How did you start cross dressing

[Cessair]

I just started this year, I never could accept being too feminine because I didn't want to be a gay-cliche'. My ex really encouraged me to be myself, though this is one of the reasons we couldn't be together.

I work at walmart, which is a very strange experience. I have a cool coworker that I trust a bit, and I asked her if she'd ring me out because I was buying some things for my "girlfriend", who doesn't exist. I had her walk around with me as I picked out a top and some very cute panties. I've always been very jealous of the underwear that women get to wear. We went back to sporting goods and she rung me out.

I got home and everything was too small and I couldn't very well return it. There's a difference between buying women's clothes and buying women's clothes where almost everyone knows you. So I kinda stretched out the panties and wore them when I was feeling down, but never ever outside the house, especially not to work.

So then I got stuck on second shift for a month. One night I noticed some lace nighties, and with my "extraordinary eyesight" I noticed a 2X in black. I bought a few groceries that night, must have walked through apparel 5 times, but there was a 3rd shift person right near the rack. So I got in line, waiting to checkout. Then I got in my own face, kinda like I used to be, thought "you march back there and get that #@%&ing nightie!" so I did.

Got home, was too tight...that's one of the reasons I hate dressing up; I just look horrible.

So, as it turns out, the first thing I ever bought that fit was at an adult store. It was this pink nightie and it was adorable. Lace top with tiny pink bows on the front, and it fit! I felt so lovable in it.

Then when I had a bit of money, I started shopping online. Lane Bryant, One Stop Plus, Amazon, I used the size chart and everything almost fit. There was this tank that was just too big. But now I have a complete set of panties that fit and are adorable and I have two complete outfits, they're just a cami/skirt combo but they fit and work.

I just started doing makeup, eyeshadow is easy, mascara isn't. I use lip gloss and this foundation method doesn't seem to make a difference.

[Guest Fran]

When I was about 12 we had a neighbor move and leave many things behind. One thing left behind was a padded bra which I quickly claimed and would stuff with foam rubber. We lived in the country so I could easily get lost wearing my bra. Later when I was about 16 I started wearing my mothers bras when no one was home. The first bra was a padded A cup, my mothers bras were a full D cup. I would stuff the cups with wash rags. In my 20's my wife was flat chested and wore padded bras. I bought her a pair of B cup breast forms and later a couple pair of C cup silicone breast forms. I wore her forms every chance I got. She also wore 4" high heels and had a number of pairs which I also enjoyed even though I had to tape them on. In my forties when we were divorced I bought myself a pair of C cup breast forms and a pair of 5" high heels.My job required traveling and I would take my shoes, bra and forms with me. Being out of town allowed me slip out of the hotel in dress. Over the years I have graduated to 6 1/2" heels and both DD forms and J cup forms. I can't dress at home very often as my current wife would frown on that. I do leave my stash at the office to wear after hours and will slip out after dark in dress for a walk or drive. My wife is out of the house tonight and I am in my heels, J cup forms and I have two kotex pads keeping my flat in front as I write this. As soon as it gets dark I will slip out for a walk minus the 6 1/2 heels. I love the feeling I get when dressed and would wear a bra and breast forms 24/7 if I could.

Franie

[Guest Monte M]

I was fourteen and I had a pair of flannel shorts that I had gotten from a Girl Scout Jamboree I went to in Minnesota. They were meant to look like boxers but be girl shorts. But they were so soft and so comfortable, that I started wearing them to bed. At first I wore them with panties on underneath, then I went without. I felt so strange without anything constricting, but it felt good too. Then I started wearing them under jeans (even though they weren't meant for that) and wore them as much as I possibly could (I only had the one pair). But when the elastic started to go, I knew I just couldn't give that freedom up, so I asked my mom if she would buy me real boxers, and she said yes. I've never looked back

Monte

[Guest Ryan+Reann]

Well, mine all started around when I was 4, I would let my mom and sister paint my fingernails when they did theirs mainly since they took care of me the most, my mom would also let me play in her heels. In a way I'm angered this happened but still so happy I am part male and female

I'm now 13, and I first really put on my mothers clothes starting with a pantyhose when I was 11. But my interest left with clothing and went to makeup but mostly nail polish I used to go and take my paint set and literally paint my nails with paint. xD Then I started using expo markers mainly since it was easier and I had a very nice red marker Red being my favorite color. And when I was around 12 was the 1st time I ever did my nails. It felt so right, I was in love. I have painted my nails, put on lipstick, curled my lashes, tried eyeshadow, but I don't really know how to do it. So I never looked good And I don't have a wig so It looked even worse I have such big dreams, my biggest dream would be to go to a place like TG nails and get a manicure, maybe do my makeup if they can. I just can't wait

[Guest Sarah Miller]

When I was 15 My sister ran away from home to live with our estranged father. I was home alone over that summer possibly for the first time I remember. One day I wondered into my sisters room and went through her things. before long I started trying in her skirts and dresses. It was thrilling. Over the next couple of years I would try on my mothers clothes when she was away. I also used to wear my sisters old school uniforms under my boys uniform to school.

Girlfriends, female housemates, no one was safe. I'd let myself into rooms when they were out and try on their stuff.

A few tImes I bought a dress or two ( always a gift for a pretend girlfriend) but threw them out from fear if being caught. It wasn't until a few weeks ago I rented a post box and have bought many outfits from eBay.

My next goal is to go out one night fully dressed to the nines and looking great. Gotta get my make up skills better first.

xxo Sarah

[Guest Rowan19]

It all started in my room at our old house very late at night. When I was twelve I started waking up in the middle of the night, a habit I've grown out of now. In fact my sleep patterns have done a 180, instead of lack of sleep I sleep too much! Lol. Anyway when I wasn't hungry I'd have some time to myself, so eventually one night began to crossdress. I tucked my hair up in a black beanie(The one in my DP which I still have), wore my very baggy monster cross T-shirt and some girl's denim shorts that looked like they were meant for boys. Not short-shorts, the ones that hit just above the knee. And I'd try and hit on my mirror in a deep voice, like: "Hey baby, how's it goin'?" XD Anyway that was the start of Rowan. I'd never heard of crossdressers or FTMs before either, only drag queens like Dame Edna. A few years later I got tempted to google it, I found pretty much everything on alternative gender including Laura's. A few monthes after that there was no denying the enevitable, I was Rowan.

[Guest Felicia Anne]

i remember being about 5 or so... and without any forethought or planning, i simply decided to put on my sisters clothes and be a girl that day. i remember putting on silky panties, tights, a slip that matched the panties (pale blue as i recall), and a blue flower dress. i put my hair up under a hairband, slipped on a pair of black mary janes, and went to greet my family.

they laughed, and thought it was delightful. until they asked me to put on "normal clothes"...

(suffice to say, temper tantrum does not even BEGIN to describe what followed...)

[Guest Svenna]

I was already pretty well involved with female clothes by the time I was 5...

A particularly fine, lacy, snow white first communion dress kept my interest until I finally and unmistakably outgrew it. My heart broke when I heard that seam give way...awwww...

I am eager to start building a great wardrobe of my own for real life use. Very eager...

Love and lace, Svenna

[Guest surifi]

well i have always had a voice that with minimal effort could sound so feminine my female friends would say i could sound more girly then them. eventaully i did my first and currently only crossdress was a female costume at an anime convention. to be honest i only did it to get them to stop teasing me that i should but to be honest i was really relaxing and i enjoyed it. probably going to again at some point.

[Guest Dori]

Shy & sexually aroused at age 14 I found my 1st pair of Girl's panties outside a motel pool, took them home real fast, locked myself in the bathroom and slipped them on in front of the mirror, thinking my derrierre looked like a Girls from behind while self gratifying. Love the females all my life, butt still get aroused when I slip on some panties and things, it just makes me feel erotic & sexy, unlike male clothes do.

[Guest Steph S.]

I cannot remember exactly how I started but I think it was when I was going through puberty and started to experiment with my sexual side. For some reason I went into my sisters room and in her drawers and found a pair of her day of the week underwear. I can still remember them being the Friday black ones with a nylon gusset in them. Well they were so soft I found myself trying them on and before I knew it I had become completely addicted to anything made out of soft, silky nylong. That was almost 30 years ago.

[Guest Annalee]

I grew up around dancers, women that always looked great and smelled fantastic, I developed and admiration for the female form. I actually wore my sisters clothes, and as I got older I wore my mom's clothes. Its something I've done ever since, I still dress up when I'm at home, and still wear panties and bra under my work clothes. There's a certain kind of 'mystique' about wanting to be a woman. The mannerisms just fascinate me, the way she talks, walks and carries herself is just a stunning thing to watch, truly the proverbial 'poetry in motion'. I wanted to emulate that, and I still do it today.

[Guest iluvalexis]

I started when I saw my stepmoms dress laying on the bathroom floor. I was curious so I tried it on I liked the way it felt. Then in my teens I did it in secret when my parents were gone.I would wear skirts,dresses, and pantyhose. I still do it now but only in the privacy of my own home. I wear skirts, dreses, tights, tops, and heels.

[Guest Clair Dufour]

My first year of High School my sister got a bunch of wigs a friend and i tried one on and went YES! I loked good, some said too good. The British Invason was is full swing so I started growing it out. Even before this I was a Pony Clubber which is mostly girls so much of the kit that gets handed down is girl cut. The combination was awsome and it sure did not hurt my scores at trials. Hanging with horsewomen has also defined to me what women should like.

[Guest heather47]

I was five years old when I started. I would sneak into her room and put on her dresses. One day she caught me ouch. I continued though. I wud steal her panties and wear them all the time.

[Guest ValerieM]

I grew up with 2 older sisters and when I was born they would take turns having me sleep with them and would put me in a nightgown until I was about 6 or 7. Then when I was about 12 I would wait until I was home alone and would try on their dresses, heals, bras, etc... I stopped for a long time but still knew that I liked it. The first time as a adult was a year ago on a business trip. I had periodically worn makeup and my wife's bras or nighty when I was home alone, but on this trip I took a long skirt, bra, flats, blouse jewelry and makeup. I did it all. It took me about an hour to musterthe courage to go to dinner like that, but I did. It was scary at first but I loved it. Since then I have cross dressed on every business trip in the evenings (2 or 3 times a year). I told my wife after the last trip. She is in couceling trying to figure out what to do about it. But, she has encouraged me to join a support group. It is a little rocky at home right now, but she lets me cross dress 2 to 3 times a week as long as the kids are not home and if she does not have to see it. Hope things improve here, but it is the most liberating thing I have ever done.

[Guest rikkicd64]

I grew up with 2 older sisters and when I was born they would take turns having me sleep with them and would put me in a nightgown until I was about 6 or 7. Then when I was about 12 I would wait until I was home alone and would try on their dresses, heals, bras, etc... I stopped for a long time but still knew that I liked it. The first time as a adult was a year ago on a business trip. I had periodically worn makeup and my wife's bras or nighty when I was home alone, but on this trip I took a long skirt, bra, flats, blouse jewelry and makeup. I did it all. It took me about an hour to musterthe courage to go to dinner like that, but I did. It was scary at first but I loved it. Since then I have cross dressed on every business trip in the evenings (2 or 3 times a year). I told my wife after the last trip. She is in couceling trying to figure out what to do about it. But, she has encouraged me to join a support group. It is a little rocky at home right now, but she lets me cross dress 2 to 3 times a week as long as the kids are not home and if she does not have to see it. Hope things improve here, but it is the most liberating thing I have ever done.

Valerie,bless you my dear,I know it took a lot of courage to start "coming out",I am proud of you. You just hang in there,there are a lot of us "sisters"whom are at differrent stages being our complete selves. At this site you will find others that understand and support you.....Rikki...

[Guest rikkicd64]

I started about 25 years ago,strictly in the closet,I started my coming out a little over a year ago when I realized crossdressing was an important part of who I am. It did not have anything to do with sexual arrousal,it was just part of the caring,kind person that I am. I now dress 95 percent of the time,wear makeup and act and conduct myself as a lady. I feel that I am a much more complete person now. Happier than I've ever been.Plus I have found that womens clothes are a lot more comfortable.

[Guest praxis]

rikkicd: its interesting to read your and so many other accounts of how they began. I'm at a point now where I realize that I have a long history of cyclic impulses of fantasizing while completely or partially cross dressed, only to purge soon after. I have recently started doing things not for arousal, but some other level of enjoyment, like wearing a waist trimmer and sitting to pee - still deeply closeted.

Anyway, my brief account...

Not sure how much it counts as cross dressing, but I remember getting into a bathroom drawer and getting into my mothers package of pads - I must have been 10 or 11. I didn't have a concept of their purpose - just that they were for girls and I wanted to try it out!. I definitely began at about 12 though when, on occassion, I 'borrowed' panties from my sister when she was away. In my 20's I stole bits of other girls laundry out of apartment laundry rooms. I feel bad about that now, both for the thievery and that I ultimately threw away their jeans or panties in shame. Have since purchased and purged online or at clothing stores several times. This web community seems like an encouraging (very diverse) group. Now at age 32, I hope to explore my 'dark side' and gradually reveal it to my significant other.

[Guest rikkicd64]

rikkicd: its interesting to read your and so many other accounts of how they began. I'm at a point now where I realize that I have a long history of cyclic impulses of fantasizing while completely or partially cross dressed, only to purge soon after. I have recently started doing things not for arousal, but some other level of enjoyment, like wearing a waist trimmer and sitting to pee - still deeply closeted.

Anyway, my brief account...

Not sure how much it counts as cross dressing, but I remember getting into a bathroom drawer and getting into my mothers package of pads - I must have been 10 or 11. I didn't have a concept of their purpose - just that they were for girls and I wanted to try it out!. I definitely began at about 12 though when, on occassion, I 'borrowed' panties from my sister when she was away. In my 20's I stole bits of other girls laundry out of apartment laundry rooms. I feel bad about that now, both for the thievery and that I ultimately threw away their jeans or panties in shame. Have since purchased and purged online or at clothing stores several times. This web community seems like an encouraging (very diverse) group. Now at age 32, I hope to explore my 'dark side' and gradually reveal it to my significant other.

Good for you dear,I've found that my"dark side",is really a very bright and colorful side.You will know in your heart when to take the next step,it took me almost a year to go even to a cafe completely dressed. It has been so long that I can't remember the last time I stood to pee,is much more comfortable to sit.

Bless you dear.....Rikki....

[Guest ValerieM]

Rikki - thank you so much. I really needed the encouragement. Hugs

[Guest brendastevens]

I started wearing my mom's panties when I was 11. But really, I so loved girls and the way they looked, the way they dressed from my earliest memories. But that was back in the 50's, when boys were supposed to be boys, and well...after years of just wanting to slip on some girls clothing, I finally did so when I was 11, taking a piar of my mom's panties off the 'clothes horse', and trying them on. I could not quit from that moment on, and just kept this all to myself, in my shame, that I was a boy who liked to wear girl's panties and pretty girly things. From that moment on I was constantly searching through the clothes hamper, or sneaking into my mom's panty drawer...and it just went on from there...my secret me... a boy on the outside...but a girl on the inside...I have not changed...I still love sliping into some lovely soft silky lingerie, now putting on dresses and heels...wearing a wig...and so enjoying the feeling, that wonderful glorious feminine feeling...that I am a Girl..a Woman...at least for a little while.

Hugs..Brenda

[Guest rita63]

Our house had a clothes shute to get laundry from the 2nd floor to the wringer washer in the basement. One day when I was about 12 or 13 I was home after school and my mom and sister were still out. I was fooing around in the basement with the tools. A pair of my sisters cotton panties had fallen out and I just had to put them on. It was very thrilling buut also guilty feeling. I continued to try on my sisters and later my sister-in-laws clothes (she had a full drawer of 50s clasic undies). When I moved out I started collecting and buying my own, aquiring and purging over the years.

Since my wife and I have seperated I have been dressing all the time at home and underdressing outside. Its time for me to find out who rita is and so far it feels wonderful.

hugs rita

[Guest akrobat]

Since I know about myself I was a cross dresser.. I stopped when I was 19 years old I guess cause I was forced to act more normal and yeah, I tried, but it doesn't worked for me. So when I made a confess to myself that I am a transgender I choose to be myself again no matter how hard it will be. I deserve to express myself no matter what it is. I am not hurting people with being transgender, if someone has a problem with it - I don't care, it's not my problem

And no matter how hard it is, I will never go against myself... So finally I feel OK with my clothe. My style - my business. That's how I see it.

[Guest Eve Caillard]

I am perhaps an odd case! I've just joined this community because this very February I crashed into cross-dressing when innocently buying some tights (pantyhose) to keep warm in the winter (I had heard plenty of men do this).

I should have noticed something was odd when I went back and bought another pack, this time of dark-coloured pantyhose, only because I preferred the colour! I have no idea what tempted me into E-bay to look at suspenders and stockings, but the floodgates opened. You'll see my recent posts. I kind of just blew into it after that.

To be frank, I think it has always been inside of me. I did experiment as a 14-15-year old but then put it aside and never thought any more. But, now it has rushed back into my life, I look back and see I always loved women, women's clothes and always wanted to be a woman for years. I am so jealous of not having breasts.

So, cross-dressing has crashed totally unexpectedly into my life just the last two months. It's amazing, exciting, warm, comforting and takes me away from my stressful male life. Girls, thank you all fofr your support. This site helped me realise where I was going and helped me settle into this new life.

Hugs

Eve