Discover crossdresser in classroom

I’ve had a desire to crossdress since my latter high school years. I can remember the first time I felt the desire to do so I was sitting in class and I thought to myself: “I’d really like to look like her”. I then started looking at other girls and dreaming I could look like them.  This all started in the late seventies. I am a married heterosexual MTF crossdresser, I have no desire to transition to a female physical body, or live female 100% of the time.  I have been crossdressing on and off since that event in high school. The desire to crossdress comes in cycles, but recently it has been beckoning me to do so even more.

I have yet to go out in public as I have a long way to go in order to pass. I have just clothing, undergarments, and shoes, but no cosmetics, or wig. When you are closeted in the house you don’t need to pass.

A few years in to my marriage, I was able to disclose to my wife that I liked to crossdress, but she felt uncomfortable seeing me in dressed. I kept it in the bedroom and out of sight from my wife. My mom,  my sister, and some of my wife’s friends also know that I crossdress and are OK with it. I have found girls to be more accepting of it. We have no kids.

Recently I was able to ask her to reconsider as I felt the restrictions were affecting me in a detrimental manner. There had been a lot of turmoil leading up to that point, but I think I was able to convince her to let me dress around the house and not be limited to the bedroom. Hopefully, this will make me feel more like myself. I don’t yet know if I will be able to go out in public. It would be a triumph to do so, but I’m large boned, 5’10 and 270 lbs. so a lot of work would be required to get me to the point where I would feel comfortable doing so.

Recently, me and my wife have been working out at the gym, and we’ve both started to lose weight. I’m hoping the weight loss will open a few more doors in the types of outfits I can wear.

Some of my challenges:

I predominately wear female shoe size 12WW. This size is very hard to find in the types of shoes I like (Comfortable strappy mid heel sandals)

I have rosacea (like W.C. Fields) on my nose.

I foolishly had my big toenails removed in my early 20’s as they were constantly becoming ingrown.

I’m currently unemployed (and possibly semi-retired) so I can’t spend extravagantly on female things at the moment.

One good thing:

I have very little chest hair and my beard is spotty.

[Ed: Thank you for introducing yourself Stephanie, and welcome to Crossdresser Heaven! I’m looking forward to more articles about your crossdressing adventures!]

The following two tabs change content below.

Stephanie Q

I'm a techie who crossdresses. I wanted to dress when I was in high school, but could not. Once I could afford my own apartment, I started "experimenting". First it was nylons and heels, and it quickly progressed to skirts and dresses.

Latest posts by Stephanie Q (see all)


Leave a Reply

9 Comment threads
1 Thread replies
Most reacted comment
Hottest comment thread
Notify of
skippy1965 Cynthia
Trusted Member

Stephanie -what a lovely story! I had similar feelings in school but though at the time I thought I was a crossdresser only, I have come to feel that there is more to my gender issues than that. But that’s a story for another day, Anyway, I am impressed that you were able to negotiate additional times to let Stephanie out to be free. Congrats on that!


A truly great story!

simone evans

Hi Stephanie,

That’s a lovely, honest piece of writing and Thankyou so much for sharing it with everybody.

I’m glad you were able to negotiate a bit and allow Stephanie to come out of the bedroom (so to speak!).

From personal experience, I know just how hard it can be to acknowledge your needs and work with your partner to make them a reality.
Rosaliy Lynne

congrats on your achievement – welcome to the group – good luck in the future. Keep that communication open with your wife – that is key here.

stacey s

Stephanie, Very nice story and honest.
Good luck !

I just don’t quite get it. How come transgender girls and crossdressing boys are always so unsually and so incredibly intellegent?


Same feelings for me! Now at least I understand them better. Happy they never leave.

Danielle Lisbeth

Stephanie, Darling dear friend. I too had the surgery on my big toes. Let’s talk. I had similar feelings like you my whole life. What I find interesting is that now that the shame is gone, I realize I just want to be a girl period. Shame and guilt were the only things in the way of being who I want to be. Keep working g out. Treadmill till it hurts. Sweat as much as you possibly can and then some more. Breath hard and heavy. You will reap the benefits over and over. Believe Steph. BELIEVE!!. it will make… Read more »

romi chambers

Experience makes the heart grow fonder !

/* Store links open in new tab */
Subscribe To Our Newsletter

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

You have Successfully Subscribed!

Log in with your credentials


Forgot your details?

Create Account