The Trouble with Henry

Story Info
Oversexed guy is enslaved by his older sister.
3.8k words
4.2
196.1k
64

Part 1 of the 4 part series

Updated 10/18/2022
Created 04/27/2006
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

It was such a small thing—just a fold laid wrong—you or I might not even notice it, but Debra was instantly aware that someone else had touched her panties. Neatness was something she prided herself in and took special pains to maintain. Not even her mother dared to arrange her clothing or put it away once it had been washed.

Debra pulled the delicate garment from the drawer and held it open, looking closely for any signs of violation. She examined the lace trimmed waistband and leg openings, and then studied the small cotton crotch panel. There were no rips or stains that she could see. She sniffed both sides of the panel, but could detect no scent other than the faint clean smell of detergent.

She lowered the panties slowly, caressing them to her cheek, then along her slender neck, finally brushing them across her firm breasts. Her hand lingered there, rubbing the smooth material against her skin until she felt her nipples harden beneath it. A stirring in her loins caused her to sit down on the bed and bring her other hand up until her fingers found the moist source of her arousal. She lay back with a sigh and spread her thighs. She would be late for class again, but college biology lectures were crushingly boring. Anyway, she thought—as she felt her clit swell beneath her busy finger—wasn't this a better way to learn biology?

Afterward, as Debra finished dressing and smoothed the front of her skirt, she felt the hem of her panties pressing against her taut stomach, and remembered. She opened her underwear drawer and made some careful adjustments, then hurried off to her classes at the local community college. Maybe her suspicions were unfounded but if they weren't, she damned well needed to know. If that little bastard of a brother was getting into her stuff she would soon know it.

Henry got out of high school at 2:00, which put him home two hours before his older sister Debra. Since his mother worked even later, and his father was fishing in Alaska, Henry had learned to use his "private time" in the manner of most oversexed teenagers. He masturbated every chance he got. Having just turned eighteen, Henry knew he should be moving on toward real relationships, but it wasn't happening. Part of the problem was physical; he was smaller than most boys his age, and his effeminate features and small penis often made him the butt of locker-room jokes. So Henry kept to himself, comforted by a line from an old Woody Allen movie that he once saw on cable: "Hey, don't knock masturbation – It's sex with someone I love."

Henry had gotten a stronger push down the road to self-indulgence than most boys his age when—three years earlier—he discovered his parent's stash of erotic literature, along with some nude Polaroids of his mother. This had fueled his fantasies like nothing before. Then, last year, he caught a glimpse of his sister's tits when her towel slipped as she came out of the bathroom. After that, Henry's sexual fantasies always included his sister, and sometimes her college friends as well.

Since the photos of his mother had been hidden in the back of her lingerie drawer, it was inevitable that Henry's interest in female undergarments grew along with his fantasies. It wasn't long before he began trying on some of the strange garments. The first time he put on a pair of his mother's panties he came almost instantly. He had to wash out the stains and then dry them before anyone got home, but unfortunately he put the dryer on "high" and scorched the panties. He hid them in the trash and prayed his mother wouldn't miss them. Debra came home and interrogated him about the smell in the laundry room, so Henry made up a story about drying out his wet tennis shoes. Debra was skeptical, but let it pass.

Eventually Henry tired of his mother's things. His mother was a big woman, and her things didn't Henry's narrow build well at all. One day, as he pranced in front of her big mirror and stroked his cock, he saw how poorly they fit and knew the illusion just wasn't good enough anymore. That's when he decided to try his sister's underwear. She was slender—except for her breasts, which were like ripe peaches—and though her hips were wider than Henry's, he knew she'd be a better fit than their mother. Then he thought about the risk. Debra was very sensitive about Henry touching any of her stuff. If she ever found out, she would beat him to a pulp.

Finally one day Henry was unable to contain his curiosity any longer, and he decided to throw caution to the wind. He crept into Debra's room as soon as he got home, and was ultra-careful not to disturb anything she might notice. He felt giddy the moment he opened her underwear drawer and saw the neatly folded piles there. He carefully noted the exact placement before he touched anything. At last—holding his breath—he took out a pair of her panties and held them out. They were small yellow cotton things with lace trim. He rubbed them against his face for awhile. His cock surged with anticipation. Henry pushed his pants down around his ankles and began rubbing the thin material along his penis.

The neighbor's car pulled in and Henry heard their door slam. Panicking suddenly, he quickly folded the panties and put them away, then scurried out of his sister's room. There was always tomorrow he thought, closing her door. Poor Henry was blithely unaware that his less-than-perfect folding job would soon be his undoing.

The next day, Henry came home and immediately resumed his exploration of his sister's underwear drawer. He took all of his clothes off first, and then tried on several pairs of Debra's panties, carefully folding each one and putting it away before grabbing another. In his excitement he failed to notice several fine hairs falling loose from where Debra had carefully placed them.

Debra came home that afternoon and found Henry—as usual—watching television. She went up to her room and immediately discovered that her trap had been sprung. Henry had been rummaging through her underwear! She suppressed the urge to run downstairs and strangle the little fucker. Instead she paced her room like a caged lioness. Soon a plan began to form. She would catch him in the act, prove his guilt beyond any doubt, and then exact her revenge.

The red lace body-stocking was a gift from a male admirer who had hoped to see Debra wear it. She was not inclined to grant his wish however, and had placed it—still in the original box—high up on her closet shelf, under a pile of sweaters. Now she retrieved the provocative garment and laid it in the underwear drawer where Henry would surely see it. Then she quietly slipped into her parent's room and grabbed the Polaroid camera, along with some film and flashbulbs.

Henry hurried home from school the next day, planning to use as much time as possible exploring the wondrous things he had discovered in his sister's room. This time he stripped off all of his clothing before beginning his explorations. The vulnerability of being completely naked seemed to excite him more. With his little penis wagging in front of him to point the way, he carefully opened Debra's bedroom door and went inside.

Something caught Henry's eye as soon as he opened the underwear drawer—a red filmy garment he had not seen on his previous visits. Carefully noting how it was folded, he lifted it out and held it open. It looked like a one-piece bathing suit except that it was so sheer he could see right through it. Examining it closer, he noticed two tiny snaps right in the bottom of the crotch. This excited Henry so much he knew he had to put it on immediately.

Debra looked carefully out from her hiding place in the darkened closet and watched Henry fumble with her underwear. She felt the rage building within her and struggled to suppress it, gripping the Polaroid camera so hard that her knuckles turned white. She wanted to rush out and beat the living shit out of her little brother right then, but she held on for the more satisfying vengeance taking shape before her eyes.

Henry shimmied the garment up over his narrow hips and flat chest, and then pulled the delicate straps over his pale scrawny shoulders. He turned to look at himself in the floor-length mirror. He was stunned at how much it made him look like a girl. His little cock stiffened and begged for release. Henry squatted and felt between his thighs. His fingers found the two crotch snaps, and he pulled on them. The snaps parted and his little cock popped free...

FLASH!

Henry whirled around to find his sister facing him, aiming a camera right at him. He froze, and everything seemed to go into slow motion. He heard the whir of the camera motor as the photo rolled out. Before he could reach down and cover himself, another bright flash caught him in a full-frontal exposure. Stunned, blinded, Henry's mouth flapped open like a fish out of water. He couldn't think of what to say. Even in that first moment of discovery Henry sensed that somehow his life had changed forever.

"You fucking little pervert!" Debra screamed.

Henry finally overcame his shock and turned to flee.

"Come back here!"

A final flash captured his white ass-cheeks in retreat, pumping hard below the flapping tail of red lace. Henry ran into his room, slammed the door, and leaned against it. He expected Debra to come banging on the door any second, but there was only silence. Finally he heard soft footsteps approach the door.

"Henry," Debra called softly, "Please open the door honey."

"No! You'll hit me!" Henry replied.

He was frantic—he knew she could force her way in if she really wanted to. He stood there shivering in the thin garment, ashamed and frightened. His sister's voice came soft and reassuringly from the other side of the door.

"Nonsense. I understand how little boys are—I won't hurt you. I just want to show you something."

"W-what?" Henry blubbered, nearly in tears.

"Why your pictures, of course," Debra replied. "They came out real nice. Of course if you don't want to see them, I'm sure someone will. Maybe I'll give them to the yearbook committee. This one here might make a nice senior picture."

"Noooo! Please don't!"

"Then come out here right now and we can discuss this." Debra's matter-of-fact tone made it clear to Henry that he really had no other choice.

The door opened a crack and Henry peered out. Suddenly his ear was being pulled so hard he felt it would come off. He stumbled out into the hallway screaming and falling to his knees. Debra pushed him down and kneeled across his back and neck, immobilizing him.

"You pathetic little bastard!" she hissed, "I should beat the shit out of you."

"I'm sorry. . ." Henry whined.

Debra pulled up the back of the garment, exposing Henry's small white buttocks. She spanked him hard with her open hand, eliciting more screaming. Henry struggled but was unable to move.

"Shut up!" Debra commanded.

Henry continued crying, so she beat his ass some more and told him to be quiet again. This was repeated until he finally learned that the only way to stop the punishment was to be quiet. By this time his bottom was beet-red and burned fiercely from Debra's blows. He sniffed and whimpered in pain then fell silent.

"Okay, that's better," Debra said. "Now we have to figure out what to do with you."

"What do you mean?" Henry whined, then cried out as she viciously struck him again.

"Shut up! You will no longer speak to me unless I ask you to, understood? Nod your head."

Henry nodded, frightened. He had never seen his sister so dominating before. She held a photo out in front of his tear-streaked face. He saw himself posing in profile, hands holding the lacy crotch-flap up to reveal his hard little cock.

"This is good stuff Henry," she teased, "You should be a model."

She held the next photo out, showing his panicked stare as his scrawny body stood fully exposed, looking ridiculous in the sheer red garment. Finally she turned to the last photo, Henry in flight, his small pale buns flexing as he ran for the door. He knew the photos could ruin him if Debra ever let them fall into the wrong hands. Life would never be the same—he would be an outcast. He turned his head aside and began sobbing.

Suddenly Debra got up and stood above him. There was another flash and whir. Henry rolled over and tried to cover himself, but the next flash blinded him again.

"There," Debra said contentedly, lowering the camera. "Our little family album is nearly complete. I just had to see how well the red in your sorry little whipped ass would show up."

Henry sat clutching his knees against his chest while his sister watched the newest photos develop. He could see from her expression that the results were good—and bad for him. She turned to Henry with a stern expression.

"Now get up and strip! And if you tear my stuff you'll really be sorry."

Henry got to his feet slowly and began peeling out of the clingy garment, intensely aware of his sister's gaze. Blushing, he handed it to her while attempting to cover his crotch with his other hand. She reached out and slapped his hand away, leaving him fully exposed again.

"Don't cover yourself in front of me! Your ass is mine now, pervert. Now get down on your hands and knees and follow me—I'm not done with you today."

Debra strode off toward her bedroom with Henry crawling along behind her. She stood by the doorway until he had crossed the threshold, then sent him sprawling face-forward onto her rug with a vicious kick to his flushed bare ass. She slammed the door shut behind them, the sharp sound startling Henry and adding to his sense terror and of entrapment.

Debra looked down at Henry with eager anticipation. Her little brother would now be her personal slave, for as long as she wanted. She saw that her foot had left a nice imprint on his ass. She ground her shoe against Henry's other butt-cheek, chaffing the already inflamed skin. He nearly choked trying to stifle his own sobs.

"My feet are tired from kicking your sorry ass," she said, kicking her shoes off and stripping out of her pantyhose. "I want you to massage them for me."

Debra sat down on the bed and held a foot out expectantly. Henry shuffled over on his knees and began to rub it. She reached down and grabbed him by his hair and pulled his head roughly upward to face her.

"Not that way you idiot!" she hissed, "Use your tongue. Wait."

She pushed him back, then slid farther up onto the bed and lay there with her feet hanging out in front of Henry's tear-streaked face. He began to lick the soles of her feet but she squashed them violently against his face and sat up.

"Careful! You're tickling me. Suck my toes—all over."

Debra lay back down and basked in the feeling of power that she now had over her 18-year-old brother. He was already adapting well to his new role as her personal slave, she thought, as his wet little tongue began stroking into the crevices between her toes. Her hand strayed up under her skirt and found the warm wet signs of her arousal. She languidly began stroking herself through her panties.

Debra felt Henry change position. She glanced down and caught him looking up between her legs, where her hand was busily engaged. Infuriated, she leapt to her feet and grabbed him by the throat. Then she remembered that any bruises on Henry's neck might be noticeable to her mother. She shoved him facedown on the floor and then peeled her moist panties off.

"Here!" Debra held up the cotton panties. The crotch was darkened with her fresh pussy juice. "Just what we need for you."

Henry was afraid to look up from where he lay on the floor. Despite his terror he kept thinking about the image of Debra's fingers buried under the edge of her panties, and the soft brown pubic hairs protruding around them. His penis stirred under him and his ass cheeks quivered involuntarily. Suddenly he felt her kneel on his back and grab his hair.

Debra pulled Henry's head back and pressed the soiled panties against his eyes, blinding him. Then she wrapped a pair of pantyhose over the panties, tying the ends tightly around her brother's head to make an effective blindfold. Jerking the terrified boy to his feet she stood back to survey her work.

Henry stood unsteadily before her, naked and shaking from fright. Interestingly his little penis showed definite signs of arousal. Debra adjusted the panties, releasing the crotch so that it hung down over Henry's nose. His face wrinkled.

"Nice, huh?" She pushed the wet stain against his nose with her hand, and then covered his mouth with her other hand so that he had to breathe through his nose—and the panties.

"Do you like that Henry?" she asked. "Isn't that what you wanted, you little pussy whore?"

Henry was hyperventilating and could not hold his breath for more than a moment. The strong scent of his sister's sex invaded his nostrils. He also felt the dampness, and he knew it was the result of what he'd just seen her fingers doing only moments before.

"I have an idea," Debra said. "Stand still."

She pulled a loose end of the pantyhose across Henry's nose and tucked the end under at the back of his head. Now the crotch stain was pressed against his nose by the gauzy material without her help. Then she grabbed Henry's penis and led him over to the foot of the bed.

"Kneel down slave, and we'll try this again," she commanded, pushing him to his knees.

There was a rustle of clothing, and then Henry heard the bed springs creak as his sister climbed back into position. With the blindfold on he was unable to see that she had stripped the rest of her clothing off. She grabbed his hair and pulled him up between her outstretched thighs. He could feel the heat as she pulled him closer ... and suddenly his mouth was buried in the soft down of her pussy.

"Lick it, you little slut," Debra commanded.

Henry stuck his tongue out and pressed it against the hot slippery folds of flesh. They parted easily and he quickly found the firm nubbin of her clit. The scent and feel completely enveloped him; it was like nothing Henry had ever experienced. He also knew immediately that he would want to experience it again, and again. He felt his little cock grow hard where it pressed against the mattress.

"That's the spot, slut-boy. Faster now! Lick!" Debra yanked Henry's hair toward until his mouth was pressed tightly to her quivering pussy.

Henry was having trouble breathing, but he obediently licked her clit as rapidly as he could. Debra's whole body began to shake as a massive orgasm approached. Her moans accompanied the wet sucking sounds of Henry's busy lips and tongue.

"Oooohhhhhh!!" Debra came hard. She threw her legs up and slammed her thighs together with such force that she nearly crushed Henry's skull. Her body spasms drove Henry over the edge too, despite his barely being able to breathe. He shot his cum all over the sheet beneath him. Debra felt her little brother shudder and moan. Thinking he might be about to pass out, she opened her damp thighs and released him. When she saw that he was still concious, she unceremoniously shoved him backwards off the bed. He hit the floor with a soft thump.

Henry knelt on the floor at the foot of Debra's bed, his face still dripping with her juices. Debra ignored him and gently ran her hands over her firm breast while her breathing slowed. When Debra finally got up, she saw the pool of cum on the bed. Surprisingly, she was not angry. This was just was further evidence of her new power over her younger brother.

"Oh, you liked that did you, my little slut? Good. Get used to it, because from now on you are my personal slave." She put on a short robe and came over to where Henry kneeled, still blindfolded.

"Now get up!" She pulled him up by his hair. "Get dressed—Mom will be home soon."

Debra opened the door and shoved Henry out into the hallway so hard that he fell down. She bent down and yanked his makeshift blindfold off. Henry rolled over to hide his weeping little penis from her. This somehow irritated Debra. She whacked him hard on his bare ass a few times, and stood over him, hands on hips.

12