Crossdressing with womens trousers

A number of years ago, I got over the idea that I could only express my feminine nature by wearing only skirts and dresses and added women’s trousers to my wardrobe. It only took a few styles to convince me that there was a world of difference between men’s and women’s trousers. The texture of the cloth and the cut are decidedly different. One of the things about wearing pants is that many styles are masculine cut and can be worn when my presentation is masculine. I started wearing women’s jeans exclusively and then found a pair of slacks that would look nice with my blazer or a sweater.

By adding pants to my wardrobe, and certain styles of blouses, I can go anywhere and be around anyone, even those to whom I’m not out, dressed in totally women’s clothes. Thus, I fulfill my need to express my feminine nature and yet still interact with my friends as a man. What’s more, my wife, who’s very cautious about me expressing my feminine nature, is quite OK with this.

Now here’s the interesting part. A couple of years ago I broke my leg and had to wear shorts everywhere. I only had women’s shorts to draw on. Actually, only two pair and only one of them had the masculine cut criteria but the other really pushed the envelope. The first pair that I wore to church had a faux fly and had the look of men’s. However, my wife had worn them to the church picnic the previous summer. My wife and I decided that if someone noticed that I could point out I had the broken leg and use the “temporary” need of shorts as an excuse to “borrow” her shorts. But no one even blinked. Well, you can’t wear the same clothes all the time, so I pressed the other pair into service. They had not the evidence of a fly and had hidden in seam pockets but most damning of all was the fabric. It was a kind of knit that would never be seen in men’s clothing. Relying on the “excuse” I boldly wore them to mid-week service at church. Again, no one blinked.

After that my appetite for more feminine pants was wetted. I did away with all my men’s slacks and began to wear only my women’s pants everywhere. I tried out wearing my pants that had no hip pockets at all and purchased some that had the fly going to the distaff side and got no reaction. To cut to the chase, I determined to push the envelope to what I felt was the max. I purchased two pair of side zip slacks. NO FLY. One pair is khaki, the same color as the slacks that I’ve been wearing most often to church on Sundays, and the other is black. I had been wearing the black pair with the feminine fly to midweek service most often. The khaki pair has the zipper inside the left pocket with a button on the left hip and the new black pair has the zipper hidden in the left seem and only has decorative small patch pockets on the front. Since we are a bit casual at our church, I don’t have to wear a tie to fit in, so I’ve worn either a sports shirt or a masculine cut blouse, both un-tucked to make the lack of fly less noticeable.

Well, I’ve got to tell you, wearing a pair of pants that make no provision to stand up in the restroom, is very satisfying. There’s just something about that aspect of femininity that makes me feel whole. I think that’s part of the attraction to skirts and dresses. Yet wearing women’s trousers, I get the same satisfaction.

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Patricia Marie Allen

I'm 72 years old and have been cross-dressing since I was 9. I'm married to an understanding woman. We've been married for 49 years, 50 come August. We have two grown children and two grandchildren. My daughters know about me, but my son-in-law and grandchildren don't. At home, I'm express my feminine side almost exclusively. I'm free to come and go in that mode as I wish. I have a good wardrobe of women's clothes and nearly no men's clothes. When it is necessary for me to appear as a male, I simply wear the masculine slacks and a "big shirt" from Woman Within that are part of my women's wardrobe. On those occasions, I wear some penny loafers I got from Zappos.

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29 Comments
  1. Tiffany Anne 2 years ago

    I too love the fit and feel of women’s pants and jeans. But I will tell you the most comfortable leg coverings in the world are leggings!! You can’t wear those to church though of course!!! 🙂

  2. Lea 2 years ago

    Wearing feminine pants makes the CD!

    Really enjoyed this article. Women’s pants are really comfortable, even the tighter fitting ones. I too ignored them during those initial stages of crossdressing, mainly in private. I discovered women’s pants when I started to want to go out in public.

    Nice details on the various differences of women’s pants. Most guys wouldn’t notice those differences, and women wouldn’t expect that guys pants are different. Luckily, even pant colors and lengths are crossing the gender divide.

    Pants are a nice solution to express that feminine side, subtly. If only women’s pants had deeper front pockets – otherwise, great excuse to carry a purse.

  3. skippy1965(Cynthia) 2 years ago

    Patricia-great article! I found that the women’s stone khakis (named Felicia” by Bandolino) are androgynous enough that can wear in place of regular men’khaki pants to work so now at work i’m wearing undies,cami, leggings or tights, trouser socks and women’s slacks–only guy clothes to work are shoes and polo shirt! I love it!
    Cyn

  4. Abbie Simons 2 years ago

    Thank you for a wonderful article Patricia, I wear female slacks as well with no fly but have an elasticated waist, i have done the same with jeans as i wear jegging’s or boot cut skinny jeans. Truly liberating is all i can say and takes the pressure off as no one seems to notice, as they are not too obvious. i love the excuse to carry a bag as most slacks and jeans have no pockets, Yeah.

  5. JaneS 2 years ago

    I get really annoyed with tranninazis who try to tell me I can’t wear pants and have to wear dresses or skirts. I find that just as narrow-minded as cisgender people who try to tell me I can’t wear dresses or skirts.

    Let’s all have the freedom to wear whatever we like. If that’s a cute pair of women’s slacks with a Empire Stormtrooper vest and helmet, then So Be It!

    • Lea 2 years ago

      Well said! Everyone should have the freedom to wear what they want.

  6. Karyn Lobelia 2 years ago

    I started wearing side zip pants to the office and in public after my hair was shoulder length and I was usually wearing a ladies jacket in a men’s style . Sometimes I wore a shirt or tunic like blouse over the top of my pants . I n the summer I wore Capri pants Bermuda shorts or clamp diggers often all in ladies styles . It was a big jump for me because my legs are waxed . Recently I often wear a tunic and leggings with ballet flats to work . I really love leggings with tunics or very short dresses .

    • Lea 2 years ago

      In all my adventures, I haven’t dared wear women’s clothes to work. I’ve worn women’s sneakers, but those are hard to tell. How do your coworkers react?

  7. Tammy 2 years ago

    I wear women’s jeans exclusively. And that’s a problem, since I need at least one pair of black pants before August. Any suggestions? I’d like belt loops and a hip pocket big enough for a wallet. Front zipper optional. Thanks!

  8. Freya 2 years ago

    I wear women’s jeans and slacks exclusively
    No one notices the difference in the office and it’s so much easier and cheaper to get my size in the ladies wear department

  9. Karyn Lobelia 2 years ago

    Most of the women in my office wear pants or leggings but dress professionally for the job . The total outfit is what gains attention and my lady friends respected me because I always try to be helpful . Actually wearing a diamond tennis braclet and gold braclets made me more femme to n their eyes than my side zip pants . Women did notice but more because of the silk and softer materials , men did not really notice . However , when I started wearing 3/4 ballet tunic tops and leggings with ballet flats I felt very femme and was treated as a lady everywhere . At work I simply told anyone who ask that I was femme and preferred feminine clothes . It was easier to dress this way for me since I wore my hair in long OVS feminine hairstyles and light natural makeup to work . Some pants were ankle length which I wore with wedge sandals . OVS I used the female bathrooms as I could not use a mans bathroom without someone saying I was in the wrong bathroom . Especially when I wore keyhole silk blouses a lot and lipstick in light colors . My nails and toenails were typically French nails and ask my hair was below shoulder length I wore hoop ear rings : Where I live in Orlando most women wear pants ,shorts , or leggings . I simply try to be in n fashion of what other young professional women are wearing . But not those men style suits anymore , be know me and polite and just b yourself . Kisses and hugs

  10. Debs 2 years ago

    Great article
    The only thing I retained after my purge were a couple of pairs of women’s trousers (a pair of jeans and a pair of faux combats) which I’ve not tried to wear again. They fit fabulously so I need to dig them out.
    I did buy a pair of girl’s Capri length cycling shorts recently and I was a bit dubious of wearing them to ride to work in. Then I tried them and realised how fab they fit and feel on. Normally when I get to work on my bike I go through emails and do a few little housekeeping jobs while I relax before getting a shower, but with my girly shorts I took a little while longer before getting changed because I didn’t want to take them off LOL

  11. Donna Wilson 1 year ago

    I love the feel of skinny women’s jeans and recently had my first public outing complete with boots, no one even looked twice.

  12. MaryJo 1 year ago

    How about jeggings? Do you have any of those? I don’t know why I didn’t add those sooner to my feminine wardrobe.

    • Janine Milburn 10 months ago

      I love leggings, i have 3 of them, i look pretty hot in them with high heels

    • Author

      Hi,

      I wrote this article some time ago. Since then, I’ve pushed the envelope a little more. I currently have three pair of women’s slacks that I wear to church. They are all elastic waist with only front pockets and not even a faux fly. I pair them with three complimentary colored “Big Shirts” form Woman Within. I’ve also added a pair of “women’s loafers” to the mix. I wore them quite by accident one day to a church function. No one seemed to notice. I call them “women’s loafers,” because when I wore them one day when I went to help my wife clean the church and on the way there she asked what shoes I was wearing and I told I was wearing the brown women’s loafers and she accepted that since they were loafers they must be masculine enough. They can be seen here, http://bigclosetr.us/topshelf/system/files/u49/20160106_155554%5B1%5D.jpg

      Also for work, since I’ve lost weight and the company quit supplying pants for our uniforms (I’m a CDL driver for local delivery) I bought six pair of women’s work pants. They are grey denim with the fly on the distaff side and only one hip pocket. I really prefer the fit as apposed to the last pair of men’s jeans I owned. I also wear Champion women’s tennis shoes at work. The only male clothing I wear at work is a polo shirt and jacket that the company supplies as part of our uniform, but then they get the same jacket and polo for women.

      I do own two pair of leggings. One is capri length and the other has a slight flare to the legs below the knee. I’ve worn the longer pair, with the flair, out with my wife and she accepts that they are just pants.

  13. Stefanie 1 year ago

    Women’s jeans for me and sweaters with pretty panties underneath

  14. Margie 1 year ago

    I’ve been wearing women’s jeans for years, even when I’ve purged, and no longer have any men’s My fav is Gloria Vanderbilt’s “Amanda” but I also wear Lee’s which had a “Sinfully Soft” but are no longer available. These have a silky waistband and inner front pockets … and wearing silky panties takes enjoyment to a whole ‘nother level! I did find my last pair on ebay but I’ll soon have to cut them down to short shorts because the spandex is wearing out. I just hope I can extend their use. Gloria Vanderbilt & Lee “classic fit straight leg” are like the skinny jeans and can be found at JCP or Kohls, they have many different styles. I actually got my wife to buy them. The part I love is these jeans “stretch” and conform to your body so much better. I wore them to work, church and now just about everywhere. They still have that dreaded small pocket issue, especially for a wallet, I’ve had it fall out often at cribbage day but it’s always been the lady’s that pick it up for me 😉 I’ve learned to keep the wallet thin and it helps somewhat. Last I looked they seem to be getting more embellished now and that has me a little skeptical, The Amanda’s always came with either a Gold or dark swan over the right front pocket but I’ve only had one question about it – from my granddaughter!I’ve always tried to be under any radar … somewhat.

    Margie

  15. Dani 1 year ago

    I haven’t owned any mens pants or jeans for over 35 years. My jeans are all patterned pocket ones, My slacks are women’s, some with the zipper on the left, some with zipper on right and some with no zipper and no back pockets. All have at least 5% stretchy material.
    I normally wear a 30 inch inseam leg length. However I typically buy 33 inch inseam so that I can wear my 2-2.5 inch heals in sort of a androgynous mode. No one notices.

  16. Michael 12 months ago

    I love to cross dress ii wish I did not have t hide it but she would not under stand but soon I won’t have to hide it we are getting a divorce the I will start to became a full cross dresser.

  17. Sandy Wright 10 months ago

    I was exposed to agent orange years ago. I developed stage 3 kidney disease and further developed fungus infection in my crotch. I have worn skirts or dresses for the last 7 years. Yes, I go to church and everywhere else wearing skirts. I have had limited problems and looks but no real problems. My VA doctor diognosed the fungus infection and told me to wear skirts or dresses and leave myself open to the air. I wear no underwear and can’t stand anything between my legs. I am very comfortable dressed as a female and doing so feel perfectly normal for me. When I was in my teens I wore female panties all the time as they were much more comfortable. I would be completely comfortable with my balls and sack removed, yes, I am 80 years old so what do I do?

    • Tamera Lynn 6 months ago

      Hello Sandy . . . . . a fellow Vietnam vet, at last; I served with the 4th Infantry Division [even though I was Air Force] in ’66 – 67, and developed a case of ‘genital herpes’–that used to flare-up, occasionally [not in many years, now]. I went through two unhappy / unsuccessful marriages, before finally admitting to myself that I’m bisexual; along with this, I realized I was a ‘closet CD,’ as well; I am truly thankful for discovering this site, which resulted in my joining. I wonder if a group for ‘CD military veterans’ would attract members, like the two of us; I served a total of 24 years, before retiring in 1991. I always new there were gays & lesbians in the military; my First Sergeant [at my very first duty station, following ‘basic’] managed to ‘seduce me, orally,’ when I was twenty, and we had an ‘oral only,’ 6-month affair–before I left for Vietnam. I never got with another man, until this past May–and have had two other ‘one night stands,’ with male lovers, since the first. I’m avidly searching for a man to settle down with, for the rest of my life, but no success as yet. Sorry for the ‘book-length’ message, but my cardiologist suspended my driving privileges for a minimum of 3 months–due to arrythmia episodes [I have a pacemaker / defibrillator installed, ever since a heart attack in '04; also a bladder cancer survivor, since December '15]. Love to you, Tamera

  18. Janine Milburn 10 months ago

    I love tight leggings
    makes me feel hot

  19. Cindy Morgan 7 months ago

    I love wearing leggings and tight jeans. It make me feel good.

  20. Tamera Lynn 6 months ago

    Hi Patricia . . . . . thank you for your informative article; you’ve provided me with some excellent ideas, regarding the purchase of women’s clothing. I’m 71 years old, bisexual, and a complete novice, to all of this–my only experience being, the secretive ‘trying on’ of my wife’s panties [we’ve been separated for a year now, and I live alone with my two cats]; since that time, I have often meandered through the women’s clothing departments, of stores like Walmart & Target–but never purchased anything. Eventually, I want to work up the nerve to enter Victoria’s Secret, in our local mall. Love to you, Tamera

  21. Diana Benard 6 months ago

    I agree completely. The fabric of woman’s trousers is much more comfortable and the cut much more stylish. I almost always wear woman’s trousers now and have never had anyone comment. I only wish that they made the pockets a little deeper, at least until the man purse is more accepted.

  22. Sara Marie Franklin 4 weeks ago

    Wow I do not know if i could be that bold I envy your courage. I will agree though i own 4 pair of jeans and one pair of caprices and I love the feel the fabric. Just takes getting use to buttoning them up on the other side. : )

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