Besides—I had nothing to be embarrassed about. That new girl looked like a girl. There was no sense in denying it—it was just the truth. She had a pretty face and a hot body. And she knew it—that’s why she was wearing that tiny skirt and that tight white blouse, tied up in a knot at her sternum. Should I have been embarrassed for acknowledging reality? Besides—it was 2019—there were probably transgender people all over the place. I’m sure my sister had been deceived by a few herself.
No matter how I justified it to myself, I was still too afraid to leave my bedroom. I was afraid of running into that trans girl. I was afraid of looking into her eyes and giving her the wrong idea. I hoped that I hadn’t already given her the wrong idea.
It was late when I slipped out of the house to have a cigarette. I was feeling bummed out—feeling like a perfectly good Saturday night was wasted because of one embarrassing little mishap. I walked far out into the backyard and took a long drag from my smoke.
There weren’t many sleepover parties left to be had—two, maybe three at most. My sister was going off to college in another state, leaving me behind. Ten years of sleepover parties would come to an end—at least in the Deniker household. Maybe she would continue to have girls over in her dorm room, but that was irrelevant as far as I was concerned. Once my sister was gone, I would have to find my pussy elsewhere. I would no longer be the only guy in the room whenever I was around pretty girls. I would have to start trying. Maybe I would have to start pushing real weights around, to build up some muscle mass, so that I could stand out from the competition. Maybe I would go through a dry-spell. How long before I had sex again? A month? A year?
I was just about done with my smoke when I noticed a figure pass the kitchen window. One of the girls had come upstairs and was heading towards the bathroom. I remained still and watched as the bathroom light came on and that figure entered. She didn’t go to the toilet. Instead, she went to the mirror, which was close to the window. I back up and tucked myself quietly behind a large bush.
It was the new girl—the trans girl—the girl who ruined my whole night just by looking convincing. She was fixing her hair, running her fingers through it and adjusting her white headband. She leaned forward and puckered her lips, checking the state of her lip-gloss. Apparently it needed some touching up. She reached into a little bag she had with her and pulled out a little tube of pink gloss. I watched as she wiped the gloss onto her lips.
I’d recently gotten a new phone with a state of the art camera built into it. One of the features, which I decided to try out for the first time right then, was the camera’s optical zoom. It could zoom in twenty-times. It was apparently perfect for spying on my sisters’ friends.
The girl was cute—I was willing to admit it. She had big, plump lips and big, flashing eyes. She had the kind of smile that I liked: a little bit mousey, curling up just at the ends.
She brushed a bit of powder onto her face and then she took a step back to admire her full frame. She leaned to one side and then she leaned to another, puckering her lips again as if she was posing for a photo. Then she gently cupped her breasts and lifted them up slightly. I carefully pressed the record button on my phone’s camera—though I wasn’t sure why. I wasn’t sure what I planned on doing with a video of my sister’s tranny friend feeling her tits. Were the tits even real? Were they the product of hormone pills? Were they implants? Or was she just squeezing some socks that she had stuffed into a bra?
She closed her eyes and look a deep breath, as if she was feeling the warm blast of euphoria surging through her body. She paused, removing her hands from her tits, and then she remained still for a moment. Next, she reached down and flipped up her skirt, exposing a large bulge—just in case there was any doubt in my mind that she wasn’t fully female.
My hands started to tremble. I took a sharp breath of air into my lungs, but I wasn’t able to expel the air out. I was frozen, seeing something that I wasn’t meant to see.
The girl pulled her panties to the side, letting her erect cock flip out. Then she just stared down at it, as if she was waiting for it to become flaccid again—and that’s probably exactly what she was waiting for. She couldn’t return to her friends with a big erection. Why did she even have a big erection? Was it from checking herself out in the mirror? Did she get herself aroused when she was feeling up her breasts? Or did she slip away from the party because of the erection—was it possible she got it from one of the girls downstairs?
She took a deep breath and looked around the room. I didn’t look away, even though I wanted to; I just couldn’t. The sight was too shocking. It was something that I felt like I would never see again—a once in a lifetime spectacle. I watched as that stiff cock slowly started to lower down, shrinking with each passing second. And while it was shrinking, I found myself staring at it, strangely mesmerized by it.
It wasn’t a manly cock. It wasn’t rigid and veiny and ugly. It actually had a smooth, feminine look to it. It helped that she was completely shaved. It almost looked like she regularly rubbed moisturizer on it, giving it an even sheen.
Once it was mostly flaccid, she stuffed it back into her panties, pushing it back awkwardly between her legs. Then she dropped her skirt back down and took another look at herself in the mirror. She smiled at her reflection, and then she slipped out of the bathroom, heading back towards the party, leaving me in that backyard with a pounding heart and a lot of confusion swirling in my head.
CHAPTER III
A wave of relief washed over me when I heard the television shut off down in the basement. The house was suddenly silent, and I knew that the girls had gone to bed. I was ready for this particular sleepover to be over so that I could start mentally preparing for the next one. I found myself wondering if the trans girl would be back, and if she was coming back, how could I convince myself to ignore her so that I could maybe get a little bit of action before the end of the summer.
I wasn’t tired. How could I be tired? I’d been sitting in my room with a pounding heart for a few hours. I found myself looking at that video over and over, still in shock that it was real. First I would look at her face and I would convince myself that she was a chick. Then I would see that cock and I would convince myself that she wasn’t actually as pretty as I first thought—so I would restart the video to look at her face, and I would restart the whole process. At some point, my mind was going to have to come to terms with reality: she was a tranny and she was pretty. And there was nothing wrong with thinking that she was pretty, was there?
My phone died, which was a blessing—forcing me to stop watching that video over and over. I thought about deleting it, and I knew that I should have deleted it, but I knew that it was a once in a lifetime recording—I couldn’t just delete it. Plus, I remembered what my sister told me when she said the girl was trans: ‘Don’t you recognize her?’ Was she someone that I knew? If so, who was she? Would my friends get a kick out of that video once I figured out the girl’s identity?
I needed another cigarette. I needed something to help relax my swirling mind and pounding heart. So I grabbed a smoke and I grabbed my lighter and I crept through the house, back towards the backyard. I walked over to the back of the yard and I lit up. Then I looked at that dark bathroom window, where I saw all of the action happen. I still couldn’t believe that it actually happened. I couldn’t believe that a girl stood in that bathroom with a big erection, pointing straight up at the ceiling.
I took a long drag from my cigarette. The nicotine was helping. I closed my eyes for a moment and tried to pull myself back together. I found myself counting the weekends left in the summer. How many more chances would I get to sleep with my sisters’ friends? The summer was over in five weeks, but I knew that my sister planned on moving out a week before the start of the semester—then there was our annual family vacation. So that left three potential slumber parties—three chances to get a little bit of snatch before I had to work for it.
I opened my eyes and notic
ed that bathroom light was on. Was it on when I closed my eyes? No—that was the first place I looked when I stepped outside, and I clearly saw that the bathroom was dark. Someone was in there now! I could see a shadow moving around. My heart leapt up into my throat and I rushed behind that bush. Then I watched as that shadow took a seat. Someone was using the toilet. I couldn’t see them from my angle—there was a small privacy wall blocking the toilet from the window. And why was I watching? Was I a pervert? Was I really hoping to catch a glimpse of one of my sisters’ friends using the potty?
That shadow stood up. Then it started to approach the window.
It was her again: the tranny, the girl with the short skirt and the long cock. She stepped in front of the mirror and went to wash her hands in the sink. I quickly reached into my pocket for my phone, and then I remembered that my phone was charging up in my room. “Shit,” I muttered. But why did I even want it? Was I going to take another creepy video of her? Why was I so obsessed with her? Why was I even allowing myself to look at her?
I felt a burning on my fingers. I looked down and saw that my cigarette was sizzling down to my fingertips. I tossed it suddenly, waving my hand as I let a loud, “Ouch!” out from my lips. I grabbed my finger tightly, though they weren’t seriously burned. Then I looked up and saw that the girl was right at the window now, squinting and looking out.
I froze. Could she see me? Was I hidden enough behind that bush? My heart raced. The girl stepped back, away from the window. The bathroom light turned off, but I still remained frozen. I finally managed to take a deep breath. “Fucking hell,” I muttered. I went to pick up the cigarette butt off the ground so that my parents wouldn’t find it when they were back from their date night. Then I started towards the house. I kept telling myself that she didn’t see me—that I was just being paranoid.
The back door suddenly opened when I was just ten feet away. There she was, standing in the doorway, just ten feet away from me. She looked into my eyes and I froze again. “Did you hurt yourself?” she asked. That slightly masculine voice reminded me that she was actually a man under that skirt.
I remained still for a moment as my heart throbbed. I tried to force a smile, but no smile came. “I just burned my finger a little bit—it’s not big deal,” I said. Finally, that fake smile came onto my face.
“I heard you shout. Do you smoke?”
“Just at parties,” I said.
She looked around and then she laughed. “This is quite the party,” she said.
I laughed too. “Yeah, well I guess I smoke sometimes when I’m stressed out as well. Maybe I’m a smoker and I just haven’t realized it yet.”
She stood still and stared into my eyes. I wondered if she was about to call me out for watching her in the bathroom like a pervert. But she didn’t look disturbed. She just looked curious. But her silence was making me feel sick. “I guess I’d better get to bed,” I said, taking a few steps towards her. But she didn’t move aside.
She leaned against the doorframe and smiled. “Were you watching me earlier?” she asked.
I cleared my throat suddenly and took a sharp breath in. “Earlier? What do you mean? No—I wasn’t watching you.” I laughed. “What are you even talking about?” But I could feel my face turning red. Did she see me? If she saw me, why did she take her cock out? Or did she not see me until afterwards? She never looked over at the window—at least not that I noticed. I took another deep breath. “I wasn’t watching you,” I said again, in case I didn’t make it clear enough the first time.
“Do you have another cigarette?” she asked. “I wouldn’t mind smoking one—if you don’t mind, that is.”
“Um—not on me. They’re up in my room.”
“You don’t mind if I go up and get one with you—do you?”
I paused and bit down on my tongue. “Not at all,” I said.
Finally, she stepped aside. She followed me closely as I moved through the house towards my bedroom. She was too close—uncomfortably close. Or maybe that was just my paranoia. Maybe she was following at a completely normal distance and I was just stirring in my own mind. I looked back at her and caught myself taking a quick look down at her skirt. I knew what was on the other side of that skirt: a big, long cock. There wasn’t much between me and that member: just a thin piece of plaid and an even thinner piece of cotton.
We went into my room and I walked over to my desk to grab her a cigarette. “Here you go,” I said, handing it to her, along with my lighter. She took both and then she stared into my eyes for a moment longer. I’d seen that look and hesitation before. I knew what it meant—at least I knew what it meant when it came from a real girl. But surely she didn’t want me to fuck her—did she?
A lump started to fill my throat. I looked down at her body and I remembered once again how many chances I had left to get easy pussy. “D—Do you want something else?” I asked.
She shrugged her shoulders. “I don’t know.”
I pressed my lips then. I was already regretting the words that hadn’t even come out from my mouth yet. “Do you want to suck my dick?” I asked. A dull pain filled my chest. I couldn’t believe that I said it. I couldn’t believe that I asked a tranny to suck my cock. My legs were suddenly trembling and my heart was stuttering and coughing in my chest.
She shrugged her shoulders again. “I don’t know. Is that what you want?” she asked with a slight grin. I hated that voice. I hated that it reminded me she was actually a boy—just a few months ago, apparently. She may have even been someone that I knew, someone that knew people that I knew. What if she went and told one of my friends that I asked her to suck my dick? What if she told my sister?
“Promise not to tell anyone?” I said.
She nodded her head. Then she walked towards me and put her fingers gently on my chest. She carefully slid her fingers down towards my crotch. I watched them. I wondered if she felt my pounding heart or my churning stomach. She slipped her fingers around the waistband of my pants and then she started to shimmy the pants down, first exposing my pubic hair, then the length of my rod. Her eyes lit up as the band of my pants passed the tip of my cock. She looked up into my eyes. It took me a moment to look back into her eyes. I found myself trying to recognize her, but I couldn’t place her—though she didn’t look vaguely familiar.
“You’re big,” she said.
“Thanks, I think,” I said.
She gently wrapped her fingers around my cock and she began to slowly tug back and forth, still with that smile on her face. She knew just where to grab. She knew where to rub and she knew where to focus her pressure. I suppose she probably had lots of practise with her own cock—even more practise than Felicity Andrews. “How does that feel?” she asked.
I nodded my head. I could feel that my face was red. “You really won’t tell anyone about this—right?”
She smiled. “Do you say that to all the girls you’re with, or just the trans ones?”
I laughed nervously, pretending like I’d forgotten all about the trans thing. I didn’t want her to think that I was a bigot or anything like that. But I was also terrified to let her know that I was into the idea of messing around with a T-girl.
But I really was into it. I started thinking about her big cock and then I suddenly felt more aroused than ever before. I found myself looking down at her skirt, waiting for her bulge to break loose from her panties so that it would lift her skirt up like a tent pole. I wanted to reach down and feel the smooth skin on her shaft. I wanted to pull her foreskin back and lick the tip of her throbbing cock. But I had to remain cool and collected.
I suppose now is a good time to admit that I’d always had a bit of a tranny fetish. I liked to fuck my sisters’ friends from behind so that I could imagine a cock dangling between their legs while I pumped them. I often tried to convince girls to let me into their assholes, so that the fantasy would be easier to muster up.
But it had always just been a harmless fantasy. I never actually planned on sle
eping with a T-girl. I never actually thought that I would touch a cock. In fact, the thought of touching a cock terrified me. I was straight—I didn’t want to be touching cocks. It was just a harmless fantasy, left to pornography—until now. Now, it was a very real fantasy, and it was coming to me with surprising ease. I didn’t even have to use any pickup lines or flirtations. I hardly said anything and she was in my bedroom, waiting for me to ask her to suck my cock.
Now, I was trying to figure out a way to ask if I could suck her cock. My heart trembled at the thought of asking, but that just confirmed that I truly was considering asking. I watched her sink to her knees and then I watched as she plunged my cock into her mouth. She sucked it until it was hard, then she started deep-throating me, getting my entire length inside of her mouth. She had her lips pressed into my pubic hair and her nose pressed against my pubic bone. No woman had ever gotten my entire erection into her mouth before with so much ease. She wasn’t even gagging, though I almost wish that she would have been. I’d always been turned on by gagging, but maybe that was just because no girl could get even three-quarters of my cock into their mouth without gagging.
My heart started racing faster as I remembered that she was one of my classmates, and I still didn’t know who. I was tempted to ask, but I was terrified of the answer. Maybe it was better left alone. Maybe I should just focus on enjoying the moment.
She gently leaned her head back, slipping my cock out from her mouth. It flipped out from her lips and touched the tip of her nose. She let a little giggle slip. She had a feminine giggle—much more feminine than her voice. She looked up at me with those glowing eyes and said, “How did I do?”
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