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.

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.

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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!

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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.

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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 Crossdresser 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 alternative motives which aren't in line with our founder’s 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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Miss Lollipop
Miss Lollipop
2 years ago

Hello, I saw your answer in a previous article, and thought I’d do some further reading myself, as I was curious. As much as that’s a well presented article with outlined ‘steps’ I still take the stance that ‘coming out’ isn’t necessary. And will always continue to do so. ~ As much as there are success stories, there are also the catastrophic results of the same, the coin always falls on 2 separate sides. We can’t forget that as a result of, ‘coming out’ people have destroyed relationships, ostracized themselves and been left completely alone and vulnerable, been cast out… Read more »

Miss Lollipop
Miss Lollipop
2 years ago
Reply to  Scarlett398

No, maybe I’m not clear. I left my ‘male side behind me when I was 16 years old. I never ‘came out’ I just ‘moved on’ to become, ‘Me’ ..Changed my name eventually by deed-poll and never looked back. My path was a journey of assertion. It wasn’t much of a surprise to anybody, I was a very ‘odd’ male. So this has led me to where I am today… Maybe that makes more sense now!?
x Miss Lolli x

Robin Wilson
1 year ago

Scarlett this was very well written, and something I needed to read. Thank you so much for sharing with us!

Robin Wilson
1 year ago
Reply to  Scarlett398

It wasn’t the prose, or literary gymnastics that caught my eye, but the content hit me in a real way, as this is what I am wrestling with right now.

Baily Marie Lovejoy
Active Member
1 month ago

I came out to my SO in the very same way Scarlett. Allow me to set the tone… My SO AND her family are dead against gays, Crossdressers, Drag Queens. To hear them talk makes me think I’m totally in the wrong family. “BUT” no the less I had to tell her. It wasn’t something I wanted to do by any means. It was what I needed to do. I can see Lollipops view however, she is living as a woman. We don’t have that luxury. We didn’t or couldn’t make that decision In Our teens. Thus “ The Talk”.… Read more »

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