His Anal Mistress

SCENE opens on Tina, a successful photographer, and her husband, Jeremy, as they are having sex in their bedroom. The couple kiss passionately as he climbs on top and starts fucking her in missionary position. Tina loves it and begs him to go deeper. At a certain point, he pulls out and eagerly asks if he can try to put it in her ass again. Her demeanor changes, as she looks up at her husband anxiously. ‘We can try…,’ she says, nervously rolling over. ‘But not if it hurts, ok?’ Jeremy gets very excited and, grabbing his lube, greases her up and starts trying to stretch out her asshole. She squirms and grimaces, clearly uncomfortable, as he slips a finger inside her tight hole. ‘Be careful please,’ she begs him. He slowly removes his finger and starts to try and slide himself inside. The camera focuses on her face, as she winches at the penetration. It hurts very badly and, after a few desperate minutes of trying to make it work, Tina finally cries ‘STOP! Please Jeremy! I can’t do it!’ Disappointed and frustrated, Jeremy pulls out and gets off the bed in a huff. He wipes himself up without looking at his wife. Feeling very guilty, Tina curls up into a ball and apologizes. She tried, she really did. He tells her to forget it. ‘I made the mistake of not doing it before we got married,’ he says coldly. ‘I should have known better.’ She apologizes again as he exits the room, leaving her naked and alone on the bed.

CUT TO TITLE PLATE
Tina, dressed professionally, sits behind her desk at the studio she runs. She is zoned out, thinking about the night before, when her perky young assistant, Carly, comes in with some mood boards. The duo is planning an upcoming wedding shoot and Carly wants to show her boss some of the ideas she has put together for their client. As Tina looks over her work, Carly senses that something is wrong. Tina seems very distracted, as she has been over the past few weeks. Even though the women have always had a very professional relationship and Tina is her boss, they’ve nonetheless grown quite close. ‘Is everything ok, Tina?’ Carly asks cautiously. Tina snaps out of her daze and smiles at her assistant. ‘Yes, I’m sorry. Just have a lot of my mind lately.’ Not wanting to push the issue, Carly goes back to the mood board. While she describes her concepts, Tina stares at her. She is so young and carefree, barely 20 years old. Tina can’t even remember what it feels like to be that outgoing. ‘Can I ask you a personal question?’ She finds herself saying. When Carly says yes, Tina asks if the girl has ever had anal sex. ‘I’m sorry, that’s probably TMI!’ She apologizes, her face blushing as she instantly regrets the question. Carly laughs and tells her not to worry about it. ‘Of course I have,’ she replies. ‘Anal sex really isn’t that big of a deal these days!’ This makes Tina cringe inside. She asks Carly if she enjoys it. Her assistant, happy to be having a friendly talk with the woman she admires so much, tells her that she loves it. It feels amazing, especially once you get used to it. ‘I don’t really get to have it very much anymore, since I broke up with my boyfriend.’ She adds. ‘But I used to have it all the time!’ Tina, loosening up a little bit, starts to share her own situation. She tells her assistant about her husband’s desires and her efforts to try and please him. No matter what toys she buys or how little she eats to prepare herself, she just can’t handle the pain. She feels like a failure, as if she’s holding him back from something. Carly asks if the couple have ever thought of having a threesome or going to a swinger’s party. Tina shakes her head nervously. She’s never considered any of that. Should she? ‘Well,’ Carly jokes nonchalantly, feeling great about the heart-to-heart they are having. ‘If you ever need to tag me in, don’t hesitate to ask! I miss anal!’ She goes back to describing her mood board, as the joke weighs heavily on Tina’s mind.

CUT to that evening. Tina comes home from work to find her husband already eating dinner. She is surprised that he didn’t wait for her. When she sits down in the kitchen to join him, he gives her the cold shoulder. She tries to small talk and ignore the elephant in the room, but the conversation soon drifts back to the night before. ‘I’m really sorry that I keep chickening out,’ she says. ‘I want to do it, Jeremy, I really do!’ Jeremy forks his food without looking up at her or responding. Feeling anxious and guilty, she adds that she’s even started asking her friends for advice. ‘Like who?’ He asks, eyes still on his food. ‘You don’t have any friends anymore. All you do is work!’ Trying her best to ignore his passiveaggressiveness, Tina tells him that she talked to her assistant about it. He should be happy to know that what he is feeling is actually very common these days. Her assistant is twenty and does it all the time. She even joked about having a threesome together. Jeremy’s eyes light up. He puts his fork down and hugs his wife. ‘Are you serious?’ He says. ‘That is such an amazing idea!’ Tina tells him that she was pretty sure the girl was joking, but she wouldn’t be opposed to discussing an open relationship if it made Jeremy happy. Her husband asks to see a photo of the assistant. Tina reiterates that it was probably just a joke and he should forget about it, but he cuts her off. Why would she get his hopes up just to shoot him down again? It’s only a damn picture. When Tina relents and shows him a photo from Carly’s social media, he gets even more excited. Jeremy tells his wife to invite her over tonight. She already said she would do it! They shouldn’t wait for her to change her mind. Besides, Tina’s her boss … it wouldn’t take too much convincing. Tina protests but Jeremy gets mad at her. It isn’t fair. Why would she even tell him about this if she didn’t want to do it too? She is constantly disappointing him. Finally, the conflicted wife agrees to text the girl and invite her over.

CUT to Carly as she is wrapping up yoga practice on the lawn outside her complex. The camera follows her tight ass as she flexes and stretches in her yoga pants. She is very surprised to receive a text from her boss, who normally doesn’t contact her unless it’s a work emergency. When she asks what’s up, she is even more surprised that Tina is inviting her over for a drink at her house to discuss some upcoming projects. Excited and proud to be included, she agrees and says she’ll be over shortly.

CUT to that night. The doorbell rings and a frazzled-looking Tina answers it, inviting Carly inside. The woman immediately asks her to sit down on the couch and leaves abruptly to get her a drink. Carly notices how odd her boss is acting but brushes it off. After all, as she said, the woman just has a lot on her mind these days. As Carly looks around the nice house, Jeremy enters the room. He warmly introduces himself and sits down beside the assistant. They small talk until Tina returns, with a bottle of wine and some glasses. She nervously sets them down on the table and asks her husband if he would open the bottle. She forgot to. He leaves to fetch a corkscrew, squeezing Tina’s shoulders tightly on the way out.

Once alone, Carly asks her boss which upcoming projects she wanted to go over. Tina smiles, her mouth quivering as she tries to calm her nerves. ‘Actually, I wanted to talk to you about what you said earlier today.’ She says. ‘I have decided that I would like you to have anal sex with my husband.’ Carly stares at her boss, awkwardly. ‘Um … I really hope I didn’t offend you earlier,’ she says. ‘I was absolutely joking about that.’ Tina remains stoic and reiterates that she isn’t offended. She wants her to do it. She wants her to do it tonight, in fact, while she watches. ‘So … I can learn,’ she chokes out. Carly grabs her purse. ‘I’m sorry Tina,’ she says getting up. ‘That really wouldn’t be appropriate for me to do. You’re my boss.’ She tries to walk to the front door but is stopped by Jeremy coming back. ‘Where are you going?’ He asks gently. Tina rushes between them and pulls Carly back into the living room. She whispers sternly into her ear that the assistant offered to do it and now she expects it to be done. Carly cannot believe what is happening. ‘I was just trying to be a friend,’ she whispers.

Tina makes her sit back down beside Jeremy. ‘Well, we aren’t friends,’ she replies. ‘You work for me. And I’m asking you to please get this done. We don’t need to discuss it.’ Carly goes very quiet, as the married couple study her reaction. ‘Like my wife said,’ Jeremy chimes in sweetly. ‘It would only be this one time. Just to help her out. Honey, didn’t you mention she was due for an increase soon?’ He is trying to help his wife negotiate. Tina swallows hard and nods. Carly looks at both in them in disgust. ‘Tina, are you really doing this to me?’ She demands, angrily. Tina starts to back pedal but Jeremy shoots her a look. ‘I think it’s important to remember how much my wife trusts you,’ he adds. ‘She wouldn’t ask you to do this if she didn’t think you were up to it. And you said you love anal sex, right?’ Carly ignores him and stares at her boss. ‘You are putting me in an incredibly bad position, Tina.’ She says curtly. ‘I have been your assistant for over a year. I’ve worked overtime. I’ve worked weekends. I’ve done things even when they were not in my job description. I’ve always tried to be the best employee.’ Tina puts her head in her hands, reeling from the guilt. Carly starts to take off her clothes. She turns to Jeremy. ‘So you want to fuck me in the ass?’ She asks, raging. Jeremy nods. Tina looks at them through her fingers. Carly rips her hands away from her face and demands that her boss watch. ‘So, you can learn, right?’ she asks, laughing in her disgust. ‘You are a pathetic woman!’ She gets down on her knees and tells Jeremy to take out his dick, so she can get it nice and wet. ‘Then,’ she says. ‘You can stick it in my ass. At least I can take it!’ BGA Sex Scene. Throughout the sex, Carly instructs Jeremy how to fuck her the way she likes it while Tina cowers in the room, watching and feeling guilty. Even time the wife tries to join in, Carly either makes her do something humiliating to her husband or wait by the sideline. It isn’t long before the satisfied Jeremy pulls out and cums over Carly’s ass.

Tina tries to apologize to Carly, as the assistant quickly throws back on her clothes and heads for the front door. She informs her boss that she is quitting. She doesn’t want anything to do with her any more.