She wasn’t super-tall for a woman, but she stood slightly better than 5’6” in her sneakers. When I saw her, it was always at work because she was the building’s custodian. She was either a very light-skinned black woman or biracial. When she spoke, her voice was on the higher end of the range — not quite child-like, but just on that edge. I figured her to be in her mid-twenties.
She always wore jeans and the T-shirt provided by the company she worked for. Her jeans were usually snug, but not so tight as to make her job difficult. Her t-shirt was always worn loose, but I guessed her tits were a 38C. She never wore makeup, and she kept her shoulder-length dark hair pulled back in a tight ponytail.
I never really lusted after her or fantasized about her like I had other custodians over the years. I learned a long time ago about dipping your pen in the company inkwell — and I always applied that rule to contractors as well. All of that to say I didn’t spend a lot of time ogling her; but I did look occasionally — especially when she bent over to empty the waste bins.
I always greeted her warmly and thanked her every time she emptied my trash. My boss had taught me to know and respect “the help.” Her name was Katie and after nearly three months on the job we had just reached the “friendly banter” stage.
Her rounds brought her through our part of the building around 3:30 in the afternoon. That meant that she had moved on well before the end of the day. Sometimes when the job required me to work late, I would be the only one on our floor.
This worked out well for me since I am a closet cross-dresser. My wife at one time supported my “little habit,” but had cooled over the years. Mainly, I dressed and played with my sissy things while on trips for work. I had dabbled in chastity and loved crotchless panties, babydoll nighties, and realistic dildos buried in my hungry boi-pussy.
After hours was my favorite time to slip into the men’s room with my latest purchases and try them on; I would primp and preen and sometimes take pictures to post on my blog. It always fueled my masturbatory fantasies to imagine what would happen should another man come into the bathroom while I was in there and catch me dressed like a sissy slut!
Over the years, I had played out every fantasy in my head — being forced to suck cock, getting face-fucked, being fucked in my ass, getting spit roasted, being gang banged — every sissy fantasy possible. In retrospect, I was wholly unprepared — mentally at least — for the reality that was about to envelope my life.
My wife was out of town visiting her family out of state. Since I was left to my own devices I was not in a hurry to get home. I knew anything I did at work after hours tonight would not be interrupted by a text from her asking where I was and when I would be home. I should have left on time and done my dressing at home, but the sissy soul wants what the sissy soul wants when the sissy soul wants it.
I had just received a new package today, full of two new sets of sexy lingerie and a new dildo. I was looking forward to getting myself alone with them and decided the added thrill of dressing in the men’s room at work (thus more fuel for the sissy-fantasy fire) was worth any extra risk. The men’s room had been remodeled when we moved onto this floor and the stall walls had been taken down so it was just one big room with one toilet and one wall urinal. Handrails ran behind as well as beside the toilet, and there were two sinks in the vanity.
Because I had all the time in the world, I went almost all-out. First was rolling my lace-top black stockings up my legs. The outfit didn’t have garters so I had to settle for stay-up stockings. There was always something so sensuous about putting on a pair of stockings. I normally liked RHT Cuban-heel seamed stockings, but for this sissy, any stockings are sexy stockings! I had not brought my heels, but I knew the floors were recently cleaned so I felt okay without them.
Next, I got out my chastity cage — a sissy pink Holy Trainer IV. I fitted the ring over my cock and pulled my balls through. Putting on a chastity cage always made me hard so I had to work fast. I used a small dab of hand soap to lube the tube and slid my shaft into it. I had to force it a bit as I positioned it to slide the lock into place. I locked it, leaving the keys on the counter.
The chemise was next, in pale sissy pink of course! The underwire cups were trimmed with a wide band of black lace that ran into extra-wide shoulder straps of black lace and pink satin. Another wide band of black lace ran under the bra cups as well and around the side. I paired the chemise with a pair of pink microfiber bikini panties. They didn’t exactly match, but they were, in fact, pink!
I admired my reflection in the mirror and lifted the hem of the chemise to reveal the outline of my cage in the front of the panties. I was leaking pre-cum and staining the front of the panties. I had been dressed and fawning and preening in the mirror for about fifteen minutes when the urge to urinate hit me.
Like a good little sissy, I lowered my panties and sat down on the toilet. I was relieving myself, feeling the liquid coming from the tip of my cage to make a tinkle sound in the bowl. Suddenly, I heard the door handle being turned! I quickly glanced over to the door. Had I remembered to lock it?
My heart leaped into my throat as I realized I had not! I tried to cry out, “I’m in here!” My voice was more of a croak and didn’t carry. Katie walked right into the bathroom, catching me on the toilet.
“Oh, I’m so sorry, honey,” she started. Then, “Wait a minute. This is the men’s room! What are you doing in here . . . .” Her voice trailed off as she recognized me.