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 beautiful, 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 fill 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 occasionally 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 penthouse 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 addictive -- 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.
So I'm in college now, I've learned to love and use porn in all its forms, I've learned to be a great cock sucker and to have my ass fucked. I've learned to tie myself up -- as best as possible -- to pee all over myself to get that humiliating feeling. I'd spread the porn mags all over the floor and spend the entire night playing, trying to shoot my cum onto a photo of a cock so that I could lick it up.
The feeling of release whenever I gave in to all of those instincts was fantastic!
I loved cock! But I was a horny 20 something and still chasing pussy. Eventually the girlfriends started to give in and I got my first handful of titty, ate my first pussy, fingered my first cunt. My girlfriends were lovely and fun, but it took until I was 23 before one finally let me fuck her. Having been on the other end of a good fuck, I knew just what I was doing and we had a great time. I couldn't help thinking, however, the whole time my cock is sliding in and out of her sweet red-headed cunt, that I wanted to be the one getting fucked -- but like her, as a girl!
The more pussy I got, the hornier I stayed. I jacked off four or five times a day on top of getting cunt once or twice a week. But even when I was getting laid all the time, the thirst for cock was still there. Sometimes after laying my girlfriend, I'd go to the bookstore and suck cock and have my ass plowed. Maybe if I had lucked on a domme girl things would have been different. But they were all nice girls, very conventional, not kinky at all. In short it wasn't enough. I needed nasty, kinky, dirty, humiliating sex and most of all I needed cock!
Then I met a girl at work and fell head over heels in love. She wasn't drop dead gorgeous or anything -- just a pretty girl next door -- athletic, with a cute face, firm legs, great smile but small tits. And, it turned out, she was a lesbian. We formed an incredibly deep, loving friendship. But with a cock instead of a dripping slit between by legs, I wasn't going anywhere with her. Knowing she was a lesbo drove me crazy! It turned me on SO much! As a homo myself, I totally got where she was cumming from, but I loved her so much and wanted her so much, all the more when I saw her with her female lovers and thought about what they were doing.
I was crazy insane for kinky sex now, even more than usual. My desire to be the girl in a relationship -- which I'd always thought about but had never acted upon, became unbearable and irresistible. That's when I started dressing -- buying cheap female clothes and shoes in thrift stores and discount stores. I got a wig at Halloween and bought makeup. Tits were a real problem. I wanted some so bad, huge ones! But there was no way I could afford them. Finally I found some cheapie faux plastic ones and didn't look half bad in a bra.
I was thin, with long legs, and when I dressed and put on the make up I thought I was very cute. Just the thought of dressing made and kept me hard! Like in high school I'd dance around in the front of a mirror, jerking off to how hot I looked. But unlike in High School, I was now a card carrying cock sucker. So I'd put on all my lingerie, stockings, etc. put my wig inside my shirt and go to the bookstores, get in a booth, pump in the tokens, strip off my shirt and jeans, put on the wig and present myself to the guys peeking through the glory holes.
As just a guy I had never had much trouble getting someone to offer me their cock. But now, dressed as a girl, I didn't even have to rub my finger around the glory hole to let them know I'd suck their dick. Hard dicks showed up almost instantly, and I sucked everyone of them. Sometimes I'd get the booth that had a glory hole on each side and wind up stroking two cocks at once or getting one in my ass and mouth at the same time (a bit tricky to do, but when you are a slut, all things are possible). Men would beg me to let them come into my booth or come into theirs. I never would -- later that would change, but not yet.
I'd suck cock for hours, but the real thrill was doing it as a girl. In fact the real thrill was the POWER I suddenly had over men. As a women I was irresistible. I was getting cock the way I had always wanted it, as a GIRL!
Unfortunately I didn't have the guts to expose myself to my girlfriends as what I was now becoming. A great missed opportunity no doubt. But my kink was going to take me in a very different direction. Could I get men outside of a porn store booth? Would they bed me in a hotel? I begin to dream about it and then determined to do it. After all, having cum this far, why stop now.
Now that I was fully versed in being a gurl, I needed to know if I could turn a man on in person, not just looking through a glory hole. I wanted to have a man treat me totally like a woman, take me to a hotel and make love to me, completely as a woman.
But where to find the guy?
The answer was a chat line. I got an account as a girl -- I signed on as Jennifer, explained what I was and what I was looking for. As you can tell my voice is very fem (listen to my voice into or watch my vid it you don't believe me, giggle) and it was pretty easy to turn guys on and grab their attention.
Of course I got all kinds of messages, most of them pretty lewd and straight forward -- the kind of stuff a guy says when he is jacking off to your voice while watching porn. I already knew I could inspire lust like that. I wanted something more.
Finally there was a nice guy who just flirted with me, treated me like a woman and tried hard to get a DATE. This was SO exciting. This was something I had been wanting, needing, longing for since I was 15, although I hadn't known it. A man wanted me as a GIRL! Like he would want any girl!
It was clear he wanted to meet me to sleep with me, but somehow that seemed secondary to our conversations. So I agreed to meet him at a local Dennys on a weekend night. He told me he'd be in a booth reading a certain book and I could come in and meet him and we'd go from there.
It was several days until our date, and I was in a constant state of excitement and anticipation. I couldn't wait!
Finally the night arrived. It was cool and a little rainy. My wardrobe wasn't very big yet, and a bit conservative, but I put on my cutest outfit. White stockings, white pumps, a pink teddy with garters, pink frilly panties -- very virginal stuff -- and wore a tight gray sweater and a long purple pencil skirt that went below my knees -- certainly not the kind of slutty stuff I like to wear now. My wig was blonde/brown in a very cute page boy style. With my nails painted and makeup on, I looked at myself in the mirror. What I saw staring back with me was a cute, virginal young girl, very sweet looking but also somehow very sexual. In some ways I couldn't' believe how good I looked, and in others I felt like I was seeing myself in the mirror for the very first time.
I drove to the Dennys, but once I parked I was seized with uncertainty. Not doubt as to what I wanted and who I was, but the idea of just walking in the restaurant as a woman. Suddenly I doubted how passable I was, how I'd feel if people stared and whispered. Today I could care less and get off to the stares and whispers, but that night I was nervous.
After setting in the car for 20 minutes I finally took a deep breath, got out of the car and began walking up the sidewalk. Halfway to the door a handsome man came walking toward me, and as he neared he asked "Jennifer?" I was thrilled and relieved; I wouldn't have to go inside, but here was my date!
I apologized for being late and explained why I was. He told me it was OK, that he was so glad I showed up. I told him I wasn't sure if I looked like he expected. He said I was more beautiful than he had anticipated and that I looked like a sexy 1960s starlet.
My heart fluttered. It was my first real compliment as a woman -- at least the first one I had gotten without having a cock inside me.
We drove across the highway and got a room at a Motel 6. We went inside, turned off most of the lights and then he took me in his arms and kissed me deeply. I swooned. It was heaven, the first time I had actually kissed a man on the lips. I almost went limp.
After we necked for awhile I had him lay down on the bed, while I stripped off my sweater and skirt. Once he saw me standing there in my pink teddy, graters and white stockings and pretty pink panties, he moaned -- I mean he moaned! Deep, lustful and awed. I can still hear it all these years later. It was a moan that told me how fantastic I looked, how much he wanted me, how much of a woman I was!
Boy did I reward him for that moan. I dove on his cock and sucked him like I'd never sucked anyone! His cock was very thick, probably about 4 round and 6 long. I had never taken one so thick, but from the way I was bobbing up and down on his meat you'd have thought I had one that size in my mouth nightly! He was moaning with pleasure, and very, very hard! I couldn't stand it anymore and begged him to fuck me!
Naturally I didn't have to beg long. He stood up, I laid down on my tummy and put my ass up in the air. I felt his hands grasp my panties and pull them down. GOD! That felt SO INCREDIBLE!!!!
With my panties down I felt him lube my cunny and then the pressure of his cock at my opening. No one that big had ever been inside me before, but in the days of waiting I had been using a flashlight as a dildo, and that was about the size of his dick, so I opened right up and in he went!!!!!
I was in total heaven as he thrust in and out of my ass. Here I was with a handsome gentlemen fucking me, all dolled up in my pink lingerie, laying face down on a hotel bed with my ass up in the air! It was so feminine! I was so feminine!!!
Finally, but too soon, I could tell he was about to cum. There was no rubber, so I told him to cum all over my ass. He pulled out and seconds later I felt a huge load of hot cum splash all over my ass cheeks and thighs! I came into the sheets as he covered me with his hot juice!
He collapsed on the bed, breathing heavy like men do after they cum, drew me into his arms and kissed me deeply. I loved it, I knew now that I had finally become for real what I had always been inside -- a woman, and in a since I had just lost my virginity as a woman!
After awhile he got up to shower, and then realization of what had just happened hit me! I got up, dressed quickly and left without even saying goodbye. It was a little rude, but I knew he was happy. I wished I'd stayed though b/c there might have been more dates later! But for now, I drove home happy and hard -- a girl for real and a new life ahead of me as a woman!
