Do you have a clear highlight among your CDing experiences?

[Tamsin Englefield]

Mine came very early in the piece. Probably too early for me to fully appreciate it at the time.

My school friend?s family was going away on holiday and he asked me to look after their cat while they were away. The key to their house allowed teenage me, at a very early stage of my cross dressing experimentation unrestricted access to his really quite glamourous Mother?s and his attractive older sister?s wardrobes, lingerie drawers, shoe cupboards and make up tables. All were so much more feminine and exciting than my own Mother?s rather functional collections.

I had 2 wonderful weeks with which to explore, experiment, mix and match, understand how all those fabulous clips and clasps worked, teeter around in too tight stilettos and a space in which to parade in my findings.

At the time my anxieties about leaving some telltale sign of my explorations probably prevented me from fully enjoying the experience but looking back now this was where Tamsin first really emerged and a lifetime?s journey began.

[Marketa]

Definitely my last weekend I described in this thread with photos of my outfits

https://www.crossdressers.com/forums/showthread.php?284890-My-first-weekend-going-out

It was amazing experience being out "in the wild" for the first time and not only in the safe of neighbourhood. I didn't feel excitement at all, but a lot of joy all the time both on Saturday in the city as well as on Sunday in the shop. Except the part when my awesome and beautiful shoes were trying to kill me : D

I really enjoyed it and I am already planning next going out :)

[NancySue]

Several years ago, a local charity held a very extravagant fund raiser.

[docrobbysherry]

I've had too many to be sure of which was #1.:battingeyelashes:

But, I'd guess my top 3 are:

Taking photos in Angkor Wat dressed as Angela Joli in Tomb Raider.
Being featured in a UK TV special on rubber CD's.
And, as the sexy woman in a professional music video.

[Jackson]

That 1st step outside. For 30 years, I never ventured outside. My girlfriend, now wife at the time decided I needed to go out as Jackson. Making that step out the apartment door was difficult. OK we went to Appplebee's and baskin Robins and walked around an outdoor mall. then she could not get me back in the apartment because I just wanted to stay out and about. I still dont venture out much, but that is one major highlight.

[Leah87]

My clear CD highlight was the first time I ventured outside of the house, which was earlier this year. That experience took my CD life to another level.

[CarlaWestin]

I'm sure there were many but one that stands out is when I simply went out and enjoyed a day out and actually went to a casino.
The images are even named That Moment.

342240 342241

[April Rose]

The last three Fantasia Fairs, or Transweek, as they are now calling it. A whole week walking around Provincetown as if April owned the joint.

[josie_S]

I have several moments that stand out, but when i first started venturing out, I was in San Diego for work and got dressed up and went for a drive. Walking in that open parking lot while it was still sunny out was a rush! But the best part was when I stopped at a gas station for cigarettes. I'd done that before, but usually at like 3am. It was a beautiful fall evening and I felt pretty, but boy oh boy was a nervous wreck. I go in, and ask for my camel lights, and the woman working there looked at me (to see if I was over 18 I guess lol) and then just...rang me up. I was so stunned that she didn't say anything. I remember the way my heels clicked on the asphalt as I walked back to my rental. I felt sexy. I turned around to go back in...I had decided to "out" myself to her and see how she would react. I walked back up and asked her if she really couldn't tell...she scanned me a little closer and then she lit up, but then looked confused again. The she did the universal cupped boobies thing with her hands and asked me how i did them. She said they looked natural. I was in heaven! And the funny part is it was just two very strategically folded hotel hand towels. I've since graduated to forms lol, but every now and again I try to recreate that fold, and I never can!

[Fiona_44]

Attending my first Keystone Conference in 2023, surrounded by 700 other trans women, was one of the highlights of my CD life.

[Sharon budd]

Wow, Carla you look amazing. You certainly hit the jackpot. Whey to go go girl!
Hugs.
Sharon x

[Geena75]

About a year and a half ago I had the chance to go to the support group meeting in Grand Rapids. I had gotten a new bodycon dress and pattern tights for the occasion. I met up with friends at a bar beforehand, then on the to meeting, then on to a club where a favored band was playing. The band loved our little group, and I danced the night away through the last set. Got plenty of compliments and felt so very accepted, even when stepping out for a smoke around strangers. What a night!

[Celine 9]

The first time I ventured outside my house was 2 years ago. I was dressed as Wonder Woman and Super Girl including dresses. This was a life changing event of my crossdressing experience. I went no further than the drive way. :) When I outside, I took selfies. After words, I did editing and the pitchers came out okay. I kept the length of my time outside short so I did't lose track of time.

[kimdl93]

I have a number of favorite memories. One of the more recent highlights began as an evening having dinner and a few drinks while listening to a band. Somewhere along the way, I struck up a conversation with a pretty 20-something woman and before I knew it I had been drawn into a bachelorette party in process. Towards the end of the evening, I thanked the young woman for being so accepting. It was only when I acknowledged being trans that she realized it. I had seemingly passed all evening with maybe 20 women and did not know it!

Granted, they were partying and had other things on their minds.

[CarlaWestin]

Thank you for the nice compliment, Sharon. I remember that the asian lady I sat next to in the second picture seemed annoyed. But, it was probably the machine erasing the dream of winning big in vegas.
Geena, I'm just a little lost for words. How do you ever go back to drab mode. Can we hook up and go shopping some day?

[Cheryl T]

Highlights for me would be the interactions I've had with women along the way.
Trying on a dress at Macy's I ventured to look for my spouse and an older woman saw me looking for her and said "He's going to love you in that dress".
Standing in checkout at TJ Maxx a lady behind us had her child in the cart. He kept throwing a ball on the floor and I would pick it up and return it. She finally said, "that's enough, the nice lady has other things to do".
Walking through a mall an older woman approached me and commented on the top I was wearing saying how pretty it was and asking me where I bought it.

It's things like this that make me feel warm inside. Nothing extraordinary, just kind words and acceptance.

[TheHiddenMe]

I've had quite a few, so I will select two.

1. My first day of really coming out. Makeover at Sephora, trying on dresses at Nordstrom. Interacted with the SAs and the MUA and they didn't run screaming. Far from it, they were accepting. I walked the mall and went to other stores (a Dress Barn & DSW) and no cared.

2. Six months later, went into Beauty Brands as a guy to get my fingernails done (for a four day train trip to Chicago). Got randomly assigned a nail tech. Her name was/is Michelle, we hit it off, I went back to the store dressed a few days later to show her girl me, and we've been good friends since and have been out together lots (most recently Tuesday).

[Christie ann]

I guess like others, I have a few to pick from and I just had to pick two. Years and years ago, I made an appointment at David’s Bridal. Oh, wow, they treated me so nice and made me feel so pretty. It really was a princess moment. Standing in front of that mirror, wearing a wedding dress was just too much. Thank God for waterproof mascara!
The second, was just a year ago, I took a class as Christie, no boy clothes, just me and my razor. and lots of lotion for razor burn. It was an outdoor class and every picture shows me in my hiking skort. I was just a girl all week and I felt that gender euphoria the whole time.

[Debbie Denier]

Going to buy a dress in drab at a small CD friendly shop .I was admiring a dress on the racks when the manageress asked me if I would like to try it on. Of course I did. Complete with nylons, heels and a wig.It was the first time dressed in front of another woman and the first time I experienced acceptance. It was wonderful. I shopped there regularly for months until it sadly closed down.

[JesseVF]

My one afternoon at Fantasia in Provincetown was great of course, but for a more real life experience went for a hike in a state park including short interactions with others. Then strolling and shopping in a nearby town where I tried on and bought a top.

[AllieBellema]

I still have to say being able to wear my favorite southern belle dress to the local Pride events the past couple of years will always be a highlight of my life. Just getting out and getting all kinds of compliments for it was wonderful!

[SaraLin]

my highlights are:
Few
Far between, and
Fleeting.

Ironically, they're these are when I'm treated as "just" another woman - nothing special. For those brief moments, I'm happy and at peace.

[IwishIwasTracy]

Top two moments for me would be trying on wedding dresses at a David's Bridal. That was a dream come true. The second was just a couple of weeks ago. It was a Saturday afternoon and I was at home alone and I thought I am going to put on a dress and go out into the world. I don't pass and I didn't even try to. I went to a Lane Bryant and tried on dresses and then off to a Starbucks for coffee. It was great to be out in the world and feel like I belonged.

Tracy

[Helen_Highwater]

I guess I'd have to pick out the first time I attended a support group meeting and came face to face with others of our community. Firstly to get there I had to park on a busy road and walk albeit a short distance to the hotel where the group met. Entering the hotel and walking on a marble floor and stairs in heels, each step sounding so loud at least to me, making my way into the room, finding the group secretary to introduce myself before asking to join a table of ladies. Chatting, it soon felt that this was the most natural thing in the world to be doing, totally at ease.

And coming to the realisation that you're not alone, that your story is one that resonates with many others, gave me such a huge boost in confidence.

On a later visit a met up with the gurl who was to inspire me to take my first steps into a shop the very next day and was a catalyst for so many adventures to come.

[Lorna]

Many responses relate to "out and about" experiences, something I have never had and am not likely to have. I imagine there are many more, like me, whose experiences are all in private. At first I couldn't even begin to pinpoint that clear highlight from the many years that are now behind me but, on reflection, it might be this.

Much of my dressing has been role-play. That is, trying to recreate situations observed in girls and women over the years where I have very much wanted to find out what it would be like to be dressed as they were and, if possible, do what they were doing. The latter is usually impossible but trying to reproduce the clothing experience could sometimes be achieved. Way back, as a teenager, I was intrigued by girls my age who had started wearing stockings. Eventually I was able to find out from a girlfriend (never mind how!) exactly what she was wearing under her dress. Her suspender belt was a long-ish one that covered her tummy and extended down from her waist towards her rear but not over it. It must have been at least twenty years later that, by chance, while visiting a town in the north of England, I came across a rather old-fashioned shop selling, amongst other things, school uniforms and women's underwear. It took a while to summon the courage to go in and see if they had anything like that suspender belt I still remembered from my past. I made up a story (probably not believed but the assistant didn't show signs of disbelief) about my wife needing to create an authentic 1950s outfit and the assistant offered me a choice of two suspender belts, one of which looked exactly like the one I remembered but was boned in the front and the other was much less substantial. She also told me that "many women wore roll-ons back then" and offered a simple elastic roll-on as well. I told her I thought the longer suspender belt looked like the sort of thing but she cautioned that my wife might not like the bones - but then added that she could easily remove them if she wished.

I was, by that time, just wanting to pay for the belt and leave the shop so I immediately settled on the deeper belt, paid (only a couple of pounds, I think), and made my exit. No, that wasn't the highlight: the highlight was a couple of days later when I was able to wear that belt with a bra, slip and fully-fashioned stockings under a shirt-waist dress and find out, for the first time, just what it would have felt like for that girl all those years before.

[DavynaCD]

The lowest and highest point was being discovered by my wife dressed up. After days of intense discussions where the relationship teetered on the brink, she gave me a hug and we had some of the hottest sex we?ve ever had. Turns out she was quite turned on by it all.