Welcome to lesson two in the sissy charm school, where we will be discussing lingerie for the occasion. Now we know about panties, bras, camis, etc…but how about putting them together? What is an ideal lingerie combo for certain occasions? We explore this now in lesson two. And if you are new to sissy stylings do some extra research check out this awesome panty guide, and review some lingerie terminology here! 

Lingerie plays a powerful role in the industry of lust, and seduction. Designed to complement the female body, exploring lingerie in everyday situations will enhance your feminity. Even doing just as little as wearing a sexy comfortable pair of panties while you sit on the couch is more erotic and fulfilling than wearing no sexy panties at all. So let’s explore some common and sometimes fun lingerie options for different occasions! 

Lingerie For The Occasion

For this, I figured it would be best to break the occasions up into categories. Casual, formal, sexy, and getting creative. For casual lingerie, we will discuss what combo is best for certain casual situations and why. Same for formal, and sexy. However, getting creative is a category where we will discuss turning drab boy clothes into something feminine and sexy! The creative section will be incredibly helpful to those who can’t really grow their collection freely.

Casual Occasion
  • Lounging around days- This is the type of day where it’s all you, no plans just sitting at home and relaxing. On this day you may be sporting a comfortable pair of panties most liking in the cheeky, boyshorts, or bikini category. Simply because lounging days are about comfort. Over these, you may be wearing sweatpants, yoga pants, or a comfortable pair of loose shorts. Personally, I would give my tits freedom on these days, so skip the bra and let the titties be free today!
  • Going To The Store- Outings for going to the store for groceries, general shopping, or even just out for lunch. Comfort is still key here, you don’t want to be worried about a ride-up your backside (unless you just like the excitement). So go with a comfortable panty fit. Next, you will want to pick out a comfortable bra fit. So nothing with just under-wire that can be uncomfortable and more noticeable. I find custom bras will normally make great casual wear bras, however, those can be expensive. Instead, you can look into affordable options such as a foam t-shirt bra. Small but sturdy so it’s great to support but not hard to cover up when you are wearing a bra.
  • Working-out- Obviously when it comes to working out your panty selection should be more about the fabric, than comfort. Here you want to go with something that is breathable cotton and stretch like spandex. There are a lot of hipster, bikini, and thong options to choose from out there. Then you will want to focus on wearing a durable, supportive sports bra. Sports bras are designed to be tight to hold your breast close and tight to your body. So a proper snug fit is what you want to go for.
  • Casual Date Night- It’s a simple dinner and movie date night. However, maybe sex isn’t exactly on or off the table. So tonight you want to be comfortable but sexy just in case. Go with either a pair of cheekies, bikini, or thong panties. Don’t be afraid to wear the more decorative pairs with lacey or carefully placed holes. Use a body-shaping camisole to provide a nice sleek figure and support to your chest, all while looking sexy when you take it off. Don’t forget to aim for matching colors with your undergarments and lingerie on date night.
  • Staying the night with the girlfriends- Perhaps it’s girls’ night, a sleep-over, but you are hanging with the girls. Painting your toenails, gossiping, sipping some wine, having fun. You can be safe with something cute, and casual like breathable PJs, with some cute cotton panties in your favorite comfortable style. Or a more sexy, skinny-strap silky slip, with matching panties underneath, with a pair of sheer stockings for a spicy flare. Don’t forget the fuzzy slippers!
Formal Occasions
  • At Work- In a work environment you must think professional, neat, and organized. Panties should be comfortable with a breathable fabric, next panty-hose to go over nice shaven legs (feels like a dream). I suggest exploring some bodysuit options for keeping your figure neat by limiting layers under your clothes. If no bodysuit, finish up with a comfortable bralette that is made of smooth, breathable fabric. Or an appropriately fitted t-shirt bra. 
  • Formal Date- You are going to a very nice romantic restaurant, followed by some drinks. This could also be used for a formal party of any kind. This night is to be elegant, so you want to show off your curves but in a neat way. You want your underwear to be sexy, but good for wearing for a few hours. I would go with a sleek pair of cheekies, bikini, or thong. Something easily form-fitting that won’t leave lines. Depending on your outfit you may want to go wear a shaper for tighter dresses, but normally on a date, you want to be natural and comfortable. So unless warranted feel free to skip the shape-wear. Next, think about your bra. Are you wearing something meant to show off cleavage? Go for a push-up bra, but avoid underwire if possible. If you need a little more form there is no shame in going for a padded bra, make sure it’s nice and snug and it will make you look great! Depending on the outfit you may want to consider pantyhose with a nice cute skirt look, or even thigh-high stockings to add a little extra sexy factor to the evening.
Sexy Occasionlingerie for the occasion
  • Seducing Your Partner- You are in the mood and want to put the flame under your partner’s ass. Of course, think a little about what they like. Are they into stockings, pantyhose, heels, sexy teddies? With this knowledge, you can cater to them but add your own flare. Pick romantic colors or bright colors. Red, pink, royal blue, and purple are great eye-catchers. Now with this knowledge don’t just settle for a bra and panties. Explore options like a sexy lace g-string with matching bra, covered by lace floral slip accompanied with thigh-high sheer stockings. Get a silk babydoll with a garter, and stockings. It’s about them, and you don’t plan on having it on for long so don’t worry too much about comfort.
  • Sexy Costumes- Not technically lingerie but I know I’m not the only girl that likes to collect sexy costumes to wear from time to time. Especially if you are a huge fan of roleplaying like me. I love collecting knee-high socks or stockings with short plaid skirts for a little naughty coed-play. Some popular ones that often come with fun accessories are maid, nurse, and my personal favorite the naughty librarian. For that last one, I use a pencil skirt (brown or black) with a pair of spicy sheer panties underneath, with stockings, a garter, a white button-up blouse, and a white comfortable bra. Followed up by a pair of black-rimmed glasses.
Getting Creative
  • Turn your male underwear into panties- Maybe you just don’t have the courage to buy a pair of underwear for yourself or want to sneak a pair from your spouse. With some creativity, you can alter your male underwear. If you’re not great at sewing go for purchasing a good snug size pair of cotton male briefs. Go to the craft section if you are brave and grab some lace. You can also pick up some cotton-friendly fabric dye of a more feminine color if you grab white briefs. Take them home, first dye them. Then you will want to cut away some of the extra unnecessary fabric that covers too much of your ass. (Fabric scissors would be best if you have them.) And cut a V- shape on the front part that cradles your clit if there is too much fabric. Next, take your lace and you can either sew it along with the waistband or sparingly use hot glue if you have no other recourse. It may not be perfect but it’s yours.
  • Booty shorts- Couldn’t resist bringing up booty shorts, they are easier to make than panties. You just need a tight-fitting pair of shorts or pants. Get your measurements, and mark them on the pants/shorts before you cut! You want to ideally only do about 2 to 3 inches down the leg. For your men’s jeans, you can look up steps on how to shrink them to make them tighter, and more appropriate for booty shorts.
  • Can’t afford lingerie- So you want to wear something cute but can’t afford to spend money on a hardly worn negligee. Then think outside of the box, get a dress shirt for yourself that is two-three sizes too big, then a rope or small belt. Use the rope/belt to tie around the middle of your stomach nice and tight. Make the shirt fit around your figure, and teasingly hide your ass. Follow this up with your sexiest pair of panties or go nude!  A good trick for teasing your mistress!

Other Accessories And Garments To Consider

When certain occasions arise there is not one right combo. So keep other garments in mind like the bustier can be great for a form-fitting but neat approach for formal needs, and a corset would be greatly suited for sexy or formal attire. We also talk about stockings, and pantyhose but fishnets make for very eye-changing and exotic legwear for any sexy occasion. Lastly, although they tend to fall more into the toy category I still consider nipple clamps part of sexy wear, so just saying doesn’t hurt to throw them in as a surprise! 

I hope you enjoyed this lesson. Please listen to the audio below and move on to the assignment posted next here! 

Your Sissy School Headmistress,


Headmistress Riley