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Caught By My Neighbor: A Crossdressing Adventure

"An innocent young crossdresser gets discovered by an understanding neighbor"

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It all started innocently enough when I stumbled upon a box of my mother's old clothes in the garage. My curiosity got the best of me and I decided to try a few things on. As soon as I put on a silky nightgown and a pair of lacy panties, I was hooked.

The way the material felt against my skin and the way the lingerie hugged my curves ignited a fire within me. I couldn't believe the rush of excitement and arousal that washed over me.

From that moment on, I found myself sneaking into my mother's closet whenever I had the chance. I couldn't resist the temptation of trying on her dresses, skirts, and blouses.

As I explored more and more of her wardrobe, I began to understand the allure of dressing in women's clothing. It was more than just the physical sensations, it was the feeling of transformation, of becoming someone else for a moment.

But as much as I enjoyed the secret indulgence, I was always careful to hide my newfound interest. That is, until one day when my neighbor, Darius, caught a glimpse of me through the curtains. I froze in shock and embarrassment as he casually called out my name and asked if he could come over to talk.

My heart raced as I tried to come up with an excuse, but my mind went blank. I could feel my face flush with humiliation as I opened the door to let Darius in.

He had a knowing smile on his face and a mischievous twinkle in his eye. I knew he had seen me dressed in my mother's clothes and I couldn't help but feel exposed and vulnerable.

To my surprise, Darius didn't judge or mock me. Instead, he shared with me that he was gay and that he had his own experiences with cross-dressers.

He even revealed that he had seen me dressed in my mother's clothing before, but he never said anything because he didn't want to invade my privacy.

I was shocked and relieved at the same time. Here was someone who not only understood but also accepted my secret desires. As we talked, Darius offered to buy me some clothes of my own and we browsed the internet together, picking out some sexy outfits.

I couldn't believe it when Darius showed up at my doorstep, unannounced and with a mischievous glint in his eyes. He held up several shopping bags and before I could even ask, he exclaimed, "I got you some new outfits, babe!"

I was taken aback by his gesture but also exhilarated by the thought of trying on the new outfits.

Once inside, I opened up the bags and was greeted with an array of sexy lingerie, dresses, high heels, and stockings. I couldn't contain my excitement as I held up each piece, eagerly awaiting the opportunity to try them on.

Darius, being the gentleman that he was, offered to help me change into the outfits. As I slipped on the first lingerie set, a lacy black bra and matching thong, I could feel his eyes on me, admiring every curve of my body. He let out a low growl of approval, making me feel like the most desirable woman in the world.

Next, I tried on a red bodycon dress that clung to my body in all the right places. Darius couldn't take his eyes off me, his gaze filled with desire and a hint of possessiveness. I couldn't help but feel a tinge of satisfaction knowing that I had this effect on him.

But it wasn't just the outfits that were turning him on. It was the way they made me feel, confident and alluring. With each new outfit, Darius became more and more aroused, his eyes dark with lust.

Finally, I slipped into a black mini-dress, a pair of strappy heels, and sheer stockings. I could feel Darius's gaze burning into me as I walked towards him, the soft fabric of the dress swaying against my skin with each step. And then he did something unexpected.

Without hesitation, Darius pulled me into his arms, his lips claiming mine in a fiery and passionate kiss. I could feel the heat between us and the electricity coursing through my body.

All of our pent-up desire and longing had finally been unleashed, fueled by the sexy outfits and the anticipation of trying them on.

As we continued to kiss, I thought about how lucky I was. Darius was so handsome and strong. His smooth, dark skin contrasted perfectly with his bright, white smile. And now, here we were, locked in a passionate kiss, his toned body pressed against my slender frame. It was like a dream come true.

As his hands explored my body, I couldn't help but feel the electricity between us. His touch was gentle yet firm, sending shivers down my spine. I could feel my desire for him growing with each passing second. And the way he kissed me, it was like he knew exactly what I needed. It was sensual and intense, leaving me breathless and wanting more.

As we moved towards the bed, my mind was filled with a million thoughts. I couldn't believe that this sexy stud was here with me. I felt like the luckiest person alive. And as Darius guided me, I couldn't help but feel a rush of excitement coursing through my veins.

As we sank into the soft, plush mattress, our kisses grew even more intense. Our bodies were entwined, our hands moving in perfect sync. It was like we were in our own little world, where nothing else mattered except for this moment between us.

I couldn't help but admire Darius as our makeout session continued. His body was toned and muscular, but also incredibly gentle and caring. There was a sense of raw masculinity about him that was undeniably attractive. I felt myself getting lost in his touch, his kisses, and his presence.

I could feel the tension building between us. Darius looked at me with those piercing dark eyes, his lips curling into a mischievous smile, and asked in a husky low voice, "So, are you ready to please me?"

My heart raced at the sound of his request and with one nod, I sank down onto the bed. His strong hand gently guided me down until I was kneeling between his legs, my eyes never leaving his.

I could feel my pulse quicken as he quickly unbuttoned his pants, then tugged them off and threw them on the floor. My anticipation grew with each passing second, knowing what was about to be revealed.

And then, there it was. His cock, hard and throbbing, standing proudly in front of me. It was like nothing I had ever seen before. Long and thick, with veins running along the shaft, and a dark, almost menacing, head. I reached out hesitantly, my hand trembling as I wrapped my fingers around it.

It was a powerful feeling, holding his cock in my hand for the first time. I could feel the heat emanating from it, and I marveled at the softness of the skin against my palm.

Slowly, I began to stroke him, my fingers exploring every inch. I couldn't help but admire the contrast of his dark skin against my own porcelain complexion.

As I continued to stroke him, the excitement inside me grew. I felt an undeniable desire to take him into my mouth and show him just how much I wanted to please him.

I wanted to taste him, to feel his length sliding down my throat, to hear him moan with pleasure. And so, with a newfound determination, I leaned forward and took him into my mouth.

He groaned as I began to suck, my tongue swirling around the tip, my hand still stroking the base. The taste of him, the scent of him, it all drove me wild with desire. I couldn't get enough of him, and I could tell from his reaction that he was enjoying every minute of it.

With each movement of my mouth, I could feel him growing harder, the veins on his cock becoming more prominent. I could sense his pleasure building, and it only fueled my desire to please him even more.

I wanted him to know that he was in control, that I was here to serve and please him in any way he wanted. It was his pleasure that brought me the most gratification.

Knowing that I had the power to bring him such immense satisfaction, to make him quiver and moan, it was an intoxicating feeling. And as I continued to please him, I couldn't help but wonder how long he would last.

Without hesitation, I wrapped my lips around his cock, eagerly sucking and licking every inch. His hands tangled in my hair, urging me to continue as he let out a guttural moan. I could feel the tenseness in his body as I continued to pleasure him, his moans growing louder and more urgent.

I could taste the saltiness of his skin as I ran my tongue along the underside of his cock. His hips bucked uncontrollably, his breathing becoming more ragged with each passing moment. I could feel him getting closer and closer to the edge.

As he begged me to continue, I quickened my pace, using my hands and mouth in perfect sync to drive him wild. I could feel him trembling beneath me as his moans turned into desperate cries.

And then, with one final thrust, he reached his peak and came hard, filling my mouth with his hot, sticky release. Without a second thought, I swallowed it all, not wanting to disappoint him.

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As we both caught our breath, I looked up at him, our eyes meeting in a moment of pure satisfaction. Without a word, I licked my lips, letting him know just how much I enjoyed submitting to him.

The next day, he returned, unable to resist the temptation. And again, I indulged in dressing up for him and giving him intense pleasure, sucking his cock and swallowing his release.

This became our routine for a while, him leaving after each encounter, only to come back for more. And each time, I welcomed him back enthusiastically, eager to feel his body against mine and hear his moans of pleasure. We had found a mutual desire that united us in a blissful bond.

Darius and I had been engaging in our usual ritual for weeks. Every time he came to visit, we would dress me up in the sexiest lingerie, have me worship his body, and then I would eagerly suck his cock until he came into my mouth.

But one day, things were about to change forever. While in the midst of foreplay, Darius stopped and looked at me with a devilish glint in his eye. He leaned in close and whispered in my ear, "Why don't we mix things up a bit today?"

My heart raced as I realized what he was suggesting. I knew what he wanted. He wanted to bring things to the next level and take my virgin ass. I immediately felt a hint of hesitation and fear.

I had never done anything like that before, and the thought of it made me nervous. Darius started to whisper all the things he wanted to do to me, how good it would feel, and how I wouldn't regret it.

He stroked my body, tracing every curve and igniting a fire within me. I could feel my desire and curiosity growing with each passing moment. Darius knew exactly how to push my buttons and he was doing just that. The more he talked, the more my hesitations and fears melted away.

I couldn't believe it, I was actually considering taking his cock in my ass. I had always been curious about it but never had the courage to try it. But with Darius, I felt safe and excited to explore this new territory. My body was aching for him and I knew I couldn't say no.

Darius had told me about his previous gay relationships, and I knew he was an experienced lover. This was not his first time. He was well-versed in anal sex and I was grateful to have him guide me through this new territory.

Before we indulged in any play, he instructed me to take a shower and make sure my body was clean, specifically paying attention to my "boy pussy" as he called it.

Once I was squeaky clean, he guided me back to the bedroom, where he had a selection of sexy lingerie and outfits laid out for me. Darius loved watching me dress up as a sexy girl for him, and I enjoyed indulging in this fantasy.

I carefully slipped into the chosen outfit, feeling sexy and confident under his watchful eye. Darius undressed, then leaned back on the bed and began stroking his cock while I posed and twirled for him.

"Come here sexy, I want to take you now baby."

Darius guided me onto the bed, then began propping pillows under my hips to give him better access. He presented a bottle of lube and then started to gently massage and tease my entrance, slowly relaxing and opening me up.

I loved the feeling of his fingers working me over, growing more and more eager for his cock to join in. I finally gave in and told him to take me however he wanted. He smirked and positioned himself behind me.

I could feel his hard cock pressing against my tight hole and I couldn't help but gasp in anticipation.Finally, with a gentle push, he slowly entered me and I felt the tightness and warmth of my anal virginity being lost.

It was a mix of pleasure and discomfort, but with every thrust, the pleasure overtook any initial discomfort. Darius knew exactly how to move and angle himself to hit all the right spots.

As our bodies moved together in perfect rhythm, I couldn't help but feel grateful for Darius's past experiences and knowledge. He knew exactly how to prepare and pleasure me, making the experience enjoyable and satisfying for both of us.

I never knew anal could feel so good, feeling his cock pressing against my prostate gland and filling my body with arousal. Darius was taking me to new heights of ecstasy, and I was loving every second of it.

In the side mirror, I caught a quick glimpse of our lovemaking, watching in awe as his dark sexy body perfectly intertwined with my own, like yin and yang. Our bodies perfectly complimented one another as I watched his dark cock slowly disappear inside me.

He moved with a steady rhythm, going deeper and deeper with each thrust. I couldn't contain my moans and screamed out for more. It was like nothing I had ever experienced before. Darius's dominance only added to the intensity of the moment.

My body started shaking and trembling beneath him. It wasn't just the physical pleasure that had me completely under his spell. It was the way he held me with such intense adoration, the way he whispered sweet words of passion and desire into my ear and the way he made me feel so wanted.

As he continued to thrust deeper and harder, I could feel my body reaching the peak of pleasure, my toes curling and my hands gripping the sheets tightly. And just when I thought I couldn't take anymore, he whispered in my ear, "Come for me, baby. Let yourself go and come for me like a girl."

His words, coupled with his skilled touch, sent me over the edge, my body bucking and convulsing as come began to trickle and leak out of my little soft clitty.

Darius and his cock were making me come, filling my body with pure ecstasy. And in that moment, I didn't care about anything else but the pleasure coursing through me and the man who was bringing me to such incredible sissygasm.

I moaned and writhed beneath him, my hips moving in rhythm with his expert thrusts. Darius, proud of his accomplishments and the knowledge of making me come, suddenly began fucking me even harder and faster than before.

I can feel his climax approaching, bubbling up from the depths of desire, and just as I reached the pinnacle of pleasure, Darius's hard and fast thrusts send me over the edge, making me sissygasm again and again.

But Darius wasn't done with me yet. I could tell he was determined to reach his own release, and no longer holds himself back. With a fierce determination, he begins to fuck me with even more intensity.

His heavy breaths and guttural moans heighten the raw and primal nature of our coupling. I can feel his desire building as his thrusts become more erratic, his body tense and his grip on my hips becoming almost painful.

Suddenly, in a desperate and almost pleading voice, Darius begs to come on my face. I can feel my heart racing as I realize how much this is turning him on, how much he wants to mark me as his own.

Without hesitation, I eagerly consent, sliding off his cock and flipping over onto my back. He shifts his body over mine as I gaze up at him with a mixture of anticipation and lust in my eyes.

Quickly, Darius reaches down, jerking his cock, his intense gaze never leaving mine, and without any hesitation, he reaches his climax. With a guttural groan, he releases himself all over my face.

His hot and sticky come lands in rivulets and splatters across my flushed skin. I relish the feeling of his warm release against my face, feeling the heat and wetness spread over my cheeks and lips.

With a satisfied smile, Darius collapsed on top of me and into my arms. I pulled him close while we both caught our breath and basked in the afterglow of our passionate love session.

The intensity of our connection, both physically and emotionally, had me in a state of pure bliss, our bodies still trembling with the remnants of our shared ecstasy.

This is a moment I will never forget, a moment of complete surrender and trust, as I gave myself fully to Darius and he rewarded me with mind-blowing lovemaking.

As I lay there, still quivering and panting, Darius leaned down to kiss me gently, his own body still trembling. At that moment, I realized that it wasn't just the physical act that had brought us together, but the emotional and intimate connection we shared.

Darius had shown me a sense of satisfaction and fulfillment I had never experienced. I had let go of all my inhibitions and trusted him to lead me into uncharted territory. And I was so glad I did.

I couldn't help but think about how grateful I was that Darius had discovered my secret. That he had helped open me up to new experiences and push me out of my comfort zone, all while making me feel safe and desired. I knew that I would always be eager to explore new things with him by my side.

This visit had definitely been one to remember, but we both knew there was more to come.

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Written by MirandaGreen
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