Master Leo

Superb!

FR: Trop bon quand @nadiatrav28.bsky.social me fourre son gros clito comme ça.

EN: so good when Nadia fuck me like this.

Diving back into the 1920s’ sissy underworld: a chastity-bound schoolgirl kneels, her lips devoted to her trans Mistress’s big cock—obedience never looked so natural.
Crafted by me, Master Leo. Fancy starring in your own scene? Message me—fee applies.

"Nnngh—! I hate how much I love this... My hole is yours, Sir, and this gag won’t stop me from taking every inch—every drop—like the pathetic sissy I am."
Another creation of mine, created and captioned to show how a sissy should be used.

Another 1920s-style scene: a sissy maid in chastity submits to the Mistress’s of the house’s firm hands, her posture a silent confession of disobedience. Discipline is not a request—it’s a necessity. Will she show mercy this time?

Want your own custom humiliation? DM me—a fee applies.

Janet’s schoolgirl defiance meets Mistress Faye’s latex-clad authority—panties down, crop raised, and a lesson in obedience about to begin.
Created by me, Master Leo, to torment sissy Neil. Watch her defiance shatter—every strike, every whimper, is what he craves.

Fiona’s humiliation is complete: ballgag stretching his mouth, chastity locking away his pride, while old men’s cameras capture every pathetic moment. Did he ever think he’d kneel so willingly? Now he knows his place.
Created by me, Master Leo.
Want your own custom creation? Message me (fee applies)

Loved seeing you used by him, he really did fuck you in all ways. A true Dom

Just took this, kind of interesting

obeytest.com/r/wOOVPoP2QX...

More 1920s-style pulp art for your pleasure: a leather-clad trans schoolmistress lounges in her chair, her cock serviced by two obedient sissy schoolgirls at her feet, while two more watch with very attentive eyes.
Want to star in your own custom creation? Message me for pricing and details.

Sissy Neil, naked and hard, is living proof of the power I hold over him. His phone, laptop, and tablet stay locked, with strict parental controls in place to keep his pathetic sissy urges in check. Tell me… are you weak enough to let me take this kind of control over you?

A reimagined photo capturing the moment Janet and Neil first met me—dressed in their piggy masks and full gear. You can read the full story here: app.box.com/s/gun29nwsj3... or fetlife.com/MasterofSiss...

As you know, Faye is my girl. She’s been taking a bit of a backseat lately, but she can’t resist it when I dust off her old photos and give them a splash of retro pulp magic. She’s already gorgeous in the originals, but the makeovers? Absolutely irresistible—don’t you think?

More 1920s-style pulp art with a twist: the leather-clad head schoolgirl hides a big secret—one her submissive lover is eagerly uncovering with her lips.
Interested in starring in your own custom creation? Message me for pricing and details.

@Uniformslut on fetlife loved my 1920s-style work so much, he’s back for more—this time on his knees, bound as a sissy schoolgirl, worshipping another sissy’s big cock. Who’s next to star in one of my vintage creations?

The moment came — sissy neil’s wife learned of his submission to me, Master Leo. Now I own them both. In this photo I hold her close, naked as I demanded — her first embrace with the man who commands them. The full story will be revealed on Saturday.

Neil and Janet, bound in chastity and pig masks, surrender to Master Leo’s cruelty—spankings, forced confessions, and strap-on degradation reshaping their marriage into pure submission. Their secrets exposed, their bodies used, their love replaced by ownership.
Posting this twisted tale on Saturday.

"@Uniformslut" on fetlife was so impressed with my work he purchased a couple of my 1920s-style creations. Here he is on his knees — a sissy schoolgirl, serving his trans Head Mistress with his mouth. Who’s next to kneel and be remade like him?

Created by me, Master Leo—your source for custom BDSM art:
‘M-Master, my chastity is aching under this pleated skirt.. I tried to focus on my studies, but all I can think about is how big you are. My cage is torture—please, teach me a lesson I’ll never forget.’"
—Want your own? Message me for prices

This 1920s-style sissy porn has proven a hit—clearly, you all have refined tastes in debauchery. In this shot, a chastity-locked schoolgirl sissy wraps her lips around the tip of her owner’s cock, savouring every humiliating moment. Expect more where this came from in the days ahead.

Made for my owned sissy Jessica Jean — used anally in the gear that exposes the pathetic sissy within. Want to be transformed — gagged, caged, latex-clad or more? Message me. Custom creations available, fee applies. @jessicajean1972.bsky.social

Here’s another taste of 1920s-style sissy smut — this time the aftermath of a blowjob, with one very exhausted sissy left with a face full of cum and a cock still locked in chastity.
All crafted with my suite of AI tools. Fancy a custom creation? My usual fees apply.

“Mmmph—! I used to have standards... Now I’m gagged, caged, collared, and posing for their filthy lenses. My locked cock throbs in frustration, but my shame? That’s the true main event.” — A helpless sissy on display, immortalised in pulp art created by me, Master Leo.

After so many kind words on my last creation, here’s more fun from my suite: back to the 1920s, where the sissy remains locked in chastity, while her leather-clad Alpha boyfriend puts her through her oral training.

“Your gagged moans are music to my ears, sissy. That tight arse is begging for it, and your locked cock? Just proof you’re mine.”
A Master Leo original — crafted in true pulp-art style. Bespoke captions and creations available… commissions taken, prices on enquiry.

Some more fun with my creation suite: it’s now the 1950s, and the control remains — the cute little sissy still locked in chastity, while her Alpha boyfriend with his big cock stands beside her, one arm possessively around her back.

Maisie the Locked-Up Slut takes it where she’s told — her useless sissy clit caged while her greedy arse gets exactly what it deserves. A perfect reminder she’s nothing but her Master’s fucktoy. Created & captioned by me, Master Leo. Fees apply for custom work.

I made this caricature of my girl Faye, featuring her in her favorite outfit—long gloves and a latex dress. Don’t forget to follow her and say hi at @Mistress_Faye69 at fetlife or @faye_mistress at x

Having some fun in my creation suite. Even in the 1920s, sissies were there — as my latest work shows. And, naturally, the well-endowed Alphas keeping their little cocks locked, tied, and reminded exactly where they belong.

Meet Jessica Jean: plump, gagged, and caged, his body trussed up in lingerie and leather. His locked cock stays empty, but his hole is always ready for service.
This image and caption were created by me, Master Leo. @jessicajean1972.bsky.social