How I Learned to Stop Worrying and Love Crossdressing

[Lily Peg]

Thanks for sharing. Tension from a female partner is basically expected in most cases, because crossdressing provokes insecurities that cause them to feel like their very womanhood is under attack. Specifically:

1) Negative stereotypes about crossdressing perpetuate the myth that all crossdressers are closeted gays or bisexual who want to transition to becoming female, which results in her feeling "deceived" about your sexuality, worried that you aren't or will stop being attracted to her sexually, or concerned that you want to transition. In reality, crossdressers come in all genders and sexualities.

2) Women with a binary view of gender may feel that you seek out femininity because she doesn't offer enough of it, i.e. "You're doing this because I'm not woman enough for you." Of course, it actually has nothing to do with them and is an internalized desire that began long before she even entered your life.

3) The overwhelming amount of "sissy"-oriented material on the internet may lead the uniformed to believe that all crossdressers are sissies who are into kink, BDSM, chastity, humiliation, group sex, etc. when in reality the vast majority of crossdressers are very vanilla and very heterosexual. Basically an all squares are rectangles but not all rectangles are squares situation.

Open communication is crucial to overcoming any challenge in a relationship, and I would encourage her to learn more about what crossdressing actually means instead of just going with what she's heard. My blog post on common crossdressing myths might be a good place to start.

I do hope that most female partners will come around and at least tolerate if not necessarily enjoy their partner engaging in crossdressing once they learn a bit more about it, but the unfortunate reality is that for some women, it is a dealbreaker no matter what. In those cases, it's time to consider if crossdressing is right for you.

Good luck!

-Jen

Spot on there l agree with you wholeheartedly.
expand...Thanks for your interesting insights into these current questions about male gender identity and the who and what is a "sissy".
From my perspective of being called a sissy by various males l enjoy fem wear and other aspects of gender fluidity.
True that for hundreds of years men and women would exchange roles especially during festivals onto public plays and pantomimes etc. Dandies in Victorian age was common amongst the upper middle classes etc. The 60s sexy revolution made unisex and camp more open as homosexuality was legalised and the pill was freely available.
The internet flooded us with porn of every kind of sexual activity and made us think and feel what we really wanted to express was an authentic and genuine sense of self.
But of course the reality is far more weirder than our fantasies and often scary to go beyond the virtual highway.
Societies especially amongst male dominance fears this explosion of gender fluidity and sissification. Men have to be men to maintain the status quo. David Bowie and the like tried to break these shackles and show men could be different and not rely on aggression to get their in own sexual way.
Being a sissy is just one aspect of being more open to change and not stuck in a mindset of masculinity and power.

 

[jboggy]

Then and now

 

[bimori]

Then and now

Mmmm so sexy love.

 

[AlexBailey]

I'm bringing this over from part of a post on another thread, slightly edited:


My CD history started early, I was in kids theater and had an older sister who liked to dress me up - my mom didn't think anything of it until I wanted to wear a girls swimsuit to the beach. My older sister was a competitive ice skater so I had a lot of hand-me-downs via the give-away box. My parents did what they could to redirect me when they found my stash of girls stuff in grade school. I was pretty crushed and confused over it. It's the first time I can think of when I felt gender dysphoria.

In high school I was slightly femme and in the closet. I got a lot of attention from girls but I think I was known as a "safe guy" - someone who was fun for girls to hang out with but wasn't going to hit on them - I just wanted to be one of them.

I think it was because of this "safe vibe* that the captain of the varsity cheer squad asked me to the prom. I felt out of place but handsome in my tux but we ended up becoming a couple for a few months. I did my best to outwardly play the guy role for her, but she seemed to like the fact that I was not very manly.

Later she and some of the other squad girls dressed me up in a girls cheer uniform for a friday school event where the girls played football (American) and some of us guys were cheerleaders. I fucking loved it and no one gave me a hard time - my girlfriend was one of the hottest girls in school - and she did look incredible in the football gear. Something changed between us after that. Our relationship cooled down and it seemed more like a friendship than lovers. We broke up before graduation but I've replayed that day in my memories ever since.

In college I had a punkish girlfriend who liked to girl me out. She would have me wear her lingerie in bed and occasionally I'd go out in her clothes. I don't think I ever really 'passed' but I got mistaken a lot. When I went to a rowdy new year concert in jeans and a girl's top I got my ass grabbed more times than I could count. Nearly got my ass kicked a few times too. It produced a lot of mixed emotions but it also allowed me to understand more about what predators can be like.

I ended up being partners for several years with a girl who has always identified as lesbian. It's funny but I only occasionally openly cross dressed then. I often got mistaken for a tomboy. Some of our friends were somewhat anti-trans (TERF?) - I often felt a strange tension from them if I was dressing overtly feminine. On the one hand I felt welcome within our community, on the other I was an outsider simply for how I was born and could never truly belong.

My wife and I enjoy lots of my fetish interests now, but I also often dress in a sort of hybrid style. I wear kilts a lot and now that our kids are adults I occasionally wear skirts over leggings or jeans. I often wear my hair in braided pig-tails. I'm still frequently mistaken for female from behind.

 

[MsNatalie99]

For me I'd always felt different. I'd begun dressing in my sisters clothes when I was eight. It was only around the house but my dad, though uncomfrtable with it, encouraged my to decide things for my self. A year later he and my youngest sister died in a boating accident. My dad was driving a little two seater he bought off of a coworker, when he had a brain aneurysm and ran ashore. From then on, whenever I was indoors I wore girls clothing. In my senior year of highschool, I'd grown tired of the dual identities, and begun dressing everywhere, all the time. The names I was called, and the bullying I endured, I cried everyday. Then my first big success. A kid at school, Jacob, who I thought to be the sexiest guy ever, asked me to homecoming. It was a magical night. We danced to more than half the songs, kissed, and made plans. He'd said his parents got him a room "just in case" and we could go there.

The tone changed in the parking lot. Jacob along with three other boys beat me up, breaking 3 ribs, my left radius, knocked out two teeth, breaking two other, and collapsed my right orbital cavity. From there they stipped away my dress, pissed on me, and left me there. It took almost a year for charges to be pressed. On the scene one of the police officers it argued that I probably antagonized them, should have read the room. Because of my injuries and Rehabilitation, I missed the rest of my senior year and had to repeat it the following year. I've never been comfortable in boy clothes. I don't necessarily identify any kind of special way, but I know who I am and how I dress. I've been openly gay since junior year. Never kissed a girl, or dated outside of my sex. Though I have topped, I've always been a bottom, not a sissy, but fem.

5 years down the road I still dress every day everywhere I go unless a job won't permit me to. I still get a hard time from time to time from people who don't understand. I don't dress because it makes me feel sexy, I dress because it makes me feel like me. I've always been Natalie, not Nathan. Nowadays my biggest problem is dating. At least my biggest problem when it comes to dressing. The world has since become a lot more tolerant than it was when I started. I find that when I'm dating it's hard to find guys who are not only openly gay, but are also fine with dating a crossdresser in broad daylight without concern of how they may appear. Usually what I get is people that only want me to dress in the bedroom, or people who wanted me specifically because I dress and that's all they need to know about me. My heart goes out to anybody out there on this journey trying to figure out who they are. It takes a lot of balls to wear a dress in public, to meet grown men, who could either be your lover, or another guy looking to kick you down. Let me say I'm sorry if my story has ruined the tone of this forum. I've always known who I was, and through dressing, I've become that person.

 

[OlderBtm4U]

So sorry for the pain Jacob and the others brought you.

 

[MsNatalie99]

So sorry for the pain Jacob and the others brought you.

Thank you. It's made me feel stronger, and my lifestyle feel earned. It was a trip when I went back home in december to see rainbow banners hanging from my school while Trump 2024 signs were staked in the grass.

 

[Patticd]

Thank you to everyone for posting their stories and experiences

 

[SPARTAN047]

Great to hear everyone's experiences. I loved the long post above which mentioned women's insecurities on seeing CDs or trans girls.

Some women who see me dressed out are nothing but kind and encouraging.

Some of the women who I was in groups with online have been vicious in attacking me, which is both amusing and sad in case their female ego was hurt. It shows that for every male insecurity or issue, there's always a female one. 100%.

I've never understood it at all, though I've had men and even other CDs be absolutely horrible and nasty to me over social media and occasionally IRL. I don't even look that convincing or pretty like most women or CDs, I just like dressing.

 

[Flanast]

Thanks so much for sharing. My own story is not all that different. Started very young dressing in my mothers dresses, always afraid of discovery. That progressed dressing in my Gf’s clothes when I was alone in her room. This continued once I got married to a different girl, many times buying and then purging my girly things because I was afraid I got caught. Once divorced (for other reasons), I had more of an opportunity to dress up fully while at the same time dating different woman. Also at this time, my interest in men increased, and had an ongoing relationship with an nearby guy. He didn’t get into me dressing up so couldn’t fulfill my desire to be someone’s cross dressing girlfriend. But I did have the chance to go out fully dresssed. I’m not passable but it may take a few looks before realizing I’m CD. Still looking for that guy that wants to make me his girl. I’m often wondering whether I should go on HRT to grow breasts and look more feminine. Courious everyone’s views on doing this at a more mature age (over 50).

 

[Escierto]

Thanks so much for sharing. My own story is not all that different. Started very young dressing in my mothers dresses, always afraid of discovery. That progressed dressing in my Gf’s clothes when I was alone in her room. This continued once I got married to a different girl, many times buying and then purging my girly things because I was afraid I got caught. Once divorced (for other reasons), I had more of an opportunity to dress up fully while at the same time dating different woman. Also at this time, my interest in men increased, and had an ongoing relationship with an nearby guy. He didn’t get into me dressing up so couldn’t fulfill my desire to be someone’s cross dressing girlfriend. But I did have the chance to go out fully dresssed. I’m not passable but it may take a few looks before realizing I’m CD. Still looking for that guy that wants to make me his girl. I’m often wondering whether I should go on HRT to grow breasts and look more feminine. Courious everyone’s views on doing this at a more mature age (over 50).

Go for it. No regrets.

 

[Bisexguy70]

Thanks so much for sharing. My own story is not all that different. Started very young dressing in my mothers dresses, always afraid of discovery. That progressed dressing in my Gf’s clothes when I was alone in her room. This continued once I got married to a different girl, many times buying and then purging my girly things because I was afraid I got caught. Once divorced (for other reasons), I had more of an opportunity to dress up fully while at the same time dating different woman. Also at this time, my interest in men increased, and had an ongoing relationship with an nearby guy. He didn’t get into me dressing up so couldn’t fulfill my desire to be someone’s cross dressing girlfriend. But I did have the chance to go out fully dresssed. I’m not passable but it may take a few looks before realizing I’m CD. Still looking for that guy that wants to make me his girl. I’m often wondering whether I should go on HRT to grow breasts and look more feminine. Courious everyone’s views on doing this at a more mature age (over 50).

In my opinion, i think you should remain the way you are. I CD some too but only a minimal amount. To me its a lot of whats in the mind and not whats on the body. I see through the clothes and my sex goggles see the inward female. I can just imagine your sensuality coming out as you please men. I mean i love your title “proud cocksucker”. Like me you dont deny the fact that you love cock and thats very erotic, breasts or no breasts. I love pussy but prefer the equipment of a man when i play sexually. Plus nipples and flatter chests are a turn on for me. I was always attracted to tiny breasted woman and your already there. Nothing hotter then sucking a guys sensitive nips getting them rock hard. I suppose the only thing i would suggest is removing excess hair. A smooth body to me feels amazing. I know opinions are like assholes, Everyone has one, so this is mine. . Any man would be lucky to take you, just as you are with your sensuality and your feminine qualities, but yet manly features. SO HOT!!! Pm me if you want.

 

[Buffalogurl]

For me I'd always felt different. I'd begun dressing in my sisters clothes when I was eight. It was only around the house but my dad, though uncomfrtable with it, encouraged my to decide things for my self. A year later he and my youngest sister died in a boating accident. My dad was driving a little two seater he bought off of a coworker, when he had a brain aneurysm and ran ashore. From then on, whenever I was indoors I wore girls clothing. In my senior year of highschool, I'd grown tired of the dual identities, and begun dressing everywhere, all the time. The names I was called, and the bullying I endured, I cried everyday. Then my first big success. A kid at school, Jacob, who I thought to be the sexiest guy ever, asked me to homecoming. It was a magical night. We danced to more than half the songs, kissed, and made plans. He'd said his parents got him a room "just in case" and we could go there.

The tone changed in the parking lot. Jacob along with three other boys beat me up, breaking 3 ribs, my left radius, knocked out two teeth, breaking two other, and collapsed my right orbital cavity. From there they stipped away my dress, pissed on me, and left me there. It took almost a year for charges to be pressed. On the scene one of the police officers it argued that I probably antagonized them, should have read the room. Because of my injuries and Rehabilitation, I missed the rest of my senior year and had to repeat it the following year. I've never been comfortable in boy clothes. I don't necessarily identify any kind of special way, but I know who I am and how I dress. I've been openly gay since junior year. Never kissed a girl, or dated outside of my sex. Though I have topped, I've always been a bottom, not a sissy, but fem.

5 years down the road I still dress every day everywhere I go unless a job won't permit me to. I still get a hard time from time to time from people who don't understand. I don't dress because it makes me feel sexy, I dress because it makes me feel like me. I've always been Natalie, not Nathan. Nowadays my biggest problem is dating. At least my biggest problem when it comes to dressing. The world has since become a lot more tolerant than it was when I started. I find that when I'm dating it's hard to find guys who are not only openly gay, but are also fine with dating a crossdresser in broad daylight without concern of how they may appear. Usually what I get is people that only want me to dress in the bedroom, or people who wanted me specifically because I dress and that's all they need to know about me. My heart goes out to anybody out there on this journey trying to figure out who they are. It takes a lot of balls to wear a dress in public, to meet grown men, who could either be your lover, or another guy looking to kick you down. Let me say I'm sorry if my story has ruined the tone of this forum. I've always known who I was, and through dressing, I've become that person.

I'm sorry you received a beating, the world is full of monsters.....

 

[stargame]

Hello everyone, I love reading every one's story I actually can't remember when I started dressing like a girl, it was from my very beginning. My sister and I shared the same panty drawer.

 

[Sigmund7]

I started wearing panties on occasion when I was quite young but began to wear them on a regular basis when I got married (over 40 years ago). My wife and I used to share a panty drawer but I prefer nicer panties than she does, so we no longer share.

 

[SPARTAN047]

I still go out dressed very regularly and use makeup, etc. I don't look that great but I'm so happy being feminine in a sense while retaining my masculine brain.