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Swipe Right Ch. 01
Hello and welcome to Swipe Right Chapter 1!
This originally was just going to be a one-shot story and be self contained. But as I was writing the length grew and I wanted to make sure it was easier on all of you to read. So I’m cutting it into two chapters.
With this story I tried to keep it as grounded as possible but obviously there is always going to be a level of suspension of disbelief.
I hope you all enjoy it and as always I encourage any feedback
All characters featured in this story are 18 years of age or older.
1. Losing track of people after college.
I think a lot of people have this idea that the people you are talking to right now will always be there. It doesn’t matter if it’s a close friend or even someone you work with for decades. There always seems to be the possibility of people just kind of fading out of your life. It’s kind of sad but it also is just one of those aspects of this crazy thing we call life.
That’s what happened to me going into college and even after. Friends I had freshman year had come and gone by junior year. A coworker I was close friends with doing IT left for another company. I thought we would be gaming every night even after he was gone. But within a month we haven’t even sent a single text.
Two years down and a promotion later it seemed like even my family faded into the background. We were never really a close family. I don’t mean that really in a bad way. We still went on vacations together and attended each other’s functions but weren’t really a family that was always in communication. None of us are super active on social media, if we even had any.
My parents both worked in academia. My father was a professor of economics and still teaches today. My mother is a former professor, now she’s the Dean of a private school. They never really pushed me and my sister into that path. They just asked that we go to school and go into something we enjoyed. Being big into computers I took the soul crushing route of going into IT and network security.
My older sister Megan took a gap year before school. Not really knowing what she wanted to do. She did some traveling and a lot of drinking. Eventually she settled on a business degree. We haven’t talked in years so I’m not exactly sure what she's doing. It’s been so long I can’t even really even remember what she looks like.
After me and Megan were off at school my parents started to travel more. Getting closer to retirement they wanted to get a head start on really enjoying life. My mom would call to set up a dinner or get together and two weeks later I’d get a call that they would be traveling to Austria or China. After a while planning didn’t even really happen anymore. Just an occasional call on my birthday.
This all might sound very depressing but to me that’s just how it was growing up. Our family dynamic just wasn’t that close. I’m happy where I’m at and I’m glad they are too.
2. The Daily Grind
I had heard that going into IT can wear you down but honestly it’s not too bad. The scales on my career path were also tipped a lot. One of my professors wrote me a glowing letter of recommendation to a company and after graduation they took me without even needing a second interview. Not having to cut my teeth doing help desk or anything like that. Pretty much went straight into network security.
My day is generally pretty easy. Start my day at 9:00 AM, usually with a meeting. Sit through that while sipping my coffee. Go to my office where I read through maybe five or six emails. Then just sit and wait for problems to pop up or my phone to ring. When 5:00 PM rolls around I walk my happy ass out the door.
I live and work in the city and was lucky enough to get an apartment within biking distance of the office. So most of the year I just bike to work. Even in the winter I sometimes don’t bother to get my car out. There is nothing that drives me nuts more than traffic.
Getting home I usually grab a quick snack and head down to the gym. Paying extra for a nicer apartment has its perks. A full gym and a very nice pool. Even have a little grocery store downstairs.
Generally I don’t workout too much. Just enough to keep me in shape but by no means am I jacked. Swimming for years has kept me lean with some nice muscle mass. I try to keep that consistent look and nothing more.
After the gym I like to sit back and relax. Usually with some video games or going to a nice bar down the street. Have a few beers while I read a book or scroll through the news.
I’ll be honest that it does hit me that the 9 to 5 lifestyle has me pretty captured. I do my little activities after work at my decent job and maybe go “crazy” by getting takeout or having a nice dinner out. Usually I avoid the clubs around here. Not that they are bad, just not really my thing.
Doing the daily grind can make time pass quickly. Sometimes I feel like I “wake up” and it’s a month later.
3. Dating in the Big City and Fond Memories
Dating for me hasn’t ever really been an issue but gaps in girlfriends isn’t too uncommon for me. I’m mostly fine living by myself but there are times it gets to me. I could easily go out to a club and probably pick up a girl. But that does get boring after a while, I’d rather have something more concrete.
The longer relationship I had was with this girl Sammy starting my freshman year of college. She was a great girl and we had a lot of great times together. We met in a very boring chemistry class. We ended up passing notes about how boring the professor was.
Passing notes turned into texts and eventually a date. I was super nervous that night. As soon as we got together I could tell she was just as nervous. We went to dinner then a movie. After the movie we walked around town for what seemed like hours. The nervousness was gone and we both just relaxed.
It was two or three dates later that I asked her to be my girlfriend. I remember asking her as we walked back to her dorm. We ended up making out on a bench for what seemed like hours. I remember she stopped kissing me and looked me straight in the eyes.
“Max, your roommate is gone right?” She asks.
“Yeah! Went to see his parents for the weekend.” I replied.
“Let’s go back to your place…” she said as she got off me. She grabbed my hand and pulled me towards my dorm.
My heart was racing the whole way. I’d had sex before but not with someone as gorgeous as Sammy. She was a little shorter than me with shoulder length brown hair. She played volleyball so her body was super tight. Breasts on the smaller side but from grabbing them while making out they were a nice handful. Her ass was beautiful. Volleyball had shaped it into perfection. It wasn’t big but in tight jeans it had a nice shape.
We snuck into my dorm while trying not to laugh. We rushed up to my room like two little spies. I quietly opened the door and we both rushed in. As soon as the door closed Sammy pulled me close.
We made out against the door for a while. I had a feeling I knew what was coming so I slid my hands under her sundress. Holding her perfect ass in my hands. She moans while kissing me but breaks off the kiss.
“Lay back in the bed baby” she says. Her voice is so sexy that I’m already hard. I step back and fall onto my bed. Adjusting a pillow under my head so I can look at her better.
Sammy sways her hips and smiles at me. Running her hands all over her body. Giving me a sexy little show. She gives me a seductive look as she grabs the straps of her sundress.
“Go ahead baby, I want to see you” I say. Her smile grows bigger and she blushes a little. In one slow and sexy maneuver she drops the dress to her feet. This tanned goddess stands in front of me in just a red lace thong.
My heart was pounding and I could tell hers was too. I had seen her nudes before but her body In person was even better. She tanned often and it was nice and even all over. Her nipples were small and looked perfect to suck on.
She started to approach me slowly. Letting her hips sway and keeping eye contact with me the whole time. She got on the bed and straddled me.
“Let me make you feel real good baby.” She says. I don’t even reply. I’m just mesmerized and wait for her next move.
She kisses me deeply and tugs on my shirt. I sit up and she helps me take my shirt off. I lay back down and we kiss again. Our tongues danced in each other’s mouths. Sammy breaks the kiss and starts to kiss down my body. The sensation is incredible. Like every kiss sends electricity through my body.
She works her way down to my stomach and slows the kisses down. Working her way carefully to my belt. Once there she looks up at me with lust in her eyes. Skillfully she undoes my belt.
She pulls my jeans and briefs off In one go. Tossing them to the side she looks down with hungry eyes at my hard cock in front of her. We have sent nudes so she had seen it before. But I think seeing my nice six inch cock in person works her up even more.
She leans down and starts to kiss my cock. I’m pretty thick and I think that’s turning her on. She kisses up and down the length while keeping eye contact the whole time. I’m so turned on I almost have to look away so I don’t cum.
When she kissed the head of my cock and started to take me in her mouth I felt like I was in heaven. I had gotten a few blowjobs before but I could tell Sammy was a pro. She started to work my length into her mouth while using her hand on my shaft.
I groaned and moaned as she started to expertly suck my cock. I had to look up at the ceiling as she did. I would have blown my load down her throat if I looked at her. The sounds of her sucking me off filled the room. She stops for a second but continues to jerk me off.
“You like that baby? You like how I suck on your nice cock?” She says. Her voice filled with lust. Her tits shake as she jerks me off.
“Fuck yeah baby! Goddamn you’re so sexy” I almost can’t look at her as I reply. She smiles knowing how well her magic is working.
“You want to fuck my tight pussy tonight? You want to make me yours?” She says. Slowing her strokes a bit.
“YES! I want you so bad!” My voice nearly cracks.
“Make me into a little slut tonight. Cum in this pussy and make it all yours.” She replies. She stops jerking me off and slowly leans back onto the bed. Legs spread wide.
I get on top of her and we kiss wildly. I play with her tits which causes her to moan. She grinds her thong covered pussy against my cock. We both moan and groan back and forth.
I break the kiss and start to kiss down her body. Starting at her neck and working my way down. Getting to her tits I start to suck on her nipples. Her reaction is immediate. She moans loudly and runs her fingers through my hair. I alternate between nipples, making sure they both get love.
“Please baby I need your cock! I’ve needed it for so long!” She says between moans.
“You want me to eat your pussy first baby?” I replied.
“Later baby, I need to get fucked right now.” She says. I don’t want to keep a lady waiting long. I sit up and as I do she pulls her thong to the side.
“Slide that thick cock in me. I need it!” She says. Sammy had told me that I would be the thickest cock she’s had. So I slide it in slowly at first. The feeling of her tight pussy parting way for my cock in mind blowing.
“Push it in babe. I can take it all, I want you.” She moans.
I slide my length all the way into her. She’s dripping wet and that’s good because she’s tighter than anyone I’ve been with. I start to slide my length in and out of her slowly.
Sammy moans and groans as my cock proves her deep. The sound of her wet pussy getting filled is music to my ears. I started to pick up the pace and she loved it.
“Yes! Yes! Fuck me baby. Make me into your little slut! I love that thick cock!” She screams. I’d never been with a girl who talks so dirty. It almost drives me over the edge but I persist.
The bed shakes as I fuck her pussy harder. It’s all instinct at this point. Our eyes are locked as my cock fills her tight pussy again and again. There is no way the whole hallway can’t hear her get fucked.
I slow down a bit but concentrate on long strokes. I want to catch my breath for a bit but I can tell Sammy wants to give me more rest.
“Fuck me harder baby! I’m a little slut for that cock and I need to get filled! She says after a long moan. So I picked up my pace again. I start using her like a fuck doll.
At this point the room is loud with the sound of our fucking. Sammy’s wet pussy getting punished. Our moans in between indiscriminate swearing. The energy is thick and the end is near for both of us. Sammy can feel it coming.
“Fuck me baby! Fuck me like a good little slut! Fill me with your hot cum!” She says.
“I need it! I’m so fucking close I need your cum!” She says after a moan.
I thrust in harder and harder. I’m exhausted at this point but I can feel my orgasm coming. Looking down at Sammy’s bouncing tits does it. I groan loud and thrust in deep. Ropes of cum shoot deep into her pussy. Still to this day I don’t think I’ve came that hard before.
I collapse on the bed next to her and we cuddle for a while. But that wasn’t the end of the night. We spent the night fucking all over my dorm room and once in the shower. I came in her and on her. It was one of the wildest nights I’ve ever had.
Sammy and I dated for another two years. The relationship was great the whole time. She ended up getting accepted into a study abroad program and we mutually decided we didn’t want to date long distance.
After Sammy I had some flings here and there but nothing really of substance. Especially as I was finishing up school and going into a career I just didn’t have the time for anything more. For the most part I’m not a one night stand kind of guy but have had a few.
4. Getting Back in the Game
Today at work a coworker mentioned a new dating app that just released a few weeks ago. I had used a few of them with very mixed results. But he seemed to swear by it. Saying that he had a date last night and the girl was great. They already set up another date next week. It’s gimmick is that profiles just use usernames so you can more anonymously browse potential dates.
The conversation quickly shuffled into the back of my brain. Work was kind of busy so I didn’t have a lot of time to think about it. It only came back to mind when I was at the gym after work. I thought “Ehhhh what the hell. Maybe I’ll try it out.” I figured there was no harm in just setting up a profile.
I finished up at the gym and head up to my apartment. In the showers I think about it more. I’m a bit more settled now so why not try to get out there. Even if I have a few shitty dates I might find someone decent. Plus I don’t mind an excuse to get dressed up and go out to dinner.
Finishing up my shower I whip up a quick dinner and grab a beer. Settling on the couch to relax and set up my profile. The download went quick and registering my account was pretty painless. The hardest part was picking a decent username.
I filled out my biography and answered some starter questions they had. Some of them I think I may have put too much thought into. Sometimes I have the tendency to get overly long. But some people find that kind of charming. So I’ll take it!
Pictures were kind of an issue. A lot of my friends aren’t the type to take pictures at events. A lot of what I have are from my freshman and sophomore years of college. At that time I didn’t have a beard and was way less tan. I’ve filled out a little more and I’ll be honest, finals aged me easily a decade. So I can’t really use pictures from college.
I scrolled through hundreds of pictures just so I could find three kind of alright ones. Plus for good measure I took a classic mirror picture in the bathroom. With pictures sorted out, I was ready to browse!
The first few profiles I saw were pretty promising. I ended up tapping the green check mark on a few right off the bat. If you aren’t familiar with the modern dating app, most use a common system. If I confirm I like a girl's profile and she later does the same, we match. From there we can start chatting.
I finish my beer and go back to checking out profiles. I don’t generally have a lot of preferences when it comes to who I date. It mostly falls into whether I just find someone attractive or not. It’s not like I have a hard line I draw in terms of looks. Which is nice because that leaves a lot of possibilities open.
Personality wise is where I’m a little more strict. I need to be engaged in conversation with someone. Not in the sense that we always need to be talking about deep matters of life and death. More so I just want to feel like some of our conversations are going somewhere. Combine that with good humor and you have the perfect girl for me.
A few beers later I think I’ve reached a point where I can’t look at any more profiles. Now it’s kind of the waiting game to see who matches with me. Getting up from the couch I clean up the dishes and do a little cleaning around the kitchen.
Putting my phone on charge, I fall into bed and drift off to sleep.
Morning always comes too quickly. No matter how many times I wake up for work, grogginess consumes me. Checking my phone before my morning shower I see a few notifications of matches. I don’t have a huge amount of time in the morning, so I tend to just go straight to getting ready. I can play on my phone at work so I’ll check my matches then.
After a quick shower and a cup of coffee I set off to start my day.
This morning's meeting was especially boring. We all are in the IT field and most of us specialize in security. Yet we have to have meetings about strong passwords and not using public wifi for work. Just the most boring stuff imaginable. Even worse this morning because I knew I had matches waiting. My boss finally closed the meeting and I rushed off to my desk.
Opening up the app I see fifteen matches. Scrolling through the many beautiful faces I’m excited by the possibilities. Checking my messages puts a damper on that excitement. So many messages from bots asking me to open up links to sketchy websites. I’m used to fake accounts so I’m surprised I didn’t spot some of these. I start deleting and reporting messages.
Scrolling through one girl's profile picture catches my eye. A blonde in a short red dress. I tap her profile to jog my memory. I remember this account! A lot of her pictures were kind of blurry and not the greatest. But her answers to a lot of the questions the site asks you were really good.
Her body in some of the pictures looks really good from what I can see. She doesn’t look that tall but absolutely not short. The dress she is wearing hugs her body and you can see every curve. She clearly keeps in shape and does a lot of squats. Her ass looks like it would feel nice in my hands. She isn’t lacking at all in the boobs department, they look rather big and perky.
Luckily she’s online now so I send her a message back.
“Hey! Glad we matched. Your answers to a lot of the questions were really good. Some honestly gave me a good laugh.” I reply.
Going back to work I feel my phone vibrate and smile when I see she replied.
“Hey thanks (: is there one in particular you really enjoyed?” She says.
One of the questions was “What is your most embarrassing drunk story?” She had a story about being in Vegas and trying to hit on a blackjack dealer while drunk as a skunk.
“The Vegas story was very funny! I’ve never been there myself but that sounds like a blast!”
“Oh you NEED to go! We had so much fun on that trip. Me and some of the girls from work went. That night we got kicked out of a casino for grinding on slot machines for good luck.” She replies.
I just keep my phone open at this point. I have my own office so it’s not like anyone is going to care.
“Did you black out? Haha” I reply.
“Pretty close! I think we went to some awful buffet and walked around the strip until 4am. I have never been that hungover in my whole life.” She says.
We continue to talk about Vegas while I finish another beer. We continued to message for a few hours. Sharing stories and laughs about each other’s past failings and triumphs. It feels great to finally feel like I’m getting back in the game again.
I finish two or three more beers and with a buzz going I tell her I can’t stop looking at her pictures.
“Is that so? (;” she replies.
“Well if you’re a good boy and play your cards right you might see much more”
My heart starts to beat faster as I reply.
“I’m always a gentleman whenever possible. I don’t think we will have any issues”
We flirt some more but it’s getting late. I need to at least act like I’m going to get some sleep before work. I message her that I’m laying down now and we exchange good nights.
As I lay in bed I can’t help but feel excited. Like I’m waiting for Christmas Day. I just want to pick up my phone and start chatting again. But I know I need to sleep. Slowly I drift off into a wonderful dream.
Morning comes too soon. My alarm blaring echoes through my head. I stop my alarm and notice a few notifications on my phone. Messages from that girl last night. My heart starts to race but I have to get ready before I reply.
Quickly taking a shower and throwing my clothes on, I open up my phone.
“Good morning! I had such a fun time talking last night. I hope we can continue…” she says.
“I had a ton of fun! I would love to keep talking. Maybe even grab a drink?” I reply.
Grabbing my coffee I head out to work. There is a nice little skip in my step this morning. It feels good to be back in the game and talking to someone so beautiful. My bike ride feels like I’m the main character of a movie.
Luckily no meeting today so I got right back to replying to her. We talk back and forth so much that I almost don’t pay attention to work at all. A permanent smile is plastered on my face as we tell each other stories and talk about how boring our jobs are.
My day passes quickly, so quickly I almost forget to leave at 5. Packing up my things I tell her that I’m about to bike home. On my ride back I’m still on cloud nine. Just full of a new energy I haven’t felt in awhile. I can’t wait to go on a date with this girl.
I don’t think I’m going to work out today so when I get home I just jump in the shower. The hot water feels so good and refreshing. Almost perfectly relaxing my body for what’s to come. When I get out of the shower I check my phone and notice a notification.
“Guess what I did today!” she says.
“What would that be?” I reply.
“I wanted to pick out a new outfit and ended up wandering into a new lingerie store…” she replies.
My heart is racing and I’m instantly hard. I hope she’s not just doing this to tease me. I find it hard to reply with my hands shaking.
“Oh really? Did you get anything?” I reply.
“Do you want to see?(;” she quickly replies.
I don’t even hesitate. My fingers quickly type my reply. “Yes of course!” My heart races and I’m hard and ready to go. She reads my reply but doesn’t answer right away. Time seems to slow and what was probably two minutes feels like an hour. Three pictures pop up and my soul leaves my body.
All three seem to be taken in a dressing room with care taken to not show her face. The first picture nearly kills me. She poses in a pink lace bra and panties. From the cut it looks like a thong. Her body is like that of a goddess. The bra can barely contain her tits. They so badly want to push the delicate lace out of the way.
The second picture she is wearing a red lace teddy. It’s just barely see-through enough that I can see her nipples. The tight teddy perfectly hugs the curves of her body. She clearly keeps herself in shape and tans often.
The third picture is of her in a mesh bodysuit that nearly has no material. She teases me by covering her tits and pussy. I can’t see her face but I know she has a wicked smile. I scroll through the pictures several times. My heart is beating so fast I think I might die. I could tell she was sexy from her profile but this elevated her to a whole new level.
“Like what you see?(;” she replies. Breaking me out of my trance.
“I won’t lie, I’m blown away. You look incredible in all of it. Just…wow…” I reply.
“What’s your favorite?” She replies.
“It’s impossible to pick honestly. It all looks so good on you. Some great choices that really show off your amazing body.” I reply as I relax on the couch. Still hard from the pictures.
We reply back and forth a bit and it’s clearly heating up. She talks about some other sets she looked at and what she likes and doesn’t like.
“I wouldn’t mind having some of this stripped off of me to be honest…” she replies.
“Oh really? Well I happen to be free” I reply.
“What would you do after you had me naked?” She replies back quickly. My cock is throbbing so I pull it out and start to stroke.
“Run my hands over that beautiful body. I'll just take you in for a while. Enjoy how sexy you look” I reply.
“You like taking it slow?” She replies
“Generally yeah! Especially with someone like you. Someone who clearly takes care of their body deserves to be enjoyed slowly.” I reply as I slowly jerk my cock.
She sends me another picture. This one is her posing in the mirror showing off her ass. Confirming my suspicion that the pink lace panties were a thong. Her ass looks amazing. Perfectly shaped and made for a good slapping.
“You like? (;” she sends with it.
“Fuck…absolutely. Your ass is perfect.” I quickly reply.
“Did I make you hard?” She replies.
“I’ve been hard for the last 20 minutes.”
“Show me.” She replies instantly.
With my cock already in hard I maneuver to get a good picture. I get some good lighting and snap a picture. Sending it to her with “you like?”.
“Wow! Nice and thick, and your length is perfect for me.” She replies.
Our messages grow hotter and hotter. Sending pictures to each other as the heat rises. It’s been a while since I’ve sexted so this is perfect. Just a slow burn.
“I’m free tomorrow, do you want to get drinks?” She asks.
“I can do that! I’d love to” I reply.
“Do you want me to wear these pretty pink panties under my sexy red dress?”
“Please do, I’ll be thinking about them all night” I reply.
“Are you going to be thinking about bending me over the bar and taking me right there?”
“I was thinking about the car after, but that works. I wouldn’t mind pulling that dress up and yanking your thong down. Just sliding my full length inside of you right there.” I reply.
“I’m pretty tight so you’ll be stretching me out. Are you going to fuck me hard?” She replies.
“Oh the whole bar and maybe the block will hear you get fucked. I’d give that ass a few hard slaps as I pump my cock deep inside of you”
“Fuck my pussy is so wet thinking about it. Do you want to cum inside of me? Right there in the bar?” She replies. The energy is getting hotter and it’s hard not to cum as I jerk off thinking about her.
“I think I’ll have you drop to your knees and have you pull your dress down. So I can cum all over your beautiful tits.” I quickly reply.
She sends me a picture that nearly makes me cum. Her tits are on full display, evenly tanned with perfectly sized nipples. They are probably DD, maybe a bit smaller.
“You want to cum on these tits?” She adds to the picture.
“I want to cover them in my hot cum.” It’s getting hard to reply. I need to cum so badly and luckily she gives me a reason.
“I want you to jerk your big cock to my tits. Cum for me baby. Cover those tits with your cum.” She replies.
I don’t need much more encouragement. My cock spasms and my body shakes as I shoot a huge load on my stomach. Rope after rope of cum spews out of my throbbing cock. My toes wiggles as an intense orgasm flies through my body. It takes me a second to catch my breath.
“Goddamn that felt good!” I reply.
“Did you cum as hard as I did?” She replies. Knowing she also came sends a shiver down my spine.
“I came a huge load. Holy shit it’s been a long time since I came that hard” I’m still catching my breath as I reply.
“Good (; I can’t wait to see you tomorrow. Maybe if you're good I’ll make your fantasy a reality.”
We talked a bit more before both saying goodnight. I jump in the shower excited as could be for our date tomorrow night. It’s hard to even shut my eyes. I'm so excited. Eventually my eyes close and I slip off to sleep.
5. A Shock to the System
My alarm going off shot me out of bed in an instant. I was almost ready to go as soon as it went off. The excitement in the air was thick. Springing out of bed I head straight to the shower. It’s like I’m floating on a cloud of good energy. A smile permanently on my face.
Getting out of the shower I check my messages. There are several from her already. Opening them I find a picture of her in a sexy red dress. Skin tight it hugs her body and just barely covers mid-thigh.
“I can’t wait for tonight (; dress to impress” she says.
“Oh I have just the outfit for tonight. You look so sexy I have to match that.” I say.
My ride to work is a blur. My bike seems to guide itself to the office. I could have been hit by a car and never noticed. Not even a two hour meeting about password safety could kill my mood.
Sitting at my desk messaging her back and forth one of my coworkers notices my happy aura radiating off of me.
“What’s got you so happy?” He says.
“Big date tonight! Met a girl who’s extremely smart and even more good looking. Just really ready to get out of here.” I say.
He just smiles and walks away. He’s an older guy so he knows that young love feeling. I continue to work diligently but can’t help but keep checking the time. Counting down the minutes until I can get out of here.
Relief comes quickly though when the clock strikes 5:00 PM. Logging off and grabbing my things I race downstairs to ride home as quickly as possible.
The outfit I picked out is smart and classy. Not too dressed up but enough to impress. With our outfits we will absolutely be the talk of the bar. I make sure to do a deep cleaning in the shower. Taking my time after to make sure every hair is just where it needs to be and my facial hair is neatly trimmed.
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.
I think about Megan and our date I’m a few days. What she might wear and how she might act. I know this is all so wrong but she seems to not be bothered In the slightest. Should I act accordingly then? Act like this is all just fine.
All these thoughts and the alcohol start to tire me out. My eyes start to shut, slowly at first. I struggle to fully get on my bed before my eyes shut completely. I slip off into a dream as my last thought of the night flows through me.
I have a second date with my older sister in a few days.
End of Chapter 1
Too much of a cliffhanger?
For a story like this I didn’t want to rush an ending. So I think a split into two chapters is a lot better. I should have the second chapter done in the next few weeks. I hope you all enjoyed it and I can’t wait to read your feedback. Don’t be afraid to reach out!
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