[Patreon Exclusive] GOING THROUGH CHANGES: Chapter 7 (Patreon)

Chapter 7

I couldn’t sleep that night. It was almost 1:00 AM and the house was dark and silent, but my mind was busy and loud. I was running through all of the possible nightmares that I could be facing if I really went into that school dressed like a chick. What if word got around to my friends back in Toronto somehow? What if someone posted my picture online in an attempt to publicly humiliate me? What if the kids didn’t really care about the zero-tolerance rule, and everyone just made fun of me to my face? They couldn’t expel the whole school, could they?

I carefully got up around 1:30 AM and got that schoolgirl outfit out from my bag. I took off my pyjamas and was about to put the blouse and skirt on when I noticed my chest lumps were bigger once again. They really were growing, and they really were starting to look just like tits. I cupped them and squeezed them. Was I going to need a bra soon? Would everyone in the school think that I was a slut, with my nipples pressing against my blouse? It was too late to raid Aunt Fey’s bedroom for a bra, so I was just going to have to take my chances.

I quietly put the outfit on, along with the wig, and then I laid myself down on the bed. I liked the way the outfit felt. They use softer fabrics for women’s clothes—it’s not really fair. I crossed my legs, rubbing my clean-shaven thighs together. I put my hands behind my head, feeling my soft hair through my fingers. Even alone, without a mirror or a camera, I still felt sexy in the little outfit. And why was it possible that I could feel sexy? Surely that was some sort of faulty wiring in my brain. Men aren’t supposed to feel sexy. Men aren’t supposed to grow breasts either.

I closed my eyes and tried to think of some potentially positive scenarios. I imagined guys ogling me, and girls wanting to hang out with me. I imagined myself sitting with one of those blonde chicks, painting our toenails together while gossiping about boys. I imagined one of the football jocks hitting on me, putting his arm over my shoulders, whispering into my ear as his stubble tickled the side of my face. I imagined myself sneaking into an empty classroom with him. I imagined him bending me over and eating out my asshole before sticking his throbbing erection into my body. I imagined him pumping me until cum was dripping out the tip of my cock.

Then I opened my eyes and saw that my plaid skirt was standing up. My cock had escaped my panties and was now throbbing and begging to be jerked off. Was that going to be a problem? What if I got an erection in the middle of class? A little pair of panties wasn’t going to save me the way a tight pair of boxer briefs and jeans could. If the class saw my skirt standing up the way it was now, then I would surely be doomed.

Thankfully, I was alone in my bedroom. I could do whatever I wanted and no one could see me. So I reached down and started stroking myself. Then I looked over at the tall candle on my nightstand. I suddenly had a naughty idea in my head—an idea that would accompany my little fantasy, in which the football jock is fucking me in the ass in the empty classroom. I reached over and grabbed the candle. I gently sucked on the base, getting it lubricated with my saliva. Then, I reached it down and pressed it between my butt cheeks. I used my free hand to hold my panties to the side. Then, with a bit of cramming and squirming, I got that candle pressed into my asshole. I gasped but managed not to make too much noise.

I took a deep breath and started plunging it in and out. I closed my eyes and pictured myself bent over a classroom desk. I could practically feel his throbbing veins inside of me. I could practically feel his shaft swelling up as he held back his warm, wet orgasm. I gripped the edge of my bed. I was fucking myself quickly, plunging that candle down as saliva squished out from my tight hole.

I had my free hand on my cock. I was jerking myself off quickly, but in my mind, the jock was jerking me off. He hand his big, muscular hand wrapped around my shaft and he was pumping ferociously, desperate to see the steamers of cum shooting out from my cock. And I was close. He was about to get what he wanted. I tried holding back, but the cock in my ass just felt too good. I ended up coming, blasting my load into the air. One shot hit my lips, the next few got my blouse, and then the last few got my skirt. I was covered in my hot load.

I sat up quickly. “Shit!” I muttered under my breath. It was the only outfit I had. I grabbed handfuls of tissues and started scrubbing the cum away. “Shit, shit, shit,” I said. I managed to get the cum out from the skirt with a little bit of water from my drinking glass. I could still feel the dried cum on my blouse, but I couldn’t see it. I just hoped that it would be invisible to everyone else as well.

I finally fell asleep around 4:00 AM, which wasn’t ideal, seeing as my alarm was set for 5:30 AM, so that I would have time to get myself dolled up out in those woods before my bus came. Thankfully, Aunt Fey had a pot of her amazing coffee ready for me when I crawled out of bed. For breakfast I only had time to eat a single piece of toast, which seemed like more than enough. It was the coffee that I really needed.

I took a full thermos with me on my hike towards the bus stop. I walked for fifteen minutes before I slipped off the road and found a private spot in the woods where I could get myself ready. I started with the outfit, then the wig, and then I spent the next thirty minutes perfecting my makeup. I would have liked to spend more time, but I was already behind schedule. If I missed my bus, then there would be no school and this whole exhausting morning would have been a giant waste of time.

Thankfully, doing my makeup was easier now that I had a little bit of experience. I was satisfied with what I came up with in those thirty minutes. I slipped back onto the road and continued towards the bus stop. I was all alone, on a back road way out in the woods, but I still felt more exposed than ever. Every little sound made me jump. Whenever a car zipped by, my joints became stiff and I found myself turning my face away, worried the driver would recognize me and mock me. My skin felt cold and beads of cold sweat were already forming on the back of my neck. How was I going to get through a whole school day with this anxiety?

I was walking up to that bus stop just as the bus was coming around the bend. I closed my eyes and made a prayer, even though I wasn’t religious. I bit down on my tongue, and then when I opened my eyes, the bus was in front of me, with its door open. The bus driver was staring at me. “Getting on?” she said.

I managed to force a smile. I took one step onto the bus and then I looked back at all of the students. None of them were looking at me—all preoccupied with their phones and their conversations. “We’re behind schedule, missy, so get to your seat,” the bus driver said. My heart leapt when she said ‘missy’. Did she really think that I looked like a girl, or was she just being condescending? I looked at her. She wasn’t making any strange faces or snickers or grins.

One of the nearby male students looked up at me. I looked at him and then he looked away quickly. Could he tell that I was actually a boy? Or did I make him shy because I was pretty in my little getup? My heart was still racing. I took the nearest seat, next to the potentially shy young man. I looked at him again. He wasn’t looking over at me, but his cheeks were dark red.

“Hi,” I said in my best girly voice. I was surprised that I had enough confidence to even look at the kid, never mind talk to him.

He looked at me with a big, awkward smile. “Hi,” he said.

“I’m Kendra,” I said.

“Danny—I mean Dan,” he said. And his face became redder. He really was flustered. Was he attracted to me?

A couple of guys my age got on the bus at the next stop. As they stepped down the aisle, one of them noticed me. His gaze connected with mine, and then he looked down my body. “Hi,” I said, and then he snapped his gaze back up to my eyes. “Hey,” he said with an increasingly familiar flustered look on his face.

I found myself sitting with a smirk on my face. I suddenly wasn’t feeling so vulnerable anymore, even though my legs were still exposed and there was still only a tiny bit of soft fabric between my cock and everyone on that bus. I felt strangely excited and flattered. I was starting to feel like this whole transgender thing was a pretty good idea after all. Maybe the next few months wouldn’t be so bad. Maybe they would even be kind of fun.