Chapter Two: The Mystery Brunette

I’ll be honest. I was a little too freaked out by the whole thing to mention it to either Annie or Chris. But it was so strange! I’ve definitely been mistaken for a girl before from behind because of my long hair, but this was almost like…an attraction. Did he really think that I was a girl?

The assembly was during the 8th grade lunch period, so we were told to have a quick lunch and then get to our next class. I finished the school day not being able to get that moment out of my head – and with the exciting event of graduation coming up, that’s saying something.

I returned home to find that my parents were out of the house. They traveled a lot and would often go on trips for a whole weekend. Being Friday, they must’ve both left.

My parents trust me a lot though. Being an only child, I’ve grown quite independent. With no bad track record, they’ll give me the house for the weekend without batting an eye.

I ended up inviting Annie and Chris over to hang out. Graduation was next Friday, so I realized this was my last Friday as a middle schooler.

Annie arrived first, and we decided to sit on the couch and talk until Chris came. However, as expected, she would not shut up about the Toned performance.

“And then when they mashed up that One Direction song with the Billie Eilish one? Ahhh!”

Times like these I really wished Chris was here. I needed some to roll my eyes with.

She continued. “I swear, I’m going to all their concerts from now on. Imagine, when we get to high school, we’ll be in the same school as them. I could run into them every day!”

“I think you’re a little too giddy about this guy group,” I replied, a bit annoyed. “You can’t get too excited just because they waved at you.”

“Hey, I didn’t say they all waved at me, but the freshman boy was totally checking me out.”

Her last few words caused my stomach to drop again. It only reminded me further how that boy looked at me.

Just as she said that, the doorbell rang. I jogged to the door. It was Chris.

“Yo yo,” he said, overly casual as always.

The group decided to play Cards against Humanity, which we play a lot. Always gets a bunch of laughs.

“So I got a text from Juan,” Chris said, matter of factly, “My cousin.”

At the sound of “cousin”, Annie dropped her cards. “OOOOH WHAT DID HE SAY?”

“Woah calm down. You’ll actually be happy to hear this.” Chris said.

Annie was squealing with excitement. Chris continued, “So apparently, that freshman singer told him that a really cute girl in the audience caught his attention.”

My heart stopped. But wait – maybe this wasn’t me that Chris is talking about. Maybe it’s Annie! Or heck, anyone else. There were 50-plus girls in the audience during that show, so it easily could’ve been them. Maybe he looked at me in addition to the many other girls.

“Eeeep! That had to be me! When I stood up and waved, he totally looked in my direction. There’s literally no doubt!” Annie said, yelling. She then began to stand up and dance around, celebrating her believed victory.

Chris stood up to calm her down. “Jesus, chill. We don’t know if it was you.” Chris started pacing the room. “I’m actually going to a family party on Sunday. Juan will be there. I could ask him who the mystery girl is.”

“Oooooh this is just like Cinderella!” Annie was beyond giddy.

“Yeah, but in this case you might be the ugly stepsister left holding the bag.” Chris said condescendingly.

I laughed at the analogy, but it was all too possible that perhaps… I was Cinderella.

========

The next week at school I got a chance to talk to Chris at lunch. Annie, Chris, and I always sat together. Usually I would draw while the other two bickered about who knows what. But we all knew that Annie was waiting for one thing in particular.

“What’s the news?” Annie said, as Chris sat down. Chris already looked exhausted by her mood.

“Listen, you’re so crazy about this guy, but you don’t even know his name.”

Chris looked at Annie, awaiting her response.

“Pfft, of course I do,” she said, “It’s…”

We both stared at her.

“Alright, fine! I just think he’s really cute so maybe I’m a bit obsessive. Can you tell me?”

“Well I know two things,” Chris began, “Number one, his name is Scotty Allen. He’s a freshman originally from Highman.”

Highman Middle School. That was the school about a 10-minute drive south of our school, McMillan. I didn’t know too much about it.

Chris continued. “The other thing I learned is that Scotty doesn’t know the name of the girl—obviously. But he kept talking about her when Juan saw him over the weekend. So I guess he’s, like, really smitten.”

“But who is the girl he’s in too! What does she look like?” Annie was on the edge of her seat.

Chris turned toward Annie, as if he was waiting for this moment. “Well unfortunately for you, she was not blonde. She was a brunette.”

Once again, my heart dropped. It had to be me. Scotty Allen has a crush on me.

My face turned red, but nobody seemed to notice. Annie was too busy pouting over the bad news, and Chris was too busy enjoying her pouting.

“Hmm, so he wasn’t into me?” Annie questioned. She shrugged her shoulders, “Oh well, there’s plenty of other cute guys on that stage I could go for!”

Chris sat down and opened up his lunchbox, “The only question now is: Who is this mystery brunette?”

========

The rest of the day went by normally. It was the last week of school, so that was exciting. We continued to watch movies in class and even received our yearbooks. Throughout the day, kids signed each others’, reminiscing of memories of the last three years.

Once I got home for the end of the day, I opened up my yearbook and read some of the notes. As expected, there were a lot of ‘see you in high school’ and ‘have a great summer’ messages. But there were also a few about my hair, mostly from girls, and how they were jealous of it. Ugh, I guess that’s what I signed up for. though.

========

Wednesday was the official last day of school, even though the graduation ceremony was Friday. Lots of tears were shed by the time the bell rang to release us from our final class.

I was at my locker, clearing it out, when Chris approached me. “Hey Jamie, you down to come over after school? I just got this new video game we could play.”

“That sounds good,” I said.

Chris eventually told me the game was the new NBA 2K game. I’m not a big sports person by any means, but I enjoyed the artistic side of basketball: creating plays, weaving bodies, driving to the hoop. Unfortunately though, I was never athletic enough to do it. At 13 years old, I currently stand 5 foot 3 inches, and weigh only 90 pounds, so I’m fairly skinny.

My doctor told me that I entered puberty last year, but still haven’t really seen any effects of it yet. So people’s voices drop a lot, and some people like myself keep a higher voice. I was starting to wonder if I was short, skinny, and hairless for life.

We arrived at the Correa household. I greeted Chris’s mother and father and we went straight to his room. Chris has a really nice family. He and his two brothers are all super outgoing, but like Chris, keep a small tight-knit friend group.

Chris and I sat down on the couch in his room and started to play the game.

“So I did some scouting on who this mystery brunette could be.” Chris said while still looking at the TV screen.

I responded quickly and might have sounded a little too defensive, “Why do you keep trying to figure this out? I thought it was Annie’s obsession.”

He looked at me briefly, and then back at the screen. “Well, Juan mentioned that Scotty brought up the girl again. He told me that he’s looking forward to meeting her in high school.”

“Well that’s not necessarily true,” I said, “She…whoever that person is…could be going to Hinsdale West.”

“Fair enough,” he responded, “but that’s where my sleuthing comes in!”

Chris paused the game and looked at me. He pulled out a notebook filled with writing.

“While signing yearbooks, I took note to ask every girl where they were going to high school.”

“That’s a little creepy,” I told him. He didn’t seem to hear me through his focus.

“As it turns out, out of the 53 girls in the grade, 25 of them are brunettes, and all of them happen to be attending Hinsdale East next year!”
Chris seemed thrilled with his breakthrough. It was totally in his character to get amped about this sort of thing. That didn’t help my nerves though.

“So what’re you saying?” I asked, nervously.

“I’m saying,” he said, focusing his attention, “that Scotty Allen WILL be meeting this girl next year."

========

I've re-edited and picked this story back up after all these years. Look out for a new chapter every week or so :)

Chapter Three: The Graduation Ceremony

It felt like being tied to the railroad tracks watching a train coming in the distance. Sure, I wasn’t screwed now, but regardless of what I did – at least according to Chris – Scotty Allen would find out it was actually a boy he was checking out, and not a girl.

What certainly didn’t help either is the fact that Chris’s cousin, Juan, had now twice mentioned Scotty’s fascination with that ‘girl’ he saw. How was I supposed to get out of this one? I must’ve been an absolute mess the next hour or so hanging out with him.

Enough is enough. I had to tell him. I paused our game and put down the controller.

“Dude! I was winning!” he yelled, quickly changing his tone when he saw my face. “Okay, seriously, what’s up?”

“I have something to confess…” I said solemnly.

“Oh no… don’t tell me you have a crush on Annie. I can’t handle friend drama right now, I just can’t.”

“What? No! Nothing like that!” I shouted back. Chris was always bad at reading the room. “Look, the girl that Scotty Allen saw… It was me.”

He stared at me blankly for a second. Then another second. And as rudely as I would have predicted, Chris started laughing in my face.

“Oh my God no WAY!” Chris was in stitches, rolling on the bed. “The hair! Holy crap it makes perfect sense! Dude, you got the eye of the most popular freshman at East!” Chris couldn’t contain himself. He could barely breathe.

But I was starting to get mad. “This is serious, man! There’s a popular boy who, if he finds out that it was a boy he was making googly eyes at, he’s gonna flip out and end high school for me before I know it! Do you not understand the stakes here??”

Chris was only starting to come down from his immense laugh attack. “I’m sorry, I’m sorry, it’s just so f-u-n-n-y…”

I let him cool down for the next 5 minutes. But each time he said he was done laughing, he’d restart.

Finally, Chris was ready to talk about this like a normal person. “Okay, okay, I’m sorry. So because of your hair, he thought you were a girl. Is that basically it?”

“I think so. There’s not really a reason for Scotty to think that otherwise.”

“Well…” Chris began.

He clearly wanted to say something. “Well…what?” I prodded.

“You’re, uh – and I don’t mean this in a bad way – not exactly the most manly guy in general, right? I mean you gotta admit that.”

As much as I didn’t love admitting he was right, he was right. “I know. I’m small, short, I always hear I have ‘delicate features’, and of course…the hair.”

Chris nodded. While I was an anxious mess, he had a refreshingly calm, curious demeanor. He didn’t have a quick solution. Nobody did. But I strangely trusted his instincts.

“Give me until graduation,” he said. “We’ll think of something.”

========

Lots of people like to hate on middle schools and elementary schools for having graduation ceremonies. “It’s not a real graduation!” they’ll say. But there’s something to be said for closing a loop on a significant period of your life – even if it’s just the early tween years.

Much like the Toned concert (and so many other school events), the graduation was held in our gymnasium. Parents and students alike filled the gym, impressed by the decor and grandeur of the space. Students were seated in folding chairs, and parents and other family were seated in the bleachers behind. My perpetually out-of-town parents even showed up!

Our Principal, Mr. Winters, gave an opening speech and then handed it off to Ms. Reznik, a Spanish teacher and favorite of the students for another ‘go forth!’ type of speech. Lastly, the student council president gave her words of ‘wisdom’, and we soon moved into the presentation of diplomas. The reading of each kid’s name was usually followed by a little ‘woo!’ from the bleachers, likely coming from the proud parents. My parents, however, stayed silent. I didn’t mind it though – it’s not their vibe to be rowdy.

All in all, the ceremony was a quick 75 minutes and we were on our way. Friends and family gathered outside the school for pictures in our little red caps and gowns. Chris, Annie, and I took a picture together as our respective parents looked on at us, all proud and tearful.

I was even approached by some classmate acquaintances, looking to chat about the summer.

“Any plans for the summer, Jamie?” this boy named Thomas asked.

“Honestly, a lot of summer reading. And I’m working on a book of fantasy illustrations.” I explained.

“Oh, that’s super dope,” he said. “Anything in particular you wanna do with it?”

“I’m still not sure. Maybe I’ll turn the characters into a graphic novel some day? Maybe I just let ‘em collect dust. Either works for me!”

We shared a laugh and Thomas shared some stories about all the sports camps he planned to do. On that front I definitely couldn’t relate.

“Well anyway man, if you ever want to hang out over summer, let me know,” he said amiably. “I’m around, and never the worst thing to get some hangs in before heading to East.”

Thomas and I exchanged numbers. I liked that he showed the initiative. Thomas was always in the more ‘popular’ clique of kids, but now that a lot of his friends were going to a different high school, he was clearly looking to expand his group. Whatever the case, it was a nice gesture.

But just as Thomas was walking away, Annie came sprinting up to me. She looked furious. “JAMIE YOU ARE A DEAD MAN!”

I threw my hands up in surrender. “What, what! I didn’t do anything!”

Annie peered left and right to make sure nobody was listening. “Chris just told me that you were the ‘girl’ Scotty Allen was looking at?? Are you kidding me!?”

I rolled my eyes and looked over Annie’s shoulder. Chris was glancing over, shrugging bashfully. “Chris told you, didn’t he…”

“Yes, he told me! I can’t believe you’d try to hide that from me. Ugh! I’m heartbroken.”

“Woah woah woah, I’d appreciate a little sympathy,” I said, checking Annie’s self-centeredness. “You do understand how much of a bind I’m in, right?”

She scoffed. “Yeah, life must be sooo hard for you, having a popular boy interested in you.”

“Yes! It is.” I had to call over Chris.

We reexplained the whole thing to Annie and calmed her down. Though she thought it was the end of the world that an older boy – that she does not know, mind you – wasn’t actually into her, Annie quickly understood the stress this case of mistaken identity was causing me.

“Well, if you hens are done clucking, I think I found a solution to Jamie’s problem,” Chris announced. “Come over tonight and we’ll walk through it, okay?”

========

Chris, Annie, and I all had our respective family celebrations. My parents and I went to Outback Steakhouse for a quiet meal (very much their decision), while Annie’s and Chris’s families had big backyard celebrations. By the time Annie and I got to the Correa household that night, his family party was still raging.

“Grab some punch, water, or whatever, and let’s go to my room,” Chris instructed us, the moment we got there.

We did as told and met Chris in the room. But when we got inside, there was another familiar face.

“Guys, this is my cousin, Juan,” Chris said. “You probably recognize him from Toned.”

I, of course, played it cool. But Annie immediately went into geek-out mode.

“Oh my god, I love love LOVE you guys!” she squealed, barreling into Juan and giving him a big hug.

“Heh, heh, thanks, Annie,” he muttered.

Her eyes went wide. “And you know my name?”

Chris groaned. “Alright, enough of this. I brought Juan in here because we have an idea on how to solve this. And Jamie, you have nothing to fear. He knows everything.”
Are you kidding me?! How could Chris go behind my back and spoil all of this to his cousin – much less his cousin who is friends with Scotty??

“I am so pissed at you right now…” I said through clenched teeth.

But Juan cooled the temperature. “Hey, listen. I’m an ally in this. I know that Scotty’s into you because he thinks you’re a girl. And none of this is your fault, okay?”

I stared at Juan. “Go on…”

“Chris can be an annoying little bastard sometimes, so I was hesitant to help him. But we’ve come up with a… transactional proposition.”

The seriousness of calling it a ‘transactional proposition’ scared me a bit, but maybe that’s just how juniors in high school talk.

Chris jumped in. “Look, we all want to start off on a good foot in high school, right? And Juan is, shall we say, a ‘popular’ guy. So I proposed that he gets us invited to things with the popular kids.”

Annie had a big smile on her face. “Seriously, Juan? You’d do that for us?”

“But I need something in return. I’m not about to just let my annoying cousin into all my parties without something in exchange.”

I had a bad feeling this ‘exchange’ involved me somehow. “What exchange…”

Juan stood up and paced the room. “Toned had a really good year, but the mood of our guys has been… lacking to say the least. And most of that is coming from Scotty.”

Chris was refusing to make eye contact with me throughout Juan’s speech.

“So when Scotty caught the eye of a cute girl that he was actually interested in, we were thrilled! We dreamed that she’d be going to Hinsdale East so he could meet her and be happy. And ever since he saw this girl, his mood has been way up. And therefore, so have his vocals. He sounds incredible! And that’s all with the prospect of meeting her…”

Juan was stumbling a bit. Even a guy of his confidence sometimes had trouble spitting out uncomfortable sentences, so Chris just jumped in. “Jamie, we need you to be that girl.”

I was flabbergasted. “What?! You guys are insane!”

Despite this clearly abhorrent request, nobody was really sharing in my shock.

“We do have a plan for this, you know. And I think it’s fair.” Juan said. “All you have to do is come to a few parties and events, pretending to be a girl. I’ll introduce you to Scotty where you guys will chat, have fun, and do whatever freshmen and sophomores do to become friends.”

I fervently shook my head. “But I’m going to high school with him next year. And I’m attending as me. Jamie. A BOY.”

Chris leaped up with his finger in the air. “But aha! Here’s the kicker. The girl version of you won’t be attending. Because this ‘girl’ is your ‘cousin’ that’s moving away. We’re thinking from Texas.”

This story was getting wilder and wilder. “Texas?” I wailed. “Are you guys insane? Seriously. We need to get a psychiatrist in here.”

“Or honestly, any lie will do.” Juan brushed off my fear with surprising ease. “Look, the whole point is this: we get Scotty’s confidence up, you get your connections at cool parties for high school. And at the end of all of that, everyone forgets all about the cousin, you’ll cut your hair–”

“I cut my hair?” I said, cutting off Juan.

“Yeah… I mean, we need a way to differentiate you for the new school year. Cut your hair in a few weeks when your cousin ‘leaves’. Then ‘boy Jamie’ can start attending the parties, and nobody will ever think you were anyone else. You’ll still have, like, most of the summer to grow your friendships and get all set for high school.”

I paused. Despite the absurd nature of this whole arrangement, I did envision a world where this all worked out.

“Well, what if I refuse?”

Juan looked over at Chris. “Then Toned will suck, and you guys will go back to being lame.”

Annie grabbed my shoulders. “This is a win-win for everybody. I desperately need Toned in my life.”

I thought about it some more. Silently.

“Three events,” Chris said, then appealing to Juan, who agreed. “Just three events. That’s all you need to do. Go to three events as a girl. Talk to Scotty, get him out of his funk, and then your ‘cousin’ can leave town forever. Toned gets its guy back, we get a whole new bunch of friends for high school, and you get to enter high school as a fresh-faced freshman with a cool new men’s haircut. I’ll even help you pick it out!”

In a life full of sighing, I don’t think I ever sighed this intensely. But trust me, it was warranted.

“...Fine. I’ll do it. I’ll be your girl.”

========

I've re-edited and picked this story back up after all these years. Look out for a new chapter every week or so :)

-Jennifer

Chapter Four: Girl Practice

My friends are the luckiest people in the world. Why? Because their good friend Jamie is willing to do all the heavy lifting, apparently.

I can’t believe I agreed to their dumb request. Pretend to be a girl? What the heck do I know about being a girl? As far as I can tell, in each of my 14 years on this Earth I’ve been a genuine, 100% BOY.

Thankfully, Chris promised it’d only be three events. And it better be. Three times I’d pretend to be a girl, hang out with Scotty, and then my ‘cousin’ gets to leave forever. Chris, Annie, and myself will be rewarded with a fun, interesting group of friends heading into high school. And maybe it’ll end up being super easy.

However, I spent much of the weekend not worrying about any of that. My true passion was drawing and illustrating. Did I want to be a book illustrator, a graphic designer, or a painter? I wasn’t sure yet. But much of this summer – outside of spending time making friends – I plan to draw freely, create characters and designs, and hopefully gain a little direction on where my art interests lie.

My favorite thing to draw was young, male protagonists. Much like myself. I was always enamored with the recluse teen that everyone doubted could save the day. I’d create these stories in my head where a seemingly unpopular, uninteresting young boy defies expectations and saves the day. They go from weak to strong, feeble to powerful. That sort of stuff. Hey, who knows – maybe I can channel some of that energy into my task.

========

At the onset of summer break, everyone rejoices in their newfound freedom. No school, little to no responsibility. But tale as old as time, about a week in, we all get bored. So I reached out to Chris about knocking off my first assignment. We decided to hang out that afternoon. And in the middle of a Madden game, Chris finally dropped some ‘good’ news.

“So listen, Juan told me one of the Toned guys is hosting a party tonight,” he said, mid-Cheetoh munch.

“Wait, seriously? That’s perfect! Can we get an invite?”

“Probably. I’ll check with Juan.” Chris reached for his phone. “Let’s hit up Annie too. She’ll wanna come.”

So while we waited for a response from Juan, Chris called Annie and invited her over. However, she seemed angry and stressed about it over her phone. Very unlike her. She insisted we come over to her house immediately.

When we arrived at Annie’s, she was shaking her head with utter disappointment.

Chris kicked off his shoes in the mud room. “Annie, what’s the deal? Why are you so pissed off?”

She didn’t reply. Just gestured to us to follow to her room. Once we sat down and she locked her door, she finally spoke.

“What do you think you guys are doing? Are you trying to get Jamie blackballed forever?”

Chris and I looked at each other, perplexed.

“You don’t see the problem here?” she reiterated.

I had to get a straight answer out of her. “No, Annie. We don’t. Would you care to tell us?”

“You want to go to a Toned party. Tonight.”

We nodded.

“Well thank god I’m here to stop you. Because if you go to this party without prep work, the whole operation will implode,” Annie was in full ridicule mode. “Tell me, what exactly was your plan?”

I shrugged and looked at Chris. “I dunno, I was gonna, like, borrow one of my Mom’s dresses and give it to Jamie? That should work.”

“My god, you guys are so dumb. You can’t just throw on a dress and call yourself a girl! There’s a nuance to it. An art. Does Jamie have long hair and feminine features? Yes he does. But do you think the moment he starts walking and talking that anybody will buy he’s a real girl?”

I guess we hadn’t thought that far. She totally had a point.

“That’s what I thought,” Annie replied proudly. “That’s why you’re gonna decline the party invite today so we can practice.”

“Woah, practice?” I quickly jumped in. “That sounds a lot to me like extra sessions. In other words… more than THREE.”

She nodded, unfazed. “Of course. If an actor agrees to do a show, do they not also agree to rehearsals?”

“I mean… I guess.”

“Perfect. Then today we’ll practice. Chris, you can stick around or not, but I’m mostly going to be paying attention to Juliette.”

“Excuse me, Juliette?” I asked.

Annie smiled. “Mhmm. I decided just now. You’re officially Juliette. Okay sweetie?”

Chris started to chuckle, but I shot him a mean glare. He stopped.

“While clothes aren’t everything, it’s important for a girl to be dressed as such. It’ll best get you in the proper mindset,” Annie said, digging through her closet. She pulled something out. “Here, try these on.”

She tossed me a pink pleated skirt and a white tank top.

I groaned. “Ugh. Pink. Seriously?”

Annie laughed. “Really? I’m handing you a skirt and your issue is that it’s pink? You know what, just for that, I’m gonna make you wear these too.”

Annie reached into a bin in her closet and threw a pair of white panties at me as well.

“No no no! I’m not wearing your underwear.” I protested.

Chris was starting to look uncomfortable. “Maybe I should leave…”

Annie was starting to lose it. “AGH! You guys are ridiculous! Do you want this to work or not? Tell me. RIGHT now.”

Chris and I were silent. Annie was dead serious.

“Juan is graciously giving us this opportunity to start high school on the right foot,” she began. “We’ll get a great group of friends. Cool friends. All we have to do is get Scotty Allen to believe Jamie is a girl. And despite this gift, you guys are making every step of the way as frustrating as possible!”

Annie turned back to me. “Jamie, who knows the most about being a girl in the room?”

“You do.”

“Exactly. So are you gonna do as I say, or are you gonna let us sulk back to the bottom of popularity…Juliette?”

Annie was right. I knew it, and so did Chris. We had to be all in if this was going to work.

Without saying a word, I respectfully picked up the skirt, top, and panties, and took them into the bathroom to change.

I took my pants off and stared at myself in the full-length mirror – naked and fearful of what was to come. But I denied every naturally male instinct of mine and slid on the panties. They fit snug around my package and were, well… actually comfortable.

The skirt was a little less so, and took me a few minutes to figure out how to position it properly with the tank top tucked underneath.

I re-emerged from the bathroom to an approving nod from Chris and Annie.

“You look adorable, Juliette.” Annie said confidently. “Now we can get to work.”

Over the next several hours, Annie gave me a complete crash course on girlhood. Much of it was aesthetic, but so much more was about demeanor, character, and attitude.

Girls move differently than guys. That’s a fact I believed, but never quite understood. Annie had me try on all different kinds of her shoes and did a full lap around the house wearing each of them. She showed me how my steps should be shorter, my upper-body posture tighter, and my hips more fluid. Thankfully her parents were out of the house for the day, otherwise they’d have seen me prancing through the halls every 20 minutes with a new outfit and shoes.

And I tried on ALL sorts of outfits. Over the roughly six hours of ‘training’ I wore androgynous items like sweaters, hoodies, shorts, and pants, as well as significantly more feminine items like dresses, stockings, nighties, and bras and panties. We’d practically cycled through her entire wardrobe.

Though skeptical at first, I found that my demeanor changed drastically based on the outfit I was wearing. With Annie’s blue tracksuit on, I felt powerful and agile. When I wore her pantsuit, I felt like a total ‘boss bitch’ (as Chris put it), ready to take down the patriarchy.

Alternatively, when Annie had me wear her soft pink panties and flowy pink nightie, I’d never felt so dainty. Just lying back on her cushy bed, stroking the satiny duvet cover with my bare, hairless legs felt like a dream.

“A woman is many things,” Annie reiterated. “Clothes aren’t all of it, but so much of a woman’s being can come from what she’s wearing. I hope that you learned that today, Juliette.”

I nodded and thanked Annie with a hug. Chris stayed surprisingly active during this whole process, chiming in with his opinions, both critical and complimentary.

It was getting late so I decided to change back into my boy clothes and head home for the night. Chris told us that Juan was confused why we weren’t coming tonight, but understood that some ‘girl practice’ might be necessary.

“What’re you guys doing tomorrow?” Annie asked us as we put our shoes on. “Because I’ve got some ideas for Lesson #2.”

“Wait, there’s a–” I began to say, but quickly cut off my protest. I promised Annie that I’d trust her with the girl prep. I was but her humble servant.

“I’m free if you are,” I replied instead.

Great. Then be at my place tomorrow at 10 AM.

Ten o’clock in the morning felt especially early in the morning for another practice session, but it’s not like I had anything else going on. Chris said he couldn’t make it, but Annie said his presence wouldn’t be necessary.

“Lastly,” she said. “I want you sleeping in these.” Annie had handed me one of the pairs of panties I’d worn earlier in the day. The pink satin ones I’d worn with her nightie.

“Are… are you sure?” I asked. “You know I’m not being Juliette full time.”

“I know, Jamie. But think of it as ‘passive training’. We only have a short time to get in as much girl practice as we can. Just try it.”

I reluctantly took her panties, but agreed nonetheless.

========

My parents were home when I returned, but were fully occupied watching some violent drama series in the living room, sipping their new bottle of whiskey. I decided not to bother them.

I still had a little of the night left to myself, so I opened back up my sketchbook. Flipping through the pages I saw a soldier, a giant robot, a sword-wielding teenage boy – each in a different art style. I also had a half-finished cyborg teenage boy that I’d been trying out.

But tonight I didn’t feel like finishing that one. Instead, I flipped to a blank page. I began with a sketch of an androgynous face and body shape. It’s usually at this point that I then add a suit of armor, a fierce weapon, or a mighty animal sidekick.

…but not this time. I graced my new character not with a masculine crew cut, but rather a long, elegant hairstyle. And I didn’t have the character attack an enemy. I had them lying on a bed, wearing a soft, feminine nightie. Was it a boy? Was it a girl? Perhaps something in between.

It wasn’t too in-depth of a sketch, and I only spent about 20 minutes on it. But it was a creative expression that grew organically from my day’s experiences.

Maybe that brief but genuine creative expression of femininity will benefit me in tomorrow’s lesson...

Chapter Five: A Trip Outside

Not that she normally does this, but it would’ve been the absolute worst for my Mom to come into my room to wake me up this morning. I think she would've about died from shock had she seen her only son sleeping in his bed wearing women’s panties. I wouldn’t even know where to begin to explain the ridiculous clothing choice.

But this is one of the sacrifices I agreed to make. Annie was totally right – there’s a lot of prep work that goes into being a girl. I couldn’t just expect to show up in some ill-fitting dress at one of the parties and expect Scotty to believe I was a real girl.

So I left my house just before 10 AM to meet Annie for the second day of practice. Funny, she never mentioned how many days of ‘girl practice’ I’d need. I guess I’m just along for the ride.

When I arrived at her place she grabbed me and quickly pulled me upstairs. “My parents are home,” she said, quickly shutting the door behind her.

“Cool… why does that matter?” I asked.

She looked at me like I was a total ditz. “Because I don’t want them to see what we’re doing.”

“I mean, yeah.” I shrugged. “Let’s just do girl practice in your room then. If they knock, I hide and you say I left.”

“Hmm… so, I was gonna wait to tell you this til you were dressed up, but it seems relevant now… I made 11 AM brunch reservations for us.”

“You what??” I nearly screamed, praying her parents didn’t hear me… or her.

Annie sat me down on her chair. “It’s okay, it’s fine. It’s only at Café Soleil. You’ll be fine.”

I couldn’t believe how matter-of-fact she was acting. “Are you insane? Café Soleil is packed like all the time! Don’t you think somebody’s gonna recognize us?”

She snapped her fingers. “Way ahead of you. I already called ahead and asked for a back booth. They said it’s where they put their ‘celebrities’.” Pfft. As if any real celebrities lived in the suburbs of Chicago… the occasional pro athlete, maybe. But still.

But with time, I started calming down. Annie pleaded and pleaded and reminded me how convincing I looked yesterday and how much of a natural I was wearing girls clothes. Maybe – just maybe – we can pull this off.

She picked out a conservative, girly-but-not-flashy, light-pink sundress for me to wear, paired with white summer sandals. I was also given a white bra and panties set to wear underneath. Annie decided to somewhat match me with her own sundress, but hers was light green and she wore navy blue summer sandals.

“My nails are already painted… but I don’t think we have time to do yours. Sorry, Juliette,” she playfully cried, knowing full well I was happy about that.

She also applied a little bit of makeup to my face for the first time. Super subtle, but she insisted makeup would only help hide my identity and make me feel more confident as a girl. Not so sure about the latter, but I rolled with it. Annie even handed me a pair of large, feminine sunglasses as an extra layer of recognition protection.

Soon enough, I was fully dolled up. Annie even took a mirror selfie of us, much to my displeasure. “God, you make for such a cutie!” she squealed.

We left the house without running into her parents, and she told them we were off to meet more friends at brunch.

========

Café Soleil isn’t too far from Annie’s house – only a 10 minute walk – but damn did it feel like a marathon. The sandals were comfortable, and I’d gotten a lot of practice yesterday with women’s shoes, but the fear that I’d run into someone was immense. We were in my hometown after all. Not on vacation, not in some fake virtual game. Nope. The real world

Annie gave me physicality tips on posture and poise along the way, up to and including arriving at the restaurant. Annie agreed to peek inside first, and if she saw any of our classmates, we’d be allowed to abort the mission. Once the coast was clear, we entered and were seated at our back booth. I wanted to keep my sunglasses on the whole meal, but Annie said doing so would probably attract more attention than if I didn’t. I think she was right.

“Okay, I see the server heading over,” Annie whispered. “Have you practiced your girl voice?”

“My girl–what? No, I haven’t practiced my girl voice!!”

“Oh… she muttered. Maybe we should have…”

But it was too late, the server had already arrived. She was a middle-aged woman with kind eyes. “What can I get for you, hons?”

Annie spoke up first. “I’ll do an omelet with cheese and spinach please.”

The server nodded. “And for you?”

She was staring at me, awaiting my response. It was my moment of truth. “Uhhh, the same please.”

The server smiled, nodded, and walked away. I let out another HUGE sigh of relief.

“Great job!!” Annie whispered. “I mean, you only said like three words, but you sounded just like a girl. Weird, I didn’t think you liked spinach though.”

“I don’t. I just thought that was the way I could order using the fewest words…”

Annie laughed. “Cheater!”

But we’d done it. We’d gotten through the toughest test.

========

The rest of brunch went super smoothly. Nobody bothered us, nobody really looked at us. We walked out of the restaurant feeling on top of the world. Hey, maybe this girl stuff isn’t going to be that hard after all. Walking home, I even had a little pep in my step for the first time.

Annie looked at me, impressed. “I gotta say, Juliette. You’re taking this so well. I mean, can you imagine if we asked Chris to take this on?”

I laughed. “He’d never. He’s too stubborn and thinks he’s soooo macho.”

“I just love that you’re sweet and sensitive. That’s a quality that’ll take you far in life.”

I kind of raised an eyebrow to that. Is it? Everything I’ve been told about men – at least from my parents – is that they’re supposed to be strong, confident, family-focused guys. I always felt a little bad about myself, knowing I wasn’t on that path. I’m not into sports. I like art. I’m scrawny with long hair. And now… this? I guess it’s something to consider. Things could get dangerous if I don’t keep my mind focused on the task: I pretend to be a girl, I cheer up Scotty and let him down easy, and boom! We have popular friends for high school.

Annie did her job scouting out her house’s foyer, and smuggled me back upstairs to her room.

“I’m probably good to get this dress off, right? Why risk things any further?”

Annie immediately pouted. “Aww, really? I was having fun with Juliette...”

“Yeah, yeah. Well you can have more fun with her at the first party, assuming we’re done with girl practice for now?”

I think reluctantly agreed with me. “I must admit, you’ve been killing it. Granted, you said three words to the waitress…but even hearing you practice your girl voice on the walk back… it’s pretty stellar.”

“That sounds like a successful day then.” We high-fived, and I went into Annie’s bathroom to change out of the dress and remove the makeup.

“I have wipes in the top right drawer. It’s super easy, you’ll figure it out.”

Annie was right. It was pretty easy to remove the makeup. But it’s interesting, even taking it off, I still saw myself as unbelievably girly in the mirror. The way my hair was hung, the fact I was wearing a dress. Kinda crazy that I probably didn’t even need makeup.

But then there was a very concerning KNOCK on the door. Not the bathroom, but the bedroom door. “Annie, did everything go okay at brunch?”

CRAP! Her mom was right there. If I weren’t in the bathroom, I’d be totally screwed. Pleeeease just send her away, Annie. But Annie waited a few seconds, then answered.

“Come on in, Mom!”

WHAT THE HELL! Annie, you’re such a dope! Did she forget I was in the bathroom or something?

I couldn’t see from my perspective, but I could sense her Mom was exploring the room.
“Do you have a friend over?” she asked.

“Mmhmm.” Annie answered confidently. “Juliette. She’s in the bathroom.”

“Hmm, I’m not sure I know Juliette.”

“Well, you can meet her in just a sec,” Annie said cheerfully. What the hell was she doing? Was she trying to screw me over?

“Oh, okay,” her Mom said. I don’t think I’ve heard you mention her before.

“Yeah, I met her through Chris,” she said normally, but then her tone sounded a lot more pointed. “I thought I’d invite her back to TRY OUT THE NEW SHEET MASKS we bought.”

What? I wasn’t trying any sheet– wait a sec… this was her way of giving me an out!

“Why are you raising your voice?” her mom asked.

“Oh, no reason,” Annie said. “I just really like the SHEET MASKS IN THE UPPER RIGHT HAND DRAWER.”

“Okay, jeez…” her mom was clearly confused.

But that was all I needed to hear. I frantically opened the drawer and found the pack of sheet masks, which I realized were those things used for facial cleansing and to remove blackheads. While Annie made small talk with her mom, I quickly scanned the instructions on how to apply it. I rinsed my face, pressed the mask on… and perfect! My face was perfectly concealed under a white sheet.

“What’s taking Juliette so long? Does she need help?”

“No, she’ll be out in a sec,” Annie said. As much as I was pissed at her, I mustered up the courage to leave the bathroom after quickly tying my hair up in a bun.

“No worries,” I said, terrified but flawlessly faking confidence. “Hi, I’m Juliette.”

Fortunately, Annie’s mom didn’t stick around too long, and only asked a few questions about how I ‘knew Chris’. Thanks to my girl voice, the dress I still had on, and the concealing white mask, she didn’t suspect a thing. And a couple minutes later, she left the room.

Never having been so stressed in my life, I collapsed straight on the bed. Annie burst out laughing. Once I recovered, I shot back up wanting nothing more than to tackle her like a linebacker. But she held her hand up.

“Nuh-uh-uh,” she motioned me back. “I told you, those three words you said to the waitress weren’t enough.”

“...what?”

“I needed to give you a real test. A real world scenario. My mom didn’t recognize you for you. And congrats, you passed.”

I stared blankly at her, but I finally realized her game. All of my anger washed away and turned into genuine respect. Holy crap, that was maybe the smartest thing she could’ve done.

“NOW you’re done with girl practice. I think you’re ready to meet Scotty.”

Chapter Six: Juliette's First Party

Annie totally played me, but I’m kind of glad she did. I had to ‘perform’ under the utmost pressure while pretending to be Juliette in front of her mom. Sure, I had my face concealed by a sheet mask, but I still had to fake a girl’s voice, move femininely, and make sure I gave off zero male impressions. Looks like I passed.

And thank God I did, because otherwise I definitely wouldn’t be confident enough to meet Scotty in person and convince him that I’m a girl named Juliette, rather than a boy named Jamie.

Chris got a huge kick out of my frighteningly stressful encounter with Annie’s mom, but he too was glad I’d be prepared for my first of three promised interactions with Scotty.

“Dude, I still can’t believe you got away with that,” he said in the middle of munching on Cheetos.

I rolled my eyes, even though we were playing video games and he couldn’t see me. “Chris, it was a week ago. Why do you keep bugging me about it?”

“I’m not bugging you,” Chris insisted. “I just think it’s hilarious that she didn’t recognize you. I mean, how many times have you talked with her mom? How many times have you been in that very house? And she still thought you were a different person – a freaking girl, even!”

Annie never even told her mom that it was actually me. In fact, we didn’t even give Chris all the details about girl practice. Sure, he knew that I was practicing walking, talking, and acting like a girl, but I conveniently left out that I was wearing panties on the daily underneath my boy jeans. Annie thought it’d be good to ‘always keep a bit of Juliette with me’. I actually kind of agreed, as much as it scared me that someone might notice a frilly yellow band poking out of my jeans if they looked at me from the wrong angle.

But to this day, still only Annie, Chris, and Juan knew about our plan to get popular. Juan, of course, being the catalyst and one who’d actually be getting us into these parties. And as it turns out, it looks like this weekend would be the time.

It was Saturday, and Annie had just arrived at Chris’s when he read out the text from Juan.

“Ben Grumman is having a party tonight. Can we make this a Juliette night?” Chris read from his phone. “Well, Jamie… is it gametime?”

It didn’t take much discussion. I was ready to debut publicly as Juliette and get one of my three parties out of the way.

“Tonight’s the night! Yes!!” she squealed. “What do you think you’re gonna wear?”

“I haven’t thought about it,” I replied honestly. “I was just gonna defer to you.”

Annie scoffed. “That’s right, you haven’t been a girl long enough to figure out your own style.”

We decided to meet at Annie’s at 7:30 to get ready for the party.

========

As we’ve done in the past, Annie scooted Chris and me up to her room without her parents noticing. But now that ‘Juliette’ has been established, if we ever got caught, she’d simply claim I’m somebody else.

Annie had already laid out three complete outfits for me to choose from.

“Damn, dude! You’re gonna look smokin’!” Chris joked.

“What’s the easiest one to walk around in?” I said, brushing off Chris’s weird remarks. “Comfort should be prioritized for the first night.

Annie stared at her selections for a bit, then settled on the middle option. “I’d say the leggings and top.”

She was referring to a pair of black leggings and a slouchy sweater. It wasn’t too girly, which I liked, and looked far more comfortable than the other two options, which looked like tighter skirts.

We decided on the leggings and sweater, and I was sent into the bathroom to change. Annie insisted I wear and stuff a bra to accentuate my figure just a bit. My ‘cute butt’ (Annie’s words), needed no such enhancement with the leggings.

Chris was impressed. “Holy shit, how do you look hot without even putting on makeup?”

“Can you quit with the objectification?” I grunted back at him. It better not be like this all night.

However, he had a point. I hadn’t done anything to my hair or face yet, and still looked almost 100% girl. Should I be proud of my naturally feminine look? Or maybe, concerned…

Nevertheless, Annie went to work on my face, giving me the works. Foundation, concealer, blush, penciling in my eyebrows, adding mascara, and a fruity, sparkly lip gloss that she claims ‘always make me feel extra femme.’

My hair was brushed, then straightened, and then run through a curling iron to add some loose waves. She topped me off with a few spritzes of perfume and the girl transformation was complete.

“You look gorgeous, Juliette,” Annie said, giving me a big hug. Objectively she wasn’t wrong. I looked like the cute girl-next-door a guy like myself would want to date.

Chris read a new text from his phone. “Juan says we should head over now. Scotty’s arrived.”

========

Ben Grumman was an incoming senior and a bass vocalist in Toned. He wasn’t the leader, partier, or particularly notable guy by any stretch. But his parents were super loaded and didn’t give a shit about parties. The ideal friend for anyone in high school.

He lived in a massive, upscale colonial-style home parked on a ton of land. But as we walked up, we noticed the party wasn’t happening in the house, but rather the gigantic, barn-like garage in the back.

The outfit was comfortable, but my nerves were bouncing off the walls. The closer we got to the backyard down the long, gravel driveway, the more I felt like I was making the biggest mistake of my life.

I violently grabbed the arms of my friends and stopped us dead in our tracks.

“Am I gonna die?” I spat out, clearly startling them both.

“Why would you die?” Chris said. “All we’re doing is attending a party.”

“But like, if someone finds out I’m a boy… they’re obviously gonna scream it out to the party. I’ll die of embarrassment.”

Annie held my shoulders and looked me right in the eyes. “Juliette, you are a beautiful, confident, outgoing girl. Keep telling yourself that. Chris and I will look out for you. Juan too. You’ll be fine.”

I guess her words calmed me a bit. Enough to make it into the barn.

As it turns out, I’m really glad she did. This place looked insane. It was a two-level barn converted into a garage. Dozens upon dozens of high-schoolers crowded the space. Some dancing, some drinking, some just chatting, but everyone was having an awesome time. String lights were strung across the ceiling, and the space was accented with vintage posters, old street signs, and other sick memorabilia.

Juan approached and dapped up Chris.

“It begins!!” Juan shouted, quickly lowering his voice. Not that anyone would know what he’s talking about. “Let me introduce you to some friends.” He did a double-take looking at me. “Damn, Jamie, you clean up nice!” I rolled my eyes.

Never before had I been so welcomed into a party. Juan was such a popular guy that his word was plenty to vouch for our coolness.

For the first 20 minutes, I mostly stuck in a group with Chris and Annie, meeting sophomores, juniors, a few seniors, but notably no other incoming freshman. My heart dropped a few times when I saw a few faces I recognized, but I guess my feminine disguise was good enough that they didn’t clock me. Amazing, the power of makeup and a good outfit!

“Hey, Juliette,” Juan came up behind me. “I got someone you should meet.”

Juan turned me around and pointed exactly where I thought: Scotty Allen, standing alone by the drinks.

“Scotty!” Juan shouted, waving him over. When Scotty looked up and over, recognizing who I was, his face lit up. The kind of excitement that you get when talking to your crush? That was the look he was giving me. It hurt me knowing that I’d have to be letting him down eventually. Who’d want to ruin a wonderful emotional rush like that?

“Meet Juliette,” Juan said, stepping away smoothly to leave me alone with Scotty.

The trance he fell into was just like the one on stage. Despite the girly clothes, hair, and makeup this time around he clearly recognized me as the girl from before. The same one who caught his eye at the Toned concert.

“Juliette,” he said. “Nice to meet you.”

I smiled back, shaking his hand. “Nice to meet you too.” There wasn’t much to say outside of an awkward pause. “I really love your music.”

“Thanks,” he smiled back, not furthering the conversation. Maybe there was a reason this guy couldn’t get girls. He was kind of awkward.

It took a while for me to pry out some answers, but we eventually got to talking about music and interests.

“So, remind me, you’re going to Hinsdale East this fall?”

“No, no,” I explained, having to keep my lies straight. “My cousin, Jamie, is. I’m moving back to Texas at the end of the summer. Love a good trip with my ‘ol Aunt and Uncle!”

Ugh. That was a lame thing to say.

I went on explaining my fictitious backstory: That I’m up here for the summer for a few weeks to hang out, but my ‘cousin Jamie’ is kind of a quiet, art-loving recluse (hey, not an entire lie) so I’m hanging out with his friends and going to parties. I may have messed up a few details here and there, but Scotty totally bought my story.

As it turns out, Scotty just needed a little loosening up. Admittedly, I was far more obsequious than I normally am. After all, my job was to get Scotty’s confidence back up – not to strike up an actual friendship. So I continued asking questions about his music, his family, his views on life, etc. He was definitely coming out of his shell. At least enough to share some more personal details.

“You seem like an honest, reliable person, Juliette,” he began. Ohhhh, the irony… “Do you ever just, ya know, feel like the stuff you’re doing now, isn’t the stuff you’re meant to do?”

“How so?”

“Well, I dunno... I’m super grateful that Toned wanted me as a freshman. They, like, never do that. But as much as I enjoy singing, it feels like I have other interests I should be trying out. Maybe I’ve, like, gone too deep into music.”

This right here was my purpose. It was exactly my job to plant in Scotty’s head that ‘NO, you DO like music!’. Maybe a pretty girl telling him that could solve it all.

But before I could muster a word, somebody called his name.

“Hey, my buddy’s calling me. I think he needs help,” he twiddled his thumbs for a moment before stepping away. “Sorry, I didn’t mean to drop all my woes on you like that.”

“It’s okay, don’t wor–”

“Could I like, get your number, maybe?”

His request totally caught me off guard for some reason. “My what?”

“Your, like, phone number. So I can… I dunno. Text you? Sorry, maybe that’s dumb. I just kinda liked talking to you is all.”

Crap. Was he really asking for my number? This wasn’t part of my agreement with Juan, but I guess it falls under the umbrella of ‘get a girl to boost his confidence’.

“Sure,” I said, reaching for his phone. I input my number, making sure to write ‘Juliette’ and not ‘Jamie’.

“I…will…text you,” he said, not really looking up at me as he left. God, was this his first time asking for a girl’s number? I’m not the smoothest guy, but even I’m not that clunky.

I caught up with Chris and Annie who were chatting with separate people of the opposite sex. It didn’t look like either of them was doing too well, so I came to the rescue.

“What? I was doing fine!” Chris insisted as Annie and I yanked him away. We found a spot in the barn to break down what happened.

I filled them in on my surprisingly awkward but overall manageable conversation with Scotty.

“Do you think he likes you?” Annie asked.

“Definitely. His face lit up when he saw me. But listen, I don’t think confidence is really this guy’s issue. At least not completely.”

Chris and Annie stared at me.

“I think he may just… not like music anymore.”

Annie gasped. Chris threw his arms up. “What!? How can he not like singing? He’s so good at it!”

“Yeah, I know. But he mentioned something about ‘other interests’…”

Chris stopped me right there. “No no no. He can’t have other interests. Because if he has other interests, he drops out of Toned. If he drops out of Toned, that means we did the exact opposite of what Juan asked us to do!”

“And if we don’t have Juan on our side, there goes our party hook-up. I mean look at this place! Do we really wanna lose all this?”

I sighed. This was becoming a lot more complicated than I thought. “Look, I gave him my number–”

“Whaaat?” Annie squealed. “Juliette, that’s adorable!”

“Shut up, okay?” I cut her off. “He asked for my number, so maybe I still have some influence on him. Maybe it’s not too late to stop him from quitting music.” I looked across the barn at Scotty chumming it up with some friends. “He said he’ll text me tomorrow, so I’ll craft a logical, persuasive text–”

Annie was furiously shaking her head. “Nuh-uh. Now way I’m leaving this high-stakes job in the hands of you texting.”

“Well, what other ideas did you have?”

“I think once he texts you tomorrow, you set a time to meet in person to discuss this. Outside of school, outside of parties.”

“Wait, like, just the two of us?”

“Yes, obviously… Pick a park or a restaurant or whatever.”

I couldn’t believe what she was insinuating. “So like… a date?”

Annie smiled. “Exactly.”

========

If you're enjoying this story, check out any of my newest release on Kindle, In Rotation! ~41,000 words, 23 chapters!

Link: https://www.amazon.com/Rotation-Gradual-Feminization-Story-e...

A Girl for Halloween: A Slow and Sweet Gender Realization Story

By: Mysterious Stranger AKA Jennifer Sweet

“Alright Dad, I’ll go to the interview!” I said, finally giving in after a long debate.

“You’re making the right decision, Jason.”

My father had recently lost his job working a desk job for a local brewery. Because of that occurrence, my parents were no longer able to contribute any more money to my college fund. So the circumstances were either I go to community college for a year, or I can go to a University right away, as long as I got a job.

Finished with the conversation, I made my way up to my room and called my buddy Kyle about the news.

“Good to hear man!” he said enthusiastically, “having a high school job will probably be good for you anyway. It’ll teach you some responsibility.”

We chatted some more about school and then said bye for the time being.

Even though it was a Friday night, my dad had scheduled an interview for me at this Halloween store chain that just opened up in our downtown area. Being a teenage boy, this was not ideal, as I wanted to go out with friends, but I told my dad I’d go. I threw some shoes on, and took the car to the Halloween store.

I pulled up and parked. The store was called 'Merlin’s', and had a picture of a cartoon wizard next to the fluorescent letters on the room above the store. It had rented space in our strip mall, so you could still see the remnants of the letters from the sign for the pizza place that used to be there.

I walked inside and the place looked surprisingly impressive. In the front were halloween decorations like fake skeletons, ravens, etc. In the back, were the costumes and a few changing rooms. There seemed to be a LOT of costumes; there were some for men, women, children, and even pets. But overall, the place was well decorated and looked like the move-in process was coming along for just being September 28th.

“Can I help you?” the woman at the counter asked.

“Yes, I’d like to speak to the manager. My name is Jason and I’m here for a 7 o'clock interview.”

“I can help you with that. I’m Sandy Hogan, store manager.”

Sandy was a portly woman with light-brown hair and kind eyes. I shook her hand and she walked me to her office in the back of the store. We walked past the decorations and the costumes on the way back. There were even more costumes than I previously thought from first glance. Only the men’s costumes, however, were hung up on the racks. The women’s ones were all piled up to the side of the store in their packaging.

We got into her office and told me to pull up a chair near her desk. “So tell me about yourself, Jason.”

We talked about school for a little while, and I explained that I’m a volleyball player at my high school, a pretty good student, and hoping to make a little money to help with college.

“Well, Jason, you seem like a nice kid, and we need workers, so it looks like you’ve got the job!”

“Thanks so much! When do you want me to start?” I inquired.

“Come in at 9am tomorrow to start with the organizing of the costumes. You’ll meet all the other workers then too.”

We shook hands again and I left the store and went home happy. For the rest of the night I hung out with my friend Kyle. I told him about my job and he seemed excited for me to start tomorrow.

========

Saturday morning came along and I woke up at 8am, got ready (showering, combing my shoulder-length brunette hair, getting dressed, eating, the works) and then drove off to my first day.

I walked inside and was greeted by Sandy. “Welcome Jason! Are you ready to work?”

“You bet!” I responded cheerily. “What should I start on?”

“Well, all of the men’s costumes are already hung up and in their place. Val and Autumn are towards the back of the store checking out the female costumes and making sure they are the size they say the packaging indicates. You can go join them.”

I walked to the back of the store.

“Hi, are you Jason?” one of the girls asked.

“Yep!"

“Cool. I’m Autumn and this is Val,” the girl said.

Autumn was a moderately tall girl, at probably about 5’7”, with blonde hair and bright blue eyes. Val was close to the opposite. She had long black hair, and brown eyes, yet about the same height as Autumn. Both of them seem very friendly and peppy.

“Right now, we are just taking these costumes out of their packaging and checking them to make sure they are the right size.”

I grabbed the first costume I saw in the pile. It was a female vampire costume. The costume was a long red and black dress, with cut fabric at the end. It came with two-or-so inch heeled black shoes and a set of fake teeth.

Picking up the dress, I scanned the dress for a size indicator. I couldn’t find one. Then I looked at the packaging. Again, no size.

“Hey Autumn, where are the sizes on these?”

“Oh Sandy didn’t mention it to you? The costumes don’t have sizes listed on them at all.”

That seemed ridiculous! “Why not?”

“Well the people at Merlin’s get them really cheap from this manufacturer who doesn’t even bother to put sizes on them. I mean the packaging is just plain plastic with the name of the costume on it. There are extra-smalls through extra-larges for all costumes, so we just hang them up to what they appear to be.” Autumn explained.

“What do you mean ‘appear’ to be?”

“Just put it up against your body.” Val exemplified, swinging the material against herself, “If it looks like it will fit perfectly on me or Autumn, then it’s a medium. We then estimate from there.”

“Okay…” I answered. I picked up the vampire dress again and placed it against my 5’9” frame.
“What do you think?” I asked the girls.

“I think it looks like you’re wearing a dress...” Autumn joked. The girls laughed.

“Very funny guys. But actually?”

“That looks like it would fit you if you wore it…and you’re about 5’9”, so call that a large.” Val estimated.

I then grabbed a Hanger with an “L” on it (signifying a large) and put the dress on it, with the heels and fake teeth underneath the dress now hanging from the rack.

The girls and I did this for the next few hours, but we only completed about a third of the costumes. We decided since it was close to noon, we’d take a lunch break.

We left the store and walked a few stores down the strip mall to a Smoothie place. Autumn and Val both ordered mango smoothies, and I had a strawberry one.

We took a seat in the smoothie shop and started talking. I found out that the girls both went to a rival high school nearby called Norridge South. I went to Norridge North. Classes came up in the conversation and then Val kinda asked an out of the blue question.

“So Jason, why do you keep your hair so long?”

“Ummm, I don’t really know. I guess I just like it that way.”

“Well you at least take decent care of it,” Autumn pointed out, probably referring to the fact that it wasn’t as mangled as other guys with long hair, despite it being kind of limp and messy.

It was a kinda curly/wavy throughout, and wasn’t as neat as it probably should be.

Val then reached towards my head and pushed the hair from falling into my face to behind my ear.

“Here!” she said, “this should help keep your hair out of your eyes." She reached into her purse and found a plain black barrette. She pulled back my long bangs and held back to the left side of my head using the barrette.

“Oh, I guess that was kinda bugging me.” I said, saying my thanks.

“No problem. I have a million of those anyway. Ready to go back to work?”

We all got up and walked back to Merlin’s.

The first costume I picked up since getting back from lunch was a ‘Fitness Girl’ outfit. I took it out of the packaging and held it up against my body. The costume consisted of sneakers, a tank top, and leggings, and was a bit difficult to tell of the size.

Autumn looked over at me, noticing my confusion, “What’s up Jason?”

“It’s just that these leggings in the costume are a little difficult to tell what size they are. They are spandex and don’t really hang well. They look really small, but maybe it’s just because they haven’t stretched out.”

Autumn grabbed the leggings from me and hung them against her body, “Hmm that’s true. My bet is that they’d be large, but you should try them on to be sure.”

I laughed. “You’re kidding, right? I’m not gonna try on leggings.”

“Val and I always test out the costumes that are difficult to size up. It’s the only way we know that they’ll be accurately marked.”

“So you’re saying I should wear leggings?” I said, not trusting her judgment in the slightest.

“Well, yes. My guess is that they are a large size and if you fit into them well, that means they're large.”

Autumn didn’t seem to be messing around. I think she genuinely thought I should try out the leggings. That’s ridiculous. I mean, have you ever seen a boy wearing leggings that wasn’t named Richard Simmons?

“The changing rooms are in the back, Jason.” Autumn added. “And don’t worry, no one will laugh. You just try them on and then show us what they look like. Val and I will determine the size.”

I sighed. “Fine. But no snarky comments about wearing them.”

We all laughed (myself, uncomfortably). I took the leggings to the back changing rooms and stepped behind the curtain. I took off my jeans and went down to my briefs. I stepped into the leggings (which are actually kind of hard to get on) and adjusted them.

I took a deep breath and walked out to the store’s costume area. Val and Autumn started to giggle.

“Hey! You guys said you wouldn’t laugh!” I snapped.

They both stopped and apologized. “Okay let me take a look” Autumn said. She had me stand still and looked at me from the front and behind. “Those fit you like a glove, Jason!”

“Yeah…they are surprisingly comfortable too.” I added.

"Well you can keep them on if you want,” Sandy said, walking up.

I turned around quickly, embarrassed.

“I…I just tried them on ‘cause…they….the girls told—“ I stammered.

“Don’t worry Jason it’s fine!” Sandy assured, “You guys can try on whatever costumes you want as long as you’re still working hard. And Jason, those really accentuate your slender legs nicely.” Sandy winked.

The girls couldn’t help but giggle at my embarrassment.

“Alright though….Jason, you can keep those on, but just get back to work and finish up the rest of the first half of the costumes.

We did as Sandy told and finished up the costumes. Once we finished, we said goodbye to Sandy.

“See ya!” She replied, “I’ll see you tomorrow from 10-3 to finish up the costumes!”

I changed out of the leggings back into my jeans and drove home.

==========

I got home around 4pm, surprisingly exhausted from work. I plopped myself on the couch.

“Hey Jason. How was your first day?” my older sister Julia asked. She’s a freshman in college, but lives at home because she attends the local community college.

“A little tiring, but fun nonetheless. I work with some really nice girls.”

Julia looked me up and down, smirking. “I see. And was it one of those nice girls who prettied up your hair just a tad?”

I gasped for a second and realized I forgot to take the barrette out! I blushed and attempted to explain, but Julia said not to worry.

She sat down next to me on the couch. “I think it looks cute.”

“Well I don’t want to look cute! I just want to keep the hair out of my eyes. That’s why Autumn and Val put it in.” I explained, flustered.

“Okay okay don’t get your shorts in a knot.”

Julia left the living room and I relaxed in front of the TV for a while.

========

The next day rolled around and I woke up again at 8, but got ready by 8:30, even though I only needed to be at work at 10. I sat down and turned on the TV.

“Hey little bro. Whatcha watching?” Julia asked. I guess she gets up early too.

“Reruns of The Simpsons,” I said, disinterested in having a conversation.

“That’s cool.” She said. “Hey I notice you don’t have your barrette in any more.”

“It must’ve fallen off while I was sleeping.” I said apathetically.

Julia left the room for a minute and then returned. While just sitting on the couch, I felt something touch my hair from behind. I whip my head around and its just Julia.

“What’re you doing??” I ask angrily.

“Just helping you out! Jeez!” She says as she continues to put the barrette in my hair.

“Fine. Go ahead.” I said. I guess she was helping me.

I just kept on watching tv while Julia went back up to her room. She returned to the couch with some sort of two pronged metal thing. She plugged it into the wall near the couch and started clamping my hair.

“Hey!” I yelled. “What do you think you’re doing?"

“I’m just straightening your hair. Trust me, this will keep the messy curls from leaning into your face,” Julia explained.

I guess that made sense. And I HAVE been tired of hair getting in my face for a while.

However, her little “hair straightening” ended up being a bigger deal than I thought. She had to use multiple clips to keep parts of it up while she straightened the rest. It took about 20 minutes, but she finally finished.

“Alright I’m done.” Julia told me.

Now that my hair was straightened, It didn’t lean into my face like it used to. However, Julia still added her own pink barrette into my hair, just to be safe.

“Does it have to be pink?” I pleaded.

“It was the only one I could find. Chill out.”

Whatever. The barrette is doing its job and I’m happy. I looked at the clock and saw it was closing in on 10, so I left for work.

========

Walking into Merlin’s, Sandy welcomed me and pointed me back to the costumes as she had the last time.

“Wow your hair!” Autumn shouted in excitement.

“What, does it look bad?” I said, sort of concerned.

“No no no…It looks wonderful!” Autumn and Val stopped what they were doing and started feeling my new hairstyle.

“It’s just straightened, guys. It’s supposed to help keep it from falling into my face.” I said, trying to cool down their interest.

“Oh I’ve been trying my whole life to get my hair to look this pretty when straightened,” Val shared. “You REALLY pull this off, Jason.”

I blushed. “Well thanks guys. I guess my hair does look well-maintained at least.”

Autumn, Val, and I returned to work for a while, putting costumes up against our body and figuring out the size. I went through mummy, Frankenstein's bride, construction worker, and many other costumes. Then, Val interrupted me.

“Hey Jason, would you lend me a hand for a sec?”

I dropped the current costume I was working on and walked over to Val. She was holding a Ice skating dress.”

“I think this is a large, but would you try it on just in case.”

The dress looked like it would be tight to the skin, so I understand why Val would want me to try it on. But it also was a super girly outfit. Should I, a boy, wear such a girly dress?

“You mind? Just try it on.” Val asked.

“I…suppose.” I said reluctantly.

She handed me the dress and I walked back towards the changing rooms, wondering what wearing this dress will feel like. What if I ended up finding it okay? What…what if I end up…liking it?

========

The remaining 12 Chapters of this story are available on Amazon/Kindle. Link is below!

Hope you enjoy, lovelies! :)

https://www.amazon.com/gp/product/B08FH75CC8?pf_rd_r=TPCHH27...

CHAPTER TWO

All things considered, I was having a nice start to the new year. I had the entire week off of work… even if Bridget wasn’t so lucky. That was one of my bones to pick with company — you can’t even give her a couple days off of travel the first week of the New Year?

But she put up with the hectic schedule remarkably well. Way better than I ever could. It’s funny, with my 100% work-from-home schedule, I felt like a stay-at-home spouse. I always did all the cooking, and because I had the lighter responsibility load, I cleaned and shopped for the two of us. Nor did I mind it. After all, I’d gotten quite good.

I’d mostly left the New Year’s party and Bridget’s conversations with Anthony out of my mind, but as they say, idle hands are the devil’s playthings. Or in my case, an idle mind.

I knew absolutely nothing about this man beyond his name. Did he and Bridget ‘keep in touch’ like he said? Maybe it was a career opportunity. Or hell, maybe it was just one of those bullshit things you say to someone you’re never gonna talk to again. He could have just been being polite.

But no. I had to know. I felt too uncomfortable going straight to Bridget with any inquiries, lest I give off ‘crazy jealous boyfriend’ vibes. So I hit up Matt, the host of the party. If there’s anyone who would know something about this man, it’d be the guy who actually invited him. I texted Matt and we set a time for brunch over the weekend.

=======

“I think I’m still hungover,” Matt joked, sipping on orange juice. “Even a week out.”

We met at a brunch spot near his place. I was happy to make the drive over his way. It minimized any chance he flakes and I’m unable to get an answer. But I tried my best to be casual about the whole thing.

“I think everyone had a good time though,” I said. “People really dig your parties. Ended up being a solid group.”

“You think so?” he said, a tad unsure of himself. “I’m always afraid of mixing friends. You never know how a bunch of random people with only myself in common are gonna vibe.”

“Seriously, you did great. I mingled, Bridget mingled… Everyone was meeting and connecting.”

Matt took another sip of orange juice, happy with my analysis.

“That reminds me…” I continued. “Bridget was chatting a ton with this one guy…” I pretended to think of his name. “Alan? Antonio, was it?”

“Oh, Anthony?” Matt finished my thought. “Cool dude. Super mysterious.”

That’s a hell of an adjective to use. “Mysterious?” I asked. “How so?”

“I dunno. He’s crazy charming, and everyone loves him. But he’s so… unassuming, ya know?”

Yeah, I knew. That’s what I was trying to figure out. “How did you meet him?”

“A friend of a friend, initially. Some guy I don’t really talk to anymore. But I run into him at the gym and we talked there. I’ve invited him to a few things in the past but this is the first time he actually showed.”

“Did he come with anybody? Or was he alone?”

“I think alone…” Matt started to feel uneasy. “Is something going on?”

“No! Totally not. I’m just, like, curious about your friends is all.”

Matt kind of bought my answer, but quickly moved on. “Yo! You know what I actually heard about him through my other buddy?”

Matt looked side to side, making sure nobody was listening in. “He’s a swinger.”

I raised an eyebrow. “A swinger? Like… he sleeps with a lot of people?”

Matt threw up his hands. “Hey, I dunno man! I just talk to the dude at the gym.” He lowered his voice again. “But that’s the second hand news.”

A swinger? Well that settles it. Anthony is absolutely trying to slide in on Bridget. And he’s probably trying to reel her into his perverted little circle…

========

The new knowledge bugged me all week. I wasn’t sure who to be angry at, or even if I should be angry at all. Honestly, I knew very little about this whole situation. I definitely saw Bridget have a good time talking with this mysterious Anthony, and I definitely heard him insist that they keep in touch. Now Matt’s confirmed he’s a swinger. Or, at least second-hand that he’s a swinger. So maybe I don’t know that for sure.

Regardless, my suspicion was enough to confront Bridget. I waited until she got home from one of her work trips and wasn’t in an abrasive mood. Getting ready for bed felt like the right time.

“Hey, babe, can I ask you something?” I muttered, still a little afraid to officially pull the trigger.

“What’s up?” Bridget was brushing her hair in the mirror, ready to get into bed.

I let out a big sigh. “What I’m about to ask you isn’t accusatory by any means. I just want the truth.”

That certainly caught her attention. “What do you mean… Justin, what are you talking about?”

“That guy, Anthony…. from the party. Are you… are you cheating on me?”

She stared at me silently for a moment. She let out a big sigh.

“No. I’m not cheating.”

Her answer felt honest, but the tone was strange.

“However,” she continued. “We’ve been talking.”

I let my head down. “Bridget… I told you, I’m working on things in the bedroom.”

“I know you are, but—“

I was starting to get pissed. “But to start talking to another guy? Like, seriously?”

“No, listen, Justin. I’ve been talking to him about… something else.”

I almost laughed in her face. “Something else? Oh, do tell!” I was dripping with sarcasm. “Do tell what other, ‘non-sexual’ stuff you’ve been discussing with the guy you were totally interested in at the party. I’d love to hear it!”

“Will you just fucking listen for a sec!?” she screamed. I calmed down to let her talk.

“Anthony approached me at the party. That’s true. But he didn’t try to have sex with me.”

I rolled my eyes. “Really?”

“He wanted to have sex with us.”

I froze. “Wait… what?”

Bridget was dead serious. “He wants to join.”

I fully suspected that this guy was a swinger. And yes, I knew what that meant. But never did I think that I'd be part of this nonsense. I thought he was exclusively going for Bridget.

I started to laugh — partly at my misreading of the situation, but mostly at the absurdity of his request.

But Bridget wasn’t messing around. “Why are you laughing?”

“Are you kidding me? Because the guy wants to have a three-way! With us! That’s fucking crazy!”

“Why is it so crazy?” she asked. “People have three-ways.”

“Ha, yeah… but like, not us.” I kept laughing, but she kept staring. “…not us, right?”

“Why not?”

This was no longer funny. Bridget, somehow, had it planted in her head that this was a real possibility.

“You can’t be serious, Bridg… You’re actually considering this?”

“Justin, it’s not like things have been going well in the bedroom. I mean… maybe we need to shake things up.”

“But… another man? Why can’t it be a chick or something?” I proposed.

“I’m sorry, but do you see any chicks lining up and offering three-ways?”

She had a point. “Okay, sure… but, who says I’m not gonna veto having another dude in my bed?”

“Our bed. And honestly, are you so insecure in your sexuality that another guy would ruin things?”

“I mean, I’m straight… So you’ll have to forgive me if I don’t want another naked man in my bed.”

Bridget was getting a little frustrated — perhaps because she knew I had a point. She scooted closer to me on the bed, and held both of my hands.

“Justin, I love you. I… I may not have shown it well recently, and maybe that’s my fault. But I want this to last. I want us to last. And God knows we’ve been teetering on the edge of trouble for a while now.”

I looked deep into her eyes. This was the Bridget I knew. This was the old Bridget.

“I’m sorry for not being transparent with you. I was going to bring this up. Honestly. I think part of me needed to be convinced it’s not crazy too.” Bridget let out another big sigh. “But fuck… I have a good feeling about this. I really feel like a spice of passion can be good. I can remember what it’s like to feel good again, and maybe you can learn a few tips. This will fix us. I know it will.”

Maybe I was losing my mind, or maybe I just missed this Bridget too much and wanted her back.

“I love you. And I love you enough to trust your instincts. If you really, truly believe this can be the spark to save us… then we can try.”

She smiled warmly back. “I love you, Justin.” She leaned in to kiss me. It was our first in many days — maybe even since the party. But this one was so much more passionate… so much more real.

“But I reserve the right to call it off after the first try,” I added. “We need to be on the same page at all times.”

“Agreed. This isn’t about Anthony. It’s about us.” I fully believed Bridget wanted our relationship to be saved just as much as I did.

“I’ll set something up for next weekend,” Bridget said, rolling onto her side of the bed. “I’ll make sure everything’s in order. All you gotta do is show up.”

We turned off the lights and went to sleep. It was another sexless night — one of so, so many. But the prospect of intimately re-connecting with Bridget was thrilling… even if it meant there’d be another man in our bed, sharing some of those thrills.

========

The remainder of this 18-chapter, ~40,000 word novel is available on Kindle. Link below. I hope you enjoy! It's my favorite one I've written so far :)

-Jennifer

Link: https://www.amazon.com/dp/B0C1PPK25S

*FYI, this is Chapter 2 of 3 that'll be shared here on BC!*

CHAPTER TWO

I don’t think Trinity realized how strange her question was. If she had, she wouldn’t be looking at me so matter-of-fact. Was this supposed to be a joke?

“I… I don’t wear lipstick,” I told her with full sincerity, though my voice was wavering a tad.

“I know. You said that. I’m suggesting you try it on and give me your thoughts. Always better to have a second opinion.”

A million reasons for why this was a dumb idea popped in my head. And still, I was blown away by Trinity’s earnestness.
My Aunt — a forty-something beauty product influencer — wanted to share her interest with me. So in that regard her proposal was actually kind of sweet. But ‘sweet’ doesn’t mean ‘rational’.

My face was stuck in this weird, uncomfortable contortion as I mulled over her question. My prolonged silence and hesitation was becoming funny to her.

“Oh, don’t be such a little wuss,” Trinity teased. “Life’s all about trying new things! It’s not like you’ll be on camera.”

Hmm... She’s right. It’s only the two of us after all. I stared across the room at Trinity, playfully twisting the tube of lipstick in her hand. The sound of the twisting tube was like a siren’s song, luring me toward disaster.

“Okay but you have to put it on me,” I said, finally backing down.

Trinity was ecstatic. “Yes! You’ll look so darling, I guarantee it.” She grabbed my hand and pulled me closer, molding her mouth into a weird shape. “Put your lips like this and try not to move.”

I did as told, standing as still as possible while she gracefully applied the product to my lips. It didn’t take long — 15 seconds at most — but her reaction suggested I looked like a whole new person. “Ah, I knew it! You do look darling.”
Enough already. I had to see myself. I scooted around Trinity to a mirror hanging in the living room and…

Wow.

I didn’t exactly look like a different person, but the bold red pop on my lips changed the entire energy of my face. It was as if my face had a secret femininity that was unlocked by the red lips. My bold, brown eyes, thin nose, and tight jawline suddenly seemed softer and girlier paired with the new lip color.

“That’s the power of makeup,” Trinity said, giggling as she watched me purse my lips in the mirror. “A good lip can change a face for the better.”

“I don’t know if I’d say ‘for the better’…” I replied cynically. “I look like a freaking girl!”

Trinity came up behind me and tugged at my hair tie, loosening my brunette ponytail and letting it fall onto my shoulders. Her eyes widened. “Nope. Because now you look like a freaking girl!”

One look at myself with my hair down and the red lipstick and I nearly lost it. I retreated from the mirror, overwhelmed by this new, shockingly feminine appearance. “Okay, that’s it! We’re done here. This is too freaky.”

Trinity was dying with laughter. “You’re so sensitive! Are you always this jumpy?”

“No, but I’m also not normally wearing lipstick with my hair down!” I snagged a tissue from the table and started rubbing my lips to get the makeup off as fast as possible. Trinity rushed over to stop me.

“Wait, you promised me a review!” she pestered, grabbing the tissue from my hands. “Just tell me, what did you think?”

Seriously? Was furiously removing it not a clear enough answer? “Freaky. That’s my review.”

She rolled her eyes. “Ugh, you boys could really learn to lighten up. I actually thought you looked pretty.”

“I know. I did. That’s the problem,” I told her firmly.

Trinity must’ve gotten the message by now because she held up her hands in defeat. “Alright, alright. You win. Thank you for trying, I guess.”

I didn’t like how things had gotten so tense so quickly after such a nice time unpacking my car and touring the house. Maybe I was just on edge after a long day of travel.

“I’m… I’m gonna hop in the shower and chill in my room for a bit,” I told her, still a little uneasy. “Go ahead and finish your work for the day.”

========

As I came to learn, Trinity was not the type to hold a grudge. She left me alone to unpack my things and set up what’d be my home for at least the next couple months. Neither the lipstick nor anything beauty-related was brought up the rest of the day. She must’ve realized her overstep and that pushing makeup on boys is not the best way to garner trust.

But that evening, she more than made up for it by preparing a lovely first dinner for the two of us — delicious tofu stir-fry. Trinity, like myself, was a vegetarian. But unlike myself, Trinity was an excellent cook. I always thought that the best cooks are able to fill you up twice: first with the smell, and later with the taste.

Already I could tell that living with Trinity would be safe, nurturing, and peaceful. In many respects that was ideal — after all, who doesn’t want a secure home life? But I had to be careful not to get too comfortable. My time in Old Buffalo wasn’t going to last forever, and I had my eye firmly on the next stage of life — a nursing job at a glitzy, downtown Chicago hospital.

These days, an ADN degree doesn’t get you much, especially in the hyper-competitive Chicagoland area. In order to get a decent job, I’d either need a Bachelor’s degree in Nursing (which I don’t have), or a passing score on the NCLEX exam — which we call ‘the boards’. Passing the boards would give me the RN designation necessary for a fighting chance. In fact, ADNs are already in an uphill battle against BSNs… but hey, it’s the hand I’ve been dealt and the one I’m gonna play. So my ‘job’ for the next couple months is to study-up and make myself the best possible candidate… whatever that entails.
I communicated this clearly to Trinity, and she was supportive of my studies. I’d have my space, she’d have hers. We’d respectfully live our separate, very different lives.

========

“Morning! Sleep okay?” Trinity asked with pep as I trudged downstairs to the kitchen. Damn, I thought that getting up at eight in the morning I’d be the first one up, but it looked like she’d already returned from a run and was halfway into cooking breakfast.

“Fine, thanks,” I said through a yawn. I peered over the pan. “Are those sausage links?”

“Beyond sausage,” she replied. “I’m in love with that fake meat stuff. It’s a vegetarian’s mistress!” Trinity flipped the links another time and determined them ready. “Want some?”

I checked the time on my phone. “Sure, but I’m eating quick today. My plan is to treat studying like a 9 to 5 job. There’s a library nearby right?”

“Good on you! And there sure is. It’s in that sleepy part of downtown near city hall. Nice area to walk around too.”

I snacked on my fake meat links and a couple eggs Trinity scrambled up as well. “Any plans for you today?”

“Gotta film a couple videos this morning. Then I’ll probably swim some laps at the club. Oh! And I got some things I need to bring down from the garage attic…”

“Jeez, active day!” I replied.

Yesterday’s dinner conversation all but confirmed that Trinity was in the ‘upper class’ of Old Buffalonians. Not only was she a homeowner, but she was a member of Golden Dunes Country Club. By the sound of it, anybody who’s anybody was a member there. Old money, new money… as long as you had money and lived in Old Buffalo, you were a member of Golden Dunes.

As tempting as an invite to her glamorous club was, I politely declined for today with my sights set on studying. One tasty breakfast later and I was off to the library.

========

My second time driving through downtown Old Buffalo was much more thought-provoking. I wondered who lived where and who belonged to Trinity’s club. What did these people think of out-of-towners like myself and the thousands of other Chicagoans who made Old Buffalo their summer home? Was it frustrating, or did they appreciate the economic boost? Still, for essentially a vacation town, Old Buffalo looked like any other in the midwest: quaint and quiet.

Exactly as Trinity said, the library was directly across the street from the impressive city hall building — but certainly not overshadowed. The twin buildings were architectural marvelous — twin gothic, limestone beasts looming over the town with matching, massive lawns out front. I wondered if that was intentional. Clearly the town took great pride in its public buildings — a quality I really appreciated, even if much of that enjoyment was given to people who only lived here three months of the year. But maybe I’m just wasting my time thinking about the locals knowing the goal of coming here is just to leave as fast as possible.

In the large main room of the library I found a giant wooden table to claim for the day. Though I tried my best to be quiet, I noisily spread out my study materials around the giant table: notecards, notepads, binders, my laptop, and several textbooks.

I’ve always been a chaotic studier. Heavy on practice materials and verbal repetition. You could argue that a public library is the worst place for this, but I also didn’t want to bother or be bothered by Trinity’s filming. A barren, mid-day library did just the trick as long as I could keep my voice down.

Outside of a 45 minute jaunt to a sandwich shop for lunch, I was pretty much trucking through the day uninterrupted. My only concern was the precipitous loss in retained nursing school information. Hell, I’d only graduated a couple weeks ago and I felt like there were so many facts and practices that weren’t immediately coming to me. But still, I knew with diligent work and focus I could pull off being fully prepared by the end of August.

I was rolling, I was locked-in… That is, until my phone rang just before 4. Not a text, a call. It was Trinity. Ducking my head and hushing my voice, I answered.

“Hey, what’s up? I’m in the library so I can’t re—” I began but was quickly cut off.

“Is this Anderson Saffron?” a voice asked. A man’s voice. It was Trinity’s number but this wasn’t Trinity.

I suddenly felt a little scared. “Uh… yes. Who is this?”

“Excellent. Just giving you a heads up that your Aunt is in the hospital. Please don’t worry, she’s gonna be fine. She just had a fall.”

“A fall!?” I exclaimed, much to the annoyance of the other library-goers. “Sorry… uh…”

Thankfully, the man jumped in with an address for the hospital. I hung up the phone in shock. “A fall?” I whispered to myself as I hurriedly packed up my things and shuffled out of the library.

========

A kind greeter directed me to the first floor room where Aunt Trinity apparently was recovering. Blessings of a small town hospital I suppose — no hour-long corridors to traverse just to find a patient room.

The floor was pretty dead when I arrived. Nothing like the hospitals I was accustomed to with nurses and physicians buzzing around, busy as bees. In fact, I was actually halted not by a medical professional, but the admin assistant.

“Hey hey hey,” she held up her hand, preventing me from going into the room. “Anderson?”

I skidded to a stop. “Yeah, what?” Ugh, that sounded harsh… “I’m sorry, I’m in a rush.”

The woman in her 60s smiled sweetly. “I imagine so! Just so you know, your Aunt is okay… but she might look a little… shocking.”

“It’s okay, I’m a nurse,” I answered confidently.

“Oh, you are? Good! I’d ask where you work but I’m sure you’re in a rush.”

“Unemployed at the moment. Studying for boards,” I answered a little dismissively and walked briskly into the room. I hate coming across as rude, but this wasn’t exactly a time for chit-chat.

I lightly knocked on the door and opened it, just as I had when arriving at Lumber Lane. But instead of a bouncy, bright Aunt Trinity, she was in far worse condition.

Amidst the jungle of medical equipment, bedding, and bandages sat a person. “Trinity?” I asked, concerned.

“Mmhm!” I heard from the body. A little muffled, but surprisingly peppy. “Hey!”

Now, I should say as a nurse, I’ve seen blood, cuts, bruises… you name it. So Trinity’s appearance didn’t exactly bother me, but she certainly didn’t look like her normal, gorgeous self either. There she sat, propped up in the bed with a bandage over about half of her face like a poorly-wrapped mummy. Her left arm was in a sling and had thick, bulky padding on her right shoulder. The other hand was resting on her lap in a splint while the rest of her body had a smattering of bandages covering up what must be scrapes, bruises, or even worse.

“How silly do I look, huh?” she muttered. I couldn’t believe she could have a sense of humor at a time like this.

“What… what happened?” Was all I could manage.

She sighed and looked at me with her one visible eye. “Forgive me if I’m not too wordy because this all hurts like hell… but I was cleaning out the attic and had a terrible fall down the stairs. Caught myself… kinda…” she gestured to her shattered arms. “And it led to a full-on face plant.”

“Oh… my… god…”

“Yep... Thankfully the garage door was open and my neighbor Andrew walked by at just the right moment. I felt like Kate Winslet at the end of Titanic, yelling for help with any breath I could muster. Except I didn’t have a whistle and it wasn’t freezing water.”

So Andrew must’ve been the man that called me. “Jesus… What’d they diagnose you with?”

Well, I haven’t seen an ortho doc yet, but my hand and shoulder are super fucked up. Must have a couple broken fingers too… And my nose. I mean, falling 12 feet onto solid concrete will do that!”

“I’m sure…” I said, still taking in the horror of her condition.

“They’re keeping me here for a few more hours while things get figured out. Mind sticking around?”

I took a step toward my Aunt and tenderly placed my hand on the side of her bed. I was afraid if I touched her, I’d only break another one of her bones. “Of course of course of COURSE!” I said emphatically. “Anything you need, okay?”

Trinity sighed and gave me her best pain-free smile. “I’ll have the doc explain more to you since you guys speak the same medical language.” Another deep sigh from Trinity, followed by what seemed like a painful cough. “Fuck! Everything hurts.”
“I know, I know…” I replied gently, still standing next to the bed. “Shitty start to the summer.”

“The worst. And right after swimming my fastest quarter mile ever,” Trinity lamented. “I’m sure you figured, but I’m gonna need a little help around the house for the next couple days.”

I chuckled. “Weeks, probably. But sure. Whatever you need, I’m here for you. I’ll mix in my studies with all the caretaking you need, okay?”

Another smile, but this one a little less sure. “That’d be great. But you know… There’s also a job I can no longer do.”
I raised an eyebrow at her, afraid of what she was about to ask. But Trinity was nothing if not earnest. “I know you’re a boy and all — and I know you despised that lipstick. But maybe you can lend a hand reviewing a few more products? Princess Trinity could really use the help…”

========

Look out for another sample chapter this week! Hope you all like this new one :)

Amazon Link: https://www.amazon.com/Can-You-Lend-Hand-Feminization-ebook/...

*FYI, this is Chapter 3 of 3 that'll be shared here on BC!*

CHAPTER THREE

I desperately wanted to help out Trinity. I mean, look at her! She’s in seriously deep shit. But just because her arms aren’t working, doesn’t mean her brain isn’t.

“Uh… let’s talk about that later,” I said, not wanting to outright reject her at the moment, but still wishing to convey sympathy. It was a punt, sure. But a necessary one. Right now, the thing she needed most was company and comfort. So that’s exactly what I provided for the next couple hours, as we talked, laughed, and kept things light.

Not wanting to be stuck with an overnight hospital bill, Trinity opted to be taken home in the late evening. She’d had an exhausting day and needed rest more than anything. The results of her MRI would be coming tomorrow, but neither of us were counting on good news. What more could I do than get her safely in bed, help rewrap her wounds, and keep her as comfortable as possible.

========

“Mhmm…” Aunt Trinity murmured, listening to the doctor as he delivered the results over the phone. “I guess it’s not too surprising… What about a timeline?”

Trinity and I were seated around the kitchen table, listening to the doctor’s verdict on speaker phone from her cell.

“You’re lucky it’s not worse, honestly,” he said frankly. “Your broken nose should heal up fine without treatment. A few weeks there. The left pinky finger will need to stay in that splint for maybe a month.” The doctor paused, then delivered the major blow. “The hand and shoulder… Those will take a while. No surgery, thankfully. But a couple months, maybe, to get back to normal. And that’s before even starting physical therapy.”

“And all the facial brushing?” Trinity asked, strangely concerned about that element the most.

“Like I said, the nose’ll heal on its own. The swelling and scratches will too. These things just take time, Trinity. Just hold off on headshots or yearbook photos for a while.”

I chuckled, but Trinity sighed. “I understand. Thank you.”

We signed off with the doctor and Trinity, for the first time, slumped in her seat. The ever-positive woman was finally beat down.

“You know, it could be way worse,” I said, parroting the doctor’s words.

“Yeah, it could…” she admitted. “There’s just so much I wanted to accomplish around here this summer. I was thinking about re-doing a bunch of landscaping, I had my swimming goals…”

“Well, I could always drag you behind me in the lap pool,” I kidded. Trinity laughed again, somewhat painfully as she clutched her shoulder.

God, did I ever feel bad for her. I could tell this physically broken woman was fighting to keep her spirit intact. A splint on her finger, a brace on her hand, and that shoulder sling made her look like an injured war vet. Not to mention her face, which hadn’t improved much since yesterday. Her lips, eyebrows, and forehead were all cut, scraped, and covered by bandages. Half of her face was a sickly, purple-yellow from the bruising.

“How about this… The mornings will be for me to study. Then when the afternoon hits, I’ll run your errands, do your yard work, and complete any chores you need.”

Trinity’s face lit up. “Seriously? That’d be lovely!” she exclaimed. “Ah! I honestly can’t thank you enough. I promise, I’ll think of a way to repay you.”

As much as I wanted to ask for money, my heart deep down couldn’t accept payment for this kind of work. She was giving me free room and board, after all. If there’s one thing my parents instilled in me, it’s that you help out your family — no questions asked. And even so, it’s not the worst idea to practice my caretaking and nursing skills.

========

For the next several days, my schedule went exactly as planned. I’d wake up and help Trinity with whatever she needed physically — dressing, bandage changing, medications… With such limited mobility of her hands and upper body, even simple tasks were a massive struggle if unassisted. So I realized a helpful daily task would be prepping for her breakfast and lunch in the mornings.

From morning to lunchtime, I’d camp at my now go-to table at the library, studying away and desperately clinging to anything I’d retained from two years of nursing school. Even if I hadn’t learned much in the short time, I’d at least gotten better at quietly shuffling my books, binders, and papers to avoid mean glares.

I’d return to Trinity’s in the early afternoon for a quick lunch, then jump straight into her to-do list. Each day brought its own unique challenge or task, though thankfully I had Trinity right there to teach or explain how to do things. I was a little ashamed how not handy I was. I mean, jeez, I didn’t think I was so sheltered growing up, but my lack of familiarity with gardening tools and lawn care trinkets was exposing all my weak points.

A great example was when the freezer door handle was busted and needed to be re-screwed.

“There’s an allen wrench in the garage—” Trinity began, to which I replied with a blank stare. “Really?” she added. “God, your Dad taught you all the wrong things…”

Funny enough, I felt like I was making more progress as a homeowner/landscaper/errand boy than I was being an actual nurse.

The best part about this rhythm though was, at the end of the day, Trinity and I would spend an hour or so in the kitchen making a delicious dinner for the two of us. With her brain and my hands, we cooked up some pretty tasty vegetarian dishes. Only one week in and I was growing more and more comfortable with her. Hell, I lived with my own mom for my entire life — and of course, I love her to death — but I never really developed an adult relationship with her. Aunt Trinity was different. Closer to me in age, similar-ish stages in life… She felt like the mix of a mother and older sibling mixed into one.

By my second week we’d already set the precedent that Wednesdays would be movie nights. A week ago, she was in much worse shape and barely cared what I threw on. This week, she put her foot down as tonight’s decider. I guess I’d call it progress.

“You ever seen ‘She’s All That’? Because if you haven’t, it's essential.”

I shook my head. “No, but even the title sounds like a shitty rom-com.”

“It’s absolutely a shitty rom-com. And that’s why you need to see it,” Trinity insisted, motioning for me to pick up the remote and queue it up. She didn’t have cable, but I found it after digging through a couple streaming services.

I’d never heard of this movie before, but it didn’t take long to realize it was basically that old musical, ‘My Fair Lady’. Essentially, Freddie Prinze Jr. bets his friend that he can transform the nerdy Rachel Leigh Cook into the next prom queen. And shocker, he starts to fall for her.

The movie was charming and goofy enough to warrant a watch, and if anything, I enjoyed Trinity quoting certain lines and reminiscing about the first time she watched it. Trinity is definitely a movie talker, too — something I normally wouldn’t have the patience for. But hey, tonight’s her night.

As the movie hits its third act, there’s a scene where Rachel Leigh Cook waltzes downstairs, beautifully transformed into a prom queen. It’s a sweet moment, they play that ‘Kiss Me’ song in the background… It's great. I looked over across the living room at Trinity, wondering if she was a movie crier in addition to a talker, but she wasn’t crying. In fact, through the bruised coloring on her face, I noticed an idea formulating.

“Can you pause the movie?” she asked. I did as told and she looked over at me.

“You never told me if you’d help me out with the beauty products,” she said bluntly. Notably, it wasn’t a question. She worded it almost as an accusation — though not that aggressive.

I admit, her question didn’t completely catch me off guard. After all, this movie’s all about transformation and letting beauty products turn you into something you’re not.

“No, I haven’t,” I answered honestly. “I kinda thought you just didn’t care.”

Trinity softened her tone. “I don’t want to seem unappreciative, but… I dunno, this movie’s making me feel like I’m missing out. I have such good momentum with the influencer thing, and I got a backlog of all these products I wanna review. But… look at me.”

Her face looked better than it did a week ago, but a shoulder sling, a brace, a splint, and bruises galore don’t exactly lend themselves to the beauty influencer look.

“So what’re you suggesting? You wanna doll me up like a prom queen and have me waltz down the stairs?” I asked, completely joking, but quickly afraid I planted a seed in her head.

“No, no… just, like I said, lend a hand in that department. I need content for my pages. I’ll do all the posting and captioning. I just… I need a temporary model.”

I thought about her request for a moment. She must’ve caught me in the exact right mood, because her words didn’t sound so absurd this time around. “Alright… What do you have in mind?”

“Well, I got this super cute nail polish that I’ve been meaning to show off. Obviously, nobody wants to look at a splint or a brace so–”

“Sure,” I answered confidently. “Nail polish I can do.”

She raised an eyebrow. “Seriously? Wow, I honestly thought you—”

I didn’t have much patience for dissecting my acceptance of wearing nail polish. “I guess you just caught me in a good mood.”

If it weren’t for her injuries, she would’ve jumped for joy and applauded. But Trinity looked as happy as can be. “Ooh! Can I paint your nails during the movie? There’s just enough time left that it’ll work out. I can use my left hand, too!”

“Uh…” I muttered, not expecting this to start so quickly. “I guess…”

Trinity had me fetch the bottle of nail polish that was boxed up in the closet near the front door with the rest of her unopened, gifted products. I grabbed the small black box she told me about, perched right on top of the looming mountain of unboxed girly products. I shut the door and returned to the dimly lit, quiet living room.

“Sit here, let me show you,” Trinity said calmly, as I took my seat next to her on the couch. I gulped, more than a little nervous as I removed the bottle from its packaging. It was a bright, baby blue color. I hadn’t been this nervous around my aunt since the lipstick moment on my first day here. The vision of myself in the mirror, looking almost entirely like a girl from only lipstick. Would nail polish create the same stomach-churning feeling of a feminine Anderson?

But just as I screwed the top off the bottle to begin, Trinity shifted away. “Phew!” she said, scrunching her face. “You, uh… Did you shower after yard work today?”

“I… Uh… I guess I didn’t,” I said mindlessly, still focused on the impending nail polish. “Sorry, we went right into cooking—”

“Oh, it’s no problem,” she assured me, giggling. “But can you blame me if I wanna avoid smelling your stink for the next half-hour?”

I turned bright red with embarrassment. Here I was about to get my nails done by my Aunt, and now she was telling me I stink. But I took the awkwardness as an escape route. “Fine, I’ll go shower. So nails tomorrow?”

Trinity shook her head. “No, still nails tonight. We have a movie to finish!”

I shrugged, accepting her request. But I took only one step upstairs before she called my name again.

“Anderson? I actually have a better idea. Can you use my shower?” she asked politely.

I stared at her, confused. “…why?”

“I want to paint all of your nails and take pictures for the page. Toenails too. So that means I’ll need freshly shaved legs for the pictures.”

========

If you're enjoying the sample, check out the remaining 20 chapters in this book on Kindle (and very soon available in paperback!) Thanks for reading :)

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*FYI, this is Chapter 3 of 3 that'll be shared here on BC!*

CHAPTER THREE: A DRESS FROM DIANA

“Olivia, this is insanity. I’m not putting it on.” I held up the dress away from my body, as if physically distancing it would do any good convincing her otherwise. “Plus, that whole house game was years ago.”

“Jesus, chill. I’m not asking to play house — we’re not freakin’ kids. I’m just saying we used to do it, so it’s not unprecedented for you to wear a dress. Maybe you’ll even look cute.”

I couldn’t believe what was happening. Olivia must know how uncomfortable this subject was making me feel, yet she persisted. In fact, one of the reasons I found her annoying in the first place was precisely because she demanded I be a girl when playing house as kids. I know it’s not fair to judge a person by their actions as a 10 year-old, but certain things stick with you.

I assumed Olivia would just give up. It’s a useless request after all. I didn’t even want her to try it on, much less myself. All I wanted was for her to put back the dress, mark it as a notable item, and set it aside in the garage. But of course nothing can be that simple.

“You know…” she began suspiciously. “You’ve been begging me to help out. And I’ll admit, maybe there’s more I could contribute.'

I laughed dismissively. “You think?”

“Well… if you try on this dress, I promise to be an equal partner for the rest of the day. An entire work day of me working just as hard — if not harder! — than you.”

Was… was she being serious? I stared at her dubiously. Olivia offering to work? That’s not like her at all. But then again, I’d be giving her something in return.

“Really? No complaints?” I asked.

“Sure, why not.”

I glanced down again at the dress. The garment still looked incredibly foreign to me. In fact, it looked more like a robe or an overcoat than a proper dress. I made an obnoxiously loud sigh. “Fine. If this’ll shut you up and put you to work, then I’ll try on the freakin’ dress.”

Olivia did a half-cheer, half-cackle which instantly made my decision sting even more. I just prayed that she wouldn’t expect this to become the norm.

Walking into the bathroom, I felt more foolish than ever. Was I really so weak that I’d put on a dress to appease my cousin rather than manning up and forcing her to work? If she weren’t so stubborn, maybe I’d be able to break through. But here she was, offering me an out. So you bet I’m taking it.

From my limited experience wearing dresses as a 10-year-old, I knew that having shorts and a t-shirt underneath wouldn’t allow for a proper fit. So I stripped down to my boxers and stepped into the dress, carefully securing it around my body and zipping up to the best of my ability.

Objectively, I looked a bit silly. While I’ve been told in the past that I have ‘feminine features’ — my long hair and smaller frame certainly doesn’t help either — I was still clearly a boy in a dress. However, for as bulky as the dress was, it was impressively swift and comfortable. And Olivia was totally right — it fit me perfectly.

Olivia’s loud knocking on the door startled me. “You done in there? How long does it take to put on a dress?”

“I’m coming!” I shouted back. Ignoring all fear and setting my pride aside, I stepped back out into the main basement area for the big reveal, trying not to trip on the skirt of the dress that hung mere centimeters above the floor.

“Ah! Adorable, Madison!” Olivia exploded. “Look at you, ya little princess!”

I growled back at her, but nearly tripped while doing so. “Yeah, yeah…”

“Well,” she began, arms crossed and looking pompous. “Give us a twirl.”

“A twirl?” I groaned. But Olivia was serious. The girl wanted a twirl, so I gave her a twirl. The dress wasn’t very flowy, but it satisfied Olivia.

“Lovely. Just lovely,” she complimented. “How does it feel to be the first person to wear this dress?”

The first person… Huh. I hadn’t thought about that. After all, the letter was addressed to Diana, not to me, and seemingly never mailed. Hell, I didn’t even exist when the letter was written.

“I’m taking this off. Time for your end of the bargain.”

Olivia sighed, but agreed. “Fine. A deal’s a deal… Wait! One more thing!” She galloped over to me and yanked at my hair that was still up in a bun.

“Hey! What’re you doing?” I tried to physically resist her, but the dress wasn’t exactly fluid.

Without a word, Olivia had let me hair out of its bun, cascading past my shoulders and down my back. Her eyes lit up.
“Holy shit your hair got long!” she exclaimed, examining my lengthy mane. “Has it always been halfway down your back?”

“I’ve been growing it out. But I keep it up in a bun for a reason. It gets everywhere.”

She was mindlessly running her fingers through my hair. “I’m sure it does… Could definitely use a brush… and some conditioner…”

I finally swatted her hand away. “Alright, you’ve done enough. I’m taking this thing off.” Olivia graciously released my hair and I stepped toward the bathroom.

“Madison!” Olivia called me again. But the moment I turned around I spotted her taking a picture of me on her phone.

“HEY! WHAT THE HELL?” I yelled at her, shuffling my feet toward her to snatch the phone away.

“Relax! I’m not sending this to anyone. I just want a little souvenir of a fun moment with my cousin.”

I stared at her. “Is that a promise?”

She looked back sincerely. “I mean, yeah. I’m on your team, Madison.”

There was no choice other than to accept her promise. So I stripped off the dress, put my hair back in its bun, and prayed that she’d come through on her end of the bargain.

========

I’ll admit it, I had my doubts about Olivia… but she freakin’ came through today. I put on the dress and she worked her butt off. The entire rest of the day, she diligently dug through boxes, sorted junk, and kept her head down without much complaint.

I was so jazzed about successfully getting her to work, that I nearly bragged to my mom about it. Though one look at her stressed out face when she stepped into the living room told me everything I needed to know.

“Good day today?” I asked from the couch.

“Fine,” she sighed, dismissively. “Never go into medicine, okay?”

She’d given me that line a lot. It’s funny how doctors always say ‘helping people is my passion’ and ‘it’s worth all the trouble’. But find an honest one and all they’ll do is complain. I guess they are like the rest of us.

After a bit more thought, I figured telling her about my Olivia triumph could be a massive backfire. The less she was involved in my day-to-day at Grandma’s house, the better. Plus, I’m sure she’d be abhorred by the idea it took me wearing a dress to convince my cousin to lift a finger. ‘Be a man and make her work!’ she’d probably say.

But as the evening went on, I couldn’t stop thinking about the curious letter from Grandma to Diana. So she sewed dresses for her. Got it. But was that all to their relationship? There had to be more to the story. And I knew if I didn’t ask my mom now, it’d eat at me for the entire summer. Against my better judgment, I decided to ask her just before bedtime as she was winding down with a mystery novel on the living room couch in her pajamas.

“Can I ask you something?” I began delicately.

She didn’t look up. “What, Madison?”

“Look, I know you hate talking about Grandma—”

“Correct. I do.” Mom interrupted.

“Okay… but listen. I found a letter she wrote to someone named Diana. Does… does Grandma have a sister?”

Whatever I said certainly got her attention, but not in a positive way. She took off her reading glasses, and looked at me squarely.

“Madison, I don’t know how many times I have to say this. Your Grandmother was not a good woman. Plain and simple. All she ever did was judge and criticize and cut people out.”

“Sure, but I just want to know if she had a sis—“

Mom stood up, pinching the bridge of her nose to keep back her frustration. “Jesus, Madison…” I could tell she was considering whether to tell me anything at all. “Yes. She did. Diana died young. Soon after moving across the country she died. It was a tragic car accident.”

“Oh my god… I’m so s–”

But Mom had more to say that wasn’t so affectionate. “You wanna know why I never talk about her? Because everything about Grandma — everything she did, and everyone she knew — well… it no longer matters. Got it? She’s out of my life! The only thing I want is to pay your ten bucks an hour to scrounge through her shit and see if there’s anything of value. Not sentimental value. Money value, Madison. That’s it.”

I’ve heard Mom rail against Grandma before, but this time felt different. It was like she’d reached her boiling point and was about to explode, finally finished with addressing the past. I understand that she truly hated this woman — she made it loud and clear — but it was aggravating not being able to discuss my own family history.

“So please,” Mom continued. “Just do your job, and don’t bring up Grandma, Diana, or anyone again. Stay out of her memories. I’m sure you’ll find nothing but trouble.”

========

I drove to Grandma’s the next day in silence. Even with a whole night to think it over, I couldn’t decide how to feel about the Diana situation. No, I didn’t think it was fair of her to be the sole custodian of my family history, keeping the keys locked away. My empathetic side insisted I honor her pain and just let things be. But damn it, if it wasn’t hard to do that for a woman like my mother…

Pulling up to Grandma’s house, I was annoyingly reminded that today wouldn’t be like yesterday. My dress-for-work deal with Olivia had expired, so once again I’d be essentially on my own, doomed to dig through garbage while she idly laid by scrolling on her phone.

But on my way to the basement, I got startled and nearly fainted turning the corner running into Olivia. I was about to yell at her for not paying attention on her phone… but she was holding a box.

“Shit, Olivia! What’re you trying to kill me??”

She raised an eyebrow and looked down at my sorry butt recovering on the floor. “Wow, I assumed you’d be happy I’m working.” I just sat there, my heart still beating.

“Just watch where you’re going, okay?” I rubbed my eyes to make sure I wasn’t hallucinating. “You’re… working?”

A smile crept on Olivia’s face. “I have some news about Diana. I’ll meet you in the basement in a sec.”

Olivia shuffled off to the garage to drop off some items while I moseyed downstairs. By the look of it, she’s been here a while. What kind of alien had possessed her? First she’s working, and now I’m seeing she came in early?

She returned from the garage and gestured toward a box she’d set aside on the covered-up billiard table. It wasn’t spectacular — as broken and as ragged as anything else we’d seen — but it had the word ‘Diana’ written in marker on the side.

“Where… When…” I stammered.

Olivia laughed. “I came in a little early. This whole Diana stuff got me psyched up to keep digging.”

Seeing and hearing her name made my gut grumble. I still felt a little guilty from pestering my Mom last night. “Listen, Olivia… about this whole Diana stuff… maybe we should just let it go.”

But Olivia wasn’t ready to give up. Not before her bombshell anyway. “What if I said I found a picture of her in that box?”
My eyes widened. “No way…”

She nodded. “Mmhmm. And it gets even crazier.” She held up an old photograph of a woman, presumably Diana. But before I could even study it, Olivia held up her phone right beside it.

My jaw dropped. The photo of Diana wasn’t too remarkable — just a simple photo of her standing by a door in a dress, no emotion on her face. But pulled up on Olivia’s phone was the photo of me from yesterday, wearing the dress with my hair down. And I eerily resembled the woman.

But in fact, it was far more than a resemblance. Diana and I looked nearly identical.

========

The rest of this ~50,000-word, 21-chapter book is available on Amazon! $3.49 or free with Kindle Unlimited. Thank you as always for your support! You inspire me to up my game with each subsequent book. Plenty more on the way :)

Amazon Link: https://www.amazon.com/Dresses-Diana-Gradual-Feminization-St...

*FYI, this is Chapter 2 of 3 that'll be shared here on BC!*

CHAPTER TWO: UNEXPECTED HELP

“O-Olivia?” I stumbled, slowly coming to terms with who it was, but somehow not truly believing it. “No way…”

“Uh, yeah?” she said somewhat rudely, then laughing. “It hasn’t been that long.”

“I mean, like, five years… but whatever. What are you even doing here?”

Olivia shrugged, pausing the music on her phone. “Jeez, I thought you’d be happier to see me. Mom said I could get paid to dig through Grandma’s shit before they sell the house. I didn’t want to get a real job, so I figured I bum around here all summer instead.”

Shit. Is she serious? All summer? Why did my mom never mention this to me? Did she do it out of spite? Or maybe Aunt Lorraine unilaterally made the call to give Olivia a job too. This family is both vindictive and horrible at communicating, so neither would be surprising. Regardless, considering Olivia had already dug out boxes and accepted payment from Aunt Lorraine, it appeared she was here to stay.

“So… I guess we’re doing this together,” I said in defeat.

Olivia paused the music and shot me a dirty look. “Yo, what’s your problem? I don’t see you for five years and the first thing you say to me is ‘no way!’, like I’m the last person you wanted to see.”

Admittedly, I didn’t much care for Olivia. Despite being the same age, we couldn’t be more different people. She’s always been that bratty, loud girl with a rebellious streak, and I can only assume those personality traits stuck through high school. We didn’t keep in touch the last few years, outside of the occasional update I’d get from my mom — usually about a toxic boy she’d start seeing to piss off Aunt Lorraine.

And just looking at her, it’s not surprising that boys wanted to date her. She’s drop-dead gorgeous. At least 5’10” and with the body of a model. She had long, straight blonde hair and piercing green eyes that stood out against her pale skin. But Olivia didn’t exactly dress like a ‘popular’ girl. She had an alternative, grungy style that made her unique. Even today, she wore a tastefully tattered, un-buttoned gray flannel over a crop top with ripped, dark-wash jean shorts and off-white Jordan sneakers. I remember my mom once mentioning that she ‘was wasting her looks with such an unflattering style’. For once, I kind of agreed.

“Maybe my tone was a little rude, I’m sorry. I just thought I’d be working by myself.”

“Ahh,” Olivia nodded. “Makes more sense. My mom only told me on the way out the door this morning that you’d be doing it too.

Must’ve been a last second thing.” She took a portion of her hair and casually flipped it behind her shoulder as she talked to me. I noticed one side of her head was shaved down to a buzz cut. Damn, she really was going for the grunge look.

There was an awkward moment of silence as we both tried to judge what to say after five years of not speaking. I could tell this was going to be like pulling teeth. “At least we have two sets of hands!” I managed to say.

She shrugged. “This place is a fucking dump, yeah?” Olivia tossed the orange dress she was holding back into one of the many cardboard boxes behind her. “I don’t even know where to start with this crap.”

Neither did I. The basement — much like all the bedrooms and the living room upstairs — was consumed by dusty cardboard boxes, loosely held together by masking tape. It’s a shame, considering the bones of the basement were quite nice. A quaint sitting area sat to the left of the stairs with a couch, two barcaloungers, and a cushy ottoman in front of a classic TV. The right side had a billiard table, an upright piano, and an old desk that my Grandpa must’ve used. I stood there, hands on my hips, surveying the basement and hoping an efficient plan would just manifest in my head.

“Maybe we take it one section at a time. It’s not gonna be quick or easy, regardless of how we split it up.”

But Olivia was barely listening. She was mindlessly digging through one of the boxes. “Uh-huh, sure.”

I rolled my eyes. She definitely wasn’t going to make this easy.

========

The next few hours made it abundantly clear who’d be the adult in the room. While I diligently worked, Olivia lollygagged and procrastinated. She wasn’t interested in the job at hand or, frankly, even the concept of work. Most of her time was spent on her phone, scrolling social media and lounging around. Not that I’m immune to phone addiction, but it was frustrating knowing our wages were the same for drastically different levels of effort. But beyond passive-aggressive comments, what was my recourse? She was my equal in this situation, and I really didn’t want to get Mom or Aunt Lorraine involved.

I insisted we start with the boxes in the sitting area and work our way around to the rest of the basement. That way when we needed a rest, we’d have a nice, clean space to turn to. The process was pretty straightforward. ‘Vintage Items and Collectibles’ were what our Moms wanted us to look out for. Again, I didn’t exactly have an eye for what was valuable, so I ended up deferring to Olivia most of the time. “That’s crap,” or “Eh, could be something,” were the phrases I heard from her most.

The variety of junk that Grandma accrued was startling. From what I remember, she frequented garage sales and was a serial ‘project-starter-but-not-finisher’. That meant many of the boxes were flooded with partially stitched clothing, cracked home decorations, and half-finished arts & crafts.

The things that were clearly waste were collected in a black bag or brought outside to be broken down and subsequently stuffed in one of her many garbage bins. Things that we believed to be valuable were brought out to the garage and set aside for evaluation by my Mom or Aunt Lorraine at a later date.

As the afternoon dragged on, I was starting to get more and more frustrated with Olivia’s share of the work. At best, our effort split was 90/10 in my favor. But I could only remind her so many times before my requests felt numb. While decent progress was made by 5 o’clock, it was demoralizing knowing I’d return tomorrow to the same struggle… and the next day… and the next day.

========

“Why didn’t you tell me about Olivia?” I confronted Mom the moment she got home from work.

She paused for a second, trying to piece together what felt like an accusation. “Oh! Yeah, she’s gonna be working with you too.”

I rolled my eyes. “Well, yeah. Now I know. Why didn’t you tell me before I agreed to do this? You know how frustrating she is to be around.”

Mom dismissively swatted the air as she put her keys and purse down on the counter. “Madison, please. You’re both adults. You can work out your differences for a summer.”

There she goes again with this selective adulthood stuff. “Mom, she barely did any work! I had to sort out everything myself. It was ridiculous.”

She shrugged and brushed past me. “Well, some jobs are like that. Tough break. Lorraine wanted Olivia to get in on the job, and I’m not gonna gatekeep summer work.”

I threw up my arms in exasperation. “So I’m fucked, is what you’re saying?”

Mom shot me a glare, then intensified her tone. “You are not to give me shit for an opportunity I didn’t have to give you. Got it, Madison? You’re lucky to have a job at all.”

I groaned, half-heartedly apologizing and retreating to my room. This was an objectively shitty start to the summer.

========

It was difficult getting out of bed on Tuesday morning, knowing I’d have to run back the same terrible day another four times before the weekend. But I buckled down. I threw on a t-shirt, shorts, put my hair up in the laziest bun imaginable, and made my way over to Grandma’s.

Impressively, Olivia arrived on time — I guess punctuality was her one responsible characteristic. We didn’t talk much yesterday beyond a few ‘catching up’ questions. This morning we talked even less. It was cathartic to arrive with a small section of progress carved out in the basement, even if there was still an entire house we had to get through.

I couldn’t help but glance back at her lazy butt with disdain every few minutes, lounging on the couch without a care in the world. God, she was maddening. But repeated passive-aggressive comments were getting me nowhere. As much as I wanted to walk over and give her a big ‘ol slap on the face, I knew I needed her help more than I needed to release my physical aggression. It’d ruin our dynamic for good.

Piquing Olivia’s interest was nearly impossible. I think when Aunt Lorraine teased her with the possibility of ‘valuable collectibles’, she assumed they’d be much more frequent and more like a jewel-encrusted medieval sword or lavish Fabergé egg. But karma must have been on my side, because beneath a stacked box — hours into the day — I found something interesting.

“Woah,” I muttered to myself, and not directed at Olivia. The fact I didn’t address her must have had an inverse reaction, as she shot right up from the couch.

At the bottom of a crusty cardboard box was another box — but not like anything I’d seen so far. This one was a pristine, pretty white box, daintily wrapped with a scarlet ribbon tied in a neat bow.

“What is it? What is it?” Olivia needled me, as I pushed her lurking body aside.

This box was a rarity. Most were stuffed with randomly assorted junk, but this cardboard box contained only this beautiful parcel — untouched and unperturbed. Attached to the box on top was a mysterious, sealed letter with the name ‘Diana’ written on it.
Olivia cracked a smile. “I think we finally found something cool.”

“Well that’s nice,” I said, killing the intrigue and lifting the box out of its decaying cardboard home. “I’m gonna put it in the garage for Mom to check out.”

Olivia grabbed my arm, nearly making me drop the box. “Are you insane? You’re not gonna open it?”

I shot her a glare, not thrilled with her forceful clutching. “Um, no. If you were paying attention, you’d know that our job is to find things of interest and have our Moms determine if they’re worth anything.”

“You’re such a sucker,” Olivia derided me. “You finally find something cool and the first thing you do is ignore it?”

I shrugged. Olivia groaned.

“Ugh, how about I open it? You won’t be blamed and if anything happens, I take the fall. I mean, aren’t you a little curious about who Diana is?”

Admittedly, I was a little curious. But based on the irrelevance of everything I found so far, I figured nothing of real interest could possibly be in this box. But while I mulled over her request, Olivia snatched the box out of my hands and sprinted upstairs.

“What the fuck!” I shouted, scurrying after her. I didn’t expect her to be so fast, considering how she moved like a sloth every other minute of the day. My chase was unsuccessful and by the time I got upstairs to the kitchen, the letter was already torn open.

I wanted to punch her so bad for deliberately ignoring our instructions, but my curiosity got the best of me. “Jeez… fine, then. Let’s read it.” I stood next to Olivia and leaned in to read aloud the elegant, hand-written message:

———

May 6th, 1965

Gretchen

———

Olivia was flummoxed. “Gretchen? Who’s that?”

“That’s Grandma’s name, idiot,” I answered. “But who the hell is Diana?”

She pointed to the last word of the letter. “It says sister. Did Grandma have a sister?”

I stared at the note intently. “I… I don’t think so. But, like, Mom rarely talks about Grandma anyway. So I guess it’s possible.”

“Well now we gotta see what’s inside,” Olivia asserted, this time with no need to snatch anything away. I was just as curious as she was, if not more.

She gently undid the lavender bow and let it fall to the sides. Olivia lifted up the box’s lid, unveiling something wrapped in delicate paper.

“Amazing,” I uttered. “This hasn’t been touched in decades.”

Olivia carefully unfolded the paper, revealing some sort of garment folded inside. I reached over to lift it out of the box, stood up, and held it out in front of me.

“It’s… a dress…” I remarked to myself. But this was more than some normal run-of-the-mill dress. This was a much older style — like something from the 1940s.

“Holy shit that thing looks vintage,” Olivia noted. “Not that it’s ugly. Just… old.”

The dress was a gorgeous, deep lavender color. It was a full-length, classic dress made from a sturdy, ruched fabric I’d never before held. The long sleeves were ornamented with cute beads, as well as the high neckline and scrunched cuffs. From the fabric alone I knew it was nowhere close to a style you’d see today, but despite knowing nothing about fashion from the 1940s — or whenever this dress was from — I was sure of its quality. This was a well-made, beautiful dress. We were simply past its time.

Olivia ran her fingers through the fabric as I held it steadily. “So Grandma made this?”

“I mean, if the letter is legit, then yeah. ‘Singer’ is a sewing machine brand after all.”

She sat down and leaned back in her seat, taking in this bombshell. “That’s so crazy. So, like, Grandma was a serious seamstress… And had a goddamn sister!”

This was all so strange. Granted, Mom never owed me — or Olivia for that matter — a full history of Grandma’s life, but to leave both a person and a passion out of her story felt a little insulting. Hell, what if I ever wanted to study the genealogy of our family? Was I expected to just leave her out of it?

My first instinct was to call my Mom. She deserved to know what we found, but Olivia stopped me from calling.

“What’re you doing? This is a huge find! Maybe it’s worth a ton of money or something.”

I yanked back my phone. “Exactly. Let them figure that shit out. I don’t need fabric valuation added onto my to-do list.”

She rolled her eyes. “Jeez you suck… Hey! If this exists, I’m sure there’s more crazy stuff. Don’t you think we should wait for more than one cool thing before getting our moms involved?”

Her comments made me laugh in her face. “Oh, now you’re interested in the job? All it took was one sick find?”

Olivia shrugged. “Eh, you’re right. Doesn’t mean there’s more.” She grabbed the dress off the table and took it downstairs. “You can keep digging. I’m gonna try this on. I wonder if it’s comfy.”

“Hey!” I shouted, chasing her back downstairs. “Don’t do that! It’s probably fragile.”

I caught up with her just outside the downstairs bathroom — yet another room that was packed with junk, only leaving room for the toilet and sink which both fortunately still functioned. She held up the dress against her body in the bathroom mirror, already disinterested. “Eh, it’s way too small anyway. Guess Diana was a shorty.”

Seizing on her disinterest, I snatched back the dress. “Yeah? Too bad,” I said sarcastically.

Olivia sighed, looking at the dress. Then back at me. Then back at the dress. For the first time since we started, a strange smile crept on her face.

“Uh… what’s up?” I replied nervously. I don’t know if she actually looked devious or if I was just so thrown off by her expressing anything but apathy.

“Do you remember when we used to play house? As kids?” she began. “Gah! You always looked so cute in those dresses!”

I immediately turned as red as my hair. “Olivia… that was a long time ago. Please tell me you’re not suggesting what I think you’re suggesting.”

She looked at the dress. “You know, it is just your size…”

========

Keep lookin' out for the first few chapters posted here on BC! Hope you're enjoying, and thank you as always for your support :)

Amazon Link: https://www.amazon.com/Dresses-Diana-Gradual-Feminization-St...

**FYI, this is the second of two teaser chapters.

CHAPTER TWO

The 16 Gold team practices four days a week — every weekday except Wednesdays. That gives the girls an opportunity to still expand their personal horizons and try other clubs and activities in the evenings, in addition to homework. It’s a healthy, important thing for anyone at any age to do.

My own free time was often spent exercising, reading, or playing video games. Not that I was completely without friends, but having practices in the evenings and tournaments on the weekends, it wasn’t ideal for a social schedule. So I mostly kept to myself.

The first week of practice was going…fine. Sure, I was mostly ignored and sometimes felt like a pack mule doing all the physical parts of running drills, hitting down-balls, and anything else Dottie needed for the team. The money, fortunately, was good. And with the low cost of living way outside of the Chicago area, I didn’t need to get a second job (just sometimes picking up extra shifts for training camps, working the concessions at our tournaments, and whatnot).

Socially, I’d somewhat befriended a handful of coaches, but now that I was coaching the girls instead of the boys, my sphere of familiarity was different. Sure, some coaches had teams of both genders, but most picked one and stuck there.

A full week of running girls' practices was starting to remind me how outnumbered I was as a man in this gym. 8 to 10 girls per team, each with a female head coach (and sometimes an assistant for the top teams, but also always female). Outside of the maintenance staff that came in, I was the only guy in the entire facility.

The one person I’d known a little bit from coaching boys was the 15 Bronze coach, Maddie Russell. She was a few years older than me with a sharp wit, fun personality, and incredibly beautiful. Maddie was one of those people who was so bubbly it was impossible not to like her. I was extremely thankful that her team practiced the same night and time slot as mine.

“Having fun so far?” Maddie ran up to me before Friday’s practice.

“It’s okay. Super different. It’s just been a hell of a week.”

“Yeah, the girls' practices are a lot more intense than the boys’, huh?” Maddie chuckled. “I always feel like a babysitter for the boys – even the high school ones.”

“Totally. But they both have perks. I’m just having some trouble getting these girls to like me.”

Maddie waved her hand, dismissively. “Ohhh they’ll come around. And as their coach, you don’t need them to like you. It’s not like you have to be friends with them. They just need to respect you as a mentor. Like a kind of big sister. Or for you, big brother.”

Maddie had a good point. It’s not like I was trying to enter a 16 year-old girl friend group. I didn’t need to be up to date on their slang and interests. After all, I’m nine years older and at a completely different stage of my life.

Dottie blew her whistle and called the girls in for the pre-practice meeting. They went through the school recap routine, had a few laughs, and practice began.

Soraya (the best of two setters on the team, just barely beating out her twin sister, Eshal) kept asking Dottie if we’d be scrimmaging after practice. “But it’s Friday! Can we please?”

“Depends on what 16 Silver wants. They’re their own team, so if they feel ready to scrimmage, we’ll be ready.”

Dottie’s response was good enough to keep the girls focused on a Friday evening. We wouldn’t start doing weekend tournaments for a few more weeks anyway, so it’s not like we needed Friday to chill.

But unfortunately for Gold, Silver was not ready to scrimmage. Their coach, a woman named Rebecca, was not pleased with the practice they had and therefore were not prepared to scrimmage.

“Noooo! So we’re just running drills for the last half hour?” Meghan whined.

Dottie sighed. I could tell she wanted to scrimmage Silver, and wasn’t in the mood to run drills for another half hour either. “We can play Fours,” she declared.

The girls cheered, celebrating that they got to do a 4v4 self-scrimmage instead of getting further critiqued on their hitting form.

Eve looked side to side and quickly realized an issue. “Coach Dottie, Kelsey’s not here though. So we can’t do Fours. We only have seven.”

“Well, maybe Coach Caleb can join in. Caleb?” Dottie looked over at me. Frankly, I was shocked to be addressed at all, much less by name.

“Oh, uh, well, I would. But…” I gestured to what I had on. Usually what I wore to practice was some sort of light athletic jacket and athletic pants. But today for some reason, I wore these inflexible jeans. I regretted it the second I got to the facility and though it didn’t affect my ability to coach, it’d severely hinder my ability to play.

The girls knew this, and immediately got bummed knowing it’d be uneven teams for the remainder of practice.

“Yeah, I’m sorry guys. Really.” I tried to apologize, but there was no quickness to forgive. I turned to Dottie. “Wait, let me just borrow some shorts from the supply closet.”

“They wouldn’t be in there. The boys are out of season, so they’ve boxed up all the extra uniforms and are packed away at South Facility.”

I was losing the girls. And I was clearly annoying Dottie. Everybody wanted a fun, 4v4 scrimmage to close out the week and I was letting them down.

“Unless…” I began. “Do we have any extra spandex shorts?”

Dottie did a double take, then whispered as if I accidentally said that out loud. “Spandex shorts? As in the women’s ones? You totally don’t need to do that.”

I couldn’t believe I was actually offering to wear tight, form-fitting women’s volleyball shorts, just to participate in a half hour scrimmage game. But here I was.

“Ha! No way! Coach Caleb’s gonna wear girls shorts?” Macy exclaimed.

“Ah! You totally should Coach Caleb!” Meghan joined in. Though the girls thought it was silly, they seemed to agree it was the best way to go.

“Hey, I’ve got nothing to lose. I want you girls to scrimmage, so spandex it is for me!”

I ran off to the storage closet to find my size and change into the tight, women’s spandex shorts. The closet itself was quite organized (I’d know, I helped organize it last year), so I knew exactly where to find the shorts in my size. You’d think that it’d be impossible for a 5’10” man to find a pair of women’s shorts in his size, but you’d be wrong. Remember, even the female volleyball players are tall — many taller than me!

Fortunately, I exclusively wear tighter-fitting briefs underwear, so the spandex shorts actually fit quite comfortably. I took off my jacket and kept my athletic t-shirt on. I’d never worn spandex before, so it was unreal how much of a difference these made on my legs. I already had slender, hairless legs, of which I was suddenly revealing a lot more of. If someone took a picture of only my legs, there’s a strong possibility you’d never know they belonged to a man.

Where the illusion definitely broke was with my bulge in the front. My t-shirt was on the longer side, so it mostly hid it, but that would be jarring to anyone watching a slow pan bottom-to-top of my body.

I ran back to practice to ‘oohs’ and ‘aahs’ from the girls. They couldn’t get enough of my new look. We were all laughing together, and it wasn’t in ridicule. We all just recognized the silliness of the situation: a male coach willingly changed into girls’ practice spandex.

“Gotta say, Coach Caleb, your butt looks pretty good too,” Dottie even chimed in. The girls giggled at that comment and when I whipped around to take a look, she was absolutely right. I had a serious dump truck going on.

I turned bright red with embarrassment, and Dottie quickly apologized for saying that in front of the girls. She whispered to me “next time, I’ll keep those thoughts to myself, Blondie.” Next time?

“Coach Caleb should also wear his hair in a ponytail to match us!” Macy suggested.

I had no issue with that, so I let my long hair down from the bun and retied it into a high ponytail to match the girls. They got a big kick out of it.

Finally, we split into teams and scrimmaged for the remainder of practice. Dottie kept score and made adjustments to both teams’ form, technique, and strategy. I did the same for the girls on my own team. But despite being a 25-year old man, I wasn’t that much better a player than these girls. Remember, they’re the best of the best in the country for their age group. By the time they’re 18, I’m sure they’ll be kicking my butt.

We had a productive, fun match, and notably the team of myself, Eshal, Harley, and the new girl, Remi, took the win! Running, jumping, and diving all over the floor felt so different in my spandex shorts. There’s a much greater chance for floor burn when your shorts only go as low as your butt.

Practice wrapped and Eshal, our team captain, led the outgoing cheer. As the girls packed up their things and disassembled the nets, Dottie wanted to speak with me.

“You made nice strides today with the girls,” she said, practicing her classic no-eye-contact conversation. Nevertheless, I appreciate the compliment.

“Thank you. That means a lot.” I replied, thinking that’d be the end of it.

“You’ll come to know this year… but these girls are already stellar. Sure, there’s room to improve, new techniques to learn, yada yada. And that’s one reason why we’re here.”

I nodded along as she looked off at the sea of eager players across the giant, converted warehouse.

“But coaching teenagers, especially at this high level, is a lot less about the actual instruction, and more about the trust and motivation you can inspire in them. Keep that in mind, Caleb.”

And with that, she walked away, leaving me alone in my spandex shorts, t-shirt, and high ponytail. I released the high ponytail and retied my bun.

Despite this peculiar, feminine episode, today seemed like a step in the right direction.

========

The entire 23 chapter story is live on Kindle! Thank you for all the support so far, and I'm hard at work on both my next novel and my serialized A Feminine Look story! :)

Link: https://www.amazon.com/dp/B0BTMNTTGK

Chapter One: A Sister’s Request

I always thought that September was the best month. Not just because it had my birthday in it (in fact I just turned 15) or because high school had just started for me. Rather, it was the leaves falling all around that always looked so nice.

The autumn scenery is so great for writing poetry, and now that I'm taking a poetry class this semester, I'll have plenty of inspiration.

Yeah, I know, poetry isn't really the most masculine attribute, but I really enjoy it. To be honest, I don't exactly have the most masculine attributes anyway. I'm 5'5" (I haven't hit puberty yet), I have long brunette hair past my shoulders, and I don't have big muscles.

I guess one masculine thing about me though is that I'm a pretty decent runner (I run on my own, not on the cross country team), so that helps me get toned.

It was my second week of school and I haven't made too many new friends yet. However, I'm still close with my best friend from middle school, Daisy. We've been friends since we were three years old, and our families do a lot together to this day.

So I'd say my life is pretty typical and boring. As of now…

========

I get home from school on a Tuesday and walk in to be greeted by my Mom, Dad, and sister, Jenna, sitting in the living room. It's the same thing every day, except this time Jenna said something pretty atypical.

"Hey Sam, can you meet me up in my room in a minute? I need a favor."

I hesitated due to the strangeness of her request. "Uhhh sure. Yeah I can help, I guess."

It was weird. Jenna had never really asked me to go into her room before. I mean we definitely have a good relationship with each other — my whole family does — but Jenna usually reserves her room as her own personal space.

I walk up the stairs and open her door. She's sitting down at her desk with a bunch of notebooks out. There are sketches on them of different clothes and hairstyles.

"Oh there you are! So you said you'd help me?" Jenna asked.

"Well I guess that depends on what it's for," I replied, unsure.

"It's for a class. Trust me, it'll take like 10 minutes."

"Sure, but what is it you need help with?"

Jenna continued to look down and sketched out something. "It's for my fashion class. Our first unit is on hairstyles: what looks good, what doesn't, and why. Just typical stuff."

Jenna then pulled out a clamp looking thing.

"So basically… I was wondering if I could style your hair and take a few pictures!"

I was shocked! Why does she need to take pictures of me? A boy!

"Aren't these girls' hairstyles you're working on?" I asked concertedly.

"Well... not necessarily..." she began, "I was just hoping I could straighten your hair and show some of the pictures in class. Most of the girls are using their own, but since I have a short pixie cut, I can't."

I paused for a second. Do I really need to do this? I mean, I already know I'm not that masculine, and this certainly isn't going to help.

"Ehhh...I don't know," I said, "I feel like people will make fun of me if they know I'm getting my hair done in a girly style."

Jenna finally looked up from her notebook and looked at me. "Nobody has to know it's you. I mean, all the people who would be seeing this are other seniors in high school, and they probably don't even know I have a freshman little brother. Plus, if they ask, I'll just say it's my cousin or sister or something."

I still felt uneasy. Jenna smiled at me pleading. She's always been so nice to me and I see her as a good sister and friend.
"...I guess I'll help," I said regretfully, but with a weak grin.

Jenna jumped up. "Yay! You're such a help!" She then immediately picked up that clamp thing (which I learned is called a flat iron) and sat me down at her vanity.

"So I know you have pretty wavy and messy hair," she began, "but I believe there's a lot of potential. You have a lot of volume and once this straightening iron does its job, it should look really good."

She got right to work and explained the steps to me as she went.

First, Jenna put some dry shampoo powder on my roots to absorb any oils that start to develop. Then, she started sectioning off my hair, after she put up part of it in a scrunchie. She would take sections of it at a time and run the flat iron through it a few times over. It took about 25 minutes, but by the end, my hair was completely straightened and shiny.
"Voila!" Jenna exclaimed, "So...what do you think?"

I stared at it for a little while, kind of surprised at how I looked. I'd never seen my hair so shiny before. I shook my head and my hair gracefully swayed across my face, neck, and head.

"...and a finishing touch." Jenna said, as she put a flowery, black clip in my hair. I gave her a semi-mean look, but let her leave it in.

"It actually doesn't look half-bad," I said, a bit impressed and surprised at myself.

"I figured you'd like it. Everyone likes being pampered from time to time." She smiled at me and I smiled back. "Oh! And now the pictures of course!"

Jenna pulled out her phone and stood about 5 feet away. I turned around, as I did NOT want my face being seen in these pictures. She took a few from the back, the top, and even a few from the side, but I made sure it was clear that you couldn't tell it was me in the pictures.

"All done...sis!" Jenna joked. I shot her another glare but she just laughed it off.

Right as we finished, our mom called us down for dinner. We went downstairs right away, as we were very hungry.

"Well well well, who do we have here?" Mom said. I looked back at Jenna but she just smiled. Then I realized that she meant me! Right as that happened, I blushed.

"Uhh...Jenna was..." I stammered.

"It's okay honey, I think it looks good." My mom said as she walked over and kissed me on the forehead.

All I could do was blush. I began to explain but then Jenna spoke up.

"It was for my fashion class project," Jenna explained. "Since I have my pixie cut, I needed someone with long hair to style and take pictures of."

"I guess your brother is a good resource..." Mom said.

"Even if it makes you look a bit girly." my dad pitched in.

Both my parents and Jenna laughed. I laughed nervously with embarrassment.

We ate dinner and afterwards, I went up to my room to do homework.

So many weird feelings went through my head today. I had straightened my hair for the first time, and it didn't actually make me feel that bad. I wouldn't say it was a good feeling, but I definitely learned more about what girls go through when they do their hair. I mean it takes a good half hour (if you know what you're doing) to get your hair all straightened and ready for the day. To relax, I wrote a brief poem about my feelings for the day:

a different experience

like none i'd felt before

soft hair cross'd my neck

causing tingling galore

t'is usually known

by girls alone

but tonight an exception

for me in my home

========

The next morning, my hair had lost most of the straightening, but I could still tell it was like that a bit.

School was pretty average as always, and I luckily didn't get any comments on my hair.

When I returned home, Jenna was waiting at the door with a big smile on her face.

"I'm assuming you want to know how my class went??" Jenna said excitedly.

"Uhm sure...I guess. The pictures worked well?" I responded.

"My class loved it! They adored how shiny your hair was and thought that they'd never seen anyone pull off straightened hair that well! Isn't that cool?"

"I suppose that's good for you, right?"

"Well yeah I got full points on the assignment, but what was really interesting was that everyone wanted to know who I took the photos of."

My heart dropped for a second. "You...you didn't tell, did you?" I said, freaking out.

Jenna sighed, "No, I didn't. I said that they were from my cousin."

I breathed a sigh of relief. "Thanks, Jenna," I said, "I'm just glad that I could help and keep my anonymity at the same time."

"Yes, thanks again. However, I'd like to stress that even my teacher was blown away by what your hair could look like. If they knew it was a boy's hair, I'm sure they'd flip out."

"I can imagine," I said. There was a brief pause. "Well, I think I'm gonna go for a run. But I'm really happy the pictures worked well."

I started walking past my sister but she grabbed my shoulder. "That actually brings me to my next point...Would you mind doing me another huge favor?"

I stopped and a skeptical look creeped on my face. "What kind of favor...?"

"...can I do your hair again?" Jenna said sheepishly.

I sighed. "Listen, I was going to go for a run..."

"Oh please Sam! You were so helpful last time!" she pleaded.

"Ugh. Fine." I said. I guess I could put off the run.

Jenna squealed and told me to run up to her room. I guess I'm just too nice sometimes.

========

I went to my room to drop off my backpack and put some things away and then walked over to Jenna's room. When I walked in, I assumed that she'd just be needing to straighten my hair again, but this time, there were MANY more products and items out on the table than before.

"What...what's this?" I asked.

"Oh yeah..." Jenna responded, "I need to do a bit more this time. Our requirement is to use curlers this time. It might take a bit longer...could you still help...?"

I guess I'd already committed, and I'm in her room now...so I nodded and sat down.

"You are going to be so pretty!" Jenna cooed, as she ran her fingers through my hair. I gulped nervously. She then caught herself, "I mean, your hair will look pretty." She smiled and giggled.

She started by spraying my hair with some sort of fragrance. "What does this do for the process?" I asked.

"Oh, nothing. It's just always nice if hair smells nice." She said, giggling girlishly.

I sighed and just accepted it. She ran the flat iron through my hair briefly to straighten it out again. It didn't take as long as last time because it was still straight enough from yesterday. She then went to work with a curling rod. She started with a few sections of my hair, the same way as she did with the flat iron, but this time, she just curled it.

She went to work on all my hair and within a half hour she was done. It was a weird sight. My hair was always kind of wavy in a messy way, but this time it was a 'coordinated wavy.'

Jenna stepped back from me to admire my hair, "I think it looks great. What do you think Sam?"

"I guess it looks...nice." I said. I mean what else am I supposed to say? 'It looks adorable' is not something a guy would ever say.

"Just nice?" Jenna asked. "Ugh boys know nothing about hair... Alright! Picture time!"

She had me stand up this time.

"Wait. That plaid button-down looks awkward," she said, "do you have an undershirt underneath?"

"Uh, yeah I do." I said, confused. I took off my plaid button down and now had my white undershirt on."

"Thanks. You can tell in the picture that that isn't a girl's shirt. See? I am looking out for you."

We both laughed and she was about to take the picture of my hair, but she had one more correction. Jenna grabbed a peach infinity scarf lying on her bed.

"Put this on. It'll look much cuter in the photo." She said, tossing the scarf toward me.

I caught the scarf. "Ehhh, I don't think so...This is too girly."

"Too girly? But nobody knows it's a guy in the picture. If anything, it'll assure that nobody will suspect it's a boy's hair."

She had a good point. She helped me put on the scarf. It was positioned delicately around my neck. It was a very feminine scarf, and it felt really weird to be wearing it. Once it was finally positioned well, Jenna readjusted my curled hair so it cascaded over my shoulders and the scarf.

With everything set, she snapped the pictures, and uploaded them to the computer on powerpoint for the class assignment.
Watching the pictures get uploaded, I noticed that they looked very good. Even though you couldn't tell it was a boy, it was weird to see the hair—my hair—look that feminine.

"Thanks again little bro. They look fantastic," Jenna said with a smile.

I hesitated, still staring at the pictures on the computer screen. I told her "no problem at all," but did I really mean that? I mean, was I doing the right thing, trying out such a girly hairstyle?

========

The first five chapters of this 33 chapter novel are available here, but the remainder has been moved to my Kindle page. Thanks as always for reading and supporting me! :)

Link: https://www.amazon.com/dp/B0BPZCV3KT

Chapter Two: A Bit More Feminine

To be completely honest, yesterday was a weird experience. I had never had my hair curled before, or worn a girly infinity scarf for that matter. I could say I was not happy with yesterday, but I'd be lying. It was a very neutral experience. I really have no strong feelings about what happened, except that I'm happy I could help out my sister, Jenna.

The morning started off poorly as I woke up at my bedroom desk. I guess I had fallen asleep doing homework! But there's good news and bad news. The good news is that I actually did finish all my homework, so I'll be fine for my classes. The bad news is that it's 7:40, and school starts in 20 minutes!

Immediately, I heard a knock on my door from Mom, "Sam, are you getting up? You're lucky I'm driving you and your sister today!"

I shot out of my chair and gathered my books. I ran downstairs to meet my sister who was already ready to go. I grabbed my lunch and a banana for breakfast and ran out to the car. Within three minutes we left.

"Damn it's really too bad I slept so late. I just had a lot of homework I guess," I managed to say while yawning.

Jenna then spoke up with a grin, "Yeah and you didn't even get a chance to fix your hair!"

WHAT? I completely forgot about my hair! It still had all of its curls in it!

"Crap!" I said nervously to Jenna, "What the heck do I do?!"

"I think it looks cute, honey." Mom said.

"Not helping, Mom!" I yelled back.

"Here's what you do, Sam," Jenna said, grabbing a hair band off of her wrist. She motioned for me to lean towards her, and she proceeded to grab my hair and put it into a bun.

"That should do the trick." Jenna said.

I was relieved, it did happen to stay pretty well, and you couldn't tell that my hair was even curled. I had never worn a bun before at school, but I suppose this is better than sporting a girlier hairstyle.

"Thanks, Jenna. I owe you BIG TIME."

And with that we scampered out of the car, into the school, and off to our respective classes.

========

The day went by quite smoothly. I got a few comments from people regarding my bun, but it didn't bother me much, as all the questions came from girls. A few of them even said they liked it.

I returned from school to, once again, Jenna sitting in the living room waiting for me.

"Hey, Mr. Bun, how was school?" Jenna asked jokingly.

"Ha ha hilarious," I remarked sarcastically, "But really, it was fine. I got a few comments, but nothing out of the ordinary. Thanks again for saving me with that hair band."

"Of course! What kind of sister would I be if I didn't help my brother when he was in need?"

We smiled at each other. Then after a brief silence, she brought up the exact thing I expected to hear about when I walked in the door.

"So you'll never believe what happened in my fashion class today!" she squealed.

"Hmm...they liked my hair?" I said dully.

"Even better! My teacher asked me to curl her hair for her in front of the class! I'll be getting an 'A' for sure!"

"Hey hey that's great news!" I said with genuine excitement, "So, is that all you really do in this class? Work on hair?"

Jenna shook her head. "No, that's just the first unit. There are other fashion units coming up soon."

We chatted in the living room for the next hour about school, family stuff, and even a little about hair, surprisingly. After that, I decided to go up to my room and get changed to go on a run.

========

I decided to do a four mile outing — relatively short in the scheme of things — but the run allowed me to reflect on this last day. I mean, what if I had been discovered? What if my bun just fell out, and the curls cascaded over my shoulders? I can't even imagine what I'd do! Kids in school are so judgmental. Something just a little out of the ordinary (like a boy with curled hair) would cause them to flip out and tease.

I got back from my run, and before I even went down, I had to write my thoughts down in a quick poem:

wavy hair

straight hair

so many options

so many styles

for girls to try and share

but a mangy ‘do

on a mangy dude

is the only option boys can choose

========

I left my room to the shower, but ran into Jenna on the way to the bathroom. She looked awkward.

"Hey...Sam?" she said sheepishly.

"What's up?"

"You know how in the car this morning, you said you'd owe me big time? Ya know, for helping you out with your hair?"

"Sure, I remember saying that."

"Well I'd like to cash in that favor now."

"Okay...what is it?" I said nervously.

"I'd like to style your hair again, if you don't mind."

I didn't think much of this, as I'd now done it twice before and I owe her a favor.

"Sure, I'll help. And you need this for class tomorrow?" I asked.

Jenna paused. "Well...we don't exactly need it for class anymore. We don't need pictures of hair styles any more. I just want to try a few things out on you before I style my teacher's hair in front of the class...would that be okay with you?"
Well this was odd. The two times before were for a class assignment, but now it almost seemed like she wanted to do this for fun. I looked at her while she waited for me to give an answer. Again, those pleading eyes stared at me...

"Fine, I'll help. But let me shower first."

Jenna squealed, "Yay! But first, let me grab my special shampoo and conditioner. It'll make your hair extra soft and make it smell flowery!"

Before I could debate that, Jenna was off to the downstairs bathroom to grab the shampoo and conditioner. When she returned, she gave me careful instructions on how to wash my hair. I never knew there was so much thought into just washing hair!

I stepped in the shower and did as she said. When I put on my robe after finishing, she came in and used a blow drier on my hair. She used a long brush to make the hair soft and shiny. Once she was done using the hair dryer, she led me to her room, where she began to run the flat iron through my hair. Just as she did last time, she sectioned it off, and within 15 minutes, my hair was straight and shiny. She then ran the curling iron to give me long, loose curls/waves throughout my hair.

"You're gonna love what this looks like once I'm done," Jenna said with a smile.

I smiled back, slightly scared to see how feminine my hair was going to look.

By the time she finished curling my hair, it laid softly on my shoulders. There I was, sitting in my sister's room in my underwear and robe, with girly, curled hair. But she wasn't quite done. She completed it by having what she called ‘waterfall braids’, which was a line of braids going across the middle of the back of my hair, and sections of my hair pulled through those braids.

Jenna stood back and admired her work. "Oh, and a finishing touch!" she said, as she ran to her closet and grabbed a pink bow to put amongst the cascades of flowing hair.

Admittedly the hair looked beautiful. Any girl with that kind of hair would get the attention of any guy. It had a tenderness and sweetness to it that just screamed…’pretty’.

Unfortunately, that hairstyle was on me.

"So it looks good?" I asked, breaking the silence.

Jenna laughed, "Good? I don't think I've seen anyone pull off that hairstyle better! Not even girls!"

I blushed. "Well I'm glad I could help you out. So this is the style you're going to be using for your teacher?"

"That's what I'm planning on," Jenna said as she rummaged through her closet.

There was a brief silence? "Hey, do you mind if I actually take a few pictures? I know I don't need them for class, but it would be a waste to never document the quality of this hair!"

I sighed, annoyed. "Sure," I said, conceding.

Jenna jumped with happiness. "Just because the pictures will be taken from shoulder up, it'd be best if you put on another one of my scarves and a white undershirt."

I agreed, and changed into my pants, but could not find my white t-shirt.

I yelled to my sister in her room, "Hey I can't find a white t-shirt. Will another color do?"

She yelled back, "Don't worry! I've got one in here!"

I shrugged and walked back to my sister's room. When I returned, she was holding up one of her own shirts.

"You want me to wear your shirt...?" I said uncomfortably.

"It's just a plain white shirt, but with a little deeper v-neck, a little tighter, and shorter sleeves."

"So...a blouse?"

"I guess, but it's just a regular shirt. You'll only have it on for a brief time, so don't worry."

I reluctantly nodded, and put on her shirt. My sister and I are pretty much the same size, so the shirt fit well. She handed me a light blue infinity scarf and I put that on as well. She helped me drape my curled, wavy hair over my—I mean Jenna's—scarf. With everything set, Jenna started taking pictures of my hair. She took probably 30 pictures from all angles (except from the front, of course), and even took a few with my hands in the picture, running my fingers through my hair.

"We're lucky that you have delicate hands, because otherwise people might think you're a boy!" Jenna said giggling.

"Yeah..." I responded uncomfortably. Boy, she really doesn't hold back on complimenting my features.

Jenna finished with the pictures and let me go back to my room. I gave her back my shirt, fixed my hair to a more normal look, and went to do homework and get ready for school on Friday.

========

School was good on Friday, and I came home after, ready to enjoy the weekend. For once, I walked in the house and Jenna wasn't in the living room. I asked Mom where she was, and she told me she was in her room. Apparently the second she got home, she rushed right up to her room and got on her laptop. Whatever it was, seemed really important.

That had confused me, but I figured I would go up to her room to see what she is up to. I knocked on her door.

"Come in!" She shouted. I walked in, and she indeed was on her computer, and seemingly focused on something.

"Oh good, it's you! I have great news!" Jenna exclaimed.

"Well, tell me!" I responded with excitement.

"So you remember the pictures that I took yesterday and the days before?"

"Umm, yeah, of course. What's up?"

"Well I showed them to some of my friends this morning, and said my ‘cousin’ has an Instagram account with these pictures."

"I don't know if that's a..." I tried to speak, but she interrupted me.

"Well I already created it..." Jenna said with a smile growing.

I turned beet red. "What!?! My hair is on Instagram? As a girl??"

Jenna's smile went away just a bit, "Well your hair looked just so pretty, and so many people liked it. I felt it just had to be shared."

I couldn't believe what I was hearing. How could I be on Instagram? As a girl?

Jenna sheepishly spoke up again, "And it's already pretty popular..."

I blushed even more, "Do I want to know how many followers it has?"

Jenna turned to her computer. "Uhh... 312 followers as of now, and it's growing. But listen, people are really in love with your hair. People are commenting and saying that it is some of the most beautiful they’ve ever seen. People love to look at and appreciate beauty, and your hair is really something special that means a lot to people. Especially to me.

Jenna then walked up to me and ran her fingers through my brunette hair.

This was insane. I guess it's good that people are enjoying it, but there's a fine line between having a small classroom look at my hair, and creating a fake person's account with over 300 followers. So do I tell her to delete it? If my hair is really that special, I guess I can keep it up a bit longer...

========

The first five chapters of this 33 chapter novel are available here, but the remainder has been moved to my Kindle page. Thanks as always for reading and supporting me! :)

Link: https://www.amazon.com/dp/B0BPZCV3KT

Chapter Three: The Fashion Expo

I had a lot to think about that night. First off, I had apparently become an Instagram user within the last 24 hours, which is not something I would have ever predicted. Probably because I'm not even a huge social media fan anyway.

But just like that, I was on my way to becoming a somewhat known Instagram ‘star’ at school...as a girl.

But now it's the weekend, so hopefully some of the hype will be going down. I woke up Saturday morning and had breakfast as usual. I sat down at the table and Mom walked up to me with a plate of pancakes.

"I felt like being nice this morning," she said, setting the plate down in front of me.

"Thanks!" I replied. It's always nice to start the day off with a good breakfast. I decided I'd go for a run, so I went back upstairs to my room to change. In the hallway, I ran into my sister.

"Hey Jenna, what've you got for today?" I asked.

"Nothing till 3, cuz that's when I'm going to this fashion convention with some friends at McCormick Place downtown."

"That's cool. I haven’t actually been downtown in like 5 years."

"What? No, I'm sure you've been down recently."

"Actually, no. I mean, when does our family ever go to downtown Chicago? There's no reason I would have."

Jenna looked shocked. "No way! Well you should definitely accompany my friends and I today."

It was a nice offer. I mean I've been dying to go into Chicago for the longest time now, and I'm getting sick of the suburbs. But a fashion convention? That doesn't really sound like my cup of tea.

"Ehhh I'm not really sure if that's my thing, Jenna."

"Don't look at it as a fashion convention, Sam. Look at it as an opportunity to go downtown!"

"Hmm...I suppose that's a good point." I said hesitantly.

"So are you gonna come?"

"Uhhhh...sure, why not."

"Awesome!" Jenna said, "The thing starts at 3, but we'll leave an hour before that, so be ready in 4 hours."

I nodded, and went back to my room to change for my run. I went a solid 4 miles. It gave me more time to think. I spent most of the time reassuring myself that there's nothing wrong with a boy going to a fashion expo. I mean, it's an opportunity to escape this quiet western suburb and finally go into the city. Who cares if it's for fashion?

I returned to the house, showered, and then chilled in my room for the next few hours. For some reason, I felt nervous about this. I really hope that Jenna told her friends I was coming. I don't want to feel like I'm inserting myself on their girl time. But she invited me! So it must be fine.

I watched Netflix for the next few hours, and before I knew it, it was 3 o'clock. Jenna knocked on my door.

"Ready Sam? My friends are already here, so we'll be leaving now."

"Yep! I'm good!" I yelled back. I grabbed my wallet and phone and headed downstairs. Jenna was standing at the door with her two friends, Kelly and Sophie. Kelly was a short, busty blonde with really pretty green eyes. From what I understand, she is a really sweet person and a lot of guys want to get with her because she's so nice to be around. And she's easy on the eyes as a bonus. Sophie, on the other hand, is a tall, thin brunette who actually looks a bit like my sister, except taller. Jenna tells me that they used to get mistaken for twins before Jenna cut her hair. She's apparently really chill to be around as well.

"Hey guys," I said to them, catching their attention.

"Hey Sam!" the girls said simultaneously. We'd met before a few times, but never got the chance to really get to know each other.

With everyone set, we got into the car to go downtown, the ride was filled with small talk and talk about school.

========

We walked from the parking garage at McCormick Place (the big convention center in Chicago) to the big room where the expo was being held. We purchased our wristbands and entered. The venue was huge! Hundreds of stands were set up with displays of new clothing trends, make-up trends, and hair booths with books and demonstrations on various styles.

And yes, it was the exact gender ratio that I expected. The place was probably 95% girls. And that's being generous. So don't get me wrong, this was strictly a female fashion expo.

"So Sam, I'm really glad you came. But I'll admit I'm a little surprised that you wanted to…" Kelly said.

"Yeah," Sophie added, "Isn't this a bit boring for you?"

Jenna interjected before I could answer, "Well actually, he said he hadn't been in the city in like 5 years, so I said he needed to come."
I nodded in agreement. The girls seemed to accept that answer.

"I'm sure we can make it more fun for you though somehow," Kelly said politely. I'm not really sure what that meant, but I just smiled and thanked her.

And thus we began browsing the booths. The girls checked out tons of things. They browsed the clothing sections for over an hour while I kinda just stood and watched them. It was quite boring. After that they moved on to make-up, testing out a few of the products. A saleslady actually asked me if I wanted to try out anything! I'm not sure if she was kidding, thought I was a girl, or what, but I just told her no thanks and moved on.

Finally, the girls left the make-up area and moved on towards the hair area.

"This should be right up your alley Jenna, speaking of all of your killer presentations," Sophie said.

"Yeah, that demonstration was awesome!" Kelly added.

"Oh, you guys are in Jenna's fashion class?" I asked.

"Yep! I mean it's only been a couple weeks of school, but Jenna is totally standing out in her knowledge of fashion and especially hairstyling. I mean have you seen the pictures of your cousin? There are a lot of girls at our school following her Instagram account, even though we haven't met her." Sophie said.

I hesitated for a second. I finally realized the cousin she was referring to was me. That was Jenna's cover for who's hair was actually in the pictures.

"It probably doesn't interest you though, being a boy though."

I awkwardly laughed, agreeing. "Yeah I don't really know much about hairstyles and stuff."

"You know...we said we could make things more fun for you..." Kelly said, looking at Sophie.

"Ooooh we could totally do your hair if you want Sam! That would be fun, right? I mean you've been bored this whole time..." Sophie said, hinting.

"Do...do my hair?" I said stammering. I looked at Jenna and she kinda shrugged. Her body language was basically saying, "Go for it. Why not?".

This would be crazy! Me, a boy, having my hair done like a girl in front of all these people. I mean, I've had it done before, but nobody knows that. This would be a whole new step.

The girls were looking at me with pleading eyes.

"Hmmm...I guess I have been bored this whole time..."

The girls jumped with joy.

"I say Jenna styles your hair! I don't know if you know, but she's really good at it," Kelly assured.

I looked at Jenna and could tell we were laughing at the irony on the inside.

We walked over to a booth with salon chairs. Jenna sat me down and jokingly spoke in a stereotypical salon-person voice, "So, Samuel, to what shall I style your hair today?"

"Hmm how bout whatever these two lovely ladies decide," I said, referring to Kelly and Sophie. They seemed so into the idea, so I might as well appease them.

They blushed with excitement. Sophie picked up a hairstyle book and flipped through it. Eventually they came across a curled, floral updo that they really liked. Jenna took a look at it and said that she could probably handle that.

With all said and done, Jenna went to work. I kinda lost track of what she was doing, as she was going so quickly. She started off with straightening my hair, and then added in some curls. Throughout the process, some other convention-goers started to come over and watch. I saw a lot of confused looks. Although there are a couple reasons why they could be confused. For one, they could be wondering 'why is a boy getting his hair done in a girly style?', but they could also be wondering, 'why is that girl getting her hair done wearing such boyish clothes? Especially at a convention like this?'. Jenna twisted the newly made curls of my hair into an updo. Right as she was about to be finished, Kelly and Sophie walked up with some small, white and pink flowers they bought at one of the other stands. They handed the flowers to Jenna, and she placed them within the curls and waves of my new updo.

And just like that, Jenna was done. Kelly and Sophie had huge smiles on their faces. "Sammy! You look adorable!" Kelly squealed.
"Really?" I said, a bit uncomfortably, "I still haven't seen myself."

Jenna then helped me up and walked me over to a mirror. And in the mirror, I saw one of the most beautiful hairstyles I've ever seen. I touched it lightly to convince myself it was real. I couldn't believe it!

"Wow Jenna! This actually looks really good!" I said, surprising myself even a bit.

"You look like you're ready for prom!" Sophie added, "All you need is a cute boy to sweep you off your feet!"

That comment made me really embarrassed and a little upset. I gave Sophie a slight glare, and I think she got the point.

"You know, Sam. Your hair is even prettier than your cousin's. It should really be you with the Instagram account!" Kelly joked.

I blushed and looked at Jenna. We had guilty looks on our faces.

"Wait...what's going on? What's up?" Kelly said.

Jenna looked at me and her body language basically said, 'should we tell them?'

I was pretty scared and couldn't make up my mind. That didn't stop Kelly's 'investigation' though.

"Wait a sec...Sam! Is that your hair on the Instagram account??"

I was beet red. They were on to me, "Alright fine! You caught me. It all started when Jenna asked for help with her project, and I guess she got carried away with it."

I expected laughs from the girls, but it was quite the opposite. They flooded me with compliments about my hair. They asked what shampoo, conditioner, and other hair products I was using.

It's amazing how overwhelming it became so quickly. I had been outed as having ultra feminine hair, and nobody seemed to care.

"You know what Sam, now that this has come out, we should add this hairstyle to your Instagram now!" Jenna suggested.

I was hesitant. This was all happening so fast.

"C'mon, nobody else knows that you're a boy. It'll be our secret." Kelly said.

She was right. I didn't like the idea of my hair being paraded as a feminine treasure, but I guess it was nice to know I'm getting some attention, even if it's anonymous.

"Sure, let's do it." I said with confidence.

Jenna then positioned me in a place where the lighting was good.

"Wait," she said, "It still looks weird if you're wearing a t-shirt. Especially with this 'updo look'. Kelly, could you go grab something for Sam to wear on top? Just so his hair looks a bit more feminine."

"I'm on it. You'll look great after this, Sammy." Kelly said in a flirtatious way. She then walked off toward the clothing section to get something for me.

So there I was, at a fashion expo, with a prom updo, awaiting a feminine garment to supplement the girly hairstyle that has graced my head.

Last week, I would have never expected I'd be here. I definitely don't love what's going on, but as a boy, I feel like I should really be hating this.

I just hope the garment she brings back isn't too feminine...

========

The first five chapters of this 33 chapter novel are available here, but the remainder has been moved to my Kindle page. Thanks as always for reading and supporting me! :)

Link: https://www.amazon.com/dp/B0BPZCV3KT

Chapter Four: What to Wear?

I was nervously awaiting what Kelly and Sophie were going to bring back. I would say that I'm afraid to look too girly, but then again, here I am sitting in a chair with a flowery updo meant for a girl on her prom night.

"Having fun?" Jenna asked politely.

I laughed. "Well it's certainly an interesting life event. Not sure if I'd say 'fun' though."

"Well you're doing great, and I appreciate you playing along. Kelly, Sophie, and I are certainly enjoying it. Maybe if you think a little more openly, you'll enjoy it too!"

She had a good point. Maybe I just have to let myself go a little. But then again, what I've been doing is so out of the ordinary, it's hard to accept it as normal.

"Hey Sammy!" Kelly yelled from across the room, "We picked something out!"

She was holding a gray shopping bag, so I could not tell what was in it. She walked up next to me.

"So everything was really expensive, so we just got this plain pink top." Kelly said.

Phew! I was thinking they'd come back with something really girly. I don't think I'm ready to take that step. However, she did manage to throw me for a bit of a curve after that.

Kelly pulled the top out of the bag, it was what she called a 'slouchy crew'. It was a light pink color and had the brand name PINK on the front (appropriately matching the color, I guess). Not the typical shirt, but what she said next really threw me off.

"So we think it'd look really cute if you wore this. It dresses down the hair a bit, which should look really cute and flirty. However, we bought you this as well, because without it, the off-the-shoulder look would look weird. I mean we only need it for the straps, mainly."

It was then that Kelly pulled a bra out of the bag and casually handed it to me with the top.

"A...a bra?" I said uncomfortably. I put it down on the chair and stepped away, "I don't know… maybe we’re taking this whole thing too far..."
"Oh c'mon, Sammy," Sophie said, "You already have your hair in an updo. This is only one more small step."

Jenna then briefly pulled me aside, "Listen Sam, you don't need to do this if you really don't want to. Nobody is going to make you. I just thought that when people act more openly, everyone has more fun, that's all."

I sighed. "You're right."

Jenna looked up, "I promise to be more open. Because hey, maybe we might all have a little fun in the process."

I forced a confident look on my face and walked over to the chair, grabbed the bra and top and walked into a nearby changing room. I took off my t-shirt, careful not to mess up my hair, and held the bra. I fiddled around with it in the mirror for a little while until I finally got it adjusted correctly.

Boy, did this look weird. Very few guys get the chance to look at themselves with a prom updo and a black bra. I thought that I might as well finish the job. I slid the slouchy crew over my head and hung it slightly off one of my shoulders, as I was told to do. This was easily the girliest I've ever looked.

I walked out of the changing room and the girls all go huge smiles on their faces when they saw me. They all walked up to me and complimented how well the top matched my skin tone, how it looked good with the hairstyle, etc.

"You literally could be a model...from behind," Sophie said jokingly. We all shared a laugh. I do wonder what she meant though. Did she think I was unattractive, or just because I didn't look like a girl from the front? I'll assume the latter.

The girls sat me down in the same chair where I got my hair done. Jenna took some shots from the sides and the back. A couple of the shots were really cool because it had my hair and shoulders, but also tons of people walking behind on the convention floor.

Jenna showed them to us and then uploaded them to 'my' Instagram account.

"Hey Jenna, by the way, what did you name the Instagram account?"

She giggled, "I actually used your name...kinda. It's Sammi_Jaclyn32."

"Wow. Hilarious," I said with a deadpan face. The pun was obviously off of my name being Samuel Jason."

She uploaded the three best pictures to the account with #FashionExpoChicago tagged.

At this point, we weren't really sure what to do. We'd already been around the full convention center, and now with my hair dolled up, I’d get a lot of unwanted attention walking around. So we decided to leave. I figured since it went with my hairstyle, it might arouse less suspicion and weird looks. I changed my shirt and took off the bra when I got back to the car, but kept the hair as is.

========

We returned home about an hour and a half later, around dinner time. The girls stuck around with Jenna and went back to our house with us. When I got home, we were greeted by our Mom.

"Hey guys! How did the…woah woah woah!" my Mom said, interrupting herself, "Va-va-voom! Is that my little Sammy?"

I blushed and got very embarrassed. Jenna stood up for me though.

"It was our idea. There was a chair with products and other hair stuff we could use to style his hair, so we thought it was too good of an opportunity to pass up."

"Well, regardless of how it happened, it really looks great!" She continued with her praise, "I can't remember the last time my hair looked that pretty...I don't even think ever!"

"Yeah it was a lot of fun!" Sophie chimed in, "We even got him some clothes to add to his Instagram account!"

Now I was REALLY embarrassed. I didn't really want my Mom knowing all about this feminine stuff going on. She'd seen my hair before, but that was the extent of it. It's like she's completely involved now.

After Sophie told her about the Instagram account, my Mom looked confused, so they filled her in. They showed her the account, and told her the whole story: everything from how Jenna originally said it was her cousin's hair, to the post made an hour and a half ago.

"Well, that's quite the journey! And how are you enjoying this so far, Sam?"

"It's been...okay I guess. I don't know, it's not really my favorite thing, but I enjoy being involved in something."

"Well I'm glad it's not too hard on you," she said. Mom then whispered in my ear without the others noticing, "and the girls seem to really enjoy spending this time with you!"

She backed away and smiled. I smiled back. It really did feel nice to be spending this time with my sister, even if it meant putting a little femininity into my look.

Jenna proceeded to ask if the girls could stay for dinner. My mom said yes, and we got ready to eat. My Dad came home, and of course, they had to fill him in on the whole story too. He seemed surprisingly okay with it. Basically my parents' opinion was if I’m okay with it, then so are they.

========

The girls hung out at our house the rest of the day but pretty much stayed together. I went to my room and stayed there.

Sunday went by as well, and was pretty boring. The only thing worth mentioning is that Jenna at some point put the clothes from Saturday (the shirt and bra) in my room, folded on my bed. I don't know what she expected me to do with them, but I just put them in one of my drawers. It's not like I'd need them again, right?

On Monday we were back at school and the day went by quickly. Class was boring as usual. But when I got home, Jenna shocked me with an update.

She ran up to me, "You would not believe what just happened!"

I was startled by her feverishness, "What? What?"

"Remember that Instagram post from the expo? I tagged it with the hashtag of the convention, and now it has been shared on the convention's twitter!"

"Uhh...is that good news?" I asked awkwardly.

"Umm, YES! Because they shared it out, we now had a huge boost in followers! When I last took a look, we were at 317. Now, we're at 2,506!"

Holy crap! 2,506? That's absurd! Why are people so interested in my hair? I mean, honestly.

"So what do we do now?" I asked.

"We're getting a lot of positive responses. Everyone wants to know who this mystery Sammi Jaclyn is."
I started backing away. "No no no no no we are not revealing my identity to two thousand-plus people. Especially since a bunch of those followers are people at school."

"Well it'd mostly be people I know. So seniors, not freshmen."

"I don't care! We are not revealing my identity."

Jenna was getting flustered, "So what're you saying? You're just going to stop this whole thing? No one is forcing you to do this Sam, but if you hate it, why are you doing it?"

"I...I don't hate it."

"So you like it?"

"Well I wouldn't say that. I do like the idea that people appreciate some aspect of me, but..."

"But what?"

I took a seat down on the couch. "Look, I've never been popular, and nobody has ever paid attention to me. I've always been that kid who's kinda in the background; never stood out as anyone who mattered because there was nothing in particular I was good at."
Jenna sat down next to me and listened.

"But I'm also a really shy person. I don't want to be well-known for something. But I'm working on overcoming that fear. Right now, in a perfect world, I'd want to know I'm appreciated but without getting the attention. Do you know what I'm saying?"

"I know exactly what you're saying," Jenna said as she put her arm around me, "and I think the situation you're in right now is exactly what you want."

"Yeah, I guess," I said, sighing, "And I guess that's why I'm actually okay with all this. It's just super different, you know?"

"I totally understand," Jenna replied. She reached out and gave me a nice hug. It really is great to have her as a sister.

"Hey listen, I don't know if this is the best time to bring it up, but I actually got another assignment in my fashion class."

"You want to do my hair again? Because I might take the day off, to be honest. If you need me to read through a paper or something else I'm happy to help."

"Well... that works out. It's not really a paper, but more of...trying stuff on."

I raised an eyebrow at her. "Like what?"

"We're starting a clothing unit and our assignment was to take a picture of us wearing something casual. I thought maybe instead of me wearing the clothes... you'd want to model something 'casual' for me?"

That didn't sound so bad. I've been enjoying spending time with Jenna and she's been so nice and understanding. The least I could do was help her out.

"I got you."

She smiled, and then led me up to her room.

It's just casual clothing...how bad could it be?

========

The first five chapters of this 33 chapter novel are available here, but the remainder has been moved to my Kindle page. Thanks as always for reading and supporting me! :)

Link: https://www.amazon.com/dp/B0BPZCV3KT

*FYI, this is Chapter 2 of 3 that'll be shared here on BC!*

CHAPTER TWO

“A salon day? You’re kidding, ” I said in disbelief. “You don’t even like salons. I don’t even like salons!”

“Relax, it’s not what you think,” Grace said, reaching into her pocket and pulling out a little orange gift card. “I won it in a school raffle. Cool, huh? I figured you could use a pick-me-up, and what’s better than splitting a little salon day with your sister? You can do a lot with 250 bucks!”

“Two hundred and fif—“ I began, but badly needed a reset. “Grace, listen. I don’t need a salon treatment to feel better. I’m doing fine, trust me.”

“Oh shut up. It’s not like they’re doing anything girly in there. I just booked a wash and a trim for you. We’ll sit next to each other, you don’t even have to talk to anyone else. It’ll be fine.”

I really, really hated the idea of being tempted with bowling only to be ambushed and brought in for a haircut. Again, I glanced at the wooden sign in front of us. A yellow, floral base with orange lilies scattered around the girliest font imaginable reading ‘Lily’s Touch’.

I sat in the car, fuming thanks to her deception. But Grace didn’t seem close to changing her mind. I sighed obnoxiously loud to assert my displeasure. Maybe I just accept my fate for the day. It’s not like I have anything else going on.

“Fine…” I backed down, much to the devilish enjoyment of my sister. “But we’re not gossiping with the barber.”

Grace groaned. “They’re not called barbers. They’re stylists. Jesus, Alex…”

Practically shoved out the car by my sister, the two of us tread the icy parking lot and shuffled into the salon just in the nick of time.

“We made it! Ha ha!” Grace celebrated, probably to the annoyance of the staff. She stepped up to the counter where a gorgeous, thin brunette woman dressed to the nines greeted us.

“Good afternoon! You two ladies have an appointment?”

Ugh. Another ‘perk’ of having long hair…

I shoved Grace aside for a moment, “Actually I’m a guy.“

She shot me a mean look, as if I was the rude one. “It should be under Grace Lester.”

The pretty brunette receptionist clicked and clacked away at the computer searching for our reservation. The searching process offered me a moment to breathe in the ambiance of Lily’s Touch. And damn was this place giant.

Right off the bat, the space felt like infinitely more than any barber shop I’d seen. Back behind the receptionist’s stand were rows and rows of styling chairs — about half of them in use by a variety of barbers — err, stylists. But it didn’t stop there. In fact, just beside the waiting area, beautified with funky-looking orange and yellow furniture, was a staircase ascending to a second floor. I meandered around as Grace continued the check-in.

“Lily’s Spa,” I mumbled to myself, reading the sign by the stairs.

So this isn’t just a salon, but a spa too? I guess that would explain the customer volume. In fact, I counted at least 10 people in the waiting area, scrolling their phones or browsing the complimentary fashion magazines.

“Coming through!” a woman brushed by me, spinning me around. The employee was balancing an assortment of powders and goops on a fancy metal tray as she ascended the staircase. “Jolene? Come on up,” she said to one of the waiting women who eagerly arose from her seat and followed her upstairs.

“Hey, space cadet!” Grace called for me back at the front desk. “They’re ready for us.”

Two younger ladies escorted Grace and I toward the back where we hung up our coats and were seated at the washing stations. My girl instructed me to lean my head back into a basin attached to the chair as she flipped on the nozzle.

“I’m Nora by the way,” the young woman said sweetly, gently soaking my hair. “This temperature okay?”

“It’s uh… yeah. It’s fine, thanks.”

Nora smiled and continued on my hair, squirting some sweet-smelling shampoo into her hands and applying it throughout my hair and softly into my scalp.

“You’ve got so much hair,” she said in what I hoped was a complimentary tone.

I gulped and squeaked out an uncomfortable “thanks?”. Grace, getting the same treatment two chairs over, chuckled at my reaction.
“Just relax, Alex. It’s fine!”

Nora and Grace both giggled at my discomfort as the two ladies started chatting themselves – just small talk about the weather and a little celebrity gossip as I sat still, mostly ignored as my brunette mane was lathered and rinsed. So much for Grace’s ‘the two of us will just talk the whole time’ promise.

This whole situation was so bizarre. I mean, sure, the washing felt good and Nora was friendly enough, but the sweet smells, the flower decor all over the walls… This was nothing like the gritty, hardware store setting I’m accustomed to. I couldn’t have felt more out of place. Not to mention the salon being almost 100% women. Though if Grace’s goal was to get my mind off the firing? Mission accomplished.

With my hair washed and patted dry, I was escorted to the main styling area. Here, it appears, is where the real magic happens. Rows of clients – notably entirely women – sat happily in styling chairs as their respective stylists worked like busy bees, snipping, curling, and styling away. I counted at least 16 chairs and stations altogether. This was a seriously impressive operation.

“Bella will take care of you the rest of the way,” Nora said. “Thanks again!”

She walked away with a smile as I stood there with my dripping brunette locks hanging flat and slouching in a black nylon salon cape. I looked less like a guy and more like the girl from The Ring.

“No way… Tarzan?” a voice said.

Wait… what?

Hearing that name could only mean one thing. And hearing it in a salon could only be trouble. I whipped around for the source and sure enough, standing right in front of me was a girl. No, a woman. An absolutely stunning, tall but curvy blonde woman who looked damn familiar.

“Sorry, Alex,” the woman corrected. “Not trying to dredge up old nicknames. It’s Bella Faison. We went to high school together.”

Holy shit, we totally did! The memories rushed back in. Not that we were ever friends or even interacted much, but sure enough that was Bella Faison — the way-out-of-my-league Bella Faison.

Upon the realization, my body started freezing and my mouth turned dry. I felt like an embarrassed high schooler all over again. Why, of all places, did I have to run into her in a goddamn hair salon?

“You okay?” Bella asked, chuckling. “Gonna be honest, I never thought I’d run into you here. But you look like you could use a trim. Come take a seat?”

I mindlessly followed her down the row of stations till we reached hers and was sat down. Cute little trinkets and photos of her with friends adorned her work shelf – including a high school graduation photo in a very recognizable robe, as if I needed any further proof.

“So how are you? God, it’s been… What, four years?”

Still dazed, I mumbled an awkward ‘mmhmm’ as I worked to turn my embarrassment into realism. I mean, what else could I do? Sprint out the salon and come off as a maniac? Just because I’m unemployed doesn’t mean I’m immune to shame.

“Have you been here before? Don’t think I ever caught you.”

I shook my wet, mop-like hair. “No no no. Never. I’m not a salon guy. My sister, Grace, had a gift card she wanted to split with me. So… yeah. That’s why I’m here.”

Bella stared blankly at me for a moment, then cracked an honest grin. “That’s sweet of her to share with you. And even sweeter of you to come.” She twirled her flashy, silver scissors through her fingers for a moment and tossed a bit of my hair. “So what’re we doing today? Just a trim?”

I nodded as Bella jumped into what was, I assume, her easiest cut of the day.

Making small talk with Bella was easier than Nora because at least we had some history to draw on. Though apparent to me immediately, Bella started realizing how little overlap we had in high school. In fact, we really couldn’t have been more unlike each other. And it was a BIG school. Bella was a solid student, a cheerleader who dated a boy on the football team, and of course, trafficked in the most popular spaces. Whereas I was a recluse with only a couple friends who unfailingly left school at the sound of the bell, retreating home to read, play video games, or do anything as long as it wasn’t with anyone.

Our lack of commonalities soured the conversation a tad, but Bella didn’t seem to care. She had a refreshingly cheery demeanor the whole time, even going so far as to compliment the length and thickness of my hair every few minutes. While sweet, I probably could’ve done without the latter.

The entire cut took no more than 15 minutes. Of my roughly 26-inches of hair, she removed maybe 5 or 6? Just a few simple snips, keeping it even and simple while adding just a bit of texturizing. No complaints.

I took a look around the styling area and noticed Grace was getting her cut done about four spots down with a male stylist — but it looked like she still had a bit to go on her shoulder-length bob.

“That’s your sister down there with Justin?” Bella asked.

“If the pink-haired man is Justin, then yes,” I answered. I always found it funny how expressive and unique people in this profession tend to look. Bella, however, was the exception. Beyond a few tattoos on her arms and a stud in her nose, her style wasn’t too eccentric. She’s evolved since high school, sure, but who among us hasn’t? Stagnation is boring.

Bella did a final minute of clean-up before unsnapping the cape’s neckline, whipping it from my body and releasing me from the chair. “Look good?” she asked.

“Same as always,” I noted. “Though I’ll admit, the shampoo was actually a nice touch.”

“Oh, so the one part I didn’t do?” Bella kidded with a smirk. “That's why salons are better than barber shops. Pricier, sure, but you can’t beat the full service.”

Bella looked at me with her kind eyes — the kind of look a genuine friend would give. “Come back anytime, Alex. I’d be honored to work on that gorgeous hair any day of the week.”

I gave a mere courtesy laugh — again, not loving these comments about my hair quality — but honestly, anything nice from a girl like Bella was appreciated.

However, her joviality didn’t last long as I watched her face do a full 180.

“Ugh…” Bella droned. “Goddammit.”

I turned around to see what was upsetting her. At a styling station a few spots down stood a 30-something man in a black button-down and black pants with sleek, short gelled hair. At the moment, he didn’t look to be doing much beyond chatting with another stylist while she sat in a chair.

“What’s wrong?” I asked, subtly gesturing toward the man. “Who’s that?”

“Tim,” Bella answered disgustedly. “He shouldn’t be there. One sec.”

I watched as Bella waltzed over to Tim, interrupting his conversation with the other female stylist — rudely, I might add. With the whirring of dryers and buzzing of razors, I couldn’t hear their discussion, but Tim seemed to echo Bella’s disdain as she came over.

For as curious as I was, I knew better than to get involved in others’ drama, so I stayed put in the chair and waited for Bella to officially release me. But instead, Bella turned toward me and pointed. Tim looked over and did the same, but with more contempt.

Shit… What did I do?? How the hell was I already in trouble? Ugh. Was it because I was the only guy in here? I knew coming here was a mistake.

Bella jogged over to me and without a word, grabbed my hand and yanked me over to Tim.

“I said, we don’t need help. The chair is fine,” Tim complained, his voice nasally.

“I’m sorry, but you don’t work here all day like I do,” the other stylist protested, much to the annoyance of Tim.

“Guys, this is Alex. He came in with his sister today for a trim,” Bella explained to the feuding duo, undoubtedly wondering who this shrimpy long-haired guy was.

“…and?” Tim sneered.

“And…” Bella mimicked his tone, “During his haircut, Alex told me he works in hardware. Maybe he could fix the chair.” Then she turned to me. “Think you could?”

A little struck by her request, I glanced around the salon. Everything was business as usual. Grace appeared to have some time to go, happily chatting away with her stylist.

“I mean… sure? I can try. Show me what’s wrong.”

Bella cheered as she and Tim stepped aside for the other stylist, Kylie, to explain the problem.

It didn’t take long to determine the foot pump was super loose, requiring triple the effort to move the chair up or down — not to mention a forceful squeak with each pump. Broken? Not entirely. But enough to infuriate a stylist over the course of a day.

“Yeah, I can fix it,” I said, fiddling with the handle. “But I’d need a socket wrench. Do you guys have one?”

All three of them looked at me with blank stares.

I sighed. No surprise these aren’t handy people. “How about a tool box?”

Tim had Bella run into the back room to grab what appeared to be the sole tool box in the entire establishment. A dusty, rusty green metal box with unorganized, random tools inside.

I dug through the box until thankfully finding a barely-usable socket wrench. Just a few minutes of adjustments later and the chair had returned to its full function.

“Voila!” I announced, standing back up. “Like brand new, eh?”

Kylie examined the chair for a moment. “Well, the cushion’s still falling apart…” she noted, shooting another glare at Tim. “But it’s so much better, Alex. Thank you!”

It wasn’t just Kylie but Bella who seemed impressed. Gloating, even. Though probably because it was her idea to fetch me.

Tim took a menacing step forward and, to my surprise, actually extended his hand.

“Killer work. Thank you,” he complimented with as much sincerity as he’s probably capable of. He then leaned in for a whisper, “Anything to get these damn stylists off my ass.”

“Hey!” Bella jeered at Tim, shoving him aside. “Alex, you’re a lifesaver. Kylie, I hope that helps. Now if only you could fix the other ten chairs…”

“I… uh…”

Tim held out his hand to shut up Bella. “You’ll have to excuse my sister. She doesn’t do the budget.”

Sister? I did a double take between the two, suddenly seeing the resemblance. I suppose the bickering makes more sense now.

“Maybe I should,” Bella snapped back. “But fair enough. I can’t accept too much free labor.” Bella smiled at me warmly, craning her neck to check on the status of Justin’s chair. “Looks like your sister’s wrapping up soon. Go chill in the waiting area. Sorry if there’s no manly tool magazines for you to read!”

I chuckled, thanking her again for the haircut but eager to retreat to the quiet of the waiting room.

I was left alone for the next 20 minutes, mostly scrolling on my phone as I waited for Grace’s cut to wrap up. As weird as it was to be abruptly summoned for a maintenance task, I actually kind of enjoyed it. Maybe it’s my unreasonable ego, but the ability to… I dunno… shine again? It felt nice. Even with the uncomfortable bickering, that was three more thank-you’s than I ever got working at Samford’s. Plus, the ability to reassert a little of my masculinity after a sweet-smelling wash and trim was an added bonus.

“What? You look the same!” Grace startled me, emerging from the coat room beside me. “I thought you’d change your mind and go short!”

“Then I guess you don’t know me,” I joked. “Yours isn’t too different either. It just looks… fluffier.”

“It’s called a blowout, you goon,” Grace teased. “Men know nothing.”

I rolled my eyes as I followed Grace out the door of Lily’s Touch. Two siblings, each with a fresh haircut and, as Grace noted, identically scented hair.

“So tell me, was it that bad?” Grace asked as she buckled her seatbelt. “I mean, I know it’s not bowling. But you did need a cut.”

I shrugged. In all honesty I didn't hate the experience. “Beats being unemployed at home.”

My sister shifted the car into reverse and prepared to pull out onto the street. That is… until we both noticed a man running out of Lily’s Touch — and towards our car. It was… Tim?

He motioned for Grace to stop the car and to roll down the window.

“Fuck it’s cold, man…” Tim chattered, coatless. “Alex, I wanted to catch you before you left. You’re jobless, yeah? Unemployed?”

Grace laughed as I dully answered him. “Uh, yes. I am.”

“Well look, I wanna take back what I said earlier. We actually could use some help around the holiday season. Especially someone with your skillset. Want a job at Lily’s through the holidays?”

I sat there in the car, frozen — and not from the frigid weather. “You’re… offering me a job?”

Tim rubbed his arms, the cold air starting to affect him. “Yes, yes, I am!” he said impatiently. “Can you come in tomorrow at 8 or not?”

I turned to Grace who was just as shocked as I was, but coaxed me to answer.

“Um, yeah! I can. I’ll see you tomorrow morning.”

“Killer. I’ll see you then,” Tim added, already backpedaling into the store. “Tomorrow at 8! Don’t be late!” he yelled.

I gave him a little salute as I motioned for my sister to keep driving. It was silent in the car for just a moment.

“Um…. So what was that about?” she asked.

I quickly summed up the brief bout of handyman work, very much to her surprise.

“Dude, that’s incredible!” Grace gleamed. “Next time don’t bury the lede, eh?”

“I’m as shocked as you. But I guess… I’m back in maintenance again.”

Grace nodded as she drove forward, chuckling to herself after a moment. “Unless, of course, they’re hiring you as a hair model!”

Her chuckles morphed into a full belly laugh, probably imagining her painfully uncomfortable brother in that kind of situation.

I laughed along, humoring her jab. I guess we’ll find out for sure tomorrow. But, I mean, this has to be a maintenance job… right?

========

One more sample chapter coming this week, but the entirety of Maybe You'll Like It is available on Amazon right now!

Really hope you all enjoy, and thank you to everyone who's already read it! I'm over the moon with the feedback so far :)

-Jennifer

AMAZON LINK: https://www.amazon.com/Maybe-Youll-Like-Gradual-Feminization...

*FYI, this is Chapter 3 of 3 that'll be shared here on BC!*

CHAPTER THREE

Several years ago during my high school graduation ceremony I heard the term ‘imposter syndrome’ for the very first time. Notably, the term came from several student speakers, each touching on how they, despite achieving and earning their successes, felt as if they don’t deserve those successes. Sure, those kids were referring to getting into a good college, but as I wake up, shower, and get dressed this morning, I’m feeling much the same.

No, it wasn’t my fault that things went south at my old job. I did nothing wrong and I was working for an objectively nit-picky asshole. But still, much of me believes I should ‘pay’ for leaving my job early — to suffer, at least somewhat, in this phase of jobless wandering.

And yet, here I am, with the quickest job turnaround known to man! Not even a full week had gone by and I’d been blessed with another gig that uses my skill set, and just when I needed it most. So of course I feel like an imposter. Of course I feel unworthy of this opportunity. The good fortune of my sister winning two free haircuts somehow landed me a job through the holidays. Not because of anything I did, but because ‘The Job Gods’ were looking down on me. Frankly, I’m not sure whether to feel guilty or grateful.

Despite Tim’s lack of instructions, I figured it couldn’t hurt to bring a few tools with me for my first day. After all, if the sad, disorganized Lily’s Touch toolbox was just barely enough to fix that one part of Kylie’s chair, I can’t imagine there’s enough equipment for the other issues Bella alluded to.

The only thing I truly knew about today was that it’d be hectic. Hectic and disorganized. But being paid to fix problems might be the best thing for me right now.

========

I wasn’t sure who to hope I’d see first at the salon. As much as I got the butterflies from spending that little time with Bella, a small part of me feared that her kindness started and ended with my haircut. Returning now as a coworker — and her brother’s hiring decision, not her own — could easily breed resentment. Tim, on the other hand, seemed somewhat erratic in his demeanor and decision making. What if he’d changed his mind overnight? What if I was just an impulse hire?

Alas, Bella was the one waiting at the front desk when I walked in at 8 A.M. and luckily, welcomed me with a smile.

“There he is!” Bella announced, hustling around the desk and greeting me with a big bear hug.

“Heh heh, yeah, hey!” I managed to mutter through her tight squeeze.

The salon was quiet, being a whole hour before opening. Only a couple employees were even in yet — mostly stylists getting a head start on cleaning their stations or charging their devices.

“So I fully intend on giving you a proper tour,” she explained. “But Tim wants to meet with you before jumping into anything.”

And so I followed Bella to the back room of the first floor, past the washing stations and the row of styling chairs I’d become somewhat familiar with yesterday.

“Take a seat,” she said, holding open the door to the bland, lifeless office. And sure enough, there was Tim, seated behind an equally bland desk with his feet kicked up.

“Alex! Welcome, welcome. Thanks for coming,” he said, though failing to rise from his seat. “I was a little afraid you wouldn’t show up.”

I plopped my butt in an ugly green chair next to Bella. “And why is that?”

“Well for one, I realized I gave you almost no details. But hey, beggars can’t be choosers, right?”

Tim laughed — not cruelly, but I found it a bit offensive making light of my joblessness. I set my personal feelings aside and gestured to the toolbox I’d been carrying. “I brought in a few more tools your box didn’t have. Just show me around and I’ll start fixing what I can. Though I may need to take some trips to the stor—”

He lurched for a second, shooting Bella a quick glance and then looking back my way. “Yes… That’ll be great, but it’s not everything we had in mind for you.”

I blinked once. Then twice. “There’s more? Sorry, I’m not following…”

Bella finally jumped in. “You wanna explain or should I?”

Tim held up his hand, dismissing her. “No no, I got it. So look, looong story short, Lily’s Touch was a salon owned and operated by our mother, Lily. However, she, let’s say…”

“She died of a heart attack. Last year,” Bella said bluntly, clearly displeased with her brother’s loquaciousness.

“Oh my god. I… I’m so sorry, guys…”

“It’s alright, but thank you,” Tim assured. “What’s important is that she left the salon for Bella and I to run together. It’s been going… fine. Besides being a stylist, Bella handles most of the staffing and booking, while yours truly handles the business side and the most important picture decisions.”

While the history lesson was nice — and certainly colored my two bosses’ personalities — I still was unsure what this had to do with me.

“So do I report to both of you, or…”

“My sister and I have differing views,” Tim continued, ignoring my question. “I personally have much more of a growth mentality while she prefers a steady ship. But respecting our mother’s wishes of a shared venture, I decided to compromise. And you, Alex, are our solution.”

“…Me?” I clarified, met with Tim’s ultra-serious eyes.

“You’ll be satisfying both of our needs. Bella wanted for an extra set of hands, and so I obliged. On the weekdays, yes, you’ll be doing maintenance work and clean-up. Sweeping hair, fixing sinks, chairs, and maybe some light carpentry.”

“Okay…” I muttered. “And the other half?”

“The moment I saw you fixing the chair, unafraid to get your hands dirty, a question occurred to me. Why on Earth don’t we have more men here? This whole fucking place is women! And listen, I’m not a rough-and-tough guy myself, but I think men of your ilk could really benefit from masculine-focused self-care services. Not to mention doubling our clientele.”

I nodded along, not necessarily disagreeing.

“And so that is my desire for you! To be an ambassador for Lily’s Touch. A hand to reach out for all the dudes out there, to get ‘em in here and show that, yes, you can treat yourself to a facial or a massage or a beard trim.”

Bella had little reaction to Tim’s speech, as I assume she’d heard it before, but she appeared to be on board.

“Of course, the details are still a little fuzzy but I’ll iron things out as we go. For now, in between your duties, Bella will be walking you through some of our services so you, as a man, can be equipped to translate.” Tim leaned back into his chair and kicked his feet back up. “How does that all sound?”

Again, I glanced over to Bella. The whole proposal was certainly more than I’d expected. I mean, what the hell do I know about self-care? As Grace says all the time, I barely even brush my own hair. The maintenance and physical labor aspects all checked out, but this whole ‘ambassador’ side felt like a lot.

“I don’t know…” I confessed gloomily.

“We’d get to spend a lot of time together, and it’ll be a great way to meet the staff,” Bella explained. “I promise, I know my shit and you will not be left high and dry.”

The prospect of spending time with Bella and maybe even being introduced to some of the other cute staffers was intriguing. Hell, more than intriguing. I thought it over for a few more moments, running scenarios through my head and weighing whether a career pivot like this — even if just for the holidays — could ever be pulled off.

“You know what? Yes,” I eventually said. “I’m a lifelong learner and I like a good challenge. I’ll do it.”

Tim emphatically reached across the table to shake my hand — the first genuine show of enthusiasm I’d seen from him yet.

All I can hope is that at this point, the twists and surprises stop in favor of some nice, steady personal and career growth. If all goes to plan, this could usher in a new era of Alex.

========

In most ways, at 22, I’m completely grown up. Recent hiccups aside, I’ve been fully employed since graduation, I rent my own one-bedroom apartment on the north side of Kankakee, and I’m financially independent. My sister is too. She’s employed, a renter with a steady income, and even starting to date somewhat regularly for the first time in her life. To the outside observer, we’re two successful siblings. But to my mother? That’s a different story. And we’re reminded of that fact every month when we go over to Mom’s for dinner.

I say ‘Mom’s’ and not ‘our parents’’ because, for the last 10 or so years, our dad has been out of our lives. He cheated on our mother with some girl in her 20s, got caught and kicked out with a divorce soon after. Tale as old as time, right? Unfortunately the whole affair turned my mother into a far more cynical and skeptical person than she was probably meant to be. She’s not a bad woman, but it's safe to say being around her has, well… lost its charm.

And yet, once a month Grace and I swallow our pride and let Mom host a family dinner. Maybe it’s because we still pity her from the situation with Dad, or we’re just guilty that she still lives alone. Regardless, the dinner always turns into the same thing: Mom getting on our case about god-knows-what and someone’s feelings getting hurt. At this point it’s unavoidable.

One might think with my fortunate new job situation that I’d be relieved and ready to gloat, and if it were a straight-up maintenance role, maybe I would. But the wildcard ‘salon ambassador’ position gave me considerable pause. There’s not a chance in hell Mom would support that kind of work. Frankly, I had enough trouble garnering her support elsewhere in my life.

On the drive over I came to the ultimate conclusion that the new job would be kept entirely secret. Not just from Mom, but Grace too (at least for the ambassador stuff), until I had a firm grasp of what I’d actually be doing.

With a plan in place, I mustered the courage to leave my car just as I saw Grace pull up in hers. Though through the blurry windshield across the street, I noticed something off. Someone with Grace.

“No way…” I muttered to myself.

“Guess who’s here?” Grace yelled from across the street, gesturing to the woman getting out of the car. “Making her grand debut…”

But I didn’t need her showmanship. I knew who that was. It was Tamara — her latest fling.

“Alex, come here. I want you to meet Tamara, my girlfriend,” Grace said excitedly, introducing me to the woman beside her. Tamara confidently shook my hand as I hid my emotions the best I could.

“Pleasure to meet you,” the tall, late-thirties woman said kindly. “Grace has told me so much about you.”

“Likewise,” I replied dully, not sure what else to say. “So…”

“Run ahead to the door, Tamara,” Grace instructed. “Give us a second.”

I waited for Tamara to be out of earshot before wiping the fake smile off my face. “What the hell are you doing??”

“What? I’m just bringing my girlfriend to family dinner,” Grace answered coyly. “Can a girl not do that?”

I slapped my forehead. “This’ll only piss off Mom! I can’t imagine you gave her a heads up.”

Grace confidently shook her head. “Nope! She’s just gonna have to deal with it. We’ve been seeing each other for 2 months now, and I feel like it’s time she met the family.”

As happy as I was for my sister, knowing her, this felt like more of a stunt than anything else. Grace has historically butted heads with our mom, and neither being one to back down from a fight, I foresee this ending only in disaster.

“Well I hope you know what you’re doing. Maybe being so close to the holidays Mom’ll take it a little better.”

“Doubt it,” Grace answered. “You know, a lot of this is thanks to you. Hearing you quit a job and boldly accept a new one? I dunno, you kinda lit a fire under my ass to be a bit more of a rebel too and to stop giving a fuck.” Grace patted me on the back and walked ahead to join Tamara. “Thanks for that.”

I stood there, bewildered and a little afraid of what’s to come. No, I was not happy that Grace thought to introduce even more chaos in my life at a time like this. But in a roundabout way, this Tamara thing might work in my favor. My sister’s 10-year age-gap girlfriend of two months might serve as the perfect distraction from my own bubbling secrets.

========

“So that’s how we met! And we’ve been very happy ever since,” Grace said, raising her cocktail into the air and leaning over to kiss Tamara on the nose.

Mom, seated in her usual head-of-the-table position, faked a smile out of politeness. “A lovely story… And ‘ever since’ meaning a whole two months! Just, wow…”

Also as usual, Mom’s bone-dry sarcasm.

She fiddled with her hair to fill the silence. The short, tight red curls on her head complimented her pinched, pointy features – only accentuated by her clear and obvious displeasure with the situation.

“I’m terribly sorry, Tamara, that we barely had enough food for you. If only Grace had given me a heads up, I could’ve fed you properly.”

“Well worth it to meet another member of the family, right?” Grace said, giddy, but reading more like an intentional dig.

Mom grimaced. “Yes… family…” She turned to me. “And you’re sure no surprise guests from you tonight, Alex?”

I shook my head, but wished instead I could bury it in the sand. “Not tonight, no.”

The person I felt the worst for was Tamara who even compared to Mom looked uncomfortable. I can’t imagine what Grace told her to expect tonight but evidenced by her strained grin, it certainly wasn’t this.

We pushed through another 20 minutes of awkward conversation before Tamara appeared she couldn’t take it anymore and politely made up an excuse to leave. Grace attempted to protest, but Mom happily allowed it. Not looking to stick around for the aftermath of her bomb drop, as well as being her ride, Grace agreed to leave with her.

“So sad you couldn’t stay…” Mom said to the girls. “Should I be expecting a Thanksgiving drop-by as well, or…”

“Heh, well… Maybe!” Tamara answered, forcing another smile as she quickly put on her coat.

“Bye Mom!” Grace cheered as she was practically yanked outside by her girlfriend, the door slamming behind them.

With the girls gone and the house quiet, Mom calmly walked up to the door and locked it. “Enough of that mess.”

While I feared the worst, I strangely never got the explosion of fury I expected after my sister’s stunt. I stuck around a little longer to help my mom clean up and do the dishes. Some sarcastic, snippy remarks, sure. But she seemed to not be too upset. Or maybe she was just off tonight.

Not wishing to poke the bear any further, I didn’t speak unless spoken to as we cleaned up and washed dishes in near-silence. No discussion of either of our lives, our jobs, or even of Grace.

Once I felt my son-duty was fulfilled, I too made up an excuse to leave. Not that I needed one. As far as Mom knew, I still had a shift at Samford’s in the morning. But not a question was asked nor an accusation made.

I didn’t receive a hug on my way out. That was never really her, or my, style. Just a simple nod would usually do as I slipped on my boots and wrapped up in my coat for the chilly drive home.

“Well, goodnight,” I said without eye contact. “Thanks for dinner.”

“Mmhmm,” Mom answered stoically. “I’ll see you at Thanksgiving.”

“Yep.”

I reached for the door handle but was suddenly stopped by Mom.

“Wait, Alex.”

I turned around, bracing for impact.

“Thank you for coming. It means a lot that you stick around.”

“Oh. Uh, yeah. No problem.”

Then Mom took a step forward and calmly placed her hand on my shoulder. “And thank you for never pulling shit like that on me. It’s nice to have one honest child.”

My skin started feeling hot, but I must’ve looked okay because Mom was unfazed.

“Sure. Happy to,” was all I said.

“Say hi to Mike for me. Goodnight.”

I stepped outside into the cold night as Mom shut the front door behind me. But unlike with my sister, I didn’t hear the deadbolt lock — comforting for now, but harrowing for my future should any truth come to light.

=-=-=-=-=-=

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CHAPTER TWO

Despite the absurdity of what had happened that evening, I didn’t immediately want to tell anyone. Galen would obviously be first in line, and though I knew he’d be thrilled for me, I think he’d be first and foremost…confused.

Frankly, so was I. Never in my imagination did I picture myself being cast as a leading female role — particularly in such an iconic musical. Maybe I should do a little more research and preparation into this role so I could better justify it to Galen, to everyone… and to myself.

When I got home that evening, Galen wasn’t even home. Good. That would give me the opportunity to research in peace.

Though there was a movie version of Phantom, I opted for one of the recorded stage versions instead. I downloaded the Royal Albert Hall recording from 2011, starring Ramin Karimloo as The Phantom and Sierra Boggess as Christine.

In addition to being a lovely performance from some of the best performers and musicians in the world, I found myself noticing Christine far more than I ever had before. Sierra moved with such grace, such elegance. In the first act when her character is called into action to take over for Carlotta in the leading role of the in-Musical opera, Hannibal, Christine is dainty, hesitant, and cutesy. But as the performance goes on she gains agency and becomes sultry, confident, and intense as she grapples with an impossible love triangle.

I never had to play a female character before, so I knew it would require much rehearsal and a good team around me. But the immediate prospect was discouraging rather than inspiring. How could I completely transform into a leading lady even close to the caliber of Sierra Boggess…

========

Galen came home later that evening as I was making dinner for myself. He looked like he had big news.

“Dude, you are NOT going to believe this,” he began, “Jocelyn apparently went to Horace enraged that she was cast as Carlotta and not as Christine. Which is crazy because they haven’t even released the cast list for it yet. I think they’re still doing callbacks.”

I gulped. Seems like he hasn’t heard the news yet. But I was not quite ready to reveal it to Galen.

“That’s crazy, man… Usually Jocelyn’s nice to me but she can be a diva sometimes,” I added. Fortunately for me I hadn’t encountered Jocelyn’s rage yet, but I can only imagine how furious she’ll be when she finds out they cast a boy in her dream role.

We gossiped about the cast list, and I went along with Galen’s kind attempts to lament my failure to be cast as the Phantom. Though rather than lie completely to him, I decided to share that I was indeed offered a role in the ensemble — that way, we could discuss the play freely and still buy a little time to tell him about my upcoming appointment to perform en femme.

We got in a few games of Mario Kart after dinner and some homework as usual. It was nice to avoid talking about playing Christine, but with the first rehearsal tomorrow, how long could I realistically hold this off?

My second thought was whether I should even be expected to perfectly transition into that role on day one. The director’s job is to coach and mold, and even though Horace thinks highly of me, there’s no way he could reasonably expect me to just become Christine — it’s going to take some work.

But then again, I’m an actor. Above all it is my duty to arrive prepared, regardless of how nerve-wracking it may be.

The thoughts raced in my head throughout the night as I laid in bed, waiting for the news bomb of my casting to the entire theatre program (and possibly all of DePaul University).

I will allow myself to withhold this information from Galen — for now— but I will make a conscious effort to do little “Christine things” here and there. If I do them right, I’ll hopefully convince Horace, the show’s producers, and the rest of the cast that I can indeed play this role.

========

Due to his early classes, Galen left before I even got a chance to see him. That gave me the opportunity to be alone in my thoughts as I waited for the Christine announcement. I knew eventually my voice would need to be ready for rehearsals later, so I sang alone in the apartment. It was incredibly strange to be singing the female role rather than the male, but with all my might I made sure to soften my voice and sing in a higher pitch.

I recorded using Voice Notes on my phone to play back and listen to my singing. Sure, it sounded higher pitched and somewhat more like a woman, but I wasn’t even close to sounding like Sierra Boggess or any other stage actress for that matter.

I walked to campus for class feeling fairly bummed out. But when I arrived in the theater building, I had no time to feel bummed. I was confronted by a fellow theater student who had a huge grin on his face.

“There’s Jesse Harris, the new girl in town!” the theater boy exclaimed to others.

Everyone in the hallway turned towards me. Obviously they had heard the news. From there it was a mix of jeers, cheers, laughs, questions, and an overall massive amount of attention from my peers. I pushed through the crowd of theater students to the posting on the wall. Right next to the original cast list was a separate piece of paper that read in big black letters, “The part of Christine Daée will be played by Jesse Harris.”

The shouts and questions continued but I yelled out to get everyone’s attention, stepping up on a crate to elevate myself.

“Alright listen up!” I shouted as the room silenced. These kids couldn’t wait to hear my thoughts on this. “Yes, I told Horace that I would accept the part of Christine. For whatever reason, he envisioned me in the role. I’d appreciate it if everyone moved on with their days, please.”

“But you’re not a girl!” correctly claimed a member of the peanut gallery.

“Yes… that is correct… but good actors can play any role. They just need to work towards it. I hope everyone can support me as I move forward.”

“Yeah, but you don’t deserve it,” said a female voice emerging from the back. I could see someone moving forward through the crowd of students. It was none other than Jocelyn Price.

“Jocelyn, what do you want? Carlotta is a great role,” I said, speaking over the rest of chatty students.

“Because I earned the role. Horace loved my audition. Until you showed up I was set to play Christine. You didn’t even audition!”

“Let him be, Jocelyn,” it was none other than Galen.

“Oh, Galen, I meant to tell you…”

“Little late for that, huh?” He rolled his eyes at me, and said so pretty much only I could hear.

“YOU are defending this?” she shrieked, “You’re the one playing Raoul. You want Jesse, your roommate, to be your love interest?”

The other students laughed. I hadn’t really considered that until now and by the look on his face, neither had Galen.

“We’ll cross any of those bridges when we get there, but for now Jesse earned the part and he’s a solid actor. His attitude is great, which is a lot more than can be said about you, Jocelyn,” Galen added triumphantly. ‘Ooooohs’ came from the crowd.

Whether she genuinely had no more to say or she was just holding her tongue, Jocelyn stormed off, and the many students scattered off to their classes.

Galen stopped briefly before me. “Guess I’ll see you at rehearsal today. Whatever that’ll be like…” And then he abruptly left.

=-=-=-=-=-=-=-=-=

CHAPTER THREE

Word spread fast around the DePaul theater department that a boy would be playing Christine, and that made many of my classes a lot to handle. My non-theater classes — which were typically the dullest of the day — were a collective relief, since nobody seemed to know or care about the upcoming production of Phantom.

My playwriting class was the trickiest of all. Many underclassmen happened to be in this class — most of whom had no idea who I was before today. Their initial introduction to Jesse Harris would be the gender-bending stage star.

A few shot questions my way: “Did you even audition for that role?” and “Do you think Horace is just doing this as a bit?” were common ones. Neither of which I had a solid answer to. All I could reply with was “I’ll learn more at rehearsal today after school.”

Everything about this wasn’t normal and I’d have to learn on the fly. But one thing I definitely knew from doing theater all my life was that cast chemistry is crucial. If a cast can’t get along, it makes the rehearsal and performance process unbearable. I had a massive target on my back from Jocelyn’s vitriol and my normally closest ally, Galen, wasn’t sure how to feel about having his roommate be the romantic lead.

========

All that we were given via email in advance of the first rehearsal were the script and songs. Nobody but the producers knew how Horace was going to tackle directing the play.

The rehearsal room was the same one where I auditioned (and where many classes were held) in DePaul’s theater building. Folding chairs were set out in a large circle so the entire cast and crew could get a good view of each other. Students trickled in and sat in their assigned seats. They were either labeled with the character names, or simply “Ensemble.” Naturally, I found my way to the one marked “Christine”.

I immediately noticed that I was to be seated between Noah Hackett (playing the Phantom) and Hannah Moon (playing Madame Giry), though neither had arrived yet. For the sake of avoiding awkwardness, it was nice not to be right next to Jocelyn, so hopefully these seating assignments would remain. I mostly kept my head down as the rest of the students arrived. Thankfully no fights or arguments.

“Alright, alright, listen up,” Horace said, quieting the chatter. “I want to begin by congratulating all of you on being selected to be in this year’s production of The Phantom of the Opera. It is an absolute pleasure to be directing you over the next couple months as we prepare for show week. Each one of you earned your roles, and I’m already proud to be working with this cast.”

As he concluded his opening statements, Jimmy and Sarah handed out physical copies of the scripts to each cast member in the circle.

“This is not a particularly easy script, but many of you have been at this for a long time, so I trust you to be off book with the dialogue as soon as possible. Having said that, once everyone has their scripts, let’s do a full read-through of the show. We will skip the songs for now. Jimmy, please read the stage directions and everyone, please be in character to the best of your ability.”

My character is not in the opening prologue, so I got to watch the others as they rid their jitters, starting off the play.

It also hit a little close to home when Jocelyn’s character, Carlotta, storms off in an early scene, frustrated with the conditions of the show and the theater being haunted by the Phantom. She read it well — almost as if she was pulling her anger from a real source (likely my own doing).

But I’m a serious actor, so I managed to not think it weird when I spoke my first few lines in a softer, girlish voice.

“I don’t know, sir…” I muttered, in character.

I could tell that several students were anxiously awaiting my debut line as Christine. Multiple heads perked up with interest and from my quick glances, they looked impressed.

Some cast members couldn’t help but smirk watching Galen as Raoul and Noah as the Phantom, directing their romantic lines toward me. Noah seemed comfortable enough, but I could tell it was a bit weird for Galen. Though he’d defended my casting earlier, I think even he was a bit uncomfortable sitting there as Jimmy read “Raoul and Christine kiss” as part of the stage directions. Even though there was no physical acting involved this time, looking over at Jocelyn, she had a rude smirk on her face — as if for the first time she could revel in the two roommates’ clear discomfort.

Though I felt I got off to a good start, watching Galen’s discomfort and the looks from the other actors started to get to me. My feminine voice didn’t waver, but I stopped reading the lines with the necessary emotion — as if I were suddenly afraid to be Christine. And as the play went on, my discomfort further discouraged his emotion, and so on.

Eventually, the read-through came to an end and after a few notes from the producers and from Horace, we were sent on our way with the specific note to begin memorizing our lines and prep the necessary songs for rehearsal.

“I’ll see you at home,” Galen said without emotion, walking by quickly. Normally, we’d walk back together from these sorts of things. Did this read-through make him that uncomfortable?

On our way out, the cast was instructed to sign up for a time slot to take body measurements, as our costume department needed as much time as possible to prep our wardrobe. All of the outfits are late 19th-century European garb: dresses, petticoats, cloaks, suits, and the like.

I signed up for a slot two days from now, on Friday. Maybe that’ll give me a good send off for the weekend. Just as I finished signing up for a time slot tomorrow evening, Horace pulled me aside for a word.

“I’m very impressed, Jesse. Very impressed.” He said, to my surprise.

“You are? Wow, I definitely had my share of nerves… I guess they didn’t show!”

“Oh, no, they certainly showed.” Horace added bluntly. “You were the most nervous in the entire cast, outside of maybe Galen.”

Ouch… I guess I wasn’t as invisible as I thought.

Horace continued. “But that doesn’t mean you impressed me in other ways. Your speaking voice is quite marvelous and when I closed my eyes, I almost envisioned Christine Daaé. Truly, truly a step above. Did you grow up with sisters or something?”

“No, sir. I’m an only child. But I’ve watched so many incredible actresses over the years… it must’ve just stuck.”

“Well I’ve heard you sing already and I’m sure the voice will stay pure on that end… But we need to do something about your manner. I know read-throughs aren’t blocked or require physicality, but I was hoping I’d see a shred of it from you, considering you’re playing the opposite sex. And unfortunately I didn’t see much that excited me.”

Horace gestured to Sarah, and she scampered across the room to grab a box.

“I’m sorry it came across that way,” I interjected. “I’ll gladly go home and study some more actresses. Is there anyone you have in mind of whom to observe their mannerisms?”

“You could, but I actually have an additional homework assignment for you,” he explained. Sarah walked up holding the box. “It is my belief that a simple change of movement has the unique power to get a person in a new mindset.”

Sarah opened the box she was holding, and revealed a simple pair of black high heels.

Sarah smiled, “I made a guess that your feet were an 8. Was I right?”

“Uhh… I’m a 6 and a half… and what? Is this part of the wardrobe? Already?”

“Horace had the brilliant idea to get you started wearing heels early. You’ll be wearing them in the show anyway, and it’s a simple trick to subconsciously move in a more feminine way. Here, take off your socks and try them on.”

She pulled up a chair and guided me to sit, untying my shoes.

“Oh, uh, okay. But like I said, I’m a 6 and a half size.”

“In men’s,” Sarah corrected, “Eight is the women’s size equivalent. I mean look at these — do these look like menswear to you?”

I laughed. “I guess not.”

“These are 3-inch black pointed-toe pumps. Not exactly what you’ll be wearing in the show, but we wanted to get you started somewhere.”

Sarah helped me take off my shoes and socks and neatly fitted my foot into the first heel.

“A perfect fit,” she commented.

“Like Cinderella!” Horace added in a rare joking tone that I hadn’t heard yet.

I stood up with both heels on and stumbled around a bit. This was the first time I’d ever worn a heel this high, as any mens’ shoes that had a heel tended to be lower and with more support. These felt like stilettos.

“No need to prance around too much right now. You’re free to go.” Horace said. “But please wear these every time you read the script, practice your lines, or rehearse your songs. I believe it will go a long way in putting you physically in character.”

Sarah told me to keep the box and walked off with Horace.

Uncomfortable read-through? Check. Rocky familiarity with the script and my fellow actors? Double check. But I definitely didn’t foresee walking out of my first rehearsal with a pair of black pumps — for me to wear at home nonetheless. I guess if it’ll help me become Christine…

========

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CHAPTER TWO

“Woah woah woah woah WOAH,” I spat out, each ‘woah’ louder and more incredulous than the last. “Erica, what the HELL are you talking about?”

My sister held her hand out in an attempt to steady my nerves, anticipating the explosion. “Will… It’s not that big of a deal…”

“NOT A BIG DEAL?” I screamed, though quickly hushing myself as other tourists walked by. “You’re saying you brought me on a girls’ trip and saying I need to wear a dress. That sounds like a big ass deal to me!”

Erica rolled her eyes. “First of all, it’s not a dress. It’s a kimono.” She waved the flowery yellow garment in my face. “See? Long sleeves. More like a robe than anything else.”

I sighed, annoyed at how she completely missed my point.

“Fine, a kimono. But a girl’s kimono. For a GIRLS trip!”

“Alright, alright… Confession time,” Erica began softly. “I registered for the trip thinking Marie and I would go. You remember Marie, right?”

Yeah… I guess I remember Marie. She’s a high school friend of Erica’s who she reconnected with when she moved back to Chicago last year. Kinda felt like a weird first choice though.

“Okay, sure. So why didn’t you bring her?”

Erica groaned. “At the last second Marie’s boss changed her mind about letting her work remotely for that long. So… I kiiinda lied about my timeline and invited you instead. But hey, maybe it’s good she dropped out because now we can do a sibling trip for the first time in… ever?”

At this point, my face had been contorted for so long it was starting to hurt.

“Look, here’s the deal,” she continued. “We’re in what’s called a ‘bachelorette suite’, meaning at check-in, they need to see two girls rather than a guy and a girl. But I promise, once we’re settled in the room, you can take off the kimono and we can pretend the whole thing never happened.”

I didn’t love how cavalier Erica was about all this. Not one bit. Plus, the fact that she straight-up lied to me felt like a punch in the gut. But I had to remind myself what I was getting in return: a mostly free, most-expenses-paid trip to a Hawaiian resort for two freaking weeks. That’s a hell of a consolation prize. Maybe in exchange — and just this once — I can be a good sport and play along.

“Ugh… fine,” I finally answered her.

Erica giddily jumped up and down like she’d just won the lottery.

“Thank you thank you thank you!” she exclaimed, shoving the kimono into my hands. “Well? Put it on!”

I briefly froze, forgetting for a moment how to even put on clothes. But sure enough, just like a bathrobe, I slipped on the kimono over my t-shirt and shorts, tying it up in the center, to cover all hints of male clothing — well, other than my sneakers.

The garment itself was extremely thin and soft. I’d never worn a kimono before and I must confess I was struck with the material. The flowers I probably could’ve done without, but the robe itself felt quite, uh… nice.

“Silk?” I asked Erica, prompting a nod from her. “You… you wear these around the house?”

Erica smirked. “Taking a liking to it, eh? Feels even better when you don’t wear it over boy clothes.

I involuntarily blushed. “No! It’s just, uh…” I paused, catching myself mindlessly caressing the material. “I guess it’s not as bad as I thought.”

“Well that’s good,” Erica reached toward me and in one motion undid my ponytail, letting my auburn locks fall to my shoulders.

“Damn your hair’s gotten long!” she said, seriously taken aback. “It’s longer than mine!”

I rolled my eyes. Hair length isn’t exactly what I want to be reminded of while wearing something like this.

Erica winked and zipped up her suitcase. “I guess that’s good too. It’ll only help with our deception!”

Luggage in hand, I followed Erica down the sidewalk and toward what’d be, I assume, the most stressful part of this beach vacation.

I was anxiously approaching the hotel, finicking with my kimono and nervously toying with my hair as my eyes darted between each person we passed. I felt like an animal in a zoo, knowing everyone was staring at me. I mean, they had to… right? A boy in a girly, flowery kimono? They’d have every right to point and laugh.

And yet, it was going just fine. Even entering the magnificent Ocean Oasis lobby — packed with eager tourists and busy hotel staff, all scurrying about the tropical, fantastical foyer — no one seemed to take issue with my appearance. Still, not looking to push my luck, I held my head down and kept mum.

Erica, confident as ever, approached the front desk where a smiling, middle-aged woman in a casual navy blazer greeted us.

“Aloha!” the woman offered cheerfully. “Welcome to Ocean Oasis. Are we checking in?”

“Yes, we are,” my sister answered. “We’re the sweepstakes winners with WATT FM.”

The woman nodded, aware of the contest as she clacked away at her keyboard, pulling up our reservation. “Erica Quinn? For the bachelorette suite?”

“Yes ma’am,” she answered. “And this is my guest, Wendy.”

Wendy? Though my eyes stayed pinned firmly to the floor, they opened wide upon hearing that name.

Wendy?

“Welcome Erica, and welcome Wendy,” the receptionist replied without missing a beat. As you know, the room is already covered courtesy of your contest.” She handed my sister a set of key cards. “These are for your suite. One of our bellhops will escort you to your room. Sincerely, girls, enjoy your stay.”

“Thank you so much!” Erica cheered, though she paused before nudging me along.

“Uh, thanks!” I squeaked out as well in a shamelessly high-pitched voice.

Perfectly on cue, a male bellhop grabbed our bags and gestured to follow him. I nodded with a little smile desperately trying to avoid any problem, but the moment he turned around I fiercely gripped my sister’s arm and pulled her in close.

“Wendy!?” I whisper-screamed. “What’re you giving me a girl’s name for?”

She didn’t hesitate to match my temper and grip. “Until we’re in the room… YOU’RE. A. GIRL. Don’t blow this!”

I huffed quietly but held my tongue, walking silently behind the bellhop as he led us through the resort and hotel halls.

As it turns out, our suite was a considerable walk from the check-in desk — though considering the impressive size of the lobby I should expect the same from the rest of the resort. Spending additional time shuffling around in this kimono wasn’t ideal, but it did give us a chance to appreciate its scale and beauty.

To its credit, the hotel was legitimately stunning. The nautical theme enveloped every nook and cranny, hammering in the ‘ocean’ of it all while being tasteful rather than tacky. Exquisite paintings of sea creatures hung throughout the halls and common areas. Majestic gold and maritime-blue color motifs were so ever-present, I wouldn’t be surprised if Poseidon himself were the designer.

“Your room, ladies,” the bellhop announced, approaching a grand, maritime-blue door with gold accents.

“You’re a saint, sir!” Erica complimented, retrieving a tip from her purse.

With Erica’s cash in hand, the bellhop tipped his cap and wished us a wonderful vacation. But as he walked away, Erica shot me a sly little smirk.

“Ladies…” she teased, imitating the bellhop.

“Ughhh,” I groaned at the unfortunate ease of passing as a woman. While my sister took a moment to reflect on the resort’s fun eccentricities, I wasted no time ripping the key card out of her hand and bursting open the door for some sweet, sweet privacy. As much as I wished to rip off the kimono the first chance I got, I couldn’t help but gawk at what’d be our home for the next two weeks. Because boy were we getting spoiled…

The suite’s interior was simple but elegant: two cushy queen beds, a small but functional kitchenette complete with mini-fridge, microwave, and gold-colored sink, a baby-blue loveseat, and of course, a sizable bathroom with – surprise-surprise – a painting of a sea turtle. The room was impressive, sure, but I’d be remiss not to mention the real selling point of the room.

“Wow…” Erica said, her mouth agape.

“Incredible…” I echoed.

Of course, the catalyst of our awe was the breathtaking, unmatched view of the ocean. Any remaining reservations I had about this trip immediately washed away looking at that crystal clear ocean, the vast, golden beach, and our adorable, private, third-floor balcony overlooking it all. Even for a Los Angeles resident like myself familiar with coastal beauty, this view blew my freaking mind.

I slid open the floor-to-ceiling door as the sweet smell of ocean breeze rushed into our room, engulfing us in its wonder. My sister and I had officially arrived in paradise.

Tenderly, Erica stepped beside me and put her arm around my shoulder. “Still mad about that kimono after getting a view like this?”

Mesmerized, I shook my head. How could I be? I’m basking in ocean serenity and Hawaiian bliss.

“I’ll get over it…” I whispered, still entranced by our sensational setup. “Could have gone without the Wendy stuff, but…”

“Cute name though, yeah?” Erica chuckled. “It just came to me!”

I shrugged, refusing to weigh in on the ‘cuteness’ of my temporary girl name. Erica reached across my face to tuck away a strand of my loose auburn hair that got unsettled by the wind.

“You did great though, Will.”

“Heh, thanks…” I answered, finally snapping out of my sea stare and turning my focus to the kimono. “I’m done with this thing, yeah?”

“Sure,” my sister answered, though with a bit of waver in her voice. “I’m gonna hang back here for a minute though. Go explore the resort. Remember, it’s your vacation too.”

========

To be completely honest, the whole ‘Wendy’ bit didn’t bother me as much as I thought it would. Partly because it was so short-lived, but mostly because it was merely a speed bump in pursuit of a restorative trip.

I did exactly as Erica recommended and took my time exploring the grounds of Ocean Oasis. And it’s safe to say I was thoroughly impressed.

The resort had everything a vacationer could want. The beautiful, golden beaches stretched on for miles, speckled with resort guests and tourists alike working on their tans. Surfers took to the water to carve up waves with the cockiest ones doing goofy dances atop their boards to impress their friends on land.

A multitude of restaurants lived alongside the beach walkway offering all types of cuisine. Some were fancy and others casual, but each spot had its own unique styles, smells, and staff all beckoning passers-by to partake in a tasty meal.

Eventually, I encountered what many would consider the calling card of any vacation resort: the pool. No legitimate resort is complete without a pool, and The Oasis Pool Club was so much more than that. Giant slides for the kids, a pool bar and cabanas for the adults, and fun, energetic music played by an extremely gregarious DJ, trying nonstop to get the loungers and swimmers to get up and dance.

I spent well over an hour wandering about and taking in the scene. Ocean Oasis felt like the perfect mix of elation and relaxation, and I couldn’t wait for Erica to see it all too. For an introvert like myself, it was a tad overwhelming at times, but at the very least I knew it was a place my sister could thrive.

After what felt like a thorough self-tour of the estate, I decided to head back to the room. But something new caught my eye. About a quarter-mile down from the turn-off to our hotel, well past the resort and beyond a stretch of rocks, was a section of abandoned beach.

Curious, I approached it, traversing the large, slippery stones to find, yes, a small patch of beach, but also a lone palm tree planted in the sand with a blue Adirondack chair nestled beneath.

“Hmm…” I muttered, approaching the tree and observing my surroundings. Being so far off the resort, it wasn’t terribly surprising no one was here. And clearly, whoever had put this chair here hadn’t used it in years. It was sandy, dirty, and in desperate need of a paint job.

But still, the serene, private set-up felt very zen. The hectic, vibrant nature of Ocean Oasis was nice, but something about this spot felt cozy and warm. Without even thinking, I slipped off my shoes, dug my toes into the sand, and sunk my butt into the chair. God this felt relaxing. Nothing around me but a vast ocean. I felt focused and dialed in.

Wait…

Was this the feeling I was searching for? Had I actually unlocked an at-peace, creative mindset ready to write?

A smile crept onto my face even as a gust of wind rushed by and messed up my hair. I had come to a decision. In this chair, next to this tree is where I will finally start my next script.

I had no idea what I’d be writing about, but for the first time in months, I felt ready to write again. And damn did it feel good.

Not wanting to keep Erica waiting, I took note of my new sanctuary’s location and returned to the hotel.

The feeling of finally taking a first step toward relieving my brain fog and writer's block was unbelievably freeing. I’m embarrassed to admit it, but I was so giddy that I even skipped a little on the quick journey. Hopefully, nobody saw.

I couldn’t wait to tell Erica about my new spot as I hurtled through the hotel lobby on my way back to our room. Until, strangely, I spotted another curious thing out of the corner of my eye.

A man. A familiar man…

Without catching his attention, I dug deep in my memory for where I knew his face. A tall man with a strong jawline and short, curly, dark hair… Heh, you know, if anything, that describes my sister’s type to a T.

Then it hit me. The man I passed… of course he’s my sister’s type – because that man’s name is Carter.

Carter, my sister’s ex-boyfriend!

My heart started to race. It wasn’t a perfect look, but long enough for the memories to rush back in. Carter was Erica’s boyfriend in college. I never met him and hadn’t seen his face beyond pictures, but I had no doubt it was him. And if he’s here in the lobby, then he must also be a guest.

Suddenly, my creative inspiration felt like the least important thing in the world as I sprinted back to the room to warn Erica. I knew telling her might drudge up bad memories and cause concern, but as her brother, it’s my duty to tell her.

“Erica!” I shouted, bursting into our suite. She was out on the balcony but whipped her head around, concerned.

“Jeez! What’s wrong? Please don’t tell me you’re already hating it here.”

I shook my head. “No, everything’s beautiful. But listen…” I paused, steadying my voice. “This may be hard for you to hear, but you deserve to know. I ran into someone in the hotel lobby. Someone from your past.”

Erica, to my surprise, didn’t flinch. She said nothing as she stood up and closed the balcony door behind her.

“You saw Carter, didn’t you?” she asked calmly.

“W-what?” I stammered back. “Yeah! How did y—“

Instead of rage or fear or dread, Erica approached me evenly, sitting us down on the edge of the bed and sighing.

“Will, I have one more confession…”

=-=-=-=-=-=-=-=-=

One more sample chapter will be posted this week, but the entirety of Two Weeks of Wendy is on Amazon right now!

Thanks for reading :)

-Jennifer

AMAZON LINK: https://www.amazon.com/Two-Weeks-Wendy-Gradual-Feminization-...

***FYI This is third of three chapters that will be shared here on BC***

CHAPTER THREE

My brow furrowed and my body tensed. We weren’t even a full day into our trip and already Erica was on her second confession.

“Erica…” I began cautiously. “What are you talking about? You knew he was here?”

It took her a moment, but Erica swallowed hard and nodded.

“Yes, okay? I knew he’d be here. But please just hear me out.” She took a deep breath and began to explain. “When Carter and I broke up at the end of college, I unfollowed him on everything — Instagram, Facebook, everything — because I didn’t want any feelings to fester. And, honestly, it was for the best considering he eventually found a fiancée who’s way prettier than I ever was.”

Already I was shaking my head with disappointment. “Jesus… So you’re here to home-wreck. Do you have any idea how bad of an idea that is!?”

“No no no!” she insisted, holding out her hand. “I don’t follow him but Marie does. And a month ago she noticed Carter’s been super active with his life updates. He got this fancy new job in Dallas, called off his engagement to that girl, and… well… he won a two-week sweepstakes trip to Ocean Oasis.”

Everything slowly made more sense.

“So this whole trip…” I began to surmise. “This whole sweepstakes. We didn’t actually win?”

“The trip is 100% real. I really did win the sweepstakes.” Erica asserted. She bashfully dangled her feet off the bed like a nervous tween. “It just wasn’t quite as, uh, spontaneous as I made it seem.”

I let out a small sigh of relief, pleased that at least some of her original story was truthful. The last thing I needed was to find out we were paying out of pocket. Or worse, that we scammed the resort. Still, my fury toward Erica was present and justified.

“Look, Will, I’m sorry I lied,” she said cautiously, likely noticing my skin reddening with rage. “But, shit… I’ve been looking back on those days recently and I really think Carter was the one! Maybe it’s my move back to Chicago or turning 30, but every fucking day I think about how breaking up with him was the biggest mistake I ever made. And winning the bachelorette sweepstakes… I honestly think it’s a sign from a higher power.”

I’d never claim to understand how my sister’s brain functions. Hell, sometimes I doubt she even knows what’s going on. But the way she was talking about Carter — whether in her best interest or not — it was clear she still cares about him. Sincerely and passionately.

“Two weeks,” I stated. “Two weeks is all you think you need for him to… to what? Fall in love with you again?”

Erica shrugged. “Maybe not ‘fall in love’, but at least show him I’ve grown and matured. I mean, I dumped him, so it’s my responsibility to make it up to him, right? I owe him that much.”

I was impressed by the level of self-reflection and maturity Erica had shown — even if flying across the country to a Hawaiian resort for a pre-planned meet-cute is still pretty insane. But for someone who’s chronically indecisive and vacillated between jobs and cities her whole life, it was refreshing to see her stick to her guns and go after what she felt was right.

After a sequence of deep breaths and convincing myself not to strangle my sister on the spot, I was able to think rationally again.

“So what do you need from me?” I asked, followed by a sharp gulp upon remembering the type of suite we were in. “The whole… Wendy thing. That’s done, right?”

“Oh, definitely,” Erica quickly assured me. “There’s a bunch of sweepstakes winners staying at the resort. Some won trips for two and some got solo trips. Was Carter with anyone?”

I shook my head. “He was alone.”

“Perfect. So he’s a solo tripper and as far as he knows, so am I.”

“But hold on. Solo trip?” I clarified. “So what, am I supposed to hide for two weeks?”

Erica put her hand on my shoulder. “Will, have you seen this place? It’s ginormous! You don’t have to disappear. Plus, he doesn’t have to know we’re staying together.”

With so much lying packed into the first day of our trip, adding yet another lie to the pile made me feel icky. Particularly one that directly involved me.

“I was gonna tell you about this before I saw Carter, but I found a little alcove on the beach a quarter-mile down. I took a seat and… I dunno… I got weirdly inspired to write again. Maybe if it’s all it’s cracked up to be, I’ll spend most of my days down there. Finally, you know, doing what a writer is supposed to do.”

“That’s incredible!” she cheered. “It’s perfect for both of us. Heh… you know, in a roundabout way, aren’t we kind of both here for redemption? I’m here to reconnect with Carter. You’re here to reconnect with your creative side.”

I nodded along, agreeing. This whole trip could be about reconnecting – even the two of us reconnecting as siblings. Wouldn’t that be something?

No, Erica hadn’t exactly earned my trust. At least yet. But there’s a difference between deception and desperation, and Erica’s scenario felt more like the latter.

I’m only 23 years old. I have no idea what it’s like to be in your 30s, still single, and yearning for the past. But I can sure as hell empathize with her fear. And the least I can do — even with how uncomfortable it makes me feel — is to cheer her on as she seeks her own redemption.

========

While the reason behind our trip may have changed, it didn’t mean our activities had to. In addition to exploring a bit more of the resort, Erica and I took the chance to read through every guide, brochure, and catalog on the Ocean Oasis resort and the Hawaiian island of Oahu. And the more I learned, the more I felt two weeks wasn’t enough time!

Though Erica and I arrived as equals, we both quietly understood that this was more her trip than it was mine. She won the sweepstakes, she’s here on a mission to reconnect with Carter – my role is merely the travel companion and vacation mooch. But I’m perfectly happy with that. The change of scenery coupled with the island’s energy was already reinvigorating me as a writer.

Our first official ‘plan’ as guests at the Ocean Oasis was a dinner reservation booked at one of the hotel’s seven — yes, seven — restaurants. Erica insisted we start off with a bang and dive right into the island culture with a traditional Hawaiian seafood meal. The restaurant she selected was called Rainbow Kitchen and apparently known for its Hawaiian Yellowtail or ‘Kanpachi’.

“I read that Guy Fieri used to come here,” Erica noted as we were seated at the table. “Surprising considering nothing here is drowned in barbecue sauce.”

“Hmm,” I replied, distracted by the overwhelmingly leafy decor. In some regards, it felt like a Hawaiian Rainforest Café — albeit with a much better menu. The restaurant was pretty crowded too, which made it excellent for people watching. In the middle of our first cocktail, I pointed toward a couple that appeared to be fighting.

“What’s their story?” I gestured subtly. “Your three o’clock.”

“Oh, those two? Hmm…” she mulled, staring at the younger woman and her much older companion while coming up with a story. “They’re on a weekend trip — one she initially didn’t want but came around on. So she put in effort to look good, and now she’s upset that he’s not paying enough attention to her.”

I peered across the restaurant toward the table. Our view was partially blocked by a sprawling plant in the middle of the dining room, but I could see her grab her dress material and shake it furiously as if to say ‘Is this not what you want!?’.

“Damn,” I chuckled. “I think you’re spot-on!”

Erica leaned back, cocky. “I’m an ace. Give me another one.”

Again, I glanced around the restaurant until I found a group of four friends — three men and a woman, all in their 40s. “Okay, do them.”

Erica cracked her knuckles and narrowed her focus. Neither of us could hear, but through expression and body language alone, she delivered her verdict.

“The balding guy is in love with the girl, but she’s dating Green Shirt. He came along on this trip hoping to get her to notice him but he’s too much of a wuss to make an actual move. Either that, or he respects his friend too much to even try. That’s why he’s so sad.”

I smiled and shook my head, deeply impressed. “And what about the third guy? Red Shirt.”

She squinted hard, trying her best to get a read on the man from behind.

“Hmm…” she muttered. “He’s not giving me much… but I get the sense he’s obsessed with his job. Can’t unplug. Ah, look!”

Erica pointed to the man who, on cue, slyly pulled out his phone beneath the table.

“He’s answering a work email. I guarantee it. The guy is a workaholic.”

I gave my sister a polite golf clap, applauding her gift of people-reading.

“You’re really fucking good at this, aren’t you?”

She shrugged and smiled. “I’m a consultant, I travel and work with new people every day. Comes with the job, I guess.”

It was at that moment that I realized something that hadn’t yet leapt into my mind. Was this the first ever solo dinner I had with my sister? I mean, think about it… She’s seven years older than me, so it’s not like we hung out growing up. Sure we ate breakfast or lunch at the kitchen table, but it’s not the same thing as going out for a real meal.

I thought about this more as we chatted and worked through our tasty Kanpachi. She’d always been my sister, but this trip was creating a whole new dynamic. Two adults. Two friends.

“So, this private beach spot,” Erica said in the middle of a bite. “You said it inspired you to write. But write what? Another alien thing?”

“I mean… I guess so,” I answered, though with little confidence. “That's all I’ve ever written.”

She raised an eyebrow and took a sip of her cocktail. “Well, why not mix it up? Write about people for once?”

The way she said it felt like she was mocking me.

“Yeah. If only it were that easy,” I bemoaned.

“I think it is,” she added with a smug look on her face. “Look what I just did. I didn’t know those random peoples’ situations — I mean, I know I’m right… but it’s just made up. Have you ever considered writing about a relationship?”

Immediately I scoffed at her. “Yes, Erica, I’ve considered it. I just suck at it.”

“How come?”

I paused, briefly weighing how much of my personal life I should expose to my sister. Maybe it was the alcohol or maybe I just felt like I owed her some candor.

“Well… I’ve never been in a relationship.”

Erica nearly spit out her drink. “You haven’t dated anyone??”

Immediately I turned red and regretted saying a single word. “Not, like, officially! Okay? So what?”

“Wow…” my sister said, shocked and sinking into her seat. “I guess we do have a lot to learn about each other.”

Ugh. I wish she hadn’t brought that up. Until now the meal had actually been quite pleasant. Though to her credit, I think Erica knew it stung.

“I’m sorry I brought it up, okay? You’re a professional writer. I’m not. But if I can give my two cents... Stories are about people, right? And you can’t sit alone and not interact with anyone and expect to be inspired.”

With our plates cleaned, Erica signaled to our server for the check.

“We’re in Hawaii with a ton of fun, cute people,” she reminded me. “Maybe try meeting some. It could help your writing.”

I didn’t exactly disagree with her, but at the same time wasn’t in the mood to be taking unsolicited relationship advice from the girl who flew across the country for an ex.

However, before I could say anything else, Erica’s face went cold.

“Shit!” she yelped, pointing with her eyes directly behind me. “He’s here!”

“What??” I quickly jumped into full alarm mode. “You mean Carter?”

Erica shot up from her seat and grabbed my wrist. “Yes, I mean Carter!!”

I stared at Erica, not entirely sure what she wanted from me.

“HE’S WALKING OVER! HIDE IN THE BATHROOM!” she whisper-screamed.

I shot up from my seat like it was on fire, juking around the restaurant foliage and scooting into the nearest bathroom which was, thankfully, right near our table.

The door locked, lights off for some reason, I could hear Erica through the bathroom Erica muttering “Shit! Shit! Shit!” to herself as a man’s footsteps approached our table.

“Well, well, well… Erica Quinn!?” Carter announced. “I thought it was you!”

“Carter Harris,” my sister replied, putting on her best, flirtatious voice. “No freaking way. What a coincidence!”

Even though there was no chance he could know I was listening through the bathroom vent, I kept my mouth zipped shut.

“What the hell are you doing here?” I heard her ask, obviously well aware of his circumstances. “Of all the resorts in the world…”

The two of them went on like this for a while re-stating the absurdity behind their run-in, offering loose details on what they’ve been up to, how she’d moved back to Chicago from New York, how Carter started a new job in Dallas… and of course, complimenting how ‘stunning’ one another looked. I found it funny how easily my sister could put on this faux ignorant persona. Though I suppose I shouldn’t be too surprised – she’d done it to me twice already.

It was pretty surreal listening to the two of them talk. Carter, who I’d only seen in pictures, was here in the flesh. Dug up from Erica’s past and, Bam! Right back in her life. I gotta give my sister credit. She made this happen. Not that Carter knows that.

“So tell me,” Carter said after an awkward pause. “Who’s, uh… Who’s here?”

I couldn’t see a thing, but it was clear the conversation had moved to the apparent empty plate and seat right in front of her.

“Oh, who’s here?” Erica repeated Carter’s question, but not like she didn’t hear him. More like she was stalling for time.

You’re kidding me! Erica planned out lies for everything except this? I mean, shit, just say you’re with a friend! But as it turned out, Erica’s answer wouldn’t have mattered a lick.

“Wait,” Carter went on. “It’s Wendy, isn’t it?”

Huh?

“Huh?” Erica echoed my thoughts.

“Yeah,” Carter said. “There was a little posting in the lobby of the sweepstakes winners. I remember reading ‘Erica and Wendy’. Though I didn’t realize Erica was you.

Shit. Shit shit shit! I wanted more than anything to sprint out of the bathroom and reveal myself to him. To put a stop to this Wendy nonsense once and for all. Just cut my losses and chalk it up as a silly misunderstanding. In fact, I did reach for the door handle, but not before Erica put the nail in the coffin.

“Oh yes! That’s right. Wendy’s my cousin. My friend couldn’t make it so I invited her instead. But she’s in the bathroom now. G.I. issues, I think…”

I slapped my forehead with such force that I was genuinely surprised she couldn’t hear me from outside.

Carter awkwardly chuckled at her overshare. “Cool…” he replied. “Well, I hope she’s feeling better.”

“She’ll be fine. Just might be a while! Girls being girls, I guess!”

I never wanted to smack Erica more than I did right now.

“Well, hey, uh… You still have my number, right?” Carter added, sounding like he was on his way out. “Text me. Would love to, you know, catch up and hang.”

“I’d love that!” My sister beamed.

Red face, sweaty palms, and fury in my soul, I spent another 60 seconds pacing in the bathroom before promptly returning to the table where my sister was done paying the check.

“Hey! We’re all cl—” she started but abruptly stopped as she saw the beginnings of my conniption.

“Don’t you dare say we’re all clear!” I shouted, even catching the attention of a few diners. Erica should be lucky we were in public because I. Was. FURIOUS.

It took her a moment, but she looked at the bathroom wall to our right and put two and two together.

“Oh… You heard…”

I nodded stoically.

She shot me a sheepish, embarrassed look. “Maybe I need a little more Wendy time than I thought.”

=-=-=-=-=-=-=-=-=

That's it for the sample chapters unfortunately :( But the entirety of Two Weeks of Wendy is on Amazon right now!

Thanks for reading :)

-Jennifer

AMAZON LINK: https://www.amazon.com/Two-Weeks-Wendy-Gradual-Feminization-...

***FYI This is the second of three chapters that will be shared here on BC***

CHAPTER TWO

Gigi looked at me for a moment, confused more than anything else.

“Shit, did I forget to put the letter in there?”

I didn’t even know how to respond. What the hell kind of surprise was this?

“You… You want me to be…” I stumbled over my words.

“A bridesmaid!” Gigi leaped in to finish my thought. “For my wedding!”

I don’t know how, but I was able to snap out of my stunned disbelief and address her properly.

“Gigi, I… What are you talking about?” I lifted the letter from the box, revealing a whole assortment of goodies beneath it. A bottle of rosé, a cocktail shaker, a candle, assorted chocolates — every bit of it bursting with pink, glittery goodness.

“Colin, I just told you. My wedding’s on the books! This is my way of asking if you’d stand up with me on the big day.”

My head and heart were torn. I was beyond honored that she considered me such a close friend. And to be with her as she tied the knot with Kyle was a deeply humbling thought.

“I mean… I’d love to, but… As a bridesmaid?”

Gigi looked at me, finally recognizing my hesitancy. “Oh, well not a maid, silly! A bridesman. The box just says bridesmaid.”

“Oh…” I said. My heart rate sharply dropped. My nerves returned to normal. “Good, because, you know…”

Gigi sensed the mislabeled box triggered the flighty response she certainly wasn’t going for.

“Check this out,” she began, pulling up a photo collage on her phone and walking me through it. “Bridesmen are pretty common nowadays. Suits and ties match the colors of the bridesmaid dresses, you wear a boutonniere that pairs the girls’ flowers… It’s great!”

She swiped through a few pictures of multi-gender wedding parties and sure enough, they looked quite normal.

As I thought about it more, I remembered stories of acquaintances doing this exact thing. It’s not the 1900s after all. Girls can be close friends with guys. Why shouldn’t they stand up in each other’s weddings?

With the gender issue set aside, a new batch of overwhelming thoughts rushed in. From everything she’d said about her social life and from what I could tell, Gigi was a super popular girl. Out of all of Gigi’s friends, why me?

“I’m… so flattered, Gigi. Like, seriously. But…”

She smiled warmly. “So you’ll do it?”

Again, I was caught in a trance staring down at the glitzy bridesmaid — er, bridesman – box and five-word proposition letter. Why was it so hard just to say yes?

The longer I paused, the more Gigi’s smile started to fade. Her joy turned to concern, which rapidly turned into embarrassment — all for asking her work husband to join her wedding party. Fuck, I needed to say something.

“Gigi, I’m honored you’d want me. But… I feel like you have all these incredible, like, female friends who’d give you everything. Why muck it all up with a guy?”

She stared at me plainly. “Because you’re a really important part of my life too. I love my girls, but I want you because you’re not like them. You’d be such a good addition.”

I hung my head, fiddling with the bright pink cocktail shaker printed with the phrase ‘For the Girls!’. How ironic.

“Look, I understand if this feels out of nowhere, but I’m serious, Colin. I want you to be a bridesman,” she leaned in closer, then gestured widely to the office. “This job’s pretty soul-sucking. You know that as much as me. But hell if you haven’t made this shitty job easier to swallow…”

I couldn’t help but blush, pushing one of my long blonde locks out of my eyes. “I mean, you too.”

Gigi leaned forward to grab my hands. “How about this? My other three bridesmaids are coming to my house Saturday night for a cocktail night. Super chill. How about you come by and see if you fit in with the group. I mean, they’re awesome and you’re awesome, so you totally will — but see how that goes and make your decision then. Sound good?”

It was clear Gigi wanted to make sure I was comfortable. For as quirky and occasionally ditzy as she could be, her sincerity and thoughtfulness meant a lot.

The thought of being a bridesman — particularly my work wife’s bridesman — gave me a good bout of imposter syndrome. But taking it one step at a time couldn’t hurt.

“Drinks would be great,” I answered happily, returning the shaker and letter to the box and packing it away. “It’s a date.”

Gigi reached forward and booped my nose playfully. “That’s the work husband I know.”

Just as she did that, another paralegal stomped into the kitchen, pissy and poised to vent about an assignment he just got. Quickly, I shoved the bridesmaid box under the table and out of sight as Gigi and I let him rant.

Maybe I wasn’t ready for the whole world to know I was considering this. It’ll be weird enough smuggling a glittery pink box out of the office tonight. But I had to remind myself that, despite its appearance, her ask was merely a gesture of friendship. Even if it does feel like a hell of a step.

All I have on the books is a casual cocktail night to meet Gigi’s friends. A simple night where, at the very least, I’d make a few new friends. Nothing wrong with that, right?

========

In LA, there’s no shortage of people who flash wealth like it’s their job. Fancy sports cars, designer clothes, and dinners with tabs that creep into the five figures are staples among that group. On the flip side, you find your humble millionaires. Basic cars, basic clothing — almost so under the radar that unless you put an x-ray to their bank account, you’d never know they were among the elite.

Gigi, I’d say, is somewhere in the middle.

I knew that Gigi not only worked in wildly expensive Calabasas, but she had a nice little apartment in town too with a wonderful five-minute commute to the office. In fact, she’s a born-and-bred Calabasian having attended a local, private high school, then to college at UCLA, only to come right back here to begin her career.

Tonight’s drinks, however, weren’t at her apartment or even at a nearby restaurant. The address she sent me was for a gated community in North Calabasas — the fanciest, bougiest area of the entire town.

‘It’s my parents’ place!’ she reminded me in a text. ‘Give the guard the code and my full name and he’ll let you in.’

I almost spit out my drink reading it. The guard? I knew she came from wealth, but a gated community in North Calabasas never crossed my mind. What kind of house were we talking?

For the entirety of my 45-minute drive from my Burbank apartment, I had swirling visions in my head of what her place could possibly look like. As if I wasn’t nervous enough meeting three of Gigi’s best friends while essentially auditioning to be a bridesman in her wedding, I now had to appear cool as a cucumber in the face of extreme family wealth.

I pulled up to her community’s gate as instructed, nervously reciting the code and Gigi’s name to the gruff, burly guard.

“Hmm,” he nodded, glancing just a tad judgmentally at my crappy, beige Mazda before ultimately handing me a piece of paper for my dashboard and saying, “Come on through.”

I followed the winding road up the hills of her community, passing progressively larger homes. But no, not just homes — mansions. There’s simply no other way to describe what had to be one of the priciest zip codes in the country.

When I finally reached her address, I wasn’t even certain I was there. The lawn itself was twice the size of my childhood home in suburban Chicago. There was a freaking fountain out front and a circular brick driveway, leading up to what I could only describe as the most extravagant house I’d ever seen.

The mansion was massive, towering over the treeline and somehow even dwarfing the other gigantic homes on the block. I could feel sweat bead on my neck and brow as I approached the door and readied my hand to knock on the behemoth front door. But then…

*CREAK*

The giant wood door opened before I even laid a hand on it. From the open space popped out a familiar, smiling face.

“Colin! Eeeee!” Gigi squealed, grabbing my hand and yanking me inside with such force that I nearly dropped the bottle of wine I’d brought as a gift.

“Welcome, welcome!” she leaned in for a hug as my eyes darted around the beautifully decorated cavern of a foyer. “Thank you for making the trip.”

“Heh, sure! Wouldn’t miss it.”

Her eyes traced to the bottle of wine. “Oh is this for me? Thank you!”

I obviously felt foolish presenting a $10 bottle of wine to a family who, by the looks of it, probably owned a vineyard. But Gigi seemed happy nonetheless.

After a bit of chit-chat, Gigi insisted she give me a brief tour of her home. Well, not her home, as she was quick to correct.

I found the space to be as marvelous as it was intimidating. Not only did it have the typical kitchen, living room, and dining room setup, but Gigi’s house had an abundance of single-use spaces like a billiard room, a craft room, and a conservatory. And that’s just the first floor.

Gigi suggested we make a quick visit to her equally sprawling basement — finished, of course — home to an impressively large sitting area, golf simulator, and most notably a wine cellar where dozens if not hundreds of wines were stacked and stored on gorgeous wooden shelves.

“We’re good on red… Let’s grab a white too so everyone’s happy.”

“Everyone?” I repeated. “The others are here?”

“Sure are! We’re just hanging around. Didn’t want to start drinking without ya!”

While I knew nothing about wine, I had a strong suspicion the white bottle she grabbed was at least ten times the price of what I brought. Nevertheless, she treated both bottles of equal importance.

Wine in hand, I followed Gigi back up to the first floor, then up the gaudy, foyer staircase and down the long, second-floor corridor. I genuinely can’t express how much this place felt like a real-life castle both in size and style. I mean, what kind of home has hallways as wide as my living room? And wall art worth as much as my car?

We approached the one open door at the end of the hallway — the only room with a light on. Girlish giggles emanated from inside.

I gulped. “Is that—”

“My friends? Yeah.” Gigi answered, though rolled her eyes. “They better not be messing up my stuff.”

I raised an eyebrow, a bit unclear where exactly we were headed until Gigi again yanked my hand and led me into what was not a lounge, a bar, or anywhere I’d expect to be making cocktails or drinking wine. No, it was her super-pink, super girly childhood bedroom.

“He’s here! Everyone, meet Colin. Colin, that’s Marie, Lizzie, and sitting on the floor rudely not paying attention, Amelia.”

I blinked for a couple of moments, motionless and accepting the strange fact I was in my adult coworker’s childhood bedroom plastered with dated One Direction and Justin Bieber posters. Though mostly, I was distracted by what Amelia, seated on the floor and leaning up against Gigi’s soft pink canopy bed, was doing holding a strange, metal tool.

“Colin?” Gigi nudged my arm. “You good?”

I guess I got caught staring a little too long, because the second Amelia picked her head up, a tiny smirk grew on her face.

“Well there you go, Gigi. Someone’s interested in your old flat iron.”

I finally snapped out of my trance and smiled for the three girls, hoping I wasn’t too impolite. But the damage may have already been done.

“I’m sorry, uh… a flat iron?”

Amelia held the blue metallic tool higher up. “A flat iron. You know, to straighten hair?”

I felt my throat turn dry, self-conscious that, already, I wasn’t fitting in. But that was nowhere near my biggest problem.

Amelia smirked again, tossing the tool between her hands. “You know, Colin, with how long your hair is, maybe it’d be fun to use it on you. Ever straightened your hair before?”

=-=-=-=-=-=-=-=

One more sample chapter coming this week, but the entire book is available right now on Amazon!

Thanks everyone :)

-Jennifer

AMAZON LINK: https://www.amazon.com/Will-You-Be-Bridesmaid-Feminization-e...

***FYI This is the third of three chapters that will be shared here on BC***

CHAPTER THREE

“Ooh! Yes yes yes!” Lizzie cheered before I could get a word in. Marie, meanwhile, sat there rolling her eyes and chuckling.

Of course, I turned red as a beet. What kind of question was that!? Have I — a boy — ever had my hair straightened? But what was I supposed to do, snap at her? Yell at a girl I just met for asking such a ridiculous question?

“Uh, no,” I answered plainly but firmly. “I’ve never straightened my hair.”

I looked over to Gigi who, thankfully, seemed to be on my side with this one.

“Guys, come on. Stop it.” She walked over to Amelia, still on the ground, and snatched the flat iron from her hand. “You’re welcome in my room, but not if you go digging through my old stuff, okay?”

Amelia groaned, annoyed by Gigi’s buzz-killing. She promptly placed it on her bright pink, glittery wooden vanity. The vanity, like everything else in her room, looked like it was bought at a teenage princess’s garage sale.

“Anyway…” Gigi continued. “Colin and I brought wine!”

The girls hurrah'd, eager to begin their Saturday night drinking. Gigi, to my surprise, reached deep beneath her bed, summoning not wine glasses or even normal glasses, but a dusty stack of red solo cups which she distributed to each of us.

“Plastic cups? For wine?” I clarified.

Gigi winked. “What, you’re not a goodie-two-shoes who has to drink from a glass, are you?”

“Oh, uh, no! I just—”

Gigi put her hand on my shoulder and looked me in the eye. “Colin, I’m kidding. You gotta relax. We’re here to have fun.”

“Relax…” I echoed. Admittedly it’s hard to fully relax in a brand new environment — particularly when it’s your coworker’s childhood bedroom in her parents’ mansion. Not exactly familiar territory.

“Yeah, relax! We’re all friends here.” Gigi leaned in. “Or at least, I’m hoping? I mean, that’s what tonight’s all about. See if you vibe with the rest of the bridal party?”

I noticed the girls had begun pouring wine and chatting like nothing was wrong. To their credit, they seemed totally unfazed by the presence of a boy. Why then should I be so uncomfortable around the girls?

Having a moment to reset and breathe helped immensely. I managed to force a smile and address the group.

“Heh, sorry about that. So are we drinking wine or what?”

Marie, a tall, beautiful brunette who must be at least 6’1”, held both open bottles in her hands.

“Red or white?” she asked.

“White please.”

As strange as it felt to sip $100+ wine from a two-cent plastic cup, I knew the little bit of alcohol would do wonders for my nerves. It’s not called a social lubricant for nothing.

“Wanna sit next to me?” Gigi asked, patting an empty spot on her bed.

I smiled and did so, plopping my butt on the bed beside her as the other girls spread out around the room with their drinks.

An inevitable awkward silence fell over the room.

“So… How do you guys all know each other?” I asked simply.

“The club,” Lizzie said plainly.

“Yeah, the club,” Amelia added.

“Same,” said Marie.

I glanced over at Gigi, confused. “The club?”

Gigi looked just as confused. “The country club. Wait, I never told you about Westie?”

I shook my head and shrugged.

“All our families belong to the same place. Westmore Country Club. We call it Westie though.”

“Huh,” I muttered, half surprised I had no idea about Westmore — er, Westie — and half embarrassed I was already such an outsider.

“Our dads all work together. That’s how we met!”

Gigi dangled her feet off the bed like an antsy child. “They’re all in banking. We’ve known each other since we were kids! Thank God, too, because we’re all only-children. These girls were basically my sisters growing up.”

“I’ve spent, like, a million nights in this room,” Amelia laughed. “Some better than others.”

I chuckled along nervously. “Heh, well, I hope this is one of the good ones?”

Amelia smiled back. “So far, so good!”

Over the next hour, I got into a rhythm of asking questions and learning everything I could about the girls, their personal lives, and their friendship with Gigi. Facts mixed with stories that went off on ridiculous tangents, but by the end of it, I had a pretty good sense of each girl.

Like Gigi, all were all in their mid-20s. They went to the same elementary, middle, and high school, and while they went their separate ways for college, all three made the respectable choice to return to their hometown of Calabasas to live and work. Though for how nearly identical these girls were in background, their personalities had some variance.

Marie — who they call the ‘big sister’ of the group because she’s both the tallest and the oldest by a few months — teaches at an elementary school and has an apartment just a few blocks from Gigi. She’s also the quietest and subsequently the most serious. If there’s a moment when everyone needs to chill out or focus, Marie’s the one to get the group in order.

Lizzie I could immediately tell was the spastic one. She’s a hyper, eager, and perpetually upbeat blonde with a petite frame. While I’m sure she could be exhausting at times, I personally found her delightful. She’s always making people laugh and laughing herself. A great personality trait for someone who, as I just learned, works in sales.

Last but not least was Amelia — the most sarcastic of the bunch. She’s fun, upbeat, and armed with a wonderfully dry wit and brutal honesty. Not to mention quite the flirt. I got the sense that if these girls ever got in trouble in high school, it was Amelia’s doing. With her deep blue eyes, long, beautiful black hair, and killer figure, there’s no doubt she can get any guy she wants.

Each of these girls seemed like not only a great person but a great friend to Gigi. And their traits perfectly complemented Gigi’s quirky earnestness. I could see why they stuck together all these years.

Not that their company wasn’t appreciated, but one thing I still couldn’t fully get is why they’d hang out with me — nerdy, scrawny, awkward Colin. Frankly, high school me would’ve done a spit-take if he knew I’d be in a situation like this. Saturday night with four beautiful women? Too bad it had to wait till I turned 24.

Nevertheless, the vibes were good and the night felt like an old-school, high school or college dorm room hang. Friends sitting around, sipping wine, and telling stories.

All of a sudden, Lizzie held up her hand, nearly spilling her wine as she remembered something. “Colin, I feel like we still don’t know you though. I mean, Gigi tells us like nothing.”

Marie sipped, smirking. “She keeps things very close to the vest.”

Gigi turned a little defensive. “What? I tell you guys things! I just don’t feel the need to talk about work all the time. But Colin’s super interesting.”

I smiled awkwardly, feeling the spotlight start to shift toward me.

“Oh yeah?” Amelia asked. “Colin, what’s the most interesting thing about you?”

My mind raced trying to come up with something Gigi-centered we could all focus on, but Gigi jumped at the chance.

“Colin loves mythology. He runs this cool little blog about history and myths from all over the world. It’s called PopMyth, and he’s got, what, a few thousand readers?”

“No fucking way!” Amelia exclaimed. “That’s so nerdy but also, like, so sick.”

Whether or not they were feigning interest, I appreciated the shoutout. PopMyth was my pride and joy and more or less kept me sane day to day. I always felt weird pitching the concept to people who weren’t in the ‘myth space’, but the girls were willing to humor me and were extremely encouraging.

It also probably helped that, by now, each girl had consumed at least three glasses of wine. And by the look of it, the night wasn’t slowing down as Gigi got up to fetch another bottle of wine from the cellar.

“I take it we're no longer doing cocktails?” I asked as she was leaving.

Gigi tilted her head. “Yeeeeah… Maybe best not to mix alcohol. And I don’t know about you, but I’m having a lot of fun right here.”

I looked at her and glanced toward the girls. Against all odds, sitting here in this girly, pink room and drinking expensive wine from cheap cups, I was somehow enjoying the night too. But most importantly, I felt welcomed. I felt wanted.

“Me too,” I said to her honestly.

“Love that. Be right back!”

Gigi scurried downstairs to get us another bottle or two.

Lizzie reached over and grabbed the cup out of my hand. “Just one cup?? Colin, you gotta catch up!”

I laughed. “Hey, I gotta drive home! I assume you’re all staying the night?”

The girls all nodded simultaneously.

“Nothing wrong with a good, old-fashioned adult sleepover,” Marie said.

Merely making conversation, I followed up asking, “And what does that consist of?”

Amelia shrugged. “Honestly? The same as back in high school. Drink too much wine, gossip, tell stories, do each other’s hair…”

Then, Amelia stopped, turning her head back to the vanity where she had over an hour ago placed the bright-blue flat iron.
Shit. I knew where this was heading.

“Uhh… Nuh-uh.” I said, though my voice wavered just enough to get all three girls laughing.

Lizzie, sitting closest to the vanity, picked it up and swiftly tossed it to Amelia.

“Oh come on, Colin. With hair like that, you’ve seriously never wondered what it’d be like to have it straightened?”

My face rapidly turned red like before, but this time Gigi wasn’t here to quickly put a stop to it. And God knows I don’t have the confidence to overrule three beautiful women.

“I, uh… I mean…”

I hadn’t given in but Amelia treated me as if I had, reaching for my hand and ushering me toward the stool at the vanity.

“It’s not like I’m doing anything permanent,” Amelia said as she gently ran her hair through my hair. She viscerally reacted. “Oh! Colin. You’re literally a hairdresser’s DREAM!”

“Wait, you’re a hairdresser?” I asked, now realizing she was the only one who hadn’t gone into detail about her work.

“Five years now. It’s a wonderful gig.” She stepped back for a moment to look at me directly. “So what do you say? It’ll be fun!”

There I sat, looking at my reflection in the ovular vanity mirror, my long blonde hair getting toyed with and tossed by Amelia who stood behind me. Lizzie couldn’t stop giggling while Marie sat quietly by.

God, what was taking Gigi so long? Surely she would’ve put a stop to this.

Or would she? The one thing Gigi wanted out of tonight was for me to get to know her friends in a fun, intimate evening. When in Rome, do as the Romans do. Here, the Romans get tipsy and play with each other’s hair. So who am I to ruin the tradition?

I took a deep, concessionary breath. “Sure. I guess you can straighten it.”

“Yesssss!” Amelia pumped her fist in celebration. “Ah! You’re gonna love it. I promise!”

Amelia started digging through the vanity drawers, scrounging together all the needed products for my hair ‘transformation’.

“Eh, good enough,” Amelia muttered, pulling out an opaque white spray bottle. “Haven’t used this in forever. Remember this?”

Amelia held up the bottle to the other two giggling girls.

“Very 2014…” Lizzie reminisced.

I sat awkwardly as Amelia spritzed my hair and ran a comb through my long blonde strands.

“God I love your hair… Super full. Very healthy.”

“Uh, thanks…” I squeaked, not sure how to respond to a compliment like that. “I mean, I just shampoo and condition like normal.”

“Hey, that’s more than most guys! None of the guys I’ve dated even knew what conditioner is.”

Amelia wasn’t overly chatty as she prepped my hair, quietly listening to Lizzie and Marie talk in the background. I’d never been to an actual hair salon in my life, but I imagine it’s not far off from this.

“Anyone know where Gigi is?” I polled the room.

Marie shrugged. “Probably just got distracted. Wouldn’t be the first time. I mean, have you seen that cellar? This whole place, really.”
The fact that even Gigi’s rich friends found her house wildly impressive made me feel a tad better. Any more time pretending this mansion was ‘normal’ and I might’ve lost my mind.

With my hair prepped and silky smooth, Amelia declared it time for the flat iron. Because I had so much hair, it wasn’t as simple as just running the clamp down my scalp to the ends. So, using a ‘sectioning clip’, Amelia bunched parts of my hair atop my head and tackled one section at a time.

The whole experience felt weirdly intimate. Amelia’s thin fingers carefully gathered and tossed my hair. The mix of her perfume with the sweet smell of the hair spray. The heat from the iron so close to my face as she hot-pressed my messy blonde waves.

For as strange as this whole thing was, I appreciated being in the hands of a professional. This was no amateur, slumber-party hairstyling. Amelia really knew what she was doing. Before I knew it, 10 minutes had gone by and my messy blonde tresses had been transformed into shiny, stick-straight locks.

“What do we think?” Amelia asked softly, stepping away and allowing me to finally touch her masterpiece.

I gasped at first contact. It genuinely felt like I was touching another person’s hair. No way this could be mine, right?

“It’s… really something…” I muttered, now able to effortlessly run my fingers through my hair.

The other girls must’ve finally tuned back in because Lizzie almost lost it.

“OH MY GOD HE’S SO PRETTY!!!”

My head whipped over to her with a grimace. “Pretty?”

Amelia rested her hand on my shoulder, easing the tension. “She means it in a nice way.”

Oddly, Marie was giggling more than anyone. “Colin, you can’t deny you’re pretty. Or, at least that your hair is.”

I couldn’t stop marveling at how soft and shiny my hair was. Not only did it look and feel different, but it moved differently. Whipping my head side to side, I was mesmerized watching the golden strands seamlessly flow across my back and shoulders.

“Colin…?” a voice said behind me.

Gigi had finally returned — a fresh bottle of white wine in her hands and her jaw on the floor.

She wasn’t laughing, or even smiling. In fact, her eye makeup looked a little smeared. And it looked fresh, almost like she’d been crying. Or more likely her makeup just looked that way and I hadn’t noticed until now.

Shit. She’d expressly told us not to touch her things and here I was — well, Amelia — borrowing not only her flat iron, but her combs, brushes, clips, and fancy hair sprays. A pit grew in my stomach and I desperately needed to apologize.

“Gigi, I… I’m sor—”

But her expression changed rapidly, and a smile broke on her face before ultimately shaking her head.

“You let them get to you, didn’t you…”

Suddenly the room erupted in laughter. All four girls dying laughing. Hell, even myself! I mean, the whole situation was pretty insane.
Gigi placed the bottle of wine on the vanity in front of me where she promptly uncorked the bottle and gathered the girls’ cups to refill them.
“I guess if Amelia’s gonna raid my vanity, I’m glad she made you look as good as you do.”

Other than a few follow-up questions and some more teasing me over how shockingly pretty and sweet-smelling my hair was, the evening hang quickly returned to normal. Here I was, sitting at my coworker’s childhood bedroom vanity with newly straightened hair, smelling like a girl, and I somehow wasn’t deathly embarrassed. In fact, I felt quite comfortable. It’s a testament to these girls.

We hung out for a while longer, trading stories while the girls reminisced about their younger years before I eventually needed to head home.
“I’ll walk you to the door,” Gigi said, rising from the bed.

By now, everyone had changed into their pajamas and seemed ready to move on to the movie portion of their slumber party. I turned to the girls who had already nestled into a mountain of pillows and blankets. Marie was hunting for a way to watch Legally Blonde, an apparent favorite of theirs.

“So nice meeting you all,” I announced to the group. “And, uh, thanks for including me in everything.”

“And thank you for letting us mess with your hair,” Amelia said. “You’re a good sport, Colin.”

“And, like, so pretty,” Lizzie added, obviously making me blush.

“Heh, well, uh… anytime, I guess.”

“Be careful what you wish for,” Marie joked.

Everyone chuckled as Gigi led me downstairs and back to the foyer.

I crouched down to put on my shoes only to have my newly straightened hair tumble into my face.

“Ach! It’s so slippery!”

Gigi giggled. “Well, that’s what you get for giving in to my friends.”

I stood up and flipped a loose section of hair over my shoulder. “Eh, I guess it’s not as bad as I thought—” I froze, realizing something. “Wait, it won’t be like this for work on Monday?”

Gigi shook her head. “Just till your next shampoo. Wash it Monday morning and you’ll be fine.”

I breathed a big sigh of relief. Maybe I didn’t mind being seen like this in front of Gigi, but I’m certain the attorneys wouldn’t be as forgiving.
“But you had a good time tonight? Seems like you liked the girls. I know they liked you.” Gigi stuck her hand out to toss the other part of my hair. “And not just cause you let them do your hair.”

“Heh, everyone’s wonderful. No complaints.”

Gigi hung her head, shyly kicking at the air. “So… will you do it then? You’ll be my bridesman?”

For a moment, I’d actually forgotten that that’s what the night was about. Were there some weird moments? Sure. Did I maybe let Amelia get carried away with some of the hairstyling? Maybe. But I really couldn’t have asked for a more chill, welcoming, down-to-earth group. And Gigi’s incredible hospitality wouldn’t be forgotten.

I smiled. “I’d be honored.”

She lunged toward me with a big ‘ol bear hug.

“Colin, thank you thank you THANK you! Yay!! My party’s complete!”

“And thank you for always being so kind to me. Seriously, it means a lot.”

Gigi pulled back and smiled. “You know, not to take up too much of your weekend, but now that you’re officially in the bridal party, Kyle is hosting a little BBQ and pool party thing for the groomsmen and bridesmaids tomorrow afternoon. The girls and I are heading over after brunch. Would love it if you came!”

A pool party? Damn, how do I turn that down? Plus, it’s another chance to get to know the girls in a presumably more sober scenario.
“I’d love to. Text me the details?”

Gigi gave me one last hug but stopped me again before closing the door.

“Colin, I appreciate you being such a good sport tonight. Seriously. That means a lot that you’re willing to put up with my weirdo friends.”
“My pleasure,” I answered confidently. “They’re each weird but wonderful in their own way.”

Gigi looked relieved to hear me say that. “And for what it’s worth, I do love the hair. Even if it gives ‘maid’ more than ‘man.’”

“Well, maybe you just gotta pick me out a suit that looks good with this hairstyle!” I kidded. “Night, Gigi.”

As I buckled up and started the car, I couldn’t remember the last time I felt this… energized. An official member of my friend’s bridal party, invited out on back-to-back days, seamlessly making friends with fun, interesting people — what’s not to like?

Even the new hairstyle didn’t tank my mood. It surprisingly made me feel more part of the group. Crazy, since if you’d told me before tonight that I’d be leaving her house with flat-ironed, flowery-scented hair, I would’ve been too scared to come.

Instead? Well, I’d never admit this to anyone — even Gigi — but I actually kinda liked it.

=-=-=-=-=-=-=

Thank you to all who have read the sample chapters and to everyone who has gone on to finish the book. So happy to report it's been sitting at #1 in the genre on Amazon for over a week now!! Thank you thank you thank you :)

-Jennifer

AMAZON LINK (now available in eBook AND Paperback!): https://www.amazon.com/Will-You-Be-Bridesmaid-Feminization-e...

*FYI, this is Chapter 3 of 3 that'll be shared here on BC!*

CHAPTER THREE: A FEW NEW ITEMS

“I’m sorry, did you just put that up or something?” I said, panicking. “That definitely wasn’t here when I came in last time!”

“It most certainly was,” Monica insisted. “It’s not supposed to be a ‘gotcha’. Simply the rules.”

I stood there for a few seconds, refusing to accept this reality. Did she seriously think I was gonna abide by this?

“Monica, I’m not about to work out in freaking drag, okay?”

She shook her head and put on her best consoling voice. “Oh shush, Charlie. No one’s expecting you to wear a prom dress. This is a gym. Our expectations are incredibly fair.”

I was peeved regardless. “Well, this sucks for both of us, because as you can imagine I didn’t pack any women’s clothing.”

“That’s okay!” Monica said with delight. “We have some for sale.”

“For sa—“ I said, cutting myself off. Jeez, she really thought of everything...

“Look, I’m sorry this is catching you off guard. But you’ve got thousands of dollars in your account, so you might as well spend it, right?”

Another woman walked in behind me and just like the last one, greeted Monica and walked down the hall.

“They’re here for the 7 PM CrossFit class,” Monica said. “You’re welcome to join. Pending your outfit, of course.”

Clearly my hands were tied. Through no fault of my own I had literally thousands sunk into this gym, and I’d already spend $150 of that on a month’s membership.

“I’d rather not have a bunch of people watching me prance around in women's clothes,” I stated.

“That’s totally fine. The Equipment Zone is all yours. It’s usually empty around now. But I’m telling you, the classes are fuuu-uuunnn…”

I didn’t care for Monica’s teasing. “If the Equipment Zone is where I can get the most privacy, then that’s where I’ll go,” I replied reluctantly. “Just… just give me the most masculine thing you have.”

Over the next 5 minutes, Monica presented each eligible item of clothing sufficient for entrance. There was a large variety of leggings, shorts, tank tops, and a few skirts. Desperately trying not to stand out, I settled on the one black tank top and some black women’s workout shorts.
“Great! And assuming your shoes are relatively gender-neutral, those will be fine too.”

I took the clothes into the single bathroom and locked the door behind me. Pfft, some ‘locker room’. There wasn’t anywhere to actually lock my things!

Nevertheless, I took off my button-down, slacks, and other work clothes and stripped down to my underwear. I held up the black shorts in the mirror and audibly groaned at how tiny they were. I’m only 5’2” and they still seemed short! I slid them up my legs and secured them over my briefs. I felt ridiculous standing in this bathroom wearing clothing designed for the opposite sex.

The tank top didn’t help me feel much better. The length was fine, but having never worn women’s clothing before, I was surprised that it narrowed at the waist and widened at the hips. I guess that makes sense given the typical woman’s build… but it looked more than a bit silly on me.

It was undoubtedly a girl’s outfit — no question about that — but I suppose it was as close to androgyny as I was gonna get. I put on my shoes, stuffed my work clothes into my gym bag, and bravely exited the bathroom.

“Fits like a glove! You look great, Charlie,” Monica pointed out as I trudged back through the lobby.

I decided to pretend I didn’t hear her. Monica offered to watch my gym bag for the duration of my workout and directed me down the same hallway I’d seen many women disappear.

There were two doors at the end of the hallway: the women’s locker room on the right, and the door to the workout areas on the left. Since I was clearly not welcome in the former, I took a left.

I’d never really been in a gym before but from the little I knew, I was quite impressed. It was a smaller space, but appeared to have everything you’d need. Machines for your legs, arms, and back, a full rack of dumbbells with various weights, and a fleet of treadmills, ellipticals, and stair machines for cardio. At least I wasn’t getting screwed out of quality.

Just as Monica predicted, the Equipment Zone was empty except for me. But every couple of minutes, a new woman would enter the space and take an immediate left through a door labeled ‘Studio A’.

Studio A was home to the upcoming 7 PM CrossFit class — and, presumably, every other class Iron Athena offers.

I took solace in knowing everyone else was here for CrossFit, so I probably wouldn’t be bothered. But there was one huge problem with the setup: The wall between the Equipment Zone and Studio A was a giant glass window.

If I wasn’t self-conscious enough already wearing a women’s outfit, I’d also be watched like an animal in a zoo. Freaking fantastic…

But I had no line of defense. I could only control my own actions. So I put my head down and got to work on the weights.

While the ladies started their class, I was hard at work on the list of exercises Brendan had put together for me. He’d linked a helpful website with short videos of an instructor demonstrating each lift. So the pattern went: watch the video, test it out with a light weight, rewatch the video to correct my form, then complete the lift.

But damn, was weightlifting hard! Brendan gave me a few weight recommendations, but he was far too optimistic with each, since I struggled to complete even half the reps.

I gave it a solid 30 minutes of effort, but fell significantly short of the goals he set for me. Oh well, I guess you gotta start somewhere.

Last on the list was 30 minutes of cardio. I knew there was no way I’d be able to run for 30 minutes like Brendan planned out, but wanted to give it a try. Well overdue for a water break, I briefly retreated to the water fountain near the door to the Equipment Zone.

“Hey!” I heard a voice say as I leaned down for some water.

I lifted my head up, terrified it would be someone who recognized me. But nope, it was just another woman taking a break from the CrossFit class. And holy shit was she beautiful…

“Are you new? Haven’t seen you around before,” the woman said, a little bit out of breath.

She was glistening with sweat from what looked like an intense 30 minutes. But despite the sweat, her long blonde hair looked beyond gorgeous in a high, feminine ponytail. She had a full face of makeup and a similar black outfit to mine.

“I’m… uh… yeah. I just joined.”

Upon speaking, something must have clicked for her. “I… oh. I’m so sorry,” she stuttered. “I didn’t realize any men came here. I totally thought you were a woman for a second.”

Fuck. This was exactly the conversation I wanted to avoid! I started spitting out nonsense, visibly rattled.

“I… Well, Monica said it was okay. And my company—”

But the woman sweetly chuckled. “Hey, hey, it’s alright! I’m ain’t mad about it. Just an observation.” The woman extended her hand. “I’m Jill.”

We shook. “Charlie,” I said. “Really, I don’t mean to invade your space. I promise I’ll stay camped in the Equipment Zone.”

“Pfft,” Jill said, swatting the air. “Nobody gives a crap about that. We just don’t want aggressive, toxic men runnin’ around. You look like you wouldn’t hurt a fly.”

I shrugged and blushed. It wasn’t exactly the compliment I wanted from a pretty woman, but I took it. Plus, with Jill’s cute, subtle southern accent, it came across sweetly.

“By the way,” I gestured to my clothing. “I’m only wearing this to follow the dress code. I don’t usually…”

She held up her hand again. “Trust me. You’re fine. Any guy who’s willing to follow our dress code couldn’t possibly be a problem.”

I stepped aside so Jill could take a sip of water.

“Seriously, welcome. Consider joining a class sometime! Monica owns the gym, but I teach all the classes — I’d be happy to introduce you to some of the regular girls.”

“Oh, you… you teach?” I stammered. I was trying so hard to avoid peeping through the glass wall that I hadn’t even noticed she was leading the class.

“Mmhmm!” she said with a smile. “Good money on the side, and I love doing it.”

Jill returned to the studio and took her place back on the elevated surface in front of the class. Wow… what a girl…

Hopping on the treadmill, I felt a lot more at ease than I had over the previous 30 minutes. Jill’s welcoming attitude actually did wonders for my confidence. Not’ 30 straight minutes of running’ confidence, but enough to get by.

The treadmills faced directly toward Studio A through the glass, so I had the displeasure of witnessing the double takes from the ladies as, I presume, Jill casually dropped that it was not a woman in the other room, but in fact a man. Though on the flip side, not a single one ran out of the gym in fear, or laughed their butts off at the fact I was wearing women’s workout gear. It was somewhat curious, but overall… accepting… reception.

Still, I feared any interaction with them, so I hung around on the treadmill until the class was over at 8. Other than a few glances my way — and one friendly wave goodbye from Jill — I was largely ignored by the women. Frankly, I’ll take it for the first day. After all, Jill’s super cute and it felt nice to get attention from a girl for once.

I scooted out the Equipment Zone and down the hallway to minimize any interactions with other female patrons. Monica was at the desk, waiting for me with my bag.

“Sorry we don’t have showers for you… Are you okay to go home all sweaty in your work clothes?”

“Yeah, it’s fine. Thanks.” I stopped for a sec and looked at my shorts and tank top. “You don’t want these back, do you?”

“Why would I?” Monica seemed confused. “You bought them, didn’t you?”

“I mean… I guess I did…”

She started to chuckle. “Then I guess you’re the proud owner of some women’s workout clothes!”

I rolled my eyes. Not the way I wanted to view things.

“You know,” she continued. “If you plan on coming back, you won’t want to do laundry each time. Would you like to buy a few more outfits?”

The idea of willingly buying more women’s clothes felt crazy. But Monica had a point. Was I seriously supposed to wash my same outfit each time? That’d be quite tedious.

“Since I got all this credit… Yeah, sure. Get me a few more of the plainest outfits you have. Something black, please. I’m not trying to stand out.”

She made a note on her computer and promised they’d be ready by the next time I came in.

I changed real quick and got back on the train home. Somewhere along the way, my phone dinged with a text from Brendan.
‘Good first workout? Feeling sore yet?’

I laughed to myself, thinking about how brutally I’d be roasted if he knew about the dress code thing.

‘Went great. Thanks for the tips. Keep sending ‘em, and I’ll keep doing ‘em!’

========

Last night's texts didn’t fully satisfy Brendan the next day at work. In fact, he wanted to hear all about the gym space, how I handled his exercises, and most of all if I’d talked to any cute girls.

“It was good. Really. Not much to say. Nice space, nice people. It’s clean… Not sure what else you want me to say?”

Brendan was clearly bored, spinning around in his chair. “So you said there was one particular girl. What’s her name?”

Ugh. Did I really have to go into this?

“Jill. Her name was Jill,” I spat out reluctantly.

“Ooooooh, you gonna bang her?” Brendan teased.

I blushed, definitely trying to avoid this type of conversation. “I don’t know, dude. Maybe she’s not into me.”

He smiled coyly. “Well, you’ve got literally zero competition. So if not her, you got the entire field.”

I hoped this wasn’t a sign of things to come, where I’d constantly be dodging questions about girls. Did I have a crush on Jill? Yeah, a little bit. But the last thing I wanted was to talk about her too much and let an embarrassing detail slip out. It’s humiliating enough attending a girls’ gym, much less having to wear women’s clothing — regardless of how androgynous it may be.

========

All week, I tried my best to avoid deep gym discussions with Brendan. I could tell he was a little disappointed with my lack of engagement, though it was worth it to not spill the beans.

But maybe fate hadn’t had enough of me lately because in the middle of work, I noticed a message arrived in my personal email inbox. I casually clicked to the new tab, and noticed it was from Iron Athena.

Immediately, I got a little nervous. Even if it’s just some dumb promotional email, I didn’t want any chance the whole office could see me browsing the website of a women’s gym.

But my curiosity outweighed my judgment. I opened the email. It wasn’t promotional. It was from Monica. It read:

‘Hey Charlie. I took the liberty of selecting some new clothing items for you to wear for future workouts. We had no more black sets of the shorts or tank tops, so I went ahead and made an order. Super high quality stuff. Two black, one pink — just because I think you’ll look good in it! Pick it up next time you’re in. - Best, Monica’

Right off the bat I was pissed. Seriously? I asked for black, and she got me pink? It’s like she’s wasting my money! But as it turned out, the color was the least of my worries.

Monica pasted a link at the base of the email. A link from the clothing supplier. And upon viewing the webpage, I nearly unplugged my desktop out of sheer terror.

The items she’d bought me? Three undeniably feminine, double-strapped, backless activity dresses.

========

That's it for my sample chapters of You'll Fit Right In, but the entire 26 chapter novel is available on Kindle eBook and in Paperback! Y'all are the absolute sweetest, and I appreciate your support so much :)

Check out my website for the latest updates on upcoming stories: https://www.jennifersweetbooks.com

Amazon Link: https://www.amazon.com/Youll-Fit-Right-Gradual-Feminization-...

*FYI, this is Chapter 2 of 3 that'll be shared here on BC!*

CHAPTER TWO: A HUGE MISTAKE

No. Freaking. Way. Did my company really just sign me up for a women’s gym?

I had a million questions and a billion concerns. So forget the giant line of people waiting — I cut right in front to confront Celine.

“Uh, excuse me?” I said more than a little assertively, holding up the card in question in front of her face.

Celine paused. She examined the card. Then looked at me. Then back at the card. Then back at me again. It took longer than I’d like, but she realized that despite my short stature and long brunette hair, it was indeed a man in front of her holding a $3000 credit for a women’s gym.

“Oh...” she looked at me, awkwardly.

========

“Isn’t this fucking ridiculous?” I shouted. It was almost the end of the work day, and I’d been venting to Brendan for several hours now. I didn’t care if either of us were distracted from work. I was pissed off.

I had explained to him that after confronting Celine, she played dumb and claimed she didn’t remember our brief interaction, jotting down the information of exactly which gym I wanted to sign up for. Of course, she then deferred to her department head, but she failed to admit any guilt.

Celine’s boss, a woman named Vicky, brought me into her office both to calm me down and deliver the news that because the purchase had already been made and I signed the forms indicating this was where I wanted the money to be spent, that there was nothing the company could do. There would be no additional $3,000 credit to spend at Iron Arena or anywhere else.

The only option I had was to beg the management at Iron Athena for a refund — a task which HR had quite bluntly assigned to me.

“I’m sure you’ll be fine,” Brendan assured me for probably the 50th time. “Just go to that girly gym and say it was a mistake. Once they realize you’re a dude they’ll obviously give you your money back.”

There was no choice but to believe Brendan’s plan would work. Small businesses are generally pretty lax on this stuff, right?

I slouched back in my chair, beyond frustrated by the whole situation. A stressful, annoying chore like this was not how I wanted to start my weekend.

========

At the conclusion of the work day, while everyone else was going out to bars, seeing friends or family, or relaxing at home, I was trekking over to a gym I did not sign up for to beg for a $3,000 refund.

While both Iron Arena and Iron Athena were on Halsted Street, Athena was several miles uptown. I was seething with frustration the entire train ride north. And yes, the irony of a wellness stipend causing this much stress was the worst part.

After what felt like hours, my phone navigation finally led me to the sleek but subtle exterior of Iron Athena. Gleaming, pink metallic letters spelling out “Iron Athena: A Gym for Women” protruded from the building, which was sandwiched in between a currently closed antique store and an empty property with a commercial lease sign.

Stepping inside, the lobby looked normal enough. Normal decor, normal everything. A lone woman in her 50s sat at the front desk, busy on her computer.

“Hi…” I said, cautiously approaching her. She looked so zoned in that I didn’t want to spook her.

“Onnnnne second…” she uttered, focused intently on typing something until finally looking up. “Hello! So sorry,” she replied.

“What can I do for you?”

“This is gonna sound weird, but I work at this company called Attention Marketing Agency, and they just started up a ‘wellness stipend’ thing. It’s basically–”

The woman cut me off. “I know what that is. We get a lot of signups from those.”

I nodded, continuing. “Well, my company accidentally signed me up here for it. They made a $3,000 credit purchase…”

Her eyes finally lit up with familiarity. “Oh, that was you?”

“Yes! And as you can see, I’m a guy, this is a women’s gym… I’d like a refund please.”

But the woman kept giggling… and giggling… and giggling…

“I gotta say,” she managed to muster between laughs, “I haven’t been in the business world very long, but that is hilarious. I’m so sorry this happened.”

“Yeah, I know. It sucks. So you’ll issue the refund?”

But the woman’s smile disappeared. “Oh… I’m terribly sorry, but we don’t offer refunds. It’s the policy we set up when Iron Athena was founded.”

I audibly groaned. Probably louder and ruder than I should have. But I managed to compose myself. “Look… I’m sure you have some policy written down that says that, but can’t you make an exception? None of this was my fault.”

She shrugged back. “We’re a business. We need to make money. I’m really sorry.”

I couldn’t believe what was happening! Was I seriously about to be out $3,000 just because of a clerical error that wasn’t even my fault? I wanted so badly to scream, but I knew it wouldn’t solve anything.

“Fine…” I replied through gritted teeth. “Thank you for your time…”

I turned around for the door, but the woman had more to say.

“I truly do feel bad for you,” she added. “Maybe we can work something out?”

I turned around. “Like what? Maybe half my money back? 75% maybe?”

“How about 100% access to the gym,” she said.

Huh? What was she talking about?

But the lady was serious. “Just purchase a membership.” She pulled up something on her computer. “Charlie Lansing, right? It’s showing you have $3,000 worth of credit in your account, so you might as well use it.”

I was totally thrown off. “But… this is a women’s gym.”

“Well, Illinois does have a law permitting single-sex gyms, but I never technically registered ours as one. There’s a mountain of fees and it’s a whole annoying process, yada yada yada…”

“But it literally says on your building ‘A Gym for Women.’ What are you talking about?”

“Yeah, it’s called ‘branding’. Plus it keeps out all the douchey gym bros that everyone hates. You don’t strike me as one of those.”
She might have meant that as an insult — referring to my shrimpy frame and long brunette hair — but I tried to take it as a compliment. Regardless, what she was offering was… bizarre. Frankly, this whole situation was.

“I… I’m sorry. No offense, but this is… insane,” I declared.

She chuckled. “Hey, I’ve never had a situation like this either. But the membership’s here if you want it. Think it over!”

I acknowledged her offer but had very little intent to think any further.

“I’m Monica, by the way,” she added.

“I’m, uh, Charlie. But you know that.”

Monica smiled. “Nice meeting you, Charlie.”

I backed out the door, significantly more confused than when I arrived.

========

I was fully expecting to be roasted by Brendan by the time I got to work. After all, why wouldn’t I be? Monica straight up looked at me and, full-well knowing I was a man, offered me a membership at a women’s gym.

And that’s exactly how I explained it to Brendan. It was embarrassing, sure, but I felt like he needed to know.

“Really…” Brendan leaned back in his seat, respecting my attempts to keep this matter somewhat private. “So what’d you do after that?”

“I left! What else was I supposed to do?”

“Fuck… I’m so sorry man. I guess it’s the company’s money, so it’s not like you’re losing anything.”

“I mean, I’m still losing opportunity. It’s three fucking grand!” I was struggling to stay quiet.

“Why not just pay the Iron Arena fee? It’s another $250 per month, but…”

“I can’t afford that! That’s the whole point of the stipend!” I dug myself further in my chair.

Brendan looked at me, thinking. I could tell he was disappointed. He was losing a potential workout buddy and, I assume, the chance to really grow our friendship.

“Maybe you just do it,” he said bluntly. “What’s the worst that can happen?”

I stared at him. “You can’t be serious. It’s a women’s gym.”

“Maybe that’s a plus? You get to meet chicks. Not like you’re dating anyone right now, right?”

I turned a little bit red. I never told him this, but I’ve… never actually dated anyone before. Sure, a college party or two I’d kissed some girls, but it wasn’t really a priority for me. And not like they were clamoring for me, either…

Brendan stayed firm on his point though. He explained that while girls are often overwhelmed by dudes checking them out at normal gyms — not to mention vastly outnumbered — perhaps a safer environment like this would actually be helpful.

“It’s like playing on Easy Mode,” he explained, twirling his pen in his hand.

Hmm… Easy Mode does sound pretty good…

========

I thought long and hard about the pros and cons of Iron Athena. I liked the idea of an easy intro to girls. I wouldn’t have a wingman or anything to help me out, but there’d ideally be zero competition. How could I lose?

But even beyond the promise of a pickup, the possibility of getting in shape was still enticing. Maybe even joining a different gym, I could still grow closer to Brendan. Just because we’re at separate locations doesn’t mean we can’t share results and encourage each other.

By the time I’d gotten home from work, I’d pretty much made up my mind. I got on the phone and called Iron Athena.

“Hello?” a woman answered. I recognized her voice as Monica.

“Hey, Monica…” I began, but she cut me off.

“Charlie! Good to hear from you,” she replied, to my surprise. “We… we don’t get a lot of guys calling, so I remember your voice.”

“Heh… yeah… So I, uh… I decided to try out a monthly membership. Do you guys do that?”

“We do! Oh, I’m so glad you’re interested.”

“Well, ‘interested’ isn’t exactly right. More like ‘desperate’. I’d still prefer the refund…”

Monica laughed. “Sorry, still off the table. So will we see you tomorrow?”

I remembered Brendan saying he planned to work out on Wednesdays, and tomorrow was a Wednesday. It’d probably be his first day at Iron Arena too.

“You know what? Yes. I’ll see you tomorrow.”

“Great! Can’t wait to show you around.”

She hung up. As nice as it felt to have closure, it felt just as strange locking everything in – a month’s membership to a women’s gym.

========

Besides informing Brendan of my decision and briefly going over his guidance list of exercises to do, there wasn’t much fitness talk. Honestly, I was a little nervous, so it was nice to keep my mind on work.

Once the work day was over, I hopped on the L Train and rode it all the way up to Wrigleyville, the neighborhood housing my fitness studio for the next month.

Just as before, I walked into the building with the flashy pink sign and noticed Monica hard at work at the front desk. She looked up from her computer with a big smile. I could tell she recognized me — again, likely because I’m the only man she’s interacted with all day.

“Charlie! Welcome! So happy you actually came down,” she shouted out gleefully. “I’ll be honest, I was thinking you’d change your mind after the call.”

“Yeah… look, I appreciate your flexibility, but I promise to stay out of your way.” I held up the gym bag I’d packed. “Just, uh… just show me the locker room, I’ll figure out the equipment myself, and I’ll be in and out.”

Monica’s lips pursed, thinking. She looked at me, then looked at my gym bag. “Hmm… so, two things to mention…”

Monica stepped aside from the laptop, greeting a woman as walked in the door behind me. The woman walked straight down a hallway to the left of the front desk.

“First of all, we don’t exactly have a men’s locker room.”

I rolled my eyes. Of course this was gonna be a whole thing. “The men’s restroom is fine. I’ll make do.”

“Well, it’s a gender-neutral restroom,” Monica noted, then pointed to the one bathroom right off the side of the lobby. “But essentially the same. You can change in there.”

“As long as it’s got a lock on the door, it’ll do,” I thanked her and started walking toward the door. But she halted me.

“Uh, there’s one more thing about our gym… We have a dress code.”

Was she blind? I held up my bag to remind her I brought a change of clothes. “I’m all set, thanks.”

But Monica shook her head. She was pointing to a chart on the wall that I somehow failed to notice.

In big, pink letters — much like the ones on the building — read ‘DRESS CODE’. Pictured underneath were three fitness models. Female models.

Monica looked me straight in the eye, but I already sensed the bad news coming. “Skirt, shorts, or leggings. Plus a tank top or sports bra. No exceptions.”

========

I'll be posting the first three chapters of this novel here on BC over the next week or two. I hope you all like the first two chapters! I'm endlessly grateful for your support.

Amazon Link: https://www.amazon.com/Youll-Fit-Right-Gradual-Feminization-...