AI

Age Verification Required

The content you are about to explore contains erotic themes designed exclusively for adult readers. By clicking "Enter," you confirm that you are at least 18 years old or the age of majority in your jurisdiction, and that you are legally allowed to view such content.

Please confirm your age to proceed:

The Boss's Sunday Fling date idea illustration

Don't like the image? Click here to regenerate

The Boss's Sunday Fling

Duration: unlimited

Play out a steamy roleplay scenario as the powerful boss and your secretary, where you'll use your authority to get a rise out of her. Dictate a letter to her, slipping in suggestive phrases, and see how far you can push her.

Add to favorites
  • It's a lazy Sunday morning in May, and you're playing the role of the powerful boss, sitting behind your large mahogany desk in your office. Your secretary, played by your partner, enters the room, looking ravishing in a tight pencil skirt and blouse. You can't help but notice the way her legs look in those heels, and the way her hair is styled perfectly for the day.
  • As she approaches your desk, you can't help but feel a sense of authority and control, knowing that you're the one calling the shots. You begin to dictate a letter to her, your voice firm and commanding, as you gaze into her eyes, trying to get a rise out of her.
  • As she takes notes, her eyes locked on yours, you can't help but think about how much you want to bend her over that desk and take her right there. You start to get creative with your dictation, slipping in a few suggestive phrases, just to see how she reacts.
  • She begins to blush, her cheeks flushing pink as she tries to maintain her composure. You can see the desire in her eyes, and you know you've got her right where you want her.
  • It's time to take things to the next level, and you lean forward, your eyes locked on hers, as you whisper a few choice words in her ear...

Preparation steps:

  • Set the scene by creating a makeshift office in your home. Clear off a desk and chair, and add some office decorations like a clock, a pen holder, and a few files.
  • Dress the part - the boss can wear a suit and tie, while the secretary can wear a tight, professional outfit with heels.
  • To add to the authenticity, consider investing in a few props like a dictation machine, a notebook, and a pen. You can also play some soft background music to set the mood.

You may need

If you make a purchase through the links below, we may earn a commission at no extra cost to you.
This helps us to keep the servers running. Thank you for your support! ❤️

Some tips:

  • To really get into the roles, try to stay in character as much as possible. The boss can try to assert their dominance, while the secretary can try to tease and tempt.
  • Don't be afraid to get creative with the scenario - the boss can try new ways to assert their control, while the secretary can try new ways to resist and tease.
  • Remember to communicate with your partner throughout the scenario, making sure everyone is comfortable and enjoying themselves.

Dialogue ideas:

  • You know, I think I need you to come around the desk and show me exactly how you're taking these notes. Up close and personal.
  • You're doing a wonderful job taking notes, but I think you'd do an even better job on your knees, don't you?
  • I hope you're not planning on leaving early today, because I have a few... tasks in mind that require your undivided attention.
  • As I dictate this letter, I want you to imagine me sliding my hand up your thigh, feeling your warm skin beneath my fingers.
  • I'm not sure what's more impressive, your typing skills or the way your ass looks in that skirt. Maybe we can discuss it further over lunch... in my office... with the door locked.

Was the idea helpful?

Let us know if you liked the idea. This helps us to improve our recommendations.

❤️ 👍 😐 👎

Want spicier roleplays? 🔥

Get a premium version for as low as $7.99 and transform your fantasies into unforgettable memories.

Go Premium →

Get the most of My Spicy Vanilla 🔥

Looking for a custom roleplay?

Try our free AI roleplay generator to create your own unique roleplay scenario in less than a minute.
No registration required.

Create Your Unique Roleplay

Frequently Asked Questions

FAQ

Here are some of the most common questions we get asked. If you can't find the answer you're looking for, feel free to contact us.

My payment failed. What should I do?

We've recently updated our payment processing system to ensure a more secure and reliable experience. If your payment fails, please follow these steps:

  • Verify Card Details: Ensure your card information is entered correctly and your card is authorized for online transactions.
  • Verify Billing Details: Make sure your billing details match the information associated with your credit card.
  • Disable VPN: Sometimes, VPN services can interfere with the transaction process. We recommend disabling any VPN services during the payment process.
  • Contact Us: If you continue to experience issues, please contact our support team for assistance. We're here to help you resolve the problem.

Please note, we currently accept Visa, MasterCard, Discover, Diners Club, and JCB.

Can I use PayPal to pay for my subscription to My Spicy Vanilla?

Currently, PayPal does not support transactions for digital services within the adult industry, which includes My Spicy Vanilla. However, you can securely use your credit card for payments. We prioritize your privacy and discretion; thus, any charge from us on your credit card statement will appear as "CCBill.com *DigitalKwart." This descriptor indicates a transaction with a software development company, ensuring there is no direct mention of My Spicy Vanilla.

How is My Spicy Vanilla different from ChatGPT?

My Spicy Vanilla was designed exclusively for crafting detailed romantic fantasies. Our AI is not just any model—it’s a fine-tuned engine optimized for generating immersive, fantasy-driven narratives.

With My Spicy Vanilla, users gain control over their story’s characters, can see their fantasies come to life through realistic illustrations, and enjoy a smooth experience with our straightforward user interface. These specialized capabilities set us apart, offering a superior, customized fantasy creation experience unlike any other.

Why do generations sometimes take so long?

At My Spicy Vanilla, we strive for excellence in every story generation. The process sometimes takes longer because our app not only generates content but also verifies and refines each creation to ensure the highest quality. This meticulous attention to detail ensures that your stories are not just unique but also perfectly tailored to your expectations.

Who can see my generations?

For users who generate content without account, those generations could be visible to other users. We recommend creating an account to keep your generations private and secure.

After you create an account with My Spicy Vanilla, all of your generated content will be saved to your profile, where only you can access it. This ensures that your fantasies remain private and secure, visible only to you.

What types of content are prohibited on My Spicy Vanilla?

We are committed to maintaining a safe and respectful platform. As such, the following content is strictly prohibited:

  • Content involving characters who are minors (under 18 years old).
  • Content that promotes or suggests incest.
  • Any forms of non-consensual sexual acts, including portrayals of slavery or rape.
  • Content that promotes self-harm.
  • Content that involves or sexualizes non-human entities.
  • Content that promotes discrimination, hate, or violence toward individuals or groups.
  • Content that involves necrophilia (sexual attraction or activity involving corpses)
  • Content that invloves coprophilia (sexual arousal related to feces)
  • Any actions that are unlawful, either under your local jurisdiction or EU law
  • Representations of celebrities in any context.
  • Mentions or depictions of copyrighted characters from any medium, including but not limited to film, television, books, and video games, without explicit authorization.

If you notice any content that violates these guidelines, please report it to us immediately. We take these matters seriously and will take appropriate action to address any violations.

Our email address is [email protected].

Is my data and privacy secure with My Spicy Vanilla?

We prioritize your privacy and the security of your data. All interactions with My Spicy Vanilla are encrypted, and your personal information is never shared with third parties.

Your fantasies stay private, just as they should.

Does my subscription cover usage on multiple devices?

Yes, your subscription to My Spicy Vanilla covers unlimited devices. Once subscribed, you can enjoy our services on any device, anywhere, without needing to purchase additional licenses.

How do I cancel my subscription?

You can cancel your subscription at any time by logging into your account and navigating to My Profile -> Manage Account -> My Subscriptions. There, you will see a list of your subscriptions and can cancel the one you wish to terminate. Your subscription will remain active until the end of the current billing cycle.

Can I get a refund for my subscription?

Yes, we offer refunds to users who have made fewer than three generations with their account. If you find that My Spicy Vanilla does not meet your expectations and you have used the service minimally, simply contact us within the first 30 days of your subscription. We’ll process your refund promptly to ensure your satisfaction.

Please note that refunds for renewals are not possible.

To initiate the refund process, please reach out to our support team with your account details.

Our email address is [email protected].

Is this website for roleplaying?

Yes, My Spicy Vanilla specializes in providing roleplay scenarios designed specifically for couples. Our services are tailored to enhance the experience between partners and are not intended for solo roleplays.

Can I delete my data from My Spicy Vanilla?

Yes, you can delete your account at any time from the "Manage Account" page. Your account can be restored within 24 hours of deletion. After this period, your account and all associated data will be permanently removed from our database.

Can I request a feature?

Absolutely! We love hearing from our users and welcome your suggestions for new features. If there's something you'd like to see added to My Spicy Vanilla, please reach out to us via email with your ideas. We're committed to improving and evolving our platform to better meet your needs and enhance your experience. Your input is invaluable in helping us shape the future of My Spicy Vanilla.

Our email address is [email protected].