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Megan’s Day Out

Pretty, pretty cool...

By Trish White

This was a very special day. It was Megan Kelly’s first day out in public. She’d been planning this outing for quite some time. Unfortunately, at this time, Megan’s wife is totally unsupportive and not at all accepting which makes it very difficult for her to go anywhere. She lives in Victoria B.C. and was going to have her outing in Vancouver, New Westminster to be exact. When she told me she finally had a date for her first outing I was ecstatic. She had been talking about this day for a long time but the past few times were cancelled due to family issues. I didn’t think it was ever going to happen but I kept telling her “just let me know the date and I’ll be there for you”. 

I first met Megan on Crossdresser Heaven. She had posted some pics and I was amazed at how nice she looked and what a feminine body she had. I told her on this her special day that I originally thought that that she may be transitioning. She looked that good. But after a lot of back and forth PMs it became very apparent that she had never been out in public and even the thought of it terrified her. So we began our journey together. Megan the terrified student and Trish the willing Big Sister. This journey was not a short one either. It didn’t take months it took years. But here we are March 16, 2024 and we are meeting at Shaivona’s Salon at noon. I had driven down that morning from Kamloops and Megan was fresh off the ferry from Victoria. If any of you have been to Diva Las Vegas or any of the others in Vegas you’ve probably heard of Amy who owns the Just You salon. She does nothing but Trans Girl’s make up. Well Shaivona is Vancouver’s counter part to Amy. She’s an amazing person and does do Cis girls but most of her clients are Trans.

When Megan’s date was confirmed I immediately messaged my girl friend Maggie who’s the president of Gurls in the Burbs. It’s one of the Trans social groups I belong to in the Vancouver area. So I filled Maggie in on what was going on and asked for her help in getting the word out to all the girls there about Megan’s coming out party. Well Maggie and Shaivona were all over that. One of Megan’s concerns was were the places we were planning on going to Trans friendly? So I checked with Maggie and she advised that all of New Westminister was very LGBTQ friendly. The day before Megan’s arrival Maggie and Shaivona got together and set up Megan’s whole day. First I was meeting her at Shaivona’s Salon for her make over and then we were meeting the rest of the girls for lunch at Judge Beggbie’s Bar and Grill. Then clothes shopping at Grand Central Consignments. After that make up shopping with Shaivona and lastly dinner at Georgies. 

There ended up being 8 or 9 girls that were able to be there to  accompany Megan and support her for most of the day. When we walked into Judge Beggbie’s Bar and Grill I could see the look of relief on Megan’s face. Being out in public in broad daylight had taken its toll on her. I could see it in her face and this was just the start. I was going to go into detail as to how things went as her day progressed but a couple of days after her amazing day out I received a copy from her diary of her first day out and in it she is very specific as to how she was feeling at each moment through out the day, the good moments and the not so good moments. So I will be adding her account of the day at the end of this post. I think it will bring back a lot of memories to each and every one of us as you read it. 

By Megan Kelly

Here is the full report of my first time out in public in full femme mode. I experienced much of what others before me mentioned they experienced on their first time out. The big difference for me was having a big sister support me throughout the experience. This day would not have happened without Trish being there along the way.

First up was getting glammed up with the makeup artist. This was a relaxed and safe experience as Shaivona works out of her home. She is personable, funny and most importantly, really good at making me look good. This is also where I met up with Trish. For those of you who don’t know Trish White she is somebody I met on Crossdresser Heaven. She is internationally known (maybe) for being supportive and encouraging of first-timers and all crossdressers alike for that matter.

After getting dolled up, and a quick photo shoot, I drove 20 minutes to the pub where I would be meeting a group of fellow CDs. The drive was enjoyable as I was driving in FULL SUN feeling very beautiful and feminine. It became stressful as I got stuck in traffic and had people in cars right beside me (at a slow crawl). I managed to get myself to the pub but had to park a good distance away. This meant an arduous walk (probably 100 meters) to get inside. Luckily Trish found where I was parked and walked with me. Walking in full dress, IN DAYLIGHT, was inconceivable to me up until this moment. With Trish beside me, however, it became doable. I was wearing the jeans outfit and found comfort very quickly. As every crossdresser who has done so before me has stated, almost everyone else just carried on business as usual. Somehow the world did not stop to look at me and comment. I did notice a few people look at me a little longer than I’m used to. I do wonder what they were thinking.

Once inside the pub, my nerves calmed quickly. There were 6 other gurls already there enjoying a drink. Shaivona joined us as well. I sat down and enjoyed being a woman out in public. Yes, a few people took a longer look as they passed by, but as I learned to ignore these glances my enjoyment grew further. Having a drink, in a pub, as a woman was a fantastic feeling.

Our group then walked (yes, once again IN FULL DAYLIGHT!!) a few blocks to a vintage clothing store run by a lovely Woman who was very welcoming. She gave us huge discounts on our purchases. The store was two floors of woman’s everything. Being able to peruse AND TRY ON anything I wanted, AND BE ENCOURAGED to do so was one of the highlights of the day. I spent a lot of time shopping as a woman and couldn’t believe how good it felt.

The group became a little smaller as we walked (yes, once again IN FULL DAYLIGHT!!) to a drug store to shop for makeup. There were a lot of people out and blending in with the crowd was something I wouldn’t have thought possible. I’m sure we were clocked: a number of times but I rarely noticed. I was too busy trying to look as good as possible, haha. I was becoming very encouraged and happy with the overall acceptance I was experiencing from the general public. All the experienced crossdressers reaping this are saying “Yes, no sh*t” to themselves right now.

Our group activity ended at this point. Trish and I made our way to our hotel. I should mention that as I parked my car near the hotel I got checked out by two men. This was a terrifying and exhilarating moment and I had to retreat to the safety of my car to collect myself and call Trish for further support.

Checking into the hotel was another highlight as the receptionist referred to me as ‘her’, OMG!

Trish and I changed into our dinner dresses and made our way to a restaurant for dinner. We walked (NOT IN FULL DAYLIGHT this time). I was wearing a dress with heels and nylons this time and felt fully feminine. I walked into a busy restaurant with 83% confidence and sat down.

Dinner, in a busy restaurant, in full femme mode? WTF!, OMG! I fully enjoyed dinner as our server continued to refer to us as ‘ladies’ and ‘girls’. She even complimented my outfit: good lord. I didn’t once feel out of place in this busy restaurant with people all around us.

Walking back to the hotel I didn’t want the moment to end. At this point I wanted to be looked at, lol. I was exhausted though. It was time to shut it down. What a first time out.

Yes, I do look forward to doing it again. My feelings of being clocked have disappeared, but looking out for my safety (one big drawback of being a woman) and a strong fear of being recognized still persist.



19 Responses

  1. Great account and you both looked fantastic. And a particular ‘well done’ to Megan; the first step isn’t easy, not least as we can always think of 101 reasons not to do it, but once we’ve done it pretty well anything seems possible.

    And I can concur that ‘ [Trish] is internationally known (maybe) for being supportive and encouraging of first-timers and all crossdressers alike for that matter’ as I live in the UK and she’s always very supportive and encouraging to me!

    1. Thank you for your kind comments Amanda. By days end Megan was a different girl thanks to all the support she received from the Gurls in the Burbs. As you said “once we’ve done it pretty well anything seems possible. Some time during her day I told that on her Ferry ride back to Victoria she’s going to be saying to herself “what was I so worried about?”. I’ve said to so many girls, “the hardest thing you’re going to find is just taking that first step out the door.”

      Trish 💖

    2. Thank you Amanda,

      As Trish has heard a million times, there is no way I would have done any of what happened on my own. Having Trish and the Gurls made it so very doable and enjoyable. My brain was struggling to comprehend how pleasurable it was.

  2. Trish and Megan – What an inspiring, uplifting account! Big congrats to you Megan – you’ve broken through the barriers of fear that have confined you, a new wealth of experience is now open to you. Your concern of safety will help protect you as you go forward, as it should be for any woman. How fortunate also that you have a big sister/mentor as wonderful as Trish as your guide for your early experiences. Trish, you are a wonderful ambassador for our community and you lead us all with your example.
    You are both beautiful – inside and out!
    All the best

    1. Thank you Kris, I couldn’t have said it better! It really was amazing to watch the change in Megan as the day wore on. To see her confidence grow and that smile appear on her face was so heart warming to me. After dinner when we were back in our hotel room talking I told her how proud of her I was and how well she’d done. From this day forward she will be a different girl that’s for sure.

      Trish 💖

    2. Thanks for all your kind words over the years Kris. Like Trish, you are a wealth of experience and support.

  3. Megan,
    Thank you for sharing your outing. You obviously had a fabulous time. The more you are out and about, the more comfortable and normal you will feel.

    I really love your clothes, heels and makeup. I’m sure the two men checking you out thought you were a hot looking babe.

    I completely understand your thinking about not wanting the night to end; that is always the way with me.

    And thanks to Trish for her great support, she is a national treasure.

    BTW, I love Victoria. What a beautiful city.

    (your Ontario sister)

    1. Hi Jocelyn,

      I am always happy to meet more Canadian sisters (I’m a bit biased that way, lol). I appreciate how each and every one of us seems to have our own particular style of dress. I’m happy to hear you like mine.

      Yes, Trish is a treasure. I hope to emulate her efforts as I become less of a rookie and more of a veteran.


  4. Hi Jocelyn,
    Thanks so much for your lovely comment. As you said, and it’s so true for me as well, once dressed and we’re out and about when it’s time for the night to end we just don’t want it to happen. I get that feeling each and every time I have to put Trish away, it never changes.

    Trish 💖

  5. Trish ,
    Megan was so lucky in having you to support her through her first day truly as Megan , it’s always amazing how quickly you cease to be less of a CDer and more just girls out on the town .

    My first time out was to a social meeting some forty miles from my home , I had no one to help with makeup or dressing but for all that I wasn’t at all nervous when I set of in my car , it just felt right . It was the first time I’d experienced people taking a second look at the blond driving her car , now I knew what women had to put up with . The social group was holding a 4th anniversary party so I wore a full length ballgown and high heels , everyone was welcoming , we had a lovely meal followed by music . I didn’t expect to set foot on the dance floor but once I did I just loved dancing in heels and my ballgown .

    Like everyone who had experienced their first time , I didn’t want it to end , yes you’re tired , your feet hurt but you still can’t wait for the next time , so well done Megan , I hope you enjoy many more .

    1. Thank you for your comment Teresa. Isn’t it amazing how quickly the memories of the early days in our journey come flooding back after reading about another sisters first time out. Reading your comment brought back my own memories of my first times out too. They were very similar to yours. I was in my late teens living in a city of 25,000 but Vancouver was only a 4 hour drive away so that’s where I went, all by myself. I would just walk around down town Vancouver and window shop or spend some time in Stanley Park. It was very nerve wracking in the 60’s especially being all by your self right?

      Trish 💖

  6. For those reading me, Trish and Megan are 2 best friends of mine. they are in my circle of besties that help me thru tough times, and maybe I pay back a little. Trish has been my compass such the first weeks of me going on line to explore others that I found were like me. We finally met last fall in Vegas. I was a basket case and she calmed me down. Megan is a close friend I share secrets with and fantasize I look like her, ( when hell freezes over). I know her, and know the world deserves her and Trish was the perfect big sis to make it happen. The only downer, I wanted to be there but couldn’t. Better I wasn’t , I would have a basket case over meeting Megan. Love and hugs to you both. Perky👩‍❤️‍👩👩‍❤️‍👩👩‍❤️‍👩👩‍❤️‍👩

    1. Hi Perky,
      Thank you for your comment. You were the only thing missing to make Megan’s day extra special. We know it’s not a short trip for you to come but as you said we’re besties so you got the invite anyways. Your Presence would have been the icing on the cake for sure. But us getting together will happen I know it, we just have to be patient.
      Have a great week end girl.


    2. Hi Perky,

      You definitely pay back and more than a little. I look forward to the day where we can get out together with Trish keeping us in check, lol.

      1. Hi Sis,
        Ha ha ha, I’m not worried about keeping you in line but remember Perky and I were roomies in Vegas and there’s no keeping her in line 😂🤣. But that said I love both of you and wouldn’t have any other roomies. Both were wonderful experiences for me that I will never forget.

        Trish ❤️

  7. Shaivona is a fantastic MUA because Megan you look exquisite, especially in that LBD.
    And Trish, I’m going to need Shaivona’s contact when(if) I ski Whistler next season.

    1. You won’t be disappointed with Shaivona’s efforts. I don’t recognize the beautiful woman in the mirror when she is finished with her magic. And that lbd is a favourite of mine.

  8. Hi Cali,
    No problem just email me when the time comes and I’ll send you all her info. Have a great weekend girl.

    Trish 💖

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