The Night She Found Out: My Crossdressing and Our Marriage

As a straight, married crossdresser, life can get pretty complicated. Typically, the “normal” setup in a marriage is that the woman is feminine and the man is masculine. In today’s world, we are much more accepting of other marriage and relationship lifestyles, but the stigma is still there.

If you are one of these straight crossdressers, it is hard ever to imagine that you could find a woman that you would be able to tell about your crossdressing side. You definitely wouldn’t imagine finding one that would be accepting.

In most cases you would assume that they would instantly get turned off and leave you. Fortunately, this is not the case. I hope that you all can learn from the mistakes that I made in my relationship with my wife & crossdressing.

Early Dating

When I met my future wife when we were in college, the relationship just happened naturally. I don’t think either of us was truly looking to be in a relationship, but we enjoyed each other’s company and eventually we began dating after being friends for a little while.

It was like any typical relationship in college where you need to balance the stresses of college and the social aspect of college.

We spent a lot of time talking about our lives and getting to know each other. But one thing that never came up was my crossdressing.

After how my previous relationship ended because of my obsessive crossdressing talk with my ex-girlfriend, I was not going to dive into that again. I felt like I needed to keep this secret to myself. After all, I wasn’t really crossdressing often in college due to having roommates and all that.

As we continued to date, I began getting more urges as I got closer to her. I think her style and looks were very attractive to me both as a crossdresser and as a man. I was still able to control my urges and I would only dress when I would have free time when she wasn’t around or if my roommate was out of town.

When I graduated, she had another few years of school left and we decided to embark on a long-distance relationship. I had gotten a job and we would try to talk on the phone every night to make up for the distance.

Now that I was getting a paycheck every couple of weeks, I was buying clothes for myself and dressing relatively often. I would take pictures and videos of myself dressed up to re-watch later and admire. All of this while still keeping the secret from her.

Engagement

After almost 7 years of dating, I finally proposed to her and she said yes. At this point, she still had no clue that I was a crossdresser. We were 1.5 years until our planned wedding date and I still had never mentioned anything about it and she had never found anything.

This was all going to change very soon.

She was just leaving my house to head back to her place after spending a wonderful weekend together and I was giving her my iPad to use since I never used it for much. I did however have my iCloud set up on it and sent myself sexy pictures of myself in panties.

I still to this day do not know why I did it this way, but sure enough as she was next to me I opened the iPad. My ass bent over in panties was the first thing that popped up when I opened the messages to get her account set up.

I almost vomited as I tried to hide it from her and delete it quickly. I was not quick enough though, she couldn’t believe what she saw. I remember her saying, “Who is that?” in a not very happy tone. I regrettably admitted that it was me. I didn’t really even know how to explain it. I just tried to play it off as an old habit and “I don’t do it anymore.”

This statement became a regular one as time went on.

Time passed by and we had recovered from that situation with minimal questions about it, but I continued to do that same behavior.

The next time she was at my house while I was at work, she found videos on my laptop of me riding a dildo.

This time, she had more questions. She asked me why and I just used the excuse of exploring it, but not really liking it. But at the end of the day, it wasn’t something that I still did from what I told her.

Unfortunately, this was just another mark against me in the trust category.

The last time I was caught before marriage was the time that she actually found my stash of clothes and feminine things that I have been collecting for years at this point. There were wigs, dresses, panties, heels, breast forms, dildos, etc. She was so angry at me for this because I had told her many times that I was over it and that I didn’t crossdress anymore.

She made me throw it all away to prove that I was done for good because I kept promising that to her.

So, I purged my stuff for the first time ever. I threw all of my things away and felt so much shame for what I ended up doing. I needed to stop, but I didn’t know how. I did not crossdress again before our marriage, but I felt like I didn’t have her trust and I had so much shame built up inside of me.

Years 1 & 2

After we got married, we moved in together for the first time ever. I was committed to stopping my crossdressing habit for good and tried to pick up other hobbies to get my mind away from it. I played a lot of video games and focused a lot of energy on my career.

Ultimately, I was just trying to bury my crossdressing desires. I was not very happy though; I felt on edge a lot and just really didn’t like who I was.

For me, I still needed crossdressing in my life, so I would secretly buy women’s clothing to be able to dress while my wife was busy or at work. I was able to successfully hide it in places around the house that I felt she would not find.

It was only there if I had an urge and needed to crossdress. But hiding all of this from her gave me a ton of anxiety and stress that made me continue to be on edge very often.

The anxiety would then get to the point where I felt like I needed to purge my things again, so I would take all of my clothes and throw them away.

This cycle occurred at least two more times during the 2nd year of our marriage. She had never found my things, but I always felt overwhelmed to the point of purging so that I would not get caught and maybe I could finally kick the habit.

I’ve thrown away several wigs, so many dresses, and more panties than I can count. I don’t even want to think about how much money I threw away over the years.

I think that is just an added element of shame that I had while I was hiding my crossdressing side from her. The lying and the financial impact caused me a lot of self-hatred during this time of my life. I just couldn’t control it, and I was stuck and lost in this cycle.

Years 3 & 4

A few years after getting married, I started planning in my head about how I would come out to her about how I still wanted to crossdress.

I would try to plan it while on my runs or while I was driving to work. In my head, I felt like I had thought about why I enjoyed it enough to explain it to her, but I still had so many concerns about how she would take it.

I had a lot of trauma from the past times that we had talked about my crossdressing. Would she feel awkward around me? Would she yell at me for hiding my feelings for so long? Would she want to leave me?

It was enough to procrastinate my confession to her each time that I was about to tell her how I felt.

In this time period, I was crossdressing again, like fully crossdressing.

I had a lot of things that I had bought since my last purge and kept in my backpack. I had wigs, some skirts, heels and a lot of accessories. It had gotten to the point where I had almost too much stuff to fit in the backpack, which is why I felt the need to finally tell her. But of course, I still didn’t tell her.

One night, she went to get my glasses for me. She thought they were in my backpack and before I knew it, I heard her yelling at me to come up and explain myself.

My heart dropped. She found it all and I should’ve told her a long time ago. I couldn’t explain myself. We were both in tears; hers were of anger and mine were of fear. She was upset that I was hiding this all from her and that I lied about being done with crossdressing.

We didn’t really have a productive talk, she needed her space, and I couldn’t make her feel any better about us that night. All I did for the rest of the night was purge my crossdressing things again and sleep alone on the couch, wondering if we would make it through this.

We didn’t talk for a couple of days. She was still angry, but she also wanted me to figure out what I wanted. I gathered all of my thoughts and tried to explain it all to her.

We talked one night after work and I finally gave her everything that I thought of over the last few days. Why I liked crossdressing, what I enjoyed most and why I wanted to continue.

She was kind of shocked that I actually enjoyed it since for years I told her that it was an addiction that I didn’t like. I don’t think she knew if she wanted to stay with me still, but this time she said you need to see a therapist about your anger and your crossdressing.

It felt like progress, even though I still needed to win her trust back.

I started therapy. I started being vulnerable more. I tried to be a better husband and after about a year of building back from this moment, I feel very proud of how far I have come and how much happier I am not hiding things from my wife.

Current Situation

At this moment, I am still working to be the best husband I can be and also be a happier person in general.

I am focusing on growing and exploring more with my wife and I feel like we have come a long way. She is now accepting of this side of me. She has some understanding of what I enjoy about it, at least as much as I do.

She still has not seen me dressed up to this point. The most she has seen is me with mascara and lip gloss. For us it is baby steps at the moment, but this year we are working together to do more. We have discussed the more sexual side of my crossdressing to explore when we are ready. I am also interested in doing more casual dressing around her at some point to avoid the hidden feeling that still exists sometimes when I dress.

At the end of the day, I am an example of a lucky man who has lied and hidden things from his wife. I am so lucky to have someone so forgiving and understanding. I continue to try to be a better husband for the best wife that a man could ask for.

If I had to leave you with one piece of advice: Be open with your significant other about your crossdressing; you should be the one to control the situation and inform them. And if they do find your things, just admit it and do not lie about it. You’ll thank me later.