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#Cheating #Mature #Teen

By HanSolo

Young skateboarder breaks his arms and his stepmother has to take care of him.

In Miles, a 16-year-old with a love for skateboarding, had recently suffered a severe fall, leaving both his arms in casts. His father was away on one of his long business trips, leaving Miles in the care of his stepmother, Emma, a woman of forty with a gentle beauty that spoke of years of self-care and discipline.

The previous night had been manageable; Miles had returned from the hospital in his pajamas and a coat, which Emma had easily removed. But this morning was different. Emma, anticipating the day’s challenges, had already changed into her bathing suit beneath a light, flowing gown when she knocked on Miles’s door.

“Miles, it’s time to get up for your shower,” she called out, her voice laced with an attempt at normalcy.

“Alright, Emma,” Miles responded, his voice slightly muffled by the door. He was already sitting up, his arms awkwardly encased in their casts.

Emma entered, the gown doing little to hide her readiness for the task at hand. “I thought it might be easier if I was already… prepared,” she said, a nervous smile tugging at her lips as she gestured to her attire.

Miles nodded, his face a mix of appreciation and embarrassment. “Thanks, Emma, that makes sense.”

They made their way to the en-suite bathroom, the air between them charged with a new kind of intimacy. Emma helped Miles stand, guiding him gently. “Let’s start with your top,” she suggested, her fingers working quickly on the buttons of his pajama shirt.

Once the top was off, she paused at his pants. Miles took a deep breath, knowing what was to come. Emma knelt down, her fingers at the waistband, and began to pull down. The moment his pants reached his knees, she couldn’t help but notice Miles’s semi-erection, her eyes widening in surprise at his size.

“Good lord, Miles, I… I wasn’t expecting that,” she gasped, her cheeks flushing with a mix of shock and embarrassment.

Miles looked down, his own face turning red. “Sorry, Emma, this is just… awkward,” he muttered, feeling the tension of the moment.

“It’s alright, it’s just biology,” Emma said, trying to regain her composure, though her voice betrayed her surprise. She helped him step out of his pants, and there it was, his size clear and undeniable.

They moved to the shower, Emma’s bathing suit now a practical decision. She adjusted the water to a comfortable warmth. With Miles under the spray, she began to sponge him down, starting from his shoulders, working down his back, and then to his legs.

Avoiding his privates for as long as possible, she finally had to address the situation. By this time, Miles’s arousal was evident, making the task even more awkward. “I’m really sorry about this,” Miles apologized, his voice strained.

“It’s okay, we’ll manage,” Emma replied, her voice a blend of professionalism and discomfort. She quickly wiped him with the soapy sponge, then used the shower head to rinse off the soap, the water colder than usual in an attempt to alleviate his condition.

Drying him off was another ordeal. Emma used a large towel, wrapping it around him but needing to dry every part. “I’ll be quick,” she reassured him as she gently patted him dry, the towel doing little to hide the contact, especially when she got to his now less erect but still sizable member.

Once dressed, they moved to the kitchen for breakfast. The silence was heavy, but Emma broke it with a light laugh. “Well, that was an experience,” she said, trying to inject some humor into the situation.

Miles chuckled, the tension easing slightly. “Yeah, definitely not how I pictured my morning,” he agreed, as they sat down to eat, both grateful for the break from the morning’s intimacy.

After breakfast, the mundane yet suddenly challenging task of using the restroom loomed over Miles and Emma. The realization hit them both at the same time; Miles needed to pee, and this task was bound to be fraught with awkwardness.

“Uh, Emma, I need to go to the bathroom,” Miles said, his voice tinged with embarrassment.

Emma nodded, her expression one of understanding mixed with trepidation. “Right, let’s figure this out,” she replied, leading him back to the bathroom.

Once inside, Miles, thinking quickly, suggested a solution. “If you just pull down my sweatpants and boxers, I can sit and then… uh, shake and call you back to pull them up again. That way, you won’t have to… you know.”

Emma appreciated the foresight. “That sounds like a plan,” she agreed, relieved at the less invasive approach. She stood to his side, avoiding direct confrontation with his anatomy as she bent down to tug his pants and boxers to his ankles. Miles positioned himself on the toilet, grateful for the privacy of this method.

He managed the task, calling out when he was done. Emma returned, again from the side, to pull his pants back up. The relief was palpable for both; the scenario of her having to hold his penis, aim, and then shake it was avoided, sparing them an even more embarrassing moment.

“That was… much better than it could’ve been,” Emma said with a small laugh, trying to lighten the mood.

Miles nodded, chuckling in agreement. “Yeah, I was dreading the alternative.”

However, an unspoken concern lingered between them – the inevitable moment when he might need assistance with something more personal, like wiping. The thought was unsettling, and both silently hoped that situation wouldn’t arise soon.

The rest of the day passed with a mixture of normal activities and the new normal they were adapting to. They watched movies, read, and Emma helped Miles with things like eating or turning pages in his book. The awkwardness was there, but they were getting better at navigating it with humor and mutual respect.

As evening approached, the routine of bedtime brought another wave of awkwardness. Emma helped Miles change into his pajamas, her actions now slightly more assured but still tinged with a sense of the unusual. She tucked him in, making sure he was comfortable with his casts.

“Goodnight, Miles,” she said softly, pausing at the door.

“Goodnight, Emma. Thanks for today,” Miles responded, his voice carrying genuine gratitude.

Once Emma left, closing the door behind her, both felt a mix of relief and apprehension about what the next day might bring, especially with the unspoken fear of further intimate care moments. But for now, they had managed the day, and that was a small victory in itself.

The next morning brought with it the familiar awkwardness of shower time once again.

“Do I need to shower every day?” Miles asked, his voice carrying a hint of reluctance.

“I think you should, Miles,” Emma responded with a gentle firmness.

“We’ll get better at it, and it’ll get less awkward,” she added, trying to reassure both of them.

“OK,” Miles conceded, “but I’ve been thinking I could hang out in my PJs all day since I can’t really go out most days. That’ll save us some awkwardness at bedtime.”

“Good idea, Miles,” Emma said, though she felt a slight pang of rejection. She’d been thinking about his big cock quite a bit and had started to enjoy seeing it, though she’d never admit that out loud. “I really don’t mind taking care of you, you know, Miles.”

“We don’t need to avoid the tasks in front of us,” she added, looking at him with a soft, understanding gaze.

“Oh, yeah, I just thought it was bad for you, and I was trying to help make it less awkward. I’m actually starting to get used to it now,” Miles said, his cheeks coloring slightly. “It seems less embarrassing every day.”

“Anyway, that shower,” Emma said, steering them back to the task at hand.

They went to the bathroom, and Emma began to undress Miles, slipping her gown off to reveal a two-piece bikini this time. Miles tried to avoid looking, but his body reacted to her physical beauty, his cock stirring. Emma started sponging him down, leaving his privates for last, just as before. But the same problem persisted; by the time she needed to wash his erection, it was fully erect.

She looked down at it and said, “Maybe we should wash that first next time.”

He smiled, apologized, and agreed, “It might be a better idea.”

Emma soaped up the sponge and began washing his erection, taking a bit more time on it than she had the day before, though not so long as to make her enjoyment obvious. At the same time, Miles tried to hide the pleasure he was feeling but accidentally let out a small sigh.

Suddenly, the awkwardness returned; Emma quickly grabbed the shower head and rinsed him off. She dried him efficiently, and they moved to breakfast.

“I’m sorry about that, I was trying to hold back – almost like a yawn,” Miles explained, his face red with embarrassment.

“Oh, was it that boring?” Emma blurted out in an attempt at humor.

“No, not at all, it was nice… I mean, you know, it was…” Miles stuttered over his words, clearly flustered.

“Yeah, I know what you mean, Miles,” Emma replied with a knowing smile, easing the tension.

The rest of the day passed with minimal fuss, except for the moment when Miles needed to use the bathroom again. This time, the necessity for Emma to wipe his backside brought a new level of embarrassment and degradation for both. It was a moment neither could laugh off, the intimacy too raw, too personal.

At the end of the day, as Emma helped Miles into his bedclothes, the air was thick with the day’s events.

“Goodnight, Miles,” she whispered, closing the door behind her, leaving him to his thoughts. The day had been a mix of awkward moments.

The morning sun streamed through the curtains, casting a warm glow over Miles’s room, he was asleep, dreaming, Emma was showering him and he had a full erection that she kept brushing accidentally…. Emma entered his room, already dressed in her bikini, ready for shower time.

“Shower time,” she announced, her voice chipper.

“Can we wait five minutes, please, Emma?” Miles asked, his voice tinged with embarrassment.

“Why, what’s the matter?” she responded, concern knitting her brows.

“Er, morning glory?” Miles admitted, his face flushing.

“Oh, c’mon, Miles, I’ve seen it before,” she said with a laugh, helping him up. They walked to the bathroom, where she began to undress him. Sure enough, his impressive cock was fully erect as she removed his pajamas.

In the shower, following their agreement from the day before, she started by washing his cock first. She soaped up her hands and, without thinking, took hold of it directly, bypassing the sponge. It was only after a few seconds of soaping his erection with her bare hands that Miles jerked involuntarily.

With his eyes closed, he managed to say, “The sponge, Emma.”

“Oh god, shit…” Emma said, pulling back, “Sorry, I’m still half asleep.”

She realized the effect she was having on him, and it stirred something within her. She continued to wash the rest of him with the sponge, but it was clear Miles was struggling that morning.

“What’s the matter?” Emma inquired, noticing his discomfort.

“Er, nothing,” Miles replied, trying to brush it off.

“Miles, you can tell me. We have to get through the next few weeks helping each other,” Emma explained, her voice gentle yet firm.

“Well, it’s just my morning glory. I had a weird dream about err, well, I’ve not been able to… you know, since I broke my arms. I can’t… you know…then you grabbed it earlier and…..” Miles attempted to explain, his words trailing off in embarrassment.

“Oh,” Emma said, the realization of his frustration dawning on her.

“Erm, okay, let’s think about this,” her mind raced for a solution. She moved to stand behind him, and he suddenly felt her reach around with both hands, grabbing the soap and soaping up her hands.

“What are you doing?” he asked, his voice a mix of confusion and anticipation.

“Look, Miles, I imagine it’s not comfortable being all frustrated like that, so… let’s just see…” Emma said as she placed her soapy hands on his very hard cock.

“Oh god,” he cried out, overwhelmed by the sensation.

“OK?” she asked, seeking his consent.

“Ahuh,” he responded weakly, his body tense with desire.

As Emma’s soap-slicked hands enveloped Miles’s erection, she felt an intense wave of arousal sweep through her. Days of tension, the forbidden allure of the situation, and the sheer size of his cock had been building up to this moment. Every stroke she made, every glide of her fingers, sent shockwaves through her own body, stoking a fire she hadn’t anticipated.

Her hands moved with a rhythm that was both caring and undeniably sensual. She could feel the pulse of his erection, the way it throbbed in response to her touch. The water from the shower cascaded over them, mingling with the soap, making her movements fluid and almost hypnotic.

Miles’s moans, soft and uncontrolled, only intensified her arousal. She could feel her own breath quickening, her nipples hardening under the thin fabric of her bikini, her body reacting in ways she hadn’t expected. The taboo of the moment, the fact that he was her stepson, the enormity of his cock in her hands – it all conspired to push her towards the brink of her own climax.

Her movements became more deliberate, her fingers occasionally grazing the sensitive tip, eliciting sharp intakes of breath from Miles. She was careful, yet thorough, ensuring that each stroke was designed to bring him relief, but the truth was, she was also seeking something for herself in this act of care.

As Miles’s orgasm approached, his body tensing, his breath hitching, Emma felt an echo of that pleasure deep within her. She was so close, the boundary between helping and indulging blurring in the steam-filled air. Her own arousal was palpable, her body trembling slightly with the effort to maintain control as she focused on Miles’s pleasure.

When he finally came, his release was like a trigger for her own suppressed desires. She felt a shudder run through her, a near-orgasmic wave that left her breathless, her heart pounding against her chest. She had to lean slightly against him for support, her body craving more but knowing this was as far as they could go.

“There, that’s better, right?” she managed to say, her voice thick with unspent desire, the words barely masking her own arousal.

“Yeah, much better,” Miles replied, his voice a whisper of satisfaction and wonder.

They finished the shower in a haze of new sensations, Emma helping him dry off, both aware of the profound shift in their dynamic. The air was thick with the acknowledgment of what had just transpired, a silent agreement of boundaries crossed and new territories explored, all under the guise of necessity and care.

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By HanSolo
#Cheating #Mature #Teen

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31 entries.
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