Harry had been in a dry spell for quite some time. In fact, other than his own hand, he wasn't 100% sure when the last time he had gotten off. It wasn't that things were bad at home, there just wasn't any spark left between him and Julie, and by the time they got into bed, they were both tired every night, so nothing ever happened. He had been faithful to her since the day they met, but it was getting to the point where all he could think about was sex 24/7.
Finally, he decided he needed to try something different, but what? He considered a strip club, but that would have just made his frustration worse. A hooker seemed like a potential solution, but there was something about paying for sex that turned him off. So he finally settled on starting to surf the personal ads on Craig's List.
It didn't take him long to discover the "Seeking" section, which seemed to be filled with both men and women looking for anonymous hook ups. Several of the ads referred to "car dates", which intrigued him, although he wasn't exactly sure what that entailed. A quick search on Urban Dictionary, and he realized that this was a polite euphemism for various sex acts performed in your car. Perfect, he thought! This solved the location issue, and frankly the thought of sex in his car was exciting! He hadn't had sex in a car since high school, when that was the best option ... and it seemed the best option now too.
Harry proceeded to text several of the ladies who had posted car date ads recently, and a short time later, he got a text back from a woman who called herself Linda. After exchanging a few pleasantries, Harry asked her if she wanted to meet sometime for a car date. She immediately responded that she was waiting for him to ask, and would be delighted to meet soon, was he available tomorrow afternoon? Checking his calendar, he saw he could sneak away, so they set a date for 3 PM the following day.
The next day seemed to drag on for eternity. Harry felt a little like he was in the scene from "Fast Times at Ridgemont high" when the clock was actually moving backwards! Finally, 2:30 came, and he walked out of his office and informed his secretary he had to run an errand, but would be back in an hour or so. Trying not to run to his car, he jumped in and drove as quickly as was prudent to the appointed meeting place, a Starbucks on the other side of town. He parked and texted Linda, who responded that she was just finishing her latte and would be out in a minute, asking him what kind of car he was in and where he was parked.
Steve sat pensively in his car, waiting Linda's arrival. After a few minutes, the passenger door opened, and he was pleasantly surprised to see the woman who climbed into his front seat. Linda was probably early 30's, reasonably attractive, with long wavy brown hair, and a cute face. She wasn't a "10" by any stretch, but not being sure what to expect, Harry was happy that she also wasn't a "2".
Linda immediately said "hi" and leaned over to give Harry a peck on the cheek. "Let's go", she said. Harry started up the car, and drove out of the lot, but suddenly realized he had no idea where they were going. He turned to Linda and asked "where to"? To which she replied "what, you don't have a plan?" Harry's face flushed bright red in embarrassment, but Linda started to giggle and comforted him with "just teasing, why don't you get on the interstate and just drive"?
Harry found the nearest on-ramp and got on the interstate headed west out of town. As they got up to highway speed, he felt Linda reach over and put her hand on his thigh. Turning toward him she asked "so have you ever done this before?", and Harry responded with a head shake no. Linda explained that she was married to an older gentleman who didn't have much sex drive, and as she was a bona fide sex addict, she had started car dates to get her fix without the complications of having a boyfriend on the side.
As she was talking, she began to run her hand up and down Harry's thighs, and eventually worked up to his groin, where his cock was steadily growing in his pants from her attention. She cooed in his ear "ooh, it looks like someone is getting excited!", and then undid her seat belt and turned slightly in her seat, reaching across the center console with her other hand and unzipping Harry's fly. She deftly reached into his fly, wriggled her fingers into his briefs, and snaked his cock out of his pants.
Harry couldn't believe his luck! They had only met 10 minutes earlier, he knew practically nothing about Linda other than her first name and that she was married to a man who couldn't satisfy her, but already she had his engorged cock out and had wrapped her lovely hand around it!
Linda then took her hand, and cupping it, spit into it several times. She then reached back into Harry's lap and wrapped her spit-coated hand around his shaft and began to slowly stroke up and down. Harry let out a low moan of pleasure as she expertly worked him with her hand, squeezing just as the ring formed by her thumb and forefinger reached the base of his cock's head to maximize the stimulation. After a few minutes, she added in a bit of a twist, which sent shock waves through Harry.
He didn't realize it, but his speed was fluctuating and his steering was a bit erratic. "Better set the cruise control" Linda advised, "otherwise you're going to find it very hard to maintain a steady speed." Harry did as she suggested and tried to concentrate on staying in the lane.