I grew up in a nice family environment with an older brother.  My personality is similar to my mother’s.  My mom is a calm, understanding, and loving type, and my dad is loving as well, but in a different way.  He is also a strong and hard man.  He is strong in his morals and beliefs and was hard on my brother and me when he felt he needed to be.

I remember as a young boy being drawn to girl’s clothing.  One of my first memories is at my grandmother’s house wearing my aunt’s black leather boots around.  At that age, I’m sure it’s normal for any boy to do that, but it felt different for me.  I was drawn to them.  I remember spending a lot of time in the bathroom trying on my mom’s clothes.  They obviously didn’t fit, but it felt good to wear them.  I was never drawn to boy’s clothing like I was to girl’s clothing.  I remember thinking how nice they looked and how nice girls looked in them.  I would often wonder why boy’s clothes weren’t like that.

My mom often wore pants to work with knee-high stockings.  When she got home, she would take them off and lay them beside the couch.  When I was in elementary school, I would sit on the couch and watch cartoons in the morning before school.  If my mom’s stockings were still there, I would put them on under a blanket.  I remember one morning my dad coming and telling me to get ready for school, and when I took the blanket off, he saw the stockings on my feet.  He rushed over to me and started yelling.  “WHY ARE THOSE ON YOUR FEET? TAKE THOSE OFF; THOSE ARE FOR GIRLS, YOU’RE NOT A GIRL, YOU’RE A BOY, BOYS DON’T WEAR THOSE.”  I remember crying and later being really scared and confused.

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The feelings didn’t go away.  I was still drawn to girl’s clothing, and I wanted to wear them, but I couldn’t.  I was a boy, and boys don’t wear those.  I couldn’t help myself, though.  What was wrong with me?  Why was I like this?  Was I supposed to be a girl?

I knew I couldn’t let my dad catch me again, so I was careful about how and when I would do it.  He was a career firefighter and worked 24-hour shifts, which provided opportunities.  I also didn’t know how my mom would react, so I needed to be careful so she wouldn’t catch me either.

I wasn’t careful enough because I remember her finding a pair of her pantyhose in my room.  She asked me about them, and I think I told her something along the lines of liking to see women wearing them, so I put them on and looked at myself.  Her approach was slightly different than my dad’s.  She told me not to wear them, brought me a JC Penny catalog, and told me to just look at the women in the catalog.  I look back, and I think it was a cute and funny gesture.

After that, I started finding better ways of hiding things.  It was mostly pantyhose because I felt my mom would definitely miss other items.  Since she already found a pair of pantyhose, I was sure I would be the prime suspect.

Once I started puberty, another feeling arose.  When I would dress and see myself, I would begin to get a sense of arousal.  That just added to the confusion, and I would rip the clothes off in disgust because I’m a boy, and boys don’t wear those.  The feeling of wanting to wear them never went away.  Once my hormones leveled out, the arousal feeling went away, and I felt more like myself when I dressed.  I was starting to date girls, which offered opportunities to buy clothes of my own.  Christmas was the best time because it would seem like I was buying a gift.

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I raced BMX bikes as a young teen, and once I was in high school, I started my first job at a bicycle shop.  Working there, I learned of road racing, like the Tour de France.  In road racing, cyclist shave their legs (not for aerodynamics as many think).  I was intrigued by this and decided to start racing road bikes.  The thought of being able to shave my legs excited me.  It made me feel a little bit more like a girl, especially when I would dress.

I remember my parents coming to my first race.  I pulled off my sweatpants to get ready, and there were my silky smooth legs.  I remember my dad asking my mom under his breath, “did he shave his legs?” and my mom replied, “they all shave their legs.”  I could tell he was bothered by it, but he never said anything to me about it.

I continued to race bicycles through most of my adult life, but not solely to shave my legs.  I enjoyed the sport and was passionate about it.  It didn’t hurt the way my legs looked in a skirt and a pair of heels either.

Throughout my young adult years, the conflict of trying to figure out what was wrong with me, why I was like this and was I supposed to be a girl still rumbled inside.  The feelings of wanting to wear women’s clothes never went away.  My dad’s words still rang inside my head, though, along with the vision of the stern look on his face, “YOU’RE A BOY, BOYS DON’T WEAR THOSE.”

After high school, I started my career as a firefighter, and on weekends when I wasn’t working, I started going to clubs with friends.  I loved the music and the people seemed to suit me.  Drugs were a big part of the scene, and unfortunately, I fell victim to that and started using various types of drugs.

In the club scene, I did, however, meet a girl, and we started dating.  We had some gay friends, and because of that, I felt she wouldn’t judge me if I told her about this other side of me.  I mustered up the courage and spilled the beans to someone for the very first time.  She was interested in seeing me dressed, so I made her close her eyes while I put on my hose, a dress, and a pair of heels.  I will never forget when she opened her eyes.  She gave a little head nod with a slightly scrunched face and said, “oh, f*ck yeah!”  That made me feel good, and I was relieved.  I considered myself a freak with a dark secret and she was accepting and supportive.

One bad trait I had was insecurity.  The drugs only amplified this, and if she was ever hanging out with her friends while I was working, I became very jealous and eventually ruined our relationship.  I was a jerk and it was one of many regrets in my life.

Quite a few years later, I would eventually meet the woman I would marry.  She pulled me out of the drug-filled world I was in and cleaned me up.  We had a child together, but unfortunately, our marriage would crumble when, ironically, she became addicted to opioids.

I never told her about the other side of me.  It sounds weird because she was the woman I loved and trusted, but I was never sure how she would react.  I think I was more afraid of losing her than I was of what she would think of me.

She eventually found out by chance after we had separated.  I had carelessly left a pair of shoes inside a bin in our closet.  When she asked, I gave her a summary of my story.  She wasn’t understanding and would later try to use it against me.

After a few more failed relationships, I’ve lost the desire to date.  The conflict still rumbles within and can be overwhelming at times.  I have periods of depression that can last for weeks.  I’m able to hide it and deal with it pretty well, though.  I’ve never had any thoughts of harming myself.

I remember my mom telling me at some point in my life when she was pregnant with me; she had hoped that I would be a girl.  I always had a feeling that I should have been a girl and would often wonder why I wasn’t a girl.  I don’t think the questions of why am I like this and was I supposed to be a girl can be answered.  I know now that there is nothing wrong with me.  I’m a boy, and boys DO wear those!

Thank you so much for reading my article and if you have any response to my article or if you’d like to answer one or more of the following questions.

April Live Sessions - cdh
  • When you were a young boy, were you ever caught in the act of wearing feminine clothing by either one of your parents and what was their reaction?
  • When someone you had a relationship with got the news you were a cross dresser, was there acceptance or non acceptance from that person?
  • If you’ve been married for many years and your wife has no clue you are a cross dresser, what do you think her reaction would be if you came out of that cross dressing closet with the big news?

Thanks again for your time and responses!

Sincerely, Deni


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Candice Ashland
2 months ago

I have been caught by my mother and father to many times to count. I was once wearing my sisters panties and fell asleep ( i have three older sisters no brothers) my father came in to wake me for a fishing trip. he came in my room and pulled back the covers and said wake up sleepy head, and I was so exhausted i just wanted to crash, he started to laugh not mean but like a chuckle.he smacked my ass and said well these are cute, covered me back up and split. I did not realize I was… Read more »

Liz Craig
Active Member
2 months ago

My dad was the same way as yours growing up and it was tough.He was nothing but a negative influence in my life.I am still lucky to have my Uncle John in my life.whom has been a positive influence in my life growing up.Him and my dad never got along.He was always on my dad how he treated me

Liz Craig
Active Member
2 months ago
Reply to  Deni

It was terrifying for me,ended up being diagnosed with PTSD when I was 13.Luckily my Uncle taught me a lot what my dad didn’t do,mom was glad he did this for me.

Liz Craig
Active Member
2 months ago
Reply to  Deni

I am now,I still have to watch it with the PTSD.Had one flashback so far.

Bobbi Watt
2 months ago

I grew up with two sisters and one brother and was always left home with my mom and sisters and I was good with that . My older sister wanted to be a hair dresser and liked working on me . Any ways if my father ever caught me he would of beat me up he did have some good names for me like little queer man and a few other names but never did catch me. When I was in high school I partied hard many nights I would come home and put something of my sisters on and… Read more »

Elayne Edwards
2 months ago

Hi Deni i can relate to everything you mentioned. My Father was a Lt Col USAF strick discipline . i got caught wearing things that i has stolen off a clothes line on the base where we were stationed. Punished severely . caught a second time i was sent to Physc’s Doctors Etc. dad could not have a faggot cross dressing son around so i was sent to live with Grandparents on a farm in the Mid West. grandfather was told to make me a man !! work was hard farm chores but i would sneak in an put on… Read more »

Amilia Tanner
2 months ago

With me it was more the shoes. My mother always wanted me to “show off her shoes (and to stretch them). I always enjoyed wearing them. I think that is what started me to dress up.

Alisha Alex
2 months ago

Growing up in the middle east where the society’s mindset is sexist and patriarchal made it even risky for me to crossdress. I totally can relate to this. Awesome article.

Kristen Smithly
2 months ago

Hi Deni, What a great article! I have been crossdressing since I was very young. My parents never said anything, though I think they knew. I am quite certain my mother knew. One time when I was a freshman in HS they took me to a world famous Chinese restaurant in Seattle, where I grew up. I got changed into some cleaner clothes with one of my mom’s girdles on underneath (I have no sisters), the kind with garter (suspender) clips. I didn’t even think about them showing an outline. Jeans were somewhat tight back then (wonder how many times… Read more »

Last edited 2 months ago by Kristen Smithly
T.J. Byron
Trusted Member
2 months ago

You look beautiful darlin’!!
Hope you are staying safe…
Enjoyed your story, similar to many thousands of others…
Love to you…
Dr. T.J.

Jasmine Honey
1 month ago

Hi Deni, I to have been dressing on and off from a very young age, my parents caught me once when I’d left some panties Id worn lying around by mistake. Fast forward years later. Been married for many years , and I tried coming out to my wife, I even started dressing when we were alone in the house, but eventually she couldn’t deal with it. So back in the closet I went. I had quite a few sets of underwear and a bit of fetish stuff. But eventually I had to get rid of it all. I feel… Read more »

Sarah Kanter
1 month ago

Great story. Do you still cycle? Do you ride en femme? I’ve always liked cycling, in part because the clothing lets you cross boundaries pretty easily.

Would love your thoughts, please comment.x
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