“Jack wouldn’t remember to water the plants even if he was there,” said Steph, laughing. “At least I can trust you.”
Steph was right inasmuch as I could be trusted to look after the place whilst both she and Jack were away, but sadly I couldn’t trust myself to keep away from her things. Steph was particularly girly, and had an enormous collection of clothing of all kinds, as well as loads of accessories, make-up, and even wigs from her former stint as an amateur actress.
At twenty-two years old I was what one could consider a skinny guy, though not at all bony. I looked rather androgynous really, which helped me inasmuch as I enjoyed dressing up as a girl for private pleasure. I say private pleasure because I had never plucked up the courage to go out in public. In fact, I had never even told anyone about my cross-dressing. I also say private because the act of dressing up as a girl invariably resulted in sexual pleasure through masturbation. Ever since I was a young boy I had cherished the look and feel of soft feminine underwear adorned with pretty bows hugging tightly at my cock.
---
I stood there in Steph and Jack’s single-bedroom apartment, looking out through the window at the courtyard, breathing heavily. I'd known ever since I’d accepted to take care of the place that I wouldn’t be able to resist. So far I had managed to limit myself to sneaking a look in Steph's underwear drawer and only briefly opening the wardrobe to see her collection of dresses. That was three days ago.
I turned around and looked down at the bed. My cock was already quivering at the thought of wearing her delicately embroidered yellow summer dress, with its frilly white hemline. I told myself that I needed to remember exactly where I had found it, and made a mental note.
I pulled the curtains shut and then stripped my clothes off before slipping the dress over my head and smoothing it down over my thighs. The back zip was a bit tricky at first, but once I had managed to pull it up, the fit was almost perfect; except for the fact I had no breasts. I thought that Steph was probably more or less the same size as me - except for my slightly taller height - but I hadn’t expected the dress to feel so natural on me. My shaft shot straight up, causing an annoying disturbance to the image before me as I looked at myself in the full-length mirror. I felt conflicted by seeing myself as a girl with an unwanted protrusion, and yet that protrusion was also giving me great pleasure. I knew there was only one way to make it go away.
Taking great care not to disturb anything, I reached into her lingerie drawer and took out a beautiful pair of silky white ruffled panties and matching ruffled bra, as well as a few pairs of silk stockings to pad the breasts. Quickly, I unzipped the dress, slipped into the underwear and put the dress back on. It fit perfectly now, my fake tits amply filling the breast pockets. In a frenzy, I rushed over to Steph's wardrobe and pulled out a curly blond shoulder-length wig from one of the boxes, and put it on.
The excitement was building; my cock was dribbling pre-cum into Steph’s pretty little panties as it tried desperately to fight its way free.
Seconds later, the girl in the mirror was smiling back at me. I knew her well. She had given me much pleasure over the years. I looked her in the eyes while grasping tightly at my throbbing rod through the silky material. She was the most exciting girl I had ever known. I watched her writhing about while I rubbed my swollen shaft, glancing at her delicate curves and admiring her femininity. She reached up and grabbed her left breast, rubbing it seductively. I could sense her every move, the softness of her delicate mound being teased beneath my wanton hand. I watched in awe as she squeezed and rubbed her titties, taunting me. I wanted her so badly.
I leaned in to the mirror to kiss her, desperate to connect. We had made love many times before, and yet we had never felt the warmth of each other’s bodies. She loved to tease, and I loved to watch her. She had a way of showing off just enough of herself to get me totally excited, like turning around and lifting her dress, just enough to show off the beautiful curves of her tight little butt, or to stand facing me and show me the tops of her milky white thighs.
I especially liked it when she wore stockings and a garter belt beneath her dress or her skirt. She was a real mistress, knowing just when to turn it on and off.
I stroked vigorously at the head of my shaft as she pulled away from my vain attempts to kiss her. She played with her breasts, stroking herself, running her hand down her stomach and across her thighs, lifting her dress, and then returning to touch her breasts. She did this a few times, until finally she raised her dress enough for me to see her bulging cock encased in frilly white panties, the head of her shaft popped out over the top, and the tip spurting a steady stream of sticky white cum in my direction. I gasped as I watched, my balls pulsating deeply and quickly draining.
---
The following morning I lay in bed, remembering the events of the previous day. Even though I’d had to take Steph’s dress and panties home to clean them, and the fact that I felt somewhat ashamed of having violated her privacy, I wanted more. The sense of pleasure outweighed the guilt, as I discovered later that evening.
---
I stood in front of the mirror, putting the final touches on my makeup. The lash curlers had worked out better than expected, and despite my nervous hands, I had accomplished a delightfully vampish look, complete with sultry ruby red lips. I smiled and admired my alter-ego, the girl who was me, with her long dark curly hair (a wig), wearing her black velvet mini-dress and thigh-high stockings. It would be almost a week before Steph came home, and I needed to take advantage of that. Several more evenings of fun lay ahead.
I went to the bedroom and flopped down on the bed in front of the television, imagining what it would be like to be Steph. I ran my fingers up and down the stockings, feeling the thread. My leg tingled in a sensual way, and I wondered if Steph would feel the same way if I stroked her legs like that. I pushed my hand further between my thighs and rubbed my inner leg. The sensation of the stocking material caused my shaft to stiffen, some pre-cum dribbling from the head. “Of course she wouldn’t feel exactly the same, but possibly similar, at least in her mind.” I said to myself.
I felt contented with idea that she possibly felt the same as me, and I was not at all inclined to jerk-off again. “It’s so unladylike!” I thought to myself.
As I lay there, oblivious to the TV programme playing on low volume and feeling contented with my evenings accomplishments, I drifted into a deep sleep.