Smile on your Crossdressing journey

Today’s crossdressing success story gives you a glimpse into one cross dresser’s life over the span of many decades.  Hannah shares the long, sometimes treacherous and sometimes thrilling journey that many crossdressers embark on. If you’d like to share your crossdressing success story please take a moment to submit your story.

Meet Hannah

I’m writing my real life story to share with anyone and everyone who has had any personal experience with crossdressing as a crossdresser, a family member of a crossdresser, a significant other such as a girlfriend or wife, a friend of a crossdresser or transgendered person in the hopes that my story will touch someone in a positive light and make someone feel as if they are not alone and that there is a true blessing in cross dressing 🙂

Hannah’s Crossdressing Success Story – A Journey of Discovery…

Hannahs Crossdressing Journey of Discovery

Hannah’s Crossdressing Journey of Discovery

It seems that of the billion or so crossdressers in the world today and throughout ancient history and “herstory”, that there are such a wide array or reasons why we crossdress. I will try my best to keep my story as short and concise and to the point as I can although I could write about this topic forever and a day. I’m from a family of 7 children and I was born as the 5th child and I have 2 brothers and 4 sisters. Both of my brothers are older than me and I have 2 older sisters and 2 younger sisters which resulted in lots of girls clothing and feminine attire in my home although I limited myself to how often I would wear their clothes because I wanted my own wardrobe eventually.

My earliest recollection of an act of crossdressing was to try on girls underwear from our laundry room which elicited a sensational feeling of comfort and non sexual arousal at the age of about 5 years young. I also remember my dear mother making me wear a panty-like garment over my cloth diapers to prevent my bed from getting wet when I slept through the night as a baby. I can remember how those panty-like garments felt with the elastic leg bands around my legs and the different colors they were such as green, yellow, purple, etc.. From that point on, I had an appeal to wearing panties and how they felt so different and how they were much more fun to wear than boring boys underwear.

En Femme Style

I was so young at that time and didn’t have a job or any income so I would indulge in my 4 sisters endless supply of panties. I enjoyed my older sisters panties more so because they were wearing the more silky and sexy styles than my younger sisters who were still so you and wearing cotton ones. My personal preference is silk, nylon, rayon, or lace materials instead of cotton. As time went on and I was becoming more and more appealed to and fascinated about femininity, girls, and girls clothes.

I knew they had something I didn’t have. I would see my sisters nude and partially nude when my mom would bathe my younger sisters and when my older sisters walked around the house in their undergarments, bra’s and panties, lingerie, pajama’s, etc.. and that would make me think hhmmmmmm I wonder how their clothes would feel on me.

So my next move was to try on a bra and when I did, once again I felt that sensational feeling of pleasure and arousal in a non sexual manner although child psychology experts and sexuality experts say that people begin to experience sexual arousal long before we ever engage in the physical act of sex. So the early days of my crossdressing we pretty much all panty and bra wearing and an then I went on to pantyhose and now I will fast forward to my teen years when I reached puberty and was more aware of my sexuality and what aroused me in that manner.

I would love seeing girls my age and older women all dolled up and dressed up looking all pretty with makeup and all the accessories that they would wear with their outfits such as bracelets, hair barrettes, and necklaces, and the many many other feminine accessories. I knew at that point I wanted to indulge in the complete world or all things feminine.

En Femme Style

I went on to start to buy my own panties and bra’s at department stores which was a lot of fun because I would tell the store clerks that I was looking around their lingerie department for me because they would always ask me if they can be of help to me and assist me in choosing something out for the girl or woman that I was looking to buy something for. I loved telling the clerk I was shopping for me.

I then eventually bought books on transvestism and crossdressing [we didn’t have the internet or this awesome website back then]. I still hadn’t totally dressed up en femme at this point in my life either. My mother and brother would eventually discover my huge panty and bra collection under my mattress or in my closet hidden away on separate occasions.

My mother also found my books on crossdressing and never confronted me or said a word about it to me other than she would take them and I have no idea what she did with all of those panties, bra’s, the few books on crossdressing, the press on nails, etc… It was obvious that she was not wanting me to engage in this behavior so she never asked me about it but I now knew she knew that I was engaging in such behavior.

My sisters would eventually say things to me such as ” I saw you sleeping and wearing my underwear and I want them back” and they would ask me things like ” do you have my gold clip on earrings because I know I had them in my jewelry box and now they are gone” but they would never really ask me if I was a crossdresser or if I had issues with crossdressing but I knew that slowly but surely that my family was seeing clues as to their brother being a crossdresser or having an appeal to female clothes.

Visit Transgender Heaven

All through my school years and through high school, I would more often than not wear panties under my boys /men’s clothing except for Gym and Pyhs Ed classes when we were required to take showers after our recreational activities. I was also regularly interacting with girls and had girlfriends since the age of 10 years old and through my school years although I didn’t lose my sexual virginity with a girl until shortly after graduating from high school so I really never had to reveal to anyone that I was wearing girls underwear most of all the time.

As a young adult when I would date a woman, I would eventually tell them or show them that I liked wearing girls underwear and I had received mixed reactions and responses from the individual girls and women that I date. By telling them about this I would become so turned on secretly in my own mind and it was my way of coming out to them in a subtle kind of way. Once I told them about it and nearly all of them were accepting of it, then I would most always wear girls underwear whether it was theirs or my own.

I finally began dressing up totally and completely as possible in my early 20’s and every crossdresser knows that this phase is a trial and error phase with lots of help needed to get it just right and how challenging it can be to dress up totally and look at ourselves in the mirror and say to ourselves that we look beautiful. This is the time too that I would begin to tell every woman I could that I was a crossdresser. It really helped to be honest and open about it and many of the women I would tell would be strangers such as store clerks at the malls and department stores but I also told every girlfriend I had too and I never found it hard to find a girlfriend.

I was also lucky that not one of these girls ever “outed” me to anyone that I was aware of. I was not wanting to come out of the closet to the world about my crossdressing hobby but I did like telling girls and women that I chose to tell in one on one situations. I too, had guilt, shame, and fears to deal with all along the way and I never really wanted to be caught or discovered my male friends or family members to the point where I would have to admit that I was a crossdresser.

Visit Transgender Heaven

I was a bit of an exhibitionist to strangers though as I would wear bra’s under my shirts so that they could be seen my anyone standing close by me. I would wear hose and no socks so that they could be seen when I was sitting down. I would wear panties and make sure that they could be seen by someone if I were to bend over and a person would see them sticking out from the back of my pants and jeans. And once again, I would continually tell any woman I ever dated.

When the internet became available, that would open up a whole new world of crossdressing portals and people that were just like me. I would eventually join social groups of other crossdressers and I would look up any and all information about crossdressing and I would still enjoy, as I do to this day, shopping for my own clothes, attire, and accessories and letting the store clerks know it was for me.

One thing that is even more fun than that is shopping with gg women and females in general. By coming out and telling women about my crossdressing, I have been lucky to have gained acceptance from nearly all of these women in my life although some come and go in my life and they have never passed any negative judgment on me or towards me.

There was one woman named Michelle that I met a little over a year ago that was the most receptive woman in my life of all the women I have ever told. She even read some books on the topic from a local library and I ended up bringing them back to the library past the due date so I have small late charges on my library account so whenever I go the library the clerk tells me I have a $2.10 late fee on two crossdressing books and they say I can pay them at a later date if I don’t have the money on me which is fun to be told that from the librarians.

Visit Transgender Heaven

Well Michelle has totally accepted my crossdressing and has been very much involved in it with me and has dressed me up in clothes she has bought for me and her friend had given me some new clothes that she had never worn. They bought me a new wig, makeup, accessories, etc… She takes pictures of me too for fun. Michelle has also gone to Tri-Ess meetings which is a social and support group for crossdressers and girlfriends and wives of crossdressers.

I am very grateful to Michelle for her tolerance, understanding, and participation in my life as a crossdresser. I believe and feel strongly that almost every crossdresser wants to be accepted as a woman even though crossdressing is an art of illusion and a behavioral pleasure. I also believe that nearly every heterosexual and bisexual crossdresser would love to have a woman in their life that they can share their feminine side with whether it be a girlfriend, wife, or a female friend that they can be amongst and present themselves in their female state and to be able to feel like a woman amongst other women.

I know that I surely love that element of being a crossdresser in a way that is like words beyond description. Many wives and girlfriends report that the men in their lives that are crossdressers are much more of a real man to them because men that crossdress are way more understanding of womanhood and are more sensitive to a woman’s needs, emotions, and day to day realities of being a woman in today’s world.

I am no less of a man just because I am a crossdresser. I love being a man and I also love being a crossdresser and I wouldn’t want to change this part of me ever. I hope all of you readers, whether you are a crossdresser or a wife or girlfriend of a crossdresser will accept who you are or who you are with if you are involved with a crossdresser. It can be a lot of fun with the right mindset of everyone involved in the world of crossdressing. I will end this now because if I don’t I will write and talk and write and talk until I cant write or talk anymore.. ~hugs! Hannah


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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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14 years ago

Dear friends, I’m glad that I found this place to share about my crossdressing life. I too have been crossdressing for a long time. i now have a wife who is accepting totally of my crossdressing, and I couldn’t be happier. I still don’t have all the acoutrements that I need and want for a complete feminine apearance, but what I do have we both enjoy.I would love to talk to others.

14 years ago
Reply to  Vanessa Law

vanessa, thanks for the nice comment. I’ve been looking for a girlfriend to talk to every so often. Hope you don’t mind. I’m 55 and like you have been crossdressing most of my adult life. My wife had a hard time at first understanding the feminine part of me, but once we were able to talk it out rationaly, she accepted it and has encouraged me to be myself whenever I would like. I’m now able to express myself and be the woman I am whenever the mood and time are right. I’d love to talk more later. Ragina

Sharon' class='avatar avatar-64 photo' height='64' width='64' />
14 years ago

That was a beautiful story Hannah,you certainly are a beautiful lady
and so fortunate to have a wondreful understanding partner.

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