A first time out crossdressed and passing

Crossdressing Success Stories are real stories from real crossdressers who have overcome some obstacle in life to achieve their own measure of transgender success. Whether it’s sharing your secret with a friend, wearing your first pair of pantyhose, or reaching out for help on the Internet. The crossdressing journey has many joys and these stories are shared to provide hope, encouragement and upliftment to all in the transgender community. If you would like to provide strength to a sister, please go here to share your own crossdressing success story, and I’ll post your story on Crossdresser Heaven within a few weeks.

This story comes from central Alabama. Thanks Teresa for sharing your story with us.

Meet Teresa

I’m middle-aged single white male, heterosexual and live in central Alabama. I have always had the compulsion to cross-dress since I was about 14 ( I just wish I knew where it came from).

Teresa’s Crossdressing Success Story

I dabbled with crossdressing during a 13 year marriage and it was a factor in my divorce 10 years ago. I still
struggle with being a Christian and the compulsion to dress up. About 3 years ago I started dressing again after about 10 years of being “dry”. I did the purge thing a few times but finally decided I’d live out the desire in hope that one day I can be over it.

Anyway, so the last year I have been working hard with clothes and make-up to look “real”. Recently I ended a several year relationship with my girl-friend, so I was no longer having to hide that part of my personality. Last night I got all fixed up and went to the local beauty supply store to see if I “passed” to the girl that was helping me with wigs, makeup, etc. It felt so good to hear her say, “you look great, you look passable for a woman, I thought that was a woman coming in”. Her co-worker gave the same agreement.

I went to Wal-Mart, Office Depot, Ross and got coffee just to walk around. A few men commented on my looks. It felt “unreal” to finally pass as a woman. What a strange and wonderful feeling. I still can’t believe it has finally happened after 36 years. It will be fun to go out more, just hope to find a support group not too far from here to go out with. My daughter accepts me so I will do some thing with her & friends in femme.

Read more crossdresser success stories, or decide to take the next step and learn how to pass as a woman.

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  1. Lynn Jones 8 years ago

    A story of highs and lows. I hope things work out for you.

  2. randy 3 years ago

    Teresa:: I am a Alabama cross dresser who has not got out in the public eye yet
    my wife is very supportive and has helped me with some dresses but I haven’t gotten
    a wig that I think would look good yet but I am looking . Would like to talk with you .If you
    would leave me a way to contact you as I am in the greater Birmingham area and would
    very much like to share some experiences with you

    • Brittney 2 years ago

      I am in the same situation,email me lets talk sometime!

  3. georgette 7 years ago

    Dear Teresa,
    Thanks for sharing your story. My big wow after your big trip and by yourself. My first time out i happened to be accompanied by 2 ladies. It really helped. Even if they were a pair of DOmmes from the other part of me that likes some parts of the BDSM world. But you said going out with your daughter and her friends, that has got to be better then going out with a spouse or other sisters.

    I understand some of ones questions etc about the church side of things, it was a block for me until the Internet. One site that i found is by Jade Catherine Devlin. She has spent a lot of time researching and studying it. Her webpage is http://alum.mit.edu/www/rebar/index.html

    If you are question your practice of cross dressing and God, a must read in my book. Vanessa please pass it on to Vickie. It should give her more strentgh and faith. Jade makes a great teaching for cross dressing not against the Bible. Has some info related to TG and the Bible not her interest at this time but will give you resources if looking.

  4. penny 8 years ago

    Dear Teresa , thank yu so very much for sharing your storey , it is great to hear from Sisters that have experrianced such a special fem out come, sorry it was a factor in devorice and relationships that went bad, but i think many of us have that problem ,i know I do. But it is very special to know that you have found understanding friends and your daughter is a wonderful lady to support and enjoy your femside god bless her and you love peny

  5. Sandra Diaz 8 years ago

    Dear Teresa, I live in Dothan Alabama. I’m happy to hear yoursucces story. If you’re looking for a support group, there is one in Huntsville call North AlabamaGender Center. Good luck. Sandra

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