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Sex with a Waitress (M/F) | 2016
This just happened yesterday, and I just woke up so I'm pretty tired but It's best to write fresh off my mind. First post here, since I love reading your experiences, I wanted to repay you guys. Sorry for spelling/grammar mistake and bad word choice, I read through it 3 times but say something if you see an error. You can skip a few paragraphs to go right into the sex.
Background (not really needed, but other posts do this so why not): I'm 21, 6'2 185lbs, no six pack, but a 4 pack and defined arms and legs.
I live in NYC, and every Saturday after my last class of the week I go to my favourite diner at lunchtime to give myself a pat on the back for all my hard work. I sit on the bar stool things, mainly because I go by myself and the couches are meant for 4 people not 1. While I finish up my fries, I look up and catch her eye.
This girl was just wow, New York has some wonderful ladies from all around the world, but this girl was just, wow. There's so many things by just her appearance, she is a brunette, white (tanned a bit), american, with long hair, but not too long, but slightly curly. Her eyes were the most beautiful I've seen, blue and bright, and the face ended with her moist, red hot lips. Her boobs were perfect, I don't know bra sizes but they were more than enough, but not too big, and it was so hot just seeing some of it stick out of her hot short dress. Her arms, legs, and stomach, were so perfectly shaped, it was obvious she spent time working out. But now onto her ass, I love curvy, round ass, as much as you do, and trust me she has one, sadly her dress ended by mid-thigh, but you could definitely see the shape of it, if that isn't a perfect ass I don't what is. She's pretty much flawless in my eyes.
Now, back on to the story, when I saw her, I immediately got a boner, and I normally have medium sex drive with good self-control, but she was something different. I like having conversations with people next to me since NYC is a very social city, but I wasn't interested in anyone but her. While I kept having a look at her while she kept serving food, she gave me several looks back with a small grin on her face. I was assigned to a different waiter, but a few minutes afterwards I saw her talking with my waiter, they nodded, and they soon split up. And then she came up to me. Lets just call her Natalie.
Natalie: "Would you like anything else?" with a smile
Me: "No thanks" with a smile back
Natalie: comes back saying "Cash or Credit?"
Me: me trying to be smooth saying "Cash, because I want to use my Credit to buy you dinner tonight" The guy next to me blurted out laughing.
Natalie: "forced laughter, haha sure, that's new one." then takes the money
Natalie: "I'll be off my shift in a few minutes, do you wanna walk around after?"
Me: "Sure" (you don't know how ecstatic I was)
Me: Me impatiently waiting
Natalie: "Alright I'm done, shall we go"
We walk out together, turns out she was a smart gal, goes to college but needs money to pay off her rent (apartments here are expensive as fuck), and she's studying business. We have a lot of things in common, and I immediately thought to myself "great, she has the perfect appearance, and personality, I can not fuck this up".
Natalie: "I gotta go change out of my work clothes, my apartment is a few blocks away, do you just wanna come with me? I have a roommate but she has late shifts on weekends.
So I go into her apartment (great location btw), The apartment is pretty standard 1 bedroom apartment, it contains a small kitchen, a living area with a tv, a couch behind it, a dining table behind the couch, a bathroom, and a bedroom with 2 beds (the bed for the other roommate). She just tells me to sit down on her bed while she gets dressed, she takes some clothes out of the closet and watch her ass out the door. Then she comes out with no pants on (sadly still with a tank top and underwear) with me seeing her sexy legs and her shape of that beautiful ass, and she says "Sorry, I just realised my jeans don't match with my shirt" (I don't really care if she did this by purpose or not, but it was so fucking hot), me stuttering "That's alright" and my dick flies upwards in my jeans so she can obviously see it.
She slowly walks to towards me while I'm still sitting and says "I know we've known each other for an hour, but you seem like a really nice guy." She jumps right on top of me and we make out for 5 minutes, her lips are so soft and her boobs are so nice as I slide my hand into her tank top. I can feel her already getting wet. After the make out session was done she kneels down and says "it looks like you need help with that". I quickly say "I sure do". She suddenly turns all dirty and she ends the convo "I am a dirty whore and I need your cock in my mouth" with a sexy grin (I was surprised at this, no girl I've been with has escalated this quickly). She unzips my jeans and slowly places her hands on my rock hard 7in cock, and starts stroking it nice and steady. After a minute of so, she wrapped her lips around the tip of my cock, licks it, goes back, and now sucks a bit further now on the shaft, wraps her lips and feel her lips go around my cock, holding it in for a few seconds, than pop out. Now she's on mid cock, slightly struggling, but she puts effort into wrapping all of it in her mouth, licks it, and pop backs out again, the teasing was a pain and pleasure. Finally, she went as far as she can go down, probably 5inch deep, and i could see her eyes in displeasure and hear her choking, she holds for 10 seconds, and quickly takes it out of her mouth and starts breathing heavily for a few seconds, than looks up to me and says "I'm your slut now"
I was beyond turned on, I wanted to fuck her hard and show who's boss, I take off her panties (her tank top still on) and I lay down on her roommates bed. She sits down right on top of my penis, shushes me, bends down, and she whispers in my ear "I want you to fuck me so hard until i feint from your thick cock", I could easily tell she was incredibly horny. I could not hold in my sexual excitement, but in the cowgirl position, I slowly inserted my 7inch dick in her nice, tight, pink pussy until I was bals deep, I was going back and forth slowly so her pussy could accumulate to it. She was moaning incredibly hard, even at going slowly, she remembered there was neighbours so she tried to keep quiet, it's so hot seeing a girl trying to control her pleasure. Her pussy was so tight and felt like I was going to explode the second I put it in. I could not control myself, so I went for it, I thrusted fast and hard, she was screaming, she gave no more fucks about anyone else around. My cock kept sliding back and forth inside her nice, juicy pussy each time under half a second, This unbelievably hot thrusting lasted 30 seconds because I did not want to ejaculate early. I stopped, she was gasping for breath, but she immediately put my cock back in her wet pussy, and rode it back in forth so perfectly, I slapped her perfectly arched ass as she went faster and faster, she was moaning hard as I kept slapping her ass to go faster. It was obvious she was near orgasm, and I was too. I quickly asked her "Are you on birth control?", she nodded in response. I went back into control and slid back and forth grasping onto her perfect ass. I threw off her tank top so I can see her boobs. Everything is coming together, me grabbing onto her ass, seeing her perfect boobs wobble, my cock getting in and out faster and faster, and her getting near orgasm. I moaned, my cock cummed into her stimulated pussy, and while I was having the best orgasm of my life, she was having it too. She was screaming and her legs were shaking with no control, she went into my body so her boobs were against my chest, and I could feel her pussy juice leak out on to my dick, which just made things hotter. My orgasm felt like 30 seconds while semen was just non stop leaking out (keep in mind I haven't fapped in 2 weeks before this). Finally after we were done, she just laid on top of me, she smells so good. Both of us trying to catch our breaths, she muffles out "oh, my, god", 5 seconds later, I respond with, "We're not over yet".
While my cock was readying up again, I laid her on the bed, spread out her legs, and immediately start giving her oral, I know I already said it, but my god her pussy is beautiful, my cock was already starting to harden again. I start licking her clit like it was my last lollipop of my life, and I can already see more juice coming out. After done with oral, I start using my talented right index finger and start rubbing her clit hard and fast. She was pleased, she was moaning and just gasping out "harder". More juice coming out, I can feel another orgasm coming. I wanted her to feel like the slut she wanted to be, so I stick my left index finger into her extremely tight asshole, and she is going crazy. My right finger rubbing as hard as it can go, and my left popping in and out as fast as I can in her asshole. She is moaning hard, then goes silent, she starts squirting and moaning even louder, now I was concerned about the neighbours. It was so hot seeing her get so stimulated and squirted, so I went even harder and faster with my fingers, she kept squirting for a good 30 seconds, it was so sexy to me, I couldn't wait to put my cock back into her now. My cock, chest, and face were all covered in her juice, which just made me horny as I was before. She laid down and decided I should give her a 1 minute, but she was more than ready after 30 seconds, while I was sitting on the side of the bed and she was still laying down, she said it nice and loud "What the fuck are you waiting for?"
I rush towards her, I go into missionary and put both of her legs upwards so I can see part of her ass. My cock slid right in, it feels even nicer than before. She moans again and says "oh my fuc..." and I go faster and faster. I thrusted in and out like I was trying to make a fire, she and I were in immense please. After a minute, she says right into my face while still being thrusted "Treat me like I'm you're whore", I smile and reply "get in doggy style", after I make my final deep thrust in missionary (and she ended with a nice scream). I slid out, and she quickly got into position. You can see her ass pop out of her, her boobs hanging down, and her wet, dripping pussy sticking out, this was a perfect position for her. I quickly kneeled and started fucking her like no tomorrow, I took her hair and pulled it back, while using my left hand slapping her god-given ass. She loved the domination, I leaned towards her and said "You're my bitch", and fucked her even harder. After thrusting my rock hard cock in and out, she was near orgasm AGAIN, I don't even know how, but I'm not complaining. I slide out and say "stay where you fucking are", and start fingering her wet asshole and pussy at the same time, she was moaning "ohh" and it just got louder and louder until the orgasm came. I popped both of my fingers out right before she was about to orgasm and start rubbing her clit hard as she squirted out her nice pussy. She was out of breath afterwards, but just after 10 seconds she said "get on the side of the bed, I have to pay you back". While I was getting in position, she went to get a rubber tie thingie from her counter and tied her hair. I had no idea what she was about to do. She looked at me and said "don't move." She kneeled down so my dick was facing the back of her head. She lifted her head backwards so her hair was touching the tip of my hard cock (I asked her what this was afterwards, apparently its called a "hairjob"). I don't know why, but this was so stimulating to me, each hair slightly touching a side of my penis, while looking at her beautiful body. Since my body needed a bit more movement to cum, she turned around grasped my cock at the bottom jacking it off with her right hand while sucking it with her wet mouth, which was more than enough to get me done, but she wasn't finished.
She took out her mouth from my cock, and said "Are you ready for this?" with a smile, I replied "I hope". She started by jacking off my cock with both hands while her amazing tits were surrounding it. I was in heaven, this was easily the best feeling I had in my life. She removed her hand and used both of her hands on each boob by squishing her boobs up and down against my cock. I was in deep pleasure and I couldn't hold it in longer. I blew up, my thick cum was going all over the place, her tits, her face, and some even on her hair. All while she was still moving her wet tits up and down. I did not want this to end, but after 7 squirts all over her sexy body, there was sadly nothing left in the tank. Afterwards, she ended the wonderful sex by sucking my cock dry for a good 30 seconds, she wiped off a piece of cum on her cheek with her finger and slurped up the cum into her throat, gargled it, then swallowed (I wanted to stay in hard mode but my Penis didn't).
We laid in bed for 10 minutes with a bit of kissing and romantic talk and after she took a shower, I joined in after 3 minutes, no sex, just some kissing. We were both completely exhausted so we planned the dinner for tomorrow (today), and I got into a taxi and went home. As for the relationship, we're texting a lot and we seem to have a lot of stuff in common, I can feel this one is going to hopefully go far. I've never felt this sort of love in a while.
Can I tell you what's better than sex? 4:30pm sex
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