How to Graduate

The next day was my 18th birthday. All of my friends knew and were ready to party, and party hard. My birthday also happened to be the last day of school before the graduation ceremony.

            After finishing a movie with the family I’d kissed both parents goodnight, and completely ignored by brother. I retired up stairs hoping to finally have some privacy for the first time all week. I took my shirt off and my boxer shorts. I brushed my teeth, washed my face and all that jazz, and then crawled under the covers. I exhaled, glad tomorrow was the day! I reached into my second drawer of my nightstand and groped around in the dark for my lube. Found it, then I searched for my anal plug that my ex boyfriend had given me about a year ago. It was hard, cold metal, with a huge jewel on the top, so when I bent over it looked like my tight teenage asshole was a valuable piece of jewellery. Surely must be the invention of a man.

            I watched the lube drip in the dark, illuminated by the moonlight seeping through the window onto the cold metal of my plug. I flipped over and stuck my ass into the air and slowly guided the oversized plug into my ass. I loved the feeling of the metal pushing against my asshole, searching for an opening, then at the biggest part of the plug came the pain as it stretched me, then comes the relief once the entire thing is in. I lay on my back and started to rub my clit through my panties. I had already grown wet; I continued to massage my clit through the cotton fabric. My back started to arch and I let out tiny moans. I could wait no longer, I reached into my panties and ran my freshly manicured fingers over my swollen clit and spread my wetness over it. I turned my head and bit my pillow to silence my moans. I started to rub faster, and with more friction. I could feel my pussy starting to contract in sync with my ass. Then came a knock at the door! FUCK!

            I quickly turned away from the door and pretended to be asleep. Light spilled into the room, my pussy was still pulsating even though this intrusion had turned me off majorly.

            “Megan, honey? Are you awake?” I heard my mom ask.

            “Megan?” my dad continued to probe. I pretended to roll over groggily and pretended to open my eyes like the light was blinding.

            “What? I’m sleeping,” I replied with my usual teenage feistiness.

            “We just wanted to let you know that we’re so proud of you and we couldn’t be any luckier to have you as a daughter,” my mom replied. She was that type, so conformist, and incredibly unaware. She was a Stepford Wife airhead, but I loved her, she is my mom after all.

            “We can’t wait for the big day, either!” my equally airheaded father added.

            “Yeah, that’s great. Goodnight,” I replied hoping to shut them up.

            “We love you darling,” my mom continued,

            “Very much,” my father added again. I grunted in reply. She slowly shut the door.  I sighed in frustration. When would I ever get my privacy? I awkwardly squeezed my plug out and threw it in the drawer and went to bed, pissed off that I didn’t cum.

            I woke the next morning and tried my hardest to get out of the door swiftly before my parents could over-celebrate my birthday. I texted my friend Casey, telling her to pick me up down the street. I got in the car with her and her boyfriend. We sped past the suburban streets, all looking like Wisteria Lane.  We arrived at school and I saw that my locker was decorated with all sorts of birthday festivities. I exchanged hugs, accepted small gifts and tossed out lots of “Thank you”s. I had English first, which was a godsend. I loved English, and my teacher was fabulous.

            We didn’t do much in class since finals were over, we just watched a movie. After class Mr. Henrich asked me to stay after class.  I did as I was told, concerned about what it could be about. He had always been one of my favourite teachers and he was a really nice guy, not to mention exceptionally handsome…but never had I been asked to stay after class.

            He perched himself on the edge of his desk, “So I hear it’s your birthday,” he said casually. I wasn’t surprised that he knew, it was a small community.

            “Yes, 18,” I replied excitedly. He smiled back.

            “I have something to give you,” he got up and walked towards his bookshelf. He searched briefly and handed me a book.

            “Catcher in the Rye?” I asked puzzled.

            “ This is a very special copy, once you take a look inside you’ll see why later.” I was honestly disappointed. Since I was 16 I’d dreamt of Mr. Henrich splaying me out on his desk and fucking me senseless. I supposed it was naive of me to think that he’d thought the same way. I was also foolish for thinking that this dream was meant to play out right after class on this very day.

            “Oh, well thank you,” I replied, forcing a smile. I had a flash in my head of this fantasy. I’d wanted it so bad; I couldn’t pass this opportunity up. I had to lure him in right now, or I’d never have a chance; tomorrow is graduation. I made my way over to a desk in the front row. I sat on the desk, and spread my legs slightly and subtly. He definitely noticed, but certainly had no idea it was intentional. My uniform skirt was rather short, and if I’d spread them even just a couple more inches he’d be able to see that I wasn’t wearing panties. I again tried to be very subtle about it. This time his eyes lingered longer on what lay beneath my skirt. I lured him closer, “Please, come show me what is so special about this edition.” He timidly moved towards me and took the book from my hands; he started to flip through to pages towards the middle of the book. I reach my hand out and brushed it over his cock. He pretended not to notice. I started to run my hand up and down my thigh and I lifted my skirt so he could see my tight, freshly legal pussy for a brief moment. I brushed my hand over his cock again, this time it was much harder. I bit my lip and our eyes met. I smiled, deviously.

            “This is not an appropriate time or place,” he stated, in a very unconvincing way.            

            “Is that so?” I asked still rubbing up and down my thigh and biting my lip. “I’m 18 now Mr. Henrich, and I’ve wanted you for years.”

            Mr. Henrich was divorced and lived alone; he was a very well established teacher, and author. There was something about his prestige that literally made me wet. Also his hands, they were weathered and stately, and I’d dreamt of them all over me for years.

            “Come back after school, and we can discuss this copy, have a look at it over lunch and tell me what you think.”

            I wasn’t sure if he was serious or not. Was he really dismissing me or was ‘discussing the copy’ code for fucking?

            All day I sat in class imagining all the filthy scenarios. Images flashed through my mind of me bent over his desk in my uniform skirt, or being fucked up against the white board with my bare tits smashed against the cold white surface.

             In History class we watched an incredibly bland film, John Adams with Paul Giamatti in it. I sat in the back of classroom. I looked around to make sure everyone had their eyes glued to the screen or were sleeping stealthily. I reached down between my thighs and ran my fingers over my pussy. I spread my legs slightly, and parted my lips gently. I started to massage my eager, rapidly swelling clit under my plaid uniform skirt. I gently smacked my clit and felt a smile spread across my glossy lips. Apparently I hadn’t been as stealth as I’d suspected, because my ex was sitting on the other side of the back row with a raging boner; he was looking right at me, smiling that smile that used to melt my heart. I stared right at him and slid my two fingers into my mouth and licked them. As I took my fingers out of my mouth I flashed him my middle finger. Luckily just as I did, the bell rang and the school day was finally over.

            I couldn’t decide whether it was worth visiting Henrich. I wasn’t about to spend my afternoon talking about a book, when my pussy was literally oozing under my skirt. With each step I could feel my wetness, as I walked towards my locker. Again I received lots of hugs and ‘happy birthdays.’ I walked towards his classroom and peeked inside the door. He was sitting at his desk marking some papers. He didn’t look up when I crossed the threshold.

            “Close the door,” he said sternly. I did as I was told, my hands sweating bit, “you’re too early,” he added.

            “Mr. Henrich, you didn’t give me a specific time.”

            “Come here,” he replied, disregarding my argument.

Before I walked towards his desk I asked him, “Mr. Henrich are you alright, you seem a little worked up.”

            “I’m fine, Megan, I said come here.” Still, he hadn’t looked up from his papers. I walked towards him, standing next to him at his desk. He slowly reached his hand out and grabbed my bare teeny ass under my skirt. He used his huge hands to pull me closer to him; he lifted my shirt and planted masculine kisses on my flat stomach as he worked his thick hands, kneading my ass roughly. A moan escaped my lips.

            “Make no sound, until I say it is safe.”

            “Yes Mr. Henrich,” I replied breathily.

            “For today, you’ll call me sir.”  He pulled me down on my knees suddenly. When they hit the floor, shock waves of pain travelled up my leg, but I paid no attention. He unbuttoned his Dockers and waved his huge cock in front of my face. I’d never come across one so huge.

            “Open your mouth,” he demanded. I did as I was told and he slid the head of his cock into my mouth.  I couldn’t believe that this was finally happening.  He started to thrust slightly, but only allowing the tip of his cock to pass between my lips. “Principle Calderon will be stopping by in about two minutes. You will position yourself underneath my desk so he can’t see you, and you will continue to suck my cock.”

This wasn’t a question. I could tell, he was demanding me to do it. I was terrified. What if I got caught? What would my parents think? More importantly, what would my friends think?

I took his cock from my mouth and said, “No, I can’t. What if I get in trouble?” I had fear in my eyes,

            “Don’t be afraid, just do as I say.” I continued to suck. I swirled my tongue around the head of his thick cock, barely able to comprehend what was about to happen. I could feel my pussy growing even wetter under my uniform skirt. I spread my legs wider, and started to rub my clit.

            “Ah ah ah,” he interrupted, “I gave you no permission to touch. Just like in class, you must raise your hand before you speak, well here and now, you must ask permission to stray from what I tell you.”

            “Yes sir,” I replied, my voice muffled by his cock driving deeper into my mouth.           

            “Under my desk,” he said simply. His timing was perfect; the principle opened the door the moment after I positioned my slim and flexible body underneath his desk.

            “Ah, Mr. Calderon!” Henrich said in his normal voice, his teacher voice.

            “Henrich, how are you? Have you finished all of the grade reports or the juniors?” he asked. Henrich slid his seat in closer to his desk. He spread his legs a bit. I’d always admired him as a teacher and I wanted to please him. So I continued to suck his cock, taking it deeper this time. I tried to take in the entire thing, but I just couldn’t it was too big. I hadn’t yet experienced such a huge cock. I massaged his balls slowly as I bobbed my head up and down on his cock. I took each one of his balls into my mouth and gently sucked on them, as I swirled my tongue around. I held on to his cock, tight, while I played with his balls. I continued to massage his cock. He maintained his cool, and I relaxed further seeing how skilled he was at hiding his secret from Calderon. His hips didn’t gyrate, he didn’t moan, or turn red. He just continued to converse as if under normal circumstances. I still couldn’t believe this was happening. Here I was barely legal, sucking my favourite teacher’s cock in my uniform while my principal was just feet away completely unaware. I’d always admired the principal as well, he was always very kind to me, and even wrote one of my recommendation letters. He was a family friend, which made this so much more naughty.

            “Do you have the final files?” Calderon asked Henrich.

            “I do, they’re in the top file cabinet over there. As Calderon turned around Henrich slickly slammed my head down on his cock making me gag and moan unexpectedly. I heard Calderon stop walking. Shit, I was about to get caught. This was it, it was over, and there was no covering this one up. The room was silent, but I couldn’t help myself, a cough escaped me, as I tried to recover from the gag. This was really over. I was done for! There was no way I would graduate tomorrow.

            “Who do we have here?” Calderon asked as he walked around to my side of the desk, “ Ah, Megan, who would have know you were so filthy?”

            “I—I—“ I stuttered, looking up from under the desk.

            “Someone is in very very very very severe trouble, now,” he stated looking me dead in the eye, very sternly, “it’s interesting,” he continued, with haunting calmness in comparison to the situation, “I’ve known your family since you were what? 7?” he finished.

I was speechless. Just moments ago I was amazed that I was fortunate enough to be down on my knees serving Henrich, but now I was beyond shocked that I had just gotten caught.

            “Megan, did you ever think how this could effect your ability to graduate?”

            “Sir, I swear I didn’t mean to, Mr. Calderon.”

            “Didn’t mean to what?” Suck his cock? Or get caught?”
            “I don’t know what I was thinking,” I replied frantically, on the verge of sobbing. The tears were falling as Mr. Calderon grabbed my arm and pulled me up from the ground. I looked at Mr. Henrich, he was very undisturbed by the situation, I could have sworn I saw him smile slightly. I stood between the two of them. They looked at each other and nodded. What was going on? I couldn’t even process how I wasn’t being yelled at, and scolded, and dealt a very serious disciplinary speech as they called my parents. None of this was happening. I was just standing there.

            “Megan, do you want to graduate tomorrow?” Mr. Calderon asked calmly.

            “Yes, please sir, more than anything. I will do anything, I swear.” I replied desperately.

            “I can let you graduate tomorrow, and your parents won’t know a thing, but there’s only one way I can make this happen,” he taunted.  I couldn’t imagine anything that I could possibly do to make this go away. I was devastated.

            “You’ll have to share,” he said. I didn’t understand.  Share what? “Stand up straight,” he ordered me. I felt like I was in the military, what the fuck was going on? My pussy was still pulsating; I couldn’t control it. With each pulsation it felt as if more of my wetness oozed out onto my inner thighs. Henrich had finally gotten up and was circling his desk smiling, and looking me in the eye.  I felt Calderon’s hand grab the back of my neck. He pushed me forward and bent me over the desk. “Let’s see what we’re working with, Henrich. Do we have any goodies?” Then I understood. Henrich had known all along that I was going to get caught. I guess he’s cut a deal with Calderon since this morning. I should have been angry, and fighting to get out. I wasn’t though; I was oddly okay with this. It even turned me on further. The scariest part was that they both knew me well enough to know that I wouldn’t protest.

            I felt Calderon’s hands lift up my uniform skirt. My bare ass and pussy were exposed. His large hands explored my ass. He spread my cheeks and exposed my tight asshole. He then crouched down, so he was level with my ass and spread my pussy lips from behind. His hand slid over my clit as his other hand helped my pussy open.

            “Spread your legs wider,” he ordered. I did and he started to massage my clit, clockwise then counter clockwise. I moaned and my eyes closed slowly. I looked at Mr. Henrich across the desk; he was stroking his cock slowly, with a devious smile on his face.  I was entranced and I looked in to Henrich’s eyes. Suddenly Calderon spread my ass even wider and spit right between my cheeks. I felt his saliva land right on my asshole. He started to massage around the rim, his huge fingers pushing to make my hole part. He spread my ass even wider; this time I could feel my asshole gaping. He buried his face between my cheeks. I felt his tongue slither out of his mouth and into my gaping asshole. I moaned and my back arched. He continued to massage my clit as he tongue fucked my eager ass.

            Henrich moved closer, he took my face in his stately hands and opened my mouth for me. His cock slid between my warm wet lips.

            “Wider,” he stated. I opened my mouth wider as he shoved his cock into my throat until he was balls deep. He pinched my nose shut and held his cock deep in my throat as I gagged and sputtered. He didn’t stop, he pushed further each time I started to gag and look panicked. Calderon shoved his tongue even deeper into my asshole. I contracted my ass, squeezing around his eager tongue.

            “Good girl,” he said in response. He explored my pussy and my clit with his tongue, eating me out, still from behind while Henrich continued to abuse my throat. Henrich’s cock was sliding in and out of my eager throat with deep powerful thrusts, it was almost painful. He continued to fuck my face without mercy.

Muffled moans escaped my throat, and Henrich smacked me across the face. I tried to smile, but his cock was still deep in my throat.

            “Over,” Calderon said. I lay down on my back on Henrich’s desk. My head hung over the edge of the desk. Henrich forced my legs open and immediately smacked my clit. My legs buckled closed in response. He forced them open again, roughly parted my lips and spat on my clit. He smacked it again, my legs shut, slightly.

            “Do you want to graduate tomorrow, Megan?” Henrich asked me.

            “Yes, sir, I do.”

            “Then you will allow me to smack your teenaged clit without shutting your legs.”

            “Yes, Mr. Henrich, sir.” He tried again; I still twitched closed a bit. He tried once more and I finally endured without a flinch. I loved the feeling of his meaty hands smacking my clit. He held my legs very wide open, to the point where it felt as if my legs would detach. He put his face close to my pussy. He hovered over it, and I felt his warm breath against my wet cunt.

            Calderon was watching and smiling, nodding with approval. My head still hung over the edge of the desk. My vision was upside down, as I saw him unbutton his suit pants and take his cock out from his boxers. Again, it was huge! He wrapped his strong hand around my throat and pressed down as he slid his enormous cock into my mouth. His cock slid deep into my throat and I loved the feeling. My throat contracted in response to the size of his cock. Henrich started to flick the tip of his tongue against my clit, which was now protruding through my lips. He flicked his tongue fast up and down over my swollen clit. My back arched and I let out a muffed moan against Calderon’s cock as he continued to fuck my throat like a machine. Henrich now spread my pussy open with his lips and started to suck on my clit gently. He sucked it tenderly, making my back arch and my hands ball into fists.

            “You’ve got a sweet little pussy, baby,” he said, before returning to suckling my raw clit. He slid his tongue down into my hole. He started to tongue fuck my pussy and as he did, he massaged my clit in circles with his thumb. My hips started to grind against his face. I could feel the stubble on his chin. It felt so good to be eaten by a man, instead of all these schoolboys. I could hear his breathing grow louder as he rolled my clit between his lips and nibbled it. This made me moan very loud, and the moment my moan escaped he smacked my clit once more. I flinched in pain and pleasure. He went back to fondling my clit with his tongue. He created a powerful suction around my clit with his lips. Then as he continued to suck, his tongue made circles around it. He put his strong hands up around my hips. I started to grind again, my hips. I started to push my clit onto his lips faster and harder. My eyes closed completely and I felt my pussy starting to pulsate. He stopped suddenly, leaving me bucking against thin air with Calderon’s cock still in my throat. He was now pressing very hard on my throat and was fucking my mouth very hard and very fast. He was grunting loudly and his thrusts grew even more powerful. He pushed his cock so deep into my throat, that he was balls deep with my spit all over his cock and balls. My mascara had run all over my face, in a mixture of spit and tears.

Then Henrich climbed up on his desk. He was squatting over my face, his balls brushing over my lips. I planted kisses on them and in return he ordered me to lick them. I tickled them with my tongue as he started to jack his cock right over my face. I watched in amazement as he smeared my spit around the head of his cock. He started to stroke his cock faster. Calderon moved around the desk. He spread my legs with the same force as Henrich did. He spit on my pussy again and I felt the head of his cock brushing back and forth over my clit. He massaged my clit in circles with the tip of his cock. I moaned, the vibrations pleasing Henrich. Calderon parted my pussy lips with his thick head. He slid his cock into my tiny, tight, wet, warm pussy. My back arched and I let out a colossal moan. He was literally destroying me as each inch slid inside me. His cock was so huge and my pussy was so tight around his thick shaft. I squeezed my pussy around the shaft of his cock as he continued to enter me. He hit my gspot finally. He started to thrust slowly, realizing that he was the largest I’d ever taken. As his thrusting speed increased he massaged my clit with his fingers and with his other hand he started to unbutton my shirt. He reached up under my bra and started to fondle and roll my nipples between his thick fingers. I was literally flat chested, but my nipples grew hard and puffy instantly. He pulled them away from my body and squeezed them hard.

            Henrich continued to jack his cock. He then hopped off the desk and lifted me up, Calderon stepped back and Henrich lay down on the desk. His cock stood up straight.

            “Sit on my cock, little girl,” he instructed. I climbed on the desk and hovered over his cock, “take it in the ass, baby girl,” he added. I slowly lower myself onto his cock. The tip of his cock parting my tight asshole. I winced in pain, it was so thick. I guided his cock into my asshole and continued to lower myself. He grew impatient and grabbed my hips and slammed me down onto his cock. He annihilated my ass right then, and I screamed in pain and pleasure. Calderon smacked my face lightly. While my mouth was still open in pain, Calderon spit into my mouth. Henrich started to thrust his huge cock into my expanding asshole. He started to thrust faster putting me in pain. I loved it though. Calderon watched as he stroked his cock. He reached out and smacked my clit again; he then started to finger my pussy with his free hand. With two fingers he parted my lips and started to massage my gspot roughly as Henrich thrusted upwards into my ass. I started to moan louder. I could feel Henrich’s cock passing by Calderon’s fingers as they both annihilated my tight teenage holes. I started to buck my hips as Calderon massaged my clit with his free thumb.

            I couldn’t take it much longer, I started to grind my hips fast as they stimulated me. Suddenly Calderon climbed up onto the desk as well. He positioned himself in front of me and pushed me back so I was laying flat on Henrich as he continued to fuck my asshole deep. Calderon slid his cock into my pussy, Henrich still pounding away. I screamed again. Their two cocks were almost literally ripping me apart. My frame was so tiny, and I could barely handle it. Calderon started to thrust faster into my tight wet pussy. I could feel how hard and warm his huge cock was as he hit my gspot over and over. I could feel their cocks slide past each other, massaging my wet insides with an indescribable ecstasy. They both started to fuck me at lightening speed while I was sandwiched in between them. Calderon slid his fingers into my mouth to silence me, but his cock started to pound me harder and faster. Henrich sped up as well, his balls smacking against me as I smiled, amazed that I could take two huge cocks. As Calderon thrusted deeper and deeper I could feel his body grinding up against my clit. They fucked me harder and faster than anyone could ever imagine, both in their own worlds. Henrich reached around and pinched both of my nipples very hard, sending me near the edge. He then reached around and massaged my clit while his hard cock slid in and out of my asshole, now gaping. He started to grunt very loudly.

            I started to cum, I could feel my pussy and my ass pulsating and squeezing around their two cocks. I couldn’t control my muscles anymore, my back arched severely, my toes curled and I let out a series of intense moans. While I came I could still feel their huge cocks fucking my tiny body even faster. They were both moaning loudly. Then I felt Henrich take two very deep and forceful thrusts into my ass and shoot his warm thick load into my asshole. He let his cock sit inside my ass and the two smaller spurts of cum filled my ass. I could feel him breathing heavily underneath me. Calderon continued to fuck my tight pussy, his breath almost stopping. He held my throat so tight, and so unexpectedly and I then felt his cum shoot throughout my pussy. The warmth of it on my aroused gspot. He slid his cock out quickly and let the remainder of his load dribble down over my clit as it stuck out from between my lips. I loved feeling their warm cum deep inside both my filthy holes.

            “Well you write papers well, but you’re an even better cum slut,” Henrich said still catching his breath, and grinning as his remaining cum dripped from the tip of his cock. I got up, feeling Henrich’s cock slide out of my ass. I tried to stand up, but I couldn’t. My legs were weak. Calderon held be up with his strong arms. He bent me over once more.

            “Have to inspect our damage,” he said looking at Henrich with a smile.

            “Ah, we’ve got a gaper,” Henrich added. My asshole and my pussy were still contracting. With each pulsating their warm cum spilled out of both holes. I could feel the cum running down the inside of my slim thighs.  Calderon slid his finger into my gaping asshole and gathered the cum.

            “Have a taste, little slut.” He put his finger in my mouth and I sucked the cum off of his thick finger. The both of them took turns gathering the cum and feeding it to me as I oozed, freshly out of my asshole and pussy.

Henrich smacked my ass once more while he sucked and bit my nipples.

            “Congrats,” Calderon said, “Looks like you’ll be graduating tomorrow.” They both composed themselves, straightening their ties, zipping up their pants.

            “Congrats, Megan, and happy birthday” Mr. Henrich added as he shook my hand as if we’d just participated in official business. I couldn’t help but smile. I could feel my ass still gaping under my skirt.

            “Thank you, “ I replied awkwardly as I tried to walk gracefully towards the door.

            “Luckily you’re a filthy little girl, other wise I’d have to tell your parents.”

I smiled awkwardly as I reached the door. I turned around and awkwardly said to them, “See you tomorrow!”

            I walked out of the room, Catcher in the Rye in my hand. I had to make sure no one saw me. My hair and makeup was a wreck. I headed for the bathroom and wiped my face clean, quickly before any stragglers wandered in.

I walked home, with a goofy smile on my face. I could still feel their cum deep inside me, and I loved it. I got home and my parents where waiting at the door with gifts in their hands.

            “Happy birthday!” they both yelled loudly as they wrapped their arms around me.            

            “We’re so lucky to have such a well behaved daughter. We love you Megan,” my dad said as he hugged me.

            “Oh, honey, we just got a call from Mr. Calderon, he said he wants to see you in his office tomorrow after the ceremony,” my mom added. My heart leaped. I guess he wanted a solo run before I left Jacoby High.

            “So how was school, honey?” my father asked.

            “Um, let’s just say I was filled to the brim, loaded, …with excitement. I left stuffed, I got so many cookies and cupcakes from my friends. All these huge gifts, crammed into my locker. It was great. I definitely overindulged a bit. Naughty me,” I said with an innocent smile.

            “Oh, that’s just magnificent honey,” my mom replied with a smile, “Like we said, we’re just glad to have such an angel for a daughter. Always doing the right thing, serving others and doing God’s work.”

            “Of course,” I replied as I felt my asshole still gaping and their cum pooling inside both of my filthy holes, “it’s what I do.”


Notes : Notes