My Braless Milfy Waitress Pt1

We drink at the neighborhood bar most nights. Our regular waitress is a nice 40 year old milf.
This current summer has been really hot and this little dive has crap a/c. We’ve been bitching at the owner for years.
All the staff are hot and sticky slinging beer and wings. It’s not a 5 star place.
Our milf waitress “Cindy” has at all times been super happy. Today she’s a bit bitchy. When she delivers our beers she’s telling us the boss is making no attempt to fix the a/c and the staff is on the verge of quitting.
The next time she comes back she looks quite different. She’s taken her bra off. Their uniform is essentially a white golf shirt, black shorts and high boot sneakers. So now her tits have a nice jiggle and you can see her big round nipples clear as day through the white shirt. I motion her to lean over. I told her you can see through her shirt. She says, good! I said, well she should get good tips! She says, let’s hope.
Near last call she’s cashing out. She comes over and tells me she tripled the usual tips and the braless thing is permanent. I said I like it!!
The next night Cindy’s braless and now she’s ditched the shorts and is wearing a short tennis skirt. Cool. She looks great. Every time she delivered drinks she’d drop something reach over and I could see up her skirt. Wow!!No panties!! She leans over and says she thinks her tips will be even better tonight and winks. I see her cashing out. She comes over and tells me she broke her all time record. She made about a weeks worth of tips in 1 night. I should have done this a year ago when I started. I’d be rich!! Lol!!
I laughed. I said well. Only thing that you could do to top that is go topless and you can’t do that.
She laughs, she eyes me over. She says she’d like to grab a drink somewhere and all she ever does is wait on other people. She asks me if I want to go to this casino that serves booze 24/7. I wondered for a millisecond and said absolutely. She’ll drive and just stand out front, she’ll pull around.
She comes around the corner driving this classic muscle car. This woman is like a bad ass from rural USA.
Okay. This is what I know about this woman. She’s about 40. She’s from the Carolina’s due to her accent. She’s about 5’7” tall. Big D cup tits that jiggle. She was likely pretty slim as a girl that put on a few pounds. Nowhere near fat but a juicy mom bum and a bit of a tummy. The car was an old Chevelle SS 396.
I said whoa. Nice ride. She said thanks. It was her dads and he left it to her along with the the farm that she rented out etc.
We get on the highway and she drives like a kid. Flooring it. Passing cars like crazy.
We hit the casino and grab a couple drinks. Late night lounge entertainment is playing. She says be right back. I’ve gotta freshen up.
When she comes back she’s pulled her hair back into a ponytail. Washed her makeup off, took out her contacts and is now wearing glasses. She looks 200% better. Hair back exposes a cute face. She looks better without makeup, and the glasses round off the girl next door look. This little doll has been hiding in plain sight. Fucken holy cute.
We’re sitting a big half circle booth and I can just sorta see her pussy. She catches me looking. She says, well? Like my little money maker? It’s almost like new!! Lol. I said. It looks good enough to eat. She looks around. Yeah. Maybe not here though, but I like the way you think. Touch it. See if you like it. I kinda laughed. Don’t girls shave where you’re from. She says likely, but she doesn’t. She says, I love my bush. Turns out she’s from Macon Georgia. I was close.
She spreads her legs nice and wide. Her slit is like a seam. Nothing on the outside right now. Never quite seen this type. It’s like a mouth closed. She reaches down and spreads the lips. Now her clit is peeking out at the top with small labia folds exposed. Wow. She is super wet. I put my finger in. Then pull it out and taste it. Mmmmmm just like I like!! I put my middle finger in her hole. Her clit is now swelling and quite erect. It’s like a little cock at attention. At this point she’s making an almost inaudible moan always keeping an eye out.
She leans into me and whispers I think I’m going to cum. Ohhhhhhh fuck it feels good. When she cums she clamps onto my wrist pushing it away. After she’s finished she got so embarrassed. I can’t believe I just did that. I’m not a slut. It’s been so long. She has a tear in her eye.
She got divorced in Georgia 15 years ago, hooked up with a guy who got a job here, 10 years ago she tossed him out after he took a swing at her. She said she kicked him in the nuts, bear sprayed him and tossed his stuff out the window. She looks at me and chuckles. I haven’t been laid in 10 years. I’ve got a lot of banked orgasms. Lol.
I looked at her. Me too. I haven’t had a girlfriend or even one night stand in 4 years!!
She asked how old I was. I said 28. She says, yeah. How old are you? 25 I say. She looks. Final answer? I said 23. She laughs. Okay. I believe that. I’m 40. You like older women? I said I’m not sure, but I like you. She says, good answer. You’re kinda cute. I think we could have some fun. That is, if you want? I looked and said, I want. Wink.
She says, let’s get out of here. I know a nice quiet place.

End part one

NSFW: yes

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