I'll always remember the first time that I........

[Rachel Morley]

Definitely one of my highlights was going out clubbing (dancing) at a nightclub with my wife as two girlfriends having fun. All my life when I was younger I was so jealous of being at a club and seeing young attractive GGs who would be there in super cute dresses, high heels, full makeup, awesome hair, looking pretty and having a lot girly fun with their friends. When I first when out and did the same with my wife (about 10 years ago) we listened to music and drank wine as we got ready together, then we took a taxi to the club and danced and had fun all night! It felt so liberating and i will never forget it.

[Lacy PJs]

A couple of "firsts" stick out in my mind. The first one would be sleeping all night in some baby doll pajamas. While I had worn them many times previously, until we were "empty nesters," they didn't stay on all night long.

The second one would be wearing a leotard & tights for most of a day while I did some work in the upstairs of our house.

One of the firsts that I'm looking forward to will be ordering my first wig and strappy sandals!

Lacy PJs

[larissa-laurie]

My first anything, my sister dressed me up totally female when I was about 13. She dressed me in her school uniform with all the lingerie possible and a nice fall type wig. Her putting makeup on me was very well done. She told me I made a good looking girl and she wanted to take me to school with her. This whole thing was exciting and when I changed clothes I kept on her panties, nylons, girdle, and slip and slept in them that night. Many thoughts and actions crossed my mind. It started a life long fling with dressing partially and totally feminine.

[Ina Girdle]

A couple of firsts after 50 years of stealth & very sporadic CD'ing. Getting, trying on and modeling my first lingerie purchase, (a Rago Long Leg Panty Girdle) after coming out to my wife, what a feeling of excitement & accomplishment.

And just recently, on a trip to see my Dr., while wearing one of the few pairs I have left of (Gender Appropriate Underwear) as I call my old BVD's, a feeling of "I just don't feel properly dressed without some form of shape-wear on. It has been 3 years of almost daily wear of girdles or moderate control panties".

Thanks also to this group, I don't post all that often, but I read posts everyday. Like many here, the feeling of not being alone in the world after YEARS of feeling that I was a solitary oddity in the world.

Cheers! Ina G.

[Matterhorn]

The first time I went to a shopping mall with the goal of buying some girly things for me, confident in who I was and ready to speak to any employee who might offer help

[Jenn A116]

First time I bought breast forms! Many, many years ago. Had been using rice-filled knee-highs for several years and finally made the decision to go for the forms. Went to a CD store (Vernon's, now defunct) in Waltham, MA and have been enjoying the boobs ever since. Well, not the original ones. Those are long gone. But since then its been real forms. Actually considering a new set now. Thinking of the self-adhesive ones.

[Meg East]

When I came out to my wife. Now the only thing in the closet are my dresses.

[lovetobedani]

The first time I dressed in my mothers clothes when I was about 12.

[brenda girl]

i was about 13 when i first put on my mother's clothes, now i have about 15 dresses of my own to do my thins

[BethanyCross]

The first time I got party nails at a salon. I used the "lost a bet" scenario and went to a nice beauty salon. I was so nervous I was shaking. I left the salon with long wine colored nails and the nail tech and receptionist thought it was hilarious. I even got the "Now you know what a woman has to do to be pretty!" line. Awesome experience.

[valerie anne]

Ordered a bra online, waited for the mailman to knock and demand a signature, rip open the package, and then to discover it didn't fit at all!

[kymberly]

for me it was the first time i went bra shopping and told sa the bra and panties were for me,I still remember going into the fitting room and trying the bra on and have her making it fit properly.

[Sometimes Steffi]

For me, it was the first time I saw a crossdresser IRL who was pretty and passable. Until then, my only vision of crossdressers were comedians like Bob Hope, Milton Berle of Flip Wilson or drag queens.

[jacques]

the most important first time for me is on its way slowly - not really worrying what others think of my choice of clothing
luv J

[Katie01]

This thread brought back many sweet memories!
Old: 15 or 16 (1980's) going into a lingerie store and the sales lady helping me select and try on panties and a bra.
New: a few months ago walking my dog late at night wearing a dress for the first time.

[Samantha Clark]

Lots of firsts. Too many to mention. But only one milestone: telling my wife. Now I don't have to hide or purge.

As for firsts, nothing tops [sic] the first wig. That transformed this guy with makeup and a dress into Samantha. Indelible memory of that first time when I said "well hello, you!"

[Vicky Peters]

After reading the threads and thinking that each thought was great, the one that still remains the first is looking in the mirror and seeing myself with a wig, makeup and a blouse.
The image that I never saw before is still vivid in my mind. Now working on my makeup skills.

[Sephone]

Seeing myself fully dressed for the first time in the mirror.

[BrittanyB]

Oh easy...buying my first wig in person. I almost vomited before going into the shop. Actually seeing different wigs on me and how they framed my face was such an important thing to becoming more passable. Halloweed wigs are NOT the same! LOL

[Flirty_Fantasies]

The thrill of slipping into stockings for the first time was immense.....and this thrill has grown ever more intense--then to sit wearing them while transforming with make-up, lipstick, and arranging ones hair with the feminine feel of my stockings around my legs always giving the sensation of being a woman.....Mmmmmm!

Janelle XOXOX

[evadan]

Telling my wife, after years of dabbling with lingerie in the bedroom, I wanted to dress completely as a woman - and she agreed. Then a month later, after 35 years of collecting lingerie, odd pieces of clothing and purging - going shopping with my wife for a complete outfit (thank you Dressbarn and Payless) and dressing for her that evening. She's so good to me!

Good Thread!

Thanks -

Eva D.

[TakaraYu]

I guess I'll always remember the day I drowned all of my nerves and bought some women clothing.

it's still a work in progress thing however

[baldy1]

Wearing a Mini-Skirt at the sea front with my wife present

Julie

[phili]

When I wore a black and white dress out for the day- it fit perfectly, and I felt happy to be me - so I didn't mind the very few stares or chuckles.

I really loved it when the friendly young women at the museum wanted to talk- I felt I had established a public niche for any man who wants to wear a dress.

[julielivingmylife]

My first time outside was just amazing - it was dark and I just walked down the main road near my house (with only the occasional car driving past). I wasn't very passable if I'd been seen close up but that 5 minutes was such a rush and I felt so free. I didn't want it to end but I heard voices of people coming towards me so I turned back.