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Office Overtime date idea illustration

Office Overtime

Duration: 2 hours
Budget: any

It's late Wednesday night in February, and the office is quiet and empty, except for you, the dedicated secretary, and your boss, who is still working late. You've been trying to ignore the sexual tension between you two for months, but tonight, it's impossible to deny. You've been working late tooโ€ฆ

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  • It's late Wednesday night in February, and the office is quiet and empty, except for you, the dedicated secretary, and your boss, who is still working late. You've been trying to ignore the sexual tension between you two for months, but tonight, it's impossible to deny. You've been working late too, and you can feel his eyes on you as you bend over to file some papers, your skirt riding up slightly, revealing more of your thighs. You can feel the heat of his gaze on your skin, and you can't help but feel a thrill of excitement.
  • Your boss, noticing your discomfort, asks you to stay a little longer to help him with some important documents. You agree, knowing that this is your chance to finally act on the chemistry between you. He leads you to his office, where the lights are dimmed, and the atmosphere is charged with anticipation. He sits behind his desk, watching you as you approach, his eyes filled with lust. You can see the bulge in his pants, and you know that he wants you as much as you want him.
  • He tells you to close the door behind you, and you do, locking it for good measure. You turn to face him, and he gestures for you to come closer. You walk towards him, your heels clicking on the hardwood floor, your heart pounding in your chest. He stands up and walks around the desk, his eyes never leaving yours. He reaches out and pulls you into his arms, his lips crashing down on yours in a passionate kiss. You can feel his hard cock pressing against your stomach, and you moan into his mouth, your body on fire with desire.
  • He pushes you up against the wall, his hands roaming over your body, squeezing your breasts, your ass, your thighs. You can feel his cock throbbing against you, and you reach down to stroke it through his pants. He groans, his head falling back, and you take the opportunity to kiss his neck, his chest, his abs, slowly making your way down to his cock. You unbuckle his belt, unzip his pants, and pull out his hard cock, stroking it slowly, teasingly.
  • He pushes you to your knees, his cock in your face, and you look up at him, your eyes filled with lust. He grabs your hair, pulling your head back, and you open your mouth, taking his cock deep into your throat. He groans, his hips thrusting forward, and you take him deeper, your head bobbing up and down as you suck his cock. He pulls your head back, his cock popping out of your mouth, and he pulls you to your feet, his lips crashing down on yours in a passionate kiss. He spins you around, bending you over his desk, and you can feel his cock pressing against your ass, ready to take you.

Preparation steps:

  • To set the scene, transform your living room or bedroom into a realistic office setting. Move the furniture around to create a desk area for the boss and a smaller desk or table for the secretary. Add office supplies like pens, papers, and a laptop to make it feel authentic. Dim the lights to create a late-night atmosphere, and add some soft music to set the mood.
  • Dress the part to enhance the roleplay experience. The secretary can wear a tight skirt, a blouse, and high heels to accentuate her curves and make her feel sexy and confident. The boss can wear a suit and tie to exude power and authority. Consider adding accessories like a name tag for the secretary and a briefcase for the boss to make the roles more believable.
  • Prepare some props to make the roleplay more interactive and exciting. A bottle of wine and two glasses can be used to celebrate a job well done, or a blindfold and handcuffs can be used to add a bit of kink to the roleplay. You can also prepare a list of tasks for the secretary to complete, such as taking dictation or filing papers, to make the roleplay more immersive.
  • Set the mood with some romantic and sensual music to create a sultry atmosphere. You can also use scented candles or essential oils to add a touch of sensuality to the room. Make sure the room is warm and inviting, with plenty of pillows and blankets to make the after-play comfortable and cozy.
  • Plan some sexy activities to keep the roleplay exciting and engaging. You can start with some innocent flirting and teasing, gradually building up the sexual tension until it's impossible to resist. Consider incorporating some power dynamics into the roleplay, such as the boss demanding certain tasks or the secretary disobeying orders to add a bit of excitement and unpredictability.

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Some tips:

  • Communicate openly with your partner about your desires and boundaries before starting the roleplay. Make sure you both feel comfortable with the scenario and are on the same page about what you want to explore. This will help you both feel more confident and at ease during the roleplay.
  • Get into character by practicing your roles beforehand. The secretary can practice walking in heels and filing papers, while the boss can practice giving orders and demanding tasks. This will help you both feel more comfortable and confident in your roles, making the roleplay more believable and exciting.
  • Use props and accessories to enhance the roleplay experience. A name tag, a briefcase, or a blindfold can all add to the authenticity and excitement of the roleplay. Don't be afraid to get creative and use whatever props you have on hand to make the roleplay more immersive and engaging.
  • Focus on building sexual tension throughout the roleplay. Start with some innocent flirting and teasing, gradually building up the sexual tension until it's impossible to resist. Use your words, your body language, and your touch to create a sultry and seductive atmosphere that will leave your partner begging for more.
  • Don't be afraid to switch roles or add new elements to the roleplay to keep things fresh and exciting. You can switch from the boss and secretary roles to explore different dynamics, such as the teacher and student or the doctor and nurse. You can also add new elements, such as a blindfold or handcuffs, to add a bit of kink and unpredictability to the roleplay.

Dialogue ideas:

  • Secretary: 'I've been waiting for you to say that. I've been so wet for you all night.'
  • Boss: 'You're such a dirty little secretary, aren't you? Always teasing me with those tight skirts and those fuck-me heels.'
  • Boss: 'I'm going to fuck you so hard tonight, you won't be able to walk straight tomorrow.'
  • Secretary: 'Only for you, boss. Only for you.'
  • Boss: 'You know what you do to me when you bend over like that? You make me want to fuck you right here on this desk.'

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