14
Feb
Stories & Testimonials

Valentine’s Day Assignment – A Romantic Date with your Dildo

Happy Valentine’s Day darling 💋💋💋 I’m sure you’ve had an eye on the calendar ever since heart-shaped objects and chocolate boxes started appearing on store shelves shortly after Christmas! Eagerly looking forward to a day of romance with your honey bear, your stud muffin, or if you’re not lucky enough to have a Mr Right, then maybe just Mr Right Now?

You might even have been worried as the day crept closer, but worry no more, you have everything you need for a romantic night in with your true love…or at least you do if you were a good girl and followed your instructions earlier this week. You should have all of the mandatory items and hopefully some of the optional ones too.

When you’re reading your instructions, anything written in the regular style font is the narrative, anything in italics is your instructions. Links to videos/audio are provided to save time but you can use your own choices if you prefer.

If you can’t follow anything exactly, then just do your best! So if all you have is your bedroom and you’re told to sit at a table, then sit on the floor by your bed. Make your date as special and memorable as you can.

Getting Ready for Romance 🥰

Finally, it’s Valentine’s Day! You’ve been getting giddier and giddier all week. You’ve made your preparations, put everything in place and you’re almost ready.

You need to prepare for your date. Put on some girly pop while you’re getting ready. Take a shower first if you haven’t had one yet today. 

Dance around your room and feel the romance building. Picture your ideal man, what color is his hair? His eyes? What is his job? What’s his body like? Get specific and make him real. How long have you been together? What is he like, is he affectionate, a bit of a flirt?

Put your lingerie on under your outfit (I hope you don’t need to be told this). Dress as feminine as you can, make sure your hair is nice and do a beautiful evening look using the makeup you have available, even if it’s only lipstick (no, especially if it’s only lipstick).

Your efforts are for you as much as they are for him. Take as long as you need to get yourself in the mood…if you’re not sure about the right outfit, try a few and think about which one your man would find the most attractive.

Wine and Dine 🍷

You hear a knock at your door. You skip to open it and there he is! Smiling, he leans in and gives you a peck on the cheek, “For you,” he says as he lifts up a bunch of flowers and a box of chocolates. “I know it’s corny but I couldn’t arrive empty-handed.”

Blushing heavily, you take the gifts and turn away. “I go and put these in watEEK,” you feel a heavy pinch on your a$$ and turn around. “I told you I couldn’t be empty-handed,” he laughs. You smile and very lasciviously wink at him before turning back to the kitchen.

You put the chocolates to one side, and the flowers in a vase, light the candle, and serve the meal as he sits at the table.

Place your dildo on a seat or on the table opposite where you’ll sit. Put your flower(s) in a vase to the side of the table. Light your candle and put it in the middle of the table and turn off the lights. Play some sensual classical music as you plate your meal for yourself and your date (a small plate for him is fine, he’s hungry for something else).

Once you’re ready to eat, play a male dirty talk video as a second audio track with the music and eat while your man tells you what he wants to do to you later, this is subtext, so keep the volume low. Remember, Mr. Right (or at least Mr. Right Now) is sitting across from you, so make sure you make a lot of romantic eye contact and lots of murmured affirmations as he talks to you (“I’m going to f*ck you so hard!”, “Ohhhh, that would be divine darling”), maintain your feminine composure! He likes that you’re sweet and girly.

You may drink one glass of wine with your meal.

Rom-com & Chill 

After you’ve finished eating, you move to the sofa. You put on a rom-com and pour another glass of wine. He opens the box of chocolates he bought you, picks one out, and holds it in front of you until you obediently open your mouth. He puts it on your tongue, smiles, and says “Good girl!”.

As the movie plays you snuggle closer and closer together until one of you, you’re not sure who initiated it, cranes their neck slightly and gently places their lips on the other.

You slowly but passionately make out while the movie continues in the background, intermittently breaking apart to cool off, drink a little more wine, and eat chocolate. When the movie is nearing its climax, you take the initiative and begin rubbing his crotch before you unzip his fly and he pops out. Ending down you take him in your mouth and begin to suck him…

Take your wine and chocolates and go sit on your sofa. Put on a rom-com (Any will do! The major streaming sites have no end of them and, as it’s Valentine’s Day, even free-to-air TV should be playing something suitable. If you have Netflix, I can recommend “Anyone but You”).

Reapply your lipstick, make sure your lights are off, and watch the movie with your date. Sip another glass of wine and after a quarter of an hour, have a chocolate and then begin to gently make out with your date (the head of your dildo) while you close your eyes and vividly picture your ideal man. His lips pressing against yours, your heart beating faster, his hand slowly moving down your back.

After a couple of minutes of action, pull yourself off him, reapply your lipstick, pour yourself another glass of wine, and watch some more of the movie. Then eat another chocolate and begin making out with him again, but this time a bit more passionately.

Repeat this cycle for at least two-thirds of the film. Make sure you finish the wine and most of the chocolates. A little drunk and a little sweet is the perfect place for your mind tonight.

When it’s nearing the end of the movie, put your dildo on the cushion, bend over and start sucking it. Take your time and do it S…L…O…W…L…Y… This is still the warm-up, you don’t want to spoil your evening with an unfortunate accident, you’re showing him a good time and revving his engine up so he can repay you later.

To the Boudoir (where the magic happens 🤞)

After the movie finishes, he kisses you passionately, drains his glass, and stands up. Turning to face you, he reaches out his hand and pulls you up off the sofa. Then firmly leads you to the bedroom. 

When you step inside, he goes to kiss you again but this is your domain and you know what you want. You put your hand on his chest and push him down so he’s on the bed, you steal a quick kiss and let your tongue dart inside his mouth before you back off, lightly slap his hand away, and move back out of reach.

“Just hold your horses, honey!” you breathily moan as your hands reach behind you to the zip on the back of your dress. Taking your time, you strip off each piece of clothing until you’re standing before him in the lingerie you purchased for this exact moment.

His eyes are bulging out of his head almost as much as his crotch is straining against his trousers. Pouting, you look him dead in his eyes and say, “I hope you like it, sweetie, I bought it just for you.”

He’s too turned on to speak but manages to nod his head in approval. If he opened his mouth, his tongue would loll out and he would drool onto the floor. You almost laugh with delight, perfect!

You move closer and start to unbutton his shirt as he begins running his hands up and down your body and squeezing your butt. Once his clothes have been removed, you fall onto the bed and begin the final act.

Move to the bedroom, take your candle as well and use it for illumination to give the moment a little extra romantic frisson.

Put your date on the bed and give him a slow, sexy striptease. He bought you chocolates and flowers, you are his Valentine’s Day gift so don’t reveal yourself too quickly, make him wait and build anticipation!

When you’re done, reapply your lipstick and get down to what you’ve both been waiting for. Play a video (or audio) of a man having sex and moaning. Don’t watch it, this is to set the mood as your date shows you exactly why you were right to go slow and build him up all evening and make him wait even longer by stripping for him.

Take 20-30 minutes with your dildo, feel free to blindfold yourself first so you can really focus on your imagination.

A Fairytale Ending?

The sex was great, but you’re still struggling to catch your breath, he really knew how to hit your buttons but…and you feel like a horrendous b*tch for even thinking it…it all felt like it was over just a little too quickly. 

One moment you were completely in sync, everything was clicking and all your nerve endings felt like they were on fire.

Then he hugged you even tighter and began thrusting really hard, really deep, and really fast into you. You couldn’t feel your legs and bolts of pure pleasure were radiating out from your p*ssy…and then he stopped, let out a huge groan and you felt him squirting inside you over and over, wow he was deep.

After a few more thrusts, he rolled off you, kissed you deeply, whispered, “I love you” in your ear and then rolled over and fell asleep.

You’re lying there listening to his gentle snoring and wondering “What if he could have kept going just a few minutes longer?” as you feel him slowly oozing out of you and soaking the sheet you’re lying on. You’re not completely disappointed, so much of the night was wonderful, perfect even, but you have a nagging sense that it should have been better.

Mentally shrugging, you let out a small sigh, roll over, away from your date, and open the top drawer of your bedside table, reach in, and…

What happens next depends on you. 

If:

  • You’ve been caged from when you started reading this post for the first time AND
  • Are still caged now 

Then you reach into the drawer and pull out your trusty vibrator. At least there’s something that never lets you down or leaves you feeling unsatisfied! Play a video or audio of a man snoring while you use your vibe to work yourself to a release.

Be quiet as you get yourself off, you don’t want to wake your date up and spoil the illusion that he gave you the perfect Valentine’s Day.

However, if:

  • You weren’t caged when you started reading this post OR
  • You aren’t still caged now OR
  • You don’t have a vibe OR 
  • You feel like you fell short at any point during the night. 

Then you reach into the drawer and…oh no! It’s not there. You could have sworn you left your favourite vibrator charged up and ready to go but you can’t find it. Quietly closing the drawer you let out a deep sigh and close your eyes. Play a video of a man snoring as you drift off to sleep. I know you feel horny and frustrated, that’s part of being a girl on Valentine’s Day 😘! Don’t worry, there’s always next year.

Have fun darling and leave a comment to let everyone know how your date went! 💋

50 thoughts on “Valentine’s Day Assignment – A Romantic Date with your Dildo”

  5. Corsette says:

    Thank you for an amazing assignment with my favorite date. I can’t wait to indulge in the romance and enjoy every moment. It’s just perfect!

    Reply
  8. Jackie Styxx says:

    omg that was so hot! loved how u had links along the way to give it an extended imaginative affect along the way. Its making me squirmy jist thinking about playing it out tonight! lol
    thank you so much Mistress!!
    xoxo

    Reply
  9. Jackie Styxx says:

    omg that was so hot! loved how u had links along the way to give it an extended imaginative affect along the way. Its making me squirmy jist thinking about playing it out tonight! lol
    thank you so much Mistress!!
    xoxo

    Reply
  27. Bree says:

    My “Date” and I had an exquisite night, until it was interrupted by my wife catching me in mid act. In the bedroom, I didn’t have a chair accessible, so I suction cupped my favorite dildo (and my biggest BBC one) to the side of sliding glass door leading to the back yard from my master bedroom.. my wofe always comes in through the garage but for some reason decided to use our back bedroom door and got an eye full of my butt being filled… she didn’t speak to me the rest of the night, luckily I was able to sleep comfy with my stainless plug in all night, she still hasn’t spoken to me this morning, I have no idea what’s on her mind now

    Reply
  28. Dunacn Forgey says:

    This was my first assignment and I was not expecting that! Love the story telling even though I was left wanting at the end! Should have been caged 🙁 This has me so excited for what’s to come

    Reply
  29. Pamala says:

    Love this concept of the date. My Mistress/Wife found very erotic to watch and assist in anything I needed. I was so turned on my clitty was dripping.

    Reply
  32. Heather Elle says:

    Thank you so much for this lovely assignment! This was such a special Valentine’s, and it’s a memory I will definitely cherish! (I’m not sure if I even remember any other Valentine’s Days, lol!)

    I really enjoyed every aspect of the instructions, especially the slow progressive buildup throughout the evening. However, I did finish the evening feeling horny and frustrated…no release for this girl! I was caged throughout the night and I did everything to the best of my ability, but I’m also in the middle of the Academy’s Masturbation Schedule class (which I also recommend!) and there was no release in today’s assignment, so I felt I needed to behave. The “there’s always next year” sticks with me…maybe next year I will be the prize of a real man, and even if I don’t get any release again next year, I can’t imagine there’s any greater satisfaction than providing a man complete and total pleasure.
    I definitely want to have another date night soon with my dildo, and he agrees!

    Reply

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