Greetings, my dear readers. First I want to express my appreciation for your responses to my blog postings. It is so rewarding to know that there are so many of you that share this common experience with me that we call, loosely, “crossdressing”. Perhaps a better term is “gender fluid.” That pretty much works for me, as we all have a sense of who we are that is much broader than the confining role of the traditional binary male. I can’t imagine going back to being the macho male I once pretended to be (I say “pretended” because that was never who I really was) and wearing those heavy, scratchy underwear. Thinking about this fascinating journey of embracing the inner femme that we know ourselves to be, I started wondering about what got us all started on this journey.
I’ve read a lot of posts on various sites, regarding crossdressing folks like us, and have found there are many starting points. Some have sisters, and got started by exploring their sister’s panty drawer, or closet in search of the perfect skirt or dress. Others went foraging in their mom’s closet and dresser. Others didn’t have a sense of their femme self until later in life and lived, or do live, in fear of discovery by their wives. Others, the most fortunate of all, have a spouse that is totally okay with the feminine side of her husband or significant other, and lives happily in the gender fluid world with him.
So, I have a question for you: what got you started, and at what age? When did you first slip on that luscious pair of panties and know you were hooked – that this was a part of who you are? When did you first try on that first bra, or blouse, or skirt, and know that this was something you just had to do? We all had some starting point that led to where we are now, and I would love to hear your stories. By reading the blogs here at Xdress, surely by now you know you are far from alone in this fascinating world of the gender fluid; you are part of a virtual community here at Xdress. Tell me your story – I would love to hear it!
Love the photo by the way!
Although I occasionally wore my mother’s silk panties in grade school, it was not until I got married after college that I really got hooked on lingerie. I inexplicably felt a very strong urge and desire to try on my wife’s sexy Vanity Fair nylon panties. Instantly I felt a rush of Adrenalin and fell in love with how the nylon felt on me. I was hooked for life. It was a very sensual experience that I never forgot,.
I got started when my girlfriend left a pair of her panties behind one morning. She left for work and I saw them on the floor and immediately tried them on. Green satin panties with the frilly little bow in front. After 20 years, I can still feel the rush I felt pulling them on for the first time! I took them off and went to work but kept thinking about them. I rushed home for lunch and tried them on again but this time kept them on while I went to work. I cannot explain how turned on I was all afternoon knowing I was wearing women’s panties while my co-worker’s had no clue! I dabbled with VS panties for years and liked their selection but sometimes the fit was more for the woman’s body than it was for a man’s but I couldn’t fault them for that. I love the styles they offer, even to this day and I still shop there from time to time. XDress has a better fit since it is designed for men. My only complaint is that the inventory runs out too quick on may of their styles. But I love the site and the selection. The Satin Hipsters are my new favorite followed closely by the Satin/Lace Brazil Panties!
My first experience wearing panties was pretty typical. I was 13, home alone, and was finishing some laundry my mom had left. I was folding laundry when I saw a pair of shiny blue VS satin panties. They were fresh from the dryer, so I decided to strip down and try them on right then and there. The warm satin felt amazing on my bottom, and I was hooked. I would sneak into my parents room once a month and steel a pair of my moms panties. For a while I would only wear them around the house when I was alone. I would strut around the house in just panties. It was amazing.
It wasn’t till I moved out a few years later that I started buying my own panties. Now I wear them everyday. I have no men’s underwear anymore.
I was so glad to come across this blog it helped me understand that im not alone in the way i feel. Mine started pretty early my parents separated when i was 5, so I pretty much was raised by my mother and my sister lived with us. My fist exploration happened with a very shiny skirt that belonged to my sister. I got caught trying that one on and my mom didn’t think too much about it she always called me sister anyway. After I tried that skirt I wanted to try more so i started sneaking into her room while she was away she was the black sheep and wasn’t usually home and my mom worked a lot to support us which left me at home with quite a bit of time on my hands. I can still remember the first pair of hers i snuck was a metallic purple thong. It was so hot this was all when i was about 6. It didn’t stop there I snuck quite a few more throughout the years discovering along the way that absolutely love string bikinis panties. I hid it from almost everyone except for one guy I slept with when I was a teenager he found out when my pants came off but he didn’t seem to mind it was a pair of silky string bikini that I lifted off my sister. It was actually really lonely not being able to tell anyone but the area of the country Im from it wouldn’t be accepted even by my closest friends. The only other person who knows about it now is my wife of almost 12 years she hasn’t known the whole time i told her almost 9 years ago and now I have an assortment of bras and panties that she’s ok with but I can tell she’s still not to keen on it. I have brought up lingerie and it started a huge fight between us and almost ended our marriage because she didn’t want me to. She’s more ok with panties than anything but i think thats because they can be pretty well hidden but I do have to say its gotten better i went with her to get a pedicure for the first time in my life 2 months ago and she loved it my tows are painted right now we plan on going again this next month she has no idea how happy she made me by not throwing a fit over my nails being painted she enjoyed the time and so did I I still feel so girly with my toes painted. I will be getting red next time they’re blue right now. Thats part of my story anyway im so glad I was finally able to share it with someone even if this is an old column. Thanks bunches y’all.
When did it all start!
From a young age I realized that I liked being a girl. Possibly in the games with my cousins and I looked at their pants and felt a great fascination. Later, also playing with a friend of mine, he asked me to be his wife. I was fascinated, I played the role as a whole. Every Wednesday, in our games, I was his wife, until the day he gave me a kiss on the mouth and stunned me. If I didn’t have a lot of doubts with less, I was a girl. It was even a first step to wear a pair of pants, on one of those Wednesdays he told me go to my mother’s dresser drawer and choose some pants to wear. I remember it as if it were today, blue with a nice touch.
Since then every Wednesday I wore underwear and never stopped assuming as a woman.
I don’t consider myself gay, but a woman!
Since then I have not stopped using underwear, although when I was at my parents’ house it was more complicated, since I went to college and now at work I use it daily and I can’t use anything else.
In addition to this relationship I had two more and I am lucky that these people encourage me to wear lingerie and pull on my feminine side. Thanks to Xdress for being able to share our stories.
I love you !!!!!
It is nice to have online access to others that wear. Years ago we did all this is without any real outlet. 61 now and times have changed. Before I share my story I will say with respect to all the reasons we wear, I wear because they make me feel sexy and comfortable, in the bedroom or day to day. I’ve also just been into wearing the panties and sometimes stockings/garters. I don’t think I every would have made a good “girl” even when I was young. So I am the male who wears undies. I have enjoyed wearing for men and ladies over the years but there is something so erotic about seeing a mans eyes looking at you while you wear and he is turned on….
Growning up in Florida I had the chance to work a summer cleaning a neighbors pool while they were out of town. So into the house and into the panty drawer curious 13 year old me went. she was an older lady maye late 50’s but she had wonderful lingerie and such sexy panties. At first I just played with myself holding them, loving the feel of the fabric and the look. Soon I had to try them on. Don’t a lot of guys in their lives try some on at one time or another? Well I was hooked.
After a hitch in the army I came back to Fla and had an apt and I would “find” panties in a laundry room or a thrift store and that was my playtime. I started going to the adult book stores and now and then wear some there to watch the movies. One day an older man maybe in his 60’s came into the booth I was in because the lock would not catch. I am standing there in only a pair of white satin with lace trim string bikini panties. I am frozen standing there and one thing leads to another. Just the feeling of seeing how excited he was turned me on so much.
I love women and I don’t see ever being totally fem but are there many of you other there that feel the same way? That sometimes its fun to try the other way so to speak. Panties make that happen for me. Just thought I’d share.
I love stories about teenagers trying on their mother’s or sister’s panties and instantly becoming aroused. My sexuality emerged slowly and it never occurred to me to do anything like that. The first I knew about crossdressing, as a student in the 1960s, was from a book called ‘Sexual Deviation’ by Anthony Storr, a psychotherapist. He mentioned how some men liked to crossdress and pleasure themselves, often in front of a mirror. I realised at once that this would please me a lot! Storr reckoned that my condition was neurotic, and curable by psychotherapy. I knew I wasn’t ill and did not want to be ‘cured’.
Fast forward a few years. I had been married for a year and found myself alone in the house. I slipped on one of my wife’s nighties, then stood in front of a mirror and did what came naturally, with the greatest enjoyment. I was now officially a sexual deviant and it felt fantastic! From then on I was hooked. I relied on my wife’s wardrobe for some years. If she suspected anything, she never said so. (Many years later, she was dismayed to find part of my stash, but at least it didn’t include anything of hers!) Later I discovered other sources of my favourite garments, which helped me realise that there must be many others who shared my tastes. It would still be more than 20 years before the advent of that godsend Apres Noir/Xdress, which enabled so many of us to buy pretty things which fitted perfectly and did not show under our clothing, to say nothing of gorgeous babydolls in satin, chiffon and lace.
I wasn’t in my teens yet when I had the chance to cruise through my mothers underwear drawer. I did find some silk panties and tried them on. Not much transpired from this adventure and many years went by until the mid 80’s came around and then I noticed and felt the urge to try wearing again.
When the 80’s hit I was into the Rock band, Hair Bands in that day. I went to many concerts and took obvious note into what the girls were wearing and how super sexy I found the look to be. The super short, tight skirts, thigh highs, garter belts, heels and lets not forget the hair. As I arrived at the day of the concerts, my neck would get a workout from looking in so many different directions and skirt after skirt. Even though the skirts made me look, they mostly drew my attention directly at legs. I have a thing for sexy legs and I received some complements about mine growing up.
So, another 20 or so years later, the chance for myself to experience trying on skirts presented itself to me and I took it. I found a Black skirt at a yard sale while browsing and decided to add it to my other guy clothing I was buying, stuck it in between the clothes and asked how much. A few bucks was said and they never looked though the items and away I went straight home. My clothes couldn’t come off fast enough as I tried on my 1st skirt. It hugged my skin tight but it had plenty of stretch to the material. I was hooked from then on. Any chance I had and was alone I wore that skirt. If I didn’t have to take it off, I didn’t. I still have it today and is still one of my favorites.
Since that 1st day I tried on that skirt I have since accumulated much more clothing. Its grown to include, lingerie, panties, bra’s, tops, dresses, and now another big interest, Heels. I haven’t yet to be outdoors while dressed up, only inside, when I get home from work and shower up, I get into dress and I feel so much better. I absolutely feel much more comfortable in femme wear than in my regular clothes. I love it.
My earliest remembrance is wearing pale blue ruffled nylon swim briefs when I was very young (about 4 years old). I only had brothers so was not surrounded by much feminine, but I believe my mother always wanted a girl, so dressed me in girly clothes while she could get away with it. One or two photos of me in a baby dress survive. I suspect this is not all that unusual, and may be why many of us have a desire to wear panties and more. I did not start wearing panties by choice until I was much older, but I do remember as a child being fascinated by girls in dresses and getting a glimpse of white panties was heaven!
I remember very well: 1986, I was 6 years old and found one my older sisters’ tap dance outfits. It was a kelly-green satin leotard with white sequins on it, not a lot, but scattered around. The finishing touch was a short white tutu. This outfit was made for boys like me! Not really caring about anything, I put it on and started dancing around. No one saw this, but I wasn’t hiding it either with my bedroom door open. I stored the outfit in my closet, which no one seemed to notice either lol! Both my sisters and brother are considerably older than me, so its not like she was going to wear it again. Now that I think about it, I wonder if my siblings and parents DID see the outfit in my closet and put two and two together? Mind. Blown! I kept wearing that adorable little outfit for several years.
At 8, my only friend was a girl my age, Tina, down the road (I live in the sticks). We were playing one day when she wanted to have a tea party, but explained I couldn’t wear boys clothes, that we had to wear dresses. She got one out for me, and I took her seriously when she said “no boys clothes” by taking off my undies too. Inevitably her mom checked on us, and we explained how I ended up in a dress. This woman was SO accepting and so nice, she just said how sweet I looked, but not to wear any of Tina’s dresses again… without undies. Mrs. K was (is) an angel, I can NEVER forget what she did for me: the next time I came over (or somewhere around there), she called us up to Tina’s room where she had cookies and Kool-Aid for another “tea party.” She had laid out two dresses for us to wear, except one dress had little pink panties laid on top, and they had small white bows on the hips. They were for me! My very first panties, and (unlike most of us), they were my size :) She sent me to the bathroom where I removed every last piece of boy clothes, and slipped my panties on. I was physically excited, if you know what I mean, but also VERY emotionally excited, and I still feel my heart racing as I asked through the door if they were ready to see me. Something took over, and I twirled around for them a few times, and did some silly poses before Mrs. K helped me into the dress. That was the best tea party ever! Nearly every time I played with Tina from that day on I was dressed as a girl – sometimes just panties, sometimes head-to-toe full dress-up, sometimes Tina’s basic shorts and T’s. Mrs. K didn’t let me try a girls swimsuit, though. Sadly, Mrs. K and Tina moved away a year and a half later and with them went my panties and any chances of dressing like a girl, or so I thought.
At 10 I was in a summer camp, and a counselor befriended me much more than the others. His motivations were exactly what you’re probably assuming them to be right now, and the relationship two years. I’m over it, and don’t hate him anymore, and my life has moved on. As unfortunate as it was, and relevant to this topic, it was with him that I accepted that I’m a sissy boy. You name the clothing, I wore it. And it wasn’t small women’s clothes, but stuff made for me (I still have no idea how). I was also able to wear girls swimsuits (both one-piece and bikinis) at a local waterpark, and go out in public in full sissy outfits. For as much work it took me to get over the other parts of that relationship, I still count being a sissy boy as a good part of it.
When that time over and he was out of my life, I rejected being a sissy boy, and denied what I wanted, and needed, and how I felt. For 20 years I told myself I was not “that way,” and I was “normal.” At 33 years old, I began to slowly re-consider how I felt, and warmed up to being a sissy boy again. I even opened up to one of my sisters, who is so cool she bought me two pairs of panties because I was too scared to go into a store and buy them myself. Now I wear a mix of panties and some really cool double-seat briefs, like I wore back in the day! I have several sissy dresses, tons of regular girl clothes (shorts, jeans, T shirts, tights). I have a leotard and tutu! I even have Ariel (Little Mermaid) fleece footy pj’s for the winter :)
I’ve accepted who I an, and what I’ve always been: Tommy, Sissy Boy, and I don’t want to hide that again, ever :)
The way I found now much I loved xdressing was different. As a total sub I connected with a dom couple, she would dress me and they would use it to humiliate me both physically and mentally. I was paraded in front of their friends and made to wait on and service them. I was tied and punished, used and abused. The whole deal was exciting but the clothing made very, very excited. Now I wear panties and thigh top stockings all the time under my "street clothes, I don’t wear bras because my nipples are pierced and I want the jewelry to show tlhrough my feminine blouses. I like make up a lot but it takes practice, I also use perfume and lots of very feminine jewelry. I’m still a sub but now it is always as a bisexual crossing make who is dedicated to “female” atire. Love your site, please keep up your work, your support is invaluable.
Like many others, I had my start by raiding my mother’s dresser when I was about 12. One day each week, I had about a 2-hour safe “window” at home by myself after school, when she took my sister to her ballet class. I usually had just enough time to go through one drawer, pick some things to try on and then “model” them in front of her full-length mirror. I must have spent several of those days trying on her bras and panties, finding whatever I could to fill the bra cups – tennis balls, rolled-up socks, or who knows what! The next drawer was where she kept her camisoles, full slips and half-slips. It wasn’t until many years later that I got as far as wearing dresses, but when I did I made sure to remember to always go with a full slip. I could never get a half-slip to stay up! Then I got to the drawer where she had several babydoll nighties and matching bikini panties. After trying them on, I knew I’d spend every night wishing I could sleep in them instead of my flannel pajamas! I didn’t think of it at the time, but it would have been fitting if I could have worn the babydolls to bed, since they may have had something to do with my being born in the first place!
I don’t know about anyone else, but for me it was another drawer that held what made me long to discover my femme side, and that was the drawer where she kept her bathing suits. As early as around kindergarten age, anytime we went to the beach or to a pool, I had a secret longing to wear girls’ bikinis or one-piece styles. It probably started at a birthday party at someone’s pool when I saw the other kids’ moms in their bathing suits. I didn’t yet understand the progression of boys growing up to be men and girls growing up to be women, so I hoped I’d become a girl by the time I was their age. I probably thought wearing enough girly things would make me turn into one! I still had that hope when I tried on my mother’s bathing suits, starting with her turquoise crushed velvet bikini. In some ways it was like wearing a bra and panties, with the top having bra-style straps, but the feel of the material took the excitement to another level! We had a creek in the woods behind our house, and I so badly wanted to find a secluded spot where I could spend the whole day swimming and sunbathing as a girl! I never got enough nerve to try that, so I settled for a safer alternative, putting a towel on the floor, lying down on it, closing my eyes and imagining myself on a beach, having turned into one of the girls I’d seen on our past trips! I had to use a lot of imagination, but the bikini did its share to make the enjoyment real!
As much fun as I had trying on her bikini, it was wearing one of her one-piece bathing suits that introduced me to the girl inside me. It was an orange and yellow floral print, with three metal rings on each side holding it together. I had to fumble around a while before I figured out how to put it on, never having seen a woman do that! I held it by the straps and kept trying to step through the leg openings, but my foot kept getting caught in one of the slits between the metal rings. After a number of tries, I finally got both feet through the right places. As I got the rest of the way into the suit and slid the straps over my shoulders, I wasn’t ready for the jolt that went through my entire body. I was pretty sure that the bathing suit would fit me reasonably well, as her other items had, but when it molded itself around me like a second skin, all I could think was that I’d instantly turned into a girl as I’d wished for so long. In a way it was frightening, because I suddenly felt totally natural wearing something that was obviously made for a woman. I went to look at myself in the full length mirror and, after just two or three steps, realized that I was swishing my hips without any conscious effort. When I got to the mirror, I kept asking myself over and over if that was really me. The bikini gave me that feeling too, but the leg openings on the one-piece suit went much higher on my hips, and the seat seemed to shape my butt like a woman’s. To top it off, the molded cups, common on most women’s swimsuits at the time, gave me a full bustline. The worst part about taking it off was knowing that the next time I went swimming, I was going to have to wear boys’ trunks again, this time knowing how it felt to wear women’s bathing suits! I thought the Speedo suits that boys wear on swimming and diving teams would give me at least some of the same enjoyment, but they didn’t even come close!
It wasn’t until some time later, but I finally experienced the thrill of wearing women’s swimsuits to the pool at my apartment complex. I usually chose one-piece styles, since they were easier to find in my size than bikinis for one thing. Also, I found that one-piece swimsuits with soft-cup bras hold artificial breast forms better than most bikini tops do! I always tried to find swimsuits in floral print fabrics that would go with either red or fuschia toenails. Going to the pool was usually the way I topped off a day of cross-dressing. After going grocery shopping or running other errands in a cami top, mini-skirt and 6-inch heeled platform sandals, I’d get back to my apartment and change into one of my bathing suits. Since I didn’t want to get my wigs wet, and knew I couldn’t pass with my own hair, I usually wore flower-petal swim caps. With makeup and lipstick already on, the effect was complete. Whether I was swimming laps, doing aqua aerobics or relaxing on a float, I found that some time in the jacuzzi afterwards wound it up nicely. As for passing, I don’t know if I fooled “all of the people all of the time” or not, but to me it was all about imagining myself as a woman, feeling natural in a woman’s bathing suit, reliving the experience I had when I tried on my mother’s, and still waiting to see if enough dressing and acting like a woman will make one out of me!
Wow, what wonderful and varied responses this blog has given rise to! I’ve so enjoyed all your responses and stories. It seems there is one common theme – those of us who are destined to explore our femme side are hooked forever when we try on femme lingerie. I share with you that sense that once you put on that first pair of panties, it connects you with a part of yourself you may or may not have known was there. Thank you all for sharing your personal stories. They are all so enjoyable to read!
I’ve always been a butt man so when I finally realized I wanted mine to look good also there were no thongs being made for men that I knew of. Now this was long ago. My wife bought me some women’s thongs and that’s where it took off. I started wearing them to work and always whenever I put on a tight pair of jeans. I really love how my ass looks wrapped in lace boyshorts, my new favorite. Just bought the Lace Brazil Brief in purple! Purple has always been my fav color. Normally always bought womens panties but usually a hole develops in the front. So excited to have a pair of lace panties w/ a pouch. I have several mens pouch panties but no lace ones and hoping these fit my butt perfectly!!
Needless to say, those first panties my wife bought me just started the whole process of me trying to have the cutest butt out there!!! Interesting when I read the blog this morning about to pouch or not. Surprised so many said no. For me though, its all about how my ass looks in my panties. Hope my order arrives before this weekend…
I am not a cross-dresser, yet! My wife likes me masculine. So, far I shave my legs, chest, and sex, and she lets me. I have chosen the sexiest men’s underwear I can find, and she lets me, so far. String bikinis are good as well are an imported thong. She objected to some lace panties. I really want to get some lace panties!
Yes, I have accepted that I am fully gay or nearly so. And, am trying to figure things out?
I started in early pubescently not knowing anything about sex except I liked girls, they have a calming effect on me. I started trying by trying a bra on in our home laundry. It was electrifying for me from head to toe. I felt warm and relaxed, all my problems went away. Still, to this day, I know something is causing me anxiety or distrust with my wife, out comes the bra. fake boobs a skirt and sweater. It’s become a form of anxiety treatment, feeling warm and secure in a bra and my private sanctuary.
Yaniv great story
As lve said before some women are into it and if they are its bliss on both sides
My lust for lingerie started at the age of 12. The trigger was stockings that blew my mind. The first time I wore my mother’s panties, stockings, robe and heels. Since adolescence I have been feeling less manly than the other boys/men around me… for years I was fighting against my inner feelings and lusts and felt shamed and even avoid intimacy with women.
In 2006 I met my beloved wife and few months after we started going out, she ordered herself a sexy corset that came with a black sheer thong… I wore it after few years of “abstinence”… i felt so sexy and knew that I must tell her… few hours later I asked to wear this thong.. she was shocked but after I wore it she was so turned on and everything is history… we’re together 13 years, got married and have 2 kids. During the last year I started to crossdress more and more and my wife supports me more and more. She love me as a man and also as her sissy… I hope to be less shy and to crossdress more and especially outside
I m no expert but trying to hide it is probably a bad idea. See if you can wearsome male lingerie thats not too obvious to get a feel for what she’d say!
But best is to be upfront and honest with her about your desires
The clothes here are fantastic
I dont look at wearing these items as crossdressing because they are mens garments with some femme styling. Women do it all the time wearing boyfriend style jeans and other male styled things
I recently discovered your blog. Have read most all of it. I enjoy your openess and breath of knowledge.
Some months ago I discovered my wife’s razor in the shower, started to shave my legs and everything else! My wife challenges me about my shaving but, so far she has accepted my excuses.
I wear some very brief and sheer bikinis to bed. My wife has not connected the bikinis with my shaving. Hope not! I want to get some cross dress items, but my wife wants me to stay masculine!
I was surprised when she told me, “See those women? They are gay!” Why? Because they are wearing the same rings! I would never notice this detail!! So, what is going on? Is my wife gay or does she just have sensitive gaydar?
I get what you ate saying
I m not gay or “femme” but i love women’s clothing and I love wearing pretty sexy stuff.
i really like the contrast of the male female
I had always enjoyed looking at all the women in panties featured in department store ads in the Sunday paper. Then one day I wanted to know what it felt like to wear a pair of satin panties. I then noticed that my older sister had a few pairs of pure satin panties. I couldn’t help myself and had to try them on. I immediately got so very excited. I couldn’t help but touch myself. Since then I have explored my lust for wearing panties everyday, at times cross dressing, and getting excited seeing other men wearing panties.
I can’t remember exactly when I started wanting to wear women’s clothing. My first attempts were with my older sister’s and cousins underwear. At first they did not have bras, but as they got started, so did I.
I have never tried to pass in public, has always been my personal secret.
Now I am blessed with a wife who accepts me as I am, and understands that I am not actually gay (although have had a couple of experiences) and not really a femm. I just like the style and feeling of female style clothing.
This site has been a real blessing, as finally I can get sexy clothes that fit me!
I was on holiday with my uncle, aunt and niece (who is year older than I am). We slept in an holiday house and shared a bedroom.
After she had a shower she came back in the bedroom ad started to get ready for bed. As she was standing in her undies I could not help getting an erection. She got cross and said It is wrong to get hot over family members. After being a bit ashamed I said it was her silk undies that made me hot. She relaxed and we went to bed. After a few days of me getting an erection and her obviously enjoying it she asked if I had ever touched a pair of panties and she grabbed a pair form her suitcase. She gave it to me and I got really embarrassed. She said it was fine and that I should try it on to see how soft it feels. So I did and slept in it that night. I have never stopped wearing panties since.
When ever I see my niece she still always asks me If I still like it.