I practically floated out to her car. I didn’t care who this Penelope was or what she had to say at this point. Heck, I could barely think straight at all! My mind was racing again but in the best way possible! I couldn’t get over my reflection, as I stared at it in the mirror on the car’s visor. Tara saw this and quietly chuckled to herself, but didn’t say a word. Instead, she started the car, turned on the radio, and we were off!

It was a bit of a drive, but it wasn’t overly long. Maybe just a bit longer than it normally took me to go see Mel. After a few minutes, I managed to come down from my euphoric high. Now that I could think, I started wondering about Penelope. I had so many questions. Maybe Tara could at least answer a few of them?

“So uh, Tara. What’s Penelope like? You said she knows what I’m going through, what does that mean exactly?”

“I really can’t tell you too much,” she said. “But she’s a sweet girl, very big into gaming and stuff. Fairly quiet though. She doesn’t talk much unless it’s about a topic she’s very interested in. She was part of the group I met with Samantha, the same one I know Jarod from. I think you could honestly learn a lot from her.”

“Gaming, huh? What kind of games are we talking about here?” I asked.

“Ah, well, she’s into Pokemon like we are. Though she makes my head spin when talking about stats and all that. Girl really knows her stuff. Then there’s one she always gushes over, a game series called Shantae. Apparently they’re action side scrollers with a female protagonist, though she does dress a bit skimpy. She insists it’s all tongue-in-cheek though. Once you get her talking about that, she won’t stop.”

We chatted the rest of the way. Before long, we were pulling into the parking lot of the pizza place. The outside at least looked pretty nice. Tara sent a text, letting Penelope know we were there. A minute later, her phone chimed. Penelope was inside, waiting. So the two of us headed in. I was a bit nervous, both from the prospect of meeting this mysterious girl and the fact that I was wearing makeup in public. Tara looked around for a moment, before spotting Penelope and waving to her. She waved back and we went over.

She stood up to greet us. A bit of a tall girl, maybe 5’9 or so with long, reddish-brown hair with purple streaks in it. Her face felt off to me, though I couldn’t quite put my finger on why. No matter. She hugged Tara before coming over to me and extending her hand.

“Hello there, you must be Michael. It’s nice to finally meet you. I’m Penelope, but you can just call me Penny. Tara’s told me a lot about you,” she said.

“I wish I could say the same, Tara’s been really coy about you. She keeps dodging my questions,” I said, shaking her hand. “It is nice to meet you though Penny. I was told you could help me.”

“Well I’m not so sure really, but Tara was insistent that we meet. So why don’t you tell me what this is about, in your own words,” she sat down and pulled out a small bottle of hand sanitizer, making sure to clean her hands thoroughly.

I looked around. We weren’t too close to anyone else and most folks were caught up in their own conversations anyways. Tara trusted her and it seemed safe enough. So I began to tell her about my crossdressing thing. How it started, how it ended up here, all of that. She listened intently. I stopped when a waiter came by to take our orders. Once they left, she spoke up.

“Now I see why Tara brought you to me. Michael, do you know what the word ‘transgender’ means?” she asked.

“Of course,” I said. “It’s someone who wants to be a different gender than the one they were given at birth. I’ve learned a lot about the subject from a webcomic called ‘Rain’.”

Her eyes widened with surprise. “Wait, you read Rain? Wow, small world! I do too!”

“Wait, really? Huh, I’ve never actually met someone else who’s read it before.”

She chuckled. “Well that’s because you haven’t knowingly met a trans person before, have you?”

I thought for a moment. “Well there was this one time in high school. Former friend of mine came out as trans, but I gave her the cold shoulder afterwards. I feel bad about it, but I didn’t know any better at the time.”

“Well maybe you could start to make up for it now? After all, I’m trans too,” she said with a smile.

It took a moment for that to sink in. “Wait, what? Is that what Tara didn’t wanna tell me?! That she was taking me to meet a trans girl?”

Tara chimed in, with a bit of a guilty look on her face. “Yea, sorry about that. I can’t just out my friend like that, it would be a violation of her trust. You understand, right?”

“No, I get it now,” I said. “I’m just a little surprised. So, what? You think I might be trans or something?”

“It’s possible,” Penny said. “But that’s not for us to decide. What I can say is what you’ve described to me sounds a lot like stuff I’ve been through myself. Especially before I realized that I’m trans. All of the envy and the dysphoria too. Have you at least considered it?”

“I’m not gonna lie, the thought has crossed my mind more than once,” I said truthfully. “But I dunno, it never quite seemed to fit me. From what I’ve seen, most seem to know at a young age. Even Rain wanted to be a mommy by the time she was 4. I’m already in my 20s, shouldn’t I know by now? And every time I look inside myself, I just don’t see a woman. I’ve never felt like a woman in a man’s body or anything like that. Hell, I don’t even hate the equipment I got downstairs! So I just don’t think I could be trans, you know?”

“Hmm, I do see your point,” Penny nodded. “But have you considered you might just be non-binary?”

“Huh? Non-binary?” I asked. “You mean like Jarod or something? Or maybe Ky in Rain? No, I don’t think I’m like either of them.”

Penny just shook her head. “No, not like them. I mean, yes, they are non-binary. But it’s a whole spectrum. Like how Ky shifts between genders, or how Jarod still identifies as a man, more or less, despite being somewhat feminine. From what I understand, there’s no one way to do all of this. Gender is complicated like that.”

“Ok great,” I said, not fully grasping this. “So, what, do you have some idea of what I might be or anything?”

She looked down. “I’m sorry, I don’t. This is something you’re gonna have to figure out for yourself. I’m not all that familiar with non-binary identities. I’m a binary trans girl, so it’s never been an issue for me to look into. I have to focus on my own transition.”

Needless to say, I was disappointed. I was no closer to finding an answer than I was when I came in here! Or was I? On second thought, I had learned a bit here, perhaps enough to put me on the right track at least. I still had no clue as to what a lot of this meant, nor how to find information on it. Surely though, someone had to know something! It was just a matter of finding where that info was, how hard could that be?

I was pulled from my thoughts by the pizzas arriving. Thank goodness, I was starving! We all split a couple of pepperoni pizzas. A nice, neutral topping everyone could enjoy. As we ate, a new thought crossed my mind. Just who was Penny? Sure, she was friends with Tara and had just told me that she’s transgender. Outside of that though, I didn’t really know a lot about her. Mainly because Tara had been so cagey with details, due to her gender identity.

Between bites, I asked her, “So Penny, how did you find Rain exactly? I mean, do trans people just automatically know about this stuff or something?”

She just laughed. “Hardly! No, I found it after some of my favorite Youtube channels directed me towards DeviantArt. I started looking at some of the TG content on there, and it was fun. But after some time, I really needed something more. My dysphoria was really getting to me and I felt really depressed. That’s when I stumbled upon Rain. It was exactly the kind of representation I needed. Just a regular trans girl, no magic, no superpowers, no spontaneous gender change, none of that. She just wanted to be a normal girl going to school. I actually just found it last year and I’ve been a loyal reader ever since.”

“Huh, that’s actually really sweet,” I said. “Yeah, I read it through DeviantArt as well. I actually joined a few years ago, cause I was looking for crossdressing art. Specifically Ash Ketchum in dresses. Never knew how popular that was until I joined. I know he’s done it a few times in the show, but apparently there are whole communities online dedicated to it!

Anyways, I did branch off and find other content like that. Then one day I was looking through a person’s favorites there and stumbled across Rain. It was kinda neat, I didn’t know much about trans stuff so it caught my interest. I actually caught it pretty much at the start. Maybe a few pages in. Something about it kept my attention and I’ve been following it ever since. What’s your screenname on there anyways?”

“Oh, I go by AmberFairy. Amber was a name that I tried before, but didn't fit as well as Penelope. And I enjoy mythical creatures, so fairy ended up becoming the next part.” Penny explained.

“Huh, I actually do recognize that name from the comments section. I can’t recall if we’ve directly interacted before though. Oh, mine is HHHFan91. A bit cheesy, but I’m a huge Triple H fan. Pro wrestling stuff, you probably don’t understand.”

She chuckled. “Well, I can't say that I do. My brother might though, he’s much more of a sports fan than me.”

“Fair enough I suppose,” I said. “I’ll see if I can find your account later and watch you, sound good?”

“I’d like that!” She said, happily. “I’ll watch you back. Your sister has been really good to me, I really appreciate her being my friend. I hope we can be friends too.”

I smiled. “I could use a good friend, especially someone who can understand my issues. You’ve been a big help already, I just need to do some looking on my own. I don’t think I’m quite ready to drop the ‘femboy’ title just yet though.”

“That’s fair,” she nodded. “You do whatever makes you comfortable. It’s a process, these things take time. When you’re ready, and you find something that really fits you, that’s when you’ll change. Not a moment sooner.”

“Thanks Penny. Only question now is, how do I tell my girlfriend about all of this?” I asked.

“I mean, it seems she probably already has a good idea about all of this,” Tara interjected. “After all, she took you shopping yesterday. She likely figured you aren't cis by now. And yet she’s still with you and supporting you. Honestly, I’m kinda jealous. After what went down between me and Rodney, it feels like I’ll never find the right guy for me…”

“Hey now,” I said. “Cheer up! I’m sure you’ll find someone. Have you ever considered potentially expanding your horizons?”

“What’s that supposed to mean?” Tara asked.

“I mean like, maybe you shouldn’t just limit yourself to men. Have you ever considered being with a woman before? You never know, maybe that’s what you’re missing here,” I suggested.

“I think I would know if I was gay, Michael,” she said dismissively. “I mean yeah, some girls can be really pretty and stuff, but I’m into guys. I’m not gay!”

Penny just gave her an odd look. “Uh Tara, you do know you can like both, right? Being bisexual is perfectly valid. You can like men and women, even have a preference for one or the other. I’m not saying that’s for sure what’s happening here, but you might wanna think about it a bit.”

“Not you too Penny,” she groaned. “Are you serious about this? One failed relationship and you both assume I’m bi? Seems a bit extreme, don’t you think?”

“Tara, you’ve been around our friend group long enough. You should know by now what denial looks like. Michael has a point, maybe you should give it a try. Not with me, of course. I’m not looking to date anyone right now. I can’t afford any distractions, not when I’m so close to my goal…”

“Your goal?” I asked, curiously. “What goal is that?”

A big grin crossed her face. “My number was finally called! I have an appointment with the endocrinologist in two weeks! I’m finally gonna start HRT!” She let out a small, excited squee.

“Wow, congrats Penny! That’s gotta be huge for you!” I said, sharing her excitement. “I’m sure you’ve been looking forward to this for a long time.”

“Oh yes, this is exactly what I’ve wanted for so long! If I can’t magically transform myself into a girl, which I still haven’t fully ruled out yet, I can at least transition into one! I can’t wait!” The smile never left her face the entire time. She looked so happy, I was kinda jealous. She knew who she was and was confident in it. She had clearly worked really hard to be able to reach this point as well. Yet I was still all wishy-washy about what I wanted, I still wasn’t sure.

“You ok Michael?” she asked, pulling me out of my thoughts.

“Huh? Oh, yea, just kinda got lost in thought for a minute there. I won’t lie, I’m actually jealous. You’re so confident and ready to move onto the next stage of your life. And yet I’m still wandering around with no idea of what I really want. You’re lucky that way. And, to be completely honest, I’ve considered trying estrogen before. You know, maybe one time, just to see what it’s like…”

Both of them stared at me in disbelief. Even under the makeup, my face grew red from embarrassment. Did I really just say that out loud? Finally, Penny spoke up.

“Are you sure you’re not trans?” she asked. “Cause most cis guys would never even dream of touching the stuff, let alone trying it out.”

I just shrugged. Not like I had a good answer for that. I took a bite of pizza so I could avoid answering out loud. There wasn’t much left at this point, and I was getting rather full. The others had noticed this as well, so we started getting ready to leave. The waiter brought over the check and we split it three ways. Once the meal was all paid for, we stood up to say our goodbyes.

“It was great meeting you Michael,” Penny said cheerfully. “ I hope we can meet up again soon. By the way, I’ve been meaning to say this for a little while now, but I love your makeup! Did you do it yourself or did Tara help?”

I froze in shock. She knew I was wearing makeup? But how? Tara promised no one would be able to notice! Was I just out here on display, for everyone in the restaurant? Could they all tell? Were they all secretly laughing at me behind my back? My mind spiraled and I felt dizzy. Tara quickly came to my side and held me before I fell over.

“Oh my gosh, are you ok?” Penny asked. “Did I say something wrong? Was I not supposed to mention that? I’m so sorry!”

“Easy Michael, you’re ok now. Just breathe,” Tara tried to calm me down. “She didn’t know, that’s all. No one else can tell, as long as you don’t make a scene. Come on, let’s get some fresh air.”

The three of us walked outside. My head was starting to feel a little more clear as the panic settled down. I could breathe a little better now that we were outside, even if it was just the parking lot.

“Sorry again about mentioning the makeup,” Penny said. “I’m guessing it was supposed to be a secret. I happened to notice while we were sitting together. I don’t think anyone else could have seen it, as I could only tell while looking closely. It’s subtle, but it looks really nice on you!”

I took a deep breath. “Thanks Penny, sorry for scaring you. I think my anxiety got the better of me there. It’s my first time wearing makeup out in public like this. Tara did it for me before we left and said no one would notice. So I kinda freaked out when you brought it up. I do at least feel pretty wearing it, and I like that feeling. What that means though, I couldn’t tell you.”

“Understandable, it’s gonna take time for you to figure it all out,” she said. “Don’t rush it, I’m sure you’ll find your answers when the time is right. Until then, don’t hold yourself back anymore. Embrace what you know, enjoy it. There’s no shame in dressing how you like. So if you wanna be a femboy? Be the best femboy you can be! Have confidence in it. I know it’s hard, but you’ll get there in time. For now, I should get going. Here, this is my number. If you have any questions or just wanna chat, don’t be afraid to hit me up.” She handed me a slip of paper with her number on it.

“Thanks Penny, I appreciate all your help! Today has definitely been informative. I can’t make any promises, but I’ll do my best. And um, just between us, you can call me Michelle. I just picked it earlier today, you’re the first one I’ve told.”

A big smile crossed her face. “I’m honored Michelle, it’s good to meet you! I hope you find everything you’re looking for!” With that, she gave me a big hug. While initially caught off guard, I embraced it. It felt nice. Then she went over and hugged Tara. We said our farewells as she got into her car and left.

“Ready to head out, sis?” Tara asked, grinning.

I didn’t even bother to object at this point. Maybe I was her sister, maybe not. But for now, like Penny suggested, I would embrace this. 

“Yeah, let's go home.” I said.

And with that, the two of us loaded into the car and headed for home. Everything that had just transpired replayed in my head, this was a lot of new info to take in. I would have to start trying to figure out what all of it meant, if I wanted these weird feelings to stop. Still, I was more confident than ever that I was on the right track! Maybe one day, I would figure it out…

Chapter 8 End

Credits: Rain belongs to Jocelyn Samara

Shantae and all subsequent games belong to WayForward