The First Time

[Toni]

The First Time I ever wore any female clothing was when I was 12 and the article was a pair of my mothers white panties. I can still remember how it felt, but all good things came to an end when my mother caught me in them and for years afterwards I was refered to as"That filthy ba@*?rd".
The First Time a girl friend saw me was in 1965 when I told her about it and before I knew where I was she was buying matching undies for both of us but unfortunately this affair didn't last very long.
The First Time my wife saw me was one night when she came home from the bingo soon and there I was in her black bra, girdle, stockings and panties. I must have looked really stupid because I am much bigger than her, anyway she asked me what I was doing as I dissappeared into the scullery and remained there for a long while, terrified to come out, but I eventually did and found that she was o/k with it - no mean thing as this was 1967 and we had only been married for 9 months.
The First Time I got trapped was one night when I went to our outside toilet just wearing bra, suspenders, nylons and panties and I suddenly realised that the man upstairs was looking out of his window and when he called his wife to come and have a look I just panicked and ran OUTSIDE into the back lane where I stayed for about an hour before I could manage to get back in, and my wife nearly wet herself with laughing when I came back in saying "why didn't you just come into the house".
Come on girls tell me about you First Time experiences.
Love and Kisses,
Toni

[Wendy me]

toni ...........ahhhhhhhhhhhhh the good old days......................

[Ariel_TV]

The first urges i got were when i was very young and saw the little red witch in Casper the friendly ghost. I didnt know why at the time but i envied her little red suit , it drove me crazy and i wanted to be the little witch in casper. It was also the first CDing dream i had , i was wendy in my dream flying around hehe


After that i also started noticing girl's swimsuits , i found them so beautiful and they look so fun to wear . Especially the fluorescent ones with a zipper in front , they were the fashion back then .

This lead to the first time i wore something feminin , it was my mother swimsuit. The first time i actually asked her to wear it when i saw it laying on her bed . I told her i was curious to feel what it was like to wear , she took it has simlpe curiosity and told me only if i finished my chores . Damn my chores never got done that fast before lol . When i was done she left me alone in her room with the swimsuit. It felt so great wearing it , i fell in love with swimsuits that day and it started me on the path of crossdressing .

*hugs*

[DeannainWI]

My first time was after my older sister went away to college.Most of her things were still in her unused room including her Cheerleader umiform.I was 13 at the time home alone for the afternnoon Bored and looking around in there when i came across it.I had allways envied how she looked in it and with her being a few years older than me we were around the same size, i had to try it on.From that time there was hardly anytime when i was alone in the house that i was not in there trying on just about everything she left behind.It was a sad day when she came back home LOL.But from then on i started gettting my own things.Still wish i had that uniform though :) Deanna

[Maddie Knight]

I don't remember the first time I dressed, but when I told my fiance she wanted to see me dressed. It took a while before I agreed but when I did I would not let her in the room till I was compleatly dressed and madeup.
I think I was more scared than her. :eek:
She loved it, it turns her on and we have a great relationship and have been together for 12 years. :D

[Tristen Cox]

Well here's just a silly episode. Eight years ago when I moved here and lived with my mom before eventually moving out and coming back, I was sitting out back one night mostly dressed in a black athletic suit (no arms and coming down only to my thighs) and black swade grannie boots. Next thing I knew I heard the front door open and mother come in. So there I was in the back yard with the only way in through the kitchen door. She started doing some things in the kitchen so I hid around the corner of the building. Mind you we are in an apartment complex and there was another neighbor's door right next to where I was hiding. The neighbor acrossed the way came home and her spotlight came on so anywhere I went I was visible, and my heart was pounding thinking I was busted for sure. I was calm enough to listen to the sounds in my kitchen and then heard some noises in her room from outside, but that still wasn't good enough as her room was right next to mine and she always left the door open. I walked along the back of the place and saw she was in the bathroom. Quickly I untied my booties and ran inside, just making it to my room before she came out. Close call :eek:

[Rikki]

I was lucky when I started dressing, I have six sisters and I had no trouble getting an out fit to wear. As I got older, and on my own, I had a few close calls. One night driving through Montana, I was wearing a black skirt and white blouse with, had to be a hundred buttons, and I come up to the truck scales that were open for the first time in years that I knew of. Well getting out a that blouse was a real trick and throw a shirt on while driving. I didn't have time to get out a the skirt though. My heart was pounding so hard that I was shaking the truck. The weigh master was standing out side and didn't bother to step up on the truck and he told me that I was okay because they were only doing inspections and I had just been inspected the day before, so he says to have a nice night. As soon as I got to the next exit, I pulled over and changed into drab for the rest a the night. That was just one a many close calls while driving truck for 27 years. I think I even felt good in drab that night.


Rikki

[derminator]

My own story started when i was such a wee boy. My mum and dad both worked hard to keep a roof over our heads so as children, me and my bro's had to spend all of our time (when we weren't at school) at our grandparent's place. It was there that I had my first ever cross-dress experience. I would have been no older than 6 or 7. I was exploring in the garage and came across an old bag of clothes.... and in it i found (amongst other things) a white dress, lots of frills and lacey stuff..... i don't even quite know why, but i felt driven towards putting this damn dress on. I can remember feeling very sneaky about the whole thing. I knew (or at least i felt like) that it wasn't the right thing to do. But, when i put that dress on, ****wow*** what a feeling. Even a strange squirming in my loins. I kept that dress on for as long as i dared, but eventually (and feeling very guilty) i quickly got out of the dress, got back into my clothes and put the dress back.

I have never been caught in women's clothing but have had a few close calls... but, have had these interesting expereinces....
* when i was a teenager i left a pair of white silk panties in my jeans pockets, which got thrown in the wash... mum, of course came across them when she checked the pockets before putting them in the machine.... I just told her that me and am friend had found them in the street (which was true) and that we were mucking around with them, you know, by weraing them over our jeans... I'm not sure she bought it
* My brother found a pair of panties in my bedroom cupboard, hidden in a false compartment... i just told him to f eff off and mind his own business
* The first girl i ever moved in with decided to do a spring clean one day and found my stash bag whilst i was out fishing one day..... she threw the whole lot out in disgust

Derminator

[Helana]

* The first girl i ever moved in with decided to do a spring clean one day and found my stash bag whilst i was out fishing one day..... she threw the whole lot out in disgust

Derminator

Ouch!!!! I hope you throw her out :D

One of my fondest memories was when I bought my first article of clothing - a beautiful and expensive white silk lacy teddy with a tight elastic waist. I was very thin then so looked feminine in just about anything. My mother is very conservative so the few things of hers I tried on were not very exciting to look at.

After taking about 2 hours to build up the courage to buy it at the department store, I rushed home and ran into the bathroom and locked the door. I flung off my clothes and with shaking hands put on my teddy. Then as I looked into the mirror I was amazed at the sexy girl looking back at me.
My knees literally gave way and I dropped to the floor. I stayed inside the toilet for about an hour in complete delirium.

For weeks I tried to wear the teddy in bed but I was so excited that sleep was impossible so I ended up having to take it off just to catch a few hours nap before getting up. That teddy just transformed my life. Alas I lost it with my first purge, something which I have deeply regretted because I was unable to ever find any teddy remotely as wonderfully sext and enticing as that teddy. BIG SIGH! :(

[Allie]

My first time was when i was around 11 or 12. I was alone in my house, and was upstaris. I had a younger sister, and i went into her room for some reason. I found a pink nightie and decided i wanted to put it on. So i went to the bathroom and put it on, and well, i was hooked. I then found a tutu later on and enjoyed that for a while until they gave it away :(

The first time i bought something was about 2 years ago. I was in my fred myers, and wanted badly to buy a pair of tights. I finally worked up the courage and bought them! i was very happy. I have since then become very comfortable with the tights section, and bought 3 more pairs. the first real article of clothing i got was a nice black formal dress that i had found actually. it didnt fit all the way, but the leanght was right :p (though ive grown and am just abit too tall now :( lol

[racheal]

My first time was 13 - an exotic one peice swimsuit from Sears, the one that makes everything hang out. He he. Then into sport bras and up to underwires and panties. Love satin - the greatest feeling material ever. :)

[angieSP]

The first time for me was when I was 8 or 9. My babysitter had something to do that day and I was out of school sick. With no one to keep me, my mother reluctantly left me at home. There was a rose colored satin nightgown that I thought was really pretty. I sat thinking of it for about an hour. Finally I tried it on. It felt so good I deceided to try some pantyhose with it. I pulled the nightgown up and down my legs enjoying the sensation. I know why women dress the the way they do. It feels so good.

[StephanieCD]

My first memory is of sneaking into my parent's room while they were sleeping and trying something on - I must have been 5 or so. I've been dressing my whole life, in some degree.

[Sweet Susan]

I've had so many first times, that I'm not sure which one counts as THE first.

The first time I even thought about it was in the third grade.

The first time I wore anything was 11, and that was a pair of women's tennis shoes that my mom bought me at my insistence. They looked wonderful.

The first time I donned clothing was age 11 when I wore my sisters slip while playing darts in my bedroom late at night. I ended up masturbating for the first time, wasn't even sure what the hell had just happened. I then began wearing her panties with increasing frequency.

The first time I had sex with a man while assuming the role of the girl was age 12. (He was about 50)

The first time I ever saw a man dressed as a woman was at age 16, (s)he was 21. 1967

The first time I ever had sex with a transvestite: see above

The first time I shaved my body was age 25. It was breathtaking and life changing.

The first time I purposely and actively pursued and found a transvestite for sex was age 27

The first time I wore an entire outfit(dress, nylons, etc), body shaved, make up, (had my own long hair) in front of another woman (my wife) was age 27. I stayed that way while in the house at all times for about two months. 1978.

The first time I went out in public as Susan was 1996. I've never looked back.

[Kate_Uhler]

I was 6 and at night under the covers I'd tuck my member between my legs. When it started to get erect I couldn't be a girl any longer and thought god was punishing me... wow guilt starts early but you know what, gods thinks kate's damn cute now... :)

I was 25 when I first shaved my legs and it was like I was reborn.. I remember being energized going shopping for men's thin white bikini briefs and feeling so fem... knowing under my sweat pants there were these sweet girly legs... When my exwife came home from her trip I told her about my legs. I remember telling her I thought i might be a lesbian trapped in a mans body.... *sigh* that was a mistake i think.


Sweet Susan, Wow!... thats some list.... :eek: I still have some of those firsts left.. :)


been up all night with my new cloths and trying makeup.. I think I might be able to do this... in public.. :D
kate.