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Glasses (37)

WLT S02E01: New Place, New Personalities

I know all about nerdy teenagers, like the one I caught today. She thought I wouldn't suspect her of stealing something because she looked so innocent, but I knew those glasses and girly skirt were just a disguise. That's why I wasn't surprised when I found the stolen R-rated novels in her backpack. That's why these girls read so much. Most nerds are virgins, sure, but they are horny all the time and too shy to live out all their sexual fantasies, so they hide behind the naughtiest books they can find. When I took off her clothes to do a cavity search, her body shocked me. It's like she had been carving it to perfection, waiting for someone to make it his, and that someone was going to be me. If she wanted to get out of trouble, she was going to bend over my desk and recreate her erotic books with me.

Case No. 8004261 - Erotic Books Taught This Nerd How To Fuck

In a crowded mall, Aria slipped some items into her bra, hoping to conceal it from the prying eyes of the store's security cameras and staff. London Ford, the mall's vigilant security guard, immediately noticed something was wrong, so he quickly moved to intercept her. As Aria attempted to exit the store, London blocked her way out and gave her no choice but to follow him to his office. The questioning began and Aria failed to explain why she had so many unpaid items with her. Eventually, London was forced to strip the girl naked to make her come clean about stuffing her bra with merch. As Aria grew nervous, London decided to change his game and play the good cop to give her a chance to redeem herself. Her perk little tits had caught his eyes and he just wanted a little release from his stressful job as a security guard. Aria soon understood that her best way out of this situation was showing London what her beautiful boobs and her young yet powerful pussy were capable of.

Case No. 8003680 - Bra Stuffing Brat

Abigail (Leana Lovings) is a teen high school student from a poor family. One day she goes to her guidance counselor's house, since the guidance counselor, Mr. Taylor (Jason Sarcinelli), has offered to give her some of his own girl's old dresses for Abigail's upcoming prom.

Abigail is grateful, but as she changes in and out of the dresses, Mr. Taylor spies on her through a crack in the doorway. But when Abigail discovers that Mr. Taylor is both spying on her AND is lying about being a parent, it's revealed that he manipulated the situation in order to seduce Abigail.

Abigail is at first livid, but Mr. Taylor manipulates her further, guilting her by reminding her of all the help he's given her. After everything he's done for her, the least she can do is show her gratitude... right?

His Charitable Act

Steve (Elias Cash), his girlfriend Cassie (Leana Lovings), and their mutual friend Danny (Victor Ray) are playing poker. When Cassie takes a break and goes into the kitchen to make snacks, Danny suggests a wild bet: whoever loses the next hand gets to fuck the other guy's girlfriend. Steve playfully accepts, not thinking the bet is serious. But when he loses, he finds out that Danny was completely serious about it.

When Cassie finds out about the stakes of the bet, she seems furious and decides to go along with it to make Steve feel bad for using her in a bet. Steve eventually leaves, dejected and humiliated, but once he's gone... the truth reveals itself.

PureTaboo - 2025.11.11 - Leana Lovings - Up The Stakes

Madison (Madison Wilde) lives with her extremely strict stepdad, Thomas (Charles Dera). He runs a tight household, where Madison is expected to live up to his rigid expectations no matter what. That's why it's no surprise that he's nearly furious when Madison comes home late from school one day. Madison apologizes, but she knows that nothing she can say will dampen his disappointment. Luckily, he lets her off with a warning, and she goes up to her room to apparently study.

But when Madison is late again for dinner later, Thomas bolts upstairs to confront her, not bothering to knock on her bedroom door and simply bursting in. He is shocked to walk in on Madison practicing giving a blowjob to a dildo, and his anger comes to a rolling boil. This is NOT how he raised her, and even though Madison explains that she wants to practice sexual acts so that she can keep up with other girls her age, he's still furious with her despite her rationale.

Seeing as it will be nearly impossible to prevent Madison from experiencing the delights of adulthood, Thomas decides that he will take her sexual education in hand himself. He whips out his dick and instructs her to get on her knees and blow him. Madison's a little hesitant, but she wants to make her stepdad happy, so she does it. What follows is an intense and energetic sex session where Thomas shows Madison the ropes, including how to deepthroat his massive dick.

PureTaboo - 2025.07.15 - Madison Wilde - Step By Step Inch By Inch

I fucking love my job. Being a security guard at the mall is such a power rush, especially when bratty little thieves like Ameena try to steal from us. I know girls like her, getting caught is half the fun for these sluts, and I'm more than willing to play my part. Now I get to have fun with her tight little holes and paint that pretty face with a fresh load of cum... what a life!

Shoplyfter - 2025.09.13 - Ameena Green - The Politicians Daughter

We hope you're ready for an episode packed with events featuring six of the most amazing talent in the industry. Barriers are down and our We Live Together girls have opened up a little, as with day three they've had plenty of time to get to know each other on a more intimate level... Besides worshipping each other's bodies, I mean. Demi starts everyone off with some home cooked breakfast as early birds Gabbie and Vina soak up some sun, pulling off clothes as they wait for rest of house to become more active. La Sirena glams it up in the make-up chair as redhead duo Lacy and Sabina prepare for quick runway show. Our girls group up and split off into various rooms for midday orgasms - kitchen, bedroom, bathroom - before reconvening for more naughty games. The girls end the night by providing funny, hot, and sometimes embarrassing commentary while sharing old content. Ever wanted to watch porn with the star? Or maybe just a group of happy horny girls? We Live Together: Season 2 has you covered.

Lacy Lennon - [WeLiveTogether.com] - [2020] - Show And Tell Her - Vina Sky, Demi Sutra

Ugh, I’m literally stuck in this disgusting, cramped office with four gross loss prevention officers who think they’re so much better than me just because they caught me shoplifting. Newsflash - I always get what I want when I want it. But now, these men have me right where they want me - naked, vulnerable, and entirely at their mercy. It’s infuriating because I’m not used to being told what to do or being treated like some kind of...I don’t know, sex toy or something. But as they’re touching me, groping me, and exploring my body, I have to admit that it’s kind of...exciting. I mean, I’d never admit it out loud, but being bent over and fucked by four different men is a total thrill, even if it is a bit degrading. And okay, fine, I’ll say it - I’m loving every second of being their little fuck toy! Being passed around and used for their pleasure…I never knew submitting to someone could be so fun. Bent over on the desk, my delicate pussy lips spread by their strong hands, all of them gawking at me, imagining all of the fucked up things they wanted to do to me. It’s wrong, but holy fuck am I wet right now… I’m just a vessel for their cum, and it’s kind of...liberating. I mean, I’m not going to start wearing a “I’m a slut" t-shirt or anything, but...yeah. Being completely and utterly at their mercy is kind of a turn-on. And as they’re taking turns fucking me, I’m just going to have to swallow my pride and admit that, yeah, I’m enjoying this. A lot.

Shoplyfter - 2025.03.29 - Angel Windell - The Officers Gangbang

It's day two here with We Live Together, and our girls are waking up after a long day of orgies, filming, and figuring out how they mesh with one another. As with last season, some are early birds and others are night owls sleeping in, but every girl is eager to start a new day of kissing, licking, laughing, taunting, and teasing! Sabina and Demi launch the morning off with some topless yoga in leggings, stretching out those lithe limbs. But girls will be girls, and soon they're showing off for the cameras and tearing off clothing. We move on to some guessing games, Never Have I Ever, and spontaneous orgasms on the kitchen counter before dinner. Quivering, squirting, jiggling... All things seem to be going well - So far.

Lacy Lennon - [WeLiveTogether.com] - [2020] - Never Have We Ever - Demi Sutra, Vina Sky, LaSirena69

Lacy Lennon - [WeLiveTogether.com] - [2020] - New Place New Personalities - Demi Sutra, Vina Sky, LaSirena69

Ms. Davies (Kiki D'Aire), a high school teacher, is having a secret affair with one of her students, Terry (Anthony Pierce). One day after class, however, Terry brings his friend Paul (Parker Ambrose) along with him, which confuses Ms. Davies. Her confusion turns to horror when Terry explains that he let Paul in on their little secret. In fact, he was wondering if Ms. Davies wouldn't mind fucking Paul as well, especially since he's a virgin and could use a bit of practice before he gets out in the field.

Ms. Davies is heartbroken, unable to comprehend how Terry could betray her trust like this and simply offer her up to his best friend as if she were some object. She thought what they had was real- not just some fling that meant nothing. Before long, she quickly realizes how stupid she was to even start something like this with Terry. After all, he's just some high school teen with barely a scrap of life experience.

Ms. Davies outright refuses to go along with Terry's plan... which is exactly when Paul steps in to take control of the conversation. He's not as much of a pushover as Terry is and has far less of a moral code. Paul manipulates the situation, convincing Ms. Davies to give him a blowjob, and then eventually the rest of her body. He even lets Terry step in to DP her, allowing him to join in on the fun. It's clear that after this, however, their friendship will forever be changed.

PureTaboo - 2025.03.04 - Kiki D Aire - Learned The Hard Way

Leana Lovings excitedly approaches a dresser, talking to herself, saying 'I can't believe Seth finally gave me an empty drawer of my own at his place... Things are getting pretty serious with us...' But as she opens the drawer for the first time, a piece of paper, which must've been stuck to the roof of the drawer, falls down. Her excitement turns to curiosity, then confusion when she unfolds the paper and sees a list of women's names, including her own. All of the women's names, except her own, have been crossed off.

As Leana reads over the names, especially staring at her own, she grows increasingly concerned. She looks a bit hesitant, as if wondering what to do, though then tucks the list into her pants and exits the bedroom.

She approaches her boyfriend, Seth Gamble, to eke the truth out of him since she's too meek to confront him directly. But all of her attempts fail as Seth brushes her off... until she suggests roleplaying a hookup between strangers (with her using a name from the list). Seth is intrigued and gives into having lustful sex, though he still seems oblivious to all Leana's attempts, giving up nothing. But just HOW oblivious is Seth, really...?

PureTaboo - 2025.01.14 - Leana Lovings - The List

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