What's your favorite memory of dressing up?

[shayleetv]

I have 3 memories about dressing. But this one I think is my favorite. It was long time ago when I was a soph in high school back in 1957. My sister was in college and was a dance major. She had solo dance that she had to perform for her grade in the class she was taking. She would be graded on her interpretation of of the music and words. In the song the girl was auburn and long haired, my sister was short blond. Solution rent a wig from the school's theatrical department. She had the wig home and out of the box and she noticed the way I was looking longing at it. She asked if I wanted to try it on. Eagerly I said YES! She said "Come home right after school tomorrow and I will be ready to let you wear the wig." She used to dress me up as her sister years ago and she knew I still dressed on my own but I guess I was too stupid to put 2 & 2 together to think what she had in mind. When I got home there was a note for me to take a shower and put on the things she had laid out for me on her bed, a bra panties a half slip and a full slip garter belt and nylons. I was so excited I could hardly contain myself. She finally showed up with her friend who taught makeup for the schools theater department. She made my face up and my sister got her hot floral dress for me to wear. It was the in kind of dress that the popular girls wore especially the hot ones, scoop neck and thin arm straps. After they put the wig on and showed me what I looked like I fell in love with the girl in the mirror, she was down right gorgeous. All dressed up and no where to go. When Beth(my sister's friend) saw me completely dressed she said we have to her off, and they did. We went to dinner at a pizza place that I had never been to so we wouldn't run into people that I knew. But we did run into a lot of my sisters friend from school and I was introduced as a cousin from back east. What a blast!!!!!

[Kathi Lake]

My favorite moment in dressing is usually the last one I had. I'm not sure if that's because I'm a guy and naturally forgetful, or I just take life as it comes to me.

Kathi

[Lucy Long Legs]

My favourite dressing up moment was about a year ago. My wife was out for the evening so I put on some of my favourite clothes which involve an open corset, black stockings, black heels and a little black dress. I also had the wig you see in the photo and full make-up. She knows I dress and sometimes is ok about it, sometimes not. Anyway, she came back early and so I called downstairs to say I was dressed and she said that's fine. What I didn't realise was that she had brought a guy from work back for a drink. I spent the rest of the evening watching him trying to look up my dress. It's not much but I enjoyed it! That's when I realised I could pass.
Lucy

[Babette]

My favorite was the first time that I fully dressed. That's right, hair, makeup, forms, awesome outfit, and shoes. It was like, OMG who is that person I saw in the mirror. Since then, dressing has been wonderful but never as memorable.

Babette

[Paula G]

My favorite memory is when I was on vacation by myself in a cabin on a lake. It was the end of the season, so no one was around, and I was able to dress all the time. It is also the only time I've been outside while dressed, and have plenty of photos to help me remember.

[Jonianne]

My wife taking me on my first outing in 2000 and last year on vacation with my wife at Niagara Falls. Later we took the Amtrak from Plattsburg to Albany which was the first time I went dressed on public transportation. I never imagined in my life that I would be able to do something like that! In my album are some pics.

[IwishIwasTracy]

I would have to say trying on wedding dresses at a David's Bridal in Seattle. I loved wearing those gowns.


Tracy

[Sally2005]

A couple decades ago when my wife loaned me her spandex little black dress and we went out to a bar on halloween, this old drunk guy practically fell off his chair at the bar to come to say hello to us at the front door. The door staff kicked him out. But I still remember feeling like a side of beef for a minute. In the bar which we thought was remote enough, we ran in to a good friend who recognized my wife (not me) until he did some simple math.

[Sarah Doepner]

I was stressed because I didn't know how my wife was going to react to my dressing after she found out. One day the topic came up and she said to go ahead and dress if I wanted to, but for the time being I needed to stay in the bedroom. She even gave me a project to work on to help her with her work. I dressed in something kind of casual, but conservative and tried to do a very good job on my makeup, just in case. After about an hour she knocked on the door and came in to see how the project was coming along and to finally meet Sarah. We got along well and have ever since.

[Christina Horton]

I love all the times that I have been out but I have two witch I think of as one big HOLY SH%T 2 weeks of fun :) Shocks:eek: and laughs :heehee:.
http://www.crossdressers.com/forums/showthread.php?t=113089
and this one.
http://www.crossdressers.com/forums/showthread.php?t=112976
The two happened starting last month form the 26 of July two the 4th of Aug . It would be to hard to right all about them again. But what a whorl wind two weeks. I still am in a high from it. I have lots of good memories of "time in dress" and will have more I am home for the week and when my car is out of the shop I will have more fun fun till daddy takes my ahhhhh "Corvette" away. Now If I could fine someone to go to the night clubs with around here I would have even more fun.:D:heehee::daydreaming:

[Shari]

My favorite time was the only time I had ever been out of the house fully dressed.
It was some years ago on halloween and I was dressed as a woman (duh).
It all felt so wonderful, especially when we arrived at the party. After the shock had worn off from those who knew me, and after a few drinks, two of the girls tried to lift up my skirt to see what I was wearing underneath. The great part is that I didn't know those two girls until that night. I loved the wrestling match.
I never wanted the night to end. There was just something so special, sitting there with my legs crossed, wearing my heels and hosiery and everything in front of everyone, half of them strangers. It felt so free to be like that.
I'd love to do it again.

[Chrissie P]

A man held the door for me as I walked in my hotel.:battingeyelashes:

[Lady Joan]

My favorit time that my SO dressed for me, was the day she came home with clothing she was not use to buying. I asked her to vamp it up, buy a few items that were more sensual and sexy.

She and a CD girlfriend went out and shopped together, she came back to my place and did a show and tell. How awesome it was to see her and how great she looked.

Since this, we have been shopping together and I have been directing her to more causual wear, so that we can just do every day things in, as evening wear is great, but not for walking the dog around the block.

Her wardrobe is expanding. Laughs... but I think she loves it, as I can see the beaming smile upon her lips.

[suspender]

i tend to agree with the last is the most memorable, even though i remember the first as a kid. most of the time i try to outdo the last thing i did 'coz its so addictive!

[Nicole Brown]

I have had many moments that stand out in my mind, but the one that is most memorable has to be the time my wife was away for a week and I was able to be Nicole 24/7 for a week. During that time, I was able to do many new things that I had never done before.

That week allowed me to drive over 500 miles round trip, go out of state and drive across 4 states, stay overnight in a hotel, eat all of my meals in restaurants for 2 days and of course use a ladies room.

I will be experiencing another week of Nicole 24/7 in early October and I am thinking of new 'firsts' for that week...

Nicole

[carrie-ann]

I have a lot of memories but yesterday for me was so great I wore a long black skirt with a purpurl blouse to work. It felt so nice and sexy to me and naturel. Every one thought I looked nice. Had good comments. And a lot of support for me being me. Like they said as long as I'm happy I am very happy. And not to forget the hosery and panteis and and make-up.

[Michelle123]

Well, I have been dressing for many yrs. And although I am able to dress with my girlfreind, I must say that my favorite memory to date was last yr. when i first was able to dress freely with my mother.
My first experience dressing in front of her was so wonderful. She was completly accepting. Just the simple things, like getting up in the morning, being able to make the coffee, in just my lovely foundation wear, with stockings, pumps, full slip, was so exciting for me.
On that first evening, I asked her if I could handwash some things in the guest bathroom. She said of course. So there i was, in my things, washing out some stockings, panties, one of my corselettes in the sink. It just felt so natural. I left the door open, and she could see me from the den. I hung my things on the shower curtain rod to dry, and everything looked so nice hanging there.
I love ff seamed stockings, and she remarked on how "old fashioned" they were. I simply stated that i really loved the look. Ane she did comment on how nice they looked on me. She also found it rather amusing that I could go all day and night in a girdle or corselette. I just told her that i loved the look and feel so much, and that these items, (along with sheer gartered stockings) were essential for me in order to feel "content" and complete when i dress. She understood how I felt after I explained it.
I think that one main reason I enjoyed being with her like this, is because the sexuall aspect of my dressing was secondary at that time. It was more a feeling of freedom to be myself with her, and how comfortable she made me feel. Of course there were times during the day when I would go into my room and close the door for breif periods, and she would respect my need to be alone. (pretty sure she knew why...lol)...
So, that is my favorite memory to this date, but My next visit with her is approaching soon, and I think it will also be most memorable, as I will take it just a bit further this time, in that I will be compltetly feminized, with wig, makeup, nails, etc. I can't wait...............

[stacy-marie hanna]

either the firsttime i was dressed at age 7,i was forced back then by my parents who dressed me in my sisters school uniform with a blonde pigtales wig for a fancy dress day
or the first time i got dressed up in my gothic lolitta style maid dress which was last week.

stacy marie

[Frédérique]

What's your favorite memory of dressing up?


For me it was simply driving to Maine all dressed up a few years ago. I was dropping off some of my artworks at a gallery there, and it was a beautiful late spring day, so I dressed extensively for the occasion. Usually my senses would be on high alert when I was out in public like this, but this trip was so relaxing I had no feeling of vulnerability at all. It seemed very natural to be dressed as a woman, and I would stop periodically to walk around, have some coffee, or touch up my lipstick. I drove back to my home in Massachusetts later that day, without incident, through the Boston traffic. I never wanted to leave my cocoon of femininity, but, alas, I had to…:sad:

[Jaclyn NM]

The best, was the first time I got all dressed, and madeup, and went out in public. What a thrill it was. I'll never foget how wonderful it was.

[allisonrn06]

Mine was when I first got dressed completely - in lace bra,panties, slip and hose(all black) and a green velvet dress, high heels,makeup, and for the first time a real wig,not a Halloween costume wig. Although I had been wearing all the clothes and dabbling in makeup since my early 20's, this was the first time I had worn a real wig, and when I finished gettting dressed, looked in the mirror, I couldn't believe it!! With the exception of my hands I think I would've passed, although I wouldn't nowadays. Wish I could get back to those days!!

[RachelDenise]

My favorite moment was my first bra fitting. It happened in a small bra salon, and I was wearing only panties at the time. Magical to say the least.

[StaceyJane]

My favorite memorie is last summer when I got to try on somes wigs at a profession wig salon. The people there are very TG friendly and they let me try on so many different wigs with so many diffrent looks. The best part was when I found some wigs that looked good and I dressed as Stacey and walked around the store wearing them. I was able to look at myself through the mirrors and it was like I was seeing myself for the very first time.

[carhill2mn]

I would not be able to pick a "favorite". I can think of a great many that would qualify.

[heatherdress]

I had never been "out" before and had only been CDing for a short period of time. I went for a transformation (make up/wig) for the first time in Las Vegas and thought I had my female clothes to change into in my car. I then found I had forgoten my dress/heels bag in my room. I had to walk from the parking lot, into the casino, past security, into a crowded elevator and back to my room in guy clothes. I was was a stunning female from the neck up but cool guy from my shoulders down. The only thing I could do was to act like this was how I dressed all the time. It worked! Not one stare. I actually enjoyed the unplanned experience.

[ToxicAvenger095]

When I was....I am not sure, maybe 12 or 13? I used to love watching the Power Rangers, and I used to dress up like Kimberly from the Power Rangers (remember? lol) and watch the show, and do the fight moves and stuff. Hahaha. Really funny memories.

[Christina Horton]

My favorite time was the only time I had ever been out of the house fully dressed.
It was some years ago on halloween and I was dressed as a woman (duh).
It all felt so wonderful, especially when we arrived at the party. After the shock had worn off from those who knew me, and after a few drinks, two of the girls tried to lift up my skirt to see what I was wearing underneath. The great part is that I didn't know those two girls until that night. I loved the wrestling match.
I never wanted the night to end. There was just something so special, sitting there with my legs crossed, wearing my heels and hosiery and everything in front of everyone, half of them strangers. It felt so free to be like that.
I'd love to do it again.


So why don't you just go out dressed. The way I did it was to go to a MAC store and have a makeover done in a very big mall so I could not leave with out being seen. I was a rush and it has been better each time out. So like the shoe said to the runner (pun) "Just Do It."



I have a lot of memories but yesterday for me was so great I wore a long black skirt with a purpurl blouse to work. It felt so nice and sexy to me and naturel. Every one thought I looked nice. Had good comments. And a lot of support for me being me. Like they said as long as I'm happy I am very happy. And not to forget the hosery and panteis and and make-up.


So you go to work dressed and now do you go every time or just that once. I hope you can do that any time you want to you go girl.

[MaryAnn40c]

The first time I got dressed and had to walk though a shopping mall to buy a pair of shoes. This was the first time I had been out in public.

[Christina Horton]

The first time I got dressed and had to walk though a shopping mall to buy a pair of shoes. This was the first time I had been out in public.

The West ED mall I bet! What color were the shoes , Height of heal , and style ?

[Lara Smith]

In my late 20's the first time I actually got beyond just panties and bras. I ordered a pair of heels, pantyhose, a kind of nylon a-line skirt, and a long sleeved cotton spandex top. When they came I couldn't wait to try them all on. Everything fit perfectly and I was completley carried away by how they felt on my body and how I girly I looked in the mirror from the neck down. I was fit, thin and trim then, a 9/10 and suddenly realized something far beyond the feelings just the panties gave me (although they are still my very fave). I walked in those heels like I had been all my life, and feeling my hips sway in that skirt was a huge, huge thrill. I didn't ever want to take that outfit off and nearly forty years later I still have it all and it still fits (although not like it did then)

[Miss Anthropic]

I guess my favorite memory is from 2 years ago or so, it was the first week or two I had told her about dressing. I was fully emfemme and we both were playing dressup with her prom dresses late into the night. At one point we both got hungry and decided we had to go to McDonalds for food.

The place would've been closed before we could change, so rather than miss out we hopped in the car, middle of summer, both in prom dresses and headed to McDonalds. Craziest thing I've ever done; we got a few strange looks in the drive-thru at 2am in prom dresses, but it was totally worth it.

It's my favorite memory because (1) it's such a silly and great story (2) I was wearing a pretty prom dress, a dream I'd had since a kid come true (3) it was something incredible to share with my girlfriend and really made me realize how much she truly loves me.

[Dawn Marie]

My favorite memory was about 15 years ago,when my roommate and I went to have our hair and makeup done and go have some professional pictures done. It was so much fun and the pics were great. Back then I had my own hair, down to my waist, and much thinner too. Wish I still had the pics to show but my present wife burned them.
One of the pics was so good that I had framed it and put it on the wall in the hallway. That week my ex-wife came by and asked who the girl was in the picture, when I told her she couldn't believe it. After that she was ok with my dressing.

[SatinSarah]

the first time a fully dressed and looked good enough to step outside. I only walked around the block in the dark but it was a rush I want to repeat!

[Jennifer Marie P.]

My favorite memory is when Im going to model wedding dresses.

[Sara82]

for me it would have to be, the day I got my first wig. I remember an incredible feminine feeling overcome me, it was very powerful experience for me.

[sue ellan]

I would have to say trying on wedding dresses at a David's Bridal in Seattle. I loved wearing those gowns.


Tracy

same here. i have serveral others but trying on wedding dress it the best one.

sue ellan

life is like a roll of tp. the closer to the end the faster it goes

[LindaMarie]

I'd have to choose two memories.

The first was when I went out fully dressed (business dress, hose and black pumps) and made up on Halloween several years ago. I really didn't have anywhere to go but I felt so good and knew that I'd get a free pass on Halloween so I decided to go out, just run a few errands and be out in the world as Linda.

The last place I stopped was at a bagel shop. The SA barely looked up as I came in and began scanning the selection. When I said, in my regular voice, "I'm ready to order," she did a double take. She looked at me and said, "I really didn't know you were a guy. You look really good." You can imagine how great I felt. She called to her friend who was in the back room and we all talked for several minutes. That was a wonderful experience.

The other time was a few years later when I went to a meeting of the Island Girls at The Edge in Blue Island just south of Chicago. I was so nervous about going in. I had heard the Island Girls were very nice, but still...it would be one of the first times I was out and mingling with people without the "cover" of something like Halloween. As soon as I walked in, girls started coming up to say hello and welcome me.

It was an amazing night. The girls made me feel so at home. After years and years of hiding an important part of myself, I was able to show this side of me and people not only accepted me but were very sweet and complimentary.

By the way, the Island Girls still meet at the same location. It's now called Club Krave. If you're a Chicago girl and looking somewhere very nice for your first time out, you couldn't do better than to go to an Island Girls gathering.

[tricia_uktv]

Memory? Isn't it the next time?

A week to wait :(

[Karen__Starr]

Many good times but last month was fantastic, spent an entire weekend out and about in Portland Oregon going shopping, out to dinner and clubbing along with spending time at a new friends place. I got to wear casual and super sexy evening gowns. What made it great was simply enjoying myself with good friends.

[Jennifer in CO]

The main one for me was my "wedding" when I was 15. Now before y'all start having a cow, It was actually a photo shoot for my Aunt (who created Jennifer). It was the summer I turned 15 and very long story short I was spending the summer with my grand parents to help out. Well, after being there for about 2 weeks, I got to go to my Aunts for a week or so and be Jennifer. My Aunt was a beautician with a shop in her home. For those of you who remember Charlie's Angels (the first time around), well, I had mid shoulder blade brunette hair and she wanted to try the style on someone and I had the best head of hair to work with so over a long afternoon I got the "Farah Fawcett" style. That was Friday as I remember. Earlier that day, my Aunt had done a girl that was getting married on Saturday and we were invited to the dress rehersal that night. That evening for the dress rehearsal, I actually got to be the stand-in for the bride during the run through. Saturday afternoon she had the bride to prep for the wedding so my 3 cousins and I went with her to the ceremony. When it was starting, I was asked to come into the brides room for a moment and there on a hanger was a bridal gown I had found at the community chest my grand dad ran the week prior. Over about a half hour she primped and prepped me and when the bride had left the church we went into the sanctuary and had photos taken (by the same professional photographer) of a "bride" and her "Farah Fawcett" hairstyle for my Aunts salon. This was actually when my GP's met Jennifer for the first time, as grand dad actually "walked" me down the isle (also part of the very long story). I had photos taken for my Aunts shop (lots of closeups), then several full "bridal" style shots and then several with the GP's (one of which grand ma kept on her bedside table for many many years) and then with my Aunt and cousins.

Other than my "real" wedding and the fun that started there, this would have to be my fondest memory.

Jenn

[matti]

I had two most memorable times:
First was when I was alo younger I was with my aunt and cousin and my cousin (female) wanted to go out to play with the kids outside and I didn't. My anut told her that she couldn't because she had her school uniform on (blue jumper, white shirt and blue tights). My cousin came to me and ask if we could change clothes and I said I didn't care I just wanted to get homework done. Cousin ask her mom and she didn't car either so for the first time I was wearing girly clothes tights and all. Studied all day in that outfit and hated to change in the evening when I had to go home.

Second time was with the same aunt and cousin when I was 16 and they dressed me up as a go go girl, short skirt, black tights, boots and a wig. I had so much fun and felt sooo wonderful. I told them afterwords however we moved and I haven't seen either of them since.

Oh well memories are great aren't they

[NicoleScott]

1. Making up and dressing up "all the way" for the first time. Wow.
2. Going out en femme to a wig shop in a mall.
3. Being approached by a man as I walked to my car, said he just wanted to talk. I skedaddled. Scared me to death, but after, found it exhilirating.
4. Went IN to a [gay/lesbian] bar dressed and made up in my preferred style (high heels, heavy makeup, deep red lipstick and nails, long thick eyelashes, etc). Doesn't pass well, but I knew that and found it very exciting. I was treated very nicely.

[Samantha43]

All of them! :daydreaming:

[Rachel Morley]

Gosh that's a difficult one to answer as I've had so many truly fabulous times out dressed. I'm doing things now that I would never ever have thought in my wildest dreams (fantasies?) that I would be doing, including one of my most favorites .... being a bridesmaid at a "wedding". It was a TG wedding vow renewal but that's close enough. :)

However, there is one thing that sticks out in my mind and that was going out dancing at a nightclub with my wife as "two girls" hitting the town. It maybe doesn't seem like such a big deal but if you understand my background you'll maybe understand why it was such a big deal for me.

All my young life I enjoyed going out to nightclubs, drinking and dancing until the early hours. When I was in my 20's I was hitting the clubs and dancefloors every weekend. For a lot of this time I was single and I had a lot of GG friends. I was kinda like the "honorary girl" because I hung out with them a lot, except I was a guy. Often we would get ready together at each others houses or that's to say I would regularly be present when one or more GGs were getting ready. They'd always seem to be having so much fun, drinking wine, listening to music, choosing cute outfits, and putting on makeup all in preparation for going out. I used to long to be one of the girls and want to get dressed up and have fun just like they were. Instead I had to wear boring guy clothes and getting ready to go out was just functional. :sad: I wanted to wear cute short skirts and dresses and sexy high heels with lots of makeup and then go out with them ..... but I couldn't.

So it was a dream come true the first time my wife suggested it. We got ready like two giggling teenagers as we did all the things that my GG friends in my 20's did. It was quite an emotional moment for me too as I felt excited but also sad that I'd missed out for so long. The nightclub we went to was technically a gay nightclub but a lot of straight people go there and so even standing in line to get in seemed like I was reliving the past except this time I was a girl. :) Inside I danced until I couldn't dance any more. It was a fantastic night and is something I will remember for the rest of my life. Even writing this post is making me feel "funny" thinking about how I felt.

(P.S. sorry about the long post).

[windycissy]

My first "date" with a guy, we went shopping at Target and then he took me to Outback, pretty classy huh? I was so nervous and excited! I can still remember what I wore, just a simple skirt and sweater, this picture from that night may be fuzzy but I remember it like yesterday:

http://im1.shutterfly.com/media/47b5ce36b3127ccecc371a77954300000010O08IatWLlw0aA9 vPgw/cC/f%3D0/ps%3D50/r%3D0/rx%3D720/ry%3D480/

[Jess81CD]

I think my favoutite memory was in my late teens. I had long hair and my body was quite hair free naturally. It was winter so it was dark quite early and a friday night. Everyone in my house was away for the night so i dressed fully. Purple dress, black stockings, knee boots, sexy lingerie and a jacket along with lipstick, mascara and eye shadow. I literally only walked down the road and to the post box and back but i walked past a couple of people and didn't get a second glance off anyone. I still remember feeling the cool night air on my legs and the sound of my heels as i walked.

Such a great moment i wish i could have shared with someone.

[angpai30]

My most memorable memory is of 4 years ago when I first went out into public dressed, but it was on halloween. I was told by my gay supervisor that I would one day make a very pretty wife. I'm not gay and I'm happily married to my wife and have 2 kids. I love being a male who wears womens clothing the feeling you get is exhilirating!!!

[karen68]

The best, was the first time I got all dressed, and madeup, and went out in public. What a thrill it was. I'll never foget how wonderful it was.

yes me too it was the best time i have had I felt sooo feminine:):daydreaming:

[christinek]

I just had mine, when that GG planted a big ol kiss straight up on my lips. It was amazing!

The full story is here. http://www.crossdressers.com/forums/showthread.php?t=116580

It was at a Waffle House on 27 Sept 2009 at the SCC. Also getting the pass from the police officer on the same night.

[sherri52]

When I was 48 my then gg helped me dress, she did my makeup and we went out to a party. It was a gay party and I was (am) straight. At the party I was hit on by a few of the guys there and managed to avoid any dislike for them or me. I was brought to the party because my gg said I was Homophobic and of course I denied it. I guess I was but I got over it that night and had a great time.

[Joann0830]

I had Two memorable times once in the 50s I didnt have a wig so I dressed as the other girls did with a curchief over my head and tied around the neck and a red sweater and a multi speckle color skirt with a wide belt and a pair of my sister in laws stocking and one piece corset , not the pants type the other which held my legs closed and a pair of my Moms shoes and I felt so confident with the blue eyeshadow and red lipstick I went for a walk in the City Lower eastside where I live and I felt so vibrant and wonderful and even had a couple of guys cat call me and whistle at me Wow what a feeling.
The second time 2007 I believe I was driving from upstate NY where I live to a TriEss Halloween party in New Jersey and I got lost and had to stop on the highway and ask directions and of course it was a New Jersey State Trooper and with my fem voice I asked him and made sure he saw my Wedding band (Ladies) and he showed me the exit and Driving all that way as Joann and walking into the hotel as Joann was Fabulous. Bu the funny thing was driving home when I had to stop at a Rest stop for a Ladies Break and when I walked into the rest stop the Cleaninng Lady looked at me and said the Ladies room is that way and I Thanked her and did my thing and when I came out stopped at a Arbys for a coffee for the ride and so well treated at the stand I was glowing. My Favorite two Days, that I will never forget. Joann0830:battingeyelashes::heehee::love:

[Yolanda_Voils]

While in Chattanooga going into a Wal-Mart, bout 10:00pm a guy was ahead of me about 30'.
He said, "WOW" and did a total flip, head towards me and feet flying :o

Later that night while getting gas, the girl at the counter got big eyes and blew me a sincere kiss.

I was in a long pink dress, 4" open toe f/me pumps, and a long brunette wig..

Musta looked OK that night:D

[Toni_Lynn]

This is quite easy. There are actually two separated by many years.

1st: Getting my first bra at age 13. I shall never forget that day

2nd: The first time my wonderful wife and I made love and I was able to explore my crossdressing in that way and incorporate into our romantic and fantasy endeavours.

Huggles

Toni-Lynn

[karen68]

2nd: The first time my wonderful wife and I made love and I was able to explore my crossdressing in that way and incorporate into our romantic and fantasy endeavours.

Huggles

Yes that is a special one isn't it:thumbsup:

[JC]

When i first got breast forms - no doubt - that was #1

[Cristi]

So many good memories, but if I had to select one right now it would probably be from halloween a few years ago.

I go out on more than halloween now, but it is still a 'free pass' day so I can go out and do things I normally wouldn't dare do. On this day, I was dressed in a mid-thigh light airy skirt, white top (which you could just see the outlines of my bra through), nude pantyhose and heels. I'd spent a lot of time on my hair and makeup, and even had jewelry that 'went' really well with the outfit. Finally, I had a nice handbag with all the things I needed with me.

So dressed like this, I decided to stop in at a real estate business where I know the owner, office manager and a few of the agents. The office manager recognized me right away, and got a real kick out of my outfit. We hung around for quite a while chatting, and I never got over the fact that I was standing there having a normal conversation with these 3-4 people that I knew well dressed as I was.

Well, the best was yet to come.

They had a new real estate agent that I'd met a few times, but didn't know very well. When I heard him coming down the stairs form his 2nd floor office, the office manager got a wicked grin on her face and just said 'lets try something'.

I had no idea what she had in mind, and figured that he would 'clock' me (even if he dind't recognize me) as soon as he entered the room.

As soon as he walked in, she stepped between me and where he was coming in and said, indicating me, "This is Karen, a friend from out of state. She's looking for a house in town and I thought you might be able to show her a few things".

Well, it almost floored me when he showed NO SIGNS of knowing I was a guy. He just smiled, offered his hand and said "Pleased to meet you, Karen. I'm Richard. What kind of property did you have in mind?"

I had no idea how to respond. After a second (which felt like an eternity) trying to come up with something I said, in my best feminine voice, "A single family home in town, something small for just me and my husband". He bought it and didn't blink. The office manager and others, who were out of his line of site, were almost doubled over in laughter that he hadn't caught on yet.

I was able to keep the illusion going for a few minutes through a few more questions and even followed him over to a desk where we offered me a chair. I sat down, being sure to be as feminine as possible while sitting. I swept the skirt under me as I sat and casually crossed my legs.

But before he got any further, the others in the room broke out laughing. As he looked around to find out what the joke was, he took a closer look at me and finally caught on. even then, he knew I was a guy but not WHO I was.

After he knew, he did say that he had thought my voice was a little masculine sounding, but not enough to give me away in this circumstance.

Well, I hung around for a while longer before heading off to do other things. From that day on, I wonder how long I could have strung it out. I imagine how fun it would be if I'd actually gotten as far as having him drive me to show me a house somewhere!

Now, when I have self doubt about going out in public, I always pull up that memory. If I could talk to him without him ever catching on, perhaps I CAN pass in a casual environment and can relax more when out in public.

Oh, and a very quick 2nd thing. About 3 years ago I was out shopping at a TJ Maxx (kind of a discount clothing store for those not familar). I didn't THINK I was passing that day. When I went to the fitting room with a dress and skirt in my hands, I fully expected to be directed to the Men's fitting rooms.

But when I walked up, the attendant casually handed me a tag for the woman's side and opened the gate to that area for me. There were 6-8 dressing rooms in that area, all being used by other women. I tried my things on and even left the room to use the bigger mirrors in the common area. I tried everything on, changed back into the dress I'd worn in, and left the area without anybody there noticing (or perhaps just not caring) that I wasn't female.

[goofus]

I have 3 memories about dressing. But this one I think is my favorite. It was long time ago when I was a soph in high school back in 1957. My sister was in college and was a dance major. She had solo dance that she had to perform for her grade in the class she was taking. She would be graded on her interpretation of of the music and words. In the song the girl was auburn and long haired, my sister was short blond. Solution rent a wig from the school's theatrical department. She had the wig home and out of the box and she noticed the way I was looking longing at it. She asked if I wanted to try it on. Eagerly I said YES! She said "Come home right after school tomorrow and I will be ready to let you wear the wig." She used to dress me up as her sister years ago and she knew I still dressed on my own but I guess I was too stupid to put 2 & 2 together to think what she had in mind. When I got home there was a note for me to take a shower and put on the things she had laid out for me on her bed, a bra panties a half slip and a full slip garter belt and nylons. I was so excited I could hardly contain myself. She finally showed up with her friend who taught makeup for the schools theater department. She made my face up and my sister got her hot floral dress for me to wear. It was the in kind of dress that the popular girls wore especially the hot ones, scoop neck and thin arm straps. After they put the wig on and showed me what I looked like I fell in love with the girl in the mirror, she was down right gorgeous. All dressed up and no where to go. When Beth(my sister's friend) saw me completely dressed she said we have to her off, and they did. We went to dinner at a pizza place that I had never been to so we wouldn't run into people that I knew. But we did run into a lot of my sisters friend from school and I was introduced as a cousin from back east. What a blast!!!!!

Sounds like such fun! Would that all of us could have had such a memory :)

[Andy66]

Awww... What wonderful memories. :)

I never could dress in guy clothes and come anywhere close to passing as a man... but I remember the first time I ever went out with a crossdresser, twenty years ago.

We met in a gay bar, both alone and bored, and started talking. She was gorgeous, tall and exotic. Neither of us had dates for Valentine's day, which was coming up in a few days, so we decided to date each other. I picked her up and we exchanged boxes of chocolate, then we went out dancing all night long. Funny, it never even crossed my mind to be self-conscious. All I could think was that I was one lucky woman, and all those men in the bar must have been jealous of me.

[Desiree2bababe]

The first time with a man. It completed my desires to be a woman in every way.