Growing up I had a strange fascination with women's clothing. We lived in a high rise apartment in downtown Detroit with a balcony overlooking the Detroit River and a kaleidoscopic view of Windsor. My parents had divorced when I was still in kindergarten and I have very few memories of my father. My mother was an executive in the banking industry, quite rare for a woman in the 60's. On days when I was home from school and she was at work, I found myself picking my way through her solid clothes hamper, sniffing and licking her soiled panties and hose, her shoes, before dressing up in her clothes and string at myself dressed up as a woman in her full-length mirror. As I grew older, as an adolescent, I would even paint my toenails with her nail polishes, usually various shades of red, but also coral and tangerine, and add mascara and lipstick. With my longish hair and hairless chest and legs, I could have easily passed as a woman if it were not for my penis, which at times like these stood at full attention, flopping to and fro as I walked along in circles wearing my mother's sexy sandals and open-toed mules, unable to stop staring at my sexy reflection, endlessly fascinated by this female self that I kept hidden from my mother, my friends, teachers, and the world at large. I would slowly masturbate myself all the whole staring at the reflection that mirrored myself.

One morning, as I pranced about naked before the mirror in and out of my mother's bedroom, I heard the sound of a man clearing his throat, and when I turned to look, there was Arthur, the middle-aged black apartment janitor standing on some scaffolding outside on our balcony, with a wiper in his hands. He had been washing windows, and had come upon me in all of my sartorial glory, long hair pulled back in a pony tail, eyes and face fully made up, my feet clad in my mother's spike heeled open toed mules, my lips and toes garishly colored a fire engine red, my cheeks rouged, smoky eye shadow around my eyes, and my long, thick cock bounding this way and that, pointing at the ceiling.

I had known Arthur my entire life. He used to give me horseback rides, shoot baskets with me in the basketball court on the apartment complex, ask me how my education was going, how my mother was doing, what I wanted to be when I grew up. Arthur had been a foundation of my life, always friendly to me, always there with a smile and a pat on the back.

Now our eyes locked. I felt like a grasshopper trapped in a spider's web. Arthur gestured at the balcony doors and smiled. I stood frozen to the spot, unable to move, unable to hide, unable to bury myself, unable to make him unsee what he was clearly staring at. Arthur grabbed at the bulge in his pants and gesticulated that I should open the balcony doors and let him in. I was frozen with fear and self-loathing. The was to be my secret. No one was to know the strange desires that lurks in my heart, but now Arthur knew, now the desires were no longer hidden, no longer secreted. The fear made my glorious erection fade quickly until my large penis hung limp between my thighs. Arthur was talking to me know, but between the thick glass doors, the blowing wind outside and the deafening roar in my ears, I couldn't make out what he was saying. Yet, there was no mistaking the leer on his face. It was evident from that leer that he wanted me, sexually. That he viewed me as a sexual plaything, a sexual slave to satisfy his carnal desires. I could make out that he was sporting a large thick erection that was bulging from his crotch upwards and to the left, and just in case, I couldn't make it out, Arthur pulled at the monstrous erection, smiled and nodded again at the door.

Wordlessly, nakedly, I walked over to the balcony doors and unlocked them. Arthur turned the handle and entered our apartment from the balcony. "I couldn't help but see you through the balcony doors," he said in his distinctive, resonating bass voice. "Look at you! God, if I didn't know better, I would have mistook you for a woman. A beautiful woman, at that." He gestured with his hand for me to turn so that he could see the rest of me, and I turned slowly 360Ëš until I was again facing him. Arthur smacked his lips and said, "God, but you look so damn good." He unzipped his green colored Dickies janitor pants, reached into the crotch and pulled out the biggest cock I'd ever seen, the thick, veiny shaft and balls, a dark chocolate brown, the head of his cock pink and mushroomed and glistening.

Arthur's was the first erect cock I'd ever seen other than my own, It was magnificent in its turgidity, its regality, its massive presence. I stood transfixed staring at it, unable to look away from it, as if my vision had been entrapped, as if it was tied magnetically to that throbbing, muscled anaconda, as if it were calling to me, and I was powerless before its majestic presence. Arthur stepped over to me and gently pushed down on my quivering shoulder, gently but forcibly pushing me down to my knees so that his cock now danced before my eyes, his huge hanging balls swaying as if laden with an uncomfortable load. He moved forward just a bit so that the glistening head of his penis brushed against my velvety soft lips, wetting them with the slime of his pre-cum and whetting my desire to suck him. "Suck it," he murmured, "Suck my big black dick," and as if from his lips to God's ears, I opened my mouth and wrapped my lips around the mushroomed head of his cock and began sucking it. Arthur let out a series of groans, "Mmmmm. . . yeah, that's it. . . Suck it, baby. . . Suck my cock. . . Aw, fuck yeah, suck it. . ." as I stretched my jaws further and further apart, allowing more and more of his cock to enter my mouth, slide against my tongue, and lodge at the rear of my throat. It was difficult to suck him as his cock was larger in circumference than my mouth. His cock tasted smoky, and musky. He placed his hands at the back of my head and began thrusting his cock deeper and deeper into my mouth until the head of his cock entered the rear of my throat and choked me. Arthur pushed forward until his cock had entered further and further into my gullet and then he began slowly fucking my stretched open mouth as if it were a woman's pussy. All the while he held my head as he fucked faster and harder, his thick erection serving as a battering ram of flesh, of muscle, a conquistador. As he fucked my mouth and lips and tongue and throat, Arthur moaned and groaned, until at the end he was grunting, and then in an explosion he shot volley after volley of thick white cum deep down my throat, on my tongue, in my mouth, massive dollops of his seed, seemingly everywhere, and then gradually his thrusts decreased until he had shot out all of his seed and he pulled his semi-hard penis out of my mouth, wiped off its slimy head against my lips and cheeks, and stood there, his face smiling, sweating, sated. "Now that was the way I like having my dick sucked."

I kneeled before him, my mouth filled with his cum, my lips and face smeared with his cum, cum in my hair and on my chest. I was exhausted, my lungs burning at the effort, at the inability to breathe as he was thrusting deep into my throat. Arthur pulled me up by my shoulders and said, "Let's go inside," before walking me back to my mother's bedroom. He laid me down on my mother's perfumed bed, then pulled off his work shirt over his head and pulled off his pants, then naked, with his long thick penis swinging to and fro, he rummaged around in my mother's dresser drawers until he found what he was looking for: a bottle of Vaseline. He pulled off the blue top and dug two meaty fingers into the yellow colored Vaseline and then removed them slathered in Vaseline. He applied the thick, slippery substance to his massive cock, and then thrust his Vaseline covered fingers at the opening between my butt cheeks, slowly working first one and then the second finger into my rectum. He yanked my legs up over his shoulders and then pushed the head of his now erect cock against my anus and pushed. I felt this intense pressure and then as his cock entered me, a blazing lightning bolt of fiery pain, as if he had pushed a thick cherry red hot poker up my ass, and the further he pushed, the deeper his cock worked inside of me, stretching and even tearing the tissues there, until the pain was blinding me, and yet he was relentless, fucking me, first slowly, and then faster and faster, deeper and deeper, until I felt myself opened wide, yielding, vanquished, his. The fucking was relentless, seemingly endless. The fire stretched from my anal opening up through my rectum. I could feel his pounding penis deep, deep inside of me, deep inside my gut, a part of the reality that I could no longer deny. I don't know how long the fucking lasted but finally I felt his cum inside of me, an endless stream of goo, alleviating but not putting out the fires raging inside of me. When he was done with his thrusting, he pulled out and suddenly I could feel his absence, I could feel a sense of loneliness no longer having his penis deep inside of me, loneliness and relief. I was bleeding from my rectum and later when I looked at my asshole in the mirror, I could see that it was torn and that the flesh was red and pulpy and violated. He wiped his dick off on the bedspread, and I could see the smear of blood and semen and shit. He quickly and wordlessly got himself dressed again, and walked over to the balcony doors, before turning and telling me, "That was top of the line c**t you've got there. Every chance I get, I will be tapping that ass of yours." He winked at me lying naked on the bed, "Bye. . . for now." And then he walked onto the patio and back on his scaffold. I had a few hours to wash out the stains to my mother's bedspread, and her sheets where the blood had seeped, to wash off the face paints and remove the paint from my toenails, to dress back as a boy, to administer cooling salves to my asshole, to endlessly gargle with mouthwash to try to kill the lingering taste of his cock and cum, and to try to remove the memories of my morning. I successfully washed out the stains, cleaned my face and fingernails and toenails of the eye shadow, mascara, lipstick, rouge and nail polish, and although I walked like John Wayne after a hard three-day horseback ride over the course of the next week, and every time I took a shit, my asshole burned like it was on fire, my mother didn't know what I'd done, or what had been done to me. But I was never the same after that. Whenever Arthur saw me in the hallways of the apartment, he would wink at me and leer. And if I was alone, he'd ask me if my mother was home and if she wasn't, he'd have me go back up there and dress for him and wait for him, a slave girl awaiting her conquering hero, and when he'd knock, I would open the door, and in he'd stride and I would prostate myself at his feet, sucking his cock and then lay in bed, on my back or on my side or on my stomach with my ass raised and he would mount me, a stallion taking his mare, with towels beneath me to soak up the remnants of his orgasm and the trickle of blood that he'd leave in his wake. I was irrevocably Arthur's fuck slave, and the knowledge of this filled me with dread and excitement, fear and loathing and desire.

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Anonymous

by Anonymous on Mar 11, 2019 at 9:45 AM

That's one heck of a way to loose your virginity.
The maintenance guy at the apartments I lived at with my mom fucked me. He was there fixing whatever my mom told him needed fixed. I was only in my tighty whities. Didn't know he was gonna show up.
He fixed what he was supposed too and afterwards we talked. Then his pants got unbuttoned and pulled down to expose his tighty whities. Only he had a big bulge in his and a very big hard cock!
His tighty whities got pulled down and his dick sprung out, it was long, thick and hairy.
He had me suck it till he asked where the Vaseline was. He came back from the bathroom, took a big glob out with his finger, pulled my tighty whities down and started fingering my ass. After about 5 minutes of that he pushed his whities down to his ankles and stuck his dick head in the Vaseline till it was coated.

Slowly he pushed his cock in, it hurt. He fucked me for a good 10 minutes before he cummed in my ass. He let out a loud moan as he cummed. Then he held his pants and underwear up around his thighs as he walked to the bathroom where he cleaned his dick off in the sink.
He came out of the bathroom drying his dick off till he tossed the towel to me and pulled his tighty whities up. He has a big soft dick that bulged like crazy. He told me to wipe my ass off before I put my briefs on.
My ass was sore the next few days. But once a week I'd typically get fucked by him.

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