I shook my head. “I don’t care,” I said.
He stared at me for a moment longer, as if he was trying to spot my bluff. “So do you—I don’t know—want to come to the mall with me or something?”
I shrugged my shoulders. “Maybe we can see a movie,” I said.
He smiled. “That could be fun. Just give me fifteen minutes to get ready.” I watched as he went over to his spot and started to get undressed. I looked away this time, giving him some privacy. I went over to a fallen tree and I took a seat while I checked my Facebook and my e-mails. My heart was still racing. I was about to go on a date with a beautiful woman—but I was also about to go on a date with a boy from one of my classes. I knew I was playing with fire—I knew a story like this was high in demand in the gossip scene. Riley would have loved to rip me apart for going on a date with a trap. The other kids at school would have loved to mock me to hell and back. And what would my parents think? My father would probably drag me by the ear to church every Sunday for the rest of my life—or maybe every day. He would probably never look me in the eyes again—
“Ready?” she said behind me. I turned around. She was beautiful, dressed in a blue floral dress, which barely extended down past her rear end, just like most of her other dresses. She had her blonde hair nicely curled and her face was expertly dolled up.
“Wow,” I said. I was taken aback. She got ready quickly, and she looked amazing. I could hardly see the boy beneath the makeup—but I knew it was there. And for our whole date, I couldn’t stop reminding myself that there was a shy boy under that floral dress and padded bra. And I wouldn’t stop reminding myself that there was a cock stuffed into those little panties. At one point I knelt down to tie my shoe, and I could see up, between her legs. I could see her red panties, and I could see the slight bulge, which could have easily been mistaken for a puffy camel toe. But I knew better—I knew it was a cock, and I still wanted to suck it.
But now I was afraid. Now it was a potential reality: I might actually end up sucking that cock. And I’d never sucked a cock before—I didn’t even know if I would be able to do it! It was one thing to see a feminine cock on a computer screen, but what about in real life? What if I couldn’t stop picturing the boy while it was there in front of me?
“Are you okay?” she asked, as we stood in line to get our movie tickets.
I forced a smile. My heart was still pounding mercilessly. “I’m good,” I said. “Just nervous—I’m a bit of a wuss with horror movies.”
“You can’t be,” she said. “I’m a wuss with horror movies. One of us has to be the brave one.”
“I’ll do my best then, I guess,” I said. But I wasn’t worried about the horror movie. I knew that I wouldn’t be paying attention to a single second of the movie. I knew I wouldn’t be able to think of anything but her beautiful feminine erection for the whole duration of the flick.
CHAPTER V
The theatre was empty until we arrived. We took seats in the far back corner, just as the film was beginning. We’d missed the ads, but the movie was already old so the ads weren’t worth catching anyway—not that I would have been able to focus during the ads. As soon as we were sitting down, my attention was locked on her.
She crossed her legs, making her dress ride up, teasing a sliver of her red panties. I tried not to look, worried I would look like a creep. I didn’t want her to think that I was gay and just using her to satisfy some weird gay fantasy—even though I suppose that’s exactly what I was doing. I really did like her—I really did think that she was beautiful. But I also really wanted to suck her cock, even though the thought of sucking it made my body tense and my heart insane.
“Hey look,” she said. “The arm rest goes up.” She pushed it up, taking away the only thing between us. “I don’t think I’ve ever seen that before.”
I forced a smile. I knew she was inviting me to come in closer, to throw my arm over her. She wasn’t shy once she was in her feminine disguise—she really did become a whole new person: glowing, confident, and beautiful. As a girl, there was no way she could slip out of a classroom without being noticed. There was no way she could have blended in with a crowd of students. She was stunning and warm and soft. I had my arm around her.
She snuggled in close. I couldn’t believe how quickly she’d accepted me, even though I’d been caught stalking her like a crazy person. Though she maybe didn’t know just how many times I’d followed her out into those woods, and she probably didn’t know how many times I’d walked behind her at the mall, dreaming about having her along in a dark movie theatre. And now I had her—and now I was too afraid to actually act on my fantasies.
I looked down at her crotch. There was only a thin layer of satin and a thinner layer of lace between my eyes and her cock. I’d seen it before, from far away, when she would get changed in the woods—though I’d never been close enough to know if it was big or small, and of course I’d never seen it erect. She looked over at me now, and I darted my gaze away swiftly. She giggled.
I looked back slowly with warm cheeks. “What’s up?” I said.
“Give me your hand,” she said.
I slowly gave her my hand. She took it and brought it down to her lap. “W—What are you doing?” I asked, my heart suddenly stuttering. She pushed my hand down between her legs, under the skirt of her dress.
“You need to just get it out of your system,” she said. I could feel her bulge. She made my hand rub the bulge. I could feel it moving. I could feel the edges of her panties. All I had to do was slip my fingers beneath those edges and I would be touching her bare cock. I looked over at her. She was grinning and staring into my eyes—she wasn’t shy. If anything, she thought it was funny. I couldn’t understand it. As a boy, she was so shy and timid. But as soon as she was in that wig and makeup, she was boisterous and shameless.
I slipped my fingertips under her panties and I curled my fingers around her cock. I wanted to stroke her, but I froze. I was touching a cock—a real cock. This wasn’t just a nighttime fantasy—this was real life. It was warm and soft and I could feel blood slowly pumping into it, and I completely blanked out. I had no idea what to do next.
“Okay, you had your fun,” she said, pulling my hand out from beneath the skirt of her dress. She placed my hand on her thigh and then she fixed her skirt and turned her attention back to the movie. She still had that smile on her face. I felt relieved and teased at the same time. And then I started thinking that it was strange that she would want me to feel her cock—as if she wanted to remind me that she wasn’t actually a woman. And why would she want to remind me that? Unless she knew that I was just some pervert trying to live out a crazy fetish…
I wanted to kiss her, but every time I would gather the courage to lean over and do it, I would remember the face of the young man behind the makeup. I would remind myself that I was straight, and then I would find myself in an internal struggle, trying to figure out if it was gay to kiss Georgia. And once I would decide that it wasn’t gay, then my courage was gone and I needed to gather it all over again, restarting the tense cycle. I didn’t end up kissing her.
The movie went by slowly, until it was over, then it felt like it was over suddenly. The lights came on and Georgia stood up. “Well I should be heading home,” she said. I walked her to the parking lot and then I waved her goodbye as I stood with so much regret. I didn’t end up kissing her, but I wished that I had kissed her. Had I kissed her, one thing would have led to another, and I would have finally gotten to taste the cock I’d been dreaming of tasting for so long. But instead I was left with nothing but a terrible fear that my classmates would soon find out about our little date. Because if I could find out that she wasn’t really a woman, then anyone could find out that she wasn’t really a woman. And surely I wasn’t the only one who knew. Surely there was someone else in that school of five thousand students who knew Mathew’s little kinky secret.
CHAPTER VI
It was late that night when
I received a text message. It was from an unknown number. “Hey Dave. Do I have the right number?” I stared at the message for a moment before replying. I figured it was someone from my biology class, seeing as we’d recently been put into groups for an assignment.
“This is Dave. Who’s this?” I replied.
And then, a minute later, my phone buzzed. The person had sent a picture—it was Georgia. And she was on her bed in a dimly lit bedroom. The photo was a bit fuzzy as her auto-exposure tried to compensate for the low light. She was in a white and pink slip—the one she had been admiring at the lingerie store—and she had her legs spread wide. She wasn’t wearing panties under the slip, and her cock was semi-erect, curved to one side.
“Looking good,” I replied.
“I thinking about you,” she said.
“What about?” I asked. My heart was racing and I couldn’t take my eyes off of the picture she’d sent—and then she sent another picture. Now her cock was fully erect and standing tall. It was just a still photo, but I felt like I could see her cock throbbing. It looked thick—too thick to fit into any pair of panties. I couldn’t believe how big she grew. “Your lips,” she said.
“I wish I was there with you,” I said.
“Me too,” she replied. “What would you do if you were here?”
“I’d suck you off,” I wrote. “And then I would fuck your little asshole.”
“This little asshole?” she said, and then she sent another picture: her on her back with her bum in the air. There was a plug pressed into her tight hole.
“That one,” I said. “And I would come inside of you.”
There was a silence, and then she sent another picture. It was of her cock, slumped on her abdomen. Her chest and abdomen were covered in streaks of cum, and there was a drop of cum drooling out from the tip of her dick. She’d finished. She sent a little winky face and then said, “If you really like me, you’ll delete the pictures.”
Of course I didn’t delete the pictures. Those pictures would be dear to me for the rest of my life. I saved them to a hidden folder on my computer and then I deleted the photos off of my phone. “Good night,” she wrote before she stopped texting for the night. And I took my computer into the bathroom and I came faster than I’d ever come before. My bathroom floor was a mess, which I cleaned up with wads of tissue paper.
And I couldn’t wait to see her again. My heart was already racing during my second last class of the day. I struggled to pay attention to my biology teacher, even though he was going over notes for an upcoming test. I made my way quickly to my final period class, so I could get a seat close to Mathew. He wasn’t there when I showed up, but I took the seat next to the seat he normally took. And then I waited, pretending to act casual. I pulled out my phone and pretended to check my e-mails. And then the class started—but he still wasn’t there. I looked around and then spotted him on the other side of the room. For the first time ever, he was sitting in a different seat, on the opposite side of the classroom. He didn’t even look over at me when I tried to get his attention. It was as if he woke up and regretted everything. It kind of seemed like he was ashamed of me.
During that class, the teacher went over how to properly format a letter. It seemed like elementary school stuff, but a shocking number of students in our class had no idea how to format a letter. So for the entire class, we wrote mock letters, using small squares of construction paper as stamps. We learned to write an address properly, and we learned to write a return address properly. At the end of the class, we put our envelopes on our teacher’s desk to be graded.
Mathew knew that I was going to try to follow him, so he got up with five minutes left in class and asked if he could use the bathroom. The teacher allowed it, and he never came back. By the time the bell rang, he was gone. I tried looking for him in those woods, but he wasn’t there. I went to the mall and looked around, but he wasn’t there either. So I sent him a text message. “Did I do something wrong?” I asked.
And she replied quickly. “Wrong? What do you mean? I’m at the park near Westmount. Why don’t you come and walk with me?” I had to take a bus to get there—using the last of the money in my wallet for bus fare. I got off the bus and scanned the park, and then I saw her long blonde hair sitting at a bench. She was watching the city skyline with her beautiful legs crossed. “Hey,” I said behind her. She turned around with a big smile on her face, as if she was excited to see me. And I just stood there, deeply confused about everything. Why was she acting so weird? Why was she so determined to avoid me during school?
“So I guess you probably just don’t want people to know about us, right?” I asked.
She looked at me strangely, as if she didn’t know what I was talking about. Then I started to wonder if she suffered from some form of split personality disorder. Maybe she really was a whole different person when she was dolled up, with a whole new mind. “I don’t mind if people know about us,” she said. “We’re just friends—there’s no harm in being friends, is there?”
“No—I mean… At school, you didn’t sit next to me,” I said. And I realized how desperate I sounded as I said it.
She didn’t say anything. She just looked back at the city, and then she changed the subject. “Don’t we just live in the prettiest city?” she asked.
“It’s pretty nice, I guess,” I said, taking the seat next to her. “Have you ever thought of just coming to school as a girl?” I asked. “People do that now, you know. There’s a girl in my English class who used to be a guy—no one cares. It’s like… normal, I guess.”
“I know,” she said with a smile. “It’s just better this way.”
“People really wouldn’t care—it would maybe be awkward for a day or two, but that’s it,” I said.
“I know,” she said, almost snapping. She wanted me to drop it, so I dropped it. And maybe it was best that she didn’t come out to the whole school—because if she came out, then I wouldn’t be able to see her anymore. Now when I saw her, I didn’t have to worry about my friends catching us together. If Riley saw us, he would think that she was a girl, and he wouldn’t make fun of me for being with a trap because he would be oblivious. And I wouldn’t want to have to see her in secret—we lived in a relatively small town. Seeing her in secret meant seeing her in the dark of the night, in private, as if she was a prostitute and I was a criminal.
But I liked sitting next to her at the park, watching the shimmering skyline, not worrying that someone behind me would recognize her or me and then leak the gossip around the school.
“What do you want to do?” I asked.
“What’s wrong with this?” she asked with a grin.
“This is fine—there’s nothing wrong with this,” I said. “I just thought that maybe we could go do something.”
“Like fuck?” she said. My heart bounced up into my throat.
“Um, I was thinking more like bowling. But if you want to, uh, do that—that’s fine, too,” I said.
She started laughing. “I’m kidding, Dave,” she said.
“Oh,” I said. I felt my cheeks burning warm. I looked forward at the city. I could hear my heart pounding. I hoped that she couldn’t hear it—I was already embarrassed enough. When I looked back over at her, she was looking at me with a big smirk. “What is it?” I asked.
“If you want, I can suck your cock. I know a private spot.”
I tried to swallow the lump in my throat. “Really?” I said. “Or are you kidding again?”
“I’m not kidding.”
“Can, uh, can I suck yours too?” I asked.
Her smile grew larger and then she stood up. She reached out her hand to help me to my feet. I was shocked by how small and dainty her hand was—as if it really belonged to a woman. Georgia really was born to be a woman; it was a shame she didn’t want to commit fully. It almost seemed like a waste, like every minute she was Mathew was a wasted minute.
CHAPTER VII
Georgia took me to a corner of th
e park that I didn’t know existed. We had to scale down a steep treed hill, and then we had to climb over a series of fallen trees—but the spot was private. “Me first,” she said, sinking to her knees. He nestled up close and immediately started undoing my belt. I’d expected some foreplay first: some kissing, maybe some fondling, and then some slow undressing. My Georgia wanted to go straight at it—she really wanted to suck my cock. And I suppose she was a male under that dress and under that padded bra. Men don’t generally care for foreplay, so why would a trap care?
She tugged down my jeans and then she tugged down my boxers. I was already hard, which I was embarrassed about. She giggled, which made the embarrassment burn a little more. She looked up at me with glowing eyes and said, “Don’t be shy. I’ll be gentle.” She slowly wrapped her fingers around my cock and then she started to gently pump her hand up and down. It felt nice: her warm hand wrapped around my private parts. She was leaning her head in closer and closer, and finally, she stuck out the tip of her tongue and teased the tip of my cock. My legs trembled slightly. She looked up at me again. “This is the first cock I’ve ever touched, by the way,” she said. “I mean—the first cock that isn’t my own.” She laughed. “You’re my first—I hope that doesn’t weird you out.”
“No,” I said, but I wasn’t sure I believed it. She was too good—she moved her hand too elegantly and she was too relaxed. The way she drew the tip of her tongue in circles—how could this have been her first time? If it really was her first time, then she was a natural.
She plunged her head down, sliding her lips down the length of my shaft. She pressed her nose into my pelvic bone as my tip pushed into her throat. But she didn’t gag. She managed to keep her throat open impressively. It felt good. Her mouth was warm and wet and she knew just how to move her tongue to make me squirm.
She pulled her head back and plunged down with an elegant rhythm. Her lips slid along the whole length of my haft without stopping. She moved quickly and gracefully, and she managed to suck consistently. Whenever her lips crossed over my throbbing tip, I worried I was going to burst. It felt so good, the way she would quickly wrap her tongue around my tip before exploring the rest of my shaft again before making yet another trip back up.
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