11.29.2006

How I Became A Faggot, Chapter 4

I still wasn't a transvestite I tried to convince myself as I drove home, my new high heels shoved under the passenger seat of my mother's car, my whole groin drenched with cum. I was just into shoes. I wasn't some dress-wearing, cocksucking faggot. I liked girls. I wasn't gay. I had a fetish for saddle shoes. And high heels. And maybe women's clogs. That's all.

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.

58 comments:

glosstights said...

Great job with the blog,transvestite!
And I love your choice of photos,the crossdressers look so ashamed of being such fags...cos well let's face it they are ;).

Katrin said...

Please keep on telling us on how you have become such a sissy faggot. Your story is really great and i am curious to read about your humiliations.

hugs

maid katrin

Anonymous said...

Shave your arms, too, sweetie. Boys like it better when you're smooth all over.

Danelle said...

I love the site.


danelle

Anonymous said...

Glad to see you're back and posting. I love what you're writing, keep it up!

bridgetm2f@hotmail.com said...

It's strange how it seems that so many of us have similar ways of getting into this and the way it all happens. The first time I masturbated was when I was plannin on a lingerie outfit to by myself. My first dressing started with pantyhose, then lingerie, then pants, blouses, and now shoes. I am always so ashamed when I get off to this so I try to enforce chastity on myself. However there seems no hope to getting over this and I am doomed to fall into doing it forever, but if there was a pill to make myself normal I would take it in a heart beat.

Miss D said...

good gurl... keep telling everyone about your humiliations - they will help to femme you even further.

But you already know that.. you savor your femming humiliations don't you sissy gurl?

Miss D

Anonymous said...

Well,My wish is for you to find a Dominant Lady that will love you the way you are and make you happy.
My opinion for all the sissies is that they are more men of every men around us.It takes a lot of courage to admit something like that and be a sissy.Personally,Ilove it and I have turned My fiance into a sissy too.In the beginning it was forced sissyfication but now he absolutely loves it!
Keep on posting
Ms Alice

Anonymous said...

My dear Idont know what shoud Icall you so I just say Ann because i feel its a good name for a sissy like you.
My dear Anny, I read your story and Iam sad toee thet your sad.Anny dont be ashamed sad or angry that your asissy beauty Anny I am a crossdresser that my family introduced me asagirl from ten years old and you dont know how it feels when I walk in street anyone looks me as girl I even had a lover who wanted to hve e and loved me so much.You know Ann you shouldn`t be shy against have more makeup beautiful clothes(But norml girly clothes against of big high heels)and go in a new place with agirly account try to be hot but not lughly like other girls get flower and say "How you dare to do it,oh..." dont be close to boys and be with girls like polite girls.No need of black stocking use girlish socks and say "Um I want a blousew,doyou have?" but when people believe dthat your a girl(and dont be like women) start with stocking and pantyhouseand...
kiss,kiss
Mariana

BettyBrooks said...

i love your "when I sealed my destiny." yes, there are all sorts of "no turning back from that" points for sissies. you speak for all of us.

BettyBrooks said...

your story is the same as that of your perverted readers, you fag. Just substitute different names and dates. i was "destined" through countless incidents too. From when I put on my sister's one-piece bathing suit and enjoyed myself in a locked summer cottgage room--until my homophobic brother spied me through a crack in the wall and called out for me to stop "playing with yourself." From there to the day recently (March 22) when I got my first sissy orgasm from being face-f*cked. yes, many points in between and yet to cum...

you are a sissy gurl among sissy gurls, though; what a great writer you are. We'll write for you too, so keep coming back, but on the other hand don't give up churning out your tales for us because it's another part of who you are and can't escape.

francine said...

I have been outed as a sissy. My wife Sherry came home and found me dressed in her underwear and stockings, playing with myself in front of the computer looking at a sissy cuckold site. I suppose I have been lucky to last for 6 years doing it at least once a week. But it was still a shock to be caught.She is quite a forceful woman, and she went berserk. Threatening to tell all of our friends and relatives. I pleaded with her to calm down, and I made the mistake of telling her I would do anything to put it right. Eventually she did calm down but demanded to know what I had been looking at. She wouldn't allow me to take any of her clothes off, so there I was standing in a black basque (padded out), black stockings, g sting and by now a very limp dick. I had to stand at her side whilst telling and showing her all the sites I go on. Sissies, cuckolds, slut brides, fem dom, gang bangs, etc. She was amazed that despite my utter humiliation that my dick still got hard whilst looking at the pictures and listening to her read some of the stories out loud. I told her that all of the sites turned me on. She ordered me to get her a glass of wine whilst she took a closer look at some of the stories, especially the femdom and sissy ones. After about 10 minutes I was ordered to fetch her two dildos and digital camera. I need some evidence she said, just in case you change your mind about putting this situation right. She then ordered me in to various poses with the dildos and took about 20 pics, the final one being with me on my back, legs in the air, a dildo just entering my ass and me sucking on the other one. I was horrified at this, but much worse was to come as she started to warm to her task. She phoned and emailed the pictures to her best friend Karen. I was then made to put on a short red dress, full make up and wig. We got in our car and drove to Karens house about half a mile away. She could not stop gigglng at me, utter humiliation. Over two bottles of wine they discussed what they would do with me. First of all they needed more evidence, so Karen suggested inviting 2 gay friends , Roger and Simon, round for a drink and some fun. They turned up and after only a few minutes Sherry was tugging at Roger's trousers, encouraging him by saying come on Roger I've heard you have a monster cock. He didn't struggle, and Sherry unzipped him and let his trousers fall to his ankles,and then got on her knees in front of him, slowly peeling off his underpants. I was shocked at her behaviour, but worse was to come, his huge cock was finally let loose to dangle right in front of her face. She had no hesitation in taking it in both hands and guiding it to her mouth. Sherry, my wife was sucking another mans cock right in front of me, and it was huge, about 8inches. I was ordered on my knees beside her and she then pushed it into my face. Lick it she demanded, and then suck it. It grew even bigger. As I was doing this Karen was taking photos from different angles making sure my face was recognisable. Sherry kept saying to me ' come on sissy boy, suck harder ' at the same time she was squeezing and tugging my cock and balls so hard it was bringing tears to my eyes. I'm going to make you pay for what I discovered to-day she mocked at me with a grin. Then all of a sudden she tore her dress off to reveal her fabulous full womanly body, she stepped out of her knickers and positioned me laying on the floor with my head arched back on to the sofa. She then knelt on the setee with my head directly under her pussy, and I was ordered to lick it. I forgot about the situation I was in and sucked and licked her pussy which was already dripping wet with excitement. I was so busy doing what I was ordered that I didn't notice Roger's cock until it began to force its way into Sherry's wide open slit. He pushed further and further in to her with slow movements until the final surge which buried him deep until I could only see his huge balls. And all the time the woman whom I thought was a tender loving wife until a few hours earlier, was talking filthy to Roger, fuck me, fuck me, make me come, yes, I can feel your cock get harder let me squeeze your balls, but in between these screams of ecstacy she was humiliating me as much as possible. 'Are you happy now sissy, is this what you wanted, all dressed up in womens clothes watching your wife being fucked, well is it' she demanded. I had to say yes because it was what I had dreamt about for years, but was too afraid to tell her, and now all of a sudden, although I was utterly humiliated and degraded I felt satisfaction and my cock was so hard I thought it would explode. Then Roger started to moan, 'oh yes said Sherry, your going to come I can feel it, just stay still' she said to him 'and I'll finish you off'. Very slowly she moved her pussy back and forward on his monster cock , slipping it all the way in and then out. 'Sissy, get ready for your first taste of cum' she demanded, 'open your mouth very wide and put your tongue out and dont spill any of it'. I had a close up of the action, being right underneath her pussy, I could see all the juices flowing from her and how wet his cock was, and then it happened, Sherry knew instinctively that this was the final thrust before he shot his cum, she lifted one leg up to give herself better access, got hold of his cock just in time, pulled it out of her gaping hole and with one stroke had guided his pulsating cock to the edge of my mouth just before he launched his first wave of sperm. I felt it hit my lips and back of my mouth, the second lot hit my cheek, nose and left eye and the further spurts all landed on my tongue. It was a fabulous feeling. Sherry took his cock in both hands and told me to suck it, and lick her juices off. ' Thats what your wife tastes like on another mans cock ' she laughed. Don't swallow any his sperm yet she ordered, until Karen has taken more photos of your cum covered face. After Karen had taken another dozen or so pics, Sherry started to use a spoon to gather all the cum that gone on my face and she spooned it in to my mouth. I was choking there was so much but she hissed at me to open wide for one last photo of my cum filled mouth. She then forced my head back as far as it would go and started to massage my throat just as you would an animal if you wanted it to swallow a tablet. I swallowed the lot. The two women could hardly contain themselves with laughing at me, you poor sissy Sherry finally said, Roger and Simon are not gay they are two of the studs who have been fucking me for ages. I have known for a long time that you have been dressing up in my clothes, you never put them back in the correct place after you've worn them. Also, they sometimes smell of your cum and you always stretch them out of shape. I can use a computer much better than you therefore I have been able to track all the sites you have been going on for ages. I knew you must have been jacking yourself off a couple of times a week because you never want sex with me. So now its revenge time. I was just waiting for the right time to catch you and to-day was it. And I've got all the proof I need with the pics. So if you don't do as I command from now on these photos will be emailed to all of your friends. But don't worry you poor sissy, you will be able to wear womens clothes every day from now on, I will make sure you do, in fact to-morrow I am going to take away all of your mens clothes and put them in a safe place so the first thing we need to do is go shopping for a full new wardrobe of girlie clothes for you, I am so looking forward to your total humiliation in front of all those young shop assistants. You are going to be my housemaid from now on. I felt numb. How could we ever get back to where we were before. All this because I could not resist the feel of womans clothing on my body. Was it worth it. Yes, of course it was because there is no other feeling like it even if it just lasts until I cum on my panties.

sissy bitch said...

Yes, when I was 16 I was a guy, I mean I went out with girls and all. When I was 21 I got married to a hot women, but because I have a 3 inch dick I could not satisfiy her. Soon after I became her BITCH!

She went out with real men while I stayed home, dressed like a sissy, tied to the kitchen chair. She often came home with men and made me watch dressed like a little sissy fag while she had her wet cunt pounded by her boyfriends.

I now suck cock on command, and I am the sissy bitch crawling on dirty hotel bebds with my ass arched high getting ass fucked by old men, and screaming like a little girl as they fuck me.

I'm sissy fag that knows her place

iamagirlnow said...

Brilliant.

Anonymous said...

Oh please don't write anymore. It makes me sooo hard when i read about what a hopeless sissy you are. When i read about your humiliation i feel myself teetering on the edge of the very same delicious abyss. It's like staring down over the edge of a slippery pink precipice, holding on to only a thin satin ribbon. i'm sooo sooo close. Please don't push me over. Please. Oh Gawd PLEASE.

Anonymous said...

While waiting on my divorce, I was deeply depressed and embarrassed about my cross dressing being exposed to all my friends, my employees, the whole town. Besides counseling, I decided to 'man up' and join a health club. I had been a superior athlete in high schook, lettering in cross country, swimming, track and tennis. but since then.. I was mostly concerned about maintaining my soft, thin, feminine, delicate look. going to this gym, turned out to be a huge shock for me. in H.S.I had been in many locker rooms and I did not recall ever noticing anyone's cock. I just did not look. But in this gym, I walked in, took off my clothes.. and I felt like a woman in a man's locker room. I was small, thin, weak, shaved smooth, delicate.. and I could not take my eyes off all the big cocks around me! I was so embarrassed every time I went, but I could not stay away, I was hooked, I tried not to stare at the big thick peckers everywhere, but I could not help it! I was such a skinny, little faggot compared to them. I understood better then how my wife had come to hate me. In time, in the shower area, I met a guy with the thickest, most 'hard looking' cock I had ever seen..it was GORGEOUS! And he started talking to me! Eventually he asked me out for coffee, eventually I told him that I thought his cock was BEAUTIFUL, eventually I told him that i was a crossdresser, eventually he asked me to a party at his house...

Anonymous said...

this is a continuation of the previous where I met 'John' at the health club, specifically we were both naked, just the two of us, in a group shower room. Our relationship was slow. John told me that he was married, but in fact, his wife left and divorced him, but he had not accepted that yet and his house was full of her pictures. He was waiting for her to return.I also understood why she left him. John is about the most boring person in the world. Tall, good body, best most gorgeous cock, only average in the face but..sooooo boring. Big guy, he hardly spoke and when he did, it was so soft you could hardly hear him. No sense of humor. But he had quickly wanted me in his life, alot. And I wanted him.. at his parties and with his friends.. soooo boring. John's friends were nice to me...mostly married and working in banking, like him. John and I spent alot of time together early on, because he asked me, and I felt.. like his girlfriend, sort of. But John hardly talked.. I talked, I tried to get him to talk, he would, a little. When I told him I loved looking at his gorgeous cock, he just sort of smiled. Finally, drunk once, nervous, I told him that I was a crossdresser. His eyes got real big for a few seconds and he said, "oh...thats interesting". I waited for him to say more...BUT HE DID NOT! I asked him if he would like for me to dress for him sometime, he answered, "if you want". WTF? But after the party at his house, I stayed to help him clean up though it was late and I had over an hours drive home. Finally, just as I was to leave, feeling sleepy, tired and a bit annoyed wondering why I was there in the first place, I walked into the living room from the kitchen and there was John, totally naked, that big huge cock of his! I did not want to...but I just stood there, awestruck. Of course, John said nothing. I walked over to him..and softly asked if I could touch 'it'. John said yes..and for the first time in my life, I reached out and put my hands, both of them, around another man's penis which was about twice as big as mine, and he was not even erect!
OOOOOOOOOH! it felt SO GOOD! Alive, warm, thick, HEAVY! I was stunned at just how heavy it was.. I could feel the blood pulsating through his cock...and, I felt it get bigger in my hands! How big would it get when it was fully erect?!

Anonymous said...

this is a continuation of the previous where I met 'John' at the health club, specifically we were both naked, just the two of us, in a group shower room. Our relationship was slow. John told me that he was married, but in fact, his wife left and divorced him, but he had not accepted that yet and his house was full of her pictures. He was waiting for her to return.I also understood why she left him. John is about the most boring person in the world. Tall, good body, best most gorgeous cock, only average in the face but..sooooo boring. Big guy, he hardly spoke and when he did, it was so soft you could hardly hear him. No sense of humor. But he had quickly wanted me in his life, alot. And I wanted him.. at his parties and with his friends.. soooo boring. John's friends were nice to me...mostly married and working in banking, like him. John and I spent alot of time together early on, because he asked me, and I felt.. like his girlfriend, sort of. But John hardly talked.. I talked, I tried to get him to talk, he would, a little. When I told him I loved looking at his gorgeous cock, he just sort of smiled. Finally, drunk once, nervous, I told him that I was a crossdresser. His eyes got real big for a few seconds and he said, "oh...thats interesting". I waited for him to say more...BUT HE DID NOT! I asked him if he would like for me to dress for him sometime, he answered, "if you want". WTF? But after the party at his house, I stayed to help him clean up though it was late and I had over an hours drive home. Finally, just as I was to leave, feeling sleepy, tired and a bit annoyed wondering why I was there in the first place, I walked into the living room from the kitchen and there was John, totally naked, that big huge cock of his! I did not want to...but I just stood there, awestruck. Of course, John said nothing. I walked over to him..and softly asked if I could touch 'it'. John said yes..and for the first time in my life, I reached out and put my hands, both of them, around another man's penis which was about twice as big as mine, and he was not even erect!
OOOOOOOOOH! it felt SO GOOD! Alive, warm, thick, HEAVY! I was stunned at just how heavy it was.. I could feel the blood pulsating through his cock...and, I felt it get bigger in my hands! How big would it get when it was fully erect?!

Anonymous said...

this is a continuation of the previous where I met 'John' at the health club, specifically we were both naked, just the two of us, in a group shower room. Our relationship was slow. John told me that he was married, but in fact, his wife left and divorced him, but he had not accepted that yet and his house was full of her pictures. He was waiting for her to return.I also understood why she left him. John is about the most boring person in the world. Tall, good body, best most gorgeous cock, only average in the face but..sooooo boring. Big guy, he hardly spoke and when he did, it was so soft you could hardly hear him. No sense of humor. But he had quickly wanted me in his life, alot. And I wanted him.. at his parties and with his friends.. soooo boring. John's friends were nice to me...mostly married and working in banking, like him. John and I spent alot of time together early on, because he asked me, and I felt.. like his girlfriend, sort of. But John hardly talked.. I talked, I tried to get him to talk, he would, a little. When I told him I loved looking at his gorgeous cock, he just sort of smiled. Finally, drunk once, nervous, I told him that I was a crossdresser. His eyes got real big for a few seconds and he said, "oh...thats interesting". I waited for him to say more...BUT HE DID NOT! I asked him if he would like for me to dress for him sometime, he answered, "if you want". WTF? But after the party at his house, I stayed to help him clean up though it was late and I had over an hours drive home. Finally, just as I was to leave, feeling sleepy, tired and a bit annoyed wondering why I was there in the first place, I walked into the living room from the kitchen and there was John, totally naked, that big huge cock of his! I did not want to...but I just stood there, awestruck. Of course, John said nothing. I walked over to him..and softly asked if I could touch 'it'. John said yes..and for the first time in my life, I reached out and put my hands, both of them, around another man's penis which was about twice as big as mine, and he was not even erect!
OOOOOOOOOH! it felt SO GOOD! Alive, warm, thick, HEAVY! I was stunned at just how heavy it was.. I could feel the blood pulsating through his cock...and, I felt it get bigger in my hands! How big would it get when it was fully erect?!

Anonymous said...

damn i wish i waas as brave as you i would love to be some mans cheap whore to use as he saw fit

Anonymous said...

i am a transvestite and i think you are hot. i wish thayt i looked that good. i am fullt dressed as tracey and just got back from a wlk in the dark. i seen only 3 cars go by while on my walk. i always wonder if they know that i am a male

Trish said...

I've purged so many outfits and wigs while attempting to halt my transvestism, but to no avail. I guess this is what I'm going to be. So I might as well begin taking it to the next step: publicly displaying my sorry self as a transvestite. Are there any men who would be willing to film me as I shame myself?

http://db.tt/LgoTcDm5

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