Taking a break from doing studies (or, more accurately, slacking off from doing them), Johnathan had booted up his Yboy to play a few rounds of Call of Honor with Pete and a couple of other friends from high school. As usual, he wasn’t doing great, not being as dedicated to the ‘craft’ as the others. They all mostly planned to coast by on their families’ fortunes, slacking at the various business degrees they were getting. So they spent many hours a week playing, while he did make some efforts to improve his portfolio to get into the California School of Art. Most nights, at least.

“You’re doing worse than usual, Johnny,” Andy announced over their voice chat.

“Yeah, yeah. I can see my score too,” he mumbled in reply.

“Seriously, though... is something up?” Pete asked. “You seem a bit distracted. Did you finally find out your prison sentence for drooling over that orc-icorn chick?”

“Kobaroian,” Johnathan hissed. “It’s not polite to call them orcs. Or orc-icorns. Or any of those other things...”

“Whatever. So, what happened?” Pete asked.

“Yeah, tell us, Johnny-boy,” Steve added.

“I... um... I didn’t get punished,” Johnathan mumbled. “My dad, uh--hey! C’mon, Andy! Don’t snipe me while I’m telling a story!”

“Don’t walk in front of my scope.”

Grumbling under his breath for a few seconds while he waited to respawn, Johnathan then continued his explanation (and keeping his character hidden behind a rock). “Anyway... my dad hired a personal trainer for me. Who’s, um, a woman. And, like... 6ft2, at least? Definitely a couple inches taller than me.”

“How old is she?”

“Is she hot?”

“Uh... I’d guess, like, 20-something? And... well, yes. She’s pretty ripped, with tattoos and an undercut,” Johnathan mumbled, feeling his cheeks grow hot.

“Have you slept with her yet?” Pete asked.

Choking in shock, Johnathan then spluttered, “What!? Pete! I just met her today?”

“What? She’s a hot twenty something who got hired to spend a lot of time with a billionaire’s son,” Pete replied. “Your dad definitely hired her to sleep with you, and she’s probably just hoping she can get pregnant to get some child support and be set for life.”

“... you’re a weirdo sometimes, Pete,” Johnathan replied.

“He’s a bit crass, but he’s got a point,” Andy said, while also getting a kill on Pete. “I’ll bet she’s aiming for trophy wife.”

“I really don’t think she’s like that,” Johnathan mumbled, feeling a bit ganged up on.

“Wait, when you say ‘undercut’,” Steve asked, “do you mean ‘long hair with one side shaved’ or ‘short hair, with both sides shaved’?”

“Uh, the latter.”

“Mhm,” Steve replied. “Yeah. Muscles, tattoos, and short hair. I don’t think she’s going to sleep with him. Sounds like a lesbian to me.”

“You can’t just say a woman’s a lesbian because she has short hair,” Johnathan protested. “Anyway, let’s change the subject before you idiots say anything else rude about a woman you’ve never even met.”

“Fine, but we want pictures,” Pete said.

“You’re not getting any,” Johnathan countered.

Why was he friends with these guys anyway?

---

After art tutoring in the morning, Johnathan found himself nervously waiting for the start of his next personal training session. Mostly because of what he was about to agree to, but also because he was excited to see Grace again.

While he disagreed with Pete and Andy insisting he should sleep with her as soon as possible, that didn’t mean he was in denial about having a bit of a crush. After all, she was roughly 100% his type. It was fairly rare to find girls who were taller than him, and even rarer to get ones who were so gorgeously... athletic. It really felt like Grace was a sort of a once in a lifetime encounter, and he did hope he wasn’t messing things up too much.

And, sure, she obviously wasn’t just going to sleep with him for his money, but that probably bought him a bit of grace when it came to flubs.

Err. Bought him a bit of leniency. That was a better wording to use. 

Anyway. He still needed to work on making a better impression, so he made sure he was dressed and ready before she arrived. Unfortunately he’d been a little over excited and had ended up being done getting ready a full half an hour before she arrived. Which meant he was left puttering around the living room, trying to do some stretches in preparation.

The maid who walked past while he was trying to balance to stretch out his leg seemed rather surprised. Whether it was because he was willingly out of his bedroom or because he was wobbling on one foot, he wasn’t sure.

Either way, he was very glad that the doorbell rang as she was watching him from the corner of her eyes. Scrambling over, he opened the door to find Grace, sleek and multicoloured sporty sunglasses over her eyes and a warm smile on her face.

“Well, you’re peppy today,” she said as he let her in.

“Trying to build good habits and all that,” he offered, while feeling like he was flubbing things.

It was hard to be smooth or charismatic when he was... himself. How did other guys manage to feel confident when they were trying to be worthy of women? The gap between the sexes was such a massive gulf.

Pushing those thoughts to the side for the moment, he led her down towards the gym again, while noticing she had a duffel bag this time. The contents were left a mystery to him as they made their way to the gym, though he had a guess for at least two things that might be in there.

If he was right then it was quite fair to keep hush-hush about them. At least until they had a closed door between them anyone who might be eavesdropping. Still, it made his heart beat in his throat for those last few steps to the sanctuary of privacy. 

Aiming for chivalry, he held the door open for Grace as they entered, which seemed to amuse her. Hopefully in a charming sort of way.

“So, are the--uh, supplements in there?” he mumbled.

“Mhm, yeah. Got some Kobaroic boosters in here and then a little estrogen to shave off the effects,” Grace replied. “Of course, my friend who worked out the doses wants me to make sure you read up on everything and know what it’ll do and any side effects it might have. She said informed consent is key.”

“Oh, uh,” Johnathan began, realising that it kind of made him seem incompetent if he admitted he hadn’t actually read anything. What had been the point of delaying his agreement if he hadn’t used the time to grow informed?

Well, there was nothing for it, if he wanted to avoid disappointing Grace.

“Definitely. Got a good idea of everything,” he lied.

“Good. Because she gave me this whole long list of stuff to go over if ya hadn’t and I really wasn’t looking forward to that,” she replied, letting out a sigh of relief. “So, yeah. Two estrogen pills and one Kobaroic steroid tablet with a meal once a day to start.”

Johnathan nodded as she handed him two small bottles, each looking like they could be vitamins or something. It was very professional and made him wonder just how above board the suppliers were. Surely something like that took quality control that you just didn’t get on the black market? But, on the other hand, it didn’t look like actual prescriptions...

Also, though, having the estrogen in his hands felt exciting. He wasn’t quite sure why, but there was just something about it that was exhilarating.

“Now, then, I will say that ya shouldn’t expect instant results, even with those. Depending on how bulked up you’re aimin’ for, it’ll likely take you months. More if you’re wanting to learn how to fight,” Grace said.

“... Fight?” Johnathan asked.

“Well, I do still do MMA practice. Just not allowed to go pro anymore,” she explained. “Once you’re in a bit better shape I can probably teach ya a bit.”

“That... that sounds very cool,” he mumbled.

“Something to look ahead to, then. Let’s run you through your first proper work out.”

---

Proper workout was indeed the term for it. Johnathan’s muscles felt like jelly by the end of it, and he was glad they were going to switch workout types each day. There was no way he’d be able to do that two days in a row.

---

That night, after having had a high protein microwavable bowl, he then grabbed a glass of water and then the pills. Staring down at the tiny little blue estrogen pills, it felt like a strangely momentous occasion for what was, really the secondary element of the medications he was taking.

He supposed there was a small chance they might help him feel more in tune with his feminine side? And then... be more confident, maybe? Since women were so much better, and all that. Being more like a woman would obviously have lots of benefits.

For a moment he debated taking a third pill, but he reasoned that there was probably a reason for the starting dose and he should just follow the instructions.

---

Matters began to grow more routine from that day. It was no longer about first impressions, so Johnathan began to feel less nervous while spending time with Grace. Sure, he was still somewhat flustered, but after about two weeks of workouts, he was reasonably certain he’d managed to embarrass himself as much as he could manage.

Plus, he really was feeling more confident. Maybe it was just a placebo effect of thinking the estrogen might help, but he was starting to actually feel comfortable looking in the mirror. It was odd, but his face was just starting to seem... almost softer?

There wasn’t any visible change in his muscles yet, but he was definitely feeling lots of soreness, and, well, the old saying went ‘no pain, no gain’, so he was sure he’d have some gain soon. Especially around his chest, that seemed the most sensitive.

Another change was that Grace’s occasional slip of the tongue, saying ‘good girl’ once again from time to time, somehow seemed to have more positive effect?

That was very odd, but he decided it was probably best just to not question it. Some things were best just left ignored. Like that time when he was six and wanted to dress as a fairy princess for Halloween... wait, why was he thinking about that again? Hadn’t he thoroughly repressed the memories of the outcome of that mistake?

Apparently there were downsides to taking estrogen, it making him remember those sorts of things. 

“You seem to be standing up straighter,” his father said one day, just after Grace had left. “There’s a good fire behind your eyes as well. I knew this would help you build the confidence you need to man up.”

Johnathan felt his mouth twitch slightly at the comment. Still, he was good at ignoring his feelings, so he gave a small nod. “Yep. Everything’s coming along well.”

“I will take it that you and Ms. Xanthopolous are getting along, then?” his father asked, still stood with a poise and authority that left Johnathan wanting to slink away.

“Oh, um... I think so? We’re mostly just talking about workout stuff and fitness, though. I’m usually a bit too tired at the end to bring anything else up,” he offered, feeling slightly embarrassed.

“Mhm,” his father replied with a small nod. “Perhaps you should try to plan some less formal time together.”

With that, John Preston III turned and left, moving with the sort of purpose he had in everything. The man was simply a force of nature that Johnathan couldn’t stand up against. Even if the ‘suggestion’ (read: instruction) sounded like he was being told to ask Grace out on a date, which was a level of confidence he hadn’t quite reached yet... Saying no to his father was also something he didn’t have the confidence to do just yet, however.

He was pretty sure he feared his father more than Grace, though.

---

The next day, Grace arrived with a mischievous sort of sparkle in her eyes. It left Johnathan even more nervous than he already was, due to the push from his father. Today was just supposed to be a yoga and flexibility day... that didn’t seem like the sort of thing that would fill her with mischievous energy.

“What’s... what’s up?” he asked.

“It’s a nice day out. Only a high of 26--er, 80? About that. We should do our yoga out on the verandah,” she replied. “Go down and grab a mat, then grab some sunglasses that’ll stay on. It is bright.”

“Um... ok,” he replied with a small nod, hurrying off to do as he was told.

Finding a yoga mat wasn’t hard. The gym was well organized. Sunglasses, though... the ones he usually wore were not designed for physical activity. They were haute couture designer things his mother had gotten him one time. They were cool, but they were for the sort of passive cool where one acted aloof of everything. And, therefore, didn’t move much.

Luckily a bit of digging helped him find the pair he’d gotten for going skiing a few years back, before he’d found out just how tiring skiing could be. 

He then hurried back, to find Grace exploring the patio. It seemed like she was trying to study every inch of it, which seemed a little odd.

“Did you lose something?” he asked, feeling a bit less self conscious with both of them wearing semi-mirrored sunglasses, so there was no risk of accidental eye contact.

“Oh, nah. Just studyin’ the feng shui feels... need to make sure we can find a place properly zen for our yoga session,” she replied, continuing to explore the extensive wrap around patio. “... Strewth. You guys have a whole second pool up here.”

“Yeah, it’s sort of tucked around the back for privacy,” he replied.

Grace nodded, then continued to explore. As she did so she muttered something about ‘rich people’, which he had no argument against. Two pools did feel excessive. Especially with how little anyone used either of them.

Rounding another corner of the sprawling house, Grace seemed to get a bit distracted by spotting the outbuilding where his father’s office was. Probably because there were a few guards patrolling around it at the moment, since his dad was in a teleconference all day today.

“Some of those security boys are cute, but they get upset if you stare too much. I learned from experience,” a feminine voice said, causing both Johnathan and Grace to turn around...

To spot Tecla Preston laying on a patio chair in only a bandeau bikini that showed off the fact that being in her mid forties and a mother of two had yet to overcome the combined powers of her having a personal trainer, dietician, and amazing Colombian supermodel genetics. Though she had started limiting how much time she spent out sunbathing like this lately.

“Mom,” Johnathan grumbled, annoyed to hear about his mother’s interest in any men (though, at least it wasn’t about his dad specifically).

“M--Mrs. Preston,” Grace stammered, and, when he glanced at her, Johnathan swore she was blushing slightly. “Sorry. We didn’t mean to intrude. I just thought it was a nice day to do yoga outside--we were just looking for the best spot. We’ll, uh... we’ll keep movin’.”

“Fair enough. Half fun, you two,” Tecla said, laying back down to soak up more rays.

As the pair left towards a more private stretch of patio, Johnathan did have to wonder about that blush. Was Grace worried about her own femininity compared to his mother’s more conventional looks? 

Maybe that made it the best moment to propose the date. Help give her a confidence pick-me-up?

Ok, so it could maybe also seem like praying on a moment of weakness, but he didn’t like thinking about it that way. It was meant as friendly reassurance.

“Are you free this evening?” he asked.

Grace paused and blinked, before turning to him. “Pardon?”

“For dinner or something?”

“Is--are you askin’ me out on a date?” she asked.

“Uhh... maybe? It can also just be platonic,” he mumbled. “Just... I don’t get many chances to hang out with someone as cool as you, so...”

A soft smile spread across Grace’s face. “Well, I’m a little busy this weekend, but I can probably do Monday?”

“Oh! Yes. That works. I’m free any evening,” Johnathan replied, nodding enthusiastically.

“Sounds good, then,” Grace said, laying her yoga mat down. “We’ll look out to the west from here. Best view.”

“Huh. That’s west? I’m not that good at directions,” he said, laying his own mat down and realising they could still just sort of see his dad’s office building.

“Ah, yeah. I have lots of practice knowing which way is--uh, any direction. Lots of hiking in the Outback. Yeah,” she replied, though it seemed like there was more to it than that.

Clearly he did need to get to know her better. There was lots to learn.