I am fairly new to this forum, at least the posting part.  Anyway, I am older (won't say my age her) and have a girlfriend for about 5 years now.  We are great together and are always trying new things.  I brought up my crossdressing early in our relationship and she has totally accepted it.  She thought it a little strange at first, but now she even buys me female underwear, bras, slips, and outerwear.  She often lets me wear her skirts and tops.  I would love to go out but would need her help.  She has promised that she will do my makeup, shave my legs, etc.  sometime soon.
    On weekends, early in the morning (5 am), I have been getting the newspaper while wearing a skirt and top.  It is fairly dark, so I don't believe neighbors would see me.  This weekend, I would love to take a stroll around the block (app. .8 miles), which would include the main road for about .1 miles. 

Question:  Should I do it? 

M

If you are happy with it, please do it. Some fears would disappear after you try several times. Girld friends are indeed best mates and advisors for crossdressers. It is always safer to going out with somebody rather than alone. I had a bad experience while going out alone.

And, do not try hard to pass. Currently I am wearing very deep red lipstick at my workplace. Some of my colleagues and visitors comments on it. All know that I am a dad. My wearing lipstick is not related with passing at all.

Good luck,

Barbie~~

Quote from: Megan2 on July 31, 2008, 04:51:28 AM
    I am fairly new to this forum, at least the posting part.  Anyway, I am older (won't say my age her) and have a girlfriend for about 5 years now.  We are great together and are always trying new things.  I brought up my crossdressing early in our relationship and she has totally accepted it.  She thought it a little strange at first, but now she even buys me female underwear, bras, slips, and outerwear.  She often lets me wear her skirts and tops.  I would love to go out but would need her help.  She has promised that she will do my makeup, shave my legs, etc.  sometime soon.
    On weekends, early in the morning (5 am), I have been getting the newspaper while wearing a skirt and top.  It is fairly dark, so I don't believe neighbors would see me.  This weekend, I would love to take a stroll around the block (app. .8 miles), which would include the main road for about .1 miles. 

Question:  Should I do it? 

M

I tried the stealth thing. I had a little bra that I put on under a t-shirt prior to going out and checking the mail. Quick in and out deal, right? Nope. Had a buddy come driving down the street at that exact moment, and he stopped to chat. Spent the entire time with my arms crossed holding the mail and hiding the bra, still not for sure if he saw it or not. I know I was acting weirdly since I did not expect in the least to get busted  So much for a little stealth fun.

All i'm saying is that is that getting busted can happen, and you need to be OK with it if it happens. I feel bad because I think I am discouraging you  Hopefully your luck will be better than mine 

    I guess part of me wants to be seen (or caught)  .  This morning, I DID go to the end of the street which is only .1 miles.  It goes to a main road, but no cars went by.  Tomorrow (Sat.), I will walk around the entire block (about 1 mile).  I will be on the main road for .2 mile.  Our block is very populated, with houses the entire way.  It is also very dark.  The only way anyone would see me is if they were driving in a car.  I plan to do this at the same time I did it today (4:30 am), which is too early for most people to be up, much less driving.
    Today when I went for my little (.1 mile) walk, I wore a knee length skirt andf white halter top  .  It felt so good being out and about they way I should be.

M

I love this subject. This brings back funny memories. When I was living back at my Dads house (I used to be in a bungalow), I was very agravated that I could'nt wear my dresses beyond my front door. I was basiccly trapped, and had no outlet at all. The only outlet I got was sneaking over to mums, while she was at work, and wearing my gowns and dresses around her house.

But, there was a few times when Dad and his wife went to bed, and I used to have a long flowing chiffon ballgown. It was very shimmering, and when I used to walk outside on a breezy night, the breeze used to feel beautiful against my gowns, and the feel against me was wonderful.

There were a few nights, I'd walk just up to the front gate, but not beyond it.
I never called it risky though, cause I was in a quiet street.

Now though, I'm living alone, and in a rather compact street. It would'nt work for me now. I'd get past the front door and I'd be seen, cause theres a high rise right next door.

But I wear my gowns everynight never-the-less....

I went out for the first time at my support group(changed there) and I was told that I passed quite well for my first time. All I that I needed to was to shave very close, style my long black hair to the point that it hide my reseeding hairline (darn it for being gb)  and a little confidence. Next time I'm going there dress in a different outfit but I need to find a why to hide it. Ya, haven't come out to my parents yet.

Well remember confidence is everything. You go and have fun with your girlfriend and try to find a support group. They are the safest place to be if it is your first time and everything.
[whispers}Man I wish I had a girlfriend who would except me.]

Amrisa

Quote from: Amrisa Jones on August 03, 2008, 12:39:34 AM
I went out for the first time at my support group(changed there) and I was told that I passed quite well for my first time.

Hi, Amrisa,

It's good news. I hope you will find good female mates who can advise on your fashion. Matured women are very experienced in fashion, and I always learn from them.

Barbie~~

If you feel comfortable about it, go for it.

Gennee

Ive never been out in public cept for a few times. Im planning on going for a run on a secluded trail in panties, a bra, spandex shorts, a thin strapped tank top and my ladies trail runners soon though. If you like to run I suggest it, because another runner running past probably wont see you for long enough to notice that you arent a real lady, or atleast thats always been the case for me.

Hi Megan,

Your post brought back special memories of my 'first outings'.
All of my CD life has been kept absolutely private.
I didn't flirt with being seen in my neighborhood, I simply took
my CD'ing elsewhere.
Yeah I would dress at home, alone. My yard is large and private.
But I always stayed out of sight.

I started out by studying and learning everything that I could about
GG's clothes, undies, make-up. I also tapped into the CD community
and gained valuable information as to the in and out's of being a CD.

After many months of trial and error with clothing, formwear, make-up,
hair, poise, etc...I arrived at a look that I was comfortable with and was
convincing.

My wife and kids were out of town for a weekend,  but I had to work. 
I had bought a two-piece dress for the occasion, and new shoes.
I got home, showered, and within an hour, Linsey was ready to go out.

I had spent nearly $200 on my long brunnette wig, which was secured to
a wig cap. I also invested in a set of full C-cup breast forms.
I also visited with a GG consultant for CD's.
This was the first time that I had dressed completely, and the result
was amazing.

I pulled my skirt up, buttoned up my blouse, and slipped on the black
pumps. The change was instant. I felt a wave of something wash over me.
All of my senses came alive as I walked to the mirrored wall, looked and
saw a good looking Latina lady looking back at me!

The rush was incredible as I turned and looked myself over, everything had
come together perfectly!
And I now had a 'figure' to enjoy!

The sun had set, I took only my ID, some money, my lipstick and essential
cosmetics, picked up my keys, locked the door, got in my car and drove
away, right through my own neighborhood.
A few minutes later, I was on the freeway, heading for my GG friends house.
I was 100% into the female mode, I couldnt do anything but be a girl.
The guys would pull up next to me for a few miles, take a good look
and move on.

I arrived at my friends house, without even thinking twice, I got out of
the car and walked up to her front door. She opened the door, she didn't
know who I was until I spoke in my male voice. She was so amazed that
she called another GG friend and told her all about me

30 minutes later we were sitting in a resturaunt in downtown Los Angeles.
Three nice looking ladies having a good time together.
They sat me in between them, made me feel a lot safer, several guys
said hello as they passed by our table.

Later on we walked down Sunset Blvd, oblivious to everyone else.

My first time out was a drive around the block...literaly. I kept my car in the garage and used the door from the house into the garage. Then I just drove around the block and back home again. Of course, it was at night...but that was a start. Next time my girlfriend had found a local bar with "trans nite" we went, that was awesome. IT Was so nice to be around others without feeling out of place. Funny thing, I ran into a guy that lives in town and works at the grocery store. To this day, 6 years later,  we always acknowledge each other and have our secret, if you will.

After a few more trips to that bar... I quit going out. Dont know why.

Im at the point now where I need to go out again...but I live in a small town and all I can think about is the a**holes I have dealt with here and what the reaction will be...I will run into them.

I think going out of your own town is a good idea...get your feet wet.
Of course I say Ill wait till I pull this off perfect, then no one will ever know...right? But, waiting for that day is like waiting for the day that never comes.

Even though I cant take my own advice well...Id recommend that you go...then tell me how it went. Maybe we will both be surprised.

Oh what fond memories. I understand the increadible urge ( drive ) to finally step out that door looking like you feel. That urge can possibly lead you to trying things you might not normally concider? So think your plan through before acting. Can you deal with running into a nieghbor? Is it possible that a friend or family member could drop by to visit while you are out? Could they drive by and see you? You can always go to track or walking trail or a drive. Soon you will get the courage to stop at a store and run in for a soda or some thing? I did stuff like that for years and then I started driving to a mall an hour away. I bought pantyhose, girdles and such but always went home feeling down because I got to scared to wear them inside. After about a year I took a dress and a pair of high heels in a bag and went in and bought a pair of pantyhose and then I went and tried on men's suits. While in the dressing room I put on the pantyhose and then took out the dress and heels and put them on. I was wearing an old shirt, sneakers and pants on purpose because I then took a pair of scissors out of the bag and cut up my guy clothes. My heart was beating a thousand beats a second! My mouth was bone dry and I was lightheaded. To make sure I didn't chicken out I went in earlier and hid my car keys at the far end of the mall so that I would have to walk the entire mall to get my keys and then walk the mall again to get to my car. I will never forget how beautiful, happy and whole I felt as I walked from the dressing room. The air on my nylon covered legs felt like magic. I walked that mall loving every single step, even though I had hairy legs under my pantyhose and no make-up or anything.
You will find what works for you, i'm sure of it. Just remember, you have every right to be you and every right to be happy. Do what feels comfortable and safe for you. You are really fortunate to have a girlfriend to help you. Best wishes and good luck!

Go ahead and do it. You'll get over the nerves. Once you go out the first it gets better.

Gennee