How I became a GURL

So how did you become a gurl?

That's the question almost everyone I meet or chat with asks me... how did you become such a sexy transvestite, when did you figure it out, when did you learn you liked cock.

I actually love the question, because it turns me on to answer it.

When I was 15 or 16 I used to sneak into my parents room, find my dad's stash of Playboys and jack off to them. The girls were sooooo beauitful, I just couldn't believe it. I wanted to see and touch one, which led -- I guess this is common among us gurls -- to digging into my Mom's stuff.

When I was left alone I would put on her panty hose, bra (stuffed with socks to fil it out), a wig, a long light blue, see through night gown, sometimes lipstick and a necklace and heels (although they were way too small) and admire myself in the mirror -- dancing around, hard as a rock admiring how pretty I looked before jacking off and shooting cum all over the pantyhose or the nightie. The loads I blew were huge and left quite the mess on the hose or night gown -- and I was too stupid to clean the mess up. I just put everything up where I found it, with dried cum smeared everywhere. How Mom or Dad never noticed I don't know!

During this period my Dad occassionally got into some harder core porn, and one day I saw a photo of a shemale -- or what they said was a shemale, in one of his magazines. It was a black and white photo of a good looking guy/girl with huge tits and long legs, starting to pull down a pair of daisy duke shorts. They were unzipped, but you couldn't see anything. Still, the photo was very erotic and it made my cock instantly hard. The story that went with the photo said: Man grows tits overnight. It was the first time I had ever heard of such a thing... I had never thought about something like that... but boy did it turn me on. Instinctively it must have triggered something deep inside me, b/c I had to stroke and cum right then while looking at that photo, all the time wishing I could suddenly grow tits!

College was, as I suppose it is for many, my true sexual liberation/awakening. At first it was getting to roam the house naked, jacking off to porn mags whenever I want. From playboy I graduated to penhouse and was always drawn to the ads in the back. More and more it was the gay and shemale ads I dwelled over and jacked off too. Finally I got up the nerve to start going to local adult book stores. It was thrilling. The first time I bought mags from one I bought a lesbian mag and a shemale mag. I never even bothered to look at the straight stuff. Guess I just knew what I was, even if I wasn't admitting it.

The lesbo mag was hot. The shemale mag, not so much. But it still got me hard as hell to see a chick with a dick. One day I swallowed hard and decided to mail order some porn VHS. I ordered one lesbian tape and one gay. It was my first pure gay purchase. I took the letter to the post office at like 3 a.m. and drove to the post office wearing nothing but a long sweatshirt, that barely covered my cock and ass when I stood up straight. I was hard all the way there and all the way back!

It took forever for the tapes to show up. Boy did I spend a lot of time naked and jacking off once they did. The gay stuff was OK, but too artsy -- so I wore out the lezzie stuff, but still there was something about those hard cocks...

Mind you, even though I had girlfriends, I was still a virgin -- hadn't even managed to cop a feel yet.

The porn thing became addidictive -- surprised huh? I got used to going to the bookstores, eventually started going into the video arcades and dropping tokens to watch porn. Mostly I watched lesbian stuff. I couldn't get over how pretty, how hot and how nasty the girls were. I wanted to be one of them!

Naturally the booths had glory holes, but I had zero interest in putting my cock through one. I just knew I was more submissive and a bottom. It didn't even occur to me.

Then it happened. One night I'm in a narrow, dirty booth, jacking off to hot lesbian action and a hard cock suddenly appears in the glory hole to my left. Just sticking out there, disembodied, hard, thick and... and... soooooo beautiful. I hardly hesitated. I didn't think at all. I just dropped to my knees and touched it, and then took it in my mouth!!!! It seemed so huge, although now I know it was just average. The taste was a little salty, but it turned me on so much to have a cock in my mouth. Somehow I knew this was right, it was meant to be, that this was something I had been wanting, needing, looking for!

I didn't suck him long, sure didn't make him cum. I freaked out after about 10 minutes and left. But I couldn't stop thinking about what I had done, or jacking off thinking about it. And I kept going back for more, and more and more. My mouth got better and better and sucking cock. After about a year or so I finally gave up my ass to a guy. It felt so deeply humiliating and wonderful all at the same time! Once again, I knew I had found something I would always want.

So was I gay now. No. I still got off to looking at girls and still loved lesbian porn! But watching women suck cock and get fucked made be long to be a cock sucking slut like them -- or a lesbian like them. Loving cock like I did, there still seemed to me something missing, an element that hadn't arrived yet. I knew what I was could be something more. But what?

I think I knew what that was, to return to my first hard ons, and dress like a women while being used by a man.

How I took that step will be my next post.

Let me know if you like this confession and I'll give you more, much more!
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Posted by jenn1
3 years ago    Views: 1,859
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5 days ago
Nice read. Your parents knew you were wearing your mother's clothes and jacking off in them. I bet it turned them on too!
6 months ago
I loved it! I know I'm not alone in my thoughts with others coming out about their sexual fantasies! Our world would be so much different if this stuff wasn't so taboo.
6 months ago
beautifsal story
7 months ago
great story - much common ground amongst many cd's I guess
1 year ago
once you get the cock in you, then your destiny is marked forever by sissy
1 year ago
yeah it is a very familiar story for me
1 year ago
wow incredible story sounds familar
Jay
1 year ago
great story. mine is similar
2 years ago
I loved it I seen one of those adds in the back of a hustler when I was about 12 and have dreamed of shemale sex every since
2 years ago
Could certainly identify with a lot of your confession. Especially when you said, "But watching women suck cock [when you watched porn] and get fucked made be long to be a cock sucking slut like them -- or a lesbian like them." That's actually how I first discovered I must not be as str8 as I thought I was too!
2 years ago
Hot Beginning Doll!
2 years ago
mmm HOT... got me SO HARD.. can't wait to read the rest...
2 years ago
Loved the story! Actually, I had a similar beginning in terms of how I began my adventures.
3 years ago
Very hot!
3 years ago
very hot and erotic...thankyou for sharing
3 years ago
I'm jacking off right now just thinking about it all, I love to dress as a slut and be played with and eventually fucked deep in the ass
jacquin001
retired
3 years ago
You got me jacking off too yhanks for the story
3 years ago
Very good.