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The Stories of Real Crossdressers

by mattie on June 29, 2008

The Conversation.

There’s a little secret within the crossdressing community that goes something like this: If people only knew how many men crossdress they’d be amazed at the stories of everyday guys who are crossdressers. It’s true. There are estimates that one out of every ten men would like to crossdress, or does so already – but as you might imagine it’s hard to pinpoint the exact number. To gauge how many, and what kinds of men like to wear women’s clothes though one only needs to look at the backgrounds and types of men that exist within the crossdressing community. What do you find? That crossdressers are EVERYWHERE!

A recent thread on the crossdressers forum reveals the variety of men that live their own adventure daily:

“I own my own electronics design biz building computer related gadgets for professional Powerpoint users.” -Christine

“I am a Paramedic and was a firefighter for 6 years.” – Amy

“Hi. I’m a plumber so am unable to dress at work although I sometimes underdress. When I’ve got paperwork to do at home I always dress as an office girl.” – Barbara

“I work in Primary Care Medicine.” – il

“I’m a carpenter doing mostly residential framing.” – Lisa

“I’m a retired carpenter/ structural maintenance mechanic/ truck driver.” – Jill

“I’m an electrical engineer.” – Pamela

“I’m a daytrader” – Seville

“Passenger Train Driver for government owned railway, I always go to work in fem panties and have worn bra, tights or panty hose in the cooler months.” – Kylie

“Cosmetologist (Hair stylist!), makeup artist, both conventional and permanent.” – Tami

“Medical Insurance Claims Analyst” – Nicole

“I’m a Firefighter and wear panties 24/7. God help me if I ever get hurt.” – Selene

“I currently overhaul hydraulic actuators for military aircraft.” -Serina

“Underground Coal Mining” – Karren

“A boeing 777 co-pilot. Nothing can explain the feelings of wearing pantyhose at 35000ft!” – KE

“I am a Computer Aided Drafter for the US Army Corps of Engineers.” – MixedEmotion

And the list goes on…

There’s this stereotype that the types of men that are most likely to cross dress are “feminine” or “gay” men that are easy to spot, that crossdressers must be underachievers and dress for the attention of other men. Nothing could be further from the truth!

In my case throughout college I was near the top of my class. I was a DJ on a radio station that covered most of a major metropolitian area, served as president of both my high school and college class – and was in the honors society of my area of study. I’ve since attained a Masters degree in my field and again graduated near the top of my class. Now I’m happily married and have started my own company. My story isn’t unique however. Many of the crossdressers you meet these days are successful fathers, husbands, men – who serve their companies, families, and country with honor and dignity – hardly the stereotype of “underachiever” at all.

If you don’t think you know a crossdresser, I can guarantee you do. Crossdresser stories aren’t hard to find at all.

Do you have a story? Share it below, or if you’d like to write something more contact me!

Image credit: malias.

{ 92 comments… read them below or add one }

avalana December 22, 2011 at 11:31 pm

my cousin babysitters dressed me in girl clothes at age 3 since the all wanted a niece,and my mom and her sisters said i was a pretty girl. so i kept dressing in cute clothes,supplied by my girl cousins and her freinds.i also dressed in boy clothes,but i really liked wearing dresses and other girl things.and then i had a baby sister, and another,and another!needless to say may cousins were happy! but they and their girlfriends were happiest when they were able to dress me up,which i loved to do!!i thought that panties and dresses were way more comfortable than stiff ,drab,boy stuff. my mom was a part time seamstress,so as my 3 sisters got older,she started sewing things for each of them for style shows, easter ,birthday parties and so on. as i was the same hight and weight i was the willing and able hemming model for all! and my sisters LOVED IT. they suggested wearing paties all the time,introduced me to training bras,full and half-slips,and later on pantyhose,and sexier panty and bra sets… and they and my cousins startedin on makeup….now, a bunch of years later, having fought wildfires,morked in underground mines and such,i still prefer dressing as a girl.. simply because girl/clothes not only feel better, but they also fit me better(sz 6/7) than male crap… it’s too bad that mid 1800 ideas,mostly due to strange religious ideas..regardless,i still prefer to wear soft,sometimes slinky things,and i ALWAYS stay in contact with my feminine side with no regrets other than closed minds/perseptions and certain religions until later may i say baraka bishad(may the blessings be)…peace to all of you, avalana

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Anne December 23, 2011 at 6:26 am

Okay, please bare with me,
I am 45, hetro, married 15 years with 3 children. My wanting to cross dress came out three weeks ago after I had (another) near breakdown. I have suffered from depression for as long as I can remember and it is something my wife has had to deal with for as long as she has known me. Let me say that she is a wonderful person who has had to put with more than I can imagine in dealing with me and my issues.

First, let me say that I am happy being born male and have no desire to change that. That being said;
It was in the course of getting me to talk that the subject of my feminine feelings and cross dressing came up. As I spoke to her, tons of long repressed memories came back and from them my desire to cross dress came to light.

The first time I put on women’s clothing I was ten or eleven, trying on my mother’s clothes when no one was home. It wasn’t a sexual thing, I just liked the look and feel of them and when I was dressed, I just felt right. I didn’t think of myself as a girl, just that wearing those clothes was something I should be doing. That continued for several years until she and my step dad divorced. After that I could no longer dress up without getting caught, and I was terrified of being outed, so I repressed that part of myself.
All through high school and while in the military I found myself fantasying about dressing up, both in secret and publicly, I often wondered if I could pass as a real woman, but I was simply too scared to actually do it. After a time I managed to repress even this much of who I was inside.
In the last few years, that fantasy started to come back, but that was all I would allow myself.

As I can see now, from this side of admitting who and what I am, that my repressing my feminine side and desire to cross dress caused me a great deal of pain and suffering, and in the least made my depression worse. I truly wish that I could have dealt with this decades ago.

Now, with the help and understanding of my wife, I am starting to address these issues. Not only has she supported me unconditionally, she is even helping me to discover the person I am inside. She wants me to be open and honest about my feelings and I am learning to do that. Not only that, but she has bought me my first few items of clothing and encourages me to wear them when ever possible.
(These are under things only, we don’t want to bring this issue up with the children until they are much older. However, she has said that she wants to see me in full dress, as soon as we can have some time alone.)
I can’t imagine going through this without her and it has brought us much closer together. I love her and trust her even more now than I ever thought possible.

Looking toward the future,

Anne

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avalana January 22, 2012 at 12:21 am

i do understand your situation. many of my girlfreinds have misunderstood my croessdressing., although having been raised the way i was,and the resoned i continued dressing in feminen clothes, is because they felt so nice,and right, not to mention way more comfortable…they fit me better…still do …may all your desires and needs hold true to you,baraka bishad…may the blessings be….with the best of wishes and thoughts love avalana

Clara January 19, 2012 at 8:56 am

I am a 56 years old, who has a wonderful wife that is supportive but careful about me cross-dressing. We call these outings. We have gone out together many times (shopping, dinner, sightseeing) mostly when out of town. I have cross dressed since my early teens. Last summer I had a opportunity of a life time. I needed to drive cross country by myself so I took the opportunity to make this a cross-dressing trip. My first day out I had my nails done and checked into a motel. The next morning I got up got dressed fully dressed (hip pads, breast form, wig, make up etc) in a tank top, skirt and blouse and head out on the road. The feeling of freedom was great. I stopped when I needed to (restroom, meals and gas) had not problems. That night I checked into the hotel totally dressed, no one seemed to care or notice. The next day was a hot one so I dressed in a light skirt and blouse (note a long sleeve one to cover arm hair, I had shaved my legs). Along the way I stopped and did some shopping and decided to purchase a bathing suit one that covered as much as it can (skirt type and high back). That evening I waited for the right time to go to the pool when there was no one around (late), what a trip. A young couple joined me while in the pool, but they stayed at one end doing there thing. I was able to get out and cover with a large towel with out incident. The next two days were again wonderful in that I was enjoying myself doing some of the day to day things dressed as a women. Being careful of course. One day when I was on the phone an calling for a reservation I could tell the gal on the other end seemed not sure when I spelled my name “Clara” with my voice, when I checked in that evening there were to gals at the counter and it was very busy and lots of people in the lobby. I over heard the one gal say to the over (you spelled it correctly “Clara” she is a women, again what a trip and whether they really noticed or not, they treated my as one.

Take some chances, be careful but be yourself.

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avalana January 31, 2012 at 12:06 am

why is it that no more humans write? do they care not? are we on a planet that cares not for ALL the inhabitants? no matter what? jeez,eh? at any rate ,peace dl

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avalana January 31, 2012 at 12:06 am

why is it that no more humans write? do they care not? are we on a planet that cares not for ALL the inhabitants? no matter what? jeez,eh? at any rate ,peace dl and avalana

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Bill. (Tammy) February 7, 2012 at 6:52 pm

My storie started when I was little I was adopted by my grand parence. I had two sisters and my grandma decited to dress me as a girl so that was the first time. I diden’t know then that I enjoyed it so much that I would go to any lenth to dress in any type of cloths of a girl.
I’m a man and I don’t have any desire to be what I am not. Althought I have wanted to have someone elce make me up and I want to see how well I can pass as a women.
My wife knows that I crossdress she dosnot care as long as I don’t tern gay on her. I love my wife and I don’t ever want to hert her so I only dress in private when she is at work. She works all day long and I work the grave yard shift so I have the day to myself when I’m. Not a sleep. For now things are working out fine and I think we all are happy so I don’t want to change a thing.
I do ware my panties and my bra’s under my work cloths also. I don’t see anything wrong with it and I enjoy it. I’m just being me. Thankyou for reading my story and I hope your story is a good one.

Tammy

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