Weekend with Olivia

Waking up the following morning Jack decided that even though the dinner he had with the smiths was quite awkward, he would reach out to Olivia and give her the option to go on an actual date. So after breakfast that morning jack called Olivia to ask her to go out for the day. She said yes and so they ended up deciding that Jack would meet her outside the store and they would head out to main street and would spend there time hanging around the shops and parks. Jack proceeded to get dressed and before leaving said goodbye to his mother who was in the kitchen. As Jack arrived at the store he was surprised to find a nicely dressed Olivia, wearing a light pink sundress and heeled sandals.

"Jack! Thank you for asking me out for the day" Olivia said jumping with a beat as she blushed.

"Well I hope to make up for the uncomfortable evening you mother **** you into on Thursday" Jack responded.

"My mother could not stop talking about it yesterday, so thank you for letting me escape that today" Olivia said as she gave him an unexpected hug.

Jack thought to himself how Olivia had never really acted like this around him, but before he allowed his mind to ponder he quickly asked "Well where do you want to go first?".

"Well there is a nice antique store nearby that I always like to browse" Olivia replied while also letting him go.

"That sounds nice" Jack replies as he gestures for her to lead the way.

The following hours had gone by like a blur as the two of them visited the antique store as well as popping in and out of several other shops on main street. They spent the time gleefully browsing the stores and getting to better know each other. Because even though Jack had somewhat grew up with Olivia as a second sister he never really spent much time with her as they got older.

Jack learned that Olivia was very self conscious and often tried to dress conservatively since she was shy of he less developed figure. Along with that she explained that she loved playing the violin in high school, which was a surprise to him as he had never seen her play. As the date went on they both found more things in common, which in turn brought them closer to each other Eventually they decided to take a break and got some lunch at small dinner along main street.

While they waited for their food they continued their conversations from earlier but Olivia also decided to play footsie with Jack. And once there food arrived the footsie had evolved as Olivia decided to play with Jack more while she ate. Sliding off one of her sandals, she raised here foot and started to gently rub around Jacks legs and eventually his crouch area. Above the table Olivia showed no face of her actions ash carried on to eat her sandwich, while Jack on the other hand started to blush as he tried to ignore her advance

This went on in silence until they both finished their lunches and Olivia suddenly got up from the table and left the dinner. Jack waited behind and paid the bill for the food before heading out of the dinner to find Olivia waiting on a bench.

He proceed to sit down next to the teary eyed Olivia, "What's Wrong?" he then said laying his arm behind her.

"Its Just... I... I acted to fast" she responded in between sniffles and tears.

"How so?" jack said leaning in closer to her.

Turning her head away from him she stated between tears, "I wanted this to be something... with some one". After a long pause she then said "I just have never been in a relationship before".

Jack sat there for a moment before reaching out with a finger to turn her face towards him and say "Why don't I be your fist" before taking her in for a long kiss. At first Olivia was caught off guard by Jacks advance but quickly she fell into rhythm with his tong as they pulled each other into an embrace hold onto each other for a time. But soon their kiss broke with Olivia blushing with a smile on her face as she stared into Jacks eyes and and saying "Thank you for the first date".

"Oh, dose that mean there will be another one" Jack responded with a smirk.

"I hope so" She said as she reach down and patted the bulge of his cock, "Why don't we meet up again tomorrow?"

"We will make it a date then" Jack said with a even large smirk then before.

Jack then walked Olivia back home to the store and hugged her goodbye. He walked home with glee as he could only imagine what the next day would bring. Arriving home he found his mother watching TV in living room as she quickly called out to him, "Oh Jack how did you date go". He did not want to deal with his mother at this moment, especially with his emotions all in flux.

"How do you know I was on a date mom?" he responded as he walked over to her.

"Nicole told me all about it when she called earlier" she said smiling, "She has been so excited for Olivia since your apparent dinner date on Thursday"

"And why do you have to care about this" Jack quickly rebuked her with a deeper tone.

"What!" is mother stated jumping up from the couch.

"Why do you have to be so involved!" he shouted at her, "My whole Life has been you getting Involved in everything"

Amanda was shocked and proceeded to say "You don't raise your voice like that, I am your mother young man" with a harsh tone.

"Well maybe you should stay out of it" Jack shouted back.

"Enough, go to your room" she said stopping her foot on the hardwood floor.

Jack angrily stormed off to his room as he left his mother flustered in the living room. He did not know what got over him, was it the recent events, stress, or had the changes he made also affected his mental status. No matter what was changing about him he spent the rest of the night in his room playing video games and eventually having to ease his swelling member as had become common place at least once a day. After cleaning up his bucket of cum he would collapse on his bed and drift off to sleep for the night.

The next morning Jack woke up feeling well rested and with a mission. Now if this mission was self driven or hormonal it did not mater to him, Jack was set on making tonight's date the best one he or Olivia has ever had. His planned involved taking Olivia out to see a movie and then seeing where the night takes them from there. The first thing he did was called her to ask her out to the movies, and she happily agreed. He then spent most of the day relaxing and mentally prepping for the evening to come.

Eventually the evening rolled around and he head out for his date, ignoring his mother who was in the living room. Meeting up with Olivia outside the store he gave her a quick kiss before they held hands and walked down to local movie theater. Arriving at the movie theater it was just there luck that one of the showings that evening was a sappy rom com, so they bought a soda and bucket of popcorn and found there seats which were situated in the back.

Once the lights dimmed and the movie started the love birds started their naughty fun. With both of them paying attention to the move there hands moved mindlessly, Jack reached over and placed his hand on Olivia's thigh, while Olivia reached over and placed he hand right on his crotch. This simple, methodical positioning lasted for about half the movie will they each tested each other. But eventual the movie tone shift and so did theirs as a sex scene started in the movie, this lead them to be more playful with one another and ramp up there teasing. Evidently the movie ended with a kiss during the finale scene, and so in the flow of it they started making out until the movie ended.

Blushing at one another as they broke apart Jack commented "You want to get out of here" while rubbing his head.

"my place or yours?" Olivia replied quickly.

"Oh? well your quick to jump to that" said before gleefully leading Olivia out of the theater and back to his house. It was now very late into the evening and as such Jack new that by this time his mother and sister would be either asleep or at least in there rooms. But he still entered the house through the back door to be as quit as possible, as to not disturb ether his sister or mom.

Entering his room Olivia immediately jumped on his bed and started to throw off her clothes before stating "Oh Jack, ever since Thursday I have dreamed of this".

"Ya, why is that?" he asked as he started removing his shoes.

"I spied on you when you took your shower" she said in a shy voice and blushing face.

"Oh what a naughty girl, maybe I'll need to punish you?" Jack replied with a cocky grin. But Olivia only responded with a slight purr as she finished stripping, and all she could do was stare in awe as Jack continued to slowly strip. He first removed his shirt revealing his lean muscles, and then his pants which quickly gave way to his hardening cock. Stepping forward Jack suddenly pushed Olivia onto he back as knelled down to start playing with her tight pussy.

Olivia let out soft moans of pleasure as Jack ate away at her, only ever seeing such things on the internet never knowing how good it would feel. And eventually this would lead to her first orgasm of the night as she let out a louder moan and shudder as she came all over Jacks face. "Oh Jack its so good!" she said softly after catching her breath.

"I am glad you enjoyed it" Jack said while giving her a few more licks before standing up laying his now fully hard 12 inch dick on top of her.

With a face of awe Olivia spit out "Fuck, is that thing even going to fit?" questing their decision.

"We wont know until we try" Jack replied while caressing her face. He then pulled her to the edge of the bed and slowly lined up the tip of his cock with her vagina. But before he could go any further Olivia placed he hand over her crotch and asked "shouldn't we maybe use some protection?"

"I did not think of that, but I don't know if they make any for my size" Jack responded now questioning going further.

"Its ok then... I am on the pill" Olivia said before slowly removing her hand.

With that confirmation Jack placed both his hand onto her hips and began to slowly push the head of his cock into her. Olivia let out light moans as her tight pussy lips parted open and the cock head slowly entered her. After a minute of pushing the head finally popped in her as she let out a load moan of please to her cherry finally being popped. Jack paused for a moment to caress her cheek as she came down from the new pleasure, "I hope you like it, cause there are 11 more inches to come" he said with a smile.

"Oh Jack I want it... please I want it so bad!" Olivia moaned out.

"Your wish is my command" Jack then said as he latched onto her hips again and continued to thrust the rest of his cock into her as she let out more moans of pleasure. He continued to thrust forward until he had bottomed out, hitting her cervix, with 5 inches of his cock left outside, and a unmistakable bulge in her stomach. After taking a breath Jack started his rhythm by pulling out his cock until just the head remained inside and then thrusting back in. He repeated this motion over and over again, and picking up in speed each time as Olivia became more relaxed.

With each thrust rhythmic thrust Olivia moaned out in pleasure as her hands clenched down holding onto the sheets. Her mind became a blur as she entered her second and then third, fourth, fifth, and so on as Jack beat away at her pussy. Eventually Olivia turned into nothing more than a convulsing mess of pleasure as Jack continued to pound away. It was not long after that Jack finally fully pulled himself out, lifting his cock above her, and letting out a load groan as he drenched her in his cum with load after load.

Staggering back Jack caught his breath as he took in the view of the convulsing, cum drenched, mess of a woman that lay on his bed. He looked on with a smile as he walked over to his closet, putting on a pair of shorts, before quickly grabbing some towels from the hallway closet. Returning to the room he cleaned Olivia off, and once she was clean enough he moved her up to the left side of the bed as he then proceeded to laydown next to her. Drifting off to sleep Jack started to dream of the days and fucking's to come with Olivia and the possibility's the machine might provide.