The Dream that came true: my weekend as Tiffany

I am a newcomer to this world, not in existence. As I think back, I’ve always been this way, but it took me a long time to realize it, partly because of upbringing. Texas in the 80s was all about repression, and partly because I was a hardhead, stubborn as the day is long. But 7 months ago began my epiphany (ironically the root of my chosen name) that I was not what I thought I was. This led me to dressing at first, something I’d done sporadically throughout my life, but now it was different. This time my goal was fully dressing, not just trying on whatever target of opportunity clothes I came across. This developed further into makeup and a wig, and two months ago, I joined CDH, using the name I’d wanted to have my whole life, Tiffany Alexis.

My self-discovery began to increase exponentially; I began to suspect that I might be transgender and not merely a crossdresser. I was able to dress a few times in private, and I loved what I saw, which felt like me. It was the me I’d always wished to be. Six weeks ago, I entered a drought. My wife, whom is currently divorcing me (for non gender issues; she’s never suspected tiffany,) had a prolonged time around the house. Then three weeks ago, she announced she was taking the kids to Shreveport for the weekend. I knew that Monday and Tuesday I was going to New Orleans for business. I would finally have my dream, five uninterrupted days to be Tiffany!

The countdown was excruciating, I had not anticipated an event this much since waiting for Christmas as a child. Days passed with the speed of geological epochs as minutes felt like years. But finally, on Friday morning the family car departed, and what I called on CDH the TiffTastic Voyage began. It was tame at the start, immersion in dressing fully and 2-4 makeup practice sessions a day. I lounged by the pool and took a couple hundred pictures. I chatted with y’all; I had a wonderful time.

Saturday night I got the wonderful surprise of being asked to join the chat crew on CDH, which I am flattered, honored, and proud to be a part of the team! One of my photos also got featured, which sure made this girl very happy! Sunday was more femme wonderland, but I had to take pause that evening when the family got home. It had been three straight uninterrupted days as tiffany…pure bliss. I started dreaming en femme at this point. But one scary thing remained…my first time in public as Tiff. This was to be Monday…..I could barely sleep the night before…woke up and was able to leave early Monday morning for the four and a half hour drive to Nola! The whole way down I had butterflies in my stomach…would they all laugh? Would they point and mock? Would I have the courage to do it at all?

Anyone who knows me might think this silly. I have voluntarily gone into natural disasters and horrors many times in my job (ems/rescue/emergency medicine), but this was different. This was baring my naked soul and true self for the first time in 43 years.

I rolled into Nola at 1:30 pm; checked in to the hotel in the French quarter. I had an ace in the hole…two friends, Samantha and Chelsea, from CDH who live there. I met them at an art gallery on Royal Street. Within minutes, I’d purchased a new wig, and within the hour, my first purse and some other goodies. Then after a critical mission to secure iced coffee for Samantha, and a side trip into a store whose temperature was set to “magma,” it was back to the hotel to prepare.

I put on my clothes, breast molds, etc., but at this point I realized Samantha was a couple blocks away at MAC, a makeup store, getting a makeover. I didn’t have any makeup on, but was determined to make it out…so I decided to meet her there. Somehow, I was able to make it out the door and into the elevator, down to the lobby, and then outside! My heart was pounding. I had tunnel vision and was terrified! I began walking in my new heels. Hair kept getting in my face. A homeless guy started heckling me, calling out, “it’s a dude in a wig” a half block down. I kept going, sweating buckets. Another guy said “hey bro nice wig.” I replied, “Thanks dude” and kept walking, reaching the MAC and entering, leaning against the door as if it’d been zombies I was fleeing. But I’d made it! And Samantha was there!

I spent the next two hours learning some makeup skills, which I think will allow me to finally beat the “applies makeup like a drunken toddler” level I’d been stuck on. By now it’s 7:15, and we take an Uber to the bar, because good God I needed a drink. The bar was the Golden Lantern, and I walked in…..and no one laughed. No one seized or pointed. Instead, a bunch of cool people welcomed us, and I had a good stiff drink. A few more followed. I may have even been hit on once or twice, but I was oblivious because I was immersed in being out as Tiffany. I was being myself and everyone was cool. Omg, I was so happy and floating on air because this was what I always dreamed of doing; finally being me!!!

A couple hours later, after using the ladies room for the first time, we departed, heading out to eat at the Mona Lisa, where a man held the door for me. The staff treated Samantha and me the same as the one gg with us (Chelsea). We swapped stories seated at the front of the restaurant in full view of everyone and no one hated on us. Some even congratulated me on my milestone!

Later, we had a nightcap at the Bourbon Street Pub, where the staff and patrons went out of their way to make sure I was treated ladylike. It was late at that point, so it was back to the hotel. On the way I was catcalled a couple times. We talked in the lobby a few minutes, and then parted ways. I went back to my room, closed the door, and wept tears of joy. This was what I’d always wanted. I’ve never been so happy, except for when my kids were born. It felt so right; it felt wonderful.

It had all been made possible by the support of two wonderful friends, Samantha and Chelsea, who truly had my back, and did it solely so that I could be me for the first time ever. I will never forget this you two. You made my dream come true.

I went to bed smiling.

I woke up still wearing the wig and still smiling despite the hangover.

Tiffany Alexis

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Tiffany Alexis

I’m pretty sure I am transgender. I’m in my 40s and live in Louisiana, and I’m still finding my way. I was in denial most of my life. I’m not anymore and I embrace what I am. I just don’t know how far I should go. I’m pretty active on cdh too, and still a bit nervous.

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20 Comments
  1. Cynthia S 2 weeks ago

    Tiff-great and inspiring story written in a style that just draws in the reader. My second person that I told about Cyn was on a trip to New Orleans ( https://www.crossdresserheaven.com/forums/topic/coming-out-the-sequel/ for those who are also CDH members). while I didn’t get out publicly on that trip it was not long afterward that I did( I had interacted in a drive thru but it was later that year that I ventured out on foot on a trip to the National Museum of Art in DC and the starting going to CD/TG conferences. For anyone who wants to go out in a very safe and welcoming environment, I highly recommend the conferences like Esprit and Keystone where you will be surrounded by many others like yourself. Tiff, I hope you’ll make it to one or both of those next year-I’d love to meet ya!
    Cyn

    • Author
      Tiffany Alexis 1 week ago

      Thanks cyn!
      I am going to try for both keystone and esprit, and will definitely be at one. I gotta put faces to the names somehow…at least non tiny avatar faces…
      Tiff

  2. Stephanie Kennedy 4 weeks ago

    Tiffany I love that story. It was like I was there with you so happy for you. What a wounderful gift you received. You all look so hot. The story brought back a memory from 35 years ago. I was visiting New Orleans on a business trip . I found a night club that had trans woman as entertainers they would sing have strip shows that type of thing. I was sitting next to 3 stewardess they were having fun they were fascinated by how pretty the girls the girls looked. I overheard one of them say to others I wonder who’s make up she is wearing. I remember how happy that comment made me. They accepted these transwoman as one of them and she used pronoun she to describe her. I
    Thought to my self at the time it was ok to be to be like that they were accepted. The girl in my head was very much hidden. I now understand she was the one telling me it was ok. I remember buying a cute a little slutty by my standards today tee top for a souvenir for my girl friend back home in Boston. When I gave it to her she said she would not wear it it was to sleezy. She made some stupid comment like why don’t you wear it you probably bought it for yourself anyway. I was in shock. The truth be known she was right on both it was little edgy at best and I did buy it for myself. She saw me. We ended our relationship not long after. Thank you for that wonderful story and thank you for a memory . With much love ❤️ for a sister Stephanie

    • Author
      Tiffany Alexis 4 weeks ago

      Thank you stephanie! My heart was in this one, and it’s a memory that still makes me smile, even with all the badness that came after.

  3. Xander Kelley 1 month ago

    Your story is beautiful and you are an excellent writter. I am just finally coming out as a transgender male but i was not treated that well. My mom supports me but that is it. My family does not accept transgenders. But i am moving to another town where people are that do accept me. And maybe one day my family will come around.

    • Author
      Tiffany Alexis 1 month ago

      Thank you! I had as much fun as it sounds…I hope your family comes around…that’s one thing I’m gonna miss when I fully come out….

  4. Amelia 2 months ago

    It is strange how I have scanned through this article so many times and yet only now have I found the right moment to read carefully. It is difficult to convey feelings with the written word without resorting to dramatic devices but I am able to share your joy Tiffany. Thank you.

    • Author
      Tiffany Alexis 2 months ago

      Thank you Amelia, this is the first thing I’ve ever written for others to read. Even after the badness that followed the next week, it still makes me smile to remember, and it makes me happy that it did so for other people.

  5. Marianne Tornander 2 months ago

    Tiffany.

    Congratulations to your wonderful experience and thank you for sharing it with us. I’m looking forward to follow your journey.

    Marianne

  6. Cloe (CC) Webb 2 months ago

    Thank you for writing your experience for us to share, Tiffany. So much emotion and the bravery and determination are an inspiration. It’s about the 2 year anniversary of my first outing and you brought up some wonderful memories. The nervousness and worry I had experienced are faint in my mind now, but were palpable at the time as I can sense was the case for you. But just he same we pushed though and found a new strength we never imagined we had. Like the Eagles song goes “So often times it happens that we live our lives in chains and we never even know we have the key”. Here’s to finding keys and using them.

    • Author
      Tiffany Alexis 2 months ago

      Thank you Cloe! This key sure unlocked something I never expected, a whole new world…one where peace and happiness is possible…not all the way there yet, but it’s the trip I think that is going to earn it. And what a long, strange trip it’s been…

  7. Deanna Lund 2 months ago

    What a Remarkable story ! I Had the pleasure of “meeting” Tiffany The first day or 2 I was on CDH Which coincidentally Was also her Debut on the site . Interestingly, at the time, We were at about the same point in our crossdressing Progress . Tiff mentioned her Desire to Go out in public but her reluctance to do so For a number of reasons . In her story Tiffany mentions 2 significant influences to her Journey, Samantha & Chelsea . They are a married couple One of whom is a cross dresser And the other a remarkable GG and are two of the nicest people I have ever met! They have been very helpful to Tiffany but she Forged this journey On her own though with strong encouragement and support. Tiff is a remarkable person with Great Compassion and strength and a story which goes much deeper than crossdressing . The beginning of her journey is Partially documented herein And I am Very interested to see how it will progress !

    • Cloe (CC) Webb 2 months ago

      My closest online friends, many of whom I have now met, are the ones i first met on CDH. the one I call my soul sister was at the same spot in her journey as myself and had recently joined CDH. It’s heartwarming to see the same is still happening.

      A lot of people have found a safe space to explore their inner selves more deeply on that site. Many find they are content in their current state, some find a balance or fluidity is their space and some realize they most go further. I’m immensely thankful to Vanessa and the ambassadors for their efforts to create a a pressure free environment to foster conscientious though with resources to draw on.

      • Author
        Tiffany Alexis 2 months ago

        This place has a wonderful positive energy to it that I’ve never encountered anywhere else. Vanessa did a wonderful thing by starting it, and it’s also the members of the community that keep it going!

    • Author
      Tiffany Alexis 2 months ago

      You’ve been my best friend since the beginning D and I never would have come this far without you, as well as Sam and Chelsea.

      • Dasia Anderl 2 months ago

        Luv ya, Tiffany! Great article. It was fun talking on the phone with you about your trip. Lovely pic of you three so thanks for posting it!

        • Author
          Tiffany Alexis 2 months ago

          Thank you Dasia! You’ve been a wonderful friend and I appreciate the support you’ve given so much. It was really cool getting to swap stories with you the other night too!

  8. Cami Jane Jansen 2 months ago

    A wonderful heartfelt tale of discovery and acceptance, I’m so proud to know you Tiff and share in a small part of your journey, Sometimes I see some part of myself in others esp here and at CDH my new home and I knew I had to have you for my chat team.. I look forward to seeing you flourish after years in the dark and I expect great things from you for our combined community at large>>You go girl xxoo

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