended to her sides, almost as wide as her shoulders. The contours of her abdominal muscles were clearly visible, narrowing in contrast to the broadening of her pelvis, where the jogging pants hung, several inches below her navel.

"I can see this is helping." the teacher said, sounding satisfied, gazing at James' erection, now pointing up at a steep angle and throbbing visibly with his quickened pulse. "Let me get you some lotion." She walked past him to the bathroom, not watching him, but she felt his eyes on her and smiled.

James admired Mrs. Meyers' firm breasts as they jiggled and swayed with her steps. He was sure his cock had never been this hard. He thought it might explode if he touched it.

Mrs. Meyers returned with the bottle of hand lotion. "I think I'd better take care of it this time." She announced "Why don't you have a seat and relax."

Slowly James lowered himself into a nearby folding chair. The metal was cold on his bare ass. Incredulous, he asked "You mean you're going to..."

"Yes, I'm going to jerk you off." She said, answering his unfinished question. "It will be faster that way. Is it okay if I rub your big dick James?"

James was too stunned to speak. The unexpected vulgar language had him trembling with excitement. He nodded his head vigorously, and watched his gorgeous topless teacher squeeze some lotion into her hand and kneel down in front of him.

Mrs. Meyers put the bottle down, rubbed the lotion between her palms, then gripped James' massive shaft with both hands. James started as bolts of pleasure tore through his body. The teacher stroked up and down on the rigid organ, lightly squeezing with both hands, feeling the thick veins rippling under her touch.

James let out a soft moan. "Try to be quiet James, but let me know when you're about to ejaculate, so we don't make a mess like last time." The teacher instructed him as she worked her hands along his hard penis. 

Mrs. Meyers was becoming extremely aroused. Playing with this boy's amazing penis was incredibly exciting. She noticed James leaning, trying to get a view of her bare chest. She raised up so her erect nipples were about the same height as the huge red-purple head of James' club-like dick.

"I'm sorry, I didn't mean to hide my tits on you. Here." The teacher held the thick member near its base and began slapping it back and forth between her boobs, making them jiggle. "Is that better?" James nodded. "Do you like my boobies?" She asked. He nodded again. "I thought so. Not too bad for an old lady huh?" James thought she was the most beautiful thing he'd ever seen.

"I have to tell you James," She started stroking him again, this time leaning forward with her breasts on either side of his dick. When she slid her hands up, her forearms lifted her breasts, making them bounce with each stroke. "I'm really enjoying this. Your huge cock is beautiful and exciting. I love touching it." The teacher squeezed it hard.

Hearing his lovely and sexy teacher say how much she liked his cock was all the stimulation James could take. He felt the stirrings of an orgasm, and remembered to warn Mrs. Meyers.

"I'm uh..." James began, urgently. 

"Just let it go honey." Mrs. Meyers said softly, then she opened her mouth and pushed her head down on the thick rod she was holding. The oversized glans filled her entire mouth, and she kept stroking with her hands as she sucked greedily on James' fat cock-head. It spasmed immediately, the throb forcing her jaw open wider. The first jet of semen gushed against the back of her throat, making her gag slightly. The warm fluid quickly filled the remaining space in her mouth, and began to ooze past the seal her thick lips formed around James' shaft to trickle down her chin.

She got her reflex under control and began to swallow rhythmically as jets of cum continued to surge against her throat. Mrs. Meyers sucked hard while rubbing her tongue vigorously against the sensitive flesh erupting inside her mouth.

James grunted and moaned, clapping one hand over his mouth to keep from crying out as his teacher continued stroking and sucking. He had never experienced anything like it. The orgasm went on much longer than either of them expected, and Mrs. Meyers dutifully gulped down everything the boy's exaggerated sex organs had to offer. 

"Well, James." The teacher said after she pulled his softening tool out of her mouth with an audible 'pop'. "I think I can skip lunch today." she smiled impishly, then wiped the dribble of semen from her chin with one finger and sucked it clean. "And look, no mess! Now stand up and we'll get you ready for class."

James was panting, unable to move. He watched Mrs. Meyers stand, then don her sweatsuit top. As she began zipping it up, James said "I love you, Mrs. Meyers." 

The teacher stopped and looked at him. She crouched down and put a hand on his knee. "Now James. None of that." She scolded "I'm a married woman, and your teacher too. I'm just helping a student with a special problem." She reached out and held his soft, but still huge penis in her hand. "You're a handsome young man with a very unique gift. I'm sure you'll have no problem finding a nice girl." James looked crestfallen, and Mrs. Meyers quickly added "If you ever need any more special help, just let me know." James then smiled "And don't be surprised if I call on you if I've missed lunch!" 

They shared a laugh, then the teacher dressed him up with the bandage as she had done before and they left for class. She with a full belly, and he on shaky legs.