18 comments/ 50120 views/ 122 favorites Futanari Academy Vol. 01 By: DesoulTales Chapter 1 7th period had ended well over an hour ago for the senior transitional class of the Westbrook School for Young Gentlemen. The after school clubs were having their usual meetings in the nearly empty school, the athletics teams out in the fields practicing their respected sports. The school was practically deserted as the students of the all-boys academy were mostly self-governed and handled things like classroom clean up by themselves after classes had ended each day. Thus there was rarely any staff about after school ended each day, save for teachers who might stay after classes to offer tutoring or might happen to be staying late to grade assignments. It was in this privacy offered by the large, empty school that the two friends met inside of the dimly lit classroom on the third floor. Jordan looked out into the hallway before softly closing one of the two doors leading out of the classroom. The other was at the back of the classroom and already shut. He was a very pale, slender young man with dark brown hair that was cut short and slicked back, his head seeming to glisten and shine. Jordan's companion, Bailey, was a petite, feminine-looking young man. With short blonde hair and a soft brown complexion he got from tanning. Like Jordan, he was 18 and a senior at the school, though while Jordan was thin and wiry, Bailey was soft and looked almost like a girl with short hair. He had been picked on for years because of his slender body and soft voice, and the notable lack of hair compared to some of the other seniors who resembled gorillas with their volume of body hair. "Did you bring it?" Jordan asked excitedly as he approached the long table with the backless bench connected to it at the rear of the classroom. Bailey glanced around nervously and nodded once, clutching his messenger bag. Both of them were wearing simple khaki dress pants and white button-up shirts with the emblem of the school on the breast pocket, the mandatory uniform of their school. "Come on!" Jordan whispered, licking his lips eagerly as he glanced over his shoulder, checking the door once more. "It's okay, no one even comes up here, and all the clubs are down on the first floor. We won't get busted." Bailey nodded shyly and opened up the messenger bag, pulling out a glossy covered porno magazine which he set down on the table. The two sat on their knees on the bench, practically shoulder to shoulder as they began to flip through the magazine. "Your dad has really good porn!" Jordan declared, flipping through the sets of pictures of various big-breasted and glamorously dolled up women. "I just don't want to get caught..." Bailey whispered. "My dad would KILL me..." The petite boy shifted uncomfortably but still bit his lip, silently looking at and enjoying the naked women with his friend, despite the danger of being caught. "Whoa! This should take your mind off of it. Look, she looks just like Miss Angeli!" Jordan pointed to the page he had just turned to. It was a double page spread of a woman with bright orange-red hair and pale, healthy skin glistening with oil. The large breasts of the woman were squeezed together by the woman's upper arms as she leaned forward and gripped her bare thighs, her legs spread open wide. She was wearing only a pair of black transparent panties and pair of tall, spiked heels. Bailey felt a warm rush of excitement as he looked at the picture, it really did look like his history teacher, Miss Angeli. He squirmed as he felt his cock getting hard in his pants, his eyes fixed on the busty, nude woman, her body coated with oil from the neck down, making her pale skin practically glow. "Mmm..." Jordan had unzipped the front of his pants and had his stiff, swollen cock out, gently rubbing it with one hand as he looked at the picture of the woman on the table. Bailey watched as his friend slowly stroked himself and slowly bit his own lip, feeling that warm tingle of excitement rush through him again, this time much, much more intensely. Slowly, Bailey reached down and rubbed the slight bulge that ran down his left thigh, his eyes half closing as he rubbed his cock, looking at the picture of the woman that looked remarkably like their teacher, the lovely Miss Angeli. "Are you ready to suck my dick?" Jordan asked softly, gripping the base of his slender cock as he pointed it slightly up at Bailey. The pale cheeks of Bailey's face flushed scarlet and he bit his lip, nodding his head slowly to his friend. "Come on, suck my dick while I look at your porn." Jordan eagerly stroked the shaft of his cock, the swelled head of his cock a dark shade of reddish purple with a bright white pearl of precum glistening at the tip. Bailey licked his lips eagerly as he pushed his short blonde hair back, tucking it behind his ear as he leaned forward on the bench and wrapped his lips around the head of his friend's cock. He hungrily began to suck on the tip of Jordan's cock, his friend's hand moving down to the top of his head, pushing him quickly up and down in his lap. "Ahhh just like that!" Jordan sighed, Bailey's head moving quickly up and down, his hot pink little tongue viciously licking up and down Jordan's cock as he sucked it fast and deep into his mouth. Bailey could feel his warm little asshole began to throb and twitch with longing and anticipation as he lubed up his friend's long, thin prick with his mouth. Bailey flicked his tongue out, licking the tip of the cock slowly as if it were a lollipop, making the dark purple head glisten with his warm, sticky saliva. "Come on, let me butt-fuck you." Jordan said suddenly, his voice a soft, hot pant of a whisper. Bailey nodded in answer and then turned on his knees, leaning down over the porno magazine, his eyes glancing at the picture of the oiled up woman who looked like their teacher, the sight sending a jolt of pleasure through his body. His rear hole throbbed madly as it hungered to taste a cock, any cock, he didn't care. As Jordan stood and dropped his pants, Bailey reached down and unbuckled his, feeling Jordan's fingers slip under his waist band at the sides as he tugged the pants and simple white underwear down around Bailey's knees. "Whoaaa. It's so pink and soft, just like a girl." Jordan said as he squeezed the soft, pale flesh of Bailey's ass, spreading it wide open as he got a look at the other boy's silky pink hole. Bailey's ass was a pale white color, the result of wearing very short shorts while he lay out and tanned. The uppermost part of his thighs up to just at the start of his lower back was a milky white color that contrasted with the smooth brown on the rest of his body. A contrast that made Jordan's stiff dick wag happily with delight. Slowly Jordan pushed the tip of his finger into the tight little pink pucker of his friend's ass, gently trying to push his finger inside. The hole was incredibly warm, and seemed to twitch and wink as he tried to probe it, Bailey letting out soft, muffled moans as he bit his lip. "Use the lotion." Bailey gasped. And Jordan moved across the room, his cock pointing the way ahead of him as he reached the teacher's desk and grabbed the little bottle of lotion with the hand pump that had been left out. Bailey cooed and squirmed around as Jordan pumped a few squirts of the cool lotion over his tight little hole. Bailey nearly came when he felt the two fingers suddenly slip inside of him, now lubed up properly Jordan was able to feed Bailey's hungry hole two fingers. "It's just like you have a pussy." Jordan said, excitedly stroking lotion onto his achingly stiff cock as he used the other hand to finger his friend slow and deep, pushing his fingers in almost to the knuckle. "I don't care what it looks like, just fuck me!" Bailey gasped, his unbearably warm little hole flexing greedily as it squeezed Jordan's probing fingers again and again. He felt the hot little tip of his friend's cock push against his smooth, lubed up little opening and he groaned. Jordan's fingers slid out with a wet 'plop,' the void instantly being filled with the urgently pulsating length of Jordan's cock as he speared Bailey's ass down to the hilt. "Ahh ahhhhh!" Jordan made an effeminate whine of pleasure as the silky soft, unbearably warm little asshole devoured his cock whole, his smooth, heavy balls resting against Bailey's very warm sack. His pants around his thighs, and his cock balls deep inside of his friend, Jordan began rapidly thrusting his hips forward again and again. His hard thrusts were met Bailey's soft, milky white little ass, his warm insides wrapping around Jordan, squeezing his cock and beckoning it deeper. "I love your dick!" Bailey gasped breathlessly, feeling the other boy's cock slide deeper and deeper inside of him. His soft little ass gladly took the strong thrusts, his little pink hole greedily swallowing the rock hard shaft as it slid back and forth inside of him, the head swelling up to gently stretch his tight, pink insides. "It's so warm!" Jordan wore a vacant expression painted with intense pleasure. Fucking his friend's tight little butt simply felt too good, and he could only focus on the act of thrusting in and out as hard and as fast as he could. Bailey bit his lip, his eyes rolling back into his head as he gripped the sides of the little table, the most perverted expression of pleasure locked on his features as he took it gladly up the ass from his friend. Bailey was a natural bottom, he was fascinated with cocks and especially with making them cum, to him there was no better sensation than feeling a nice, hard cock slide into his tight, sensitive hole. He had learned early on that he needn't even touch himself during sex, the sensation of being fucked but his tight little butt would often be more than enough to make him cum, giving him an intense, brain-numbing orgasm without ever having to touch his cock. It was because of this that he willingly took to the role of being a bend-over-bitch so easily. "I'm gonna cum!" Jordan announced suddenly and much too soon. "Do it! Do it! Bust inside of me!" Bailey quickly pushed his little butt backwards, grinding it back and forth against Jordan who cried out and gripped Bailey's hips very tightly. Bailey could already feel the cock swelling up, threatening to blow inside of him. Jordan made a sound that was half moan, half gurgle as he came hard inside of his friend's tight little ass. His cock erupted almost violently as he shot jet after jet of his hot, creamy cum deep into the unbearably warm walls of the tight boy's ass. Flustered but not yet fulfilled, Bailey sighed, slowly folding his arms in front him where he promptly rested his cheek, softly panting for breath, his cheeks flushed. Jordan's cock continued to spasm, the other boy grinding weakly into him until every little last drop of cum had been squeezed out from his rapidly softening cock. Bailey heard the hard click of the lock being opened on the front door of the classroom, his heart skipping a beat as his head jerked up. At the same moment Jordan had heard it too, unceremoniously pulling his flaccid cock from inside Bailey's ass as he tugged up his pants, dashing for the rear door of the classroom. Bailey turned quickly to plead but his friend was already out the rear door, leaving him alone with his pants down, a light trickle of cum touching his thigh and a porno magazine, all in plain sight. The door swung open and in stepped a woman with light, orange-red colored hair. Her large breasts pushing against the dark red fabric of her blouse, and a tight black skirt hugging her narrow hips over her long, black stocking-clad legs. It was his English teacher, Miss Angeli. "Bailey?" She perked a slender, red eyebrow, quickly glancing over the nude boy, the porn magazine and the person who had just fled. She shot the boy an amused, predatory smirk, one that the inexperienced boy mistook for anger and he tensed visibly. Miss Angeli pushed the door shut behind her, leaning her back against it as her professionally manicured and painted fingertips twisted the lock with an audible click. "What the fuck?" The woman grinned, her voice as angelic and gentle as her features. She walked towards Bailey, the boy flushed, breathing quickly, he looked like a deer in the headlights, just absolutely stunned and uncomprehending. Bailey tugged his white, button up shirt down, trying to cover his hairless erection, his eyes darting to the magazine which he immediately grabbed for, only to find that Miss Angeli was too fast, snatching the magazine up first. "N-no..." his voice caught sheepishly in his throat. Miss Angeli said nothing and merely shot him a warning glance, her bright green eyes raking over his nearly naked form for a moment, taking in the side of her student that she hadn't seen before. She had to keep from licking her lips as she surveyed him, he was very yummy looking. The woman slowly sat down on the edge of the table, one silk stocking covered leg crossed over the other as she flipped slowly through the magazine. "So you like slutty-looking girls huh?" She tilted her head as she reached the double page spread of the redhead, she perked her brow. "Heh, looks like me. Though my skin is a lot healthier and I don't have those worn out lines under my eyes. This poor girl is already used up, city miles." "I-it's my dad's." Bailey said, still horrified. He had been caught it was all over, this was the end of his life as he knew it. "Mmm so what were you doing with it?" "Ju-just looking..." Bailey lied. "Just looking huh? Weird, I am looking at it right now and I don't have my pants off, lotion on my thighs and nobody sitting in here with me." She glanced up at the back door and Bailey tensed. "I-I-I uh..." His cheeks were flushed scarlet and he looked as if he would burst out into tears without much more pressure. "You're in deep trouble. You realize that this magazine alone gets you tossed out of here. Not to mention what your parents will think. Tsk. It's too bad really." She said, moving a hand up to toss her mane of light red hair over one shoulder. "It was so close to graduation and now look what you did." She teased. "No Miss Angeli! Please! Please don't tell!" Bailey's bright blue eyes filled with tears as he pleaded with his teacher. "Don't tell! My parents will be so mad at me! I don't want anyone to find out and make fun of me! If-if-if you tell I will get thrown out, I won't be able to go to college..." Bailey brought his hands up and covered his eyes, weeping uncontrollably. Miss Angeli perked her brow again. She had been only teasing the boy, having a bit of fun with him, no way did she expect him to react so strongly when she never really had any intention of turning him in. "Okay, okay shush. It's okay Bailey. It's not the end of the world." She folded up the magazine and set it down beside her on the table before she stood. "My dad is really strict; you don't know how he is! He'll probably kill me for getting thrown out of school!" Bailey sobbed. "It's okay I won't tell." She said, delicately putting a hand on his shoulder. "P-promise?!" He asked, pawing his tears away with the backs of his hands. "Yes, I promise." She said sharply, still taken aback by his strong reaction to her teasing. "H-how do I know you won't just go tell on me right after you leave or wait until tomorrow and do it then?" He had been so caught up with his weeping that he now failed to cover his groin with the little white shirt, his hard, hairless little cock standing up despite what was happening. He must be some kind of masochist, Miss Angeli thought as she reached up, pushing her fingers back through her hair. "I'll make a trade with you." "T-trade?" Bailey asked, the panic slowly settling into the background as he began to calm down. "Well I seem to know one of your secrets, if not more, judging by the lotion smeared on your tight little butt, your nakedness and the porn here. So I think I have plenty of dirt on you. Everyone has their secrets; you shouldn't be scared about that Bailey." She said her hands moving down to the zipper on her left hip. "What are you doing?" Bailey asked, stunned as he watched slowly unzip the skirt. "Well you showed me yours, I'll show you mine." Miss Angeli said softly, wiggling her hips, her black skirt falling to the ground and pooling around the glossy, black spiked heels she was wearing. Nothing could have quite prepared Bailey for, well, anything that had happened the last ten minutes, this only serving to cap off the whole surreal experience. His eyes were drawn up the insides of his teacher's smooth, tanned thighs. She had a short, flat tuft of red pubic hair shaved into a neat vertical stripe that was just above an otherwise hairless, and easily the biggest, thickest cock Bailey had ever seen, even in porno books. He gasped, his eyes widening. "Wh-what..?" He bit his lip, staring at the pale, meaty cock hanging between his teacher's legs. Her groin and cock were pale, the result of wearing a thong while sunbathing. The dark red pubic hair seemed to contrast especially well with the patch of creamy, white flesh. "You just had one of these up your ass a few minutes ago. Don't pretend that you don't know what it is." She said, stepping out of her the skirt that lay at her feet as she reached down, one hand gently cupping her large balls, the other gripping the thick shaft of her semi-hard cock as she very sensually stroked it. "You-you have a dick?" Bailey blinked in disbelief. Miss Angeli smiled sweetly. "Shhh. I'm just a lady with something extra. It really isn't that uncommon you know, especially around this place." Bailey felt a little twinge between his legs. His pink, cum filled little hole was left unsatisfied by the first cock, now here he was, presented with a second and far superior specimen and he couldn't help but mindlessly rub his thighs together and squirm. "You didn't get to cum earlier did you?" She asked, her hand moving off her cock and over to Bailey's, giving it a soft squeeze as she slowly began to stroke it up and down. She licked her lips as he squirmed around; she could feel the intense throbbing of his cock without even squeezing it all that tightly. "N-no.' Was his stammered reply. "Well then I suppose I could help you out, seeing as I was the one that kept you from reaching your climax..." Slowly she began to unbutton her dark red blouse pulling it open to reveal her pink lace bra which pushed up and supported her large breasts. Much like between her legs, her breasts were pale from wearing a bikini top while tanning. Bailey bit his lip, though very excited as he watched the woman disrobe. Once her top was open she caught him by the wrists, pulling his hands up to her large, pale breasts that were straining against the fabric of her bra. He gasped as he squeezed her breasts, his small fingers slowly rolling her very warm flesh around in his hands. "It's so soft." He marveled as his fingers seemed to sink into her supple flush. "Mmm you just play with me and I will play with you cutie..." She reached down, her hand again gripping the boy's smooth, hard little dick as she slowly began to stroke up and down the length of his slender shaft. Bailey moaned out and squirmed a little, the very soft hand gripping his cock and hitting his most sensitive spots with a practiced ease. "M-my ass!" He blurted out suddenly. Miss Angeli perked a brow. "Mmm what's that now?" She asked, slowly moving her hand faster and faster, her thumb brushing up against the throbbing underside of the tip of his hard little dick. "I usually cum...with my butt..." Bailey announced, his cheeks flushing again. Futanari Academy Vol. 01 She took pause at that but didn't betray her surprise as she continued to urgently stroke his sensitive shaft. She certainly hadn't expected her student to be such a little slut. "With your butt hmm?" She slowly released the grip on her student's cock and sighed, leaning back against the table. She was considering just what to do with him when he suddenly sunk down to his knees on the floor. Before she knew it, his warm little mouth had enveloped the tip of her cock, eagerly sucking with, she noted, some level of skill. "Ahh shit!" She sighed, slowly tossing her head back, one hand moving down to grip the back of the boy's head, the other reaching up to squeeze her left breast. "You're a good little cocksucker aren't you?" She gasped, the nearly 9 inches of thick, pale cock quickly stiffening to full attention, Bailey not once taking his mouth from it as he leaned back to better accommodate her growing length. She was surprised at the ease that he was able to take the first several inches of her cock, rapidly bobbing his head up and down her fat shaft, leaving it streaked with saliva as his hands moved up to paw at her large, smooth balls. Despite all his whining, he was obviously a very talented cocksucker, and one only got that good through lots of practice. Her hand moved from her breast to clutch the edge of the table, the fingers of her other hand pushing through the soft, blonde strands of his hair as she gripped his head tightly, pushing it up and down her intensely throbbing cock. The sensation was just so intense that she was caught off guard and nearly overwhelmed by his soft, warm little mouth and tongue. She felt her red-painted toes curling, her breath catching in quick gasps and hot sighs as she squirmed under the skilled mouth, of all people, her student. She felt a warm swirling pleasure in her stomach, her balls tightening as she felt her orgasm slowly building up to its limit between Bailey's talented lips. Suddenly, the boy pulled his mouth off of her cock with a soft plop, a thin line of saliva connecting the tip of her huge cock to the smooth, pink lips of his mouth. "Ahh! Why did you stop? I was so close!" Miss Angeli pushed off the table, sighing, her massive cock still standing at stiff attention while it bobbed excitedly up and down. Bailey merely answered by turning around, putting his knees up on the bench as he bent over the opposite table, his face going down as he reached back and spread open his pale little cheeks for her. The rim of his pink little hole was glistening with cum left behind by his last partner, his passage throbbing and twitching, visibly excited as she shot her a pleading look. There was just no way he would be able to cum without being penetrated. Despite herself, Miss Angeli's cock twitched rather strongly at the sight, Bailey slowly dipping his middle finger inside of his puckered little ass, pushing it knuckle deep before pulling it out glistening with sperm and lotion. It would seem, to her experienced eyes that the crafty little bastard was trying to seduce her. Well, it worked. She reached forward, her hand gripping his wrist as she sucked his finger into her mouth, down to the knuckle. Her tongue swirled over the mixture of sperm, lube and the taste of his delicious pink little hole; it was as intoxicating as it was yummy. "Spread your cheeks for teacher like a good little boy." Miss Angeli instructed her pupil as she spit into the palm of her hand. Slowly she stroked her shaft with one hand, spreading the warm, natural lube over the thick, dark blue tip of her aching cock. Bailey obediently moved his hands back, gripping his smooth, pale cheeks as he spread them open wide for his teacher, his small, puckered hole standing out like a pink little target painted out on his milky flesh for her thick spear. He held his ass like that and slowly arched his back, his pert little ass sticking out towards her, completely exposed and vulnerable. Miss Angeli bit her lip and groaned as she gently rubbed the thick, throbbing tip of her cock against his very warm hole, Bailey cooing with delight at the sensation. She gasped as much in shock that her huge cockhead was able to slip inside of him so easily, as she was just how tight he was, despite being able to take her length. "Oh that's fuckin tight!" She snorted. Amazed as she was able to push her entire length inside of him with one slow, steady push. By the time she had reached the base of her cock, Bailey tensed and then cried out. She began to quickly pull her cock back, afraid that she had hurt him until she seen the warped expression of pleasure on the boy's face. His smooth little cock was spurting cum violently from the tip, its thick, milky white jets streaking across the surface of the table. She gripped his hips and slammed her cock back in, slipping him the full length and not resting until her smoothly waxed balls were resting against his, Bailey crying out loudly now as he splattered the surface of the table with cum. His hands still gripped his cheeks, holding them obediently open for his teacher's thick cock. "You're so tight, yet it slipped right in. You are some kind of special little slut aren't you?" Miss Angeli grunted, her large breasts bouncing heavily and swaying slightly as she thrust her thick, meaty cock back and forth inside of her student's unyieldingly tight little asshole. Bailey could only tremble, he had taken her cock easily enough, but it had filled him so completely that it felt like his insides were being tugged out, and in the most intense, orgasm-inducing way possible. His tight grip could feel every throbbing vein in her magnificent cock, each thrust put pressure on his prostate, the poor little power bottom feeling his balls ache with pleasure, he had cum twice already just from the stimulation, and was sure he was nowhere near done yet... "How many dicks have you taken?" She asked, one hand lashing out, eagerly slapping his pale little ass, leaving a warm red hand print as she grabbed his hips, holding him down against the table as she began to thrust faster and faster, her nipples stiffening to diamond hard little peaks of arousal. "J-just one!" Bailey answered quickly, his head swimming dizzily as he felt the urge to cum rising yet again, the delicious sensation of the biggest cock he had ever taken threatening to overwhelm him and perhaps literally blow his mind. "Don't you lie to me! Lying to a teacher will get you a month's worth of detention. And while we are at it, I suppose we could give your Mom and Dad a call to let them know how unruly you are being..." "17!" Bailey cried out, gripping his cheeks very tightly, his fingers digging painfully hard into his supple flesh as he came again, a trio of thick, healthy spurts rocketing from the bright red tip of his cock to splash onto the table with the others. "17? You're such a little slut! Tell me more!" She ordered, her balls tightening with a deliciously painful sensation as she thrust harder and harder now. All notions of being gentle leaving her mind as she began to rapidly pump her hips, plunging her cock deep into his well-used little ass. "I let boys fuck me bareback in the bathroom after school!" Bailey confessed, head swaying dizzily as his teacher's tight, heavy balls bounced against his from behind, her huge shaft stretching him out in most intense, and pleasurable way he could possibly imagine. "They fuck me bareback! They say I look like a little girl and they like to fuck me since they can't get sex from the girls! I love dicks so I let them fuck me every day!" Bailey's body shuddered and he nearly came again, his head quickly becoming light with the excitement. "You little boyslut! You're such a greedy little bitch aren't you?!" "Yes teacher! Yes!" Bailey replied, his eyes clenched shut as he tried to keep from losing his mind. "Let me hear you say it! Say it you little bareback bitch!" She was much more enthusiastic now, her entire body was already tingling and she hadn't even cum yet. She left one hand on his hip, the other reaching up to pull on a handful of his hair, using her dual grips to ride him brutally hard. Their bodies clapped loudly together, the teacher and her little bitch, already twitching and covered in his own cum as she used his insatiable little boycunt from her pleasure. "I'm a dirty cumslut bitch! I love dicks and I will let anyone who has a dick stick it inside of me! I am little bitch!" Bailey cried. This was enough to catapult them both straight past the finish line. Miss Angeli tossed her head back, her massive cock expanding as she came hard inside of her student. Thick, almost endless coils of hot, sticky cum came roping out from the tip of her cock and deep into Bailey's ass. The little bottom bitch whined, almost convulsing as he had yet another orgasm and then collapsed into the little mess of cum staining the table top, his face down as he panted hard for breath. Miss Angeli slumped forward over him, her arms hugging his waist as her soft, warm breasts pushed against his sweat-soaked back. "Mmm you are a natural little bitch, did you know that?" Bailey nodded his head slowly, his ass had never felt as well fucked, nor his stomach filled with so much cum, and he couldn't be happier. ***** Chapter 2 "Is our son in trouble?" "Are is his grades slipping, is that it?" "No, no, no, nothing like that. In fact, your son is an exceptional young man." Miss Angeli practically purred the words as she felt Bailey's warm little mouth eagerly moving up and down on her stiff, throbbing dick. Bailey was on his knees, hidden underneath his teacher's desk as he attentively sucked her cock. Sitting across the desk from Miss Angeli were Bailey's parents, oblivious that their son was a cocksucking little slut, much less that he was concealed under his teacher's desk, expressing that sluttiness. "Your son..." She smiled, a hand clutching a handful of Bailey's hair at the back of his head, moving him so quickly up and down her cock that she had trouble keeping a straight face. "Is a bright and, umm, skilled young man." "So he isn't in trouble?" Asked Mr. Hudson, Bailey's father. "Oh far from it, he's doing fine, just fine." Miss Angeli smiled, her cock tickled by the sensation of Bailey's silky pink tongue lapping at the thick tip of her cock. "Well what is it then?" Asked Mrs. Hudson. "Oh your son has quite the talented little tongue. For speaking. His grades are excellent; he'll be staying after school periodically for advanced tutoring, kind of like an honors program." Miss Angeli smiled, her cheeks ever so slightly flushed as she felt her balls tightening with the pleasurable sensation of near-release. Even now thick droplets of her creamy precum leaked from the tip of her cock, Bailey's tongue obediently lapping up each and every last little drop. "Well I suppose that would be alright if he stayed after, if you think it would help." Mr. Hudson nodded in agreement. Miss Angeli smiled, licking her lips. "Oh I insist. I promise his talents will be cultivated and put to good use, don't you even worry about that." Her hand pulled back on Bailey's head, reluctantly slipping cock from her student's mouth. Bailey responded by nuzzling his soft, smooth face against the thick, glistening shaft of her cock. His lips lightly kissing her tight, swollen balls as he rubbed her cock gently against his cheek. "Well sorry for calling you in like this, I just find that sometimes these meetings are better face to face so I might address any questions you might have." She pushed Bailey's face against her cock, sighing softly as he shook his head from side to side, his tongue lapping at her balls as he worshiped her cock. "Well if that's all we'll be going, thank you for your time Miss Angeli." The pair stood and Miss Angeli leaned up, shaking each of their hands. "No, no, thank you. And you have a wonderful boy, you must be very proud." The teacher smiled and watched as the two left, sighing heavily as the door shut behind them. "Oh, you little slut! I nearly popped in your mouth!" She tenderly put her hand on Bailey's cheek and gave it a soft pat. Her thumb gently brushed over his lips and he parted them, sucking her finger into his mouth and attentively sucking it with the same tenderness he had been using on her cock just moments before. "Mmm notta swut!" He said, his words muffled as he sucked on her finger. "Oh you aren't are you? You were just sucking a dick 2 feet in front of your parents. If that isn't a slut, I don't know what is." She gently slipped her finger from his mouth and reached up, ruffling his hair as he pouted up at her. "Still denying it?" She asked, briefly raising a brow. He nodded a simple yes. "Hrmm. Fine then, stand up, there is one quick way of proving that I am right..." Miss Angeli kicked her heels gently on the floor, her chair coasting backwards as Bailey climbed out on his hands and knees from under the desk and stood. She reached out and slowly unbuckled his black uniform pants and let them fall down to his ankles. She gave his thigh a gentle swat and he turned around, his back to her. "Now let's see here... Ahhhh..." She licked her lips as she tugged down his boxers, her hands groping his soft, pale ass as she spread open his tight pink hole with her thumbs. "Mmm look how warm and wet your little boypussy is. You were sucking a dick and craving one in your ass. I bet you would have sat right down on my cock in front of them and not even cared, you are so bent and slutty." Bailey responded by pushing his hips back, her fingers spreading open his pink little opening. "It's so warm, it's driving me crazy." "Like I said, slutty." Miss Angeli sighed, gently slipping her middle finger into his asshole, effortlessly pushing it in down to the knuckle before she twisted it around, causing Bailey to coo happily. She quickly moved her finger back and forth, pulling back until just the tip was inside, only to plunge it back in knuckle-deep while twisting her wrist during each movement. "Mmm this little asshole was just made for cocks, Bailey." She whispered, eagerly licking her lips as she watched her finger slip effortlessly in and out of his little pink hole. His insides were intensely warm and slick with moisture, his inner walls seeming to clamp onto her finger and try to pull it in deeper, even as she was pulling it out. Bailey's cheeks flushed and he half closed his eyes, his hands gripping the edge of her desk as she fingered him nice and deep. "I want your dick teacher." Bailey pleaded, his warm little hole tightening around his teacher's finger as he bit his lip and groaned. "Oh I guess. You sucked me for well over 20 minutes so I'm about ready to pop." Miss Angeli complained as she gripped the base of her very thick, meaty cock. The head a bright, swelled up purple as it throbbed gently, yearning for release. Her 9 inches of stiff cock was more than ready, so she stood and gripped the head of her cock, angling it against the warm, pink little asshole of her student before pushing forward. Bailey moaned loudly, his hands tightening their grip on the desk as his greedy little cock-hole swallowed all 9 inches of his teacher's rock hard shaft, taking her balls-deep inside of him. She groaned and leaned over him, her lips kissing slowly at the side of his neck; her hands resting flat on the desk on either side of him as she bucked her hips forward, humping his tight, little bent over ass with deep, powerful thrusts. "You're such a beautiful little slut Bailey, all soft and warm, just like a girl." She said, nibbling at his ear, causing the schoolboy to whimper lustfully as he was drowned in the sensation of his tight little butt being filled by his teacher's huge dick. The boy remained mostly passive, only responding by tilting his head to the side, giving her better access to his sensitive neck. The warm, wet kisses she was planting on his flesh made his stiff little prick tingle almost as much as the thick cock plugging his asshole. He slowly arched his back, pushing his ass up and out a little more. She was already slamming balls-deep inside of him, but the angle made it much, much easier. Now her groin slapped loudly against his pale little butt as she slammed her body forward again and again, her huge cock looking as if it would turn him inside out as it glided rapidly in and out of him. He could feel her warm, incredibly soft breasts pushing against his back through the thin fabric of her blouse, her nipples two hard little peaks that pushed into his shoulders, causing a sudden jolt of pleasure to shoot through his petite body. "Deeper! Deeper! Fuck me harder teacher!" Bailey cooed, his eyes shut as his teacher gently sucked on his neck, her hips moving with an animal-like roughness that kept him pinned against her desk. "I've fucked whores that couldn't take it as deep as you." She replied, arching her back as she roughly slammed her body against his, the movements so rough and violent now that it looked more like she was trying to push him across the room with just her hips and upper body rather than fucking him Sweat dripped down her neck and chest, her partially unbuttoned blouse showing the soft tan lines of pale and light brown flesh. Suddenly she pulled back, gripping the base of her cock as she roughly pulled it out of him, stifling a giggle as she watched his pink little hole gape and then close in the blink of an eye. "W-why did you stop?" Bailey asked, gently wiggling his pale little butt from side to side. "You act like my cock isn't enough for you. If you think you can do a better job of getting fucked, I'll just lie back and let you do all the work." She said, slowly sitting down on the carpet behind her desk, her black stocking-clad legs wide open, her massive cock still at attention as she slowly stroked it from base to tip. It was glistening with his warm ass juices, a pearl of precum forming at the tip before cascading down the underside of her shaft as he watched. "Sit on it." She instructed simply, slowly lying on her back on the soft, red carpet. Bailey moved over to her quickly, leaning down as he faced her, gripping the thick base of her huge dick as he put one leg on either side of her and slowly lowered himself down. He watched as she unbuttoned her top. Her big, perfectly round breasts with the large, rose-pink nipples springing into view as his pink little asshole opened wide, swallowing her cock once again. He began to bounce quickly up and down, his soft little ass sliding up and down her shaft rapidly, reaching all the way down her balls and grinding back and forth on them at the bottom of each movement. Miss Angeli watched with amusement as her student clamped his eyes shut, moaning like a cheap whore as he rode her cock as fast and as deep as he could manage in the position. Bailey gasped suddenly at the sensation of something warm smothering his cock. He opened his eyes and looked down, seeing that his teacher at pushed her large, soft breasts together around his cock and was quickly moving them up and down, stroking him. "Ahhh teacher!" Bailey gasped, his cock almost spurting then and there from the sudden rush of pleasure over his sensitive dick. "It' okay, just shoot it whenever you are ready." She said sweetly, her hands cupping her breasts, her thumb and index fingers pinching her rosy nipples even as she rapidly moved her breasts up and down, milking his cock with them. Even then she could feel her own cock getting ready to blow. Bailey wiggled around awkwardly, his movements torn between thrusting forward into the softness of her breasts and back down the length of her huge, stiff dick. But he managed, rocking back and forth as he cried out, his hands pushing down on the floor on either side of her as he rode her faster and faster. His smooth, slender cock eagerly pumping her breasts as his ass continued to take her full length. Futanari Academy Vol. 01 "UGH!" Miss Angeli grunted loudly, her next couple of breaths coming in sharp hisses as her cock erupted with a hot torrent of cum, shooting it deep inside of Bailey's bouncing little femboy ass. Her thick cock pumped load after load into his tight little ass, spraying each jet of her wonderfully thick sperm with almost violent force deep inside of him, breeding his eager little ass as he obediently bounced up and down on her. Bailey's head spun with perverse delight as he felt his teacher cumming inside of him, her cock throbbing powerfully as she swelled up inside of him. The sensation of all that hot cum coating his innermost walls made the boy cry out, his eyes clamped shut as he swiftly moved his hips, fucking his teacher's deliciously soft breasts until his toes curled in delight. He moaned loudly as he too came, his cock spraying out thick wads of his milky sperm that roped out over the tops of her breasts and neck, a few even shooting up to splash on her chin. The little buttslut trembled, his knees growing weak as he half collapsed onto her, panting for breath. Miss Angeli grinned, moving her fingers through the thick mess he had coated her with, slowly smearing the sperm around on her skin as if it were an expensive skin lotion. "Mmm did that feel good Bailey?" She purred. "Y-yes! T-thank you teacher!" Bailey hissed, still breathing quickly as he slowly sat up and leaned back, resting his weight on his knees, his teacher's cock still sunk down to the balls inside of his now cum-filled little ass. The two were so caught up in the pleasurable daze of their mutual orgasms that they both failed to notice the soft sound of the partially cracked door shutting, or the sharp sound of heels clicking as someone walked away down the empty hall... A few days later, Bailey was spaced out in the middle of class, his warm little hole already aching for the cock he knew he was going to service right after school. Miss Angeli kept the boy very busy, fucking and cumming inside of his ass and his mouth multiple times during their after school fuck sessions that could sometimes last up to 3 hours. Bailey liked getting fucked up his tight little butt, but it wasn't until Miss Angeli came along with her meaty 9 inches that he finally became a complete, cock-addicted buttslut. He could feel his slender cock stiffening and he squirmed in his chair, reluctantly rising from his seat before walking over to the teacher's desk. "Umm, Miss Gordon. I don't feel well, may I have a bathroom pass?" Bailey quietly asked his teacher, biting his lip shyly. "Mmm your face looks flushed, you should splash some cool water on it." Replied his teacher, sliding a simple foot long ruler over towards him that read GORDON-PASS in black magic marker on each side. Bailey nodded and took the pass, quickly heading out of the classroom and into the empty hallway. Bailey rounded the corner, walking quickly but not quite running as he neared the boy's bathroom, his stiff little cock and pink, sensitive little asshole craving stimulation so urgently that he found it hard not to run. "Just where are you going?" Chimed a cold, female voice from behind. Bailey stopped and whirled around, greeted by the sight of another one of his teachers, Miss Roberts. The woman stood nearly 6 foot tall in her gleaming, black spiked-heels. A simple white blouse was buttoned up over the swell of her large, firm breasts, the uppermost curve of which was exposed to invite lustful glances. A simple black skirt reached her knees, the pale skin of her legs gleaming with a healthy shine. She moved her hand up, tossing back her short, raven black hair, her bright blue eyes regarding the boy coldly. "Well?" "I have a pass!" Bailey explained quickly, fearing that he was trouble. He held up the ruler with the black marker on it and showed Miss Roberts who merely frowned back at him. "Pass or no, there is something I wanted to discuss with you Bailey. Come with me, NOW." She was cold and to the point, and with that tone, Bailey was surprised she hadn't snapped her fingers for him to follow like little puppy. Still he did, he followed silently behind her as she stopped and unlocked a door and stepped into the darkness beyond. Bailey followed and then looked up as the door clicked shut behind him, a bright light flicking on in the small bathroom. "Where are we?" He asked as Miss Roberts turned and snapped the deadbolt shut, the little placard on the door would read 'occupied,' ensuring their privacy. The woman turned and leaned back against the door, the only exit out as she glared at him. "This is the female faculty bathroom. It's quiet private and clean and will serve our purposes." "P-Purposes?" Bailey asked, confused. "I know about you and that ginger-haired slut." She stated coldly, her blue eyes locked on his as his face instantly flushed, damaging any attempt he might make to deny it or play stupid. Bailey was terrified, it felt as if his wobbly knees were going to turn to jelly as he stood there under her cold, condemning glare. "I ah, well, we uhh..." "I'll make this very simple for you Bailey, you're a smart little boy and obviously you have some talent to take that much cock like it was nothing. So here is the deal: you service me the way you service that slut and I will keep your secret. I'm a woman with needs that only a deranged little cumdump like you can fill." "Well I..." Bailey began to speak but quickly shut up as she narrowed her eyes at him. "You misunderstand. I'm not asking." Miss Roberts snapped, and Bailey cringed fearfully at the cold way she acting towards him, though strangely he felt his cock tingle with perverse delight at being spoken to so degradingly. He watched silently as the woman hiked up her short skirt to expose a simple pair of mesh panties that looked more like black, see-through pantyhose than actual panties. Coiled up in the front of her provocatively transparent panties was a thick, veiny cock and pair of large, perfectly smooth testicles sitting inside of her tight sack. His eyes widened but he said nothing as Miss Roberts put her hand on his shoulder, firmly pushing him down onto his knees on the tilted floor in front of her. The boyslut quickly licked his lips, feeling an urgent, aching need to be filled coming from his tight boycunt. "I'm not going to baby you like Miss Angeli. I need it rough and I won't take any crybaby shit from you, understood?" She asked, slowly pulling her panties down to her knees, her huge dick and large, tight ball sack swelling now that they were free from their cloth prison. He figured her cock was just a bit shorter than Miss Angeli's nine inches, and not nearly as thick, though it was still a big, meaty fuck-stick by anyone's standards. "O-okay." Bailey replied, he was a bit scared at being confronted like he was, but seeing her huge, rapidly stiffening cock distracted him with only pleasant thoughts. "You will refer to me as Mistress when we are alone like this. Understood?!" She asked sharply and Bailey quickly nodded, feeling his warm little hole practically throbbing for attention. As if treating him roughly and being stern were all it took, Miss Roberts' cock now stood at full attention, a thick, enticing pearl of precum forming at the tip as Bailey licked his lips hungrily. "Lick it, spit it on it if you have to, but I want it glistening with spit because I am going to throat-fuck you. Once I start I am not going to stop until I blow my load, so you better make sure I am nice and wet if you want your job to go more smoothly." She groaned softly, her thick cock had proportionately thick veins throbbing urgently along the length of her shaft as Bailey quickly, sloppily licked at her cock. He slathered his tongue across her cock like it was a rapidly melting scoop of ice cream, his tongue frantically lapping at her shaft. "Mmm that's right." Miss Roberts purred. "Savor the taste of a real cock." Her thick dick twitched excitedly as Bailey sloppily licked and sucked at it, coating it in a sticky, glistening layer of spit which he smeared around with his pursed pink lips and equally pink, hot little tongue. He moved his mouth up and down her veiny shaft and over the thick, throbbing head, polishing it to the point where it practically glowed, his little mouth ceaselessly moving up and down her shaft, worshipping it. "Put your hands behind your back. Then open wide and say 'ahhh' you little slut." Miss Roberts ordered the femmy boyslut, snapping her fingers sharply as she issued the command. Bailey licked his lips, settling back on his heels as he opened his mouth wide, saying 'ahhh' just as she had instructed. Miss Roberts unceremoniously pushed the tip of her fat prick between his lips and pushed forward, stuffing his mouth with the pulsating tip and first few inches of her shaft. Her fingers laced into the blonde hair on the boy's head, gripping twin handfuls as she slowly pushed forward, suddenly slamming the entire length of her cock into the back of his hot, slippery throat. "Urgh! Fuck! Your little mouth-pussy sure is tight. Let's see how hard you can take it!" She grinned almost feverishly as she began bucking her hips back and forth, her firm breasts jiggling slightly from the harsh movements as she drove her cock deep into the back of the boy's throat, moaning loudly as the slick, pink flesh wrapped around her cock, fitting her like a custom made cocksleeve. "Oh yessss." The Mistress from third period hissed, her thick, heavy balls roughly slapping the boy's chin at the bottom of each thrust. Bailey breathed sharply in and out of his nose, his eyes watering and tearing up, though he didn't gag as the huge cock was rammed in and out of the back of his throat, his teacher fucking his mouth like it was her own personal cocksleeve. Actually, it was now... He even found himself suckling at her thick, delicious prick, despite the way it was gliding in and out of his throat, causing to it feel bruised and sore. He kept his tongue firmly pushed against the underside of her shaft, the rough Domme hissing with delight at the way his tongue caressed the sensitive underside of her neglected cock. Her cock moved so quickly back and forth in his stuffed mouth, that it churned up his saliva into a thick, sticky white foam which dripped obscenely down his chin and splattered against her balls each time they slapped against him, giving them a warm, sticky coating of his mouth-pussy juice. Bailey was torn between not believing just how roughly she was using him, or how surprised he was that he was able to keep up, so far not gagging from the very intrusive throat fucking that he was just loving. Her big prick pumped in and out of his mouth, his cock tingling, he wanted to stroke himself so bad, but she had ordered him to keep his hands behind his back and he dared not move them. "Al-almost!" Miss Roberts hissed, her balls slapping loudly against her student's chin as she moaned obscenely. He could feel her cock thickening inside of his throat, knowing it wouldn't be long before she emptied her load into his eager mouth. He wiggled his tongue back and forth as best as he could, his cheeks caving in, the elastic flesh hugging her cock as he sucked as hard as he could while still managing to breath. Miss Roberts came with a throated, breathless grunt, her huge balls grinding against Bailey's chin as they tightened. Her cock spurted thick, gooey wads of her ropey cum down his well fucked throat and into his stomach, spurting again and again as her entire body violently shuddered. The Domme trembled, having easily the most intense orgasm she could recall having in recent years. She sighed hard, grinding her smooth, hairless mound against his face as her cock pushed out the last drops of cum. Slowly she pulled her cock back, Bailey suckling at the tip and quickly swallowing the excess cum before she pulled it from his mouth. Her cock was glistening, perfectly polished with the slutboy's spit as it dangled just in front of his drooling mouth. "Mmm that could have been better, but I suppose it's not bad, for a start." She frowned, pulling her see-through panties up over her limp, twitching cock before pulling her skirt back down and smoothing it over her pale, firm thighs. Bailey squirmed, his little prick rock hard as it pushed roughly against the cloth of his black uniform pants. "M-mistress?" Bailey said suddenly, biting his lip as he wiggled around, still seated on his knees at her feet. "Aww what's the matter slut?" She asked, pressing the open-toed tip of her heels between his legs, grinding it slowly back and forth, causing the boy to gasp. "I suppose I could give you a small reward." She sighed, irritated. "Hold out your hand." Confused, Bailey held up his right hand and his teacher leaned forward, her cherry-red lips pursed as she spit into his palm. "There you go. I trust you can your make your pathetic little cock cum and then let yourself out." She said, carefully checking her hair in the mirror before she turned and unlocked the door, strolling out into the hallway as she left Bailey behind. Bailey looked down into his hand and then up at the woman who walked away, dismissing his presence entirely as she left as if nothing had happened. He felt confused, ashamed and somehow even more excited than before. He unzipped his pants and grasped his twitching cock with his spit-lubed hand and began furiously masturbating... ***** Chapter 3 Bailey's eyes rolled up again and again, the most perverted look of delight painted across his flushed face as he bit hard into the sleeve of his jacket. It was just after school and the rush of students leaving could still be heard in the hallways just outside of the boy's bathroom. While, inside, Bailey was leaning against the inner wall of a stall, his head buried in his folded arms as he bit his sleeve, trying to remain quiet as he was taken from behind. "Ahh Gwen! Fuckkkk!" Moaned the overweight jock behind Bailey. The bottom tried to hold still as his slippery boycunt was pummeled by the thick cock. It was common practice, especially for the jocks to lay a porno magazine on his back to give them something comfortably female to focus on; his tight little hole just an emulator for the fantasies in their heads. Bailey didn't mind though, the jocks pretended he was whatever girl they wanted to fuck and he got nice, hard dick. Everyone cums and everyone wins, as far as he was concerned anyway. "Yeah take it right in your pussy! Yeah! Ahhh!" The jock moaned loudly as he swung his hips roughly forward again and again, each impact jarring Bailey's slender frame. The 300lb football player was named Dave. His large, well-muscled frame moved quickly as he fucked the twinkish Bailey, his large belly lapping slightly over onto Bailey's ass and lower back as the footballer thrust and ground hard into his little pink hole. Something about getting fucked by Dave every other day after school really turned on Bailey. He figured it was the size difference; Dave towered over him in both girth and stature, the football player both muscular and stocky. But Bailey's small frame seemed all the more smaller while he was being used by the 6'2" jock and his equally meaty cock, something about the rough, dominating way he acted, paired with the size difference just made Bailey tingle all over. Dave looked down, watching his unprotected cock slide easily back and forth inside of Bailey. Bailey's bright pink little hole wrapped around his very thick shaft like a pair of pink painted lips trying to suck him off. The football player shifted his gaze between the sight of Bailey's tight boy-hole expertly taking the big, stiff dick, and the neatly folded porn magazine lying on his back. Bailey honestly didn't mind, maybe he savored it even more because it was degrading, but in any case, when these jocks pumped and dumped him after school while focusing on their titty magazines, the inclusion of the porn usually made his tops much, much more enthusiastic. He really didn't care who they were pretending to be fuck, as long as he got it deep and hard, that's all that mattered. "Ahh yeah take it bitch! Take it! I'm gonna pump your little pussy full of cum!" Dave grunted, his hands roughly squeezing Bailey's narrow, hourglass-shaped waist as he roughly fucked the other male. Bailey bit his lip hard, feeling his cock drip cum down onto the tilted bathroom floor as he clenched his hole tightly again and again, using his pink little hole to massage the jock's cock as he was roughly fucked. Bailey whimpered, feeling pleasantly lightheaded as he had his second, but still very powerful orgasm that session. His cheeks where flushed bright red as he sighed out a hot breath, biting his coat sleeve harder to keep from letting out a girlish whimper, though he was sure the jock would cum then and there if he did that. "Ahhhh!" Dave moaned suddenly giving a few more powerful thrusts to Bailey's slippery hole before going balls deep. He could feel the meaty tip of the thick cock swell as a flood of cum exploded from the tip, shooting forcefully into his ass. The jock moaned out almost continuously, breathing hard as his cock spurted over and over again, his balls tight and red hot as they pressed against Bailey's. Dave yanked his rapidly softening cock out, Bailey's pink, puffy asshole gaping for a moment before it magically closed up, trapping the sizeable load of cum inside of him. Bailey sighed happily as he pulled his pants and underwear back up over his well fucked little rear end, his hole feeling warm and stretched, not to mention all the hot natural lube now plugged inside of him. It would certainly help him take Miss Angeli's huge dick as soon as he got to her classroom. "Right you see you later." Dave grunted breathlessly, tucking his cock into his pants. "Just text me next time you need a hole to cum in, kay?" Bailey sighed, slumping weakly against the stall wall, his knees feeling like they were made of jelly as a warm, pleasant feeling burned at the core of his stomach. Dave left without another word and Bailey swayed dizzily, his entire body seeming to throb with pleasure in time with the beat of his heart as he tried to catch his breath. Bailey found himself conflicted as he pondered his next move, he really liked Miss Angeli, she knew just how to fuck him, and that dick of hers, mmm. But on the other hand, there was Miss Roberts. Her cock wasn't nearly as impressive as Miss Angeli's, and she didn't have nearly as much stamina, but the way she treated Bailey like an object and quickly discarded him as if he were nothing but trash... Well, for some reason that made Bailey crave another encounter with the woman even more. Bailey's slippery boypussy throbbed pleasantly at the thought of being used again as he strode through the quiet halls of the mostly empty school, heading towards Miss Angeli's classroom for their daily session. As he rounded the corner to the staircase leading up to the third floor, he heard door open somewhere behind him, followed by a soft, sing-song voice calling out to him. "Why hello Bailey." Bailey recognized the strangely sweet voice of Nurse Joy before he even turned to face her. The short, mousey blonde nurse wore a slinky pink uniform that hugged the curves of her athletic little body. Her bright green eyes gleamed almost mischievously as she placed her right hand on her hip, her left pushing back through her curly blonde hair. "Oh. Hey Nurse Joy." Bailey smiled, biting his lip slightly as he shifted uncomfortably. He was incredibly horny now, and hadn't expected to run into anyone at this time of the day, which had startled him ever so slightly. The heels of Nurse Joy's glossy white shoes clicked quietly with each step as she approached Bailey, her hips swaying ever so slightly as she walked over to him.