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The Step-Dilemma

"Eric finds his relationship with his new step-sister to be...complicated"

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It had been chaotic several weeks for Eric. He had just moved all of his belongings into his new bedroom at his new home. He closed the door, sat down on the bed, and took a moment to gather his thoughts.

His mother was very recently remarried and that event suddenly forced him to relocate in the middle of his senior year of high school. The new home was in a different school district and there would have been significant travel time for him to drive to his old school every day, so he was forced to switch schools mid-year.

Eric was happy for his mom. His father had already remarried, so there wasn’t really any hope for them getting back together. He just wished that she could have waited for another couple of months.

Eric’s mother interrupted his moment of reflection to call him to the dining room for their first “new” family dinner. He took a deep breath and headed to the table with the best smile that he could present at that moment.

Eric’s new stepfather, Jim, welcomed him to the table. He seemed like a genuinely nice guy. Eric had met him on several occasions and he was always cordial.

Jim told Eric and his mother to go ahead and eat while the food was still hot. He said that his daughter, Kendra, would be home soon but there was no need to wait. Eric wasn’t quite sure if she still lived there or not. There was still a bedroom down the hall from him, but he wasn’t sure if anybody still occupied it.

Just as everybody at the table had filled their plates, the door from the garage swung open. A young woman charged into the kitchen in a flurry of expletives and long, dark hair that was flying in every direction. As she settled at the kitchen table, Jim apprehensively said, “Eric, this is my daughter…Kendra.”

Eric wasn’t sure how to respond to that introduction, but he gave a tentative “hey” in her direction. She didn’t seem to pay much attention to him until she asked him to pass the potatoes in her direction. As he grabbed the bowl and passed it to her, he finally gave her a good look and almost dropped the bowl.

He had seen a few pictures of her previously, particularly as they were moving in, but they certainly had not done her justice. Eric stared at her for a few seconds, mesmerized by how beautiful she was.

He was knocked out of his trance as Kendra aggressively tugged away at the bowl of mashed potatoes. From that moment forth, he mostly stared directly at his plate of food. Any glances upward were directed almost exclusively at Kendra just to affirm that she was as attractive as previously advertised.

After dinner, Eric helped his mother and Jim clean up. Kendra headed to her bedroom, he assumed. He was glad that she had left the room. She was making him feel quite uncomfortable and he feared that he was destined to feel that way far too often.

After he finished cleaning up, Eric settled in on the living room couch. His mom and Jim were watching some sort of detective show that didn’t interest him in the least. He mostly just played on his phone and texted with some of his friends.

After roughly an hour, he decided to head to his bedroom. He said goodnight to the new parents and headed toward his bedroom. As he neared the hallway, Kendra appeared from her bedroom. She seemed to have recently left the shower as her hair was still fairly wet, but that was not what really caught Eric’s attention.

She was wearing a slightly oversized t-shirt. It didn’t seem to be a nightshirt since it wasn’t really an appropriate length to be worn as a nightshirt. The material was also either very thin or it was well-worn. Eric could see virtually all of her body through the shirt except for the area of her breasts that were covered by the decal. Kendra was very slender, but her breasts were unusually large for her frame.

The bottom edge of the t-shirt rested at roughly hip level. That meant that there was a considerable area of her turquoise-colored panties exposed even with her arms and shoulders at rest.

Kendra passed Eric in the hallway. Eric crowded toward the right side of the hallway so they could pass each other. He thought to himself that any contact with Kendra would have been inappropriate considering her distinct lack of clothing.

He found himself creeping tighter against the wall every second that passed. Kendra gave him a strange look as she slinked past him.

He heard her mumble, “Jesus! I don’t have an STD or something,” as she headed into the kitchen.

He thought about apologizing, but he decided to go into his room and close the door instead. After he closed the door, he quickly wondered to himself what Kendra was picking up in the kitchen. He quickly pictured her reaching for something on the top shelf and her shirt being pulled up to her navel.

Eric briefly thought about opening the door and peeking out that way, but he couldn’t work up the courage to do it. He wondered if she always was dressed like that or if he had just wasted his one good opportunity. Then he realized that he was talking about his step-sister. He felt guilty about his desires and tried to think about other things.

For the remainder of the night, Eric remained in his bedroom, with the exception of one trip to the bathroom. There were three rooms off of the hallway at that end of the house. The first was Eric’s bedroom, there was a bathroom in the middle, and Kendra’s bedroom was at the end. As he headed to the bathroom, he could see that Kendra’s bedroom door was closed and a light was still on.

As Eric was standing at the toilet, he realized that Kendra and himself shared this bathroom. He opened up a few of the drawers. They were filled with mostly cosmetics and hair care products. He stopped dead in his tracks when he found her feminine hygiene products.

Eric closed the drawer quickly and found himself embarrassed. He stopped looking through drawers immediately. He quickly realized how familiar the two of them were going to be with each other's personal hygiene. Then he noticed the clothes hamper in the corner of the room. As much as he was tempted to look through it, he refrained.

He returned to his bedroom, but now he couldn’t get Kendra out of his head. He kept picturing her in that t-shirt and turquoise panties. It became apparent that his cock was not going to take no for an answer this time.

Eric removed his shirt and yanked down his shorts. He hobbled over to the nightstand and grabbed a tissue with his left hand as he started stroking away with his right. It didn’t take very long until he was on the verge of orgasm. He tried to frantically wrap the tissue over the head of his cock, but the cum flowed too heavily and quickly. Several large droplets headed toward the floor but were intercepted by his shorts and underwear which were resting at his ankles.

Eric finished mopping the cum off from his cock and grabbed an additional tissue to pat everything dry, including his shorts. He tossed the tissues in the trash can and pulled his shorts up which now had an uncomfortable wet spot on them.

The wet spot was a nagging reminder of what he had just done. Each time that he thought about it, he would think about Kendra. It wasn’t long before he pumped out a second round of cum.

Once he had cleaned up after the second time, Eric decided to go to sleep. He turned the light off and slid into the bed wearing just his shorts and boxers.

Eric had to continually stop himself as he continued thinking about Kendra and rubbing his erect cock against anything that it could find. He finally fell asleep but he woke up a couple of hours later. He was face down on the bed and he had been grinding his cock against the mattress as he slept.

He could tell that he had been doing it for a while because his cock was getting sore from the friction. He was also just seconds from orgasm. Eric flipped over on his back, pulled his shorts down, and kicked the covers down.

Eric hoped that the previous two orgasms would limit the volume of cum this time. His load was thin and watery, but there was still quite a bit of it. He didn’t even get to completely finish before he felt the cum begin to trickle off of his body. He reached for a tissue, but it was already running down onto the sheets.

The following days were an exercise in sexual torment for Eric. Almost any time that he saw Kendra he would get an immediate erection. He tried to avoid her as much as possible, but that wasn’t working out very well. He also quickly found out that her nightwear that first night was pretty standard.

Eric had not had a lot of experience with girls at that point. There had been a few girlfriends, but there had been little more action than some over-the-clothes touching or an occasional drift underneath.

One evening, Eric had been doing some homework in his bedroom. As he left his room to use the bathroom, he caught a brief glimpse of Kendra as she had left the bathroom. She had just finished her shower and was walking to her bedroom with just a towel loosely draped around herself. Since she was walking away from him, he only saw her backside, but it was basically in full view.

Eric hurried into the bathroom; the air was still damp from Kendra’s shower. Eric quickly decided to try to pee first, but he knew what else he had to do. He aimed his stiff cock down in an uncomfortable fashion. After a prolonged wait, he managed to get a flow going although it went all over the toilet.

The cleanup was going to have to wait a while, though.

Eric turned around and began to stroke his cock furiously. Even though he had been masturbating very frequently, he never seemed to feel satisfied anymore. As his eyes drifted, he saw that the lid on the laundry bin was open. He stepped over and looked down to find Kendra’s recently removed clothing.

He ceased stroking his cock as he reached a trembling hand into the bin. He pulled a mismatched cotton brassiere and panties from them and quickly inspected them. The bra was white and he found a tag that said 30C on it. The panties were black bikini panties with a silver Calvin Klein embroidered on the waistband.

Eric gave them both a quick sniff before placing the panties in his right hand. He started stroking his cock with the panties and before he could even think about what he was doing, he ejaculated all over them. His head rocked backward and he experienced the first brief moment of satisfaction that he had felt in days.

Feeling freshly content, Eric slowly gazed downward and then he realized that he had left evidence of what he had done all over the panties. He thought about getting rid of them, but he finally decided to tuck them inside a pair of Kendra’s jeans. Hopefully, they would not fall out on the way to the washing machine.

Eric cleaned up the bathroom as much as possible and headed back to his room. He was still nervous about getting caught playing with Kendra’s undergarments, but that didn’t squelch his libido in the least. After catching a look at Kendra’s amazing, little ass, nothing was going to put out his fire for very long.

The following morning, Eric was taking a shower before school. As he stood under the shower gently stroking his almost perpetually erect cock, he heard a noise. He pulled the curtain open slightly and then let out a squawk when he saw Kendra sitting on the toilet just steps away.

“Uh, I…I’ll be out in just a minute if you need to use the bathroom,” Eric shouted.

Kendra replied, “That’s okay. You aren’t bothering me at all. Continue doing whatever you were doing. I’ll be done before you.”

Eric didn’t answer back. He wondered what she had meant by that comment. Had she seen him jacking off in the shower? There wasn’t much visibility through that shower curtain, but you could probably see a shadow image. Eric stood there frozen with his back turned to the curtain until he heard the door close again. He was pretty sure that she brushed her teeth also before leaving.

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Once he finished his shower, Eric scampered over and quickly locked the door. He normally locked the bathroom door. It was strange for him to have forgotten to have done so.

He spent the entire day at school thinking about that interaction. One part of his brain said to make sure that he locks the door every time from now on. The other side wanted her to walk in on him, but it more accurately wanted for him to walk in on her sometime.

He wondered if she locked the bathroom door. He bet that she didn’t. He was kind of surprised that she even shut it at all.

The following several days were more of the same. Eric was beginning to question how much more he could take. Thoughts of Kendra were dominating his entire life and although he knew that his obsession with her was unhealthy, he didn’t know of any way to make it better.

He had caught her walking from the shower to her bedroom several other times. One time he got a particularly good look at her ample breasts. Eric, on the other hand, made quite sure to keep the bathroom door locked after the one intrusion.

One night, Eric was doing his usual evening ritual of hanging out in his room while Kendra showered, hoping to bump into her as she walked to her room.

He actually worked up the slightest bit of nerve on this occasion and was going to attempt to see if she locked the door when she was in there. He didn’t intend on walking in, just yet, but he really wanted to know if she kept it locked. He reached his hand out and held it on the doorknob as he tried to work up the nerve to give it a turn.

Just then, the knob spun in his hand and then pulled away as the door opened. Only halfway paying attention, Kendra stood there with her towel on her head and one hand drying her hair.

Eric stood there wide-eyed as he finally got the full-frontal view that he had wanted to see for so long. After several seconds of aggressive, titty-shaking toweling-off, Kendra saw Eric standing there seemingly waiting to use the bathroom.

“I’m done in here. It’s all yours,” she said casually.

Eric turned around and nearly sprinted to his room. He slammed the door behind him and stripped completely nude within seconds. He grabbed onto his already rock-hard cock and started to pound it aggressively.

He barely got started when his bedroom door swung open wide. Kendra stepped inside, now with the towel wrapped around herself.

“Eric, are you alright? You didn’t seem like...”

Kendra paused briefly as she absorbed what was going on.

“Holy shit! That is a huge fucking cock!”

She turned around and closed the door behind her. Eric tried to somewhat cover himself up with his hands.

“I mean…I could tell that it was big, but I didn’t know that it was that big. Fuck! Your girlfriend is a lucky girl.”

Eric stammered, “Yeah, uh, she loves it.”

Kendra challenged, “Okay, you don’t have to lie to me. I can tell by that answer that you don’t have a girlfriend.”

“Yeah, I don’t have one right now,” Eric admitted.

“That’s a shame, Eric. That thing should be getting lots of exercise, and not just the kind that you are always doing by yourself.”

Eric’s face immediately turned bright red. It was bad enough that he was caught once, but it also seemed that she knew what he was doing all along.

“Don’t be embarrassed. It’s something that guys do all of the time…and girls,” Kendra confessed. “Well, I can see that you are doing just fine, so I’ll leave you and your large friend to continue the party."

Eric was in a state of shock. She didn’t seem to care about anything that she had just seen other than the size of his cock.

He wasn’t sure why she thought that it was so big. He didn’t think that it was.

Eric had been a bit of a late-bloomer. He had always been quite undersized in that department. By the time he hit his late growth spurt, he was already through with athletics and gym class. He had just assumed that the other guys kept growing as well.

Without other young men the same age as himself to compare with, he had turned to internet porn. At eight and a half inches long, he seemed to be average at best.

He did have a large pair of low-hangers, though, so maybe that gave him a more impressive-looking wingspan, so to speak.

Just as Kendra was exiting into the hallway, she turned back around and charged back into the room.

“Wait a minute. Were you jerking off to me?”

Eric was mostly silent, other than some stuttering.

“You were, weren’t you?”

She started to chuckle.

“It all makes sense now. That’s why you always have a hard-on and are always jacking off. You have a little crush on me, don’t you Eric?”

She walked over to the bed and sat down, still wrapped in her towel. She patted the bed and invited Eric to sit next to her.

His face was still bright red, but he finally managed to be honest with Kendra.

“Yes. You are the most beautiful girl that I have ever known and I can’t stop thinking about you.”

“Aww!” Kendra moaned. “You are so sweet.”

Kendra leaned over and gave Eric a peck on the cheek. He wasn’t sure what that meant, but he liked it anyway. 

Eric’s cock was still fully erect. He noticed that Kendra couldn’t stop looking at it.

She quipped, “Boy, that thing doesn’t go down without a fight, does it?”

The two chuckled for a moment. Eric added, “Very rarely.”

“I have never seen one that big in person before. Is it okay if I touch it?”

Kendra didn’t wait for a response, she just started to reach over.

Eric jerked away. Everything had happened too quickly for him and as much as he wanted it, he freaked out.

“Oh, okay. I’m sorry. I took it too far, didn’t I?” Kendra asked.

Eric blurted, “No, no. It’s fine. I just don’t know if we are supposed to be doing this.”

“Why? We aren’t related any more than our parents are. I’m pretty sure that they are fooling around in their bedroom right now.”

“Ugh, gross,” Eric groaned “But, yeah, I guess it is fine. The step-sister thing just kind of makes me feel kind of dirty.”

Kendra sent an ultimatum, “So, do you want to fool around then, or do we each lock ourselves in our rooms and masturbate while thinking about each other?"

Eric leaned in and whispered, “Please, stay.”

Kendra smiled back at Eric. Then she ran over and locked the door. By the time she arrived back at the bed, her towel was on the floor. Kendra slinked in between Eric’s legs and crouched over. She grabbed ahold of his cock and gave it several long strokes.

“Fuck! You are a fucking man!” Kendra groaned as she started to touch herself.

Eric reached in and started to caress her breasts with both hands. Kendra slowly lowered herself down. She started to lick the length of his cock and suck on the head. She struggled to get much past the head without having to back away, though.

Clearly frustrated with her oral technique, Kendra sprung up and climbed on Eric’s lap.

She squeezed him tightly, pressing her firm breasts against his chest. Eric’s cock was pinned in between them. Kendra started grinding her wet pussy against his cock, covering it with her juices.

She leaned back and pressed his cock against her midsection. In that position, it went about two inches past her navel. She taunted Eric, asking him if he thought that he could fit all of that cock inside of her.

Kendra started to climb upward. As she grabbed ahold of Eric’s cock, he tried to steady her. She could feel how aggressively he was trembling. She lowered herself back down onto his lap and stared at him.

Eric had quickly learned that he could not lie to Kendra. She saw through it every time.

“I’m a virgin,” Eric confessed.

Kendra gave Eric a hug and a kiss. He feared that his confession would bring this encounter to an end.

Instead, Kendra told him that they were going to do whatever he wanted to do. Eric, of course, said that he was happy with the way that it was going, but Kendra insisted that it be Eric’s fantasy. She failed to get much feedback out of him until she pushed the right buttons.

“When you fantasize about fucking me, what position are we in?”

Eric thought about it for a second. Then he told her that she was usually on her back on the edge of the bed, and he was standing. He added that he wanted to see her face and her breasts while they were sexually entwined. Kendra responded that it sounded perfect.

As the two gathered themselves and repositioned. Kendra asked Eric to take it slow at first. She clearly wasn’t sure how well she would be able to handle a cock both thicker and longer than she had previously experienced. As Eric was approaching her, she let him know that she was on the pill.

As Eric was lining himself up, it was clear that he wasn’t completely confident that he was in the right spot. He pressed softly against Kendra and the tip of his penis guided gently to its intended target.

He gave a single shove and managed to just get the tip inside of Kendra.

“One more thrust like that,” Kendra directed.

Eric complied and the next thrust pushed him in almost halfway. Kendra’s head rocked backward and Eric gave her a minute. Kendra was exhaling deeply and her legs and toes were curled up at each of his sides.

Kendra gave Eric a signal and he started to slowly rock back and forth. Kendra continued to lay flat on her back, staring at the ceiling until Eric said, “Kendra, look at me.”

She raised her head up from the bed and locked eyes with Eric. Eric increased his thrusting to a moderate pace. Kendra exhaled deeply with every thrust. As Eric went deeper, tears began to appear in Kendra’s eyes.

With little advance notice, Eric felt a surge shooting through his body. He stopped immediately, but it was already too late. He continued on for a brief moment until the pleasure overwhelmed him and he had to stop.

Eric’s head and shoulders slumped for a moment. Once he regained his posture, he seemed upset.

“I…I’m sorry. I know that wasn’t very good. It was too quick. I was too quick.”

Kendra sat up partially.

“That’s okay, baby. That was long enough for the first time. It’s going to take me a few times to be able to handle you anyway.”

Eric’s eyes lit up.

“So, we can do this again?”

Kendra chuckled, “Well, only if you want to.”

Eric fired back, “Can we do it again later?”

“Uh, sorry, but I think that I am going to need a couple of days to recover. There are other things that we can do in the meantime, though.”

Eric started to withdraw his softening cock. As he did, a trickle of cum dribbled out of Kendra’s gaping vagina.

“Fuck! By the time that I can take all of that, you are going to have me completely ruined,” Kendra exclaimed. “Well, at least I get ruined in the fun way.”

Eric nodded in agreement, but he didn’t understand what she meant by that.

Over the following months, Eric and Kendra became quite comfortable with each other. They each strutted around their end of the house with little or no clothing on. They moved freely from each of their bedrooms and both used the bathroom simultaneously quite frequently. They often enjoyed teasing and tormenting each other under the radar. 

Kendra started to refer to Eric as Arod. They were relatively certain that their parents wouldn’t get the reference as they weren’t the type to watch The Lord of the Rings.

It took over a month for Kendra to be able to handle Eric’s girth comfortably, and it took a bit longer for him to learn how to control himself. Once he had, though, they were a force to reckoned with.

They kept their romantic nature secretive, of course, but when they were alone in the house it was not uncommon for them to romp their way from room to room.

And, yes, Kendra did get her vagina wrecked…in the good way.

Published 
Written by SuccubusSlayer
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