WALLFLOWER - CHAPTER TWO [PATREON EXCLUSIVE]

Chapter 2

Josephine took me back to her place since she lived walking distance from the club. Her apartment was on the fourth floor of a mixed-use building and had spectacular views of the city. I stood in the window, taking in the sights as Josephine fixed us a couple glasses of water.

She came up behind me, making me jump a little when she put her hand on my shoulder. She chuckled and passed the glass of ice water to me, rubbing her fingers against my earlobes. Fuck, my dick had just gone down after our walk over to her place, and now it was going right back up again.

“I’m so happy you came home with me,” Josephine said as she pushed her fingers into my hair.

“Yeah?”

“Mhm,” Josephine purred as she gripped a bunch of my hair, pulling my head back slightly. She stuck out her tongue and licked along my neck, sending chills across my body.

I never thought much about my shoulder-length hair until Josephine was running her hands through it, telling me how cute it would look once I shaved the fuzz off my face and applied a little makeup. She even complimented the plumpness of my lips, which was something else I’d never considered about myself.

“How do you feel, Gerald?”

“I don’t know,” I admitted.

“Are you afraid?”

I shook my head. I wasn’t afraid of dressing up as a girl. There was something about Josephine that made me trust her, even if that was foolish, as we’d only met a couple hours ago, but she had a positive energy about her. She didn’t seem like the type to cause drama. She seemed like she simply wanted to have a bit of fun.

“Great! You needn’t be afraid, but I’ll need you to turn that frown upside-down! I can’t feminize you if you’re not happy about it.”

“Feminize me?”

“Fancy way of saying turn you into a girl,” Josephine said with a laugh.

My heart dropped to the pits of my stomach as I stood there by the window, hardly feeling it when Josephine pulled me away to guide me to the couch. She sat me down and took the glass of water from my paralyzed hands, placing it on the coffee table.

“Don’t be so nervous, Gerald! It’s not like putting on a pair of panties will hurt you!”

My stomach stirred as Josephine cackled. I could tell that she was enjoying making me squirm, but what was so wrong about a guy wearing a skirt? What was so wrong about a guy shaving his legs or putting on a little makeup? If that was the price I had to pay to slide around inside of Josephine’s pussy, it was the ultimate discount.

“Yeah, I guess you’re right.”

“I am right! You can do it, handsome! Should we get started?”

“I guess,” I said through a groan.

Everything I’d been taught in life told me that wearing women’s clothing would make me gay. It would make me less of a man, but Josephine was all woman, and this was her idea. I wanted to please her. I wanted to be inside of her. Nothing about that was gay. I didn’t have any problems with gay guys, not at all, but I couldn’t stop hearing my father’s machismo ringing in my ears. He would push me to take steroids or whatever supplements I needed to beef up and become the alpha man he wanted for a son.

We didn’t even talk much since the divorce since he was busy traveling around the world and banging whatever chicks would get into bed with him, which were plenty, but I didn’t want to be like that. I didn’t want to act like I was someone I wasn’t. Every time I tried acting like an alpha, I ended up feeling sick with myself.

“Come with me,” Josephine said as she stood from the couch.

I nodded and followed her to the bathroom. She grabbed a few supplies, and I knew this was my last chance to leave. It was my chance to tell Josephine that she was crazy for thinking she could dress me up as a girl, but then I saw the excitement and anticipation in her expression. She wanted this.

“Why are you doing this?”

“You’re cute.”

“Yeah, but why do you want to dress me up as a girl? Don’t you want an alpha guy?”

Josephine laughed and shook her head as she continued gathering the supplies that she would need to feminize me. She had a razor, shaving cream, a feminine shower gel, and body butter. She had all those supplies sitting on top of a plush towel.

“Why would I want to deal with all that toxic masculinity? I hate alpha guys. Guys that think they rule the world just because they’re men are not my cup of tea. I prefer guys who aren’t afraid to experiment or play around with their feminine sides. That doesn’t mean I only like thin guys. There are plenty of beefy, muscular guys who are worlds away from being toxic.”

“Yeah, I guess.”

“Why are you asking this?” Josephine asked as we stood in her bathroom.

I shrugged, not wanting to get into the details of my personal life. I hated how my father’s ideals had such a hold over me after all this time, but he had spent my entire childhood drilling them into me, telling me how men should act. How they should be powerful and controlling. I also saw how his actions drove my sweet mother to madness, so maybe he’d been wrong.

Maybe I shouldn’t be afraid to get in touch with my feminine side, especially not for a girl as sexy as Josephine. I only wished I could be as comfortable as Josephine. She seemed so sure of herself and what she wanted, and I couldn’t even feel halfway like that.

“Why are you so conflicted, Gerald? I can see it in your eyes.”

“It’s nothing,” I said with a shake of the head.

“It doesn’t seem like nothing,” Josephine said as she pressed herself up against me, still wearing that dress that hardly covered her breasts. I loved their softness against my chest, pushing into my body like a head against a pillow. “You can tell me what’s going through your mind, Gerald. I won’t judge.”

Josephine stared at me with her pretty blue eyes. Looking at her made me feel safe. It was weird since we’d only just met, but I felt like I could trust her with my doubts and conflicted desires. I told her a brief history of my father and his ways, spewing word after word until Josephine placed a hand on my shoulder to bring me back to the moment.

“Your father isn’t here right now. I’m sorry that he put all those negative thoughts into your head, but you don’t have to worry about him. You know why?”

I shook my head.

“You’re with me, handsome, and I like boys like you. I like boys who are sensitive and caring and unafraid to be themselves, even if it goes against the ‘ideal’. Do you understand me?”

I nodded, casting my gaze to the floor, too embarrassed to meet her eyes, but then Josephine lifted my chin to look at her. She stared at me with unrelenting eyes. I was thinking about giving up and leaving until that moment our eyes met. Josephine would be as crushed as I would be if I left, so I sighed and asked her what I needed to do.

“Trust me, it’s not as bad as you think.”

“We’ll see about that.”

“Get in the shower and shave your entire body. Everywhere a girl would shave, and then we can work on the rest once you’re out. Make sure to wash your hair too. I have some plans for it.”

I had no idea what Josephine had planned, but I stepped into the shower and followed her command. I lathered my legs with the shaving cream, freeing them of hair for the first time in my life. I couldn’t believe how much they glistened when the water washed over them and removed all the extra hairs.

I kept going, shaving my chest and ass and underarms. I turned off the water to step out of the shower and shave my face at the sink, admiring the rest of my work as I did. I didn’t look too girly yet, but I was halfway there. I liked the smoothness of my skin. I liked how my body looked without hair, so when I stepped back into the shower to wash myself with the girly body wash, I was whistling a song!

I lathered myself with the foamy shower gel, doing a little dance as I stepped into the stream of water to rinse the soap suds from my body. I didn’t know what it was, but I was getting excited! I couldn’t wait to see what else Josephine would do with me, so I was practically running out of the bathroom with a towel wrapped around my waist once I was finished in the shower.

“How did you do?” Josephine asked. She was sitting on the couch with a bunch of stuff next to her, stuff I could only assume she would use to doll up my face.

“I think I did okay,” I said.

“Drop the towel,” she said.

“What?”

“You heard me, Gerald. Drop the towel!”

I swallowed my breath and did what she said. She’d already felt the outline of my dick, so what was the big deal if she saw it? What shocked me is how much her eyes widened once she got a glimpse of my manhood.

“My, you’re a big boy, aren’t you?”

I chuckled and shrugged.

“Come over here and put on this thong before I lose self-control.”

Josephine didn’t take her eyes off my dick as I walked over to her. She patted the spot next to her on the couch. I took a seat there and moaned a little when Josephine placed her hand on my exposed thigh, staring into my eyes with that seductive gaze of hers. She handed me a tiny black thong that looked like it wasn’t anywhere near big enough to hold my dick.

“Put it on before you get hard!” Josephine said and snapped her fingers.

I nodded and put my feet into the thong, and then I pulled it up my legs. It barely held my cock, but somehow it fit. The strangest part of all though was the little string that disappeared between my ass cheeks, and that really made me feel like a girl.

“Is this what you guys deal with? Fuck.”

“You’ll get used to it,” Josephine said with a laugh. “Next is your bra.”

“A bra? You can’t be serious,” I said.

Josephine gave me a look that told me she was indeed serious. She stood to help me with the bra, hooking it into place. She slid in two breast forms after that, which made me feel even more like a girl once they were in place. There was no mirror to see what I looked like, but I could only imagine.

“Here, put on this skirt and crop top too. They’ll look so cute, I’m sure of it.”

I groaned, but I put on the skirt and crop top, anyway. Josephine patted the couch to sit next to her, so I returned to where I’d been, now wearing a skirt and a crop top, which made me feel more than a little awkward, but then Josephine pulled out a bunch of makeup.

“Are you going to put that on me?”

“Duh! You’re so silly,” she said with a laugh. “Close your eyes.”

I didn’t want to wear makeup, but I closed my eyes anyway, letting Josephine apply all the different creams, liquids, and powders that she wanted. Her last step was to add two barrettes to my hair, and then she told me that she had finished. I didn’t know how long had passed, but I couldn’t believe it when Josephine held up a mirror to let me see my reflection.

I looked like a completely different person!

I looked like a girl!