Daddy's Girl Pt. 01

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Mike's crossdressing gets him much closer to his stepdad.
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Mike, 19, still lived with his mom, Jana, and his stepdad Peter. Mike wasn't your typical man. For years, he struggled with his identity. He didn't enjoy wearing overly masculine clothes or participating in sports. Instead, he had a deep passion for feminine fashion without ever trying it on.

Jana worked long hours and was rarely home. As for Peter, he could never really connect with Mike due to their differing interests and personalities. While Peter embodied traditional masculinity, Mike was the complete opposite.

One day, while doing the laundry as usual, Mike entered his parents' bedroom to put away their clean clothes in the wardrobe. As he carefully hung up each item of clothing belonging to his mom, something caught his eye--a beautiful and flowing negligee that seemed new. Intrigued by its allure, Mike couldn't resist getting a closer look.

The neglige was made of a delicate, sheer fabric that flowed like water as Mike held it up to examine it. The garment was a pale pink color with intricate lace detailing along the edges and hemline. The straps were thin and dainty, adorned with small satin bows that added a touch of femininity to the piece.

As he ran his fingers over the fabric, he could feel its softness and silky texture. It looked like something out of a dream, and Mike couldn't help but imagine how beautiful his mom would look wearing it. He hung the neglige back in the wardrobe, feeling a mix of fascination and desire for the feminine garment.

He never tried that before but he wanted to know what it feels like on his skin. His mom was at work, and his stepdad was sleeping in front of the TV in the living room. He peeked out just to make sure.

Mike quickly grabbed the neglige and went to his room, feeling a rush of excitement and nervousness. He closed the door behind him and quickly undressed. As he slowly slipped on the garment, careful not to damage the delicate fabric, he felt a sense of liberation and joy wash over him. The soft fabric hugged his body, making him feel beautiful and feminine.

He never experienced anything like this before, and it was both exhilarating and terrifying. He stood in front of the mirror, admiring how the neglige looked on him. The pale pink color complemented his fair skin, and the lace detailing added a touch of elegance to his appearance.

Mike didn't understand why he felt so drawn to feminine clothing, but in that moment, he didn't care. All that mattered was how beautiful and free he felt while wearing it.

He changed back and brought the neglige back to his mom's wardrobe, feeling a mix of guilt and excitement. He knew he shouldn't have taken it without her permission, but he couldn't deny the rush he felt while wearing it.

Mike's curiosity about feminine clothing only grew from that moment on. He started to sneak into his mom's wardrobe more often, trying on different pieces and experimenting with different styles. At first, he only did it when he was home alone, but eventually, he started doing it even when his stepdad was around. Peter spent most of his time in the living room, so Mike had enough opportunities to try on different pieces and admire himself in the mirror.

As Mike was responsible for all the laundry, he could wear his mom's clothes without her noticing. Mike felt like he was living a double life, and it was both thrilling and terrifying.

Peter loved seeing Jana in lingerie, so she owned a large collection of it. She always made sure to wear something sexy and provocative for him, knowing how much he loved the way she looked in lace and silk.

Mike was drawn to all of his mom's lingerie, but he couldn't bring himself to admit why. He tried on different pieces, admiring how they hugged his body and accentuated his curves. But he knew that this wasn't normal, that boys weren't supposed to like wearing women's clothing.

He felt guilty and ashamed of his secret obsession, but at the same time, he couldn't help the rush of excitement he felt every time he slipped into one of his mom's bras or panties. It was a forbidden pleasure, one that he knew could get him into trouble if anyone ever found out.

But still, he couldn't resist the lure of those delicate fabrics and feminine designs. They called out to him like a siren song, tempting him with their beauty and sensuality. And try as he might, Mike couldn't ignore their pull.

One day Mike wanted to dress up again, but this time he didn't want to wear just any piece of lingerie. He wanted to try on something more daring and provocative, something that would make him feel like a true seductress.

He snuck into his mom's wardrobe, searching for the perfect outfit. And then he saw it: a black satin corset with matching thong panties. It was unlike anything he had ever seen before, and he knew he had to try it on.

As he slipped into the tight corset and fastened it in place, Mike felt a surge of electricity run through his body. It took him a while to adjust to the tightness of the corset, but once it was on, he felt like a different person. The sensation was intoxicating, and he couldn't help but admire himself in the mirror. He looked like a dominatrix, powerful and alluring at the same time.

Mike occasionally listened for his stepdad snoring in the living room, that's how he knew he had enough time to dress up without getting caught.

That day Mike wanted to take his dress-up game to the next level. He decided to add stay-ups and a short skirt to complete his outfit. Quickly, he found the stay-ups and carefully slid them onto his legs, making sure not to tear the delicate material.

Then he looked for a short skirt, finding one that matched perfectly with his black satin corset. He slid into it, feeling the soft fabric caress his legs. It felt good, a rush of excitement surging through him as he admired himself in the mirror. The combination of the corset and the skirt made him feel powerful and seductive, like a true femme fatale. Mike couldn't help but smile at his reflection, reveling in the forbidden pleasure of his secret dress-up game.

Even though he knew that what he was doing was taboo, he couldn't bring himself to stop. Mike loved the feeling of being transformed into someone else, someone more daring and adventurous than his everyday self. He loved the power that came with wearing women's clothing, the way it made him feel sexy and desirable.

And as long as nobody found out about his secret obsession, Mike knew that he would keep indulging in this forbidden pleasure for as long as he could.

Mike didn't notice that Peter had woken up. He was too lost in his own world, admiring himself in the mirror and reveling in the feeling of being dressed up like a seductress.

But then he heard a sound behind him, and he turned to see Peter standing in the bedroom door. The color drained from Mike's face as he realized he had been caught. He scrambled to find words, but they escaped him. Peter's eyes widened with shock and confusion, his mouth agape.

For what felt like an eternity, neither of them spoke. The silence was suffocating, thick with unspoken questions and judgments. Mike felt exposed, vulnerable in his feminine attire. He braced himself for the inevitable backlash, the ridicule and rejection that would surely follow.

Before Mike could come up with an excuse or explanation, Peter spoke up.

"What the hell are you doing?" he asked, his voice filled with shock and confusion.

Mike's heart raced as he tried to think of a response. Should he lie and pretend that he was just trying on clothes for a costume party? Or should he come clean and confess his true desires?

"I can explain," Mike said, his voice shaking with fear and embarrassment. "I just wanted to try something different, you know? To see what it felt like."

Peter stared at him for a long moment, his expression unreadable. Finally, he spoke again.

"Look," he said, his tone softer this time. "I'm not going to judge you or anything. But you should probably talk to your Mom about this."

Mike felt a wave of panic wash over him at the thought of his mother finding out about his secret obsession. He knew that she would never understand, and that she would probably be horrified by what he had done.

"Please don't tell her," he pleaded, his eyes pleading with Peter's. "I promise I'll stop doing it if you won't say anything."

Peter responded, his voice gentle yet firm. "Look, Mike," he began, his eyes meeting Mike's with understanding. "I think the first step here is for you to undress again."

In his nervousness, Mike pulled the wrong strap in the corset and created a knot he couldn't get out. Panic set in as he struggled to undo the tangled fabric. He felt his heart racing with every passing moment, knowing that Peter was still standing there watching him.

Mike tried to remain calm and composed, hoping that Peter wouldn't notice anything. But as he fumbled with the knot, he could feel his hands shaking uncontrollably.

"What's wrong?" Peter asked, noticing the panic on Mike's face.

"I messed up the corset," Mike admitted, turning around to show Peter the tangled fabric. "I can't get out by myself."

Peter sighed and stepped closer to Mike. "Let me help you with that," he said, his hands reaching for the knot.

As Peter worked to untangle the corset, Mike couldn't help but feel a mix of embarrassment and gratitude.

Peter's thick fingers fumbled with the knot in the corset, unable to untangle it. Frustrated, he reached around Mike and grabbed him by the hip, trying to pull with more force. Mike gasped at the sudden contact, surprised by Peter's touch.

As he pulled and twisted the fabric, his hands brushed against Mike's skin, sending shivers down his spine.

Mike couldn't believe what was happening. Now, as Peter's hands roamed over his body, he felt a rush of desire unlike anything he had ever experienced before.

It was hard for Peter to focus on the task at hand. As he worked to untangle the corset, his eyes kept wandering over Mike's body, taking in the feminine curves and delicate features that were usually hidden away.

He couldn't deny the attraction he felt towards Mike, even though it went against everything he had been taught about appropriate behavior.

Finally, after what felt like an eternity, Peter managed to untangle the knot in the corset.

As soon as the knot was undone, Mike turned around to face Peter, feeling a deep blush spread across his cheeks. He could see the awkwardness in Peter's eyes as he looked down, trying not to make things more uncomfortable than they already were.

But then Peter noticed something sticking out from beneath Mike's skirt and his eyes widened in surprise.

Mike had a mild erection, and he could feel his face turning even redder with humiliation. He tried to cover it up by quickly adjusting the corset and pulling down on his skirt, but he knew that Peter had already seen it.

Peter's expression was unreadable as he stared at Mike, taking in the unexpected sight. For a moment, neither of them said anything, and Mike wanted nothing more than to disappear into thin air.

But then Peter surprised him by reaching out and gently placing a hand on his shoulder. "It's okay," he said softly. "There's nothing wrong with feeling aroused."

Mike couldn't believe what he was hearing. Here was his stepdad, someone who had been nothing but strict and distant with him for years, suddenly showing him kindness and understanding.

Mike had tears coming to his eyes, touched by Peter's unexpected kindness. He couldn't remember the last time someone had shown him such compassion.

Without thinking, he threw himself into Peter's arms, feeling a deep sense of gratitude and relief wash over him. For a moment, they stood there in silence, holding onto each other as if they were the only two people in the world.

As they pulled away from each other, Mike could see a softness in Peter's eyes that he had never noticed before. It was as if a weight had been lifted off both of their shoulders, allowing them to finally connect on a deeper level.

"I'm sorry," Mike said softly, feeling like he needed to apologize for something even though he wasn't sure what it was.

Peter shook his head. "Don't be. We all have our secrets and desires. It's okay to explore them, as long as we're not hurting anyone."

Mike nodded slowly, feeling like he was learning something important about himself and the world around him. Maybe things didn't have to be so black and white after all.

"I'm actually surprised," Peter said, looking at Mike with a newfound sense of appreciation. "The outfit looks great on you."

Mike felt a flush rise to his cheeks once again, but this time it was from the compliment rather than embarrassment.

"Thanks," he managed to say, feeling shy but pleased nonetheless.

Peter smiled warmly at him, his eyes crinkling at the corners in a way that made Mike's heart skip a beat. He couldn't believe how much things had changed between them in such a short amount of time.

It was as if they had both been living in their own little worlds, unable to connect until this moment. And now that they had finally broken through those barriers, there was no going back.

The next day as Mike's mom left for work, Mike felt guilty for what he had done the day before.

He was sitting at his desk, scrolling through social media when he heard a knock on the door. He looked up to see Peter standing in the doorway, a serious expression on his face.

"Hey, can I talk to you for a minute?" Peter asked, stepping into the room and closing the door behind him.

Mike nodded, feeling a sense of trepidation as he watched Peter make his way over to the bed and sit down beside him.

"I know yesterday was probably overwhelming for you," Peter began, looking at Mike with a mix of concern and understanding. "But I want you to know that you don't have to hide who you are around me."

Mike's heart skipped a beat as he looked at Peter, unsure of what he meant by this statement.

"I educated myself a bit and I know that wearing women's clothing is something that makes you feel comfortable," Peter continued. "And I want you to know that it's okay if you wear them here in the apartment. You don't have to stay cooped up in your room all day."

Mike felt tears prick at the corners of his eyes as he looked at Peter, feeling an overwhelming sense of gratitude and relief wash over him.

"Thank you," he managed to say, feeling like words weren't enough to express how much this meant to him.

Peter smiled warmly at him, placing a hand on his shoulder in a gesture of support and encouragement.

"Just be yourself," he said softly. "We will find a way to tell your mom."

After Peter left his room, Mike couldn't help but replay their conversation in his mind. The weight of Peter's words hung heavy in the air, and Mike found himself grappling with a mix of emotions. He knew that this was a pivotal moment in their friendship, and he didn't want to let fear hold him back any longer.

Finally, after much contemplation, Mike made up his mind. He decided to take Peter up on his offer. It was time to embrace who he truly was and stop hiding behind closed doors.

Jana was at work all day, so Mike and his stepdad had the apartment to themselves. He made his way into his parents' bedroom, feeling a sense of nervous excitement as he looked through Jana's wardrobe for something to wear.

As Mike rummaged through Jana's closet, he stumbled upon a matching black bra and a pair of stay-up stockings. He hesitated for a moment, but then he remembered Peter's words of encouragement and decided to go for it.

He slipped on the bra and adjusted it until it fit comfortably. Then he carefully rolled up the stockings and pulled them up his legs one by one.

As he looked at himself in the mirror, Mike felt a sense of pride and freedom reflecting to him.

Now, with Peter's support and acceptance, he finally felt like he could be true to himself. And that was a feeling like no other.

He spotted a black lace dress hanging in the back of the closet and felt drawn to it. He pulled the dress over his head. It fit him perfectly, hugging his delicate body.

Mike stood in front of the mirror, admiring himself in the dress. He couldn't believe how beautiful he looked, or how happy it made him feel to finally be able to express himself in this way.

As he twirled around in front of the mirror, Mike knew that this was just the beginning of a journey towards self-discovery and acceptance. But for now, in this moment, he was content simply being himself.

Mike reached up and removed the hair band from his chin-length hair. He ran his fingers through it, trying to shape it into a more feminine style. It wasn't easy - he had never been much of a hairstylist - but he was determined to make himself look as beautiful as possible.

He spotted the small desk in the corner of the room, adorned with an array of makeup products. It was a treasure trove of colors and possibilities, waiting to be explored. With his mom still hours away at work, he knew he had ample time to experiment and delve into this new realm.

Mike approached the desk cautiously, his heart pounding with anticipation. He picked up a tube of mascara, feeling its weight in his hand. Uncapping it, he carefully pulled out the wand, coated in jet-black liquid. Taking a deep breath, he positioned the brush near his lashes and hesitantly blinked.

As the wand touched his eyelashes, he felt a gentle tickle against his skin. Slowly, he swept it through each lash, coating them with the black pigment. With each stroke, Mike watched as his lashes transformed before his eyes, becoming fuller and longer.

Excitement surged through him as he continued applying the mascara, layering it on for that extra pop. He marveled at how it accentuated his eyes, giving them a captivating allure. It was as if a whole new world had opened up before him.

Admiring himself in the mirror, Mike couldn't help but smile at the transformation. The mascara had added depth and intensity to his gaze, enhancing his natural beauty in ways he had never imagined.

"Peter, is it really okay for me to come out like this?" Mike shouted out, his voice shaking slightly.

"Of course it is, Mike," Peter responded firmly.

Mike took a deep breath and nodded to himself. He knew that Peter was right - he couldn't keep hiding who he truly was from the world. It was time to embrace his true self and let the chips fall where they may.

Feeling emboldened by Peter's support, Mike stepped out of the bedroom and into the living room, ready to face whatever came next.

Peter smiled at Mike as he entered the living room. "How do you feel?" he asked, his voice gentle.

Mike took a deep breath and smiled back at Peter. "I feel amazing," he said. "It's like a weight has been lifted off my shoulders. I can finally be myself."

Peter nodded in understanding. "I remember when Jana wore that dress to a party a while ago," he said, gesturing towards the black dress that Mike was wearing. "You look just as beautiful as she did."

Mike blushed at the compliment, feeling grateful for Peter's support and encouragement.

Days went by, and Mike spent much of his time experimenting with different outfits. He tried on everything from skirts and dresses to jeans and t-shirts, exploring what felt most comfortable and authentic for him.

Through it all, Peter was there to offer support and encouragement. He would sit with Mike as he tried on various clothes, offering feedback and compliments along the way.

As they spent more time together, Mike felt more and more comfortable being himself around Peter. He opened up about his fears and insecurities, and Peter listened with empathy and understanding.

Mike was lucky. His mother's clothes fit him perfectly, as if they were made for him. He knew not everyone was that fortunate.