Note: This story covers over 5 years. Some of the back story is a little disjointed as I wanted to include the history that lead to the final event, but as that history got too long I kept removing parts for brevity.
Lisa and Gary met cruising the strip. 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 a more petite figure than he was used to, but it was just cruising and she had an equally-cute friend, Tracy, who liked his copilot. That night Gary learned Lisa was about to start her senior year in high school where should would have over 2,000 public-school classmates - a far cry from the 34 very close friends in her private school up north.
At the end of the night she wanted to exchange phone numbers. He was hesitant but single - and she she was younger than he wanted to date seriously. But it was just summer and he could date college girls again in the fall. Besides, her flirty, outgoing personality made it worth trying a few dates.
Their second night together he got her naked in a hot tub, and even though she didn't have the curves he normally liked, she was very sexy naked. She was also very outgoing once naked and very willing to ask for him to do things for her. For the first time in his life, not everything that happened between them had to be initiated by him.
Within a few weeks he had met her family. Lisa had a brother, two sisters, a fairly normal dad, and mom who was a short drive from totally crazy. Mom could be fun at times but was constantly in to some new self-exploration that seemed to be at the expense of everyone else in the family. The older sister had started college up north and always wanted to discuss the infinite ways Michigan was better than their current home. The brother was the youngest and training to be a juvenile delinquent. The younger sister, Kristy, was taller than Lisa, blonde with a curvy body and excellent, full tits. Dad was a regular guy who just tried to keep food on the table while not going insane.
The rest of that summer went by fast. He learned she was on the pill, and and for the first time in his life got to have sex without condoms. He could enjoy the intense pleasure of being inside her while cumming instead of the frenzied panic of pulling out and worrying if it was on time. He also learned the joy of sneaking in her bedroom window and having sex in a real bed instead of the back seat of his car. When it was time to head back to school in the fall, he didn't care that she was a senior in high school 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.
Their summer fling quickly became a relationship. She made the trip to visit him at college and he made the trip home to see her. The first year Lisa taught Gary what incredible foreplay it was watching her masturbate with her finger or a vibrator. Their second year she gave him his first (and second, and third, and...) sixty-nine. The third year, in a time before digital photography, she would pose nude for him and let those pictures go through the Walmart film developing lab. The fourth year she showed him the incredible pleasure of having his cum flow into her willing mouth and down her throat while sitting in the jacuzzi tub in the house they had bought together.
As they went from being a fling to being a couple the older sister graduated, got married, and distanced from the rest of the family. Mom was always taking a class or at some women's retreat, and dad worked as much as he could to stay away from home. As a result, the two younger kids mostly raised themselves. Brother stayed in trouble in school and Kristy ran away from home more than once. The family eventually enrolled her in a boarding school to keep her supervised, but on her 18th birthday she aged out and the school sent her home.
When Kristy got home Gary and Lisa went to visit. Kristy was taking a shower and called out to Lisa to come talk to her. Lisa stood in the doorway of the bathroom and chatted with her sister while Gary was in her bedroom just a few feet away. She got his attention and did a discreet "come here" motion which he willingly followed. From just outside Lisa's bedroom door he could see the bathroom vanity mirror reflecting Kristi's naked body in the shower. It was only a couple of blissful seconds, but he got to see her amazing tits, small waist, long legs, and excellent ass. When Kristy turned toward the bathroom door she saw him looking and covered up, so Gary pretended he was just walking by on the way to the den.
Gary never really paid much attention to Kristy, and never once said anything about her to Lisa, so he was surprised at this treat she gave him. That night they went to his parents old house that was mostly vacant while it sold. Gary volunteered to stay to make sure the house was safe from vandals, so he had a partial bedroom, and bath, a microwave and some bachelor food. It was also closer to Lisa's house than their new home and gave them a secluded place to have unlimited sex.
"Why'd you call me over while Kristy was in the shower?" he asked her as he opened the front door for her.
With visions of naked Kristy so fresh in his mind, Gary was desperate to cum. Even though his bedroom was just a few steps from the front door, he had Lisa naked before she entered it.
"I've seen you looking at her before," Lisa said as she crawled in his bed and laid on her back.
Her boobs were smaller than her sisters but still more than enough to rise proudly up as she laid naked on her back waiting for him. Her legs were shorter but spread wide waiting for him, and her bush was dark and curly compared to Kristy's very blonde tuft. Gary's erection was already busting out of his boxers and eagerly sprang out when he hurriedly ripped them off.
"Did you like?" she teased as she looked at his erection bobbing as he came toward her.
At 24, Gary's dick got hard when the wind blew. Having briefly seen his sexy sister-in-law naked a few hours earlier, and now looking at his naked, very-willing (but less endowed) girlfriend waiting on him in bed, he was about to explode. But he also was reasonably smart enough to know how to not ruin the mood.
"She was OK, but all I could think about during dinner was getting between your gorgeous legs..."
As he crawled in bed she giggled at his comment and opened her legs giving him willing access to her womanhood. He normally loved foreplay and spent much time probing her wetness with his tongue, but tonight he needed relief sooner rather than later. She pulled her knees up, grabbed his hard dick and placed the head at her opening. She was already wet with anticipation, and as soon he felt her wetness he pushed it inside her.
"...and there's no way her pussy is as amazing as this!" Her smile grew as she glowed in his desire for her. He pulled out then quickly forced his hardness deep inside her again. When he hit that special spot her eyes opened wide and she screamed in pleasure. Motivated by her screams and the house empty of any possible parental intervention, he did it again and again.
"Oh my god this feels so incredible!" she screamed as she spread her legs as wide as she could. "Fuck me HARD!" she screamed as he rammed his erection in her with even more intensity.
They were both experiencing a frenzied passion fueled by a sexy game of voyeurism. With his eyes closed Gary fantasized it was Kristy's longer legs spread on either side of him, and her sweeter voice begging him to fuck her hard. He imagined it was her larger breasts bouncing inches away and her wetness taking his furious pounding. And when Lisa's body tensed he pretended it was her cumming as he shot stream after stream of cum inside her. And when he thought he was done he pulled out and shot even more cum on her stomach and even was so excited he was still able to get some on her chest.
"Wow, you must be really horny," she teased tracing a tiny line in one of the globs of his sperm on her stomach.
"Couldn't help it seeing you naked in my bed," he responded. "You always make me hot - and I'm ready for more, NOW!"
