Fantasy vs Reality (Chapter 1: Pool Day 2/24)

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
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Re: Fantasy vs Reality (Chapter 1: Pool Day)

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Chapter 1: Pool Day

It was a hot, sunny summer day. A perfect day for the pool. We had already planned on going to grandma’s house that weekend and I was looking forward to swimming. I already knew Jen was going with us. She had come over the afternoon before and slept over so that we wouldn’t have to wait for her to get there.

I got up that morning and got a bowl of cereal. Mom walked in and greeted me as I was eating. “Good morning Sam.”

“Good morning Mom.” I said between mouthfuls of cereal. As I was finishing up my breakfast, Lucy and Jen both walked into the kitchen.

“Morning Sam” said Jen as she looked toward the table I was sitting at. I responded in kind. Lucy seemed to ignore me as she came in to talk to mom.

“Hey mom, Katie just texted that she’s on her way over.”

“Oh, ok. When she gets here we can head over to grandma’s. Sam, if you’re done eating then go ahead and go put your swimsuit on.”

This was the first I had heard that Katie was coming. She had come over to swim a couple of times before, but it wasn’t very often, and she hadn’t swam with us at all the year before, so it was a bit of a surprise.

I didn’t like Katie very much. She was Lucy’s “pretty and popular” friend. I will say she was definitely the former. Between her blonde hair, slim figure, and confidence to flaunt some of what she had, she wasn’t starved for attention.

None of that is why I didn’t like her. In fact, that was one good reason to look forward to seeing her at the pool, in a swimsuit. But being one of the “popular” girls had given her a somewhat nasty attitude. While Jen might go along with Lucy picking on me, Katie would encourage it. She thought I deserved it for being “a nerd.”

Oh well. Katie being there was unexpected, but swimming would still be fun, even if there was an extra bully to deal with.

I washed out my bowl and went back to my room to change. I made sure the door was closed and got out my swim trunks. I had grown some from the previous year, but they still fit. The elastic felt tight enough that I wouldn’t have to worry about them falling down accidentally. I checked again that the door was closed before undressing and slipping them on. As usual for me, I got a small thrill from leaving the drawstring untied. I headed back out in my t-shirt and shorts.

We hung around for another 30 minutes or so while Lucy and Jen ate breakfast. Katie showed up with a bag in one hand and a towel under her other arm.

“Ready to hit the pool Katie?” Jen asked.

“I do still need to change, but I figured there was no need to keep you all waiting for that. I’ll just do it at your grandma’s house.” Katie replied. She then looked at me, waiting around. “Of course he’s coming too. Lucky little nerd gets to see me in my new bikini. He’d better not stare.”

“Oh don’t worry about him. I’m sure he’ll remember his place. If not we’ll remind him.” Lucy said, emphasizing the part about reminding me in case I missed her threat. I didn’t. At that point mom came in, car keys in hand.

“You all ready to go?” She asked.

“Wait” said Katie “Where’s Amy? You said she was coming too.”

This was an even bigger surprise than Katie joining us. Amy had been friends with Lucy for several years but had never come to swim with us. I’m not sure if she had been invited before or not, but this would be her first time at our pool.

Amy always seemed kind of out of place with Lucy and her friends. She was very smart, straight A’s, and also just a nice, sweet person. She was always nicer to me than Lucy’s other friends. I’m not sure why Katie didn’t consider her a nerd, but I suspect that in her eyes only boys could be nerds. On top of all that, there was another reason why I wanted Amy in particular to like me.

Lucy answered Katie’s question “Amy actually lives closer to grandma’s house than here, so she’s just going to meet us there.”

Hearing that Amy would be there raised a question in my head that I just had to ask. “What about Sarah? Is she coming too?”

I probably should have kept my mouth shut. Lucy answered me without hesitating. “Sorry lil bro, but it’s just Amy coming, your crush can’t make it.” I blushed at being called out and Jen looked a bit surprised at that comment, but Katie jumped on it.

“Awww, the little nerd has a crush on Amy’s sister?” And she started giggling at my obvious discomfort.

“Yeah, she’s in his grade so they know each other. They might even be classmates again next year.” Lucy added.

“In that case we should definitely tell her. It only fair that she be warned.” Katie responded.

That’s when mom ended the conversation.“That’s enough, leave your brother alone and get in the car, it’s time to go.”

We piled into the car without any further delay. The drive was over quickly and soon enough we had arrived. Grandma welcomed us and we exchanged some pleasantries. Mom said “There’s a few chores around the house I need to help grandma with, so you’ll be kind of on your own for a little bit. Just make some noise if you need me, but you girls are in high school and Sam’s smart enough to avoid drowning under all of your noses. Have fun!”

With that, Lucy, Jen, and I went out to the pool while Katie went to the bathroom to change. I pulled of my t-shirt and jumped into the pool while Jen and Lucy were getting in at the stairs. My tomboyish sister’s choice of swim wear was unsurprising. Lucy had on a modest green two piece, but I could only see the top as she had some shorts on over the bottoms. It didn’t show very much as the top looked more like a sports bra than a bikini top. Jen was wearing a tight purple one piece that showed little skin but still left little to the imagination.

Some minutes later Katie came outside with her towel wrapped around her. She set her phone on the table with the others before unwrapping her towel and throwing it on the back of a chair, revealing her new bikini in the process.

Earlier she had said I was lucky to get to see her new bikini. She hadn’t lied. It was quite the skimpy string bikini, the kind most parents probably wouldn’t let their daughters wear. I’m guessing she may have wrapped herself in the towel on her way out to avoid the adults seeing it. It didn’t take long for her to notice me. “What did I say about staring twerp?”

Jen responded to her “Can you blame him? That’s probably more female skin than he has ever seen! At least in person.” She was right, but I had the good sense to not say anything to confirm it.

“You’re one to talk Jen, that suits looking pretty tight, maybe it’s time get you a bigger one.” Lucy remarked.

“What’s that mean?”

The question had been directed at Lucy, but it was Katie that answered. “It means that even with all the fabric covering you, it’s still not really hiding much.”

It was true. Jens one piece wasn’t showing that much skin, but it was still quite apparent that her figure was a bit more “feminine” than the other two. That fact hadn’t been lost on me either.

“Yes, I have no doubt my pervy little brother will be fondly remembering this pool day for a long time.”

We swam for a little while after that. Sat on some floats, sprayed water guns at each other. After about forty five minutes of us enjoying the pool and trying not to bother each other, we all heard the back door of the house open, and out came Amy. She had her red hair in a ponytail and was wearing loose fitting jeans and a baggy t-shirt along with her glasses. She greeted us warmly. “Hey girls, nice day for a swim. Oh, and hi Sam, how are you doing?”

“Hi Amy! I’m doing pretty good.”

“Good, I hope these three haven’t been giving you too much trouble.”

“Eh, no more than usual.” I tried to act casual but that wouldn’t last for very long.

“Well, it’s hot as balls out today and I just rode a bike here, so I’m going to get in that water and start to cool off.” Amy said while starting to unfasten her jeans. When she pulled off the shirt to fully reveal her one piece swimsuit I couldn’t help staring. I knew she’d probably notice me and get annoyed like Katie had. As it turns out I had nothing to worry about, seeing Amy in her swimsuit had the same effect on the other girls.

While Katie was hot and wearing a skimpy bikini, neither of those was a surprise to us. Amy, however, was a smart and well mannered girl who always dressed rather unflatteringly. She didn’t seem that interested in getting attention from boys. I don’t think any of us were expecting to learn that she was hiding such a smoking hot body. A moment passed in silence before she noticed everyone staring.

“What? What is it?”

“Nothing, just never realized you were secretly hotter than Katie.” said Lucy, always happy to stir a bit of drama.

“Hey!” Katie reacted before looking back at Amy. “Definitely hotter than I expected, though.” Then Katie looked over at me, saying “I get it now, nerd. You’re wasting your time, but I get it.”

“Get what? What are you talking about? What is she talking about?” Amy asked, confused. That was all the invitation Katie needed, getting a cruel smirk on her face.

“Sam has…”

“Katie!” Jen tried to interject but it was too late to stop her.

“Sam has a crush on Sarah. And if she turns out to be even half as sexy as you then he has good reason.”

“A crush? On Sarah? Huh…” Amy’s response was rather neutral. I just blushed again and sank into the water to hide from the conversation.

We all just got back to enjoying the pool for a while after that, though Amy continued to seem a bit awkward toward me. It was like she wasn’t sure how to respond to finding out I liked her sister. Honestly, I wasn’t too sure how to respond either. This morning I had thought my crush was a secret, now it was the hot gossip for my sister and her friends. How long until one of them told Sarah? I genuinely wasn’t sure if Amy would, but Katie probably wouldn’t hesitate.

About an hour later, mom came out of the house. “Hey, hope you’re having fun out here. There has been a bit of a problem. Grandma’s vacuum cleaner has broken down and we have to go get a new one. We might be gone for a bit so don’t get yourselves in trouble. Amy, you’re smart and usually level headed, try to keep them from breaking anything, ok?”

“No problem, we’ll be fine here.” Amy cheerfully responded. And mom and grandma left. Now I was in the pool with three hot girls in swimsuits with effectively no supervision. Even my sister being there only slightly dampened the fact that this scenario would be a dream for any adolescent boy. I didn’t yet realize how much it was going to become my recurring dream.
My True Story: viewtopic.php?t=4978

The Fictionalized Version: viewtopic.php?t=5014
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Re: Fantasy vs Reality (Chapter 1: Pool Day 2/24)

Post by Jeepman89 »

Love this setup for embarrassing things to happen to Sam at the hands of those girls.
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Re: Fantasy vs Reality (Chapter 1: Pool Day 2/24)

Post by IdentityUnknown »

Jeepman89 wrote: Mon Feb 24, 2025 7:03 pm Love this setup for embarrassing things to happen to Sam at the hands of those girls.
Yeah, it’s been a lot of laying groundwork to introduce the main cast and set up for the main story. Hopefully I’ll get the next chapter written this week. If not, then look for it this weekend.
My True Story: viewtopic.php?t=4978

The Fictionalized Version: viewtopic.php?t=5014
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