"You want to what?" Tammy tapped her ear. "Come again?"
"I've come twice and it hasn't help."
"Don't get smart with me! This isn't funny."
"Please?"
"Stop begging like you're asking me to lend you money or swap chores. This is sick shit you're asking." On the note of sick shit, she pulled her eyes from his disturbingly impressive bulge.
"You don't have to touch me."
"I know I'm not going to touch you."
"I'll just do it myself, but have you to look at."
"Pay attention." Tammy spoke with exaggerated slowness. "I am your sister. Brother's don't jerk off on their sisters."
"I know who you are, but you're a super sexy girl."
"Who happens to be your..." she raised her eyebrows.
"I won't see you that way. Look, Tammy, I've never been with a girl. Just having one in front of me might be enough so that I can make it happen."
"This is nuts." Tammy muttered. "And I don't want to see your nuts." Although she was curious about his dick in the sense of how big could it possibly be? The kid was six feet and weighed 150 pounds if he were lucky.
"You don't have to. Come on, Tammy. I'll do anything you want! Your chores, your homework. I'll wash your car!"
"I can't, it's just not right."
"What Kim did wasn't right either! This isn't my fault, and I wouldn't be in here if I thought I'd be okay. Please help me? Please? I don't want to go to a doctor! Even if I'd end up okay, you know how humiliating that is?"
Tammy nodded, and he went on.
"Then Mom and dad are going to see the bill for whatever medical doesn't cover, and they're going to ask why I went, and I don't want to tell them the truth. Please sis? I Had people laughing at me, I'm scared it won't go down, and I'm so low I'm begging my sister to help. I don't have much dignity left. I don't need an ER Doctor thinking I'm a loser and making me a story he tells his friends for laughs!"
Tammy put her hand up to stop him. "You're right, its not your fault. That was a mean thing to do to you and I get you feel pretty low right now, but..."
"Tammy, all I need is to get off!"
"You got off twice and look at you. What if it doesn't work?"
"Then I promise I'll let you take me to the ER. Just give me one more chance to take care of it. Deal?"
He stared at her imploringly, and she wavered. This was wrong on so many levels it wasn't funny. On the other hand, the poor kid was the victim of nasty prank that now had him feeling even worse about himself, and she couldn't imagine how bad he felt.
Coming to her couldn't have been easy, and he'd made a good point about their parents wanting to know why he'd gone to the hospital. Tammy could spin a lie, and stick to it, but Jimmy would end up blurting out the truth.
Their parents would be ripshit and want to talk to Kim's parents, setting Jimmy up for 'snitches get stitches" at school This was his freshmen year at URI and he'd just been the butt of one joke. All the jerks would have him in their sites if their parents found out and took action.
"Okay," she said quickly, before reason took over and made her keep saying no.
"You'll help?"
"I can't believe I'm doing this, but yes. How are we doing this? I am not watching you whack off."
"I get it."
"And I'm not getting naked for you. Or..."
"I get it!" Jimmy raised his voice to interrupt her. "How about," his hand trailed down to touch himself through the boxers and she wondered if he were aware he was doing it.
"You wearing anything under that nightshirt?"
"Why?"
"Tammy if you're going to help me, please just help me."
"No, only thing under this shirt is me."
"Then roll over, and just um, pull your shirt up enough for me to see your ass."
"You are not seeing my ass!"
"Its just your ass! You can keep your legs together so I don't see anything else."
"That's nice of you." Tammy replied sarcastically. "How about you jack off on my feet?"
"What?"
"There's a lot of guys into feet. I got a pedicure so they're soft and my toes are painted red."
"Feet don't do anything for me," Jimmy protested. "I need to see something, that, you know, would really get me going."
"My ass will get you going? I hope a side effect of those pills is making you so horny you can't think straight, because you shouldn't be saying shit like that to me."
"I've never seen a girl's ass except for porn." Jimmy kept trying. "You said you'd help."
"I did, but I'm already regretting it."
"Please don't change your mind." When Jimmy saw her waffling he add, "Come on, sis, we had a deal!"
She took a deep breath. "Okay, but you better not tell anyone about this."
"Being so pathetic I asked my sister if I could jack off over her ass, isn't something I'd brag about."
"True." Tammy drew her leg up and kicked the sheet off. "I'm not exactly going to consider this a high point in my life either."
She rolled over onto her stomach and rested her chin on her folded forearms. She crossed her ankles to keep her legs pressed together and make sure he couldn't see between her thighs.
"Can I take these off?" he asked. "If you want me to keep them on I will, but it'll feel better if..."
"Do whatever you have to, I'm not looking."
She heard Jimmy sliding his boxers down his legs and a moment later felt him get on the bed behind her. Her eyes widened when the bed shifted, and she felt his legs pressing against the lower part of her thighs as he straddled her.
"Can't you just kneel on one side of me?"
"I don't want you to be able to see me out of the side of your eye," he said behind her. "Besides this'll be a better angle and..."
"Whatever, at this point I guess it doesn't make things any worse."
"Can I?" He tugged on the sides of her shirt.
Tammy closed her eyes and took a few seconds to tell herself there was no turning back now.
"Go ahead," She lifted her hips so he could slide her shirt up.
She held her breath as she felt the soft material of the shirt going up the backs of her upper thighs then her ass. He stopped when it was over her hips, and she felt her face flush from the idea her brother was now staring at her bare ass.
"There's lotion on the nightstand," she said. "Use it, it'll feel better and you'll be quicker."
"Trust me, I've got more than enough lube, I've been dripping for the last..."
"Okay, okay, just you know, get it over with."
"Damn, you have a fine ass," he said softly. "Like holy shit, fine."
"Less yapping, more fapping." She replied, wishing she'd thought to grab her phone and her earbuds during this so she couldn't hear him.
"Taking the sexy right out of this," he sighed.
"There was never any sexy in it, get going before I change my mind."
Jimmy didn't respond but the bed was now shaking slightly and she could hear him breathing louder over her. He hadn't been kidding about having enough natural lube because she could hear a wet slapping sound as he stroked his cock.
Tammy knew if she looked to her right she'd see their reflection in the mirror and was annoyed to discover a small part of her wanted to look. Unlike the decision to let this happen, the right thing to do won out and she focused on the headboard in front of her.
She jumped when Jimmy grabbed her left ass cheek, squeezing it.
"Wow, your ass is tight! That Yoga stuff must really work."
"Don't touch my ass you little perv!" Tammy caught herself moving her head to look over her shoulder. "I didn't say you could touch."
"But it helps!" This time he lightly caressed her cheek with the palm of his hand. "Please?"
"This is crazy," she muttered, then spoke so he could hear. "If it helps you get off faster, fine, but keep it to my ass, you try to get your hand between my legs, I'll kick you out of here."
"Don't have to be mean."
Jimmy's hand slid over her ass fondling her other cheek, then giving it a squeeze. His breathing was louder and heavier, and wanting to get this over with, she wiggled side to side, shaking her ass for him.
"That's so hot," he breathed. "You got the finest ass I've ever seen."
"It's the only ass you've seen that's not in a porn," she sighed. "Please stop telling me I'm hot."
"You are though," he gave her ass a little smack that made her yelp more in surprise than any type of pain.
"What the fuck?" she hissed. "You do not spank me!"
"Your ass barely moved, god it's so firm!" he gave her another swat that had Tammy vowing she was going to smack his face when this was over.
But she didn't say anything. At this point any protest on her part would make this last longer. He shifted behind her, and Tammy felt something soft and hairy slide along the back of her thigh.
Christ, his fucking balls were rubbing on her. The little shit was going to owe her big time for this. The sound of him beating off grew faster and his hand trembled where he now had it resting on her left ass cheek.
She wiggled faster, trying to help him along and she heard him whisper. "So fucking perfect," as he switched his hand over to the other side of her ass.
Tammy's body jerked when something sticky poked into the left side of her ass. She grimaced when it slid across, tracing the curve of her ass and leaving a sticky trail.
"Get your dick off me, you little jerk!"
"Sorry, I'm close and I'm just trying to get over the edge," Jimmy said. "Just a little more, promise!"
"Whatever." Tammy mumbled, trying to find something else to think about other than her brother whacking off while playing with her ass.
She flinched again when this time Jimmy didn't just press his dripping spongy head into her cheek, but slid his dick over her ass. His flesh was hot and hard. Very hard, and as repulsed as she was to have his dick on her, she couldn't help notice how long it seemed.
Tammy's head turned towards the mirror, but she stopped herself, and lowered her forehead onto her arms. The bed rocked as Jimmy was now thrusting his hips, sliding his hard dick over her soft cheek.
"Come on," he whispered. "Please finish, please!"
He sounded more frustrated than aroused and Tammy realized he wasn't exaggerating about not being able to get himself off, and how frustrating it must be. He was young, but if he'd already come twice, maybe his body was too tired to do it again, but the drug was keeping his dick from deflating.
Maybe she needed to do something to help him get through. An image formed in her mind, something she'd seen in a couple of porns.
"Put it between my cheeks," she blurted.
"Huh?"
"Slide your dick through my crack, you know, like you're fucking my ass cheeks."
Jimmy didn't hesitate to slide his dick over, and Tammy inwardly cringed at the feeling of it nestling between the cheeks of her ass. He slid his cock through her crack several times, then put his hands on her ass, pressing her flesh tightly around his cock. He pumped his cock through her soft skin, moaning loudly as his hips thrust faster.
"They call this hotdogging." Jimmy said, his voice coming out in a breathy wheeze as he fucked her butt cheeks.
"Of course you'd know that," Tammy shook her head.
"This feels good!"
"I asked you to stop talking." She released a long breath. "I was hoping I'd have a naked guy behind me tonight, but wow did that take a wrong turn."
"S...sorry," Jimmy wheezed. "You think I wanted to be the first girl's ass I ever touched to be my sisters? I'm more pathetic than you."
"Stop that woe is me shit, and just fucking come, okay?" Why did she have the feeling none of her friends had ever uttered that line to their brother.
"Yeah," Jimmy pumped harder, the bed now rocking from his efforts.
Tammy tried not to keep thinking about not just how hard his dick was and that there was now no doubt there was more than a few inches working her cheeks. Why did she keep thinking about it? Note to self, don't mix hard liquor with weed.
"Yeah," Jimmy moaned, his fingers tightening on her cheeks to the point it hurt, but she didn't want to stop him. "Fuck, I'm so close!"
His thighs trembled against her legs and his cock rapidly thrusting into her as he sped up in an effort to finish. Tammy frowned at the thought of where did he think he was coming? This was bad enough, she didn't need his load on her ass, or her nightshirt.
But he seemed to be right there, and she didn't want to interrupt him, she was just going to have to deal with an additional layer of shame when he squirted all over her.
"Come on," he groaned. "Come on!"
His thrusts were shorter and harder and both them, and his voice, had an air of desperation. Gritting her teeth, Tammy pumped her hips as much as she could with his weight on her legs, shoving her ass into his strokes.
He released a pathetic whimper and she winced when his fingers were now gouging into her and he was moving his hips so hard the headboard was hitting the wall.
"Right there, right there," he gasped. "Please, oh, please."
The poor kid was begging to come, and she felt her annoyance giving way to pity. She'd been thinking of herself and how gross and wrong this was. She hadn't considered what he'd said to her a minute ago, that this had to have him feeling pretty low, asking your sister to help him and knowing she was doing it reluctantly.
"Fuck!" he shouted, and rolled off of her. "Fuck, I can't, I fucking can't!"
"Easy, easy!" Tammy sat up, pushing her shirt back down over her sticky ass. "Relax, maybe you're trying too hard."
She turned to see him sitting on the edge of the bed, his back to her. He was breathing hard and he had his head in his hands.
"It's not going to happen. Your ass looked and felt so good, and I know it sounds bad, but doing that was the hottest thing I've ever done. I was close, but I'm too tired. My frigging balls are aching."
"Take a couple minutes, catch your breath." Tammy spun on her knees so she was behind him and put her hands on his shoulders. "I'll let you try again."
"I don't think I can again." His shoulders slumped beneath her touch. "We made a deal, and this didn't work. Will you take me to the ER? I don't want to go alone, especially if they have to...do that to me."
Tammy's heart broke at the dejection and fear in his voice, and she squeezed his shoulders.
"No, we're going to take care of this here, I promise."
"No offense, sis, but I don't think that was enough. I don't know what I need, but it's more than what you did, and we can't do more than that."
"Maybe we can," Tammy spoke slowly, wondering if she could go through with what she was thinking.
"I'm going to stand up and put my underwear back on. You might want to look away."
"Thanks for the warning, even though I should get to see your ass because you saw mine." She tried to joke, but he shrugged.
"If you want to look, I don't care."
He rose from the bed, and Tammy did turn her head. She'd lost track of where she was on the bed and when she looked away from him, she was confronted with their reflection. Her kneeling on the bed, and Jimmy standing there naked looking on the floor for his underwear. Tammy's eyes widened and she gasped.
"Oh, my god, bro!"