Gays Erotic Story


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How I Became a Ladyboy
by Girlie Ellender (

* How I Became a Ladyboy*

An adolescent boy discovers a penchant for cross- dressing. One afternoon, while masturbating in his mom's high heels and lipstick, he is caught by her boyfriend. That's when the boy and the boyfriend proceed to have sex. During the course of which the boy is beaten and raped.

I've been getting hard-ons and playing with my dick almost since I can remember. I recall one fantasy in particular that I indulged in when I was 7. It involved a cute little girl in my catechism class. Her name was Lucinda. She was a bouncy little blonde, and my fantasy involved stripping her nude and whipping her with thorns. I had such erections over that.

I was pretty much of a sissy growing up. I never knew my father. My mom told me that he had died soon after I was born, but I was later to discover that my mother had never married, and that the space on my birth certificate for "Father" was typed: "UNK."

Mom was basically a slut. She worked a succession of factory jobs, and had a succession of boyfriends. I used to watch her on Friday nights in her tight dresses and high heels, applying her lipstick before going out for the night. Sometimes she would bring men home, and later I could hear them making love in her bed.

When I was around 12, Butch moved in. We lived in a triple-decker apartment house on the east coast. Our apartment was on the first floor. Butch and Mom would sit around drinking and watching porno movies. Then they would fuck, usually in Mom's bedroom, but sometimes right there in the living room. I began masturbating then, thinking about them having sex.

Butch was in his late 30s. He had spent time in prison, and though he wasn't very tall, around 5", 8", he was heavily muscled and had lots of tattoos. Sometimes he would grab me and pretend to wrestle with me. I remember feeling really turned on by the feel of his arms around me. He kept a stack of fuck magazines in the basement.

Sometimes I'd sneak down and watch him masturbate while looking at the pictures in the magazines. He would strip naked and jerk off for hours sometimes, before finally blowing his load all over his hairy belly. I could see the semen on his fingers. He had a big cock; I'd say about 8 inches.

After a few months, I began going to the basement to jerk off to Butch's magazines. The girls were gorgeous and so were the men. Looking back on it, I realize I was identifying with the women in the photographs. Once, I was in my Mom's room, and on impulse I took her lipstick and applied it to my mouth. It was a cherry red and when I looked at myself in the full-length mirror I was shocked.

I looked like a woman! Not a girl, but a sexy woman! I got an instant hard-on. My hair was shoulder length then, and blonde. I immediately stripped nude and grabbed a pair of Mom's high heels. Oh fuck! I was as sexy as any of those bitches in Butch's magazines. After that I never jerked off unless I was in heels and lipstick.

One rainy afternoon, when Mom & Butch were at work, I went down to the basement to jerk off. I stripped nude and stepped into the pair of 4-inch heels I had appropriated from Mom's closet, & applied a thick coat of sexy red lipstick. Then I lay back on the ratty old sofa to jerk off. Occasionally I would get up and strut around in front of the big mirror. I was doing this when suddenly I heard a long drawn out wolf whistle, like the way construction workers whistle at girls in miniskirts. I froze, my heart beating wildly. Then Butch stepped out from behind the doorway. I tried to grab my robe from the couch to cover myself, but Butch was quicker. He snatched it out of my hands and threw it behind him. "Please, Butch," I begged. "Don't tell Mom, please!"

Butch was rubbing his crotch and looking at me strangely. He shook his head. "Like mother like son," he said. "Or should I say daughter?"

"Butch, could I have my robe please?" I asked him.

"Why would you want to cover up that beautiful body, girl?" Butch said. "I mean it, you are fine as fuck."

Before I could answer butch stripped off the tight t- shirt he was wearing, and stepped out of his jeans. He pulled down his jockey shorts and kicked them aside. His dick was rock hard. He crooked his finger toward me. "C'mere," he said.

I walked toward him, my head reeling. When I got closer he grabbed my arm and pulled me close up against him. I gasped as my soft nude flesh came up against all that hair and muscles. He held me close, crushing me up against his bare chest, his big hands squeezing the flesh of my ass. He bent his head and his mouth found mine, his tongue snaking into my throat. Oh god, my dick was hard again. My hand reached down and felt of his erection. "Oooh, yesss, baby," he moaned.

"You gonna to suck it? That's right, baby, get down and suck my cock," he said, pushing me by the shoulders to my knees. His hard cock brushed up against my cheek. I took it in my hand and the head was close to my mouth. Cum was forming on the head and I flicked my tongue and lapped up the beads of pre-cum from his cock. 'MMM! Cum tastes good,' I thought. I engulfed the entire head of his penis into my mouth and began sucking his cock.

He was groaning in pleasure as I ran my mouth up and down the entire length of his glistening cock and sucked his balls up into my mouth. Butch's hands were entwined in my blonde hair and he was using his fist to control the movements of my bobbing skull. He sat down on the sofa and lifted his legs, exposing his hairy anus. I wasn't sure what he wanted. "Eat my ass," he said. I put my face close and drew back. "What's the matter?" he said.

"It stinks," I told him. He still had his fingers entwined in my hair, and he pushed my face up into the cleft of his ass.

"You love it," he said. And he was right.

It did stink a little, but the intermingled odor of sweat & the faint scent of shit had an aphrodisiacal effect on me, and I began eating out his bare anus with abandon. I must have eaten his ass for 10 minutes – I mean – my fuckin' jaws were getting numb, when Butch told me to suck his balls and cock some more. I was knobbing his cock really hard when he pulled my head back, his saliva glistening penis withdrawing from my hungry yap as he did so. "Why, Butch?" I whimpered. I had assumed that Butch wanted to cum in my mouth and I was working really hard for that reward.

"Because, baby," he said. "I'm gonna fuck you." And he pulled me up from my knees so that I was lying up on his big chest. Again his mouth found mine and our tongues were snaking around one another.

As we kissed I was squeezing and choking on his erect cock. One of his big hands was on my ass. He removed it briefly and put one of his fingers in my mouth. "Get it wet," he whispered hoarsely, and I sucked his finger, coating it with saliva. He reached down and I felt the finger at my anus. Butch began kissing me again, and his finger worked into my ass.

Fuck! I felt like such a fuckin' whore! I mean, I was wiggling my ass on his thick, calloused finger, just like any horny puta! Butch kept whispering, "You want some cock, baby?" And I kept whimpering, "Yes, Butch, I really need some cock, daddy!"

Finally Butch said, "Ok, sissy. There's a tub of grease in the dresser over there. Go and fetch it to me."

I stood up and started to step out of my heels. "Uh huh," Butch said. "You keep the fuckin' high heels on. I want to watch you walk in them. And put some more lipstick on."

I applied a fresh coat of lipstick and walked as sexily as I could across the room to the dresser where Butch said the grease tub was. I opened the drawer and saw it. It was a big jar of Vaseline. The jar was dirty and had no cover. It was half empty. And there were pubic hairs all over the Vaseline. I was thinking, oh god! This guy is gonna stick that big thing in my ass! I just know it's gonna hurt! But I wanted him to fuck me so badly that the thought of the pain I was going to have was outweighed by the desire to have this man inside of me.

I walked back to where Butch was sitting straddle legged on the sofa. I could hear the rain coming down outside. Butch had his dick in his hand and was jerking off. As I got near him he reached out and ran his hand up and down my bare legs. I shivered with anticipation.

"Damn, sissy!" he said. "You got some silky ass legs!" He laughed. "Fuck! Do you know what they do with people like you in prison?"

I didn't answer; I was enjoying the feel of his rough, strong hands on my silky legs.

"Get down and suck my dick some more," he told me.

I didn't hesitate to obey him. The feel of his erection in my mouth was heavenly! As I blew him he took a couple of fingers full of the grease and reached back to finger fuck my ass. Now it felt wonderful! The Vaseline made his finger slide in and out, right up to his big knuckles. I was wiggling my hips as he finger fucked me.

Finally he said, "Ok, sissy, grease my cock up."

The grease tub was sitting next to him on the sofa. I took a gob of the grease in my fingers and coated his penis with it. Butch gave me an old towel and I wiped my hand off. "Get up on the couch," Butch said, instructing me to kneel on the sofa, facing the backrest.

Butch climbed up behind me and began kissing on my neck and bare back. I could feel his big strong arms around me as he was kissin' on me. I could feel his dick pushing up between my thighs and oh! I wanted it in my ass so badly. I could feel Butch's sandpapery face up against mine from behind. He was whispering in my ears as he nibbled on the lobes, "I'm gonna fuck you, you little ho!"

His words thrilled me. I reached back through my legs and grabbed hold of his erection. "Oh FUCK! It was SO fuckin' HARD!" I guided the head of his penis to the mouth of my hungry anus, and he began to push, to thrust.

Suddenly it found the hole and tore in. "OH – FUCK!!" I screamed in pain as the head of his dick, as big as a plum ripped into my ass hole. I began to instinctively scramble to get off the sofa but a big muscled arm got me in a headlock, while his other arm grabbed my left arm in a wristlock that was so painful I forgot about the pain in my ass. When I stopped struggling he let go of my arm, but kept me in the headlock.

"Don't FUCK with me, bitch," he growled in my ear. He got back on me and again I felt the probing erection searching for my hole. I tried to press my legs together, but Butch shoved his knee in between my thighs and forced them apart. Then I felt a searing pain as he tried to push the head in. I squirmed violently and screamed.

That's when he hit me, hard, with his fist on the side of my head. So hard I saw stars. A knot quickly rose, shutting my right eye almost completely. Then he hit me again, just as hard in the mouth, causing my upper lip to swell grotesquely. Then he mounted me like an animal, like a steer mounts a cow, and forced the head of his cock into my ass. I was screaming, but no one could hear because Butch had his big hand clamped over my mouth.

He was grunting like a savage animal as he worked his throbbing cock inch by inch into my ass. Finally, when he was in me balls deep, he relaxed the headlock and put his arms up under my arms and grabbed me by the tits, pulling me close to him, my back up against his big chest. He was growling and slobbering on my ears, neck, and bare back. Slowly he began to fuck me, all the way out, all the way in. At first it hurt like hell, but as he increased the tempo of his strokes, it began to feel good.

As Butch ass fucked me his hands were all over me – my tits, my belly, my bare legs – everywhere. My dick was hard again and I was wiggling my ass to meet his down stroke. What a WHORE! I was totally writhing naked in my boyfriend's big muscley arms as he raped me on the dirty sofa.

Butch was fucking me and ramming his dick into me so hard you could hear the slap of bare flesh on bare flesh. His dick felt like it was actually swelling inside of me, getting bigger, thicker. I began to use my ass muscles to bear down on his erection. On every down stroke, when his cock was buried up to the balls, I would squeeze down and grip his cock with my ass muscles, and when he withdrew I would maintain my grip, so that I was literally milking him with my anus.

Finally, his entire body tensed and I could feel his penis jumping and twitching uncontrollably inside of me. He had his arms around me under my arms and he yelled loudly and ejaculated deep into my belly. As he came his arms tightened around me and I thought my ribs would crack. I began milking his cock from inside and Butch was shouting out in hot pleasure as I milked every last drop out of him into me.

Slowly Butch relaxed his grip and lay exhausted on my back. Then he eased his big greasy cock out of my anus. It felt exactly like I was taking a big, constipated shit. I turned around and Butch took me in his arms and kissed me. "Oh, baby," he said, kissing my battered face. "Why'd you make me get so pissed off? I'm sorry baby, I promise I'll make it up to you, honey. I swear!"

"Oh, Butch, I love you so much!" I said, crying. "I'm sorry, too, honey," I told him. I lay in his arms on the sofa for the rest of the afternoon, and just before Mom came home, I gave him a blowjob.

We made up a story for Mom to explain away the beating. Butch told her that I had gotten in a fight with a bully at the mall. "You should have seen the other guy," Butch told her, mussing my hair.


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