LGBTQ+ | Slice-of-life | Voyeurism | Masturbation
Pro Bono — Part 1
A Tale of Transsexual Voyeurism
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There I was again, working late. I spend way too much time at the office. I’m a lawyer at Wilkins & Stein, a prestigious law firm, but the office I work in is a part of their pro bono operation, which means we’re tucked away in a less desirable part of the city. The whole thing is just one big tax write-off, but we do good work here regardless. A lot of my colleagues consider the position a punishment and not a privilege, so they don’t do their best work — or their best work just wasn’t that good to begin with. Since I’m one of the few people who actually gives a damn about the job, I find myself spending late nights at the office checking on other people’s work, or sometimes just plain doing it for them. I’d complain, but the truth is I love my job. And when I leave the office, it’s to go home to a drab, empty apartment and an equally lacklustre social life. So I might as well be here doing something worthwhile. Right?
Besides, during the days the place is packed with empty-suit lawyers who act like they’re royalty. Even the paralegals seem to think they’re too good for this place — except the ones who make it seem like they’re doing hard time.
I had just finished correcting a particularly poorly written brief when the janitor poked his friendly, bearded face through my doorway. He would be finished cleaning up by now and about to lock the place up. Even though most of the snobs who worked here showed no appreciation for his work or barely even acknowledged his existence, he kept his spirits up. I admired him for it.
“G’night, Miss Williams,” he said.
“Please, Aleksy, I’ve told you to call me Aisha. We’ve worked together half a decade.”
“Sounds a long time when you say it like that.”
“Maybe it is. No need to clean my office tonight, I’ll just mess it right back up. It’s going to be a long one,” I said and nodded towards the pile of folders on my desk. “Now get home to your wife.”
Aleksy nodded and smiled. “That’ll be nice, Miss — Aisha. Ma’am. Thanks.”
A few years back he had loaned me a spare key card so that I could let myself out of the building after hours without setting off the alarm. In return, I would sometimes log him out of the system so he could head home early. Company policy was he had to stay until the minute he got off, but I know he takes pride in his work and won’t leave until the place is spotless.
I did envy him a bit for having someone to go home to. I had never met his wife, but it seemed from the way he spoke of her that they genuinely enjoyed each other’s company. And sometimes I envied her for having found such a kind and caring man. Even though he was twenty years my senior, I found Aleksy more attractive than any of the men I had been briefly involved with on my increasingly desperate stints of dating. The last guy had been self-centred and smug and had left me unfulfilled both in conversation and bed. Judging by the way he spoke of his work at a local bank, those weren’t his only areas of incompetence. But he was confident, and for a man that’s often enough.
I listened to Aleksy’s footsteps fade away down the corridor, then I sighed and set myself back to work.
I looked up from my computer screen. The stinging in my eyes and the crick in my neck told me I had zoned out, hyperfocused on the work. Indeed, over half of the briefs lay stacked in the ‘done’ pile, even though I barely remembered doing the work.
My body screamed for a break, so I stood up and stretched out by reaching my hands towards the roof and getting up on my toes. Then I dropped my arms and clasped my hands behind my back, arching my arms backwards. There was a satisfying click from my neck. If I was going to keep this up, I would have to get back into a habit of regular physical exercise, or that crick in my neck was going to become a permanent fixture. I drank the last of my stale coffee and picked at the pastry crumbs left on a napkin on the desk. I could do with a better diet, too.
I grabbed my water bottle and walked over to the window. This part of town was mostly run-down offices, but I was on the top floor, just high enough to see the city over the closest buildings. The city lights spread out before me, an artificial constellation of LED and neon.
In the nearby streets, most of the lights were out at this time of night. Dim street lights battled the darkness, aided by the occasional passing car and an around-the-clock corner shop that catered to an odd crowd of late-night strays, me among them. A few offices were still lit up by my fellow workaholics. I knew the repeat offenders well: third from the left on the fifth floor across the street, corner office on floor three down by the junction, and two more further down the street. An anonymous union of people too lonely, sad, or desperate to go home.
But tonight a window straight across the street was also lit up. It was on the top floor, which meant I could look straight down into it. The street was quite narrow so the room wasn’t all that far away, and I could see a young blonde woman in a black tube skirt leaning against a copying machine. Her posture oozed boredom. The copier cast a wan green light as it ran back and forth, projecting an eerie play of shadows on the walls.
While the machine worked its way through a huge pile of documents, the woman casually flipped through something on her phone with her thumb. Occasionally she glanced up at the copying machine, and I could just about make out the exasperation on her face. Probably a paralegal; they always got stuck with the boring grunt work and often had to pull all-nighters. After another look at the copy machine and the huge pile of papers it was working its way through, she pulled over a chair to slump into, her attention back on the phone.
I was about to walk back to my own pile of papers when the woman moved her hand up to her breast and started caressing it. Even though all I was doing was looking out my office window, I felt like I was intruding on her privacy. The woman’s white shirt stretched tightly over her petite chest, her nipples poking through. The woman began pinching at a nipple while she kept swiping on her phone, and now it was obvious what she was looking at. I could feel my face getting warm. My instinct was to draw the blinds and walk away, but something made me stay still. Sexually, I had always been what people referred to as ‘vanilla’, but I suppose I had never properly explored that side of myself. Still, I assumed it was morbid curiosity that stopped me from walking away.
The petite woman was unbuttoning her shirt now, exposing pale cleavage and a purple lace bra. She caressed the exposed top of one breast absent-mindedly while her thumb flipped over her phone impatiently. I was surprised to find that watching her quickened my breath. Surely, that was from embarrassment or shame.
The show went on, and it seemed likely I was the only audience member. The blonde plopped one firm, round breast partway out of her bra and began rolling the nipple between thumb and forefinger, her face starting to flush red. I shouldn’t be looking, I thought. Yet I made no move to leave. When the woman’s hand moved from her exposed nipple to her crotch, I knew it was time to stop gawking, and I reached for the string that controlled the French blinds. Then I saw something that made my hand freeze. There was a bulge there. Like, a man-bulge, pressing up against the fabric of her skirt. At first, I couldn’t quite parse what I was seeing.
Then it struck me. Oh, I thought as I watched her stroke that bulge slowly, making it rise, a stiff length struggling against her tight skirt. Ooooh. I felt a brief tinge of disgust, but I quickly rejected it. She was as valid a human being as anyone else. And whatever disgust and shame society had force-fed me melted away as I watched this stranger stroke her erection through the fabric of her skirt. I was transfixed, all thoughts of stepping away evaporated in an instant by the tingle in my belly. This was beautiful.
My heart skipped a beat when she began pulling her skirt up, and I found I had unconsciously grabbed the hem of my skirt and was slowly sliding it up along the dark skin of my leg. I stopped myself, aghast as I took a step back.
“What is happening to me?” I said out loud.
Even though I knew it wasn’t possible, it was as if the woman had heard me, because she turned around and looked right up at me. I realised my movement must have been fairly eye-catching to her, seeing as I was standing in what was probably the only lit window across the street from her. I held my breath, stupidly thinking that if I just stayed quiet and immobile, she wouldn’t notice me. It became quite obvious I had failed when she waved at me with a shy, uncertain smile on her face. Her makeup was sharp and bright, like she was trying a little too hard, but she had a cute, somewhat angular face.
For a few seconds, I just stood there. I had any number of sensible reasons to remove myself from this situation. But I wasn’t acting on any sensibilities. That same desire that had moved my hand to my skirt returned, stronger than before, and it stirred something inside me. I moved my hand up and waved awkwardly back.
The woman’s smile broadened and grew warm. Then she reached back to her skirt and kept pulling it up until it was bunched up at her waist. She wore purple lace panties that did little to contain the bulge she was now sporting, and with a deft flick of her wrist her gorgeous cock flopped out and stood to attention. It was average-sized and hairless, a little crooked. She put her phone away so she could stroke it with one hand while holding her skirt up with the other. Soon she realised the impracticality of that and hoisted her stretchy skirt up to cling around her belly, out of the way. Then she grabbed her cock again and started stroking it. But instead of picking up her phone again, she put her other hand to her exposed breast, playing with the nipple, and looked up at me. And she smiled invitingly.
I was in heat. It was inexplicable, but I wasn’t about to question this warmth spreading through my tummy. Any intention of shying away was evaporated by the hot desire rising through me. I have no idea what had gotten into me, but I had never been this horny. I unzipped my skirt at the back and let it drop. When I put a hand to my sex, I gasped. I usually had a hard time getting wet and often had to use lubricant for penetrative sex. Now my plain black panties were soaked, and when I brushed my outer lips through the wet fabric the touch sent an electric jolt of pleasure coursing through my body. It caught me so off guard that I let out a high-pitched little squeak, and I had to steady myself with a hand on the stone window sill. I giggled at the absurdity of the situation.
For a moment, I thought I was losing my mind, but then I saw the woman looking up at me, smiling, stroking her cock a bit faster, and I knew I wanted her to see me like I saw her. So I quickly stepped out of my panties — they clung to my wet sex for a moment before detaching — then I moved close to the window and lifted my leg so I could put my high-heeled shoe on the window sill, angling myself so that the woman would get a full view of my sex as it parted wetly. I hadn’t groomed for a while, but I didn’t care, and I didn’t think she would either.
The reaction I got proved me right. Her eyes widened with eagerness and her smile was hungry. She sprang up from her chair and walked up to the window to sit on the broad sill, leaning her back against the side of the window so she was half-sitting. I was looking right down at her cock, rising wet and hard from beside her panties. She looked up at me as she ran her fingers over the head, squeezing it a little before stroking the shaft, now slick with her pre-cum. It looked so incredibly hot, and I couldn’t wait any longer. I plunged two fingers into my wet folds, eliciting another surprised gasp from myself as my pussy instinctively clamped down on them eagerly. As I pushed my fingers deeper, pleasure began strumming from the walls of my cleft and out into my body.
The young woman was apparently equally aroused because her strokes were picking up speed, and she plopped out her other breast so she could squeeze both with her free hand, pinching at the nipples. Our eyes met as we fondled ourselves with increasing intensity, locked in a beautiful moment of shared pleasure. I was moaning loudly by now, and sweat was beading on my forehead. Her head threw back and I thought she would cum, but instead she began rubbing her shaft even more intensely. Then she slapped the side of her ass cheek once, twice, three times, her lower body jerking with the impact, forcing her cock into her clenched fist. The strobe effect from the copier made the scene surreal, green light flashing as she stroked and slapped herself.
Somewhere along the way I had thrown off my jacket and begun unbuttoning my blouse, wanting her to see as much of me as I did of her. I struggled impatiently with my bra, settling for unclasping it and letting it settle loosely under my blouse, oblivious to any discomfort it caused. My breasts dropped out in the cleave of my open blouse, heaving with my excited breath. I had often felt self-conscious about how they weren’t as round and firm as in my youth, but once more I found I didn’t care; this woman wasn’t judging me. My breasts were beautiful, drooping just a smidge but with broad, dark nipples perking up in excitement. I squeezed one firmly, cherishing the slick softness, imagining it was her hand on me.
As the blonde kept picking up the pace, I followed suit and dropped my hand to play with the bud of my clit while pushing another finger inside my soaking canal, then another, sloppily fucking myself with four fingers, gasping at each frantic stroke. Before today I had never even dreamed I could be turned on by a trans woman, but now all I wanted was to be in that room, fondle her cute tits, strap on a rainbow-coloured dildo and fuck her tight little ass until cum burst from her smooth cock, then lick it off her limp member and let it mingle in our mouths as we kissed.
The young woman climaxed first, throwing her head back as her cock threw out a stream of white cum, arching through the air before landing back on her legs and skirt. Another shot geysered out with less force, landing on her panties. The final burst pooled in her hand as she cupped the tip of her cock. She brought her hand up, letting the cum run over it sluggishly for a moment, then pressed her palm up against the window. She looked straight up at me as her cum smeared onto the glass. The intimacy of the gesture brought me over the edge, and I was shaken by tremors of pleasure so forceful my body lurched forwards and I had to steady myself against the window sill as I cried out. Juices surged between my fingers, dripping onto the floor and running down my leg while my body shuddered with blissful aftershocks.
I had never experienced anything like it. My hand was soaked, I was panting as if I’d just been out for a run, and even now my sex was twitching with something that I might once have called an orgasm.
I looked back up, and the woman still held her hand up to the window. I put my hand up as well, smearing my juices onto the window pane and feeling a strange relief as I put my shame away and soaked up the intimacy of the moment. We watched each other, and though we were separated by distance and glass, it felt like we were right next to each other, a fraction of an inch away from touching.
A passing car honked its horn at an ambling drunkard, and the spell was broken. We started fixing ourselves up, though we both kept peaking at each other with the same awkward smile on our faces. I put my soaked panties back on. It’s not like I usually brought extra pairs to the office. Maybe I should start? I laughed a little at the thought.
I picked up my other clothes and scrambled back into them, feeling a bit self-conscious even though I was certain no one else was in the office. When I was doing up the final buttons on my blouse, I turned back around to look out. The room was dark.
I didn’t want to explain to Aleksy how that particular stain had gotten on the window, so I fetched some napkins and doused them with water from my bottle so I could wipe away the handprint. I found I was parched and drank the rest of the water, then sat back down at my desk. I still had work to do. As I got back to it, I found I could focus more easily, like a tension I had been holding inside for a long time had begun to release. Like I was just a little bit more myself.
(Link to Part 2.)
