I watch as my Uber gets closer to my place. Each minute feels like agony. Finally though my driver arrives I’m off to the bar.
The bar we picked is pretty classy. Not the kind of place you hear loud music or anything like that. The kind of place where a cocktail can cost twenty five dollars. I walk in and the place is pretty slow. I’m also earlier than I thought.
The place is classier than I thought. Nice moody lighting and soft piano playing in the background. I walk up to the bartender and order a drink. Finding a nice spot where I can see the door but also gives us some privacy.
Time seems to slow as I wait. I tap the table again and again. My leg bounces as the anticipation builds. I look at my phone and only a minute or two has passed. Goddamn this is going to be torture.
The door opens a few times and my head shoots up to look. Only to find it’s a couple or an employee coming in. My foot tapping grows louder and louder. I almost can’t stand it.
The front door opens and my heart nearly jumps out of my chest as I see a hint of red coming around the corner. Following up from the mid thigh I follow the curves of her body. It’s absolutely her. The dress follows her curves up to her perfectly perky tits. Following up I get to finally see her face. The face that has been hidden for so long.
My heart nearly explodes followed by my brain. I can’t really process what I’m seeing. I feel the blood leave my face and the sound of the piano fades. My focus is purely on her face.
The face of my older sister Megan.
I don’t even know how to react as she walks towards me. Not a hint of confusion on her smiling face. Walking over to the table her hips sway perfectly. Her tits have a slight bounce.
“Hello Max! I see you have already started with a drink.” Megan says with a smile.
I just keep looking at her. My mind is racing with too many thoughts. I swear steam could be coming out of my head. Just looking at my sister I can see her nudes flash in my head.
“Are you going to offer me a drink? Vodka soda would be great.” She says.
I look around and continue to try and process. Robotically I get up and order her drink. Promptly bringing it back to her. Sitting back down I continue to stew in my disbelief.
“Are you going to say something or is this going to be a one-sided date?” Megan asks. Sipping her drink.
“How…did…I’m not sure…” I stammer.
“Haha seeing you flustered is kind of charming. Go ahead and ask.” She says.
“Did…did you know it was me?” I ask.
“I didn’t at first but you told a story that I recognized. After you sent some nudes I noticed a birthmark on your hip. By then it was too late.” She says.
“I haven’t dated anyone in years and we had already gone that far. So I figured a date would be fun.” She says.
“This…this is wrong. We can’t do this at all. We can’t do what we have already done. I…” I say.
“I find you attractive Max.” She says bluntly.
“I didn’t know it was you at first. Body type looked familiar but I wasn’t sure it was you. But once I heard the story you told and saw the birthmark I knew it was you. By then I was already attracted to you.” She says.
This is all so much to take in at once. I nervously sip my drink. Trying to think of the words to say. Trying to come up with something that can make sense of this. Megan breaks my train of thought.
“Are you attracted to me?” She asks.
What a question to hit me with at a time like this. Already processing that I sexted my sister and have jerked off to her nudes. Now she sits in front of me in a sexy red dress asking if I find her attractive.
What do I even say? Yes, I find her attractive. But it’s wrong. I can’t say that about my older sister. If I say no it could hurt her and she would know I was blatantly lying.
“I do, but not in a weird way.” I reply after a long pause.
“Hahahah okay, now we are getting somewhere. Not in a weird way though.” She says. Slowly sipping her drink after. Never breaking eye contact with me.
“How was work today?” She asks.
The very normal question kind of catches me off guard. It almost perfectly breaks me out of my train of thought. I switch back into a normal headspace.
“It was pretty good! Work is never really that hard. Just very boring most of the time. I’ve automated large aspects of my job so it’s mostly just plugging holes that happen along the way.” I say.
“Do you plan on staying there forever or do you want to move on to something more?” She asks.
“That’s honestly a good question. The company I work for is pretty solid. I can move up into senior positions and at times it feels like I’m being prepped for that. On the other hand I’ve seen a lot of good people get burned out at this company. So I’m kind of in a wait and see phase.” I reply.
“I’m so happy to see you doing well for yourself. You even shop like you’re doing well for yourself. That outfit fits your body perfectly. You look so handsome that I could almost see you before I walked in.” She says with a devious smile. She won’t let forget this is a date.
“How has your work been?” I ask. Attempting to change the subject.
“Ehhhh kind of on and off. I’ve been looking for a new opportunity and a friend reached out about a position at an airline. I would get to travel a lot and work on my tan. It’s a little less than I currently make but honestly the office is killing me.” She says.
I can’t help but notice how pretty Megan looks in the soft light. It makes her skin look perfectly smooth and really highlights the nice areas of her face. She must have noticed me looking because she gave me a warm smile.
We talk casually for a while. The conversation feels very natural and the awkwardness starts to fade a bit. The conversation swings back to how our messages were. Funny stories and talking about the future. By the time we are a few drinks, I’ve relaxed completely.
“So do you usually take a date home the first night or are you a second date kind of guy? Maybe even a third date guy?” She asks with a devilish grin.
“What do you take me for? Some kind of man-whore? Always a second date at least.” I reply, slightly slurred. I don’t drink often so I’m a little buzzed.
“I was hoping to see your place tonight but I can wait for another one, if I’m getting another one…” she says.
The combination of relaxed conversation and alcohol has numbed me to the fact that this is my older sister. I’m in the mindset of this being a date now.
“How about dinner and a walk along the pier. My treat, of course.” I say.
“I’ll be busy the next few days but how about Sunday?” She replies quickly.
“Sunday would be great.” I say as I finish my drink.
We both finish our drinks and it’s gotten rather late. Both of us have work tomorrow so now comes the awkward moment where one of us has to propose leaving.
“It’s getting a bit late for both of us I think. Should I pay the tab and walk you out? Or do you want another drink?” I ask.
“I can’t be too hungover tomorrow so I’m ready to go haha. I have some very long meetings tomorrow” she says.
I get up and pay the tab. Walking back over to Megan I’m struck by her beauty again. Sister or not she is truly stunning. The red dress she wears just shows her off perfectly. As she gets out of her seat I can’t help but give her a once over. It’s like time stops to admire her.
As I approach her Megan reaches out and grabs my hand. Pulling me close to her and gripping my hand tight.
“Let’s go, my handsome date.” She says.
We walk out of the bar where her Uber is waiting already. I turn to Megan to say goodnight and as I do I’m shocked by her slick and swift move. In one motion Megan slides her hands to my sides and pulls me close. She kisses me deeply.
This isn’t a sister kiss or even a first date kiss. This is a “I want you to rip this dress off kiss.” The energy she gives off is intoxicating and I can’t help but kiss back. I know it’s wrong but having such beauty gives you a deeply sexy kiss makes it hard to resist.
The honking of the driver breaks our kiss. Megan pulls away and her face is flush. She smiles at me in a way I haven’t seen before. She kisses my cheek and lets the kiss linger.
“Thank you for the wonderful date. I can’t wait to see you again.” She says with that warm smile. Getting into her ride for the night.
As she drives off I shiver. What even just happened? Even on my ride home I don’t even really have time to process it. I thank my driver and stumble up to my apartment.
Jumping in the shower I let the warm water bring me back to earth. The steam just takes all the weirdness away and lets me think. That was one of the best dates I’ve had in years, with the strangest person possible to have it with. I have a mix of excitement and confusion running through me.
Getting out of the shower I hear my phone ding. Wrapping a towel around my waist, I go to grab it. There is a message notification from Megan. I open my phone quickly to check it out.
My heart nearly bursts into a thousand pieces. She sent me a picture of her dress pulled up. Exposing the pink thong she promised to wear. Her ass is near perfection. I’m surprised her dress could even contain its size.
“It’s a shame you couldn’t see this in person tonight /:” says the message she sent along with it.
My cock was hard as soon as I saw the picture. I need release really badly. Walking over to the couch I grab my lube and start to get to work.
My eyes are fixated on my sister’s thong covered ass. I stroke slowly thinking about all the things I want to do to her. I know it’s so wrong but when you’re this horny it doesn’t matter.
I’m already close to the edge after just a few strokes. But Megan wasn’t going to let that be it. Another picture arrives. She pulled her dress down exposing her big tits. My sisters smiling face and tits are exposed in one picture. I explode all over my stomach. My orgasm sends waves of pleasure from the tips of my toes to my brain.
Ropes of cum spray all over my stomach. I groan so loud I’m sure the neighbors can hear. It takes me a few minutes to catch my breath and clean off my stomach.
The message with the last nude reads “Goodnight my sweet and handsome date.” I close my phone. When I stand up I’m seeing stars. Holy shit that was a powerful orgasm. Tossing the cum soaked towel I stumble into my room and fall onto my soft bed.
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