3.29.2006

How I Became a Faggot, Chapter 1

A lot of transvestites with webpages have a section discussing how they started crossdressing. Offering an explanation seems natural enough. After all, what guy wants to end up in a gold dress, blond wig, lipstick and high heels? I know I didn't.

But I did anyway. I ended up trying on 4-inch white pumps at Bakers while two giggling teenage girls took my picture with their cell phones. I ended up with my first serious girlfriend walking in on me while I was masturbating in her bra and panties. I ended up on my knees with another man's dick in my mouth.

So how did this happen to me? How did I ruin my life?

It started with a pair of saddle shoes. I went to an all-boys school. We didn't have uniforms, but the all-girls sister school did. White blouse, plaid skirt, and black and white saddle shoes. The two schools ran a joint, co-ed kindergarten at the girls school, which I attended. In black and white saddle shoes. Yeah, that's right. Thanks to my mother's fashion sense, I began my education as the the only boy wearing saddle shoes amid a sea of girls in them. At first I hated my saddle shoes and the teasing they brought me. But slowly, over the course of the school year, I began to like wearing them. So much so that when I went to the boys school the following year for first grade, I asked my mother for another pair. Somewhere inside of me, in some way I didn't understand, a switch had been flipped.

But was it really that simple, that innocent? Did being made to wear saddle shoes in kindergarten turn me into the sissyboy I am today? If I'd worn sneakers instead of saddles then, would I be wearing boxers instead of panties now? Would I fantasize about fucking women instead of being fucked by men? Would I never have become what I am: a humiliated transvestite faggot?

53 comments:

Anonymous said...

See you can't fight fate!!! You were doomed to be a pathetic pantiwaist sissy from such an early age. By now dressing as a cock sucking sissy should be second nature for you

Anonymous said...

Listen Sissy, you don't even deserve the right to refer to yourself in the first person. Anyone who behaves like you do should refer to herself as a girl and in the third person.

Anonymous said...

How the hell can you deal with being the subject of ridicule for everyones amusement? Dont you have any self respet at all? Go out totally en femme and try on a dress.Leave the dressing room and ask for help..for possibly a better dress for you. Get the salespersons input(no matter who sees it! stand there and wait! Only when you have recieved the advice you desire(and crave you pervert) At that time, ask for some advice on better bras and panties. Change back to en femme and take the bra and panty advice from the sales girl. Purchase the outfit she recomends. ask for her approval and that of her friend. Do it! Write of your adventures blog boy****blog sissy! Good Luck!

Anonymous said...

I love your black and white saddle oxfords I got a pair just like them . They are a lot of fun to wear. I would recomend them for both male or female. It dose take a few days to break them in , but after that they are sooo comfortable to wear. When ever you go out remember to take your saddles for a walk your shoes will love you for it. I have gotten many complements on my saddle shoes.

Anonymous said...

What guy wants to end up in a gold dress, blond wig, lipstick and high heels?

Moi.

Well, i wouldn't have to be blonde...

Chrissie

Anonymous said...

I would fuck you

Anonymous said...

can you tell us more about how you ended up on your knees with another man's cock in your mouth?

bill said...

Hi,

I love your discussion about saddle shoes. I have been attached to these shoes all my life. If you would like to discuss our mutural interest, e-mail me at bllbolen@netscape.net.

Bill

Anonymous said...

Please tell us the story about how your girlfriend walked in on you masturbating in her bra and panties.

Would also hear about your first cock in your mouth.

Please?

Anonymous said...

I don't know what the rush from humiliation is, but I am addicted as well

chrissie.nola@yahoo.com

Anonymous said...

Hi. It is funny, I lived the exact same situation you did, but with sandals instead of saddle shoes. So, nowadays I really love my girlie sandals, have a collection and sometimes wear them in public... I really can't help it. When I was younger, I also had the feeling of regret after I came. Not any more. I learned to accept myself for what I am, and to love being me. Even if I also ended up with a cock in my mouth! Cheers!

melissandal@gmail.com

Anonymous said...

First of all; you look great. Wish I could say I enjoyed my first experience. My first true love along with two of her friends caught me in her sisters bedroom wearing her sister's underwear; I'll leave out the details. She told me to get out (as dressed).
A week later she said she wanted to see me fully made up. I was real nervious and didn't know what was in store for me. When I got to her house she took me down to the basement rec room and I got the shock of my life. There was over a dozen of her friends there and the boys had been drinking. In front of everyone they made me a real girl. An hour or two later though I could just about stand up and I stunk of cum they threw me out of a van in the middle of town. I was told if i ever said what happened they would finish the job. My parents ended up sending me to live with my grandparents and to this day I still have the taste of cum and I will never be able to have children.

sissy becky said...

I love your blog, HT, and I can feel your humiliation as a cock sucking pathetic sissy boy faggot. I was faggotized in the Boy Scouts when I was fucked by another scout. I had been sucking some little white boy cocks then. I didn't start wearing panties and lipstick until years later but once I wore my first panties I was sissified and loved it. My bureau was soon filled with bras and panties, which were daily wear. Of course, shaving my legs, little dick and balls followed. My fantasy is to be dommed by a Big Black Brotha and to worship His cock. But I digress. I'll try to return and enter some of my humiliating episodes as a homo faggot sissy.
kisses,
sissy becky

Anonymous said...

I'd love to f**k you on your back, treat you like a woman. For me the turn on is knowing that you're a boy and that I'm making you take the girls part, I'm raping your mind and your body.I'm conquering you. You are completely defeated and the idea is you'll want it again pretty soon.

Anonymous said...

Only when you're on your knees with a mouth full of hot cock will you feel a woman x

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Anonymous said...

I remember my first pair of sadde shoes they were white and red. My black boyfriend had me buy them and some pink tights. he also wantedd me in cotton briefs with flowers,princeses,all girly things on them.
when we were no together i was to always be in the tightests girdle and seamed garter stockings over my tights.
The most humiliating thing we did was I was dressed as he wanted and he said we were going to a party.
we got to his house and I saw about 10 black men watching a football game.
I was made to serve them snacks,beers or whatever they wanted.
I was introduced to my first gang bang of many more to cum. My tummy was so full of black sperm,my face caked with it. I had to let it dry on my face and thank them.
it was video taped and copies made.
so I am on call by any off the guys to serve them and thier friens or the vieos woul go every place.
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