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A Crossdressing Sissy Guide : How to Do Sexting With Boys


What comes to mind when you hear sexting, as a crossdressing sissy?


Does your boyfriend tell you that you are not feminine enough while texting, or do you get blocked by online hotties because you don’t know how to be spicy and slutty in DM’s?


Don’t stress, babe; it happens to the best of us.


We pull them in with our sissy figures and glam makeup, but sometimes, when the chat gets real, our feminine side kind of gets scared, and the guy side sneaks out, which isn’t something we’re going for.


Sexting With Boys 


Now, if you’re thinking, “How do I keep those guys DM’ing and keep things spicy as a crossdressing sissy?”, don’t you worry, sis, your sassy sister, that is me, will teach you everything.


Step by step. Okay?


Forget that you are a crossdressing sissy or a guy sitting in panties trying to get boys’ attention online, and things will become much easier for you.


Approach the guy with a full feminine mindset, and you can easily make him horny.


Although this has some rules, and you might take some time, I am sure after reading this blog, you will definitely become an Insta DM hoe and make those guys want you so hard.



What is Sexting?


Sexting With Boys


Alright, for all my nerdy sissies out there, let me tell you what sexting is first.


It’s pretty much when you’re using texts to seduce and charm someone.


That someone can be anyone: your boyfriend, your online mystery stalker, or maybe even someone you’ve got a little online crush on.


So basically, sexting is digital sex.


crossdressing sissy 


Now, big reality check: sexting doesn’t mean an instant meet-up and get physical, okay?


Like, for me? I do it when I’m in my full femme mood and feeling a tad horny.


Chatting up with these online dudes is so fun; they totally make me feel feminine.


It’s like a safe space to roleplay, something which is very hard to do in real life, especially as a closeted crossdresser.


So, no room for shyness and embarrassment.


You’re a sissy; after all, you deserve sissy-like fun that ignites your fabulous, feminine feelings.


Introduction to Feminine Sissy Sexting


crossdressing sissy 


Masculine and feminine sexting are different?


Um, totally, yes!


So, babe, you already know which side you’ve to lean on – Feminine Sexting.


As a crossdressing sissy, you need to play it ladylike.


Rule number one?


Only send spicy texts after some persistent nudging.


Make him want you.


That’s what girls do.


We are talking about feminine sexting here, so patience is very important.


I mean, we all know boys, right?


Quick to jump to the finale, even in their texts.


But not us sissies.


We’re a bit more sophistiquée.


Kick things off with a little tease, maybe drop a sultry voice note or two, then jump to the main show.


crossdressing sissy 


Hold up on showing too much eagerness.


Even though you might be like, totally ready to, you know, show some ahem assets.


Keep it chill.


Let him chase a bit.


Have him put you on a pedestal, treat you like a woman, and then give him a little reward for his effort.


It is like playing a long game, babe.


Set the mood, Feel vulnerable, and then go with the flow.


It’s like sissygasm – a bit of a tease, let him lead, and then please your man.


You see where I’m going with this, right?


Things to Consider Before Starting


Sexting With Boys 


Okay, first off, right out of the gate, let him know: you’re a crossdressing sissy.


Be straight-up open about your sexual choices.


Trust me, I’ve been there.


Chatting with a dude, things start heating up, he asks for a boob pic, and I tell him, “Sorry, I don’t have boobs; I’m a crossdresser,” and next thing?


Blocked or trolled for being feminine.


So, for all my crossdressing pals, a little advice: if you’re texting someone you don’t know or chatting for the first time, give them hints on your crossdressing personality. Stay authentic.


Second thing, babe: if you’re still closeted, never reveal too much about yourself.


I mean, I get it; he’s like super hot and makes your sissy heart flutter, but if Mr. Charming is asking for the real name or anything, and you’re not ready for that, then zip those lips.


We sissies crave validation, and some of these boys can exploit that.


If you’re not ready to come out, keep details to yourself.


Sending pictures is romantic, but don’t include your face.


Because if god forbid, those pics leak online, no one needs to recognize you, right?


And girl, as tempting as it is, don’t let a little dick pic make you go crazy and do something which shouldn’t be done.


Sexting With Boys


Taking Initiative


When it’s someone you’ve been with for a while, like your boyfriend, you can just check in and ask when they’re free to chat.


But for those stalkers and sissy lovers?


They’re usually sliding into DMs at night, which is the best time to spice things up a bit.


Trust me, I am telling you by experience.


Not sure if he’s free to chat?


Start off easy with a “Are you busy right now?” If you’re feeling a bit romantic, try one of these:


“I wish you were here right now.”


“Sleeping alone is the worst…”


And for those looking to chat with new peeps, here’s a little trick: Post a spicy pic or a reel and add these hashtags:


#sissylover #crossdressing #sissydm


Lots of sissy lovers and gay dudes use these hashtags to search.


So, use this trick, and trust me, they’ll come running.


Sexting Tips for a Crossdressing Sissy


Compliment Your Boy


crossdressing sissy


Just like we sissies love a good compliment, sissy lovers are also the same.


So, if you wanna make that dude feel extra masc, drop a compliment that’ll boost his confidence and turn him on.


Because when he’s feeling all manly-man, he’s gonna take the lead, show off some dominance, and make you feel feminine.


And that’s what you want, right?


How to make him feel more masculine?


Here how:


“Still thinking about our date last night. That fitted shirt? Uff, you look so hot.”

“Saw that gym pic of yours, and boy, it’s making me touch myself.”

“You’re so so tall. Bet if we stood side by side, I’d be right near your heart.”


Use Double Meaning Emojis


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Babe, let’s talk about emojis, okay? Using emojis is so much fun while texting.


They’re the perfect way to express your emotions and how you’re feeling.


Wanna tell your man that you’re feeling a little… horny?


Use Emojis.


Pick a couple of emojis with sexual meanings and send them to your guy; when he knows you’re in the mood, he’ll get horny too.


Sexting With Boys 


You can use naught emojis like the oh-so-naughty eggplant 🍆🍆🍆, the sultry taco🌮, the sassy peach 🍑, and, of course, the flirty tongue 😛.


My favorite is  🍆🍆.


Just saying.


Tease Him a Little


Sexting With Boys 

How do I tease my man?


I just say, “I had a dream where I was giving you a BJ,” or tell him that “his abs are driving me crazy” Of course, these are made-up things; the plan is to tease him and make him horny.


The more you boost his masculine ego, the better he will make you feel feminine.


Experience girl.


Share Your Fantasies


Sharing fantasies while sexting, oh wow, it’s the best way to go.


You gotta ask him about his sexual desires and tell some of yours.


Tell him all the things you’re daydreaming about doing with him, and get him to tell you, too.


feminine fantasy


But, like, if you’re wondering what exact fantasies to share?


Just say whatever your dirty little mind has, spice it up, tell him everything, you go sissy.


For example?


Oh, no examples here.


I only share my fantasies with my man.


You share with yours, okay?




Send Bold Pictures


Sexting With Boys 


Boys are so hungry for pictures, especially sissy pics, because, let’s be real, we are the rarest bitches on planet Earth.


So, why not give that little puppy of yours a juicy visual treat?


Show off your feminine body parts. Which ones, you’re asking? 


Your fat sissy ass, for sure, darling.


Slide him some booty pics, and tease him with a glimpse of your sissy clit, if he’s asking for it.


Pelvis pictures can drive him wild in seconds.


And those thighs?


Pure magic. If he’s asking for your sissy chest pictures, put on breast forms and snap a pic.




Tell your guy not to share or leak.


Oh, and a big tip?


Keep your face out of it; it’s the safest way to go.


And, like, if sending full nude isn’t what you like?


Totally okay?


Just a cute pic in panties can have your man excited.


Final Words




Sexting as a crossdressing sissy is so much fun, right?


It helps you feel all cutie and feminine.


It allows you to explore all sexual fantasies without the extra drama.


The best part is it is so convenient way to speak with boys.


No pressure of being judged, harassed, or anything that causes anxiety.


All you need to do is just feel feminine and go with the flow.


Get into his DMs and get the know the guy first. Like, does he like sissies?


What are his turn-ons? And is he willing to explore his sexual fantasies with you?



Once you’ve got that intimate connection, spice things up a bit, send over some flirty voice notes and cheeky emojis, or, if you’re feeling bold, send him nudes.


But sis, just make sure you don’t get carried away and share things that you shouldn’t.


You know what I mean, right?


If you’re ever unsure about anything or have any doubts about sexting?


Comment down below, and I will respond to you.


Sending you all the love, babe!

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