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FROM STRAIGHT BOY TO CUMDUMP IN ONE NIGHT ----the story of my transformation---- The summer between my freshman and sophomore years of college started out as the most boring summer of my life. I had stayed at university to take summer classes and was subletting a room in a shitty four-bedroom apartment of which I was the only resident. I worked at a local movie store fifteen hours a week and was taking two classes both of which were over by two pm on Mondays and Wednesdays. The rest of the time I just spent watching Netflix going for runs, and jerking off. I had run track in high school and still kept up with my workouts keeping my lean frame in shape. At that time I was five eleven, one hundred and fifty pounds, with short-cropped black hair and the starting of a rather thick pelt of hair across my body. Puberty had come a little late to me and I had been hairless all through high school for the most part, but freshman year it had struck with a vengeance and I now grew thick coarse black leg and arm hair, my pits long bushy shrubs, and my chest hadn’t sprouted a patch in the middle but rather was slowly becoming carpeted in black hair. I loved it, I thought all the hair made up for my slight build and made me look manlier so I showed it off every chance I got. Normally when I went for a run I just ran round the campus, but on this particular day I was in a mood, bored with my solitary routine, sick of not seeing any of my friends cause they had all gone home for the summer, and over feeling trapped on campus so I made my way to a bike trail that ran through most of the town and started to run as far away from campus as I could. It was a hot day and the sweat ran down my bare torso and I jogged along for several miles. Most of the trail was bordered by trees, but every once in a while there was a gap and you could see into the back gardens of the people who’s houses back onto the trail. I had run the trail before and there was almost never anything of interest happening on it, in fact the only real appeal of the trail was that it was away from the school. I suppose before I continue with my story that I should mention that at this point in time I believed myself to be straight. This is in fact the story of how I came to realize that not only was that not true, but just how very much of a fag I really was. Despite believing myself to be straight I had always been interested in the male form. I could never help but to look when I saw a real manly man out and about. So what happened next really should have been no surprise. As I ran round a bend in the trail I found myself facing one of those patches where the trees thinned and you could seen to some random person’s back garden. This back garden however didn’t belong to just anyone. There in the clearing pushing a wheel barrow full of dead plants was a six foot six inch tall sweat soaked muscle bear. He had a strong pronounced jaw line sprinkled with salt and paper stubble, his head was shaved but the skin was tan from the sun. His arm muscles flexed under the dark bronze skin and hair as he moved the wheel barrow across the yard his bare chest glistening with sweat from the heat. Though I was staring intently at this perfect specimen of manliness I was still running until suddenly I caught my foot on a root and tumbled ass over elbow over the small bush that separated the trail from the Adonis’s backyard and landed sprawled face down on his perfectly kept grass. “Holy shit,” I heard him call out, “you ok kid?” “Yeah, I’m fine… just tripped… sorry.” I wanted to get out of there as quickly as I could even and though I was already flushed from the heat running I felt my cheeks burning with embarrassment. I rolled over and started to stand up when the ankle that I had caught on the tree root gave way underneath me. “You don’t seem ok kid, come on… let’s get you inside and make sure that ankle’s not broken.” As he walked over to me I was overwhelmed by his smell, a thick pungent musk that I found to be intoxicating. My head was swimming as I tried to focus through the haze of his sweat stink and I hardly noticed him picking me up and helping me to stand so that we could hop back to the house. He took me into the kitchen, sat me at the table and started to unlace my shoe to look at my ankle. I barely paid attention to anything that happened, till he said it was just a bad sprain and that I should just rest my leg for a while. “How far did you run kid?” “From the north side of campus,” I replied. “Shit that’s half way across town, tell you what. I’ll drive you back later so that you don’t have to run on that twisted ankle.” I graciously took him up on his offer, and sat in the kitchen icing my ankle and watching the man, who’s name I had learned was Eric finish up the yard work before he drove me back to campus. I couldn’t take my eyes off of him and I didn’t understand why, I thought that it was because he looked like the man I whished to become, but I was wrong. When Eric had finished the yard work a little over fourth five minutes later he came back into the kitchen bringing with him that glorious smell once more. “Ok, let me grab a shirt, and right a note to my husband telling him I’m out in case he comes home from work while we’re gone, and then we’ll be off.” He said off of this as though it were the most natural thing in the world, but my head was spinning: HUSBAND? Was this perfect specimen of man a homosexual, could that be? I didn’t have much time to think before Eric had returned with an white a-line t shirt one along with the same basketball shorts he had been wearing to work in the yard. I set my foot on the ground gingerly, and Eric leaned in to help pick me up, but once he had pulled me upright he just held me for a minute and stared into my eyes. His eyes were slate blue and stood out against his tanned skin and dark hair. After what seemed like an eternity he said, “So why did you trip kid?” “Ummm…. I…” I spluttered. “I thought so,” and he leaned in and kissed me. Several things all happened at once within my body: I panicked; I tried to push him away; and my cock sprang to life becoming instantly hard. I staggered away from him for a moment my brain screaming. And then it all stopped and all that I wanted to do was be in that man’s arms, I wanted to feel him against me. I dove back into his arms, grabbed his face and stuffed my tongue in his mouth. His hands wandered up and down my back, grazing but being careful not to go past the waist band of my short bright yellow running shorts, as we kissed and I clung to him as if I never wanted to let him go. Eric broke away, “I guessed that that’s why you tripped, but I wasn’t sure till you sat in here and practically drooled as you watched me work in the garden. Plus your cock hardened every time I touched you. Your brain my not be ready to admit it but your cock certainly isn’t” He said all this staring into my eyes, his hands still roaming over my back, but with that last part he reached forward and grabbed my throbbing cock through the thin nylon on my shorts. I gasped. He smiled, “You ever been with a man, kid?” “I’m straight.” “And I’m the Queen of England,” he said, kneeling in front of me, “don’t worry boy I’ll teach you hot to please a man.” With that he pulled my shorts down exposing my rock hard cock and before I could protest further he swallowed my whole seven and a half inch cock to be base. Within seconds he had me moaning and groaning and holding on the back of his head to keep my cock from slipping out of his mouth. I started to feel my balls tensing up and seeming to sense it too Eric pulled off of my cock and stood up again. “Now you try.” “I’m straight,” Eric pulled of his shirt revealing his massive hair covered chest in all its glory. “You want this I can tell. Now get on your knees and suck my cock.” I don’t know what made me do it but I sank to my knees, Eric pulled his cock from the waistband of his shorts, smacked me in the face a few times and then I opened my mouth wide and began blowing this beautiful man. As I emulated what he had just been doing to me his cock began to grow and engorge until I was convinced that it wouldn’t fit in my mouth any longer. “Good boy, you work that man cock, get it good and hard.” What the hell was I doing? I was gagging this man’s ever hardening cock down my throat and loving every second of it. This was better then anything I had ever down with a girl. The smell of Eric’s sweat burned in my nose and I could taste the sweet salty liquid on his cock and I swallowed. He placed his big strong hands on the back of my head and guided me to begin bobbing up and down on his shaft. His cock brushed against my tonsils and I heaved for a moment before swallowing hard and feeling his cock slid down my throat. Everything was perfect. My jaw stretched as wide as it could, I felt pubes around my nose and balls against my chin and opening my eyes I found that I had slid Eric’s entire massive cock down my throat and was now sucking it with ease. I looked up at Eric and saw that he had his phone in one hand and the other holding my head in place as he started to thrust in and out of my mouth. I panicked a little, but never thought to take his cock from my mouth. There was the click of the camera and I widened my eyes in shock. “Don’t worry boy, just a pic for my husband to show him what’s waiting for him at home.” My brain was screaming at me to spit his cock out, pull my pants up and run, but my cock was throbbing, my mouth was drooling and for the first time in my life I felt an itch grown inside of me that I did not yet understand. “You’re a hot little cock sucker aren’t you.” Without knowing why I nodded, and grabbed Eric’s well built thighs pulling his cock into my mouth completely once more. “I’m gonna have some fun with you tonight.” Eric let go of my head and grabbing me under the armpits pulled me to my feet and kissed me again. This time was rougher, he shoved his tongue into my mouth and held my face close to his with his rough hands. I melted into him, feeling his warm sweaty body pressed against mine, his massive cock trapped between up. “Turn around,” he whispered in my ear. Don’t do it, my brain told me, you’re not a fag. What the hell are you doing? I turned around obediently. Eric hugged me from behind, his hands resting on my pecs as he kissed my neck. I could feel his cock nestled in my ass crack, and I couldn’t help myself, I rocked back on it rubbing his cock with my tight furry ass. Eric began to kiss down my body, his tongue tracing my spine as he once more sank to his knees. His tongue came to my tailbone and I shuddered, it was as if a bolt of electricity had gone through my body. I involuntarily arched by back. “A natural bottom,” Eric muttered and with one hand between my shoulder blades and one on my hip he forcer me to bend over so that my chest was resting on the table. He spread my ass cheeks with his hands and I felt cool air on my hole. Then something warm and wet touched my hole. Two reactions shot through me, the one from my mind of RUN, the second from my ass: GOD NEVER LET THIS STOP. It was as if the way I thought about myself and my body and what I wanted was at war with what my body was experiencing. That itch I had started to feel earlier began to become a burn and find a home in my ass Eric’s tongue brushed against my tight hairy little virgin pucker. Eric pushed down on the small of my back forcing me to push my ass out more and I felt his tongue make it’s first attempt at entering my hole. The war raged on inside my body but I made no attempts to stop Eric, I just kept moaning loudly. I could feel my hole becoming slick with his spit and weather it was from the spit or the warmth or his breath or the repeated darting actions of his tongue I could feel my hole slowly starting to relax and bloom allowing more of Eric’s tongue to dip inside. My cock was hard as a rock and dripping precum but I felt no interest in jerking off my focus was on my internal conflict and on the waves of pleasure that emanated from my steadily loosening hole. “God you have a beautiful hole, tight, pink, and furry. I love it. Nice virgin hole.” Something rough pressed against my hole for a moment along with Eric’s tongue I looked over my shoulder trying to see what he was doing and I gasped when I realized that it was his finger. He briefly sucked on his finger and then pressed it again to my hole. Now slick with spit his finger didn’t just rebound off of my tight pucker but pressed inward a little bit, but my hole resisted. Eric returned to working my hole with his tongue but kept a steady pressure on my hole with his finger. My mind was becoming foggy and the argument between my brain and my body was becoming less and less. I started to think things like: if it feels so good how can it not be what I want. Eric increased the pressure of his finger on my hole, hocked a big glob of spit onto my hole and suddenly something gave way and his finger just slid inside of me. I gasped, it didn’t hurt, not at all, it was like a when you finally manage to scratch a really bad itch on your back that you couldn’t reach; and there ended my internal strife, a decision had been made, my body won and silenced my brain. I pushed back against his finger trying to swallow more of it up. Eric responded by slowly and deliberately sliding his finger in and out of my hole making me moan loudly. I felt sweat spring up on my back and it was hard to catch my breath. Eric chuckled softly to himself and withdrew his finger. I felt empty and alone for a moment and then I felt the finger return but it was thicker this time; two fingers. He repeated the same process until over the course of the next half hour he had worked all four fingers into my hole and was slowly twisting them in and out of my now loosened hole. Eric kissed my ass cheek and stood up with drawing his fingers from my hole. God I missed his fingers, the transformation that had taken place within me over the past forty minutes was complete. I no longer questioned what I was feeling and I knew that I wanted to keep his fingers inside my hole forever. That is until what happened next. Eric rapped an arm around me and pulled me up from my bent position, kissing my neck, his warm musky body pressed against my own. “You have such a sweet virgin hole boy,” he shifted his weight, “but I think you’re hole is ready for more,” with his free hand he bent his cock down from where it rested in my ass crack and aimed it at my now slick and loosened hole, “what do you say we bust that cherry?” I was grinding my ass back against his cock, relishing each time I felt his cock snag on my ass ring, but this was not enough for Eric. He let go of my chest and pushed me back down on the table so that my ass was once again spread out before him. My whole body seemed to have become electric and I sensed every tiny shift that Eric made as he shifted himself into position and began to ever so gently press his thick mushroom headed cock against my hole. His four fingers had opened my up a lot but my hole as still far to tight for Eric’s cock, he pushed harder, hocking up another big glob of spit right onto where his cock head met my hole. The itch I had felt earlier was getting worse, I felt as though there was a burning inside of my hole and only getting Eric’s monster cock inside of me could make it stop. I flexed my ass muscles and twitched my hole like I was taking a shit and felt for a brief moment my hole open up and a tiny bit of Eric’s mushroom head slip inside. I did it again this time pushing back against his cock and felt a little bit more slide inside. “Jesus, you can’t wait to pop that cherry can you boy? Alright then lets do this. When I push you flex your hole.” Eric grabbed me by the hips and started to push hard against my hole, he managed to force a little bit of the head inside without my help but then I flexed my hole and between his pressure and my open hole the head of his cock shot into my ass with a pop. It felt like a soda can had just been shoved up my ass, but I loved it, I wanted more. Eric stopped pushing for a moment, then spat on his cock and pushed hard again sinking about another inch of his cock inside me. He did this several more times till at long last I felt his thick black pubes against my ass and his balls resting against mine. Sweat covered my whole body and I was shaking a little. My hole was twitching around Eric’s cock trying to pull more of him inside of me. After what seemed like a glorious eternity he began to pull out until only the massive mushroom head remained in my hole, and then just as slowly he pushed back in again. A whimper escaped from my lips. “You like that thick cock deep inside you boy? You like feeling your cherry disappear as my cock invades your sweet wet boy cunt?” “Yes,” I said breathlessly. There was no denying what I wanted, no claims of being straight, no claims of wanting to be a top either, my cock was hard as a rock but I had no interest in it, all that mattered was Eric’s cock. “What do you want now boy?” Eric pulled out to the tip again, “Do you want me to fuck your boy cunt?” He plunged back in, harder then he had before, “You want me to pound your hole?” “Yes,” I moaned. “Yes what?” He withdrew again. “Yes I want you to fuck me.” And there it was, there was no taking it back, I had admitted what I wanted. “Good answer boy.” Holding me by the waist Eric started to make me grind forward and back on his cock and he pulled in and out picking up his pace rapidly until in a short while he was hammering away as though he were fucking a well broken in hole. I was moaning like a bitch in heat and I knew it. Everything else in my mind had gone blank and all that I could focus on as my hole and his cock. Faster and faster he went, now slamming his cock in hard so that the room filled with the sound of flesh smacking flesh. He grabbed my shoulders for better leverage and I started to buck back harder, meeting each thrust with equal force. By now I was practically screaming my vocabulary reduced to three phrases: Yes; Please; and Fuck me. “You wanna ride my cock boy?” “Fuck yes” Eric pulled his cock from my ass with a soft squelch and layer down on the floor his cock sticking straight up to the ceiling. I practically flung myself on his cock, positioning it at the opening of my no longer virgin hole and sitting down hard. I bounced up and down letting gravity pull me back onto Eric’s cock each time. Both of us were covered with sweat and it was as if the whole world smelled of sex. Eric’s breathing began to change and he started to buck his cock up into me as I rode. Quicker and quicker he pounded till after ten more minutes he growled, “I’m going to cum, I’m so fucking close. I’m gonna breed that sweet cunt and make you into a real bottom boy.” “Yes breed me,” I groaned, not really knowing what I was saying. “You want my seed boy?” “God yes!” “Ok, well get ready cause…. FUCK!” He never finished his sentence he just grabbed me by the shoulders and forced me to bottom out on his cock while I felt his shaft pulse and throb deep in my guts and a new kinda warmth spread through my body. His cum filled my hole and started to leak out a little down his cock onto his balls. I was panting, but my lust was unslaked. I leaned in and kissed Eric as he had kissed me before he started eating out my hole, rough and hungry. I ran my hands up and down his hairy body feeling the mixture of the hair with the sweat. Eric pulled me close and kissed me too before just hugging me to his chest, his cock still buried deep in my stretched out hole. “Jesus when you sent me a picture of some cock sucker on your tool I expected to find a twink waiting at the door to suck my cock, not find you with your cock still inside of his cunt and your load leaking out.” I sat up, dropping down all the way on Eric’s cock in so doing and gasped, when I heard the new voice. “I took one look at this cherry hole and I had to breed it.” Eric said to the new comer. “Cherry hole you say. Well then I’ll need to taste it too.” “Kid this is my husband Matt. Hope that hole’s feeling good cause it’s in for a long night.”
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[Note: This story was inspired by an erotic cartoon] “Almost ready,” my wife whispered in my ear, as she led me from our bathroom into our bedroom. “Keep your eyes closed.” “Wait,” I said. “Do I hear someone?” “Trust me, Andy,” she replied. “I have a wonderful surprise for you.” *** It had started earlier in the evening as a game. Or so I thought. My wife had told me she wanted to dress me as a woman. Well, not just dress me – she used the word “transform” me. I thought it might be fun. A couple of weeks ago, after a few too many drinks, I had confessed to her that I had an inner feminine side and often fantasized about have sex with a man. Since then she had been teasing me about it and urging me to express my femininity. I have to admit it turned me on when she coached me to make womanly hand gestures or walk with a wiggle. Then tonight she announced it was time to try the next step. It started in the shower, where she helped me shave my body hair, including my armpits. Then she sat me in a chair to cut my hair. She likes to style her girlfriends’ hair so soon I had a pixie cut with ringlets on the side, all very cute and girlie. Of course, I had a raging hard-on the entire time, and since I was naked she could see it. Next she told me to dress sexy like I would if I were going to bed with a guy. She gave me a clingy black camisole top, a black thong, and black thigh high stockings. Finally, she produced a set of high-heeled black pumps. “I bought these for you, honey,” she had said with a big smile. They fit me perfectly. “Now for the finishing touches,” she declared. “Nails and make-up.” She had told me not to cut my fingernails for the past two weeks. She filed them into a rounded shape and painted them with her most trampy deep-red polish. At her direction, I had shaved closely just before we showered. As I sat on her make-up stool, she did my face, with base and shading, eye liner and mascara, and then red lipstick. “Wow!” she exclaimed when she was done. “You’re really quite pretty. Take a look.” I stared at myself in the mirror. I was amazed at how different I looked. I was utterly feminine and surprisingly cute. It felt wonderful but also kinda weird. My wife admired what she had done to me, “If we went out to a bar, honey, men would be hitting on you. I’m actually jealous of how sexy you look.” “You need some pretty jewelry, too.” She took off her wristwatch and told me to put it on. I admired the thin black leather band and small round face – it was unmistakably effeminate. Then she slipped off her diamond solitaire engagement ring and slid it onto my ring finger. Our hands are almost the same size and it fit me perfectly. I felt so sexy! At some point my wife had closed the bathroom door. She instructed me to come with her into the bedroom, walking so my hips would wiggle just as we had practiced. Then she took my hand and told me to shut my eyes tight as we went into the bedroom. I heard the bed creak. *** “Kneel here by the bed,” my wife said. “I’m getting nervous,” I said. “Who is it? One of your girlfriends?” “Um, not quite. You can open your eyes now.” I gasped: sitting naked at the edge of the bed was a very handsome, incredibly well-built man, with a rope tatoo on his right arm. “Andy, meet Kyle from my office. You told me you’d like to try it with a guy.” She had often spoken about him as her gay office boyfriend. I blushed red with embarrassment but didn’t move. “A pleasure, Andy. Your wife’s been talking to me a lot about you lately.” My wife giggled. “You’re not angry with me, sweetie, are you?” Instead of speaking, I reached out for Kyle’s dick, which was already erect. I could see pre-cum glistening on the tip. I brought it to my lips and then swirled my tongue around it. Kyle moaned, I then opened my mouth and began to suck it as I pumped it with my hand. From the corner of my eye, I saw my wife’s pretty watch and the sparkle from her ring on my finger. I felt like such a cock teaser and loved Kyle’s reaction. “My, someone is very eager,” my wife chirped happily. “God, it’s so hot looking at you going down on him. You’re a natural at this.” It didn’t take long. Kyle was soon thrusting deeper into my mouth, hitting my throat. I gagged a couple of times but refused to quit. As his moans and grunts got louder, I knew he was close. I pumped his cock harder and suddenly he erupted into my throat. The taste was strange but I couldn’t seem to get enough. I tried to swallow it all, but some of his warm cum dribbled from my mouth. My wife leaned in close. “I guess you liked my little surprise, huh?” I didn’t speak. I grabbed her face and thrust my tongue into her mouth. She doesn’t like the taste of cum but I guess she was so into the scene she responded with a passionate tongue kiss. “I suppose I should be angry,” I said, “but I’m too horny to complain. Kyle, are you ready to go again? I need to be fucked.” “Not yet, Andy.” “Well, I can help,“ I replied, as I gently pushed him onto his back, my mouth poised again above his now-flaccid tool. I turned to my wife. “Honey, I want you to lube my ass. Use your tongue.” She chuckled. “Whatever you say, sweetie.” She joined us on the bed, kneeling behind me and spreading my ass cheeks. I felt her warm breath on my virgin hole and then her tongue started to work around it. It made me quiver. I placed my hands on Kyle’s thighs and again noticed how pretty they were with my red nail polish and my wife’s jewelry. I started to lick his dick and balls very gently, sometimes moving up to suck and nibble on his tits, which I discovered were very sensitive. In just a few minutes I was rewarded as his penis stiffened and stood tall. My own cock, not nearly as big, was hard as a rock, poking out from my black thong. “Good to go,” Kyle said with a big smile. I straddled his waist and lowered myself onto his thick cock. I winced at first when he hit my sphincter but I didn’t hesitate. After all, a woman has to be able to take her man without complaint! That’s what I wanted to be – Kyle’s bitch, my ass a cunt for him to use as he pleased. I felt myself open to him, and then an amazing warmth and fullness spread from my ass to my entire body. So this is what it feels like to be fucked! I had never experienced anything so wonderful. It was much, much better than when I was inside my wife. Soon I felt Kyle deep, deep inside me, as my ass resting on his pelvis. I had taken all of him. I whispered in his ear, “Kyle, I think I’m gay.” I didn't want my wife to hear -- I wasn't ready. He responded by pulling my face to his and kissing me deeply. My first kiss with a guy, and I knew at once it wouldn’t be the last. "Oh, yes," I heard my wife say. Then I began to move my hips up and down, pulling most of the way off his cock and then settling on it. I did it slowly at first, then I sped up the pace. With each in-and-out movement, I felt an electric shock that started in my ass and spread outward. My wife came close to my ass, staring. “Ride him, Andy. Yes. Just like that. Ride his big cock. God, this is amazing. He is drilling your ass. It’s so sexy.” But Kyle wasn’t able to get the leverage he needed to finish. Suddenly I felt his strong hands grip my waist and pull me off him. “Turn around, baby,” he ordered. “On your belly. Ass up, face down,” In moments he was behind me. He pushed his dick back into my gaping hole, meeting no resistance. I grunted at being taken so forcefully. Now he was in charge, setting the pace. “Fuck me, Kyle,” I said softly. Then, louder, “Fuck my ass. Fuck my boy pussy. FUCK ME HARD!” His weight pressed me down onto the mattress. His thrusts were long and deep, and his balls slapped my ass with each inward plunge. “Cum inside me!” I begged. My wife came around the bed, placed her hands on either side of my face, and looked into my eyes for a moment. I was in a world of pleasure beyond anything I had ever imagined. She kissed me passionately, and I think we both knew it was the last time. And then I felt it, an orgasm that began somewhere in my ass and spread thru my entire body. “Oh, my husband is having an actual sissygasm!” My wife was beside herself with what she had done to me. Only seconds later, I heard the satisfying sound – the deep, manly grunts – of a man cumming as Kyle reached his climax. There was one final momentary pause and then a series of pounding thrusts into my boy pussy. He collapsed on top of me. I turned my head to the side and we exchanged a deep kiss, our tongues dancing. “God, that was fantastic,” Kyle murmured into my ear. There was complete silence in the room. Slowly Kyle softened and finally slipped out of me. I felt empty and very wet inside, and then the odd but delightful sensation as his cum start to dribbled out of me, though I clenched my hole to keep as much inside me as possible. He held me in his strong arms. I never wanted him to let go. Finally my wife spoke. “You two looked so good together. So natural. Andy, I know that Kyle is single. You’re my husband, but I really you should be his boyfriend. What do you say?” I paused. I knew she was right. Our marriage was over at that moment. “Yes.”
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This is a true story of the first time a man fucked me and changed my life. I had had a curiosity about having sex with men for many years before this happened. My perversion and lust is the cause for this life altering interaction, of which I have no regrets; only a longing to dive deeper and deeper into depravity. Masterbating to the thoughts of sucking a man's cock and possibly knowing what it felt like to be fucked as a woman would be was no longer good enough. I wanted to try sucking cock very badly. I was really only turned on by women and transsexuals. A woman's cock would have been preferred yet unlikely attainable. The desire to have a cock down my throat was much too strong so I placed a Craigslist ad in search of a man who I could suck off. It didn't take long before I was exchanging messages with a man much older than myself; I was maybe 22 or 23 he was 48. After some emails had been exchanged we spoke on an instant messenger. I expressed my desire to be fucked by men but afraid to actually do it. Fearing that it would hurt or worse, that it meant that I was gay. He suggested that I start by just sucking cock and after I've had a load shot down my throat I would know if I really wanted to be fucked by men. His logic made sense and I agreed to leave immediately to meet him. He lived 30-40 minutes away and for reasons I didn't understand I felt obligated to get to him as quickly as possible. We agreed that we'd only try oral since I was too timid to commit to penetration and I left. Upon arriving he met me outside on his porch as he was letting his dog out. He instructed me to wait on the porch with him so his neighbors could see me. When the dog finished he made his way inside with his dog and told me to wait while he locked the dog up. I did as I was told. The door reopen and he told me to strip down fully naked and follow him on all fours if I wanted to be allowed in. This surprised me and I tried to resist the request, to which he replied, "I won't wait long" and began closing the door. Immediately I said, "no please" and began undressing. I crawled on all fours into his home, following him to his living room where he sat down pulled out his cock and said, "put this in your mouth." Eagerly I approached his cock and put it in my mouth and started to suck. It was instantly obvious to me that I really liked what was happening! I wanted his cock all the way down my throat and I didn't care if I could breathe. I had been sucking his cock and on his balls for 10 to 15 minutes, all while on my knees still from the floor which was wood. He asked if I'd like to be more comfortable to which I happily said yes. He told me to follow him to the bedroom and that I could stand up and walk now. I followed him down the hallway and into his bedroom towards his bed. I remember feeling very nervous but I wanted to keep sucking his cock. As we got close to the bed he fell behind me, put his arm around my neck and threw me on the bed. He pulled my ass up an placed his cock against my hole and told me to push myself onto him. At this point I was really scared but didn't know what to do so I listened. I did as he said gyrating and rocking my ass onto his cock. It didn't take long before I felt his cock head breach my anus, followed by him fully forcing the rest of his cock inside of me as he told me not to scream. He got really into it when I realized he didn't put on a condom and I got really scared again but once again felt obligated at this point to let him do as he wished. He came inside of me which caused my cock to explode out of sheer excitement. He told me to get dressed and leave, as he was done with me. I drove home wondering what had happened and why I let it happen without any objection. I remember leaving that man's cum inside my guts until the next morning. Ever since this happened I long for men who will use me, hurt me, force and control me. I want to be raped again. Over and over. I want to serve a Master and become his property.
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In September of 2004, I got a message from a guy I knew who lived near Columbia University - seems he had started getting party favors for a couple of guys who were from the Northern Burbs of the city. One was a Professor at Columbia, the other a low-level attache at the Italian Consulate (from Italy). Both were married to women, and both loved to play with big, and I mean BIG toys. Somehow they had met and got together every two weeks at a Hotel in Westchester to spend 6 or 7 hours opening up their up-until-recently straight holes with huge dildos and other fun accessories. And both recently discovered that inviting Miss T to the sessions made them even more intense and fun after the Prof was introduced by some of his students at a non-sexual party. My buddy who provided for them told them he knew someone else from up that way (me) who also got into that kind of play and might be able to show them a thing or two as well. He also told them that like them, I was married but implied that it was to a woman as well. I am not straight (though I sometimes play one on stage, and have fucked enough women) but I was begged to not reveal to them that I had a male partner not a wife, as my bud wanted to see how far along I could bring these guys. They got in touch and I said I'd be happy to play with them - I actually met up with them a number of times over a few months. First time I met up with them, I arrived and they'd been playing for almost an hour. They were each on one of the king-sized beds, surrounded by toys,lube, poppers and the glass cock on the nightstand between them. There was gay bb porn playing, HOWEVER it seems that they barely ever would touch each other. They'd assist in inserting toys, but no kissing or blowjobs or rimming or fucking each other had ever taken place up to this point, it was mostly watching each other. I thought "WTF??". The member of the Italian Consulate was early thirties, hairy, with a wiry soccer player body, modest dick and nice hairy ass. His buddy was a bear-type around 50 plus or minus, caucasian, salt-n-pepper hair, 'stache, chest hair and pubes, and a beaut of a cock. He also happened to be a bit more heavy-set than I tend to go for (no offense!) but was one of those guys that has some kind of chemistry/attitude overshadowed that and so the weight thing never bothered me. They fired up the torch and tried to get me caught up, then gave me a moderate sized toy to begin opening up. Both of their holes were filled with really thick and long dildos and I must admit to being considerably impressed for "str8" guys. Hmmm. This not touching thing was going to be a problem for me, so I needed to figure out a way to bypass that without freaking them out. Shotgunning turned out to work well - something each had done in college with 420 but had almost forgotten about. Taking big full hits on the pipe transferred the tweak-smoke back and forth from my mouth to theirs and their mouths to mine. I confessed to them that I was very oral - "no matter which sex I was playing with" - which led to each allowing me to suck their dicks and rim their holes (neither had ever been rimmed and BOY! did that go over well) so long as I did not mind if they did not reciprocate, which this first time, they did not. It would take a couple of sessions in total, but eventually I got them to the point where they would kiss me and each other, shotgun each other, and suck my dick and rim my ass (though not each other on the last two, oddly). In return, they got my hole more open than it had ever been before and has ever been since, and I continued to be astonished at the girth and length of the toys they would use on themselves and assist each other with. At my second session with them, my suggestion of booty bumps for all of us (which they'd not yet done) led to me getting a fist into both of them, again a new experience for each but my hand and wrist while not small were still smaller in diameter than some of their toys, so I knew that they could handle it. The professor confessed he'd fantasized about that, and the Italian shot wildly when I started a twisting motion in him, laughing and crying as he pumped a load all over the three of us. This was all very fun (though I felt sneaky) but as a top/versatile not fucking was bothering me a bit, I must confess. They both agreed we could all "give it a try" the next time, for without my saying so, they seemed to think that I'd never fucked or been fucked by another man and that it would be new for all of us. Cool. Except they insisted that of course we would all want condoms. So the next time, along with toys and ff we all bottomed and all topped. Surprise, surprise, they liked it. As we got more tweaked that session I would occasionally allow my hole to be in contact with a bare cock while we were doing something else and have the head just kind of pop in for a second or two before "noticing". And if I were behind one or the other, somehow the tip of my dick would brush across the entrance of their holes and teasingly linger for a moment. That was where I left it for that session, allowing them the choice. From then on fucking and fisting were always on the menu though toy play still made up about 50% of the sessions. The amount of favors per session increased as well. Then, a session or two later, the time got changed when I got the call and I arrived to find just the professor. I asked where our Italian was and he told me he was coming at the normal time, but the Prof had reserved the room early because he'd been fantasizing about getting fucked bareback and wanted an hour for me to fuck him prior to the full session. It seems since we'd begun sucking and fucking, he'd been visiting glory holes and ABS locations to do oral. And now he said he just had to feel a raw fuck - so we did, in a very intimate fashion and he shot from being fucked. The rest of the session was much like usual, until the Prof went to clean up around the time the sessions normally broke up and the Italian asked me if I had to be anywhere immediately. Responding in the negative, he told me to go out as if I was leaving then circle around and come back and meet him back in the room 20 minutes after we all "left". And get this, the same damn session, the Italian wants me to stay late for the very same reason the Prof wanted me early! Another hour, a much more animalistic fuck and an exhausted me dragged home after topping that hot hairy euro-hole. Odder still? I never was invited to another session, though my buddy down by Columbia told me they were both meeting each other much more frequently. Did I break the ice for them? Wish I knew!
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I knew from an early age that my ass needed action. As a kid, and young teen, I would stick things in my ass, play with ass and even fashioned a dick from a large carrot. My first time getting fucked half way was when I was 18. It was OK, but not what I imagined. When I was in my late teens and early 20s, I discovered the bathhouses (this was the mid- to late "70s). The first time in a bath house was in Washington, D.C. Now, I had been with women, but I was amazed at the variety of and shapes of guys and cocks! Although I felt more of a bottom, as a good looking young guy, I was hit on frequently. In the steam room , guys would reach for my cock and engulf the thing. I am not huge, about 6 inches cut, but the guys said it was a nice cock. Who am I to argue? The bath houses were and on- and off-again thing. There would be months with no visits, then weekly. For the most part, I led a very vanilla life. During the process, I graduated from college and ended up in Cleveland. After about a year in Cleveland (this was 1980), the urge to hit the bath houses again was strong. So, one night , I ended up at the Club Bath on West Ninth Street - no longer in business (there were two Club Baths in Cleveland then, the downtown one and one on Detroit Avenue). Anyway, I digress. The Club Bath had a street entrance, with three levels. The basement level had the showers, steam room, orgy room and was where the action got hit. Friday and Saturday night were packed from 10 p.m. until 4 a.m. or do. Guys, guys, guys. Cocks, cocks, cocks. Whew. About six months in into my weekly visits, I decided to try a Sunday afternoon. My purpose that day was to get fucked. I got a room, bought some lube, and went hunting. From my room on the main floor, I walked down to the orgy room - which was a maze of interconnected rooms, with small mattresses, glory holes and little nooks for public or somewhat private action. It was slow, but in one of the rooms was a very tall blond-haired guy with silky hair and a trim body. Slowly, I walked over, and before I could even make a play, off came his towel to reveal the best cock I have ever seen. He had been stroking and was semi-erect. A nicely shaped mushroom head meant for sucking, and long - oh-so-long. At least nine inches. He could have been a cock model (as it turns out, he was a hand model). He had a nice low hanging ball sack. We stoked each other, and then he simply put a hand to the back of my head. I knew what he meant. So, dropped to the knees and began licking his balls, and sucking them gently in my mouth. Then, I licked up his shaft and let my tongue slowly dance around the glans. "Enough," he said, grabbing me and pushing that perfectly shaped mushroom head into my mouths. I sucked on it and then took him as deeply as possible. Damned, this was one long cock! Then, he stooped me. Pulled me to my feet, and grabbed my cock, and whispered in my ear, "I want to fuck. Have a room?" I nooded, and we replaced our towels and slowly walked the one flight to my room. When we entered, the door shut quickly and I once again started to suck that monster. It was long, hard and almost angry looking, pointing 45 degrees plus upward. For the second time, he said, 'Enough." He pulled me up and motioned to the bunk. Now, I had already taken the precaution to lube myself...but i wondered if it was enough. As if reading my mind, he grabbed the lube and started to slowly open me up with his fingers. In my mind, I wanted to scream, "be gentle," but his instinctively figured my inexperience. He placed me on all fours, lubed his cock in front of me, and then got behind. For the longest time, he rubbed his mushroom head over my anus, prepping me for the assault to come. All the while, he was breathing heavy while I was moaning. Without warning, he pushed. With a pop. the headed entered my tender ass! I groaned. Loudly. He just rocked a bit, wanting me to feel his cock. The pain was searing. But at the same time, I was so exited. Hard as a rock. Wanting more. This guy was great. He sensed when I was ready for more, and started to slide in, deeper, deeper. Then he stopped. Suddenly, I recall saying, "Shit, shit, shit...oh man, I can take it! I can take it! Fuck me." There was a mixture of pain and pleasure, with the pleasure winning out! But he kept slowly penetrating, until, at long last, I could actually feel him hit bottom. "Now, I am going to fuck you," was all he said. He then pulled out a bit, and went back inside. He pulled out some more, and pushed back inside. Then, suddenly, he pulled back with just the still inside, and he shoved hard, one long thrust. "Ugh," was all I could say. Then, a voice from somewhere in the room said, "Fuck me with that monster. Fuck me. Fuck. Fuck. Fuck." I started to push back with each thrust. Again that voice in the room, "Make me your bitch. Fuck me!" I will never forget what came next. He started to hit something deep inside me (I would later learn my prostate). The faster and harder he fucked, the hotter harder I got. "Gonna cum, boy, gonna cum," he yelled. His thrusts were like a piston engine. In. Out. In. Out. The, a huge thrust and he started to grunt. I clamped my ass. I could feel his cock pulsating, and could actually feel his shoot (darned few times in years since). As he was shooting and pulsating, deep inside, I felt a surge of energy and I started to cum. With no touching my dick. In the almost 32 years since, that has not happened often. After we finished, I was spent. He told me that I was a good lay and had potential as a bottom. :-) We chatted briefly. He was pushing 40, married, and was a hand model on the side. I ran onto him a few times after that, and we fucked, and there were always fireworks. But that chilly March afternoon in Cleveland, I learned what it was like to be "really" fucked.
