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!
Fondest regards,
Angie
48 comments
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).
What got me started?
It could have been a number of things really.
I was raised in an all female household and , as the youngest sibling, I was constantly surrounded by my mother and sisters’ feminine attire.
I’ve always had a “thing” for stockings and garter belts. I believe this may have started when my sisters were putting their stockings and garter belts on. At a young age, this obviously had a lasting impression on me. I suppose I sub-consciously equate female lingerie with a feelings of love, comfort and a pronounced feeling of protectiveness from those early days.
Since then, I’ve always admired the superior qualities of lingerie (its diverse design, range of different materials, the way it enhances the female form and … its ability to provoke and excite!!).
Over the years, I’ve enjoyed buying my ex-girlfriends, and latterly my wife, all manner of sexy underwear and stockings. If I’m honest, I’ve probably bought them for entirely selfish reasons in that I derided an equal (if not greater pleasure) from seeing my partners wearing it. Deep down, I suppose I only wished that I could have worn the lovely items.
More recently, my wife and I were having fun in the bedroom when she playfully suggested, “I’d bet you’d like to wear some of my panties?”
I couldn’t believe what I’d heard and acted somewhat coyly. I took it that her suggestion meant she was comfortable with any future decision I would make to go ahead and plunge straight into wearing panties.
I finally took the step and have enjoyed shopping for some “racy feminine-styled panties”.
I’ll never forget wearing my first pair of panties – a pair of boy shorts in black lace. Since then I’ve never looked back having now acquired a sizeable collection of panties in all sorts of designs, shades, patterns and materials. I simply love the feel of the silky smooth materials against my skin (especially when the panty is more figure-hugging than say a pair of French knickers). I like the thrill of wearing them without anyone other than my wife knowing what lies beneath my outer clothing. I’ve always baulked against social conventions and stereotyping and wearing “non-conventional” underwear is my way of sticking two fingers up!!
Wearing ladies-styled underwear is so exhilarating. Before my conversion, I never realized just how much freedom my new found underwear could provide. Wearing it always makes me feel raunchy – which my wife heartily approves of. She is appreciative of the efforts I have made converting to a panty wearer.
I’m not interested in going the whole way with cross dressing, but I’d be more than happy to take the next step and wear a garter belt and stockings to compliment my panties. I love both the look and feel a pair of Fully Fashioned stockings provides – the welt, RHT, the seams … and the rustle of the nylon as one leg brushes against the other! This is a step that will need careful discussion with my OH but, given her acceptance and mutual enjoyment of my underwear choices, I don’t think it will be a problem – especially since tonight she asked if I’d like to try on her sheer nylon babydoll. Who knows, I might be tempted to buy my own from XDress Collection!!!
What got me started?
It could have been a number of things really.
I was raised in an all female household and , as the youngest sibling, I was constantly surrounded by my mother and sisters’ feminine attire.
I’ve always had a “thing” for stockings and garter belts. I believe this may have started when my sisters were putting their stockings and garter belts on. At a young age, this obviously had a lasting impression on me. I suppose I sub-consciously equate female lingerie with a feelings of love, comfort and a pronounced feeling of protectiveness from those early days.
Since then, I’ve always admired the superior qualities of lingerie (its diverse design, range of different materials, the way it enhances the female form and … its ability to provoke and excite!!).
Over the years, I’ve enjoyed buying my ex-girlfriends, and latterly my wife, all manner of sexy underwear and stockings. If I’m honest, I’ve probably bought them for entirely selfish reasons in that I derided an equal (if not greater pleasure) from seeing my partners wearing it. Deep down, I suppose I only wished that I could have worn the lovely items.
More recently, my wife and I were having fun in the bedroom when she playfully suggested, “I’d bet you’d like to wear some of my panties she’d been wearing