Date: Tue, 8 Jan 2013 18:31:46 -0500 (EST) From: Wolf Pomo Subject: Daniel Choses Boarding school, (gay/adult youth, oral, anal, doc, b/b, bb/MMM) DISCLAIMER: This story is a work of fiction and contains descriptions of explicit sexual acts of boys and men discovering their sexuality. It contains graphic scenes of sex between consenting underage boy and adult males... If this type of content offends you or you are under the age of 18 do not read it. Author's Note: This story is the property of the author. It can be downloaded for personal reading pleasure or sending to a friend, but if you wish to re-post them at your own site, please contact the author for permission. If it is illegal to read such material where you live or if you find the topic distasteful the please leave now. If you enjoy the story or if it evokes memories of your own, please let me know. I am happy to write stories from outlines. Copyright 2012 Wolf, All rights reserved. You may contact me at whitewold999@icqmail.com if you like. All flames will be ignored. Daniel Chose Boarding School By Wolf My name id Daniel or Danny to my friends, and my family lived Fairfield Connecticut, on Reef Road, just off of Old Post Road, back in the early fifties, when I was eleven- years-old. Our home was more than a hundred years old, but it had been remodeled times to include indoor plumbing, bathrooms, and enough electrical upgrades to accommodate the latest electrical appliances for the time. The house next door was just as old and had been upgraded too. Their family had a son a year or two older than me. His name was Ralph, his was my best friend, and the only male nearby close to me age, so we played games with each other, but now and then we would be at his house. His mother worked so we often had the house to ourselves. Like most homes in the areas his house had a basement that was completed not only for storing storm windows and canned fruit jars, it was the most comfortable room in the humid summers. It was far more than a recreation room. We would retreat down there to look at old automotive magazines and the occasional 'National Geographic' magazine with naked native women. One such afternoon Ralph reached up into the beams and pulled out a paper bag that contained three decks of playing cards. He selected a pack of cards and opened the pasteboard box and selected the deck of cards to hand to me. The face of each card not only contained the value of the card, each one had a picture of men and women sucking and fucking. The pictures were of poor quality, and the men had on black socks and masks. Their bodies had a lot of dark pubic hair, as did the mostly chubby women. I vividly remember feeling my little 4-ich cock getting stiff while looking at the cards. I couldn't help rubbing my crotch slowly. When I was finished examining all 52 cards I asked Ralph if I could look at another deck of cards. Ralph had been watching me and had been rubbing his own crotch. He said, "Maybe next time!" as he put the cards back on the paper bag, and returned it to the hiding place. The next few days I kept thinking about those pictures on the playing cards, just thinking about them pictures in my bed made me so horny that I had to rub my crotch. About five days later I had to ask Ralph if he would show me the other decks of cards. He escorted me back down to the basement, and retrieved the bag again. We sat together on the couch, as he handed me the second deck of cards. As I started flipping through the cards I found it hard to hold the deck of cards and rub my crotch at the same time. Ralph took the deck from my hand, and said, "I will had you each card one at a time!" We were both looking at each card in turn, while rubbing our dicks. Ralph would whisper his comments in my ear, like look at his cock, and what a nice ass she had. All of the visual and oral stimulation had its effect on me. I would say, "Oh yeah, oh yeah! Ralph said, "Look at that he's got his tongue right in there, I bet that tastes wonderful!" The woman in the picture was sucking the cock of the man. Ralph whispered in my ear, "I would love to have my cock sucked like that, wouldn't you?" "Oh yeah!" I said. Ralph leaned even closer and licked my ear. It tickled, but it felt good too. He took hold of my hand that I had been rubbing my crotch with and placed it on top of his crotch. I felt his cock throb, and I pulled my hand away. He quickly pulled my hand back to his crotch. I could feel just how hard his cock was. He assured me that my hand felt good on his cock, and then he inserted his tongue back into my ear. While he was doing that I felt a tingle through my body. I whispered in his ear, "Take it out I want to see it!" He casually unzipped his pants, and his cock sprang out, because he didn't have any underwear on. I would have guested that it was 5 or 6 inches long, with a large mushroom head that he was stroking slowly. He took hold of my hand again and placed it on his hard cock. I wrapped my fingers around the shaft. He was whispering in my ear just how great it felt to have me jacking him off. He continue licking and kissing my ear. Soon there was a clear liquid drop appeared at the opening of his cock. I asked, "What is that?" He wiped it off with the tip of his finger and placed his finger on my lips, and said, "It's cock honey!" I ran my tongue over my lips and it was sweet. Ralph licked my lips and kissed me on the mouth. I actually liked the smell and taste of it all. Another droplet appeared at the opening, so Ralph told me, "bend over and lick it off and them kiss my cock!" I didn't even stop to think about what he was asking, I just bent over licked the drop up, and then have the knob a wet kiss. Ralph pulled my face to his and kissed me on the mouth. He actually slipped his tongue into my mouth. About that time we heard the sound of the door upstairs opening. Obviously his mother was home, we jumped up, and pulled up our pants, before returning the cards to their hiding place. Every night I would think about what we had been doing while I was playing with my cock under the covers. I was eager to repeat what we had done. It was a few days before we worked up the nerve to get back together again. This time Ralph's mother was away for the weekend at her sister's home in Southport. We headed straight for the basement and sat together on the old couch, Ralph had already retrieved the bag of cards. This time he pulled out the third deck of cards. He told me that this deck was a little different from the first two. Before he put his arm around my shoulders and kissed me on my ear. When I opened this deck of cards my mouth fell open. The photographs were all of young boys no older than me and some even younger. They were on their knees sucking the large fat cocks of old men with pot bellies. Ralph was running his hand up and down my leg while he whispered, "How do these pictures make you feel?" I really was unable to answer the question. The following pictures were of close ups of the fat cock deep in the boy's mouth. Ralph kept the cards coming, while he rubbed my cock. While I was busy studying the pictures, Ralph stood up and removed his pants right in front of me. Again he didn't have on underpants, but he did have on women's dark nylons and black garter belt. His cock was bigger than mine and he had some hair above his cock, not as much as the old men in the pictures though. He told me to kiss it like before. I leaned forward and kissed it, and started to lick it. He said, "I want you to put in in your mouth like the boys in the photos." I opened my mouth and took it into my mouth until my nose was pressed against those few hairs. "Now suck it!" he demanded. He placed both of his hands on the back of my neck and slowly began to slide his cock in and out of my mouth. I can't say why, but I loved it. I had no problem doing exactly what he wanted. I actually like the feel of the nylons as I ran my hands up and down the backs of his legs, while sucking on his cock. Ralph suddenly pulled his cock out of my mouth and turned around. He presented his butt to me as he bent over and spread his cheeks open. His rosebud of an asshole was just inches from my face. He had applied lipstick to his asshole, while he was puckering his rosebud he demanded, "Kiss my lips!" I couldn't resist leaning forward and partly opened my mouth on his ass lips and kissed it. I was kissing it for two or three minutes, before he wanted me to lick it and stick my tongue into the open hole. I not only enjoyed doing it and actually produced my own pre-cum for the first time while I was playing with myself. I really enjoyed sucking on Ralph's cock and licking his ass. I still remember the first time he cum in my mouth, he tried to warn me that he was about to shoot his load, but I just kept sucking until he filled my mouth with three strong squirts of cum in my mouth. For me it tasted wonderful as I swished it around in my mouth, so that I could savor the flavor. I liked the slimy texture, and the distinct odor. I sucked his cock clean every time he used my mouth. I noticed that the longer I tongued his asshole the bigger my reward when I sucked his cock. I couldn't get enough of his cum. Whenever I visited him we stared by looking at the decks of cards. He preferred the ones with the men and boys sucking and fucking. My favorite card was of two men and a boy, the boy was sucking one man's really large cock that filled the boy's mouth, while the other man had his cock buried deep in the boy's ass. I even showed the card to Ralph several times, and assured him that I would love to suck a big cock like that. Ralph asked me, "Would you like to get fucked by a big cock like the kid in the photo?" I said, "I guess so!" Ralph said, "It will hurt like hell at first, but it gets better and better with each time you get fucked!" "How do you know?" I asked. Ralph just said, "I know, believe me!" We plaid every chance we got. I loved licking his asshole and sticking my tongue deep into his open hole. Ralph always me sucking his cock and swallowing his cum afterwards. One afternoon we started had the cards out while playing with each other. Ralph and I were kissing while we were sucking on each other's tongues. I unfastened his pants so they could fall to the floor. He had on his nylons and garter belt. He lifted and half hard cock up, so that I could squat down and start licking and kissing his balls, while I caressed his nylon clad legs. His cock grew hard, and I licked his pre-cum from his cock, while he moaned with pleasure. While I was clinging to his hips, I turned him around because I was eager to get at his sweet asshole. He bent over and used both hands to spread his cheeks open. I noticed that his asshole was red and inflamed, so I asked, "What happened to your hole?" He calmly said, "A man had just fucked him, and filled him with hot cum just for you! Do you want to eat it out?" Without another exchange of words, I clamped my mouth tightly on his swollen asshole, and sucked as hard as I could, as I worked my tongue deep inside. I could taste what was left of the man's cum and savored it. Later I sucked Ralph's cock and he shot the biggest load ever into my mouth. Later after we calmed down I questioned Ralph about the man he and mentioned about depositing the load in his ass. He said that he had this older friend that lived in one of the beach cottages down at the end of the Reef Road on the sound. I asked how old he was, and Ralph told me that he thought that he was in his forties, and he had some gray hair. I asked, "You said that he fucked you?" Ralph said, "Yes! Sometimes his friends also fuck me." "Does he have a big cock?" "Yes, they all do!" he said. All I could think about was all that hot cum. Ralph said, "He wants to meet you this Saturday if you can go with me!" "I will make sure that I can go with you!" I was anxious for Saturday to arrive the rest of the week. I had arranged with my parents to go bike riding with Ralph in advance, so we rode our bicycles south to Reef Road towards the beach. I followed Ralph up the driveway leading to a large beach house in gray with white trim. We parked or bikes on the fence and walked to the side door and knocked. Ralph whispered, "Don't speak to him unless he asks you! Got it? "Yea, I've got it!" I responded. When the door opened I was looking up at a tall man with a dark tan and graying hair. The man spoke directly to Ralph without taking his eyes off of me. "I take it this is your young friend that loves cum." "Yes Sir." Ralph said. "Well come in and have a seat son, and Ralph go get dressed, while I entertain your young friend here." The man ordered. Ralph went down the hall, while the man took me by the hand and walked me over to the couch. He sat down and had me stand in front of him. He casually spread my legs without saying a word. As he pulled me straddle of his knees he asked, "Would you like to get naked for me boy?" His size and manner frightened me more than a little, so I started stripping down to my shorts and underwear by removing my T-shirt. I had to struggle to pull down my shorts and my underwear past his legs, but eventually I was standing naked in front of a grown man with my little hairless 4-inch cock sticking out in front of me. It was an exciting thing for me, because I didn't know what he was going to do to me. He reached out with his right hand and took my dick and balls in his hand, to pull me closer towards him. He placed his left hand on the back of my neck as he pulled my head down so that he could kiss me on the mouth. He practically drove his tongue down my throat. When he pulled back he licked my ear and said, "You're a hot little cock sucker!" His left hand slid down the back of my body to my round butt, and his fingers entered the crack of my ass, seeking out my puckered sphincter, and a he toyed with my puckered sphincter. He whispered, "You have never been fucked have you?" I said, "No!" He said, "Well this hole is mine! I'll take your cherry when I'm ready...GOT THAT?" I contritely said, "Yes Sir." "I'm going to tell you what is going to happen today, I'm going to fuck Ralph, and you're going to watch! I might let the two of you play around a little!" At the end of his statement he withdrew his finger from my ass, and placed his finger against my lips. "Suck it...and get it good and wet!" Then he returned his finger to my puckered sphincter and worked it into my hole. My sphincter clamped tightly shut causing me instant pain. I squirmed under the constant pressure, and let out a painful plea for him to pull it out. He said, "You're going to be a hot piece of ass, and my horny friends will love you!" At that point I hear footsteps as Ralph reappeared, and I almost didn't recognize him. He was standing there with his nylons, high heels, garter belt, lace panties but he also had a wig with a little girl's two braids, makeup that included lipstick. The man still had his finger in my ass, as he ordered Ralph to come over and stand next to me. "I want you to start kissing this sweet little boy on the mouth." We embraced each other while Ralph started kissing me passionately. After a while the man ordered me to pull Ralph's panties down and suck his clit! When I pulled the panties down, Ralph's cock was rock hard. The man told Ralph to assume the position on the couch on his knees and cross his arms on the back of the couch to rest his head on his arms. When Ralph assumed the position, the man told me to pull down his panties, and eat his asshole! While I did as ordered the man moved behind me and told me to get Ralph's asshole really good and wet. I was enjoying following his orders. Eventually he ordered me to turn around. When I did as ordered my face was less than a foot away from the biggest man cock I had ever seen or hope for. The man ordered me to make love to his cock with my mouth. I started licking the head of his cock, and wiping up the pre-cum oozing out of his hole. His pre-cum was even sweeter than Ralph's. I was doing my best to impress the man, while I was sucking his cock. The man handed me a bottle of baby oil and instructed me to oil up his cock. I opened the bottle and poured a generous amount of oil into the palm of my hand before spreading it all over his cock. When I was finished, he told me to oil up Ralph's asshole- pussy. Ralph turned his butt towards me and bent over, while I applied oil to the opening and stuffing greasy fingers up his asshole. As soon as I finished the man pushed me aside, and told me to have a seat, and watch closely what he was doing to Ralph. I sat on the couch only a matter of a couple of feet from their hips as I watched the man pressed his massive cock head against Ralph's puckered sphincter. It entered with a wet popping sound as the man suddenly push his hips forward. Ralph let out a cry and whined "OH GAWD, OH GAWD, please!" I would have never thought a asshole could stretch that much, but there it was as the man's cock disappeared in the hole. Ralph was wiggling his but around as the cock slid balls deep into his ass. The man remained motionless for a short time while Ralph got accustomed to the way his asshole was stretched. Eventually the man started stroking in and out of Ralph's ass. Ralph's ass lips had a tight grip around the shaft of the cock. Ralph's moans became moans of pleasure. I moved my body until I was close to Ralph's head and whispered, "Are you okay?" He said, "Yea, you can't believe how good it feels! He let out another moan, and said, "Suck my cock...please." I slid off of the couch and onto my knees under Ralph and took his cock into my mouth and started sucking on his cock. From where I was perched I had a great view of the man's balls swinging as he fucked Ralph. It didn't take long before Ralph's cock swelled up in my mouth, and he moaned as he dumped his load of cum in my mouth. I didn't swallow it right away. I wanted to savor the taste for a while. The man said, "Get up here Danny, I'm about to breed your friend's ass!" I got out from under Ralph and sat on the edge of the couch, leaning forward close enough to their hips that I could smell Ralph's ass, as the man began to jerk a little as he pumped his load of cum deep into Ralph's bowel. The man held tightly to Ralph's hips and pressed his crotch tightly against his butt for a while before he relaxed and pulled back. His shinny cum coated shaft slowly appeared, coming out of Ralph's asshole. Ralphs sphincter clung to the shaft as the man pulled his cock out. As soon as the man turned his body towards me I began to lick the nectar off of the shaft. I eventually got my mouth over the knob. His cum was very white and creamy textured. It was like swallowing snot. Ralph's cum was a little more translucent. As soon as I finished sucking the man's cock clean the man grabbed my head and shoved my face into Ralph's open asshole. He commanded, "Suck every drop of my cum out of his boy pussy!" I happily complied with his command. When the man was satisfied that I had done a good job, he allowed the two of us to set down while we discussed my inclusion into their world. He told me that I was to address him as Daddy. Ralph was to be addressed as Rachel within the house. I was to be known as Daniela. To emphasize his point he told Rachel to go get me the appropriate attire. When he reappeared he was carrying a blonde wig, high heels, nylons and a garter belt. Ralph and the man helped me pull up the nylons. They were cheap looking dark fishnet stocking that looked like something a cheap hooker. They were panty hose, but the large nets allowed my balls and cock poked through the mesh. While ralph put my feet into the pumps, the man fitted the wig onto my head. Getting me all dressed up was enough to give me a hard-on. When I was dressed up like Ralph the two of them led me to a sturdy cocktail table and placed me on my back. Rachel (Ralph) sucked my dick while Daddy applied copious amounts of lubricant to my asshole and his cock again. When he was satisfied with his efforts to grease me up in preparation of my first fuck, the two of them positioned my body on the table like a sacrificial lamb. Daddy picked up my nylon clad legs and placed my heels against his shoulders while he aligned his cock with my rosebud of an asshole. He cushioned me to push like I was taking a shit or it would hurt even more. When he started inserting the head of his cock into my ass it did hurt terribly, but he was also assuring me that after a few fucks I would crave cocks in my ass as much as Rachel. While Daddy was slowly inserted his big cock into my ass, Rachel turned his back to me and sat on my face. He was in effect muffling my sobs and moans of pain with his asshole. As painful as it was to have my sphincter stretched so much there came a point that I sprang a boner and ejaculated pre- cum all over my belly. Daddy explained to me later that while he was fucking me the head of his cock was rubbing against my prostrate, which caused me to have an orgasm. Afterword's Daddy applied something to my asshole that stung for a moment before my asshole went numb. Daddy cleaned Rachel and me in a tub before we put our clothes back on before we rode our bikes home. I can tell you that it was hard to sit on my bike's saddle for a couple of days. Regardless of the pain I relived the experience every night while in bed. I even kept an old towel handy just in case I produced pre-cum or had my first cum. When my asshole stopped throbbing is when I asked Ralph about visiting Daddy again. He called Daddy and made a date for us to visit. He selected a weekend when our parents thought we were going on a camping trip. We packed up our gear and tied them on our bikes, before we headed for Daddy's place. We parked our bikes I back and knocked on the back door. When Daddy admitted that we change clothes before we came to the living room. We used the extra bedroom to get doll up as Rachel and Daniela again. We even put on makeup, before we made our grad entrance into the living room. When I entered I pulled up short, because I had expected that Daddy would be the only adult in the room. It was a shock to see another man sitting there on the couch. The second man was a portly man I would have guessed was at least in his fifties. He had a rugged build, and a full beard matching his gray hair. If I were to guess I would have suspected that he was a local cod fisherman. His hand were callused and scared by healed cuts. He was dressed in working class clothes including rubber soled non-skid deck shoes. Daddy said, "Come in girls an meet our guest for the weekend. Girls this is my friend Michel O'Bryan. Mike this is Rachel and Daniela my little girly boys. Girls come here and welcome our guest!" When we approached the man he grabbed both of us and sat us on his lap. We were perched on each of his thighs, so that he reached around our waists and played with our clits. It was very strange to me to be kissed by a fully bearded man. His whiskers tickled my face. We were encouraged to undress the man. When we got his work shirt off I saw that he was very hairy. He had clumps of hair on his shoulders and back. There was plenty of hair between his man tits. The only bald spot was his big round belly. We had to stand up to get his pants off. When we pulled down his pants we exposed his big baggy boxer shorts. The front of the fly was stained slightly yellow. When we pulled down his shorts I was fascinated by the sight of his genitalia wedged between his thick thighs. His cock was as short as mine, but it was thick. His little cock was perched on top of the largest pare of balls I had ever seen. His balls were as large as a softball. They were like on big pink ball with a seam running down the middle. He casually explained that he had a hydrocele in his balls. He had to explain that he had injured his balls as a youth causing the scrotum to be filled with fluid. It felt so strange to hold such large balls while bending over to suck his cock. Rachel had to work hard to spread the fat man's butt so that he could lick his asshole before inserting his cock into the fat man's asshole. We had a great time making love to him. Sucking on his tits were like a woman's except for the hair around his nipples. As the evening approached Mike excused himself and got dressed to leave. Daddy instructed us to put our panties back on, because there was another guest arriving soon. It was only a short wait before there was a knock on the door. When Daddy opened the door I was struck by how much the tall man reminded me of Disney's Ichabod Crane from "The Legend of Sleepy Hollow." He was a tall very slender man. His face was very angular. When we were introduced to him, his long fingers engulfed our hands. When we joined him on the couch he was so tall that Rachel and my head rested under his armpit as he wrapped his arms around us. He hands rested on the bulge in our panties. He had to bend over to kiss us on the mouth, as Daddy introduced our guest as Mr. Clark. He was dressed in a dark three piece business suit. When Daddy gave us permission to help our gest out of his clothes it took us a lot more time to remove his clothes. I was impressed that his body was almost hairless. His body didn't seem to have any fat on it. When he stood up so that we could remove his shoes before his pants I could feel how slender his legs were through his pants. He also had on boxer shorts, but they were clean. We were both truly impressed when we got his shorts off. His pubic area was shaved smooth, but we didn't see a cock at first. When he spread his legs we saw that his cock was tucked between his legs. It was held there because he had his cock stuffed into his own asshole. When we pulled it out we were amazed because his long slender cock was the longest thing either of us had ever seen. His cock dangled almost all the way down his thigh. His cock head was covered with foreskin that dangled well beyond the end of his knob. I had never seen a cock with so much foreskin before. I asked him about his foreskin. Mr. Clark smiled as he said, "I was born with plenty of foreskin, but I also worked hard to stretch it so that I can dock with lovers!" Rachel and I were both confused with the term 'Docking.' He saw our confusion and offered to demonstrate how to dock. It took some maneuvering for him to get me perched on my knees on the couch to elevate my hips level with his hips. Then he lifted his cock up and pulled back his foreskin and placed the tip of his cock against the tip of my little boner, and proceeded to pull his foreskin over the shaft of my cock. Then he wrapped his hand around our cocks and proceeded to jack me off. It felt as good as when Rachel let me fuck his asshole. I even ejaculate some pre-cum. Rachel was excited about him doing the same to him. When Rachel cum, Mr. Clark pinched the end of his foreskin tightly before presenting his cock to my mouth. I opened my mouth widely to allow him to place the foreskin my mouth before slowing the cum to spill into my mouth. I used my tongue to clean out all of the cum under the foreskin. When Mr. Clark wanted to fuck my ass, I was apprehensive about the prospect of a cock so long being stuffed into my ass, but after he got the knob past my sphincter the rest of the shaft entered my ass without any more discomfort than any other time. I found myself becoming very attracted to him. When the evening drew late I maneuvered the bedding arrangements so that Rachel slept with Daddy and I slept with Mr. Clark. I found out that he actually was a teacher like Ichabod Crane in the story. I learned that he taught in a boarding school. He told me that almost all of the graduates were admitted to the finest colleges. I sucked him several times and he fucked my ass several times too. By morning I was convinced that I had to convince my parents to send me his boarding school. If you enjoyed the story and have a story you want me to write about your introduction to the world of male sexuality, please send your outline to whitewold999@icqmail.com