20yo Aspiring Sissy Seeking Online Dom and Feminization Coach for Makeup & Training

Hi there,

I'm a 20-year-old guy with very little real experience beyond occasionally wearing girls' clothes in private. I'm looking for an experienced online dom plus feminization coach to guide and train me properly into becoming a pretty girl with blackmail.

I'm seeking a structured, ongoing dynamic focused on:

Makeup skills, styling, and feminine image advice (helping me look convincingly cute and passable)

Progressive sissy training and tasks

Sexual elements and play as part of the dynamic

Creative commands, such as ordering me to create and run an Instagram account under my new feminine persona for posting progress, outfits, etc.

I’m very eager, obedient, and ready to put in consistent effort. Hard limits: anything illegal or involving non-consenting third parties, anything that could cause social suicide/exposure, scat, boring/pointless tasks, and anything permanent or non-reversible.

If you're a dominant who enjoys mentoring sissies with a focus on makeup/feminization and enjoys controlling the transformation, please message me. Let me know a bit about your experience and approach.

Excited to hear from a potential Dom💕

reddit.com
u/Reasonable_Manner330 — 2 days ago

[M4A] 20yo Aspiring Sissy Seeking Online Dom/ Feminization Coach for Makeup & Training

Hi there,

I'm a 20-year-old guy with very little real experience beyond occasionally wearing girls' clothes in private. I'm looking for an experienced online Mistress or feminization coach to guide and train me properly into becoming a pretty girl.

I'm seeking a structured, ongoing dynamic focused on:

Makeup skills, styling, and feminine image advice (helping me look convincingly cute and passable)

Progressive sissy training and tasks

Sexual elements and play as part of the dynamic

Creative commands, such as ordering me to create and run an Instagram account under my new feminine persona for posting progress, outfits, etc.

I’m very eager, obedient, and ready to put in consistent effort. Hard limits: anything illegal or involving non-consenting third parties, anything that could cause social suicide/exposure, scat, boring/pointless tasks, and anything permanent or non-reversible.

If you're a dominant who enjoys mentoring sissies with a focus on makeup/feminization and enjoys controlling the transformation, please message me. Let me know a bit about your experience and approach.

Excited to hear from a potential Mistress 💕

reddit.com
u/Reasonable_Manner330 — 2 days ago

20 [M4A] Slowburn Feminization

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I'm currently searching for someone that feels genuinely excited for this idea, I wanna be blackmailed and feminized but my current living situation doesn't work that well for it so I thought like for this month and until starts of August we will have a lighter blackmail play where you make me learn all I need to do to feminize myself like makeup, dressing etc, my goal is to become convinxingly female and go for the egirl archetype aesthetic, and give me like "lessons/educational" videos that teach me something and at the end of each week you make me an exam and so and if I fail get punished etc. I hope someone interested

reddit.com
u/Reasonable_Manner330 — 17 days ago

Question for Blackmailers?

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Why some of you are so reserved on the way of like not letting know themeselves, now I do get it a bit, about you dont want to show yourself or show weakness, but isnt Blackmail or at least should be a very trusts based kink, maybe its just my rpeference but I would like it more to know the person is blackmailing me is also human sometimes, I think it makes it hotter but when the blackmail has more of a persona, than just blabbing and ordering around? What do other subs and blackmailers think? Lmk

reddit.com
u/Reasonable_Manner330 — 2 months ago

Like I wanna learn all the possible methods I can do to make myself to looks passable but also as hot as possible, I know its best with paid services and so, but where can I find those online?

reddit.com
u/Reasonable_Manner330 — 2 months ago

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The idea is that I’m basically turned into a picture model by force, more like a curated IG or TikTok persona than a person making their own choices. You decide the look for the day, clothes, makeup, vibe, and I follow it and send a photo to show it’s done. It’s less about roleplay and more about being managed and shaped into an image.

The styles can rotate depending on what you want. Sometimes it’s simple and feminine, sometimes more provocative, cute, stylized, or themed like cosplay. The point is consistency and control, not improvising or doing what I feel like. I’m there to be presented, not to decide.

I'm not interested in the sexual part or anal, I'm okay with being caged though, but I feel the sexual arousal from being dressed up not being fucked, if you're someone that's extremely girly, I think you would be the best fit.

Blackmail is what keeps it grounded, with you holding the pics. It adds real leverage and structure, so it doesn’t feel symbolic or optional. The image, the routine, and the compliance all tie together into the same system.

reddit.com
u/Reasonable_Manner330 — 2 months ago

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I have been experimenting with this kink a bit, and I always pussy out, but also when I feel brave enough the situation isnt right, like right now, I'll let you know from start I will be limited on what to do, so Im in search of a creative domme, so first of all, I would like to get into feminization but in the kind where the main objective is that with effort and training I look hot and look like a girl, not a guy in a dress, but genuinely look like a girl, now I understand that this entaols probably buying clothes, makeup, etc. But...my situation doesnt let me do that yet, in next months probably could but in the meantime maybe I could have a mistress that gives me tasks or homework or even then makes tests I have to pass meanwhile or other creative ideas I can do on my room alone, hypnosis, whatever comes to mind that will help into the feminization part, also Im not trans so not into HRT or anything permanent. Hope to hear back to you.

reddit.com
u/Reasonable_Manner330 — 2 months ago

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Im looking for a blackmail dynamic where you enforce me to feminize myself further each time, but its alsoba slow burn so its almost doesnt feel like a change until is too late, and force me to look each day into looking more convincgly like a girl and be pretty at that, also you can eventually lock me in chastity and techdom if you wish so, I would like to also mention the caveat of I prefer to paly weekdays Mon-Thu, and keep the other days separate where i will not be active, if this catches your attention DM me, also currently just have lingerie clothing

reddit.com
u/Reasonable_Manner330 — 2 months ago

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Im looking for a blackmail dynamic where you enforce me to feminize myself further each time, but its alsoba slow burn so its almost doesnt feel like a change until is too late, and force me to look each day into looking more convincgly like a girl and be pretty at that, also you can eventually lock me in chastity and techdom if you wish so, I would like to also mention the caveat of I prefer to paly weekdays Mon-Thu, and keep the other days separate where i will not be active, if this catches your attention DM me, also currently just have lingerie clothing

reddit.com
u/Reasonable_Manner330 — 2 months ago