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DATE NIGHT! - bosswife - Sex Roulette
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DATE NIGHT! - bosswife


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Panty Day - For one day (at first) make him wear panties under his regular clothing. Now go on your date! Tease him about it incessantly. You can’t believe how easy it is turning him into your slut, he’s such a cute toy, make him go take a picture in the bathroom, Grab his ass, snap the waistband etc. Just have fun with it! When out on your date order him some some fruity cocktails! He’ll be overwhelmed with excitement and embarrassment and it’ll be sooooo fun to watch lol.

Description
Femdom Date Ideas! I wanted to make a wheel with a bunch of ideas for femdom style dates.

You should use number 1 as a kind of guide for how to behave for the rest of them or make it the starting point and let the rest build onto it!…. “Date Night! Take him out for dinner or drinks. Be ready and spring it on him when he gets in. Tell him to hurry up and get cleaned up. Pick out everything he’ll be wearing. EVERYTHING! Pick the place. Order his food/drinks for him. You Pay! Be bossy and lead. Drop some hints that you expect to get lucky for all the effort. Make sure you phrase it as you fucking him!… You’re basically role playing a “traditional” powerful man and treating him like a “trophy wife”. The whole night is so simple but he’s probably never had an experience even close to it! (Bonuses: Make him wear a thong under his clothes, something uncomfortable :)”

Hopefully I’ll be adding to it regularly! Some ideas are more things to do on/before/around the date but still fun! Combine them with another!

RULES *

  1. READ MY HINT BELOW ABOUT HAVING FUN!
  2. NO SKIPPING! (This is basically the only one of my games where you, the Domme, are going to have a real rule set in stone. This is more of a feel it out kind of introduction, so feel it out! Nothing in here is dangerous or insane. Try it, have fun with it, and talk about it! Be open!
  3. YOU CONTROL THE PHONE! Don’t let him see and keep him guessing. Unless it’s more fun to show him some things ;) or if he doesn’t believe you lol. The challenges are what they are, blame it on bosswife! If it’s a game without a lot of twists and surprises for him you can use the share feature on the site to start a private game. It will record every turn! Great for long distance, remembering which challenges you have already done, and to make sure no one’s cheating! (Once you’ve gotten comfortable or have completed all the items try moving on to the Intro Games.)
  4. IMPORTANT: The very first time you start this adventure tell him his very first task is to google “gentle femdom” and read it to you. Talk about it! Lookup “aftercare” while your at it. It’s important you both always comfort each other if needed and keep lines of communication wide open! (If he’s unaware and your using this to introduce the topic then make sure you are well researched on it! It’s your job to bring him into the fold and conduct yourself responsibly)

HINTS/ADVICE *

  • Most of the ways people get started is with Gentle Femdom or GFD. This definitely made sense and worked best for us as well. This will focus on the following themes/kinks. Worship, Teasing, Orgasm Control, Edging, Fun Little Mind Games/Tricks, Anal Play, Mild Denial, Mild Embarassment/Humiliation, and overall bossy wife shit! But in a sweet way ;) He will be wrapped around your finger. You’ll love the power, especially seeing how much he loves it!
  • HAVE FUN! I know I’m insane with caps lock but it’s important. DO NOT TAKE YOURSELVES TOO SERIOUSLY! There is going to be awkward and funny moments as you start exploring this. Don’t be afraid to laugh and talk about it! It’s all part of the fun and learning. What worked, what didn’t work etc. You will read it in every article you research and it is so true….Hubby and I had an great relationship but it has seriously skyrocketed to Amazing. We are so much closer, our communication is so much better, and we have SO much fun. Plus it’s sexy af ;P
  • I basically hated dirty talk. (Notice the past tense) I found it a lot easier to use words of encouragement and praise. “You’re so cute like this, It’s so sexy having you under my control, I love when your a good boy for me, you better not be naughty or I might have to punish you” etc. This teasing was fun and we both still love it all of the time….The humiliation/degrading aspects can still be part of GFD (and we both had a ton of fun with them ;), it was like our favorite part lol) but do it with the same attitude of encouragement and praise. If your hesitant to use words like (slut, bitch, whore) like I was, just soften it up by switching to (my slutty boy/toy, my cute little whore, my horny little bitch etc.) It’s all about teasing, fun, and love with GFD! We were basically cracking up when I told him to put on panties for the first time. Then when I got just a little bit serious and told him he better do what he was told… he jumped right in! It’s all part of the fun and it will drive him absolutely nuts, trust me!

MORE FUN (All My Games) *

Don’t forget to scroll down to “more by author” to see my other fun Femdom Games! Or follow the link https://naughtygrin.com/users/5523031
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  1. Date Night! Take him out for dinner or drinks. Be ready and spring it on him when he gets in. Tell him to hurry up and get cleaned up. Pick out everything he’ll be wearing. EVERYTHING! Pick the place. Order his food/drinks for him. You Pay! Be bossy and lead. Drop some hints that you expect to get lucky for all the effort. Make sure you phrase it as you fucking him!… You’re basically role playing a “traditional” powerful man and treating him like a “trophy wife”. The whole night is so simple but he’s probably never had an experience even close to it! (Bonuses: Make him wear a thong under his clothes, something uncomfortable :)
  2. Make him feel your dominance! Go to a local adult shop. Tell him he must pick out an anal lube and a crop/flogger/paddle and that you will be picking a cheap slutty bodystocking/costume/lingerie for him to get fucked in! And he’ll be paying lol :P (Look around and have some fun! Grab other things if you want. The whole experience is just about putting him on edge for later. Nobody knows what it’s for and it’s probably the most normal purchase the employees will see that day lol… but he’s still going to be soooo nervous and submissive knowing he’s gearing you up to dominate him.)
  3. Kinky Little Secret. Want to watch your sub squirm?! The answer is yes if you are new to this lol. Get a remote controlled cock ring or butt plug and put it on before you go out. You own him tonight and will tease it as you wish! Randomly turn it on throughout your date night! For a male sub, have them wear some of your uncomfortable panties on top of it! No one will know except the two of you. Watch them melt under your control!
  4. Professional tour guide -- Take your Domme to a museum, an art gallery, or around a historic neighborhood. Do thorough research ahead of time. Choose some exhibits/sites to study and learn about - focus on ones that match her tastes/interests. Then, treat your Domme to a tour that's even better than the kind you pay for!
  5. At-home luxury spa -- Treat your Domme to a romantic spa pampering session that rivals the kind you pay hundreds of dollars for. You can include things like massage, foot rubs, drawing a bath for her, and manicure/pedicure (only if you've been trained!). Make the place spotless ahead of time, use candles and amber bulbs to set the mood, have calming ambient music in the background, and speak in a hushed, soothing voice. Cater the night to her specific tastes and preferences.
  6. Rigged game night -- Pick out a game you both enjoy (Scrabble, Monopoly, poker, Settlers of Catan, anything!), and add your own Dommey twist to it - have a playful "bet" based on who wins, and stack the odds in your favor in a fun way. For example make them take shots before playing Jenga. Play Scrabble and set a timer for their turn, while you mercilessly grope and tease. Add a "findom tax" (lol) for them in Monopoly - every time (s)he passes Go, (s)he has to pay you. Get creative! For bonus points, actually rewrite the rules and put them in the box, so if they get cute and challenge you, you can pull out the "official" rules.
  7. Shopping trip -- Select a piece of apparel that you know turns your subby on, and go on a relaxed-pace shopping excursion to buy it. It can be for you or for them. Maybe he's really turned on by leather, and you take them to shop for new boots. Have them help you try different pairs on like they do at dressier stores, and see which pair makes them the most helplessly aroused. Or maybe you want to see your subby hubby in some revealing sexy lingerie or panties! Take them to buy a few things they can model for you when you get back home! Even better… let them think they are picking stuff out for you! I LOVE doing that switch up, it’s such a mind fuck lol. Of course whatever you buy, make subby carry the bags.
  8. Put it on video: Grab a video camera or a phone that can shoot video. Ask your partner (on camera) if he wants you to be in charge of him sexually, when he agrees order him to then get undressed. Keep him naked or wear something humiliating like frilly panties or lingerie. On video, have him masturbate. Play with him, spank him, walk around him and tease him verbally about what he’ll do for you, how much fun your going to have with him etc. When he cums, ask him if he still wants you to be in charge. If he says yes… have him taste it! If you’ve never done this you can take just the tiniest dab of it on your finger and rub it on your pussy/ass and have him kiss/lick you. (You can just cut it out entirely and have him lick you but it’s an amazing way to test your power. When he’s done, turn off the camera and tell him he’s yours now and will do whatever you say. (Don’t really blackmail him, just roleplay the threat. Have fun with it, tease him!)
  9. Put it on his body: Sit down together and do a little online shopping together. Have him pick out some pretty panties or lingerie and before you order it, ask him what size he wears informing him that the panties (or lingerie) is actually for him! Then tell him that the day his new sexy girly things arrive, he will be your bitch… and and also, not get sex until then. Have him choose how fast the shipping should be.
  10. Put it subtly: Send him a text message during the day asking him out on a date. When he agrees, text him a few times during the day to tell him what time the date is, where you will be taking him, and be sure to tell him to dress nice. When date time arrives, you drive, order his food for him, and pay for the meal. Be sure to tell him how pretty he is too! By the end of the date ask him how it feels to be a girl on her first girl date. Make a toast to him now being your property.
  11. pick Panty Day - For one day (at first) make him wear panties under his regular clothing. Now go on your date! Tease him about it incessantly. You can’t believe how easy it is turning him into your slut, he’s such a cute toy, make him go take a picture in the bathroom, Grab his ass, snap the waistband etc. Just have fun with it! When out on your date order him some some fruity cocktails! He’ll be overwhelmed with excitement and embarrassment and it’ll be sooooo fun to watch lol.
  12. Edging - This is more of a technique than an individual event. Just do it for the entire time leading up to the date, and give him some over the pants stimulation while your out whenever you can! This is the technique of bringing your man to the brink of orgasm and then backing off before he cums. You can do it or order him to do it to himself. You decide when or if he gets sweet relief. Make sure he communicates with you when he is close to orgasm. You can also make it a rule that whenever he is about to orgasm he has to look deep into your eyes to show his love for you and his gratefulness for being allowed to cum. Be sure to comment on what a pathetic puppy he is.
  13. Dinner With A Plug - When you get a chance, why not surprise your sub with dinner? I know you want to make it special, so pick out something sexy! When he’s getting ready order him to strip naked. Get a plug and some lube and tell him you’ll need to keep him in check tonight and ready for your strap later. Have him bend over so you can plug him! Then proceed to pick out his date night outfit. Make sure he’s wearing panties underneath like the slut he is! Now hit the town!
  14. Codename: Do It Now - Another fun public game is to give your sub a public nickname that means you are his Goddess and he will do what you are asking. Perhaps you are at a picnic at a friends house and you would like your drink refreshed. When you use the keyword “sweets” your sentence becomes order, not just a request. “Sweets, can you make me a new margarita?” Roleplaying in public and nobody knows! How hot is that?
  15. Hard On Demand - At random times throughout the date demand that your sub show you his erect cock. You can set a time limit on how long he has to get fully hard, or leave it open ended so that he has to keep trying till it happens. On the occasions where he cannot perform (and most men can’t get hard whenever they want) you will be open for some humiliation play! He’ll be teeming with excitement and fear about whatever funishment is waiting for him at home!
  16. Makeover! Take him shopping somewhere you can buy makeup. As a special treat you’re going to try something new and sexy for him. You can make it cheap stuff….hint it’s not for you! Pick out stuff you would never use to keep the ruse going. Bright red or pink lipstick and nail polish, purple glitter eye shadow etc. Whatever you think will be fun! When you get back find a fun way to spring the surprise that he’s the one getting a makeover! Tease him incessantly about how pretty he looks, how slutty he looks, how your going to make him look like a whore and then use him like one! I like to pair this with the lingerie shopping date :). It’s sooo funny to turn the tables like this. Maybe now he’ll appreciate all the work you put in!
  17. At-Home Fashion Show. Self explanatory. Have him pour you a glass of wine and take him through the closet. Pick out some of your sexiest clothes for him to model for you. Tease him incessantly!

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Everyone is a winner when you give love making a new spin by playing this amazingly fun sex dice game.

Men will love the gambling feel of this game and women get rewarded with hot foreplay.

A whole collection of sensual foreplay activities, from the vanilla to the down right kinky.

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