I encounter a trailer park cutie, what could go wrong?
Not sure if this belongs in LW, but here it is.
Bobbi Jo grew up in a mobile home park. Her Dad was a drunk and seldom home. Her mother liked to drink but managed to take reasonably good care of her four children. By that I mean they had enough to eat most days and usually had clean clothes to wear. Not the latest fashions, of course, just whatever they got from the Good Will store.
I met Bobbi Jo at the diner where I sometimes had a quick lunch. She had just turned 19 and completed her third year as a waitress. She was popular with her customers, especially the men, which helped her earn decent tips each day.
I watched her moving about the diner. She stood about 5'7" and weighed no more than 125 pounds. Her constant motion kept her shapely legs trim and firm. Her tight uniform accented her plump heart-shaped ass as she swished past me. Her belly was flat and hard, making her c-cup breasts look gigantic on her slender frame.
Her wild mass of dark hair framed a plain face that usually sported a wide smile. She was not pretty, but with that incredible body, the boys, and even the old men, liked to watch her work.
"Another refill, Mr. C," she asked as she held up the coffee urn.
I stuck my hand atop my cup, "No thanks, sweetie, I've had enough." As she walked away I dropped a twenty on the table and headed out. I knew my bill couldn't be more than 7 or 8 bucks, but I didn't care.
I'd been coming into the diner for about six months when Bobbi Jo plopped down across from me one day. "Mr. C, you've been coming in here for some time now and each time you leave me a big tip. I know you like me, so why ain't you asked me out?"
I smiled as the youngster. "Bobbi Jo, you are a very attractive young lady, but I'm way too old for you. Besides, aren't you seeing that young man who drives the yellow pickup?"
"First off, you're not too old for me. I like older guys, they is far more interestin'. Secondly, the yellow truck is Billie Bob's. He ain't my boyfriend, It's just we've been together since I was 14. He grew up in the Park where I live, I've known him forever."
I looked at her. She took a deep breath and those big tits strained against her tight uniform. If she was trying to sell me on the idea of asking her out, it was working!
"Okay Bobbi Jo, we can go out but you have to call me Dave, not Mr. C."
"Her smile widened. I'm getting off early tomorrow, so pick me up here at 4:30. I'll need to run home for a few minutes then we can go wherever you want."
The next afternoon she directed me to stop in front of a poorly kept trailer. "We ain't got air conditioning, so you can just wait here for me. I won't be but a minute."
She dashed inside and moments later stepped back outside. She had on an impossibly short denim skirt and a red and white halter top that showcased her bountiful breast. On her feet, she wore cheap little white sandals.
She jumped into the car and slammed the door. "Okay, I'm all yours."
We drove over to the next town to a nice little Italian restaurant. The senior citizen waitress thought nothing of serving my young companion wine with dinner. Bobbi Jo was feeling pretty relaxed when we headed back to home turf.
"You got any more wine like that at your place?"
"Sure, but maybe you've had enough for tonight."
"Phoo! Just one more glass while we watch a movie or something. You got cable, right?"
She was very impressed with my house and about went crazy when she saw my pool.
"Oh my god! You have a pool! Can we go swimming?"
"Uh, you don't have a swimsuit."
She looked around, my privacy fence and shrubs blocked out all of the neighboring houses. "Looks like that won't matter none, nobody's gonna see us."
She gulped the rest of her wine down and then began to strip off. I was shocked when she dropped her skirt and I realized she had gone commando to the restaurant. She whipped off her top, kicked off her sandals, and then turned to me.
"Well come on, slowpoke!" She chided me before turning and jumping into the pool.
I fumbled out of my clothes and dove into the pool. I swam around for several minutes and then sat on the pool stairs. The water came up to my armpits, so it was comfortable sitting there. Bobbi Jo swam up to me and climbed up onto my lap. She wrapped her arms around my neck and pulled me down for a kiss.
I kissed her softly and hugged her to my body. As we kissed my dick began to react as she squirmed around on my lap. My boner poked at her pussy and she wiggle against it.
"I'd say someone is glad to have me in the pool," she said and giggled.
"I wouldn't trust him, he likes to be naughty when he is around sexy young women."
She giggled and squirmed some more. I spread my thighs a bit and pushed up at her. She moved a hand between her legs to direct my dick to her opening. I push the head of my dick into her.