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
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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 :)