Resort to Change Ch. 04

Day 5:

It was 8 AM, and Tyler was wide awake.

The first thing he did was text Miguel to invite him on a date.

They both agreed to have dinner at the resort's restaurant instead of going out and exerting themselves.

Before he turned his phone off, he noticed a notification from Shawn.

He felt bad ignoring him, but things felt complicated.

He decided to get back to him at the end of the day, or maybe even pay a visit.

With that cleared up, Tyler jumped out of bed, twirling around the room in his negligee. He stopped to look at himself in the mirror, loving what he saw.

The first thing he did was shower and shave again, to make sure.

Next, it was time to get dressed.

He rummaged through his new clothes, excited to put anything on.

Finally, he made a decision.

It was a bathing suit.

Yes, Tyler was going to swim, and he needed to test out the big guns first.

This was sure to get attention, he thought. And boy was he right.

It was a simple pink two-piece with matching strappy sandals.

Tyler loved how they felt. He noticed an erection growing as he had it on.

''I have enough time for breakfast; I can quickly rub one out.''

He said, as he took out his phone and loaded up the porn.

Without thinking about it, he searched for gay porn, clicking on the first video that popped up.

Two men, one twink and one gym bro, were on the bed, shirtless.

The twink started things off by licking the muscular guy's nipples, as he slowly stuck his finger in the twink's ass.

It had never occurred to Tyler that he could feel pleasure from his nipples.

As he watched, he began twisting his nipples, copying the porn.

His free hand began stroking his cock as the two men were now on top of each other, making out.

Tyler's mind wandered to Miguel, imagining the two of them in the same position.

The twink then got on his knees and began blowing the other.

When the guy in the video started cumming, so did Tyler, letting it all out.

He got up, relieved, cleaned himself, and headed out.

On his way there, he noticed all the stares.

Everyone's loving the new look. He thought to himself.

As he sat in the pool, he noticed a group of female friends laughing amongst themselves.

''Julia, stop. I'm over that asshole.''

One of them said, as she playfully tapped Julia's shoulder.

''You're over him and under him; be so for real.''

One of the other girls said, flicking her hand in the air as she did, making them all laugh out loud.

Just as he was absorbing what he saw, he noticed a guy staring at him from just a few feet away. He was undressing Tyler with his eyes.

The guy was well-built, giving that Jesus look, especially with the long hair going past his shoulders.

Tyler swam to him, hoping his hunch was right.

''Hey, my name's Tyler.''

He said, offering the man his hand.

The guy took Tyler's hand and gave it a little peck before introducing himself.

This surprised Tyler, in a good way. As he felt the man's lips touch his skin, he felt his cock harden in his panties.

''My name is Alberto. You look very pretty.''

He said, seducing Tyler with his stare alone.

''So, are you from around here?''

Tyler asked.

''Yes, I was born and raised in this city. I'm at this resort to see a friend.''

''Oh, I'm from America, just here on a trip.''

''I see, so you have some time before your departure?''

''I have two days left.''

''That's enough time to have fun. Would you like to go back to my room?''

Tyler thought about it as he looked at the attractive man in front of him.

As much as he wanted to be with Alberto, he knew he wasn't ready for that.

''I can't right now. Give me your number, and I'll text you when I'm free.''

Alberto was fine with that.

''I'll be waiting.''

He said before getting out of the pool.

Tyler watched as Alberto walked away in his swimming briefs.

His cock was still hard by the time Alberto was out of sight.

As he got up to go back to his room and put on some clothes, someone stopped him.

''Tyler? Is that you?''

It was a woman's voice.

Tyler turned around to see Cynthia, one of the girls he had approached.

He actually hit it off quite well with her, but was interrupted by his Mistress.

''Yes girl, it's me.''

He said, flicking his wrist.

She was a bit thrown off by everything. She thought he was hitting on her that day.

In all fairness, all he did was compliment her and ask to hang out.

I got him all wrong. She thought.

''I love the bikini; it's cute, and your body's Tee girl.''

She said, now matching his energy.

''Says you. That dress is so cute; I love it.''

He said, as he slightly tapped her shoulder, copying what he saw the girl do.

''Well, I'm going to go put on some clothes so I can have breakfast. Let's stay in touch, though; here's my number.''

He said, as he quickly handed it to her and headed off.

She watched as he walked with a feminine stride, like he was on a runway.

She was slightly disappointed, since she really thought he was flirting that day.

She really didn't expect him to be gay, but it was nice to make friends, she thought.

As soon as Tyler got to his room, he picked out something less revealing.

Before he could put on the clothes he wanted, he had to put on a bra first.

Without it, the look just seemed off.

He picked up a black laced bra to match the panties.

Thanks to Olivia, it fit like a glove.

Finally, he could put on what he wanted.

He chose a navy short dress and stuck with the strappy sandals, choosing to save the heels for his date with Miguel.

As he stepped back out into the public eye, he couldn't help but walk in a way that would attract attention.

His hips swayed with each step he took, as he had a slight tilt while he walked.

When he was in the restaurant, he noticed loads of eyes on him.

But he couldn't feel the judgment they were giving.

All he cared about was looking good enough to attract the male gaze.

As he waited in one of the lines, somebody called out for him.

''Tyler, over here.''

He looked over to see it was Olivia, with a woman he hadn't seen before.

He went over to them, taking a seat.

''Hey, this is my new friend, Zoe. Zoe, this is my friend Tyler.''

They shared an awkward glance at each other, giving a slight smile.

''Don't be shy, guys. Just wait here; I'm going to get some more fries.''

She said as she quickly hurried off, leaving the two in awkward silence.

''I'm wearing the same sandals you are, just in a different color. Look.''

Zoe said, making genuine conversation.

Tyler looked underneath the table to see, and she was right.

''Wow, you do! That's so cool; they look so good on you.''

He said, slightly tapping her shoulder.

''I also noticed that you got your nails done; they look really good.''

''Oh, thanks. I got them done with Olivia, actually. We went to the mall in the main part of the city. We should all totally go together one of the days.''

He said, showing off his manicure and giving her a closer look at his hands.

Finally, the ice had been broken, and the two were really hitting it off.

Olivia had come back and was happy to see them so friendly.

Once they had all finished their food, Tyler got up to leave.

''Tyler, Zoe and I are going to the resort's spa. Do you wanna come?''

He thought about it; he had time to kill before his date, and other than that, he was free.

''Yes girl, I'd love to!''

He said, waving his hands around in excitement.

On the way there, they were stopped by a group of men.

One of them approached Zoe.

''Hey, you are beautiful. Do you think I could get your number?''

He asked.

She looked at him like she wished he wasn't there. Tyler noticed her discomfort.

''Get lost, boys; she's not interested.''

One of them looked at him, sizing him up.

''Shut up fag, I almost mistook you for a girl until you spoke.''

He said, laughing at Tyler.

''Let's go, girls.''

Olivia said as she walked off, with Zoe and Tyler following.

They all sat down together, Olivia and Tyler checking on Zoe.

''Men are so disgusting.''

Olivia said as she stroked Zoe's hair.

Tyler was staring off into space, lost in his head.

They thought he was a girl? Why'd they call him a fag?

He was confused and insecure, not understanding where their comments came from.

Of course, to anyone else, it was obvious, but all that was lost on him.

To him, he was just following his role model's lead and trying to get men's attention.

''Tyler, they were jerks; you know what they said was stupid.''

Olivia said.

He needed to hear that, as it snapped him out of his daydream.

Olivia knew best, he thought.

''You're right, let's not let them ruin our day.''

He said as he stood up.

Zoe and Olivia agreed as they followed suit.

Tyler was a little hesitant about the whole spa thing.

He felt it was a more feminine activity, but that justified his reasoning for going.

If it was something women did, then he definitely had to do it too.

He respected and looked up to all women, and so indulging in their activities felt much easier. It felt right.

While he was at the spa, he noticed that a lot of the women, if not all, had makeup on.

This included Olivia, who always had hers done. This wasn't judgment, but an observation.

He started thinking about having makeup on his face.

It made his body tingle.

Maybe it would impress Miguel. Maybe it would impress all the men.

As the three of them waited for the service, Zoe noticed a board with prices.

''Wow, it's actually quite cheap. I think I'll get a bikini wax. What about you, Olivia?''

''Oh, no thanks. I already got one done before I came to Spain.''

''What about you?''

Zoe asked Tyler.

He thought about it. Olivia had gotten it, and Zoe wanted it too.

It was clearly something women here did.

''I'd love to!''

He said excitedly.

Zoe was relieved he didn't take offence at her question.

He was exactly the type of person she thought he was, in a good way.

''I got the spa prepaid, as part of the all-inclusive deal.''

She said.

''Oh, I didn't do that.''

He was not worried about the money, but still felt left out.

''Why wouldn't you think of that beforehand, silly? Well, next time, you know to check that.''

She said.

''Yeah, I will.''

''Tyler, is this all for your date tonight?''

Olivia asked.

''How'd you know about my date?''

''You told me. Are you drunk?''

She laughed.

He figured he must have, and that, like last night, his memory was just a bit blurry.

''My date's name is Miguel, and I wasn't initially going to do this until you two asked. But now that I am, I'm glad.''

He said, and he meant it. Because now, he'd look even better for Miguel.

Even though he still wasn't ready to be seen naked, he knew it'd come in handy. Especially for all the other men.

30 minutes later, Olivia was already out. Zoe and Tyler had come out an hour later.

When the two of them got out, they found Olivia was talking to some other woman.

Tyler noticed her immediately. It was his Mistress.

''Oh, hey Tyler, I was just talking to Olivia over here. I was asking where you were.''

''Yes, I'm here, Miss- I mean, Linda.''

He said, hoping the girls didn't notice.

''Don't worry, I'll leave you to it. Come to my room afterwards. Bye, have fun. It was nice meeting you, Olivia.''

That was odd, Tyler thought.

Maybe she had just coincidentally run into Olivia and asked about him?

But how did she know what Olivia looked like? Maybe she saw them together before. He decided that he was overthinking about nothing.

''Okay, it was nice hanging out and getting to know you both, but I have to go. I've got Olivia's number, so if you guys want to hang out again, just let me know and we can set something up.''

Zoe said before taking her leave.

''Olivia, if you're free, could we go back to your room, please? I want you to teach me how to do my makeup.''

He couldn't deny the fact that a lot of these women walked around with makeup on, and they looked incredible. He knew he needed that lesson for himself.

''Yes, I'd love to. Is this for Miguel by any chance?''

She asked.

''Well, you could say that.''

Once they got to her room, Olivia got out all the necessary tools to help him look right and to teach him how he was supposed to do it.

She got him introduced to all the different lipsticks, then brushes, creams, sprays, and more. By the end, Tyler was familiar with most of what Olivia had shown him.

Next, it was time to apply it. This took some time, but it was worth it.

She wasn't just applying it to him, but teaching him as she did.

Tyler looked at himself in the mirror, all dolled up.

He then looked at Olivia; this was what he wanted.

''Thank you so much. It looks so good. I'm going to buy my own products.''

''Yes, you totally should. Keep practicing.''

After that, Tyler headed back to his room to prepare for his date.

He applied some perfume Olivia had gotten him and quickly slipped his feet into his heels.

He had to make one more stop, though.

KNOCK KNOCK.

''Come in.''

He walked into the room to find his Mistress sitting in the same spot on her bed.

Except this time, she was naked.

He didn't say anything, or even really notice it.

''I couldn't say much in front of your two friends, but I love the look. The outfit looks good on you.''

''Thank you, mistress.''

''Is that makeup? That looks really well done; I'm impressed.''

''Thank you, mistress. Olivia taught me.''

''On your hands and knees, crawl to me.''

She said, her voice so alluring that he couldn't say no if he wanted to.

Tyler obeyed.

''Good boy.''

She said, noticing his cock get excited by the compliment.

''So, Tyler, do you like what you see?''

She asked, pointing to her body.

''Yes, Mistress.''

He said. But, of course, he just meant she looked pretty. No sexual intent.

''Now, eat my pussy.''

She said, stretching her legs apart.

Tyler paused. He didn't want to do something like that to her; he knew he didn't deserve it, but it didn't excite him either.

''What's wrong? Lick it.''

She ordered again.

She knew exactly what was going through his head; she just wanted to play around with him. Maybe get him to admit that he didn't want to do anything sexual with a woman. Maybe he hadn't realised it himself yet.

''Oh, I see, you're not into women.''

She said.

''Why would I be into women?''

He asked, confused.

''Oh, so you're gay?''

Again, Tyler paused.

''No, no, I'm not gay, I just.''

He had no idea how to respond. He didn't know the answer himself.

''Tyler, just, SUBMIT.''

Tyler's body went limp as he slowly fell over to the side.

''Good boy, so deep, so relaxed. Now, no lying, full honesty, why didn't you want to eat my pussy?''

''I felt like I didn't deserve it, and that I should treat women as sacred beings that are meant to be respected.''

''Good boy, as you should. But you know what it also tells me? That you aren't attracted to women either. Do you agree?''

No response.

''Tyler, how would you describe a gay man?''

''Someone who's attracted to other men.''

''Aren't you attracted to other men? Answer truthfully.''

''Yes.''

''So, what does that make you? You don't need to answer; you already know. There's nothing wrong with being gay; you simply discovered yourself on this trip, and you're having a hard time coming to terms with that. I'm here to help. Tyler, do straight men wear women's clothing?''

''No.''

''They can, and they do. But straight men are attracted to women. You aren't straight. Not because of how you dress, or how you carry yourself, but because of what your brain has chosen in terms of sexual interest. That's men. So, I ask again, are you gay?''

No response.

''Okay, we don't need to go through what you did today; I already know. Let's skip to your instructions. When you go on that date with Miguel, have fun, let loose. Through your own sexual needs, you will choose whether or not you want to take that extra step with him. You know what you want, you know what arouses you, what excites your body. At the end of the night, you will know who you truly are.''

To be continued.