Notifications
Clear all

Welcome to Crossdresser Heaven, a safe and welcoming place for everyone in the crossdresser community.

Join Crossdresser Heaven today to participate in the forums.

First Time story

10 Posts
9 Users
0 Reactions
266 Views
Posts: 63
Lady
Topic starter
(@iarmstrong)
Trusted Member     Bangor, County Down, United Kingdom
Joined: 5 years ago

Hey girls,

Just wanted to share the stories of the first two times I went out dressed.

The first time was my first time in Belfast (NI) at age 18 alone.  I grew up in a very rural part of the country and was moving to 'the big city' for my first full time job after school.  It was February and I would be moving in the summer, so told my parents that I needed to go on my own to familiarize myself with the area.  I had called a lingerie shop and booked a fitting in advance.  At that time, I had no femme clothes of my own, so went in my male clothes and borrowed one of my mum’s bras.  Even though I didn't know anybody, and nobody knew me I wasn't brave enough to wear it when walking around.  It wasn't until I went into the shop that I started to relax.  The girl who did the fitting was very friendly, but I didn't buy anything that day because I was living at home for the next few months and trying to hide something from my mother is like hiding food from a mouse.

However, roughly 18 months later, after moving house, I went out fully en femme for the first time.  I was still wearing my male trainers and plain black fleece (which was long enough to hide, you know) but I had on a padded bra, panties, black leggings, a white t-shirt and wig.  I went to the local shopping center, got my make-up done at the beauty counter of the pharmacy, bought make-up for the first time and then went shopping.  By far my favourite part of the day was while browsing round the lingerie section of M&S, a woman (who looked to be of pensioner age, approached me from behind, tapped me on the shoulder and said, "excuse me young lady, can you help me?"

I couldn't help but beam.  I explained that I didn't work there, she apologised and moved on.  It gave me a feeling that I passed.  Had it not been for her, I may not be where I am now.

Hugs,

Isabel

Reply
9 Replies
Posts: 482
Guest
(@Anonymous 57460)
Reputable Member
Joined: 5 years ago

Such a cute story Isabel! I’m still trying to pluck up the courage to go out fully dressed.

Sera x

Reply
Posts: 150
Lady
(@missey)
Estimable Member     Orlando, Florida, United States of America
Joined: 5 years ago

Hi Isabel

Isn't it a wonderful thing when you are spoken to as a female?.It's happened to me quite a bit and I always get giddy when it happens. It's saying that you pass as a girl. Isn't that what we strive for? It never gets old no matter how many times it happens  Have a great day and stay safe when you are out dressed en femme .PS.I absolutely love the name that you choose

Jannie

 

Reply
Posts: 249
Lady
(@sammatha)
Reputable Member     BELFAST, County Antrim, United Kingdom
Joined: 6 years ago

An amazing passage .

Your are very brave.

Hugs

 

Samantha

Reply
Posts: 435
Duchess
(@terrim)
Reputable Member     Long Island , New York, United States of America
Joined: 9 years ago

My first time out was in 1979 or 80. I remember how nervous I was. After that each time got easier and so exciting and relaxing at the same time. Now I really dont care if someone reads me. The feeling of being who I am is unexplainable.

 

Reply
Posts: 482
Guest
(@Anonymous 57460)
Reputable Member
Joined: 5 years ago

Interesting how time changes things.  I remember the first time I ordered some movies from a catalog over the phone.  I was 11 and my voice hadn't changed yet.  When the order taker called me "young lady", I got very angry at her, corrected her and then cancelled the order.

Fast forward to today.  I wish I could disguise my voice to the extent that I would be called a feminine pronoun when 'dressed' in public.  I'll have to work on that.

Reply
Posts: 91
Lady
(@helenalovelady)
Estimable Member     Texas, United States of America
Joined: 8 years ago

I love stories like this. Always takes me back to my first time out, and I think we all remember our first time out fondly. I sure do because it happened at a cemetery one early morning. I know how it sounds, but there was a reason I chose that over somewhere so public.  It was both my first time out dressed and the first time I was befriended by a groundskeeper. But that is another story for another time-LOL!

Reply
Posts: 91
Lady
(@helenalovelady)
Estimable Member     Texas, United States of America
Joined: 8 years ago

Thanks,  Tami-it was quite cute and charming actually. He really took me for a woman, and it might have helped that he was  a senior, so I didn't feel threatened (but I was very nervous-lol!). He engaged me in conversation and even complimented on my dress. I remember that it was early in the morning and well, being a cemetery, not very much going on, ha! Best place to go to where there isn't anyone and where I was able to be out in the fresh air and enjoy some outdoor Helena time.

Reply
Posts: 482
Guest
(@Anonymous 57460)
Reputable Member
Joined: 5 years ago

That is a great story Isobel.I hope my first time goes as well as yours.Hugs to you.You are amazing.I love your name too.

Reply
Posts: 13
(@rebeccamay)
Active Member     Santa Maria, California, United States of America
Joined: 5 years ago

I was twelve so in 1992 I guess.My Mom moved in A dresser of hers into my room who was moving things around and just stayed there.One night,I was watching A movie called "Death Becomes Her" and Goldie Hawn was wearing this very sensual red dress and suddenly A switch snapped in my brain.

I then opened the drower and saw my Mom's panties,bra and A dress in it.So I put them on.Goldie also was wearing these gorgeous red heels-wanted to wear them.I looked in A bag nearby and saw A similar pair though more roughed up.I of course tried them on and yes they didn't fit,but I hobbled around in them.

As A child I was just goofing around at the time,but in retrospect I did geninely enjoyed being in those clothes,especially the heels.I own none at the moment since I only have two ill fitting dresses and that's it.However,that sensation of wearing those heels makes me want to own A pair and wear them again.

So,yeah that was my first time. 🙂

Reply

©[current-year] Crossdresser Heaven | Privacy Terms of Use | Link to usContact Vanessa | Advertise with Crossdresser Heaven

 
[kleo_social_icons]
Subscribe To Our Newsletter

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

You have Successfully Subscribed!