11.28.2006

How I Became A Faggot, Chapter 3

Well, you don't need me to tell you what happened next. After discovering the joys of masturbation and the key to my arousal in one fell swoop, I repeatedly beat off while wearing my new saddle shoes. And somewhere deep in my psyche a terrible, unbreakable bond was formed. You see, I didn't have the good fortune of masturbating for the first time while looking at pictures of naked women. I got off for the first time while wearing women's shoes. And for the second time, and for the third time... and for the 100th time.

As guilty and ashamed as I felt about my behavior then, I consoled myself with a temporary truth. I was only interested in wearing saddle shoes. I couldn't be a transvestite because I had no desire to wear any other article of women's clothing. Saddle shoes and that was it. It could be my little secret.

But that comforting truth didn't stay true for long. By the time I entered high school I was tormented by powerful urges to wear other types of women's shoes. I went to a co-ed high school and I would look at the girls in my class and wish I was wearing their suede clogs or their pointy-toed flats. After school, I would masturbate in my saddle shoes and fantasize about wearing high heels. But they were only fantasies then. I couldn't act on my perverted impulses because I had no way to shop in secret. And my mother's shoes were both unappealing and too small.

When I finally turned sixteen my world truly changed forever. Normal guys can't wait to get their driver's license so that they can go on dates and drive around with their friends. For a budding sissyboy like myself, though, it meant something entirely different. I could finally buy my first pair of high heels. I can still remember almost everything about that day.

I went to a Payless shoe store not far from my house. The store was completely empty except for the salesclerk, a young black guy probably only a few years older than myself. I remember how nervous I was to leave the men's shoe aisle and walk down the women's aisle. I remember willing myself to do it because I wanted to wear high heels so badly. I remember hurriedly scanning the shoes in what I thought was my size, wanting desperately to get out of there but wanting equally desperately to stay until... until I saw them. The object of my desire. Not a new video game, or a hot car, or a busty girlfriend. No, not for me. Here was what I wanted. Sissy pink three inch pumps. A fairy's first high heels.

I picked up the open shoe box and clumsily put the lid on it, hoping this might somehow conceal what I was buying. I could literally hear my heartbeat as I walked to the register. I put the box on the counter in front of the black guy. He looked at me, then at the box. And then, without saying a word, he opened the box and looked back up at me. Although I've seen it many times since, I'll never forget that first time, that first look. He looked at me and he knew. His look said I know these high heels are for you, fag. I know exactly what a sick, pathetic, crossdressing homo you are. You disgust me, queer. He picked up one of the high heels out of the box and checked its size. Then the other. Then he put them both back in, closed the lid, and rang up the sale. My whole arm was shaking when I handed him the money. I was utterly mortified at what I was doing. At what I was becoming. And then, before I could even really process what was happening, the transaction was completed and I was out of the store, racing back to my car.

As soon as I started to drive away I knew I couldn't wait a minute longer. I'd been jerking off in anticipation of this moment for almost two years. I had to know what it felt like to wear women's high heels. I had to put them on right then. So instead of leaving the strip mall I circled around behind it, to the back of the stores where the trucks unloaded and no one parked. The coast looked clear, so I parked next to a large dumpster, pushed the driver's seat back as far as it would go, tore off my socks and sneakers, and picked up my new pink pumps. It isn't just saddle shoes anymore, I thought to myself. But I didn't care. My pathetic excuse for a cock was harder than it had ever been. I put them on.

There I was, just turned sixteen, sitting in my mother's station wagon parked behind a strip mall, wearing normal sixteen-year-old guy's clothes, and bright pink three-inch high heels. I was no normal sixteen-year-old guy I suddenly knew. I looked around to see if the coast was still clear. I had to know what it felt like to stand and walk in high heels. I got out of my car and took a few terrified steps. And then, without so much as touching myself, I came as hard as I have ever cum in my life. It literally caused me to double over as if I'd been punched in the stomach. What an unbelievable pervert I am, I can remember thinking immediately after I came. Standing there in the empty lot in women's pink high heels. My warm, sticky spoo soaking through my underwear and my pants. The door to any sort of a normal life slamming shut behind me. I am a fucking pervert, I realized with astonishment. I am a sixteen-year-old sexual pervert.

41 comments:

Anonymous said...

Your blog is without a doubt the most intense recollection of a descent into the life of a humiliated transvestite.

I'm no where near where you've approached, but I already see the reflections. I hope you continue this series onward.

young asian cutie said...

Wow....

Our desires are so similar...

Instead of shoes however, my first fetish was makeup, and i didn't think i was a tranvestite because i wasn't into women's clothing. However, because of the nature and the underlying reason for why i had a fetish of being beautiful and wearing makeup, it soon, translated into other things just like you.

However, i have never taken the bold step like you and doing anything in public indicative of being a transvestite. So, props to you!

Anonymous said...

I NO WHAT YOUR FEELING BABE I WENT THROUGH THE SAME FEELINS NOW I WEAR EVERYTHING THAT I CAN ESSPECIALLY CLEAR PANTYHOSE I LOVE TO GO TO PAYLESS SLIP OFF MY SNEAKERS AND TRY A PAIR OF BALLARINAS OR PUMPS ON MY STOCKING FEET

Anonymous said...

I wonder if there's something specific about that first orgasm that imprints so strongly that you can't escape it.

Mine was while wearing a pair of white panties, when I was eight. I had no idea what was going on, and haven't a clue why I put on the panties...but i was rubbing my sissy stick through them, and voila. It shocked me...and delighted me...and I can't help but wonder if it made me or helped make me what i am today - a pansy faggot sissy just like you.

Chrissie

pascal44 said...

I like your blog.

For me it started out with a pair of shoes too. I was being drawn to look at women's shoes in shop windows and finally I just had to have a pair of my own. The pressure was too strong to fight.

I wanted a very girly pair of three inch pumps with ankle-straps in colour 'pearl'. The shop was in a very busy mall and full of windows to passerbys and so I went there early one morning just after opening time. My heart was beating so fast, my face so red with embarrassment while trying to look casual as a young lady racked up my purchase.

I was shaking by the time I got out of the mall. When I got home I got a hard just looking at the shoebox. I took out the shoes and they smelt wonderful. I went to my bedroom and put them on and lay down and masturbated. The shoes felt as good as they looked.

Well that was the start. Then I wanted lingerie so one day I was waiting in the checkout lane of a department store with an ensemble of black ligerie lacey lingerie (in large size !) and two women, friends or sisters, arrived behind me and one said 'that's disgusting'. I knew they were talking about me.

I don't cross dress much, certainly not in public, but there is something about the humiliation fix in publicly buying feminine stuff. Shoes and boots remain my favourite femme things. I bought some via mailorder once - but it just wasn't the same as purchasing them in person because that is half the fun.

Browsing ladie's shoes recently in a store two elderly ladies walked past and one said 'oh, a man looking at women's shoes, how unusual' and I said 'I love women's shoes, there's lots of us who do, its not as unusual as you may think'.

Anonymous said...

we all have the same experiences -the anxiety, stress and excitement of shopping for our passion. maybe deep down you may really love to dress, but your shoe fetish is dominant- who knows...just enjoy it... guilt is for those who do something wrong to others

this may be a good thing since you dont have to go thru the hassle of a full wardrobe and makeup.

"Perversion?"...I like to think of it as a erotic hobby...no different than those millions millions of men and women who buy sex toys and lingerie to stilulate erotism....

feminine attire stimulates the senses like no other...i can see why women love it....
the feel of silk...lace, etc
why should girls have all the fun?

Heels for me: the way they hike up ones back side and instantly transform you to a feminine stance. the pull on your calves as you walk each step..

Anonymous said...

hmmm...this post reminded me alot of of when i was a very young sissy. the first time i ever came was when i was playing with my nipples (i didn't even touch myself "down there"). i was sooo confused, it wasn't long however until i came to the realization that i was different from boys. i still liked girls, as a matter of faggot i ADORED them so much that i wanted to be one. it all started out innocently enough, with lingere, heels, make-up, and just wanting to be pretty. but in the long run my dressing has evolved into sick desires that are sometimes even repulsive to me.

Veronica said...

Oh the memories, as I sit here reading these comments I reflect on how I got hee and how it started. My legs are encased in black stockings attached to my garter belt. I have 4 inch heels on that match my mini skrt and louse My bra pushes my breasts up to form a nice vee between them. I was 7 years ld when I fiwsrt slid on a pair of my mother's stockings and her high heels. I didn't know what an orgasm was but I kept coming back for more.

TvTrixie said...

I bought my first pair of High-Heels from Wards, black 4" suede with angle straps. I was so excited, embarrassed buying them. I quickly drove to a park and put them on, then walked around close to the car with then on, I had the hardest hardon and dripping cum everywhere. Looking around for a guy because I felt so womanly. It just felt right to wear them which eventually led me on further into my transformation and acceptance.

Anonymous said...

Like so many I started when I bought my first pair of women's Spalding Saddle Shoes and then Keds, lace stocking and panties. Great sex but always with women.

Mary Kay said...

Oh I have been there. You are young and you put on a relatives heels and that makes you as hard as you can be. Later you get some shoes of your own. Then pantyhose which are easy to come by and which makes the shoes feel different.

Then you dress up in a garter belt and stockings and shoes and jerk off and the orgasm is terrific.

Its a short leap to panties and a bra with breast forms and the next thing you know you are leaving a comment while you are wearing some nice gold hoop earrings, a blond chin length bob-style wig, a black corset tightened to the max with 4 garters attached to your pink seamed stockings. Your sheer black panties have rows of red ruffles. You have on a red bra with B cup breast forms. You can see the bra through your sheer blue blouse that you recently purchased from HSN. The color matches your short blue pleated miniskirt. On your feet you have on a pair of pointy toed side zip black Croft and Barrow shoe boots with three inch heels that you recently purchased from Khol's. Or maybe that is just me.

Unknown said...

This is a familar story. When I was young, I was horrified to find myself attracted to my older sisters clothes, especially her shoes. I tried to resist, but my will power broke when she brought home a pair of white patent leather mary-janes, with a very high chunky heel. As soon as I was alone, I went to her room and put them on. I danced around, ecstatic with the new feeling of satisfaction I felt by giving in to my shameful but irresistible desire.
That was, of course, the beginning of a delightful, humiliating and intense life of fufilling my desire to act and dress as a sissy boy. High heels remain my weakness, I can't get enough, especially patent leather high heel mary janes.

Anonymous said...

I love this posting, especially her lovely face being made up!

Anonymous said...

Im still in a bit of denial. After reading your blog I realize I am the same. Shopping in person is a must. Hardly contain myself when playing dress up. My girly fem thoughts and feeling are evolving. Who knows some day I might end up with a Dick in my mouth just to fullfill some womenly lust. I consider myself hetrosexual, closer to bi curiouse.

Anonymous said...

For me it all started with nylons when I was about 5 and from there it just eventually went to dressing as a woman totally and having a deep longing to become one. Eventually I became attracted to men and even though I've yet to do it I think about sucking cock and getting fucked constantly. Your experiences shopping for clothes really hit home for me. I used to really stock up on everything around Christmas time hoping people would think I was buying presents. Now I'm just such a transvestite sissy that I don't care anymore.

Women leather pants said...
This comment has been removed by a blog administrator.
Anonymous said...

I too started dressing in my mothers clothes at a very youn age, and got sexually aroused by it long before I knew about getting sexually aroused. I now regularly dress completely, trying to pass as a woman, but I still get hard at the thought of frilly nighties and pretty panties, and desire to experience sex with a man, so really I'm just a pathetic sissy.

vikkicdts said...

I loved seeing women in dresses and heels since I was 4-5 years old. I would browse catalogs checking out womens pages looking at various dresses and high heeled shoes.I would masturbate while scoping them out.When I got into my teens, a man that I worked with invited me to his apartment. After a few drinks he brought out some womens clothing and told me to try them on. He helped me apply make-upand after I slipped into a pair of high heels and looked at myself in the long mirror he had, I creamed in those panties.

Anonymous said...

i had a similar occurance, but it was with a pair of red high heels. I too parked in the rear of the store and put them on.It felt so satisfying and feminine. I was also aroused knowing that when I got home I would pair them with my new red dress.

vikkicdts said...

I am finally coming to terms that I am a Sissy faggot, and when transitioned completely relish going out in public and showing myself. I am also looking at good looking men and the bulges in their pants.

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the stringman said...

I don't think you're pathetic. I think that the fact that YOU think you're pathetic is what is truly awful. But not pathetic. I think that you showed amazing courage by going and getting what you needed. And if your photo in your blog is really you... WOW!! You... Are... BEAUTIFUL!!! I wish that I could be where you are in life. I am very large and cannot hope to pass for female. But that isn't going to stop me from trying, from doing the hormones and from getting as much feminine clothing as I possibly can. Yes, it's also extremely erotic for me as well. Any boy dressing up will get a boner from it, and then need to come so exquisitely! Just keep on living as a femmed male, and no one will ever know. As long as you ACT THE PART, you will fool them all!! You go, gurl!!!

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