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How I lost my virginity to a Man, and became a total slut!


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Posted (edited)

I'm 23 years old now, and have been with many men, but the man who showed me that I was gay will always have a special place in my heart. His name was Ryan, and he was a neighbor who lived just down the block from my family. We'll pretend his last name was Thomas, 'cause I never called him Ryan. only Mister 'Thomas'. I was still living at home, just out of high school and yes I was 18 :P. In my younger days I would sometimes mow his lawn for him or rake leaves, shovel snow, stuff like that for cash because, at that age, I didn't have a job. I remember him always being really cool, friendly, and he'd tip me big for doing those chores. He'd even buy me gifts for my birthday, at Christmas, and sometimes just out of the blue for no reason. He told me not to tell my parents about them. He never told me why I wasn't supposed to, but I was happy to comply since I was very fond of him, so I never told my parents about the gifts. On my 18th birthday though, all I received was a letter, in which Ryan said he wanted me to come over to his house on a day I wasn't busy, and that my gift was there. Naturally I was excited, speculating he was going to give me something big - maybe even a car!

Now before I tell you about the day I went over cause of his beckoning letter I'll tell you about about the two of us. I am a white guy, a bit of a jock tall, cute, and athletic, have dark hair and dark eyes. I was a wide receiver on my high school football team and got a bit of attention from the ladies, but after having a few girlfriends in high school, I never really got past third base with them, and truth be known, I didn't really want to. When I'd masturbate, it would always be to girls getting it up their ass, and getting creampied, but my focus was always on the cock, the cum, and the asshole. I realized quickly I wasn't really into pussy at all, eventually I started looking at gay porn, and found it amazing, but I was ashamed of myself. I found myself drifting off into many, many erotic fantasies about being with men, and of course, Ryan featured in many of them. At roughly 6' 2'', Ryan was clean-shaven, quite muscular, had short brown hair and I imagine he was around 230 lbs. I had no idea at the time but he also had been fantasizing about me.

So anyway, onto the birthday letter. I have a summer birthday so I turned 18 right after graduation. So a few days after my birthday when I had nothing planned, I decided to stroll over to his place. I just told my mom I was going over to a friend's house, so it was no big deal. I walked up to his front door and rang the doorbell. He didn't know I was coming over so he was very happy to see that I had gotten his letter and decided to see what my gift was. He let me inside, and asked if I wanted a drink. I asked if he had Pepsi, and he said "No I meant like an alcoholic drink, Ian. You won't tell your parents, right?" I chuckled "Ha ha no, Mr. Thomas, that would be great though!" I was always blushing around him, and he always smiled when he saw me doing it. "You must do pretty well with the ladies. You're quite the stud, you know?" he commented. I blushed wildly, and a grin crossed his face. "Yeah, I guess so" I replied. At this he was a little confused, asking "What do you mean by that?"

So now I came to a hurdle. Mr. Thomas was the only person who I could trust with my secret, that I was into men, but how would he take it? We were now standing in his living room, I was drinking down my glass of an unknown alcoholic beverage that tasted great. I told myself, Well fuck it, I know I can trust him. "Well Mr. Thomas, can I tell you something, and promise not to tell my parents?" I asked. "Of course Ian, you know you can talk to me." "Well," I nervously said, my face beet red, "I THINK I LIKE MEN AND I DON'T KNOW WHAT TO DO."

He was a little shocked by this and so was I. How could I just come out and say something like that, and to a man to whom I was attracted, and about whom I had fantasized? Then he took a deep breath, clearly having made-up his mind, smiled, and replied, "Ian, haven't you ever wonder why a good looking man like myself doesn't have a wife? I'm gay. Why do you think I always bought you gifts, and had you do chores for me? Your are the most beautiful person I've ever met!" He was so casual as he said this, I was frozen, but he wasn't, he walked over to me and kissed me strongly, his tongue pierced my lips as he wrapped his arms around my body, holding me tightly. I could feel a huge bulge in his pants, but couldn't focus on it, my mouth relaxed. I was being kissed by a man! It felt so good, so right! I started kissing him back now, sucking on his tongue, our mouths engaged in a deep kiss. After a minute or so, he broke off the kiss, looked at me and smiled, he grabbed my ass with both hands, and pushed me with his big masculine body onto his couch. I found myself on my back, he was laying on top of me, groping me, and devouring my mouth. I was so horny now, and our bulges were up against each other. He lifted himself off of me, took off his shirt, and I instinctively did the same, then my hands wondered down to me pants, he saw this, and immediately removed his belt, unzipped his jeans, and out of the part in his boxers, his huge cock sprang out. He was straddling my hips now, and the monstrous cock was about 2 feet away from my face, It was amazing. Mr. Thomas' cock must have been around 8 inches, slightly darker then the rest of his pale complection and really think, like really thick. With a fucking sexy purple mushroom head that perfectly complemented the rest of it. I was entranced. I just lay there staring into it's glory. My hands still stood by my zipper, he's strong hands removed them. And he undid my pants, and my smaller, 6 inch cock sprang out, hard as a rock. He then lunged back onto me, fucking my mouth with his tounge again, He began fucking my cock and balls like I was a girl. His huge member plunged wherever it wanted up against my sac, pushing at my balls, and then it sprang forward and lay atop my own cock, just as Mr. Thomas lay upon me. This cock fucking, and extreme make out session went on for awhile. I felt like I was in love, I had never felt this way before! He then sat up again, and removed his pants completely, I did the same thing, and suddenly we were both naked. once again, on his big couch, he was straddling my higs, with his huge cock hanging there, over my own and my eyes once again locked onto it.

"I want to make you feel good Mr. Thomas!" I nudged my body so that his cock was now hanging over my abdomen, and kept creeping under his legs until it was over my chest, then mouth. He lowered himself down, I opened my mouth and felt that amazing head, wet with precum touch my tounge for the first time. I then envelepod that delicious head completely into my mouth, I felt like my mouth was full from that alone! I just lay there milking that sexy goliath of a penis. He groaned loudly and oftenly, "aaahh Ian, my sexy little bitch" "oooooH" He then grabbed his shaft with his right hand, and the back of my head with the left, I had so far only been able to fit the head in, but now he began fucking my mouth, I couldn't breathe, but I didn't care, and soon I realized I could still breathe through my nose as he used my mouth for his pleasure, he kept fucking my mouth, working his thick cock deeper and deeper. It tasted so good. It was oozing precum, and he must have been working out or something before I came over cause it was sweaty, and I loved the taste. He continued his conversion of me into a faggot. Eventually his cock head was pressed up against my tonsils, and a good half of his huge shaft was in my mouth. It was hard to concentrate on breathing and being fucked in the mouth but I did it cause this was the best thing that had ever happened to me. Drool ran down my cheeks and out of my mouth, along with precum. He was turning my mouth into a pussy! Eventually the whole thing was down my throat. His pumping speed increased, as he kept groaning, "oooh baby your my little boy toy, your my little slut, you love cock don't you boy?! I couldn't respond, I could only lick and slurp at the base of his cock with my tounge. I couldn't see anything either, his pubes pressed against my nose now. His huge balls slapping my chin. "ooooooooh" here it comes boy. He pulled his dick out, and I got a breathe, then he plunged that huge sexy head back in, jacked his shaft for a few minutes with his cockhead just resting in my mouth.

Then it happened, I felt his cock head pulsating in my mouth, and I was flooded with hot, warm, gooey, tasty man sperm. The jets of cum hit my tongue, the back of my throat, stream after stream after stream. Until my mouth was completely full of cum. He pulled his cock out and said, "Swallow it like a good faggot" He lowered himself and his think member lay on my chest, oozing a little bit of cum and saliva on me. I just lay there with that thick seed, that puddle of sperm in my mouth. I was enveloped by the taste, I never wanted to swallow it cause I loved how I felt. A grown man just used my mouth and fucked it like a girl's pussy. But it was so much better than a girl's pussy. Fuck women I thought, this was all I wanted now. Cock and cum! I then swallowed it all down, his seed impregnating my stomach. I was his. I didn't even want to cum, i mean i did, but it was more important to me to service him, that's all I cared about, he just showed me who I was, and I just wanted to be owned by him now.

I started spending nights at his house, I gave him at least 10 blowjobs like that a week probably.I didn't want to go to college anymore, I wanted to live with him and be his. For his use only. I no longer cared about a career, my career was being a cock slut. I don't know how he produced so much semen, but sometimes I'd get full from all the cum I drank of his, and just knowing his seed was in me, I felt like I was on top of the world! I loved being used and depraved by him. He started getting violent with me, sometimes he'd have me kneeling on the floor and would just pound my mouth for hours on end. He was violent with me, but he really loved me. He started buying me stuff all the time, flowers, lotions, and dildos! He told me to train my asshole when I was at home from now on, and I did. He told me that after a week of me training my hole, he'd take my virginity for real! I was so excited. so everynight id go home and play with my tight hole, he told me after my sessions, to put an inflatable butt plug he got me into my hole and sleep with it inside of me, pumped up a little the first night, and by the end of the week I was sleeping with the butt plug in me fully expanded. The next mourning I decided to look at my asshole turned boypussy in the mirror. It still looked tight, but then i lubed up a penis shaped dildo he bought me, and slid it in, it was big, but not as big as Mr. Thomas' cock. It hurt a bit, but I just kept pumping, and after a good 10 minutes, I let it out, my hole looked so fuckable, It didn't quite gape open, but it was no longer an asshole, this was now meant for men's cocks. And the first cock to enter was going to be Mr. Thomas'.

So we set up a night for our next sleepover, all of the sleepovers we had before were just oral, me going down on him for hours on end, some nights i'd fall asleep in his bed with him, his cock in my mouth, sometimes i'd wake up with liquid in my mouth and running down my face with a wet puddle in the sheets, like he jacked his cock off in my mouth while I slept, or maybe even pissed a little bit in me, It was so nice to wake up to my mans cock in my mouth and the thought of his seed and piss being able to have a nice warm place to be released into! But anyway, it was now August, and we were pretty much officially boyfriends, or rather, master and toy.

We watched a movie together that night in his bed, toying with eachothers cocks all the while, he usually didn't show too much interest in my cock but tonight he did play with it quite a bit. The movie ended, he didn't turn off the tv. Mr.Thomas leaned over to his night stand, and asked, "is your hole ready for tonight boy?" I replied "yes Mr. Thomas, i've been training it all week, I even got the 7 inch black dildo all the way in me this mourning and it was amazing!, I can't wait to really pleasure you!" He smiled, grabbed a bottle of lube out the droor. "well not only does your hole after be ready for a cock to be in it, but we have to be sure you don't have to take a dump or anything" I knew my hole was clean, I made sure of it before I came over, I would never let down my man!" My hole is as clean as any girl's pussy, i made sure of it" I said blushing and smiling. "Well i should hope the fuck so, those things are filthy, but I know what you mean, good"

He lubed up his fingers, and while jacking me off gently, he reached under my butt, and stuck a finger up my hole, he didn't have to work to hard at it, I was horny as fuck and ready to go, I started fucking his finger with my asspussy, he then extended, a second finger, then a fourth, he started ferociously masturbating my sexhole, in and out and in and out!, he then lay down on his back, fingers still up inside me, and told me to lay on him the opposite way, I knew he wanted to 69, I straddled his chest, with my ass facing his face, and lay down upon him, that big sexy meatpole looking me right in the eyes, and he turned my ass into his own personal plaything, I sucked his cock down my throat, the past weeks had made me and adept blowjob slut and deepthroater, I went to town on his massive cock for about 10 minutes. From his end, my smaller cock and balls rested on his chest, oozing precum with a small puddle of it soaking into his chest hair. He suddenly removed his fingers that had been working over my now slutty hole, exposing a modest gape, but not an ugly one, just a thin part that almost resembled a pussy, but way better cause it was a boy's asshole turned into a hungry virgin sex hole that craved cock. He lifted his head up and plunged his mouth up against my butt, his tounge probing me, he did this for awhile, and it felt amazing, his toungue slushing around in my insides, in my pussy. God damn I was a horny faggot!

"Okay bitch your ready now" he told me, he slid up, his cock plopping out of my mouth, my cock being ran down his chest, then abdomen, then for a moment, rubbing up against his much larger, sexy mammoth cock. He pushed me over to a doggy style position, with my butt in the air, I felt him push his cock up against my hole, and even though my hole had seen alot of action from dildos, my butt plug, and his fingers over the past week, It wasn't ready for even his think purple mushroom head, but he forced it in, grabbing me by the hips I felt his head plunge into me, I felt it, and I felt as the rest of his cock slid in me, the difference in widith I felt from his cock head to his shaft was very noticable, as his head slid deep inside me I felt it rubbing up against my insides, It hurt so much, but my hole was being fucked! It was so awesome, so amazing, the pain didn't matter, I pushed my ass against him untill he was all the way in, my cunt relaxed around his cock, his balls resting up against my gooch, his pubes tickling the top of my ass! Wow this was amazing.

Then the fucking started, 30 solid minutes of pumping, precum, ass juice, and lube oozing out of my asshole, my god did I feel like a slut! In and out he pounded me, wrecking my hole, he wouldn't stop, he only got faster and rougher, I cried out, not in pain, but I was being impaled on a cock I thought was only 8 inches, it felt way bigger inside of me, now that it was fucking a hole it probably got even bigger, and instead of being slightly flaccid when i sucked it, it now felt rock hard, and the already big head felt huge inside me, It was clear he had penetrated me all the way past my rectum into my second hole (is that whats its called) fucking me over and over and over, suddenly his balls tensed up, and a flood of semen shot into my bowels, endless jets of seed, impregnating me, seeding me, making me even more his than I already was. But he wouldn't stop fucking me, I thought after he came he'd be done, but he wasn't, "Ooh fuck yeah boy, i'm gonna stay in for another round" "Oh no i thought, my asshole was already wrecked" With his semen now lubing my now slick hole he kept on pumping, in and out, in and out, now he started a new technique, that was torture for me, he'd slide his whole cock out of me, exposing my stretched hole, and plunged back in, this continued for and hour now, and he finally had his final orgasm of the night, pumping even more seed into my already saturated hole, I belonged to him now, my hole was his, for his use forever! There must have been a good 2 cups of semen that had been fucked into me, absorbed into my body because after our fuck, He kept himself inside me, reached over and turned off the light, and flipped us on our side, spooning one another, entwined, his massive cock in me all night while we slept together, both exhausted.

To Be Continued!

Edited by Hotload84
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Posted (edited)

Where my story left off, my asshole had finally been taken by a man whom I'd known for a good part of my life, Mr. Thomas. He had left his massive cock inside me for remainder of the evening. I awoke in the morning with a very sore and very wet feeling in my ass and my lover's hot breathing on the back of my neck as he spooned with me while he slept. I had to pee badly but I had this huge penis impaling my asshole. God, it felt amazing to know that a grown man had fucked me in my hole, erupted an enormous load deep inside me, and that his cock had plugged-up my hole the entire night, all that seed inside my tight slutty hole, as if just to completely drain me of any remaining masculinity.

I had been made into a total slut over those past few weeks. Happily I was giving a near endless supply of blow jobs to a much older man who lived down the street, ingesting copious amounts of semen from him. He had persuaded me into playing, with reckless abandon with my hole, using dildos he had purchased for me. He even persuaded me to sleep on a nightly basis with a butt plug in my ass. And now this.

I decided I had best try to push him out, as big as his dick was, Mr. Thomas' cock was flaccid, so it shouldn't be hard to push out, damn was I wrong! I tugged my ass away from him, and relaxed my hole. The massive member slowly inched out of me. I could feel it with my sphincter and anal muscles but it was very numb down there so my whorified hole probably wasn't pushing it out with much effort. I grabbed the edge of the bed with my hand and pulled myself away, and his huge dick popped out of me with a loud wet plop. As I pulled away from him, his arm that had been resting on my hips slowly fell to the bed.

I awkwardly arose from the bed and stumbled as I walked. It was then that I really understood what he had done to my body. He had totally wrecked my hole. My cunt was filled with a man's seed. Cum oozed out of it as I walked to the bathroom, it was sticky and smelly and soon covered my butt cheeks and thighs as I finally made it to the bathroom. It was a large bathroom and the toilet was on the far side from the door, I couldn't make it, my pussy was about to let out everything that Mr. Thomas had deposited the night before! And I couldn't bear losing his precious cum! The sink was surrounded by a low obsidian counter top with large mirror behind it.. I scurried over there and placed my asscheeks on the edge of the counter, spread out. The mirror gave me a perfect view of my flayed pussy.

Looking now like a sex organ in it's own right. My asshole's lips were swollen from all the fucking it had been getting. And it gaped open so that a trail of thick smelly semen could be seen oozing out in a channel. This all happening in a matter of seconds, my small flaccid dick sprayed out all the urine in my body and my hole immediately gave out a loud, wet gurgle and opened even more and ounce after ounce of semen burst out of it and onto the counter top near the sink. And I gazed at my asshole, looking better than any woman's pussy I had ever seen. It was growing more adept at pleasuring men.

Just then I saw saw in the mirror the reflection of a sexy older man, with his once again rock hard cock peeking through the crack in the door. "You had better clean up your mess" he said with a smile. I knew what he wanted me to do. I turned around and slurped up all of the warm stinky creampie, my neglected cock immediately became erect at the ingestion of another man's sperm. For being deep in my pussy all night, it sure was thick. Mr. Thomas came up from behind me as I was bent over and shoved his huge cock up my slutty hole. My boyhole gurgled and bubbled wet with semen and as it was forcefully penetrated and even more ruined by a man's penis. I thought to myself of all the things I could be doing with my life if I hadn't gotten addicted to this. College, marriage, kids, a legacy. None of that will ever matter to me again. I want to make a living pleasing men and being a slut!

Around the base of Mr. Thomas' enormous cock my thick juicy ass lips clung tightly. Gaped as I had been, my body was now being violated very deeply and my spasming asshole provided everything my lover's organ wanted. I turned my head around, wanting his tounge in my mouth, he couldn't resist my teenage lips. His tounge like a burrowing animal in the throws of winter crept deeply into my mouth, his saliva invading my own. He began lurching into me, he couldn't take how sexy my holes were, he was cumming much quicker than usual. I felt hot jets of semen covering my boy womb.

"I'm going out of town for awhile, I'm not sure how long it's for business and they may need me there for quite sometime." he said suddenly as he pulled his dick out, spilling our juices on the floor. "Clean up this mess, slut"

Cleaning up the mess I didn't mind at all, I was a slut for him now and I'd do anything he'd tell me. Being apart from him for a whole week though wouldn't settle. I'd have to be away from cock for that long! And spending all that time with my family seemed dreadful. I felt so faggotish, my parents would realize right away I had been changed, or rather awakened. It was now late July, and they likely thought I was to be going off to school. I resolved right then and there to tell them about my sexuality and my intent to not go to college. Not because of courage, but because a man had fertilized my asshole like it was a girl's sex organ, and I had completely fallen love with the though of pleasuring men. I didn't care what they thought.

"And then go home and pack up some clothes, you won't be needing them but untill we buy you some new threads in San Fran" he said with a smile on his face, washing off his cum and anal juice covered man meat. My worrying turned into a great burst of excitement that I had never known before. I leapt into his arms, he grabbed my ass with both his strong arms and tounge fucked my mouth, the same mouth he bred with his cock countless times. "We leave on August 1st, I hope you know what your getting yourself into with this"

I didn't know what he meant by that, but it excited me to no end. I wonder what he has in mind!! I quickly cleaned up the mess in the bathroom, my piss and creampie spill about the floor. He had hopped in the show and I had it all cleaned up and was out the door with only him saying to come back over tomorrow morning for our early flight.

As I walked home I realized that I didn't get to take a shower there, my usefulness to him for the day had passed and I trotted home reeking of sex. I also realized that I had not cum the night before nor this mourning, nor was I hardly ever allowed to. I suppose I never really wanted to, I felt the urge to, I was rock hard and had been most of the past 24 hours. But my small erect cock was nothing, it was never meant to please a woman, or a man, or to reproduce, or even to be pleasured. It was like a woman's clitoris, a nub above the hole that would take an insurmountable amount of cocks in it before my life was done, before even my 20's were done likely. I realized that I loved the fact Mr. Thomas showed no interest in it, he loved me for my hole and my submissiveness. I was his faggot.

I returned home, seeing both cars in the driveway, and remembered it was Sunday, so they would both be home the whole day. I walked inside. My father waiting up the steps from the door barked; "Ian where the fuck have you been!"

"I'm sorry I was at someone's house" I replied, nervously and stuttering a bit.

Well that's just great, what a great excuse to not tell us anything, and it's not just last night, you've been gone half the summer! And your high school counselor just called yesterday, and said you never even went to orientation and U.W. La Crosse, isn't that where your going to school or did I miss something?" He shouted rhetorically.

My mom came to the door too, motioning for my Father to stand to the side.

"Let him come in and sit down before we talk" she said, catching the whiff of my body the first time. I could feel semen and cunt juice roll down my legs from a very juicy and sore boy pussy. My father smelled it too.

"What is that smell and what's on your legs?" He yelled.

"Well I wanted to talk with the both of you too, I hope we can be civil" I said, I was still nervous. But I sad legs apart in from of them on a kitchen chair, they remained standing.

"I've met someone, it's the reason I smell this way, it's the reason I've been away so much this summer, and it's the reason I have no intention of going to school, not at this point in my life at least" I actually got calmer as I said it, remembering I don't care what they thought.

My father exploded, "What kind of woman would not even want you to go to school! Whoever she is she's no good for you!"

"How dare you Ian, we've saved up so much for you to go off to school and you don't even intend to go, because of some girl?"

"Well that's the thing right there, it's not a girl, it's a man, a grown man" I smirked a bit as I replied, no longer nervous or stuttering.

My parents just gazed at me, jaws to the floor, eyes wider than the moon.

"He's taken my virginity and made me realize who I really am, I'm his. I will do anything he asks. And I have been too. If I were born a girl, I'd be pregnant now, without a doubt. And now that I think of it, I really wish I had been born a girl. For him I'm submissive and I've forgotten all about my own male needs. I have the needs of a bitch in heat, and that's what I want to be, his bitch, forever."

There was no response. A huge boot kicked me in the gut. "Get to your room you pathetic waste of a son." he said grimly. My mother began sobbing and ran off. I walked away from the room too. And upstairs I went. My father followed me, for what reason I don't know why. As I entered my room I tried shutting the door. "Please, tell me this is just some stupid joke, boy." He pleaded. But before he even finished speaking I yanked my pants down and bent over, taking a finger I reached into my hole, scooping up a fingerful of the sex juices that my lover and I had made.

"This is his seed, I'm not crazy dad, but this is the life I have chosen, if there were any going back I'd still choose to be an object of male lust and desire" My smirk from before had returned as I said it.

The door slammed shut. I packed up some clothes, and my sex toys and was out without so much as a goodbye to either of them. You see I was raised very conservative, and my parents didn't care for gays, blacks, or a number of other perfectly decent human beings. So although you may think me heartless, understand that whatever else could be said to them, would have no effect. They can cling to Jesus, Guns, and Money. I had Cocks, Cum, and Men.

To be continued once more! Sorry for the delay!

Edited by Hotload84
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