Ellen Maesick and Jackson Montgomery share an erotic conversation after school.
Ellen Maesick was a Spanish teacher at Brookfield High School. She was twenty-five years old, and she had had long curly black hair and big brown eyes. She had big lips (all the boys referred to them as “blowjob lips”) and a slim, fit build, though she was only 5’2. She could thank the four years of soccer she played in college for her plump, round butt.
She was beloved by her students. She was kind, patient, caring, smart, and very funny. She would tell stories about her life during class, and sometime she would overshare just enough to make it funny and exciting for her adolescent students. She would never say anything that could get her in trouble, but she would insinuate the transpirings of certain events that were certainly “not school appropriate”, as she’d say.
Earlier today, she told her class about a dreamy man she met a few weeks back. She said that they met at a bar and hit it off right away. She described him as having short, well-cut brown hair and a very well-maintained beard. The man, whose name she said was “Jonathan”, bought her a drink. They got to talking and after not-too-long, she took Jonathan back to her house. “What happened next,” she told her class with a devilish grin, “was not school appropriate.” This was met by a few whistles, some claps, and of course lots of laughter. Half the boys in the class were hiding semi-chubs imagining “Ms. Maesick” having sex with “Jonathan”.
It was now 4:00pm; the school day ended an hour earlier. Ellen had stayed after, as she usually does, to help students with their Spanish work. There wasn’t a huge crowd today, though. Ellen had just given the second test last class so most students were not focusing as heavily on Spanish. There was just one boy, Jackson Montgomery, left in the classroom. He had stayed to ask questions about topics he thought he missed on the exam. Jackson was just over 6’, and he was fairly muscular. He was on the schools lacrosse team.
Jackson was getting ready to leave, but he decided he wanted to see if Ms. Maesick would give any more details about her encounter with Jonathan. “So Ms. Maesick,” Jackson began.
“What happened after you took Jonathan home with you?” Jackson smirked.
Ellen blushed at the question. She was taken aback by Jackson’s forwardness. “I told you, it’s not--”
“School appropriate. Yeah, I know,” Jackson interrupted, “but school ended an hour ago.”
“We’re still in school, aren’t we?” Ellen retorted.
“Oh, come on,” Jackson protested, “there’s nobody else here. I’m not saying you should spill all the details; I’m just curious.”
Ellen didn’t reply. She knew that she shouldn’t share anything else; she could get in trouble, though it would just be a students’ word against hers at this point. Plus, she liked talking about the stories -- it was exciting.
Jackson could tell she was considering it so he pressed forward, “Just share a little more. I won’t tell anybody. I promise!”
“Alright,” Ellen said, “I’ll tell you a little more. But keep it to yourself, alright?”
Jackson smiled and sat down in front of her desk. He was wearing sweatpants, and he knew that he was liable to get a boner from whatever Ms. Maesick was about to say.
Ellen knew why he sat down; she wasn’t born yesterday. She knew it was wrong, but the idea that her stories were hot enough to actually turn people on was quite flattering. If she gave it too much thought, then the value would be diminished slightly given her audience was a bunch of horny, hormonal teenagers, but nevertheless she enjoyed the attention.
“Well,” she said, a little nervously, “obviously he and I had sex.” Oh God, she thought, why did I say that? That’s already too far.
That’s all it took for the blood to start rushing to Jackson’s crotch. He felt his heart start to beat faster. Holy shit, he thought.
“I think we all figured that,” Jackson said, pushing the envelope even more, “but how did it go down?”
“How did it go down?”, Ellen laughed, “how much detail are you asking for?”
“However much you’ll share,” Jackson said.
“There was some foreplay,” she said.
“What kind of foreplay?”
“I’m not sure I know what that means,” Jackson grinned again, “what does ‘the usual’ consist of?”
Ellen wondered how much detail she should give. The conversation was already incredibly inappropriate, and she knew it was unlikely that Jackson wouldn’t blab about this to all his friends.
“Tell you what,” Ellen said, “you can ask me three questions and I’ll answer them with answers that will satisfy you. Just three, though. Then the conversation is over.” She figured Jackson wouldn’t have the balls to ask anything too graphic.
Jackson blushed. “Deal,” he said, “but you can’t use some bullshit loophole to get out of answering a question. And you have to give decent answers”
“I said you’d like my answers,” Ellen replied, smirking, “and I’ll answer, don’t wory.” She leaned back in her chair.
“Alright, first question,” Jackson said, his voice trailing off as he contemplated what to ask. “How big was he?”
Ellen couldn’t hide that she was a bit surprised by the question, even if she did just sort of give Jackson free reign to ask anything. Jackson laughed. She was not expecting him to be so bold, but then again, she should have known not to test the limits of a hormonal teenager.
“Pretty big,” Ellen said, “maybe six-and-a-half inches or so. Neatly trimmed and everything too.” She held out her fingers to denote the size. This is fun, she thought to herself. Though she would not have admitted it, she could feel herself getting turned on by Jackson’s questioning. “He was nice and thick too,” she added.
Jackson could feel himself getting harder. Ms. Maesick was actually giving decent answers. He decided to ask something a little more personal.
“Not bad. Okay, second question,” he cleared his throat. “Did he make you finish?”
Once again, Ellen was taken aback by his forwardness, but she recognized that he was going to try his luck and see what the limits of the questions were.
“Yeah,” she said, twirling her hair around her index finger, “I think I finished twice? Once during foreplay, and then again while we had sex. He was really good.” She could feel herself getting wet, and her nipples were hard. She wasn’t sure if they were visible through her shirt.
Jackson was now completely erect. He shifted around in his seat, trying to adjust his boner so it wasn’t obvious. His efforts were futile, however. Ellen had already noticed he was hard.
“Wow,” he said, “I wasn’t sure you’d answer that one, honestly.”
“A deal's a deal,” she shrugged, smiling. “You get one more question.”
He thought for a moment and then said, “what positions did you guys do?”
“We did a bunch, but the best was doggystyle,” Ellen said, “it felt great. He said the view was fantastic which is a plus, too.”
“Is doggystyle your favorite position?” Jason asked, his voice shaking a little. Precum was oozing from the tip of his cock.
“I told you there questions,” Ellen grinned, “I’m going to get going now; it’s quite late.” In reality, Ellen was just incredibly horny, and she wanted to go home and masturbate before she said anything more. She realized that Jackson may not be too eager to stand up, though.
“Uh alright,” Jackson said hesitantly, his erection throbbing heavily in his pants, “that’s probably a good idea.” He began to slowly stand up, but his erection was quite obvious. He turned bright red.
Ellen pretended not to notice the large bulge in Jackson’s pants as he got up, “I’ll see you tomorrow, Jackson,” she smiled.
They walked out of her classroom together. Jackson turned left, walking in an awkward manner in an attempt to conceal his throbbing erection, saying goodbye as he went. Ellen locked the classroom door, said goodbye in return, and went right.
She walked to her car, unlocked it, and sat down, sighing heavily. She could not wait until she got home to take care of this. She drove her car to the back of the parking lot. In front of her was a thick forest; nobody was in there. She reclined her seat most of the way back and unbutton her shirt. She pulled her bra down, revealing her perky C-cup breasts. Her small, pink nipples were rock hard surrounded by a medium-sized puffy areola. She squeezed and pinched her nipples before unbuttoning her pants, pulling them down to her ankles. She reached her hand down into her panties and felt her already-wet pussy. She began to rub her clit up and down at first, savoring the feeling, moaning softly to herself. She found herself imagining what Jackson’s hard dick would have looked like outside his pants, throbbing with precum oozing from the tip and two delectable balls hanging beneath it. She began to rub her clit faster, now in a circular motion, while pinching her nipples. She swiftly found herself on the brink of a powerful orgasm. She bit her lip and slipped her other hand down into her panties, sliding two fingers into her tight, wet pussy. She massaged her g-spot as she began to come, moaning loudly and bucking her hips as she fucked her cunt with her fingers. She massaged her clit wildly as wave after wave of pleasure radiated from her pussy. Finally, her orgasm subsided. She took a moment to catch her breath before sucking her juices off her fingers, buttoning her pants, tucking her breasts back into her bra, and buttoning her shirt. She began to experience some regret having the conversation with Jackson, but there was nothing she could do about it now.
Jackson drove himself to school. He quickly drove home, replaying the conversation in his head. Upon arriving home, he quickly went up to his room, dropping his pants and boxers as he walked in. He shut the door behind him, kicked off his clothing, and laid back on his bed. His dick was still oozing precum as he took it in hand, closing his eyes and imagining what Ms. Maesick must have looked like as that man fucked her from behind. His stroked himself to a powerful orgasm within two minutes. He took hold of his balls and massaged them as they emptied themselves onto his stomach. He groaned as rope after rope of thick, white cum erupted out of the head of his pulsing cock. Finally, his orgasm subsided. He sighed, smiling to himself. He couldn't wait to go back to school tomorrow.