Chapter 3: Changing
Trying on his first item of clothing from the vast new selection Tyson had purchased for him, Oli felt giddy with excitement and horniness as he pulled the sheer thigh high nylon stocking up his now silky smooth leg. He could feel the cold material against his skin as the stocking slipped up his thigh, his eyes glued to the mirror, watching the transformation unfold. He let out a sigh of relief as the garter belt finally clipped into place around his waist, holding the stockings securely.
He turned to look at himself in the mirror, seeing the person he had always dreamed to be. He felt a rush of exhilaration, a sense of freedom and liberation. He was finally letting go of the boundaries he had placed around himself, and it felt incredible. He took a step back, admiring the way his body looked in the new outfit. Tyson handed him a matching black lace thong ready for his transformation to continue. The thong snugly pulled into place was followed by the pink mini skirt, Tyson’s favourite, and a shiny little pink satin crop top to match. Oli looked at himself in the full-length mirror in the bedroom. The transformation was almost complete. He looked back at Tyson who had moved to sit on the bedroom chair, his eyes lit up with satisfaction and a hint of mischief. He pushed up his glasses and smiled, “You look stunning, sissy. Now, let’s make this face match the body.”
Oli’s heart skipped a beat. He knew what was coming. He had never worn makeup before, never even tried to apply it before. He didn’t know where to start. Tyson noticed his apprehension and offered a reassuring smile. “Don’t worry, baby girl. I’ve got you covered.” Tyson rose from the chair and walked over to the vanity, opening the drawer and pulling out a variety of makeup products.
Oliver furrowed his brows, a mix of apprehension and curiosity playing across his face. “I’ve got a face to paint,” Tyson said with a playful wink, “and I’m not talking about a clown here.”
Oliver blinked, unsure of what to expect. His heart was pounding in his chest like a drum, each beat echoing the word “sissy” in his head.
Tyson wasted no time, musing to Oli that his years of theatre camp over his summer holidays were finally coming in handy as he almost expertly painted Oli’s once masculine face into a soft, feminine glow that any girl would be pleased to wear. Oli watched, mesmerised, as Tyson lightly dusted a shimmering eyeshadow onto his eyelids, blending expertly to create a soft smoky look. He carefully lined Oli’s lashes with a dark, defining mascara, accentuating Oli’s already long and thick lashes. A touch of highlighter on the cheekbones and cupid’s bow, and Oli’s face looked as if it had been kissed by the golden rays of the sun.
Oli hardly recognised himself in the mirror, his reflection staring back at him with wide, curious eyes.
He reached up, touching his cheek, feeling the smoothness of the foundation, the softness of the blush. The sensation was both foreign and exhilarating. Tyson stepped back, admiring his handiwork, a smug grin on his face. "What do you think, sissy?" he asked, his voice brimming with pride.
Oli bit his lip, trying to find the words to describe the swirling emotions inside him. "I... I look different," he finally said, his voice barely above a whisper.
Tyson chuckled, ruffling Oli's short dark hair. "That's the point, dear. You're supposed to look different. You're my little sissy now, remember?" Tyson replied, his voice as warm and comforting as his touch. He pulled Oli to stand up, taking his hand and leading him towards the bedroom door. "Let's go have some fun, shall we?"
Oli's heart pounded as he followed Tyson into the living room. The high ceilings and open spaces suddenly felt claustrophobic, the minimalist furniture and erotic art did little to calm his nerves. The apartment was bathed in the soft, warm glow of the setting sun, casting long, dramatic shadows across the room.
Tyson led Oliver to the couch, the leather creaking slightly as they sat down together. Tyson's hand rested on Oliver's thigh, his fingers tracing idle patterns on the shiny fabric of the iridescent pink mini skirt. Oliver couldn't help but squirm under his touch, a mix of arousal and apprehension coursing through him.
Tyson leaned in close, his breath hot on Oliver's ear. "You know, your stories really got me excited Oli, you have quite the wild imagination" he murmured.