This is primarily a romance with not a lot of explicit sex. If you're looking for a good stroke story, this may not be it.
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"You like bad girls", she said with her lipstick askew. "I'm a bad girl."
I looked at the young woman standing in front of me. She appeared to be late teens or early twenties, with bleached blonde hair, too much makeup, not always well applied. She wore a skin tight top cut very low, no bra, a very short skirt, and very high heels. She had the perkiness of a teen, along with the awkwardness.
"Good girls go to heaven", I replied. "Bad girls go everywhere."
She looked like she was waiting for something, so I gestured for her to sit on the stool next to me. I got just a flash that told me she wasn't wearing panties, before she clenched her legs tightly together. She squirmed a bit trying to get comfortable, before smiling at me. She had a little lipstick on her teeth, besides the lipstick that managed to go somewhat beyond her lips.
"Buy a girl a drink?" She asked.
"Are you even old enough to drink?" I replied with a wry smile.
"I have an ID that says I am."
"Real, and yours?" I asked.
She squirmed in her seat again, then tugged on her top to show a little more of her b-cup cleavage.
I should introduce myself. I am Matt, middle aged straight male, graying a bit, but still with most of my hair. I'm in decent shape - trim at least with a little muscle from light weights a couple times a week along with extended workouts on an exercise bike to keep up aerobic fitness and keep my weight down. I was wearing khakis and a long sleeve shirt - business casual attire, having come from work.
I work as a number cruncher - real title financial analyst. Basically I work on financials for my employer, budgeting and comparing results to budget, then revising forecasts based on recent results. Hardly exciting, but it paid the bills comfortably. I'm divorced, for the past three years. She had a good job, so I got away with no alimony, but she got the house. She got remarried, to a high flier, and now has a child.
I haven't done much dating since my divorce. I never was exactly a great ladies man, even before I met my ex-wife. Now I just go out for the occasional drink and take in a few social events, just so no one, including me, thinks I'm some kind of hermit. Once in a while I do some light flirting, but haven't gone home with anyone since my ex-wife left.
At times, women flirted with me, but I had never had quite so blunt an approach as this young woman seemed to be making. I didn't really expect anything to come of it, but figured I might as well let it play itself out. No harm in that, as long as she was of age, not that I expected that to matter. She was starting to look just a little antsy, so I tried to make small talk.
"My name is Matt, what's yours?"
"My name is Tracy."
"Is that your real name, or just your nom de guerre?"
"My what?"
"The name you use when you're out having fun."
She squirmed a bit before replying. "My parents named me Donna, but that's so dull. Donna is a boring girl, Tracy is an exciting one."
"May I ask how old you really are/"
She squirmed again. "I'm nineteen, but I have an ID that says I'm twenty one."
"And what does a nineteen year old woman want with a fifty year old man?"
"You're still held together pretty well, and you look better than most of the sleazes around here."
"You've seen a lot of those sleazes?"
She turned red, and squirmed in her seat again. "I don't want anything to do with them, but they do hit up on me a lot."
"You do look like you want a certain type of attention from men."
"My parents would die if they knew I was out anywhere dressed like this."
"This isn't really the place to talk, and you shouldn't be drinking anyhow. Have you eaten dinner?"
She shook her head but looked a little uneasy.
"Let's get a bite to eat and talk. I promise not to attack you. I might not even attack you even if you want to be attacked."
She looked a little shocked. "Where... did you have in mind?"
"There's a little Italian place a few blocks down. We can walk unless you'd rather I drive you there."
"I trust you to drive."
I took the last swig of my beer, then stood and held out my hand to help her. She looked surprised and pleased as she hopped down, then tried to smooth her skirt to maintain some sense of modesty. She had a small purse, and I put my hand at the small of her back to guide her out the door of the tavern. As we got there, I stepped ahead and held the door open for her.
She smiled and I put my hand on her lower back again to lead her to my car. I have an Accord, about five years old, charcoal, with a six cylinder engine and a sunroof. Hardly exciting, but clean, practical, and functional. I opened the passenger door for her and held out a hand to help her sit. I got another brief flash of her pantiless crotch as she sat.
I sat down in the driver's seat and started the car. "We're going to Lorenzo's on Florida Avenue if you want to let anyone know."
"You seem like a decent guy."
"I think I am, but appearances can be deceiving, you know."
"For some reason, I trust you."
"So what are you doing, out at a tavern, dressed like that?"
"I don't think I wanted to go home with anyone, but I wanted to let loose and have some fun."
"Too many guys could get the wrong impression."
"And did."
We talked as I drove and at the restaurant. It seems Donna, or Tracy, was the only child of some very religious parents. Her parents had sent her to a strict church school until she got to her teens and started to act up. They pulled her out of school and home schooled her through a high school degree. She'd taken some equivalency tests to grant her a diploma.
Her parents wanted her to quickly marry a good church-going boy and settle into being a wife and mother. She wanted to go to community college, get a degree and a job and have some fun before settling down. Against her parent's wishes, she enrolled in college and got a job. She refused to let her parents set her up on dates with boys they thought were suitable.
She had gone on a few dates and found that the guys fell into two groups - those who only wanted sex, and those who wanted her to be a proper housewife and mother. She wasn't really ready for either. She fought with her parents until she moved out. Now her folks decided she was some sort of fallen woman or slut and wanted nothing to do with her.
She worked at a coffee shop and at work and school she dressed very dowdy and plain. Every once in a while though, she felt the urge to dress sexy and try to have some fun, which only seemed to attract more guys who only wanted sex. The impression I got was that she was still a virgin, but conflicted about losing her virginity.