The three reasons I couldn’t stop myself from crossdressing.

I admit it. I started crossdressing before I was a teenager. I found myself sliding down a slippery slope that led first to shame and guilt and later to an acceptance of the unique individual — and unique pleasures I could enjoy!

The first time I pulled on a pair of panties I can’t have been more than 5 years old. They belonged to my cousin and she’d left them at my house after a sleepover. My mother mixed them up with my things in the wash, and they found their way into my drawers.

It’s remarkable, but even then I could tell those little black panties were different. I felt guilt and knew what I was doing was wrong, and yet still derived a guilty pleasure from putting them on for a few moments.

Right from that moment I knew it felt great. The fact that it was a guilty secret made it all the more interesting. So, there was strike one.

I probably didn’t wear anything feminine until I was sixteen, and already had left home. I found myself with a girlfriend who loved the dress up style of the new romantics. That was a movement that’s largely been forgotten today, but stepped into the realms of gender fluid style in the early 1980s. It was almost pushing back against the punk world, and my little girlfriend loved to go out with me after having applied makeup to my face and painting my nails.

All that was innocent enough, except that when we’d get home after a night out, my girlfriend would undress me, revealing the panties and bra she’d secretly asked me to wear, tapping in on the thrill I’d learned so early in my life. Gradually, over the years she would dress me more and more elaborately until now and then I’d be going out completely dressed as a woman, and getting away with it. When we’d make out at a club or a concert onlookers would be convinced she was a lesbian, adding to the already heightened thrill of being a highly sexualised teen. Keep in mind that two lesbians making out together at that time was not something you saw in public very often. Strike two.

My dressing went into abeyance after that relationship ended. I found myself following a life of conformity and conservatism. I felt something was missing, but was trying so hard to conform I don’t really think I had any idea what was lacking. By my early thirties I was on the treadmill of mediocre marriage and depression. Only when that structure disintegrated in divorce did the world begin to reform itself.

And then came Monica. In the post marriage landscape I looked for new connections and experiences, and with new found sexual confidence found myself asking for the things I actually wanted instead of attempting to follow a norm made concrete by society. As lovers came and went life drifted toward a better resolution. Then, one day, I found a lover who shared my appreciation of lingerie. Only she asked me to put it on, and then make love to her. The passion was heightened for us both, in a breathtaking flurry of nylon, and and silk.

Immediately the thrill returned. Then came the makeup, the heels and new delights in the bedroom. Having shed the shame and feelings of hesitation, it was like diving into a pool of stardust, and coming out sparkling with excitement. And there it remains.

The breathtaking intensity of dressing is something that never ceases to amaze me to this day.

Three strikes, and I am out! Completely out!

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37 Replies to “The three reasons I couldn’t stop myself from crossdressing.”

      1. I have never been able to stop I have wanted to dress Spencer my older brother dressed as a girl for Halloween
        But I did not where panty hose till 7or 8 then my sisters dresses I scared the little neighbor boy after Put my sisters dress on in front of him he ran home. But I have been very discrete over the years. I can’t stop and the more I dress the the more I won’t to have a cock to serve. I do like wemon but I have come to the conclusion that I like men to but only in the sence that I’m sexy enough for him and can turn him on by being as feminine as I can be. It is strangely a dicktive oh no did I say that, I have wanted a another girl to dress with but I’m thinking I wil from now on serch for men to please. Only as I have explored further I find that I can come with out a hard on. It surprised me at first, then I realized it was natural for me to feel this way as I’m emulating what a woman thinks while having sex and that’s what’s on my mind as well. Thanks for letting me cry out and try to be as sexy as posable.

  1. That last comment says it all!
    “The breathtaking intensity of dressing is something that never ceases to amaze me to this day.”
    I couldn’t have said it any better!!!

    1. I concur with this comment that “the breathtaking intensity of dressing” continues to amaze me. I so often wrestle with it because it seems like I am wasting time, but, at other times, my ability to focus while dressed almost seems to make up for the loss. Sometimes, when I find a particularly compelling item of clothing or even a new combination of clothing I’ve had for some time, my euphoria is overwhelming.

      Last week, I bought a short black tailored suit jacket from the closeout rack at the thrift store. It was half off day, so I paid $.50 for the jacket. I brought it home, combined it with simply panties, white skinny jeans, black high heeled pumps, and a pearl necklace. I was in extacy. Who could know that after a lifetime of crossdressing, I could still find such satisfaction in so little?

  2. This back and forth of the mind…
    I totally agree eventually you can’t help getting more and more into dressing up properly, because for me at the end of the day, it makes me feel less weird, more complete, being simply myself, in a wonderful acceptance…
    I am Lola, and she blooms, slowly but surely… I won’t stop until I can be fully myself. This is beyond the thrill, it is totally me and I’m such a beautiful lady when it comes to be fully shaved, dressed, perfumed, and i know one day people (both women and men) will stare at me like “oh la la”

  3. i started to try on my 3 older sister’s clothes when i was 5 or 6 – it was a cowgirl’s skirt. I loved it.

    Then came the underwear hanging on the clothes line – had to try that. I have been crossdressing for 55 years and i am 62 now. I love the mind shift that happens. I went thru the purge of all gurl clothes only to go out and buy more – did that a few times.

    I got married at 40, then when wife stopped having sex with me I started to dress again. She finally asked for divorce 3 years ago and I have ramped up my dressing activities now that I am single again. Slowly going out in public more and more.

    I get ladies clothes that can pass for guy clothes so as not to draw much attention to myself. Even met a guy on line and had sex with him dressed as Tina – wow what a rush that was!!!!

  4. Flat out love it… what can I say?
    How about the thrill.. For me its in the shopping… Love thrift stores. The ladies get all freaked out. Either going through gowns or lingerie, they look and wonder. Eh, let em wonder. I look great in a gown…
    I spend time looking at labels, checking sizes, looking for the right style for me. As Fiona says,”create yourself as you wish.” I like split leg open gowns that show a little leg. Long length dresses add to allure. Still looking for the right mini skirt.
    The rush is walking toward the registers. I know I am going to run off and try it on. The cashiers get really strange. Some get curious, most are appalled. Standing there paying for it, I get an adrenaline rush… followed by a sense of moving into being me. Its not sexual but sensual…
    Now its relax and get comfortable time. Try on this and that, enjoy the new looks and decide on hair or make up. Get into the Femme Me… Out comes Liberty…
    This is the last time… no more trashing my collection. no more hiding it all.
    It is me… Liberty Bell

  5. Ex gf was bi gal she pushed me to dress fem and roleplay. At first i wasnt keen but as privately, i grew to enjoy. Made to act girly around home fully dressed and seduced by gf, it became second nature and i loved feeling smell and look.

    After a row before xmas she let on to a crowd of friends, and all of a sudden her girl pals and guys kept pestering me to go out with them in fem attire. After a bit i gave in it was so different being out and open. Garments felt so sexy, i seemed to fit in and girls guys kept complimenting me and buying drinks. Suddenly i was a girl, flirty, teasing and loving every time i was brushed against or hands touching my body. I was loving all and suddenly i loved being the girl and being wanted by guys. I long to do it agian!

    1. Wait untill you make out with your first man and he squeezes your ass and bites your neck you feel his cock harden and rub against your thigh or crotch you will feel your Boy clit begin to leek and the desire to have his cock in your mouth or pumping a hot load of his sweet cream in your tight boy pussy I did and still do go for it girl

  6. My moms stockings hanging after being washed attacted me at age 7, and I had to try them,,,,then came bath powder, and her undies when mom and dad were out. College, girls asked if I wore tights and pantyhose, marriage, she sensed I was different,,divorce, a shock, but we remain good friends….And now, I really want to discover my femme side,,,Trina is part of me

    1. How I learned how to put on my nylons from watching my Mom. First you roll them up in both hands almost to the toes. Then you insert your toes and pull the nylon over your heel. You can do this with your legs crossed. Or while sitting at the vanity or n the bed. Once the nylon is over your heel you point out your toes and raise your calf out horizontal. The you hold your nylons tight while pulling it over your calf. Continue and pull it up over your thy. You the rub both hand up your calf and thy to get the nylon nose and thigh the on your leg. Only after you have it nice and tight can you attaché it to the front strap of the garter belt. Oh my what a turn one I get ever time I do it. I have a feeling you’ll love it too.

  7. It is so reassuring to hear that so many others have trashed all their clothes only to start all over again.
    Already I have discovered likes and dislikes, and made changes.
    I truly love dressing, the thrill, the feelings both physical and mental, just sitting at my desk in my femme Carinya self.
    My wife has been away for two days and short of the time spent on a golf course I have been Carinya for hours.
    I love wearing my breast forms both bra less or in bra. And heels? Oh my.

  8. You are so lucky to have found a woman who enjoys this part of you . I am so jealous . I have just recently discovered you and your website . I am intrigued but more than a little hesitant to indulge these lifelong desires .

  9. The urges began at 14 although my sister, older by 3 years dressed me as a girl so she had a sister, i was 1 to 2 then. Whole lot of sneaking around in my teens and yes there was shameful guilt too. Same here, trashed all of it 3 times only to start over. 3 times divorced and only the second one was never told, have a daughter with her, last girlfriend encouraged me and we had many nights of dress up and going out. It is so exhilarating to get dressed fully and go out, I get many compliments even at 57.

    My girl wardrobe is bigger than my mans!!! I love to shop and depends on the person working but i just go about what i am doing like it is natural. Sometimes i have a list and make like i am sent to get things. Most clerks just smile and some are really helpful. The only way is forward for me and yes, no more trashing the stuff, i have too much invested now LOL and it is too much fun.

    1. Trashing is a part of Fem life guilt and new love as a girl going out Enfem guys buying you drinks as you flirt with them an occasional hook up is nice if your into it like me if your not its ok as long as dressing up makes you feel good do it be happy

  10. 3 reasons…hhmmmm

    1. I love the attention (and other things ; D ) I get from men
    2. The clothes LOOK so much better than man clothes
    3. IT WAS ON SALE!!!

  11. I love having my boyfriend (oh, yes, I now have one!) put his arms around me, and kiss me! I cannot describe it, but it is so warm and loving! I adore being his source of pleasure, and want him more and more every day! I could be his all day woman, id only he would decide to live with me! I would do everything for him, and love him daily!

    Roxanne Lanyon

  12. The first time I was in the 7th grade my sister 3 years younger than me needed a baby sitter on weekend and mom called a friend whose daughter was looking for work her name was Stephanie and she was so hot. Well, she would take showers at our house and leave her clothes on floor in bathroom. I needed to go pee so bad when she turn off the water I pounded the door so she let me in and that’s when I found my first pair of panties and after that every weekend it was the same thing and i got braver and I took a pair that’s when my life turn and i have been looking for since.

  13. I’ve tried to g quit a few times. I don’t know how many bras,panties and stockings I’ve trown out, only to go out and buy some more. That is why i’m tring to accept my feminine self.. feminine clothes especially panties, bras and stockings!

  14. Wow! You said it: “The breathtaking intensity of dressing is something that never ceases to amaze me to this day” I feel that every time I dress pretty, put on makeup and wig. The moment the door opens and I go out, there is an excitement found no where else! I have yet to experience the uninterrupted week of dressing exclusively as a woman, and doing everything publicly in femme mode. It is still a goal.

  15. I’ve heard that once a crossdresser, always a crossdresser. And it’s true.

    I’m a man who struggled with cross dressing fetishes for years- buy women’s clothes, wear for a few days, throw them out, then buy again, repeat. I finally got to a point when I accepted my need to dress as a woman- I’ll occasionally wear clothes like skirts, blouses, and dresses at home- and only wear nylon panties, 100 percent of the time. Life is so much better now that I’ve accepted myself. I am much happier now that I’ve come to terms with my need to dress as a woman.

  16. I feel strongly that a part of me is definitely feminine and this is what I have explored over many years, usually in secret although my wife knows about my lingerie dressing and accepts it, even though she is probably perplexed as to why I want to wear ladies undies. Just let me say that I continue to be thrilled to select and put on a pretty lacey bra and matching panties – it’s almost daily now – and even more excited when I can wear one of my blouses, pair of ladies trousers and ballerina shoes. So far I have not gone so far as the final steps of makeup and wearing a wig, but they will come, I am sure. It is truly fulfilling and natural for me to be a woman, and I would love to reveal this to family and friends.

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