Note: This story is based on earlier story 'Sister-In-Law' (Literotica, June, 2021). That story was true, but this story expands into a fantasy based on one part of that story. Like in the original story, all characters are at least 18 years of age.
It was a warm Friday night in the summer, and Russ and Gary were bored. Like most guys in their early twenties, they wanted to be around other people their own age, and hopefully meet some similar-aged girls. But it was too hot and too muggy to put on dressier clothes needed to get in local clubs. Tonight was a shorts night. And beer night. And car night...
The best place to meet girls without getting dressed up was at one of the local strips frequented by others their age. They loaded into Gary's Mustang, and 15 minutes later they were surrounded by cars popular with young people, and those borrowed from young people's parents. They knew most sporty cars would be piloted by guys, so they timed each trip up and down the two-mile stretch where they would be surrounded by Mom-mobiles.
On their third time up the strip, a blue four-door sedan slowed down next to them. The driver was a cute brunette, and even in the limited light of oncoming cars they could see she had a big smile and vibrant green eyes. Her passenger was an equally-cute blonde who wasn't quite as outgoing as the driver. After quick introductions the sedan followed Gary and Russ to a parking lot where they could get out of their car seats and to get to know everyone better.
When they all exited their cars, the first evaluations took place. Gary was 6' 2" and slender while Russ was 5' 10' and stockier. Lisa was 5' 5" and petite where Tracy was 5' but curvy. There was enough attraction that no one was eager to leave, and by the end of the night, Gary was talking more with Lisa while Russ and Tracy were hanging out. Each new couple set up dates for the following night.
Gary was in college, home for the summer, while Lisa had just moved south from a small town in Michigan. She was a cute brunette with those bright green eyes, but was nothing like other girls he had dated -- she was shorter, and with a more petite figure - than he was used to. But he'd been single for a while, and the way she kissed him after he asked her out - with some heat and a ton of seduction - was definitely intriguing.
'What the heck', he thought as his erection grew in his shorts while her tongue probed his mouth and her body pressed against his, '...it was just cruising and maybe a summer fling'. He'd done the girlfriend thing a couple of times, going out for months before trying anything sexual. Lisa's flirty, outgoing personality had tons of potential and was worth trying a few dates.
On their second date when he kissed her 'good night' at her front door, she ground her hips against his, her forbidden mound of pleasure pressed hard against his dick, which quickly stood at attention. He needed something -- anything -- more than a kiss to get him through the night until he could get home and enjoy the seduction of his right hand.
"You kiss really, really well," he said shyly.
"Really?" she asked.
"Uhhh... YEAH!" he whispered trying not to wake her parents.
He pushed his erection harder against her stomach again for emphasis.
"Better than the girls at college?" she asked teasingly.
"None of those girls ever did this to me with just a kiss..." he said as he again pulled her close and pushed the erection she caused into her stomach.
He kissed her again, and as she ground her body into his, he moaned in pleasure. But there was also desperation in the sounds he made. He was 21 and got hard when the wind blew, but her teasing was much more intense than a blowing wind.
"My first girlfriend would sometimes let me come to her window and watch her change into her pajamas before I went home," he said, trying to not sound like he was begging. "Any chance we could do that? You've gotten me pretty worked up."
Lisa never answered, but again kissed him even more passionately than the first time. She made sure he was even more aroused before whispering, "Good night!".
Gary wasn't sure if that was an invitation or not, but she never said 'no', so he drove around the corner, parked, and snuck back to her window. The light was on and the blinds open, and when he peaked in, Lisa was standing naked waiting on him. It was so much more than he was hoping for, and he quickly took in every part of her body. Her brunette hair was long and fell down her back, and her green eyes seemed to sparkle at the thought of teasing him. She wasn't athletic, but there was not a single ounce of fat on her body. Her boobs were probably 34Bs covered with dark pink nipples that weren't as large as his previous girlfriends but big enough to make his mouth water. Her waist curved sexily into her hips which framed a perfect triangle of dark hair between her legs. After she was sure she had teased him enough, she ran to the window and opened it.
"Wow, this is incredible - you are so sexy!" Gary whispered excitedly as she leaned out and again kissed him. "I was just hoping to see some pajamas, or maybe panties, but this?! SO much better!"
Lisa said nothing, but waved 'good night' as she backed to her bed, giving him a few more seconds of a show. She smiled seductively and she pulled the covers up over her naked body then turned out the light.
If the kiss hadn't been arousing enough, Gary was now about to explode. As he snuck back to his car, he wondered if he could survive the 30-minute drive home before relieving himself. Since his erection was making it difficult to walk, he wasn't sure he could survive the drive. He also didn't want to drive -- he wanted to jack off while the image of his sexy, naked date was still on his mind.
Gary entered his car and looked around. The street he was parked on was a side street with no houses on it. It connected two of the numerous parallel streets of comfortable homes in the comfortable suburban neighborhood. He could see streetlights on the main street ahead and behind him, but neither cast light on the connecting street where he parked. His tinted windows were the final level of security as he decided to undo his shorts and slide them and his underwear down.
'Hello old friend,' he thought as his hand wrapped his erection. 'Something tells be you're going to get to meet Lisa VERY soon...'
He closed his eyes and remembered her naked body. He wanted to fantasize about how she felt to his touch, and how they would get to know each other physically, but after he moved his hand up and down his erection a few times, he knew this would be too fast for much fantasizing. He thought about trying to prolong his orgasm so he could imagine sex with the petite brunette, but that wasn't going to work tonight. He decided his best bet was a quick, rapturous release to enjoy the vision still fresh in his mind.
Gary closed his eyes, and as he remembered her smooth, pale skin, his hand pumped up and down his shaft like so many times before. He remembered her tits, and though they weren't as big as recent girls he'd been with, they were still noticeable for her more-petite body. Then he remembered the hair between his legs and wondered if she would let him taste her womanly essence. Then he remembered that mischievous smile, and the way she kissed him at the window, naked, and oh-so close. Then he felt the familiar pleasure, then tingling he loved so much, and he opened his eyes in time to watch stream after stream of warm, white, sticky fluid shooting out of his purple head. Then the pleasure became too intense, and the streams of ejaculate were mostly done, and he lessened his grip and coaxed the last few drops of cum out. Much of his many streams had landed on his shirt, a few on the car seat, and one even hit the headliner. He took the shirt off, cleaned as best he could, then started the car.
* * * * * * * * * *
On their third date Lisa and Gary got into a hot tub at a friend's apartment complex. It was mostly dark, and they were alone, and when he teasingly tugged at the string holding her bathing suit top in place, she took it and her bottoms off. After watching her at her bedroom window a few nights ago, she was now naked and available for him to touch. She was also very affectionate and never hesitated touching him or asking him to touch her. She sat in his lap facing him, and ground her pussy against his erection, tempting him with the possibility of being inside her. After first seeing her naked a few nights earlier, he could finally touch her body, feel her boobs, put a finger inside her, and have her touch him. There had never been so much promise so soon after meeting someone, but he still believed that women wanted relationships before sex. He didn't realize that she wasn't teasing him - she was offering him everything he wanted. He was aware, though, that for the first time in his life, not everything that happened between he and his sex partner had to be initiated by him.
Gary quickly realized this relationship would be different. There was no trying, then being rejected, then trying again, and maybe getting lucky a few days later. Lisa wanted sex as much as he did and never hesitated to offer herself to him. The next date after the hot tub she got naked in his car and gave him their first blow job, and then asked her if he wanted to fuck her. He desperately wanted to, but the tightness of his back seat stopped them from being together for the first time. This became especially annoying to Gary when he learned she was on the pill.
