Sissy PRIDE!

I'm just sitting around, painting my toenails, and thinking how blessed I am to have been born a sissy. Of course, it wasn't always that way – I wasted so much of my life trying to fight my reality. It wasn't until I went through puberty and I saw that I was not developing physically like the other guys my age that it really began to concern me. I saw them, with their voices deepening, their jaw lines becoming bigger, hair on their arms, chests and legs, and all that, while I still had my heart shaped chin and small boned delicate features.

And while they were putting on muscle, my skin stayed soft and – worse – I began to grow breasts! Mom took me to a doctor, and she said that my body was producing estrogen, and not testosterone. She advised that we wait and give it time to maybe sort itself out. It never did. I was SO ashamed of myself. I'd look at my bare body in the full-length mirror and what I saw was a girl, a girl with a small penis. I really hated myself. I also began experimenting with cross-dressing then too.

I remember the first day it happened; I was 18. It was almost as if something was guiding me. Mom was at work and I was lying around naked and jerking off to sex magazines. I used to convince myself that I was straight because the girls in the magazines made my dick hard. Anyway, after cumming on my sheets, I began wandering around the apartment and found myself in Mom's room. I began rummaging around in her dresser and opened her panty drawer. Mom was single, and at that time was in her late 30s. She was always sexy and had a lot of boyfriends. On impulse I picked up a pair of her lacy black panties and put them on. I could feel my dick stiffening. I went to her closet and selected a pair of 4-inch high heel pumps and slipped my small boned feet into them. Then back to the dresser, where I grabbed a red lipstick and applied a generous coat to my full, pouty lips! OH MY GOD! I was a sexy WOMAN! I couldn't believe it. I masturbated furiously and shot cum all over the full-length mirror! I was immediately disgusted with myself and couldn't get the underwear, shoes and make up off quickly enough. But, as you probably know, this began a routine I would follow - off and on - for the rest of my life.

My first sexual experience was homosexual. He was an older guy who hung out with us. Most of the guys looked up to him because he was older. He was always pretending to wrestle with the guys, and some of them joked that he might be gay! He didn't LOOK gay to me. He was big – about 6, 2 – and had a lot of muscles. He was half black and had spent a couple of years in jail for something. He came across as a tough guy. A lot of times I caught him checking me out when he thought I wasn't looking. One time our eyes locked and he smiled and I turned beet red and looked away. After that all I could think about was Jay – that was his name – Jay.

I began going over to his apartment by myself, and making excuses about how I thought the guys were there, even though I knew damn well they weren't. Jay used to let us hang out at his place. Sometimes we'd watch porn. One night I was there and Jay put on some interracial porn. It was a hot night and Jay had the windows open. It was dark, and only the lighting from the television cut the darkness. Jay was on the sofa next to me. He was just wearing a pair of boxers and I had shorts and a t-shirt on. The porno was really hot. A cute blonde whore was having sex with 8 big black men! I heard Jay sigh loudly and when I glanced over, he was squeezing his huge boner through his boxers! He saw me looking and he took it out. It was fuckin HUGE! I looked away – intrigued and embarrassed. "Feel of it, Keven," he said, reaching out and taking my small hand and bring it to his erection.

He groaned loudly as my fingers encircled it and squeezed. "Oh, KEVEN!" he said. "Stand up, honey."

I stood up and he told me to strip for him. Now I was horny too, and I stripped off my clothes and stood completely naked in front of him. "Fuckin' BEAUTIFUL body!" he exclaimed, as his big rough hands went to my buttocks and he ran his hands up and down my bare legs! I shivered and put my hand on his hairy thick wrist. He raised his buttocks up off the cushion and slid his boxers off. What a MAN! All big naked MUSCLES! So fuckin' HANDSOME!

I got down between his knees and ran my fruity little hands all over his BIG HAIRY LEGS, and bent my head to give my first blowjob. I had seen enough porno to know what to do, and I eagerly began sucking Jay's sweet hard cock. I was so eager that Jay had to stop me a few times. "Watch the teeth," he admonished. Gradually I learned to ease up and after a couple of minutes I felt his legs trembling and he shouted out, flooding my pretty mouth with cum juice!

We had sex 4 more times that night. No fucking, just a lot of making out naked and me sucking his cock. I awoke in the morning with the bright sun in my eyes, and my sweaty bare body next to Jay's I was half lying on his chest and I was shocked. What the fuck had I DONE?? I'm not a QUEER! But I knew now that's exactly what I was. Jay and I went out and he bought us breakfast at the diner. We didn't talk much, just kept looking at each other. We drove around and got back to the apartment around 8 p.m. As soon as we got into the staircase and out of sight of the public, I felt Jay's arm encircling my waist, his hand on my ass. I smiled to myself. I was getting horny again.

We put on some more porn only this time there was no pretense. We both got naked and I curled up next to my boyfriend. We watched the video, my hand playing with his cock. We began making out and I knew what I wanted. I wanted to suck that sweet cock!

Jay picked me up, like I didn't weigh anything, and carried me into the bedroom, placing me gently on the mattress. I wanted to blow him badly, but he kept telling me, "later." We made hot love and romance and Jay's thick fingers were in my ass hole. I was squirming around. I wanted to be fucked! "Oh, Jay – wanna fuck me, honey?" I begged.

He lay back, naked and muscular, and pointed to his cock; "Suck it first, sissy," he said. Well, I didn't have to be told twice. I was all OVER that hard boner! As I blew him he kept feeling of my bare ass and legs. "You ready to get fucked?" he asked me.

I was MORE than ready. The room was dark and the windows were open, and I could hear the cars and people talking on the street below. The only light was from the bathroom, which adjoined the bedroom. "There's a tub of grease in the medicine cabinet," Jay told me. "Go fetch it."

I got up and went toward the bathroom. Jay was saying things like: "Oh, BABY! That is so fuckin' SEXY! That's it – walk like a girl, sissy! Wiggle that ASS, girl!"

You have NO idea how his words inflamed me as I walked to get the grease – the grease that was going to enable that big hard cock to go in my sexy fuck hole! I grabbed the jar of Vaselino and looked at it; there were black pubic hairs on it – JAY'S pubic hair!

I walked as sexy as I knew how to put on a show for Jay. He took the tub and set it on the bed. We began making out again and I was suckin' his cock and hairy balls, when he took my arm and pulled me up. "Get on your hands and knees," he said. I obeyed him, trembling with a mix of fear and anticipation. I felt him mount me from behind, like a big animal on his female, his erection poking near my anus. Jay had lubed me up good when we were kissing and now I shook as I felt the big plum head of his cock begin pushing into the pink, moist, toothless mouth of my greasy anus.

Jay was kissing on my neck and bare back, his big hands feeling up my soft belly and tits. Jay LOVED my tits! He told me that my tits were bigger and better shaped than his ex wife's! Then I felt his arms around me flex and I was being held really tight. Suddenly I felt a discomfort that quickly turned into almost unbearable pain as the head of his cock began penetrating my ass cunt. I tried to shift my weight and twist away from his grasp, but I couldn't move.

That's when he raped me. I call it a rape because, even though I had not only agreed to it, but actually begged him to do it, I now was unable to refuse. Jay was no longer a civilized man; now he was an animal with a hard dick, obeying the call of nature – IF you could call what we were doing on that bed, "natural!" He was grunting and groaning like a beast and I felt him take my slender neck in his jaws, felt his teeth bite into the soft flesh of my neck, and suddenly – woosh – he sank into me, balls deep.

For a few seconds I didn't realize what had happened, though I know now that Jay had made it past the tightly clenched "jaws" of my rectum, causing them to relax and engulf his entire cock. He was in me now and he rested on my back – just briefly – before beginning to hunch me - to frog fuck me with long, slow strokes. Now I was in absolute HEAVEN! I reveled the sexy thought of being naked in a man's arms, wiggling my naked buttocks up against his groin to meet his increasingly quickening thrusts. I could feel his cock pushing up against my bladder, and it made me feel like I had to piss. Now he was reaming me with jack hammer like strokes, his big nuts slapping up against my thighs. Suddenly he tensed, and said: "Oh, baby – I'm gonna CUUUUMMM!" I felt his groin mash hard up against my bare buttocks as he emptied himself deep into my bowels. He rested himself on my back, breathing heavily for a few seconds.

"Didja cum, honey?" I asked over my shoulder. I felt a whoosh of breath against my face as he rose and eased his greasy cock slowly out of my ass hole. It felt almost like I was taking a big SHIT! As the head popped out I had a feeling like I had to fart. I tried to stifle it but it came out – not loud – like I was expecting, but bubbly and I felt warm semen running down the backs of my thighs. My first cream PIE! I felt totally like a sexy WOMAN! That's how I thought of myself – not as a man who just got fucked by another man – but like a feminine little missie, just cherried by her hot lover!

Turns out Jay and I were on the same page. He told me that in the joint guys have sex with sissies like me as women substitutes. He said that as long as you don't suck another guy's cock, or take it up the ass, you're considered straight. As long as you're fucking a shemale, it's not considered a homosexual act. Only the sissy was viewed with a mix of scorn, and lust. He told me that if we were in prison together, I could make him a lot of money, because I could actually pass as real female. At first I was a little hurt by the suggestion that he would whore me out, because I thought we were in love – I knew that at least I was in love! But he explained that if a bitch truly loves her man, she will do whatever he asks of her.

After a few months Jay broke parole and went back to prison. I promised to write and visit him – and I did – for a couple of months. But gradually, away from Jay's influence, I began to try to reassert myself as a male. This went on for a few years. Every so often I'd lapse and end up blowing some stranger in a men's room, but for the most part I played it straight.

I discovered from viewing porn online, that Asian women turned me on. I still had yet to have sex with a woman, but I wanted badly to be a man. I began visiting online Asian dating sites, and that's where I met Jinky. She was interested in marriage. I know - everybody told me that she was just using me to come to the U.S., but I had made up my mind. Eventually I went to the Philippines, where we not only met for the first time, but also were married. Then I went back to the states while Jinky did the immigration paperwork. We still had not had sex because Jinky said we must wait until we live together in America. It didn't really make sense but I didn't mind, because the prospect of having sex with a woman made me very nervous.

When Jinky arrived and we actually did have sex, it was a mess. I was so nervous. We finally did it and I felt like a real man for the first time in my life! Jinky loved to fuck and soon my dick was sore! But it wasn't long before I would fantasize being with a man when Jinky and I were having sex. Jinky told me later that she made me for a queer the minute she met me, but put aside her concerns because she wanted to come to America.

I mean, we actually got along pretty well. We seemed to be on the same page in most things. For example, Jinky was extremely sexy and a real girly-girl. Women like her are most compatible with really manly type men – which I most definitely was not! She liked to dress very provocatively, something I actually encouraged, because, as I see now, I was trying to live vicariously through her. She would wear the most revealing butt baring short shorts with high heels and halter tops. It could be embarrassing sometimes, like if we were out and guys would hit on her right in front of me. And we did have some arguments about it because I told her that she shouldn't be so responsive – it disrespected me as a man. But she would always laugh incredulously and say, "What? You're the one who told me to wear that outfit. What do you expect?" Then we would go in the bedroom and fuck. I'm a babbler in bed – I love sex talk! That's when I'd bring up whatever guy had hit on her and ask her stuff like, did she think he was handsome – stuff like that. And she would always say, "Of course! Did you see him? He was so fuckin' CUTE!"

Jinky was honest about telling me that she wouldn't mind dating other men. I was shocked at first, but she explained that in her culture it was accepted and really not considered all that unusual. Then the idea of my sexy little wife fucking other men began to turn me on, and I actually began going along with her when she talked about it, even going so far as to give her subtle encouragement. Jinky had been a nude dancer in Japan, and when she suggested that she apply for a club job, here in the U.S. I initially refused. But then I lost my job, and I was no longer in a position to tell her no.

When Jinky was at work I began masturbating to online porn – mostly interracial. It wasn't long before I began going out to adult video stores, where I had sex with guys in the video preview booths. One night, a guy I met in the arcade asked me to accompany him to a gay bathhouse. I had sex with ten guys that night - blowjobs and bareback anal sex! I didn't really feel guilty, because Jinky was honest about how the dancers made their money - having sex with the customers at the club, in booths! Eventually she entered a relationship with a guy named Neron, a bouncer at the club.

As time went on, Jinky began spending less and less time at our apartment. Her work hours were long as it was – she'd leave around 4 p.m. and come home about 4 a.m. That is, when she DID come home. As she got deeper and deeper into her relationship with Neron, she began staying at his crib, and maybe I'd see her once a week, if that. Eventually Jinky found my gay oriented magazines, and used it as an excuse to dump me and move in with Neron.

As time passed we became friends again. By that time I was living full time as a woman. Because I can pass as a woman, Jinky and I would spend time at malls, shopping and talking about MEN! It was sexy when we would flirt with men at the mall. It never went any further than flirting though, because the last thing I needed was to have some shocked guy reach down and find out that the "girl" he's been kissing was really a BOI!

Oh well, It's almost 3 p.m., and on Sundays, I like to get to the video store between 3:30 and 4. I'm wearing black tights, high heels, and a jeans jacket tonight. When I'm in the video arcade I usually just wear heels and a string bikini. I have a collection of these lacy string panties of various colors that I buy at Adam and Eve. They have a sale bin and I always grab a few every time I shop there. I like them because men enjoy stripping them off me when we fuck.

Last night I had this married guy – a real dreamboat – and he was really nervous. He's been coming in for a few months now. At first he wouldn't even let me blow him! He kept babbling about being married and didn't want diseases – "blah, blah, blah!" But just by virtue of his inability to stay away, I knew it would just be a matter of time. Last month he agreed to jerk off while I watched. I asked him if I could masturbate him but he said no. So I got down like I would if I was gonna suck him off and watched as he jerked off. When he was ready to cum I told him to aim at my mouth and shoot it in. He did, and there was a LOT of really sweet cum - which I gobbled right down.

A few nights later he had had a few drinks, and he agreed to let me blow him. He wouldn't undress, just took it out of his pants. I gave him the best blowjob he had ever had in his life! That's what he told me! I knew he was mine now. He began showing up every night, around 8 p.m. Last night, we fucked! He had been drinking again – I could smell it on his breath – and he was really relaxed. He agreed to get naked with me. All I had on was my high heels and a pair of those purple string panties. He is a FINE ass MAN! He's about 35, 6 foot 3, nice hairy body, muscley legs – all he had on were his work boots! I was sucking his cock and balls and playing with his hairy legs – you know – just running my hands lightly all over his legs – and it got him SO fuckin' HORNY! "You want to fuck me honey?" I asked. I stood up and got up close to him. He grabbed me and kissed me – right on the mouth. I was squeezing his cock in my hands. "Let's fuck," I whispered.

He kept telling me no, but he finally asked me if I had a rubber. I did, and I really wanted to get fucked by him badly, but I took a chance and told him I didn't. I wanted THIS big hunk BARE BACK! He told me, "No rubber - no fuck."

I turned and rubbed my ass up against his hairy body, reaching behind me and grabbing his hard dick and rubbing it between my ass cheeks. "Come on, daddy – you want to fuck me! Honey, I KNOW you want it!"

I felt him strip the panties right off my ass and bend down to take them off my shoes. They got caught in my left heel, and he got up behind me and I felt him so horny all over my nude back. His hands were EVERYWHERE - feeling up my silky legs and titties! Telling me what a fine ass bitch I was. I stuck my ass out and grabbed his cock and placed it up against the wet pink glistening mouth of my anus. I always keep myself lubed up, and his nice big cock just glided right in! He kept babbling about his wife, how he shouldn't be cheating on her, and I was thinking: ' Fuck HER! you're MY man now!'

I was standing facing the door, my legs spread wide, slightly bent over, as he began fucking me and slobbering all over my ears, neck and back – like some big ANIMAL! He fucked me until he couldn't stand it, and he pulled out. "Get down! Get on your knees!" he said in a choked voice. I knelt between his legs and he released his grip on the base of his cock and shot string after gooey string of hot SNOT – all over my pretty face!

There was so much CUM! I had his snot dripping from my nose and chin, and down my forehead! He began to laugh nervously, happy that I had made his fantasies come true. He told me that in a million years his wife would never allow him to fuck her in the ass and cum all over her face like that. He had shown me a pic of his wife, and she was fine – very sexy – but what these bitches don't understand is, that if they don't cater to their men – some bitch like me WILL!

After Jinky left me for Neron, she got pregnant by him and gave birth to a beautiful half black - half Filipino baby girl. When she got too big to work she went on welfare. Neron broke up with her but still spent time at her place, to see his daughter. Jinky now is the mother of 4 half black kids, all from different baby daddies, and they all call me "Auntie Finesse!" Jinky's still fine and sexy, although she has put on a little extra weight, and has tattoos all over her body. When we were together she had just a neck tattoo that said, "Andre," in cursive, and a larger Yakuza tattoo on her back.