I smiled and nodded my head. I looked around for an exit, so I could get away from her before I did something stupid, like ask to try on her skirt. But she was blocking the only way out, unless I wanted to go back into the bathroom. “I’m sure you’ll do just fine. You’re a very beautiful woman.”
She laughed and her cheeks turned red. “I can’t remember the last time my husband told me I was beautiful. He always said that he didn’t need to say it—that it was implied. But it’s just so nice to hear sometimes—you know?”
I nodded my head. I did kind of know, because for the past few days, a part of me had wanted to hear those words. I wanted to feel beautiful, even though it seemed so ludicrous. She took a step towards me. “Please don’t make fun of me for this, but I’ve always wanted to have an affair. But I never wanted to cheat on my husband. I loved him—and I still love him—but I always just thought it would be so exciting to sleep with someone else in secret. And now, him and me are still technically together. Maybe—I don’t know—you could help me tick a box off of my bucket list.” She put her hand gently on my arm and held it there, as if she wasn’t sure what to do with it. It really had been a while since she’d been flirty with someone.
I awkwardly looked around, and then back down at Martha. She was pretty—a few years older than me, but still quite beautiful. She had big, round cheekbones, and cute lines around her eyes from smiling all the time. I gently brushed back a strand of her hair. My heart was racing. I couldn’t help but smile at the thought that my feminine urges were about to indirectly get me laid.
“You know I keep a vibrator in my desk?” she said. “Sometimes I put it in my pussy while I’m working. The other day, when you came up to my desk about that file, it was inside of me and I was trying to hold back my orgasm. My panties were wet for the rest of the day.”
“Show me,” I said. So we went together back to the office, which was empty as everyone was off for lunch. She opened her drawer and pulled out a long purple vibrator. She pressed a button and it started to gently hum. “It’s supposed to be one of the quietest ones you can get.” I stared at it with an excitement growing inside of me.
“I want to see you using it,” I said.
Her face became red and she looked around. She had a big smile on her face. “Oh my God, I feel so naughty,” she said as she gently lifted up her skirt. She turned it on and started rubbing it up and down her white cotton panties. I wanted to take those panties off of her and put them on me. I wanted to feel her dampness against my crotch as if it was my own. But I resisted the urge to do so. I just watched as she rubbed the dildo up and down, and eventually down the front of her panties. She let a little moan slip as her face turned an even darker shade of red.
“Show me your pussy,” I said.
She looked around again before pulling her panties down, revealing her clean-shaved snatch. I watched as she rubbed that dildo between her plump lips. “We’re going to get in trouble,” she whispered.
“No one will find us,” I said. I reached out and grabbed the dildo from her. Then I started to rub her pussy with it, using my other hand to feel her warm clit. She gasped and squirmed. She stumbled back, against her desk. I lifted her up and sat her down on that desk, and then I dropped down to my knees. I held the vibrator against her clit and then I went in with my mouth to eat her out. She was already wet, getting wetter fast. She grabbed my head tight and started to moan. She had a sweet taste to her, and she smelled amazing. I got my tongue deep inside of her and squirmed it around as she twitched and pressed her thighs in on me. I looked up and saw that she was looking around with dark red cheeks, worried someone would walk into the office and see us together. And with our lunch break just ten minutes from being over, that wasn’t an unrealistic anxiety to have.
“Just fuck me,” she said, almost whispering as she pushed my head back, out from her crotch. So I stood up, got my cock out, and then I turned her around and bent her over the desk. She took a deep breath and closed her eyes, ready to be plugged by a cock that didn’t belong to her husband—the first cock that didn’t belong to her husband in nearly a decade. I pressed it into her. She let a little shriek out, and then she said, “Oh God!” I sunk in deep and then I started to pump her sweet pussy. It felt nice, especially when her vaginal walls started to clench my cock over and over, as if she was trying to suck me up inside of her.
I spread her butt cheeks wide so that I could see my cock clearly. I watched her squirm and moan, and then once again, I felt jealous. I wanted to be the one being dominated. I wanted to feel that incredible pleasure. I wanted a man to press down on my back, holding me down on a desk while he pumped my little hole.
Then I got an idea. I could see that vibrator resting on the desk. She had her eyes closed, so I snatched it quickly. She didn’t notice. I brought the toy around my back and I gently started to press it into my asshole. It took a moment to penetrate myself, but once it was in, it was in properly. I tried not to gasp. It was shockingly tight. It was thinner than a cock, so I had a hard time imagining how people took cocks in the ass. I was slow to push it in further. But after a minute or so, I had half of the thing inside of my asshole. I gently pressed the button on the base, making it vibrate.
And immediately, my legs started to tremble as a strong euphoria began to pulse through my body. “Fuck,” I groaned, nearly falling over. I held on tight to her hips and managed to continue pumping her dripping wet pussy. The vibrator was stimulating the perfect spot inside of me—what I assumed was my prostate. I gave it a little push, pushing it just a little bit harder against that sweet spot, making my legs tremble harder. I had to lean forward and put some of my weight on Martha, so that I wouldn’t topple over. I was biting down hard on my tongue, trying not to scream out in absolute pleasure.
I managed not to scream, but I didn’t manage to hold back my cumshot. I ended up filling her tight pussy with a massive load of hot cum. She wasn’t able to hold back her scream. She bellowed out while she reached around for something grab onto, knocking papers and stationary off of her desk. I quickly pulled that vibrator out from my ass and put it back down on the desk, before she had a chance to open her eyes. My asshole felt strangely empty and agape. I just hoped she planned on cleaning the sex toy before using it again.
I stumbled back and watched as the creampie fell out in thick globs, out from her gaping pussy. She was slow to peel herself off of her desk, but once she was upright, she was quick to get herself and her desk cleaned up. She looked at me and smiled with dark red cheeks. “That was exactly what I needed. Thank you,” she said with a professional sounding voice, as our co-workers started to trickle into the office.
“Thank you,” I said, turning around and heading back to my desk. I couldn’t help but wonder if a real man’s cock would feel any different from that vibrating dildo. A part of me was tempted to steal that vibrator while Martha was in the bathroom, so I could stick it up my ass while I worked, just to see if I could make myself come without touching myself. I resisted the temptation, reminding myself that my feminine urges (if that’s even what they were) would soon pass.
And if they didn’t pass, maybe I needed to stop the drug trial.
CHAPTER VI
It was four days later when I started to think that my cock and ball sack were smaller. I stood in front of a mirror and held up my flaccid penis. It didn’t just look a little bit smaller—it appeared to be half the size. My heart fluttered. I started to massage it, getting the blood flowing to it. I figured I’d possibly slept on it funny, or maybe it was colder in my apartment than it felt. But even erect, it certainly seemed to be smaller. I was fairly certain that my cock could touch my belly button before. Now, it hardly rose up past my mane of pubic hair.
But that wasn’t the only thing I noticed while staring in the mirror. I’d always had a flat chest: not much muscle but no fat either. Now, there appeared to be too small lumps. I was able to push them up, and when I dropped them, they jiggled slightly�
�like small tits. A cold sweat started to form on the back of my neck. Maybe I was just putting on weight. Maybe my cock looked smaller because the rest of my body was bigger. Maybe the tits were just the early forming of man-boobs.
It was another two days later when I began to realize this wasn’t the case. My tits were now proper A-cups—maybe even bordering on B-cups. My nipples were larger and started to push out further than ever before. And my cock was even smaller, hardly larger than my pointer finger when erect. There was only one possible reason for the changes: the drug trial.
I ran over to the bottle of pills and I read the name on the label. I searched that name online and couldn’t find anything about any side effects. Had I been taking sex reassignment drugs? Was my male body turning into a female body?
I should have beer terrified. I should have been nauseous. But instead, I was curious. I wanted to see how I would look in one of my little outfits, now that I had real breasts. I went into the bathroom to shave my legs and do my makeup. Then, I put on a pair of panties, a little skirt, and a white blouse. The blouse felt tighter around my chest; without a bra, I could see my nipples trying to poke through the thin white fabric. I just a little bounce up and down, and I watched as my tits jiggled under that blouse.
I had no way of contacting my drug rep. I didn’t want to stop my trial, though I was afraid the changes my body was seeing were permanent. I couldn’t just stop the trial. I couldn’t just let that crippling tinnitus come back to haunt me. And a part of me was curious to see just how much my body would change if I continued the trial.
It wasn’t until I was fully dolled up that I started to notice the other changes: my skin appeared to be softer and less blotchy. My hips fit the skirt better, probably because they were wider. When I spoke aloud, my voice sounded softer; it was much easier to do a female voice. I even recorded myself speaking for a minute, just to see how convincing I sounded. And surprisingly, I sounded very convincing.
And then I found myself standing at my apartment door, with my hand on the handle. I was curious to see the rest of the world’s reaction. I knew that there might never be another opportunity—if I decided to stop taking that drug, my life would return to normal and my sissy days would be over. Though maybe that was for the best. Maybe I needed to stop before I embarrassed myself. I knew going out was a bad idea. What if I ran into someone I knew? What if one of my neighbours saw me? What if my brother saw me out on the street and told my parents and they disowned me?
But what if I went out and I actually turned some heads? What if I proved that I actually looked like a chick, and I wasn’t just losing my sanity?
I opened that door and stepped out slowly. I wobbled slightly in my stolen heels, and then I made my way to the elevator. My heart was pounding. I felt incredibly stupid but strangely free. I let out a sigh of relief when the elevator door opened and I saw that the elevator was empty. I didn’t see another person until I was out on the street, a block from my building. I didn’t recognize the person, but I still froze up, waiting to see their reaction. They didn’t even look at me as they walked by—though I wasn’t sure if that was a win or a lose. I kept walking, feeling a little bit more comfortable in my heels with each step.
I liked the feeling of the cool March breeze teasing up my skirt. I felt so naked, so I kept tugging down my skirt, worried it was riding up, showing off my tush to the world.
The streets were quiet that afternoon. Even the main drag was relatively silent as I continued my casual stroll.
I got my first look about ten minutes after leaving my apartment: I met eyes with a man across the street, and he smiled at me. I forced myself to continue walking, though I was tempted to freeze up. My heart skipped a beat and my mind started to spin in fast circles. Was that a mocking smile or a genuine smile? Could he tell that I wasn’t really a woman?
I got my second look a block later: another man with another smile. Men had never smiled at me before, so why were they smiling at me now? I looked back at the man and I saw that he was looking down at my tush. His eyes gazed up and he saw that I was looking back at him, so he looked away quickly. A little giggle slipped out through my lips. I felt flattered. Surely he wasn’t staring at my ass in a judging or mocking sort of way—right? Surely he genuinely believed that was a woman!
Now I had a stupid smile stuck on my face as I walked through the small downtown core. I was catching a new smile every couple of blocks. And it was becoming increasingly more obvious that the men thought that I was the real deal. I even caught a second guy staring at my butt. I couldn’t blame him. My skirt was short and it occasionally bounced high enough to show off the bottom curve of my rump.
I didn’t spend long outside—just long enough to fill me with a warmth, knowing that I wasn’t crazy—at least not crazy enough to think that I was something I wasn’t. Maybe I was crazy. Maybe dressing up like a girl is crazy—but at least I knew I looked the part. And now, the possibilities seemed endless. There was so much I wanted to do, so many experiences I wanted to experience.
But more than anything, I wanted to know the thrill of being dominated, the way I dominated my ditsy neighbour and my horny co-worker.
I quickly found myself on a hook-up website, designed mainly for horny men. As a woman, there was no fee to signup. I created a profile using nothing more than a selfie I took that afternoon, and within minutes I was getting messages from horny men in my area. My heart was pounding ferociously. Some of the men wanted to take me out on a date—others just wanted me to meet them for a quickie. I was quickly discovering how easy it is to get laid as a woman.
There was a handsome-enough man named Ken who asked me if I wanted to have a drink at his place. He had a firm jaw and big eyes. I didn’t feel any attraction towards him (or any man), but the thought of his big cock sliding into my asshole made my heart thump and my cock hard. Maybe I was insane after all.
CHAPTER VII
I didn’t park in front of Ken’s house. I parked two houses down, hoping he wouldn’t see my car as I rolled up. I still wasn’t sure I wanted to go through with it. I wanted to make sure I had an easy out.
I turned off my engine and I stared out at his large house. It was three stories tall with a small fountain out front. In his profile he mentioned that he was very wealthy—though I didn’t fully believe it until now. He also said that he was open to new adventures, but I was still surprised when he had no problem with the fact that I was ‘transitioning,’ even though I wasn’t—at least not in the way that transgender people transition. I suppose I was technically transitioning as a side effect of a drug trial that I was on, though I’m not sure that counts.
I took a deep breath. I could see a male silhouette moving from window to window inside of the house, waiting for my arrival. He could probably see my car and he probably knew it was me. My car was the only car worth less than eighty thousand dollars on the block—and mine was probably only worth five grand at the very most. I opened the door and stepped out, wobbling slightly in my heels, but only because my legs were trembling with nerves. I was fully comfortable walking in heels—it’s not the hardest skill to pick up, especially with a little bit of motivation.
All of the typical anxieties you would expect ran through my mind: what if he’s a serial killer? What if he has some sort of disease? What if he’s just setting me up to humiliate me? But it was almost just as scary to think that he may have been completely genuine, and I was about to walk into a stranger’s house to be fucked in the ass while dressed up like a slutty woman.
I had my pink lingerie on underneath my little dress. I was wearing a perfume sample that I sprayed on myself in the little drug store beneath my apartment. I’d spent that whole evening practising my voice, though I’m not sure any of those details mattered. Ken was just looking for a tight hole to fuck, and there was no tighter hole than mine.
I crept up to his door slowly. I could hear my own heart pounding—I still wasn’t used to hearing sounds so clearly. Ev
en the sound of my nervous breath was distracting as I hovered my finger over the doorbell. I took a long, deep breath, and then I pulled my hand away. I could see my reflection in the tinted glass on his front door. I could see my feminine figure, and it terrified me. How did this happen? How had I fallen so far away from normalcy in such a short period of time? I needed to get out before I made a massive mistake. I needed to get home and I needed to get myself cleaned up, before I did something I would regret forever.
But before I could turn, the door opened. Ken stood in the doorway, looking down at me with a smile. He was so tall—I felt so weak in his presence. “Come on in,” he said with a deep voice as he stepped aside. I took a slow step into his house, feeling the warmth of his large fireplace on my exposed legs. “You look stunning. Can I get you a drink?” he asked.
“I’m okay,” I managed to say in a soft, weak voice. His presence was overwhelming. I felt like he could pick me up and snap me in half if he wanted to—and maybe that’s how most girls felt in the presence of men. It was a strangely arousing feeling, and it was exactly why I was in that house to begin with. But it still left me with fluttering butterflies in my stomach.
“Are you sure?” he said, grabbing a bottle of whiskey.
“Yes,” I said. I looked back to make sure the door was still in sight. I didn’t want to lose sight of that precious exit. I wanted the option to back out at any moment if I wanted to. I still couldn’t figure out how I ended up in that house. I couldn’t decide if it was my own conscious doing or if it was some sort of demonic possession. I remembered the series of events that led me there, but was I in control?
“I suppose you probably just want to get right down to business then?” he asked.
I was silent. My lips parted, but not words came out. Did I open my mouth to protest or was I about to agree? Why couldn’t I pull myself together?
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