This is my first work, as such, there is much room for improvement. If you any recommendations for this story, or critiques on my writing style, let me know in the comments. This story is loosely based on my own life, with a some of my fantasies and dark thoughts thrown in.
Enjoy! The alarm buzzed, Jake glanced at the clock, 6:00 AM, "Just 5 more minutes, it's my birthday" Jake Stevens mumbled to himself, before rolling out of bed, starting his morning routine.
Jake sized himself up in the mirror, those morning workouts for baseball had improved his body the last few years. Where he had been a tall, gangly teenager, he developed a lean athletic build with just the hint of a six pack.
With his tousled light brown hair and stunning green eyes, Jake never really had a hard time meeting girls. He threw on his workout gear and headed out the door. Jake fired up is Jeep and headed in for the baseball team's Friday morning workout.
Entering the weight room, Jake received a few friendly pats on the back from his teammates, wishing him a happy birthday. Jake was happy with his progress in the gym, he wasn't the most talented of ballplayers but he hustled, had heart, and was a student of the game.
Jake was hoping for an athletic scholarship to a school in the South, where the weather is warm and the girls dressed accordingly.
He was in the zone and cruised through his workout. After exiting the weight room, Jake drove back home, showered and changed, before heading downstairs to the kitchen to get some breakfast. His twin sister, Alexis, was sitting at the table, chewing on her breakfast while she was reading a book.
"Happy Birthday!" Jake congratulated his sister, she barely lifted her spectacled eyes and half heartedly returned a happy birthday before returning to her book. Alexis had always the more studious of the two, preferring studying over socializing and books over athletics.
It's not that she was a typical "geek" or "nerd" she was just as attractive as anyone of the cheerleaders, but she tended to wear conservative clothes that hid the 34C breasts and round bubble on her 5'4" 115lb frame.
Her brown hair and hazel eyes typically done in a sloppy bun and hidden behind her glasses. "Hey tell mom and dad that I'm working on the application essay for College with my friends after school. So I dinner will have to be a little bit later." Alexis told Jake, not looking up from her book.
Jake finished up his breakfast and told his sister "see you at school" before walking out the door. As Jake stepped in his Jeep, his phone vibrated. His girlfriend of two months, Katie, had sent him a message. "Happy Birthday sweetie, Can't wait for tonight! I have a gift for you, I think you'll love it ;) XoXo see you at lunch!" Jake smiled as he sent sent his reply. Their schedules always conflicted, they never got much alone time together, besides getting a hand job as he rubber her clit on their second date, he hadn't done much with Katie.
He hoped he got to fuck her tonight, his dick jumping at the thought. He made the short drive to school, walked into the building and found his first period English classroom. Ms. Dyers droned on about the boring book they were reading as Jake just stared at her and pretended to listen.
Ms. Dyers was a pretty hot for a 32 year old, she was the schools cross country coach and kept herself in nice shape, leading the cross country runs herself.
She had worn a black summer dress, which fit nicely against her 5'6" athletic frame. Her breasts looked great today, her ass just barely defined in the loose fitting waist of the dress. Jake wondered what kind of underwear she was wearing, thinking that she was probably wearing cotton briefs.
As the class bell sounded, Jake got out of his seat and attempted to head to his next class. Ms. Dyers called him over to her desk, "Mr. Stevens, I have finished reading your book report, I was not impressed, stop by my office after school so we can figure out how to improve your studies" Jake flinched, "But Ms Dyers, I already have baseball practice, that won't be over until around 4:30.
And I have to shower and change, I have dinner plans tonight, It's my 18th birthday! Can't we just do it some other time?" Jake pleaded "I'll see you at 4:30" Ms Dyers said curtly, "I'll be dirty," Jake interjected "That's fine, it'll only take a few minutes" Ms Dyers said calmy, before dismissing Jake. Jake went on with his morning, it was a complete snooze fest, it was the Friday before spring break was and it was mostly busywork or reviewing material learned so far.
Lunch finally came around, it was his favorite point in the day, It was the only period he shared with his girlfriend.
He waiting at his jeep for his girlfriend, Katie Collins, the 5'3" Blonde bombshell cheerleader. Her shoulder length hair swaying as she walked, her C cup breasts looked huge against her small frame.
Jake kissed her on the cheek as she walked up.
He opened the car door for her and watched her as, round from cheerleading and gymnastics, step into his car. As he got into the car, she wished him happy birthday. They stepped into Jakes favorite burger bar, Katie toyed with Jake, "ooh maybe I want the Italian sausage," she cooed into jakes ear, "or maybe i should save that for tonight" she said as she winked at him. After finishing their lunch they still had a 15 minutes to kill until they had to be back at school.
So they went to a secluded parking lot and started making out in the back of his Jeep, Jake started his hands on Katie's outer thigh, running up to her hip, fingers sliding underneath her shorts, he squeezed the side of her thigh before moving up to her abdomen, and gently pushed her down in the backseat, he continued his way up to her perky breasts.
He started necking her, and moved down to her breasts he pulled down the straps of her tank top revealing her strapless yellow lace bra, he pulled the cup down and freed her hefty breasts. Jake stared into Katie's eyes, licking his lips, before moving down licking each of her nipples. Jake alternated between licking and sucking on each of her nipples, gently blowing on each before he moved onto the other.
His cock was strained against his jeans, Katie reached for his groin, gave it a playful squeeze. "We should get back to school, I have plans for him tonight" Katie said with a wink. Jake had to take minute to compose himself, then started the Jeep and headed back to school.
The couple kissed in the parking lot as they went to their next classes. The rest of the day was uneventful, finally the last bell rang. Jake changed, and headed to practice. As he walked up to the field, Jake noticed a few scouts in the bleachers. They were all talking to his coach. "They're probably here for Daniels," Jake thought to himself. Daniels was the stud Shortstop on the team, everyone knew he was going pro someday.
Jake started to get loose before Coach Hendricks came up to him. "Jake, these scouts are here for Daniels, you know that, but I talked them into looking at one of your bullpen sessions" Jake nodded, realizing this was his chance. A half a dozen scouts from top college programs and professional clubs. Jake got loose and gave it his all in a bullpen. "Not bad" one of the scouts said, "Hopefully I'll get to see how you do in a game." Jake was elated, his hard work was finally paying off.
He went on and continued practice moving onto fielding drills. 4:30 came along and he was spent. Coach Hendricks walked up to him "You'll be on the mound tomorrow, bring your A-game, the scouts will be there too." Tired, sweaty and dusty, Jake changed out of his cleats, put his sneakers on and walked back into school.
He found Ms Dyers sitting at her desk, she looked different. She must've put more make-up on Jake thought to himself, the scent of fresh perfume carried in the air. Ms Dyers noticed Jake, stood up, and motioned him to follow her. She was still wearing the sundress, but had changed into a set of heels that made her ass scream 'spank me.' Jake followed, her staring at her swaying ass as she led him to an empty classroom.
"Mr. Stevens, please have a seat," She said, pointing at a desk, Jake took a seat in the empty chair. Ms Dyers sat on the desk across from him, and crossed her legs.
"As I mentioned earlier, your book report was less than satisfactory, you really need to improve your efforts in this course if you expect a passing grade" Jake looked down at his lap, knowing that if he didn't get a C average he wouldn't be able to play ball.
No ball, meant no scholarship, no scholarship meant no college, no college meant, well he didn't know exactly. "What can I do Ms Dyers?
I'm giving all that I can, whatever I can do I'll do it" Jake pleaded.
"Well Mr. Stevens, I suppose we can work something out. I can use some help grading freshman quizzes "Jake shuddered, "It's my birthday Ma'am, I already have plans tonight!" Jake exclaimed. "Ah, yes, I remember" said Ms Dyers "Finally legal" "Well uh, I guess you can say that" Jake replied Ms Dyers uncrossed her legs, letting Jake get a good look at the outline of her covered mound, Jakes cock started to stir looks like Ill find out what kind of underwear she's wearing Jake thought to himself.
"Well then I have another opportunity for you, Mr.
Stevens" Ms Dyers said as she stood up and walked to the doorway. She looked out into the hall, came back in the room, and locked the door. "what is it?" Jake asked. "Right, Mr Stevens, stand up, let me get a look at you" Jake stood up, Ms Dyers walked around him admiring the way his tight undershirt clung to his taught torso, the way his baseball pants hugged his muscular legs and butt.
"We are both attractive, consenting adults, why don't we help each other out, I'll help you with some extra credit, and you help me in a more&hellip.
physical way?" Jake clued in, "I think I can find time for that" "Good, now take off your pants" she instructed. He fumbled with his belt, pulling his zipper down he slowly slid his pants down past his knees. "Now your shirt" he removed his shirt, Jake was now standing in the middle of the classroom wearing nothing but a jockstrap, his pants sitting at his ankles.
Ms Dyers walked close to him, placing a hand on his chest and slowly walked around him. Her fingers dragging around his chest, across his abdomen, his sides, and down to his butt. She gave his buttock a nice squeeze, Jake felt it as her nails dug into his buttock. Ms Dyers, completing her walk around, came back to his front, facing him.
"Let's see what you've got hiding behind here" she said sinking to her knees, pulling his jockstrap down to his ankles. Jakes 7" cock sprang free, fully erect in anticipation. Ms. Dyer's eyes widened, "Well this is a pleasant surprise" She held his cock in her hand sizing it up with her eyes, "I just got done with practice. Sorry I didn't have a chance to clean up" "Nonsense Mr.
Stevens, I've always enjoyed the musk of a man after he's worked out!" She looked him in the eyes as she put the tip of his manhood into her warm mouth. Jakes head rolled back "Fuck! That's good" he moaned, Ms Dyers stopped, looking Jake look in his eyes. "I will not tolerate that language in my classroom." "Yes ma'am." She continued sucking him to her heart's content, slowly working her way up and down his shaft, licking his balls while she caught her breath. She kept sucking and as she sensed Jake nearing climax.
Ms Dyers slowed down, kissing his shaft and licking his scrotum, then suddenly stopped. Ms Dyers stood up and turned towards the desk, and bent over slightly at the waist. She hiked up her dress, revealing a black thong. Ms Dyers pulled it down, stepping out with her left leg, and placed her left leg on the desk.
She looked over her shoulder, seductively saying, "Fuck Me." Jake waddled over to her, his pants still around his ankles, he noticed her pussy lips were smooth, with just a tuft of pubic hair emanating from her mound.
Reaching her, he placed his right hand on her hip, and his left hand on the base of his manhood. Jake guided it to the entrance to her vagina plunging in.
He inserted himself slowly at first, letting her adjust to his girth until he was fully inside her. Fully adjusted, Jake started picking up speed, placing both hands on her hips. Ms Dyers used one of her hands she used to stabilize herself as the other frantically rubbed her clit. As his speed increased so did the ferocity of her clitoral stimulation.
Jake slowed down slightly, feeling his own climax approaching, and wanted this to last as long as possible. Ms Dyers breathing quickened, Jake knew she was close, so he started to pound away with all that he had, sweat dripping from his forehead to her ass, trailing down to her pussy, adding to the slickness of her depths, he could feel his own orgasm coming.
"I'm gonna cum" he cried, trying to pull out. But Ms Dyers used her leg to pull him back in, as he shot his seed into her now gushing depths. He could feel the last few ropes of his cum being milked out by Ms Dyer's vaginal muscles. Satisfied, Ms Dyers pushed him away, immediately pulling up her panties before his cum could drip out. "That was hot" Jake exclaimed through panted breath. She pulled down the hem of her dress, flattening it out against her body, trying to make herself look presentable.
"Your phone" she demanded.
Jake, pants still around his ankles, cock starting to droop, unlocked his phone and handed it over. Ms Dyers entered in her number as Jake put his clothes back on. When she was done she tossed the phone back to him. "I'll let you know if any more extra credit opportunities arise." Ms Dyers flatly stated "Oh, and if you thought that was hot I've sent you a link, check it in 10 minutes. Now if you'll excuse me, I have another student who needs my assistance." Ms Dyers unlocked the door, and walked back to her office.
Jake was still in shock at what had just happened, he checked the time on his phone before heading out the door.
He hopped his car and drove home, his parents asked how his day was, and Jake said that Alexis would be running a little late for dinner, that she was working on her acceptance paper with some friends, before he walked upstairs. He got to his room, set his book bag on his bed, and checked his phone, 9 minute after he left school, he pulled up the link, and was surprised to find a live video of Ms Dyer's office. Ms Dyers was sitting on her desk legs crossed. Suddenly another body walks in the room.
Jake couldn't tell who it was, just that it was a female. The girl hands something to Ms Dyers, who glances it over, nods and sets it to the side. They appear to be talking about something, but there is no audio. The second female appears to nod solemnly and gets on her knees in front of the desk, Ms Dyers stands up and hikes up her dress.
Jakes cock stirs, he gets up and locks the door to his room, once locked he pulls off his dirty pants and jock strap, never taking his eyes off of his monitor. Ms Dyer has removed her thong, and motions the female towards her cunt. 'Now this is HOT!" Jake thinks to himself, cock surging to full rigidness.
It's hard to see but Jake could tell that the female started licking at Ms Dyers seeded pussy, seemingly invigorated with the act. Jake spits in his hand as is rubbing his erection furiously. After a few minutes, Ms Dyers is close, he can see it in her face. Ms dyers takes her phone and does something with it. Jakes 2nd orgasm is building, his phone buzzes, its Ms Dyers, he sees her point of view, damn it's hot, she sends him a few more in a few different angles. As he gets to the last picture, the girl looks directly at the lens, he shoots his load all over the floor.
He knows those hazel eyes from anywhere. "That's Alexis" he gasps. Spent, he sags back in his chair watching the aftermath on screen. Ms Dyers hands his sister the black thong, demanding something in return. His sister takes her jeans off revealing a white and pink thong. Alexis grudgingly takes her panties off and gives them to Ms Dyers before puts on Ms Dyers soaked black thong on before pulling her jeans back on before leaving the room.
Jake cleaned his mess up and just as he's about to get in the shower. "I'm home!" he could hear Alexis shout from downstairs. Jake stood under the water, cleaning the filth off his body.
Drying off, he checks his phone, a text from Katie. "Can't wait for tonight! I know you have dinner with the fam, but dessert is with me :* XoXo" with an accompanied kissy face selfie showing off Katie's luscious cleavage. Jake responds "can't wait, about to get dinner see you in a few!" "Jake! Your sister is home, we're going to dinner!" His mom called from downstairs.
Throwing on a pair of jeans and a polo, Jake had opted to go commando, thinking ahead to his dessert date with Katie. Dinner was&hellip.
awkward, to say the least. Jake had a hard time maintaining eye contact with Alexis, considering the show he had just witnessed a half hour before. Jake had noticed that his sister hadn't changed, meaning she was still wearing the soiled panties Ms Dyers made her wear.
Alexis disposition was more cheerful as she informed the family she finished her essay. "Ms Dyers said she'd make improvements over the weekend, and even write my recommendation letter for me!" Their parents were thrilled. Dinner commenced, Jake talked about his day, letting the family know about the scouts, but left his encounter with Ms Dyers out of his days tale.
After dinner was completed, the family went their separate ways, Jakes parents went home, Alexis went to hang out with her friends, while Jake went to pick up Katie. It was 7:45 when Katie walked out of her house. She wore a tight black miniskirt that hug tightly to her ass, a pink tank top with her breasts spilling out, and light sweater as she stepped out in the cool spring weather.
She hopped into Jakes jeep, pecked him on the cheek and suggested they get ice cream. They drove to the local ice cream parlor, Jake ordered a hot fudge sundae, and Katie got a banana split. As they ate their ice cream, Jake had some hot fudge, on the corner of his mouth, running down his chin. "I'll get it" Katie said, and leaned over, licked the fudge off his chin and gave him a kiss.
They finished their dessert and got back in Jakes jeep. "Let's go somewhere romantic" Katie said, Jake nodded in agreement and drove off towards the scenic outlook that looked over town. On the drive to the outlook, Katie removed her sweater, and rearranged her tits so they looked more presentable.
She placed her right hand on Jakes lap, stroking up and down his thigh. His cock started to stir. Her fingers eventually reached the zipper of his jeans, and mischievously looked at Jake while starting to undo his pants. Jake got the hint and lifted up his hips so she could pull down his jeans. His semi hard cock, released from its constraints, fell against his thigh. "Ooh no underwear, kinky, I like it" cooed Katie, as stroked stroke his now hardening cock.
She unbuckled her seatbelt and leaned over, first gently kissing the head of his erect penis, and then licking her way up and down the shaft, before starting to bob her head on his cock, he arrived at the outlook, and there was nobody else around.
Katie stopped sucking him for a just long enough to mutter to "lay back and enjoy this." Jake reclined his seat, pulled his shirt off and pulled out his phone and started filming his blonde beauty of a girlfriend sucking his thick cock.
She had skills, even rivaling that of Ms Dyers. She would change her pace, quick then slow, fondling his balls. He reached over to her back, pulling down her tank top and revealed her pink bra. His hands quickly unhooked her bra, her breasts, released from their jail hung free. He fondled them as she picked up her pace, responding to the stimulation on her breasts. Katie slowed down as she attempted to deep throat Jakes 7" cock.
She was only able to get halfway the first few times, then slowly made her way closer and closer to his pubic mound. Jake resumed filming with his free hand, he received a text. It was from Ms Dyers, "got new panties, what do you think?" Showing front shot of the Pink and white panties she took from his sister, it was a Hello Kitty thong, with a bow on the front with a small picture of hello kitty, and an ass shot with a small cotton ball on the fabric like a little tail.
Simultaneously, Katie finally worked her way down his cock, her nose touching his trimmed pubes, and her chin against his balls.
The overload of stimuli was too much, he set down his phone and came. His orgasm caught Katie completely by surprise, his first spurt went clear down her throat causing her to choke slightly, she tried lifting her head off his cock to cough, but his second shot hit the roof of her mouth, after her mouth was clear of his cock Jake jerked his cock to finish his orgasm, the next spurt hit Katie squarely in the cheek, catching her off guard again, she tried to pull back but Jake had stopped playing with her tits and placed his hand over the back of her head, his last two ropes of cum splashed her nose and forehead.
"You Asshole!" Katie screamed, her face covered in cum, Jake snapped a picture of her frosted face, wanting to savor the image. Katie slapped him across the face, "At least have the decency to tell me when you're about to cum, and why the fuck would you cum on a girls face?." She screamed.
Katie grabbed Jakes polo, and wiped her face off before getting dressed "Take me home" she pouted. Jake put his jeans back on, leaving his cum soaked polo in the back seat, and fired up his jeep.
The 15 minute ride back to Katie's house was dead silent, as soon as the car stopped she opened the door, and left. "Goodnight!" Tried to call out to her, but it was ignored.
Jake's phone buzzed "you musn't keep a lady waiting" it read from Ms Dyers. "This is what i thought" Jake typed as he attached the picture of Katie's frosted face. Ms Dyers sent a single picture in return. The crotch of her panties were pulled to the side, and she had two fingers deep in her pussy.
Jake through the phone on the passenger seat and drove home. Jake pulled up to his house, grabbed his cum soaked polo from the back seat, his phone and walked into the house.
His mom noticed him walk in shirtless, and asked what happened to his shirt. Jake lied, "Oh I got some hot fudge on it, I'm about to throw it in the wash". He went upstairs to his room, threw the stained polo in his hamper and sat down in his computer chair. Jake sent an apology text to Katie, who didn't respond. So he changed into a pair of shorts and laid down in his bed, "what a birthday it's been." He thought to himself.
He closed his eyes and fell asleep.