Categories: Crossdressing Success Stories

A Crossdressed Outing on Wings

Comments: 3 Comments
Published on: May 13, 2010

Going out in public for the first time can be daunting. In this week’s crossdressing success story Laurelanne shares her passing victory with us out in public.

For all you ladies who have never been out in public before Esprit - which is just four days away! - is a great opportunity to spend a week as a woman in a safe and supportive environment. If you’re heading to Esprit stop by and say, ‘hi!’, it would be wonderful to meet you in person.

Now on with this week’s crossdressng success story…

Laurelanne’s Crossdressing Success Story

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Laurelanne Passes As A Woman

After many years of NOT appearing outside my home I had a terrific success.

I used to go out many times for many years en femme and with no problems , yet for awhile as I aged i felt I was somewhat too “old” to do it. I didnt return to being out en femme until all the kids were grown and out of the house.

Recently about 3 months back after having been out numerous times alone and with my wife. I ventured out to see a friend (who knew me as both ) and went out as Laurelanne. Having arrived at his apartment building I parked my car, had some guy walk by me and say “sweet”. I was wearing a top with alot of cleavage showing, made me feel great.

Entering the building I waited for the elevator, and when it arrived a young man said to me, Go ahead Ma’am, wow (2 at once) I visited and left a few hours later, and upon entering the elevator again, a little boy rushed ahead of me, his mother, a younger girl, said dont be so rude, you should have let the “lady” go first, now apologise. He did and I said in my best femme voice its OK, , and the mother said its not mannerly I’m sorry too. And I said I have 3 boys and theyre all the same we laughed and exited the elevator. I was on wings I had a triple header, accepted and more.. Wow. I guess still not too bad for an old girl.


If you’d like to spend more time out in public passing I highly recommend the World’s Best Crossdressing Guide –  it’ll whip your femininity into shape!

Michelle's First Outing Dressed

Comments: 8 Comments
Published on: April 29, 2010

I’m excited to share Michelle’s crossdressing success story with you, dear readers. I thought it was wonderfully timed, given how we’ve just been talking about feminine voice, and how it can sometimes prove a daunting challenge to even the most courageous among us.

If you’ve had a crossdressing success please share your story. Even if it seems like a small triumph, your words will bring comfort and inspiration to other readers. So without any additional preamble, I’m pleased to introduce Michelle.

Meet Michelle

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Michelle's First Crossdressed Outing

I am 38 years old and married. I just recently been dressing with the support of my wife. I remember when i was a kid trying on my moms clothes. But as i grew up I stopped mainly because of my family and friends. I live in a small town that does not look favorably on it. My wife and I started roll playing and I finally admitted to her I like dressing in femme. She accepted fairly quickly and is very supportive with it. We buy clothes and jewelry together. It has been great doing this with her.

Michelle’s Crossdressing Success Story

I have been just dressing at home not really going out. If we go out it was always after dark when no one would see me. I finally decided that Michelle needed a day out. Being that we live in a small town where everyone knows everyone. We decided to hit a near by bigger city. Where we could go out to eat and shop. I picked a nice spring dress out. Put my makeup on and fixed my hair with alittle help from my wife. Put on some low heels that would be more comfortable for a day of walking. Michelle was ready for her first day out. Our first stop when we got to our destination was some food. So we stopped at a nice sit down reetuarant. When we went in I became really nervous. It felt like everyone in there was staring at me. Even though they payed little attention to us.

The hardest part was trying to talk to give the waiter my order. My voice as been the hadest for me. Well with a very uneasy voice I ordered which gave me away. But he took it well and was very nice and stayed with us till the we payed. After that having been made was tough on me. So we just drove around alittle then made our way home. I am not going to give up though just work harder. It was a blast being out as Michelle. And looking forward to the next time. Hopefully with a litte more success.

Following God's Guidance – A Transgender Success Story

Comments: 3 Comments
Published on: April 8, 2010

Dear Readers,

This week I’m pleased to share Sarah’s transgender success story. Her story shows the loving embrace of a church family, a personal journey of discovery and fulfillment in living who she is every day. Sarah’s tale of joy and heartache was published in her church newsletter.

If you have a story you’d like to share with the readers of Crossdresser Heaven, please take a moment to share your transgender success story.

Sarah’s Transgender Success Story

Sarah has been a member of St Aidan’s congregation for over a year now and has been singing in the choir for almost as long. On August 16th last year, Bishop David came to St Aidan’s to baptise and confirm Sarah: she is the first adult to be baptised at our church for some years. I talked with her at Claudelands Motel which she runs.

Sarah first came into contact with St Aidan’s when she approached Andrew to use the hall for a meeting of the Agender Group, a support group for transgendered people with which Sarah is involved. Sarah said to Andrew, “You need to know that we are all cross-dressers and trans people.” Andrew responded, “You are people of God and you are most welcome.” It was not the response that Sarah had anticipated.

It blew me away. That made me revisit my attitude to religion. I thought, “Maybe some churches don’t mind and some churches do mind and I was just lucky I picked the one that has no concerns about people like me.”

Sarah was brought up in “probably a Presbyterian church from memory” but didn’t go regularly. She was married for 33 years. “When I got married, my wife had a family and the family always went to mass so I started going to mass with her. I did it for her and I was very happy doing it.” Sarah describes her family: “I’ve got a family of ten: my wife, three children, four grandchildren and a son in law and a daughter in law.”

She speaks warmly about that period of her life. “I loved it. Being married and having a family made me feel normal. I was very isolated before that: lonely, introverted. I got free of cross-dressing for a year or so but it reared its ugly head again.”

After her marriage broke down, Sarah felt it was time to leave Whakatane: “About a year later the whole town knew I was a cross- and it was a small town. All of a sudden I wasn’t flavour of the month.” Sarah saw the Claudelands Motel advertised while she was in Tauranga “funnily enough”. Having had a motel in Hamilton in the early seventies and after accounting for 30 years, Sarah thought, “That’s something I could do easily. I’ve done it before”.

Since being in Hamilton Sarah has embarked upon the process of transitioning to a female.

(more…)

A Morning Paper Run – In Drag!

Comments: 1 Comment
Published on: March 31, 2010

Have you ever felt the urge to wake up and face the day as a woman? Perhaps spending a few beautiful hours before the masculine reality of your day sets in? Today’s crossdressing success story comes from Vicki, our very own guest author on Crossdresser Heaven. You can read many of Vicki’s writings about Crossdressing and Christianity on this website as well.

Before we share Vicki’s success I also want to let you know about another success story we have coming up soon from Sarah. Sarah transitioned two years ago, and has a heartwarming story to share with all of us about her journey into womanhood, her loving friends and supportive church. Her words will be a blessing to you – take a moment to subscribe to Crossdresser Heaven so you don’t miss out!

Vicki’s Morning Crossdressing Success Story

Well, it’s a small step but a step nevertheless. My cross dressing success story involves a decision to just go out and get the Sunday paper this morning. I was still in my makeup and had nail polish on from my day off Saturday which I spent most of lounging around the house and indulging my feminine side. I had slept well, and when I woke up, I was just enjoying the feeling of still being dressed, in a nightgown and still having traces of makeup and my bright red nails. My usual routine is to go out in the dark, and take a walk, or if my tired knees will handle it a short run, come home, scrub any leftover makeup off, remove the nail polish and drab off to the store for the paper and maybe a bite to eat. But I was enjoying the luxurious feel of the nightgown and I decided this was it, I’ll freshen up, fluff my hair, put on something discrete and just go get the paper while the coffee brewed.

Still in panties I pulled on a pair of pantyhose, a pair of faced blue jeans, a bra and a pink blouse. I decided on a pair of ankle boots and with a quick makeup touchup, I was ready to go. I put my wallet in a purse I borrowed from my girlfriend; put on her denim jacket grabbed the car keys and headed out the door. I was up pretty early so it was still dark and my plan was to head for a fairly remote, (for the city, 7-11. Tucked away in the northeast part of Seattle and across from Magnusson Park, I felt that the only eyes I would have to deal with were the clerk’s. I drove off, got to the store and parked and without any hesitation got out and went in to grab a paper, pay, and leave. The clerk looked at me briefly as I walked to the paper stand. Dang!. The Sunday edition had not reached this part of town yet. The Advance Bulldog was there but no Sunday edition. I turned around, smiled at the clerk, muttered something about the wrong edition, and went back to my car. Whew… that was pretty easy. Well, I’m out to get a paper so let’s just do this.

Giving up the cover of remoteness I drove a short distance to a better traveled road, a more central 7-11 and parked the car. I was the only one there, as it was still pretty early, but I got out, went in, found the paper, went to the counter and paid for it. I looked the clerk in the eye, if he had any reaction he was very good at concealing it, and said in my best feminine voice, “just the paper today”, and “thank you, have a good day” and headed back to the car. I drove home, shed my outside clothes, put the gown back on, grabbed a cup of coffee and sat down to enjoy my morning paper and the satisfaction of making one more bold step out.

Peace At Last

Comments: 8 Comments
Published on: January 28, 2010

Dear readers, I think we all have something we can learn from Anne’s crossdressing success story this week. I’m particularly impressed by the patience, love and consideration with which Anne shares her crossdressing with her wife. Credit is also due to her lovely wife – she gave Anne the opportunity to share, was open enough to learn more about crossdressing, and accepts Anne for who she is. Truly this story is like oil on the troubled waters of our souls.

If you would like to share your crossdressing success story, please take a moment and submit your story here: http://www.crossdresserheaven.com/contact-vanessa/submit-your-crossdressing-success-story/

Meet Anne

I am early 60′s with a wife of 40 years, 3 children and 4 grandchildren. I was raised in a Christian family, spent most of my career in the aviation field, and actually pastored a small church for a few years. I retired 5 years ago and we live in BC, Canada. My interests include golf, boating, biking, gardening and learning more (from your pages as well as books etc) about this crossdressing thing.

Anne’s Crossdressing Success Story

The latest chapter of my life began just over a year ago (Dec 08) when I emerged from the closet (literally, as we have a walk in closet) with a bra on and asked my wife what she thought! We had just finished an evening of sex, and I had probably put on her nightie at some point in the proceedings, as I had done here and there during lovemaking over the 39 years of our marriage. She had always taken it to be just an extra turn on for me and had never really objected to these momentary aberrations on my part.

Little did she know that I had been crossdressing in secret over the previous 6 years or so, and that now I was making a statement about who I really was. She was totally shocked as I began to open up about my desires to wear women’s clothing, as she had barely heard of such a thing before, our family being good Christians where such behaviour would have been viewed as sinful.

But to her credit she listened as I poured out my heart, then she began to ask questions, then listened some more. We talked until dawn, then steadily for the next few days. I brought out my stash of clothes and she watched in amazement as I modelled for her right there in the kitchen. By then we were able to have a laugh or two over the whole business, and both of us began some research into the “condition”. We scoured the internet and bought Peggy Rudd’s book which shed much light on the subject, then to my wife’s great credit she consented to letting me dress while in the house, and to keeping a drawer and some hangers for my “stuff”.

It felt like I had died and gone to heaven and still does as I write this while seated at the kitchen counter dressed in a pale blue skirt over patterned stockings, and white knit top over pink camisole and rather nice, lacy white bra. No makeup or wig at present, and generally I wait until my wife is out of the house before doing all that, as I try to be respectful of her at all times. Sometimes we just know when enough is enough!

I do get out of the house a bit while dressed , but covered. This afternoon it was raining pleasantly, so I put my rainpants and jacket over skirt and top and went for a long walk. What peace was mine as I stopped in the woods to observe the birds, while being very aware of what I was wearing and the effect it had on me.

Who knows where I go from here, but I feel that the freedom my wife has given me to excercise some of my innerself has been a huge blessing. My secret has gone no further than her , and yet we both believe that I am a more open, compassionate person with all the members of our family. Over the years I have been a moody person and even diagnosed with depression, which I felt as a Christian I should have been able to overcome. Since I have been free to dress, whether I actually do or not, I have been of a more even and contented temperament. It seems amazing what a bra and slip can accomplish, and I believe that God might just have been waiting for me to discover that!

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