A full 48 hours passed from my last message to my younger sister:
***** {“Just asking for less subtlety
”} *****
I was kicking myself for sending that message so quickly and not putting more thought and patience into it. I was hoping to run into Maddy in person, to try and clear the air. Not that I had the slightest clue how to go about doing that, but in-person interactions were so much simpler. You had real-time reactions and there was nothing lost in translation.
Message from Maddy
Yes! Nevermind!
{“Butttt we’re bro n sis…and you’ve seen me in person anyway! Without subtlety lol”}
Alright, I processed. Not as bad as I thought. And she still had an “lol” in there which was a good sign. Just keep things playful. I decided to sit on this one, even though she would know I read her message already.
Katie invited me out with her and Amy. The three of us were hitting up a rooftop pool party at some ritzy hotel. It was a private event, but there was no surprise Amy got an invite. Jordan and Kelly were out of town visiting family. Who knows what Ed was up to.
“Kelly told me EVERYTHING,” Katie smirked as we took the subway to the hotel.
“Oh, God,” I said. “I dunno what happened.”
“Uhhh, heatstroke? Dehydration? No endurance? All the above, haha”
“I guess. Never happened before, though.”
“First time for everything….speaking of which,” Katie leaned in close, but the train wasn’t very full. “Kelly wasn’t TOTALLY disgusted by her first looks at your peen!” She teased.
“Yeah, you weren’t either,” I smirked.
“Had to act like it when talking to her, though,” she laughed. “So, how come you didn’t make a move?”
“How come I didn’t make a move? I had just passed out for fuck’s sake. Not even sure I could’ve stood up.”
“True, haha.” There was some silence. “But
would you have made a move? If you felt better?” Katie’s voice came off more curious than jealous.
“I mean the moment wasn’t really right. What was I gonna do just stand up, ass naked with a hard-on, and approach her? Little aggressive.”
“See, that’s your issue. Not EVERYTHING is aggressive, Drew. You overthink things.”
My thoughts went to Maddy. Did I need to be more forward with her? That could be a slippery slope.
“Well, we’re in the me-too era. Guys have had their reputations destroyed for less,” I said.
“That’s cause they don’t stop when we ask them to,” Katie said. “Or they make their advances at COMPLETELY inappropriate times. Like, right in front of everybody. We like sex too, dude. If you hadn’t noticed.”
“So what, I just walk over to her, kiss her, and she strips naked?”
“I can almost guarantee that’s what would have happened,” Katie answered.
I was starting to regret letting that moment with Kelly pass. But I was preoccupied at the time. And legitimately did not feel well.
“You think
we would have ever hooked up had I not
constantly made the first move?” Katie continued. “Flashing you, feeling each other up, FULLY coming on to you in Mexico?”
“Okay, it’s a little different with you, you’re my sister!”
“And you’re my brother!”
“Exactly! If we read things wrong with each other it would’ve fucked us up for life.”
“Didn’t stop me,” she said.
“Didn’t it? You denied everything for like the first 4 months of this shit!” I argued.
“Okay, touché,” she laughed. “But then I came around.”
“Only cause
I made it obvious I enjoyed it.” I said.
“Well, your
penis made it obvious. Thing went six-to-midnight anytime you even saw a hint of me,” she snickered, and bent forward, close to my groin. “Are you gonna wake up tonight wittle guy?” She joked in a baby voice, giving my cock a playful grope. “I’ll be in a bikini,” she whispered sensually.
“Shut up,” I said. “Why are you trying to help me with Kelly anyway? Thought you didn’t want us hooking up?”
“I don’t,” Katie said, plainly. She left it at that.
I let out a sigh. “You can be real annoying sometimes, you know that?”
Katie said nothing.
We arrived at the hotel with simmering tension in the air. Amy greeted us in the lobby, and we put on some fake smiles.
“Whatsup you guys, long time no see!” She said. She gave each of us a hug, and we got onto the elevator and rode up to the 27th floor, chit chatting along the way.
We got off and two large security guys nodded at Amy. “These are my two guests,” she said.
The burly dudes checked out Katie and barely even glanced at me. The girls split off to go change and I was left alone to check out the party. There was a large, rectangular pool in the center of stone pavers. The water was a deep navy shade, and entirely still, with no one in it. There were surrounding plants and trees that created a rooftop oasis in the middle of the city. High glass stretched around the edge of the building, to prevent any jumpers or stumblers from giving the hotel unwanted publicity.
It didn’t take long for me to notice that this was not my crowd. A bunch of pompous looking dudes with haircuts that probably cost more than my two-week salary. The women were modelesque, but not in a good way. Tall, boney, and expressionless – not my type at all. I considered my family well off, but these people were on a whole other level, seemingly detached from reality. They all had shades on, so I couldn’t tell if they were looking at me and judging me on my peasant attire. Whatever. I was gonna have fun whether they joined in or not.
I went over to the bar and ordered some champagne. Time to reply to Maddy’s last message. I thought back to her last message, which mentioned that I had already seen her in person and that we were brother and sister. Perhaps it was Katie’s lecture, perhaps it was the expensive booze, but I was feeling frisky.
{“Doesn’t mean I wouldn’t like to see again!
”}
Sent.
Katie and Amy finally came out to join me. The golden hour sun beamed down on my sister, making her look positively radiant in her pink bikini. Her curves never seized to amaze me. Amy was no slouch herself, in a tiger-striped one piece. It was a breath of fresh air seeing them in their colorful outfits, breaking up the black and white sterility of the “party.”
“What’re you so cheesy about,” Katie commented.
“Nothing, just enjoying the views. Ready to get this thing going,” I said, finishing my first champagne and ordering a second.
“Haha, knew you guys would bring the fun! These things get so stuffy sometimes,” Amy said.
“Amy, thanks for helping out with Kyle, by the way,” I said. “Don’t think I’ve seen you since.”
“Oh, don’t mention it! Dude’s a creep, I noticed that at Halloween.”
“Yeah, everyone picked up on it. Except Drew!” Katie said.
“He’s alright, as long as girls aren’t around,” I said. Amy smiled at me.
“but uhh….you guys should prolly cool it with your ‘pranks’ up here tonight, k?” She winked at us. “If you haven’t noticed, not really that type of crowd. And they can make things miserable for you, if you piss them off.”
“Not that type of crowd until the 8 balls come out,” Katie muttered.
“Haha true. Then all bets are off,” Amy said.
The three of us continued to chat and drink and eventually were the first people to get in the pool. I was surprised a couple of others actually joined us. They didn’t seem too bad. Perhaps I misjudged these people. From the water, I noticed my phone lighting up. I swam over and climbed up the ladder.
Message from Maddy
I dried my fingers and opened up the app. I noticed Katie glancing over at me, but opened the message anyway.
{“Lol. What do u want to c?"}
Oh my God. My dick twinged in my swim trunks reading that one.
{“Hmmm. You’ve sent everything separately…..can I see it all at once?”}
Sent. I was feeling way too bold for my own good at this point. I tossed my phone aside and dove back into the pool. Once I re-emerged, a dude in a black suit was standing over me.
“Monsieur, there is no diving in the pool.” He said curtly.
“Oh, errr….sorry.” I said. He didn’t reply, and strode away with swift elegance.
“Way to go, Gatsby,” Katie mumbled. “Hey, you wanna try kicking it down into fourth gear for a bit? You’re doing a lot right now.”
“Sorry for partying,” I said.
“Who ya texting over there?”
“Don’t worry about it,” I said.
“Oh, you’re gonna be Douche Drew now? Okay, that’s cool.” Katie swam away and climbed out of the pool. I admired her behind with discretion. She waltzed over to some rich dude and began chatting him up. I laughed at her childishness. These dudes were the FURTHEST you could possibly be from Katie’s preference and everyone knew it. She wasn’t fooling anybody.
“Don’t worry, that guy’s harmless,” Amy whispered in my ear.
“Whaa…oh…I wasn’t” I stumbled over my words.
“Unless he bores her to death, that is. Just another pretty face with deep pockets. Dime a dozen, in this city.”
“Right.”
Amy and I climbed out of the pool ourselves and relaxed in the lounge chairs.
“So, heard you guys got a big wedding coming up, huh? You’re bringing Kelly?” She asked.
“Yeah, should be a good time. We’re excited for it and heard the venue’s badass.”
“Thanks for the invite,” she said.
“Err, sorry, I just…hadn’t seen you, and was hanging out with Kelly - ”
Amy interrupted me with laughter. “I’m just joking Drew!” She patted my thigh in a friendly manner. “But we all should start hanging out more. Maybe recreate some of that first night magic, huh?” She got up and walked to the bathroom. She had a nice ass for such a slim figure. Though it may have just looked better compared to all the flat, shapeless women at this party.
Message from Maddy
I placed a towel over my lower half. Wasn’t about to be caught sitting here with a boner. I opened the app and was thrilled to see a red square. That meant one thing: Pic!
The only thing behind me was the glass edge of the building and the streets below. I opened the message, but was quickly disappointed.
Maddy was fully dressed, and took the selfie from her shoulders up. Still, she looked cute as ever. She was smiling with her tongue out but the caption on the pic said {“Noooooooooo”}
Fuck. This was becoming an aggravating game. I didn’t even know how to respond.
I had passed the peak point of drunkness and was now on the way down where you become less energetic and euphoric and more tired and grouchy. I began devouring some of the hors d'oeuvres. It wasn’t long before Katie noticed me sulking and came over to me.
“What’s up, you good?” She asked.
“Yeah, fine,” I slurred.
“Think, we should head back, this thing’s pretty lame,” she said.
“Agreed.”
“I’ll meet you back out by the elevators. I’m gonna change and say bye to Amy.”
“k.”
I said my own goodbye and thanked Amy for inviting us. She seemed bummed we were leaving, and was probably about to take off herself.
Katie and I rode the train home without much talking. Partially because we were still annoyed with each other, partially because we were tired, and partially because it was prime weirdo hour on the subway. It’s best to stay as inconspicuous as possible in these situations.
We got home, and Katie went right to the bathroom and turned the shower on. I waited in my room, wanting to shower myself. I pulled out my phone. Goddamn I was horny and frustrated, which wasn’t the best state of mind to reply to Maddy. But fuck it.
I took a few selfies of myself, until I captured one where I thought I looked good.
I typed out a message: {“How’s it different from the other pics you texted? At least it will disappear on here!”}
That seemed aggressive – even with Katie’s advice echoing in my mind. I fixed the wording a bit and ended up sending this:
{“No worries!
I like the other ones and those won’t disappear!
”}
The shower turned off and I heard Katie make her way to her room and close her door. Her words continued to play.
Well, if you want aggressive this is what I’ll give ya.
I dropped trow and slapped my dick around until I worked up a chub. Despite feeling extremely horny, the alcohol caused this to take some time. I walked naked over to Katie’s room, turned the handle quietly, and entered. Katie was standing in front of her mirror wrapped up in a towel. She was startled at first, but then began snickering. Not the reaction I was going for.
“What’re you doing?” She said in-between laughter. Her amused gaze at my penis made me self-conscious. I palmed my cock-n-balls with my hands.
“Was thinking maybe we could….you know..”
“Bang? Hahaha” She continued to laugh.
“Why are you laughing?” My face turned red. “I thought you said you wanted me to be more forward?”
“Did you miss the part about inappropriate timing?” She chuckled. “I
just showered. And Maddy is right next door and Mom is right downstairs.”
I just stared at her like an idiot.
“We’re not having sex, Drew. Get out of here,” she said. “Have a cold shower.”
I didn’t move, or say anything.
“Can I least
see something?” I asked “I’m horny AF right now!” I tried not to sound too whiny.
“No!” She laughed. “Get out of here, perv.”
Dejected, I slumped my head and turned to walk over to the bathroom.
“Drew?” Katie said behind me.
“What?” I turned back to her. She wore a sly smile.
To my utter thrill, Katie unhooked her towel and spread it wide open, granting me a full frontal look at her banging boobs and shaved kitty. She did an enchanting little “one-two” move where she moved her hips to her right then back to her left. Then she closed her towel again and shooed me away. I fapped in the shower and came within 20 seconds.