Timmy and his daddy go to a family do…
The lacy thong was chaffing a little, but Timmy managed to ignore it as we walked into the grand ballroom. He looked adorable in the frilly little dress and makeup I had picked out for him, his cheeks still a bit pink from the blush. The wedding was a whirlwind of color and sound, with relatives we hadn’t seen in years all dressed to the nines.
“You look beautiful, Timmy,” I whispered, giving his hand a gentle squeeze. He glanced up at me, his eyes sparkling with excitement. “Thanks, Daddy,” he murmured, his voice just a little higher than usual.
The reception was in full swing, the air thick with the scents of flowers and expensive cologne. The chatter of adults and the laughter of children filled the grand ballroom as we made our way to our table. Timmy’s eyes darted around the room, taking in the unfamiliar sights and sounds.
As the dinner was served, the conversations grew more muted, and the clinking of silverware against china became the background music to our evening. Timmy picked at his food, his gaze frequently returning to my plate. The curiosity in his eyes was unmistakable, and I knew what he was really hungry for.
“Daddy,” he whispered, leaning into me, “I need to use the bathroom.” His voice was filled with a sense of urgency that didn’t quite match the situation. I nodded, and we excused ourselves from the table.
Once outside in the cool evening air, Timmy took my hand and led me away from the bustling reception. “Where are we going?” I asked, slightly confused. He just giggled, his eyes sparkling with mischief in the moonlight.
He stopped in a secluded part of the garden, the tall hedges providing us with a private little nook. The scent of roses filled the air, mingling with the sweet aroma of his sister’s perfume that still clung to him. “Here,” he said, turning to face me with a shy smile.
Without a word, Timmy dropped to his knees, his little dress pooling around him like a puddle of silk. He reached for my pants, his small, trembling hands fumbling with the zipper. I helped him, my heart racing as I felt the fabric part and my cock spring free into the cool air.
Timmy looked up at me, his eyes filled with a mix of excitement and apprehension. He licked his lips, and I could see the desire in them, the want to taste me again. I stroked his cheek gently, feeling the softness of his skin against my thumb. “Go ahead,” I murmured, giving him the permission he so desperately sought.
With a eager whine, Timmy leaned in, his mouth open wide as he took my cock in. He was sloppy at first, his inexperience showing as he tried to fit all of me in his mouth. He gagged a little, his throat contracting around the head of my cock, but he pushed through, his eyes watering with the effort. His saliva coated my shaft, making it slick as he pulled back and then took me in again, deeper this time.
The sound of his muffled moans and the sight of him in his sister’s dress with my cock in his mouth was almost too much to handle. I had to bite my lip to keep from coming immediately. He was like a greedy little whore, his eyes never leaving mine as he sucked with a passion that belied his age. His cheeks were hollowed out, and his tongue danced around the shaft, exploring every inch of me.
Timmy’s small hands found their way to my balls, playing with them gently. He rolled them in his palms, his fingers exploring the soft, sensitive skin. The sensation was exquisite, and I had to resist the urge to grab his head and fuck his face. His touch was tentative at first, but as I moaned in pleasure, he grew bolder, tugging and squeezing them just enough to send bolts of pleasure through my body.
I placed my hand on the back of his head, guiding him, showing him the rhythm that I liked. His eyes never left mine, full of trust and yearning. The moon cast a soft glow over us, painting his dress in a silvery light that made him look even more ethereal. The sound of our breathing and the occasional smack of his lips against my shaft filled the quiet night air.
Timmy’s sucking grew more confident, his movements smoother as he took more of me in. His cheeks were rosy with exertion, and his eyes watered slightly, but he didn’t stop. He was eager to please, eager to learn, and I couldn’t help but feel a twisted sense of pride in his determination.
I stroked his hair, guiding him gently, whispering words of encouragement that seemed to spur him on. His tiny hand gripped the base of my cock, his other hand still playing with my balls, and I knew I wouldn’t last much longer. “Timmy,” I groaned, “I’m going to cum.”
He pulled back slightly, his mouth slick with saliva and precum, and nodded eagerly. “Can I swallow it?” he asked, his voice a mix of innocence and lust. I nodded, feeling a strange sense of excitement that he was so willing to take this step with me.
The tension grew as I felt myself getting closer to the edge. Timmy’s eyes never left mine, his focus unwavering as he took me back into his mouth. His little hand pumped faster, and his other hand squeezed my balls in a way that was surprisingly pleasurable. I could feel the pressure building, my cock swelling with each passing second.
With a growl, I pushed into his throat, watching as his eyes watered and his nose squished against my pelvis. He gagged, but I held his head firmly, not letting him pull away. His throat convulsed around me, the sensation unlike anything I had ever felt before. His nails dug into my thighs, but I didn’t care; the mix of pain and pleasure was intoxicating.
Timmy’s hands gripped me tighter, his little body shaking with the effort as he tried to keep up with my rhythm. His cheeks were tear-stained, but the look of determination in his eyes was unmistakable. He wanted this, needed this, and I was going to give it to him.
With a final thrust, I released my load into his eager mouth, watching as his throat worked to swallow down every drop. His eyes watered, but he never pulled away, taking my cum like the good little slut he was becoming. I could feel his body tense up as he struggled not to choke, and I knew that this was a moment he would remember for the rest of his life.
As my cock grew soft in his mouth, I pulled him to his feet, his dress still hiked up around his waist. “You did so well, Timmy,” I murmured, kissing his forehead. He looked up at me with a mix of satisfaction and excitement, his eye make-up running.
With a playful smirk, Timmy turned around and lifted his skirt, exposing the little hole. His asshole was a perfect little rosebud, winking at me from between his cheeks. “Do you like it, Daddy?” he asked, spreading his cheeks apart to give me a better view.
I couldn’t believe the transformation in him. The shy, scared boy from earlier was now a confident, eager little whore, eager to please me in every way. “I do, Timmy,” I said, my voice thick with desire. “You’re a natural.”
I stepped closer, positioning myself behind him. His skin was soft and warm, and I could feel his heart racing as I spread his cheeks apart. His asshole was tight, inviting, and I knew that I had to be gentle. I reached down, my hand shaking slightly, and rubbed a finger against his hole, feeling it give way slightly.
Timmy whimpered, his body tensing with anticipation. “Ready?” I asked, and he nodded, his eyes fluttering closed. I leaned in and spat on his asshole. The wetness added to the slickness, and I lined up my cock with his hole.
With one firm push, I felt the resistance give way, and I slid into him. His gasp was muffled by the fabric of his dress, and his body stiffened. “Easy,” I whispered, giving him a moment to adjust.
He nodded, his breath coming in quick, shallow pants. I began to move, my cock sliding in and out of his tight little asshole with a wet squelch. The sound was obscene in the quiet of the garden, but it only served to turn me on more. His body was so warm and welcoming, and I could feel him loosening up with each stroke.
Timmy leaned back into me, his hands braced against the brick wall of the ballroom. He was taking me so beautifully, his small frame shuddering with each thrust. I reached around and found his hard little cock, stroking it in time with my movements. His whimpers grew louder, and I knew he was close.
“You’re doing so good,” I murmured, my voice strained with the effort of holding back my own climax. I leaned in closer, my teeth grazing his ear. “You’re going to make me cum so hard in your ass, baby.”
Timmy’s body tensed, and I knew he was just as turned on by my words as he was by the feeling of my cock stretching him open. He pushed back into me, urging me to go deeper, harder. I complied, my strokes becoming more forceful, my grip on his cock tightening.
The slap of skin on skin grew louder, mixing with our heavy breathing and the occasional moan. His little asshole was like a vice around my cock, clenching and unclenching with each thrust.
Timmy’s whimpers grew more frequent, his breath hitching in his throat as I hit that perfect spot inside him. His body was trembling, his legs shaking, and I knew he was close to cumming. I reached around and pinched his little balls.
With a high-pitched squeal, Timmy’s body went rigid, and I felt his asshole clamp down around my cock as he shot his watery little load. It was a beautiful sight, his small dick pulsing in my hand, spurts of cum landing on the silky fabric of his dress. The sensation was too much for me to handle, and with a roar, I emptied myself into his tight, warm ass.
Timmy’s body went limp, his knees giving out slightly as I pulled out, my cock still pulsing with the aftershocks of my orgasm. He turned to me, his makeup smeared and his dress a mess, but he was smiling. He dropped to his knees, eager to clean me up. I watched as he took my cock into his mouth, his tongue lapping up the remnants of our shared pleasure. His eyes were closed in concentration, and I could see the pride in his expression as he swallowed every drop.
Once he was finished, I helped him to his feet and adjusted his dress, smoothing out the wrinkles as best as I could. “We should get back to the party,” I said, trying to keep the tremor out of my voice. He nodded, his eyes sparkling with excitement.
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