Jennifer’s First Time

Note from the Author: This short story is a bit different than my typical short stories. Caution: Not for anyone under the age of 18 or if sexuality or erotica offends you. I may continue writing these type of stories depending on the response by my readers. Please let me know your opinion of this type of story. Thanks.


As Jennifer lay back onto her bed, she spread her legs to show Benjamin the soft, supple folds of her vagina, as she enjoyed the coolness of her bed coverings. A shirtless Benjamin pulsated with desire: a desire to taste this forbidden fruit.

Jennifer knew she had to be quiet. Benjamin had brought Jennifer home to her house after their date promptly at 10:45 PM, but had waited another 3 hours in order to climb in her second-story window after Jennifer’s parents had gone to sleep.

Jennifer began to wrest in anxious satisfaction. Benjamin could smell the sweet aroma of her virginity, which would soon belong to him. He began to move towards her, and reached underneath her shirt and felt her small, soft breasts. Benjamin began kissing Jennifer between the thighs, starting at one knee and slowly kissing a trail, until reaching between her legs when he would gently kiss and suck, satisfying his thirst of many years pursuit.

Benjamin began to focus exclusively on Jennifer’s satisfaction: stimulating, massaging with tongue and fingers, Jennifer began to writhe in excitement, her anticipation began climbing to new heights.

Jennifer could no longer contain a desire filling her entire body: “Be gentle, this is my first time.”

As Benjamin began to slide his penis inside Jennifer, she immediately began to grip him with a soft wetness.

Benjamin was now face to face with Jennifer. He slowly began to explore deeper as she continued to struggle to stay silent, Jennifer began slowly kissing Benjamin on the lips.

Jennifer’s fluid surrounded Benjamin as he continued pushing deeper and deeper inside Jennifer. Jennifer began to spasm as an orgasm filled her body. Benjamin continued thrusting as he turned Jennifer into a doggy-style position. Benjamin could feel Jennifer’s juicing flowing uncontrollably around his dick, and he continued to fuck her until a mountain of pleasured filled Benjamin’s body and flowed into Jennifer. Jennifer gripped Benjamin as a life-giving force. For a few short seconds, Benjamin and Jennifer melted in to one, each breathing heavily after satisfying a desire that was ignited over 12 years before.

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Benjamin Survives the Coffee Shop

Benjamin had no time to consider his next move as he sat in a Starbucks on 88th in New York City. Benjamin had been in this situation enough times to know he could handle it, but he would have to be quick.

“He’s got a gun!” One of Benjamin’s fellow Starbucks patrons exclaimed, a full 4 or 5 seconds after Benjamin saw the familiar outfit, whom Benjamin immediately recognized: a white button up long sleeve shirt, tucked into black dress pants upon black shoes, pulled together with a blank tie. When Benjamin first saw the illuminati, he thought they looked more ready for a job interview than elite assassins.

Before the assassin could detonate his deadly payload, Benjamin had unveiled a .45 model 1911 from underneath his suit-jacket, a skill which had proved vital for Benjamin in situations exactly like these.

Benjamin fired 2 shots into the assassins ankles, hoping to reduce the threat while keeping the man alive for questioning.

As the assassin fell to the ground, Benjamin could see the assassin was reaching for his detonation device.

In a split-second Benjamin knew he would have to take this man’s life, and fired 2 rapid shots. As the assassin slumped on the ground lifelessly, the entire Starbucks was quiet except for slow, soulful solo guitar-singer.

Benjamin and Jennifer Date Night (Part I)

Benjamin drove his father’s 1987 Honda Accord speedily through the stop-lights and stop-signs of Murphysborough, Georgia. Benjamin was leaving for Marine Corps boot camp in less than 2 days, and this would be the last time he would see Jennifer, because she had a volleyball tournament in Atlanta, Georgia the next day.

Benjamin hastily came to a stop in front of Jennifer’s house, triple-checked his appearance in the rearview mirror, collected himself, and opened his car door to head up to Jennifer’s door, where he knew her dad would be waiting for him.

“I want her home by 10:45 and not one minute later.”

“Yes sir. Of course. When have I ever brought her late?” Benjamin replied in the most professional demeanor he could muster.

After a few more minutes exchange between Benjamin and Jennifer’s father, a prominent business attorney in Atlanta, Georgia, Jennifer appeared flowingly from the second floor of her 5-bedroom, 6 bathroom mansion. Benjamin’s attention suddenly focused drastically and intensively on Jennifer as she walked down the 14 steps to appear on the same level as Benjamin and her father.

Jennifer was wearing a flowingly white silken dress which emphasized her small waist leading to large, developed and muscular hips, legs and thighs.

Benjamin only became aware that he was standing next to his fiance’s dad when Benjamin was bumped on the arm and brought back to reality.

“Now Jennifer, you be good. Big Volleyball tournament tomorrow.”

“Yes, Daddy.” Jennifer dutifully responded.

As the door closed behind Jennifer and Benjamin as they headed to the car, Benjamin breathed a sigh of relief.

Jennifer looked at him and smiled, and without a word the beautiful young couple walked hand and hand until Benjamin opened the side door of the car for Jennifer, and after she was in the car, Benjamin closed the door, entered the driver’s side and sped off towards the direction of the mountains.

Envious

In response to The Daily Post’s writing prompt: “Green-Eyed Monster.”

Benjamin was always a rebellious boy, Jennifer noticed. By this time in 3rd grade, Benjamin and Jennifer had been classmates for over 6 years, and although he thought she didn’t notice him all these years, Jennifer had been quietly watching Benjamin ever since Jennifer’s mom warned her about him.

But Jennifer was slightly envious of him. While Jennifer lived in a comfortable but strict household, Benjamin had survived only by bouncing between family members when his parents could no longer handle his rambunctious energy. Jennifer envied the way Benjamin was care-free and undisciplined. Free to do what he wanted, when he wanted, a caged spirit inside of Jennifer ached for this freedom.

Every day to school Jennifer’s parents ensured she represented her family history in both dress and attitude.

“We come from a great, long line of Glass. Why, my great grandfather fought for the Confederacy during the War of Northern Agression.”

So Jennifer was required to wear a pearl-white lace dress to school every day, with white leggings and white buckled-shoes, and to return spotless home from school.

Jennifer envied Benjamin’s wardrobe. Benjamin had never matched clothing one day in his life, and often looked as though he was wearing someone else’s dirty clothing. Oftentimes too large, Benjamin would inevitably head home covered on mud from head to toe from playing football with the other boys at recess.

Jennifer would watch Benjamin make tackles and get tackled, both cheering and then fearing for his safety. Jennifer often fantasized about running into the mud-pit the boys were playing in with her pearly white shoes and dress, knowing exactly the punishment she faced if she were to return home in that condition.

The Benjamin Has No Clothes

In response to The Daily Post’s writing prompt: “The Clothes (May) Make theĀ (Wo)man.”

When Jennifer walked in, she immediately noticed Benjamin standing holding the hand-rail of the 135th floor balcony, overlooking a great number of office buildings. Jennifer’s attention was immediately drawn to Benjamin’s clothing.

Wearing a 3-piece, black suit with a black tie, Benjamin looked more like a 1950’s movie star than her boyfriend for the previous 6 years.

Jennifer immediately noticed a shimmer of white hair on Benjamin’s temple, giving him a distinctly more mature and rugged appearance.

Jennifer suddenly realized she had stopped walked and was simply staring at him, when Benjamin must have noticed the same thing because they looked directly into each other’s eyes from across Benjamin’s large, open and finely-furnished apartment.

As Jennifer began to walk towards Benjamin’s warm embrace, he surveyed what she was wearing.

Benjamin’s first impression of Jennifer’s dress was that the dress accentuated and emphasized the right areas of Jennifer’s athletic, slightly muscular, 6’1″ tall body. The dress consisted of a black flowing cotton garment draped around Jennifer’s lovely hips, highlighting the muscular shape gained from 13 years of women’s soccer.

Above a bare midriff, the dress separated and continued on a gold scarf wrapped around Jennifer’s petite A-cup breasts, firmly grasping, revealing that Jennifer wore no bra.

Benjamin began to notice that Jennifer resembled a flower, blooming before his eyes when immediately she closed the distance between her and him and Jennifer’s soft, caressing dress fell on top of Benjamin’s sleek, modern suit and Jennifer pulled Benjamin in for a kiss, having not seen him for over 3 months.

Benjamin’s Land of Confusion

In response to The Daily Post’s writing prompt: “Land of Confusion.”

As Benjamin and Jennifer laid on their backs and watched the stars above, Jennifer turned to face Benjamin, and asked him “What’s your favorite school subject?”

Never the studious type, Benjamin’s stomach reflexively knotted up anytime people discussed anything related to academics.

“I’m planning on joining the Marine Corps after high school, so that stuff doesn’t really matter to me.” Benjamin stated, in his best tough-guy voice, hoping Jennifer would be intimidated and stop down this line of questioning.

“Of course you need to know Mathematics and English, haha!” Jennifer replied, mistakenly thinking that Benjamin was joking. “We’ve been together 4 months and you still won’t open up to me! This is our junior year of high school, so we need to start thinking about colleges together. Maybe we can both go to Georgia Tech together!”

“I-I…I’m not very good at school, and Mathematics is my worst subject.” Benjamin confessed to Jennifer. Benjamin suddenly felt a lightness between the two of them.

Benjamin continued: “Do you remember the 3rd grade with Ms. Carter?”

“Yes, with the pet iguana that got out of its cage and Ms. Carter found it in her desk 3 days later?” Jennifer asked.

“Yes, Well that year I was struggling with math but still doing pretty well. I asked Steven to help me with my homework and he ended up telling all the other boys that I couldn’t read or count. After that they all made fun of me and I never cared about learning math from that day on.” Benjamin looked at Jennifer, who was watching him the whole time.

Jennifer scooted her body to where Benjamin was laying down on his back, and when she was right next to him, gave him a kiss on his forehead.

A Short History of Benjamin Arbor and Jennifer Glass

Even before either Benjamin Arbor or Jennifer Glass ever set foot on this earth, their relationship was already forming. Jennifer’s Dad, Bruce Glass, and Benjamin’s mother, Anita Arbor, had been classmates at Georgia Tech, when on the first day of English 101, Bruce sat next to Anita, and in a startled moment, knocked his cup of coffee over, covering Anita’s entire bookbag.

“I-I-I-I’m sorry ma’am! Let me help you with that.” Bruce Exclaimed as the class went silent and the teacher investigated the commotion.

“No need for worry, I keep a handkerchief for such an occasion.” Anita Replied, as the teacher continued to lecture and the students returning to their slumped-over positions.

And so began the initial contact which would result in a tumultuous relationship between Benjamin and Jennifer, which would unfold over the three next decades.

Jennifer and Benjamin were born 6 months apart, and when they were 3 years old, they attended the same day care and would be in the same classes from day care until Jennifer left to college at the University of Kentucky with a volleyball scholarship.

Benjamin’s first words to Jennifer were:

“Hi Jennifer! How’s your Dad’s…” as he slipped and fell in the hallway at their middle school between first and second period, nearly breaking his arm as he fell and Jennifer helped him up.

“Are you okay?” Jennifer asked when Benjamin regained his footing.

“Y-Y-Yes.” Benjamin stuttered before collecting his books and walking away feeling completely embarrassed, with his hand still hurting from the fall.

This experience was the first and the last time Benjamin and Jennifer were to speak, until they both were seniors in high school.

After Benjamin and Jennifer had been dating for almost 11 months, high school graduation would take each of them on very different paths: Jennifer was to attend the University of Kentucky on a full athletic scholarship after being heavily recruited during her high school volleyball career, and Benjamin had enlisted in the United States Marine Corps.

After returning from 4 years active duty, Benjamin returned to the United States to find Jennifer engaged to a lawyer in Lexington, Kentucky.

Benjamin continued to work various jobs in San Francisco, Seattle and New York City.

Benjamin would not cross paths with Jennifer for another 7 years, until one fateful day would bring both of them together.