Crossdressing in the Snow

Crossdressing fashion: A mid-length skirt

Fall and Winter fashions are a crossdresser’s dream come true. Gone are the short breezy skirts and skimpy tops that all but scream masculine at your too broad shoulders. One of my fall favorites it the mid-long skirt paired with a good pair of boots. In the fashions shown here the floral skirt (on special at almost $55 off the original price now) has a femininity about it without sporting too small a floral pattern. As you know, small patterns make you look even larger – not something any girl wants

A Crossdresser's Favorite: High Heel Boots

I love shoes of all types, but I have a particular fondness for boots. My favorite are ankle boots, though in Northwest winters ankle boots will leave your legs cold and wet. This week’s crossdressed outfit features a stylish mid calf leather boot. I’m trying hard to resist buying this one (I just sent back a pair of boots that didn’t quit fit, but even then my lovely wife is looking at my growing shoe collection with … concern).

Have fun with the last few weeks of fall while the remaining few leaves cling to the trees and the snow is held at bay.

—
P.S. I apologize for being a bit quiet these last few weeks. Between work, family drama and home projects it’s been a bit tricky to do one of the things I love the most – spending time with the lovely ladies at Crossdresser Heaven.

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Shh... Keep your crossdressing secret

Halloween yesterday was a blast! I hope your crossdressing Halloween escapade was similarly awesome!

I dressed up as a witch, and had fun sharing candy, scaring kids and looking wretchedly evil (in a feminine sort of way). Some of my friends remarked in glee at the dark purple / almost black nail polish I was wearing. Even though a late night wine run had other shoppers calling us ladies while admiring our costumes I don’t think anyone suspected. Noone knew about my crossdressing secret (mwuahahaha).

I wouldn’t be too awfully sad if I had been outed, but I’d like to think I pulled off a crossdressing escapade without a hitch. What about you? Was your Halloween a successful crossdressing experience?

Did you keep you crossdressing secret?

Let me know, in this week’s crossdresser poll.Note: There is a poll embedded within this post, please visit the site to participate in this post's poll.

What is our favorite Halloween look?

From last week’s poll, it looks like the woman of Crossdresser Heaven like to femme it up! Feminine and ‘Sexy and Sultry’ win out over ‘Plain Jane’. Note: There is a poll embedded within this post, please visit the site to participate in this post's poll.

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Don’t give up just because the 31st is almost upon you! Here’s three costume ideas that make use of your natural manliness and allow you to crossdress at the same time!

The frumpy housewife

Crossdress as a frumpy housewife

Don’t feel like shaving? Starting to grow a beer belly? No problem, your physique is perfect for our first costume idea – The frumpy housewife. Throw on an old gown and some slippers, and let your five 0’ clock shadow complete your look. If you have long hair you can crank your costume up to the next level with some large rollers, and don’t forget a dab of poorly applied makeup. Noone will ever suggest that you’re trying to achieve feminine perfection, and you’ll save hours on hair and makeup!

The biker Babe (Almost)

Not every biker babe is blessed with a curvaceous body. There are some that ripple muscle or attempt to ripple with too much body cushion. You can use this to your advantage! Just throw on your knee high boots, a pair of jeans and a tight t-shirt. A wind-ruffled wig is all you need to finish off your outfit. You’ll give folks a good laugh, and don’t even need to remove your body hair to do it.

The Transvestite

Last but not least you could choose to go as a slightly sexed up version of you. Your tightest mini-skirt, some deep red lipstick and a sultry strut. If you’ve been crossdressing for a while your wardrobe will probably contain all the necessary items. But watch out! You’ll definitely get questions, and you might even find some people circling dangerously close to your secret.

Even if you don’t decide to crossdress, the most important thing is to go out and have some fun this Halloween! Scare yourself sexy…

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If you’d like to share your own real life coming out story, please take a moment to share your story and give other’s the courage to express their femininity to the world!

Coming Out – Sandy’s Crossdressing Success Story

Dear Vanessa and Sisters, My name is Sandy and I started dressing when I was 12 years old. One night I was baby sitting my younger brother and after he went to bed, for some reason I became interested in seeing what was in my mother’s dresser drawers. First thing I found were her soft panties. I took off my pajamas and put them on. Every few weeks I added something up to the silk stockings. Within a few months I had all her clothes on, her lipstick on (a bright red color), saw myself in the mirror all I could think about was how great it felt.

Over the next 35 years this experience was stuck in the back of my mind. I did enjoy reading about it when ever I could find something. Sometime around the age of 47, the feelings started taking root again, and over the next 10 years I started dressing in my home bedroom. Soon I started dressing and going out to the nail salon & spa’s and enjoyed the good times being pampered as well as looking forward to spending time making new friends each week. Sometimes I even went out to dinner and spent the night in a hotel.

I know I didn’t completely pass but it made me feel good anyway. The only thing my family knew is that my toes were always painted and in fact they still are. At 57 years old I retired & moved south. After spending 1 ½ years getting healthy after a near death car crash. I have now started buying new fem cloths and makeup.

I spend most of my time in something E Fem or dressed completely Fem. A few weeks ago during a trip up north to see family, I found a new web site called FemmeFever. The owner Karen, a real sweet lady, showed me how to do my makeup. We spent all day putting different looks on and took plenty of pictures. The experience has helped me be more relaxed and confident about my fem side. That evening Karen and a group of sisters from the area gave me a coming out party in a local restaurant. I had the greatest fem day ever and it felt so good that I will soon be going to Las Vegas for a fem Halloween party next month. Maybe my experience can help someone else overcome their fears. With love, Sandy

—
If you want to look your feminine best you have to read this Crossdressing Guide. It’s chock full of excellent tips on how to look and act more feminine.

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• Living between the man I am and the girl I want to be (22)
• Learn how to cross dress (22)
• Are You Ashamed Of Being a Crossdresser? (21)

Wear a sexy nurse outfit this Halloween

As I was writing this post my beautiful wife popped her head in to see what I was doing. She thought it was strange that I would ask you – do you know how to crossdress? Since, most of the readers of Crossdresser Heaven are crossdressers, presumably you would have some idea how to crossdress Questioning your ability to dress en femme was not my intention. Rather I wanted to ask – Do you know how to crossdress at Halloween? In some sense it’s easier to crossdress at this time of year, but you can’t rely on everything falling into place at the last minute. A successful Halloween crossdressing adventure requires at least a little bit of planning.

Have you planned your crossdressing escapade?

Do you have your outfit all planned out? Have you coordinated your makeup with your outfit, and checked to make sure you’ve got the perfect earrings to go with it? You can’t just wear any old jewelry with a sexy nurse outfit. Some outfits demand a certain kind of shoe. Whether it’s a spiked stiletto boot or sexy white pump you’ve got to be prepared.

A Halloween Princess

I’ve always wanted to dress up as a princess for Halloween. A princess like in the Disney movies in a flowing ball gown. To dream, if just for one night, that I was a

Crossdress as a princess this year

beautiful damsel living in a tower. With each day filled with sunshine, signing birds and elaborate outfits. If you’re planning to go as a princess, well – that would require a bit of planning. Your jewelry will need to look as expensive as your outfit. This is also the perfect time to try a new updo – it looks extremely sexy when you’re in a formal dress.

So, who are you going to be this year?

Other Transgender Posts

• Why do men cross dress? (117)
• I married a cross dresser (45)
• Living between the man I am and the girl I want to be (22)
• Learn how to cross dress (22)
• Are You Ashamed Of Being a Crossdresser? (21)

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…

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.

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.

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.

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.

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.

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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Last year at Halloween time I wrote a post describing some of the many crossdresser halloween costumes that men can choose from during this season. I thought this year I’d share some more of my favorite costumes and inspire you to take a bold step out crossdressed this year!

Crossdress as Marilyn Monroe this Halloween

Who doesn’t want to look as glamorous as Marilyn Monroe in her heyday? When you crossdress as Marilyn you’ll get to dress to the nines and show off your flirty side. As an added bonus, you can coordinate this costume with your loved one, who has the choice of many public figures who had steamy relationships with Marilyn.

Cross dress as a naughty school girl this Halloween!

After years of trying to convince my wife to go as a sexy school girl, I figure that perhaps she wants me to lead by example If you decide to crossdress as a schoolgirl this Halloween, be warned. This costume will require a feminine physique to pull off well. If you’re looking for a school girl costume a bit more forgiving of the male figure, try this still sexy yet less revealing schoolgirl costume.

Halloween Crossdressing Advice

A few things to keep in mind when you’re out crossdressed this Halloween. The most important thing is to have fun! Don’t worry what people will think, everyone is dressed up. Don’t worry about being too feminine – you can just say you’re getting into character. If you’ve nervous of revealing your secret, don’t dress in everyday woman’s clothes! The more backstory you can provide about your costume, the safer you’ll be. Having to explain why you just happen to have the perfect matching blouse and skirt could be…interesting.

Trick or treat!

Other Transgender Posts

• Why do men cross dress? (117)
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Crossdresser Heaven gets a makeover

The improvements should make it easier and faster to find the information you’re looking for while reducing clutter and making the articles easier to read. At least that’s the theory

Let me know what you think!

While browsing the site you might also find some quirks and unexpected behavior. Or perhaps there’s something about the site you just don’t like – it’s too slow for you, difficult to find information or a page fails to show up. Please share your feedback on where Crossdresser Heaven can be improved, as well as what you like most about the new site (I’m a sucker for praise ).

Thanks in advance, and stay gorgeous!
Vanessa

Other Transgender Posts

• Why do men cross dress? (117)
• I married a cross dresser (45)
• Living between the man I am and the girl I want to be (22)
• Learn how to cross dress (22)
• Are You Ashamed Of Being a Crossdresser? (21)

If you’d like to share you crossdressing success story, please take a moment to submit your story. I’d especially like to encourage wives and girlfriends of crossdressers to share their successes. Even if you’re still struggling with your loved one’s crossdressing your small successes will bring encouragement to many others who are walking the same journey.

Meet Amy

Hello, I’m Amy; I’m a 36-year old female who lives in a small town in Georgia.

Amy’s Crossdressing Success Story – A Wife’s Perspective

I don’t know if I can publish a story being a female, but I am so inspired by all of your stories that I had to tell mine. I met my husband about 5 years ago at a pizza restaurant where we both worked at the time. I had identified myself as a lesbian for 10 years, but hadn’t found the right woman. I had had two boyfriends, both of whom validated my reasons for choosing the lesbian lifestyle, even bearing a child from one of them.

But this one, 9 years younger than me, there was just something about him I couldn’t put my finger on, but I knew I had to have him. I heard was a preacher’s son and had a good reputation, unlike the last one who’d left me and my son 5 years earlier. Anyway, we hit it off and dated for 4 years before getting married. I always felt like he was more of a woman in bed, which naturally I liked, having been a lesbian before.

Now I had a kid, plus living in the Bible belt is not easy when you’re not living the "straight" and narrow, so I no longer had the desire to seek out a woman. So he was perfect, the best of both worlds. Little did I know just how perfect.

I knew he liked wearing my tank top I once put on him, but I thought it was no big deal since it never came up again. Later I found out that he was attracted to me from day one, having listened to my lesbian escapades. It seemed a part of him identified with/wanted to be one of those women. This might sound strange, but one night 3 years into our relationship, I heard in a dream or vision from a beautiful goddess (crazy, I know) telling me that I needed to tell him that it was ok to wear women’s clothes; that it was an ancient part of him that would be very healing if he would just allow it to happen.

I told him this, but he said nothing and I forgot about it. It wasn’t until our wedding night that I experienced the full extent of my husband’s desire to cross dress. We went and bought lingerie that I was hoping he would especially love on me. It seemed he cared more about himself wearing the clothes than me. I was actually jealous of a robe!

This was such a downer for me on our honeymoon. But how could I have known? We hadn’t been able to live together during our engagement, between his conservative background, and my not wanting to shack up only to be abandoned again. And he’s quite shy about such things.

Well, I am happy to say after nearly 2 years we have adjusted and grown together, and through a lot of communication and encouragement have created a beautiful relationship that is like no other. Thanks to Vanessa’s website, Vicki’s wise words for Christian Cross Dressers, and all the CD stories, I have come to understand why my husband feels the way he does; it even endears me to him more.

The stories have made me cry at times. One day I saw on Oprah a transgendered man (woman now) and her wife who would shop for jewelry together, and something about their story, their kinship made me cry as well. It wasn’t tears of sadness, but more of a cleansing and a relieving. It felt like, "Yes, that is it", like a resounding truth.

Now I dress him up all the time. Occasionally he will put something on, but he is more passive and the thrill for him is someone else doing it to him. I no longer see his desire to wear women’s clothes as taking away from me. In fact, I think this has strengthened me to be more, to explore my masculine side, my dominating side (grin), and now I play video games with him and fix things around the house.

I’ve even explained to my 11 year old son that his step dad feels good in women’s clothes, and he was ok with that. He actually said it explained a lot and seemed relieved to now know the truth. (I’m sure he’s noticed him wearing my jeans and pj’s from time to time.)

My dream is for us to move to a place where he could be comfortable to be himself, be it in women’s clothes or makeup or even transitioning to transgendered. This whole experience has taught me that gender is a very complex thing and that we all have a varying degrees of masculinity and femininity in us.

It has taught me to question, what makes us a man or a woman? Doesn’t our Creator create us to express ourselves the way we want? Isn’t there a feminine aspect to our Creator that he/she wants to shine through us? What would the world be like if we were more free to express both male and female sides of us, or just one if that’s what gives us joy? I think it would be an infinitely better world.

Amy

Other Transgender Posts

• Why do men cross dress? (117)
• I married a cross dresser (45)
• Living between the man I am and the girl I want to be (22)
• Learn how to cross dress (22)
• Are You Ashamed Of Being a Crossdresser? (21)

I spent most of my time working on some exciting improvements that will be coming soon to Crossdresser Heaven. Stay tuned, I’ll take the wraps off them in the next week or two.

This was a brief crossdressing intermission for Crossdresser Heaven, and if anything I know that crossdressers understand those brief or long periods between your feminine expression. Thanks to all the ladies who recently submitted Crossdressing Success Stories, or sent me email – I’m working to catch up over the next week or two, you should hear from me soon.

A Pause in Your Crossdressing?

Crossdressers purge at their peril!

We take a breather from crossdressing for many reasons. For some the summer months are so filled with family activities that it’s hard to find some feminine time. Others may be intimidated by the more revealing summer styles (more on this in a future post…). Perhaps it’s the ritual purge performed in search of a cure for crossdressing, or the natural waxing and waning in the desire to crossdress.

Whatever your reason, I’m willing to bet that you’ve spent some period of time not crossdressing – not even thinking about it. As strange as it sounds, perhaps you’ve even felt guilty about not crossdressing. You’ve thought to yourself, ‘if I don’t feel like crossdressing now, perhaps it really is just a phase I’m going through?’.

There’s nothing wrong with a brief respite from crossdressing as long as you don’t feel forced or coerced into it. And trust me, there’s nothing quite like an overactive sense of shame and guilt to force you into an unwilling crossdressing vacation.

Have you taken a break from crossdressing recently? Why did you do it?

Other Transgender Posts

• Why do men cross dress? (117)
• I married a cross dresser (45)
• Living between the man I am and the girl I want to be (22)
• Learn how to cross dress (22)
• Are You Ashamed Of Being a Crossdresser? (21)