πŸ“š boyfriend lessons Part 9 of 9
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Boyfriend Lessons Ch 09

Boyfriend Lessons Ch 09

by fpat97
20 min read
4.36 (14000 views)
adultfiction

Chapter 9 - Midterms

It was a long week for Eric. Very long. He thought the prior week was intense, but this time there would be no midweek release. Every time he sat down to write his "mid-term" he was so horny that he couldn't focus. He'd look at porn to distract himself and end up so horny he had to step away. Whatever happened, he knew he couldn't have another "accident"

To make matters worse, Kevin kept walking in on him. Kevin tried to talk to him once about it, but got so frustrated that he gave up and walked away. Eric didn't even notice when he started giving him the cold shoulder.

Eric couldn't stop thinking about sex and what it would take to get Mona to let him cum again. The two texted all week, exchanging pleasantries and flirting, but any time he tried to sext she ignored him. She reminded him a few times about the assignment and stressed how important it was.

Finally, Friday morning he buckled down and did his best to write the paper. As he wrote, he realized just how much he had fallen for Mona. Sure, she was beautiful, but it was more than that. He poured his heart out, writing with abandon about how much he enjoyed being ordered about and how fulfilled he felt when she was happy with him. He talked about how relaxed and content he was to sit at her feet while she worked. He even hinted that he enjoyed her punishments, but was too embarrassed to elaborate. He wrapped up the paper by talking about how much he appreciated Mona's lessons and how he was committed to becoming her perfect boyfriend. It was rushed, but he hoped it would be good enough.

Eric managed to finish the paper, print it out, and put on nice pants and a button down shirt just in time. Mona pulled up as he was exiting the dorm. He hopped in the car the two drove off. Mona was a pretty girl, but he had never seen her like this. She was wearing the classic "little black dress" and it hugged every curve she had to offer. From her pert breasts to the slightly revealed tops of her stockings and her absolutely perfect makeup, with bright red lipstick, Mona looked sexier than he could have imagined.

"Good, you printed it out," Mona said as she tapped the steering wheel, "I hope it's good." She stole a look his way and smiled. "You do clean up nice." The two drove in silence, the only sound Mona's arrhythmic tapping. Mona pulled up in front of a brownstone in one of the nicer neighborhoods that ringed the university. They rang the doorbell and waited at the red mahogany door.

Eric wasn't sure what he had expected, but it was not a young, blonde bombshell in a maid's outfit. Standing no more than 5'1", with perky C-cup tits, she wasn't wearing the slutty maid costume of Halloween fantasies. Instead, she was wearing an impeccably tailored domestic servant's outfit. It was understated, but the plain black choker with a ring made it clear she was here to serve, however one wanted.

"Hi Mona!" She bubbled. "The Mistress is waiting for you in the parlor." She didn't acknowledge Eric's presence before turning to lead them on. Turning the corner into the parlor, Eric got his third major surprise of the night. Sitting in an armchair by the fireplace was Professor Jessica Lande.

Eric looked from Mona to the maid and back to Professor Lande. He had been cautiously optimistic about tonight, but now all he felt was panic. Professor Lande taught materials science and he had not done well in her class. Further, she was emphatically not his type. She was fit for her age, but severe and old enough to be his mother. If he had to guess, she was probably in her mid fifties.

And yet, he had a crush on her. When she was up front lecturing, full of energy, smart, and in control, he was drawn to her like a moth to a flame -- just like every other female teacher he had. He flashed back to jerking off to her and his face grew hot. Eric hoped she might not remember him, but that hope died when he finally met her eyes. She knew who he was. She knew he was a mediocre student. He was pretty sure she could smell his fear.

"Mistress, I've brought my new boy, Eric, for your approval. I think you'll like him. If you approve, I'd like to continue his training."

Professor Lande rose and the two embraced. Eric was dumbfounded. Mistress? He numbly walked over and took Professor Lande's outstretched hand to kiss it. When Mona sat in the other armchair, he knelt next to her. Both women smiled at this, and Mona tousled his hair.

Eric was in shock while the two women talked and gossiped about people and things Eric didn't recognize. Mona recounted some of her adventures with Eric, talking up what a quick learner he had been. The maid brought drinks for the ladies, ignoring Eric completely.

"She's beautiful, isn't she?" Lande said, drawing Eric's attention.

"Ye.. yes, she is."

"Stand, boy. Let's see what we're working with." Lande instructed.

Eric stood with his hands behind his back. Professor Lande inspected him like a prize animal, or a piece of meat. She addressed Mona, ignoring him.

"How is he at oral?"

"He started out poor, but he's gotten better. He needs more practice."

"I see. Does he take correction well?"

"Well so far, though he does need more reminders than I'd prefer. Especially after an orgasm."

"I warned you about that. When was the last time that happened?"

"Last Saturday."

"Hm. Boy, the paper." Professor Lande held out her hand. "Rub my feet while I read."

Eric obliged, thankful for something to do, slid off her black pumps and got to work. He was gentle with her black stocking, and thankful that he could only smell the faint vanilla of her body wash. He cock swelled in his pants and, against his better judgment, he couldn't help wondering what they would be like after a run.

He looked up when the maid walked by, but it was only to hand Professor Lande a red pen. She tutted at him to focus on his task. The maid walked past, and he heard her chatting with Mona, but he didn't dare look. He focused on her feet, sneaking an occasional glance up her skirt. She was wearing full pantyhose, rather than the stockings her maid wore, and Eric daydreamed about nuzzling his way up her legs. She had to be a runner with such slim legs and strong thighs.

Professor Lande finished reading his paper and put it on the table. Eric caught a glimpse as she put it on the side table. It was covered in red marks. His heart sank.

"Take a look, boy." Professor Lande pointed over his shoulder.

Eric turned and his heart sank further. Mona, the woman he was falling utterly and completely in love with, writhed in the armchair. One hand grasped her tit while the other ground the maid's head into her sex. Mona had been biting her lip, trying to remain quiet, but when she saw Professor Lande was finished, she let out a long-stifled moan.

"You wish you could eat pussy that well." Professor Lande stroked Eric's head. Only then did he realize Mona wasn't giving corrections like she did to Eric. The maid knew all the right points to hit to drive Mona wild -- and he didn't. "In my house, we all share. Besides, would you really want to limit her pleasure to your meager skills?"

"No...," Eric dumbly shook his head. She was right, of course. Mona deserved nothing but the best.

"Good boy. Before we talk about your paper, a lesson in sharing." Prof. Lande leaned forward and was whispering in his ear. "Mona is enjoying Sasha. You want to too, don't you?"

"I... I do."

"Go then. Fuck her. It's what she's there for."

As if on cue, Mona caught his eye and nodded. She seemed less anxious now, and her nod was more command than invitation.

Eric crawled over to Sasha. She's a sub like me, he thought. His heart fluttered as he admitted to himself that he was a sub. Then he realized how stupidly obvious this was. He hiked up Sasha's skirt, planting kisses on her ass before sliding down her panties.

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He was surprised to find a pink, heart-shaped jewel sticking out of her ass, but he was more surprised when he didn't see a vagina. Instead, Eric found a cute, pink little ball sack. It was encircled by pink plastic attached to a pink tube which encased Sasha's cute little cock. Eric assumed it was little, considering the size of the chastity cage. Eric recoiled, but caught the warning in Mona's eyes. Another test, he thought. He steeled himself, bent down, and kissed the smooth skin of her scrotum.

He had to admit, it was kind of nice. Her sack was taut and smooth as he toyed at her balls with his tongue. His heart soared when he looked up to see a smile on Mona's face. Then he noticed a bottle of lube had been put under the chair. He removed the small plug and lubed his rock hard cock before lining it up at her entrance. He hadn't cum in almost a week and his need was palpable.

"You cum when I cum," Mona said, meeting his eyes.

"Yes, mistress," Eric replied.

Eric pressed the head of his cock against Sasha's waiting backdoor, and it slid in easily. After a week without orgasm, he almost lost control when he bottomed out and felt her soft ass against his hips. Sasha moaned as he plumbed her insides, but never lost focus on her task.

Eric fought his orgasm, gasping for breath as he slowly fucked Sasha. His pace was ponderous and it must have shown on his face, judging from how much it turned Mona on. Soon, Mona was gripping Sasha's head as she rode her orgasm. It was too much for Eric and he grabbed Sash's hips, fucking her with wild abandon, pushing her face deeper into Mona's pussy, as he emptied his balls.

As his head cleared from the intensity of the orgasm, Eric realized his mistake. Good boyfriends always clean up their mess.

"You don't have to," Mona laughed when she saw the fear on his face. "This time."

"Thank you, mistress." Eric replied. He replaced the plug, sealing away his deposit, and pulled up Sasha's panties.

"Thank you, sir." she said breathily before kissing him. Eric could taste Mona on her lips as the two made out. Their hands roamed over each other's bodies as their tongues explored their mouths.

"That's enough," Professor Lande's stern voice rang out. "Sasha, assist our guest in cleaning up and get him ready for the next portion of the evening."

"That was pretty good," Sasha giggled as she led him through the kitchen to a washroom. She kissed him again and grabbed his crotch. "You almost know how to use this. I was sure you'd lost it before Mona came, but it's good for you that you didn't. Mistress Lande wouldn't have taken that well."

"Have you... worked for Professor Lande for a long time?"

"You could say that." Sasha smirked. "She's owned me since I was just 19, and I couldn't be happier with our arrangement. It's been a wonderful five years."

"And... uh... I don't know how to ask this. Did she... is this... part of it?"

Sasha rolled her eyes and gave him a pitying look. "No, Eric. I've been a woman since long before we met. Don't worry, she's not going to "turn" you or whatever you have going through your head. Unless, of course, that's what you want." Sasha winked.

Eric let out a breath he didn't realize he had been holding. He laughed nervously. "You're beautiful, but I'm not sure that's for me."

"Mistress Lande is demanding, but she's good to me. She's helped me through a lot and she helped me get these." Sasha put Eric's hand on her chest. "Nice, right?"

Sasha leaned in close and kissed him again, letting Eric explore her body. He ran his hands up her thigh and brushed against her confined member. Sasha grabbed his hand and let him feel her straining against the cage.

"Easy tiger. Let's get you back out there. You aren't done yet." Sasha grabbed a washcloth and cleaned the lube and cum off his cock, and told him to undress. She laughed when Eric hesitated. "You just fucked me in the ass and now you're getting bashful?"

Chastised, Eric took off his remaining clothes and followed her back to the parlor.

Eric heard the snap of the crop before he entered the room. Mona was bent over the table with her skirt hiked, panties down, and ass covered in angry red marks.

"Eighteen," she said through gritted teeth.

Eric's heart raced and he started to her side, but Sasha's hand stayed him. She shook her head slightly. He watched, helpless, as Mistress Lande finished her last two strokes, Mona's backside, the backside Eric had so often lovingly kissed, was covered.

Mona pulled up her panties, smoothed her skirt, and knelt down in front of her Mistress. "Thank you for the correction," she said, far more meek than Eric had ever heard her. She kept her eyes downcast before her Mistress.

"It was a poor paper and you should never have let him submit it." Professor Lande began. She looked to Eric, "just like with your poor grades last semester, your TA bears some responsibility. Now you see exactly how she bears it." Eric blushed and fidgeted at the reminder of just how badly that class had gone.

"Further, you've been far too nice to the boy. He may not understand our expectations now. He's had more orgasms in the past month than Sasha has in the past year!"

"I'm sorry, Mistress. I didn't want to scare him away."

"Boy, are you scared?" Professor Lande looked back to Eric.

"No, Mistress." That wasn't true, but Eric knew he needed to show up for Mona.

"Hmph. We'll see." Professor Lande walked up to him and looked him up and down like a piece of meat. "Your paper was trash, but you already know that. If you choose to stay with Mona, you will revise and resubmit it by the end of the week. Understood?"

"Yes, Mistress."

"Enough of that. I'm not your Mistress. You haven't earned that, boy. You will call me Professor until I tell you otherwise."

"Yes, Professor."

"Good. Now. Let's get some things straight." Professor Lande pulled a simple leather collar off the table. It had the same sort of ring as Sasha's choker. Only now did Eric really look at the table. While he was out of the room, someone had arranged all manner of sex toy and torture device on it. He sucked in his breath as he realized what they were for. If Professor Lande noticed his reaction, she didn't comment on it.

"This," she said, indicating the collar. "Is the next part of your training. It means that, until the end of the semester, Mona owns you. Everything you do, everything you say, everything you fuck, is up to her. If she wants to spank you, she will. If she wants you to go down on her, you you. If she wants you to spend an afternoon eating her chubby roommate's ass then your jaw better be up to the task."

"Yes, Professor."

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"Easier said than done, but I appreciate enthusiasm. I would add that you cum when she says, but that won't be an issue. My own requirement is that you not have any orgasms until your final exam. That is 12 weeks away. Do you think you can do that?"

"Y... yes, professor." Eric stammered, just a little.

"Hah! No, you can't, but we can help with that. Sasha, if you would be so kind."

Sasha walked forward carrying a small silver platter with a ring and cage on it. Eric didn't need to look to guess what it was. She knelt in front of him and grabbed his package.

"Don't worry, boy. You'll get used to it within a few days. Mona will have the key and will decide when to let you out. Though, Mona, I would advise he not be allowed out for anything but hygiene for those three months. I've found that a long initial lock up helps them lose hope they'll ever control their cock again."

"Yes, Mistress." Mona replied.

At this, Eric cock started involuntarily stiffening. How the fuck am I getting excited at this? He thought. But deep down he knew. He loved the idea of Mona owning his manhood, owning him. He blushed and looked away.

Sasha saw Eric's cock getting hard and giggled. He heard the snap of the cold pack activating right before she pressed it on his member. He yelped in surprise, but kept his composure as his cock shrank. Sasha slipped on the cage, locked it, and handed Professor Lande the key. Eric looked down at the jet black cage, his cock visible through the bars. Part of him was shocked, and part oddly serene about it.

"Good, that's better. Where were we? Oh, right. Going over things Mona should have made clear." Professor Lande shot Mona a look of her continued disappointment. "Mona owns you and your body. She will use it as she pleases. You have no such claim to hers, understood?"

"Yes, professor." Eric whispered.

"It won't be easy, but you need to get over it. Consider it personal growth. She is going to fuck who she wants, when she wants, how she wants. You won't be fucking her," she said, nodding to his encased member, "but that doesn't mean she's going to be denied."

Eric looked away, embarrassed and not sure what to say.

"Do you understand what I just said? If you agree to all of this you will be Mona's property through the end of the year. At that point, I will decide if she can keep you. If she still wants you, that is."

"Yes, Professor." Eric mumbled.

"Beg for it."

Eric looked up. Professor Lande was staring at him while Mona was the picture of submission, staring at the floor. "Please?" he croaked.

"Please. What?" her voice was stern, unyielding.

"Please. Please let Mona keep training me" Eric met Professor Lande's eyes and the dam broke. His eyes start to sting. "I'm sorry my paper was trash. Please, let Mona own me. I'll do whatever she wants. I want to make her happy and... and.."

"And...?"

"I want to be her... slave?" he searched for the right word, on unfamiliar territory.

"Pet will do for now." Professor Lande corrected. She snapped her fingers and Sasha brought over the collar. "Kneel."

Eric knelt so Professor Lande could properly collar him. Her hands were warm and tender on his neck. He felt her closeness as she fastened it and a breathless "thank you," escaped his lips.

"Mona, your pet." Professor Lande bid Mona to rise and handed her the key to his chastity cage. "I think you should give him a lesson, don't you?"

"Yes, Mistress. He disappointed you, and embarrassed me. Pet, do you think that deserves a lesson?"

"Yes, Mona." Eric squeaked. He could tell how angry she was at his poor showing.

Mona walked over to Eric and slapped him across the face. Hard. He saw stars and yelled out.

"What the fuck?" Eric cried as he massaged his cheek.

"You will refer to me as mistress!" SMACK! Mona slapped him again.

"Ow! Fuck! I'm sorry, Mistress. Yes, Mistress." Eric cowered before the women, aware of the collar around his neck, his confined member, his nakedness, and how deep down this rabbit hole he had fallen.

"Good boy. Now, bend over the table."

Eric wordlessly complied. Out of the corner of his eye, he saw Mona consider the crop Professor Lande had been using not twenty minutes ago, and choose a cane instead.

No amount of bracing could prepare Eric for getting hit with that cane. No warmup. No warning. Just pain. It painted a searing line across both cheeks and he yelped in pain.

"One," he croaked when he had regained some composure.

"Two," and another line of fire across his ass. Every thought was driven from his mind, crowded out by the pain. Sasha stepped to the other side of the table and stroked his hair.

"Deep breaths. You're doing great," she said. He looked up at her, took a couple deep breaths, and got ready for the next.

"Three!" he yelped. Four and five were bad, but not as bad with Sasha comforting him. Her presence shone through the fog of the caning. He could focus on her instead of his abused backside.

By the time he hit ten, the pain was ramping up again. It crowded out Sasha and left him in a daze. It hurt, but it was a new kind of hurt. It was so intense he wanted more of it at the same time that he wanted it to stop. He couldn't think straight and didn't know what he wanted.

Mona noticed the change and picked up the pace. She was at fifteen before it fully registered, but by the time she reached twenty the intensity was too much. Eric could feel the tears welling up in his eyes, threatening to burst.

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