“I don’t want to scare anyone,” he said. And it was a good point—it was scary. I was terrified of sticking it into my body. I wasn’t even sure if it was going to fit or not—but I had to try. I reached down and moved my panties aside under my skirt. Then I climbed up and lined the huge cock up with my asshole. I just hoped there was enough saliva along his slick shaft so that it would go in. I took a deep breath.
“I’ve never done this before,” he said.
“I know,” I said. “Me neither.”
“No—I mean, I’ve never been with a guy before,” he said. And then my heart stopped momentarily.
“What did you say?” I said. My ears were suddenly ringing and that nausea had finally made its return to my gut.
“Sorry, I shouldn’t say a guy. I’ve never been with a trans girl before.” He stared into my eyes, as if I should have known that he knew. “I mean—I know who you are. Don’t get me wrong—you look good.”
“You know who I am?” I asked, my voice shaking. I could still feel his warm throbbing tip pressed up against my tush hole.
“Yeah,” he said. “I don’t mind though. Like I said—you look good.”
My heart was racing. My identity had been compromised. Would Jimmy tell anyone? Was he the only one who could tell? Why didn’t he say anything? Why didn’t anyone say anything? “Do you still want to do it?” he asked.
“Um, yeah,” I said. Though I wasn’t sure what I wanted. I couldn’t even remember how I’d ended up in his bedroom, straddling his giant, saliva-covered cock. I looked down and found myself taken aback by how big it was all over again. I closed my eyes and tried to push away all of my anxieties. He wasn’t going to tell anyone—and so what if he did tell anyone? Could they make fun of me? They’d spent the whole night checking out my ass and asking for my phone number—how could they turn around and pretend like I should be ashamed of myself?
Maybe there was nothing to be ashamed of. Maybe I was better off dressing like a girl. Everyone seemed to like me when I was a girl—and I had more fun wearing makeup and skirts and dresses and panties. So what was really the big deal? So a few kids at school might make fun of me—but they would get over it. Kids were always making fun of one another and then getting over it. In fact, there was a trans girl in one of my classes—no one ever made fun of her—so what was I so worried about?
I started sinking down, feeling his cock sliding up into my asshole. It was a tight squeeze, but somehow he fit. He sunk deeper and deeper. I clenched hard but that didn’t stop gravity from pulling me down. I could feel his cock up in my throat—at least it felt like it was in my throat. I couldn’t believe I was actually able to accommodate his massive length.
“Does it hurt?” he asked.
“No, it feels amazing,” I said. And it was true—it felt beyond incredible. My ass was pulsing with warm euphoria. I could feel my cock twitching with that same ecstasy. I wanted more of him inside of me, so I sunk down even further, until my butt was pressed against his lap. And then I started to bounce. It felt so much better than the suction-cup dildo, and so much better than the vibrating egg. This was a whole new feeling: warm and real. I could feel his skin pulling up and down his shaft. I could feel his veins pumping blood. He was really inside of me—a part of his body was inside of my body!
I kept bouncing. His hands held my hips and guided me up and down his long shaft. “Shit,” I muttered. I could see a slight bulge in my stomach every time I came down: the tip of his cock pushing against my gut. Maybe it was a concerning sight, but I just thought it was erotic. I felt my cock getting harder. And I kept bouncing—I kept massaging my anal walls with his long curved dick.
“Can I stroke you?” he asked.
“Yes. Stroke me,” I said. “Please stroke me.” He curled his fingers around my cock and he began to stroke my length. My cock looked tiny compared to his, but I didn’t mind. He was the man, after all—and I was the woman. Women don’t need to have giant cocks.
“You’re going to make me come,” I said. He was aiming my cock right at his chest while he pumped. He didn’t seem to mind the idea of getting coated in my jizz. “Any second now,” I said, giving him a second warning, but he didn’t react. I clenched and tried to hold back, but I couldn’t hold on for long. I ended up spraying his chest with warm cum. He let out a loud elated sigh. “I want you to come inside of me,” I said.
“Okay,” he said. His face was dark red and I could tell that he was close. I kept bouncing, up and down, massaging his shaft with my tight anus. I could feel him bloating up and getting ready to burst—and second…
He grunted, and then I felt it: a hot burst deep inside of my body. He squirmed and groaned and I’d never felt fuller in my entire life. And then he pulled out and suddenly I felt empty. I flopped over next to him, and we both lay on our backs as we caught our breath. “That was amazing,” he said between breaths.
“Yeah,” I said. “We should do it again sometime.”
“I would like that,” he said.
I looked over at him and smiled. I stared into his eyes and then I asked him what he thought of me coming to school as a girl. He liked the idea. He had no problem with people seeing him and me together in the halls, holding hands. He even seemed to think people would embrace him. And then I asked if I could borrow some of his sister’s clothes until I got my own.
“I don’t mind,” he said with a big smile. I couldn’t remember the last time I’d seen him smile—it had been many years. It was a nice sight to see, and it was a nice way of letting me know that I was making the right choice. My sissy punishment had turned out to be the best thing that ever happened to me.
THE END
MAKE HIM MY GIRL
When Dave sneaks into the women’s bathroom at the mall, because the line for the men’s bathroom is too long, he doesn’t expect to spot one of his male classmates getting dolled up in a blonde wig and makeup. And he certainly doesn’t expect to find himself so attracted to her, once he sees her perusing the mall with her tall heels and her short dress.
He’s always wanted to be with a girl just like her, with a little extra between the thighs—so he begins to hatch a plan to make his cross-dressing male classmate his girl.
CHAPTER I
It wasn’t my proudest moment, but I really had to go. I’d been holding it for hours, hoping I would be able to get home to use my own bathroom—but I ended up getting stuck at that mall with my buddies for far longer than I’d anticipated. I realized while we were in the food court that I would piss my pants if I had to hold it for another five minutes.
And I sure as hell wasn’t going to wait in that line, squirming with my hands between my legs like a three-year-old who still had no idea how to control his bladder. According to the man in front of me in line, two of the stalls were broken and all of the urinals were broken, leaving just a single toilet for the entire male population in that mall to fight over. I attempted to stand in the line, but after two minutes of standing still, I caved. There was no line for the women’s bathroom. Everyone in the line kept talking about slipping into the girls’ bathroom quickly, but no one was brave enough to do it—no one but me.
Though I’m not sure ‘brave’ is the correct word. I wasn’t brave. It was either piss in the women’s bathroom or piss in my pants, and maybe I didn’t think I was brave enough to piss in my pants in a crowded shopping mall.
The women’s bathroom was nice—painted a muted pink colour, and it smelled like flowers. The floors were impressively clean and the counters were shining with lemon Pledge. I ran into an open stall and I threw up the toilet seat. I nearly pissed standing up when I remembered I was in the girls’ bathroom—if a woman saw my front-facing feet, she would know they’d been infiltrated. So I sat down and went about my business in a ladylike sort of way. And I’d never felt more satisfied in my life.
I felt another large wave of relief when I saw another man enter the stall next to me—apparently I wasn’t the only one dying
to use the toilet. I didn’t know for sure that it was a man next to me, but those were men’s sneakers (white sneakers with three neon green stripes on the side), and what looked like a pair of men’s jeans.
I couldn’t help but notice when he slipped out from those shoes. I saw him reach down and pull off his socks. He stuffed his socks into his empty shoes, and then his pants slid down to his ankles. His belt hit the floor with a clunk, and then he stepped out from the pants. And that’s when I saw that his ankles were hairless—so I assumed the rest of his legs were hairless. And then I began to wonder if it was actually a man beside me.
So I remained still on the toilet seat, even though I was finished my business. I didn’t want to sneak out until I knew the bathroom was empty. I checked my phone for new messages and then I looked back down at the feet of the stranger next to me. Now she was slipping a skirt up her legs. It was a black skirt, and I only saw it for a couple of seconds. Next she slid on a pair of white stockings, and then she slipped her feet into a pair of black heels with deep red soles. Her sneakers and jeans and her thick black hoodie were now stuffed into a bag, which I could also see, leaning against the stall door. I figured she would be done at any second.
My phone buzzed. I checked it again. I had a message from my buddy. “Where the hell did you go?”
“I’m stuck in the bathroom,” I replied. “I’m waiting for this chick to leave before I sneak out.” I looked back down and saw that the girl was now digging makeup supplies out from her bag. I watched as she picked up a small makeup mirror, and then I realized she was going to be a while—and I could probably sneak out without her noticing. So I flushed and then I took a deep breath before bolting for the door.
I met up with my friends back in the food court. They were already finished their lunches, and I hadn’t even bought mine. They weren’t keen to wait for me, so I told them that I would meet up with them. I went and bought a couple slices of pizza, and then I started to wander the mall while eating, in search of my friends.
I peeked into a few stores where I thought they might be. Terry was always lingering in the video game store, and Riley was always wanting to look at hats in the cap shop. But they weren’t in either store.
Sometimes Riley would go into women’s clothing stores and pretend to be shopping for his non-existent sister’s birthday present—it was an excuse to hit on girls. He would say things like, “You’re actually her exact size by the looks of it. Do you mind trying this on for me?” He would get girls to try on the skimpiest outfits, and then he would compliment them and offer to buy them the outfits. It was a surprisingly effective strategy—women seemed to love it… So I found myself looking in women’s clothing stores, trying to locate my friends.
I was peeking in a lingerie store when I saw a familiar sight: a pair of black heels with red soles. The woman with the shoes was a tall blonde—her hair was so blonde, it was almost white. She was wearing a black skirt—the same one I saw the girl in the bathroom slip up her legs, and she was carrying a backpack—the same one I saw propped against the bathroom stall door. She was admiring a sheer white slip with pink embellishments. Her lips were shining pink with gloss, and her eyes were large and stunning. I was certain it was the girl from the women’s bathroom.
She looked strangely familiar—perhaps I’d seen her around the mall before, maybe even before she changed out from her sneakers and jeans and her black hoodie… But why was she ever wearing such a boyish outfit? She was a beautiful blonde—why would a beautiful blonde put on a pair of baggy jeans and a baggy black hoodie? I’m sure she had her reasons. I was surprised Riley wasn’t in the store, trying to get her to try the slip on for his imaginary sister.
She looked over at me and smiled. My heart skipped a beat and I found myself looking away quickly, like a shy child. It was a strange sensation—one I hadn’t felt in years, since I was a little virgin who was completely terrified of women. When I finally gathered the courage to look back at the pretty blonde, she was gone—she’d slipped into a change room to try on the white and pink slip. So I carried on, and eventually found my buddies in the bookstore. They weren’t looking at books though—they were looking at the girls reading the books. Riley had a theory that bookworm girls were the easiest girls to pick up, because they weren’t used to being complimented. I’d always thought it was a stretch of a theory, but that afternoon he proved me wrong by getting a pretty girl’s phone number in a matter of minutes.
“You’re just lucky because you’re six-five and you look like a goddamned quarterback,” I said. Riley had impeccable genes. He never stepped foot in a gym, yet he was still built like a professional athlete. He was tall and he was naturally handsome, even though he rarely showered and never bothered to style his hair.
“It’s all about confidence. It had nothing to do with the way you look. You can get any girl in the world if you’re confident, even if you look like The Hunchback of Notre Dame,” he said. I didn’t believe him—it was easy for him to say because he certainly didn’t look anything like The Hunchback of Notre Dame. He could have been a model; in fact, he’d been approached numerous times by modelling agents on the streets. He didn’t know what it was like being short and skinny, with an average face and a long torso that made most shirts look unflattering.
“Yeah, sure,” I said.
“That girl there. I want you to go get her number,” he said to me. He was pointing at a short brunette with long bangs. She was cute, sitting with a warm smile on her face as she read a book about politics.
“She’s out of my league,” I said.
“There are no leagues. Just go talk to her. Tell her she looks beautiful and then ask for her number—don’t say anything else. Just don’t stutter. Be confident, and it will work—I promise.”
“She’ll probably give me a fake number,” I said.
“Call it in front of her—you’ll hear her phone ring. I promise.”
So I dragged my feet over to the girl. My heart was racing. I knew I was about to be rejected—and a part of me was hoping to be rejected, just so I could prove Riley wrong. But another part of me was hoping Riley was right, that I would land a date with a gorgeous brunette who was way out of my league. I stopped in front of her and she looked up at me. And then I froze. I forgot what I was supposed to say, and now I was standing in front of a beautiful woman with parted lips and tense shoulders.
“Can I help you?” she asked.
“Uh,” I said. It took a minute before I remembered my lines. “You look beautiful,” I said, sounding like a robot. “I would, uh, really like it if I could get your number.”
She looked horrified, as if my teeth were falling out while I was talking. She stared up at me and then stood up slowly. “I’m sorry, I have to go. It was nice talking to you,” she said. And then she was gone. I could hear Riley laughing behind me.
“What the hell was that?” he said. My heart was still pounding and my lips were still stuck parted.
“I did what you said,” I said.
“You call that confidence? That was hard to watch. I thought you were about to piss your pants in front of her.”
“It’s a catch-22, isn’t it? I have to be confident to get her number, but how can I be confident if I’ve never gotten a girl’s number? It’s like the Peter Pan fantasy land—you can only get there if you believe in it, but how the hell are you supposed to believe in it if you’ve never seen it?”
“Well it helped that the kids saw Peter Pan flying about, didn’t it?” Riley said with a laugh. “I’m your Peter Pan, Dave. You’ve seen me do it.”
“Again, you’re six-five and look a bit like Brad Pitt. I’m five-five and I look more like Steve Buscemi.”
“I bet Steve Buscemi gets laid like crazy,” Riley said.
“Yeah, because he’s rich and famous.”
“There’s always going to be an excuse, Dave. We’ll try again later. Let’s go find Terry. I’m not sure where he wandered off to, but I’m going to bet
we’ll find him buying video games.” So we wandered off towards the video game store. My heart took a few minutes to relax and accept the rejection. As we approached the video game store, I spotted that pretty blonde again. She was walking towards the food court with a small lingerie store bag at her side. I wondered if she bought the white and pink slip that would have looked so cute on her. I wondered if she planned on wearing it for someone, or if it was just something she planned on enjoying alone.
CHAPTER II
I had an embarrassing moment at school the next day. I was at my locker when a girl came up to me and said, “I heard you asked out my friend, Madison yesterday. I heard you were practically drooling while hitting on her.” I’d never talked to the girl standing before me, but I’d seen her around the halls. Of course, with my luck, the brunette I’d hit on was someone my classmates knew well.
“I was dared to ask her out,” I said. “It’s not a big deal.”
“She’s way out of your league. No offense,” said the girl. She had a big smirk. But she was nothing special herself—probably in my league, which wasn’t exactly a compliment.
“None taken,” I said, and I was happy when she walked away. After my next period, another girl came up to me to rub my blunder in my face. “I’ve never seen Madison look more disturbed,” she said.
“Well you can tell her I’m sorry—I only talked to her because Riley dared me to. I couldn’t actually care less,” I said. Though my cheeks still burned warm with embarrassment.
As I walked into the cafeteria during lunch, a whole group of girls looked over at me and started to snicker. My heart fizzled down into my gut, so I turned around and went the other way. I ended up buying my lunch at the 7-11 across the street, and then I ate it in the parking lot with the other kids who were too embarrassed to eat in the cafeteria.
My food wasn’t fantastic. It was a ‘pizza sub’, which I’m pretty sure had been sitting on the shelf for a couple weeks too long. It was very saucy on one side and then completely bare on the other side. I still ate it because I didn’t have any other options. While I was taking my last bite, I noticed the young man sitting across from me in the parking lot, eating an equally disappointing sandwich. He had short scruffy hair. But what caught my attention was his sneakers: white with three neon green stripes. They weren’t terribly unusual sneakers, but he was wearing a black hoodie and baggy blue jeans—the same outfit I saw in that women’s bathroom.
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