An Interview with Rachel, Crossdresser

By Kendra Holliday | June 19, 2014

I'm just a sweet transvestite...

I’m just a sweet transvestite…

Last night I saw the musical Billy Elliot. In it, a boy experiments with wearing female clothes. I was interested to see older men in the audience show visible discomfort/disgust at the concept. It’s crazy how men dressing in women’s clothing is still so taboo in our society.

Meet Rachel, a 48-year-old man who is getting more and more in touch with his/her feminine side…

What is your sexual orientation?

I’m attracted to women. But being trans can blur what it means to be hetero or ‘normal’. Bi or lesbian? It’s a weird sensation being two genders at times.

How long have you fantasized about CD?

Since I was about 6 years old. I can remember having a Spiderman comic book that also had Wasp Woman and Black Widow in it. I liked Spiderman a lot, but I always wanted to be the Black Widow in her tight black outfit.

I also had very vivid dreams about being able to ‘wear’ a girls body. In the dream I would be a girl until I heard someone coming and I would change back instantly. After that there were only a few instances of trying on pantyhose. I mostly buried all desire to crossdress until about 7 years ago.

Are you married?

Yes. I have been married for 20 years to my one and only love. She has had a difficult time adjusting, I’m trying my best to be sensitive to her feelings while also true to myself.

What does your wife think?

At first she thought I might be kidding. Then there was anger and distrust. She wanted to know why I had lied to her all these years. I had repressed my transness so well that even I didn’t know fully.

Since then, we have talked about it, cried over it and have decided to take it a day at a time. She doesn’t completely like the idea but she tolerates some of my crossdressing. We continue to talk about it every day. By keeping communication open we not only grow to understand what transness means to us but we also strengthen our relationship as a whole. Take my word for it, this is hard work but ultimately satisfying for both of us. If normal couples put in this much time on their relationships I think we’d see happier people and fewer divorces.

On your blog(, you touch upon this. What did your wife mean when she said, “My husband isn’t my husband anymore”?

When I came out I decided it was going to be an all or nothing thing. I not only told her my desire to dress, I showed her my things. She knew about the underwear but not the shoes, makeup, wig and clothes. I felt that I couldn’t hide those things from her.

I also had shaved my mustache which was a shock to her since it made me look more androgynous. Nobody I know has ever seen me without a mustache since I was a teen. For a time after all this happened, my wife could barely look at me without seeing her vision of Rachel and not the man she married. When I realized that I was causing her such confusion and pain I decided to give of myself so she could see me as her husband again. I am growing the mustache back. This is part of the give and take in our relationship. I can’t expect her to accept this process if I shove it in her face. Also she allows me to dress a little so she can get used to it in small doses. So far this is working out for both of us.

Does she have any fetishes?

Not that she has revealed. My wife is very conservative but I hope that my crossdressing might help break the ice some way. If she is open to my transgendered activities I am just as open to her wants and needs.

Do you have a good sex life?

Our sex life was pretty normal after we married. Then it became more sporadic with the arrival of the kids. Then it died off quite a bit with other issues we were having to deal with. Actually since I came out our sex life has been re energized.

Are you monogamous?

Completely. We made that vow when we were married and have upheld it ever since. It has been one source of strength for us.

Are you into role reversal or pegging?

My wife and I have done a little informal role reversal. We can take turns being the seducer or the seduced. It just seems normal to us. I read a long thread in ‘Savage Love’ about pegging before I was completely aware of my trans tendencies. It intrigued me but I’m not sure my wife would be into it. Maybe she would I have never asked.

Are you a man who enjoys roleplaying female, or are you a man who wishes you were a woman?

In my case, it’s more than roleplay. If I were to go out 100% en femme I would rather be treated as a woman because I feel like a woman.

I know you are growing mustache back for wife, but for your ideal scenario – if it were only about you – would you be Rachel 24/7?

No. I do want to spend more time as Rachel, though. If I were to persue a more active role in the transgender community, I would most likely do that as Rachel. Sometimes I find that being the only ‘male’ in my TG support group can be a makes me feel a little out of place. However I find that I feel a bit more protective of the other women while I am there. Chivalry never dies I guess.

Do you like the option of going back and forth?

Yes, but it’s a challenge as I get more in touch with my feminine side I do find that it can be hard to come back to a more male presentation. Sometimes I have to ask my wife if I am acting ‘normal’. She’s my touchstone. The only place she demands that I be my old male self is in bed.

Do you ever blend the genders?

I under dress everyday, panties and hose, sometime with a garter belt. My toes are painted most of the time. And I have snuck a little mascara a few times. I do run around in ballet flats while doing stuff around the house. It confuses my boys but they don’t seem disturbed by it.

Do you want any surgery or are you content with how your body is now?

I’ve discussed transition with my wife, and neither of us would like me to go that route. I am quite comfortable with the parts I was born with. After 20 years, my wife is, too. However, I can’t in all honesty rule out transition completely because I don’t know how I would feel being Rachel for long periods of time. But the idea does scare me. I just can’t imagine just throwing away the male half of my life like that.
Laser hair removal or electrolysis might be options at some time. I hate shaving and epilating.

Do you have kids?

We have three children. One girl and two boys.

Do your kids know?

Only my daughter. She is cool with it up to a point. I told her because we have been very open with each other. A rare thing between a parent and teenager. I didn’t want to betray that trust by keeping it from her. My wife and I decided not to tell the boys since they are still at that point of discovering themselves.
I don’t want my gender issues causing any confusion or harm to them.

How did you tell her?

I asked my daughter if she could handle anything I might tell her that could effect our relationship as father and daughter. She said yes and I told her straight out that I like to wear women’s clothes. She wasn’t that surprised. She had noticed that I have been more interested in those things when we were out shopping.

What is your male side like?

Shy, funny, loyal, considerate, analytical, Sometimes depressed and/ or short tempered.

What is your female side like?

Confident, emotional (although that seems to be spilling over into the male side recently) happy, fun, outgoing, smart, lovable.

Do you envy women?

No. I admire them. Being a woman is hard work. Society puts tons of pressure on women to be “more like men” or “more like women”. That can be just as confusing as transgenderism. In fact I have found that some women envy crossdressers because the can ‘pretend to be women’ and can go back to enjoy the privileges of being men.

What things about being femme particularly delight you?

I feel free to be beautiful and sexy. En femme I have a confidence that is I have trouble explaining. A “fuck the world, I’m trans and proud!” feeling. I want to go out and show off my other side. To be flirty and dance. It also has a calming effect on me. I can dress away the stress. Showing a bit of my femme side has also helped me to connect with my family better. I am more compassionate with my kids. Less prone to anger and judging when things don’t go right. I think it makes me a better father and husband.

Before embracing the transgender community, what homophobia, prejudices and preconceptions did you used to have?

I was homophobic in the way many hetero guys act. They are afraid to get near them for fear of catching gay cooties. I used to make fun of gays or those we thought to be gay. However, I was lucky to have met George Takei. I had no knowledge that he was gay at the time. That meeting really opened my eyes. Since then I have found out several people I know are gay and I’m proud to call them friends.

I once worked with a man who decided to transition. Many of my coworkers would laugh and make derogatory remarks behind his back. Of course I had to join in to be part of the “normal” group. I now realize that that one man had more guts to come out and transition than anyone else I knew until recently.

Transgender people have to be brave. They have a lot to lose. Friends, families, jobs, etc. They have still not earned the respect that gays, lesbians and even genetic women have fought for. They most often go it alone in their quest to find their true selves. That takes a tremendous amount of courage. I am proud to be considered one of them.

Can you recommend any online resources?

Helen Boyd’s site (both of her books should be required reading for crossdressers and their significant others) a southern California resource. Tri-Ess a nationwide group for hetero crossdressers and their so’s google them for local chapters.

Do you feel guilt or shame when it comes to CD?

I did which is why I had to come out. Even if it was just to my wife. I was born and raised catholic so shame and guilt come easy.

Do you ever go out in public cd? Fetish clubs, vanilla, gay bar, parties?

I so desperately want to. Even if it is just to go to the supermarket. Unfortunately I can’t at the moment. Not until my wife can accept me dressing let alone going out in public.

Do you have any tips to share?

Be honest to a fault. To yourself first and to your significant other next. Many crossdressers seem to live life in the shadows. They hide their transgender feelings from those they care most about. I have read their posts on CD forums, most seem very lonely and fearful. Try coming out.

If you are brave enough, lend your voice to the transgendered cause so we can earn acceptance. The alternative is loneliness, unhappiness, an regret. This is the motto I have decided to live by:

Without honesty there is no trust. Without trust there is no chance for unconditional love.


Sonora 2011-06-03 20:43:43

“Do you envy women?

A. No. I admire them. Being a woman is hard work. Society puts tons of pressure on women to be “more like men” or “more like women”. That can be just as confusing as transgenderism. In fact I have found that some women envy crossdressers because the can ‘pretend to be women’ and can go back to enjoy the privileges of being men.”

Thank you for that. It brought a tear to my eye. And thank you for sharing your experience. :heart:


Stephen 2014-06-20 07:50:44

Something I’ve found, unfair tho it may be, is acceptance in society comes with how good the trans/cd looks out in public – and by that I do NOT mean ‘attractive.’ I mean well put-together, confident, and experienced.

In my home town I never noticed the male version of Fran, even tho she was a frequent guest at the same hangs as I was – but when Fran came out, she was more open and gregarious. You could see her visibly concerned with how she was going to be perceived, always paranoid and pointing out stares where there were none, but she was great – like Rachel here, more confident as Fran.

What also helped was how Fran needed to discuss the transition to help her through it, so any question was open-season while she was in public at our local watering holes. Equally important was, like Rachel, Fran is smart, talented, and already an important member of society. She took forever to come out at her job, and eventually chose to move from here, which likely helped her to start anew fully as Fran.

We miss Fran here, her super-smarts at Pub Quiz, and her ebullient personality as Fran. Again, she wasn’t what anyone would call ‘super attractive,’ but even on casual days she just looked so well composed as Fran.

I guess I’m saying all that to say “You GO, Rachel!” If anyone doesn’t accept you or if they get uncomfortable around you, you don’t need them in your life. And in my opinion. the younger your kids are, the more adaptable they’ll be to your choices…tho I completely agree with your reason for not coming out to your boys.


Michelle 2015-03-26 10:59:00

Rachel is very fortunate in her situation, despite some of the obstacles she faces.At least her wife allows her to express her feminine on occasion,and she gets to crossdress in her wife’s presence. My wife knew about my crossdressing before we were married,and I was in the hope I could progress with it, and incorporate it into our marriage.However; no such luck.She just totally blocks out my feminine side,and doesn’t have any interest in my crossdressing,so I’m totally left to my secret lifestyle.I’d so much love her participation and encouragement,to the point that I’d gladly allow her to pursue any activity she might desire.Even to the point where she might enjoy an intimate relationship with a ” real man “as they say.Fair enough I suppose.Thus my thoughts.All comments and suggestions would be welcome.


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