Chapter 6: Rocking the Boat

~ February 9th, 2019 ~

It was just over a month since the trio of girls met in the very diner they found themselves in again. It was another warm Saturday night compared to the rest of the continental United States. The girls were sitting in the darkened corner conversing about the status of their wager. Everyone was sitting in the seats they had occupied last time. Mystery girl number 1 was sitting on the left side of the bench, Mystery girl number 2 was in the middle while the 3rd Mystery girl was sitting to the right just listening to the other two talk back and forth about where they stood.

"And why haven't you done anything?" Mystery girl number 2 asks the lackadaisical girl number 3. "It's been weeks since I gave you the advantage and yet you've done nothing! What are you waiting for?"

"I'm waiting for the wire." The third girl answers smugly.

"What?" Both of her associates ask in astonishment.

"I have a plan, I know what I'm doing. All I need to do is wait for the right moment. As it is I'm working on another angle to make my plan come to fruition. The two of you just continue going about as you are and do whatever it is you're doing and I'll see you both at the finish line... as the winner." The smug girl states placing her arms behind her head.

~ February 14th, 2019 ~

Valentine's Day... no day in his life has made Jackson Fuller sweat so much as this Hallmark holiday. Under normal circumstances, Jackson could schedule time with one of the girls for a specific day. Today however they all seemed to want a piece of him at the same time. Seeing the conundrum coming early enough Jackson approached the girls before February. Jackson has informed Casey, Trinity, Corissa, Chelsey, Rocki, and Sienna that he is seeing other girls. Casey and Corissa seemed to take it the hardest and Jackson felt bad about the looks on their faces. He left the situation in their hands, telling them (all) that if they didn't want to have anything more to do with him he would understand. He wasn't trying to play any of the girls. He really liked spending time with each of them, getting to know them, and having a nice time. Making out and the other physical stuff was just a bonus that they were able to take off the table at any time should they wish to. As of noon none of the girls took him up on this.

Jackson seemed to spend the least time with Rocki. They got together to study and work on joint projects which is usually when they would stop to kiss. Rocki was the one girl Jackson never went farther than kissing as he was quite sure she would belt him, probably in the face, if he touched her without her first giving him the go-ahead to do so. As Rocki wasn't big on this particular holiday, she was one less girl that Jackson had to worry about.

This left the other five though. Jackson decided the only fair way to resolve the issue was to draw names. He later explained to the girls that he had his brother Max write out the initials of the five girls in question (Jackson didn't tell him what the initials stood for or how they corresponded to the dates in question. Jackson shook up the names in a hat and then Max pulled them out. Max then placed them on key dates starting with February 24th, going to the 23rd, then the 17th, and 16th until the last girl's initials were placed on February 14th.

Jackson would give each girl a special dinner date and event of their choice on their specific date if they so chose to. None of the girls were told who got what other date, which was nothing new as Jackson's schedule was known only by himself. Corissa's date was on the 16th, Chelsey on the 17th, Casey on the 22nd, and Trinity on the 23rd. This meant that Sienna would be Jackson's date on Valentine's day. Of course, Jackson sent each girl (save Rocki) a single red rose and a personalized card. It was a bit cliché but each girl was special to him and he wanted them to know they were in his thoughts even if he wasn't with them on Valentine's Day.

~ 5:45 PM ~

"Do NOT stay out late tonight Jackson!" DJ Fuller informs her oldest son as she stood in the kitchen with her arms crossed over the front of her breasts. Normally she would not let her oldest son go out on a school night but now that he is older, she has to trust him and let him experience things. Her father trusted her, now it was her turn.

Jackson knew his mother was not pleased he was going out during the school week but as this was a special occasion she had conceded. Her father and guardians had been lenient with her during her high school years so she felt obligated to do the same with her son (until he proved unworthy of that trust).

"As I don't want to be grounded I promise to be back before 11:00," Jackson states.

"At 11:01 you're grounded." DJ reminds her son.

"Understood," Jackson replied. He blew his mom a kiss as he made his way out the back door and headed for his car.

It was 10: 35PM and Jackson was contemplating breaking his word and risking being grounded. His evening had gone as planned. As it was Valentine's Day (it didn't start out as a special day to him it was to Sienna so that made it special to him) he wanted to look his best for Sienna. Jackson opted for his dark blue Armani suit with a white dress shirt. Sienna likewise wanted to look her best for Jackson so she chose a Jovanni Navy off-the-shoulder strapless evening dress. It was knee-length and made of lace and very form-fitting.

Jackson drove up to Sienna's house and as soon as he put his car into park the striking blonde exited her home and Jackson could see her setting the house alarm from her cellphone. The house looked very dark which seemed odd to Jackson but the sight of his date made him quickly forget that line of thought. Jackson didn't even have time to properly open the car door for Sienna, she was at the door and in the car looking stunning as ever.

"Happy Valentine's Day," Sienna stated before she leans over and kisses him softly as she didn't want to ruin the work she put into her lipstick (at least just yet).

"Happy Valentine's Day," Jackson says and he presents her with a single red rose and a Valentine's themed corsage that he had made just for her.

"Thank you, Jackson..." Sienna says as he slides it on her wrist. This is something someone usually does for a formal affair. That he did it for her for tonight had her on the verge of tears as it was very beautiful.

"I had it made from fabric and given floral scents. That way you would have it until you decide you don't want it anymore as opposed to one made of flowers.

Jackson took his date to a nice restaurant that was a little more upscale than he was used to. He did his research and picked this place as it had a dance floor so the two could dance the night away. Dinner itself was nice, a little pricey in Jackson's opinion but this was Sienna's night. Jackson had been avidly seeking out computer repair work to make as much money as possible to cover the expenses for the next two weeks.

Across the room, unbeknownst to either party Ramona Gibbler and her best friend Rocki Mahan were sitting at a table for four with two guys from Central High School. Ramona's mother had needed help for a party and the two girls were recruited to be her assistants. The guys (Barry and Walter Reed) were the older brothers and struck up a conversation with the pair. While Rocki was only along to go double with Ramona she was having a nice time and a very nice meal.

Ramona was laughing at one of Barry's witty remarks when she caught something out of the corner of her eye. She picks up her drink and begins gulping it down while she peers in the direction and sure enough, across the floor is Jackson Fuller. But that wasn't what initially caught her attention. It was Sienna Logan leaning over to kiss Jackson that caught her attention.

Ramona knew that Jackson and Rocki were not dating and had come to a mutual agreement to be friends who occasionally kiss. She has walked in on the pair several times and every time it kind of weirds her out. She doesn't know how Rocki can be so glib and casual like that but to each their own.

"Would you guys excuse me, I have to run to the lady's room," Ramona states giving Rocki a knowing glare.

"Ramona, I think I will join you," Rocki says a bit sarcastically.

The brothers move to stand but Rocki says, "We got this guys."

Rocki and Ramona push themselves away from the table and push their chairs in before leaving for the lady's room. "You know they're just trying to be gentlemen," Ramona tells her bestie.

"The question you have to ask yourself is, are they always consummate gentlemen, or are they just aiming to get in our good graces because they think that they might get into something else?" Rocki states.

Ramona lets out a laugh but Rocki continues as they make their way to their destination. "While not as obvious as say, Brady, Barry has been looking down the front of your dress every chance he gets. I've even caught him looking down my dress when he thought he could get away with it."

"You're kidding!" Ramona says.

"Do I kid?" Rocki asks her best friend.

"Very rarely," Ramona replies. She will have to be much more observant the rest of the evening when they return to the table.

Jackson paid the bill and left the tip for the server and escorted Sienna onto the dance floor. Taking hold of her left hand in his right and placing his left hand at the small of her back, Jackson and Sienna were soon moving to the music with several other couples. The young couple (well, not really but everyone around them thought they were) were by far the youngest on the dance floor and even though the men were with their wives or dates he caught several of them eyeing Sienna's spectacular figure. Her long, toned, shapely legs. Her thin waist and ample bust. The dress she was wearing was almost a second skin and it flattered her figure greatly. Yes, Sienna was a sight to be seen.

Jackson decided to let these men know that Sienna was taken. Leaning in, he gave the beguiled young woman a kiss informing all that were watching, that the young lady was his (at least for tonight). Everyone present got that message, even the young women who just happened to be heading back to their table at that exact moment.

Rocki Mahan stopped in her tracks at the sight of Jackson Fuller swaying with Sienna Logan in his arms. She could see the megawatt smile on Sienna's face as they moved together. She felt bile forming in her mouth as the two were pressed together as they moved to the music and just about lost her dinner as she watched (almost in slow motion) as the couple closed their eyes, leaned in, and kissed. First slow and softly, and then she could tell they parted their mouths and shared a French kiss before parting. Rocki forced herself to get over the shock of seeing the two together, composed herself, and walked up behind Jackson. The young man felt a feminine hand tap him on the shoulder. Sienna saw Rocki first but before she could say anything Jackson turned to see who was disturbing him.

"Rocki," Jackson says in disbelief.

"Do you mind if I cut in?" Rocki asks Sienna.

Sienna, wanting to show Rocki that she was unfazed by her presence said, "But of course."

Jackson turned to Sienna, kissed her on the cheek, and whispered he would be right back. Returning his attention to Rocki, the two begin dancing while Sienna moves toward Ramona.

"Sooo, who's idea was this?" Both Ramona and Sienna say at the same time. The two feel silly and return their attention to Jackson and Rocki.

"You look very nice tonight," Jackson informs Rocki.

"Is that the same suit from your car commercial," Rocki asks ignoring his compliment.

"It is."

"Couldn't spring for something newer?"

"This is Armani, a bit out of my normal price range. I'm also not a fashion nut so I don't feel the need to have a different suit for every day of the week." Jackson says starting to get annoyed.

"No, just four out of five days of the week." Rocki reminds Jackson. Before he can counter Rocki continues, "Sooo, is she one of your... six did you say?" Rocki asks him.

"That is none of your concern. I don't put my life on display for all to see. What I do and whom I do it with is my own business, no one else's." Jackson states.

"But it was ok for me to kiss you in public." Rocki reminds Jackson.

"As I recall, you were the one that made that matter public knowledge. While I appreciated the gesture, and still do to this day, I didn't ask you to kiss me in front of everyone. That was all you." Jackson reminds Rocki.

Rocki let everything going on here sink into her head. Her heart was pounding. Not from love or lust, but from anger. She was angry that Jackson was having this kind of effect on her. The one thing she noticed was that Jackson had an aura of confidence around him that he didn't have the last time she turned him down. She wasn't sure if it was from football, the fact he became a local celebrity (for a short time), or because of the girls (besides herself) that he's been spending time with.

"That is a new look," Jackson says snapping Rocki out of her daydream.

"What look?" Rocki snaps at Jackson.

"One that I've never seen before... are... are you, Jealous?" Jackson asks.

Rocki wants to scream. The only reason she doesn't, besides the fact that Jackson may be right, is that she doesn't want to give him and by association, Sienna, the satisfaction. "As if Jackson. You are free to see as many girls as you like and do whatever you want with them. Just don't expect the same from me."

Jackson is trying to read Rocki but much like her name, she's stonewalling him. Her expression is unreadable at this time. Before he can say anything else the song ends and everyone around them is clapping. "Thank you for the dance." Rocki states.

Sienna comes back and wraps her arms around Jackson. "Would the two of you like to join us?" Sienna asks Ramona and Rocki. She doesn't mean it but feels she has to at least offer.

"No thank you," Ramona says. "We are here with those two guys over there." Ramona points out their dates.

Jackson sees the guys glaring at him jealously and just chuckles. They consider him a threat which he finds hysterical as not only is he not a threat, but they just don't realize that neither of them has a chance with either Ramona or Rocki. Jackson can read their intent and they will be lucky to get another date with Rocki and Ramona.

"I hope you have a good night," Jackson tells the girls as he returns his full attention to his date.

Ramona and Rocki watched as Jackson and Sienna went back to the dance floor hand in hand, wrapped in a loving embrace, and tuned out everything and everyone around them. They danced every slow dance that played during their time at the restaurant. Sienna was keeping track of the time and when she saw that it was almost 8:30 she asked Jackson to take her home. Before the song ended Sienna saw Rocki watching the two intently and feeling a flash of her old self. With Rocki's eyes locked intently on them, Sienna leans in and kisses Jackson. Not like last time, but a long passionate kiss. Only when the music ends do the pair separate and leave the dance floor.

Jackson leaves to collect their coats. Sienna goes to Rocki and Ramona's table and politely wishes them and their dates a good evening. Sienna makes eye contact with Rocki and she can read the animosity between them. While she had a moment of glee during the kiss she's not looking for trouble with Rocki.

"Take care Rocki. Ramona, I'll see you at Dance Team tomorrow." Sienna says waving to the pair.

Jackson arrives and helps her into her coat. He then escorts Sienna from the restaurant to his car. Jackson let Sienna pick the music and the two listened in silence as they made the journey from the restaurant to Sienna's home.

Jackson pulls into the drive like he normally does and notes that the house still looks very dark. "The house lights are on but the house itself looks unoccupied," Jackson says.

"Yeah, my parents and Selene are out of town for the weekend. They went to Aspen for a ski weekend with some of my father's business associates. Selene got to go because one of them has a son about her age that my father is hoping to entice." Sienna explained.

"Nothing like using your daughter to make a deal happen," Jackson says. Deep down he is disgusted that Sienna's father would use his daughter in this fashion. Not so much because it's Selene, but because if he would do it with his oldest daughter, how much longer until he tries to do the same with Sienna.

"Are you worried about me?" Sienna asks seeing something in Jackson's eyes.

"Yes. I care very much and very deeply about you." Jackson informs her.

Disengaging her seatbelt, Sienna leans over and plants a soft and loving kiss on Jackson. Jackson kisses Sienna as intently as she kisses him until Sienna ends the kiss. "Come with me," Sienna tells Jackson when he opens his eyes again. The oldest Fuller shuts down his car and once the pair is out of it he locks the doors and follows Sienna who is going up the drive toward the back of the house.

Sienna's pool house is very similar to Trinity's, but a little bigger lengthwise and with a slightly different layout. Like her teammate, Sienna's guest/pool house has an Alexa unit inside wired to the lighting and sound system. With two commands the lights come on (once again in a red tint) and soft music fills the room.

Taking Jackson's hand Sienna moves to the center of the main room and allows Jackson to lead her in a dance. It isn't long before the couple moves in and resume kissing. Sienna purrs when Jackson's lips leave hers and land on the nape of her neck. Jackson's eyes are closed as he does this but moves with Sienna when he feels her leading him away from the common room.

"I can't tell you how much this evening has meant to me," Sienna says breaking the kiss and looking Jackson in the eyes. Jackson opens his eyes now and sees that they are in the guest bedroom. The pair sit down at the foot of the bed. Sienna inches closer to her date and their knees come into contact.

Jackson feels his pulse race a bit as this is the first time that he and Sienna have ever been alone in this kind of setting. They have been out in public, they have been alone in his car, but never in a house, and especially nowhere with a bed. Taking a deep breath, Jackson sees the same expression and emotion in Sienna's eyes. Jackson brings his hand up and caresses Sienna's face. "I'm glad that I could do this for you. I've never been a big fan of Valentine's Day. Trading cards with your classmates was cute as kids. As you get older and realize what it's supposed to represent... it just isn't the same when you don't have someone special to share the day with." Jackson tells her.

"And now?"

"Now... now it makes me see how having multiple someone doesn't feel... right. I still say that each of the girls I see is unique in their own way and deciding between you all is near impossible... but seeing the joy I brought to your face today, makes me realize that I have to have a heart to heart with the others... sooner rather than later."

"Do you mean..."

"That I have to make a decision... the life-changing kind... yes," Jackson informs his date.

Sienna's heart is fluttering. All night long she has been contemplating if she could or should do what she has been dreaming for the last five months. Now is the time when she has to either send Jackson home or follow through with her desire. She takes a deep breath and Jackson watches her breasts rise and then she exhales. "I know that I wasn't the kind of girl you saw yourself with that first day in the cafeteria. I've learned a lot since that time. About myself and about the kind of person you liked and liked being with. I didn't like what I learned about myself so I made it a point to change... hopefully for the best. During Winter Break, after you helped me with Brady, you told me I was now someone you wanted to get to know... and we have gotten to know one another with the odd make-out session thrown in to keep your skills in practice." Sienna states blushing.

Jackson takes her left hand and kisses the back of it as a gesture of intimacy. She knows based on his comments the other girls all keep his skills sharp but she is determined to outdo those mystery adversaries. "Sienna, in the time we have spent together I've gotten to know you, really know you. You are interesting, entertaining, funny, and stunningly beautiful." Jackson states.

"Jackson... you are the nicest, sweetest guy I have ever had the pleasure of spending time with." Sienna begins. "Most guys are so anxious to get their hands on me and get me on my back that they don't take the time to get to know me. Brady is a good example, he pawed at my tits and shoved his tongue down my throat every chance he got. You didn't do that. You took me out, we talked, and we spent time just getting to know one another while doing things together. You took the time to get to know my likes and dislikes. As far as intimacy goes you let me set the pace. You didn't rush me or do anything that I wasn't comfortable with. Most guys can be a bit too aggressive."

"There is a big difference between assertive and aggressive and most guys don't know that," Jackson states.

"I feel comfortable with you Jackson," Sienna tells her date. She places her hand on top of one of his and leans in to kiss him. "I know that of all the guys at Bayview, you would never press me into doing something I'm not comfortable with."

"Never." Jackson agrees and kisses her on the cheek.

"Which is why I'm comfortable doing this." Of all the things Jackson thought that Sienna might do after saying those words to him, Jackson didn't expect what came next.

Sienna reaches behind her back and Jackson hears the distinct sound of a zipper being pulled down. Jackson's pulse was racing before but as Sienna stands and lets her dress fall from her body and pool at her feet Jackson sees more skin on a woman than ever before. In the past five months, he has had the luxury of spending time with some of the most beautiful women in Bayview High School. With each girl, he has made a certain amount of progress romantically. He found that being a consummate gentleman got him farther than following his baser instincts. Sienna straddles Jackson's lap and Jackson's brain finally acknowledges the fact that she is adorned in only black lace panties and a matching sheer black lace bra. Sienna plants dozens of kisses on Jackson's face as she goes to work divesting him of his clothes. Soon Jackson's suit is being placed on a nightstand and the young man is standing beside Sienna, holding her close in only his boxer shorts.

"Are you sure? Are you absolutely sure this is what you want?" Jackson whispers into Sienna's ear. He is holding her ever so close, memorizing the feel of her body in his arms.

Not wanting to let doubt creep into her mind (or mouth) Sienna nods her assent and then reaches behind her back (again) and unfastens her bra. Sienna slides the garment from her body exposing her upper body to Jackson. Deciding to take the last step together, Jackson and Sienna slide their underwear down at the same time exposing themselves to one another.

Sienna moves onto the bed, sliding backward as Jackson follows closely behind her. The covers are pushed back with their feet as the two teens press their warm, naked bodies against one another. Limbs become entangled and lips reconnect as they start the slow process of intimately getting to know one another. Sienna and Jackson are excited, really excited. As Jackson's engorged member is pressed firmly between his lover's legs, he can feel how drenched she is.

The soon-to-be lovers know that time is a luxury so they decide not to waste theirs. Sienna kisses Jackson for several long moments before she ends the kiss and has Jackson sit up. Sienna moves back against the pillows so that she is arched just right. "Please make love to me." Sienna requests.

Jackson moves in and melds his body against hers. His pulse is racing, his heart pounding. As he moves his hips forward Sienna watches as the head of his cock moves toward her opening. Sienna groans as Jackson slowly parts her folds and slides as gently into his lover as possible. Jackson knows that his lover is about to give him her most precious gift and wants to make this experience as pleasant and memorable as possible. Likewise, he is sharing his first time with her. Continuing to move slowly forward until the head of his cock touches her innocence. The contact earns him a gasp and Jackson doesn't move any further, in fact, he starts to withdraw. Sienna, feeling this wraps her arms around Jackson's back and locks her legs behind his ass.

"No... wait..." Sienna pleads. "Getting used... to this." She informs her lover. Releasing her leglock, Sienna says, "Do it, make me a woman."

Jackson pulls his length back until the head is almost out and seeing Sienna ready for what comes next he suddenly remembers something he once heard in a movie. Leaning forward, Jackson begins nibbling on Sienna's earlobe. The action sends a sensation all thru Sienna and she begins to moan in pleasure, right until Jackson thrusts his hips forward and shatters her Hyman. Sienna groans as her innocence is taken and her death grip once again is locked around her lover. As blood seeps from her pussy Jackson kisses Sienna and whispers how much he loves what she has given him and that he feels so special that she shared this moment with him. Sienna likewise kisses him in between whimpers and thanks Jackson for all he has given her.

Only when she tells him that it is ok does Jackson begin to move. Sienna's legs are parted and soon she is feeling the express pleasure of having a lover fill her insides and show her what it's like to be loved and to be made love to. Jackson is going slow and methodical as this is his first time and he is trying to make this last as long as he can. He has heard that if a guy rushes too quickly that he will come just as quickly. Not sure if he will ever get this chance with Sienna again he wants them both to remember it.

In the beginning, Sienna just lay flat and still, first from the shock and the pain, and then from not knowing what to do. Jackson, while going slow, was making her feel amazing and she only hoped that he felt as good as she did. Eventually, she began thrusting her pelvis up trying to meet his thrusts. It took her a while to find a rhythm to match his and there was some awkwardness at first. Eventually, they stopped and explored together, trying to figure out their timing. Once they did that Sienna decided to pull her legs backward so her knees were almost touching her head. This opened her up even more and Jackson felt like she was sucking him inside her whole body.

The two teens began to moan and groan until lost in their sensations, they picked up the pace. Jackson didn't even realize he had begun moving faster or harder against his lover as he gave into his mating instincts. The sound of their skin slapping together began to drown out the soft music playing in the background. Sienna lifts her legs back and Jackson uses his arms and pins them back, giving him a better angle. He drives his member forward and really pounds away at his whimpering lover. Sienna pulls Jackson's face to hers and they kiss deeply as they make love. In only a few more strokes Sienna reaches her peak and came first, squeezing Jackson's chest against her breasts and her legs locked behind Jackson's ass again holding it against her core. Thanks to Sienna's walls clamping tightly around him Jackson was only seconds behind her and felt strange as his testicles tightened and then he felt something flowing out of them, through his cock, and into Sienna's womb. Both teens knew what was happening but never having experienced the sensation before, they screamed and groaned as the sensation overcame them.

Sienna refused to let go of Jackson who needed air but didn't want to separate from Sienna either. The pair rolled on their sides and loosened their hold momentarily. As air came back into the lungs and the breathing returned to normal the two teens leaned in and kissed one another passionately. Jackson was the first to roll onto his back and Sienna snuggled into his loving embrace.

Jackson walked into his house at exactly 10:59:59. His mother was waiting for him at the kitchen table. When the door clicked shut she was looking at him holding her cellphone and he could see that he just made it home.

"Back with a second to spare," Jackson says quickly walking past his mother and tossing his car keys into the key bowl.

"Did you have a nice time?" DJ Fuller asks her son.

"Valentine's Day is a day just a day like any other," Jackson says not looking at his mother. "However, my date appreciated your generosity though and told me to thank you. So, thanks mom for letting me go out tonight and make someone's Valentine's Day special."

Jackson's statement to his mother was a bald-faced lie, but one easier to tell not looking her in the face. This was the best night of his young life, and he was trying to keep the grin on his face concealed until he was in the shower washing the smell of sex from his body.

DJ wanted to question him more but she remembered how forthcoming she was at that age about her dates so figured it was best just to let him be. She only hoped that Jackson was making good choices.

To Be Continued