How did you start crossdressing?

[mightytim]

I recently was clearing up some stuff and found some lace panties that a girl left behind which I'd left at the back of my wardrobe.

I've never thought about doing it before, but I decided to try them on and boy... wow, did they feel (and look) great!

My cock looked so fantastic, I couldn't actually take my eyes off it!

My question is: for you other crossdressers, how did you start? Is it a slippery slope - am I soon going to be in full make up?

 

[Paintbox]

In a rental beach house one summer as an early teen I found some clothes that a previous occupant had left behind. I still recall my fascination and delight. I guess that was the start of my interest in women's wear and how women chose to dress. As for it being a slippery slope, who knows, could just be a phase you'll move through (and perhaps return to occasionally).

 

[t1m1d1]

I used to love dressing up when I was 16 . A real confused teenager, and short and generally petite.
A relative , I had keys to her house to let her dog out, used to do charity work. She'd collect lots of ladies clothing for jumble sales. I loved dressing up in stockings , tights , knickers etc my favourite was a pretty , stretchy pink dress , which seemed to fit me perfectly ..... I looked great ( so I thought!). I had long hair back then , when fully dressed I looked very girlie.

My cock used to get so hard in tights!

I was heartbroken when the pink dress was sold!

 

[Paintbox]

...

I was heartbroken when the pink dress was sold!

lol. Tragedy!

 

[naughtyinsilk]

I started dressing in my early teens, as I could look a few years older when made up, to get into clubs and gigs to see bands in the 70s. I used to be well protected by other people I went with, so never got harassed, and completely carried off the act of being a teenage girl.

As for it being a slippery slope, my advice shoes can be addictive

 

[Surprise_6924]

The first time for me was in my teens. It was a womanless beauty pageant for charity. My mom and aunt dressed me and I was hooked. Can still remember the details today!

 

[bluesky496]

I recently was clearing up some stuff and found some lace panties that a girl left behind which I'd left at the back of my wardrobe.

I've never thought about doing it before, but I decided to try them on and boy... wow, did they feel (and look) great!

My cock looked so fantastic, I couldn't actually take my eyes off it!

My question is: for you other crossdressers, how did you start? Is it a slippery slope - am I soon going to be in full make up?

i started dressing when i was about 8 or 9 , i tried on my mothers wedding dress and it felt so nice and i thought i looked so pretty that i wanted to try more and i never looked back ,is it a slippery slope ,well for some yes ,for others no ,

 

[stickygirl]

It's a good question and I've found the other replies interesting. I actually started by making my own clothes because borowing my sisters felt a bit gross. I used to escape to some secret locations and did it entirely for sexual kicks - I was just at that age. Pretty soon though I began to to feel there should be more to it and I started to question myself and realise the clothes were just one part of the jigsaw. These days I'll wear dresses when it suits me, but a blouse or a shirt with jeans is more me…. if the weather would reset back to summer I could show off my legs a bit more…brrr

 

[naughtyinsilk]

It's a good question and I've found the other replies interesting. I actually started by making my own clothes because borowing my sisters felt a bit gross. I used to escape to some secret locations and did it entirely for sexual kicks - I was just at that age. Pretty soon though I began to to feel there should be more to it and I started to question myself and realise the clothes were just one part of the jigsaw. These days I'll wear dresses when it suits me, but a blouse or a shirt with jeans is more me…. if the weather would reset back to summer I could show off my legs a bit more…brrr

Summer in the UK, did I blink and miss it? Its freezing here down south, still got heating on.

I never took clothes behind anyones back, the girls I knew enjoyed me dressing up and gave me stuff that no longer fitted them, especially the PVC minis and dresses which I could never have afforded, I did buy new underwear, when out shopping with the girls. It was not sexual to start with it was a means to an end, but I did enjoy the attention I got when dressed up, still do,

These days with doing it for both work and pleasure, I feel like my gender has slipped and find that others as well as myself don't look at me as being male or female, I have been accepted as being me outside of the gender system. I can be out watching the football with my mates, or dressed up on a girls only night out.

 

[ShyBiGuy954]

I started when I was in my mid 40's, did it for a friend, was part of my intro to the sub side of things.

 

[LucyH]

Halloween. Grade 1 (I think). Darth Vader.

 

[Allyourbase]

I enjoyed wearing my dad's stuff, a lot, and I can't remember things otherwise. I know I tried to wear his heavy, knee high work boots when my legs were too short to actually be able to walk in them.

I grew up in a family with a bit less money than the rest of the village, so me and my sister usually didn't get new clothes, rather people gave us bags of their old clothes. We took out what we could use and passed on the rest to charity. Good basis for getting picked on, alas, but also perfect opportunities for dressing up.

There's this pic of me in a men's suit, carrying my sister, who's wearing a dress. From the genderqueer identity I'm trying to accept these days, looking at that pic gives me that painful 'funny because it's true' feeling.

 

[OpenMouth]

I think I was early to mid 20s.

I remember an ex-uni friend of my girlfriend came over to stay for a weekend. My girl warned me that this girl was a goth, talkative and about 5ft tall with huge boobs.

After a few glasses of wine they got a bit giggly and this friend related a story of a 3rd uni girl who had come home to find her boyfriend in her underwear. The giggles and horrified gasps, and this girl's low-cut top (she truly was well built) kind of made me squirm a bit; I didn't know where to look.

They went out the next morning, leaving the sofabed folded out. Within minutes I was writhing on the bed in this girl's flimsy knickers and big, lacy black bra, narrowly avoiding spunking on them as I brought myself off in a super-intense orgasm...

I still do it; it is addictive. It just feels so dirty; the massive potential for embarrassment and humiliation just turns me to jelly.

 

[Mbiguy77]

I don't fully cross dress. I do wear women's panties quite a bit though. Started doing it when I was married to my first wife. Just wanted to see what they felt like. Ended up wearing them more times than not. Then between wives, I wore some when I went to play with my boyfriend and he liked the idea. For that 4 years or so I wore them exclusively. Now that I'm married again, my wife doesn't know about any of my gay affairs. I wore her panties to work with her knowledge and she got kinda turned on at the thought.

 

[bluesky496]

I recently was clearing up some stuff and found some lace panties that a girl left behind which I'd left at the back of my wardrobe.

I've never thought about doing it before, but I decided to try them on and boy... wow, did they feel (and look) great!

My cock looked so fantastic, I couldn't actually take my eyes off it!

My question is: for you other crossdressers, how did you start? Is it a slippery slope - am I soon going to be in full make up?

the first time i dressed was in my mothers wedding dress, it felt so nice and i thought i looked so pretty and i never looked back .

 

[sisscindy]

I had experimented a little with pantyhose and panties and loved the feel and the sensation. I found it so easy to cum when wearing but one time me and a girlfriend where invited to a fancy dress I took the chance to go as a Tennis star female of course. Short tennis dress but i made the most of the chance with stockings panties heels the lot. My girlfriend did my make up and out we went. The highlight of the night tho was when stood at a crowded bar some guy fondled my ass I just wish he had played with it a little longer. From then on I was hooked.

 

[z3r0kool]

ex girlfriend dressed me up

 

[bicuriouscd]

My crossdressing all started when I was six years old , I was a little on the chubby side and my breasts where as big as my older sisters so after seeing her in her bra one day I decided somehow that I should try wearing one , I took one of her bras and put it on and it fit me perfectly and it felt so good on me that it wasn't long before I was wearing her panties , skirts , dresses , slips and swim suits .
I started buying and wearing my own feminine clothing as soon as I got my license to drive and those feminine feeling have never gone away , today I'm a full time underdresser and a mostly gender neutral dresser .

 

[jakelc]

I started crossdressing when I met my first boyfriend. I think, like a lot of guys, that I had always been fascinated by panties. I'd seen my cousin in her underwear when she was 17 and getting ready for a date, I was 13 and turned on by the sight of her in her pink satin underwear. I was always curious and had sometimes used panties in my teens as a masturbation aid. When I moved away from home I was able to indulge my need to explore sexually and living alone for the first time gave me the opportunity to do so unobserved. I wore panties to jerk off with and into but never wore them until I met Tom. Tom was my first real boyfriend and he had told me from the start that he liked guys in panties. During the course of our relationship I went from using panties to jerk off with to wearing them daily and having my own collection. Now I wear all kinds of lingerie, have a good wardrobe of my own stuff as well as wear my wife's. I don't usually go out dressed but I do wear panties most days instead of my own underwear.

 

[janetsexy77]

I did a little bit of CDing as a teenager, nothing spectacular, just tried on some of my older sisters lingerie. Much later as an adult, I wound up in a relationship with a pre-op transsexual who lived in a city a couple hours away. The granddaughter of a very famous celebrity, she was 100% passable, with the tight, toned body of a teenage girl. We would have sex in my motel room, and she would come so hard that it would hit us in the face. After that we would shower and go off to dinner...One day she dropped a bombshell on me: She told me she was going to Canada to get a sex change operation and was getting married. Totally fucked my head up..... Never heard from her again. Started cross-dressing seriously after that, can't explain why, maybe someone who understands psychology could explain. Learned how to do make up from a lady that does T-girl makeovers, bought a bunch of clothes, and the rest is history...

 

[paulman999]

Interesting Story Janet

Sounds like you have learned a lot!!!

 

[bisexualsmoker]

.

I just began trying on things my girlfriend left around my place.
Such fun.

 

[blubyuf6]

I don't "dress" but I have worn bra and panties, I do it so I can act like the slut I want to be.

 

[Layne]

started (dabbled) early in college - i was seeing (ok, just having sex on occasion with) a guy (my first and only) - who was very top/dom, was great in bed (only guy I've been with so I guess he was great), but always got that "I'm super straight" attitude as soon as he would cum..

he started to break it off, not dealing well with his mixed feelings, but suggested that if I were "dressed" it would be different.

he actually went out and bought the first few outfits and it worked for us for a while. he still dated girls, as did I, but on occasion (with some regularity for a while), we'd plan a night or weekend where I'd dress and well - he'd have his way with me

I've sort of been a bit hooked since

 

[planplan]

Great thread, I love the variety of answers.

I've only dabbled a bit myself. I've worn panties on a few occasions but mostly used them as a masturbation aid. I find panties quite a turn on but more so when they are on someone else. In the past that was mostly girls but recently I am really turned on by a cock in panties. So arousing. Really gets me hard. I have had the opportunity once to remove a pair of panties and find a delicious cock inside and it damn near blew my mind.

Keep up the good work all.