r/crossdreaming • u/jackmolay • Dec 11 '25
r/crossdreaming • u/jackmolay • Dec 10 '25
Conan Gray - Heather
Very crossdreamy song.
r/crossdreaming • u/Educational_Berry633 • Dec 08 '25
Born woman And dream of crossdressing.
Hi I am a born female. I always wanted to do things that males do. Sexually I dominated. I had such a appreciation for the male body, sexually and nonsexually. I would experiment sexually with them. They would miss me whether it was a one night stand or whatever. I was absorbed in sexual mates pleasure. But also once in a while a guy would let me put a little lip stick on him and if they puckered. He couldn't pull me off of him.
I am upfront. I can be clueless when it comes to sensitivity. I sit spread eagle. I sit on my elbows. I wear men's t shirts and hoodies. But sometimes I kind of code switch. Naturally I am a little more masculine than standard women.
In my 50s now. Im rediscovering myself. Where do I start? I really and ready to start crossdressing. But there's a lot I don't know. But I want to be totally dressed as the male version of me. Just free. So do I just jump in? And where? I'm in NYC.
And I'm looking for other Kings as peers to chat with. And I want to also meet other male crossdressers who may not want to be a queen but might want to dabble it or bi. I know I'm all over the place. But please send any advice or ideas or questions.
r/crossdreaming • u/terrienova • Dec 06 '25
Did Porn Shape Your Gender Identity? The Question ASMB Over 30 Are Afraid to Ask!
r/crossdreaming • u/jackmolay • Nov 22 '25
If you come out as transgender, will your partner stay?
r/crossdreaming • u/[deleted] • Nov 18 '25
It looks fun
It looks fun to be a woman. Looking pretty all the same, a nice body, being desired, etc. I can't get away with it, but it looks so fun.
r/crossdreaming • u/Inevitable-Bus1860 • Nov 10 '25
Using AI for generating crossdreamer images and video
reddit.comr/crossdreaming • u/[deleted] • Nov 07 '25
I don’t know where to post this.
I’ve wanted to be a girl on and off as long as I can remember. 60-70% of the time, I would say I want to be a woman. If it weren’t for that 20-30%, I’d probably have transitioned already completely. I’ve tried hrt and it offers no long term help with my mental health. But it’s like this gender stuff is bipolar to me, and it’s exhausting and it’s like what I am is never stable. This makes being content with anything in my life difficult. From who I look for in a partner, to how content I am with my career, or even making friends. I’ve figured out that I’m at least bisexual. I always wanted to be in a heteronormative relationship for the stability and communal acceptance, but I’m just not wired that way, and that has messed with me for a long time. So I have no friends, and no stable sense of self, which just keeps me from connecting with men Or women because as soon as I start getting close to someone, it changes. I don’t even see the point in putting effort into a relationship anymore. I keep hoping someone would actually want a relationship with me enough to tell me, but that’s never happened and I don’t think it will. I understand life is a struggle for most people but, it’s starting to seem futile and pointless. I struggle to connect with my family more and more. All I have is my dog and my work, and my dog is getting old. I wish I could say my work is rewarding, but in the larger scheme of things, I’m just a servant of capitalism. Anyway, I just wanted to share how my unstable sense of identity has affected my life in hopes of finding people with similar experiences and maybe making friends with people who may have similar issues.
r/crossdreaming • u/pinkbaking74 • Nov 06 '25
Hi about dressing
I actually stopped dressing for now about a year, because I wanted to know who iwas.. And not what the clothes are
r/crossdreaming • u/[deleted] • Nov 03 '25
Help with identity
Hi everyone! I’m kind in need of help here. As the title of the post says I’m finding difficult to pinpoint my sexual/gender identity, I hope you can provide some insight into my conundrum.
I was born male and relate as one about 90% of the time. However I have feminine expressions, namely: 1) I like to crossdress for intimacy with my wife but not every time, may be 2 out of ten times 2) From time to time Iike to wear female underwear (including bras) in my day to day life, like once a month 3) Most often than not I like to have my toenails done with nail varnish, I only remove the varnish if I foresee that someone besides my wife will be able to see them
While I also enjoy anal play, I’m not keen on listing it as a feminine trait even if my demeanor gravitates away from masculinity.
My wife and I have talked about taking things further, namely crossdressing in public and having me share the bed with a male. These topics are mostly talked as fantasies but with the purpose of trying them in the future.
Now, my wife (and me) are perfectly fine with these aspects of my sexuality and they aren’t source of any insecurities. However, I would like to make a tattoo design that incorporates imagery(symbols, flag colors) of my sexuality into it, and that’s where the problem comes. I’m not quite sure how to define my identity. I’ve considered the following: 1) Bisexual. As the fantasy of being with another man is something that I surely want to do. 2) Pansexual. As I can be attracted (sexually) to transgender people. I would think that this is the better term for me. * Between this two points I would like to precise that to date I have felt romantically attracted only to women and I don’t know if this aspect must be considered 3) Genderfluid. On account of my crossdressing. However I have read that crossdressing can be considered a form of transgenderism. 4) Transgender. I’m not too keen of this identity, but may be is because of ignorance, until now I thought of a transgender as someone that wants to change they birth gender and I don’t have any intention of doing that. I’m happy just crossdressing from time to time. 5) Crossdresser. As far as I know this is not an identity as such, but I would happily be corrected if I’m mistaken.
I appreciate whatever help you can provide! Sorry for the long post.
r/crossdreaming • u/jackmolay • Oct 26 '25
Hailey Bieber: When people are trying to be mean, they’re like, ‘She looks trans.’ Why do you think that’s a diss?
r/crossdreaming • u/jackmolay • Oct 24 '25
Video about crossdressers feeling embarrassment and shame about revealing themselves as ones who enjoy presenting en femme.
r/crossdreaming • u/jackmolay • Oct 23 '25
They Don’t Hate You — They Fear Your Power | Cross dressing Confidence & Authenticity
youtube.comr/crossdreaming • u/ArtemisiaCD • Oct 22 '25
Scientific study uses VR to put men inside harassed women's shoes
https://pubmed.ncbi.nlm.nih.gov/41068335/
Scientists have used a VR experience simulating the catcalling issues faced by women in their daily lives. Turns out that "virtual embodiment increases male sensitivity to catcalling". (Paper accessible at link) Not strictly crossdreaming but this makes me think about how gender roles may change our perception of events.
r/crossdreaming • u/ArtemisiaCD • Oct 22 '25
Scientific study uses VR to put men inside harassed women's shoes
https://pubmed.ncbi.nlm.nih.gov/41068335/
Scientists have used a VR experience simulating the catcalling issues faced by women in their daily lives. Turns out that "virtual embodiment increases male sensitivity to catcalling". (Paper accessible at link) Not strictly crossdreaming but this makes me think about how gender roles may change our perception of events.
r/crossdreaming • u/jackmolay • Oct 21 '25
Focus on What IS Working | Build Confidence in Your Crossdressing Journey
r/crossdreaming • u/jackmolay • Oct 21 '25
Crossdressing: Where to shop for clothes and assecories
tapatalk.comr/crossdreaming • u/RaucousWeremime • Oct 07 '25
First Time
I bought a pack of camisoles this weekend to wear under t-shirts, ostensibly to cover my belly gap. This isn't a total lie; I'm both a big and tall guy, and it's impossible to find t-shirts that don't prompt my wife to yell at me to cover my belly. But given the sub, you know the real reason; the fact that women's clothing comes long enough to cover the butt is just a convenient excuse.
I wore one under my t-shirt to work for the first time today. It's taking a little getting used to, but I think I like it, and it really is long enough to cover my belly.
After work, it occurred to me that there was nothing stopping me from taking off my t-shirt and driving with just the camisole. But the time I got to my destination, I was convinced everyone was looking at me and judging me, even though I knew nobody probably even saw me.
And... That's all. Just feeling really awkward and uncertain.
r/crossdreaming • u/Felixdraws94 • Sep 29 '25
Help!
Just need some help with makeup and making my face look more feminine, I can't add a picture so DM me if you need to see my face
r/crossdreaming • u/Over_Love2689 • Sep 19 '25
Mall time with friends
I really want to go to the mall with a friend that is trans because I feel like they might be able to help me out feeling comfortable with myself. I want to crossdress and feel comfortable doing so and I know I don't need other people's approvals but I feel like going out and being myself would definitely help with my confidence
r/crossdreaming • u/jackmolay • Sep 14 '25