Master Leo
@masterleocreator.bsky.social
Dominant creator and exposer. Only on a fee paid basis
My services here - https://app.box.com/s/b015jmc3wf4k6z5mehombh9mu5ffvjhf
allmylinks.com/masterofsissies for the links to all my profiles.
My services here - https://app.box.com/s/b015jmc3wf4k6z5mehombh9mu5ffvjhf
allmylinks.com/masterofsissies for the links to all my profiles.
Mistress Faye asked me to create something special for her—and here it is. A vintage-style scene featuring her in full latex, boots, and gloves, pegging a desperate sissy into submission. It captures her dominance perfectly, and I couldn’t be prouder of how it turned out. What do you think?
November 30, 2025 at 8:27 AM
Mistress Faye asked me to create something special for her—and here it is. A vintage-style scene featuring her in full latex, boots, and gloves, pegging a desperate sissy into submission. It captures her dominance perfectly, and I couldn’t be prouder of how it turned out. What do you think?
Here’s a piece I crafted the other night—a vintage-style scene featuring a dominant trans mistress in leather, taking her gagged, collared sissy from behind. His chastity cage keeps him helpless, just as she demands.
November 30, 2025 at 6:59 AM
Here’s a piece I crafted the other night—a vintage-style scene featuring a dominant trans mistress in leather, taking her gagged, collared sissy from behind. His chastity cage keeps him helpless, just as she demands.
Kim Nylons commissioned me to sharpen and caption her blurred photo—and the result speaks for itself. Need your images transformed with my expert touch? Message me. A small fee applies, because even sissies like you know quality is worth paying for.
November 29, 2025 at 8:46 AM
Kim Nylons commissioned me to sharpen and caption her blurred photo—and the result speaks for itself. Need your images transformed with my expert touch? Message me. A small fee applies, because even sissies like you know quality is worth paying for.
Mistress Victoria takes her rightful place upon the porcelain throne, her delicate lace lingerie contrasting with the cold steel of lucy’s chains. There’s nowhere for her pathetic sissy to hide—collared, leashed, and sitting precisely where he belongs.
November 29, 2025 at 6:36 AM
Mistress Victoria takes her rightful place upon the porcelain throne, her delicate lace lingerie contrasting with the cold steel of lucy’s chains. There’s nowhere for her pathetic sissy to hide—collared, leashed, and sitting precisely where he belongs.
Head Stewardess Margaret looms over Trainee Stewardess Linda, bound, gagged and kneeling in her lingerie, cock exposed—punished for flirting with passengers instead of serving them. A firm reminder of airline protocol, 1960s-style.
All created by me Master Leo, from photo to caption.
All created by me Master Leo, from photo to caption.
November 28, 2025 at 7:46 AM
Head Stewardess Margaret looms over Trainee Stewardess Linda, bound, gagged and kneeling in her lingerie, cock exposed—punished for flirting with passengers instead of serving them. A firm reminder of airline protocol, 1960s-style.
All created by me Master Leo, from photo to caption.
All created by me Master Leo, from photo to caption.
I do enjoy showing off my talents — especially when Faye is my inspiration. I took one of her old fetish modelling photos and, with a little AI and video editing work, turned it into a short video of her in motion. She didn’t need the help, of course… she was stunning then, and she still is now.
November 28, 2025 at 7:19 AM
I do enjoy showing off my talents — especially when Faye is my inspiration. I took one of her old fetish modelling photos and, with a little AI and video editing work, turned it into a short video of her in motion. She didn’t need the help, of course… she was stunning then, and she still is now.
Another Master Leo creation in a 1950s style, from photo to caption all done by me.
November 27, 2025 at 6:55 AM
Another Master Leo creation in a 1950s style, from photo to caption all done by me.
sissy neil with his task of 100 lines saying "Despite the device locks of the last fortnight neil is still looking at naughty pictures , perving over his relatives and their underwear . He is also getting unauthorised erections and playing with his small cock far too much " @neild64.bsky.social
November 26, 2025 at 10:14 AM
sissy neil with his task of 100 lines saying "Despite the device locks of the last fortnight neil is still looking at naughty pictures , perving over his relatives and their underwear . He is also getting unauthorised erections and playing with his small cock far too much " @neild64.bsky.social
Just me and Dizzy Miss Sizzy—though we’ve never actually met in person. A little fantasy of what we might have looked like yonger. But some things never change—the Alpha masked male with the big cock in charge and the sissy locked tight in chastity, exactly where she belongs.
November 26, 2025 at 7:55 AM
Just me and Dizzy Miss Sizzy—though we’ve never actually met in person. A little fantasy of what we might have looked like yonger. But some things never change—the Alpha masked male with the big cock in charge and the sissy locked tight in chastity, exactly where she belongs.
Dizzy Miss Sizzy asked me to create a military-style 1940s pin-up girl, complete with uniform and stockings, posing beside a plane — and this is what I came up with. It turned out really well, and she makes a stunning vintage pin-up, don’t you think?
November 25, 2025 at 6:46 AM
Dizzy Miss Sizzy asked me to create a military-style 1940s pin-up girl, complete with uniform and stockings, posing beside a plane — and this is what I came up with. It turned out really well, and she makes a stunning vintage pin-up, don’t you think?
sissy neil has had his phone and laptop use more restricted, and his tablet privileges completely revoked for the next few days. He’s also been assigned 100 lines to write as corrective discipline. No tablet until every single line is completed properly. @neild64.bsky.social #linewriting
November 24, 2025 at 9:09 AM
sissy neil has had his phone and laptop use more restricted, and his tablet privileges completely revoked for the next few days. He’s also been assigned 100 lines to write as corrective discipline. No tablet until every single line is completed properly. @neild64.bsky.social #linewriting
Pathetic thing still twitches when I adjust your suspenders, doesn’t it? Six more months locked—but first, let’s milk that useless cock. The managing director’s waiting, sissy. Remember his cane last time? Hurry… or he’ll punish you worse.
Fancy your own humiliation? Message me—small fee applies."
Fancy your own humiliation? Message me—small fee applies."
November 24, 2025 at 7:13 AM
Pathetic thing still twitches when I adjust your suspenders, doesn’t it? Six more months locked—but first, let’s milk that useless cock. The managing director’s waiting, sissy. Remember his cane last time? Hurry… or he’ll punish you worse.
Fancy your own humiliation? Message me—small fee applies."
Fancy your own humiliation? Message me—small fee applies."
sissy neil’s pathetic little cock just won’t stay soft—is it the six months of denial, or his filthy habit of stealing relatives’ panties and fantasizing about them? Likely both. Either way, icing that useless thing down seems the perfect solution for his persistent problem. @neild64.bsky.social
November 23, 2025 at 9:33 AM
sissy neil’s pathetic little cock just won’t stay soft—is it the six months of denial, or his filthy habit of stealing relatives’ panties and fantasizing about them? Likely both. Either way, icing that useless thing down seems the perfect solution for his persistent problem. @neild64.bsky.social
Dizzy Miss Sizzy asked me to create a retro pin-up portrait—glamorous, sultry, and dripping with vintage charm, complete with lingerie and sheer stockings. I’m rather pleased with how it turned out—what’s your verdict? Fancy your own custom piece? Drop me a message; a small fee applies.
November 23, 2025 at 8:39 AM
Dizzy Miss Sizzy asked me to create a retro pin-up portrait—glamorous, sultry, and dripping with vintage charm, complete with lingerie and sheer stockings. I’m rather pleased with how it turned out—what’s your verdict? Fancy your own custom piece? Drop me a message; a small fee applies.
I took inspiration from a still photo I took many years ago when we met and created this video of samanhta walking and then kneeling. I think it turned out quite well don't you?
November 22, 2025 at 3:01 PM
I took inspiration from a still photo I took many years ago when we met and created this video of samanhta walking and then kneeling. I think it turned out quite well don't you?
Sissy Maids magazine cover: Bound and denied in a vintage pin-up pose. This retro magazine cover stars a sissy called cleo, dressed in a latex uniform, her chastity glinting as she kneels in submission. Created by me, Master Leo.
November 22, 2025 at 8:56 AM
Sissy Maids magazine cover: Bound and denied in a vintage pin-up pose. This retro magazine cover stars a sissy called cleo, dressed in a latex uniform, her chastity glinting as she kneels in submission. Created by me, Master Leo.
Sissy Schoolgurl: Bound, tease-worthy, and locked in vintage pin-up perfection. This 1950s-inspired magazine cover created by me stars a pigtail-clad sissy in a blouse, sheer stockings, and a chastity cage—restrained and ready for detention. Custom creations available, contact me for details.
November 21, 2025 at 8:01 AM
Sissy Schoolgurl: Bound, tease-worthy, and locked in vintage pin-up perfection. This 1950s-inspired magazine cover created by me stars a pigtail-clad sissy in a blouse, sheer stockings, and a chastity cage—restrained and ready for detention. Custom creations available, contact me for details.
Poor sissy neil hasn’t been allowed to cum since the start of the year, so his pathetic little cock just won’t stay soft. To fix his problem, I told him to ice it down—next thing I know, the eager sissy is outside defrosting his car naked, freezing his tiny thing off. @neild64.bsky.social
November 21, 2025 at 6:53 AM
Poor sissy neil hasn’t been allowed to cum since the start of the year, so his pathetic little cock just won’t stay soft. To fix his problem, I told him to ice it down—next thing I know, the eager sissy is outside defrosting his car naked, freezing his tiny thing off. @neild64.bsky.social
Mrs. Blackwood smirks, her handprint blooming on ‘Geraldine’s’ spanked bottom as he whimpers into the chair, his cage glinting under the vintage lamplight. ‘Dared to meet my eyes?’ she purrs, adjusting her pearls. ‘You’ll serve my every need—intimately—once I’ve finished teaching you manners.’
November 20, 2025 at 8:38 AM
Mrs. Blackwood smirks, her handprint blooming on ‘Geraldine’s’ spanked bottom as he whimpers into the chair, his cage glinting under the vintage lamplight. ‘Dared to meet my eyes?’ she purrs, adjusting her pearls. ‘You’ll serve my every need—intimately—once I’ve finished teaching you manners.’
This is one of my 1920s-inspired sissy creations. Here, Miss Whitmore, the commanding and effortlessly poised Dominatrix, asserts her control over violet, her devoted sissy. With a firm grip on his shoulder, she smirks and reminds him of his purpose
November 19, 2025 at 8:24 AM
This is one of my 1920s-inspired sissy creations. Here, Miss Whitmore, the commanding and effortlessly poised Dominatrix, asserts her control over violet, her devoted sissy. With a firm grip on his shoulder, she smirks and reminds him of his purpose
sissy neil woke with a stiff, aching cock—denied release or even the touch of his wife for nearly a year. To put an end to his little problem, I instructed him to cool his desires… with a bag of frozen peas. @neild64.bsky.social
November 19, 2025 at 7:53 AM
sissy neil woke with a stiff, aching cock—denied release or even the touch of his wife for nearly a year. To put an end to his little problem, I instructed him to cool his desires… with a bag of frozen peas. @neild64.bsky.social
In this 1960s-inspired office, the formidable Director Vanessa delivers a stern lesson to her bound and gagged secretary, sylvia. Tied to her chair, legs spread, and utterly exposed, sylvia is reminded—yet again—of her place and the consequences of incompetence.
November 18, 2025 at 8:45 AM
In this 1960s-inspired office, the formidable Director Vanessa delivers a stern lesson to her bound and gagged secretary, sylvia. Tied to her chair, legs spread, and utterly exposed, sylvia is reminded—yet again—of her place and the consequences of incompetence.
Corinne (@colblue) from fetlife spotted my post about unused creations and picked the two maid scenes—both in chastity, being taken anally by a well-endowed alpha. All I did was add her face and name, and honestly? It turned out fantastically—don’t you think?
November 18, 2025 at 6:57 AM
Corinne (@colblue) from fetlife spotted my post about unused creations and picked the two maid scenes—both in chastity, being taken anally by a well-endowed alpha. All I did was add her face and name, and honestly? It turned out fantastically—don’t you think?
When Ms. Ashley assumed Judith Taylor would be getting a cock, he never imagined it would mean she’d end up in chastity too—just as trapped and frustrated as he was. Now, both wait in their girly bedroom, dressed as slutty schoolgirls, for Headmaster Leo to arrive and deliver their punishment.
November 17, 2025 at 7:48 AM
When Ms. Ashley assumed Judith Taylor would be getting a cock, he never imagined it would mean she’d end up in chastity too—just as trapped and frustrated as he was. Now, both wait in their girly bedroom, dressed as slutty schoolgirls, for Headmaster Leo to arrive and deliver their punishment.
I’ve uncovered 20 unused creations from past projects—some abandoned, some rejected. Instead of deleting them, snag one for half my usual fee. Pick your favorite, I’ll add a custom caption and your chosen face, and it’s yours.
Interested in a bargain? Message me for details!
Interested in a bargain? Message me for details!
November 15, 2025 at 9:43 AM
I’ve uncovered 20 unused creations from past projects—some abandoned, some rejected. Instead of deleting them, snag one for half my usual fee. Pick your favorite, I’ll add a custom caption and your chosen face, and it’s yours.
Interested in a bargain? Message me for details!
Interested in a bargain? Message me for details!