#“classy crossdresser” | Explore Tumblr Posts and Blogs

tracylprince · 14 days

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tracyai · 14 days

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francoise333 · 11 months

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Feeling femme after my make up session in Madrid …

#transisbeautiful #elegant crossdresser #classy crossdresser #crossdressing #feminizationtraining #boy to girl #maletofemale

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cindycross-39 · 11 months

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Me Cindy Cross crossdressing - my outfit for an afternoon at the country club

#crossdressing #skirt #classy

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classycrossdressing · 2 years

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1960s look skirt suit in powder blue. I feel like Kate Middleton!

#classy #pretty #elegant #crossdresser #blue #skirt suit

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libby-for-life · 2 months

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Lucifer and Adam goes clubbing/dancing for late night date and while their on the dance floor some random demon came up and slapped on Adam's ass or just starts aggressively flirting to Adam who's slowly losing patients, but one look from Lucifer and that random demon will n o t be living the place alive. Lucifer drags that poor soul out in the back of club, threw an alley way, while Adam is following them on a slower pace, instead of Lucifer's fast one. So as you know Lucifer kills the demon, unnoticed to everyone that is near/inside the club do to the music being blasted top volume. Adam gets hot and bothered by the possessive/demonic look on Lucifer's face, so he turns him around and sensually kiss him, begging him to fuck him.

Blood and Violence, Possessive and Rough Sex, Crossdressing?[adam wearing a short dress; easy access, lol], Semi-Public/Alley Way Sex, I saw that you did a Queen Adam one, can you do that for this one too?

Nice! I live for possessive Lucifer. It gets my creative juices flowing.

Let's begin, Anon.

Adam was doing well all things considered. Sure, the club had nothing on Heaven's clubs, nothing would, but for Hell's standards it was high-peak. The sheep demon pulled his short dress down a bit with a blush. The only reason why he was even wearing the thing was because he lost a bet. His husband was the original trickster so, though he would never admit it, it was Adam's own fault for believing that Lucifer would ever play fair.

"Don't worry so much, my lamb." Lucifer had purred out in a sultry way that had Adam's body melting. "You look beautiful."

"Of course I do." Adam had grumbled, but he preened at the praise, which made the whole thing much more bearable.

Adam sighed to himself as he looked in the direction his husband had gone. Lucifer had gone to change the music to something a bit more classy to dance with. Adam just shrugged but smiled nonetheless. The former archangel looked so starry-eyed at the thought of dancing with Adam that he just nodded along with him.

But he had been gone for a while now.

"Where are you?" Adam muttered, his eyes sweeping the dance floor. He got up from his seat at the bar and looked around a bit. He let out a yelp when he felt a stinging slap to his ass. He quickly turned around and glared at the tall demon before him. Adam was used to being the taller one in Heaven when he wasn't counting the seraphim.

Hell was a whole other story. Many demons towered over Adam and it always made him feel small in every sense of the word.

"Hey there, sweet thing~." The demon flirted making Adam recoil in disgust. It was a tall-looking dog. "Not interested." He didn't want whatever this demon wanted. He flashed his ring for good measure.

"Oh, come on." The demon said, pushing him into the counter. "I know you want this." Adam glared harder, his eyes burning gold. "No, I don't. Fuck off, asshole." This didn't seem to deter him in the slightest. A hand found its way to his ass and squeezed. "Let go!" He tried moving away but gasped when the offender was dragged off him. Lucifer held the dog demon by the throat and he looked livid.

"How fucking dare you," Lucifer growled, a few sparks leaving his mouth that would soon turn to flames if left unchecked.

The sinner gulped, as much as he could with his throat being squeezed, and began babbling about how Adam was asking for it and how he didn't know he belonged to the King of Hell.

Lucifer had heard enough and began dragging him away. Adam watched in a bit of a daze as his husband left him by the bar. No one had even glanced in their direction, too busy dancing to the slow music that Lucifer picked out for them to dance with.

Without thinking too much about it, he followed after them, making sure he wasn't bumping into any couples on his way. He had just caught sight of Lucifer barging out into an alleyway. Adam jogged up to the door and slowly opened it.

Lucifer was going to town on this sinner. The dog was yelping and yelling for mercy which his husband didn't seem too keen on giving.

Adam could feel himself blush, a tent forming in his silk underwear. His dress was doing nothing to hide it. Lucifer looked so hot being protective and possessive. He watched as a hole was punched through the dog demon's chest and he finally slipped to the floor of the dead.

The sheep demon walked up to his husband who was breathing heavily and was quick to turn him around. Lucifer looked surprised but moaned when Adam kissed him hard. It didn't take much time for his husband to take control with a growl.

Strong hands picked him up and slammed him into the wall. Adam moaned in slight pain but immediately moaned high and loud as Lucifer attacked his neck with kisses and bites.

"How dare someone touch what's mine?" Lucifer said, hands fondling Adam's silk-covered ass. "Only I can touch you. I should remind you of that."

Adam moaned at the gruff voice. "Really? Because I've seen you do better." He breathed out.

Lucifer growled harder, his chest vibrating with power that Adam could feel.

"Oh? Then allow me to show Hell's Queen what he's been needing."

Adam was flipped around and his dress was hiked up his ass. The panties were ripped off showing him bare for Lucifer to see. Adam didn't even need to be stretched, Lucifer made sure he was loose for himself and plunged his dick all the way in.

Adam mewled and even let out a few bleats of pleasure as Lucifer took him roughly in the alleyway. Tears fell down his cheeks and Adam felt the growing need to cum.

"Please, I-I."

Lucifer chuckled. "Does my little lamb need to cum? Beg for it."

"Please! Let me cum! I'll be good! I-I'll, oh God, be you're good little lamb!"

"Then cum."

Adam came with a scream. He loved this feeling of possessiveness, the furious protective nature, and the fact he wasn't the only one who got jealous. He loved his husband. And from the gentle look he was being given, the feeling was reciprocated.

#adamsapple #hazbin hotel adam #hazbin hotel #hazbin hotel lucifer #send asks #oneshot #smut #short

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miss-conjayniality · 3 months

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another submissive dilf!jay thought that randomly jumped out of the blue….crossdressing with dilf!jay.

imagine that you and jay are about to attend a social function and he sees you getting ready. and there’s something that truly gets to him whenever he looks at you getting ready. he thinks you look absolutely stunning from start to finish. whether you’re bare-faced or full faced, it doesn’t matter. he’s always starstruck by your beauty.

being the inquisitive, knowledge-seeking man he is, jay has always had a casual interest in makeup. tinkering around with makeup tutorials and seeing how it looks on him, learning about its rich history spanning all the way back to ancient egypt…..he’s fascinated by how both women and men used cosmetics for millennia as a way to beautify the self.

as jay sees you blending your eyeshadow, he has a certain desire in his mind - he wants you to put makeup on him. to him, the creation of glamour sounds like such an intimate, romantic experience. you see, glamour starts from within. and depending on who you are inside, it outwardly shows up differently and uniquely on everyone. for jay, he is the embodiment of a classy, vintage, gentlemanly glamour. but he’s also open to experimenting towards something different and not boxing himself to just masculine dapperness.

dare we say it? he envies you. he loves and relishes in his dapperness dearly. but as stated before, he’d love to tap into his girly, feminine side without the rigid social repercussions. and what better way than to do it with his lovely, endearing wife?

on that same note, he loves your lingerie….and not only does he find it incredibly sexy on you, but he would love for you to put it on him. sometimes, when he gifts you new lingerie, he wishes he could share them with you too. he wants you to do unspeakable things to him as he wears your pretty pink silk nightgowns, pink laced lingerie, sparkly pink stilettos, and more.

“p….princess?” jay nervously asks, “may you put your makeup on me sometime? and maybe your lingerie too? ehehe. daddy thinks it sounds real fun.”

jay didn’t mean for those last two sentences to come out. his mind-to-mouth connection vanished for a moment because of his desires flooding his mind. he hopes you don’t find him weird or anything…

“ah! princess oh my god I’m so sorry if i-

“daddy,” you interrupt, “i’d be more than delighted to do those aforementioned things to you. i think you’d look stunning in my skimpy little clothes. i have never seen this side of you come out but i’m glad it is.”

“r-….really princess?” he blushes, “thank you for the kind words. I love you so much. thank you for accepting this side of me. for a long time i thought you’d find it strange.”

“well all I must say is that you’re sexy and beautiful regardless if you’re wearing blue calvin klein boxers or pink victoria’s secret lingerie. that’s how deep my love runs for you. you are valid as is. and you are my stunning, beloved daddy no matter what.”

he gets even more flustered by your kind, affirming words. you give his cheek a peck and you two head off for the night. but jay is anticipating tomorrow far more than this event because he’s been dreaming of this for so long.

he’s excited for you to dress him up and beautify him, only for the lingerie to be taken off afterwards and the makeup to be smudged in tears after a good hard fuck from his pretty princess.

#enhypen smut #jay smut #enhypen hard hours #enhypen hard thoughts #sub!enhypen #dom!reader #sub!kpop #enha smut #enha hard hours #xoxo heidi ♡

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tracylprince · 12 days

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tracyai · 14 days

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francoise333 · 9 months

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Black and red my two favorite colors together for lingerie

#crossed legs #classy crossdresser #elegant crossdresser #crossdressing #panty bump #cd #transisbeautiful #sissy cd #sissy gurl #sissi femboi #mtf trans #boy to girl #feminizationtraining

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classycrossdressing · 2 years

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Teaming casual with smart.

#crossdresser #elegant #classy.#casual #shirt #pencil skirt

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prettysissyacademyblog · 9 days

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You can call me mommy I’m an image stylist and femininity advisor who works with crossdressers and MTF transgender women.

I help people just like you achieve images that express who they truly are.

I’ve used my years of experience as an image stylist, fashion designer, and former professional dancer to transform hundreds of clients into the classy, beautiful and confident women they’ve always wanted to be…

Now I want to help you.

Creating a Convincing Feminine Image Requires Special Skills I believe that anybody – even the burliest truck driver – has the ability to pass or blend in as a woman. But it doesn’t happen by

Do you fantasize about being made to dress like a woman, look like a woman, think like a woman, and act like a woman? Have you imagined yourself as each of the beautiful women on the gallery pages? Do you like the humiliation of being made to wear women’s things in public when you’re still obviously a man? You’ve come to the right place, sissy. Below, you will be given a series of assignments and sissy tasks that will take you on a journey through humiliating sissyness and on towards your total feminization.

Looking for a Mistress to feminize you near ? You want to be feminine, don’t you? To hear the clicking of your stiletto heels as you walk, feel the swish of pantyhose as your nylons rub together on your smooth thighs, beneath your tight, lined miniskirt which slides over your ass, your heavily-styled hair and heavy earrings brushing your neck, your shoulders feeling the pull of heavy breasts in your bra, tasting lipstick on your lips and smelling your perfume, makeup and hairspray. You want it, more than anything, don’t you? One day, sissy, one day.

Follow the assignments and tasks here. Telegram: @prettysissyacademy1Even if you are an experienced sissy with your very own, feminine wardrobe and you dress regularly, the discipline of having your femininity enforced by these assignments will still be thrilling. So, are you ready?

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demonichikikomori · 2 months

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Switching things up a little- crossdressing Vil except we don't recognize it's him.

SEXXYYYYYYYYY WOMAN VIL SCHOENHEIT.

Okay. Okay. Okay.

I am so glad I can talk about crossdressing now omg thank you for sending this anon. I LOVE crossdressing Vil. Again, for my personal enjoyment/headcanons/smut reasons. Vil already is very comfortable wearing heels as to our gorgeous queen of pomfiore, beauty is genderless.

Follow me on a romantic journey in the beauty of crossdressing sexy woman Vil Schoenheit.

You go on a trip onto the island to shop for... I dunno, groceries. Sam sells everything but you want to see the little island town! You're shopping without Grim and you see a GORGEOUS woman shopping near you. She looks classy, rich, far too elegant to be living on the island. Large diamond earrings, her champange colored hair is in a neat ballerina bun, a floral style face mask, her eyelashes are long and wispy... Her sense of fashion is impeccable. A long A line skirt, making her appear modest and refined, a gorgeous long sleeved top in a royal purple shade, exposing a hint of her cream colored skin along her abdomen, black boots to make her even taller, and she has a chiffon, floral patterned shawl hanging from her arms and along her back as she patiently observes the fruit...

She must be a princess... Right? You've never seen a girl... No. A woman like her on the island before. She catches you staring, and her amethyst colored eyes widen for a moment in surprise. Then she holds a beautifully manicured finger to her hidden lips. A secret between you and her that you wouldn't talk about this moment.

She must be a princess in disguise. You told yourself that story in your head when you went home and dreamed of seeing her again... When you brought up the beautiful princess to Vil, he only hummed in interest at your tale. "I'm sure you'll see her again. But she might be a queen, not a princess." He joked.

You want to see her. You need to see her.

#ask the devil #vil schoenheit propaganda #i love crossdressing #wlw almost?#sexy woman vil schoenheit #vil schoenheit x reader

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deirdreskye · 1 year

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Girl who got into crossdressing when the black skater skirt was in style making fun of the very classy ladies who got into it when the church dress was all the rage. It's me I'm girls, and I'm paying my penance by chaining myself to the rocks at the shore and you better believe the tide is slapping my face as I type this

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cindycross-39 · 1 year

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Me Cindy Cross crossdressing - a gorgeous classy green bra with lace edges, center bow and little gemstones at the straps.

#bra #green #lace

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tracylprince · 15 days

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Bohemian Rhapsody

Found a lovely Hi Lo dress that reminded me of the 60's/70's. Paired the up with some High Heeled Platforms.

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