Lessons Ch. 01

"Umm, Jayden, listen, lemme just think this over and I'll get back to you in a few days or so, okay?" Jamilah said as she got up and started packing up her things.

"Okay cool, can I give you my number?"

"Sure." She said as they were both standing up now. Even when they were sitting down she knew he was tall from the where his knees lay, but now that they were standing she was basically looking up at him to speak. He had to be at least 7 or 8 inches taller than her, and she was 5'4 .

He pulled out a white business card and handed it to her.

"Cool, so here just call this number and let me know what you think. Hopefully I can help you out."

"Thanks Jayden."

"No problem, umm oh I didn't get your name..."

"Jamilah." She said as she cracked a smile. She didn't even mean to smile either...

"No problem, Jamilah. Talk to you later."

Jayden left the room, and Jamilah took a glance at him, wearing a black t shirt with grey sweatpants.

There's no way I'm going over there. Absolutely not! I cannot call him even. I won't.

But he was nice, and she wondered if she was overthinking it. Plus, she would get to see him again...

***

"Jamilah, just go! It'll be fine."

"You always say that about shit that you don't have to go to, Alicia!"

Jamilah and Alicia were back at their dorm late at night, discussing the encounter Jamilah just had with Jayden. Jamilah was laying on the bed in her usual boy shorts and t-shirt, while Alicia was sitting in a chair across from the television. Even though Jamilah tried to deny it, she thought about Jayden her entire trip back to her dorm. No matter how much she was attracted to him, she couldn't shake the weird feeling from going to his place to do private lessons on the software. That's why she had to ask her best friend for advice.

"I know I don't have to go, but it really doesn't seem that bad, Jam. And he doesn't sound bad at all."

"Yea I mean he doesn't seem bad from what I saw, but-

"What do you mean, from what you saw?" Alicia said with a little smirk.

"You know what I mean, Alicia, hush!" Jamilah annoyingly replied.

"Look, all I'm saying is that it seems like he knows his stuff. I mean in that one encounter he was able to teach you something that you didn't know at all when it comes to the software, right? Imagine what two, maybe three sessions could do for you. You could become an expert if you work with this guy."

"...I mean yea..."

"Plus, you know you have that job interview soon..."

Shit she was right. In all the confusion from meeting this guy and possibly finding a tutor, she forgot about all the jobs she applied for months ago, just hoping to find something that worked for her and got her foot in the door. Some of them were for graphic designing and editing positions that she figured wouldn't give her a second look. But she did fill her resume with skills that she planned on acquiring but hadn't exactly acquired yet. But now one of the jobs called her back and scheduled an interview for 2 weeks ahead, and she needed to at least have some entry level experience as they said on the qualifications.

Jamilah looked around and stayed silent.

"You can look around all you want, but taking these sessions with this guy might be the difference between getting a new job and struggling for a little longer."

"Yea, yea I know..."

"And I mean what's the worst that can happen anyway?"

"Umm I can get drugged, raped, or kidnapped! Are you serious?"

"Are you serious? Come on, Jamilah, that is not going to happen. You said he was nice and it's not like he's lying about knowing his shit."

"Okay, okay. I'm getting sleepy, please leave my quarters and let me ponder." Jamilah jokingly said in a royal accent.

"Shut up your highness. Alright, just think about it. It might be good for you."

"I know, thanks Alicia, I'll think it over. Night."

"Night." Jamilah lay her head on her pillow, curled up under the covers, and turned on some relaxing music to fall asleep to. She tried to clear her head and just relax, playing with her dreadlocks and not thinking too hard about Jayden and these sessions. The decision would just come naturally.

***

Okay, you got this. Just relax, nothing bad is gonna happen.

Jamilah was riding on the train, in her usual secluded spot in the corner, thinking over her decision. In the past few days, she just went through her usual schedule and tried not to think about Jayden too much. Eventually, she decided that it was a good idea to at least try it once. What's one time, she figured. That way, she might learn some new skills and techniques, and if she felt like it wasn't working out, it was just one session and she could back out.

Since Jayden gave her his card, she texted him that she was interested in having him be her tutor, and he sent her his address. Surprisingly, he didn't live far from campus either, and she wondered if he went to the same school as her, or at least used to. It was a huge spread out campus, so she wouldn't have known if he went there. Still, she felt like he was a little older than her, and she was 21.

As she exited the train, she walked towards some small apartments, and realized that Jayden didn't live in some lavish, huge house, but something similar to how she would live. She didn't know why she was picturing him as something vastly different from herself, or living in some crazy weird place. But he was just a normal person, it seemed, trying to make a living by offering sessions to people. She tried to calm down and stop thinking too deep into it.

As she knocked on the door softly, she looked at her body to think about what she was wearing. It was a warmer spring evening, so she decided to wear another one of her tank tops, this one a sunny yellow that contrasted with her dark brown skin beautifully, and some more black leggings and running shoes. She wanted to be comfy, and didn't dress up or anything. But she did think about what Jayden would see and wouldn't see. She wasn't showing a bunch of cleavage, but the tank top was cut low enough so that he would see something.

"Hey Jamilah, come on in." Jayden said as he opened the door. He also liked to dress comfortably, she realized, as he was wearing something similar to before, this time a light blue shirt with black sweatpants.

At first glance, his place confirmed what Jamilah already knew and what her friend told her as well: this guy was really into this. After they walked through the kitchen and living room area, which seemed fine and neat, his room had computer parts all over the floor. There was a huge desktop, and other tools and stuff to take them apart apparently.

"Sorry about the mess, I get so busy sometimes and forget to clean up."

"No, it's fine, I understand. I'm a painter so I definitely leave messes all over my dorm."

"Oh really, you're a painter? That explains why you were opening Illustrator the last time I saw you." Jayden said as he sat down on his bed and gestured for Jamilah to sit on a nearby computer chair.

As she sat down, he noticed the way her big round ass fit in the chair, and couldn't help but glance at her plump thighs before quickly looking away. She looked so good, and he felt the beginning of a bulge growing.

"Exactly."

"So, what are you trying to learn this stuff for anyway?"

"Well, I figured since I'm a painter and an artist, and I want to work with art in my career, I should probably learn something new to make myself more appealing on the job market."

"Yea that makes sense, that's actually a great idea. That's kind of how I got into this stuff. It can be rough out here looking for a job."

"Tell me about it."

"Right. So, I thought that we would just continue with Illustrator, since you're a visual artist and that's the one that you booted up the other day, and then move to some other graphic design apps, and then maybe Photoshop and some film editing? A lot of them are similar, so learning one usually helps the transition to another."

"Cool, sounds good." Jamilah said, wondering how many sessions he expected them to have.

"Awesome, alright so let's go ahead and-

"Actually, Jayden I need to say something first before we start."

"Oh, what is it? Did I do something wrong?"

"No, no. I just needed to apologize for the way I was acting the first time I saw you, especially when you offered to give me lessons. I was just being super careful, I always am, but I didn't mean to paint you as a bad person or anything. Cause you seem really sweet and stuff."

"Nah it's cool, Jamilah, I understand. You were just being cautious, I can't blame you for that."

"Cool." Jamilah smiled and Jayden followed. Their dark brown pools met each other in a momentary glance, and then Jayden commenced the session, showing Jamilah all of the ins and outs of the software. Being that it was a new software, she was finding it difficult to keep up, and would often have to stop Jayden and ask him to repeat something or slow down.

A few times, when Jayden would lean over and type on the keyboard, he would look down at her soft chocolately breasts in her tank top and bra, then look up to see if Jamilah was working with the software correctly. Jayden originally told Jamilah that the session would probably just be an hour, but before she knew it the darkness filled the night sky. It had been over three hours since she arrived, but she kept wanting to learn more and found it interesting. After she got the basic controls down, she would try it out using an idea she had for a painting, and Jayden would be amazed at her creativity. By the end of the session, she knew more, but would still need a lot of work before she could work professionally.

"Wow, I can't believe it's been that long since we started. It's like dark out." Jayden said as they found a stopping point.

"I know, it feels like I just got here. But I do need to go, I've got schoolwork to do and class tomorrow." Jamilah said as she packed up her things and got ready to leave out.

"Wait, umm well there's one thing we didn't really talk about yet..."

"What's that?" Jamilah said, almost halfway out the door.

"Well the payment."

Riiiight. He wasn't doing this for free. She put her hand on her forehead and held it down. How could she forget to ask him his rates? She barely wrestled with the decision to come here at all, and now she didn't have a dime to give him.

"Shit, well I don't have any money to give you right now, I barely ever have enough money to take the train and eat. I'm not sure how I would pay you."

"Oh...well I guess we'll have to stop the sessions then. It's cool if this one's for free, but I don't have a bunch of money either and I can't give out that many free sessions."

"No, no of course. But this did help a lot and you do know your stuff. I don't really want to stop these sessions, I was looking forward to learning some of the other apps."

Jayden looked down and started twiddling his thumbs, looking a bit nervous.

"Well, there is one way that you could probably pay me..."

"There is? What?" Jamilah exclaimed, optimistic about continuing the sessions.

"Well, you could...please me..." Jayden gestured downward as he nervously made his suggestion.

"What do you mean please you?" Jamilah said, but as she thought about it she suddenly zipped backwards and gasped. He couldn't mean that, it couldn't be what she thought it was.

"Well, you know..." Jayden couldn't be any more nervous at this point.

Is he serious!? There was no way she was going to do anything to him, not fuck him, not suck his dick, not even let him cop a feel on her ass or breasts. It was a crazy idea to her, and she couldn't believe he pulled that one out of his ass.

"Umm no, absolutely not! What kind of girl do you think I am?"

"Well, don't you want to continue the sessions?"

"I don't want to continue them that badly!"

"And don't you have that job interview in a few weeks? You don't want to go to them not knowing the software you told them..."

"I mean yea but that isn't worth all this."

"It's that bad huh? I'm that bad?" Jayden looked down in disappointment.

Even though Jamilah was astonished at the idea, she didn't mean to hurt his feelings. Jayden was a good-looking guy for sure, she couldn't deny that. But the idea was just too much to wrap her head around, and it surprised her beyond belief. It just seemed to come out of nowhere.

"Look Jayden, I don't mean to say that you're a bad-looking guy, or even that you're mean or nasty or anything. You're really nice and you've been helpful, but it just caught me off guard. I mean, you're asking me to do something sexual for you, in exchange for lessons on software. And sure, I need it, but how can you expect me to really do that?"

"Well, you haven't said no."

"I mean-

"Just think about it. Does it really seem that bad when you visualize it?"

She had to admit, when she did what Jayden said, it didn't look that bad. In fact, she'd thought about how he looked with his pants off a few times after first meeting him. She was definitely attracted to him, she just hadn't done anything like this before...

"I mean it doesn't seem that bad, it's just-

"I know, it's weird and I probably seem weird for even asking. I'm sorry, Jamilah, I didn't mean to freak you out."

His shyness was starting to turn Jamilah on more. There was a cuteness to how awkward and lost for words he sounded. His nervousness was met with her subtle smile, and some moisture in between her legs, building slowly but surely.

"It's okay, you don't have to really explain it. So, if I do this, that means I won't have to pay you, right? You're not bullshitting me, are you?"

Jayden looked shocked, his eyes and mouth wide open almost in disbelief.

"Umm...yea definitely. You won't have to pay anything..."

"And I'll get free sessions for the rest of the time, however many I want? There's not limit or number to this is there?"

Jamilah started to think about the possibility of being able to have an unlimited amount of sessions and learn all the software she wanted, making her resume and skillset way more marketable to companies. For free. The idea began to seem more enticing and advantageous to her...

"No, of course not. Y-You're good..."

Jayden could barely get the words out as he responded to Jamilah's line of questioning. As she listened and watched him respond, she could see his bulge in the grey sweatpants growing bigger and bigger, which made her even wetter and even start to salivate, despite the outlandish nature of the request and the situation.

"You better keep your word." Jamilah said as she smirked and then, to Jayden's surprise bent down on her knees in front of him until she was eye level with his hard bulge. She started rubbing it slowly, feeling its hardness and shape against the palm of her hand, and making her more curious about what he looked like with the sweatpants off. Jayden began flinching and shivering as she rubbed him.

"This is what you wanted, isn't it?"

"Well...yea but I didn't..."

Apparently, he didn't expect Jamilah to actually accept the offer, but as she tugged at his pants to imply that she wanted them down, he realized she must have been serious.

"Do you want me to take these off now?" Jamilah said as she looked up at him.

Jayden hesitantly nodded, and Jamilah slowly pulled down his pants and boxers to reveal his already throbbing hard dick. It was bigger and thicker than she imagined. She began stroking it in her soft hands, taking her time to feel the warmth and hardness of it. She stroked from the shaft to the head, feeling the smoothness of the head and even felt some of the pre-cum start to ooze from the tip. Jayden started moaning and breathing deeper as she increased the speed of her stroke.

She couldn't believe she was doing this, it still seemed surreal to her and the salivation in her mouth surprised her even more...

"Hmm, you like this, don't you?" Jamilah slyly said as she continued to stroke faster and faster, making more pre-cum ooze from his tip. She felt his engorged dick begin to pulse in her hands, signaling that he might cum soon.

"Y-yea I do. Shit." Suddenly, Jayden grabbed Jamilah's locs and thrust forward, trying to push his dick into Jamilah's mouth.

"Whoa, whoa, wait what's going on here?" Jamilah said as she tried to back away, surprised by Jayden's sudden action. Although shocked, she couldn't help but be titillated by the forcefulness of it, and she did want to take him in her wet mouth.

"Sorry, I was just..." As he struggled to explain himself, he suddenly felt her soft, full lips around his hard dick, massaging it up and down as much as she could go. Once he felt that sensation, he proceeded as before, thrusting his dick deeper into her mouth while grabbing her hair, pushing her into him as she began to suck. The motion caused her to salivate more and more, making her mouth even more wet and making his throbbing hard cock slid in her mouth more easily. Jamilah couldn't help but suck his dick, despite her trepidation at the force he was using. He wasn't going too hard so as to hurt her or completely dominate her, but the forceful gesture was different than what she was used to, and it excited her moist pussy even more.

As Jayden continued to thrust into her mouth slowly, Jamilah patted his thighs, telling him that she needed to withdraw his dick from her mouth for a moment. As he did, the saliva produced oozed out of her mouth, running down her chin onto her breasts, then to the floor, and made a popping sound. Jamilah took a few breaths, not expecting to feel that in her mouth, and then continued sucking, this time without Jayden having to thrust into her mouth. As she sucked, her mouth already wet, it made a slurping sound as she enclosed her full lips around his hard dick and sucked faster and faster, almost making a vacuum with her mouth.

After a minute or so of this quickened pace and intensity, she withdrew herself from his cock, with some much-needed effort due to this grip on her head, and began licking and kissing it softly, tracing her wet tongue from the head to the base, tasting every inch. Jayden once again shivered and flinched from the sensations, especially when she traced her tongue around the sensitive mushroom head and his pee hole, which was still gradually secreting pre-cum.

"Wow, you must really like that huh?"

"Yea I do, who told you to stop?" Jayden replied as they both chuckled.

"Well, sorry."

After teasing and licking him, Jamilah resumed sucking his big hard cock, taking almost half of his length inside her mouth. It was too big for her to take it all without gagging, but she fit as much as she could. Jayden, who was grabbing her locs with both his hands now and almost guiding Jamilah into him, began tightening his grip on her hair and moaning louder and harder, signaling to her that not only was he enjoying this, but that he was about to explode. He felt that strange sensation in his heavy balls, and knew he wouldn't last much longer. And as Jamilah increased the speed of her bobbing, slurping and sucking as much as she could and rubbing his balls as well, he couldn't hold his load back any longer.

"Oh, fuck! I'm cumming!"

Before Jamilah could withdraw herself from his hard dick, he began spurting rope after rope of his thick creamy load, filling her mouth up. She couldn't believe how much he was cumming, as it began to shoot down her throat and seemed like it never ended, lasting almost a minute. As he came, his body quivered and his knees buckled, and he moaned loudly. She took as much of his warm cum as she could, but he was releasing so much that some of it dribbled down her chin. It felt really good to have his warm seed fill her wet mouth though, and taking his load was making her pussy dripping wet, almost soaking through her panties and her leggings.