Date: Wed, 11 Jan 2012 09:56:56 -0800 (PST) From: Beautiful Creamer Subject: Sissyboy Matchup (gay adult-youth) Sissyboy Matchup By Beautiful Creamer Josh Pantydropper shook his head when his mother gave him the news. Could she have really said what he thought she said? She could. "It's time you started dating, Josh. My special friend, Carlos, and I need some time together and it'll do us all good if you're dating while Carlos and I are...talking about things. You're plenty old enough to date." Old enough? Josh would be eleven in five weeks. He hadn't even really thought about dating. Though he was starting to feel the rumblings of puberty in his pretty, pink testicle bag. Josh knew that boys and girls..."did it"...to make babies. Though "it" was a concept still unclear to the boy. Girls weren't looking in Josh's direction yet. The ones who were looking at boys were looking at the bigger, muscular, jock boys. Especially the older 12- and 13-year-old boys at their middle school. Josh didn't get that kind of attention. He was smaller. Skinnier. Not really manly handsome. Josh was pretty. As pretty as the girls. Prettier. As pretty as his gorgeous mother. All of which could have distressed him if he'd overthought it. Josh didn’t. He had plenty on his mind already. His single mom was young and sexy. Men were circling the house in packs. And Josh knew that he was a cramp in her style. But he never thought she'd be matching him up with some girl he didn't know, handing him a $20 bill and dropping them off at the mall for eight hours while Mom and her latest mantoy did the dirty. That was how Josh envisioned his fate. He couldn't fight Mom. So he surrendered. Working with her to fill out accurately the matchup.com questionnaire about his likes and dislikes. Even the age part. Which Josh figured would end things right there. No reputable online dating service would match a 10-year-old boy with anyone. Wrong again. Three weeks later, at four o'clock on a Saturday afternoon, Mrs. Pantydropper gave her son the news. “You have a date tonight, Honey. And so do I. So get ready. Your date will be here at 5:30. And Dieter, my date, will be picking me up at 5:45. Take a nice bath and put on the clothes I left on your bed. Let's go now. Move it!” Move it? Josh was frozen with fear. Matchup.com had arranged a date with Josh through Mom? How was that possible? What kind of girl would be showing up in 88 minutes? And who was “Dieter?" Wasn't Mom dating Carlos? Mom could be quite insistent. So Josh proceeded to his bathroom and took the ordered bath. Filled with dread and confusion, the boy then wrapped a towel around himself to go to his room and get dressed in the clothes Mom laid out. Until he saw them. It had to be a mistake. No girl, addled enough to use an online dating service at age ten or not, would want to see Josh in that! Mom had purchased an ensemble that screamed "Sissyboy!" Tiny, denim short-shorts that would barely cover Josh's bottomcheeks. A frothy-pink baby tee that was at least a size too small. Sandals with thin, girlish straps. And, worst of all, a pair of what looked like the kind of panties a girl would wear. And they were pink! Josh's knees were weak with fear! Mom wanted to humiliate him in front of a girl. But why? Josh rarely confronted the Pantydropper matron, but enough was enough. Still wearing the towel from his bath, Josh knocked on Mom's door, waited for permission, then entered. Josh loved his Mom, Amber Pantydropper. The sight of her in full feminine battle array still stunned him now and then. She was seated on her vanity stool in front of a large mirror that was probably enjoying what it had for reflection. The 29-year-old woman was stupefyingly beautiful. Her magnificent visage was framed by a thousand natural-blonde curls. Men would gaze upon her full, red lips and instantly envision the presence of those lips on their cocks. Mrs. Pantydropper was dressed only in her lingerie. Lacy, black bra that was straining to contain her 44-DD breasts. Black, seamed, fully-fashioned, reinforced-heel-and-toe stockings that encased her long, shapely legs. Matching panties and garter belt. An ensemble that would probably inspire...Dieter, was it?...to unmatched achievements later that evening. Josh sighed. His Mom was so beautiful. The boy imagined what it would be like to be the object of so many men's sexual desire. Josh knew he would never have that in his life. From girls, anyway. And the thought had never formed of men desiring him in ways that men desired his Mom. "Yes, Honey. What is it?" Mrs. Pantydropper asked her son as she interrupted the finishing touches of her makeup application. Josh decided to play the sniffle card. "Mom," the boy sobbed, "I can't put those clothes on. I couldn't leave the house like that, let alone go on a `date' dressed that way." Mom smiled. “Of course you can, Honey. And you will. The people at matchup.com suggested those clothes for maximum success on your date. Now run along and get ready." One last try. "But, Mom. I'll be humiliated. No girl would want to be seen with me dressed like that. Who is this girl anyway?" Mom patted her son on the head and said, "All in good time, Josh. Don’t be so impatient. Scoot. Now!" Having no apparent choice, Josh surrendered. He dried his hair and combed it. Then slid on the panties. Which felt surprisingly good. Silky. Rubbing nicely against his boy's things. Then the short-shorts. Which looked even shorter on him than they had looked on the bed. Ick! He was showing double bumcheek. And while he had very lovely bumcheeks, Josh was going to be mortified to show them off to his "date." And everyone else they would see. Maybe they could go to a dark movie. A really bad, long movie with almost no one in the theater. Then skitter home to end the whole fiasco. Josh put on his shirt and strappy pink sandals and looked at himself in his full-length mirror. Which was mostly depressing, except that... Josh saw something in that mirror that he didn't expect at all. Josh was hot. Really hot. The wrong kind of hot. The most wrong kind of wrong hot. But hot. Some of the people Josh saw that evening, Josh concluded, would see that wrong hotness as well. Which was 90% terrifying and 10% thrilling to Josh. Who wanted to be desirable. But certainly not in a faggy, sissyboy way. Josh pondered this and that for a while until he heard, "Josh, your date's here." An icepick of fear stabbed Josh's heart. He took a huge breath, disconnected himself from the mirror, and slowly walked downstairs to meet his date. Where was she? Mom was standing in her big heels and little black dress, talking to a man. Who had to be Josh's date's father. The man was the right age for that -- 40-ish. Too old to be Mom's boyfriend. She liked them aged 18-23. Prime spunking years. Good, Josh thought. The girl's father would see Josh tarted up, recognize that he was bad for his daughter, and abort the mission. Mom would call one of the regular babysitters, who would sit and text all night while Josh watched TV and played video games and that would be that. But there was a disturbance in the Force. Josh could sense it. The man was standing two feet from Mom and he wasn't aroused by her. No lump in his pants. No fawning admiration. No dreamy smile aimed in her direction. Oh no. The man was turning his head and looking at Josh. Giving Josh that dreamy smile that Mom always got. And Mom was saying, "Oh, there you are, Josh. This is Mr. Longthrust, your date for tonight. Say hello, Honey." Josh couldn't say anything except emit a loud gasp. Through the frozen fog of fear, Josh could hear Mom saying to Mr. Longthrust, "...my emergency number, but I trust you won't need it. I see you brought a bag with everything you need. Dieter and I should be home around ten tomorrow morning. I'm sure you and Josh will get along very well on your date." Then Mrs. Pantydropper kissed her son-statue goodbye, shook Mr. Longthrust's hand and scooted out to the curb where Dieter was waiting with both the car's and his motor running. Leaving her ten-year-old, virgin son alone for 16.5 hours with a dating-service-avowed boylover. Josh's every corpuscle was alert to opportunities for flight or fight. Neither would be necessary. But Josh didn't know that yet. "I'm very pleased to meet you, Josh," the man said to the boy. Josh's eyeballs unlocked just enough to allow the boy to see Mr. Longthrust's hand extended for a shake. Reflexively, Josh took the crazy pervert's hand and shook it. Oh my! The man's palm was sweaty. He was as nervous as Josh was, Somehow that relaxed Josh just enough that he was able to breathe without mechanical assistance. Why was Mr. Longthrust, if that was his real name, nervous? Men were nervous around Mom all the time but that was because she was so gorgeous and sexy and desir... Wait! Did this man think that Josh was gorgeous, sexy and desirable? Apparently so! Josh was getting his wish. But in the wrongliest wrongness of wrong ways. Josh released Mr. Longthrust's hand. And waited. Warily. “Your mother told me you were beautiful,” the man said, “and I saw the pictures she posted of you on the matchup.com web site [WHAT PICTURES!?!?!], but you are just miles prettier than any prettiness I could even imagine." Josh blushed crimson at what was the greatest single compliment of his life so far. Which was not entirely unpleasant. The boy knew he deserved praise for his beauty, but not from a man. A man who was probably figuring out a way to kiss Josh. Right on the lips! And maybe even [gasp] try to do other stuff too. Like the kind of stuff Mom and her men did on their dates. When Mom would roll in at three a.m. with her hair and makeup all messed and walking stiffly. But really happy. Well Josh wouldn't be one bit happy if this man tried anything with him. But apparently, his "little man" had other ideas. The man's praise of the boy's beauty had "stirred things up" a bit in Josh's pubic area. And despite all the boy's rational thoughts, Josh's already tight short-shorts had tented. Not a Barnum and Bailey's Big Top. More like a pup tent. But a tent. A shameless tent. Mr. Longthrust noticed. The boy's blush deepened. How would he ever survive the next 16.4 hours? Maybe if he grabbed a butcher knife, he could defend himself and his honor for a 16.4-hour standoff. Mr. Longthrust changed the subject. "I'm not much of a cook. But I thought we could go out for pizza. Unless you want to order pizza in. Do you like pizza, Josh?" How to answer that? Josh liked pizza. He didn't like going out in public looking like Miss July on that year's sissyboy calendar. Nor did he relish the thought of staying in with Mr. Pervo all night. What to do? As Josh pondered his response, Mr. Longthrust said, "I want to thank you so much for spending some time with me, Josh. The computer at matchup.com said we were perfect for each other, but you never know until you meet someone. I guess your mother told you that she was worried that you were entering puberty and had no Daddy to teach you what a boy should know about sex. So I guess the computer sent me to be your stand-in Daddy." There was a new wrinkle, Josh thought. If it was true. Mr. Longthrust went on. "When girls reach puberty, they need a Mom to tell them about menstruation and breast care and the nagging, manipulation and emasculation of every man they meet. Boys need to learn about their changing bodies too. And your Mom, who does your laundry, says you've been having wet dreams for a couple of months now. So it was time." Did Josh have no privacy? It was true. He was ejaculating. Involuntarily at first. But then, three days earlier, Josh had been in bed thinking about the girl he would be meeting if Mom's date craziness ever came through. He touched himself that night. And it happened. And then... "Do you ever play with yourself, Josh? The man was a mindreader. And a nosy beast! But maybe, just maybe, Mom was right about him needing a grown-up male advisor at that time in his life. So taking a small leap of faith, he answered truthfully. "Just once. Three days ago." Mr. Longthrust beamed. That was the icebreaker. By his estimate, his manly rammer would be splitting this young beauty's peach in less than three hours. "Did you make boy's cream?” Josh nodded shyly. His face beet red and his cock at its full, glorious 4.27-inch stand. "Did you enjoy it?" Another shy nod. "Of course you did, Buddy. Every boy needs relief. Your Daddy would have told you all that. I'm sorry you never has a Daddy. But now we're going to get you on the right path. Did you use any kind of lubricant when you were rubbing yourself down there?" Josh looked puzzled. Mr. Longthrust smiled. "It's better with lubricant. Even if you just spit on your hand. Wait just a minute. I have some stuff right here." The man reached into his bag and extracted a plastic bottle of "Slickyboy Masturbation Cream" (a Spermbutt Industries product). "This stuff is great. Let me show you. Are you circumcised? [Chuckle] I guess I'll see for myself in a second. Let’s just pull these down. Oh my! Nice panties!" THE MAN HAD PULLED JOSH'S SHORTS DOWN! EXPOSING HIS PANTIES! AND JOSH HAD LET HIM! It had just seemed so natural. Mr. Longthrust was here to help Josh mature. Step one was better masturbation through lubrication. Practical exercise to follow verbal instruction. Before Josh could form a proper objection in his mind, his panties were down to his knees and Mr. Longthrust was admiring the boy's stiffie with a look and manner that, had Josh a better vocabulary, the boy would have defined as "lupine." Josh was alone and half naked in the house, for 16.3 more hours, with a man whom he had just met and was smearing some creamy stuff onto his hand in order to... Oh!! The man was running his strong, warm, slippery fingers all along Josh's erect penis. In ways that Josh had never imagined. Nor had the boy ever imagined the delicious sensations he was feeling as the man handled his precious parts lovingly and expertly. Despite his usual good sense, Josh surrendered to the man’s attentions. The boy groaned softly as he felt his foreskin pulled this way and that. And the rubbing of the exposed pink knob fired his libido in a way he had never known. Josh actually whimpered when the man interrupted his "molestation" to apply more lubricant. Then he was surprised to feel the man's relubed hand cuddling his testicles. Which was also incredibly thrilling. The man even made a small joke. "I was a basketball player in high school, Josh. A good ballhandler." Josh wanted to snicker in socially dutiful appreciation, but he felt the first delicious pang of an oncoming crisis. The man recognized what the boy was feeling and returned his hand to Josh's tender knob. Reveling in the boy's squeaks and grunts until, 15 seconds before the arrival of Josh's legshaker orgasm, Mr. Longthrust did two naughty things: He entered Josh's bottomhole with the middle finger of his free hand. And he leaned forward and kissed Josh -- right on his cherubic lips. Josh screamed. Not in fear. In a lustful agony of delight. Shooting his boy's cream in thick arcs. All over his own belly and the shirt of the fully clothed man whose tongue had just entered Josh's startled mouth when he opened it to scream. Ecstatically confused, Josh's brain desperately sought to sort out what was happening to him. The tongue in his mouth. The [blush] finger in his bottomhole -- the most confusing act of all. Who knew that a violation of one’s boyish anus would be so terrifyingly thrilling? The man was a horrid beast for taking advantage of the boy. Josh knew that. And he knew that many would see what just happened as stunningly gay. So why did it all feel so good? So much better than anything he had ever experienced? Josh's orgasm reached his toes. He wiggled them to make sure they were still attached. Then he whimpered and grunted his way through the indecent reward for gay behavior until only a feeling of perfect relief was left. At which time, Shame and Guilt made their unwelcome appearance. Mr. Longthrust knew them well. He had met them on all his first dates with a boy. They had met their match with Mr. Longthrust, however. The man finished the kiss and said, "I've been wishing I could meet someone like you all my life. You're a perfect angel. I hope you liked that. There's lots more where that came from if you want it. I'll be in your room when you're ready." At which point, he grabbed his bag and went upstairs. Leaving Josh, naked from the waist down, stomach wet with sperm, chest heaving with excessive breathing, to his choices. Mr. Longthrust found the boy's room and went in. Slowly, unhurriedly, he undressed. All the while thinking about the old joke about the young nun who was seduced by a man. They were both naked, lying in bed, having just fucked and the enormity of her sin had just slammed into Sister Ann. The man watched as his lover fell to her knees and begged God's forgiveness. Crying and sobbing, Sister Ann said, "Please forgive me, Lord, for my two horrible sins!" Puzzled, the man asked her, "What two sins?" Her answer: "Well, we're going to do it again, aren't we?" That was what Mr. Longthrust was counting on with Josh. Fear and loathing at the "sin" he had just committed, but an irresistible urge to "sin" again. The man folded his clothes neatly and laid them on a chair. Then he extracted a fresh bottle of Spermbutt Anal Lubricant from his bag and laid it on Josh's nightstand. Mr. Longthrust sat on Josh's bed. Naked, hairy, erect and expectant of Josh's imminent arrival. He didn't wait for long. Josh had considered his options. The most "practical" being to get dressed in his panties and short-shorts and make a run for it. Perhaps to the police station. Where he would report Mr. Longthrust and his Mom. Then watch as they were hauled off to the slammer. Then he would live with a foster family for seven years or so. In seven years or so, Josh would find a girlfriend who would do some of those things Mr. Longthrust had done so well moments earlier. Seven years? Or right now? Hmmmm. Mr. Longthrust watched the door. And smiled to himself as he saw Josh peek in, then withdraw when he saw the man's hairy nakedness. Seven years? Or right now? Josh chose right now. Tentatively, the still-half-naked boy entered his own bedroom. Shyly avoiding eye contact with his ravager-to-be. While getting a good look at the man's toned body and massive cock. Oh! Was it too late to run? He could just... "I'm glad you joined me, Josh," Mr. Longthrust said. “You're my every dream come true. And I want to be yours. Let me help you out of that shirt." Docilely, Josh raised his arms and allowed the man to remove his last item of clothing, the sandals having been kicked off before he climbed the stairs. So they were both naked. And Mr. Longthrust was gently seating the boy on his hairy lap. They were kissing again. Open-mouthed and hungrily that time. Both fully into it. Josh felt Mr. Longthrust's erect cock rubbing his thigh and, without considering further consequences, he laid his soft, warm hand on the man's stiff beast. Mr. Longthrust groaned in appreciation. Which delighted Josh. And the ice was completely broken. Man and boy kissed and wanked each other slowly. Making it all last. Pulling foreskins just the right way for maximum pleasure. Josh felt his pleasure warnings and welcomed them. Mr. Longthrust felt Josh feeling his pleasure warnings and stopped pleasuring him. Which made Josh whimper, until... "I'm not wasting any more of your delicious cream, Baby. Stand up and face me. That's it." What was the man doing? He was slicking up the three middle fingers of his right hand with some stuff from a new bottle. Then, as the man stayed seated, Mr. Longthrust was positioning the standing Josh right in front of him. "You're going to like this a lot, Sweetie," Mr. Longthrust said. And then he took Josh's cock into his mouth and began to lick and suck it! Josh squealed with surprised delight. He had never felt anything half as good in his life. And then it got better. Way better. Mr. Longthrust entered Josh's anus with his lubed middle finger. Still rolling his tongue over the boy's exposed knob, the man found the boy's prostate. No one had ever touched Josh's prostate. Josh didn't even know he had a prostate. And no one had ever sucked his cock. The effect was nuclear. With additional megatons when Mr. Longthrust slid the other two fingers into the Forbidden Zone. And began to prostate-massage and cocksuck in rhythmic earnest. Josh's testicles detonated. As the boy emitted both a loud squeal and a creamy spurt. Right into Mr. Longthrust's delighted mouth. Josh didn't know such pleasure was possible. It was so intense, it was almost painful. The boy shuddered and spasmed as he shot his seed into his man's throat. He was exhausted. Yet eager for anything the man would propose. In fact, when Josh became capable of rational thought, he realized that, rather than wait for the man's next move, it was time for Josh to do something for Mr. Longthrust. But what? He decided to show Mr. Longthrust that he was "giving himself" to him. Best way to signal that would be to get onto his knees. Between the seated man's legs. Which brought Josh eye to eye with a very large, very stiff object. A pearl of clear liquid was oozing from the man’s peelips. Josh knew that it was the stuff that came out when one gets aroused. It pleased Josh that Mr. Longthrust was fully, almost agonizingly aroused by being with Josh. Maybe he and Mom weren't that different after all. In for a penny, in for a billion dollars, Josh stuck his tongue out and licked the liquid off the man's pouting peelips. Which wasn’t half as yucky as it could have been. Mr. Longthrust's nice, deep moan made it a pleasure for Josh too. The kneeling Josh pushed his luck. He gave the man's cockhead a nice, all-over suck, removing his mouth with a loud "pop." Mr. Longthrust liked that too. Experimenting further, Josh used his tongue to "polish the knob" over every hot pore, then added a bonus bit by cuddling the man's fat, hairy balls as he tongued his cockhead. That, as little extras often do, did the job. "Oh, shit!" the man called out as he lost control of his "cargo." Josh wasn't allowed to use words like that, but he didn't blame Mr. Longthrust for saying it. The things Josh and his date were doing were pretty exciting, and one could be excused for minor transgressions like spontaneous swearing. But attempted drowning of one's cocksucker was a more serious offense. And Mr. Longthrust was fortunate to avoid indictment on that charge. Josh choked as he suffered the first hot blast of manly seed into his mouth. He withdrew reflexively, then felt blasts numbered two through seven coat his face and chest, then dribble all the way down to the pillow he was kneeling on. Men, apparently, make a lot more sperm than boys do. To his surprise, Josh wasn't put off by any of that. He looked at Mr. Longthrust's sperm deluge as an expression of his manly admiration for Josh's beauty, charm, and growing capability as a lover. And swimming in sperm was kind of sexy -- not yucky at all. It appeared that Mr. Longthrust shared that view, since he had drawn Josh to a standing position, laid him oto his back on the bed, and covered him with kisses all the way to each pretty toe. That was cool! Josh really liked when Mr. Longthrust licked and sucked his boyish nipples. Unlike his prostate, Josh had always known that he had nipples. He just didn’t know until that Saturday evening WHY he had nipples and a prostate. So much to learn. But Josh was pretty sure that anything else he and his "manfriend," Mr. Longthrust, did that evening would be variations of wanking, kissing and cocksucking. Which was a delightful prospect to the newly awakened lad. But the best was yet to come. After a delicious half-hour of surrendering to all-over kisses, Josh was hard and needy. But how to ask Mr. Longthrust for "relief" without seeming "slutty?" Relief was not on the man's immediate agenda. "I'm going to call for pizza. We can get cleaned up, including changing these sheets, have our dinner, then see what else you might like. OK?" Well, it wasn't fully OK to Josh. He would have rather had his cock sucked than eat pizza. And cleanliness was still not his highest need. But the man was the man. "OK, Mr. Longthrust," the sweet angel said. "Baggiagalupe's has the best pizza and I like sausage. On my pizza." He giggled. Double-entendres are the most fun when you're ten, almost eleven. Mr. Longthrust smiled, kissed Josh on the lips, and ordered an extra-large cheese and sausage pizza for delivery. "It'll be here in 35 minutes, Honey. Just enough time for a nice shower. You go start the water and I'll change the sheets. Your mother left us three clean sets, bless her." Josh winced. He wasn't happy that his mother thought he was such a sissyboy slut that he would stain the sheets three times. But he was eager to stain them three more times at least. Josh got the shower water just right then stepped in. He would hurry so that Mr. Longthrust would have plenty of time to shower before the pizza delivery man... Whoa. Mr. Longthrust was getting into the shower with Josh! They were both naked and were soon erect. Another sweet surprise. Two washcloths were well-soaped and there was lots of kissing and cuddling and fingers in Josh's bumhole. But the man stopped short of making Josh cum. And didn't cum himself, even though naughty Josh slid a naughty finger into his man's bumhole during one passionate shower kiss. Bummer. Josh was a bit heated up and unsatisfied after they dried off and padded downstairs naked. Mr. Longthrust hastily put on shorts and a tee when the pizza came, then got naked again as they ate. The pizza was good. And so was the conversation, mostly about Josh's life, likes and dislikes. But Josh wanted more. Soon. After all, Mom would be back in only 14.3 hours. After the last morsel was eaten and cleanup was underway, Mr. Longthrust asked, "Do you know what `fucking' is, Josh?" A startling question, even in the midst of what they had been doing. "Fucking is when a man puts his penis into a woman's vagina and they make a baby," the boy answered with schoolbook precision. Mr. Longthrust smiled broadly. "That's one kind of fucking, you're right, Sweetie. But there are more kinds. Men don't just fuck to make babies. They fuck for fun. And they don't just fuck vaginas. They fuck women's bottomholes. [pause] And boys' bottomholes." Josh saw where this was going. And it scared the poopie out of him. Did Mr. Longthrust intend to try shoving that colossus into his tiny bum? Oh!!! That sounded awesomely dirty! Thrillingly sexy. And life-threatening. If Josh hadn't been so needy for relief at that point, he probably would have run to his room and locked the door. But the notion of "being fucked" seemed like a way to please his man as he pleased himself. Still, he had to ask. “Does it hurt?" Mr. Longthrust smiled, sat, and drew Josh to his lap. "I'm afraid so, Baby. But only at first, I understand. Then it's pure pleasure for both of us. And I really want to make you happy." Josh was beginning to think that he wasn't the first boy Mr. Longthrust had ever "dated." But he trusted Mr. Longthrust. A man would never lie just so he could fuck someone, right? So he kissed the man's lips and said, "Whatever you want, Mr. Longthrust." And thus Josh put his ass into Mr. Longthrust's hands. And cock. The naked couple retired to Josh's room once again. And the preparation began. "I'm going to get you ready in two ways that I know you'll like, Baby," Mr. Longthrust said. "I'll just lie on my back and you just kneel, facing my feet, straddling my shoulders. That's it, Honey. Just lower your bum down and sit right on my face. That's it. MMMMM!!!" Oh my goodness!!!!!!!!!!!! Mr. Longthrust had his tongue up Josh's bumhole!! Licking it out!! So nasty. So exciting. So dirty. So thrilling that, after grunting and squealing his way through five minutes and 36 seconds of expert, loving analingus, Josh shot his boy's cream all over Mr. Longthrust's hairy chest. Which pleased them both. And began Josh's real education about the delights of the anus. Josh eased off Mr. Longthrust's face after his shudders subsided and offered to suck his man's cock in gratitude. "No thank, you Sugar," Mr. Longthrust said. "I'm saving that stiffie for a bigger occasion. Gosh, Josh thought. Did 40-year-old men need to husband their erections? Josh seemed to have one all the time. Hmmm. Anyway, the lovers lay side by side, kissing deeply as Mr. Longthrust lubed three fingers with Spermbutt Anal Lubricant, then slid them into the boy's well-eaten asshole. Josh cried out as the man found that prostate thing again and tormented it as they kissed. Making the boy puddle-weak and coaxing yet another creamy load from his aching balls. No one has ever had a date as good as this one, Josh thought. But the first bump was about to appear in the date's superhighway. Mr. Longthrust had prepared the boy's anus as well as he could and he meant to fuck him or expire in the attempt. But as a man who had introduced 26 boys to the joys of anal sex, he knew what was imminent. The man positioned the boy face down on the bed, then slid three pillows under his tummy. The position was right. The boy eager for his first fucking. Lubrication and dilation were accomplished. Check, check, check and check. What a beautiful, loving boy, Mr. Longthrust thought as he lined up his cock with Josh's gorgeous asshole. What a privilege to take his virginity. But wasn't it only fair that he, the founder of matchup.com, would have first choice of all the boys whose moms sign them up to his service? Best investment he ever made, Mr. Longthrust reminded himself. He grabbed Josh's hips firmly -- critical to prevent escape -- and pushed hard. Lodging the head and two inches of shaft inside the sweet canal. Wait for it. The moment of shock and then the scream of near-death agony. There it was. With the boy distracted by his own scream, Mr. Longthrust shoved the other six inches into paradise and was in to the hairs. The man held the boy's hips firmly as he screamed and bucked and tried to get away. To no avail. "It's OK, Baby," the man said as he leaned forward and kissed Josh's neck. "I won't move it yet. Just letting you get used to it. There we are." The fires in Josh's bowels were subsiding a bit. And the man had reached around and was wanking him very nicely as he said sweet things about his beauty and charms. Soon the pain was bearable. And then it was gone. Replaced by a lovely feeling of pressure on that prostate thing. Josh sighed with pleasure as Mr. Longthrust proceeded to active measures. Running his thick log back and forth in Josh's stretched boypussy. Josh was pleased to hear Mr. Longthrust's grunts and moans of pleasure as he fucked the young beauty. Josh was every bit as beautiful and desirable as his Mom. Which would give him the confidence he needed to get through life. Though the rest of his life wasn't what was on his mind at that moment. The boy felt yet another orgasm brewing. A big one that time. Prostate-centric. Only pillowcase friction on his penis. Mr. Longthrust had picked up the pace as well. Which told Josh that the man was about to shoot a big load of that stuff he had shot on Josh's face inside his bottom. The thought of that naughty nastiness pushed Josh off Cum Cliff. The young angel squealed and squirted. Though all he could manage was a few watery drops, his spasms were severe. Mr. Longthrust was delighted that he had given the beautiful boy such first-fuck pleasure. Which set him off. Through an orgasmic haze, Josh felt his bowels being filled with sperm. And a good time was had by all. Five minutes later, Josh lay in Mr. Longthrust's loving arms. Both their chests were heaving. Both cocks were limp and drooling. Josh's asshole was drooling sperm. What a great first date this was. Ten minutes later, Mr. Longthrust said, "I think you like being fucked." Josh giggled. "I like it all, Mr. Longthrust." And to prove it, he slid down and took the man's limp, poop-coated, cum-dripping cock into his mouth and nursed on it, rather than sucked it. Both lovers fell asleep at that, even though it was only 9:12 p.m. And 12.8 hours until Mom came home. Josh awoke at 12:37 a.m. with a raging stiffie and an urge to do something with it. Mr. Longthrust was snoring lightly and his manly rammer was at half-staff. Time to raise the flag. Josh located the bottle of Spermbutt Anal Lubricant and lubed three fingers of his right hand with it. Then he entered his man's anus with his tiny fingers as he capped the man's cockknob with his wet mouth. Mr. Longthrust awoke in what had to be the most pleasant way a man can awake. Oh my. The little scamp liked anal games with his man. Maybe on their second date, he'd offer Josh's cock his hairy hole. Should he let Josh suck and swallow a nice, thick, three-hours-in-the-making load? Or should he call a timeout and shove his new stiffness into that heavenly channel? He decided to be lazy. "That's so good, Baby. So sweet and loving. So generous. Move your fingers left. That's it. Right there! Oh!" Mr. Longthrust "endured” the sweet agony of a simultaneous knob-licking and all-out prostate assault. Josh enjoyed it almost as much as his man did. Giving pleasure can be as much fun as getting it, Josh discovered on his first date. The boy was more prepared that time for the inevitable sperm tsunami. He managed to swallow a million or so spermies before another million dribbled out of both sides of his pretty mouth. Mr. Longthrust drew him for a deep, long kiss, then had Josh straddle his shoulders, kneeling in a position where he could fuck the man’s mouth as the man finger-fucked the boy's anus. That was very nice indeed! When all that was duly entered into the history books, Mr. Longthrust insisted on changing the sheets and showering yet again. Which gave the man additional time for recovery. Since he intended to give Josh's anus another nice fucking before they went back to sleep. And a very nice, clean-sheet fucking it was. Long and slow. Thirty-four minutes of in and out. With the boy on his back, on the bottom, calves on Mr. Longthrust's shoulders. There was slight pain that time. But it passed quickly. And the fucking that followed was one for the ages. The innocent sheets suffered. OK. Time for another snooze. Which ended when Mr. Longthrust awoke at 4:28 with a stiffie and a dream. He awoke Josh with kisses and, lying on his back, eased Josh down until the boy was sitting on the man's cock. They kissed and fucked for 43 minutes that time and, when they orgasmed, stayed in position until they fell asleep again. Until 8:24. Only 1.6 hours until Mom's return. Mr. Longthrust sucked Josh to a creamy conclusion, then put him on all fours and doggie-fucked the boy until he screamed out his love for Mr. Longthrust. "I love you too, Baby," the man said truthfully. But in truth, he loved just about every boy he fucked. "I'll ask your mother for another date. Maybe next Friday." Friday!?!?!?! Josh couldn't wait for sex until next Friday. How would he ever... And then it hit him. Josh could have sex any time he wanted. With just about any man...or boy...he wanted. He would just have to wiggle his bottom and bat his eyes. Which was exactly what he did with Mr. Longthrust at 9:01 to eke out one last fuck before they hurriedly showered and changed the sheets one last time before Mom's arrival. Life is good for a beautiful sissyboy. I welcome your comments at beautifulcreamer@yahoo.com. Other stories on Nifty: "Sweetyboys" (gay young friends) August 31, 2007 "Boarding-School Bedmates" (bisexual adult-youth, though it's quite gay) May 5,2008 "After-School Stroke Club" (gay high school) May 28, 2008 "Pretty" (gay adult-youth) May 21, 2008 "Hotel Management" (gay adult-youth) June 2, 2008 "Dating Pretty Boys" (gay young friends) July 2, 2008 "Sissyboy Stepson" (gay adult-youth) July 30, 2008 "Sissyboy Showoff" (gay adult-youth) August 14, 2008 "Sissyboy Sleepover" (gay incest) August 26, 2008 "Cockteaser's Comeuppance" (gay adult-youth) September 5, 2008 "Schoolboy Pleasures" (gay adult-youth) October 23, 2008 "Home-Schooled Sissyboys" (gay incest) October 25, 2008 "Sissyboy-Daddy Reunion" (gay incest) November 24, 2008 "Sissyboy Shooting Lessons (gay adult youth) December 4, 2008 "Stepson Seduction" (gay incest) December 13, 2008 "The New Sissyboy" (gay incest) December 22, 2008 "Sissyboy Hangout" (gay incest) February 13, 2009 "The Little Prickpleaser" (gay incest) February 20, 2009 "Twelve" (gay incest) March 10, 2009 "Sissyboy Facts of Life" (gay incest) March 11. 2009 "Lord Upcock's Darlings" (gay adult-youth) March 12, 2009 "Sissyboy Spunk Party" (gay adult-youth) March 20, 2009 "Corporate Cockpleasers" (gay adult-youth) April 1, 2009 "Sissyboy Nephews" (gay incest) May 5, 2009 "Sissyboy Pediatrics" (gay adult-youth) May 14, 2009 "Next-Door Sissyboy" (gay incest) May 19, 2009 "Sissyboy Sanctuary" (gay adult-youth) May 20, 2009 "Model Sissyboy" (gay adult-youth) November 5, 2009 "Sissyboy Restitution" (gay adult-youth) January 27, 2010 "Sissyboy Spinoffs" (gay adult-youth) January 28, 2010 "Sissyboy Wives" (gay adult-youth) February 3, 2010 "Secret Sissyboys" (gay adult-youth) April 8, 2010 "Sissyboy School Spirit" (gay adult-youth) May 5,2010 "Try Men" (gay adult-youth) June 21, 2010 "Teaching Sissyboys" (gay adult-youth) July 26, 2010 "Sissyboy Princesses" (gay adult-youth) September 11, 2010 "Sissyboy Swap" (gay adult-youth) December 26, 2010 "Sissyboy Psychology" (gay adult-youth) January 12, 2011 "Sissyboy Island" (gay adult-youth) January 28, 2011 "Sissyboy Prom Night" (gay incest) February 8, 2011 "Sissyboy Workout" (gay adult-youth) February 12, 2011 "Naughty Sissyboys" (gay adult-youth) February 19, 2011 "Society Sissyboys" (gay adult-youth) February 28, 2011 "Sissyboy Sodomy" (gay adult-youth) March 22, 2011 "Sissyboy Stripoff" (gay adult-youth) April 5, 2011 "The Sissyboy and the Ruffboy" (gay adult-youth) April 5, 2011 "Sissyboy Superiority" (gay adult-youth) May 26, 2011 "Sissyboy Sex Education" (gay adult-youth) August 6, 2011 "Sissyboy Justice"(gay adult-youth) August 16. 2011 "Sissyboy Summer"(gay adult-youth) August 23, 2011 "Sissyboy Dreamer" (gay adult-youth) September 8, 2011 "Try Boys" (gay adult-youth) September 12, 2011 "Sissyboy Scenes" (gay adult-youth) September 19, 2011