Playgirl's Obsession Ch. 01 by Dash91830,Dash91830

Elizabeth is hanging out at her place with a bunch of other people from her school, hosting a party. The popular girl’s parents are out of town, which made the whole thing much easier to organize. She is now tapping her foot on the floor very nervously, waiting for her boyfriend Josh to arrive. It makes her feel edgy as she thinks about something important she is going to have to tell him, a thing that she has been trying hard to avoid thinking about and pretend never that it happened. If only she used her brain back then, she wouldn’t be in this deep shit right now, Elizabeth tells herself sullenly.

Suddenly, she can hear the sound of familiar footsteps. Turning around, she sees her childhood friend and smiles. Christine Brennason is walking to her, arms around two handsome male strippers from one of her mother’s new night clubs. The blonde lacrosse player is notorious for philandering, also banging waiters at the hotels that her family’s business acquired over the years. She even hired some male prostitutes. Christine doesn’t need to do that, of course, since she’s more than hot enough to get sex without paying for it, but she just likes the power trip it gives her, to be able to use the men and pay them, sending them away once she is done.

“Hey, Lizzie. What are you up to?” she asks her brooding best friend, using the affectionate nickname only Christine and Josh are allowed to address her with. They’ve all grown up together, along with Josh’s best friend Carter, who went on a trip around the world with his parents. Christine has always been the wild one, as seen by the presence of the two male strippers she is clearly planning to do the deed with later. It’s obvious from the look on her face that she is horny. As a matter of fact, you wouldn’t even have to look since Christine is turned on most of the times.

“Waiting for Josh to be here,” Elizabeth answers, making Christine frown. She doesn’t notice this though, still being preoccupied with her earlier thoughts of guilt and shame. Elizabeth then tries to distract herself by saying “I am just thinking of making him eat my pussy. What about you? Any plans with these two fine gentlemen?” She doesn’t know if they are waiters, strippers or hookers since she has never met these two lads before and doesn’t want to embarrass herself by guessing incorrectly, hence why she referred to them as gentlemen.

Christine smirks. “These two guys are strippers,” she tells her best friend who rolls her eyes. “I just thought you might want to know. Their names don’t really matter. Only their cocks do. One of them will be shafting my pussy while the other impales my ass. You know how much I enjoy double penetration.” Everyone in their friend group know that, not just Elizabeth. The amount of guys she brought to her suite at her family’s flagship hotel in New York is just staggering. Not even Christine’s mom who was said to have been very adventurous in her youth fucked around the much.

Elizabeth still shudders as she thinks about the time she walked in on her closest friend lying on the bed naked and letting seven guys ejaculate all over her bare tits. “Well, make sure the one who fucks your cunt wears a condom. I know you’ve got an IUD in but he could still be carrying diseases. How you managed to avoid herpes after fucking 100 guys I’ll never know.” The crazy bitch actually kept a tally record of the number of men she took to bed. 100 fucking guys. She is a playgirl like no one else.

As Christine walks off, Elizabeth thinks of the reason she is feeling so jittery at the moment. It was a terrible mistake that the girl made a month before her boyfriend’s best friend left on the trip. She and Carter got together and they had sex. Even worse, it was Elizabeth’s first time. So not only did she cheat on her boyfriend with his best friend but she also lost her virginity to him that night. It’s been on her mind ever since, filling her with guilt. She loves Josh so much and doesn’t want him to find out what she did, afraid that she would end up losing him.

Suddenly, the girl sees him turn up in his Mickey Mouse T-shirt and pants, looking very cute like he always does. “Hi, sweetie!” he says to her as he walks up to Elizabeth and they embrace. “You look wonderful today.” She leads him to her room where they sit on her bed together, making out. The dorky teen’s parents were school friends with Elizabeth’s father, and they met when they were little kids. Right now his mom and dad are executives in her parents’ large corporation. Everyone says that the two have been dating since kindergarten. It is why she feels extra guilty for cheating on him since they have so much history and attachment together.

Josh suddenly makes her lie down on her back and starts kissing her thighs, making a trail leading up to her short skirt. He then kisses her searing pussy through the cloth, making her very horny. “You don’t have to give me head so often,”she tells him, even though she enjoys it so much. “I’m more than happy enough with just a few times a week.” She feels very guilty about getting oral so often especially after fucking his best friend behind his back.

“It is my duty as your boyfriend to help you get your rocks off,” he informs her, rubbing her genitals through the skirt, teasing her first to get her more turned on. Reaching underneath, he raises his eyebrows in surprise. “Had no idea you are not wearing underwear today,” he notes, feeling her shaved vulva on his hand. He removes her fingers from on her womanhood, returning to kiss the skirt. She feels so aroused now from how he is worshipping her, despite the earlier guilt still nagging at the back of her mind.

Elizabeth sighs as he lifts her buttocks and slides her skirt down her legs. She kisses him when he moves up so that they are face to face. Josh is doing what he always does, fingering her cunt and rubbing her clit to make sure she is so aroused that by when he actually eats her out, her pussy juices would be gushing all over her face. “You are way too good for me,” she mutters. “I really don’t deserve you.” Josh believes she is only saying stuff like that from being so horny, not knowing that the girl really means it.

“But you do deserve me,” he whispers to her as he thrusts his fingers in and out of her box. He is kissing her on her shoulder and therefore can’t see just how embarrassed she is when he says “You’ve been the perfect girlfriend, always there for me and caring about me so much. This is the least I can do for you.” She highly doubts that he would be such a caring lover if he finds out she cuckolded him with Carter, whom he trust. It would devastate him and she would certainly lose all the oral privilege she gets from dating Josh.

“Thank you so much for this, sweetie,” she exhales as he finger bangs her and kisses all over her face tenderly, and then removes his fingers from inside her pussy. Bringing them to his lips, he licks each finger clean, sucking them and withdrawing with a pop, giving her a seductive look that almost makes her squirt. It is getting her very close now when he decides to stop and moves back down her body again, bringing his face back into her crotch. He smiles up at her cutely.

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