Tag: Anal Virginity

Lola Fae Gaping Training

GAPING TRAINING
SUGAR DADDY MAKES HIS TEEN GIRLFRIEND TRAIN FOR ANAL SEX

A teen, Tracy (Lola Fae), walks uncomfortably outdoors towards her sugar daddy boyfriend (Bill Bailey)’s house. Her movements are slow and careful, although once she arrives and is greeted by the older man, he’s pleased to see that she’s wearing the butt plug, just like he asked. He even removes it to get a good look at the little gape while Tracy squeaks and blushed. He knows it’s uncomfortable, especially since it’s Tracy’s first time, but she wants Daddy’s dick, right? Then she has to keep up with the training…

Back at home, while having dinner with her actual father, Tracy’s father shows concern for how awkwardly she’s holding herself. She tries to insist that there’s nothing to worry about and encourages them to just have a nice meal.

That’s when her sugar daddy sends a text, demanding to see her pussy. No, better yet, he wants her to send him pictures of her fingering herself under the table. Although she’s nervous about being caught, there’s a certain thrill there as well as she does what he asks, then sends the picture. Although her real dad almost catches her, she just barely escapes his notice.

Tracy, eager to please her boyfriend, continues to wear butt plugs in her everyday life, even in public. While she’s at work as a waitress, she tries her best to concentrate, almost getting caught by a coworker for looking so uncomfortable. Fortunately, she’s able to get away from the situation by pretending she has cramps. It’s perfect timing since her daddy messages her, demanding to see how she’s progressing. She excuses herself and rushes to the bathroom. Once she’s there, she takes pictures of her gape and sends them to her daddy.

Finally, her sugar daddy declares that she’s ready for the wicked evening he has in store for her.

The Anal Virgin, Scene #01

THE ANAL VIRGIN
INNOCENT TEEN OBSESSED WITH HAVING ANAL SEX WITH STEP-BROTHER

SCENE opens early one morning. Jennifer, an 18-year-old girl, slowly wakes up to the sound of slapping coming from down the hall. Confused, she gets out of bed and goes to her doorway. Her step-brother, Jason’s room is on the other end of the hall and his door is ajar. The sounds are coming from inside. Nervously, she tip-toes over and peeks inside, seeing her brother, sitting on his bed, with his back to the door, and his laptop open. He is watching a hardcore anal sex movie and feverishly masturbating. Jennifer doesn’t know what to do. She watches transfixed as he pumps his cock and dirty talks to the movie, saying how much he likes and wants to fuck anal virgins. Embarrassed, Jennifer slips back to her room and gets into bed. She doesn’t know how to feel. She crawls under her covers and lays there in silence, biting her lip. Her thighs squeeze together, and, in an under the cover shot, we see her slide her hand between them and start to touch herself.

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Jennifer walks home from school, staring wide-eyed into space. She can’t stop thinking about what she saw. She walks up her driveway briskly, enters the house, goes straight to her room, locks her door, and starts masturbating again. This time, she positions herself by a mirror, so she can get down on all fours and see how her asshole reacts when she touches herself.

Cut to several days later. Jennifer has snuck into Jason’s room to watch the same movie she caught him with. She stares transfixed at the girls in the movie being plowed from behind. You can see how turned on she is getting.

Cut to several days later. Jennifer is masturbating again. She keeps hearing her brother’s dirty talk as she rubs her pussy and starts touching her asshole too. It’s so tight. She needs something to loosen it up. She pauses and goes over to her dresser where she examines a few different bottles before settling on a tub of petroleum jelly. This should work. She goes back to bed and uses the jelly to slowly get up to two fingers inside her ass. As she works herself up, she begins to repeat the same dirty talk she heard her brother saying … except, in her version, she is the anal virgin that he desires. She fingers herself (first her butt and then both holes) until she cums down her legs.

That night, Jason comes home from a class he’s been taking at the community college. He walks right past where his sister is sitting in the living room, ignoring her as usual. The step-siblings have never had a very close relationship. Jennifer hears him go into his room, put down his things, and start the shower. Their parents are out for the evening and she knows that tonight is her only chance to make something happen. She sneaks to his room, strips out of her clothes and gets onto his bed, her ass arched out in the direction of his bathroom. She hears the shower stop and closes her eyes nervously.

Jason walks out of his bathroom in a towel and is horrified to see his younger step-sister in such a compromising position on his bed. ‘WHAT THE FUCK ARE YOU DOING?!’ He yells, trying to cover her up. Not knowing exactly how to react, Jennifer tries to repeat some of the dialogue she heard the girls saying in the porno movie. Her brother is grossed out and tells her to stop, asking where she heard shit like that. She’s only 18-years-old. They’re family! This is inappropriate! Jennifer sits on her butt and confesses that she saw him masturbating the other morning. She saw what he was watching. Jason is offended that he spied on her. He is a grown man. He’s allowed to watch porn. She tells him that she can’t stop thinking about what she saw. Awkwardly, Jason explains to her that it was just a movie. He sits down beside her, trying to act like a good older brother. ‘Guys watch porn because it’s a fantasy … it’s not real. It’s just meant to help you get off,’ he says, trying to comfort her. ‘You shouldn’t think too much about it or be offended.’ She stares down at the bulge in his towel. ‘I saw how big your dick was,’ she whispers, looking back up at him with doe eyes. He awkwardly covers himself and gets back off the bed. ‘That’s gross,’ he tells her. ‘I don’t want to hear you talking about my dick. You’re my step-sister!’ She keeps pushing, telling him about all the things she’s been doing the last few days since she caught him. She tells him that she masturbated at school, at home, that she worked up to two fingers in her ass, and that she has been stretching herself out. ‘That’s what you’re supposed to do, right?’ She asks. ‘Stretch yourself out for a big cock to fill you up?’ Jason turns away, adjusting himself. He tries to hide the erection forming and she can see he is getting excited. She crawls over to him on the bed and begs to become his anal virgin. She knows that this is his ultimate fantasy, based on everything she heard him say. He tries to get her to stop talking like that, but she is persistent, reiterating that no one has ever fucked her ass before and that she wants him to take her anal virginity. Finally, it gets to a point where Jason can’t handle it anymore and he gives in, throwing her down on all fours, licking her asshole till it is wet, and then shoving his dick inside of her. BGA Sex Scene. At first, Jennifer reacts realistically to it being her first time, with a mix of pain and pleasure, but eagerly encourages her step-brother to keep going. He ends up pulling out and cumming on her ass.

After they are done, the mood dramatically changes in the room. Reality has hit. Jason nervously tries to clean his sister up and make her swear not to tell anyone. He feels very guilty and worried about their parents. They really shouldn’t have done that. It’s pretty gross, if you think about it. Jennifer assures him that she won’t tell anyone, slowly deflated by the realization that her step-brother feels more regret than satisfaction after fucking her. He tells her to get out of his room, so he can clean himself up. She probably should too. She smells like ass. Man, this was such a stupid thing for them to do. With an awkward look on her face, she limps out of the room and slams the door.

The Pickle, Scene #01

THE PICKLE
Step-Brother Must Comfort Sister after She Gets Stuck Trying Anal Sex

SCENE opens on a Sshot of Jenny, an 18-year-old girl, as she leans up against the kitchen counter, arms crossed, while her parents get ready to leave for the day. As they weave around her collecting their things, her father reiterates the house rules: no friends over, no boys over, just a quiet day alone. They will be back before midnight. Jenny rolls her eyes and reminds them that she’s eighteen, fully capable of being left on her own. Her mother hugs her and tells her that she can always call her older brother if she needs something. Jenny rolls her eyes again and mutters ‘step-brother’ under her breath. The parents say goodbye and Jenny watches them leave, a fake smile on her face. As soon as she hears the door close, her smile turns into a smirk and she struts over to the fridge. She leans in and starts pulling out various food items including a cucumber, a bag of carrots, and a pickle jar. She picks each one up and studies them before settling on a carrot. Biting her lip, she collects the rest of the food and walks back to her bedroom, closing the door.

Gary, Jenny’s older step-brother, sips a drink with his buddy at a local bar when his phone starts blowing up. It’s Jenny calling. At first, Gary ignores her but when she calls repeatedly, he excuses himself and answers the phone. She is hysterical, begging her brother to come to the family house because of an emergency. Gary tries to calm her down and understand what’s happening, but the sister is in such a panic that he agrees to come right away, believing there has been a serious accident. He gets off the phone and rushes out of the bar.

CUT to Gary running into the family house. Everything is quiet. He yells for his sister and, after a moment, hears her moaning from the back bedroom. The worried brother storms down the hall and bursts open the door, to discover his younger step-sister squatting in a corner … wearing only a bra. A carrot is sticking out of her ass. Shocked, he covers his eyes and demands to know what’s going on. Jenny begs him to close the door and come in. She doesn’t want anyone to know what’s happened, but she needs his help. Gary, his hand still over his eyes, asks where their parents are. Jenny explains that they have gone out for the day and left her in charge of the house. She thought it might be fun to … experiment … while she was alone. Gary slowly removes his hands from his face and stares at his sister, as she hobbles and crawls towards him. ‘What the hell did you do, sis?’ He asks. She explains that she wanted to know what anal sex felt like because all her friends are doing it. She thought if she tried to practice herself then she wouldn’t be scared for the real thing. She heard about girls using cucumbers, so she tried to work herself up to that … but now they’re stuck. Gary looks horrified and awkward, trying to avoid looking at his sister in such a state. There is a long silence. ‘What exactly did you put up inside of you?’ He mutters. Jenny buckles over and groans, begging her step-brother to just help her get them out and then he can lecture her afterwards.

A Study In Gaping, Scene #01

A STUDY IN GAPING
STUDENT SUBMITS TO INVASIVE ASSHOLE GAPING FROM HER OBSESSED PROFESSOR

SCENE OPENS on a professor’s lush, old-fashioned-looking university office. Professor Claremont (Mick Blue) stands at an ornate window, looking out lost in thought onto the university campus. On the visitors couch across the room, his teacher’s assistant Annabelle (Adriana Chechik) sits, waiting and fidgeting in the awkward silence. The ticking decorative clock on his desk is the only sound for several seconds. Finally, Annabelle breaks the silence — ‘umm, you were saying, professor?’ Professor Claremont snaps out of his reverie and turns to face her. Ah, yes, sorry, he apologizes. His thoughts had whisked him away to unknown places, he says playfully. The professor appears eccentric but charming, like a man from another era. Annabelle seems used to his odd behavior, even a bit enamored by it. He says that they’ve done enough for the day and dismisses her. But as she’s leaving, he calls her back to get her thoughts on a new biology project he’s working on. He trusts her like he trusted her sister, who he taught years ago. Annabelle is flattered, but tries to act nonchalant about it. He continues, saying that the project would be controversial but of great interest to him on both a professional and personal level. She asks him to go on, but before he does, he moves to sit beside her on the couch and switches to a very serious tone. He insists that she swears she not tell anybody what he’s about to tell her. He repeats that it’s quite controversial, and it could jeopardize his career if anybody were to find out about his interest in the subject. Annabelle looks a bit taken aback, but promises that she won’t tell anybody. ‘Marvellous!’ he says, switching back to a lighthearted tone. He pats her knee with his hand innocently. ‘Now then, tell me – what do you know about ‘gaping’?’

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Annabelle tries to recoil a bit from her professor without being obvious about it, moving away from the couch to the desk to make some distance between them. Gaping, she asks incredulously, you mean like the sex thing? Yes, precisely, he answers. He explains that he finds it fascinating… from an anatomical point of view, of course. He remarks that so much of human sexuality is driven by a lust for external body parts — breasts, legs, butts. But those who are interested in gaping want to see the beauty of the insides. He says that it’s remarkable, doesn’t she agree? Annabelle looks quite weirded out, tells the professor that she’s not the right person for this, and moves to leave. But the professor stops her, grabbing her roughly by the throat. Realizing immediately that he has gone too far, he releases her and apologizes. Annabelle gets her bag and is leaving, but something stops her. Despite her hesitance, something has…intrigued her. The professor regards Annabelle for a moment and then, opening up a desk drawer, slowly and silently removes a magazine and sets it on the desk. Annabelle tentatively looks at the magazine, which is filled with dozens of gaping photos. The professor moves behind her. ‘Isn’t it beautiful?’ he whispers in her ear. Annabelle looks scared, but also a little turned-on. He asks her if she trusts him. Reluctantly she admits that she does trust him and she wants to be a part of something important. The professor is pleased to hear that and reminds Annabelle how her sister trusting him proved very beneficial for her. What they’re about to do will change the world, the professor says. Annabelle is ready, and asks the professor what she has to do. In response, the professor silently unbuttons the first few buttons of her blouse before sitting back down on the couch. Annabelle takes the hint and unbuttons the rest of her blouse, taking it off as the professor watches.

As she turns to him and begins removing her pants, revealing her perfect ass, he breaks the silence, saying that as soon as he heard about the phenomenon of gaping, he was intrigued. He’s since researched thousands of videos on gaping, but none of the videos get it right. That’s where Annabelle comes in. Together, she and the professor are going to make it perfect. He leads her over to his desk, where she gets on all fours, sticking her ass up in the air. Slowly, methodically, he slips her panties off. He caresses her ass approvingly, complimenting her on her beautiful asshole. The professor gets to work, lubing up Annabelle’s butthole. This is the first step in creating a beautiful gape, he continues. Sliding his thumb in her lubed up ass, she moans in pleasure. The professor begins to get to work in earnest, and his invasive study doesn’t stop with just his thumb. With the implements he has at the ready to probe and penetrate her (previously) tight asshole, Annabelle’s faith in her professor is about to be stretched to its absolute limits.

Stretching for Daddy, Scene #01

Dominant father Tim (Tommy Pistol) and his stepdaughter Chloe (Kimber Woods) have been having a secret affair for months, right under her mother Erica Lauren’s nose. It’s getting to a point where they keep pushing the boundaries and almost getting caught. But the gullible mom remains clueless. Now, dad wants to fuck his daughter’s ass and she agrees, but she’s never done it before. So, he goes out and buys her a butt plug to stretch herself out for him. She slips it in and then they go upstairs to have lunch as a family. All during lunch, the teen girl twitches and squirms in her short skirt, as she stretches her asshole out for Daddy. He sits beside her, touching her under the table and working himself up … while they both talk innocently with Mom. Finally, when they can’t stand it anymore, the father asks for his favorite pie and his wife offers to get some for the family. As soon as she leaves, he grabs the teen and pulls her to the couch. They have anal sex. As the teen assgasms for the first time, Mom comes back home. They keep quiet and continue fucking while Mom goes into the kitchen to fix their post-lunch treat. The daughter blows him till he shoots his load all over her face. When Mom comes back with their dessert, the semen is dripping from her daughter’s chin.

Good Girls Don’t Do Anal, Scene #01

GOOD GIRLS DON’T DO ANAL
18-YEAR-OLD RELUCTANTLY GIVES HER ANAL VIRGINITY TO HORNY BOYFRIEND

SCENE OPENS as Rick, a college student, is watching TV one afternoon at his girlfriend parents’ house. Gina, who recently turned 18, is housesitting for her folks and casually enters the room with a snack for her boyfriend. She is madly in love with him … and her parents approve too. Even though they are a few years apart, Rick has always been accepted as part of the family. Now, with them away for the whole week, it’s the perfect opportunity for the couple to play house and Gina is soaking up every minute of it. She sits beside her man, snuggles up, and watches while he eats. After a few minutes of small talk, a look comes over Rick. ‘Hey, do you want to do something else?’ He asks coyly. Before Gina can respond, he pulls her onto her lap and starts to kiss her. She smiles and kisses him back, unbuttoning his shirt. The young couple tear each other’s clothes off as they make out. After a few intense minutes of foreplay, Rick flips Gina onto all fours to mount her. The camera focuses on her reaction, as she eagerly waits for her boyfriend to enter. He kisses down her back and leans back to penetrate, when suddenly, her expression changes. ‘WAIT!’ She yells, and Rick pulls out and sits back. ‘What?’ he asks, a sly smirk on his face. Looking irritated, she stands up and starts gathering her things in silence. ‘What?!’ he asks again. ‘Like I told you last time, Rick!’ she says sternly. ‘You keep trying to put it in the wrong hole!’

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The next morning. Gina steps out of the shower, wrapping a towel around her body. She goes to the vanity and starts brushing her teeth when she begins to hear sounds coming from her room. She left her boyfriend sleeping in there. Spitting out her toothpaste, she struts back into her room to find her boyfriend watching porn on her laptop. ‘Rick!’ she interrupts. ‘What are you doing? It’s 10am!’ He acts aloof and she walks over to the screen, peering down to see what it is he’s watching. It’s an anal sex scene. ‘That’s disgusting!’ she says. Rick slowly pulls off her towel, cooing ‘This is what I always do in the morning, babe. I thought you wanted to play house this week? I’m just trying to keep it real!’ He charms her onto the bed and, trying to hide her smile, she sits down. ‘I don’t know why you need to watch that stuff when you have me right here,’ she says quietly. Rick looks her right in the eye. ‘Because I’m a dude and that’s what we do.’ Awkwardly, she kisses him and asks that he not watch it at her house. Leaning in close, he whispers that he wouldn’t have to if she just let him try it once. The camera lingers on Gina’s conflicted face.

One day later. Gina is cooking in the kitchen when Rick comes home from class. He drops his backpack and jokingly says ‘honey, I’m home!’ before running in to kiss her. She seems very happy to be playing house and asks him to help her finish dinner. While they cook together, she asks about his day and reiterates how fun it’s been this week to live together. Now that she is 18, they should start to talk about doing it for real. Rick appeases her, agreeing to everything, as his hands start to run down her waist and around her ass. The more she talks, the more distracted he gets, kissing her neck and start to rub himself up against her backside. At first, she finds it cute but soon gets frustrated at how focused her boyfriend is on her butt. She stops him and demands respect. How many times does she have to tell him: good girls don’t have anal sex. This time, Rick reacts differently. Rather than brush it off or make light of it, he looks genuinely angry. Blowing up at her, he tells her that he doesn’t understand why she’s such a prude. They’ve been together for three years. He has always been a gentleman. All his friend’s girlfriends give it up no problem. Why is she holding him back from trying something he’s always wanted to try? Does she want to push him away? There are plenty of girls at his school who’d been willing to help him out! Gina is dumbstruck by her boyfriend’s reaction. She asks him if that’s an ultimatum and, shaking his head, he tells her that he can’t do it any longer. He’s breaking up with her. He storms out of the house, grabbing his bag on the way out, and leaves the girl to crumble into tears in the kitchen.

One day later. Gina sits, heartbroken, on her bed. She opens her laptop and finds the last page viewed on her browser: the anal sex scene her boyfriend had been watching. She stares at it coldly, pressing play and watching in silence as her room fills with sounds of anal orgasms.

Two days later. Gina opens the door to let Rick inside. It’s been three days since he stormed out of her parent’s house and she is beside herself. She has texted him and asked to talk to him. Taking his hand, she leads him back to her bedroom and sits him down on the bed. He isn’t sure how to react.

She takes a long deep breath before breaking into a speech, something she clearly spent the last few days preparing. She tells him that she loves him, that he is her best friend, and that she wants to spend the rest of her life with him. She knows how much he wants to try anal and, after thinking it over, she will agree to try it for him. But only once and ONLY if he promises to leave it alone afterwards. Rick’s face lights up. He asks if she is sure. Looking at him coldly, she tells him yes. She’ll do it … for him. This descends into the BGA scene. It takes a long time to get the first successful anal penetration and Gina resigns herself to the ‘painal’ feelings that come with having anal sex for the first time. Rick eagerly talks her through it, every step of the way, taking great pleasure in the experience. The more she loosens up, the more he enjoys it. Overall, the sex scene should accurately portray a first-time anal experience with hyper-realism in terms of reactions.

After he has pulled out and cum on her ass, Rick happily curls up beside his girlfriend in bed. He kisses her and tells her how much he loves her. He thanks her profusely for letting them try this together. Overwhelmed by the experience but happy her boyfriend is back, Gina grimaces and tells him she loves him too. As they fall asleep, Rick whispers softly in her ear that, next time, they should try it with one of his friends. Her eyes pop open, as she realizes what she’s gotten herself into!