Before we dive into how to sissy your boyfriend, let’s first establish what it means to be a "sissy." In simplest terms, a "sissy" is a guy who wants to be dressed up as a girl, referred to as a girl, and treated as a girl in bed. He may want to do this every time he has sex or is being sexual, or he may want to explore it only some of the time, and he’s opened up to you about it because he wants to explore it with you.
Maybe you are unsure how you feel about your boyfriend’s newfound desires- or rather, his preexisting desires that he’s just now shared with you- and that’s okay! You do not need to do anything that makes you uncomfortable or that you simply don’t want to. If that’s the case, at the minimum acknowledge your partner’s bravery for opening up to you and allow him the opportunity to experiment with these kinks without you, whether that be through watching porn, playing with another partner, hiring a pro-dominatrix, or another avenue that works for you two.
If you’d like to try playing with your boyfriend in this way- aka. sissifying and feminizing him- I’ve created 4 basic ways to get started that can be fun for you, even if the idea of sissying him doesn’t exactly turn you on. My suggestion is to open your mind to the possibility that you, too, may enjoy this kink, or at the very least you’ll enjoy how much your partner is enjoying it.
Step 1 - do his skincare routine
I’m gonna take a guess and assume you already have a skincare routine you do for yourself, and that you at least somewhat enjoy doing it. What do you think about doing your routine on your boyfriend? Make a little spa day/night out of it: slide a headband on him, lay him down, and apply the skincare products on him that you typically use on yourself. You can even clean up his eyebrows (which you may have been wanting to do regardless!), do a face mask, and even a lip mask.
*Insider tip- while you’re applying the products, make it a point to emphasize that these are the products you use your yourself, that you perhaps bought at Sephora/Ulta, where all women shop.
Step 2 - do his makeup
The skincare routine is really a primer for doing his makeup routine, which is probably something he wants done, too. For a sissy, playing with makeup can be a fun and exciting way to be feminized by you. Now, you don’t need to do your exact makeup routine on him. Instead, do a simple routine with emphasis on the colorful, girly products, like eyeshadow/eyeliner/mascara, blush/highlighter, and lip gloss/lipstick.
Insider tip - go with a glossy pink or bold red lip.
Insider tip - throw in phrases to humiliate him for wearing makeup (“I can’t believe you’re wearing my makeup / can’t believe you’re wearing lip gloss”).
Step 3 - put him in your underwear
Wearing women’s panties is the most common thing a sissy will want to indulge in. This can definitely feel like a big jump from doing your boyfriend’s skincare and makeup, so I suggest putting him in your panties, instead of buying new ones just for him, to start. This is because by putting him in your panties, you’re emphasizing yourself and his strong desire specifically for you.
Insider tip - dirty talk about how you’re so wet thinking about getting fucked by him (or whatever turns you on about him / your sex life) and take off your panties for him to put on so he can feel your wetness on his cock.
If you’re comfortable, or dare I say, turned on by all this, you can take it a step further and dress him in your bras, stockings, mini skirts, and more!
Step 4 - switch up the words you call him
Odds are, your boyfriend wants you to use feminine terms for him when you’re playing in this type of way. Some general examples include calling him a “good/bad girl” or a “slut/whore/bimbo,” describing him as “pretty,” and referring to his penis as a “clit.”
Insider tip - if you’re bisexual, pansexual, or queer, this step may come easier to you because you may have already enjoying using these terms with your female partners.
With this step, and with each step before, ask your boyfriend what he wants. These tips are meant to guide you, but they are not meant to replace basic communication with your partner. Ask him what words he’d like you to use, ponder how you feel using them, and go from there. Maybe some of the terms he likes, you do not, and vise versa! Sissying your boyfriend will require you both to utilize your communication and negotiation skills, and it will hopefully open the door for more honest discussions about sexual desire- for the both of you.
xoxo
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