Getting some help from mom

[StephanieR]

I'm going to visit my mother in November, and I told her that I might participate in a Womanless Beauty Pageant fundraiser while there (with some old college friends). But, I said that it is expensive to do, and she offered to pay for it if I wanted to do it. So, I said "yes." Since then, we've texted quite a bit about it. She encouraged me to ask my sister about borrowing an evening gown (which I did), but they were all too small. So, at this point, it looks like she and I are going shopping when I get there. She's going to take me out looking for a dress, wig, shoes, etc. She wants to enlist the help of a girl friend of hers, too. So, I'm imagining going to a Bridal boutique, where I go into a dressing room with a bunch of gowns, and come out and model them for my mom and her friend, and maybe my sister, too. I told her that the shops recommend that I come in wig & make up with nude strapless bra & underwear. (This is often recommended.) I had contacted one store who sent a reply thinking I was a girl/daughter shopping for homecoming. My mom got a kick out of that, and I signed the email with a girls' name just as a joke. Then she replied using the girls name (not Stephanie). In my next text, I talked about shopping for a few things before dress shopping, and said "you're the best mom a girl could have," and signed my girls' name. She replied "I love my girls!"

I'm starting to wonder if she's going to enjoy this as much as I am!

[lexivanderpump]

The 64 thousand dollar question. Does your mom or sis know you crossdress? Just wondering. Other than that, it sounds like fun. My dad would have been supportive, but not my mom. Your sis and mom sound great.

Love,
Lexi V.

[kimdl93]

I had the same question. I know that if I asked my mother or sisters for help in this manner, they would have no doubt why I was interested in it.

[StephanieR]

No, I don't think she knows. But my sister dressed me up when we were kids, and I think my mom didn't mind. She always kept my hair long and I sometimes wonder if she liked seeing me dressed up because I had such long eye lashes. (I was often mistaken for a girl.) My sister was never a girly-girl, so I'm hoping that I can be that daughter-I-never-had.

[Beverley Sims]

Stephanie, a great response from your mom.
With the bridal boutique I would suggest you let them know your gender as they will still be accomodating and you won't be giving them any shocks.
I used to love the boutiques I visited years ago as they knew I was looking for dresses for mock weddings.
I have literally spent days and tried on hundreds of gresses looking for suitable stock.
I always bought clearance stock and items that could not be sold.

[bridget thronton]

Great mom and a fun time ahead

[Stephanie47]

Since your sister dressed you up in your youth and your mom did not object, I suspect your mother would not be surprised at all if you told her. If she strongly objected to cross dressing on religious or moral grounds, I doubt she would have permitted the dress up sessions. My mother was so anti anyone who was not pure vanilla it would make me sick. Enjoy.

PS: My local Goodwill's have dragged out all the prom dresses for Halloween. But, I think having the chance to model a lot of dresses would be something you cannot pass up. Why don't you find a pretty dress, heels, hosiery, etc to wear to the bridal shop? I agree you should tell the staff ahead of time you're a guy.

[Marcelle]

Hi Stephanie,

It sounds like a fun time. My one word of advice if you don't want your mom and sister to know about your cross dressing . . . don't enjoy this too much as it could raise suspicions. Have fun by all means but fun in the sense that you are having fun because they are and not that you really enjoy trying on gowns. Don't forget to let us know how it went.

Hugs

Isha

[StephanieR]

Should I really wear hose to the shop? I was thinking going bare legged. (I'm shaving my legs.) I don't think most younger women wear hose with a gown unless all black maybe. But if I go bare legged then I can paint my toe nails. : )

[kimdl93]

Turn this around just a bit...do you want your mom and sister to know?

[BLUE ORCHID]

Hi Stephanie, Don't forget your camera.

[Rachel Morley]

So, I'm imagining going to a Bridal boutique, where I go into a dressing room with a bunch of gowns, and come out and model them for my mom and her friend, and maybe my sister, too.

I have done this but with my wife and friend not mom and friend and I can tell you that going into a bridal boutique is like doing into Aladdin's Cave .. there is a multitude of "puffy feminine-ness" in there! My experience was something I will never forget as long as I live, and that I believe was because of the huge amount of encouragement and support I got from all the GGs around me (wife, her friend, store owner and her assistants etc). Hopefully you are going to have a similar awesome experience too!

[StephanieR]

They don't know, and I kinda would like my mom to know. We just texted again today and I asked if she wanted to help with makeup. She said makeup isn't her forte, so I may go to a salon for a makeover for the event. But she did say she would "absolutely" help me with some basic makeup when we go out dress shopping! My mom loves taking people out shopping, but my sister and my nieces aren't really girly girls.
I suppose the ideal would be that she gets me to admit that I enjoy it and says, "That's ok, sweetie. It can be our secret." May be a pipe dream, but I don't know.

And you can bet I'll have TONS of pics!!!!

[Rachelakld]

Sounds nice,
In my situation I would ask her nicely after she did my makeup if I could wear pretty clothes so I could have a full girls day out.

[darla_g]

Loved reading this, sounds like so much fun.

I was just thinking of this in terms of my own mother, Never in a million years would this have been my mom!

[Dena]

Sounds like fun. Absolutely go to the salon for your makeup for the event, you'll be glad you did! You'll have time to relax and focus.

[StephanieR]

Sounds nice,
In my situation I would ask her nicely after she did my makeup if I could wear pretty clothes so I could have a full girls day out.

I'm kind of thinking things might go that way -- first thing will be to buy the wig and an outfit. Then maybe go home to get dressed/made up for dress shopping. What will we do for lunch? Eat out somewhere I hope. : ) Then that evening? Maybe I can convince her to go to a movie or something. Haven't figured out the schedule yet -- I'm letting her be in charge. We really just have one full day to shop, so I might have to get the wig & outfit the day before. Not sure.

[Badwolf]

Sounds like fun! Enjoy!

As for what it means, don't over think it. She thinks it's fun and is open minded enough, and confident that she raised you well enough to do something outside of the mainstream. That's it.

It might be a hint that she'd be OK with it if you came out, but by no means is it a clear signal. Her reaction may help, but you never know.