Summer of Discontent

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Sister catches her brother masturbating and offers her help.
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Series 6
Series 6
145 Followers

Jeff sulked on the couch, half-heartedly watching a college baseball game on ESPN. It was supposed to be his final summer of fun before college. He had turned eighteen just before the end of his senior year of high school, which meant that he was too old to officially be a Boy Scout. But he was still able to work on staff at Camp Baden, the Boy Scout camp that he had attended every summer since he joined the scouts seven years ago. That was how he wanted to spend his final summer as a kid, one last time at the camp that gave him a lifetime of great memories. One final summer of fun with all of his scouting buddies until it happened.

"It" was the fall from the climbing course at camp. Foolishly, he had neglected to clip himself onto the safety line. After all, it was a strict rule that all scouts and staff members had to wear a helmet and clip their body harness onto one of the safety lines to prevent injury from an accidental fall. But for some reason Jeff didn't follow the rules that day and now he was to spend the rest of his summer at home with both of his wrists in casts.

When Jeff fell, he put both arms out to break his fall. The hard landing resulted in two badly fractured wrists. The casts started at his elbows and extended all the way up to his hands, encasing both of them up to the first knuckles of his fingers. His thumbs were put in a cast with just the tips poking out. With just two knuckles of each of his fingers poking out from the edges of the casts, it left him with very limited use of his hands. He could still bend his elbows, so his arms were not completely immobilized, but that small bit of good fortune was lost on him. He hadn't left the house since the injury happened a little over two weeks ago, spending his time sulking around in a pair of cut off sweat pants and a t-shirt.

The sound of the doorbell roused Jeff from his torpor. Slowly he rose from the couch and walked to the foyer. His clumsy fingers struggled but managed to unlatch the door. He was met with a pleasant surprise as he swung the door open.

"Jeffrey Porter?"

"Yes?" He replied.

Standing before him was a woman wearing the familiar brown uniform of a UPS delivery person -- short pants that came to about mid-thigh, a short-sleeve shirt that buttoned down the front with a collar, and a brown cap with the UPS logo on it. She greeted him with a pleasant smile as his eyes played over her body. She was petite and very cute. Her strawberry red hair was tied back in a long ponytail that stuck out from the back of her cap. She was curvaceous, but not fat. Her legs were a little thick, but shapely and very well defined. As he looked her over, Jeff's eyes lingered a little too long at her large breasts that strained the buttons of her uniform shirt with a name tag that read "Amy." He managed to pry his gaze from her plunging cleavage. When his eyes met hers, she smiled at him knowingly.

"I have a package for you. Can you sign here?"

"Um...I broke both of my wrists recently and I'm still having problems grasping things. Do I really have to sign for it?"

"Oh, you poor boy. Can you just scribble something the best you can? I'm required to get a signature for delivery." Amy asked sympathetically.

"I can try." Jeff replied as Amy handed him an electronic data pad and stylus. Clumsily he managed to scribble a few loops and lines that remotely looked like it could be his signature.

"Thank you. Will you need any help?" Amy asked as she took the pad back from Jeff and handed him a medium-sized rectangular box.

"No, no. I'll be fine."

"OK, have a good day." She said with a smile as she turned back to her truck.

"Thanks." Jeff said as he watched her jog back to her brown delivery van, enjoying her nicely rounded ass and bare legs as she disappeared into the vehicle.

As the van pulled away, he shut the door. A smile came across his face.

"It finally came. This isn't going to be such a bad day after all." He said to himself.

Excitedly, he ran to the kitchen and placed the package on the counter. He opened the utility drawer in the set of cabinets so fast that it caused the contents to noisily rattle around.

"Knife, knife, knife. Damn it, where is the fucking thing?" Jeff muttered as his eyes scanned the chaotic clutter that filled the drawer to its limit. He grinned with satisfaction when he found a well-worn penknife among the hodgepodge of tools, trinkets and other items. He grabbed it and tried to open the main blade, but his fingers still lacked the dexterity to grasp the thin metal in order to swing it out.

"Shit!" He exclaimed as he threw the tool back into the drawer and slammed it shut. Frantically, he looked around the kitchen to the set of expensive steak knives that rested in the wooden storage block on the counter. He grabbed the knife with the thickest handle and carefully slipped the sharp tip into the taped seam of the package. The work was difficult due to his limited dexterity, but he finally managed to open the brown cardboard shipping box.

He breathed a sigh of relief when he slid his new possession out of the box and saw that it was not encased in some impossible to open plastic package. Thankfully it was in a thin cardboard box that could easily be opened with his clumsy fingers.

Jeff's lips stretched into a wide smile as he looked at the thin, cardboard packaging. The Fleshlight, read the box. He could feel his nervous, sexual tension grow as he looked at the box, knowing he was going to have an afternoon of pleasure.

Jeff saw it advertised while surfing the internet. In addition to his injured hands costing him his summer at camp, it prevented him from being able to pleasure himself. Sitting around the house all day, surfing the net and looking at porn left him very frustrated. His horniness was driving him insane without a way for release. When he saw the Fleshlight advertised on one of the adult sites, he felt that getting one was going to be the only bright spot to an otherwise disappointing summer.

It was a male masturbation toy shaped like a very thick flashlight, thick enough for him to grasp between his injured hands. One end had a bright pink opening that looked like vagina with lips and a little clitoris. The inside was made of a very soft rubber-like material that felt "life-like" according to the website's testimonials. The exterior of the toy had a hard plastic shell, much like a flashlight.

Jeff grabbed the boxes and jogged from the kitchen, bounded up the steps, and into his bedroom, tossing the Fleshlight along with a small plastic bottle that was included in the package onto his bed. Quickly he pulled his shorts down, kicking them across the room and practically tearing his t shirt when he struggled to pull it off. His cock was steely hard. It bobbed up and down while he struggled to get his shirt off and hopped onto his bed. He knew he was starting to get hard while he was staring at Amy the delivery woman. He figured she could see his shorts beginning to bulge from his erection, but he didn't care. He was finally going to have some relief and a little fun.

Jeff was flat on his back, completely naked with his stiff cock pointing up to his belly. The toy came with a bottle of lubricant -- HeatFlesh, read the label on the small plastic bottle. Using the nail of his thumb, he was able to flip the cap open and pour a little into the vagina-like opening to the toy. He managed to close the cap without spilling any and tossed it to the side of the bed.

Now came the moment of truth. His hands were shaking with nervous excitement as he brought the opening of the artificial pussy to the engorged tip of his penis. A rivulet of precum had leaked from the little slit and ran down the purple head of his cock, pooling at the raised rim. He pressed his bulbous head between the faux lips of the fabricated pussy. His cock jumped with an involuntary reflex when it touched the soft rubber of the toy.

Holding the cylinder with the fingers of his right hand, he managed to guide the head in with the index finger of his left. Jeff gasped as the tip of his penis popped inside. Penetration! It felt heavenly as he grasped the toy between his casted hands and slipped it all the way down, bringing it to the base of his thick shaft. He grimaced with pleasure as he slowly moved the toy up and down, his hips bucking slightly as he fucked himself with the cylinder.

Jeff closed his eyes and thought about Amy, the UPS delivery woman. As his fantasy played out in his mind, he slowly pumped the Fleshlight up and down his hard cock. He imagined Amy standing at the foot of his bed, unbuttoning her UPS uniform to reveal a brown bra that pushed her round breasts together and accentuated their size. She unzipped the fly to her shorts as the front split in a jagged "V," allowing her to slide them down her toned thighs to reveal a tiny pair of matching brown thong panties

"UPS issues us our entire uniform for the day, right down to our underwear. I love the feel of the thong. It's spandex. It feels so smooth over my ass and pussy." Amy smiled.

Jeff could see the thin strip of brown material arc over her hips and disappear between the curved cheeks of her ass. He wanted to feel her thick legs wrapped around his body, pulling him close as he drove his cock deep into her hot pussy.

Amy climbed onto the bed, crawling over Jeff's body to straddle his waist. She was on all fours as she let her breasts drag along his belly, up his chest, letting them rest against his face. His lips kissed the warm flesh of her cleavage, dragging across the satiny fabric of her bra. He could feel her nipples hardening against his lips through the soft fabric. Her warm body felt incredible pressed against him.

He reached up, his hands free from the constraints of the casts and palmed her round breasts. She arched her body, pushing her chest forward to encourage him while gasping at his touch. Her large breasts overflowed from his grasp.

As Amy straddled his body, she could feel his throbbing cock resting against her round ass. She reared back, letting his cock slip between her thick cheeks without going completely inside her. The warmth and smoothness of her skin made him gasp as his cock jumped and flexed with little spasms. He thrust his hips as the length of his shaft rubbed between her thick ass. Her soft skin and the silky thong felt great against his virgin cock.

"Oh fuck yes Amy! You feel so good. Please let me fuck you." He said aloud.

"Well, well, well. What is going on here?" A voice said, trespassing into his fantasy.

The image of Amy straddling his body shattered and fell away like broken shards of glass. Jeff opened his eyes to see his sister, Samantha, leaning against the doorway to his room. Her arms were crossed and she was smiling as she watched Jeff.

"What are you doing here!" Jeff exclaimed.

"I live here, bedroom across the hall? Certainly you remember me sitting across the dinner table from you at mealtime, though I can see how you may have forgotten. The blood flow to your brain must be severely limited with it going to that massive erection you're sporting."

"Fuck." Jeff grimaced with humiliation.

"So, who is Amy?" Samantha teased.

"Stop!" Jeff angrily replied.

"Jeff, this can go easy or it can go hard. Who is she?" Samantha continued to torment.

"Just fucking leave me alone, goddammit!" Jeff exclaimed.

"I'm sorry Jeff. I just couldn't resist..." Samantha started to giggle.

Jeff looked as if he was close to tears from frustration and humiliation.

"You don't understand. This was supposed to be my last summer, my best summer at camp. But it all got trashed after I broke my wrists in that stupid accident. Now I can't even jerk off, and to top it off I have to live with the humiliation of you catching me with this fucking stroke toy." Jeff said as he shifted to sit up on the edge of the bed, pulling the Fleshlight off and letting it fall to the side of the bed as he stared at the floor.

For a moment, the two of them shared and uncomfortable silence. Jeff feeling defeated while Samantha feeling sympathetic and guilty. She moved to sit next to Jeff on the bed.

"Jeff, I'm sorry. I just thought it was friendly teasing. I never wanted to hurt or humiliate you. I would never tell anyone about this, you know that. I didn't realize how badly the accident and losing summer camp was affecting you. If it's any consolation, I'm having a shitty summer too. I broke up with Dave at the beginning of the summer, I haven't been able find a full-time job so I don't have any money, and Jennifer has been away all summer on a study program in Canada." Samantha said as she put as sympathetic hand on his shoulder.

Jeff and Samantha had a very close relationship. She was nineteen months older than him. They were practically best friends and frequently confided in each other. Jeff was the only person who knew that Samantha had dabbled in a little bisexuality with her best friend Jennifer.

He had always admired his older sister. She was confident, friendly, popular, and pretty. His friends would tease him because they all wanted to date his sister, well actually something much more graphic than just a date. She was almost as tall as Jeff, and had a thin waist that curved down into a nicely rounded ass. She had a pair of larger than average breasts that always drew men's attention. Her thick black hair was cut very short, but looked cute in a punky kind of style. Her wide green eyes and captivating smile completed her beauty.

"I guess this looks really ridiculous." Jeff said, managing a sheepish grin.

"Hey, we all do embarrassing stuff when we're alone and really horny." She offered as she gently brushed his shoulder.

"Yea, like you've done something like this."

"You just never caught me." Samantha smiled.

"Now I'll have to catch you so we're even." Jeff replied.

"And why would you want to catch me?" Samantha teased.

"I don't know. I'm just trying to be funny." Jeff mumbled.

"Do you think it would be hot to catch me?" Samantha asked.

"Well....I don't....." Jeff stammered.

"Because honestly, watching you was hotter than I expected." Samantha grinned.

"What? How long were you standing there?" Jeff said surprised.

"Probably a minute or two. It was hot watching you fuck that rubber pussy thing. You were really letting loose the way you were writhing and moaning and pumping it, especially when you started saying Amy's name. And I have to admit that you have a gorgeous cock: long and thick, nicely shaped head. It's quite tempting."

Jeff was absolutely shocked. Did his sister really admit that she was turned on by his cock? But what surprised him was how her admission turned him on. He felt himself just hoping she would reach over and touch him.

Jeff slid back so that he was lying flat on his back on the bed. His cock was still hard and coated with some of the lubricant.

"Tempting for what?" Jeff asked.

"I think you know." Samantha replied hesitantly, feeling a little unsure about her growing desire to touch her brother. But she couldn't resist the compulsion to stare at Jeff's erection as he lay back on to the bed.

"Go ahead if you want to."

"You're crazy." She said, looking him in the eye. But the look on her face told Jeff that she was having a hard time resisting temptation. Both of them nervously looked away, trying to avoid each other's glance. Samantha was fighting her tremendous urge to look at Jeff's swollen member. The tension hung in the air as they silently fought with their thoughts.

Finally Samantha looked back at Jeff's penis. With a quick breath, she bit her lower lip and reached down to his crotch. Her fingers encircled the slick shaft, leaving generous lengths extending from either side of her fist.

"Oh, yes!" Jeff managed to gasp at her touch.

Slowly Samantha pumped, running her hand the entire length of his staff from the tip all the way down to the base with slow, deliberate strokes. Up and down, her hand twisting around the thick knob when as she reached the head at the end of each stroke.

Jeff just arched his body and closed his eyes. This felt far better than the Fleshlight or even his own hand. He was panting and gasping as Samantha slowly and purposefully worked his cock, stopping every so often to prevent him from cumming too soon. She wanted to make him last as long as she could. Each time she paused, she would gently squeeze his shaft, milking a stream of clear precum from the little slit. It would pool at the tip before the droplet ran down her knuckles, trailing a shiny thin stream down the back of her hand.

Rubbing and pausing. Rubbing and pausing. Samantha would repeat the cycle, bringing Jeff just to the edge of climax before stopping. Her fingers and hand were now glistening with a glaze of his juices. Jeff was flat on his back with his arms splayed out to his sides. He alternated between closing his eyes and watching Samantha. She loved it when he would watch, licking her lips and exaggerating her twisting motion which made him practically whine. She could tell by the way Jeff was writhing that he wanted her to let him release.

Faster she stroked, her hand quickly curled up and down his throbbing shaft. Jeff's groans were more vocalized and urgent. His hips bucked and Samantha could feel his prick grow even harder and pulse within her grasp. Her hand was a blur as she pumped the head with short, fast strokes. Her eyes widened with surprise when he she pushed him over the brink.

Jeff could only manage a final ragged gasp as a torrent of white cum erupted from his cock in a long arcing stream, splashing on Samantha's shirt just below her neck. Jeff's hips tensed and bucked as string after string of cum sprayed from his spasming prick, landing on his sister's hand, arm, and shirt. His pent up release seemed to last for almost a full minute. Finally spent, his body went limp as he lay on the soft bed, gasping to regain his composure.

As Jeff's racing heart calmed down and he was able to catch his breath, he opened his eyes. Samantha was smiling as she leaned over his spent body. She released him from her grasp as she lowered her face and tenderly kissed his cheek.

"I was glad to do that for you." She said softly. She looked at him lovingly as she got up and left him alone with his thoughts.

Jeff's mind was reeling from what just happened. Silently, he struggled to reconcile his feelings. Everything he knew, all the societal mores told him that what they had just done and how he felt was wrong. But it conflicted with the overwhelming feeling that he liked it. He got up from his bed and went to Samantha's room.

The door to her room was open, inviting him to enter. The shorts and now soiled shirt Samantha had been wearing were in a pile next to the bed. She was nude, lounging on the plush cushion of her circular papasan chair in the corner of her room. She watched Jeff intently as he walked to her. She smiled as he stood over her.

"I love the way your dick swings when you walk in like that. Makes you look like you might mean business." She said with a lascivious grin.

"Might?" His eyebrows rising as he asked his response.

"You look a little unsure, but it's fine." Samantha said as she reclined back, sliding her hips forward and spreading her thighs wide, urging Jeff on by exposing the pink of her pussy for him. He could see that she was glistening and wet.

Jeff knelt down in front of his sister. As he looked up at her, their eyes locked for a moment.

"You've never done this before, have you?" She asked.

"No." He admitted as he turned away abashedly.

"It's nothing to be ashamed of. Do you want to stop?" Samantha asked soothingly.

"Not at all." Jeff nervously admitted as he looked back up at his sister.

Series 6
Series 6
145 Followers