"Put this on," I said, holding out the lacy pink bra. "And don't even think about arguing."

He hesitated, his eyes darting between the bra in my hand and my unwavering gaze. I could see the internal struggle playing out on his face, a mix of embarrassment and curiosity. But I wasn’t going to give him an out. Not today.

"Come on, you know you want to," I teased, pushing the garment closer to him. "Besides, it’s not like you haven’t done this before."

His cheeks flushed a deep red, but he finally reached out and took the bra from me. I watched as he fumbled with the clasps, his fingers clumsy and awkward. It was almost endearing how much he struggled with something so simple.

"Here, let me help," I offered, stepping behind him and taking over. My hands moved with practiced ease, snapping the clasps together and adjusting the straps until they fit snugly against his chest. He stood there stiffly, like a mannequin, as I worked.

"There, perfect," I said, giving him a gentle nudge towards the full-length mirror in the corner. "Now look at yourself."

He glanced at his reflection, his eyes widening slightly as he took in the sight of himself in the delicate lace. The bra pushed his small breasts up just enough to create a hint of cleavage, and the soft fabric contrasted sharply with his pale skin.

"Not bad, right?" I asked, leaning against the dresser and crossing my arms. "You make quite the pretty girl."

He didn’t respond, just continued to stare at himself in the mirror, his expression unreadable. I decided to push a little harder.

"Now for the rest," I said, pulling a matching set of panties from the drawer. "These should fit you perfectly."

He turned to look at me, his eyes pleading for mercy. But I just smiled sweetly and handed him the panties.

"No arguments," I said firmly. "Just put them on."

With a resigned sigh, he took the panties and stepped into them. I watched closely as he pulled them up his legs, the fabric hugging his hips and ass tightly. When he was done, I stepped forward and adjusted them, making sure they were sitting just right.

"Much better," I murmured, running my hands over his hips and giving them a playful squeeze. "Now we’re getting somewhere."

I reached into the drawer again, this time pulling out a pair of thigh-high stockings. They were sheer black, with delicate lace trim at the top. I handed them to him, watching with satisfaction as he sat down on the edge of the bed and began to roll them up his legs.

"That’s it," I encouraged, kneeling beside him and helping to smooth out the wrinkles. "You’re doing great."

Once the stockings were in place, I stood back up and surveyed my handiwork. He looked incredible, all dressed up in feminine attire that highlighted his slender frame. The contrast between his masculine features and the delicate clothing was intoxicating.

"Now for the final touch," I said, reaching into the drawer one last time. This time, I pulled out a short, frilly skirt. It was a vibrant shade of pink, with layers of tulle that would bounce and sway with every movement.

"Put this on," I instructed, handing it to him. He took it reluctantly, his hands trembling slightly as he held it up to his waist.

"Do I have to?" he asked, his voice barely above a whisper.

"Yes, you do," I replied firmly. "Now hurry up."

With a deep breath, he slipped the skirt over his head and let it fall around his hips. The fabric clung to his body, accentuating his curves and making him look even more feminine. I couldn’t help but smile at the sight.

"Perfect," I said, clapping my hands together. "You look amazing."

He glanced at himself in the mirror again, his eyes wide with disbelief. I could see the conflict raging within him, torn between humiliation and arousal. It was a heady combination, and I felt a surge of excitement at the thought of what was to come.

"Alright, now for the fun part," I said, pulling out my phone and turning on the camera. "Time to make a little video."

He froze, his eyes widening in panic. "What? No, you can’t—"

"Oh, yes I can," I interrupted, pressing the record button and pointing the camera at him. "Say cheese."

He stared at the camera, his mouth opening and closing like a fish out of water. I could see the fear and uncertainty in his eyes, but also a flicker of something else—something darker, more primal.

"Come on, say something," I urged, tilting the camera slightly to get a better angle. "Tell me how much you love dressing up like a sissy."

He hesitated, his face flushing with shame. But then, slowly, he began to speak.

"I… I love dressing up like a sissy," he stammered, his voice trembling. "I love wearing these clothes and feeling… feeling pretty."

I grinned, pleased with his response. "Good boy," I cooed, lowering the camera and walking over to him. "Now let’s see if you can keep that pretty little hands busy with something else."

I reached into my pocket and pulled out a small bottle of lube, tossing it onto the bed beside him. His eyes followed the movement, confusion and anticipation warring on his face.

"put this on your cock and stroke yourself," I commanded, pointing to the floor in front of me.

He hesitated for only a moment before applying the lube, his hands stroking his cock while wearing the sissy dress. I watched as he elongate his cock with pleasure.

"That’s it," I purred, unbuttoning my jeans and sliding them down to my ankles. "Show me how much of a good little sissy you can be."

I stepped out of my jeans, pulled my panties down made him lick my pussy while jacking off on camera.

"Take it," I ordered, pressing my pussy against his lips. "Suck it like the slut you are."

He hesitated, his eyes flickering up to meet mine. But I just tightened my grip on his hair, forcing his mouth open and made him lick my cunt.

"That’s it," I groaned, his tongue thrusting between me. "Such a good little sissy you are."

His lips wrapped around my pussy, warm and wet, and I felt a thrill of pleasure slides through me. I started to move faster, making him fuck me with his mouth with increasing urgency.

"Mmm, you feel so good," I moaned, gripping his hair tighter. "So tight and wet."

He stopped slightly to catch some air, but he didn’t pull away. Instead, he grabbed my ass and kept eating me.

"Fuck, yes," I growled, thrusting my pussy harder. "Take it all, you dirty little whore."

I could feel my orgasm building, the pressure mounting in my clit. I knew I wouldn’t last much longer, but I wanted to make sure he remembered this moment forever.

"Get ready," I warned, pulling out of his mouth and grabbing him by the cheeks. "I’m gonna squirt all over your pretty little face."

He looked up at me, his eyes wide and filled with a mixture of fear and anticipation. I could see the desire burning in his gaze, the need to submit and be used.

"That’s it," I whispered, my hand holding his head and making him lick me faster. "Take it, take every drop."

With a final, powerful thrust of my pussy to his tongue, I came, squirting all over his face. He gasped, his mouth opening as streams of white liquid splattered across his cheeks and chin.

"Fuck, you look so good covered in my squirt," I panted, still playing myself as I watched the last few drops ooze from pussy onto his lips.

I leaned down, wiping the liquid from his face with my fingers and smearing it across his lips. Then I pressed my thumb into his mouth, forcing him to suck it clean.

"Good boy," I murmured, pulling my thumb out of his mouth and wiping it on his skirt. "Now stay there. I’m not done with you yet."

Part 2? just let me know