I just thought it was a strange coincidence more than anything, until I saw the young man reach back and stuff the rest of his sandwich into his backpack—which was the same backpack I saw that pretty blonde carrying around at the mall. Now I was beginning to think there was more than just coincidence at play. So I followed the young man once he got up to leave. I kept my distance, so he wouldn’t become suspicious. I followed him all the way to his locker, and then I cautiously hid around the corner, where I had a decent view into his locker once it was open.
I saw him put his bag down. He unzipped if briefly to slip out his chemistry workbook, and that’s when I saw a glimmer of blonde hair—what looked like a wig from my vantage point. And now the coincidence was just too great, because it wasn’t a coincidence. The young man was the beautiful blonde at the mall.
I didn’t follow him any further. I’d seen all I needed to see. I felt like I had to tell someone, but I didn’t know who to tell. I didn’t even know the young man’s name. And I wasn’t sure that I wanted anyone to know what I knew: that one of our classmates was living a double life as a beautiful blonde woman.
I didn’t realize until later that afternoon that I had a class with the young man. He sat in the far back corner of the class and he never raised his hand. He remained quiet and invisible—and he did a good job of it. We were almost halfway through the semester and I’d never noticed him before. When the bell rang, he managed to slip into the stream of exiting students, and then he managed to disappear. I lost track of him until I found him back at his locker. He grabbed his bag and then he left the school through the back door. And once again, I found myself following him.
He cut across the field and then he navigated through the wooded area between our school and the mall. I used to hang out with Terry and Riley in those woods after school—when we first started smoking cigarettes. I kept my distance from the hoodie-clad young man. I occasionally lost sight of him and then caught up again. He was headed for the mall. I lost sight of him as I climbed over a ledge. Then I saw him sitting in the distance, pulling his feminine outfit out from his bag. I stopped and crouched down to watch.
He got undressed in the woods—completely nude—before slipping into a pair of black lace panties. His legs were shaved smooth. I could see his soft skin glistening from a quarter mile away. He then bent over and slipped into a cute skirt: made with pink tulle. It looked like something a ballerina might wear. Then he slipped a padded bra onto his chest. The bra had flesh-coloured pads built into it, which jiggled slightly, like real tits. He put a fitted black sweater on over the bra, and then took a moment to adjust straps and whatnot so that everything looked proper. Then he got his wig on, and then he started doing his makeup.
He worked surprisingly quickly—as if he’d done it many, many times before. It was an impressive sight, and an impressive transformation. I even found myself wondering if I was truly staring at the same person at the end of his dress-up, even though I’d watched the whole thing from afar. He finished his transformation with a few sprays of perfume, which I could just smell once I started pursuing him again, as he continued towards the mall.
Once we were in the mall, I cut my distance in half. I even got within ten feet of him at one point, when he meandered into the bookstore. I wanted to get a closer look, to see if I could tell that he was truly a man from up close. I knew that it was true, but I still had a hard time believing his transformation could have been so impressive. But I couldn’t see any signs of manliness on his face or on his body. His Adam’s apple was non-existent, and his shoulders were narrow. He had wide hips and a narrow waist, and he had nice thick thighs that looked perfect beneath his tulle skirt. He really was gorgeous—she really was gorgeous. And I really wanted to suck her cock.
CHAPTER III
I’ve always had a secret fantasy to be with a beautiful, well-hung woman. In my fantasy, the girl has big perky tits, but I wasn’t about to be picky. The only problem was, the beautiful blonde was way out of my league. She was an easy ten out of ten. While I followed her around the mall, I witnessed three men hitting on her—one man even asked her for her phone number, but she didn’t give it up. Of course she didn’t give it up—because she probably didn’t own a phone just for her feminine persona.
So how was I supposed to get with her? How could I convince her to go out with me, over all of the other guys flinging themselves at her? I could have told her that I knew her real identity, but I didn’t want to make her feel uncomfortable. I didn’t want to scare her away—and I definitely didn’t want her to stop dressing up.
Over the next week, watching her transform into a woman became my secret favourite pastime. I would follow her out into those woods and then I would excitedly watch as she slipped into her outfit. My own personal favourite was a green dress with a long V cut down the chest. She had a special strapless bra for the dress, also with fleshy built-in cups, like her other bras. The dress was short, and the right breeze would expose just a bit of her bum—enough to get my heart pounding. I’d always dreamed of getting with a girl like her, but I’d never actually seen a girl like her in real life—at least I’d never seen one that I knew was the real deal.
I don’t know why I was so obsessed with my trap fantasy. I don’t know where it came from or when it started. I didn’t like cock—at least not male cock. I hated the thought of a cock dangling between two muscular thighs. I hated the image of hairy legs, and I hated the thought of a muscular jawline. Whenever I watched porn, I always looked away when there was a close-up of the guy’s cock. But if there was a close-up of the girl’s cock—then my gaze was fixed to that screen and my fingers were curled around my own throbbing erection. And then I would think: One day, I want to suck one of those.
And now I felt like I had my chance, though I wasn’t even sure where or how to start. How could I approach her without revealing that I’d been stalking her for days? How could I compliment her without making her feel horribly uncomfortable? Was she even interested in getting with a man? And if so, wouldn’t she be more interested in getting with a guy like Riley, and not a short, scrawny guy like me?
I found myself sitting closer to the young man in my last period class. By the end of the week, I was sitting just two desks away from him. I still hadn’t talked to him—I didn’t even know what his name was, until the next Monday, when the teacher called on him to read a paragraph of a book out loud. He stood up, as instructed, and read quietly from the book. The teacher asked him to speak up. “A little bit louder, Mathew,” she said. And he hardly raised his voice at all. His voice wasn’t particularly feminine—not until he was dolled up. I overheard him that afternoon talking to a cashier at the mall, in his girly voice. His girly voice was convincing—beyond genuine. It was obviously something he’d practised rigorously—along with his posture and his body language. When he was dolled up, he was a completely different person. He really did become a woman.
It was that Monday afternoon, while I was watching her from across the food court, when I noticed Riley was sitting and eating some fries and gravy. He had his head up and his gaze locked on the blonde trap. He watched her as she moved from store to store, and then he got up to pursue her.
My body became tense. He was walking with that confidence he loved to brag about—and he was determined. He stopped outside of the bookstore, which she was inside of, and he took a deep breath. My heart was pounding. I didn’t want him to ask her out. What if she said yes? What if they actually started dating? What if Riley stole her away from me? I suddenly found myself regretting my hesitation. I should have just asked her out as soon as I found out who she was. I should have just tried—at least thrown my hat into the ring while she was still available—if she even was available. At least then I would have had a chance. But now, with Riley as my competition, I had no chance.
I didn’t want to intervene, but my body wouldn’t allow me not to. I ran over to Riley and I caught him right before he tapped on her shoulder. “Hey,
” I said, panting and suddenly out of breath. “What are you doing here?”
He looked at me with a strange grin. “Hey,” he said. “I thought you said you had to go home to do homework.”
“I finished early.”
“Why didn’t you call me?” he asked.
“I, uh—I tried to. But you didn’t pick up.” He looked at his phone and shook his head.
“I’ve got nothing,” he said.
“Anyway, do you want to go see a movie or something?” I looked over and saw the beautiful blonde at the counter. She was buying a book, and about to take off for the next shop. Riley saw me looking at her and then his grin grew bigger. “Do you like her?” he asked.
I shrugged my shoulders. “Who?”
“You know who,” he said. “So I’ll take that as a yes. Why don’t you go and ask her out?”
“She’s out of my league,” I said—and I said it instinctively, as if I was painfully used to saying it.
“Let’s not have this conversation again,” he said. “If you’re confident, you can have any girl you want. I know you don’t believe me when I say it, but it’s true.”
The thing was, I did believe him. I knew he was right because I’d seen some weird-looking guys with some beautiful women before, but I just couldn’t figure out where that confidence could possibly come from. I was still a student. I wasn’t a great looking macho man. I didn’t have a job. I hardly had enough money for lunch, never mind a nice date. So what did I have to be confident about?
“Go and ask her—c’mon. What do you have to lose?” he asked. But I had a lot to lose—I had my whole first impression to lose. And this wasn’t a case of ‘there’s plenty more fish in the sea!’ Because there weren’t too many well-hung beautiful blonde fish in the sea that I was aware of. Riley gave me a shove, but I became tense. “If you don’t ask her out, I will. You’ve got thirty seconds to walk over there.”
I was suddenly regretting my decision to intervene. I should have just let Riley make his move. She probably would have rejected him. I’d watched her reject many dudes over the past week—many of whom were perfectly confident. But now I felt like I had no choice—I had to make a move and it had to be a good one, otherwise I would lose my chance to suck her perfect feminine cock.
He gave me another little shove towards her. I started walking but my legs were shaking. My heart was pounding. I brought my hands up to straighten my shirt and then I noticed my hands were trembling. I was a mess—far from confident. I tried to control my breathing and then I found it hard to control my strides. It seemed like I could only pick one or the other. I went with breathing, and found myself stumbling constantly. She stopped walking as I stepped up behind her, and I nearly barrelled right into her. Luckily I managed to stop myself. I cleared my throat, accidentally grabbing her attention. She turned around to face me, and my heart stopped beating. My lips parted and I felt like a complete fool—like I was wasting the one and only opportunity I would ever get.
“Hi,” she said with a smile that melted my heart.
“Hi,” I managed to reply. I took a deep breath. “Just wanted to say that I really like your dress.” I was thrilled that the words managed to manifest in my mouth without any stutters. She smiled and her cheeks turned a shade of pink.
“Thanks,” she said.
“I really mean it. And I like your hair, too. It’s really nice. It looks soft.” I realized I was starting to sound creepy, but at least I was speaking. At least she didn’t look at me like I was some sort of deranged animal.
“Thanks,” she said again. “I really appreciate it.”
“Have a nice day,” I said. She smiled and nodded and went off towards another shop. I didn’t ask her out like I was supposed to, but I’d made a reasonable impression. I didn’t make myself look like a complete fool—at least I was fairly certain that I didn’t look like a complete fool. So I turned around and I went back to Riley, who was eagerly awaiting the tale of my rejection. “So—where’s her number?” he said.
“I didn’t get it,” I said.
“Because you aren’t being confident enough. You need to be more confident.”
“If you say the word confident one more time I’m going to kick you so hard in the junk.”
“Okay—fine. So you got rejected—it’s not a big deal. You’ll bounce back and it will only get easier. I promise. So do you mind if I go and ask her out?” He had his gaze locked on her—down on her butt. He was watching with a hypnotic glare as her skirt danced from side to side, occasionally teasing a hint of her rump. Even I found myself staring.
“If you ask her out, I’ll never talk to you again,” I said. And it was the first time—maybe in my life—that I spoke with absolute confidence. Riley looked at me with a big smile. He nodded his head.
“I like it. That’s the con—that’s the energy I’m looking for. Talk to her like that and you’re golden—I promise,” he said. That big smile only became bigger. And I felt strangely empowered, with the image of her cock still dangling in my mind’s eye.
CHAPTER IV
I was as stiff as a board when I took a seat next to Mathew in my final class of the day, the next day. I had no idea what he knew—but surely he remembered me as the guy who hit on him at the mall the day before. I wondered if he’d told anyone—if he even had any friends to tell. I’d looked around for him throughout the day, but I hadn’t spotted him, not even out in the parking lot at lunch. He was shockingly good at remaining hidden, blending in with crowds, and slipping out when no one was looking. It wasn’t uncommon for me to lose sight of him when I was following him from the school to the mall. Thankfully I knew where he liked to get changed, out in those woods.
As we sat in class, I looked over at him. He didn’t look up from his desk, but I’m sure he noticed my head turning in his direction. I tried to get a read on him. Was he tense? Was he relaxed? What was on his mind? And then I started trying to see that beautiful blonde. It was hard to believe I was looking at the same person, but I could see the similarities. He had big eyes, which looked even bigger when he was wearing eye shadow and eyeliner and mascara. He had soft features and a cute nose. His skin looked soft—he probably moisturized regularly.
He looked up at me, staring into my eyes. It took a second before I looked away. I’d zoned out while staring at him. In my peripheral vision I noticed him looking back down at his desk quickly. Had I given myself away?
With five minutes of class still left, I noticed him slyly packing his bag, getting ready to bolt out of the classroom as soon as that bell rang. I tried to subtly do the same, but I wasn’t quite as stealthy or as quick as him—he must have had tons of practise slipping away. So when the bell rang, I wasn’t quite ready. I looked down at my bag for two seconds, and when I looked back up, he was gone—nowhere to be seen. I hurried out and zigzagged around the crowds of students towards his locker, but he wasn’t there. I’d lost him. But I knew where he was going—the same place he was always going. So I started out into those woods. But he wasn’t there—his little nook was empty. “Shit,” I muttered.
I really had set off his alarms—he really must did suspect that I knew his secret. And had I ruined everything? Would I never be able to find her again? Would he start being more cautious? Would he find a new mall and a new place to get changed?
“Hey,” a voice said behind me. I turned and looked back with a jump. My heart rate soared. He was standing behind me, holding his bag close to his body—as if his backpack would double as body armour in case I started swinging. “So you were just mocking me yesterday, right? You and your friend were just having a good laugh—is that it?”
I took a step back. Everything was ruined. “No—I—I really was complimenting you.”
“Bullshit. Then how do you know about this place? You’ve obviously followed me here before.”
“Yeah,” I said. “I mean—I was just curious. I saw you changing in the bathroom the other day, and then I recognized you a
t school. What’s the big deal?”
“So why would you follow me?” he asked.
I shrugged my shoulders. “I don’t know,” I said.
“What do you mean, you don’t know?” he asked. He looked like he was ready to bolt, like a tense rabbit with his eye on a hungry hound.
“I don’t know. I guess I like you, or whatever. I mean—not you. I like you when you’re… you know—a chick.”
“You like me?” he asked, and then the woods became silent. I slowly shrugged my shoulders. I felt horribly embarrassed, though I wasn’t sure why—I had no more reason than him to be embarrassed. Although I had been caught stalking my male classmate, so he probably knew that I’d seen him getting changed before, which meant he knew I’d seen him naked. The silence lasted at least a minute—it felt like an hour. “Is this just another joke? Is your friend hiding in the bushes taping all of this or something?” he asked, looking around.
“No—it’s no joke. There never was a joke. My friend thinks you’re actually a chick. And I—I don’t know. I guess I have a crush on you, or whatever.”
There was another long, painful silence. “On me?” he said.
“I mean—on her—whatever her name is,” I said.
And there was yet another terribly long silence. “Georgia,” he said.
I smiled. “I like that name.”
“Me too.” He stared at me, finally letting himself relax, but only a little bit. “And you don’t care that she has—or I should say, doesn’t have—real lady parts?”
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