Masquerade - Where "BOYS have FUN being GIRLS!"

Masquerade - Where...
" Boys have FUN being GIRLS"

Q) I'd love to join your group. However, I worry about being seen by someone I know. How do I overcome this???

A) That has to be the biggest fear we all have through our lives. Being "found out". We all share that same fear in one way or another and as a group can help each other overcome that fear. We make our meetings and outings as comfortable as possible for our members. Perhaps the biggest comfort our members find when crossdressed is that they are so different in appearance from their male selves that it would be very difficult to recognize the person underneath the makeup and hair. Knowing this helps our members relax and enjoy their girl-time!

Q) You don't post your meeting location on your web site. Why ??

A) We don't post our meeting location to respect our member's privacy. This helps make Masquerade a comfortable place where our members can go to enjoy their girl time.

Q) How much of my personal information do you require for me to join Masquerade ??

A) Mary, our "Den Mother", takes care of our membership records. And to further protect the privacy of our members all that is required is...

1) Your "female" first name
2) Your "male" first name
3) Birth date
4) The address you wish to receive a printed issue of Lipstick & Lace or the e-mail address you wish to receive Lipstick & Lace in .PDF format.
5) Be recomended for membership, "Sponsored", by a Masquerade member or a "Big Sister".

To ensure a comfortable environment for our members and yourselves, we prefer to get to know prospective members prior to meetings or events. That way, we can answer your questions, and make it a lot more comfortable for you to when you do attend your first meeting or get together, since you will already know someone. Plus, it will make it a much more pleasant experience for you.

If you are interested you may write to us at Or contact Mary at Lady Godiva Boutique at 1-204-275-3871.

Q) Can I just "Show Up" at your meeting??

A) We prefer to get to know prospective members or have them refered to us before they attend a meeting. This protects our members privacy, and yours if you chose to join. We can answer any questions you have and it makes it a much more comfortable experience for you to attend our group since you will have already know someone there. As well our members will be expecting a new face, and be ready to welcome you!

If you already know one of our members you would most certainly be welcome to attend our meetings as their guest.

Q) Does my picture or name have to be posted on your web site if I join Masquerade??

A) No. The pictures you see posted on our web site are posted with the member's permission and only the girl's femme names are posted with them. There are members who do not want their femme names or pictures posted and we respect that 100%.

Q) I'm worried my wife will find out if I join Masquerade. Do I have to tell everyone who I really am??

A) Since we have all "been there before" we do understand your concern and the kinds of stresses you go through worrying about spouses finding out. Mary, our "Den Mother", maintains our membership records and that is where they stay. We won't be calling your house or sending you mail by post unless it is what you request. We want Masquerade to be a place where you can let the girl inside you come out and play!

Q) Just who are "Crossdressers" in Winnipeg, and everywhere?

A) We are loving parents, spouses, fathers, grandfathers, brothers and sons. Everyday normal people. The neighbor next door, the golf partner on Saturday afternoon, the fishing partner on the weekends. We are teachers, managers, business owners, mechanics, truck drivers, police officers, security personnel, doctors, nurses, lawyers, city workers, politicians, military personnel, and the list goes on. We simply share the need to express our feminine sides by crossdressing, to understand ourselves and feel complete.

Q) Are Crossdressers always men?

A) No, not always. Just look around and you will see that women also crossdress and society has become more accustomed to it over the past few decades. It wasn't that long ago that you wouldn't see a woman out in public unless she was wearing a dress. Yet now you often see a woman going to the office wearing pin stripped suit and flats or wearing a t-shirt, jeans, a tool belt and work boots on a job site. So in a way, the woman's desire to express herself in a historically masculine masculine way, is not much different than the man's desire to express himself in a feminine way. And yes, society is more accepting than expected as we have found out first hand!

Q) Do I have to attend the meetings crossdressed?

A) If you are not comfortable attending your first few meetings crossdressed we do understand and you would be most welcome to come in drab. We are about helping people become comfortable with themselves and do encourage you to come dressed after your first few meetings. That's the fun part! If you are new to crossdressing you will not be judged on skill and presentation. We all have to start someplace and Masquerade offers a safe place for you to meet others who share the same feelings as you do. Indeed, all our members, as with "real girls", have varying styles and levels of skill. Attending our meetings is a great way to learn more about ourselves by learning from and talking openly with others. If you wish to arrive in drab, and change at the meeting, we have change facilities available for your convenience.

Q) I don't feel very passable. Will I be accepted in your group??

A) Absolutely. What is important is that you are happy about yourself. Joining Masquerade is a wonderful way to learn from others. Like having a "Big Sister", which will greatly help your confidence level. Besides, many of our members present themselves much better as a woman than a lot of them think they do. You GO Girls!

Q) Is it against the law in Winnipeg to Crossdress?

A) No. Not in Winnipeg nor in many jusisdictions in North America and globaly. And that comes from the Winnipeg Police Service! Sgt. Ron Johannson of the Winnipeg Police Service "Diversity Unit" who spoke with us at one of our meetings about how our crossdressing relates to the law. We are not in any way breaking any laws and he said we are to be treated as anyone else, with respect.

Q) Will I have to go out in public if I join Masquerade?

A) No. You can participate only in the activities you are comfortable with. Many of the pictures on our web site show our girls out and about dancing the night away. However, most of those pictures are taken at our meetings and house parties which are great places to go out without really going out.

Many of our members are indeed comfortable going out in public because it really is a lot of fun and you would be most welcome to join in that fun too, but only when you choose do do so. Before joining Masquerade, many of our members were by themselves with no one to talk with, or trapped behind the confines of their computer screens. Being a member of the group gave them the opportunity to make friends with whom to do all the things they had dreamed about.

Q) I'm not very good at make-up. Can someone help me??

A) Absolutely! That is the best part of being a member of Masquerade. Learning from others and having friends you can talk to about girl stuff! Plus, we often have make-up presentations at our monthly meetings which are great learning experiences.

Q) I have a beard/moustache that I can not shave fearing my wife will wonder why I want to, but I love to dress up??

A) We have members in your situation who find being accepted by the group very rewarding under those cercumstances.

So here is a little hint.. If it is something you truly wish to do what many girls do is wait until "Movember" when men shave starting in November in support of cancer research. Then ask how you look without it and go from there. Many people change their look over time. Just look at women's hair styles, from long, to short, to blond and brunette!

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All photos are used with permission.

© Masquerade 2009