Miss Wong stood at the front of the classroom, erasing her notes about Crime and Punishment in order to make more room, but all I could focus on was her plump, shapely ass wiggling back and forth underneath her tight, charcoal pencil skirt. I had had a crush on her from day one of my senior year, when had I first walked into her classroom at the end of the day and saw her sitting behind her desk, her ruby red lips wrapped around an utterly enviable pen, her dark, crescent eyes slightly obscured by her glasses. It felt like I had been struck by a thunderbolt, and ever since then, she had haunted my thoughts, took center-stage in all my wet dreams, and starred in a number of masturbatory fantasies.
At times, I wondered whether she knew. I wasn’t nearly as subtle about my interest as I should have been, but she didn’t exactly make it easy on me. During the first few weeks of school, she wore button-down shirts, against which her ample breasts strained vigorously, and she often stood at such an angle that I could peek between the gaps of her shirt and get a fleeting glimpse of her overflowing bra. Once winter arrived, the tight sweaters came out, emphasizing her every curve, highlighting the swell of her breasts. How could I possibly tear my eyes away from such temptations? You wouldn’t blame a cat for eyeing a canary, would you?
She never did anything explicit, but the number of times she bent over in front of me and touched my arm gently while explaining a difficult concept couldn’t simply be a coincidence. At times, she leaned in close, and her full breasts pressed against my shoulder while her perfume surrounded me, and I felt as though I were in heaven. Was I delusional, to imagine my teacher had an interest in a boy ten years her junior? Maybe, but if it were a delusion, I’d gladly reject sanity to hold onto it.
I knew the older teachers were jealous of her; we all did. It was no secret that they resented all of the attention she got, not only from her students, but even from the male teachers and fathers. I looked at the silver lining, though: my English grades had never been so high. My mother had even bought her a gift basket after seeing my first report card, after she had stopped crying tears of joy. Yes, there was definitely a bright side to being unable to tear my attention away from my teacher.
And now, as she spoke to the class and gestured dramatically, describing the murder of the old woman, her chest jiggled slightly, and I found myself yet again wondering what she looked like underneath that cherry red sweater, what color her nipples were, how they would feel between my lips were I to gently suckle them to hardness… Were her breasts sensitive? Was she shy? Would she cover her nude body and blush, averting her eyes from me? Or was she bold and brazen? Would she encourage me to drink her in, proudly displaying her body to me? Suddenly, her voice interrupted my daydreaming.
“Jason, can you come up to the front and help write down everyone’s thoughts for me?” she asked.
My eyes widened. My jeans bulged from my earlier thoughts, and now she wanted me to get up in front of the class, in front of everyone. I looked from side to side hastily, praying that another Jason had joined the class within the last five minutes without my knowing. “Me?”
“Yes, you. Come on,” she beckoned. “We don’t have all day.” She held the chalk out to me in her palm, waiting for me to take it from her. I gulped, but there wasn’t any way out of my predicament but time, time and diligent concentration on the topics on baseball, hobos, and that one time I had walked in on my father on the toilet.
I stood up and made my way to the front of the room as though there were a guillotine waiting for me, keeping my eyes bolted to the board. So long as I could keep my back to the other students, no one would be able to see my dong trying to escape through the front of my pants. I thought I heard a slight giggle as I passed Amy Medeiros, but it might have just been my overwhelming paranoia. I took the chalk from Miss Wong’s hand, and my fingertips brushed against her palm. My stomach fluttered from the touch, and I nearly dropped the chalk in surprise, but I had made it without everyone discovering my erection: mission accomplished.
I positioned my hand an inch away from the board, ready to take down whatever notes my peers said. I looked over to Miss Wong to wait for her to begin calling on pupils, but her eyes were focused on me, about three feet lower than I was expecting. I turned slightly, hoping to hide my arousal, but she just looked back to the class with a self-satisfied smirk on her thick lips.
I was thankful that no one else could see my cheeks; I was certain they were as red as they felt. But what about Miss Wong? Had she seen my hard-on? God, she must think I’m a pervert… Was she going to tell the principal? What if she called my parents? I wrote mechanically, my mind miles away from the classroom, specifically, at the top of an unusually tall cliff, high above an acre of jagged rocks, tipped with diamonds, wired to dynamite, and at ground zero of an incoming thermonuclear ICBM.
The next ten minutes were pure torture. I had no way to hide myself, not without calling everyone’s attention to me, anyway, and if having Miss Wong staring at my bulging crotch was bad enough, it’d be even worse with another forty eyes focused on me. At least teachers weren’t allowed to tease me…were they? I was pretty sure she’d get in trouble if she called me Boner Barry or whichever clever nickname my peers would bestow upon me if they learnt of my predicament. Every time she turned to me to tell me what to write, her eyes glanced downwards for the briefest of moments at my lap. I could feel her stare burning into me, and I wondered what was going through her mind. Her face was inscrutable. She could be hiding her disgust with a fake smile, she could be amused, she could be turned on, or flattered, or she could simply be remembering an especially delicious sandwich.
Finally, blessedly, my prayers to every deity I had been able to remember from Mister Katze’s ancient history class were answered by a ringing bell. I scurried to my seat, my cock throbbing within my boxers, while everyone was distracted with putting away their things. I was free, free as a bird!
“Jason?” asked Miss Wong sweetly.
Free as a turkey, in an oven, on Thanksgiving Day…
“Do you mind staying after class? I have something to discuss with you,” Miss Wong said. A chorus of “oooh’s” followed as my classmates laughed at my misfortune. I was in trouble, and they knew it, even if they were fortunately ignorant of the details.
My last classmate left the room and the door closed. The ticks of the clock thundered in the silence. I stood in front of her desk, waiting for her to say something to me. She looked up at me and adjusted her glasses. She took a deep breath and steepled her fingers. My heart fibrillated wildly in my chest. I just wanted her to say something. Anything was better than this deafening silence.
“Jason, I was going over your notes from last week, and I happened to notice that in the margins, someone wrote ‘Miss Wong’ in a heart.” Okay, I’d like to have silence back now… “Do you know anything about that?”
I tried to speak and failed. My lips fumbled about, but no words came out. My mind raced, trying to imagine excuses. “I have a crush on a different Vivian Wong.” “That’s not a heart, it’s an upside-down ass. I think you’re an asshole.” “Someone broke into my house, stole my notebook, wrote that in the margins, and then slipped it into my folder just before I turned it in.” I sighed in resignation. Nothing for it but the truth.
“I wrote it, Miss Wong…”
“I see… There was something else I noticed today, about which I wanted to ask you. When you were at the board, it appeared that you were…how should I put it…over-excited? Now, I understand that you’re a healthy young man, but I’m afraid I must ask you to attempt to avoid it in the future. It’s extremely distracting.”
“I’m sorry, it won’t happen—” My brain rewound her last sentence in my head. “Distracting?”
She rested her head on my hand and looked down at my crotch intently. “Extremely so. How am I supposed to teach when your cock is distracting me like that? Do you have any idea how difficult it was for me not to get down onto my knees and take care of that myself? Do you have any idea how wet I was getting watching you struggle with your hard-on, trying to hide it from me?”
“Call me Vivian, Jason. I’ve noticed your stares all semester, and I have to confess, I’m flattered that a young, handsome stud like yourself would pursue an old woman like me when your pert little classmates are surrounding you.”
“You’re not old, Miss, I mean, Vivian. You’re gorgeous! I’ve had a crush on you ever since I first saw you,” I confessed.
She purred with delight. Her dark, crescent eyes looked up at me from over her glasses. “My my, you’re already such a heart-breaker. You’re going to be such a Lothario when you’re older. Tell me, Jason, do you have much experience yet?”
My cheeks burnt. “Well I mean, I made out with Danielle at the movies once…”
“So you’re a virgin? Have you ever received a blowjob? Have you ever even seen a woman nude? And on your computer doesn’t count; I know all about what you high school boys use the internet for.”
“I, well…not exactly… No…”
She giggled, and I could feel my dick shriveling up, trying to hide from this humiliation. “Oh, I’m sorry, Jason. I wasn’t laughing at you being a virgin. It’s just that you’re so serious. It’s no big deal to still be innocent. You’re still young. How old are you, eighteen?”
“Ouch, please, Jason, anything’s better than ma’am.”
“Much better. As I was saying, most eighteen year olds don’t have much experience. You shouldn’t be ashamed.” She stood up and walked across the room, her stilettos clicking with each step. She reached the door, thrust a key into the lock, and turned it. She had locked us into the room together. My heart began to pound. “However, innocence is like ignorance: it’s not shameful to have it, but you should rid yourself of it at the first chance you get.”
“What are you saying?”
“Have I been such a poor teacher as that, Jason? Can’t you read subtext? I think you know exactly what my meaning is. There’s no need to play coy.” She strode up to me. Her hand reached down to my thighs. I shuddered as she grazed her fingernails up my jeans until she reached my cock and squeezed. “Mmm, I had almost forgotten how good a hard, thick shaft feels in your hand… Care to help refresh my memory, Jason?”
“S-sure,” I stammered, trying desperately not to finish in my pants then and there. Miss Wong wanted to fuck me?! I must be dreaming… I couldn’t believe this was happening to me.
“Good,” she cooed. “Get onto your desk. I can’t tell you how many times I’ve fantasized about this…” She leaned in closely to me, so that her lips were brushed against my ear, and continued in a husky whisper. “I masturbated to you last night in the bath. I plunged my vibrator between my thighs and imagined it was you, and I orgasmed five times, until I was too exhausted to continue. It was the best orgasm I’ve had in months.”
I lifted myself onto my desk. Vivian took hold of her sweater with both hands and lifted it up over her head. Her full breasts bounced gently, clad in only a black, cupless bra. My cock stirred at the realization that she had been wearing such naughty lingerie under her sweater all day, while I was completely oblivious to what was underneath. Did she always wear lingerie like this under her sweaters? It was no wonder her curves were so well displayed… Her pink nipples were already hard, jutting out eagerly. Her tits were even larger than I had imagined, and I had estimated pretty high.
“Do you like my breasts, Jason?” she asked as she reached between her cleavage and undid the clasp. The bra burst away, beaten by the tension under which it had so valiantly struggled.
“I love them, Vivian. They’re amazing. C-can I touch them?”
“Of course,” she replied, jutting out her chest towards me invitingly.
My hands shaking, I reached out slowly and grabbed her breasts. She moaned softly, her eyes fluttering, her lips parted. They felt so soft, so smooth, so warm and heavy and heavenly in my grip. I slowly massaged them, gently caressing her nipples between my fingers. I squeezed softly, relishing their heft in my hands. I couldn’t believe the first breasts I had ever felt were my teacher’s!
She gently removed my hands from her chest, but I barely had time to pout before she slid down onto her knees in front of me, dragging her fingernails along my chest and thighs on her way down. Was she really going to..? She rested her breasts on my thighs, and with her eyes locked onto mine, she unzipped my fly and tugged my jeans down. “Ooh!” she cooed at the sight of the bulge in my boxers as my cock strained against the thin, white fabric. She slid her finger along the length of my shaft a few times. “You’re so big, Jason… I can’t wait to feel you inside me…” She undid my button. My cock sprang free. Her lips were just inches away from its tip. She tucked her long, sleek, black hair behind one ear and wrapped her hand around my cock tightly. Then, slowly, teasingly, she opened her mouth and engulfed my cock.
I watched, entranced, as her lips worked her way up my shaft and my manhood disappeared inside her. She moaned with satisfaction as her lips reached the base of my cock. Her tongue caressed my cock, swirling around my shaft. I moaned, unable to keep my ecstasy inside. “Oh god, Vivian, you’re so good at this…”
She purred softly. Her eyes locked onto mine. As I stared into her dark brown eyes, she slid her lips and tongue along my cock, moving her mouth back and forth. My shaft glistened with her saliva. Her tongue wrapped around my cock. She grabbed my ass with both hands, pulling me deeper into her throat. Her mouth embraced my manhood tightly, as she fucked me with her face, passionately forcing my cock inside of her.
With a wet gasp, she released my cock from my lips. She wiped her lips with one hand. “I can feel you throbbing between my lips…. Your cock is so hot… God, it’s been so long since I’ve had a real cock in my mouth. I just love the feeling of it squirming and pulsating inside of me… Can I have you between my tits?” she asked, pushing her breasts together, creating an inviting crevasse. I nodded eagerly.
She took the head of my cock between her lips and held it gently while she smothered my shaft with her soft breasts. She bobbed her head vigorously, massaging my cock with her tits. The tip of her tongue danced against the underside of my shaft. My cock was surrounded with new, exquisite sensations. I had never felt anything like this before in my life.
I wanted to surrender to her entirely, release myself inside her mouth. I wanted to watch my cock cum between her lips, I wanted to watch her swallow every last drop from my manhood. “I’m gonna cum…” I warned her.
She stopped suddenly. “Not yet. It’s too soon for that. I want you, Jason. I want your cock inside me. I want to be the woman to whom you lose your virginity. I want you to remember this day for the rest of my life.”
I could scarcely believe my ears. “You want to fuck me, Vivian?”
“I do. I want to deflower you right here in this classroom, just like I’ve been fantasizing about all year.” She stood up and turned so that her back was to me. “Will you unzip me?” she asked sweetly.
I gripped the zipper to her skirt and slid it down, taking the opportunity to caress my hand against her ass. Her skirt fell to the floor, revealing a thong underneath, exposing her firm, tight ass. I swatted her bottom playfully, emboldened by her greatly she was catering to my desires. I felt like a sultan in his harem, having his every need taken care of by his odalisques. She giggled at my spank and turned back around to face me. “You’re very bold, Jason. I always knew you were an excellent student. Sit down in your chair,” she ordered. Still stunned by how events were going, I could only comply.
I slid off the desk, pulled out my chair, and sat down. Vivian stood in front of me, straddling my thigh. My wet, hard cock pointed straight up towards the front of her thong. She looped her thumbs under its waistband and played with it, sliding it down almost far enough for me to glimpse her pussy before pulling it back up. I couldn’t wait any longer. I reached out, eager to tear her thong from her body, eager to thrust myself inside of her.
She slapped my hand awayShe bent over me so that her pendulous breasts hung in front of my face. I kissed them softly as I reached down and delicately removed her thong, exposing her bare, shaved pussy.
Finally, I could see it, my first pussy. It looked so smooth, so sleek. I softly caressed her slit. It was already moist with dew. Her pink lips beckoned invitingly. She stepped out of her thong and climbed into my lap. I kissed her earlobes, and was rewarded with a whispered “Jason…”
She took my cock into her hand and pressed its head against her warm, wet labia. Her thighs clenched. I bucked my hips, trying to force myself into her, but she pulled back slightly with a smirk and a playful laugh. “So eager… I bet you’ve fantasized about this hundreds of times, haven’t you, Jason? Did you ever imagine your first time would be with your teacher?”
“No way. This is like a dream…”
“Don’t wake up too soon, then,” she countered. She kissed my neck passionately. My eyes closed as I felt the tip of my cock slowly penetrate my teacher’s pussy. She guided me into her expertly, slowly, teasing me with each inch, until she had engulfed my shaft. Her warm, moist quim tightly gripped my manhood. I couldn’t believe this was happening to me… I thought back to porn I had seen, trying to think of what I should do, and began to move my hips back and forth, thrusting myself deeper inside of her.
She moaned loudly. Her fingernails clawed into my shoulders. She pulled herself against me, her firm breasts pressing forcefully against my chest, her hard nipples energetically drilling into my skin, rubbing in small circles against me. Panting and moaning, she began to circle her ass around my lap. I gasped from the sudden sensation of my cock being handled so exquisitely.
I grabbed her firm bottom roughly and guided her around my cock. She exhaled passionately, she began to nibble my neck and earlobe while I moved her body against me, thrusting into her. “You feel so big inside me, Jason…” she gasped into my ear. “Your cock is amazing. Keep going, don’t stop,” she begged as she rode my cock. I’m almost there, I’m about to cum…”
She impaled herself upon my shaft, riding me, sliding up and down my cock. Her firm breasts bounced with each thrust I made into her. A wave of ecstasy was building inside me. I knew I was close. I was reaching the plateau, just seconds away from the familiar cliff edge of orgasm. I wrapped my arm around her head and pulled her lips to me, kissing her deeply, passionately. After a second of surprised hesitated, she reciprocated, thrusting her tongue between my lips as our hearts beat together, our chests pressed against one another, our lips locked…
My cock spasmed inside her, releasing my seed inside her as I continued to thrust away. Blasts of pleasure exploded across my psyche. The only thing in my mind right now was the pleasure I was feeling, the sensation of cumming inside my teacher’s pussy, losing my virginity to such a beautiful, older woman as my cock surrendered its essence to her moist quim.
Just moments later, Vivian’s body quivered. She embraced me tightly, her pussy clenched tightly around my satiated manhood. Her whole body shook rapidly back and forth against my crotch as she let loose a loud, wordless, primal scream. I could only hope the school was empty, for I was certain she was audible from the roof to the basement.
Slowly, she came to a halt. My ivory semen was dripping out of her, down my shaft, and onto the chair. Our bodies glistened with sweat. We sat there, exhausted, content, satisfied, for a few minutes, catching our breath.
She sighed contentedly. “That was amazing, Jason… But I’m afraid I’m going to have to give you detention.”
She adjusted the glasses on the bridge of her nose and huffed. “You’re supposed to always show respect for your teacher, and ladies, as well.” She delicately lifted herself up off of my soft dick, stood up, and walked to her desk. She removed a cigarette from one of the drawers, and lit up. She inhaled deeply, and puffed out a ring of bluish grey smoke. “And that includes orgasms. Always let ladies cum first, Jason.”
“Yes, Miss Wong…”
* * * * *
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