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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I’m passionate about creating a safe space for everyone in the transgender community to find laughter and friendship on their journey. I completed my physical transition in 2011 and through it I lost everything, and gained everything. I am blessed that I was forced to gaze inward and embark on the journey to discover and live my authentic self. My deepest wish is that all who wander here may find peace, happiness and freedom.

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Lynn Jones
Lynn Jones
15 years ago

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

9 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

9 years ago
Reply to  randy

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

Would love your thoughts, please comment.x
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