A Lesson in Pegging

Story Info
Kevin gets a quick lesson in Pegging from his teacher, Latif.
3.3k words
4.37
42k
41
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Pegmaster
Pegmaster
125 Followers

Kevin walked into campus taking more deep breaths than naturally required. This was a big day for him; Result collection. After a disastrous first semester where he failed four of his eight courses and narrowly passed the other two.

He not only had to avoid failing a course but had to score high in 6 out of his 8 courses to score a high enough GPA that would put him on the right path to graduate. This was a Herculean task he couldn't achieve on his own and many of his female comrades in class supported him in studying. However, the main catalyst in all of this was his general course advisor, Miss Latifah.

Angela Latifah was a well-educated woman who knew how to bring out the best in all her students, had an appealing physique, always wearing a tightly buttoned shirt (mostly white) and a perky skirt, both of which revealed her sexual assets. She usually wore a pair of glasses and her whole attire matched perfectly with her dark skin.

She was very kind, friendly, and down to earth with her students, but hated disorderliness.

Disorderliness was Kevin's pseudonym in first semester, hence he constantly dodged her approach but after seeing his results in the first semester, he crawled back to her like a dog, tails in between his legs, and she was more than happy to offer him a bone of knowledge. She became his private tutor and brought so much positive discipline to him that he felt confident in what he wrote. What truly gave him anxiety was whether he had done enough.

He walked into the campus and then towards his classroom. The air conditioner cooled down his sweat and relaxed his mood. The sight of girls giggling and celebrating their results filled him with hope and dread simultaneously.

Anna University was a small private university, and had a female majority which made Kevin stand out like a sore thumb several times. He got to his class where students queued to take their results. It was a short queue so in five minutes, it was his turn and he met his teacher.

"I'm here for my result, ma." Kevin said with a smile. Latifah, who was signing off on the last person who took their result, raised her head and beamed once she saw her student.

"Oh Kevin. How are you doing this afternoon?" She said with a nice grin, she was dressed in her standard clothes except this time the shirt was much tighter that an extra button was open, opening a cleavage of her huge breasts.

A sight that was appealing to Kevin as he zoned out for seconds while staring at it.

"Hey Kevin. Are you there?" She snapped her fingers and he came back to reality, immediately hiding his face in shame.

"I'm so sorry ma... It's just -" he couldn't finish his statement, telling his teacher he was admiring her boobs was too much even for him. "My result, please." He bowed his head, she responded with a chuckle.

"I want to speak to you later about your result so you'll be the last person I'll attend to. Take a seat at the back and wait for me. Okay?" He nodded and went to the back where he was sad.

Thoughts flooded his mind from every area... What had he done now? Did he fail? Would he not graduate? Would Miss Latifah fail him for the stupid thing he just did. He pondered until it was 4pm when the last person collected their result. His phone beeped, it was a text from his friend, Hannah.

"Kate, Rose and I have collected our results. How was yours?" The text read. Those three ladies were the musketeers who helped him the most in his studies and he was afraid he would let them down by failing.

"Kevin?" Miss Latifah coughed and he threw his phone in his pocket. He sat at the very end of the classroom. "Come over please."

Kevin dragged his feet from his seat at the back to her desk in the front and sat on a chair facing her. She stood up, locked the door and sat next to her, lowering her chest to the table, making her breasts visible. "So, your result." She pulled out a sheet of paper from her file and handed it to Kevin. "Well done. You were able to pass your courses and do well enough to graduate with a decent score." She joined her hands together and smiled.

Kevin grinned like he won a million dollars "oh my! Thank you so much ma. I can't believe it."

"Yes indeed. I told you all you needed was some hardwork and determination and you would score high... There's just one issue." She said, and Kevin's smile instantly turned to a neutral one, something that made her smile. It was exactly what she wanted.

"What's the issue ma?" He asked softly.

She feigned a sad sigh. "You did well but unfortunately because of your first semester failure, your score will only be able to get you a middle class job. You'll score 3.2 which is less than a second class lower. I'm sorry."

Kevin shook his head, his happiness at seeing his result evaporated. She shook her head. "But you do know I'm a big figure in this school, Kevin. I can help you tweak a few things and your GPA will rise."

He immediately leapt from his seat and knelt down, hands together. "Please, Miss Latifah. Please help me."

"Calm down, please." She requested with hand gestures. "If this semester has shown anything, it's that you are dedicated to passing and I'm impressed. But you'll have to perform some tasks for me."

He stood up, and sat back down, dusting his trousers. "Yes, I'll do that ma. Is it money... or?"

"Oh no no no. I want the best for all my students meaning I'll help without charging but..." She tsked and tapped her foot on the ground, arousing and terrifying him. "You trying to offer me money shows how you don't believe I can help you for free. That's an offence and a strike. And you know our strike system, get three, get punished." He nodded in agreement. The strike system was one of the things that motivated him the most to study, Latifah never revealed her punishment and so it could be anything. He avoided getting strikes at all until today. "Now I'm going to ask you something and I want you to be fully honest with me. Can you do that?"

"Yes ma'am."

"Good." She smiled. "If you remember the last time I came to your place to tutor you... Has anything been missing since then?" Kevin paused, trying to avoid saying something that would get him another strike. Nothing came to mind, well except one thing but she didn't need to know that.

"Nothing." He answered. She asked him if he was sure and after a moment of reluctance, he affirmed it.

"Alright then." She opened her drawer and put a fat black dildo on her table. Kevin's eyes and mouth widened but quickly he pretended not to be surprised that his teacher had his dildo. "Have you ever seen this before?"

"No, I've never seen that in my life." He muttered, already preparing to pee himself, his penis had begun to harden and he didn't like it. Once again she asked him and he affirmed it.

She stood up and laughed in a sinister way, circling around the chair with the dildo in her hand. She bent behind him and whispered in his ear, "I don't like liars. Do you know that? You've earned yourself a second strike." His face received a dirty slap from her as she laughed back to her seat. S

"I'm not lying." He coughed out, he was already starting to feel humiliated and wanted to run away from there but showed anger on his face. She picked up her phone and showed a picture to him, the picture of the dildo in its box in his room. All the anger in his face disappeared and became fear, she laughed out as she held his face close to hers.

"I gave an instruction to be honest, and you disobeyed... And of course that means..." She looked at him and blushed at his trembling face. "It's punishment time." She quickly unbuttoned her shirt and forced his face into her giant tits, smothering him as he struggled. She pulled his face out. "Do you need air darling, do you?" She asked softly as he coughed out. "Awww, don't you like big breasts? You enjoy staring at them." She forced his face into them again. "Lick them, suck them." She commanded and he drew his tongue all over the boobs crushing him.

"Oh yes, oh yes lick them all. I'm going to have a fun time with you today haha" she threw him back on the floor and walked around him as he lay on his back. "Now, you're going to use your toy right here and please me. Do you hear me?"

"Yes ma'am." He said, already lacking the will to get up. She sat next to him, handed him the dildo, took off her panties leaving the skirt and spread her pussy wide.

"Now fuck me with that rubber dick." She ordered and he did it until she finally came to orgasm, all over his body. After she finished cumming, she stood and saw him licking her cum which triggered an idea in her, she instantly turned on her phone's sound recorder and answered him.

"Are you licking my cum?" She said, startling him and he turned to her standing over him. He was already trembling, he knew this was strike three and had no idea what was in store for him. His penis stays hard but his heart beats faster and he sweats.

"Please, I'm sorry." He went on his knees.

"I don't want to hear it." She interrupted and lifted him up. Physically he was a smaller guy while she was a powerhouse of a woman, no biceps but she still lifted him easily and rested him against the table. Her shirt was still on but she aggressively took his off, and turned him around, then she took his trousers and his underwear off leaving him stark naked. "Bend over"

"Do I have to?" He murmured hoping she wouldn't hear him but he heard him loud and clear.

"Well... If you want me to help you boost your grade then you take your punishment nice and well. Okay? Now bend over!" She said fiercely. He groaned before eventually bending over her desk, putting his hands in front. "Good." She ran her hands along his ass. "Now this is one beautiful ass, at least for a man. She observed along his butt and back, every touch sent an electric signal to his brain, she. As he revelled in the feeling even starting to moan, a large slap hit his ass cheek.

"Damn!" He screamed, two more slaps followed before he decided he could take no more and placed his hand to cover his butt.

"Are you covering your butt? The same butt I'm trying to turn red. Oh no no. Now you've just earned yourself a harder set of spanks" she slapped his ass repeatedly, and once again he tried to cover. She gasped. "You're still trying to cover?"

"I'm sorry mistress but it hurts." He realized he immediately fucked up after uttering the statement.

"Mistress?" She scoffed. "Oh wow. You really are loving this? Maybe I should spice this up a little."

"No no please. I want to go home!"

"Oh but honey, we're just getting started. You're not going anywhere." She went to her drawer and brought out a pair of handcuffs. " You see, ever since I saw that dildo in your room. I knew what that punishment would be when you got three strikes." She went behind his back and handcuffed him, spanking him when he tried to struggle against the cuffs. "Stop fighting it. This is going to happen."

"Stop! I want to go home." He cried again but she only spanked him harder.

"Oh your brown ass is getting so red." She chuckled and moved in front of him. "Now it's fun to hear you, but I want to block your mouth with something." She leaned to his ear. "Something that belongs to you."

"No no!" He screamed but she was already laughing away... She returned a few minutes back wearing nothing but a strapon harness with his dildo attached to it.

"Well, how do I look?" She teased him but he looked away. "Come on." She lifted his head and looked into his eyes. "You can't deny that I don't look hot?" He only sniffled. "Okay, suck this dick, it still has my pussy juice on it."

"No."

"Come on, we both know you want this, stop pretending!" She groaned playfully. "Anyways, I wasn't giving you much of a choice." And with that she pulled his head and began fucking his mouth with the dick. "Yeah, boy. That's a good boy." He pulled his mouth out, and she slapped his face hard. "Suck it!" She forced his mouth back into the dick and jammed it into his throat until he started to cough and spit. "Ohhhh there's a slut." She laughed and continued pounding his mouth while stretching her hands wide. She her hips to control the cock into his mouth and fuck it properly, until she pulled out of his mouth. His face was already drenched in spit and tears.

"Awww... Are those tears of joy I see." She looked at him. Kevin begged for no more but she could barely care, she was having the time of her life and deep down Kevin was too but he didn't want her to know that hence the constant fake struggle but Latifah knew when she had people hooked and Kevin was soon to be in that spot.

"Now I want you to suck it yourself... Understood?" He slowly nodded and only licked and sucked the tip, doing it with minimal effort. "Are you serious now? If I put this effort into tutoring you, do you think you would've even passed?" But he continued sucking like a lazy sloth. Latifath got frustrated, and after facepalming, removed her penis. She held his head "now look at me, I don't know why you're being lazy but know that I'm not using any lube, this is the only wetness you will get. Now unless you wanna cry when this goes in. You'll suck this dick now." Immediately Kevin transformed into a professional cocksucker, much to Latifah's amusement who even laughed multiple times, telling him he deserved an A in dick sucking.

"Hahaha. You're a wild one aren't you?" She laughed out and pulled the dick out as he spat on it, giving it the final wetness. "It's butt time." She walked over to behind him and smacked his ass a couple times. "Relax darling. I'm not cruel, I'm still going to use lube, I just wanted to turn you into a whore for me." She giggled and brought Vaseline out of her drawer, applying it on the dick and all over the hole. "Take a deep breath. It's pounding time."

"I can't take it." He whimpered like a bitch as she put it closer to his hole. "It's too big"

"Oh but you can and you will..." She gently slid the penis into his hole.

"Fuck!" Kevin screamed and Latifah laughed out loud.

"Relax, I'll be very gentle." She said, and forced the whole dick in. Once it was in, she started with slow strokes to get him used to it. "How does it feel?"

"Oh it's so big." He sobbed.

"Yes it is baby, yes it fucking is." She started swinging her hips and laying him down with the pipe at full speed, after all he was comfortable wasn't he?

"Oh! Fuck! Shit! Oh my gooood!!!" He screamed and she laughed every single time at a higher volume than him, making him feel more sore. "I can't take it, please slow down."

"Slow down! I'm having way too much fun here to slow down." She said, pulling his hips and jamming him harder, making him scream more.

"It's too big." He wailed. "My asshole. It fucking hurts!"

"Oh I'm sure it does but you like it don't you? Tell me how much you like it." She said but he just continued screaming and pleading. She hit him with the hardest snack so far. "How much do you like my dick?"

"I fucking love your dick!"

"Louder!"

"I love your dick! Thank you for your dick!"

"Such a grateful slut!" She laughed louder at this and spanked him more, pounding the shit out of him till he began to cry. "Crying already? But I used the lube haha."

"It's too much mistress."

"Thank you very much!" She spanked him again and removed her hands from his hips. Only throwing her dick in him but flinging her hands in the air like a cowgirl in a rodeo riding a horse or in this case, pounding on. "Yeah baby yeah. You back up on my dick!" He pushed slowly as she stopped pushing in. "Oh, you're so hungry for the dick. Yeah, twerk it." He pushed faster and faster, enjoying the pain and the pleasure. "Oh yeah, drop it while it's hot, drop it. Oh you wiggle your ass baby" she spanked him harder until it finally turned red. "Yeah, jiggle your ass on my dick. "

She pulled her dick out of him "Oh good boy, good cock slut. Come taste your ass on your own dildo."

He knelt in front of her and sucked his ass out of her dick, this time she didn't need to force it in. He was sucking the dick like his life depended on it. This turned her on so much, he finally made him her slave. She had turned her student to her slut.

"That's enough." She said and pulled her dick out. "Go outside and freshen up in the bathroom. I'm done with you for today. Once you're done, I'll drive you home." He hurried into the school bathroom two classes away while still naked. The whole school was empty, it was night time and Latifah had used her connections to get her privacy.

Once he was in, he prepared to bathe but before he could do anything, he heard footsteps entering the bathroom wearing the strapon and holding her phone.

"On second thought, I'm not done. Put your hands on the wall in front of the mirror." He instantly obeyed and she slid the dick into him from behind. "Fuck my dick!" She spanked him. "Ride it good like that." She opened the camera on her phone, and recorded the whole sex encounter through the mirror. With her camera facing the mirror, she recorded his moaning face, her dominant eyes and she even pulled his neck to kiss him on the forehead for being a good boy. He was truly at his mercy. She also recorded his ass going in and out of that dick before finally ending the video and giving him the chance to masturbate and cum.

Once all was over, they entered her car and drove it out. He requested the videos and she sent them to him.

"Now. You'll meet me thrice a week and we'll work on building you up to a 4.5 and above, and bring a bottle of lube okay?" She dropped him at his place and he waved her off. This was his fantasy come true and while it was rough, he loved it. Far more than Latifah knew.

Pegmaster
Pegmaster
125 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
2 Comments
wwaldripwwaldrip5 months ago

Really enjoyed your story look forward to more chapters, very erotic

AnonymousAnonymousabout 1 year ago

I enjoyed the story, keep up your writing!

Share this Story

Similar Stories

Prom Night Pegging Prom date reveals how naughty she really is...in First Time
Sexy Doctor Gives Prostate Exam Guy is surprised when female Dr. shows up for prostate exam.in BDSM
Tamed by Meg Megan introduces me to the pleasures of being penetrated.in Anal
Easy First Date Girl uses strapon to peg a boy.in Anal
Strap-On Roommate Two guys are done by women with strap-ons.in Fetish
More Stories