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. The early parts of this story are true, but anything after the shower is the fantasy...
Lisa and Gary met cruising the strip. He 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 bright green eyes, but was shorter, and with a more petite figure, than he was used to. But the way she kissed him that first night, 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 and told her a previous girlfriend would let him come to her bedroom window and watch her change into her pajamas. She thought that sounded fun, and by the time he parked his car around the corner and snuck back to her window, she was naked waiting on him. She opened the window and kissed him, her naked body tempting him just inches away. After she had him ready to explode, she crawled into her bed, still naked, and waved to him as she turned off the lamp next to her bed.
On their third date they 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. Even though she didn't have the curves he normally liked - she had an athletic build, tight butt, and nice boobs - she was very sexy naked. She was also very outgoing once the swim suit came off and never hesitated touching him or asking him to touch her. She sat in his lap facing him, and ground her pubic hair against his erection, tempting him with the possibility of being inside her. There had never been so much promise so soon after meeting someone, but his false belief that all women wanted relationships before sex prevented him from understanding what she was offering. 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.
By their second week together he knew Lisa was not going to be his typical girlfriend. There was no trying, then being rejected, then trying again, and maybe getting lucky a few days later. She wanted sex as much as he did and never hesitated to offer herself to him. By their fifth date she got naked in his car and gave him a blow job, and only the smallness of his back seat stopped them from fucking for the first time. This became especially annoying to Gary when he learned she was on the pill.
A few nights later she asked him to again come to her bedroom window. Again, she was naked when she greeted him, but this time she opened the window enough for him to crawl in. He fucked his third girlfriend for the first time, and for the first time in his life when he said "I'm about to cum", she said, "you can cum inside me."
* * * * * * * * * *
At 18, Lisa had a basic job, but she was a shift manager at the fast-food restaurant she worked at. Most of the people working for her were a few years older, but they were close enough in age that they liked to party with her. One weekend Lisa and Gary were at a party at a coworker's apartment when the subject of masturbation came up. At first, all of the six guys and three girls denied masturbating. Lisa usually enjoyed being the center of attention, but when one of her workers asked her if she did it, like everyone else she denied, denied, and denied some more. But during her answer she began stumbling over her words, and eventually the alcohol gave her extra courage - she was the first person to admit she masturbated.
This was a very different party than the ones Gary attended at college, and he couldn't believe how hot it made him hearing her tell a bunch of people he didn't know that she enjoyed self-pleasure. On the drive home, he couldn't wait to talk to her about it.
"So, you masturbate?" he asked her.
He already knew the answer from her admission at the party. Now, he wanted to get in to the details.
"You know I do," she said teasingly. "How about you?" she asked, turning his question back on him.
"Yeah, I do," he said, a little embarrassed at admitting it to her. He never admitted to doing it at the party, but it felt sexy admitting it to her. He also wanted to do whatever it took keep the discussion going on the ride home.
"I do, too..." she said again before adding, "...pretty often."
Even in the near darkness of the car, he could see her green eyes coming alive, and a smile that made him even harder than he already was.
"The first night you came to my window and saw me naked?" she continued. "I did it as soon as I turned off the light. But it wasn't the first time I did it thinking about you."
"Really?" he said a little shocked. "I would loved to have watched that! What if I told you I did it too, in my car around the corner?"
"Seriously?" she asked. "Wasn't there a mess?"
"You had me so horny I couldn't wait. I had to use my shirt to catch the mess. And definitely not the first time I did it thinking of you."
They didn't change topics during the drive to her house, and by the time they arrived they knew how long they'd both been doing it, how often, favorite places -- Gary knew more about her than either of his first girlfriends. When they got to her house, Lisa again opened her window and let Gary sneak into her bedroom for the second time. It took every ounce of his willpower to quietly fuck her with her parents less than 25 feet away -- just two interior doors separating their moans from her parent's hopefully-sleeping ears.
* * * * * * * * * *
The rest of that first summer went by very fast. They talked every night, and were together most days. Gary wasn't in love, but he was definitely in lust, and Lisa being on the pill was life-changing for a guy whose dick got hard when the wind blew. He realized how pretty she was -- dark hair, those green eyes, small, button nose, and smile with a hint of mischief -- as he spent so much time face-to-face with her, their naked bodies pressed tightly together. For the first time in his life, Gary got to have sex without condoms. He could enjoy the intense pleasure of being inside her while ejaculating. With his first girlfriends there was always the constant, frenzied panic of pulling out and then weeks of worrying if it was on time.
Gary also learned the joy of sneaking in Lisa's bedroom window and having sex in a real bed instead of the back seat of his car. She even occasionally let him fall asleep after fucking her, as long he woke up and left before her parents got up for work. At the end of the summer when it was time to head back to school, he didn't care that she didn't have a great job or that she didn't have the voluptuous body of previous girlfriends - he loved her nice, tight ass and willingness to spread her legs at any time. They were definitely in a relationship.
With his first two girlfriends Gary learned much about relationships but only the basics about sex. With Lisa, there seemed to be no limits on what they could do naked. They sometimes showered together in her parent's bathroom hoping her mom or dad didn't come home early. Watching her masturbate with her finger or vibrator was next level, but seeing her do it with the tub faucet was amazing. Any chance they got, he wanted to see her on her back in the tub, her feet in the air on either side of the faucet while a stream of warm water caressed her clit to other-worldly, leg-shaking orgasms. They skinny dipped in their pool in the middle of the day, and he learned to sit on the side of the pool with Lisa between his legs sucking his dick. He loved feeling his cum pulse into her mouth as they listened to the sounds of neighbors doing less-exciting things on the other side of their fences. Their sex lives were way beyond what they had experienced with previous partners, and Lisa even suggested doing a threesome with her friend Tracy, her copilot the night she met Gary. In their only setback, Tracy's family moved out of state before they could arrange it. It had been a nearly perfect summer.
In September, Lisa took the three-hour drive to visit Gary at college for the first time. His apartment gave them unlimited opportunities for sex, and since she never told him 'no', they made up for time apart. She taught her boyfriend what incredible foreplay it was watching her masturbate, and later that year she gave him his first (and second, and third, and...) sixty-nine. Then, in a time before digital photography, she would pose nude for him and let those pictures go through the Walmart film developing lab. That first summer and the following year at college, Gary learned more about sex than he had during three years with his first two girlfriends. He and Lisa were a couple -- a couple whose relationship could sometime be stormy, but also one where they enjoyed making up after fights.
