Fucking the wild big-titted waitress who wouldn't stop talking about her situationship

This was a story that I've had on my "don't tell this one" list basically since I started writing and sharing my experiences because it's a little bit on the weird side with lots of dumb decisions. Like I'll admit, I should not have done this. Recently I've been thinking back on it and kind of laughing because it's a little silly, so I'll see what you all think of it. It's a long one though I'll admit, with lots of back story, so if you wanna get to the good stuff go to the ---.

It starts when I was on a business trip back east in around September 2023. The actual business portion of it was fairly uneventful but because of delays with my first flight, I ended up missing my second flight from St. Louis back to LA. It's Delta so of course I'm told "well, there's no flights until the morning, but we won't put you up in a hotel, so just sleep in the terminal tonight." Fuck that. I have family in St. Louis. I rescheduled the flight for Sunday (it was Wednesday), called my boss to tell him I wouldn't be back until Monday, and Ubered to my cousin's place.

It was a nice little impromptu vacation and a much-needed slowdown as I was having trouble back home. See this was around a time in my life when I was really caught up on one particular girl who wanted nothing to do with me romantically. We all know that feeling, and it sucks. I was fine staying friends, but I needed time away to rewire my brain.

One day my cousins and I all decide to get lunch at the restaurant that one of them worked at since she gets a discount when she eats there. It was a very expensive, upscale kind of place. Caviar on everything, and the best steak I've ever had. Not my usual vibe, but the bartender made an amazing Old Fashioned and our waitress was obscenely hot.

We'll call her Hannah. She had subtly dyed red hair that faded into brown at the top of her head, a cute little nostril piercing, and red lipstick to match her hair. She wore a white button-up shirt that fought for its life to contain her massive bust.

"I'm surprised this place lets you dye your hair," I said.

"Oh, that's a whole story in and of itself," she said. Her and my cousin both rolled their eyes and laughed.

"She walks in with hot pink hair and the manager freaks the fuck out," my cousin says.

"Told me I couldn't come back until it was a natural color. Red's natural, right?"

"That it is. It looks good," I said.

"Pink looked better," she said. She pulled out her phone and showed me a picture of her with the pink hair.

"I like it, but I think you look great now," I said.

"Well thank you," she said with a cutesy smile before running off to the next table.

"That girl might be a little too wild for you," my cousin warned. She told me the whole story: she'd been dating another waiter there on-and-off for a few months. Always fighting, doing crazy shit, making up, being generally toxic. She was 25, he was 21.

"Oh believe me, I've been there with a coworker before," I said.

"Yeah but this is the second guy she's done this with."

"Well, a little flirting won't hurt anything," I said. "I'm back to LA in a couple days anyway and I need to keep my mind off that girl, what's the worst that can happen?"

A little while later, she comes back and starts complaining about her boyfriend with my cousin. They're on a break but her best friend says she saw him with so-and-so from their community college, blah blah blah. I won't bore you with all the details. There will definitely be more time for that later in the story, anyway. I tried to give some advice of my own, keeping things light-hearted.

Now I should say I'm not one to flirt with waitresses under normal circumstances. They're just trying to do their jobs. This was a little different in my mind because we immediately established a rapport through my cousin where conversations were deeper than just "what do you want to drink?"

The flirting absolutely continued throughout the meal when I knew it shouldn't, but she was clearly into it so even though I thought twice about it, I definitely didn't think three times. Maybe that was the alcohol talking. It was easy because we were both into video games and other nerdy shit that my cousins aren't really into.

When the check came, I took the hit and offered to pay the hefty bill as thanks for taking me in at the last minute. Of course I tipped generously, not just because the waitress was attractive but because it's the right thing to do. For the first time in my life I decided to be "that guy." I scribbled a note to her with my username on an app that allows you to send pictures that disappear after viewing. (There's a spam filter on this sub that prevents me from saying the name of the app, but you know the one.)

The cousin I was staying with worked the night shift that day, so she left for work a few hours later. I didn't really think too much of my note until later when I was laying in bed doomscrolling or something. My phone vibrates with a friend request that I immediately accept.

My phone vibrates again. A picture. I open it up to see Hannah, clearly in the bath despite only being visible from the shoulders up, looking up and to the side, her hair up in a bun. All it said: "hey."

I respond with a photo of my own and, "I was worried you didn't see my note."

"I saw it but I had to make up my mind about messaging you lol"

"What was it about being in the bath that made you change your mind?"

"I'm so relaxed rn," she said alongside a picture of her stomach and legs sticking out of the water, strategically hiding her lady parts beneath the bubbles.

"Rough day at work?"

"Rough day at everything," she said, followed by, "idk what I'm doing lol"

"I don't think anyone does tbh"

"you seemed to know when you left that note lol"

"you miss 100% of the shots you don't take"

"then shoot your shot," she said along with another selfie that was similar to the first one, only a little lower. Low enough that I could get a good look at how large her breasts really were outside of the nice white shirt she wore at the restaurant, but not so low that I saw too much. They were mostly obscured by bubbles, anyway.

"you eaten yet?"

"nope"

"what's a good place around here?"

"I've been craving this one pizza lately"

"wanna come pick me up after your bath?"

"sure lol"

It must have looked so strange seeing us out together as I was wearing business attire (the only thing I had with me) and she had on a very revealing black tank top, short black skirt, and a jean jacket. Okay now that I type it out, I know exactly what it probably looked like, but we had a good time and she seemed to like the overdressed look. She also had no issue pushing her tits up and showing off some deep cleavage.

There was just one problem: about halfway through the meal, the topic switched up to her ex(?)-boyfriend and went on... and on... and on. I did my best to follow along with all the drama and offer some sincere advice in between "uh huh" and "wow that's crazy". It got to the point that I felt more like we were just two friends hanging out instead of strangers on a date, and I guess that was fine, because the companionship was good with me. I even started opening up about my own issues with my most recent ex and the woman that had recently rejected me. By the end of the night, I was expecting to just have her drop me off back at my cousin's place without even so much of a kiss, but she had a different plan.

"So, my mom's out tonight, you wanna come back to my place?" she asked.

I was a little startled. "Uhhh... yeah, if that's what you want."

We hopped in her car and drove back to her mom's house. We made a quick line to her bedroom, which was like a perfectly decorated e-girl type room. Christmas lights and fake leaves hanging over her bed, a color-changing lamp, stuffed Pokémon and other characters all over, and a big gaming setup. She mentioned wanting to start either a streaming career or... other kind of online career, but as far as I know it never panned out into anything. She pulled out a bong and we smoked for a while, just sitting on her bed and talking about our lives and plans. We got reasonably high just enjoying each other's company.

\---

"Here, lay down," she eventually told me with a smile. I did as she said and got down on her bed, pushing some pillows around to get into a comfortable position. She crawled on the bed after me and started kissing me. I quickly unbuttoned my shirt and opened it up. Her tits hung down and weighing heavy on my bare chest as we made out, then dragged across my body as she lowered herself down to my pants.

"This what you want?" she asked with a smile as she pulled down my slacks.

"Yes," I said. She pulled down my boxers and put her tongue on my cock right away. She had a cute little mouth that admittedly struggled to work around my above-average girth, but she did her best to pop her jaw open as wide as it could go. I moaned words of encouragement for her. "Fuck, baby, that feels so good."

She lifted her head up. "I had to stop giving blowjobs because he always complains I'm not good enough," she said. Jesus, that didn't take long.

"He doesn't know what he's missing," I said, putting my hand on her head to get her back down. She rolled her lips across the shaft and kissed it up and down all the way to my balls. She sat up and pulled off her tank top so she had just her skirt and a black bra, then leaned over and slipped the band of her bra over my cock and slid it between her tits.

"I know you like that," she said. "You've been staring at them all night. I can tell you're a tits man." She looked up at me with a seductive, knowing smile as she said it. Her eyes softened as she stared deeply into my soul, enjoying how much pleasure she was giving me.

She spit a little on my dick to help lubricate it a bit and squeezed her tits between her hands. Watching them bob back and forth on my dick was absolutely hypnotizing. We sort of had to adjust the position so I was on the edge of the bed and she was on her knees, but she titfucked me until I told her to switch spots. I reached a hand between her legs and stuck my finger in her pussy. Without even needing to be touched, she was already soaking wet.

"I'm ready," she said. "Fuck me. I want it raw. I'm on birth control."

I got on top of her and slid my cock inside of her. She let out a loud moan as it stretched her walls and I pushed until my hips connected with hers and I couldn't go any deeper.

"You feel so fucking good," I said. I get extra sensitive when I'm high so it was an incredible sensation. She was the same way, so she was moaning with each and every thrust. I started picking up the speed, going faster and harder.

"Slow down," she said.

I listened. "Am I hurting you?"

"No, I just like it slow. I want to feel every single moment."

It was a little odd to go the slow and sensual route with a hookup, but I respected her request and slowed it down, making every motion with purpose. She reached her hand down between our bodies and made slow circular motions on her clit. Her fingernails grazed against my body whenever I pushed in deep. I could feel every little pulse and spasm in her pussy, and she felt every time my cock twitched in pleasure.

"Let's take this off," I said, fiddling with her bra. I reached my hand around and unclipped it. She slid it off and her huge tits spilled out.

"I'm used to keeping it on. He said he doesn't like the way they flop to the sides when I'm on my back," she said.

"It sounds like he barely likes you," I said, still a little weirded out by her bringing him up again.

"That's how it feels sometimes," she said.

I grabbed one in my hands and began licking and sucking her nipple. She bit her lips and let out a squeak. She was a bit ticklish about it, sending her into a little giggling fit and causing me to start laughing as well.

"Oh my God, aah!" she squealed, kicking and smiling. I'm pretty certain I've had full-blown relationships with less sexual intimacy than what was happening here, even though I think it should be clear to everyone reading that our heads were not fully in the game at all. Everything about it was just so... wrong.

"Okay, you can go a little faster," she said. I picked up the speed while she continued fingering herself. Within 30 seconds, she was cumming. I wasn't far behind.

I pulled out almost immediately because I didn't want to risk it. Even in the heat of the moment I think I knew that cumming inside this girl was bad news. I started jerking myself off, trying to finish the job.

"Let me help," she said, motioning me up toward her tits. I straddled her body and she grabbed her tits to place them around my cock. I fucked her tits while she bounced them up and down. "Cum for me baby. Cum between these big fucking tits and all over my face. I want you to cover me."

All the dirty talk worked wonders on me, as I soon felt the urge to cum. I reached down and gave her tits one last squeeze against my cock as I started shooting my load out, with a couple of shots spraying up to her nose and in her mouth but mostly against her chin and dribbling down between her tits.

I ran off to get her something to clean off with, and when I came back, she had her phone out and was taking selfies of her cum-covered face and messy sex hair.

"I like having keepsakes when I look this good," she said. Yeah, okay. Sure. It wasn't the weirdest thing that had happened, so I simply asked for a copy and handed her the towel. She licked up the cum from her lips and used the towel to try her chest and neck.

We laid in her bed on our phones for a little while, showing each other stupid funny videos and occasionally chatting about other things.

"That was great, when are you leaving again?" she asked.

"Sunday," I said. "But I've got plans tomorrow with the fam."

"What a shame," she said. "That was a nice little distraction from it all."

"Yeah, it was."

I called myself an Uber before her mom got home and we bid farewell. We continued texting and sexting Saturday night, but by the time I got to the airport on Sunday she had unfriended me. Fortunately for her, the last time I talked to my cousin and asked about Hannah, she didn't end up getting back with that boyfriend. I don't know if she just needed someone to not treat her like shit for one night to get it in her head or what, but I'm at least happy to hear that based on all the shit she told me about him.

I guess it was the same for me: I went back home and completely forgot about that rejection because I couldn't stop thinking about this night and laughing at the absurdity of it all. Maybe that's just me, so I hope the humor comes across in the story as well otherwise I look like a crazy person!