The First Time I Plucked Up Courage To Go Out.

after many years of dressing up and perfecting my look the clothes and the makeup and the right type of wig to suit the shape of my face i finally plucked up the courage to go out dressed up
the first time was quite late at night as i didnt want to many people around so i went out at 12.30 at night i wore a black blouse and a black pencil skirt bra and nickers and stockings and suspenders and a pair of low heel shoes so i didnt trip and break my ankle at first i was very scared and kept looking around every time i heard a noise then as i got further away from my house i started to feel more confident.
then after walking for a while i saw a man coming towards me so i started to get a bit worried and i almost turned and ran but if i did the game would be up and it would be obviouse i wasnt a i kept on walking and tried to act normal as we past each other i was really nervouse but the man just said goodnight and kept on walking.oh the relief after he past so i walked a little further and then headed home when i got home i felt really elated and wanted to go straight back out again but it was getting on for 3am so just got undressed and went to bed.
so after that i started to go out a bit more often and always late at night untill i felt really confident then i went for a walk around town at 8pm but always when it was dark.
margaritacon margaritacon
51-55, M
7 Responses Nov 19, 2012

Be careful at night, women would never walk at night alone. I only go out in the daytime now, and will go out at night unless there's a lot of people around. Could go very bad if you met the wrong people, and I'm in petty good shape as I work out to keep up strengh.

Good advice dear ... ;-)

It was not my first time out but around the third or fourth. First couple of times outside the house was up to the main road and back again. Anyway, the next time out I plucked up courage to go a little further as it was only about 9.30pm.So I decided to walk around a bit and walk around my housing estate. Well that went ok so I decided to go and post a letter. Back home to get the envelope, (a stamped reply envelope to some insurance company or other), into which I put in a piece of paper to make it look as though the envelope meant business. So out I went again for a half mile walk to the post box. That done and I did not want to go home so I decided to walk about a half mile up a gully to my old school. That went ok so I still did not want to go home, so I then decided that I would walk around the other housing estate that bordered the gully by my old school. That completed it was back home for a well earned cup of coffee. By this time it was just after11pm and I was undecided about trying another walk, but decided not to push it.
So now when I go out I have found myself a man friend who has a car and look forward to riding out instead of walking.
If you do get the chance to get out of the house take it and you will not regret it. I didnt.

good on you hun well done xxx.

Im gay but not into cross dressinh but have a friend who is and i say great story. be out and proud!

Wonderful. Taking a stroll, dressed to the hilt!
Pretty courageous walking that late hun! I've ventured out in the dark, but never that late or early, how ever you see it. Be careful! You are actually out as a woman, and open yourself to unwelcomed advances. Love you!

That sounds exactly how I started going out. Once I got brave enough to go out dressed during the day it opened up a whole new world. I now go out anywhere dressed and don't give it a thought. Just ignore any stares. I enjoy being a woman in the daylight.

well thank you for that reply hun its very encouraging xxx.

tank you tghubby for that advice yes it would look a bit strange but as i said there would be less people about at night but i walked so far time just slipped away before i knew it it was going on for 3am suppose i will have to take shorter walks.but after i did that a few times i did go out a bit earlier but thanks tghubby for caring.

Yes it is fun to be out and about, but be careful. Women wouldn't do what you did, going out late at night and into the early morn unless they had to. Even then women would give it a second and third thought ... then only if there was no more safe alternative and would walk with a purpose. Just a word of advice, Margarita, and when you are out dressed you too are a woman.