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Chapter 5: Chauffeur Duty

~ Saturday, January 5th, 2020 ~

It is nighttime in San Francisco, California. The setting is a quaint diner. On this particular night, the establishment is exceptionally busy. While the temperature is a balmy sixty degrees outside inside it is very warm, even more so thanks to the large clientele ordering food, drinks, and ice cream. In a corner toward the back of the open floor diner, a small group of girls is sitting in a C-shaped booth. The lighting is dim, just how the trio wants it as they are doing their best not to be noticed or overheard.

"Are you sure about this?" The girl in the center asks her associates. "It hardly seems fair with the advantage I already have admitted to."

"In my honest opinion, your two-month advantage hasn't yielded you any great advantage, nor do you seem to be in a hurry to get to the agreed upon goal." The girl to her right tosses out.

"Are you sure?" The third and final girl asks the one across from her. "From where I'm sitting you seem to be at a disadvantage. Are you willing to take a chance on that?"

The girl in the center pauses for a moment. She ponders her words carefully and then makes an offer. "How about this... I'm so confident in my abilities that I promise to not press forward beyond my already stated point for six weeks starting this Saturday."

"Why wait so long to stop your advancement?" The girl on the left asks.

"Well... to be honest, I don't have time to see him again until that then. But, just to be clear... that's six full weeks. The following Sunday I have a date with him so all bets are off!"

"I'm game... how about you?" The girl on the right asks the girl opposite her.

~ Friday, January 25th, 2020 ~

High School has been back in session for just over three weeks and Jackson has gotten used to driving his soon-to-be stepfather's Audi A6 as opposed to his Acura NSX. While both cars are manual transmissions the difference in feel and horsepower are drastic, to say the least. Jackson is not a lead foot (speed freak) but having gotten used to keeping his car at a modest speed limit feels different than Steve's car. Jackson had to laugh when he learned the joke at Steve's workplace now that he is driving Jackson's Acura NSX is that despite the fact that he is the boss, his stepson owns a better car than he does.

Jackson was sitting in front of Bayview High School listening to music as he waited for the three girls to make their way out of the school to the car for their rides home. Jackson was relaxing after his mixed martial arts session which he started taking to help with his conditioning post-football session and for self-defense reasons. Until Ramona can legally drive Jackson volunteered to be her chauffeur as all of the adults save Stephanie have full-time jobs (Stephanie doesn't have her own car anyways) so he said he would do it. Of course, since they were on the way, that also entailed giving members of her dance team a ride home which was why Steve's Sedan was more ideal than Jackson's sports car for transporting more than one person.

The normal routine was to drop Chelsey Kirkland off first, followed by Casey Richards, and then return home with Ramona before he went out with one of the girls he was seeing (depending on whose turn it was in the cycle). Before going to training, Ramona asked Jackson to be dropped off first as she had a big project for school to complete and wanted to get it done right away. Jackson told her to run it by her teammates just to be considerate but he had no problem with that. Ramona had already done so and informed Jackson that Chelsey didn't mind and as Casey would be second to be dropped off anyways so she didn't care either.

As it was Friday afternoon the girls came out happy and full of energy after their dance practice. They all happily greeted Jackson and chatted as they drove. Ramona and Casey sat in the back which was normal for the people getting out first and second. Jackson stopped at home and let Ramona out. Everyone said goodbye and then Jackson was on his way to take Casey home. Casey sent Jackson several texts that he could not answer but knew it was her as he could see her in his rearview mirror grinning like a Cheshire cat. When Jackson pulls up in front of Casey's home she thanks him like she always does but sent him one last text before climbing out of the car and making her way into her home.

Jackson puts the car into gear and heads to Chelsey's home. The ride starts out quiet before Chelsey, who was sitting next to Jackson says, "So... any big plans for the weekend?"

"I'm going out with a friend tomorrow all day. It will be fun as I get to drive my car on the weekends. Sunday I will be working on my homework but other than that, nothing special." Jackson answers.

Chelsey notes that Jackson is not giving her the identity with whom he is spending his Saturday with. She is familiar with most of the guys that he hangs out with but Jackson didn't say he was hanging out with the guys. Also, if it was his car he could only take one of his guy friends. No, Jackson is going out with a girl... or older woman. With his looks, current popularity, and a fancy car he could easily be a catch for someone college level or older if they didn't care that he was still a minor (if they knew).

"I was wondering..." The cute brunette dancer begins to say. "If you didn't have any plans tonight if you would like to go out to dinner." Jackson stops at a stoplight and turns to face the pretty girl. His blue eyes meet her brown eyes.

"Dinner?" Jackson repeats in surprise.

"Sure, after all... you've been my chauffeur for the past three weeks, the least I can do is take you out to dinner as a thank you.

"Dinner sounds nice. What were you thinking, Arby's, Sweet Tomato..." Jackson says throwing out something fast and lower price as Chelsey was buying.

"I was thinking more Lonestar or Red Lobster," Chelsey tells Jackson.

"Are you sure? Those can be a bit pricier." Jackson states trying to be frugal as he is not paying.

"Yes, I'm sure. I can afford it." Chelsey states as Jackson pulls up to her house. While no mansion the house is very large and in one of the upper-middle-class neighborhoods of San Francisco. Jackson doesn't know what Chelsey's family does but he will be sure to ask over dinner.

"Well, as you are treating I say it's lady's choice where we go," Jackson says to his date for the evening.

"Great. I'll think about it while I'm cleaning up. Can I see your phone?" Chelsey asks. Jackson quickly clears the notifications from Casey and then clicks on his phone icon. Chelsey puts her number into the phone and hits dial. Once registered on the phone she hangs up and allows Jackson to take a picture of her. She does a quick little saucy pose for her contact photo and then said she would call him when she was getting ready.

Jackson watches as Chelsey makes her way up the sidewalk to her home. She is wearing her dancer's clothes, which are skin-tight save for her jacket. As he keeps an eye on her to make sure she makes it safely into her home, he sees the girl suddenly popping her hips to show off her shapely ass. Jackson groans at the sight and Chelsey turns and coyly waves goodbye before she unlocks her front door and goes inside.

Jackson shifts the car into gear and makes his home. The thought of Chelsey's ass in those leggings has him excited and in need of a cold shower... "A VERY COLD SHOWER!" Jackson says aloud.

Jackson is in the middle of washing up and is contemplating how he should dress for the evening. Steve would be home with his car shortly meaning that Jackson could take Chelsey out in style, much like he would Casey the following day.

"Casey..." Jackson says remembers the text messages that she had sent him.

Jackson quickly finished up his shower and once he is all rinsed off turns off the water. Climbing out of his shower, he dries off and then wraps a towel around his waist and returns to his room. Closing and locking the door, Jackson walks over to his cellphone which is on his nightstand charging, and disconnects it from the charging cable. Unlocking the phone with his fingerprint, Jackson goes to his text messages and pulls up Casey's messages.

The first message reads:

Dance class was fun but what I look

forward to the most is seeing you

every day before I go home.

The second message sent a few minutes later says:

I wish we didn't have to take Chelsey home,

You and I could have spent the evening together

after dropping Ramona off to work on her project.

Looking at the time stamp of the third message, this was the one she sent just before leaving the car:

Chelsey is making eyes at you.

I think she's finally worked up the

courage to find out if you are

Full Lips Fuller or not...

She arrived late to the party...

Casey then ended it with a kissy face emoji.

Some time during his shower Casey sent her last message.

It's funny how fate can work against you.

As soon as I walked in my door I got a text from

my mom saying that she got me a dance audition

for 7:00 PM tonight for a dance competition so

I can't spend tonight with you. I know I will be

exhausted when I get home so I will text you

tomorrow when I rejoin the land of the living.

Know you are in my thoughts and dreams.

Heart Emoji, Casey

Jackson smiles that Casey is following her dream of being a professional dancer. She works very hard and deserves to be in front of a crowd showing them how good she is. Right after tossing his phone down the stupid thing chirped again signaling that he had another text message. Sighing in frustration, Jackson picks it up but sees that it is Chelsey. She sent him a video. Jackson clicks on it and as she is wearing the same clothes he last saw her in it was made before she got cleaned up.

"Hi Jackson, getting ready for dinner and I thought I'd let you know what I was wearing to dress accordingly. Jackson watches as Chelsey shows off what Jackson has come to learn is known as a dinner/party dress. Definitely fancier than anything she would wear to school every day. It was a black midi-dress that went mid-thigh was sleeve and strapless with a bustier style bustline. "I will call you when I am getting into my dress as I will only have to put my shoes on at that point."

"Well, that answers that question," Jackson says as he tosses his towel into the hamper. Jackson steps into his boxer shorts and then walking over to his closet, opts for his light grey Hugo Boss suit and white dress shirt. Only on special occasions does Jackson wear a tie but there is no need for one tonight. The suit and shirt speak for themselves.

It was 6:30 PM when Chelsey came down the steps of her family house. Her mother and younger brother and sister were in the family room discussing something when they heard her heels coming down the steps.

"I thought prom was in May." Chelsey's twelve-year-old brother inquired upon seeing his older sister.

"Ha, ha..." Chelsey retorted walking past him and ruffling his dark brown hair.

"You look hot Chells!" The younger girl offered. Chelsey's younger sister was a spitting image of her, only six years younger at 10.

"Thank you, Mina," Chelsey says.

"Isn't that dress a little much for a dinner date honey?" Chelsey's mother inquires.

"Just trying to look my best for my date mom," Chelsey replies as she puts her stud earrings into place.

Johnny snorts and adds, "More like trying to impress him by showing off your..."

"Johnny!" The boy's mother screeches.

"I was going to say goods." The young boy states. Before anyone could say anything further the doorbell rang.

"I'll get it," Johnny says running for the door. He is very curious to see who merits his sister putting on makeup and pulling out such a fancy dress just for a simple dinner date. "Woah." The young boy says after the door is all the way open and he sees the rather dapper young man before him. Johnny Kirkland knows who this is. You would have to have been living in a cave or without a TV to not know.

"Hi, I'm..."

"Jackson Fuller... Bayview High's MVP. I... I... uh... please, come in." Johnny says moving out of the doorway and allowing the young man into his home.

Mrs. Kirkland watches as Johnny comes in and plants himself to watch her reaction when his sister's date enters. Jackson enters the family room and sees his dinner date, a woman who could only be her mother, Chelsey's younger brother, and younger sister (looks too much like Chelsey not to be).

"Hello." Jackson greets the room.

"Hi..." Mrs. Kirkland says in disbelief. Very few of her daughter's dates have ever come inside to meet her family. Absolutely, none of them have ever looked so dashing.

Jackson introduced himself, not that anyone in the room didn't know who he was. He allowed Chelsey to introduce him to each member of her family and they all told him a bit about themselves and he did so in return. Chelsey looked down and saw a look of admiration on her brother's face as well as the fact her baby sister was smitten by Jackson's good looks, kind demeanor, and nice dress.

"Ok family, Jackson and I are going out to eat now," Chelsey says before her family steals her date from her.

Jackson takes Chelsey's arm and leads her away. "It was nice meeting all of you." Jackson offers.

The family follows the teens out and when they make their way to the drive Johnny sees Jackson's car. "Oh my god... you got to keep the car?"

Jackson grinned at the boy's comment. His Acura NSX appeared in all of the commercials that were shown over the holiday. "I got it on a discount after the commercials," Jackson tells him as he helps the young boy's sister into the passenger side.

"I'll be home about 11:00." Chelsey Kirkland tells her mother. The Kirkland family watches as Jackson climbs into the driver's seat and drives away with the smiling oldest daughter.

Chelsey opted for a non-franchised steak house on the outskirts of San Francisco that had a giant salad bar in addition to their various meat menu. Chelsey wasn't a vegetarian by any means but she liked the option to be healthy and loved the salad bar at this restaurant. The couple chose the option to dine at the salad bar while also choosing something from the menu. Chelsey ordered a small sirloin steak to complement her salad while Jackson, not wanting to overdo it as Chelsey was paying for dinner, ordered the same but got a 10-ounce steak as opposed to the 6-ounce one that Chelsey ordered.

After dinner, the teens went to a club to dance for a good portion of the night. The clientele at the club was mid-teens to twenty years old, no adults save for the owner and staff (who were clearly marked by their wardrobe) were present. The DJ present was cycling through various types of music. The dancing was a mix of fast pace club style to slow songs to allow couples time to get romantic for a little while on the dance floor.

"You're a very good dancer, better than you were at Homecoming," Chelsey tells Jackson as they take a break from the fast-paced song currently playing.

"Thanks, I've had a good teacher since then," Jackson tells Chelsey. Truth be known, he has had three.

"Anyone, I know?"

"Can't say," Jackson tells her.

"Can't or Won't?" Chelsey asks.

"Both." Jackson answers.

Chelsey lets the topic drop and just enjoys his company and the way their bodies moved in synchronicity. After dancing for a good hour Jackson goes to buy the pair a couple of sodas to help cool down. When he comes back Chelsey is not alone. From the tone of her voice, the guy is not taking no for an answer and he starts grabbing for her. The guy looks to be older than the two of them, either late teens or twenty.

"I'm not interested," Chelsey tells the guy pulling away from his hand.

The guy reaches for Chelsey's arm again but before he knows what is happening, the man finds himself face down on the table. Jackson has handed off his drinks to a waitress passing by, grabbed the guy's wrist, and forced it behind his back. Now controlling the large man by his wrist, arm, and neck (Jackson put his other hand there) tells the rude guy, "The lady said no. When you act like this you insult the young woman you're accosting... and the man she is with." Jackson says putting pressure on his arm.

Security arrives thanks to the waitress that had Jackson's drinks. Jackson releases his hold on the guy and holds his hands up indicating that he isn't planning to do anything further. Chelsey hugs Jackson and the two watch as three large men, larger than Jackson's adversary, escort him out of the club. The pair down their sodas and after things calm down Chelsey decides that she has danced enough after that incident and asks Jackson to leave. The pair go out a side exit just in case the guy is waiting for them outside of the club.

"Well, that was exciting," Jackson announces as they pull into Chelsey's driveway. Jackson climbs out and makes his way around to open the door for her. It is still early for the teens as it was just past 9:00 PM. Jackson exits the car and runs around the car and helps Chelsey out of the car and holds her hand once the door is closed. Jackson starts for the front door but Chelsey stops him. He gives her an inquisitive look as she pulls him toward the back of the house. Jackson didn't think that a house this size would have a pool and a pool/guest house and he was right. What it did have was a decent-sized yard (bigger than his) and a basement with access to the basement from the back of the house.

Chelsey leads her date down the steps to the basement and then disengages the Bluetooth lock with her cellphone. Jackson walks in and finds a very nice furnished basement. The room looked like a personal movie theater with a C-shaped couch large enough for six average-sized people. The flat screen tv had to be at least 70 inches and he could see the speakers and home theater underneath the tv.

"Very nice," Jackson admits.

Chelsey closes the door, locks the doors to the house, and the two sit in the center of the couch. Chelsey then says, "Alexa... red moon ambiance."

The smart device responds and the lights in the room come on but in a low, reddish tint. Once the lighting was set soft music begins playing through the speakers around the room. The volume is just right to set the mood for the two and not disturb anyone upstairs.

"So... I haven't heard much... if anything, of the exploits of Full Lips Fuller, since Rocki kissed you in the cafeteria back in September. Why is that?" Chelsey asks her date.

"That is because generally, I'm a private person," Jackson explains. "Rocki is bold, brash and to some, she can be abrasive. She was willing to put her life on display for all to see, not everyone is like that... particularly me."

"Soo... are you seeing anyone special?" Chelsey asks poking for information.

"I am seeing several special someones, Chelsey. I'm not exclusive to anyone, because the girls in question are not willing to commit to me, so I am single." Jackson tells the dancer.

"Do I know these special someones?"

"Sorry, the girls and I have an understanding for personal reasons." Jackson reminds Chelsey. "So in the grand scheme of things, I don't kiss and tell."

"Then how did the Full Lips Fuller rumor go viral at the beginning of the school year?" Chelsey inquires.

"Honestly, Rocki started it to save my reputation after the Baloney Boy incident. However, what she could never fathom happening is that other girls might not take her word that I was as good as she claimed, even after the kiss." Jackson tells Chelsey.

"Ok, if you won't give me names how about a number. No harm in that right?"

"You can count them on one hand," Jackson tells Chelsey. "While I'm sure there are guys and girls that would say that isn't that many I haven't had any complaints from my partners over the past three months so I must have some skills."

"Well, if you don't mind, I would like to find out for myself if you live up to your moniker." Chelsey nervously requests.

Before Jackson can give his consent Chelsey moves onto his lap and straddles Jackson's waist. As she moves Chelsey hikes the bottom of her dress up around her waist to give her the ability to do this comfortably. Jackson lets out a low groan as he can feel Chelsey's warm moist sex through the sheer material of Chelsey's panties as it is pressed against his crotch. Chelsey's lips graze Jackson's as she leans forward. While doing this the sexy Latina begins to grind against Jackson's cock which is already very stiff. Chelsey's arms come around Jackson's neck and draw him into a deep kiss.

"Mmm..." Chelsey moans as she and Jackson ravish one another mouths for a good fifteen minutes before stopping to catch their breath. Once they've done so Chelsey squeaks in surprise as Jackson draws her back in for another long, passionate soul-searing kissing session.

Jackson's tongue soon probes Chelsey's lips and the girl willingly allows her date access to her mouth. Chelsey's arms begin to pimple with goosebumps. She is quite surprised at Jackson's prowess and by the fact that he is not pawing at her as so many other guys (the one at the dance club for a more recent example) have tried. Jackson is assertive without being overly aggressive. A fact that Chelsey likes.

Jackson is surprised when Chelsey takes his hands by the wrist and slowly moves them up from her waist to the sides of her breasts. At this gesture, Jackson stops and looks at the sexy dancer. "Chelsey, are you sure this is what you want? It seems a bit fast." Jackson doesn't actually mind if she wants to move a little fast, but he doesn't want her to feel like she has to do this if she wasn't ready or comfortable.

"Mmm..." Chelsey moans in contentment. "Jackson, a girl knows if and when she wants something... or someone," Chelsey informs her date. "Nobody here is forcing me to do anything I don't want to... but I appreciate you asking me." The pair resume kissing and with her blessing, Jackson moves his hands from the sides of her breasts to the front. Chelsey moans her approval as her date's hands gently cup her B cup tits.

Somewhere in the back of his mind, Jackson wonders if Sienna selected her friends based on their statures because they almost all have the same type of figures. Sienna is the tallest, and most filled out of the team (and he can't be the only one who noticed this). Still, Chelsey is very beautiful and quite unique in her own right.

Time goes by and Chelsey is extremely worked up but the one thing that has her annoyed is that Jackson hasn't taken the clue and pushed further than where he is at. By now she would have had to beat any other guy with a club to stop from pawing at her clothes. Jackson was almost too good to be true. Chelsey stops her liplock with Jackson and scoots back from him so that he is looking straight at her.

Jackson watches as Chelsey reaches behind her and he hears the sound of a zipper being tugged down. The young man gulps as the sexy dancer reaches for the hem of the top of her dress and pulls it down slowly. Chelsey watches as Jackson's eyes follow the top of her dress as she pulls it down until her naked tits are in full view of Jackson's eyes.

"Ummm... wow," Jackson says just above a whisper. He has touched four girl's butts, he has touched Corissa, Casey, and now Chelsey's breasts on top of their clothes, but this is a new first for him.

"I'll be honest, I've never let anyone see this much of me before," Chelsey tells Jackson. She is being honest. But there is something about Jackson and the way he treats her that she is more willing to take this chance. Based on how guarded he is about the girls he has kissed she has no doubt in her mind that he won't go tell anyone that she showed him her tits.

Jackson's hands nervously come up and feel Chelsey's naked breasts. While most of the feeling is the same as a moment ago the sensation of feeling her skin in his hands makes it feel even more amazing than before. It isn't long before he feels her nipples poking into the palm of his hands. The dark brown nubs are stiff and Jackson moves his hands back and begins gently pinching her nipples.

Chelsey bites her lower lip as Jackson begins playing with her nipples. He watches as the girl, eyes closed, begins to moan and whimper as he does this. "Ahhhhh... oh my god... mmmm!" Chelsey moans.

Jackson decides to be bold and leans in and kisses her nipples. First the left, then the right. Chelsey moans when his lips touch her nipples. She really gets into it when he sucks her right nipple into his mouth as he massages her fleshy tit with his left hand. With his free hand, Jackson places it on her ass which sends another shockwave through her body as he went to touch her cheek and it landed very near her soaked core. Chelsey absolutely loses it when Jackson's teeth bite down on her protruding nubs. As she has never had this much stimulation before Chelsey actually achieves her first orgasm just from having her nipple sucked and being touched. As she had never played with her nipples before she didn't know how sensitive they were until this moment. Chelsey wraps her arms tightly around Jackson as she rides out the sensation. Soon she is gasping and goes limp in his arms.

"Have mercy!" Chelsey finally says when she can speak again.

"WOW!" Jackson replies. Chelsey had slid off his lap and was straddling his leg when she grabbed hold of him. The crotch of his gray pants had a visible wet spot from where the sexy Latina was sitting. Jackson, being a gentleman, helps pull up the bustier of Chelsey's dress so she is covered and then finds the zipper and zips it up for her. Once she is decent he leans in and kisses her and she returns it.

"I... ah... I've never..." Chelsey babbles.

"Shhhhh..." Jackson says placing a finger on her lips. "You are very sexy. You are so very sexy and strong. I like that you know what you want and go for it when you want it." Jackson tells her.

"I... I think I'm good for the night." Chelsey tells Jackson. Originally she was planning to go farther, maybe even all the way but realized she can't do it, at least not yet.

"I understand. I think you're amazing. I'm not going to push you farther than you want and I'm willing to let you set the pace. I want you to be comfortable and not feel pressured to do anything you don't want." Jackson tells Chelsey.

Chelsey says nothing. Her voice would betray her. If her panties weren't already soaked from her orgasm she would have after Jackson's heartfelt admission to her. Jackson helps Chelsey to her feet so that he can stand and she walks him to the back door. Steps away Jackson spins about capturing his beautiful date in his arms. Chelsey lets out a little yelp in surprise when Jackson dips her before his lips reconnect with hers again. Chelsey fists Jackson's hair as she moans loudly into his mouth as their tongues duel. Only when they are verticle again does Chelsey release her hold on Jackson and break the kiss.

"Good night Chelsey," Jackson whispers.

"G... good night," Chelsey replies. She watches as Jackson exits her house and as he leaves she realizes her heart is pounding like never before.

After what they have done tonight Chelsey decides that she will spend the night in the basement as she feels too weak to make her way up two flights of stairs and walk down the corridor to her bedroom. Pulling out a sheet, blanket, and her favorite downstairs pillow, Chelsey makes up the couch before she goes down the short basement hall to the laundry room where she collects one of her nightshirts. It's nothing special, or sexy, just something comfy.

Chelsey unzips her dress and slides out of it. After picking it up from the floor she puts it on a hanger. She then slips out of her soaked black panties and tosses them into the laundry hamper. Grabbing her nightshirt she pulls it on over her sexy frame. Chelsey waddles back to the couch as she is utterly exhausted and covering herself up, passes out for the night. The last thing she sees in her mind's eye is Jackson Fuller and in her mind, the two are naked and snuggled up in bed like the lovers she dreams they will be.

Jackson Fuller is a little winded as he drove home for the night. Having been practically smothered against Chelsey's chest, Jackson had to learn (quickly) how to breathe in such a situation. Tonight was a new first for him and Jackson didn't quite know what to make of it. Even more puzzling to him, he didn't know how he should behave tomorrow and so on when he goes out to dinner with Casey and the others. He has touched her tits over her clothes, does he press her or wait and see if she lets him go further. Of all the girls Casey is the only one that he seems to set the pace with more often than not. Is he pushing her into uncomfortable territory or is he being too cautious?

"No, the last thing I want to do is be a guy like Brady. I have earned the trust of the girls that I've been with by not being that type of guy." Jackson says aloud. With newfound confidence, Jackson decides that tomorrow he will let Casey decide where they will go out to eat and what they will do in the evening afterward. Jackson knows that there is a chance that Casey might not even want to make out. Not that that has ever happened. If they do pick up where they last left off Jackson will do a little light probing and be a little assertive.

To Be Continued