The events in this story are the basis for the first two chapters of "Fun with Sara."
-There is some truth in every lie.
Cindy
Dave and Cindy had, ironically, met at a church function. Her husband, Tim, would often help out with the Youth Group because his younger brother, Dan, was a member, and Tim didn't have much else to do on Sunday evenings. Dave was 16 when he and Cindy first met, and from the time that they'd met to the time that Dave had stopped going to the youth group about a year and a half later, he'd mostly had very little to do with Cindy. She was in her early 20's, too old for him, and Dave was too distracted by trying to bang high school girls to aim his sights any higher. Plus, Cindy was married, so she was automatically out of bounds.
After Dave graduated from high school, and turned 18, things changed. He continued to hang out with Tim and Cindy, spending a good amount of his time at their small, but nice, trailer that sat in a field surrounded by thick-trunked pine trees. He'd spent a many a night sleeping over, and subsequently sleeping off drunken nights of partying by the time he'd been 18 for a few months. One night in particular sticks out quite often in Dave's head when he thinks back on those days.
It was Dave, Tim, Cindy, and Cindy and Dave's friend, Tiffany, all hanging out and drinking. Dave knew Tiffany from high school, and had messed around with her quite a bit, regularly feeling her up, and making out with her in the backseats of cars belonging to friends who were nice enough to give them both a ride home. He had never got around to sealing the deal with her though. She'd been a virgin throughout her high school career, and even though Dave was a year younger than she was, and had already been with two other girls, he didn't want to be the one to pop that particular cherry. Tiffany was sweet and all, but just a little on the clingy side. Dave knew that if he were to be the one to take her virginity, she'd probably want a relationship, which was something that he just didn't want at the time. She was however, deflowered shortly after she graduated, and since then, she'd developed quite an affinity for cock, which brings us to the night of the party.
On this particular night, the four of them were several sheets to the wind by 11:00 that evening, and Dave was having trouble keeping his hands off of Tiffany's 38DD tits. Her plump, 5 foot 3 form was soft, and inviting, and lucky for Dave, Tiffany was loving the attention that he was giving her. By 11:30, Dave's right hand was over her shoulder, and in her shirt, cupping her glorious tit. Occasionally he'd pinch one of her large nipples and she'd shiver, and let out an almost inaudible moan. Her hand was also creeping every so slow up his thigh, and it was at the tip of his cock when Tim decided to speak up.
"Well," Tim said, abruptly getting up off of the couch. He grabbed Cindy and she got up with him. "Me and my girl here are gonna, go back into the bedroom so..." He stopped and pointed his finger at Dave and Tiffany and wagged it. "You two are on your own! Just don't fuck up my couch!" Dave nodded, and then Tim and Cindy turned away, and headed towards their room. Tiffany was on Dave's lap by the time Tim and Cindy's door had shut.
Dave distinctly remembered that her white bra was as sexy as it could be for housing DD tits. It had, an industrial look to it. There were four hooks in the back, and pale blue butterflies bedecked the front. Dave wasn't focused on the design of the bra though. Instead, his eyes were locked on the deep, inviting cleavage that it had so effectively created. Reaching behind her back, he unhooked it with relative ease. When the last hook was undone, the garment went limp, and started to fall from her shoulders. He pulled it off, setting her massive tits free. Dave grabbed her by the shoulders and brought her back slightly so he could take her in for minute or two. Tiffany's tits were huge, and surprisingly perky for their size. Then again, Tiffany was childless, and she was only 19 at the time.
When he was done ogling them, he pulled her close to him once more, pressing her chest against his own. His hands went between their bodies and he grabbed both of her fleshy orbs, squeezing, and kneaded them. They felt so warm in his hands. Tiffany's moans of satisfaction told Dave to keep going. "Put one in your mouth," she said between ragged breaths. Acquiescing, Dave took a thick, crinkled nipple into his mouth, gently sucking and chewing on it, sending Tiffany deeper into subdued ecstasy. He wrapped his arms around her as Tiffany pulled him in closer to her chest, cutting off his air supply, but her pillowy tits had him hypnotized, and no long aware of his need for breath.
"Fuck me," she pleaded, getting off of him and standing up. Her hands went straight for her hips, tucking her thumbs into the waistband of her pants; and to the chorus of moans coming from Tim and Cindy's bedroom, Dave and Tiffany took all of their clothes off. Dave's shirt had somehow managed to come off at some point when his mouth was latched to one of Tiff's nipples so he had only his shorts, and his underwear to contend with. Tiffany too was already shirtless, and her pajama pants, and white thong slid off her round hips so easily, that Dave could've sworn that gravity was trying to get laid along with him.
When they were both naked, they paused and gave each other pensive stares. Dave was mesmerized. Disappointment and glee bled from him as he looked between her legs. He would not get to see if the hair on her pussy matched the dusky crimson of the shoulder-length locks on her head. Tiffany's puffy cunt was freshly shaven bald. She'd come prepared, Dave thought to himself. Luckily, they were both on the same page because before he had made his way to Tim and Cindy's, he too had made sure that the hair that surrounded his cock was trimmed near the top of his shaft, and non-existent around his balls.
Her skin was pale, and her shoulders, like her face, were dusted lightly with freckles. A pale bulge of a belly sat below her generously proportioned tits. Trailing lower, his eyes reached again the fat, bald mound above her puffy, hairless cunt lips. The very same cunt that he would hopefully be stuffing his cock into soon.
Dave's eight inch manhood was half hard when he'd gotten his shorts off, and he was worried that it was going to stay that way. He was horny beyond reason, but he was also nervous. It was his first time with Tiffany, and he'd in the past had a tendency to get a little stage fright with new partners. Tiffany did not look discouraged though. In fact, she looked a little intimidated by his size, even if it only was half-hard, it was still the biggest cock that she'd ever seen. She grabbed his dick and pulled it towards her while she sat back down on the couch, bringing his half-staff member level with her other pair of puffy lips. She took his cock into her mouth to see if that would help his situation. Immediately, she could taste his masculinity, and his precum. It was a taste that she'd come to enjoy over the past few months, and the added mixture of sweat and pheromones made her pussy absolutely drool.
She was not the best cocksucker he'd ever experienced, David thought. But his cock was still stuffed in a girl's mouth, and to him, back then, that was all it took. He was rock hard in less than two minutes. Tiffany pulled him from her mouth and she leaned back onto the couch, simultaneously spreading her legs for Dave. Even with her legs spread, her "innie" was plump. She was so fucking wet, Dave thought as he looked down at her crevice. He got on top of her and their lips met again. Her kisses were soft and tender, much like the way she sucked his cock. There was also nervousness in the kisses, and Dave thought briefly that she was probably just as nervous as he was. He felt her right hand go between them and grab onto his manhood. When she found it, she guided it to her wetness.
When the tip of Dave's cock pressed against Tiffany's tight hole, he immediately pushed forward, sinking about three of his eight inches inside of her. He pulled out, and then pushed all of himself inside of her. She was tight! So incredibly tight, Dave thought. Fresh, clean, teenage pussy, and he had his cock buried inside of it. His thrusts were slow, deep ones, and Tiffany sucked in breath after breath as she got more and more used to his size.
A squeal escaped her pouty lips, and her freckled, plump face showed pain and pleasure as his pace quickened. "Fuck your dick feels good! It's so fucking big," she said to Dave, who was only half-listening while he rooted himself into her. He slid right into her, as if she were made for him, and he pulled out, only to immediately thrust back in. Dave loved the sensation; the contrast of her tight cunt with the cool air that hit his cock when he pulled out of her. He pushed back in as if his life depended on it, and Tiffany moaned in ecstasy.
The two fucked for the better part of ten minutes, saying almost nothing to each other. Only soft moans and grunts escaped their lips. Their thrusts synced up together, and the two worked diligently to get themselves off. Thanks to Dave's inherent nervousness, he'd managed to almost make Tiffany cum. But when he felt his cum start to boil up in his balls, Dave knew instantly that he wasn't going to be able to last much longer. He'd known in advance that she was on the pill, thankfully, and when he was finally ready to cum, he did so in thick, copious ropes; each of which he spewed unhindered into her tight, teenage cunt.
Tiffany felt Dave's cock start to jerk, and spasm within her, and a rush of non-orgasmic pleasure reverberated through her curvaceous body.
"Oh my god that felt good," Dave said to her, trying to catch his breath. "Did you enjoy it?"
"Yes," she muttered with a heaving chest.
"Did you cum," he asked.
"Yes," she replied once more.
Convinced that she was telling the truth, he didn't bother with asking her again. They got off of the couch, and she asked him if he wanted to take a shower with her. Dave of course gave her a resounding "yes," and they made their way to the small bathroom that was designated for guests. He watched her jiggling ass as the made their way to the bathroom, and he felt his cock start to harden once more.
Dave and Tiffany fucked in the shower once more, and this time, a powerful orgasm racked through her body, and she screamed loud enough for Tim and Cindy to have easily heard. When they finished, they went back into the living room. They were both still naked, and after placing two towels on the couch, they each sat down. Dave once more got on top of Tiffany and their lips met in hot and heavy make out session. Dave decided that he would finish their session by tasting Tiffany's pussy. He slid down between her legs, getting a good look at her juicy cunt. He licked each lip slowly, and teasingly, and Tiffany's legs went up instinctively to give him more access to her. She grabbed under her thighs and pulled them back even further. Dave could taste his own cum as his tongue made its way from her perineum to her clit, and Tiffany had yet another screaming orgasm. They had to have heard that one, they both thought. There was only silence coming from their room now.
After Tiff came for the third time, she laid on the couch while Dave took the floor. Neither managed to stay awake ten more minutes.
II
A few days after Dave's night with Tiffany, Dave found himself bored one hot, summer day. So, he took a drive to look for something to do. His "something to do," came in the form of hanging out with Cindy Price.
That is how it all started... Just hanging out. Dave would come over and they'd spend a couple of hours together, talking at first. Talking about Tim, and talking about how her marriage was falling apart. Cindy told Dave that they'd probably end up divorcing because she wasn't happy with him, and she didn't think that he was happy with her. Dave, being only 18 at the time, wasn't sure what to say to Cindy, so he just agreed with whatever she had to say. "Do whatever made you happy," he'd tell her. That's all he knew to tell her. He was only 18.
The flirtation between the two of them gradually increased. Cindy would hold him just a little longer than she should've held him whenever they would hug when no one else was around. Or they would sit just a little too close to each other when they were watching TV alone together. It was the little things—as usual—that started the affair, and finally, after weeks of flirting innocently, the sexual tension over took them.
"So, Tiffany told me something about you," Cindy said to Dave on a day that had been just like any other whenever they hung out. They were sitting on the couch together, close, and Dave could smell the tanning oil that she'd been using before he had come over. Cindy had been tanning in the nude behind their small trailer that was in the middle of nowhere when he'd arrived. He didn't catch her naked though. She yelled from behind the trailer for him to wait, and since Dave was a gentleman—sort of—he waited. When she answered the door, she was wearing a pair of loose fitting boxer shorts, and a loose fitting, white tank top that made it obvious she was wearing nothing underneath it. He could see just a hint of her brown shaded nipples.
"What did she tell you," Dave asked nervously. He squirmed on the couch, trying to hide a semi that had come up almost every time he sat next to her.
"I'm afraid to tell you," she replied. Her eyes shifted from his face, down to his crotch.
"Why?"
"Because if I tell you what she said... Things might... Happen."
Dave was confused. He became worried that Tiffany might've said that he was no good in bed, or that he was small, by why would that have anything to do with Cindy, he asked himself. Maybe she said something to Cindy that disappointed her. To Dave, Cindy was authoritative. She was older, and wiser. She knew much more about life than he and Tiffany put together did, in spite of the fact that she was only a few years older than they both were. She'd been through so much, and so much of what she'd been through was so fucked up. She was forced to grow up, and quick.
"Come on," he pleaded, trying not to sound nervous. "What did she say?"
