~ Saturday, May 22nd, 2021 09:12 hrs ~
When Jackson woke up that morning he found himself in the master bedroom, naked, and alone. Rubbing his eyes he looked about and listened and seeing that the bathroom was open, as was Daniella's closet he realized that she had already gotten up and made a hasty exit. Jackson sighed as he sat up and cursed himself for being so tired after the events earlier in the morning. He had hoped to wake up first so that when she woke up she wouldn't freak out... which she apparently did as she was nowhere to be found.
Tossing off the blankets Jackson walks naked into the bathroom and proceeds to wash off all of the reminders of the events of earlier this morning. As the water cascades down his head and over his body, he still has difficulty believing he actually lived the events. He was awoken from his deep sleep by the most amazing feeling. It was very hot, very wet, and centered around his dick. When he was finally able to open his eyes and focus them in the darkness his gaze fell upon the blonde hair of Daniella "DD" Delgado giving him his first ever blowjob.
Keeping his eyes open was very hard as her mouth felt magical as she took him deeper and deeper with every movement up and down his cock. He didn't know what led her to do this but no man in his right mind would ever stop this sexually alluring woman from initiating them into the world of sex. When Jackson felt himself on the verge of blowing his load he allowed it to happen but found the will to not give her all of his seed.
As soon as she inhaled his cum Miss D moved onto him and once she notched his cock into place, she sunk down on his rod and rode him for all he was worth. Fortunately, Jackson had given her a bit of his seed so he was not so sensitive that he would shoot off again so quickly. DD was quiet for some time to the point Jackson wasn't sure that he was pleasing her. That all changed when she finally released her lower lip and began moaning and groaning. Now content that he was up to the task Jackson let his hands come up and feel his former teacher's naked breasts. As he soaps his own body he can clearly remember the heft, the weight, the feel of her enormous tits in his hands.
The next big thing he memorized was the feel of his first woman as she came on his cock. Her pussy squeezed his stiff member for all it was worth as she came. If they had managed to do so in unison he was quite sure it would have milked his cock of all the seed he still had stored in his balls. As he was still hard and ready to go Jackson grasped his lover and flipped her onto her back. She let out the cutest shriek as he did so and that just spurred him on. The feel of her warm sweaty body against his as she leaned down and plowed into her with reckless abandon was exhilarating. If his body could have he would have made love to her for the rest of his life but alas, he eventually recharged his load and gave his lover every last bit of his seed that he had stored in them.
This time it was not two quick blasts down her throat, this time he delivered five massive blasts that he had stored up since before his senior prom. Daniella's pussy did indeed squeeze his cock when he brought her to her second orgasm of the morning. The head of Jackson's cock was lodged firmly at the mature woman's cervix and while not big enough to penetrate directly into her womb it did deliver his baby batter so that it didn't have as far to travel. Daniella's legs were wrapped firmly around her lover, ankles locked just above his bare ass and her arms were holding him firmly against her tits. The two kissed passionately in between breaths until Jackson, needing more air, rolls off DD and onto his back. The last thing he remembered before passing out was the two of them snuggling together, kissing, and then darkness.
Jackson finishes rinsing off and turns off the water. Stepping out of the shower he dries off and then makes his way to his closet to pick out his clothes for the day. He opts for gray Cargo shorts and a white button-down shirt. He plans to walk about the ship and hopefully find Daniella so that they can talk about last night, and hopefully, hopefully she will be inclined to see where they can go from here.
~ 18:45 hrs ~
Jackson was a bit put out as he has traversed the entire ship and managed not to find his roommate anywhere. He has seen all four of his travel companions, bumped into Clara, and asked her to keep an eye out for DD, and is actually on the verge of making a shipwide announcement when he walks into his room and finds Chelsey sitting on the couch waiting for him. She has her carry-on bag with her as she sits watching TV. The moment he enters the room she turns it off and smiles at him. Jackson leans back and looks into the main bedroom and doesn't see anyone or anything out of place. He can tell the bedding has been changed out but other than that nothing save his guest seems out of place.
"Hello, Chelsey," Jackson says greeting the young Latina.
"Hi," Chelsey replies. Jackson can see she is a bit nervous.
Chelsey is one of four female graduate seniors from Bayview High School on this particular cruise. Jackson was gifted this trip by his mother at the suggestion of Fernando Guerrero, Ramona's father. While he trusts his 18-year-old daughter implicitly he does not trust all of the single (or not) men on the cruise. Until a few years ago Fernando was one of those men that hit on every beautiful woman he encountered, despite being married to Ramona's mother. Knowing what scoundrels men like he used to be can be he wanted Jackson along to watch over Ramona, and her friends (but mainly Ramona).
While Sienna and Ramona were less than enthusiastic about having Jackson along as a chaperone/babysitter, Chelsey was quite ecstatic. For four years Jackson Fuller has been the exclusive property of one Roxanne "Rocki" Mahan. The goth-like girl was two inches taller than herself, they had long dark hair but Rocki's was naturally black while hers was dark brown. Rocki tended to dress in dark, not conformist type clothes while Chelsey was more into bright cheerful colors and tended to wear what was fashionable. Both women were lean and far from voluptuous but they both had very respectable figures. The difference was that while Chelsey was coy and waited for guys to approach her, Rocki went after the guy she wanted, in this case, Jackson Fuller.
Chelsey was over the moon excited when before prom Ramona informed her that Rocki was not only not going to prom with Jackson, but that she was planning to break up with him immediately after graduation. By this point in time, everyone going on the cruise knew that Jackson was joining them and this was the best news that Chelsey could have asked for. Her master plan was to spend as much time with Jackson as possible and hopefully "convince" him that the best thing for him would be for the two of them to start dating.
Until now that plan has been a bust. She had managed to get in a few fleeting moments with him by the pool but it seemed that whenever they had a moment by themselves Clara, Jackson's personal steward (and her rival) was around. Then, to add insult to injury, Jackson went all gentlemanly, and when their former teacher broke up with her boyfriend and needed somewhere to reside Jackson gave her his bedroom. While Jackson had a separate room he spent quite a bit of time with the two older women at this point.
Chelsey had all but given up hope until Miss D came pounding on her door after breakfast. It was a fluke that she was even in the room as Chelsey had only returned to drop off a momento that she had bought. It was just a simple little trinket the ship sold but they were almost out of them and so she bought it and returned to drop it off. The older woman was an emotional wreck for some reason (again) and while she didn't want to go into details, the gist of it was that she couldn't be in close quarters to Jackson any longer and begged her former student to swap rooms with her.
Chelsey didn't answer the woman at first. She took in her words, absorbed what was said, and then got up, and with Daniella pleading with her to trade she pulls out her bags and pointed to the drawers, and instructs the older woman to start putting them in the bag. In no time Chelsey was packed up, and the two women were on their way to Jackson's to do the same thing for Daniella. Once the older woman's bags were packed the pair traded room keys and Chelsey waved goodbye to the super sexy teacher.
