When I knocked on the motel room door, all fagged out in a pencil skirt and satin blouse, bra and panties, garter belt and stockings, wig and stilettos, I knew I was a transvestite. When the middle-aged guy from craigslist looked me up and down and smiled, I knew I was a sissy. When we started kissing on the bed and he slid his hand up my skirt, I knew I was a pansy. When he unbuckled his belt and started pushing me down to his groin, I knew I was a fairy. When he said "Suck it good" and I put his dick in my mouth, I knew I was a cocksucker. When he pushed down the back of my head over and over and said "You like that, don't you?", I knew I was a faggot. When he started to cum in my mouth and then pulled his dick out and spunked the rest in my face, I knew I was the most pathetic sissy transvestite cocksucking fairy in the world, and always would be.
But you know what? So do a lot of you. A lot of sissy queers come here and read my confessions. I know it. And I bet some of you are sitting at your computers right now rubbing your loser cocks through your skirts and your panties, your high heels digging into the carpet, trying not to cum too quickly, trying not to blow your faggot's load until you can't hold it in a millisecond longer. What a bunch of losers we are. What a bunch of fairy transvestites. Hey buddy, wanna fuck that hot chick over there? No, but can I put on her dress and take it up the ass? God, we suck.
So anyway, quit being so anonymous, sissies. Quit just coming here hoping for a new post to beat off to and then leaving without contributing in any way. Do us all a favor and describe your most humiliating experience - or one of them at least - in the comments to this post. Tell the world how shitty it is to be you. And be descriptive. Try to get me off for a change.
But that wasn't all. A week at most passed before I found myself standing in line at Walmart with a pair of thigh highs in my sweaty sissy hand. The cashier was a young girl and, like the clerk at Payless, barely older than myself. She smiled broadly and almost giggled when I put the stockings - my only purchase - down in front of her. Who could blame her? I would have laughed at me too. A sixteen year old guy buying sexy black thigh highs and nothing else? What a fag!
But I was desperate to know what it felt like to wear my new pink pumps in pantyhose. I wasn't a transvestite I still thought. Pantyhose was just part of being into women's shoes. I didn't want to wear other lingerie or dresses. I wasn't going to end up on all fours in some cheap motel room while a hairy forty-five year old man shoved up my miniskirt, pulled down my panties, and whispered into my pierced ear "Are you ready for some fat cock, you little sissy bitch?" That wasn't going to happen to me.
And for a while all that was more or less true. I managed to get through the rest of high school without ever trying on a bra or a pair of panties. I even had a girlfriend my senior year. Before I went away to college I threw out my women's shoes and pantyhose and told myself that I was normal again.
Of course, it was already far too late for me to ever be normal again. I didn't know it yet, but I had forfeited my right to be a real man the night I ejaculated for the first time in my life while wearing girls black and white saddle shoes. I sealed my destiny again and again in a thousand beat-off sessions in my saddles and high heels. That cheap motel room and that hairy man were waiting for me. Waiting for a little sissy bitch in fuck-me lipstick and fuck-me pumps to climb onto a dirty bed and spread his shaved legs. My shaved legs. My red lips. My stripper heels. Me.
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.
But of course I did wear saddle shoes again. The desire never left. In eighth grade I asked my mother to drop me off at our local library. When she drove away I walked to a nearby shopping center and bought a pair of girls black and white saddle shoes. I told the saleswoman that they were for my sister and I'm sure she believed me. I mean, odd as it was, she could never have suspected that I wanted the saddle shoes for myself. She could never have guessed that I would bring them home hidden in my bookbag. That I would wait for my parents to go to sleep and then try them on, feeling their stiff, uncreased black and white leather on my feet for the first time in five years. That I would become almost instantly aroused and instinctively start rubbing my tiny penis, still in my underpants, against the sofa in our living room. That I would suddenly and unexpectedly explode in the first orgasm of my life while kicking the air in girls black and white saddle shoes.
1. Having a large black woman sing "Tutti Frutti" when I walked by her wearing Bakers high heeled boots at the mall.
2. Watching a college-age woman whisper to her boyfriend in the next aisle at a DSW shoe store and then having the boyfriend laugh out loud and make a beeline for me. The woman had noticed my high heels and now I had to just stand there and "take it" as the boyfriend checked out my pathetic public sissiness. I felt like such a faggot.
3. Having the salesgirl who had just fitted me for "fuck me" black pumps ask if I was interested in one of the purses they had on sale. I'm not sure why exactly, but it caught me off guard and drove home what a total fairy I really am.
4. Walking up a staircase at the mall in high heeled women's loafers while four or five teenaged girls followed behind me giggling and guffawing. Then, when we reached the second level, one of them said very loudly "Nice shoes fag!" and they all broke out in hysterics.
5. Trying on a wig in a wig store when the male Fed-ex delivery person stops in with some packages and looks at me like I'm the biggest queer he's ever seen.
6. Having a very attractive middle-aged saleswoman at an upscale women's clothing boutique stare at my black and white saddle shoes and say"I'm sorry, but we don't cater to crossdressers" as I was standing in front of her holding a little black dress and before I could ask to try it on.
7. Being asked in the lingerie section of a department store by a cute salesgirl if I was looking for "Bras, panties..." When I answered "Just panties" she smirked and said "I thought so. There some nice pink panties over here."
8. Being told I had to use a different dressing room at a women's clothing store after I had tried on a tight, short skirt and having to walk across the store to another dressing room while wearing the skirt and carrying my pants and knee-high women's boots in front of half a dozen female customers.
9. In my early days of public sissiness, catching my reflection in a wall of mirrors at the mall and being shocked at how sissified I looked in a pink blouse, tight women's bootcut jeans, and barely concealed high heeled clogs. I felt instantly mortified and simultaneously wildly aroused and started walking for the nearest exit almost in a panic, only to ejaculate in my panties without touching myself before I'd managed half a dozen steps.
10. Having to walk across a mall food court directly in front of a huge group of high school male athletes while wearing black women's pants that fully exposed the three and a half inch heels of my noisily clicking and clacking pointy-toed women's boots. Utterly humiliating.
I always feel the same reluctant anticipation as I approach the mall's highway exit. Part of me doesn't want to go through with it. Part of me wishes I had just beat off at home instead of deciding to expose myself to the humiliating ridicule another part of me craves. Sometimes I say little mantras out loud as I look for a space in the parking lot. You're a sissy. This is what sissies do. Face the shame.
Getting out of the car is often the hardest part. I usually have to wait - nervously, pathetically - for whoever is nearby to pass. I can't just "hop out" and stroll inside. I need a minute alone, standing between parked cars, to pull my jeans down so my high heels are as concealed as possible. I need to adjust my bra straps from the car trip. And I have to push my tiny, half-erect, half-limp dick down in my already-damp panties. I'm such a fucking pervert, I think, as I wipe the precum from my panties off my hand and onto my jeans. God, I hate myself.
And then, when the coast looks clear, I'm off. Out in the open. Heels clicking loudly on the pavement. Eyes focused on the mall entrance. Trying not to look to the left or the right. Trying not to notice if anyone's noticed me. If I'm already being gawked at. If some college-age woman and her boyfriend have stopped dead in their tracks to stare at the fag in women's clothes. At the sissy transvestite on parade.
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?
Second, because I haven't found much else like it on the web. There are tons of crossdressers on the internet these days who say things like "I love being a girl" and who claim their motivations to wear wigs and skirts are non-sexual. Maybe it's true, I don't know. But when I slide my breast forms into my pink Victoria's Secret Second Skin Satin bra, I'm not "loving being a girl." I'm concentrating on not getting an erection until I pull up my matching panties. And I'm trying to decide whether to masturbate on my bed or downstairs in front of my computer.
Third, to get your feedback. This blog is all about the unvarnished truth of being a sissy transvestite. I really hope those who visit will add to the project by leaving brutally honest comments.
Often, by the time I get home from the mall, I already want to change into clean panties. The frilliest, laciest ones I own. Then I'll put on that negligee, or my new pumps, or the skirt I tried on at The Gap. I'll look at myself in the mirror and think about the smirking saleswoman who asked if I needed help, or the teenage girls who burst out laughing the instant they saw me. I couldn't be more pathetic. I couldn't be more of a sissy. And then, because I am what I am, I lie on my bed, lifting up my legs up so that I can see my high heels in the mirror. I'm such a faggot transvestite, I tell my reflection out loud. I arch my ass up until I can see the bottom of my panties under my skirt. I'm such a sissyboy, I say, shoving a pillow under my small, now hard-again cock. Lust and self-loathing swirl in me as I start to rub my pantied-clad dick into the pillow. Fucking it up and down, back and forth. Faster and faster. Curling my toes in my pointy high heels. Feeling my bra straps dig in my shoulders. Mouth open, gasping, crying out softly. Until I'm cumming in my panties again. Cumming the only way I can. A masturbating transvestite. A sissyboy faggot.
This is the only way I'll ever be.
Before I cum, dressed in woman's clothes at the mall, the shame of it all turns me on. Gives me the courage I need to embarrass myself that way. But the split-second after I spurt into my panties all that turn-on is gone, vanished. Instantly I become this pathetic pervert who just beat off in women's clothes. I want nothing more than to go home and take off these things, hide them away, forget what I did.
The humiliation I feel then is very different from the humiliation I feel when I first enter the mall. It's painful and shameful and completely devoid of any eroticism. Right then, I see myself as others do. As a pervert and a freak. A sissy and a fag. Right then, I know who I really am.
But I do. I am.
It gets worse. Just being a pathetic crossdresser isn't enough for me. Sometimes wearing a tight, leather skirt and fuck-me pumps doesn't make me hard. Sometimes I need to face the humiliation of being what I can't deny I am: a perverted sissy transvestite. So on go a pair of women's jeans or black pants. On goes a pink shirt with 3/4 sleeves and a pair of high-heeled boots. Or women's loafers with a three inch stacked heel. Or saddle shoes. And then it's off to the mall. No wig. No makeup. No hiding. Just a sissyboy trying on stilettos at Steve Madden. Buying a bra at Victoria's Secret. Taking a dress into the changing room at Hot Topic.
The stares. The whispering behind my back. The pointing and giggling. Look at that faggot. Oh my god, he's wearing high heels. There's a guy in there trying on skirts. The burning shame. The total humiliation. Can't look up, can't make eye contact. I'm too embarrassed. I don't believe what I'm wearing. I can't believe what I am. I hand the pretty, young cashier my money. She smiles and neatly folds the negligee, places it gently in the bag. What must she think of me? What does she say to her co-workers the minute I'm gone? Why can't I be a real man like her boyfriend? Why are my panties getting wet?
Then it's back to the car. Quickly, hurriedly. I have to get out of here. I got what I came for. My god, I'm a sissy. My heels echo loudly in the parking garage. I'm so utterly ashamed. But I'm so hard now, too. So hard I can barely put my key in the car door. Barely start the engine and pull out before... before I'm rubbing my tiny little dick through my pants and my panties. Telling myself to wait but knowing I won't, knowing I can't. And then suddenly it's too late. I'm cumming in my panties. Cumming and cumming like the humiliated transvestite I am.