His lights were on, but I couldn’t spot any movement in his apartment. The lights were on in the other apartments as well, so I knew I had to be careful. I nestled myself into the same bush as the night before. At least the air was warmer now, so my arms and legs weren’t going numb—but they were still trembling, now just with fear of being caught. Or maybe it was a different kind of fear. Being caught wouldn’t have been so bad. I could have run away, or just lied and said that I was pulling a prank on my friend.
I was more afraid of why I was there for the second night in a row. I’d spent the day convincing myself that it didn’t matter what Dave did with his own free time—yet there I was, staring into his flat, hoping to catch another glimpse of him all dolled up.
I saw a shadow moving at the end of his hallway. He was in his bathroom. Was he doing his makeup or his hair? Was he getting ready for another night out?
And why was I watching? What demon had possessed me and brought me back to that tall bush behind his building? Did I like the way that he looked all dressed up? Was I hoping to get another look at him all pretty? Was I hoping for more than that—a repeat of the night before? Maybe he had other toys stashed away in that flat: more phallic objects that would explore the depths of his sissy asshole.
I bit down hard on my tongue as a tingle crawled up my spine. I shook my head and took a deep breath. No—I was just there to see if it was true, and not just a drunken fever dream I had the night before. It seemed hard to believe, even though I’d already seen it with my own eyes. I needed to have a second look with a clearer mind—though I wasn’t sure if my mind was any clearer now than it was the night before…
That shadow moved again. He was coming out from his bathroom. I sunk down low, even though it was dark out and I knew he couldn’t see anything past his own reflection in his window.
And there he was again: wearing his wig and some makeup around his eyes. It was a more minimal look tonight, but it still did the job. Now, he was wearing a red satin nightie. It looked comfortable, though it wasn’t quite long enough to cover his ass. He walked down his hallway in a feminine way, with a straight back and long strides. He went into his kitchen and pulled a bag of popcorn out from his cupboard. He tossed it into the microwave, and then he poured himself a glass of white wine.
Though I wasn’t convinced it was him. It was definitely the girl from the night before, with her long strawberry blonde hair—but maybe she was just Dave’s secret girlfriend. Maybe that’s why Dave hardly ever had me over at his place—because there was a girl living there with him. But that didn’t explain what I saw the night before, when she took off the wig, revealing the scruffy brown hair underneath—hair that looked exactly like Dave’s hair. And that also didn’t explain the fact that Dave and the girl had the same eyes, the same nose, and the same jawline. Dave was the girl, though it was hard to imagine that she could be a dude.
Once her popcorn was popped, she poured it into a bowl and moved towards the living room. She put the bowl down, turned on a girly reality TV show, and then she leaned back, relaxing, letting her smooth, pretty body sink into the soft blue couch cushions.
She was just watching TV—not getting ready to go out, not getting ready for company. She was just enjoying some time alone… as a girl. She sipped her wine and ate a few small handfuls of popcorn. Then, she pulled a little bottle of nail polish out from her side table drawer. It was white and glossy. She reached out her long, smooth legs and started to paint the polish onto her toenails. Her feet looked soft and petite. And when I looked close, I could tell that her legs had recently been shaved—or maybe waxed. They had a glisten and a softness to them. I just wanted to go into that flat and run my fingers up and down those smooth legs.
I shook my head. What was I thinking? Why was I allowing those silly thoughts into my head? I was still looking at Dave. That girl was Dave, even with her long smooth legs and her tiny red nightie.
She painted her nails slowly and meticulously. But she didn’t paint the nails on her hands—though she did pull out a file, which she used to round the edges on all of her fingernails.
And why was I still watching? What exactly was I hoping to see now? Was this not enough? Was this case not settled? The girl was Dave. Or was she? How could I really know for sure?
I had the brilliant idea to send Dave a text message. I grabbed my phone and typed out a simple message. “Have you seen the new season of True Detective?” I asked.
Then I looked up and watched as the girl looked back. She stood up and walked back to her bathroom. Then she emerged with her phone—the same phone that Dave owned. She typed away as she made her way back to the couch. Then, as she put her phone down on the side table, a message dinged on my phone. It was fro Dave. “Not yet. Should I watch it? Any good?”
And that settled it. The girl was Dave. Dave lived a second life as a beautiful woman. And apparently it wasn’t just something he did when he went out—it was something he did even when he was just lounging at home. Maybe he was dolled up for most of the day. Maybe the Dave that I knew was just the occasional persona that he wore when he was around me, and when he was around the office. But when did it start? Since the third grade, I’d been seeing Dave constantly. I would spend entire weekends at his house, but I never saw any signs of cross-dressing. I slept on the floor of his bedroom more than once, but never did I see a pair of panties underneath his bed.
I even helped him move into the apartment he was living in now. I loaded that U-Haul truck and I unloaded it. I even helped him unpack, but I didn’t see any boxes filled with lingerie or clubbing dresses. Was this a new thing? Was it just a phase? And why didn’t he want me to know about it. Well, the answer to that last question seemed obvious enough. It was an embarrassing little hobby. I desperately wanted to make fun of him for it, but at the same time, I didn’t want to ruin my best friend’s fun. Maybe he was depraved—maybe he was even a bit of a pervert—but he was still a free man to do whatever he wanted to do.
At least he pulled it off. At least he wasn’t some tall, butch dude with a stubble beard wearing some undersized dress. At least he had the legs of a goddess and the hips of a supermodel. That wig looked good on him—I couldn’t just pretend like I didn’t spend the whole previous night fawning over him—fawning over her. I wasn’t fawning over Dave. I was fawning over Dave’s female persona. It’s not like I wanted to ask Dave out on a date. It was her that caught my attention, not him.
And now, she was looking good, once again, with seemingly very little effort. She had her cute toenails freshly painted white and she had a big smile on her face. She looked peaceful. It was almost too bad that she wasn’t a real woman. I could imagine myself sitting next to her on that couch, with my arm over her shoulders. I closed my eyes and imagined her cuddling into me with her small, soft body. I imagined her slight fingers reaching over and slipping onto my lap: teasing my bulge gently and flirtatiously.
Then I opened my eyes and shook my head, shaking those thoughts away. They weren’t welcome—that wasn’t a normal girl sitting on that couch. That was Dave sitting on that couch. And that was something I couldn’t allow myself to forget.
I watched like a total creep for the next hour, even though she didn’t move from her seat. I was strangely mesmerized—at first because the sight seemed so bizarre and ridiculous, and then because I found myself in a state of wishing she was real. She was, after all, still the girl that I spent that whole night trying to talk to.
Her show ended and she started flipping through the channels. She finally landed on a movie that was half over, and she stopped just as a sex scene started. It was a romantic sex scene—the characters were silhouettes and everything was in slow motion (and of course they didn’t show any private parts—not even the girl’s tits). But the show made the strawberry blonde bite down on her bottom lip. I watched as she took a deep breath in, and then she stood up and turned the television off. She grabbed her laptop off of the counter and she made her way t
o the bedroom, closing the door behind her.
I perked up. What was she doing? Why did she leave so suddenly? I stood up slowly and crept around the building. The bedroom window was near that garden gate—up high, so I had to awkwardly climb up the nearby fence to see in. The blinds were mostly closed, but there was a slit that I was able to see through. And through that slit I saw the girl on her knees, on her bed, still in that red nightie. She had her laptop set up in front of her, playing a vanilla porn movie. In the movie, the couple was making out and the girl was reaching down and stroking the man’s large erection.
The girl I’d spent the night watching had a phallic vibrator in her hand. She had it pressed between her legs, buzzing against her bulge. Her cheeks were dark red and her gaze was fixed on that porno. She slid the vibrator gently up and down, stimulating the length of her shaft.
I was holding onto the edge of the fence awkwardly, letting the old wooden splinters dig into my skin—but I hardly even noticed. I was too obsessed with the sight of my best friend, on her knees, bringing herself closer and closer to orgasm.
It was only a few minutes before her body was trembling. Her eyes closed and her body twitched suddenly. Then, I saw that dark spot growing against her satin nightie. She was coming! She was filling her panties with jizz, and that jizz was soaking through the panties and the satin gown she had on top.
I heard the slamming of a nearby car door. The noise made me jump down from the fence. My heart was pounding, though I’m not sure of the exact cause. I looked around and decided to make my escape. I’d already overstayed my welcome. And now, I had far more swirling through my mind than I knew what to do with.
CHAPTER III
It was the next weekend when I waited with a pair of sunglasses and a baseball cap down the block from Dave’s apartment. I lingered on that street corner for over an hour before he finally emerged from that front door: in his cute feminine form—or maybe I should say, in her cute feminine form.
I knew that she was getting ready to go out because I’d slipped into that garden and I saw her doing her makeup, and she wasn’t just doing her minimal look. I also saw a white glittery dress draped over her kitchen island—and she was wearing that dress now.
I kept my distance as I followed her—though I had no idea why I was following her. I’d already determined that she was Dave, so there was nothing left for me to discover. Now I was just a crazy stalker—though I kept telling myself that I wasn’t a stalker, that I was just curious to know what she was going to do. That excuse wasn’t going to last very long. I’d already used it five times as I sat in her garden, staring through her apartment windows.
This was the first time she’d gone out as a girl since I first saw her out at the club. Now, she was headed back to the clubbing strip. But this time, she went to MAX, the hot new club that had been all the buzz for the past few months. I’d never been inside because there were always long lines to get in, and I never had the patience. I was surprised when the strawberry blonde vixen slipped into the long line. Did she really want to spend the first hour of her night off waiting to get into a club?
Well—she didn’t have to wait. The bouncer walked up to her after just five minutes and said, “You can come with me.” He took three other girls with him—all babes. The rest of the line groaned and sighed, but the bouncer didn’t seem to care. The club was hot for a reason—because it was filled with the hottest girls in town. Apparently Dave was one of them.
I felt awkward as I waited in that line, with my green coat and my blue cap. Everyone else was dressed up: collared shirts, pressed pants, plenty of bling—but not me. I wasn’t even wearing nice shoes, just my old runners. I wasn’t even sure the bouncer would let me in once I reached the front of the line. And he almost didn’t. He looked down at my feet and then he looked slowly up my body before saying, “No hats inside.” So I took off my hat.
The club was large and loud. Coloured lights were flashing in all directions, and nearly everyone in the place was dancing. I fought my way towards the bar, looking around constantly for the trap I was following. I figured I would get myself a drink while I stalked her—and I only say ‘stalked’ because I can’t think of a better word… So maybe that means that I was stalking her. But my curiosity was overwhelming. I just had to know what she got up to when she was out with that wig and makeup. Did she just go out dancing, or was there more to it? Did she flirt with men? Did she ever go home with guys? Would she use the women’s bathroom when she had to go pee?
I had to fight my way to the bar, and then I had to wait almost ten minutes to get the bartender’s attention. In case that wasn’t enough, it took the bartender another ten minutes to get the simple beer that I ordered. I spent the whole wait looking around, scanning the female faces in the bar, hoping to find her. And then she appeared, just as my beer was handed to me. She was headed to the bar, coming from the dance floor. I spun around quickly so that she wouldn’t see my undisguised face. She stepped up right next to me and waved at the bartender. The bartender didn’t hesitate. “What can I get you?” he asked, without making her wait the ten minutes that I had to wait.
“A gin and tonic, please,” she said. Her voice was shockingly convincing—though I could hear that slight male tinge. I could hear the little bit of Dave that she would probably never be able to get rid of. I continued to keep my face turned away from her. My heart was pounding. She was so close to me—almost touching me. All she had to do was look over and she would probably recognize me just from the side of my face.
The bartender immediately mixed her drink. Then he didn’t charge her. “It’s on the house,” he said as she tried to hand him a bill. And suddenly, I could see why someone would leave the house all dolled up like she was. Free drinks? Why didn’t I ever get a free drink?
“You’re so sweet,” she said.
“Don’t mention it,” said the bartender. “What’s your name?”
“It’s June,” she said.
“Nice to meet you, June. Randy.” The bartender reached his hand over the bar and Dave—or I should say, June—shook it. “I get off work in an hour. Will you be around?”
June shrugged her shoulders. “Maybe,” she said with a grin that I could see in the mirror behind the bar.
The bartender grinned back, as if they had just agreed to something that flew right over my head. Then June slipped away from the bar, back towards the dance floor. The bartender looked up at me and said, “Is something wrong with your beer?”
I shook my head. “No. Why?”
“Move away from the bar. You’re taking up space.” He wasn’t nearly as nice to me as he was to June. I was tempted to tell him that he just hit on a biological male: a dude in drag. Sure, that dude happened to be convincing, but he was still a dude. But I said nothing. Instead, I just slipped away from the bar and went to find my friend out on the dance floor.
I had to circle around the busy floor. I managed to spot her near the middle, dancing with that drink in her hand. She had a big smile on her face and a crowd of eager men hovering around her. One of the men got very close on the next song, putting his hands on her hips and grinding his crotch against her bum. She didn’t seem to mind. My heart throbbed and ached at the sight. He wasn’t a terribly handsome man. He was balding and he had terrible tattoos all over his arms and even his hands. June could do better. But it’s not like she was going home with the guy—she was just dancing with him.
After a few songs, she went back to the bar. The original bartender was gone, and now there was a woman mixing drinks. But June still got her drink for free. Before she could pay for it, a man in a red dress shirt tossed a bill towards the bartender and said, “It’s on me.” The man in the red shirt was much more handsome than the tattooed man—though I still think June could have done better. This man had a charming smile and a full head of hair. He chatted with June at the bar for the next ten minutes. I tried to get close so I could hear what they were saying, but that club was just t
oo loud. Though I did hear when he said, “Let’s go out back where it’s quiet, so we can talk.”
I followed them to the back door, which I don’t think was meant for clubbers. There was a sign on the door that read, ‘DOOR WILL NOT OPEN FROM OUTSIDE.’ Still, the two slipped out, letting the door close behind them. I wasn’t able to follow them out into the alley—I knew June would see me. So I fought my way through the club and went back to the front door. I jogged around the building, into the alley. But the alley was clear—at least it seemed like it was clear, until I heard a quiet groan.
My heart stammered. I crept slowly towards that back door. I could hear the booming bass of the music inside. That groaning was getting louder now. I crouched down next to a dumpster. Then I peaked around the bend.
And there was June, on her knees in that cute white dress. The handsome man was standing with his hands in June’s hair. He had his head tilted back and his eyes closed. He was getting his cock sucked.
I nearly gasped. Was Dave gay? He never acted gay. He’d had a few girlfriends in the past few years—cute girls, too. Was he one of those bisexuals? I had to put my hand over my mouth to stop myself from uttering a sound in disbelief.
She sucked that cock in a graceful way, bobbing her head back and forth slowly, using her hand to hold the cock straight outwards. Her other hands was fondling the man’s ball sack.
“Shit, that feels so good,” the man whimpered. His legs were trembling. “I think I’m going to come. Fuck—you’re going to make me come.” He let out another long gasp, and then he groaned loudly. June let out a muffled gasp, but she didn’t take that cock out from her mouth. She froze and clutched that cock firmly. Then, after a moment, she slipped the cock out from her mouth, swallowed a big load, and then took a deep breath as if she had been holding her breath for four straight minutes.
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