“With who?” I said.
“Aren’t you watching that ginger chick? She’s dancing all by herself. Just go dance with her before someone else does,” he said casually, as if it wasn’t any more complicated than that: just go dance with her. Who cares if she looks at me with revolt and tells me to screw off? Who cares if I end up looking a complete fool in front of everyone, including Larry, who would certainly tell everyone at the office about my embarrassing blunder?
My heart stuttered and I forced a smile. “I’m not much of a dancer,” I said. “Besides, she’s not really my type.” I don’t know why I lied. It was something that I did occasionally when I felt like I was under pressure. I didn’t want Larry to know that I was infatuated with someone but I was too afraid to approach them. I wanted Larry to think that I was cool and confident, even though my body was tense and my face was probably dark red.
“Whatever,” Larry said. Then he looked at the redhead on the dance floor. “I thought she was kind of cute.” Larry walked away, back towards the bar, to continue his process of getting blackout drunk. And I found myself once again at the back of the room, watching the girl of my dreams swirl around on the dance floor with the cutest smile on her face.
It was an hour later when I lost track of Larry. When I went to use the bathroom, I heard someone barfing in one of the stalls, and I’m pretty sure that was him. So I was on my own. I thought about going home, but another little bout of confident swelled inside of me. The image of that strawberry blonde in the green dress flashed through my mind, and I bit down on my tongue, remembering what Dave told me. I just had to do it. I would probably never see her again, so what difference did it make if I embarrassed myself? If I asked her out and she said yes, that could be the beginning of a whole new era of my life—an era that didn’t involve living in my parents’ basement, sleeping alone every night, constantly wondering when my life would stop sucking.
So I went back out towards the dance floor to make my move. I looked around for the girl, but I couldn’t see her. Was she gone? Did I miss my chance? Suddenly, I spotted her walking to the door from the coat check. She had a faux-fur coat on and she was leaving alone. I rushed through the crowd to catch up with her. But people weren’t letting me through. I pushed and shoved and finally reached that front door. I poked my head out and saw that she was halfway down the block, holding her fur coat tight as the summer night’s breeze was cooler than usual. I made note of which direction she was heading, and then I hurried over to the coat check. I skipped the line and handed my ticket to the woman. “Hey! Get to the back of the line!” one of the girls in the line said to me. But I ignored her. I only had a couple of minutes before that girl was out of sight, and I wasn’t willing to let that happen.
The coat check woman brought me my coat. I snatched it and took off, without leaving a tip. I had no time to dig a tip out from my pocket. “Sorry!” I said to the line of angry people as I dashed for the door.
I slipped outside, but she was gone. I started rushing towards where I saw her last. I got to the street corner and looked both ways. She must have turned, seeing as she wasn’t straight ahead—but she wasn’t down either of the roads. Did I lose her? Did I lose my final chance to make my move?
I had to pick an option: left or right? I took a deep breath, closed my eyes, and then my intuition took me to the right. I jogged down the road towards the next intersection and I looked both ways again. And then I saw her, to my left, walking down towards the apartment cluster where my friend Dave lived. So I kept following.
I got within thirty feet, and then my joints started stiffening again. I could smell the trail of her amazing perfume: hints of vanilla and hints of lavender. I found myself almost hypnotised by the way her green skirt danced from side to side as she took her long strides in her tall heeled boots. Maybe she was out of my league. Maybe I was just going to make a big fool of myself. My hands started trembling and a lump started forming in my throat. But I wasn’t going to let my low self-esteem get the better of me again. I was going to do what Dave told me to do: I was going to bite my tongue and I was going to talk to her.
Suddenly, she turned towards one of the apartment entrances. It was the building Dave lived in. She lived in the same building! I wondered if Dave knew her—maybe he could set me up. Maybe that gave me an in. But just in case Dave had no idea who she was, I needed to make my move. I started hurrying towards her, hoping to catch her before she slipped inside. I tried to think of what I was going to say—how I would break the ice. No words came to mind, but I was sure that I would be able to muster something up once she was staring into my eyes. I got a bit closer, then a voice shouted out behind me. “Hey!”
I looked back and saw a man waving something in the air. “Yeah—you!” he called out. “You dropped your wallet!”
I checked my back pocket and realized he was right: my wallet was gone. He jogged towards me. I looked back at the stunning strawberry blonde, but she was already gone: already inside of the apartment building. I let out a long sigh and turned to get my wallet. “Thank you,” I said.
“Don’t want to lose that,” the man said with a smile and a nod. He walked away and then I groaned. I was so close. Why didn’t I just talk to her at the club? Why couldn’t that bout of confidence fill me up when I was actually close enough to talk to her?
I walked up to the apartment building door and I looked through the window. The lobby was empty and I had no idea where the girl went. I waited a minute, staring up at the structure, waiting for a light to turn on, so I would at least know which unit she was in. But no lights came on. Maybe she was in one of the back units, just like Dave.
I slipped around the building, opening the gate to the garden. On my way, I pulled out my phone and shot Dave a text message. “Are you home now by any chance?” I asked. I stood for a moment and waited for a reply. I figured if Dave was home, then I could tell him to come out and have a smoke with me while I looked up at his building for that beautiful woman. But Dave didn’t reply. “Damnit,” I muttered.
I made my way into the garden, keeping my distance from the windows so people wouldn’t think that I was some sort of vagrant. I looked up at the building for lights. It was late—probably past midnight. But the only light in the building was coming from Dave’s garden-level flat. So I checked my phone again. If his lights were on, then surely he was home. Why wasn’t he replying to me? Was he ghosting me? Did he have his phone turned off?
I saw a shadow moving inside of his flat. A figure moved from his bedroom to his bathroom. I figured it was Dave, so I started approaching his back window. And I was just about to knock on his window when that beautiful woman suddenly emerged from his bathroom.
She was taking out her earrings. Her tall black boots were already laying flat on the floor in the hallway. I suddenly jumped back and crouched down. Did I have my buildings mixed up? Was this not Dave’s apartment?
I looked over at the living room and saw the framed Caddyshack poster above his blue couch. It was the very same poster and the very same couch. And I could even see the framed degree above his office computer. I squinted and could make out his name: ‘David Anderson’. So what was the beautiful strawberry blonde doing in Dave’s apartment?
What I saw next made my heart stutter. She reached up and nestled her fingers into her hair. She shimmied her hands gently for a moment, and then the hair slipped off of her head—or I should say: off of his head.
The beautiful girl was Dave, my long-time best friend.
CHAPTER II
It was almost 2:00 AM when I finally returned to my place on the other side of town. My heart was still pounding when I walked through the door and my stomach was turning when I plopped down on the couch. It was late, but I wasn’t tired. I couldn’t even wrap my head around the possibility of sleeping. I still couldn’t believe what I’d seen: Dave in a little dress and makeup and a wig. And worse, I couldn’t believe how obsessed I was with him all night. I practically follo
wed him around that club like a moth following a bright light. I stared at his ass with wonder glowing in my eyes—and at one point I even had to excuse myself for the bathroom because I could feel my cock getting hard.
Now, as I sat on my couch and remembered all of that, I shuddered. I felt like I needed to take a shower. Could it really be true? Did I really spend the whole night crushing on Dave?
It was around 2:15 AM when Dave finally texted me back. “Hey, sorry, I just got your message. I’m home now. What’s up?” he wrote. I stared at the message for a long time—I have no idea just how long to be honest. I tried to figure out what to say. Was I supposed to tell him that I saw him? Was I supposed to call him out? Was this something that he did all the time?
Surely it couldn’t have been his first time. He wore that dress so naturally, and he moved with so much grace… Does that not take a lot of practise? And his makeup—don’t girls spend years learning to do their makeup like that?
Dave was an experienced cross-dresser, but it didn’t seem possible. Dave was a normal guy. He liked to play video games and he went to the gym all the time. He was always in and out of relationships with beautiful women—women who were far out of my league. We drank beer together and talked about sports with one another. Dave couldn’t possibly be an effeminate cross-dresser on the side… Surely he had just lost a bet or something. Maybe he was just playing some sort of joke. Maybe he knew that I would be at that club, and he thought it would be funny to mess with me. But how exactly was he messing with me? It’s not like he made me have a giant crush on him…
“What did you get up to tonight?” I finally wrote back to him. Then I found myself sitting and staring at my phone. My heart was pounding as I awaited his reply.
“I just stayed in and caught up on some work,” he said. “Nothing interesting. What are you doing tomorrow? Want to grab brunch?”
My heart stuttered and coughed. I felt beads of cool sweat forming on the back of my neck. I cleared my throat before responding. “Sure,” I said.
“Great. It’s a date,” he said. And I knew that he was joking because he was the joking type—but that little joke made my gut turn and gargle. I’d spent the whole night trying to approach him to ask him on a date, and now I was getting what I wanted. Be careful what you wish for, I guess…
And my God! What if I had built up the confidence to talk to him? That would have been so embarrassing! Surely he would have rejected me, and then I would never have discovered that I’d asked Dave out on a date. The thought alone made me feel ill.
I only got a few hours of sleep before our brunch. My heart was still throbbing when I pulled up to the busy restaurant. I found myself sitting in my car, staring at the front door of the establishment. The thought of going inside made my legs tremble. What if Dave saw me at that club the night before? What if he knew that I followed him home like a lost puppy? What if he could tell that I was trying to build up the confidence to ask him out? He knew that I had a hard time talking to girls. Maybe he was going to use this brunch as an opportunity to laugh his head off at me. Or maybe he really just didn’t see me at that club. I was invisible to all of the other girls, so why not him as well?
Dave suddenly appeared in my car window. He ducked down and knocked on the glass. “You just going to sit there?” his muffled voice asked. I jumped and pressed a hand firmly against my heart. It was a moment before I broke free from my frozen terror. I opened the door and stepped out.
“Long time no see,” Dave said.
“I saw you last week,” I said.
“Yeah—and that’s a long time. What’s the matter? You look white. Feeling okay?”
I nodded my head slowly. I found myself staring at him, trying to figure out how it was possible that he was the girl in the club. But now that I was looking carefully, I could see the similarities: the deep green eyes, the small nose, and the soft jawline. But when Dave was dolled up, he used a few little makeup tricks. He used contouring to make his cheekbones more prominent, and the long hair of his wig helped to shape his face in a more feminine way—though now that I was staring at his face, I couldn’t help but notice that it had a natural feminineness to it.
“Why are you staring at me like that?” he asked.
I looked away quickly as my heart was sent aflutter. “I didn’t get a lot of sleep last night,” I said.
“I know. You were texting me at, like, three in the morning. What were you doing last night anyway?”
We walked into the restaurant and managed to get a nice table by one of the big windows. “Last night?” I said, trying to think up a lie. But my head was filled with those final images I saw in Dave’s apartment before I took off for my house. The night before, I hid behind a bush and watched as Dave took off that dress. Underneath, he was wearing lingerie: a lace one-piece that hugged his shaved crotch and extended up to his shoulders. Inside of that lingerie he had two pads, which he pulled out and placed on his TV stand. But he didn’t take off the lingerie right away. Instead, he walked over to his mirror and did a couple of poses. He grabbed his wig and got it back on his head.
It was a confusing and awkward sight. Even without the cups giving him a bust, he still looked like a chick; he still looked like the cutie that I’d had my eyes on all night. But I knew that he was Dave. I could see the bulge of his sissy cock in his little one-piece. And no matter how hard I tried, I couldn’t look away. I stayed and watched—and I ended up seeing far more than I anticipated.
He put on some music and started dancing alone in his flat. The cool summer night’s air was starting to numb my arms and legs, but it wasn’t enough to get me to move. I watched as Dave danced over to a drawer under his television. He dug in deep and pulled out a long dildo. My heart stopped momentarily as he reached it down and rubbed it against his crotch bulge. I still couldn’t believe what I was seeing. I even closed my eyes at one point and tried to convince myself to wake up, half-convinced that I was in the middle of a very strange dream. But I didn’t wake up. What I was seeing was real.
Dave nestled that dildo between his couch cushions, so that it was standing straight up in the air. Then he reached down and pulled aside his lingerie one-piece, exposing his butthole and getting it ready for penetration. He spat onto his fingers and he rubbed that spit up and down the fake cock. I knew that it was beyond my cue to leave, but I just wasn’t able to look away. I kept watching. I watched as he sat down on that cock, taking the whole thing up his ass. Then I watched as he bounced, still in that sexy lingerie.
Now, Dave waved his hand in front of my face. “Hey—earth to Ryan. You alive in there, buddy?” he said. I snapped back to reality, but that image of Dave all dolled up refused to leave my head.
“Huh?” I said. “Did you say something?”
“I asked what you got up to last night. I’ve asked like five times now.”
“Oh. I went out with this guy from work. His name is Larry. You don’t know him.”
“No—I think I met Larry at that house party last year. Remember?” Dave said.
“Oh—right. Maybe you did,” I said. I took a long sip from the coffee that was in front of me. I didn’t even remember ordering it. It was hot and it nearly burned the inside of my mouth, but I needed the caffeine desperately. “And what did you get up to last night?”
He laughed. “I already told you. I caught up on some work,” he said. “I’m hoping to take a few days off of work next week—not for any reason in particular, just a little staycation—so I need to make sure I’m all caught up with work.”
“Right,” I said, nodding my head slowly. And now I was looking down at his body. I’d never noticed how slight he was. He had narrow shoulders and thin arms. Even his neck was thinner, and there was hardly an Adam’s apple to be seen. How had I never noticed his feminine figure before? I suppose it wasn’t that out of ordinary. Even my own figure wasn’t so different. I was thin without much muscle mass on my shoulders. Maybe I could fit into that same lingerie and t
hat same dress… Maybe I wouldn’t have looked as ridiculous as I assumed I would have.
Dave laughed. “You’re acting really weird today. Do you work tomorrow?”
I shook my head.
“Well you should go definitely sleep in then. I think you could use the rest.” He picked up his menu and looked down. “I think I’m going to get the pancakes. I got the waffles last time we were here and I got the French toast the time before that. What do you think?”
And I just nodded my head, unsure of what to say. I was still trying to figure out if I should tell him what I saw. I didn’t want to put him on the spot. And I definitely didn’t want him to know that I saw him riding a dildo until the lacy lingerie around his cock started to become wet with what I assume was cum. So I decided to keep my mouth shut. Maybe it was just none of my business. He was a free man in a free country and he could go out clubbing as a chick if that’s what he wanted to do. Everyone has their thing, and that was just his thing.
But even once I was back home after our brunch, those images were still on my mind. I found myself on Facebook, looking through Dave’s pictures—but I wasn’t sure what I was looking for. I kept looking closely at pictures of his face. He had some feminine features, but his face wasn’t obviously feminine—not until he was wearing makeup.
And how often did he get himself dolled up? Was this something he did every weekend? Was it something he did every night? I tried to remember the last time I saw him at night. It had been a while. He always wanted to hang out during the day. He always had plans at night—and did those plans involve makeup and that strawberry blonde wig?
The sun was just starting to set when I decided to head back over to his flat. I put on an old green coat and a navy blue baseball cap. I was going undercover—going to spy on my long-time best friend, to see if this was something that he did often. I waited until the street in front of his building was clear, then I slipped through that back gate, into the garden behind his flat.
Womanized Page 73
