Hi Girls, Scarlett here!

Now these stories and suggestions are strictly based on my own cross dressing history and experiences with my wife, along with my readings from two cross dressing sites. And girls, I could write a novel on this subject, however, considering the number of word restrictions placed on these articles, I’ll keep it as short and succinct as possible.

With my wife, she was extremely reluctant to have “The Talk” and it didn’t take place until years after she first found out about my thrill of cross dressing. I finally had to insist she sit down and listen to me from start to finish, and to let me answer any questions that may arise from our discussion.

Makeup Magic

1) I felt it was very important to let her know when and how my desire for wearing lady’s clothing all began. And for most of us, it starts as a very young boy with our mom’s or sister’s clothing. Regarding me, I told her it started with me discovering two full drawers of the sexiest black lingerie I ever saw in my life in my mom and dad’s off-limits bedroom while snooping around while the entire family was gone. This black lingerie of my mom’s was found in two full drawers in her main chest of drawers right in their bedroom.

I told her about selecting and putting on my mom’s black thigh-high hose first and then the black garter belt and a sexy black bra. After finding my dad’s secret stash of Playboy and Penthouse magazines, I spread some of them around me on their bed, opened the magazines to their centerfold pictures, and then had my way with myself for over an hour. After that session, I carefully put everything back exactly where I found it. And that’s how it all began.

2) I told her my cross dressing continued after that specific day but with huge gaps of no cross dressing at all for long periods of time. I either didn’t have the time or the urge with the responsibilities of working full-time, going to school full-time at night, and coaching my two sons’ baseball teams in between my semesters of college. During those many years, I had never taken it to the level of full-up cross dressing which is where I’m at with it now.

3) Several questions came up from her during our discussion. I don’t have the luxury of noting each one of her questions that came up because there’s just not enough space in this article to list them all. However, as a result of her questions, I had to assure her I wasn’t gay, I had no sexual interest in other men or women, and that I loved her more than ever. And most importantly, the fact that she would always be my first love. In my opinion, you must make this perfectly clear to your wife or SO. Remember that your own personal cross dressing wardrobe can’t ever love you back, however, your wife or SO can always love you back. Please remember that fact girls! If your cross dressing is more important to you than your wife or SO, you probably had some serious issues with that person prior to having “The Talk” and there’s no telling how much longer your relationship will last!

4) One thing I had to drive home hard was the fact that if it came to choose between my sexy redheaded wife and Scarlett (the name I use when I’m getting my total girl on), Scarlett would have to go! Unless your marriage or relationship is on the rocks, your wife or SO must know that your cross dressing serves as a distant second to your love for her or him!

5) After getting that cleared up, I had to describe in detail to my wife how important it was for my mental well-being and total happiness to continue on by exploring my feminine side and by continuing to cross dress. Shopping for all the items pertaining to being dressed as a cute, pretty, sexy, and classy girl named Scarlett was also an important part of the process to continue as well.

I told her and showed her that my thrill of cross dressing was not related to becoming some version of a “drag queen.” My ultimate mission with cross dressing was to become 100% passable as female when I made the total transformation from me in Handsome Husband mode to Scarlett with my total girl on in that dress or cute outfit.

She wanted to know where I learned my expert makeup skills, and I told her my skills were all obtained by watching YouTube videos on my laptop which were videos produced by professional makeup artists. I also told her I had never had a professional makeover done in person by anyone.

6) I made it clear that my admission to her of my thrill of cross dressing increased my ability to relate to her as a beautiful woman so much easier. I also told her my coming out helped me steer clear of any depression, guilt, or shame I had experienced in the past by keeping my thrill of cross dressing a complete secret from her and others over the span of so many years. I suggest you tell your wife or SO the same thing.

7) I also told her I simply wanted her to accept me exploring my feminine side and in no way was I going to shove this cross dressing issue down her throat. I told her the acceptance by her of my cross dressing could go as slowly as she wanted it to go. I also assured her, I wouldn’t be cross dressed in her presence if she was uncomfortable seeing me dressed as Scarlett, which in fact was the case. The comfort level with that issue will vary from one wife or SO to another for sure! Some wives and SOs will even let you get your girl on while going out shopping or on a date with them. Those cross dressers, based on my research, are in a small minority. It appears most wives and SOs – especially long-term wives are not comfortable with this at all! My sexy redhead sure won’t be going shopping or out on a date with me dressed as Scarlett anytime soon!

To my amazement and surprise, she decided to accept me and love me as I was. She assured me that my cross dressing would never, ever lead toward what I was afraid it might lead to and that was either a separation or worse yet – a divorce. She let me know that her love for me would maintain and stay as strong for me as it always had, and I could continue my cross dressing with only two conditions. One condition was that I didn’t dress up as Scarlett in her presence and condition number two was that the neighbors and her coworkers from her high-level position/job in our county would never find out about Scarlett.

After showing her about 50 of my best photos of Scarlett, I simply got up and gave her a big hug and kiss and told her the limits she placed on my cross dressing were more than reasonable and just fine with me!

After seeing plenty of the photos of Scarlett, she more than confirmed that I would totally pass 100% as a girl. She even admitted Scarlett was just as pretty and cute as she was!

Well girlfriends, I have almost met my word limit with this article so it’s time to bring this one to an end.

I’m sure you have further suggestions to add with mine, so please feel free to expand my limited list!

I would also love to hear how you broke the news to your wives or SOs and to tell me how your version of “The Talk” went with them.

To all my CDH girlfriends – I love you all and hope you enjoyed this entertaining subject. I so look forward to your responses to this article!


XOXOXO 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.
  1. Misti 1 week ago

    Does she allow you to go out in public?? That was one of my wives questions and restrictions… Misti

    • Author
      Scarlett398 1 week ago

      Good question Misti! And the answer is: “Not Really”.

      However, my sexy redhead goes to quarterly seminars associated with her work four times each year. She’s gone for three days and two nights. I pick one of those nights to go out in public as Scarlett. I’m 100% passable as a girl so no one has a clue I’m a guy when I’m out.

      My first stop is usually to our nearest mall which is about 15 miles from our home. I’ll walk up and down about four long hallways and then go into the Sephora shop where the girls know me as Scarlett. I will also go into Victoria’s Secret and buy 5 pairs of panties and some perfume.

      Then it’s off to either a movie or downtown to the safe part of town is where there are about 7 bars hooked together by a long wide common hallway where once you enter, you don’t have to go outside. I usually stroll through everyone of those bars just doing a bunch of people watching. Sometimes I’ll have a seat at an empty table or a table of accepting looking girls and have a conversation or two about a variety of subjects. The one I enjoy the most is “What’s it like to be a cross dresser!”

      Finally around 11 pm I go to one of my favorite photo locations in town. It’s a brightly lit up outside mechanic’s garage that looks like a scene from the 1940s or 50s. It has a couple of mechanical car lifts with cars usually up on them and a bunch of 55 gallon drums, air tools, some products like oil and antifreeze and a bunch more items. There’s also two old Coke machines and about 4 or 5 fascinating angles to take photos from. I pull my Honda SUV in there, pull out my Nikon D3100 which is already mounted atop an expensive Vivitar tripod and set the self timer on the camera for 10 seconds and then start taking photos of Scarlett from different angles with a variety of such interesting backgrounds I’ve ever seen. It’s a real rush!

      That’s it for now…Let me know if you have any questions Misti and thanks for the question. I enjoyed answering it!

      XOXOXO Scarlett

  2. Anne Preuss 6 days ago

    Hi Scarlett,
    I love how you thoughtfully lay out your points for addressing one’s crossdressing with their spouse/SO. Every one of your articles is so thought provoking that it’s sometimes a bit scary to read them because you open up raw emotions within me.
    I am different from you from the standpoint that if I were to be completely honest with my wife, I would have to tell her that I have wanted to be a woman ever since I tried on my mother’s underwear at age 11. It’s a long story to tell about how I reached this point….there’s no room to say it all and nobody would want to read it anyway. What keeps me closeted is that I love my grandkids so much that I would die if I were not allowed to see them. You make excellent points within your article that I would definitely use if my wife ever discovered my dressing. I cannot thank you enough for that.
    On a whole different level, you are why I wish I were a woman. You always come across as the woman whom I would have as my best girlfriend. To me, you exhibit the qualities of intimate sisterhood that women share amongst themselves that I would share with you in my “perfect world”. There is nothing sexual about this. It’s entirely on a female psychological/emotional level that your articles make me feel like this. In a different dimension, we would be attending PTA meetings together, sharing recipes, meeting in a coffee shop for conversation….. Please do keep on sharing your thoughts. As always, I look forward to your next article.

    • Author
      Scarlett398 5 days ago

      Well, Anne, I must say that’s one of the sweetest responses I’ve ever received to any of my articles! And it’s so well written! I really think you need to start writing articles to post in this section and ask me to the editor on your articles. They would be so easy to edit. I did’t know if you knew I’m an editor in this section as well as a writer.

      Thanks for the lovely compliments, Anne. “The qualities of intimate sisterhood that women share amongst themselves” – that’s so sweet to hear from you, Anne.

      And by the way, I would love to hear the story about you wanted to be a woman ever since you tried on a pair of your mother’s underwear. You should have seen the two drawers of the sexiest black lingerie I found in my mom and dad’s bedroom when I was about 9! That’s how I got hooked on wearing women’s clothing. She had black everything in there. My dad must have loved seeing her in all of that sexy stuff when he made love to her. There were sexy black garter belts, black silk thigh high hose, black shear bras, and black shear panties. I had to put on one of everything and have my way with myself for an hour.

      I found out I didn’t want to be woman full time when I started to perfect the world of makeup. After I took it all off, it took my face two days to heal. It still does to this day and I use the best makeup remover Neutrogena towletts around! I couldn’t be a full time girl because my face couldn’t take the makeup on and makeup off every morning and every night. I’m really good at putting it on as you can see from my photos. And, Anne, I’ve never had a professional makeup or any help from that sexy redhead of mine. I learned it all from watching You Tube videos I found by putting search words in Google search blocks.

      You hit on something really important about being a member of this site. I’ve built a couple of really strong girl relationships and when I go into the chat room, the girls really love my sense of humor. The whole chat room kinda lights up when Scarlett goes in there. I don’t go in there very often but when I do, the girls think it’s party time – Scarlett’s here! We’re gonna have some fun for a couple of hours!

      There’s one girl named Danielle who absolutely loves me. She kept asking me questions through the use of private messages to help her take her cross dressing skills to higher levels. And know she’s just as pretty as she can be and gives me all the credit. She’s one of my groupies who always sends me a sweet response to one of my photos when I post a few after a photo shoot. I’ve never posted photos and not gotten some sort of sweet response from her. She she’s my BFF right now on here.

      One thing about the chat room is being able to talk girl talk. One thing really bad about the place is if you mention sports of any kind, they will all sign off like rats leaving a sinking ship! It’s not a prohibited subject like sex, politics, or religion, but if you mention sports, most of these girls simply aren’t into them. They would rather talk about what brand and color of panties they like to wear the most for two hours! I’ve been in and around sports at the highest levels my entire life. You wouldn’t believe the stories I could tell you! Even if you saw my photos, you would think I photo shopped my way into those photos with all of those sports stars! My wife has to tell everyone that’s really him and all of his photos are real with no photo shopping done!

      That’s it for now Girl Friend! I feel like I can call you that after that wonderful response you sent in reply to my article.

      Gotta run, and we’ll talk again soon!

      XOXOX Scarlett

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