It had been a few days since I hung out with the boys and I was awoken at nearly two a.m. to a response from Isabella about my question.

 

I’d love that! We can talk more about what you are looking for in person, how’s the 27th work?

 

I, of course now feeling extremely nervous, responded to her message in a tired stupor.

 

That works for me thx

 

I didn’t see her follow up message until the morning.

 

You should totally wear that sundress you got during our last shopping trip! If you are comfortable with it, obv, if not it’s totally cool!

 

That last text filled my mind pretty much every waking moment until the day would finally arrive. I stressed about it day in and day out, on one hand I really really wanted to wear it but on the other I still didn’t quite feel like I deserved to wear it yet.

But then again, if I was trying to test all of this out wouldn’t it make sense to wear it out in public? If anything goes wrong Isabella is there to help me. But her seeing me in that sundress sounds… both amazing and terrifying.

The days all seemed to melt together while I was waiting for the shopping trip, I continued to grow accustomed to bathing and getting used to pretty much everything I do daily in this body. By now it had been so long since I’d been in my previous form that this was starting to feel quite a bit more natural to me.

 

Of course eventually the day had finally come, I found myself standing before my bed with two outfits laid out on it, debating internally which I would wear. One was a more casual outfit that I had already worn numerous times before, of course the other was the sundress. 

I knew that Isabella was due to arrive pretty soon and I was still standing here in my panties not sure what I was going to wear! The words kept playing in my mind though ‘jump into the abyss of femininity’. In a few short days I’d have another appointment with Dr. Samantha, trying this on in public, letting myself be seen as a woman… that seemed like a valuable next step for me. It was a crucial step in figuring out just what in the world was going on in my head.

With my classic burst of confidence I flung the dress up over my head and slid into it before I could even have a second thought. By the time I realized what I had done the dress was already on, a bit of a chill ran up my spine at the continued thought of everyone seeing me like this.

 

I walked over into the bathroom to get a look at myself again in this dress. Even though I was used to my face and body by now something still felt so surreal about it when I stared deeply at myself. It was hard to believe the pretty girl looking back at me in the mirror was… me. Or rather, that she was Robyn. Of course I was also Robyn… No, no, Robyn is just an alter ego for this experiment!

That was my latest denial mechanism, viewing this all as some elaborate roleplay allowed me to feel a bit more comfortable with all of the girly things I was doing.

While I was still deep in thought about all of that, suddenly there was a knock at my front door that made me involuntarily gasp and yelp! Now sufficiently embarrassed I slowly made my way over and swung the door open, turning my head away before I could see Isabella’s reaction.

 

“Oh wow” she almost sounded stunned

“H-huh?” I said but didn’t look back at her, my face slightly red

“I was just a little caught off guard” she giggled, “you look beautiful”

“Wh-whaa?! tH-THAT! I! I!” I stuttered and stammered, immediately nearly falling backwards from the shock of what she had said.

I could tell by the familiar burn on my cheeks that my face was well beyond a deep blush.

“Y-you c-c-ca-can’t j-j-just say that!” I stammered out in a yell, hiding my face behind my hands

“I can’t tell you a factual statement?” I could tell she smirked when she said that by her voice

“NNnnnn…” my whine was the only response I could muster, in my embarrassment I started to retreat.

 

I started to slip as I was retreating backwards into the apartment yelping as I did so with a clearly shocked look on my face. To my surprise Isabella reached out and caught me just before I fully collapsed. Before I knew it I felt her big strong hands holding me as she very easily lifted me back into a standing position.

“You alright?” she asked, crouching a bit to meet me eye to eye

“U-Uhhhh… y-ye-y-yeah” I said with my face burning red, my eyes wide open and my heart beating in my ears

“Good, you should try and be more careful” she sighed while letting go of me, “Now come on, get some shoes on and then we can head out!”

I nodded and grabbed a pair of cream toned flats, slipping into them rather easily and following her out of my apartment and downstairs to her car.

 

Isa’s car was an older truck that was fairly beat up but still ran like a dream. She had that car for as long as I could remember, since it belonged to her mom before her. I got up into the passenger seat and awkwardly fiddled with my hair while she started driving towards the mall.

“So, what kind of makeup are you thinking of trying out?” she asked once we were well on the road

“Uh… I don’t know honestly… probably pretty subtle?” I replied while looking out the window, “at least to start with”

“Yeah, that makes sense, we can get you some of the basic easy stuff and I can help you put some of it on” there was a slight pause, “after that you should probably practice it yourself over the next couple of weeks so you can get better at applying it”

“R-right… did it take you a long time to figure it all out?”

“Eh, probably not any longer than normal for girls” she shrugged, “of course I wear quite a fair bit of makeup so I think I’m pretty good at it by now”

“Yeah, I think it looks good on you” I said without even thinking, the embarrassment catching up to me right after!

“Heh, glad you approve cutie” she smiled but kept her eyes on the road.

 

Surprisingly we were in and out of the store rather quickly, Isa immediately picked up what seemed to be a rather simple and basic starter kit for makeup and we immediately went straight to check out. It was there I had finally realized a grave error I had made, my dress didn’t have pockets! So I hadn’t grabbed my phone or wallet on the way out!

“Oh… shit…” I said under my breath

“Hm?”

“I uh… forgot my wallet… could I just give you cash once we get back?” I asked

“Nah, I’ll cover this for you” she smiled at me, “you’ll quickly realize how expensive this stuff can be, so at least to get you started I’ll buy you this”

I didn’t even realize it when I was looking for my wallet but she was already in the process of paying, so it’s not like I had much of a chance at all of arguing back with her about it.

“Y-you don’t have to do that”

“You’re right, but I want to” she then patted my head, reminding me of the height difference between us

“H-hey…” I shyly looked away from her but didn’t move my head away from the pats, “that’s embarrassing…”

She just giggled in response and suddenly we were heading back to the car to get back to my place. All in all our trip probably took less than half an hour, of course now the real trial would begin. The whole way up the stairs I was consciously holding the hem of my dress, worried about it swaying too much and exposing my panties. Of course it was fairly long so that wasn’t much of a concern but still.

 

When we got back into the apartment I was honestly kind of surprised, after the initial shock of Isa’s reaction to my dress I wasn’t really freaked out by it, probably because she was with me the whole time but still. It was quite a relief to have that trial out of my way, now I could focus all of my attention on the new trial of femininity!

“Alright, I figure we’ll do these one at a time so you can get a look at yourself with it on before I apply the next thing” she explained while opening up the box of makeup

“Th-that sounds like a plan…” obviously I was still highly nervous.

I took a seat on the couch and crossed one leg fully over the other, the very feminine way of crossing my legs that I had always wanted to be more comfortable sitting in. Without anything between my legs it felt infinitely better than it ever did before in my life. I was so preoccupied with those thoughts that I hardly noticed Isa getting pretty close to me.

She was on her knees on the ground in front of me, holding a… tube of some sort?

“I think this would be a good one to start with” she said while pulling out the strange… brush thing, “it’s mascara, it’ll probably feel pretty uncomfortable the first time you wear it”

“Wh-what do you need me to do?”

“Just hold still for me is all” she got even closer to me.

 

I can certainly say the feeling of mascara being applied was not a feeling I at all was prepared for. It didn’t feel bad per say but it certainly felt alien to me, throughout all of my life I’d never paid much mind to my lashes. I know my sister was rather proud of her lashes since she had always said as much while we were growing up but I suppose I never really got invested enough to check my own eyes and see how mine looked. Once it was fully applied to all of my lashes, blinking felt a bit off.

“Alright, that should do it I think” she was looking rather intently at my eyes, or more accurately my eye lashes, “go and take a look”

I nodded and got up off of the couch, straightening out my dress and walking over to the bathroom mirror to see what I looked like.

It certainly popped, that's for sure, they looked a lot thicker and fuller as far as I could tell. I wasn’t super knowledgeable on what each piece of makeup was meant to do specifically but it did feel like it helped my eyes look a bit better? I spent some time moving my head around and looking at myself from a couple of different angles to see while all the while my cheeks were turning pink.

 

“I think it looks good” Isa’s voice nearly made me jump out of my skin, I was so focused that I didn’t even notice her walk into the door frame!

I yelled while dramatically putting my hand over my chest. My yell even caught her off guard as I noticed she jumped slightly at the same time.

“S-sorry…” I said with an awkward giggle, “I was… just focused”

“Oh no, I should be saying sorry to you” she awkwardly giggled back, “I figured you heard me approaching you”

“L-let’s just get back to it” I said, to which she nodded and we walked back over to the couch to start the next step

“So, what color of eyeshadow would you like?” she asked while holding up a pallet

“Uh… how do I know which one would look good?” I cocked my head in confusion

“Well, since you’re wearing a pink sundress, maybe a lighter pink color would look good” she pointed to the tone on the pallet, “it’s a bit subtle but I think it should compliment your outfit”

“Then let's go with that one” I nodded

I may not have known much about makeup but I at least knew that I had to close my eyes so she could properly apply this one. The feeling of the brush against my eyelid was yet another foreign sensation for me, it didn’t feel quite as weird as the mascara did but it was certainly just a tad bit more forceful than I was expecting.

Eyeshadow was one of the types of makeup that I had especially been looking forward to. I remembered my sister usually tried some pretty creative color schemes with her makeup when we were younger, I was always so jealous of her for that. 

“Alright, that should do it for that” when I heard her say that I opened my eyes back up, “Yeah, that looks cute”

My body tensed up a bit when she said that, growing red again, I wanted to argue back but honestly I was too curious to see how I looked with this on to fight against her on it.

 

I quickly got up to my feet and half ran to the bathroom, partially from excitement and partially from embarrassment. I could hear her giggling slightly as I did which really only embarrassed me further and made me feel even more weak in the knees.

But when I took a look at myself in the mirror I couldn’t help but agree with her assessment. It did look… rather nice on me, I felt like my bright green eyes were really starting to pop with this look. Out of paranoia I didn’t allow myself to get as enthralled by my reflection as last time so I managed to step away without having the life scared out of me.

I awkwardly made my way back to the couch and sat down silently

“Well? What do you think?” Isabella asked with bated breath

“I l-like it… I guess” I didn’t look at her as I answered though

She snickered in response, “glad to hear it! Now, let’s try the next thing”

She had another tube of some kind in her hand, though this one wasn’t the same as the mascara. 

“This one will go on your lips, it’s a pretty subtle lip gloss but I think it suits the kind of look you’re going for” her knowledge was certainly impressive

“I’m… surprised you know this much? This is a bit different from your style isn’t it?” I asked shyly

“What do you mean?” she asked while taking the little… brush thing? Out of the tube

“Like, your makeup is usual more dark or purple, but you know exactly what to do for mine even though it’s a lot lighter”

“Oh, that? It’s not that impressive” she shrugged, “now keep your lips still for me”

I did as she said and didn’t answer while she was applying the gloss to my lips.

“I mean, I’ve dressed more traditionally feminine before” she put the lip gloss away, “I didn’t realize this was my real style until I was a teenager after all”

“My style is traditionally feminine?”

“Well yeah, a pink sundress is about as girly as it gets” she giggled, “now go take a look and let me know what you think”

I nodded and did just that, walking over to the bathroom mirror yet again.

 

Girly huh? I-I guess Robyn can be pretty girly… I shook those thoughts out of my head and looked at myself in the mirror again. The gloss was pretty subtle as well, much like the eyeshadow, but it did make my lips look quite a bit better. I believe I had always had somewhat more plump lips than the average guy and turning into a woman only made them stand out even more. They weren’t like… dramatically big or anything, it definitely didn’t look like I had work done on them, but they were very… nice?

This time I heard Isabella walking before she even said anything.

“I’m coming over to you” she called out to not frighten me again

“Alright” I called back

She stood in the doorway and looked at me in the mirror, “What do you think?”

“I… I like it” I couldn’t contain a slight smile from appearing on my lips

I could see in my peripheral vision in the mirror that she also smiled, “that’s good, to be honest I was a little worried I’d mess it up for you”

“Not at all, you did great!” I turned to face her and smiled fully

“I’m glad I could be a help to you” she crossed her arms and leaned against the doorway, “You’re quite the girly girl, you know that?”

“I!... uh… w-well… you-you’re not wrong I guess” I knew I couldn’t really argue considering what I was dressed like

“I think it’s fitting for you”

“H-huh?” the blush was back yet again

“Just sort of your general vibe” she shrugged, “You’ve always seemed cute and feminine to me”

“Al-always?!” I gasped and dramatically stepped back

“Absolutely, though we didn’t really talk all that much before” she sighed, “you always did look sort of sad, but now? You’ve been smiling so much more”

I couldn’t muster up a response, I just stammered a bit awkwardly with my heart in my throat and my face flushed cherry red. 

“This may sound a bit weird coming from me but, I’m proud of you Robyn” normally I’d consider this to be a tease or a joke but her tone was too genuine for that

“Uh… th-thanks?” despite how nervous I was I could feel a happy warmth spread through my body

Isabella sighed with a smile on her face, “Well, I’d say we could try putting some blush on you but you’ve pretty much got that part handled”

“Wha?! I! I…” her pointing it out only made it grow stronger, all I could do was turn away from her.

 

The two of us hung out for a little while after that, just talking about more casual things like shows and gaming. It was a little strange how quickly I was able to act like this was all so normal in spite of my body and how I looked.

Eventually though it was time for her to leave for the day, so she gathered her things and stood by the doorway.

“It was great seeing you again Robyn” she smiled and pulled me into another hug

“Y-you too” I whimpered out while hugging her back awkwardly

She then released me and looked me in the eyes, “How about we hang out again next month? Maybe we can go and grab some dinner?”

“Oh that sounds nice!” I said back, still sort of reeling from the hug

“Awesome, I’ll text you later with the details” she grinned

“Sounds good, just let me know, I’m pretty much free whenever”

“It’s a date then” she said in a teasing cocky voice before leaving, leaving me in a shocked silence.

 

A…A date?! Wait… THAT’S what she was asking? She wants to go on a date with me?! Did she mean a date date or just a friend date?!

I spent the rest of the night reeling from that revelation… I’d certainly have a lot to discuss with Dr. Samantha in our next appointment.

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Been awhile yet again, I'm pretty rusty so I hope this chapter was good. Just to fill you all in I was in a little bit of a rut and my good laptop is currently broken. But I had an influx of inspiration to write so I painstaking wrote this all out on a 10 year old laptop that can barely handle a browser, lol.