Hi Girls! It’s Scarlett again and I’ll be writing this from the perspective of a situation that many crossdressers more than likely have in common.

Now Girls, you may already know I spent years and years deep in the closet with my crossdressing. It wasn’t until a year and half ago, right before we moved into our new home with lots of storage space, I was finally able to talk my sexy redhead into having “The Talk” with me. I’ll later write an article on how to bring up “The Talk” and what to say to bring about a modicum of acceptance of your crossdressing from your wife or SO.

Now to the specifics of the article. Most of us have only released our thrill of cross dressing to our wives or significant others. We have no plans of ever sharing this little secret to anyone else on our side of our family, on our wife’s side, or SO’s side of the family. We’ve known them for years, and they have known us for years, and it’s the last thing other family members would guess about us; that fact that we all love to dress up in pretty clothes and become pretty girls. Let’s face it, if we dared to offer up that bit of information to those folks, the next time a family reunion was in order, we might not get invited. At the very least, it would be an extremely awkward get-together compared to others in previous years!

So, Girls, I’m recommending not to share our thrill with other family members as a result of the above notes. Besides, when you release your little secret to one family member, the next thing ya know, everyone on both sides of your family might think you’re some sort of freak or weirdo!

Now if you’ve already released your little secret to some family members and they are accepting and considerate towards your crossdressing – lucky you! You’re in a distinct minority of crossdressers. There are still many of you out there who are still deep in the closet and not even your spouse or significant others know about your thrill of wearing pretty femme clothing. Been there and done that as noted above, and I wouldn’t want to go through that phase ever again!

Here’s what I did to share my CDing with others, and I recommend you all might want to give it a whirl as well!

My first sharing of my CD secret came with the customer service ladies at JC Penny’s in Pensacola where I used to have all my heels, boots, and booties shipped in order to keep things out of the sight of my sexy redhead prior to her acceptance of my crossdressing. So, my first public sharing of my thrill outside of our home and outside of an online CD site was when I took my crossdressing secret to those girls at the Penney’s customer service department.

I had about 50 of my best pictures of Scarlett loaded on my IPad and took the IPad to the customer service girls, asking them if they wanted to see photos of Scarlett. They couldn’t wait to see them! I opened the IPad to three women in that department ranging in ages from about 25 to 65 and showed them 30 of my top photos. My God, the reaction was off the chain incredible! Next thing ya know, they had passed the word on to some other employees in departments on the second floor and in less than ten minutes, I had a crowd of at least 10 ladies absolutely loving every photo of Scarlett and wanted me to stop in with more every time I came to the store – which I continue to do to this day!

Here are the next places I went over the next two weeks with my IPad, and later with color 8×10 photos in a folder and got the same exact reaction with each set of girls clamoring for more as I left each place!

1  1)    Sports Clips where I have my hair cut. The manager and all the hair stylists have seen loads of Scarlett photos, and they won’t even let me get my hair cut now unless I bring some Scarlett show and tell pictures!

2   2)    Sephora where I buy some of my foundation liquid and powder. The girls who work at these places are on the liberal side, open minded, and quite accepting of the LGTBQ folks, and now you can add CD to that list of letters as well!

3   3)    Ulta – See Sephora notes above. And I should have added kind, considerate, caring, inquisitive, and full of answers to a wide variety of makeup questions you may have!

4   4)    Plato’s Closet which is our largest consignment shop in Pensacola. With such a huge selection of girl’s clothing, footwear, and jewelry available at next to nothing prices. You would assume they would have admitted crossdressers in there all the time, but the first time I told them I was a cross dresser the girls were in shock until I busted loose with a pile of Scarlett photos. Then every girl in the place wanted to see my pictures. Some of them didn’t believe it was me, so I had to point out a small brown dark birth mark in the middle of my right shin. Then they were all believers that those photos were of me as a girl named Scarlett! Now those girls won’t let me shop unless I bring some Scarlett show and tell photos!

Other places to share your thrill of crossdressing with other employees are as follows: Stores in a mall or not in a mall you regularly frequent, thrift stores where you may shop on a regular basis, brick and mortar stores where you may buy lady’s shoes, wigs, purses, clothing, and other accessories.

And of course, the #1 place to share your thrill of crossdressing is right here with the wonderful girls in the greatest crossdressing site in the world – our very own Crossdresser Heaven – which is our way to get ourselves out of the closet or house on a regular basis and share our thrill of crossdressing with all of the CDH girls who share the very same thrill of wearing cute, pretty, sexy, and classy lady’s clothing! I get excited as soon as I put on a pair of heels! I just love being a girl as most of you know!

Girls, thanks for taking the time for reading another one of my informative articles. If you have other places you love to share your thrill of crossdressing, please send them in your responses to this article so that all of our readers of this article will have an exhaustive and complete list on how and where to share their own thrill of crossdressing with as many other accepting folks out there as possible!

 

Sincerely, Scarlett

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I love the thrill of cross dressing and based on the CDH girls' comments in response to my posted photos, I must be pretty good at exploring the feminine side of myself. I find it sexy, sensual, exciting, challenging, and ever changing. I'm so very blessed now to have as much money as I want to spend on Scarlett and can now, for the very first time in fifteen years, actually purchase dresses, tops, and skirts while shopping with my wife! I never thought that would ever come to fruition! I can now store all of Scarlett's things in our huge dream home when just a short period of time ago, it would all have to be kept in a temperature controlled storage unit. I love Crossdressing Heaven and know it's the classiest and most tasteful cross dressing site on line. All the girls are full of support and encouragement and if folks come to the site with alternate motives that aren't in line with our founders rules and regulations, they are quickly deleted from our site. Vanessa Law, our founder, keeps this site classy at all times. She has much help from her Ambassadors, Chat Room Monitors, Photo Monitors, Article Editors, and many more personnel to keep this site classy, encouraging, and supportive.
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94 Comments
  1. Vanessa Jones 2 months ago

    Oh thank you Scarlett for the wonderful article! You have some wonderful ideas. I guess I am one of the lucky ones as my wife and stepdaughter know and have been out with me dressed as Vanessa. Some women co-workers know as well since I came out to them last year. I must say, they are very accepting. Some girls at the spa/wellness center know as I have had my makeup professionally done there the past two Halloweens. They have encouraged me to have my makeup done anytime of the year. But enough of me, I have to say that your photos are just gorgeous…you are just gorgeous! Thanks for sharing

    • Author
      Scarlett398 2 months ago

      Thanks for such a sweet note, Vanessa! I put a lot of work into my photo shoots and do them all at home by myself with my Nikon D3100 sitting atop a Vivitar tripod with the self timer on the camera set for 10 seconds. This gives me plenty of time to grab a prop, or strike a pose, or jump up on a counter top and grab a prop or two. I don’t like my photos to be all about me in front of some blank wall canvas. I give them a bit more life by moving to various parts of our new home and using a variety of props and poses to add interest to the entire photo. Heck, I even added an alien from outer space to a couple of my last few photos. They are way back several pages now in the All Crossdresser photo section.

      Wow girl friend, you are very lucky and in a very distinct minority of cross dressers if you can go out in public with not only your accepting and encouraging wife, which most cross dressers don’t have, but also with your stepdaughter as well! Lucky you girl friend!

      My fantasy of a girl on girl date with a dinner and shopping involved with my wife will probably have to remain just that – a fantasy – as with the majority of cross dressers.

      Keep spreading the news of your thrill of cross dressing with as many folks as possible. We hope one day in the near future we will be as accepted as the groups of people represented by the letters – LGBTQ. Notice there’s not a “C” or a “D” in sight yet! Maybe one day we’ll see CD added to the list of letters!

      Have a wonderful weekend ahead, Vanessa, and thanks so very much for this lovely note and response you sent to me!

      XOXOXO Scarlett

  2. Carolyn Kay 2 months ago

    Hi Scarlett, I believe you are right in about telling others in your family and long time friends. If you do take the step things are going to change. I have not told anyone in my family except my wife who is tolerant. However, to show your point, we were at a family reunion last year and one of my sister-in-laws were selling pink bras to support breast cancer. She looked at me and laughing said do you want one, what your size. There was some laughs then I came back with – I am not sure, do you want to measure. There was an awkward silence then laughter. She came back with I will sell you one but then you can never come here again. I was all a joke but jokes have underlying truths in them. My wife was not happy I said anything.
    Great article, hugs, Carolyn Kay

    • Author
      Scarlett398 2 months ago

      Thanks for the thumbs up on my article and sorry about that awkward situation with a family member at a breast cancer event involving a family member.

      None of my family members, with the exception of my wife will ever know about Scarlett.

      Just yesterday I shared some Scarlett 8x10s with a new girl at DSW shoes in Pensacola. She was very impressed and didn’t believe it was me at first. I had to show her a tiny brown birth mark on my right shin to prove it was really me!

      I also had a very interesting interaction with an elderly lady who was working at Marhall’s checking the number of items taken back to the fitting room. A couple of weeks ago, I had a two Tommy Hilfiger dresses and they were exactly the same other than the size. I told her I needed to try both of the dresses on and she looked at me like I was absolutely crazy! I didn’t tell her I was one of the top cross dressers in the world when I went into the males side of the dressing rooms. I came out after trying on both dresses and I told her “This is the one of the two that fits me perfectly”. She looked I me like I was crazy again.

      So two weeks later, which was yesterday, I happened to have about 40 of my best photos of Scarlett with me and I saw her right there checking the number of items again. So I went right up to her and I asked her, “Do you remember me? I was the guy who was trying on those two black Tommy Hilfiger dresses and you were looking at me like I was crazy!” Well, I happen to have some photos of me dressed up as girl I call Scarlett would you like to see some of my photos of me as a girl?” She said sure and I pulled about 40 of them out and I think she was really jealous because as a girl I was a whole lot prettier than she was and she really didn’t know how to apply makeup properly.

      We exchanged pleasantries and I told her she would be surprised how many millions of guys out there were cross dressers. I told her that probably one out of every ten guys that comes into that store are probably wearing a pair of sexy girl’s panties. And then I invited her to come and check out our CDH site. She didn’t seem interested at all of seeing guys dressed up like girls. Anyway, I told her she would probably feel way different the next time I came up to her to try a dress on in the male side of the fitting rooms!

      XOXOXO Scarlett

      • Abby Lauren 2 months ago

        You are a very beautiful CD, Scarlett. I just love your wardrobe and your makeup skills.
        Abby

      • Author
        Scarlett398 2 months ago

        Thank you so very much, Abby! You always send me such lovely and sweet notes!

        Sorry it took me three days to get back to you!

        Love ya! XOXOXO Scarlett

  3. Linda Weest 2 months ago

    thanks for this article and sharing. I wait eagerly for the next how to bring up talk with SO.

    • Author
      Scarlett398 2 months ago

      Linda, that’s the article I’m not really an expert on but I’m probably gonna give it a shot. I hope I do the subject justice but it took me over a decade to talk my sexy redheaded wife to finally have “The Talk” with me!

      Have a super weekend girl friend! XOXOX Scarlett

  4. Author
    Scarlett398 2 months ago

    Leonara, you know my sexy redhead is the same way. I can’t be dressed as Scarlett while she’s present. I kinda like it that way. I usually get my girl on those days when she’ll be at work all day and then has her two hour hair appointment right after work. That gives me about 10 hours to get my girl on and do a decent photo shoot with 200 to 400 photos taken. The more outfit changes I do results in the least amount of photos!

    My sexy redhead has come miles forward with her acceptance of my cross dressing in just the last two years. She’s even purchased me a couple of classy sexy tops to be worn with shorts or skirts while out at shopping trips to our favorite stores – TJ Maxx and Marshalls. I probably get close to 90% of Scarlett’s clothing items as those two stores. My heels, boots, ankle booties, and wedges at DSW.com or JC Penney.com and then have them delivered to those two stores about 15 miles from my home and I pick all of them up there.

    Love ya girl friend! And so glad your wife of so many years is very accepting of your cross dressing and gives you your time and space to get your girl on!

    XOXOXO Scarlett

  5. Stephanie Kennedy 2 months ago

    Hi scarlette it is not fair that you have those gourges legs . i am accustomed to to be envious of cis woman but those legs. Wow now i have to deal with the woman in my. own community You look lovely and I will get there one day youare a inspiratio luv Stephanie

    • Author
      Scarlett398 2 months ago

      That’s sweet of you to say Stephanie and I get a lot of that from the lovely girls on this site. They tell me I’m their inspiration often and it makes me proud to serve as an inspiration to others!

      XOXOXO Scarlett

  6. ChrissyBee 2 months ago

    Someday I want to be as confidant as you, although I don’t usually or haven’t yet presented myself directly to others outside my comfort zone the idea is very exciting and I will be trying to more often.
    I’ll let everyone know how it turns out : )

    Kisses, Chrissy

    • Author
      Scarlett398 2 months ago

      Thanks a bunch, Chrissy! I’ve been at this thrill of cross dressing of mine for quite some time now. About 7 years I’ve been dressing full up about once every other week and I do my photo shoots on those days right here at our home all by myself with Nikon D3100 camera sitting a atop a very fancy Vivitar tripod and the camera is set on a 10 second self timer which gives me plenty of time to get in front of the camera and strike a pose with or without some sort of prop.

      It does take a lot of effort and work to transform into a 100% passable cute and sexy girl.

      Take care and please stay in touch, Chrissy! XOXOX Scarlett

  7. Tammie Swenson 2 months ago

    WOW! Scarlett do you live 24/7 fully ENFEMME with your SO? U look fabulous!

    My SOGGF when she first discover me wearing an outfit of hers was Royally PISSED off. Being that it was 3 weeks b4 Halloween (as I was sharing her house with her) she required me to dress FULLY ENFEMM in Public thru Halloween, thinking it would be fitting punishment, but I think by Halloween she realized that I was really enjoyed being Tammie. During the 3weeks she usually woke me up about 5am and would pick out what outfit of hers I was to wear that day, and b4 she went to work work would do my makeup and hair.

    Day after Halloween she didn’t wake me up as usual. I woke up about 8AM. Forgetting It was day after Halloween, as usual I went to dressing room area expecting to find her and the outfit to wear… she wasn’t there nor any outfit… so I went to her clothes closet and found hanging on a hanger on a wall hook an outfit I had worn a few days before. So I put it on along with some new pantyhose and flats.
    Went down to kitchen for breakfast,… there was my SOGGF at table, … I wasn’t expecting to see her… she said Good Morning Tammie.. I took off today and rest of week…I was hoping I would see Tammie again this morning.. .. it’s obvious u really enjoy being Tammie rather than Jammie so I think we should continue with you living as Tammie thru New Year’s but it’s time u have your own Feminine Wardrobe and makeup. So after breakfast we are shopping and get you professionally fitted for ur own bras and panties. Then she said now that your hair is rather long it’s time for you to have your haircut and styled feminine.

    Come New Year’s eve we went out to a Formal NYE party and I was wearing a nice tight fitting Formal evening gown. Between Halloween and NYE we had been shopping several times.
    Like you, the many sales Associates my SOGGF and I dealt with were amazed at how wonderful I looked.

    The hairstylist my SOGGF & I go to has always taken a smartphone photo or 2 of me
    since my 1st female haircut and styling. By the third styling session 3 other stylists were getting very interested and making suggestions. Matter of fact one of them suggested I let her wax and shape my rather bushy brows more feminine and slender.

    At my last hairstylist appointment one of the other stylists at the salon asked me I I had ever considered going blond or getting blond streaks in my brunette brown hair. Nope I told her.

    say the transformation is phenomenal. The

  8. Elaine Hamilton 2 months ago

    Oh my goodness I loved your story and you look stunning in that outfit …I am so jealous ..hehehe. Would love to go shopping with you, you sound like so much fun …yay !!!❤️

    • Author
      Scarlett398 2 months ago

      Thanks Elaine! I knew this article was going to get a huge response and it did!

      Yeah, I really liked my first try with girl’s shorts. I think it’s a real sexy look on me. Of course you had to pair the jeans shorts with the right tops and heels to make the look extra sexy!

      I am a lot of fun by the way. When I enter our chat room here at CDH, the girls get really pumped up when I go in there. They really appreciate my keen sense of humor which I let fly while in the chat room. I have a good time in my rare visits in the chat room. The reason, Elaine, why I don’t go in there on a more regular basis is that fact that it’s very time consuming. It’s usually about a 2 hour visit which most of the time, I just don’t have that much time to spend in there.

      By the way, is that you in your profile picture? If it is, you are so pretty and very sexy and definitely have the body to pull the full transition from guy to girl rather easily! It’s a dynamite photo and I love that dress or that top and skirt you’re wearing.

      Please feel free to check out my other articles and my public photos on here. The girls on CDH come to me on a very regular basis looking for tips and knowledge on how to take their own cross dressing skills to their highest achievable levels given their individual issues they have to overcome in an attempt to achieve that 100% passable level as a girl.

      Thank you for your sweet note and yes, I believe we would have a blast out there on a shopping trip together!

      XOXOXO Scarlett

  9. Lindie Moore 2 months ago

    Thank for the article. Amazing . I wish someday I will be able to as you say “Have the talk”. And thaks for all the advice you share
    Lot of love Lindie

    • Author
      Scarlett398 2 months ago

      Thanks Lindie, I’m expecting a huge response from this particular article. I addressed as much as I could on the subject considering the word limit placed on our articles!

      XOXOXO Scarlett It took me years and years to get my wife to finally sit down and have “The Talk”!

  10. Abby Lauren 2 months ago

    I waited through 10 years of marriage and a trip to Yosemite to finally have the talk with my wife. We were situated in a motel just outside Yosemite so my wife, in a sense, was a captive audience. I spent quite a while discussing everything about my CD’ing with her and assured her of what you spoke of in your article (eg. I’m not gay, etc.). Her response, after several months, was that she had gone into a state of total denial and hadn’t remembered anything at all!!! Ultimately, I insisted she hear me out totally and we came to an understanding that is quite similar to yours.
    In those years, we lived near NYC where I worked and I went to CDI (crossdressers international) every Wednesday night to dress and had a locker there with my clothes, shoes and makeup. She insisted that she NEVER see me as Abby and I’ve kept to that.
    Loved your article, BTW.
    Love
    Abby

    • Author
      Scarlett398 1 month ago

      Thanks Abby for loving my article. And for a few years after my sexy redhead came home from work unannounced two hours early and caught me in full up Scarlett mode, I thought I would be right where you’re at now with your wife Abby.

      I got the silent treatment for two days and nights and then date night rolled around and we got in the car and started down the road to dinner and a movie and I asked her if she wanted to talk about it and she said no just make sure to keep it out of my sight. And that’s all that was said about cross dressing that night. We had a super date and some super sex when we got home from dinner and a movie. I knew after that night there was going to be plenty of room for improvement towards acceptance.

      Now it took a few years to finally have “The Talk” and after the talk she was almost all in as long as I didn’t dress as Scarlett while in her presence. Since then, she’s purchased me two sexy tops, a dress, and three pair of sexy Ellen Tracy panties. I get to talk about this site and about cross dressing on a regular basis now. The conversations aren’t long ones because it’s not one of her favorite subjects. But her acceptance level has grown exponentially since “The Talk”.

      Now, if we are out shopping together which is something we both enjoy a bunch, I can purchase anything I want for Scarlett and we can even go up to the same cashier and she’ll buy her dresses, tops, and skirts and I can purchase Scarlett’s dresses, tops, and skirts – and panties and Silk Reflection hose too!

      XOXOXO Scarlett

      • Abby Lauren 1 month ago

        Hi Scarlett
        Thank you so much for your candor and personal information. I value it highly.
        My wife has offered me whichever clothes I want that no longer fit her (I now weigh less than she does) but, after the offer, never raised the subject again. So, I’m in a sort of limbo. In the beginning, I took her up on her offer and got some amazing clothes (that no longer fit me}. But, i have a fairly large collection of beautiful dresses (mostly from Rotita in China) that I wear when I go out- both in Jerusalem and FL.
        Thanks again, gorgeous.
        Love
        Abby

      • Author
        Scarlett398 1 month ago

        You’re welcome Abby! I was wondering where you’ve been. Losing close to $100 on football bets today. Not good. Will be my last weekk of betting. I usually bet $10 per game and this week is not going well at all. I’ll go double or nothing with the Cowboys tomorrow and if I lose that bet, I’m done for the year!

        Clothes – I’m totally out of room for anymore. You girls have seen about two thirds of them so far. Sounds like you’ve got plentye of pretty dresses. Wish I had room for more!

        Love ya! XOXOX Scarlett

      • Abby Lauren 1 month ago

        Sweetheart, you already look incredibly beautiful in whatever clothes you have. I have to try to find some room in my downstairs storage area as I’m expecting my kids soon. The trouble is I don’t know if there’s any room left for more stuff. (I need to make room for my kids and grandkids to store some of their stuff.)
        Love
        Abby

      • Author
        Scarlett398 1 month ago

        Find that storage room. Thankfully, my kids and grand kids live far far away which is super for me and the sexy redhead. After teaching middle school math and algebra after I retired from Eglin AFB in Civil Service purchase the highest tech weapons that went under our highest tech jets, I actually became allergic to children of any ages. I really hate them all and my wife doesn’t have any kids and never wanted any kids thank God!

        Now that we live in a palace. We host Sandy’s annual Thanksgiving family reunion each November now. We lived in shacks for years and years and never were able to host any family reunion. Now, when our neices and nephews show up, they are all old enough to drive so they are all 16 and up except for one who’s quiet and extremely respectful and well raised by a set of super parents. He’s 14 and a super kid.

        I don’t move any of Scarlett’s things because they just think it’s more of Sandy’s things because we wear the same size and wear the same style of clothes.

        Gotta run. Have a wonderful rest of the weekend, Abby!

        Love ya! XOXOXO Scarlett

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