New to crossdressing at the age of 64, I'm shy and unsure of what to wear , makeup etc

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It's been a while since my last post. How's everyone doing? Today I practiced my makeup. 💄 ✨💕 I feel like I'm getting closer to my ideal Latex Doll look. Next week I'm heading to a fetish event. I wonder what kind of encounters await?

I think i look good without makeup, what do you Think 🤔❤️

Not happy, had to report another member for harassment today, for trying to discredit me, its no secret that some of my pictures are AI , however its my face feminined, a lot of us wear masks on here, some wear silicon masks some wear makeup two hide the face, I hide behind my AI image because I am not ready to show the world who I am, my wife and daughter know anout my cross dressing its created a mountain of problems more with my wife than my daughter, I almost have a non existent relationship with my wife now, two people know of me as Zara outside of here, however there are members on here I have seen out and about while I am the male version of me, I live in a very small town where a lot of people know each other being found out can destroy more than I am willing to loose, but if it means I will need to leave this site for my safety then that's what I will do

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Picking up some makeup bits from Boots later. Hopefully try a full face tomorrow. Prepare for Pennywise lol

Heavy makeup

This is one of my favorite bras. I still need to learn how to do makeup and wear a wig right or style my hair to be more female, but this bra helps with the illusion. http://chrissyinsd.hotviber.com/ #sissy #sissyboy #sissies #sissyboys #sissygirl #sissygirls #femboy #femboys #femman #gurl #crossdresser #crossdressers #crossdressing #tgirl #shemale #shemalechrissy #sissychrissyinsandiego #chrissyinsd #trans #transgirl #transwoman #transfemale #transgender #lgbt #queer #gay #dancing #twerking #pantyboy #meninpanties #dress #menindresses #bra #meninbras #bramodel

Makeup off going to bed ❤️ 😍 Dawn

I have a date tonight! The guy wants to tie me up and spank me! I have to shave my whole-body smooth again to be fem, take a good shower with lots of girly bodywash, put on my most girly lingerie and perfume along with a wig and maybe even some makeup? I'll share the details afterwards. I can't wait! I haven't been with a man in a couple of weeks! Kisses! http://chrissyinsd.hotviber.com/ #crossdresser #sissy #sissyboy #crossdressers #sissies #shemale #ladyboy #femboy #femman #femboys #crossdressing #gurl #trans #transgirl #transwoman #transgender #tgirl #gay #lgbtq #nsfw #adultsonly #adultcontent #sissygirl #transfemale #tgirl #model #modeling #gay #bi #lgbtq #queer #genderfluid #pantymodel #panty #panties #meninpanties

Omg I might have a date in the new year!! Omg I need a dress....and somewhere to get my makeup done!

Any other cross dressers have any fantisese to share, I want to be submissive and be controlled, yeah get shaven smooth and clean and put in chastity then a corset, fake breast fake nails and makeup wig and some sexy lungrie stocking suspenders high heels and clothes and then getting pimped out to make money, xxx

Makeup practice, what you think?, any tip on how I could improve, any flaws I may have missed? x

Went out at about 5pm and I spent nearly 2hrs doing makeup and getting dressed. All the girls were wonderful, I spent most of the night chatting to them about makeup, hair and how beautiful I looked which made me feel like one of the girls, had so many offers of having girly days out with them which made me feel like I was accepted by them. That was an amazing feeling, at one point I almost cried from happiness. All in all a wonderful magical night

No makeup today

First time showing my face and trying on makeup. Hopefully you all like it 😘

Hi sweets, I use the name “ShemaleChrissy” because I’m male and deeply identify with femininity and the desire to be female. I haven’t started transitioning yet, so I still look male. I’m also still learning makeup, hair, and styling, so I don’t always present as feminine as I’d like in everyday life. Sometimes I use face filters online to explore and express that feminine fantasy. That said, my body is always my real body, and I always include at least one natural, unfiltered photo. I do that intentionally so I’m not misleading anyone and so people know exactly who they’re talking to. Recently, someone told me I’m “not really a shemale” and should change my username. I’m open to honest feedback, but the way it was delivered was rude and disrespectful, so I blocked them. I welcome fair suggestions and thoughtful discussion, but I don’t tolerate harassment or abuse. So here’s my genuine question, asked in good faith: How would you describe me? Shemale? Sissy? Crossdresser? Something else entirely? I’m still figuring out my identity and language matters to me. If you have thoughts, I’m happy to hear them as long as they’re shared respectfully. Thanks for reading, Kisses, Chrissy 💋 #crossdresser #sissy #sissyboy #crossdressers #sissies #shemale #ladyboy #femboy #femman #femboys #crossdressing #gurl #trans #transgirl #transwoman #transgender #tgirl #gay #lgbtq #nsfw #adultsonly #adultcontent #sissy #crossdresser #crossdressing #femboy #sissyboy #sissygirl #trans #transgender #shemale #transgirl #transwoman #transfemale #tgirl #model #modeling #gay #bi #lgbtq #queer #genderfluid #pantymodel #panty #panties #meninpanties #ladyboy More: http://chrissyinsd.hotviber.com/

Hope you all had a great day yesterday 👄 Different hair and todays chosen wear no makeup except for eye shadow have a great day 😍😊

Hello sissys, whanted to share with you my little trick. When i have little time for a dressup. An hour or so, (egx. Kids gonna return soon.) And have no time to do a makeup. I use this face mask. 🖤 it gives such a sexy powerfull femine look. Without make up (just lips) what do you think. Leave a comment, do you use such masks? 😘❤️

Take me! You got my back against the wall! I have nowhere to go! I enjoy looking like a woman. I am too old and too set in my ways to fully #transition, so while I do dress #feminine in private and under my boy clothes, I don't do it in public and I haven't learned how to use makeup and wigs yet. So for now I live my life as a #woman in fantasy, online, using face filters from Snap chat. But t be clear: that is my real body, I am that smooth (I shave weekly), and I do this not to fool people I always show my true self, especially to potential dates. #gurl Thoughts? Kisses! - Chrissy #sissy #crossdresser #crossdressing #femboy #sissyboy #sissygirl #trans #transgender #shemale #transgirl #transwoman #transfemale #tgirl #model #modeling #gay #bi #lgbtq #queer #genderfluid #pantymodel #panty #panties #meninpanties #ladyboy More: http://chrissyinsd.hotviber.com/

A little no "makeup" photo sesh earlier 😅 dont really like all the moles on my face but the two beauty marks

Good morning, sisters.💋💋💋 Some tips on how to make your photo look better without resorting to AI. 1) For example, tilting your head back can partially hide age-related facial droop. Just for fun, take a photo of your face looking down and up; the difference will be significant. 2) The light source and its location are very important. Light can make a face look younger, or it can age it. Light can hide imperfections, or it can highlight them. 3) Makeup, at least foundation, and especially under-eye concealer. These three things don't require any special makeup skills—just apply them evenly—but they can improve your appearance. Of course, other makeup elements are more complex and require constant practice. But then, there's no need to use AI, although AI is certainly good. Interested in these tips?😊🤐

Last pics for the night, goodnight everyone 😴🥱 "No makeup"

Good evening! I enjoy looking like a woman. I am too old and too set in my ways to fully #transition, so while I do dress #feminine in private and under my boy clothes, I don't do it in public and I haven't learned how to use makeup and wigs yet. So for now I live my life as a #woman in fantasy, online, using face filters from Snap chat. But t be clear: that is my real body, I am that smooth (I shave weekly), and I do this not to fool people I always show my true self, especially to potential dates. #gurl Thoughts? Kisses! - Chrissy #sissy #crossdresser #crossdressing #femboy #sissyboy #sissygirl #trans #transgender #shemale #transgirl #transwoman #transfemale #tgirl #model #modeling #gay #bi #lgbtq #queer #genderfluid #pantymodel #panty #panties #meninpanties #ladyboy More: http://chrissyinsd.hotviber.com/

This is my first time wearing makeup, what do you think, girls?

Good evening, my dears. 💋💟 In this photo, a friendly woman helped me do my makeup, and she also took the photo. I only removed the background so as not to show how messy it was.😆🙈

Good morinig. Did you know that women have more color cones in their eyes, which are responsible for enhanced color perception? In other words, they distinguish color shades better. For example, if you ask a man to name shades of red, he might usually say, "This is dark red," "This is light red," or, at best, he'll remember a few more shades. But if you ask a woman, there are so many shades: red, scarlet, ruby, blood red, crimson, the color of ripe cherries, the color of young wine, the color of tomatoes, and so on and so forth. And they can give these shades to any color. Why am I saying this? Sometimes it can be very difficult to choose the color of makeup or clothes.🤔🤪

A little more from me👀 😋...😘 here i am showing my self 🌹 Love to do makeup,wigs, colour effects etc hehe love it 🫵☺️

I enjoy looking like a woman. I am too old and too set in my ways to fully #transition, so while I do dress #feminine in private and under my boy clothes, I don't do it in public and I haven't learned how to use makeup and wigs yet. So for now I live my life as a #woman in fantasy, online, using face filters from Snap chat. But t be clear: that is my real body, I am that smooth (I shave weekly), and I do this not to fool people I always show my true self, especially to potential dates. That is why the first two pics show me as my fantasy, as a #gurl, and the other two show me naturally. Thoughts? Kisses! - Chrissy #sissy #crossdresser #crossdressing #femboy #sissyboy #sissygirl #trans #transgender #shemale #transgirl #transwoman #transfemale #tgirl #model #modeling #gay #bi #lgbtq #queer #genderfluid #pantymodel #panty #panties #meninpanties #ladyboy More: http://chrissyinsd.hotviber.com/

I enjoy looking like a woman. I am too old and too set in my ways to fully #transition, so while I do dress #feminine in private and under my boy clothes, I don't do it in public and I haven't learned how to use makeup and wigs yet. So for now I live my life as a #woman in fantasy, online, using face filters from Snap chat. But t be clear: that is my real body, I am that smooth (I shave weekly), and I do this not to fool people I always show my true self, especially to potential dates. That is why the first two pics show me as my fantasy, as a #gurl, and the other two show me naturally. Thoughts? Kisses! - Chrissy #sissy #crossdresser #crossdressing #femboy #sissyboy #sissygirl #gurl #trans #transgender #shemale #transgirl #transwoman #transfemale #tgirl #model #modeling #gay #bi #lgbtq #queer #genderfluid #pantymodel #panty #panties #meninpanties #ladyboy More: http://chrissyinsd.hotviber.com/

First but not the last photo ... It was one of my first open trips as Kate, one of the first successful photo. All as I trully wanted blue lashes, choclate lipstick, long hair... I publish it now as I do not know if I am able to continue Almost a year of photo work came to sudden problem Security Seems to have camera in where I change Against any law and ordinary human sence Every time I lock to change late in the evening they immediately come to ask if anything OK with me... No it is not OK with me I want peacefuly lock myself make make up and chose dress. And live that little time as Kate... At First I thought an accident now I know not And I may easily loose my job too.For that I soend time in loo aftwr honestly done work... I need to make a pause Stop desining May be train myself better makeup somewhere The oublic baby changing room do not allow to lock yourself I would never fo it at home... Just nowhere to do what I like if only Kate on a trip... Wish you all peaceful time I might still write something or work on old photos but they are not so good any more for me Lots of Love Good Health and strong pleasant tights... Love Light and Joy. Kate

Passport photo......rejected! Come on, I put the minimum makeup on possible!!! 😁

Good makeup day ❤️

When I was choosing a makeup primer, I was puzzled by the color; it turns out every primer is different. So what should I choose? Who should I ask? Who should I find out from? White is the most popular color, and if you choose one with a radiant effect, it's great for aging skin, helping to conceal wrinkles. But if you have bags under your eyes, a yellow primer will come in handy. Pink and peach colors are suitable for those with a dull complexion. A green primer is ideal for those with rosacea (protruding blood vessels through the skin), redness, or very fair skin. But if you have pigmentation or yellowness, a purple primer is best. It's especially useful when shooting with a flash. Such knowledge can sometimes be difficult to keep in mind; manufacturers have now started releasing universal primers for trial, where all colors blend together when applied. I prefer generalists, although generalism isn't always better than more specialized knowledge. I hope you found it interesting.

Got dressed last night before playing but didn't take the time to do a quick makeup session 😅

Hi ladies. The need for proper makeup skills is clearly a pressing need. I don't know if linking is allowed here, so I won't. But I can recommend a good app that can be very helpful in determining your skin tone, undertone, and so on. Just take a selfie in good lighting (this is important), and the app will then determine it for you. It will then select the appropriate colors for makeup, clothing, and hair. I'm not promoting it, but I use it myself. You can find it on many platforms, such as Google Play and the App Store. It's called Dressica. The logo for the app is included in the post to avoid confusion.

My makeup isn't the best, I lack the necessary skills, and my makeup bag is missing a lot. Then there's age, which causes facial drooping, and my significant weight loss, which has had a significant negative impact on my face. 🥺 Nevertheless, I wish you a good day and send kisses to all of you, ladies, sisters, and secret admirers. 💋💋💋

You've probably seen an old video about how masterful makeup application can transform your appearance beyond recognition. Frankly, I admire such mastery. It's a level I strive to reach. However, when I try it myself, it doesn't always turn out quite right. Makeup artists make it look easy and simple in videos, but in practice... it's all just not quite right.😆 Yes, I know, practice makes perfect. But you don't get the chance to practice often. My point is, if I post a photo of myself with poorly applied makeup, please don't judge me harshly. In the meantime, enjoy the video; it's worth the time to be amazed and admired.

Everything you people get from the news is a lie. Donald Trump hasn't done anything to anybody. Besides, what kind of a man would vote for a woman as executive chief of the military? We never had fakes news until we had a fake president. Anyhow, it's been a year since I was in jail and lost my entire wardrobe, makeup, and shoes. Nothing's been right since then. Everybody else is getting hotter while I'm left far far behind in the competition. I'm not late. It's just that I'm in competition with self-absorbed narcissistic men who really aren't worthy of the spiteful admiration they receive. I know of plenty of self centered hetero men who deserve equally dreadful fates as legit trans women. Oh, and it'll be almost 8 months since I began hrt. I believe my body is rejecting it and my outward male appearance is too dominant for serious feminine changes. Oh well. The world is cruel. An eye for an eye. I know exactly who deserves my jealous revenge. Nobody deserves to feel safe.

Greetings to you, my dear sisters. And to you, Admirers. I wanted to tell you a little about myself. I started crossdressing relatively recently, about five years ago. I'd been wanting to do it for a while, of course, but I only got around to trying it recently. What did it give me? Well, it motivated me to lose weight, from 130 kg to 78, although my body is still not perfect; my body fat percentage is excessive, in my opinion, and such a significant weight loss couldn't help but negatively impact both my face and body. I also began to better understand women and how they think. When you look at yourself in a dress in the mirror and realize it doesn't suit your figure or the color... Oh yes, now the thoughts of women in the same situation are much clearer.🙂 I've discovered things men don't think about, like how to determine my body type to match it with clothes, my face type to match a wig, my skin tone and undertone to choose the right makeup colors, my overall complexion, and its level of contrast, which helps me choose clothing colors. I'm really interested in exploring all of this. Of course, I'm not perfect at everything. I'm not very good at makeup; for example, I'm still working on my body despite having suffered numerous injuries. Losing weight isn't always a good thing; it exposes problems I never even suspected. 🤔Sometimes my looks look a bit slutty, my wardrobe isn't very large, and I can't find shoes in the right size. I also have to hide my hobbies, like hiding my face in photos, because I get more negativity and threats from the world than positive ones.🤐 But at the same time, there's a sense of harmony and inner peace when I have the rare opportunity to transform myself, even if only temporarily.☺️ My English isn't very good, I use an online translator, and the text may be a bit awkward, so please excuse me. Kisses to you all, sisters, wherever you are.😚😙😚💝

Sitting here alone wearing a satin thong and matching bra heels with ankle straps a black blouse with a short red Minnie skirt, I've just put on fake nails and makeup and wig, I feel so sexy, and I want someone to share the experience with, yeah would love to be submissive and be a discreet gurl for the right person xxx

🌸 Between Silk and Skin: Understanding the Line Between Crossdressing and Being Transgender By Chrissy “Maybe I’m not one or the other. Maybe I’m something in between—and that’s okay.” 🧠 What’s the Difference? When people hear “crossdresser” and “transgender,” they often picture the same thing—or get the definitions confused. But these words speak to different experiences, identities, and emotional landscapes. In simple terms: Crossdresser: A person (usually male-assigned at birth) who enjoys dressing in clothing typically associated with another gender, usually for self-expression, fun, comfort, identity exploration, or even erotic reasons. This doesn’t necessarily mean they want to live as that gender full-time. Transgender: Someone whose gender identity is different from the sex they were assigned at birth. A transgender woman was assigned male at birth but identifies as a woman—and may or may not take steps to socially, medically, or legally transition. 🩷 My Journey (So Far) I’m still figuring it all out. For most of my life, I lived as a man—because that’s what the world expected. But in quiet moments, in safe spaces, I allowed my femininity to surface. At first, I called it crossdressing. I liked how I felt in soft clothes, in cute outfits, in long hair and smooth skin. It was sensual… empowering… liberating. But it wasn’t just the clothes—it was me, underneath them. I still don’t know where I fall on the spectrum. Maybe I’m a crossdresser. Maybe I’m genderfluid. Maybe I’m a transgender woman still waiting to be born. What I do know is this: I feel most alive when I’m Chrissy. I feel most whole when I’m seen. I feel most me when I stop trying to choose sides. 🫶 A Spectrum, Not a Binary Gender is not black and white—it’s fluid, rich, and deeply personal. Some crossdressers live full, happy lives identifying as men who occasionally (or frequently) express femininity. Some transgender women started out crossdressing because it was safer than admitting the truth. Others—like me—are still discovering who they are. You might ask: Am I a crossdresser or something more? What does it mean if I like being called “she” sometimes? Do I want to be a woman or just look like one? The answer might be “yes,” “no,” “sometimes,” or “I’m not sure yet.” And all of those are valid. 💬 A Note on Shame and Freedom Growing up, I repressed my feminine side. I feared being laughed at, rejected, or labeled. I used filters to feminize my face online—not to trick anyone, but because I liked how I looked. It made me feel beautiful. For now, it’s my way of being seen. One day, I’ll do the makeup. The hair. The outfit. One day, I’ll walk outside and own her. For now, I’m just beginning. If you feel the same—if you’re navigating the space between crossdressing and being trans—you are not alone. 🎀 Final Thoughts You don’t need to rush toward a label. You don’t need to transition or explain yourself to anyone. You don’t need to choose “male” or “female” like you’re checking a box. You just need to be—whatever that means, however that looks, however long it takes. You’re not broken. You’re not confused. You’re becoming. And I’m becoming right there with you. What are your thoughts? With love, — Chrissy

Some screenshots from my latest video!: https://photos.app.goo.gl/RQucHsycTcgMboQR8 Hey sweets! I undress for you in this video! Yes, I'm sorry, I didn't put any makeup on or use a filter to feminize or soften my face, so I still look "manly," but I hope you enjoy this anyways? Please "like," leave a comment, and share! Sharing is caring! And you can message me too. I'll reply when I can. Thanks! Kisses! - Chrissy #crossdresser #crossdressing #sissy #sissyboy #shemale #ladyboy #femboy #tgirl #gurl #trans #transwoman #transgirl #transgender #nsfw #panty #panties #pantybulge #pantymodel #underwear #underwearmodel #underwearbulge #model #meninpanties

https://photos.app.goo.gl/RQucHsycTcgMboQR8 Hey sweets! I undress for you in this video! Yes, I'm sorry, I didn't put any makeup on or use a filter to feminize or soften my face, so I still look "manly," but I hope you enjoy this anyways? Please "like," leave a comment, and share! Sharing is caring! And you can message me too. I'll reply when I can. Thanks! Kisses! - Chrissy #crossdresser #crossdressing #sissy #sissyboy #shemale #ladyboy #femboy #tgirl #gurl #trans #transwoman #transgirl #transgender #nsfw #panty #panties #pantybulge #pantymodel #underwear #underwearmodel #underwearbulge #model #meninpanties

I really enjoy looking like a woman. Yes , some of those photos are obviously filters , but I would look like that if I learned how to use makeup and a wig. Which hairstyle do you like better? #crossdresser #crossdressing #model #modeling #sissy #sissyboy #femboy #femboys ##shemale #gurl #tgirl #trans #transgender #transgirl ##transwoman ##lgbtq #gay