SISSY & FAMILY - 1

17 JANUARY

Dearest Diary,

Today Mistress Evelyn surprised me with a new outfit – a darling little maid's dress in the softest shade of lavender! The moment I slipped it on, all those layers of ruffles and lace, I felt like a princess in a fairytale. Mistress helped me with my hair, teasing it into soft, bouncy curls that cascaded around my shoulders, and she even let me wear a touch of her favorite lipstick - a shade called "Sunset Kiss" that makes my lips look plump and inviting.

I couldn't resist twirling in front of the mirror, the skirt of the dress swirling around my legs like a lavender cloud. I felt so pretty, so feminine, so utterly unlike the person I used to be. It's amazing how clothes can transform you, how they can unlock parts of yourself you never knew existed.

Mistress Evelyn watched me with a knowing smile, her eyes twinkling with amusement. "You look absolutely delicious, darling," she purred, and I felt a blush creep up my cheeks. Her praise means everything to me. I want to be the perfect sissy for her, to fulfill her every desire, to be the embodiment of her fantasies.

Later today, she's taking me shopping for new shoes and stockings. I can't wait to see what treasures we uncover!

... We didn't go shopping for shoes after all. Mistress Evelyn decided it would be much more fun to stay home and play dress-up! She brought out a whole box of treasures from her own collection - stockings, garter belts, and the most divine pair of sparkly heels I have ever seen.

After I helped her undress, her eyes twinkling with that familiar mischievous glint, she instructed me to try everything on. It was like a fashion show just for her, a secret performance for her eyes only.

Oh, and I have to tell you about the panties she chose for me! Lavender satin, trimmed with delicate lace – they feel absolutely decadent against my skin. She says they make my bum look especially cute, which made me blush, of course. But a happy blush!

She helped me put on the garter belt and stockings, her touch firm yet gentle, her fingers lingering on my skin just a moment longer than necessary. When she stepped back to admire her work, her eyes raked over my body, lingering on my legs encased in the sheer nylon. "Exquisite," she breathed, and I felt a thrill shoot through me.

Then came the shoes - sparkly, silver heels that make me feel taller, more powerful, more womanly. They pinch my toes a bit, but I don't mind. The pain is a small price to pay for the joy of seeing Mistress Evelyn's eyes light up with pleasure.

I know I shouldn't be thinking this, Diary, but... I kind of like the way these clothes make me feel. Pretty and delicate, but also powerful, like I can conquer anything in these heels. Maybe that's part of what Mistress sees in me, what she's trying to bring out. And I have to admit, I'm starting to enjoy the journey.

...The rest of the day was a blur of excitement and anticipation. Mistress Evelyn let me model all my new finery for her, walking back and forth, twirling, and posing just like she showed me. She even let me touch her dress – a sleek, black gown that hugged her curves like a second skin, the fabric shimmering with tiny sequins. I imagined what it would be like to be wrapped in that dress, to feel its luxurious texture against my skin.

Then, she asked me to do something unexpected. She wanted me to kneel before her, to kiss her leg, to worship her. It felt strange, humbling, but also thrilling. The feeling of her smooth skin against my lips, the scent of her expensive perfume filling my senses, it was intoxicating.

As I knelt there, gazing up at her, I realized something: I didn't just want to wear her clothes, I wanted to be her. I wanted her power, her confidence, her absolute control.

She saw the longing in my eyes, I know she did. And as she leaned down, her fingers tracing a line along my jaw, I knew this was just the beginning of my journey.

I can't wait to see where it leads.