Chapter 5
Tristan was still bent in half with his sister’s phone in his hand, peering into his sister’s backpack at the concerning text message from Jacob, when Jacob came rounding the corner of the building. “There you are!” he said, sounding happy to see her. “I thought I saw you walking this way.”
Tristan jolted himself up, looking startled, as if his bare ass was exposed in his compromised position, but he was more in shock and horror—frozen with fear at the thought of how this could play out. In that instant, he considered revealing himself to his sister’s boyfriend. It wasn’t like they hadn’t met before, so it would be just a little awkward, but then again, ‘What would Jacob say?’ Tristan thought. ‘Would this get around campus? Would Jacob tell everyone and turn him into the school joke—the school freak?’ Tristan didn’t know what to do. He bent forward and tossed the phone in her bag, but then suddenly he was lifted in the air.
“Come here,” Jacob said, as he wrapped his muscular arms around Tristan’s waist, pressing his pelvis into Jacob’s rear and easily lifting him the air like a rag doll. Tristan braced himself on Jacob’s arms, as he straightened himself out. “How was the final? Easy?” he asked, as he held Tristan in the air. Jacob squeezed a nod and a high pitched ‘Yes!’ out of Tristan before loosening his grip. As Tristan returned to earth, dragging down Jacob’s body, his sister’s skirt rode up and caused his bare ass to pass over the crotch of Jacob’s jeans, while Jacobs arms worked their way up to Tristan’s chest. Jacob was supporting Tristan’s body by cupping his sister’s bra. Tristan gently pushed Jacob’s hands back down to the clench of his waist before fixing the skirt back over his butt. Jacob wrapped his arms around what he believed to be his girlfriend’s chest and buried his nose in Tristan’s neck. “Mmmm, you always smell so good,” he said, as he took in the sweet, vanilla scent of Tristan’s neck.
Suddenly, Tristan became acutely aware of the warm breath of Jacob’s mouth just an inch away from the tender skin of his neck where it met the edge of his jaw. It sent a chill up his spine, awakening his senses. He was still petrified, so he didn’t move, even when Jacob brushed back Tristan’s hair, founding his mark and began to gently kiss his neck. At first, Tristan felt horror at the idea of a boy kissing him. What was worse, this was her sister’s boyfriend. Then he felt Jacob’s tongue begin to caress his neck, while he nibbled and sucked on Tristan’s flesh. ‘Mmm, that actually feels kinda good,’ he said to himself. He could feel some of the tension leaving his body, even if his heart was still pounding. His mind recalled the imagery of passionate kissing from movies and from the porn he watched. His mind placed him in the female roll, and he opened himself more to the moment. Tristan could feel his cock beginning to quickly grow. Within seconds, Tristan released himself of the awkwardness and engulfed himself in the sensation of Jacob’s hot, eager mouth on his neck. He turned his neck, opening it so Jacob’s mouth had better access. Tristan’s mouth parted, releasing his hot breath. He surprised himself when he instinctively uttered in the perfect tone of his sister’s voice a tender sounding moan followed by encouragement, “Mmm, that feels good.”
Jacob was really sucking on Tristan’s neck now. He was certainly going to leave a hickey, but Tristan was in virgin territory, so his mind was lost in the moment. Jacob’s hands moved back up to his girlfriend’s breasts, cupping them firmly. Tristan could feel the pinch of his nipples in the palm of Jacob’s hands. With each squeeze, he felt a jolt of painful pleasure shoot through his body, but Tristan feared Jacob would be able to tell the difference between his chest and what he was expecting to grab; his sister’s chest, so he guided Jacob’s hands back down to his waist, but Jacob continued down to Tristan’s hips and pulled Tristan’s hips back into his crotch. Even through the thick wool skirt, Tristan could feel Jacob’s hard bulge in his pants, as Tristan’s rear was firmly pressed against Jacob’s crotch. Jacob began rhythmically thrusting his hard-on into Tristan’s plump bubble butt, smashing it between their bodies. With each thrust, Tristan could better feel the outline of Jacob’s growing member. Tristan’s clammy, hot hands were resting on top of Jacob’s firm grip still locked to Tristan’s hips.
Tristan could hardly help himself now. The lust was quickly building in the young teens loins. He twisted his shoulder and strained his neck around to will Jacob to him. Jacob took the bait, following the scent of strawberry lipstick where he found Tristan’s hot mouth waiting. The two locked lips and slid each other’s tongues across one another. It was Tristan’s first kiss, but it felt right in that moment, dressed as his sister’s clothes and receiving it from a hot stud who was seemingly kissing a girl. Jacob started to twist Tristan around, but Tristan feared being face to face, so he instinctively pressed his ass back into Jacob’s crotch, grinding his ass against the boy’s hard cock. That did the trick. Jacob pressed back, and then he started to move his hands towards his girlfriend’s pussy, but Tristan instantly sensed their motion and gripped his hands. He diverted them back, encouraging them to go the other direction. Jacob worked his hands down Tristan’s hips to his thighs, finding the bare skin with his warm hands. Jacob slid his hands back, digging his fingers into Tristan’s flesh before working them up to Tristan’s ass. Jacob worked the skirt up over Tristan’s ass, so his bare flesh was now grinding against Jacob’s jeans. He found the meat of Tristan's booty and squeezed it firmly, causing his cheeks to separate in the process, which only allowed Jacob’s bulge to sink between Tristan’s ass that much more.
Jacob released his lips from Tristan’s. “You’re so fucking hot,” he whispered in Tristan’s ear, as he nibbled on Tristan’s neck. “You were amazing last night.” Tristan assumed that meant Trisha and him fucked. He had seen their condoms when he stole her dildo, and he even had seen a few used wrappers in her trash before, so he knew they were having sex, but knowing their conservative parents, there was no way she was going to be on birth control, so what he said next was initially surprising. “I can’t wait for tonight…” he continued through his kisses, “…and maybe I can finally cum in you this time.”
Jacob’s hands were still busy squeezing and kneading Tristan’s ass. He almost didn’t notice that Jacob had worked his hands lower until suddenly he felt a finger brush against the thin cotton that covered his sphincter, followed quickly by a second finger that stroked the cotton covering his hot taint, or what Jacob thought, was his girlfriend’s pussy. Tristan instinctively tensed up, afraid Jacob discovered the truth and pulled Jacob’s hands back to the side of his hips. “No!’” Tristan had blurted out, but that just got Jacob confused. Nevertheless, Tristan was thinking things might have gone too far.
“You said maybe?” he asked, with a tone of disappointment to his voice. He was no longer kissing Tristan’s neck. “Babe, I thought we agreed it was the only way.” Then the sound of his voice got cute and playful. He whispered back in Tristan’s ear, “I’ll be gentle and go slow. Just until you ask me not to go slow.” He slightly chuckled, humoring himself. “Hey, it was your idea,” he said, as he returned to kissing Tristan’s neck. “As I recall, you said you wished there was a way you could feel me cum in you…” Jacob went back to gently trusting and grinding his swollen cock against Tristan’s bare ass. He continued, “…since we couldn’t do it the other way.”
Tristan realized what Jacob was going on about now. ‘My sister is such a slut,’ he thought to himself. She was no different than him. She acted like he was the sexual freak in the house, but here she was planning to get fucked in the ass tonight, or rather, she was considering it. Tristan felt a little bitter at that moment and preoccupied with deciding how he was going to get out of this situation before it went any further, that he didn’t notice that Jacob was fumbling with his jeans. Then Tristan’s mind was suddenly pulled form his thoughts back to reality when he felt Jacob’s hot, thick member smack between his bare cheeks. Jacob had wrestled his jeans button open and unzipped his pants, fumbled with his boxers and produced his gorgeous, young cock. A jolt of energy shot through Tristan’s body, as the feeling of Jacob’s flesh touching his flesh.
Tristan savored the moment. Jacob’s cock felt amazing pressed against his cheeks like nothing he had ever felt before, so much better than the dildo he routinely sat on. It was so soft and hard at the same time. It was tender and silky, yet it stood tall with purpose. Tristan could feel his own hard cock aching for attention, so he understood the pain probably building in Jacob’s balls. He thought about how bad he always wanted to fuck a girl and cum in her, so he knew Jacob’s torment. This line of reasoning was weighing on him, breaking down his will. Tristan began to press his ass back again into Jacob’s crotch, grinding his ass this time with more precision along the length of Jacob’s shaft. He was clearly much longer and thicker than Tristan. Jacob’s kisses were getting hotter on Tristan’s neck, which was building the lust in Tristan too. He couldn’t help himself; it just came out of him. “Okay,” he muttered.
Jacob stopped. “Really?” he questioned, with a rise in his voice that sounded like joy.
Tristan nodded and pulled Jacob’s face back to his neck. ‘What did he sign his sister up for?’ he thought to himself. ‘What if she said no later? That would be torture.’
The hot, humid day, and their steamy embrace was causing Tristan to perspire more. He could feel the heat from his core causing the sweat from his ass to coat Jacob’s member, which allowed his cheeks to spread over Jacob’s shaft and sliding all the way against his sphincter. The clenched tissue felt like it was on fire, as he rubbed the cotton thong soaked in his sweat against his sister’s boyfriend’s hard cock. Tristan couldn’t help himself. He arched his hips, working his ass up, so the head of Jacob’s cock was rubbing right against the door of his anus. The thin material of the thong just barely covered the entrance. Tristan could feel the smooth, warm head against his tender, young flesh. He was aching to be penetrated. Jacob adjusted the tilt of his hips back, so his rod was directed more towards Tristan’s entrance. Jacob pressed forward, willing the material to move out of the way. Tristan could tell his jabs were intentionally missing the mark, so his cock would sweep past the material. Their sweat and lust was building. The dewey precum from the horny teen was making the crevasse deep between Tristan’s cheeks to become slippery, and Tristan could feel the torment and lust in his kisses. He was feeling it too.
With each jab of Jacob’s cock, it was finding its mark more and more. Tristan could feel his sphincter releasing its tension, opening itself, as it familiarized itself with the welcome intruder. With a press forward, Tristen felt Jacob’s cock push some of the cotton thong into his anus. He pressed again, and the head pressed more material in. Jacob’s cock was finding the hot center—seeking it out—and with another push, more material worked its way in, making the thong cinch down on his hips. Jacob squeezed Tristan’s ass, as Tristan arched his hips up and down and the material pulled free. It was loose now, and with another thrust, Jacob’s cock pressed against the inner wall of Tristan’s crack, sliding along the length of his slippery flesh until it slid past the loose, thin, cotton material and found its mark. The head smashed itself against Tristan’s sphincter, which gently parted against the pressure. Jacob adjusted his position just slightly and pressed forward against, causing the slippery head to slide into Tristan’s rectal canal. Jacob moaned against Tristan’s neck, as he felt the burning hot flesh from within. Tristan could feel the lust in his loins. Jacob slowly glided the head back a fraction of an inch and then pressed forward again, sliding just slightly further forward. He firmly squeezed Tristan’s ass again, spreading his flesh, willing Tristan’s sphincter to accommodate more of his hard cock. He pressed forward again, and the head slid as deep as it could go, smashing against Tristan’s inner sphincter, which was clenched tight. It was a tease. Tristan’s asshole was hot, willing and open, but his insides were still unwilling to comply to their lust.
Jacob’s mouth was sucking hard on his neck. Surely there would be lots of hickies. The two boys were still grinding against each other, but it was clear that progress had halted. His inner walls were hot and tender, but they were too dry and his inner sphincter was not ready for the eager intruder. ‘What were they to do?’ Tristan thought.
“Oh my god. You are so hot,” Jacob said. Tristan could feel the lust in his words; it was palpable. “I can’t wait for tonight,” he said, thinking about how much cum he was going to dump in his girlfriend’s ass, but Tristan had other ideas.
Tristan was on the verge of cumming himself, and he wanted to feel Jacob in his body. Plus, if Jacob was like him then there was no way he was going to survive to the evening without cumming, so he set aside his better judgement, as the words just found their way out of his lips, “Why wait?” he whispered.