The Trouble with Henry Ch. 03

The pain was almost unbearable. Henry knew he had stayed out in the harsh sun too long, and now he'd pay the price. The tender skin of an eighteen year-old could only take so much punishment. It wasn't merely the pain of the sunburn that concerned Henry, it was his older sister, Debra. Henry knew that she would use it as just one more excuse to humiliate and abuse him. But there was nothing he could do about it. As soon as he offered any resistance Debra would drag out the photos and remind Henry that he was literally her slave. Henry knew that if he ever refused her orders, the very next day those same photos would show up at school. He would be ruined.

The whole family had come up to the lake-cabin for the first weekend of spring break, but their parents had been unable to get away from their jobs for the entire week. When Debra had asked if she and Henry, along with Miko—their Japanese exchange student—could stay at the cabin during the week, the parents had happily agreed. They stocked the refrigerator and left instructions for Debra, who was to be in charge while they were gone. They planned to drive up the following Friday, spend the weekend, and everyone would return home together.

Henry was a little worried about spending all that unsupervised time with his sister and Miko, but there was plenty to do outside, with swimming, canoeing and exploring right at their doorstep. Now that was out; this sunburn would keep him grounded for awhile. And it was only Monday. The only consolation was that by Friday, when his folks returned, he'd have healed and his mom wouldn't give him hell for not wearing sunscreen. What he hadn't counted on was his sister's reaction.

Henry sighed and stepped out of the shower. The cool water had felt good while he was standing under it but now he had to get out. There was only one bathroom, and Debra needed to use it now. She'd already knocked several times, each one louder than the last. An angry Debra was not something Henry wanted to face anytime, but especially now.

He dried off quickly but the rough towel abraded his burned skin. He let out a small whimper. Debra—standing right outside the door—heard it.

"Henry? Are you all right?"

"Unh. Y-yeah."

"Henry, you don't sound good. Let me in. I need to look at you."

"Can't. No clothes on," he replied in a small quaking voice.

"Henry..." Debra's voice softened. "It's okay. I just want to help. Come on honey, open the door."

Debra could be pretty persuasive when she wanted to. Maybe she wouldn't be as mad as Henry feared. He unlatched the door and held the towel in front of him. The door opened and Debra whisked in. she gasped when she saw the color of Henry's skin.

"Oh Henry! What have you done?"

She reached out to touch his inflamed skin. Henry flinched and drew away.

"D-don't!" he yelled. "It hurts!"

It was the wrong tone to use with Debra. Her face hardened and her hands went to her hips.

"Of course it does. And the whipping I give you for not wearing your sunscreen is going to hurt even more." She stepped in front of the toilet and unzipped her jeans. "Turn your back, Henry. I can't hold this any longer, thanks to you."

Henry started to turn away, but then remembered that his bottom would be exposed. He struggled with the towel, dropped it, then quickly picked it up and wrapped it around himself.

Debra ignored her brother and pulled her pants and panties down. As she sat on the toilet Henry stole a glimpse of her soft brown patch of pubic hair. It wasn't the first look he'd ever had, indeed she'd had his face buried in it several times since that day she caught him wearing her lingerie, but Henry was still fascinated every time he saw it.

Henry listened to Debra's pee splash into the toilet. It sounded like someone had opened a faucet. Boy she was really holding it in, he thought, regretting the delay he'd caused her.

Debra wiped herself, then stood and pulled her clothes back up. Henry kept his back turned, but his brief peek, combined with memories of his earlier sessions with her, had a predictable but undesired effect. He felt a bulge growing under his towel.

"Okay, you can turn around now," Debra said.

As soon as Henry turned, Debra saw the lump under his towel. "Why you little pervert! You were peeking weren't you? Well you must have liked what you saw."

If Henry weren't already sunburned, Debra would have noticed him blush. His fantasies involving his big sister had begun long before she'd caught him trying on her underwear. He still recalled those stormy nights when she let him share her bed, and they would innocently clutch each other tightly at every clap of thunder. He remembered the fresh smell of her hair and the soft warmth of her skin against his.

It all ended that awful morning when they woke up together and noticed a sticky wetness under the sheets. Debra was as puzzled as Henry at first, until she pulled the waistband of his pajamas open and peered inside. Furious, she'd dragged him out of bed and pulled his soiled pajamas off, exposing the sticky evidence of Henry's first wet-dream. Before he could even get over his shock, Debra bent him over her knees and spanked his bare bottom until. Afterward she cleaned him up and made him wear one of her sheer teddies around the house all day.

Henry was mortified of course but even worse, he'd not been allowed back into her bed since then. That loss, combined with his introduction to wearing frilly lingerie, had most likely motivated Henry's later transgressions. Soon afterward he discovered his parent's stash of erotic literature in the bottom of the nightstand drawer. The stories strengthened his sexual urges more than any Playboy ever had, but the shy and awkward Henry still found himself unable to approach any girls at school.

As Henry's social world withered on the vine, his private fantasies grew. Eventually he needed more stimulation than just the stories. He recalled the erotic feel of Debra's nightie on his bare skin; he wanted to experience that feeling again. He began making forays back into her room, where it had all begun, only this time it was without his sister's knowledge. Or so Henry had thought, until that first flashbulb popped and Debra stepped out of the closet to take over his life.

"Here Henry, give me that," Debra said, grasping the edge of the towel. "Don't be embarrassed. I'm your big sister. I've seen your body before."

Henry reluctantly released the towel, and Debra pulled it aside and hung it up. Then she began to examine him. The small area that had been covered by his swim-trunks was stark white in comparison the inflamed skin covering the rest of his scrawny frame. Henry trembled under her prodding fingers, and kept his hands clutched tightly over his genitals. Debra pulled them away and lifted his arms to examine them. She pretended not to notice his little penis sticking straight out.

"Shit!" she exclaimed as she turned to look at his backside. "This is a bad burn. I need to get some lotion on you. Then we'll find something loose and comfortable for you to wear around the cabin while you heal. You're not going outside for a few days."

Debra opened the medicine cabinet and retrieved a bottle of sunburn lotion. "This will get messy," she said, unbuttoning her blouse.

Henry watched in disbelief as Debra stripped down to her panties and brassiere. She poured a generous amount of lotion on her hand and gently applied it to Henry's shoulders. The lotion was cool and soothing. Henry closed his eyes and enjoyed the feel of his sister's hands on his bare skin. He felt woozy and started to fall.

"Whoops!" Debra caught Henry and pulled him against her strong lithe body. "You're in worse shape than I thought. Let's get you out of here." She took his arm and helped him out of the bathroom.

The cabin was rustic, with wood-plank floors and log walls, but also quite large. There were three bedrooms in addition to the large open area shared by the kitchen and family room. Miko was sitting on the living room sofa, reading a magazine. She looked up as Debra entered with Henry, and her eyes grew large as she took in his naked and badly sunburned body.

Henry glanced over at Miko could swear that he saw her lick her lips.

Debra led Henry into the bedroom that she and Miko shared. Henry suddenly felt self-conscious. He had not been inside in Debra's room—here or at home—since that last night they'd slept together. He reached down to cover himself as she turned and crossed over to her dresser.

"Now let's see what we have for you," Debra said, rummaging around inside a drawer. "I think one of my loose cotton dresses would be best."

A dress! Henry got a strange fluttery feeling in his stomach at the thought of wearing his sister's clothing once more. Debra saw his lip tremble and mistook it for fear. She tried to comfort him, placing her hands on the only place she could find that was not burned—his pale skinny hips. She bent close to his ear and spoke in a confiding tone, almost in a whisper.

"Now Henry, relax. No one will see you in the house, and you'll be more comfortable this way."

No one except you and Miko, thought Henry as Debra turned her back and resumed searching through her clothes. He resigned himself to wearing a dress or whatever else she came up with. The sunburn had made him weak and dizzy to even think about resisting. In fact it was hard to even remain standing. His knees began to shake and he started to sway.

Debra continued pawing through her clothes, unaware of Henry's rapidly deteriorating state. "Yes, a dress will be best for you. Then you won't need to wear anything underneath. Underpants would just chafe you and make it worse. Henry? Are you listening?"

Debra heard a noise and spun around. Henry had fainted. He was sprawled halfway onto her bed and sliding off toward the floor. Trying to avoid his burnt areas, she caught him with one hand under his buttocks and the other under his arm and lifted him gently back up onto the bed.

"My god you're hot," she exclaimed. "I can't tell whether it's the burn or if you're running a fever."

Debra ran into the bathroom and returned a moment later with a thermometer. She rolled Henry over onto his side so that his back was facing her.

"Ohhh..." Henry groaned. "What happened?"

"You fainted. Now lay still. I need to check your temperature. This is a rectal thermometer, which means I have to poke it in down here." She ran her finger lightly between his buttocks.

"No. Please." Henry squirmed and buried his face in the pillow.

"Be quiet! You think I like doing this?" If Henry could have seen Debra's smile he'd know that in fact she did enjoy it, just as she would enjoy the spanking she'd give him later. "This is your entire fault, so be still and don't it any worse."

Debra shook the thermometer down and swabbed some Vaseline on the end it. Holding one of Henry's butt-cheeks open with one hand, she pushed the slender rod into his puckered little anus. Henry twitched and whimpered.

Smack! Debra's hand across his butt cheek had the desired effect, and Henry lay still at last.

Debra held the thermometer in place for awhile, her other hand resting on his bottom. Her anger grew as she thought about how much hell she'd catch if their mother saw the sunburn. She had specifically told Debra to make sure Henry wore his sunscreen. Now she and Miko would have to play nursemaid and make sure he healed before Friday. Why couldn't the little bastard stay out of trouble? Well, she thought, maybe we can have some fun at his expense. She began moving the thermometer around inside of Henry, rotating it slowly as she pulled it in and out.

Henry was really feeling strange now. The cool glass thermometer sliding into his ass was a shock at first, but when she began moving the tube around in him it felt good. He felt himself getting erect and moved his hands down to hide it.

Debra finally pulled the thermometer out, wiped it with a tissue, and examined the reading.

"You do have a small fever Henry," she said, "but it's not too serious."

She laid the thermometer aside and looked down where Henry's hands were trying to hide his erection. She rolled Henry over onto his back and pulled his hands away. His fully erect penis sprang into view, the tip already glistening with the first clear drop of pre-cum.

Now it's time to have some fun, thought Debra. "My goodness! You seem to have enjoyed that, little brother.," Debra grasped Henry's rigid shaft and wrapped her long fingers around it. "Do you like having things poked in your ass?"

"N-no."

"Oh, I think you do." Debra slowly stroked his cock as she spoke. "I think you just love it. Here, I'll prove it to you."

She pulled Henry's knees up and pushed his thighs apart. With her free hand she dug down between his buttocks, probing for his hole. She touched her finger against it, lightly at first.

'Ohhh..." Henry felt himself wracked by waves of intense pleasure. His breaths came in short hard gasps. His jaw slackened and he opened his mouth. "Oooo ... Ahhhh...."

"That's it," Debra purred, "Just let yourself go."

She thrust the tip of her finger into his greased hole and wriggled it. Then she plunged it all the way in and hooked it against his prostate. The effect was instantaneous. Henry cried out and shot a small load of sperm onto his belly. Debra kept pumping his cock while he thrust his hips upward to meet her and then down again onto her insistent finger. She kept him like that until she had milked him dry. Finally, Henry's cock softened and his breathing slowed. He sighed and closed his eyes.

"Wasn't that fun Henry? Now you have to clean it up."

Debra scooped the puddle of cum off Henry's stomach. She lifted his head with her other hand. "Open your mouth," Debra commanded.

"Wh-what?"

"Do what I say Henry. Don't argue!" Debra dribbled the sperm into his mouth, then forced it shut. She watched his expression with obvious amusement as he swallowed the slippery mess. Afterward she made him lick her palm and fingers clean, then pushed him back on the bed. He was asleep within minutes.

When Henry woke up it was dark outside. He was naked, but the window was open and the gentle breeze felt good on his bare skin. He lay there on the cool sheets for a long time before it dawned on him that this wasn't his own bed – he was in his sister's room! He shifted and tried to get up. The sheets rubbed on his burned skin, and then he remembered what had happened.

Debra walked in, carrying a tray. She was dressed in shorts and blouse again.

"I thought you might be awake. Here's some soup and toast."

Henry reached down and pulled a sheet over his lap. He wondered why Debra was being so nice to him. He decided to just relax and enjoy it while it lasted. Henry had finished the soup and was sipping the last of his lemonade when Debra came back in. She had the thermometer again.

"Gee, Debra, do we really have to—"

"Shut up. I'm in charge and you'll do as I say. Do you want me to bring Miko in here to help?

Henry shook his head and meekly handed Debra the empty glass. Miko looked like an angel but she could be even crueler than Debra. He vividly recalled her standing over him in the shower as her pee streamed out and hit him in the face. And later, her soapy finger digging into his butthole.

Debra took the glass away and pulled the sheet back exposing Henry's backside. Henry rolled over on his side so she could insert the thermometer. Debra was rougher than before, and this time she offered him no relief when he became aroused.

She pulled the thermometer briskly out and took it into the bathroom. As soon as she left, Henry grabbed his throbbing penis. Debra was back within seconds though, and caught Henry in mid-stroke. She slapped his hand away from his cock.

"Stop that!" she said sharply. She whacked his bare ass with the flat of her hand. "Get up! It's time we got you outfitted."

Debra went over to the closet and pulled out a long cotton dress in a yellow flowery pattern. It had a wide neck and billowy short sleeves. Henry could see no buttons or zippers in front or back. Debra held it up for him expectantly. Henry shook his head, no.

"Henry..." Debra warned.

Henry arose painfully, holding a corner of the sheet in front of him.

"Put that damned sheet down!"

Henry dropped the sheet and tried to cover himself with his hands.

"Now raise your arms. Up! That's it."

Debra slid the dress over Henry's arms and pulled it down into place. She stood back to look at him and barely managed to keep from laughing.

She turned and shouted toward the open doorway. "Miko! Come in here. You have to see this!"

Miko sauntered in, munching on an apple. "Oh, Henry! You look very pretty."

"We need a new name for him ... I mean 'her'," said Debra. "I know! How about Henrietta?"

The next two days passed slowly for Henry/Henrietta. Debra made him stay indoors, wear a dress and submit to several applications of lotion every day. The second day she switched to a moisturizing lotion. To Henry's chagrin she insisted on applying it everywhere, including his genitals. She even rubbed it up between his buttocks and around his anus.

Henry of course was kept in an almost constant state of arousal by all of this, but Debra refused to give him any more relief for his throbbing cock. In fact she gave him strict orders not to touch himself down there, except to go to the bathroom. Even then he was required to ask first, and either Debra or Miko would accompany him and watch. That first night he had looked forward to masturbating in the privacy of his room, but Debra had anticipated this and fastened his wrists to the bedposts with cloth restraints.

Debra also got rougher with him each time she applied the lotion. She plunged her finger deep into Henry's ass every time she did his bottom, and then she used two fingers. If he moved or complained she slapped his bare flesh hard enough to bring tears to his eyes. In between applications of lotion she also kept taking his temperature rectally, even though he didn't feel feverish.

By Thursday morning, Henry was getting better. He was looking forward to the weekend, when their parents would return and the girls could no longer control or tease him. He lay in bed listening to Debra and Miko whispering in the living room. He had no doubt that whatever mischief they were planning would involve him, and it wouldn't be fun. He was right of course.

A few minutes later Debra came in and unfastened his restraints. "Get your ass out here, now!" She spun on her heel and strode out.

Henry shuffled out to the living room, wearing the flowery yellow dress. Debra flopped down onto the sofa and gazed coolly at him. Miko—sitting across from her—winked at him.

"Take that goddamned dress off!" Debra ordered.

Henry started pulling it up over his head. He must have taken too long because the next thing he knew Debra had leapt up and yanked it off over his head. Underneath the dress, he had on a pair of his own underpants.

"What the hell is that?" Debra shouted, pointing.

"M-my underpants," Henry replied.

"Oh yeah? Who said you could wear those?"

Once again, Henry was too slow with an answer. Debra reached out and yanked the cotton briefs down around his ankles. "Do you know what we do to boys who don't follow orders?"

"No, please—"

Henry tried to run, but Debra stomped her foot down on his briefs and he tripped. He fell and lay sprawled on the floor at her feet. Miko laughed cruelly, as Debra pulled a sturdy wooden dining chair out into the middle of the room and sat down on it.

"Come over here, Henrietta." she commanded.

Henry started to get to his feet.

"No. Not that way. Crawl on your hands and knees."