If you havn't done so already, read the previous chapter before continuing.
Jake awoke early the next morning, he rolled out of bed went to the bathroom and went about his morning routine. He tried his best to shake last night’s events with his girlfriend out of his head. Once ready, Jake drove off to the High School and walked up to the baseball field. He was the first player there, and ran a few laps to get warmed up. He noticed the scouts started showing up, and took their seats in the bleachers. Jake finished his jog as his best friend and catcher Chris Archer showed up. "About time man! I was just about to call you!" Jake jokingly shouted. The two started throwing and got loose for the game. Just before Jake started to throw his pre-game bullpen, he looked to the stands trying to scan for Katie, no sign of her. Was she really that mad at him? He pushed her out of his head focusing on the game. Jake was lights out on the mound. Throwing a shutout and struck out 14 batters. It was Jake’s best outing of the year. His coach talked to him after the game, "the scouts were impressed, they will be back in a few weeks, keep pitching like that and the offers will be rolling in!" Jake was ecstatic, he had been working his ass off over the last four years for the chance to continue playing ball after high school. He sent a text to Katie, informing her of the news and said he wanted to see her before he went to Mexico with his family for spring break.
Sunday came and went, and he had still got nothing back from Katie. "Fuck it," Jake said to himself, "If she wants to be mad at me then so be it, I won’t let it ruin my vacation." Jake finished packing his bag for the 5 day trip. Monday morning came, and a cab picked the family from the airport. A few hours later they were in Playa del Carmen, dropped off in front of their hotel. They went to the front office to check in. "Im sorry," the concierge said with a hint of a Mexican accent "It appears all we have are queen beds at the moment.”That’s fine, the kids can share a bed for a few nights, besides, we're in paradise!" Exclaimed Jakes dad, who slapped him on the back.
After getting settled into their room, their parents came by, and informed them that they would each get $500 to spend during their time in Mexico. "Thanks!" The twins exclaimed in unison. Alexis went off to the information center to book a trip to some Mayan ruins, while Jake pondered what he wanted to spend his money on. He went to the balcony, and saw some divers gearing up near the resort dive shop. "That’s it!" Jake said he had always wanted to learn to dive, why not now? He changed out of his travel clothes and put on board shorts and a tank top, hoping to work on his tan over the next couple of days, he put on his flip flops, grabbed his shades and walked down to the dive shop.
"As luck would have it, we have a class starting in a half hour" said the clerk, "fill out this paperwork, and we'll get you started" Jake sat in the classroom and found one other student in the room, olive skin, brown eyes, wavy brown hair, she was beautiful. Jake sat down and introduced himself, the girl replied in broken English, with the sexiest Italian accent, "I am Valentina, nice to meet you." They shook hands, and chatted for a little bit. Jake learned that she was from a small villa outside of Pisa, and was in Mexico with her family for a few weeks. The Instructor, Matt, came in and set down his books. "So you guys want to dive, I’m here to teach you how" he said energetically, before teaching the basics of SCUBA Diving. Matt talked about the physics of diving and covered the basic gear, the class watched some videos and took some quizzes. Jake found it pretty simple, but Valentina was struggling a little bit. They moved onto the pool, and did some basic skills, clearing a flooded mask, recovering a regulator that came out of their mouth, and went through the procedures in case they ran out of air. By 5:00pm they were done with everything for the day. “We’ll meet at 9:00am in the classroom,” The instructor said “Finish reading the book and do the problems at the end of the remaining chapters, and we’ll finish up the quizzes and test tomorrow” They were dismissed and Jake started walking away from the dive shop.
Valentina caught up to Jake and asked for his help with the remaining book-work, he readily agreed, eager to spend time with this Italian beauty. He explained everything to her in a way she could understand, at the end of the night when she understood the material she thanked him, giving him a kiss on the cheek as she said goodnight.
The next morning they covered the remaining material in the classroom which they both excelled at. “Good Job,” Jake told Valentina, “I have good tutor” she replied with a wink. They moved onto the pool where they finished up the rest of the pool dives. Jake noticed Valentina was a lot more hands on then yesterday. Whenever the instructor wasn’t looking he felt her resting her hand his arm. Jake even swore that she pinched his butt he got out of the pool. They went on to do one dive in the ocean, where the instructor had them perform some of the same skills they did in the pool and led them on a tour, during the underwater tour, Jake noticed Valentina stayed very close to him. This time he definitely felt her squeeze his butt a few times, and he could have sworn she deliberately tapped the head of his penis. He played it cool and continued with the dive. At the end of the day, Valentina gave him a hug before wishing him goodnight.
The next morning the finished up with their last ocean dives to get their certification, Valentina was much flirtier today. She definitely grabbed Jake's junk twice when the instructor wasn't looking. “Two can play that game” thought Jake, and proceeded grabbed her butt and then one of her breasts a few minutes later. After the dives were done they completed the last paperwork and rinsed off. The sun was starting to set and Jake suggested they should go for a walk on the beach, to which Valentina readily agreed. They walked hand in hand, Jake in his board shorts and bare chest, and Valentina wore red and gold bikini. Her B cup breasts barely contained by the thin fabric, her round cheeks only halfway covered by her bottoms. Jake had a hard time not staring at her assets. The two teens sat down in the sad and watch the sun set. Jake felt her get close, her arm wrapped around his, as she rested her head on his shoulder. Once the sun set, they laid down and gazed at the emerging stars. Valentina snuggled close, first laying her head on his arm, then resting her head on his muscular torso. Her right hand rested on his toned stomach, before she traced her fingers down reaching the waist of his board shorts. Her hand moved lower, her fingers teasing the inside of his leg before sliding down to his knee. In one quick movement, slid her hand up his shorts, grabbing his now hardening genitals, simultaneously she moved her head up and gave Jake a passionate kiss.
She continued kneading his cock in her fingers, making him stiffer and stiffer, once she was satisfied with his hardness, she broke the kiss, and said "I want to repay you for helping me the other night." She slid in-between his knees, kneeled between them and started to kiss her way down his abdomen, her hands untied his drawstring, she peeled back the two flaps, his erect member freed of its prison, slapping onto his belly. She smiled at its size, before taking it in one hand. Valentina gripped the base of his shaft and started sucking his member. She wasn't the most talented, Jake thought, but she made up for it with enthusiasm, she would take three long deep bobs down his shaft, slurping on the way up followed by six fast shallow bobs focusing solely on his sensitive head, swirling her tongue around his knob, Jake let out a feint moan, his balls started to tingle. Valentina sensed his primal urge, and lifted her head from his cock. Still gently jacking the shaft, she says "I want you" before rolling onto her back and untying the sides of her bikini bottom freeing her pussy. Jake could barely see trimmed bush in the moonlight. She beckoned to him, her eyes begging him to fill her up.
Jake rolled over, got between her legs, and slid his cock into her hot pussy. He marveled at how wet she was as be began to slowly slide in and out of her depths. She cradled the back of his neck. Pulling him down closer to her, wanting their bodies to touch, her legs interlock behind his lower back. "You feel so good" she whispers into his ear before releasing his neck. Jake raises himself up, increasing the speed of his thrusts, her breasts bouncing, barely being restrained by her top. She pulls the fabric restraining them to the side. Her breasts bounce freely every time he thrusts his manhood into her, Jake could feel himself getting close. "I’m gunna cum" he grunts, Valentina pushes him out and jacks him off. As her silky hands wrap around his shaft, stroking his cock slick with her juices, he shoots six thick sticky ropes of cum over her tight Italian body. The first lands on her right breast, the second falls in between them. The remaining spurts, not nearly as powerful, land on her belly, she slows her pace on his cock, milking his remaining seed, now dripping onto her bush. Her free hand slides along her belly, scooping his semen with her fingers, bringing it to her mouth "delizioso" she exclaims in Italian after savoring the flavor.
She stares into Jake's green eyes, sucking her fingers clean. Jake smiles, and says “it’s getting late, we should get to bed." Valentina frowns, but understands. She ties her bottoms, trapping his semen in her bush, and covering her breasts with her bikini. As they get up, Valentina walks towards the water, and rinses the semen off her stomach. The two teens walk back to the resort, and give each other a quick kiss before parting at the elevator. As Jake walks into his room, he notices lights are on, but doesn’t see Alexis. Intent on showering Jake shucks off his shorts and walks into the bathroom. As he walks through the partially opened door, he sees Alexis drying herself from the shower. Her back towards the door, Jake could see full well that his sister had developed, and nicely. He had never thought about her sexually, until a few days ago, with the text he got from Ms Dyers. She threw one leg on the toilet drying off her legs when she looked over her shoulder and saw him. "Jesus Christ Jake, haven’t you ever hear of knocking? And why the fuck is your penis out!" She exclaimed, wrapping the towel around her. "Sorry, the door was ajar, and I didn’t hear you" Jake stammered, covering himself up "Well get the fuck out!" Jake stepped back into the room, and quickly threw his board shorts back on. He sat on the bed and waited for Alexis to finish. His mind flashed back to the link Ms Dyers had sent him, he couldn't get that picture out of his mind.
Alexis walked out fully dressed "it’s yours," she said coldly before sitting on the edge of the bed. Before Jake turned on the shower he made sure the bathroom door was locked. He stepped in and cleaned all the sand and sex off of him. He sat under the hot water and tried to get the image of his naked sister out of his head. Drying off, he changed into a pair of shorts and went to lay down on the bed. Alexis was watching TV, but Jake just rolled over and fell asleep.
Alexis was out of the room by the time he woke in the morning, good, he didn’t want to deal with what had happened last night.
Jake rolled out of bed and walked to the bathroom to take his morning piss. As he brushed his teeth he replayed last night’s encounter with Valentina, pushing his sister out of his mind. After he was done, he called Valentina’s room to invite her out for breakfast. She politely declined as she had to go out with family for a day trip, but agreed to dinner. Jake went down to the dive shop and was able to hop on a boat dive to kill some time, after the boat docked he headed to the resort gym to get a workout in before returning to his room to shower. He heard a knock on the door as he stepped out the shower. He threw a towel around his waist and slowly opened the door.
Valentina wore a flowing orange and red sundress, a pearl necklace fell around her neck, standing in a set of white heels. Jake’s jaw dropped, he stared at her for a minute before inviting her inside. She smiled as she walked in. She gently touched his bulge through the towel as she walked past him, “Boop!” she said with a giggle. "Well I’m a little under-dressed. I suppose I should put some clothes on.” said Jake. Valentina went to the balcony and gazed out on the ocean, while Jake threw on a pair of khakis, and a striped dress shirt. He walked out to the balcony and wrapped his arms around Valentina’s waist, his chin cradled in her neck, sharing an embrace for a moment before heading out for dinner. They arrived at a local seafood restaurant, and enjoyed a fabulous sunset dinner, before returning to the Jake’s room.
They resumed their embrace on the balcony, as Jake started necking her, his hands roaming up and down her body, his hips gyrating into her butt. They stayed like this for a minute before she turned around, and they kissed passionately. She stopped the kiss, and walked back into the room. After she stepped inside, she untied the knot behind her neck and her dress fell to the floor. She was now in nothing but her heels and necklace. She seamlessly stepped over the dress, doing a 180' twirl and beckoned Jake to her. Entranced, he followed her, she took his hand and sat him on the bed. She removed his trousers and as he removed his shirt. She pushed his torso down onto the bed as she started to suck his semi hard member. She sucked him at a slow pace, until she was satisfied with his rigidness. "I want you to remember this night, to remember me forever, I want you to in my ass" she said. Standing up, she got on all fours in the bed, and playfully shook her ass side to side. She sank her chest down, so that she was resting shoulders, ass up. Her hands moved back and grabbed her buttocks spreading them. A hand slid down, so that her finger could slide along her slit, slicking it with her juices before inserting a finger into her own anus. Jake got up, stood behind her and started to finger her pussy, getting his finger lubed up, he replaced her finger with hers, slowly penetrating her virgin anus. She began to whimper in pleasure. He slowly added a second finger, more whimpers.
He soon felt that she was ready, and removed his fingers, he spit on his hand, rubbing it along his phallus. Guiding his cock-head to her rosebud he entered her slowly, she let a small cry of pain as she adjusted to his girth stretching her sphincter. Once she had adjusted, she started to push back onto his cock. Until he bottomed out in her, they both moaned in pleasure. He slowly picked up his pace sliding his cock in and out of her newly deflowered ass, soon her legs started to go weak.
The two lovers rolled into a spooning position his cock never leaving her ass. As he increased his pace Valentina used her free hand to vigorously rub her clit. Jake reached his arm around, roughly grabbing her breast, then pinching her nipple. Eliciting a moan of excitement from Valentina, before lightly wrapping his hand around her neck. He held a light grip on her, toyfully choking her as he picked up the intensity of his thrusts. He let out a low moan, he was getting close, Valentina sensed this and increased the attack on her clit, and inserting three fingers of her other hand into her vagina. Jake could feel her fingers through the thin membrane between the anus and vagina. The additional stimulus was too much, he emptied his seed into her bowels. She felt him erupt and cried out in ecstasy.
They laid together, still joined as one for a few minutes. He left his now softening cock in her ass as long as he could, until it finally plopped out, a small amount of cum oozing out, soaking into the sheets. They laid in each other embrace until Valentina noticed the time. She had to get going, she rolled over, kissed Jake on the cheek, saying "thank you" as she got dressed. She wrote her email and told Jake to keep in touch. Jake walked her to the door, and gave her one last kiss before she walked out the door. He could barely see the traces of cum running down her leg.
Exhausted, he laid down back down, falling asleep immediately. He stirred from his slumber when he heard the door open, and felt someone get in bed, "Why is the bed wet?" The voice muttered before falling back asleep.
The next morning he felt a body against his, instinctively he threw an arm over, his arm resting just beneath the breast. His groggy mind flashed back to last night’s encounter. His cock hardened, instinctively he thrust his hips forwards, meeting the meaty flesh of a juicy ass. His arm pulled the body tighter. Eyes closed, his arm trailed down, reaching the waistband of the bodies shorts, he slid a finger, then two down the front of the waistband, before sliding his fingers along to the hips, before moving around to grab the meaty flesh of the ass in front of him. Jake moaned aloud as he gave the cheek a squeeze. Alexis stirred, the words waking her from her slumber. Jake squeezed her butt cheek again as he thrust his erect penis against her backside.
Alexis, now fully awake, rolled over, "Jake, what the fuck are you doing!" she exclaimed. Jake snapped out of his semi conscious state. His eyes opened, his cock softened, seeing his sister, his mind registering where he was. "Oh shit!" he replied, quickly removing his hand from her shorts. Embarrassed, he meekly tried explaining he thought she was someone else.
"Yeah right, you’re just a fucking pervert, first watching me in the shower and now this?" Alexis rolled out of bed, retorting "Groping and dry humping your twin sister? That will go over well with mom and dad." "Please don’t tell them" Jake pleaded, "I’ll do anything"
"Anything?” Alexis pondered, “That’s a pretty big favor. I’ll let you know when it’s time." She said, walking towards the bathroom. Jake, now relieved, rubbed his eyes and stretched, "Fuck, what have I gotten myself into?" He thought to himself, staring at the ceiling. Alexis got out of the bathroom, fully dressed, and started packing her bags. Jake rolled out of bed, went to the bathroom, showered, changed and did the same. 30 minutes later they were in the lobby of the hotel leaving for the airport. The twins were seated next to each other the flight home "Awkward…." Jake thought to himself. This was going to be a long flight.