I caught her eye as I walked across the city square. I looked up from my phone and her eyes met mine with a warm gaze. We both had a hint of a smile and broke the gaze as soon as it started. My afternoon felt lighter and the time flew by. I kept thinking about that fleeting glance, a shiver ran up my spine at the thought of improbable scenarios.

I threw my keys on the side table in my hallway after locking the door and kicked off my heels. Even after two years of daily wear, the relief of kicking them off after a full day never got old but I wouldn’t change it; my heels made me feel powerful and “me”. I judged a good pair by a combination of the clack of the heel tip and the comfort to my feet. The sexy but sensible ratio. As enjoyable as 7-inch stilettos are, I had yet to find a pair I could last a workday in. I hadn’t seen what the mystery woman was wearing on her feet, a tan jacket was all I remembered.

I hung my own jacket on the hook and walked into my bedroom. “I really must start clearing up before work,” I chastised myself as I surveyed the mess from this morning.

A dress, two skirts, a blouse, and a pair of tights littered the floor along with my nightwear. After picking up a takeaway on the way home, at least I didn’t have to cook. I started running a bath and tidied the room, I’d been thinking of a long soak all afternoon. I could feel a stirring in my panties.

As I unzipped my hip-hugging pencil skirt, the urge grew more. I unbuttoned my blouse and dropped it on the floor. Stepping out of my skirt and pulling down my tights, I caught sight of myself in the full-length bathroom mirror.

I still do a double-take when I am in my lingerie, the woman in the mirror didn’t always match what I thought should be there.

“You’re sexy, you’re a woman, you’re powerful,” I said to myself in the mirror. I walked over to the bath, unclipped my bra and breast forms, slipped down my and pants, and untucked myself.

“Fuck.”

I took my growing member in my hand, reached for some lube in the bathroom cabinet, and collapsed on my bath rug.

After showering, I put on a cute silk camisole and shorts, tidied up my bedroom, and then wandered through to the living room for my evening in fluffy rabbit slippers.

I enjoy living by myself, I can be myself and not double-check every small piece of life. I’d lived as Imogen for a number of years now, my friends were very welcoming and work equally so. What started as casual cross-dressing and a wank turned into my lifestyle. I was still exploring who Imogen was and what came next. I sorted my outfit for the next day, checked my bag, and retired to bed for the night. There was a comfortable routine to my life which was very welcome.

The next morning I sorted my hair and makeup, then put on my clothes for the day. Trouser Tuesday as I called it, a secret nod to my former self I liked to think. A full lace thong did a great job of no VPL when I pulled up the arse hugging maroon trousers. I buttoned up the high-waisted loose-legged piece, enjoying the fabric as it brushed against my bare shaved legs and flared open from the thighs down. I buttoned up a plain black blouse and matching blazer for my jacket, the lace of my bra making a pattern through my blouse.

“That’ll excite the old man,” I laughed. The old man being the office boss, getting on in age but oddly still a flirt with the paralegal he knew to be a future transsexual. He knew I could shut him down for any possible harassment, but it was innocent and excited me to know he might fantasise about me. I’d caught him with a hardon more than once.

My trouser hem was brushing against my hardwood hall flooring so I knew I’d need to raise it up today. I pulled a pair of tan heels; pointed stilettos with barely enough leather to contain my feet, but a heel click to set a cock straight. I grabbed my bag and my tan coat, hoping to make an impact if I ran into the same woman from yesterday. Touching up my lipstick, I headed out the door with a strong strut… Click click click.