Chapter 1: The Deflowering of Lily

Lily Lockhart’s mom wasn’t usually forgetful. Usually her mom was organized and buttoned-up. But she had forgotten the bottle of wine when she went over to the Phillips’s house. Something was off about her today. Lily’s dad was out of town on business, but that wasn’t it. He traveled a fair bit, and both Lily and her mom were used to him being away. But there had been some whispered phone calls, and her mom seemed distracted. Anyway, she had forgotten the bottle, and Lily had decided to walk the two blocks to deliver it.

It was a pleasant October evening, unseasonably warm, just after dusk as the fourteen-year-old walked up the path to the Phillips’s front door. The house was set back from the road, behind some trees; you couldn’t really see it well from the road. So what Lily saw when she passed by the living room’s big, bay window shocked her. There was her mother, naked, on her knees, with Mr. Phillips’s cock in her mouth. She almost dropped the bottle onto the pavement but caught it just in time.

Lily was both appalled and fascinated. Appalled that her mom could be cheating on her father like this. Fascinated by the sex. She had never seen an erect penis before, let alone a blow job. Of course she had seen porn, although only once or twice, but she had never seen such a thing in real life. Mr. Phillip’s cock looked huge, although she would later come to know that it was really pretty average in size. And her mom was beautiful, slim with big, round breasts and pert nipples like pencil erasers. Mrs. Phillips was nowhere to be seen. For a moment Lily was afraid that they would see her, then she realized the lights from inside the room would prevent them from seeing anything outside. She was as good as hidden.

The girl could feel herself getting damp between the legs as she watched. Then her mother slipped the cock out of her mouth and laid down on her back as Mr. Phillips got down with her and put his face between her legs. He was eating her out. The teen just stood and stared. She wondered and a few minutes later she was watching her mother convulse with an orgasm. Lily’s hand, the one not holding the bottle slipped, almost involuntarily, into her jeans, as her mother, finished with her trembling, got on her hands and knees, and Mr. Phillips entered her from behind. He was fucking her mom.

Lily could feel the rush of warmth down to her pussy, telling her that her own orgasm was on the way. That freaked her out a bit. How could she be getting off on her mother cheating on her dad? But that thought was quickly overwhelmed by her lustful desires; this was really turning her on.

Then she saw the buxom Mrs. Phillips get up from the couch, which had been hiding her from Lily’s view, and walk over to the coupling pair. She sat down in front of Lily’s mom, and Lily watched as the redhead pulled her mom’s head down to her pussy.

Lily lost it and went over the edge, her pussy contracting again and again. Lily didn’t know how she managed to hold onto the bottle, but she did.

When she recovered, the trio in the living room were snuggling together. Lily, unsure of what to do, ran back home.

She put the bottle back on the kitchen counter where her mother had left it and retreated to her room. She thought about calling her bestie, Alex, but didn’t know what she would say to her, and besides, she couldn’t get the image of her naked mother out of her head.

She had always known her mother was beautiful, but for the first time she understood what that really meant; there was now an undercurrent of lust as she thought about her mom’s naked body. Her breasts were so perfect, firm but hanging down just enough. Not like those fake, perfectly round boob jobs on the women she had seen in porn. Her mom’s areolas were pink and rising out of them were the little cylindrical nipples, just waiting to be suckled.

A wave of desire swept over Lily, and she knew she just had to diddle herself again. She had been masturbating for as long as she could remember, starting by rubbing her pussy against a pillow. In the last few months she had started inserting her fingers into her vagina, something she had been afraid to do as a little girl, and she discovered the joys of stimulating her clit from both inside and out. She needed a release.

Lily stripped and lay down on the bed, closing her eyes. She thought about her mom’s breasts as she circled her own nipples with her hands. Thinking about her mom was so wicked, but that realization only intensified her need for release. Then leaving her left hand to continue playing with her nipples, she slipped her right down between her legs.

She wondered what her mom’s pussy looked like. She hadn’t got a good view of it from the window. She thought about the times she had visually explored her own pussy with a mirror—like a penis, she had never seen a pussy in real life, other than her own of course, and that was difficult to see even with a mirror. She knew that her mom’s was neatly trimmed, a small triangle of hair above—that much she could see from the window—and she imagined the hair along the sides was shaved, leaving a slit with an orchid-like bloom of labia bursting out of it.

Lily rubbed her own labia, turning her thoughts to Mrs. Phillips. She was bigger than her mom, a statuesque five-ten, with long red hair. Her boobs and hips were bigger too. Her areolas were lighter than her mom’s but had the same pencil-eraser nipples. Down below she had a dense, red bush. Lily brought her hand to her mouth and tasted her juices. Did her mom and Mrs. Phillips taste the same? Her hand moved back down south, slipping her index and middle fingers inside her, while her thumb circled her clit.

Was she a lesbian? Why was she fantasizing about the two women? Was this incest? She forced herself to think about Mr. Phillips. He was good looking, in an older guy kind of way, just starting to go gray, slim, well-muscled, but not overbuilt like a bodybuilder. He definitely didn’t have a dad-bod; from the neck down he could pass for a twenty-year-old. He was hot.

She imagined her fingers were his penis, thrusting into her. She imagined what it would be like to feel the weight of his body on her. She wanted it so bad. So much for being a lesbian. What it would be like to take his cock into her mouth? What did a man’s cum taste like? Was it like her own pussy juice?

Enough of the questions, back to imagining a man inside of her. She felt the warmth flow down into her pussy, and she started frigging herself in earnest, pushing herself over the falls. She started convulsing as waves of pleasure washed over her. Unbidden nude images flitted through her mind: her mom, Alex, her English teacher Ms. James, Mr. Phillips, Alex’s brother Trip, her dad. Then her brain shut down, locked in ecstasy.

When her head cleared, she breathed deeply and just lay there, trying not to think about what had just happened. But eventually she came down to earth. The fantasy was over. Her mom was cheating on her dad. What to do about that? Should she tell him? Should she confront her mom? She had no idea what to do. The one piece of advice that came through clearly was that she should sleep on it.

Lily got up, washed in the bathroom, and dressed, going into the living room and turning on the TV. She would lose herself in mindless television.

But it was no use. She was frustrated and unhappy. She knew she had no reason to be. She had a good home, lacking nothing material of importance. Her parents loved and cared for her, and while she had the usual teenaged issues with them, she knew deep down that those weren’t really important. It wasn’t that her mother was having an affair; her disappointment predated her discovery that night. She knew that it was something sexual, but masturbation didn’t really help. She felt better for a little while afterward, but the frustration would inevitably soon return. Maybe a boyfriend would help, but that might be like masturbation; nice while he was around, but not a permanent solution.

Her mom came home an hour and a half later. Lily heard her say from the kitchen, “damn, I forgot the wine,” and then come into the living room. Her mom kissed her on the forehead, asking about her evening. Lily gave a teen grunt in response, and her mom, now used to her teen daughter’s nonverbal responses, rolled her eyes.

“Don’t stay up too late,” her mom said as she headed to her bedroom.

“It’s not a school night,” retorted the teen.

“I know, but you shouldn’t stay up too late anyway. Night.”

“Night, mom,” said Lily.

The next morning Lily decided to confide in Alex, her best friend. She texted her and then cycled over to her house. Alex’s brother Trip answered the door and ushered Lily in.

“Alex is in her room.”

“Thanks,” said Lily as she quickly glanced Trip over. He was limping, probably the result of some minor injury from Friday night’s game. Trip—real name Eric the third, hence “Trip”—was seventeen, a senior, and the school’s star running back. He was also one of the best-looking guys in the school, not that he ever gave Lily the time of day. He was nice enough to her, to be sure, always smiling and saying hello, but she was his little sister’s friend, not his.

Alex—Alexandra—was, as Trip said, in her bed scrolling through Instagram on her phone.

“Hey, girlfriend. What’s up?”

“My mom is having an affair,” Lily blurted out without thinking. “And I don’t know what to do,” tears coming to her eyes.

“Oh, I’m sorry,” said Alex, getting up out of bed and giving Lily a hug. “Tell me about it. How do you know? With who?”

The two girls sat on the bed, and Lily continued. “With Mr. and Mrs. Phillips. I saw them together.”

“Both of them?”

Lily nodded, suppressing a sniffle.

“What did you see exactly?”

“They were having sex.”

“All three of them?”

Lily nodded again and then said, “I don’t know whether I should tell my dad or tell my mom that I know. I just don’t know what to do.”

“Maybe it’s not an affair.” Lily shot her a quizzical look, and Alex continued, “I mean maybe your dad knows. Your dad travels a lot, right?”

Lily nodded again.

“Maybe they have an arrangement. When he’s away, they have their needs met by other people. Or maybe your dad chooses not to know. Lots of couples do that.”

“Really?”

“Yes. But you shouldn’t do anything, at least not until you know more. You could make it worse. If it is an affair, maybe telling your dad will mean they get divorced.”

“How do you know all this?”

“Can you keep a secret?”

“Of course,” Lily nodded again. “You know I can.”

“My parents are swingers. They have sex with other people. Maybe your parents are too.”

Lily’s eyes widened. “How did you find out?”

“They told Trip and me, once they figured we were old enough to understand. They didn’t want us to find out like you did.”

Lily imagined Lexi and Eric Carter having sex with others. It was easy enough. They were both very good looking. Lexi—that is Alexandra senior; the Carter names could be confusing, hence Eric and Trip and Lexi and Alex—was an older version of her daughter, same long black hair, only bigger boobs. She didn’t have glasses like her daughter, but Lily knew she wore contacts. Eric had the same brown hair and eyes as his son, Eric—that is Trip—and the two men were the same size, both very athletic.

“You think my parents are swingers, too?”

“I dunno. Maybe. It would explain what you saw. What did you see, exactly?”

Lily described what she had seen through the bay window, with Alex listening with rapt attention. Lily noticed Alex’s hand strayed to her breast once or twice before she caught herself. The tableau that Lily was describing was clearly turning on her friend.