Sissy Date Ideas for Connection, Fun, and Identity Reaffirmation

Let’s talk about going on a sissy date.

If your submissive enjoys forced feminization, crossdressing, or sissy play, you, as the femdom, might want to take them out on dates to reaffirm their feminized status. Not only can this be a fun “scene” to play out, but it can also be a fantastic way to share a date with your partner where they feel seen, heard, and understood.

It’s a win-win!

However, as you start to plan out different sissy dates you both can enjoy, you might find yourself at an impasse. It’s not like sissy dates are regularly featured in TVs or movies, and it’s unlikely that most of your friends have talked about taking their husbands/boyfriends/partners/submissives out on feminized dates either!

So, with that in mind, let’s talk about ideas for a sissy date – because it can be a blast for everyone involved!

A Note Before We Begin

I hate, hate, hate the term “sissy”. It isn’t a good fit for me or my dynamics – and I know a few other femdoms feel similarly. However, this is the most popular term that people are searching – and I wanted to ensure that the information ended up in the hands of the people who want it.

So assume these sissy dates work just as amazingly for feminization dates or crossdressing dates.

10 Sissy Date Ideas

Ready? Let’s dive into these sissy date ideas to give you a good plan for your next date night. I’ve tried to pick date options that require legwork from the submissive – as well as some options that rely on the dominant to put things together. All of the planning should not just fall on your shoulders.

Since all of us have our own comfort level with being out en femme, I’ve also included an “Exposure Level” for each sissy date idea. Choose dates with lower levels of exposure if you’re not into others knowing about your feminization, or go with higher exposure levels if that’s part of the fun for you. It’s all about how you want to play!

Get Your Nails Done Together

Going to a nail salon can be an amazing way to reinforce femininity without requiring a submissive to leave the house entirely en femme. A nail salon is used to servicing a wide variety of clientele, and if you’re nervous, you can specifically seek out a nail salon in a LGBTQ+ part of town (if available).

As always, never include the unexpecting service staff in your kink, but when it comes down to it, there’s no need to. When we’ve done this in the past, when the staff asks my male-presenting partner what color they want, my partner looks at me with a “What do you think I should do?” or says “Whatever my partner wants”. Definitely not the standard nail salon color selection process, but it never includes the salon employees in our kink dynamic – which can be a great workaround.

If your submissive is not ready for colored nails, they can simply have the manicure/pedicure with strengthening polish only. This can be a great way to fit a feminized activity into a lifestyle where the submissive can’t have colored nail polish.

If your submissive is open to a feminized style but doesn’t want it to stand out when they’re not en femme, we’re fond of french tipped manicures and pedicures. They’re cute if someone is paying attention (and he feels amazing in them), but they aren’t something most passing strangers pick up on.

I’m partial to receiving a pedicure and/or manicure at the same time so I can sit next to my partner and talk, but it’s really up to what you and your partner want to do on your sissy date.

For extra fun, when you both get home, pick out an outfit for your feminized submissive and take a few pictures to memorialize the experience. This can be extra fun for Fetlife pictures.

Exposure Level: 2/5

As this sissy date has the two of you hitting up a local nail salon to get your nails done, it isn’t without exposure. You can minimize this concern with clear-coat polish or with a masculinely-dressed submissive. If necessary, you can even state “he lost a bet” too – but honestly, every nail salon has given us a quirked eyebrow when we show up but quickly had no issue with it.

If your submissive is extremely shy, this can even be done at home with the femdom as the “nail salon artist”. All up to you!

---

Go Lingerie Shopping

Do you have a lingerie shop nearby? Depending on where you live, that may be as “basic” as a bra store, but you might be lucky enough to live near an LGBTQA+ erotic superstore.

Regardless of what you have nearby, your next femdom date can have you both heading there. Not only does this give you some fun, new accessories to play with when you both get home, but the shopping experience itself can be a blast.

Simply walk through the lingerie store and whisper about potential options between the two of you. Let your submissive partner touch and feel the different materials. Depending on how long they’ve been wearing feminine clothing, this can be a great opportunity to explain different things about lingerie – like underwire, lace, push-up cups, different bra and panty styles, and more. (Assigning “The Lingerie Handbook” for reading before you both head out can be an extra fun way to extend this date.)

Depending on how comfortable you both are – and whether humiliation is part of your dynamic, this lingerie visit can also include holding up pairs of lingerie in front of your partner’s frame, setting up your partner for a bra fitting, your partner trying on bras or pajamas, or simply making your sissy date partner obviously carry all of the items you’ve already picked out.

As always, ensure you’re not non-consensually involving the store staff in your scene. It can depend on where you live. In more progressive areas, staff may not bat an eye to masculine-presenting people purchasing lingerie, but that won’t be the case in all areas.

Practicality-wise, if you’re planning on making a purchase in-store and know which store you’ll be heading to, take your partner’s measurements ahead of time if they’re uncomfortable trying on lingerie in-store. This will let you compare online size charts to your partner’s measurements to figure out which sizes are best for your partner.

Exposure Level: 3/5

Just like getting your nails done, shopping for lingerie is another sissy date that can be done without going out en femme. However, as your discussions will likely involve discussion of what will fit their body, it has a slightly higher exposure level than simply getting your nails done.

---

A Girl’s Night with a Sleepover

Remember the sleepovers of our teenage and childhood years? (And totally okay if you’re only remembering the stereotype of one as you never did one yourself) At-home, pampering spa days with your friends were all about bonding over feminine activities while treating yourselves – and sharing secrets with people you wanted to get closer to.

Recreate that with your feminized partner for an intimate, feminine-focused bonding experience.

This can pretty much look like anything you want, but some suggested starter ideas include:

• Romantic comedy and a movie (with wine/popcorn/beer/snacks now that you’re adults and you control the food!)
• Play a “get to know you” board game or even a teenage-focused board game
• Talk about your celebrity crushes – and possibly watch movies or social media videos featuring those crushes
• Play Truth or Dare (some of my femdom Truth or Dare options might be a good fit here)
• Paint each other toenails and fingers
• Swap clothes or share closets (if you’re similar sizes) to see what looks good on both of you. Simply share accessories if your clothing is different sizes.
• Challenge each other to stay up as late as possible with a “punishment” for the loser (feel free to make the femdom’s “punishment” a reward for her, actually. This is a femdom sissy date idea list, after all!)

Exposure Level: 0/5

As you can do this entirely at home, there’s no exposure here unless you choose to leave the house or open the curtains.

---

High Heels Training as a Sissy Date

Is your en femme partner comfortable with their high heels? If not, this can be a lovely date idea! Instead of focusing on heading out, surprise them with a pair of high heels (one they already own or a new pair for them).

Make high heels the focus of your date time together. Come up with high heel drills (YouTube can be a great resource if you want to actually add strength training). Make your feminized partner fetch your drinks and other items while in their heels. Make them walk across areas while you watch and critique them.

While the “focus” of this sissy date is the heels, it doesn’t have to be the only thing you both do. Consider an at-home meal while your partner needs to sit properly and gracefully with their heels. Let them practice their make-up while wearing the heels. Go through their closet together and come up with a great outfit with their heels – then take photos. It’s really up to you and what sounds fun!

Some tips for high heels:

• Be careful with carpet. Hard wood floor or cement will be the safest bet.
• Hallways can be fantastic places to learn how to walk in heels. The walls on either side can be a catching point if someone loses their balance.
• If you’re purchasing high heels just for this purpose, look for something that has an ankle strap and isn’t too tall. Avoid standard pumps. The Pleasers Pink Label brand goes up to a women’s size 16 if you’re having issues finding “sexy” heels for your feminized partner.
• Remember that high heel familiarity comes with time – and with ankle strength. Make a judgment call about what your high-heel-wearing partner can attain during your date. They may not be safe to serve you a beer – especially if this is a fresh, unbroken pair of heels. Expect blisters for the unaccustomed and be ready to tap out early. You can always repeat the date later.

Exposure Level: 1/5

If you choose to head outside to take advantage of sturdy outdoor cement, you might be risking a bit more discovery.

---

Pick Them Up for a “Date”

In this sissy date, you’re setting up your submissive to receive the full “teenage girl on her first date” experience – something a lot of submissives into feminization really, really wish they had gotten to experience!

Weeks in advance, you’re going to pick out a complete outfit for them to wear. I recommend adding something new to the outfit (maybe a necklace they haven’t seen or some heels?), but you can easily do this with all of the items that are already in your submissive’s closet if budget is a concern. Just don’t show them the outfit.

Then get to planning a traditional, “heteronormative” date that fits within your comfort levels. I highly recommend “taking” them somewhere to get the full date experience of picking them up at the door, but you can certainly “pick them up” at your front door and then stay in too.

Some general ideas:

• Dinner and a movie
• Drive-thru meal and parking somewhere scenic for a more private option
• Walking around a local bookstore
• If you’re so lucky, heading to the local LGBT-friendly area and walking around there
• Staying in with an action movie
• Head out for ice cream – and sit in the parking lot
• Mini golfing
• Heading to a local coffee shop

The times we’ve done this, I’ve simply “taken him out” to dinner – including one time when that “dinner” was simply an empty conference room at the hotel we were staying at with take-out food.

Remember, this date is all about completing the entire experience, from beginning to end, with the submissive feeling like a pampered, feminized “woman” who is being woo’ed by her partner. That means I’d recommend an outline that looks like this:

• Tell your partner to block off the date time on their calendar. Tell them they’ll need to be femininely groomed (whatever that means to you) and ready for make-up that day.
• Day of, ask them to go in another room while you set out one room with all of the items.
• Lay out all of the items you picked out for their outfit. Feel free to go all the way. We’re talking heels, jewelry, purse, undergarments, make-up colors, lotions, etc. If you want to really make a statement, get a large box and “wrap” it like you see the rich men send their partners a dress in the movies.
• Invite them into the room, and tell them you expect them to be dressed and ready by a specific time. You’ll be back to pick them up then.
• I recommend giving them an hour or two to get ready and let the butterflies form. You can head out and do whatever you want, really. Depending on what your date is (to-go food, etc.), you might have a specific plan in mind.
• I will go out and pick up a bouquet of roses (maybe even chocolates too) then settle in to read a book at a coffee shop.
• Around the scheduled time, show back up at your front door with your roses/chocolates/gift. I usually like to show up 10 minutes early just to fuck with him, but that’s up to you.
• Knock on your own door – or ring the doorbell. Remember, it’s about the experience – and “awkwardly answering the door” is a big part of that.
• Enjoy the magical transformation you get to see right in front of your eyes. Provide liberal compliments and embrace the slight awkwardness. It’s part of it.
• At some point, use the classic “Well, let’s get going, huh?” line, and head out to the rest of your date, treating them like a semi-new partner that you’re trying to impress the entire night.

It’s generally a really fun time!

Exposure Level: ?/5

How “exposing” this sissy date idea is really depends on your plans. If you take them out to a local diner and a movie, you can expect this to rank high on the exposure level.

---

Fruity, “Feminine”, Sissy Date Cocktails

Depending on what social circles your partner hangs around in – and how they were raised (I’m noticing a more carefree attitude on cocktail selection in younger generations), your sissy date partner may have a limited experience with fruity, “feminine” cocktails like “Sex on the Beach” or Pina Coladas.

Use this as a fun femdom crossdressing date idea!

Task your submissive to find the most feminine, tasty cocktail recipe they can find. Multiple drink recipes can ensure you both have options. Since this is a femdom date idea, you can then task them with ensuring you have the drinkware and recipes to make the drink. I highly recommend looking up over-the-top cocktail options that include tall, colorful garnishes.

Day of the date, you can lay out a cute, femininized outfit for your forced feminization submissive to wear. A short, flowy dress can be a fantastic fit – especially as drink prep will leave them bending over often. (I speak from experience!) If they have familiarity in heels, adding high heels to their outfit can also be an erotic addition.

If they’re into chastity, this can also be a great time to throw in a mini BDSM scene where you put on a chastity cage.

Once they’re all outfitted, you can make it clear that they’re expected to make their feminized drinks, serve them to you, and enjoy the drinks themselves too. You both can sit and talk as you both enjoy your cocktails. Depending on your dynamic, you can include various verbiage about how they’re “one of the girls” – or make fun of their “beta status” because they’re drinking their playful cocktails too.

Or simply let them enjoy how awesome some of these cool cocktails can taste – free from aggravating gender norms. It’s all up to how you want to do it.

Exposure Level: 0/5

You can do this sissy date idea entirely in the privacy of your own home. It’s virtually zero-risk; just ensure your intoxication levels don’t lead to making some poor choices about leaving the house!

---

Outdoor Picnic

Okay, this one is as cheesy as it is cute, but that’s because it works!

Simply plan an outdoor picnic for you and your feminized submissive. This can be as elaborate – or chill – as you’d like. Grab your favorite take-out dinner and a blanket for a simple option – or go all-out with a picnic basket, pourable drinks, a mini table, blankets, pillows, and more. Just remember: glass is usually a no-go at most outdoor areas!

My ideal feminized picnic sissy date would look like:

• Doing “secret” digging ahead of time to suss out how comfortable my submissive partner would be being feminine in the area I have in mind
• Asking friends to help me set-up an adorable, romantic picnic on the beach
• Waking up my submissive partner before sunrise with their feminine outfit all laid out
• Commanding them to get dressed in it (and brush their teeth because morning)
• Blindfold them
• Guide them to my car while they’re blindfolded
• Still keep the blindfold on as I go get us both coffee
• Drive them to the romantic picnic spot
• Guide their blindfolded self to the picnic area – and unblindfold them overwhelm them with a single glance!
• Drink delicious coffee and snuggle them while the sun rises

You certainly don’t have to go that way. You can have a mid-day picnic (though accept that there will be more people around!) or an evening picnic (but make sure you’re within the park’s open hours and in a safe park).

For the ultra-shy, you can even park your car somewhere cute – and have that “picnic” inside the safety of a car.

Exposure Level: 3/5

Because you can select the area for your picnic – and the time – you can control the exposure level as best as possible. You can also control how en femme – or not – the submissive is for a comfort level that’s challenging without being overwhelming.

---

At-Home Fashion Show

This sissy date requires a bit of pre-planning, and that pre-planning can be a separate date! The femdom (or you can make this a couple’s activity!) is going to head to a lingerie store (or shop online) for a wide range of lingerie that they think will fit the submissive’s body well. Depending on your budget and how new your submissive is to feminization, this might be 2-4 pieces of clothing – or it might be 10-15.

Pay close attention to the Return policy, please! The end goal of this date is to return the pieces that don’t work!

Once you have all of these items in hand, you’re ready for your date!

Sit down on the couch with all of your new pieces hidden from your submissive’s sight. Pick out a piece (or two) from the comfort of your spot on the couch, and send your submissive off to the privacy of the bedroom to wear the piece – and style the piece with their current closet to the best of their abilities.

They, then, are to come back out, with their sassiest walk, and model the item for you. You’ll then make a choice as to whether you both will keep the item or return it.

And hand them the next item.

Not only is this good practice for learning how to pull together an outfit (something a lot of raised-as-male submissives may not have experience with for feminine items), but it’s also a fun way to fit in some of your other kinks too. Playful praise kink? That fits perfectly. Prefer humiliation? That also fits. You also can easily play the part of the stern schoolmistress with biting commands and critique of their every choice.

When the two of you have gone through the entire pile, one of you will return the “rejects” – and the rest of the items will now be part of your closet. It’s a win-win!

Exposure Level: 0/5

This is another great sissy date option for couples who are trying to keep their sissification and feminization kinks on the discreet end of things. Since all of the items can be ordered online, there is no need to go outside en femme.

---

Breakfast in Bed

Task your submissive with gathering all of the ingredients for a mimosa bar. Let them know that you’ll be judging them on their thoroughness, so they should have a nice spread of different flavors to work with.

Make sure you have the next morning (and probably next afternoon, as this involves alcohol) free for this date.

The night before the “date morning”, treat your submissive to a new nightgown. This might be something cute and comfy – or something racy and exposing. It’s up to you! Feel free to make it an entire experience and erotic scene – or just present it to them and lavish them with compliments as he falls asleep in it. Up to you!

In the morning, both of you will lounge in bed, enjoying friendly chit-chat, instead of hopping into your day. I recommend some “girl talk” conversation points – like which male celebrities he’d have sex with if given the chance. Or the hottest action movie lead. Any discussion points, including sex chat, would work fine here!

At some point, yawn and tell him that he should go make both of you mimosas. Feel free to pick your own flavor – or even get out of bed yourself and enjoy making an entire mimosa “flight” for both of you to enjoy.

Head back into bed, and spend the morning chatting and enjoying each other’s company. Make sure to bring his new nightie into the conversation on a regular basis. Consider bringing the hairbrush into bed and brushing out his hair – or making him brush yours. If you have a morning skincare routine, consider bringing those bottles into the bed and putting him “through it” – especially if you have a mask or other long-set items.

Continue to send him out of bed, as needed, to grab mimosas or other items. Don’t forget to make him grab something off the floor a few times for additional compliments. ;)

Some other things you can do in the comfort of your bed:

• Talk about those hot celebrities – then pick out a movie that features them
• Do a crossword puzzle or other puzzle
• Compare and contrast mimosa flavors and strengths to figure out what you both like
• Apply lotion to yourselves or one another and let it dry
• Spankings with your hand or that aforementioned hairbrush
• Lots and lots of snuggles
• “Oh my god, you look so cute! Let me take a selfie to make sure you always behave!”
• Braid/do their hair into an updo or teach them how to do it to yours

Depending on what your plans are and how erotic you want this to be, this can be a good place to add other kinks as well – like putting on a chastity cage or diaper first thing in the morning, or adding a bit of rope bondage while they snuggle and talk to you.

(Feel free to make these virgin mimosas if you have plans for the day, too!)

Exposure Level: 0/5

You do all of this from the comfort of your own home. No need for any exposure at all.

---

Make Your Own Personal Care Product

You’ve probably seen those “Make Your Own Lip Balm” or “Make Your Own Bath Bomb” kits. Well, get enough for two people to enjoy the kits – and voila! You have an entire date in a box that’s ready to go.

Depending on what you both like for your dates, adding snacks and cocktails can add a bit of extra socialization to the experience. Make up, high heels, feminized outfits, remote-controlled sex toys, and perfume added ahead of the date can also make things feel more like a feminization date – just remember to plan ahead for the mess level (and resulting mess on your clothes!) the kit might end up in.

Considering the time commitment and how long your products need to “rest” to take on their final shape, you can also follow up your personal care production with a cute little spa day experience.

Either way, each time your crossdressing submissive goes to use their homemade personal care item, they’ll remember the sissy date you both had to create it. It’s just plain cute.

Exposure Level: 0/5

As you’re probably doing this from the privacy of your own home, there’s no risk of exposure. Yay for a comfy space at home!

---

An Ideal Sissy Date: Anything “Feminine” and Romantic!

The thing about feminization and sissification is that it’s partially about the experience of getting to be feminine and desired.

So most of the romantic, “I want to woo her” dates that you’ve seen in romantic movies and romcoms can work amazingly for your sissy date too. It’s really all about knowing the personality of your submissive – and coming up with ideas that can work fantastically with it.

So, while these crossdress date ideas might be a fantastic start, with your intimate knowledge of your partner and who they are, you’re the best expert at your partner – and I know you’re going to come up with something amazing.

Originally Published: January 2, 2023
Updated: January 2023, December 2022, October 2022.