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 appleid 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 ccnform 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 intesity 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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20 Replies to “The three reasons I couldn’t stop myself from crossdressing.”

  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!!!

  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. 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

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