Dear Gabi,

My name’s Angel and I have a crossdressing boyfriend, “Sullie”. We’re still in highschool, and have been dating for two years, but I’ve only just found out that he’s a crossdresser because he has been afraid to tell me because of how I may have reacted. I fully accept him, and try to encourage him to be himself no matter what. I am 1 of 5 people who know, but none of his friends or family know.

I’m almost sadden by the fact that he had took so long, after I’ve been very vocal on my opinions about Gay, Bi, Lesbian and etc decisions in life. I myself am Bisexual, but Sullie’s the only person for me.

He’s become a shell of himself and is still nervous when he dresses around me. He feels he is a freak, and “not normal.” This is what saddens me the most. His acceptance in society won’t be felt for a while. Like said, I fully, 100% support him in any way possible. He is himself, and that’s what I fell in love with, nothing less.

Our first year together, he wasn’t the most faithful, but something held me to him. Something told me to stay. After he came out, things have been so much better. We are stronger, and I can honestly say, I have never ever felt closer to him.

Sully has always had a quality about him, a shy nature. But as he has progressed in his nature and sexuality, he’s become ashamed of himself – not at all times, but it’s definitely a mental state of depression that I hate to see him go through. He’s never been sure of himself, inside and out. Now that I know, it’s boosted him slightly, but not enough for him to come out as Sullie to other people.

I sometimes get frustrated because some of the comments his friends make without knowing honestly offend him, but he can’t say anything. He’s 16. Do you have any advice for us? And advice for confidence for him?

Angel

(more…)

Posted by Gabrielle | 4 Comments »

Dear Gabi,

I am a straight SWF and actress. Can you explain why some dressers are straight, some are bi, and some are gay? Do they find dressing sexual at all? Do they have a special id with their mothers or sisters? Does each prefer specific items of clothing, or soft, silky fabric? Is the attraction to the clothing, or the idea of being a sexually appealing or soft female? Would they be more attracted to a more feminine or masculine looking and acting woman?

I have encountered many cross-dressers in Las Vegas, in and out of the entertainment industry. Most are very shy about revealing their preferences. Most surprising is that most focus on one specific garment ie shoes, lingerie, mini-skirts, that is associated with female sexuality. That is why I was trying to understand the psychology behind it.

Thanks for your response. Many girls are just curious.

Davida-Rochelle

(more…)

Posted by Gabrielle | 15 Comments »

Dear Gabi,

I have just approached a therapist about some sessions as I feel my crossdressing is starting to effect my relationship. My girlfriend is understanding in a way but is still not overly keen.

It is just me who will be attending, as we both feel there are issues I need to address which could all be linked. Short temper for no apparent reason like I get really mad about the most silly things. My girlfriend thinks it’s always before I need to dress. She does not want to see me dressed though. I think I need to get a good understanding of why I need to dress other than “I love that dress!!”. I feel I’m rambling on a bit so apologies for that. I don’t wish for it to go any further than our home but I don’t want to always be alone when dressed but not sure she will ever want to get involved.

I just wondered what is the main objective of this type of therapy. I am nervous and not sure what to expect.

Best regards,

Tina
(more…)

Posted by Gabrielle | 10 Comments »

Happy Halloween 2009 (a day early) from your friendly neighborhood crossdressing Vampiress. Hey rides, bobbing for apples, haunted houses, costume parties, and trick-or-treating will be among the activities enjoyed by folks on this candy-filled holiday.

Halloween is often regarded as the “crossdresser’s holiday”. On this single day of the year, it is generally socially acceptable to venture out into public en femme without being ridiculed, harassed, or facing harm (from haters). Because a man dressing up as a woman is regarded as a simple “costume” rather than a social deviation, the rules are changed, if only for a short time.

In years past, I remember some of my male friends dressing up as women on Halloween. Their costumes consisted of ridiculous looking dresses, mismatched jewelry, a bad wig, over sized breasts, and absurd makeup (applied almost clown-like). I observed similar displays at various costume parties. In addition, the men behaved very much like men with only occasional feminine behaviors displayed, and usually highly exaggerated for comical purposes.
(more…)

Posted by Gabrielle | 14 Comments »

This an old argument among male to female crossdressers. Why can women dress in clothes that are considered feminine or masculine, whereas men can only dress in clothes deemed masculine? There are no laws about this kind of thing, but the socially acceptable factor has a lot of weight on how we can live our lives in the public arena.

Extending well beyond just clothes, it encompasses total physical appearance, behavior and mannerisms. I’ve put together a very basic chart to illustrate the socially accepted gender expression norms:
(more…)

Posted by Gabrielle | 11 Comments »