Abbie's Guide To Becoming A Sissy

Read the story

5 chapters · 5667 words · Read 0 times

Abbie discovers that Ewan is a wannabe femboy. She catches him browsing lingerie on his phone, and helps him dress pretty, use a dildo, and eventually pegs him before they both have a threesome with a bisexual man.

Chapter 1: Introduction

Abbie stood in the kitchen, humming softly to herself as she meticulously sliced ripe tomatoes for their dinner. Her gaze drifted towards the living room, where the glimmer of her laptop screen shimmered invitingly. With a knowing smile, she placed the knife gently on the countertop and made her way towards the enticing light.

As she neared the computer, her heart surged with curiosity and anticipation. The screen illuminated her face, revealing the sultry features and sparkling green eyes that captivated those fortunate enough to cross her path.

Abbie scanned the open browser window, her eyes widening at the unexpected sight. Lingerie ads filled the screen—an array of colorful panties, lacy bras, and delicate stockings tantalizing her senses. She knew each piece was carefully selected by the one person she least expected to see them on: Ewan.

"Ewan?" she called out, trying to gather her thoughts. "You home?" The sound of rustling paper from the other room answered her question. Her heart raced in her chest as she took a deep breath, preparing for what lay ahead.

She heard him shuffling nervously behind the door, and with a gentle touch, she pushed it open. There he stood, hunched over the computer, his face flushed and eyes darting back and forth between Abbie and the screen.

"Hey," he said awkwardly, "I didn't know you were there. I just... I just wanted to look at some stuff."

Abbie smiled warmly, her voice soft but confident. "It's okay, Ewan. I saw what you were looking at.

" Abbie stated calmly, placing a reassuring hand on Ewan's shoulder. "I understand. And you shouldn't feel ashamed. It's natural to have these feelings."

Ewan stared blankly at the floor, feeling exposed and vulnerable. "How could you understand?" he mumbled weakly. "I mean, I'm a guy... It's not like it's normal or anything."

Abbie arched an eyebrow, her gaze steady and unwavering. "What do you know about 'normal'?" she challenged him.

"Normal is subjective, and what may seem strange to one person can be liberating and empowering to another."

Ewan gazed up at Abbie, his eyes welling with tears. "You really think so?" he meekly asked. "That I can, you know, explore my feelings further?"

Abbie nodded confidently, her voice soothing and reassuring. "Of course, Ewan.

" Abbie replied softly, her emerald eyes filled with understanding compassion. "I've known you for quite some time now, and I know how brave and open-minded you can be. Embracing our authentic selves isn't easy, trust me. But if we don't take risks, we never truly live. This is something that resonates deeply within us both—we both enjoy exploring boundaries and seeking pleasure."

Ewan listened intently, his gaze locked onto Abbie's mesmerizing green eyes. He swallowed hard, trying to muster the courage to voice his deepest fears.

"But people won't understand. They'll judge me, call me names..."

Abbie reached out and cupped his cheek, her fingers brushing against his skin like a tender caress. "Let them," she whispered fiercely. "If they can't accept you for who you truly are, then they aren't worth your time."

Ewan looked down, a hint of uncertainty clouding his dark eyes. "And what about you?" he finally managed to ask. "Will you still respect me, even though I'm...

I'm scared

," Ewan finally admitted, his voice a whisper.

Abbie gazed at him, the corners of her lips curling up slightly. "Don't be," she said firmly. "There's nothing to fear when you're acting authentically. People might stare, gossip, but ultimately, they're envious of your bravery."

Ewan looked skeptical, but Abbie could sense a change in him. He was beginning to soften, to let go of the rigid shell he had built around himself.

Abbie's confidence and openness seemed to resonate within him, driving away the fear and judgment that had been haunting him for years.

"Abbie," he began tentatively, "would you... would you ever consider..." His voice trailed off, the words seeming too impossible to utter.

"Consider what?" Abbie prompted gently, watching his face closely. "I need to know where you stand before I promise anything."

Ewan bit his lip, gathering his courage. "Would you accompany me...

as in, um, you know," Ewan stammered, his hands nervously fidgeting, "as in... as in a friend?"

Abbie studied Ewan's face, her eyes tracing every line of anxiety etched upon it. She could tell he was struggling to find the right words, the right way to phrase his request. Finally, she decided to give him a nudge toward the truth.

"So, you want me to be your friend and guide as you explore your femininity?" she asked, her tone soothing yet firm.

Read on DreamPress

Write your own erotic story with AI